PL91820B1 - - Google Patents

Description

The invention relates to a manufacturing process of azo dyes derived from 2,6-diamd- nopyridines.

The method according to the invention produces barium Formulas I in which D is the remainder of active ingredient, R is optionally sub a substituted alkyl group or an optionally substituted alkyl group a converted phenyl group, X is hydrogen, group cyano optionally substituted with carbohydrate by mol, R1 is a group of formula C6H5, or an optionally substituted carbamoyl group, R1 is a group of * formula CeH5, a group of formula 4, of Formula 5, Formula 6, Formula (CH 2) 3 (CH 2 OH, (CH2) 3Oi (CH2) gOH, formula VII, formula VIII, formula or (CH ^ OC ^ R7, (CH2) ^ (OC2H4) (zOR8, (CH2) 3OR9, of formula 9, formula C2H4OCeH5, C2H4OC6H4CH3, of formula 10 or 11 or groups of formula 12, ex containing hydroxyl groups, R2 is hydrogen, R 1 or 11b optionally substituted with ali fatic, cycloaliphatic, aryilaliphatic or ary- Low, R3 represents an alkyl group of 1-3 atoms carbon or hydroxyalkyl, R 4 is water hydrogen, alkyl group having 1-3 carbon atoms or b a hydroxyalkyl group, R5 is hydrogen or a hydroxyl group, R 6 is hydrogen, the group al keel with 1-4 carbon atoms, methoxy group, ethoxy or chlorine, R7 is an ethyl group, propyl, butyl, cyclohexyl, benzyl, phenylbetyl or methylphenyl, R8 is hydrogen, alkyl group with 1-4 carbon atoms, cy- 2 clohexyl, phenyl, methylphenyl, petrol linear or phenylethyl, R9 is cyclo hexyl, phenyl, methylphenyl, benzyl . or phenylbetyl, m is 1 or 2, n o- means 0, 1 or 2, q means 2, 3 or b 4 and p is 1, 2, 3 or 4.

The dyes of formula I are prepared by reaction diazo compound of the amine of formula II with the coupling component of formula 3, where D, R, X, R1 and R2 are as defined above.

The rest of the D components of the coupling are derived from amines of the benzene, naphthalene, and diphthalene series nylon, benzthiazole, benzisoithiazole, thia- sol, thiaditrogen, thiophene, triazole- it, benzitriazole, indazole, pdrazole, azobenzene or anthraquinone.

As substituents for D residues, for example, in the benzene series: chlorine, bromine, nitro group wa, cyano, trifluoroimethyl, methylsulfony- Iowa; ethylsulfinyl, phenylsulfonyl, P - (/? - hydroxyethyl) phenylsulfonyl, carbomethoxy wa, carboethoxy, carbobutoxy, carbo - /? - methoxyethoxy, carbo-4-ethylhexoxy, carbo - /? - hydroxyethoxy, possibly N-mo- no- or N-disubstituted carbo- or sulfonamide, a methyl, ethyl, methoxy or ethoxy group xylow.

The non-substituents for carbon- or sulfonamides are e.g. methyl, ethyl, propyl, butyl groups 3o wa, jff-eitylbhexyl, cyclohexyl, /?-.methoxy- 0182091820 Iowa, n-methoxypropyl, or? -Ethoxypropyl and - tholidide, piperidide or morpholide.

In the azobenzene series: chlorine, bromine, the ni- frpwa, cyano, carbornethoxy, carboethoxy- Iowa, methyl, ethyl, metholxyl, ethoxy- 5 wa, hydrotttisytlowa, acetylanninowa, phonmylowa /? - hydroxyethoxy or ethoxycarbonylamino.

In the heterocyclic series: chlorine, bromine, group nitro, cyan, methyl, ethyl, phenyl, methoxy, ethoxy, methyflomerkapto (6 -car-10) lK) metoJcsyetylomerkapto, ^ carboethoxyethylomer- kapto, carbamethoxy, carboethoxy, acetyl low, methylsulifonyl or ethylsulifonyl.

The rest of D is derived e.g. from the following amines: aniline, o-, m-. or p-toluidine, o-, m-, or p-ni-15 jroanilines, o-, m-, and p-cyanoanilines, 2,4 ^ dicyc- Ianoanilines, o-, m- or p-chloroanilines, 3,4- or J ^ -dichloroanoliaiy, 2,4,5- or 2,4,6-trichloro aniiin, o-, m- or p-bfomoaniline, 2,4,6-tribrach moaniline, 2-chloro-4-nitroandline, 2 ^ bromo-4-ni- 20 troanilines, 2-cyano-4- nitroa nyl-4-nitroaniline, 2H-methyl-4-nd1xanilines, 2nme- toxy-4-nitroaniline, 4Hchlorone, 2-nitroaniline, 4nme- tylo-2-nitroaniline, 4-methoxyH2-niitroaniline, 1-a- mino-2- -5-amino-benzonitrile, 2-amino-6-chlorol> enzonitrile- lu, n-butylim! idu of l-amino-2-nitrbenzene- -4-sulfonic or N-methoxyethyl amide l Haauino-2-nitrobenzene-4HSuiphonium, 2,4-dini- troandliny, 2,4-dinitro-6-chloroaniliny, 2,4-di-30 nrtro-6H-bromoaniline, 2,4-dinitro-6-cyanoaniline, 1-amdno-2,4-dinitrobenzene-6-methylsulfone, 2,6- H -dichloro-4-natroainiUine, 2,6-dibromo-4-nitro aniline, 2HGhloro-6Hbrpmo-4-nL-trroaniline, 2,6-di- cyano-4-nitroaniline, 2-cyano-4Hndtro-6Hchloroani- 35 ropes, 2-cyano-4-yttrium-bromoaniline, 1-aminobene- eeno-4HmetyloisiuliflonRi, l-aim! ino-2,6-dwiubroimoben- ifcn © -4HiM0tylsulfomiu, lHaimino-2.6Hdichioroben- zene-4-methylsyphonium, an acid methyl ester 1Haimdno-2.6ninine; trobenzene-6Hcarboxylic acid or 40 1-amino-2,6-di- niitrobenzeneH6-carboxylic propyl ester and 3 N -dichloroanthranilic acid, ester, metho% 3,5-dibromoanthranilic acid xyethyl, N-benzoyl-phenylenediamine, NHacetyl-p-phe- nylene diamines, N-phenylsilphonyl-p-phenylene- diamines, N-phenylsulfonyl- ^ m-phenylenediamine, 4-a'minoacetophenate, 4- or 2'amiiriobenzophenone, 2-aminodiphenylsilphone, methyl ester, ester ethyl ester, propyl ester, butyl ester, 50 isobutyl ester, ^^ ethylhexyl ester, e- cyclohexyl string, benzyl ester, ester phenyl, β-methoxyethyl ester, β-α-ester methyl ethyl, butoxyethyl ester, ester methyldiglycol ester, ethyldiglycol ester, 55 methyltriglycol ester, ethyltriglycol ester WftK of hydroxyethyl ester, ester / phylaceto- of the methyl ethyl ester of the (jff'-hydixDxyethoxy-ethyl - (hydroxypropyl ester, γ-hy- droxypropyl, ca-hydroxybutyl ester, w 2-, 3- or acid n-hydroxyhexyl ester 4-amdnobenzoic acid, methyl ester, iso- butyl, methyldiglycol ester, ester ^ -methoxyethyl, jff-butoxyethyl ester, 5-nitroanthran-acid, 1-acetoxyethyl ester 66 lylic acid, dimethyl ester, diethyl ester, dipropyl ester, dibuty acid acid ester su 3- or 4-aminophthalic acid, 5-aminoiisofta- amine or aminoterephthalic, amide, methylamino du, propylamide, butylamide, isobutylamide. cyclohexylamMu, 4-ethylhexylamide, y-metho- xypropylamide, γ-ethoxypropylamide, anilide 3- or 4-aminobenzoic acid, diethylaimi- du, pyrrolidide, morpholide, N-methyl-N - ^ - hydroxy- 2-, 3- or 4-Haminobenzoic acid ethylamide> diamide, bis-γ-imethoxypropylamide of 5- Haminoisophthalic acid bis-diethylamide aminoterephthalic, imide, hydroxylimide, yH-hydroxypropylimide, phenyldid, p-tolylimide 3- or 4-Haminophthalic acid, N-hydroxy- 3-amino-6-] jiitrophthalic acid ethylimide, di- methylamide, diethylamide, pyrrolidide, morphol 2-, 3-, or 4-amino acid du, N-phthylnaphthylide benzenesulfonic acid, 2'-, 3'- or 4, -aininofe- ester nyiic methylsulfonic acid, 2 '-, 3'- ester or 1- aminophenyl ethyl sulfonic acid, buty-, 2'-, 3'- or 4, -ampinophenyl ester sulfonate, 2'-, 3'- or 4'Haminophenyl- ester of benzenesulfonic acid, ethylimide, bu- tyloyimide, /? - imethoxyethylimide, y-riethoxypropyl- 4-aminonaphthalic acid imide, 1- or 2-amino- naphthalene, 1-amino-2-ethoxynaphthalene, 2- or 4- -aimdnodiphenyl, l-aminoanthraquinone, l-aimino- -4-chloroanthraquinone, 3- or 4-amino di-oxide phenylene, 2-amdnobenthiazole, 2-amino-6-methylsul- fonylobenzitilazole, 2-amino-6-nitrobenzthiazole, 5,6- or 6,7H-dichloro-2-aminobenzithiaisole, 4-amino-5- -ibromo-7-nitro-1 ^ 4> enzisothiazole, 3-amino-5-nitro j2,1H-benzisoiaazole, 3-amino-5-nitro-7H-bromo-2,1- -ibenzisothiazole, 2-amariothiiazole, 2-amino-5-nitro thiazole, 2-Aimino-4-methyl-acid ethyl ester thiazole-5-carboxylic, 2-amino-4-methyl-5-ace- tylthiazole, 2-amino-3-cyano-4-methyl acid ester lotiophene-5-carboxylic acid, 2H-phenyl-5-amino-1,3- -4-thiadiazole, 3-imethylmercapto-5-amino-1,2,4-thia- dliazolu, S - ^ - kanbomeltlokisyetyilomeTikapto-S-amiino- ^ ly2,4-thiadiaizol! U, 3-amino-1,2,4-triazole, 4-amino-7- -niltroibeniztriaiz ^ lu, 3-amimodindazole, 3-amli! no-5-chJlo- irojindazole, S-amino-S-nitroindazole, 1-toenzyl-5- Hamiinopyrazoki, 1-phenyl-5-a'minoplrazoliu.

Suitable two-phase components in series aminoazene are e.g. 4-aminoazobenzene, 2,3-di- methyl-4-aminoazobenzene, 3R, 2-dimethyl-4-amino- azobenzene, 2,5-dimethyl-4-aminoazobenzene, 2-me- tylo-5-imethoxy-4 Haminoazobenzene, 2Hmethyl-4, 5- ^ dimethoxy-4-aminoazobenzene, 4'-chloro-2-methyl- lo-5Hmmethoxy-4-amdnoazobenzene, 4 H -nitro-2-methyl- -5-.methoxy-4-aminoazobenzene, 4 H -hydroxy-2H-methyl- 1-S-dimoxy-amino-azobenzene, 4'-i (Jtf-hydroxyetho- xy) -2-methyl-5-methoxy-4-amanoazobenzene, 4'-hy- Droxy-i2,2'-dimethyl-5- zen, 4, -hydroxy-4-aminoazobenzene, 4, -hydroxy- -2'nmethyl-4-amLnoazobenzene, 4, -hydroxy-3, -meth- lo-4-amirnoiazobenzene, 2, -hydroxy-5-methyl-4-aimi- noaEobenzene, 4'-hydiro] ^ sy-2 ^ metaxy-4 ^ a'miinoazo- benzene, 4'hydroxy ^ 2 - 'ch) 0: ro-4-arr: inoazobenizene, 4'- '-by droxy-2,5-dimethoxy-4-iaminoazobenzene, 4'- -hydroxy-2,6-dichloro-4-aminoazobeinzene, 4-hy- droxy-3-imethoxy-4-aminoazobenzene, 4'-chloro-2- -netyl-4-aminoazobenzene, 4-formyl-2-methyl -4-91820 -aminoazobenzene, 4M -toxycarbonylamirio) -2-non- tylo-4-aiminaazo azobenzene, 4'-chloro-2l5- wumethoxy-4-aminoazo- l> enzene, 4'-ni> tri-2,5'vumethoxy-4-am4noazobenzene 4Xhydroxyethoxy) H2,5% wumethoxy-4-aminoazes benzene, 4 'chloro-2,5-dimethyl-4-aminoazobenzene, 4'-methoxy-2,5-dVumethyl-4-amiinoazobenzene, 4'-ni- tro-4-aimiinoazobenzene, 3,5-dul, »omo-4-aminoazo- benzene, 2,3V-dichloro-4-aminoazole> enene, 3-imetho- flax, 2- (phenylazo-3-ethoxy-4-aminone: phthalene.

R groups are, for example, ethyl, n- or iso groups propyl, butyl, pentyl, a-ethyl pentyl, phenyl or methylphenyl and especially methyl low. 15 Substituted carbamodel groups X sa, e.g. N-methyl, N-ethyl-, N- butyl-, N - 4 - groups -hydroxyethyl-, N-y-ethoxypropyl-, N, N-di- methyl, N, N-diethyl, N, N-dibutyl- or TTHmethyl-N - ^ - hydroxyethylcarbimoyl. Step 2 » generally advantageous because it is easy to do the step is an unsubstituted carbamoyl group - wa.

In addition to the already mentioned R1 groups, you can eat Please indicate specific groups, such as: (CH2) 3-25 OC2H4OC2H5, (d ^ jOCy ^ -OCH (CH3) 2, (CH2) 30C2 ~ H ^ OC ^ g, (CH2) ajOC2H4OCH2C0H5, (CI ^ EGOC ^ H ^ pC ^ - H ^ CeHs, group of formula 13, 14, 15, 16, (GH2) 3- (OC2H4) 20CH3, a group of formula 17 and equivalents not groups in which moieties of formula - 30 OC2H4, formula 18 or 19, there are two-, three- or l fourfold and compounds in which C6H5 can be replaced by C ^ CH * Then you can turn off change more: (d ^ OCeH ^ (CH ^ aOCH ^^, (GH2) 30C2H4CgH5, groups of formulas 20, 21, 22 and 35 groups containing C6H4CH3 instead of C £ l5.

R2 is in addition to hydrogen and R 'groups, e.g. groups alkyls of 1-8 C atoms, including those that are inserted oxygen atoms and which can be substituted with hydroxyl, alkoxy, acyloxy groups, 40 carboxylic acid esters carboxylic acid groups cycloalkoxy, arylalkoxy or aryloxy- optionally substituted with a hydro group xyl, chlorine, hydroxyalkyl, chlorine roalkyl or alkyl, cycloalkyl group of 45 - 8 carbon atoms *, an aralkyl group of 7 - 15 C or B atoms, a phenyl group substituted with chlorine rem, hydroxyl, alkoxy, alkyl, hydroxyalkoxy or hydroxyalkyl and alkenyl, piTolidonylalkyl and carbo-50 groups xyalkyl.

The individual groups R2 sa, e.g. possibly substituted alkyl groups: CH3, C2H5, n- or iso-C3H7, n- or iso-C6g, C6H7, a group of formula 23, CH2CH = CH2, CHiCHpH, (CH2) gOH, group 55 formula 24 and 25, (CH2OH, (CH2) eOH, (C3l2) filGR2) - OH, (CH2) formula 26, (CH2) 3- OC2H4OCH3, (CH2) 30C2H40C2H5, CH2CH2OCH3, CR ^ CH. ^^ 3 ^ 7) CH2CH2OC4H9, (CH2) 30CH3, (CH2) 3- OC2H5, (CH2) 30C3H7, (CH2) 30C4H9, group of formula eo 27, (CH2 OC2a, (CH2) 30C & H17, a group of formula 28, 29, 21, 30, 3i, 32, 33, 34 and 20, carboxyalkyl group I and carboxalkoxyalkyl of the formula CHa — OOOE, CH2 ^ CH2- ^ OOOE, (CH2) 5 — OOOE or -HCO-H (CH2) a-HCXX) E, with E being 65 It combines, for example, hydrogen, methyl, ethyl and propyl groups wa, benzyl, /? - hydroxyethyl, co-hydroxy- hexyl, # -hydroxybutyl, N-methoxyethyl, f γ-M-methoxypropyl, γ-ethoxypropyl, (1-tevm- xyethyl or bul -hydrolkisyethoxyethyl, groups acylpcsyalkyl of the formula CH2 — CSH2 — O — Acyi " Acyl, {CH2) 2—0 ^ (CH2) t ^ O- ^ Acyl or (GH2) 3 — O— CX> -> C2H5, gurupe of formula 36, OO, CHaCl, CO- —CHz — CO— ^ GHz, CO ^ CH = and GH2, group of formula 37; CK> ^ CH = CH- C 1, 2, 2) 2, CXDOC 2 H 5, a group of formula 38, 30, 4fi or 41; wherein R1 groups contain groups hydroxyls can also be esterified acyl.

The acyl groups are hereinafter groups with the formulas COOP and OONHB, wherein B is e.g. a group alkyl or aryl. Individual groups are, e.g. groups OOOCH3, COOC2H5, COOC4H9, CONH- CH3, C5QNHC4H9, CONIK ^ Hs, CONHCeH4a or GONHCgHaCl.

Then there are pyrrolidonylalkyl groups with the formulas: 42, 43, 44 or 45, cycloalkyl groups of the formulas: 46, 47, 48, 49, 50, 51, 52 and 53, aralkyl groups with formulas: CHz — Gtfls, C ^^ Ce ^ h ^ CH2CHOH— —Cg ^ s and groups with formulas CoH ^, CeHjfOLj, C ^ a4CH3, CgHrfCHak, C6H4CN, CeH ^ H, CsH4OCH2- CH2OH, C6H /) CHa, C6H4OC2H5 or CeH ^ COCH *, groups containing CoH4 — CH3 instead of CgjHs, As inert diluents and solvents mono-, double or trichlorobenzene is used, tetrahydrofuran, dioxane, dimethylformamide, N-methylpyrrolidone or pyridine.

Preferably for esterification with free acids inorganic or organic catalysis is used thorium, e.g. HO gas or p-phboluenesulfonic acid and is formed in the reaction mixture water evaporates. Oh, but to esterify a hundred acid anhydrides or chlorides are used, e.g. time can in special cases as a resolution solvents use the respective acids. May so the reactions with acetic anhydride led to day in acetic acid. When using chlorides acidic esterifying agents, co Preferably, sro is added to the mixture acid-binding deco, e.g., carbonate or sodium acetate, magnesium oxide or pyridine. As ester agents In general, there may be changes to it, e.g. acid formic, acetic acid, chloroacetic acid, and esters, anhydrides or chlorides of these acids, ester chloronic acid, dicetene or isocyanate nannies. Carrying out of hydroxyl groups in carboxylic acid ester groups as well the finished dyes are converted into a conventional manner me from literature by methods.

Particularly valuable in any way with various dyes and dye mixtures: there are compounds of formula la, where per nitro, cyano, chlorine, bromine, ka'rt group |) - methoxy, carboethoxy, methoxy carbor ethoxy, methylsulfonyl, ethylsulfonyl, methyl, methoxy, phenylazo, g-1 ^ is hydrogen, nitro group, chlorine, bromine, cyano group wa, methyl, methoxy, carbomethoxy, 91 820 8 carboethoxylpwa, methylsulfonyl or ethylsulf- ionyl, a cyari; methyl, methoxy, carbomethoxy- low or carboethoxy one of the symbols A1 is one of the groups corresponding to R1 and the other g and A1 represent hydrogen or a group containing dgr p hydroxy or alicoxy, where the group is The hydroxyl group may be an esterified group formyl or acetyl.

Preferred groups R 1 are, e.g. the groups C 6 H 5, o formula 54, 55, 56, (CH2) 3 -4OC2H4OH, (CH2) 30CCH2) 6- OH, 'of formula 57, (CH2) zOC2'H. ^ OC2H.5f of formula 10 (C12)> C2H4CM2H2C6H5, (CH2) 3i (CX: 2H4) 2OR8, of the formula rze 9, OC2H4'C8H5, R8 is as defined above. Other¬ m and are preferred groups A1a, e.g. hydrogen, group co-hydroxybuityl, ctf-hydroxyhexyl, /? - hy- droxyethyl, β-hydroxypropyl or o the formula C2H4OCH3, Cy2OCH., CHfiHjOGHO, CHaCH ^ CHaOCHO, CHa- ^ CH ^^ OOOCH ^ (CH2) - £> - (CH2) 4fOH, (CH2 OCH2 pH, CH2CHOH- ^ C6H5, (CH2) 30R10, 0CH2) 3OC2H4OCH3 or (CH2) 30CjH4OC6- H5, with R10 representing hydrogen or an alkyl group Iowa with -1 ^ 4 C.

Preferred acyl groups are, e.g., CHO, COCH3 ltilb COC2H5. Then they are preferred groups with formulas 43, 45 or 46.

A further preferred group are dyes o formula 58, in which D, R 1 and X are above-mentioned given meaning.

It is advisable to select the groups R1 and R2 so that they contain at least one hydroxyl group or 1 or more oxygen atoms and sum of C atoms it was 5-30, preferably 5-16.

Dyes are also particularly valuable containing optionally as two-phase ingredients substituted nitro group, chlorine, bromine, cyano, methyl, imethyl mercapto, fi- -Jcarbomeitoksyethylimerkapto, /? - carboethoxyethyl- mercapto, carbomethoxy, carboethoxy es carboglycol terre or substituted acet- half benzthiaizole, benzphotozothilizole, thiazole or thiophene.

Among the particularly valuable ingredients diazo, replace 4-nitroaniline, 2 ^ - ichloro-4-mitroainiiJline ^ 2Hbromo ^ Hnitroani! liine, 2-cy- jano-4-nitroaniline, 2-imethoxy-4-nitroaniline, di- 2-amino-5-nitrophenylsulfon-acid methylamide 2-amino-5-nitrophenylsulfuric acid butylamide. phonic acid, /? - 2-amino-5- acid imetholxyethylamide -nitrotphenylsulfonic acid, 2-aminobenzonitrile, 3- -ehloro-4-aiminobenzonitrile, 2-chloro-5-aminobene- zonitrile, 2 Hamino, 5, chlorofoenzonitrile, 2.5, dihal- ro-4-aminobenzonitrile, 1-aminobenzonitrile, 1-ami- nó-2; 4-dicyanobenzene, 1-amino-2,4-dicyano- - E -chlorobenzene, 2-chloro-4-amino-5-nitrobenzene, 2Haamno-3-chloro-5-nitrobenzonitrile, 2-amino-3- -bromo-5-nitrobenzonitrile, 2,6-dicyano-4-nitro apifine, 2'-dichloro-4-nitroaniline, 2,6-dichloro- ro-4-nitroaniline, 2,6-dibromo-4-nitroaniline, 2- -chloro-6-ibroimo-4-nitroaniline, 2,4-dinitroaniline, 2,4-dinitro-6-chloroaniline, 2,4-dinitro-6-bromo moaniline, 2-amino-3,5-diinitrobenzonitrile, 1-amino no-4-nitrobenzene-2-methylsulfone, 1-amino-4-nitro benzene-2-ethyls, ulphon, 4-methylsulfonylaniline, 1- -amino-2-cVorobenzene-4-methylsul? qn, 1-amino- -2,6-cVv ^ mbromo.benzaio-4-methylsulfone, l-amino ~ -2,6-dichlorobenzene-4H-methylsulfone, acid ester 2- and 4-aminobenzoic acid, 2-aimino- ester -5-nliltroibenzoic acid, 2-amlho-3- acid ester ¦ 5-chloro-5-nitro-benzoic acid ester and 2-amino acid -3 * 5H-dichlorobenzoic acid, 2-amino acid ester -3.5% vubromobenzoic, methyl ester or 2-amino-3,5-diini- acid /? - methoxyethyl ester trobenzoic acid, 2-ami- acid duteyl ester and naterephthalic, 4-amdnobenzene, 2,3'dumeityl-4- aminoazobenzene, 2 ', 3-dimatyl-4-aminoacin 2,5-idwuanethyl-4-aminazobenzene, 3,5-dibromo-4- -aminoazobenzene.

Among the particularly valuable heterocycles cumulative two-phase components can be exchanged 2-amino-5-nitrothiazole, 2-amino-4H-methyl-5-nitrothia- sol, 2-amino-4-imethylthiazolo-acid ethyl ester -5-caiboixyl, 2-amino-5-phenyl-1,3,4-thiadiaisole, 3-phenyl-5-amino-yl, 2,4-itiadiazole, 3-methylmercapto- -S-amino-1H-thiadiazole, 3N / -Hcarbomethoxyethyl- mercapto- (5-aiminoHl, 2,4 ^ thiadiazole, 3 - ^ - carboethoxy- ethylmercapto, 5-amino-1,2,4-thiadiazole, 2-ammo-6- -cyanobenzothiazole, 2-αimi methyl ester no-i6-carboxyoyl ibenzthiazole, 2-amino-6-nitro benzthiazole, ester, 2% amino-3-cyano-4-methyl- lotiQphenH5- carboxylic acid, 3-amino-5-nitro-2,1- -benzisothiazole, 3-aminoH5-nitro-7-chloro-2,1-benzi zothiazole, 3-amino-5-nitro-7H-bromo-2,1-ben, zisothiazole. 4-1aimino-7-nitro-ly2 ^ benzisothiazole, 4-aimino-5-pho- ' mo-i4H-benzisothiazole, 4-amino-5H-bromo-7-nitro-1,2 benzisothiazole, 4-amino-5-cyano-7-nitro-1,2-benziso- thiazole, 4-aim! ino-5-chloro-7-nitro-1,2-benzisothiazole.

The new dyes produce a color from yellow to blue and suitable for dyeing fabrics from afcrylonitrile polymers, synthetic polymers lamides, cellulose esters such as 2V2- or triacet- new moon, in particular of polyethylene glycol terephthalate new or chemical analogs of polymers Strong, distinctive dyes are obtained 40 August with special durability.

The diazotization of the amine of formula DNH2 carries out in a known way, but also as usual takes place in an aqueous environment, possibly with the addition of a solvent, with a reaction 45 because it is very acidic.

The preparation of the coupling components is described in notification NRF (P 2062717.2).

If produced by the method of the invention dyes of formula 1 contain W groups R * 50 µl of R2 ester group can be produced compounds of the formula (I) lead essentially to the In the following manner,% y is the appropriate ester group wa is already included in the * coupling component. IN Many, however, are preferably the rest Add 55 acid (acyl) to the finished dye formula 1. Free acids are suitable for this purpose, anhydrides, chlorides or esters.

The following examples will explain the invention in more detail beds, with the parts and percentages given in them 60 are parts. and percentages by weight, if not. is stated differently.

Example I. iMixture of 187 parts 2.6 ^ two- clhloro-3-cyano-4-methylpyridine, 200 parts iso- propanol and 30K), aniline parts mixed through 65 8 hours at 90 ° C 100 ° C, then -91,820 Table 1 Example no 1 1 II III IV V VI VII VIII IX X XI XII XIII XIV XV XVI XVII XVIII XIX XX XXI XXII Xxiii Xxiv xxv XXVI XXVII Xxviii XXIX | xxx [XXXI XXXII XXXIII XXXIV xxxv XXXVI XXXVII XXXVIII XXXIX XL XLI XLII XLIII XLIV XLV XLVI XLVII XLVIII XLIX L. LI LII LIII LIV LV LVI LVII LVIII LIX LX LXI LXII LXIII | LXIV Ingredient two-phase 2 pattern 90 " , " » pattern 91 " pattern 92 5J pattern 93 " pattern 95 ,, pattern 96 ,, pattern 97 " 5J ,, pattern 98 and) ., " pattern 99 " pattern 100 ,, pattern 101 ?, pattern 102 pattern 103 " pattern 104 jj R2 3 —CH2 — CHo — CHo — O — CH3 - ^ CH9 — CH2 — OH —CH2 — CH2 — CHo — OH pattern 94 -CHo-CHo — O — CHo — CHo — OH —CH2-CH2 — O — CH3 H. —CHo — CHo — OH —CHo — CHo — CHo — OH pattern 94 —CH2 — CHo — O — CH2 — CHj — OH —H —CHo — CHo — OH —CHo — CHo — CHo — OH pattern 94 —CHo — CHo — O — CHo — CHo — OH —H —CHo — CHo — OH —CHo — CHo — CHo — OH pattern 94 —CH2 — CH2 — O — CHo — CH2 — OH H. —CHo — CHo — OH —CHo — CHo — CH2 — OH pattern 94 —CHo — CH2 — O — CH2 — CHo — OH H. —CHo — CHo — OH —CHo ^ CHo — CHo — OH —CHo ^ CHo — O — CHo — CHo — OH H. —CH2 — CHo — OH —CHo — CHo — CHo — OCOCH3 pattern 94 ^ CHo — CHo — O — CHo — CHo ^ OH ^ CHo — CHo — O — CH3 —CHo — CHo — CHo — O — CH3 —CHo — CHoOCHO - (CH2) G ^ dH —H —CHo — CHo — OH —CHo — CHo — CHo — OH —CHo — CHo — O — CHo — CHo — OH. pattern 94 —CHo — CHo — CH> —O — CHo, —CHo — CHo — CHo — OCOCHo —CHo — CHo — OH —CH2 — CHo — tH2 — OH —CHo — CHo — O — CH2 — CH2 — OH ^ CHo — CHo — OH —CHo — CHo — CHo — OH —CHo — CHo — O — CH2 — CHo — OH —CHo — CHo — OH —CHo — CHo — CHo ^ OH —CHo — CHo — OH —CHo — CH2 — CHo — OH —CHo — CH2 — O — CH2 — OH —CHo — CHo — OH —CHo — CHo — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CHo — CHo — OH —CH2 — CH2 — CH2 — OH —CHo — CHo — O — CHo — CH2 — OH Coloring j 4 1 yellow with a red tinge golden yellow yellow with a red tint 'l> »> •» a >> »» 5) yellow . , yellow with a red tinge »J> >> >> >> »> w. . ; ; » >> l> 5l r> yellow with a red tinge golden yellow / >? 1 golden yellow » you red-orange scarlet » scarlet with a brown tint | red-orange scarlet > » Orange scarlet red-orange-scarlet scarlet red with a tinge of yellow # " fiery red si scarlet " Red >> scarlet " yellow with a red tinge >> >> l> '> > »5? J> J) red-orange tf " Orange " • j> 191820 11 12 c. d.-table 1 1 1 2 | 3 | 4 \ ; lxv LXVI LXVII LXVIII 1 LXIX LXX LXXI LXXII LXXIII LXXIV LXXV LXXVI LXXVII LXXVIII LXXIX LXXX LXXXI LXXXII LXXXIII LXXXIV LXXXV LXXXVI LXXXVII LXXXVIII LXXXIX XC XCI XCII XCIII | XCIV pattern 105 pattern 106 »» pattern 107 > » > » »» pattern 108 pattern 109 pattern 110 pattern 111 pattern 112 pattern 113 pattern 114 1 »> H. —CH2 — CHa- ^ OH —— —CH2 — CH2 ^ —CH2 — O ^ —CH3 ^ CH2 — CH2 ^ OH '- ^ CH2 ~~' CH2 — OH2 — On - ^ aH2- ^ CH2-O-CH2-CH2-OH —H —CH2 ^ - * CH2 — OH —CH2 — CH2 — CH2 — OH -nCHa- ^ CHa — O — CH2 — CH2 — OH —CH2 CH2 — O — CH3 —CH2 —'CH2 — CH2 — OH ^ CHa — CH2 — O — CH2 — CH2 — OH —CH2 --— CH2 — CH2 — OH ^ CH2- ^ CH2-O-CH2-CH2-OH ^ CH2-hCH2 — OH - ^ CH2 ^ CH2 — iCH ^ OH - €% —CHjj — O-hCHjt-OH ^ CH2 — CHs- ^ OH —CH2 — CH2 — CH2 — OH pattern 94 ^ CH2 — CH2 — O — CH2 — CH2 ^ OH —CH ^ CHr- ^ OH —CH2 — CH2 — CH2 — OH ^ CH2 ^ CH2 ^ O-CH2-CH2-OH —CHa- ^ CHa- ^ OH —CH2 — CH2 —'CH2 — OH —CH1) - 1 — CH2 — CH2 — CH2 — OH Orange 99 l golden yellow 99 99 f golden yellow Orange Red [ scarlet » post-orange [ »1 orange l "1 > »[ golden-yellow-orange "1 »1 Orange Orange Table 2 Components of the interval of formula 115 f example no 1 XCV XCVI XCVII XCVIII XCIX c CI CII CIII CIV cv ¦ cvi CVII CVIII CIX ex, CXI CXII CXIII CXIV cxv Ingredient two-phase 2 pattern 90 • pattern 91 pattern 92 pattern 97 pattern 95 pattern 98 >> pattern 106 pattern 107 >> 3 —CH2-CH2- ^ OH —CH2 — CH2 — CH2 — OH —CH2 ^ -OH2 — O — CH2 — CH2 — OH —CH2 ^ CH2- ^ OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — CH2 —O — CH2 — CH2 - ^ OH —CH ^ CHj ^ OH —CH2 — CH2 — CH2 — OH —CiH2 ^ —CH2 ^ - 'O — CH2 — CH2 — OH —CH2 — CH2 ^ OH —CH2 —- hCH2 — CH2 — OH ^ CH2 ^ CH2 — O — CH2 — CH2 — OH —CH2 ^ CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH.

—CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 ^ OH —CH2 — CH2 — CH2 —'OH —CH ^ —CH2 — CH2 — O ^ CH3 Coloring l % 1 4 yellow with a red tinge ti a a a golden yellow | ii 1 golden yellow [ scarlet • ii scarlet with a brown tinge ii »> ii a Red golden yellow a | Orange »> L18 91820 AT is left to cool and poured while stirring it binds to about 1500 parts of water, 200 parts concentrated it is hydrochloric acid and 200 parts of ice, and it still mixes for 1 hour, sift the precipitate, probably similarly of formula 59 and washed with water until 5 indifferent. After drying, you get olcolo 240 parts of a colorless powder, of [temperature mp 135-140 ° C. 12.2 parts of this powder are mixed with 40 parts m and y-hydroxypropylamine for 6 hours at tern-10 temperature 145-160 ° C, after cooling it, the mixture is mixed Shanine with 100 parts of water and * acidified with acid salt to a pH value of about 0 to 1. Receives possibly after adding a small amount of glacial acetic acid or dimethylformamide, solution 15 formation of the coupling component, probably of a pattern at 60. Solution (or suspension) of this product it is cooled by adding ice to a temperature of 0-3 ° C and he inflicts with a solution of the diazonium salt obtained as follows: 20 6.9 parts of p-nitroaniline are dealt with about 30 parts of concentrated (30%) hydrochloric acid and 80 parts water, and then cooled the mixture to temperature temperature 0 ° C and add 15 parts by volume in portions essential 23% sodium nitrite solution; He mixes for 2 hours, removes the event in a known manner total excess of nitric acid and salt.

The filtrate is added to the coupling mixture and gradually adding as much acetate 30 with stirring sodium or sodium hydroxide to adjust the value The pH of the fusion mixture is up to 2-3. If the mixture is difficult to mix, you can add ice cold water. After completion of coupling the mixture heated to 70-80 ° C, filtered, and heated washes and dries. You get about 20 parts of red a tawny-brown powder, probably of a pattern at IT, dissolving in dimethylform- tears with a red tint and tinted fabric nine from polyethylene terephthalate to strong, 40 pure scarlet with a very high degree of durability losci.

Dyes are produced in a similar way, characterized by the following ingredients two-phase and coupling components. 45 Example CXVI. 24.4 parts of the reaction product anilines from 2,6-dichloro-3-cyano-4-methylpyridine (example I) mixed with 80 parts y-methoxy- of propylamine for 3 hours under pressure, at temperature 140 ° C 160 ° C, then 50 after cooling adds 8 parts of 50% sodium liquor and distilled excess γ-methoxypropylamine and water. Mon. the residue is treated with 100 parts of 85% acid within 5 hours at temperature 100 ° C. After cooling, it is blown into a mixture of 55 about 500 parts of water, 600 parts of ice and 100 parts 50% sodium lug. To chilled to temperature 0 ° C of the mixture containing the coupling component, possibly Formula 116, a batch is added m and a solution of diazotized 3-amino-5-nitro-2,1-60 -benzisothiazole, prepared as follows way: 19.5 parts of 3-amino-5-nitro-2,1-ibenzisothiazole do passes while mixing, at tempe-fiateze - ^ 25C ° in portions to from about 75 to 85 hours 6% sulfuric acid is cooled to ¦ 0-4 ° C. Then it drips at this temperature \ J2.5 parts of 23% niitrosyl sulfuric acid. Two- Azization is completed after about 4 hours: stirring at 0- ^ 5 ° C. Because the task is to 1 s failure of coupling with a diazonium solution, pH value (the mixture is adjusted by adding; An acid binding agent, such as sodium acetate (or lye: sodium), down 1.5 ^ 2.5. For a good home At a temperature of 0-5 ° C, ice is added in the mixture ice cold water. After the coupling is completed, The shisha is heated to a temperature of 60-80 ° C.

The lost dye is filtered off and washed with it-: white water. After drying, you get about; 40 parts of black powder as a dye; probably formula 117, dissolving, in dimethylformamide with a blue tint - ' and dyeing 'polyethylene terephthalate fabric' blue with a shade of green, O; very good durability.

Example CXVII. 122 parts of the reaction product the aniline ionization from 2,6-dichloro-3-cyano-4-methydopyrid-; dyna (example I) is treated with 150 parts N- ^ methylpyrrolidone and about 1000 parts of 25% aimo-j niacin for 15 hours at 180 ° C; autoclave * - Lost product after cooling! possibly Formula 118, is removed, translated; washes with water and dried. You get around 108 parts of a colorless product. 22 parts of this pro-1 the duct dissolves in about 100 parts of the ice acetic acid, cooling it by adding ice to temperature 0-2 ° C and a small amount is added sulfamic acid. The mixture is diazo solution is added in portions at 0 ° C 2-amino-5-nitrobenzonitrile, produced -: it as follows: ¦ ¦ ¦> 16.3 parts of 2-amino-5-nitrobenzonitrile are added chilled to 0 ° C in portions a mixture of about 90 parts 96% sulfuric acid and 3 and 2.5 parts of 23% nitrosyl sulfuric acid. After! Stirring for 4-5 hours at 0-4 °! diazotization is complete.

For quick and complete connection of property a shackle that can be diluted with ice cold and cold water is brought in at a temperature 0-5 ° C by adding sodium acetate solution, to pH values around 2.5. After the spell is over The mixture is heated to a temperature of approx 80 ° C, lost dye probably of the pattern It is drained and washed with hot water. • You get about 38 parts of dark brown a powder that dissolves in dimethylforma mid with a red tint, and IJkanine with The color of polyethylene terephthalate is very pink red to red, very durable.

Analogously to examples I, CXVI and CXVTI | the dyes characterized below are produced; given tables by means of two- azo and fusion. 15 91820 l « Table 3 Coupling component of formula 80 Example no 1 CXVIII CXIX cxx CXXI CXXII CXXIII CXXIV cxxv CXXVI CXXVII CXXVIII CXXIX cxxx CXXXI CXXXII CXXXIII CXXXIV cxxxv CXXXVI CXXXVII CXXXVIII CXXXIX CXL CXLI CXLII CXLIII CXLIV CXLV CXLVI CXLVII CXLVIII CXLIX CL CLI CLII CLIII CLIV.

CLV CLVI CLVII CLVIII CLIX CLX CLXI CLXII CLXIII CLXIV CLXV CLXVI CLXVII CLXVIII CLXIX [CLXX CLXXI CLXXII CLXXIII CLXXIV CLXXV CLXXVI CLXXVII CLXXVIII CLXXIX CLXXX CLXXXI 1 Ingredient two-phase 1 2 pattern 120 1 jy 1 yy pattern 121 pattern 122 pattern 123 fy yy pattern 124 ? » pattern 125 yy > pattern 126 pattern 127 > y formula 1.28 pattern 129 pattern 130 pattern 131 yy "1 pattern 132 pattern 133 pattern 134 yy y> 'R2 3 —CHo ^ CHo ^ OH ^ CHo ^ CHo — CH2 — OH pattern 94 - ^ CH2 — CHo — O — CH2 — CH> —OH —CH2 — CHs- ^ CHj — OCHO —CH2 ^ CHo — O — CH3 - ^ Cair-OH ^ CH2 — CH3 — O — COCH3 —CHo — CH2 — OH - CH2 — CH2 — CH2 — OH pattern 94 —CHo — CH9 — O — CH> —CHo — OH —CH2 — CH2 — O — CH3 —H [- < $ I2-hCH2- ^ OH and ^ -CH2-CH2-CH2-OH f pattern 94 —CH2 — CH2- ^ O — CH2 — CH2-OH —CH2 ^ —jCH2 ^ —O —'CH3 —'CHo — CH2 — CH9 — O — CH3 —CH2 — CH2 — O ^ COCH3 —H —CHo — CH2 — OH —CH2 — CH2 — CHo — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — O — CH3 —CH2 — CH2 — OH ^ CH2 — CH2 — CH2 — OH ^ CH2 — CH2 — O — CH2 — CH2 — OH —CH ^ CH, —OH —CH2 — CH> —CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CHo — CH2 — OH —H —CHo — CH, —OH —CHo — CH2 — CHo — OH ^ CH2 — CHo — O — CH2 — CH2 — OH —CHo —'CHo — O ^ —CH3 —CHo — CHo — OH —CHo — CH2 — CH2 ^ OH —CH2 — CH2 ^ O — CHo — CHo — OH —CH2 ^ CH2 — O — COCH3 —CHo — CHo — OH —CHo — CHo — CH2 — OH pattern 94 —CHo — CHo — O → CH2 — CH2 — OH —CHo — CH2 — OH —CHo — CH2 — CH2 — OH —CHo — CHo — CH2 — O — CH3 —CH2 — CH2 — O — H —CHo — CH2 — CHo — OH —CHo — CH2 — O — CHo — CH2 — OH CHo — CHo — CH2 — O — CH3 —CHo — CHo — OH —CHo ^ CHo — CH2 — OH —CHo — CH2 ^ OH —CH2 — CH2-CHo — OH —CH2 — CHo — O — CH2 — CH2 — OH —CHo — CH2 ^ OH ^ CH2 — CH2 — CHo — OH ^ CH2 — CH2 — O — CHo — CH2 — OH 1 1:: '-: -: - v: 1 Coloring ! 4. pink 1 "'I ¦ •» ¦ 1 i> 1 Red pink | Red ¦ w red with a shade of yellow [ ruby I »> [ »» '| »1 "1 j »1 yy | ruby L yy 1 yy 1 Red Red yy "1 Red red dark red fy l yy red with a shade of brown [ "1 red with a brown tinge red with a brown tinge "- 1 "1 Violet "1 "1 "I red with a blue tint red with a blue tint Orange "191820 17 18 c. CL Table 3 1 and 2 j 3 [4 "* | CLXXXII CLXXXIII CLXXXIV CLXXXV CLXXXVI CLXXXVII CLXXXVIII CLXXXIX CXC CXCI 1 CXCII CXCIII CXCIV cxcv CXCVI CXCVII CXCVIII CXCIX cc CCI CCII CCIII CCIV ccv CCVI CCVII CCVIII CCIX ccx CCXI CCXII | CCXIII CCXIV ccxv CCXVI CCXVII CCXVIII CCXIX ccxx CCXXI CCXXII CCXXIII CCXXIV ccxxv CCXXVI CCXXVII CCXXVIII CCXXIX ccxxx CCXXXI CCXXXII CCXXXIII CCXXXIV ccxxxv ccxxxvi ; 5cxxxviii CCXXXVIII CCXXXIX CCXL CCXLI CCXLII CCXLIII CCXLIV CCXLV | CCXLVI pattern 135 pattern 136 and) pattern 137 pattern 138 pattern 139 pattern 140 pattern 141 pattern 142 pattern 143 pattern 144 pattern 145 pattern 146 pattern 147 pattern 148 pattern 150 pattern 151 pattern 152 pattern 153 pattern 154 1 J5 pattern 155 pattern 156 pattern 157 —CH2 ^ CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2--0 — CH2 — CH2 — OH —H —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 - (CH1HHCH4-OH —CHa — CH2 — OH —CH2 — CH ^ —CHo — OH pattern 94 —CH2 — CH2 — O — CH> —CH2 — OH -h (CH1) 6-OH -h (CH2) 3-O— ^ CH2-CH2-CH2-O-CO-CH3 —CH2 — CH2 — O — CH2 — CHo — OH —CH2 — CHo — CH2 — OH —CH2 — CH> —O — CH> —CHo — OH —CH2 — CHo — CHo — OH —CH2 — CH2 — O — CHo — OH - ^ CHo-CHo — O — CH > —CH2 — OH -h (CH2) 3-O — H —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH - (CH1) 3-OH ^ CH2 — CHo — O — CH2 — CH2 — OH —CHo — CHo — CH2 — OH —CH2 — CH2 — O — CH2 — CHa — OH —CHo — CHo — CHo — OH —CHo — CH ^ —O — CH2 — CH2 — OH -ICHo-hCH, 1CH 2 3 OH _CH2 — CH2 — O ^ CH2 — CH2 - OH —CH ^ —CH2 — OH —CH2 — CH2 — CH2 — OH —CHo — CB) -O — CH2 — CH2 — OH - (CHaIa — O— (CH2) 4 — OH —CH2 — CH> —CH2 — OH —CHo — CH ^ —O — CHo — CH2 — OH -h (CH2) j-O-; (CH2) 4A) H —CH2 — CHo — CH2 — OH —CH2 — CB2-O — CH2 — CH2 — OH —CHo — CHo — CH2 — OH _CH2 — CB2-O — CHo — CHo — OH —CH2 — CHo — CHo — OH —H —CHr-CH2 — OH —CHo — CHo — CH2 -— OH —CH2 — CH2 — O — CH2 — CH2 — OH 1 —CH2 ^ CH2 — OH —CH2-CHo-CHr-OH pattern 94 —CHo — CH * —O — CHo — CH2 — OH —H —CHo — CH2 — OH —CH2 — CHo — CHo — OH _CH2 — CHj — O — CHo — CHo — OH —CHo — CH2 — OH —CH2 — CHo — CHo — OH —CHo — CHj — O — CHo — CHo — OH pattern 94 -CHr-CH2-OH —CH2 — CHo — CHo — OH 1 —CH2 — CH2 —O — CH2 — CH2 — OH orange 1 in 'i * '1 dysentery with a blue tinge ruby '' 1 red with a blue tint navy blue navy blue with a tint of blue | nielbdeskli (blue) | red brown »» 1 golden yellow "1 golden yellow "1 purple 97 1 »J | Violet scarlet red scarlet red "! red with a tinge of yellow ruby "1 "1 violet | » purple 1. » Violet ruby red-orange scarlet > 1 » scarlet red-orange Violet "1 "1 red with a blue tint red-violet 1 * ' | »| red-violet 1 "91820 19 20 c. D. Table 3 1 1 f CCXLVII CCXLVIII • CCXLIX CCL CCLI CCLII | CCLIII 2 | 3 pattern 158 pattern 159 pattern 160 pattern 161 --CH2 — CH2 — CH2OH —CH2 — CH2 — CH2 — OH —CH2 — CHj — O — CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH --CH2- ^ CH2-CH2-OH 4 I Red \ Violet ( blue with a red tinge st [ ** 1 blue | Table 4. Coupling component of formula 115 Example no 1 CCLIV CCLV | CCLVI CCLVII CCLVIII CCLIX CCLX CCLXI CCLXII | CCLXIII CCLXIV CCLXV CCLXVI CCLXVII CCLXVIII CCLXIX | CCLXX CCLXXI CCLXXII CCLXXIII | CCLXXIV 1 CCLXXV CCLXXVI CCLXXVII CCLXXVIII CCLXXIX CCLXXX | CCLXXXI | CCLXXXII CCLXXXIII 1 CCLXXXIV CCLXXXV CCLXXXVI CCLXXXVII CCLXXXVIII | CCLXXXIX | CCXC | j CCXCI I ccxcn 1 Ingredient two-phase 1 2 pattern 121 pattern 120 pattern 136 pattern 122 pattern 123 11 11 11 pattern 162 pattern 147 11 pattern 150 pattern 163 pattern 164 pattern 165 pattern 127 pattern 142 pattern 159 pattern 124 Ri 3 —CH2 — CH2 ^ OH —CH2 — CH2 — CH2 — OH | —CH2 — CH2 — O — CH2 — CH2 — OH —H ^ CH- ^ CH, —OH —CH2 — CHo — O — COCH3 —CHj — CH2 ^ CH> —OH _CH2 — CH2 — O — CH2 — CH2 ^ OH —CH> —CH2 — O — CH2 — CHoOCHO - (chVoh —CH, —CH, —CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —H —CHi — CH9 — CH —CH2 — CH2 — CH2 — OH pattern 94 _CH, —CH2 — O — CH? —CH2 ^ OH —CH2 — CH2 — CH —CH, —CH2 — CH2 — OH —CH2 — CH2 — O — CH ^ CH2 — OH ^ (CH2) 3-0 ^ (CH2) 4-OH —CH2 — CH2 — CH2 — OH ^ CH2 — CH9 — CH2 — OH —CH2 — CH2 — O — CHo — CH2 — OH —CH2 — CH2 — CH2 — OH —CH, —CH2 — O — CH, —CH2 ^ OH —CH2 — CH2 — CH, —OH —CHc — CH2 — O — CH2 — CH2 — OH —CHs — CH2 — O — CH2 — CH2 — OH —CHr — CH2 — O — CH2 — CH2 — OH —CH> —CH9 — CH —CH2 — CH2 — CH2 — OH —CH, —CH2 — O — CH2 — CH2 — OH —CH, —CH2 — CH, —OH —CHs — CH2 — O — CH2 — CH2 — OH —CH2-CH, —CH2-OH —CH2 ^ CH2 — O — CH2 — CH2 — OH —CH2-CH, —CH2-OH —CH ^ —CH2 — O — CH2 — CH2 — OH | Coloring 1 4 Red pink Red pink dark red pink 99 dark red ruby t> ruby r> . » t) ruby » 19 Violet ruby Violet navy blue 1 "1 blue blue dark red Violet *> Violet Red and I91820 21 22 Table 5 The coupling component of the formula 166 1 Example no 1 1 CCXCIII CCXCIV CCXCV CCXCVI CCXCVII CCXCVIII CCXCIX ccc CCCI CCCII and ccciii CCCIV cccv CCCVI CCCVII CCCVIII CCCIX CCCX CCCXI CCCXII CCCXIII CCCXIV cccxv CCCXVI CCCXVII CCCXVIII 1 Component two-phase 1 2 pattern 98 pattern 120 pattern 122 > •> pattern 163 91 pattern 165 R2 1 and 3 —CH2 — CHo — O — COCH3 —CHo ^ -CHo — CHo — O — COCH3 —CHo-CH2 — CHo — OH —CH> J — CH2 — O — CH3 —CHo — CH2 — OCOCH3 —CH2 — CH2 — CH2 — OCOCH3 —CHo — CH2 — CHo — OH —CHo — CH2 — O — CHo — CHo— OCOCH3 —CH ^ CH, —O — CHo — CHo — OH —CH2 — CHo — O — CH3 —CH2 — CHo — CH2 — OCOCHn —CH2 — CHo — CH2 — OH --CH2 — CH2 — O — CHo — CHo— OCOCH3 —CHo — CHo — O — CHo — CHo — OH —CH ^ CH3 —CHo — CH2 — CHo — O — CH3 —CH2 — CH2 ^ O — COCHo — COCH3 —CHo — CHo ^ OCOCH3 —CH2 — CH2 — CH ^ O — OOCH3 —CHo — CH2 — CHo — OH —CHo — CH2 — O — CH3 —CH2 — CHo — CH2 — O — CoH5 —CHo — CH2 — O — CHo — CH2 — OCHO —CH * —CH2 — O — CH2 — CH2 — OH —CH> —CHo — O — CH2 — CHo — O— COCH3 * "\ —CHo — CHo — O — CHo — CHo — O— COCH3 | Coloring 1 4 Red \ »\ red with a blue tint a »J "1 >> J Violet ;> 1?> 1 "1 »I blue with a green tinge in 1 » 99 1 99 I 99 "\ blue with a green tinge Table 6 Coupling component of formula 167 Example no 1 1 CCCXIX CCCXX CCCXXI CCCXXII CCCXXIII CCCXXIV cccxxv CCCXXVI CCCXXVII CCCXXVIII CCCXXIX cccxxx CCCXXXI CCCXXXII CCCXXXIII CCCXXXIV CCCXXXV CCCXXXVI OCCXXXVII CCCXXXVIII CCCXXXIX 1 Ingredient two-phase 2 pattern 98 pattern 120 • 9 • 9 pattern 122 pattern 163 ¦> 5 pattern 165 »» 1 pattern 164 »J 1 Hi 3 —CHo-CH, -CHo-OCOCH, —CHo — CHo — CHo — OH —CHo — CH ..— CHo — OCOCH3 —CH, —CH> —CHÓ — OH —CH2 — CHo — O ^ CH2 — CHo — OCOCH3 —CHo — CH2 — O — CHo — CH2 — OCHO -CH, -CHo-CH, -O-COCH3 —CH3 — CHn — O — CHo — CHo — OCHO —CHo — CHo — O — CHo — CH, —O — COCH3 —CH2 — CHo — CH2 — O — COCH3 —CHo — CHo — CHo — OCOCH2 — COCH3 —CHo — CHo — CH, —OH —CHo — CHo — O — CHo — CH, —OH —CHo — CHo — O — CHo — CHo — OCHO —CHo — CHo — O — CHo — CHo — OCOCH3 —CHo — CHo — O — CHo — CHo — OCHO —CH.2-CHa- ^ O ^ CHa — CH2 ^ O ^ GQCH3 CH2 — CHS — O — CH2 — CH2 — OH -h (CH2) 3-0- (CHo> -OH —CH2 — CHo — O — CH2 — OCOCH3 —CH2 — CHo — CH2 — O — CH3 | Coloring 4 I Red red with a blue tint "1 69 Violet blue with ode ierr: stung 91 1 "1 blue with a green tinge 9) I "1 blue with a green tinge j> L91820 23 84 Table I Coupling component of formula 177 " Example no 1 CCCXLVI CCCXLVII CCCXLVIII CCCXLIX CCCL CCCLI CCCLII CCCLIII CCCLIV 1 CCCLV CCCLVI CCCLVII CCCLVIII CCCLIX CCCLX CCCLXI CCCLXlt CCCLXIII CCCLXIV OCCLXV CCCLXVI ¦- CCCLXVII s CCCLXVIII * ¦ CCCLXIX CCCLXX CCCLXXI CCCLXXII CCCLXXIII CCCLXXIV OCCLXXV CCCLXXVI CCCLXXII 1 CCCLXXIX CCCLXXX CCCLXXXI CCCLXXXII CCCLXXXIII CCCLXXXIV CCCLXXXV CCCLXXXVI CCCLXXXVII CCCLXXXVIII OCCLXXXIX CCCXC 4 CCCXCI . CCCXCII CCCXCIII CCCXCIV cccxcv CCCXCVI CCCXCVII CCCXCVIII CCCXCIX CD CDI CDII CDIII CDIV CDV CDVI CDVII And CDVIII Ingredient two-phase 2 1 pattern 90 *> l f> l "1 ** 1 pattern 91 "1 pattern 92 pattern 93 pattern 95 pattern 96 >> >> pattern 97 * ' ti 1 '* pattern 98 loam ii ii 1 a 1 » pattern 99 ii Jl pattern 100 1 " pattern 101 pattern 102 1 9J pattern 103 pattern 104 R2 3 | H. —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —CHfj — CH2 — O - * - CH3 1 H. —CH2 ^ CH2 — OH —CH2 ^ CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —H —CH2 ^ CH2 — OH —CH2 ^ CH2 — CH2 — OH pattern 94 —CH2 — CHa — O — CH2 — CH2 — OH —H —CP2 ^ CH2 — OH —CH2 — CH2 — CHa — OH pattern 94 —CH2 ^ CH2 — O ^ CH2 — CH2 — OH | H. ^ CH2 — CH2 — OH —CH2 ^ CH2 - <: H2 — OH pattern 94 —CH2 ^ CH2 — O — CH2 — CH2 — OH H. ^ CH2 — CH2 — OH —CH2 ^ CH2 — CH2 — OH ^ CH2 — CH2 — O — CH2 — CH2 — OH H. —CH2 ^ CH2 — OH —CH2 — CH ^ —CH2 — OCOCH3 pattern 94 —CH2 ^ CH2 — O — CH2 — CH2 — OH —CH2 ^ CH2 — O — CH3 —CH2 — CH2 — CH2 — O — CH3 —CH2 — CH2OCHO ^ (CH2) G — OH —H —CH2 — CH2 — OH —CH2 ^ CH2 — CH2 — OH —CH2 ^ CH2 — O — CH2 — CH2 — OH pattern 94 —CH2 ^ CH2 — CH2 — O — CH3 —CH2 ^ CH2 — CH2 — OCOCH3 —CH2 — CH2 — OH ^ CH2 ^ CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 ^ CH2 — OH ^ CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 - OH —CH2 ^ CH2 — OH _ ^ CH2 ^ CH2 — CH2 ^ -OH —CH2 ^ CH2 — OH —'CH2 —— CH2 — CH2 — OH —CH2 — CH2 — O ^ CH2 — CH2 ^ OH —CH2 — CH2 — OH ^ CH2 ^ CH2 — CH2 — OH —CH2 — CH2 — O ^ CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 ^ CH2 — CH2 ^ OH | —CH2 ^ CH2 — O — CH2 — CH2 — OH and Colors \\ 4; | 1 1 46lte li : ii, ti M \ yellow ; m 1 a 1 ii t and 1 yellow "1 "1 ' yellow ^ \ ii 1 ii In 1 Orange mp t and i ti Orange » Orange ii lf 1. a 1 a i a 1 \ a 1 scarlet "1 "1 a 1 l a 1 scarlet l a 1 \ a red with a tinge of yellow 1 ** 1 Orange yellow 1 ** Orange n yellow 91 820 26 c. 1 1 1 2 CDIX CDX CDXI CDXII CDXIII CDXIV CDXV CDXVI CDXVII CDXVIII CDXIX CDXX CDXXI CDXXII CDXXIII CDXXIV CDXXV CDXXVI CDXXVII CDXXVIII CDXXIX CDXXX CDXXXI CDXXXII CDXXXIII CDXXXIV CDXXXV CDXXXVI CDXXXVII | CDXXXVIII pattern 105 pattern 106 pattern 107 pattern 108 pattern 109 pattern 110 pattern 111 pattern 112 pattern 113 pattern 114 3 H. —CK., - CHo — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — CH2 — O — CH3 —CH2 — CHo — OH —CHo — CHo — Ca — OH —CH2 — CH2 — O — CHo — CH2 — OH —H —CHo — CHo — OH —CH2 — CH2 — CE2-OH —CH2 — CHo — O → CHo — CH2 — OH —Ca-CHo — O — CH3 —CHo — CHo — CHo — OH —CH2 — CHo — Otf —CH2 — CHo — CH “—OH —CH2 — CH2 — O — CH2 — CH2 — OH - ^ CH2-CHo-OH —CHo — CHo — CHo — OH —CHo — CHo — O — CHo — CHo — OH —CHo — CHo — OH —CH2 — CH2 — CH2 — OH pattern 94 | —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — OH * —CHo — CH2 — CHo — OH —CH2 — CHo — O — CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CHo — Ca — OH —CHo — CHo — OH —CHo — CH2 — CE, -OH | AND yellow > 5 yellow yellow red with a tinge of yellow Orange yellow golden yellow > and " yellow and yellow » yellow Table 2 Coupling component of formula 178 Example no 1 1 CDXXXIX CDXL CDXLI CDXLII CDXLIII | CDXLIV CDXLV CDXLVI CDXLVII CDXLVIlt CDXLIX | CDL CDLI CDLII CDLIII CDLIV CDLV CDLVI CDLVII CDLVIII 1 CDLIX Ingredient two-phase 2 pattern 90 pattern 91 pattern 92 pattern 97 pattern 95 pattern 98 pattern 106 pattern 107 Ri 3 —CHo — CHo — OH —CHo — CHo — CH, —OH —H —CHo — CH2 — OH —CHo — CHo — CH> —OH —CH2-CHo-CHo-O [theta] (CH2) 2OH —CH2 — CH2 — OH —CHo — CHo — ca-oh —CHo — CHo — O — CH2 — CHo — OH —CHo — CH2 — OH —CHo — CHo — CH ^ —OH —CHo — CHo — O— (CHo) 2OH —CH2 — CH2 — CH2 — OH —CH2 — CHo — O — CH2 — CHo — OH —CHo — CH, —OH —CH ^ —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2-CHo-O [beta] (OH2) 2OH —CH2 — CH2 — OH —Ca — ca — ca — oh —CH2 — CH2 — CH2 — CH Coloring 4 yellow yellow * ' >> yellow golden yellow yellow 1 * Orange "1 post-orange scarlet > yellow loam yellow } »191 27 iAruflogically, dyes with patterns are produced and given in conjunction with the relevant examples give me: Example CCCXL, Dye Formula 168, red color, example CCCXLI, dye pattern 169, red tinted color ! blue, example CCCXLII, dye with formula 170, orange color, example CCCXUII dye formula 171, color scarlet.

Example CCCXLIV. 11 parts of the dye o formula 172 is heated with 100 parts by volume formic acid, under a reflux condenser for 4 hours. After cooling, add while "mixing about 100 parts of water, it is lost product of formula 173, washed with water and dried.

You get about 11 parts of dark brown a powder that dissolves in dimethylform mid with a red tint and which fabric of polyethylene terephthalate dyes pink red to red, highly durable.

Example CCCXLV. A mixture of 187 parts 2.6 Dichloro-3-cyano-4-methylpyridine, 200 jun isopropane and 300 parts of 2-n-phenylpropylamine it is stirred for 8 hours at 45-55 ° C.

After cooling, the mixture is poured in during the mornings to about 1500 parts of water, 200 parts of water hydrochloric acid and 200 parts of ice. He mixes for 1 more hour, sift the sediment, possibly Formula 174 and washed with water until it is neutral. After drying, it is replaced about 240 parts of a colorless powder, approx mp 100-105 ° C. parts of this powder are mixed with 40 parts N-hydroxyethylamine for 6 hours at room temperature rush i45-160 ° C. After cooling down, it is asked to do shanine with 100 parts of water and acidified with acid salt to a pH value of 0-1. I get optionally by adding a little glacial acetic acid of wadded or dimethylformamide, composition solution no coupling, probably of the formula 175.

Cool the solution (or suspension) of this product by adding ice to a temperature of 0-3 ° C and stopping gives the solution of the diazonium salt which is obtained is spoken as follows: 6.9 parts of p-nitroaniline are sold around 30 June with concentrated hydrochloric acid (30%) and 80 parts water, and then cooled the mixture to temperature of 0 ° C and administer 15 parts in portions by volume 23% sodium nitrite solution. Have Shanine is mixed for 2 hours, removed if necessary found in excess nitrogen in known way and sucks.

Praesacz is added to the coupling mixture and as much sodium acetate is added when mixing soda lye to get the pH value of the mixture the coupling was 2–3. If mixing is done It is difficult to add ice water. After After the coupling is completed, the mixture is heated to 70- ^ 80 ° C, filter, washed with water. and dries. You get about 20 parts of brown a powder, possibly of Formula 176, which was dissolved it runs in dimethylformamide with a color orange, and terephthalate fabric 820 28 of polyethylene, it turns a strong, clean orange black color with very high durability.

Dyes are produced in a similar way characterized by the components of diazotization and coupling components, given in tables 1 and 2.

Example of CDLX. 19.5 parts 3-amino-5-ni- tr-2,1-l-benzisothiazole is added with stirring options at 15-25 ° C to about 75-85 parts of 96% sulfuric acid and a mixture of and white to 0-4 ° C, then 32.5 drops parts of 23% nitrosyl sulfuric acid. Two-phase It just ends with pfe 3 to 4 hours in another city at 0-5 ° C. A mixture of salt The diazonium salt is added to it cooled to 0 ° C solution or suspension of 34 parts of the coupling component Runs formula 179, 50 parts of 30% acid salt, 500 parts of water, and 150 parts of ice watery acetic acid. When pairing up to¬ ice and sodium acetate are added successively, so that the the temperature of the coupling mixture did not exceed and 5 ° C and the pH was finally 2. The precipitate the dye of formula 180 is filtered off, washed with water wa hot water and dried. You get around 53 parts of the black powder that dissolves in blue dimethylformamide with a red shade.

Example CDLXI. Get 50 parts of the powder in the GDLX example, mixes with about 200 parts of 80-95% sulfuric acid by 5 hours at BO-100 ° C, then poured, a mixture of up to 1500 parts of ice water, lost dye of formula 181, washed water and dried. About 40 parts of moth are obtained a powder that dissolves in dimethyl formamide with a blue tint and dye fabric made of polyethylene terephthalate per color blue.

Further two-phase ingredients from the examples of CCC—> DCLXII give with the coupling components of the formula 40 191 (dyes that fade away from the corresponding dyes of 2-phenylpropylamine group differs its properties slightly.

Example DCLXXXIV. A mixture of 187 Jun sci 2,6-dichloroH3-cyano-4-methylpyridine> 150 45 parts of triethylamine, 200 parts of isopropanol and 160 parts of 2-aimino ^ 6-imethylheptanol-6, mixed for 8 hours at 55-80 ° C, cooled and poured about 1500 parts of water, 200 parts concentrated hydrochloric acid and 200 parts of ice, under- 50 mixing time. Stirs for 1 more hour, decant from the separated oil, lead Salt icing to a pH of 0-1. Receives possibly after adding a little acid acetic acid or dimethylformamide solution 55 of the coupling component, possibly of the formula 192, containing a small amount of the 2,6-double-double isomer- loamines. • '.

The solution of this coupling component cools by adding ice, to a temperature of 0-3 ° C and adding 60 with the diazonium salt obtained as follows dashing way: 6.9 parts of p-nitroaniline are added around 30 June with concentrated (30%) hydrochloric acid and 80 parts water, and the mixture is then cooled to a 65 at 0 ° C and add 15 parts ob-91820 in portions 29 30 Table 3 Coupling component of formula 177 Example no 1 CDLXII CDLXIII CDLXIV CDLXV CDLXVI CDLXVII CDLXVIII CDLXIX CDLXX CDLXXI CDLXXII CDLXXIII CDLXXIV CDLXXV CDLXXVI CDLXXVII CDLXXVIII CDLXXIX CDLXXX CDLXXXI CDLXXXII CDLXXXIII y CDLXXXIV CDLXXXV CDLXXXVI CDLXXXVII CDLXXXVIII CDLXXXIX CDXC CDXCI CDXCII CDXCIII CDXCIV CDXCV CDXCVI CDXCVII CDXCVIII CDXCIX D DI 1 DII DIII DIV DV DVI DVII DVIII DIX DX DXI DXII DXIII DXIV DXV DXVI DXVII DXVIII DXIX DXX DXXI DXXII DXXIII DXXIV . DXXV Ingredient two-phase 2 pattern 120 pattern 121 » pattern 122 ? 7 formula 12.3 93 "'1 pattern 124 pattern 124 pattern 125 pattern 126 pattern 127 pattern 128 pattern 129 9) 1 pattern 130 J5 j pattern 131 pattern 132 pattern 133 pattern 134 R2 3 —CH2 — CH2 — OH —CH2-CH2-CH2- ^ OH pattern 94 —CH2 — CHa — O — CHa — CH2 — OH —CH2 — CH2 — iCH2 — OCHO H. ^ CH2) 6- ^ OH —CH2 — CH ^ O — COCH3 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH H. "H" —CHa — CH2 — OH —'CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — O — CH3 —CH2 — CH12 — CH2 — O — CH3 ^ CH2 — CH2 ^ O — COCH3 —H —CH2 ^ CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — O — CH3 —C2H5 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHs ^ CHa — QH —CH2 ^ CH2 — OH —CH2 — CH2 — CH2 ^ OH —CH2 — CHa — O — CH ^ CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — CH2 ^ OH —H —CH9 — CH2 ^ OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHs — CH2 — OH —C-'H2 — CH2 — O — CH3 ^ CH2 — CH2 — OH —CHa — CHo — CH2 — OH —CH2 — CH2 — O — CHa — CH2 — OH ^ CH2 — CH2 — O — COCH3 —CH2 — CH2 — OH —CHa — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CHa — CH2 — OH —CH2 — CH2 — OH —CH → CH2 — CH2 — OH ^ CH2 — CH2 — CH2- ^ 0 — CH _ —CH2 — CH2 — O — H -hCHs-CH2-CH2-OH - ^ CH2 — CH2 — O — CH2 — CH2 — OH —CHy- ^ CHa — CH2 — O — CH3 —CH2 — CH2 — OH -CHa; -CH2-CH2-'OH —CH9 — CH2 — OH —CH2 — CH9 — CH2 — OH —CH2 — CH2 — O — CHa — CH2 — OH —CH2 — CH2 — OH —CHa-- ~ CH2 — CH2 — OH - ^ CH2 — CHa — O — CHz-£ Ep — OH Coloring 4 red with a tinge of yellow > »L »> 1 scarlet red with a tinge of yellow 1 »» 1 scarlet "1 "1 "1 "1 ruby »! 1 "1 »1 »» 1 "'1 1 "1 ruibinowe [ "1 "1 "1 »» 1 in 1 >>. . AND red 1 Red Red > and 1 red I 4 red I 91 1 93 f 99 i scarlet with a brown tinge "1 "1 "»> 1 scarlet with a brown tinge I. * »1 >> i "1 scarlet with a brown tinge 1 9 * l red with a blue tint "1 "1 red I Red > »¦ ¦ 99 yellow l>, 131 91820 32 c d. Table 3 1 and 1 a 1 3 1 DXXVI DXXVII DXXVIII DXXIX DXXX DXXXI DXXXII . DXXXIII DXXXIV DXXXV DXXXVI DXXXVII DXXXVIII DXXXIX DXL DXLI DXLII DXLIII DXLIV DXLV / DXLVI DXLVII DXLVIII DXLIX DL DLI DLII DLIII DLIV DLV DLVI | DLVII DLVIII DLIX DLX DLXI DLXII DLXIII DLXIV DLXV DLXVI DLXVII DLXVIII DLXIX DLXX DLXXI DLXXII DLXXIII DLXXIV DLXXV DLXXVI DLXXVII DLXXVIII DLXXIX DLXXX DLXXXI DLXXXII DLXXXIII DLXXXIV DLXXXV DLXXXVI | DLXXXVII pattern 135 pattern 136 pattern 137 pattern 138 pattern 139 pattern 140 pattern 141 pattern 142. * • pattern 143 pattern 144 pattern 145 pattern 146 pattern 147 and, pattern 148 pattern 150 pattern 151 | pattern 152 pattern 153 i * j pattern 154 1 ii pattern 155 pattern 156 1 f> » —CHo — CH2 — OH ^ CHo — CHo — CHo — OH —CHo — CH2 — O — CH2 — CH2 — OH —H —CHo — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 - (CH2) 3 — O— (CHo> —OH —CHo — CHo — OH —CH2 — CH2 — CH2 — OH pattern 94 —CHo — CHo — O — CHo — CH2 — OH - ^ (¦CH2) 6 - ÓH —CHo — CH2 — CHo — O — COCH> (CH2) 3 ^ O- (CH2) ^ OH —CH2 — CHo — O — CHo — CHo — OH —CHo — CHo — CHo — OH —CHo — CHo — O — CH2 — CH2 — OH —CH2 — CH2 — CHo — OH —CHo — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — O — CHo — CH9 — OH ^ (CH2) 3 — O — H —CHo — CHo — OH —CHo — CHo — CHo — OH H. —CHo — CHo — O — CHo — CH2 — OH - (CH>) 3-OH —CHo — CHo — O — CHo — CH2 — OH H. —CHo — CH2 — OH —CHo — CHo — CHo — OH —CHo — CH2- ^ OH —CHo — CHo — OH H. —CH2 — CH2 — OH —CHo — CHo — CHo — OH —CHo — CHo — O — CHo — CH2 — OH - (CH2) 3-O- (CH2) 4-OH —CHo — CHo — CHo — OH —CHo — CHr-O — CHo — CHo — OH —H —CH2 — CHo — CHo — OH —CH2 — CHo — O — CH2 — CHo — OH —CH2 — CHo — CHo — OH —CHo — CHo — O — CHo — CHo — OH —CH2 — CHo — CH2 — OH —H —CHo — CHo — OH —CH2 — CHo — CHo — OH —CH2 — CHo — O — CH2 — CH2 — OH —CHo — CHo — OH —CHo — CH2 — CH2 — OH pattern 94 —CHo — CHo — O — CH2 — CH2 — OH —H —CHo — CH2 — OH —CH2 — CH2 — CHo — OH —CH2-CH2-O — CH2 — CHo — QH —CHo — CH2 — OH —CH2 — CHo — CHo — OH —CHo — CH2 — O — CH2 — CHo — OH | pattern94 4 1 yellow "1 >> 1 Red } 7 1 "1 > »I V> 1 blue with a red tinge • blue (blue) yellow-brown »| yellow » yellow >? red with a blue tint red with a blue tint scarlet scarlet scarlet red with a blue tint and* Violet 1 red with a blue tint Violet _> » Violet ruby Orange Orange 1 n »' '»> | »> Violet | >? red with a blue tint 1? J91830 34 c. d. table 3 1 1 DLXXXVIII DLXXXIX DXC DXCI DXCII DXCIII DXCIV DXCV DXCVI DXCVII 2 pattern 157 pattern 158 pattern 159 ? » pattern 160 pattern 188 1 S. —CH2 — CH2 — OH —CH2 — CH2 — CHa — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — CHa — OH —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH H. —CHa — CH2 — OH —Cli2 — CH2 — CH2 — OH —CH2 — CH2 — CHa — OH 4 | red with a tinge of .nieibieskhi * In 1 red | • red z Violet blue z shade of blue "1 »> 1 shade of red. J. Table 4 Coupling component of formula 178 Example | no 1 DXCVIII DXCIX | DC DCI DCII DCIII DCIV DCV DCVI j DCVII DCVIII | DCIX DCX DCXI DCXII DCXIII | DCXIV DCXV DCXVI DCXVII 1 DCXVIII J DCXIX DCXX | DCXXI DCXXII | DCXXIII DCXXIV 1 DCXXV DCXXVI DCXXVII 1 DCXXVIII DCXXIX | DCXXX | DCXXXI DCXXXII DCXXXIII DCXXXIV | DCXXXV | DCXXXVI | Ingredient two-phase • 2 pattern 121 pattern 120 pattern 136 pattern 122 > pattern 123 pattern 162 pattern 147 pattern 150 pattern 163 pattern 164 pattern 127 pattern 142 pattern 159 pattern 124 > »1 R \ 1 3 —CH2 — CH2 — OH —CH2 ^ CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —H —CH2 — CH2 — OH —CH2 — CH2 — O — COCH3 —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHa — CH2 — OH —CH2 — CH2 — O — CHa — CH ^ OCHO - (CH2) oOH —CH2 — CH2 — CH2 — OH —CH2 — CHa — OH —H —CH> —CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CHj — O — CH2 — CH2 — OH —CHo — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CHa — O — CHo — CH2 — OH _ ^ (CH2) 3--0— (CH2) 4-OH —CH2 — CH2 — CH2 — OH —CH9 — CHo — CH2 — OH —CH2 — CHj — O — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CHa — OH —CH2 — CH ^ —CH2 — OH —CH2 — CHa — O — CH2 — CH2 — OH —CH2 — CHo — O — CH2 — CH2 — OH H. —CH2 — CH2 — OH —CH2 — CH2 —'CHa — OH —CH2 — CHa — O — CH2 — CH2 — OH —CH2 — CHa — CH2 — OH —CH2 — CHa- ^ O — CH2 — CH2- ^ OH | —CH2 — CH21 — CHa — OH —CHa — CHa- ^ O— (CH2) 20H ^ CHa — CHa — CH2 — OH —CHa — CHa — O — CHa ^ OH | Coloring | 4 scarlet red with a tinge of yellow Red Red ruby »> L »•> 1 Red »1 rufbdnowe "1 Violet ruby »1 Violet "1 blue with a red tinge »1 blue red 1 »1 "1 a 1 red with a blue tint red with a blue tint '»'; red (5 91820 Table 5 The coupling component of formula 189 1 Example no 1 1 DCXXXVII DCXXXVIII DCXXXIX DCXL DCXLI DCXLII DCXLIII DCXLIV DCXLV DCXLVI DCXLVII DCXLVIII DCXLIX DCL DCLI DCLII DCLIII DCLIV DCLV DCLVI DCLVII DCLVIII DCLIX DCLX DCLXI DCLXII Ingredient two-phase 2 pattern 98 * » > j >> pattern 120 »> and* 11 »> 01 pattern 122 » " " » " pattern 163 »> " " » ,, *> »> « pattern 190 R2. 3 -> CHy-CH2 — O — COCH3 —CH2 — CH2 ^ CH2 — O — OOCH3 —CH2 — CHa — CH2 — OH —CH2 — CH2 — O — CH3 CH2 ^ CH2 — OCOCH —CH2 — CH2 — CH2 — OOOCH3 —CH2 — CH2 — CH2 — OH ^ CH2 — CH2 — O — CH2 — CH2 — OCOCH3 —CH2 — CH2--0 — CH2 — CH2 ^ OH —CH2 — CH * —O — CH3 —CH2 ^ —CH2 — CH21 — OCOCH3 —CH2 — CH2 — CH2 — CH — OH —CH2 — CH2 — O — CH2 — CH2 — OCOCH3 —CH2 — CHa- ^ O — CH2 — CH2 — OH —CH2 — CH3 —CH2 — CH2 — CH2 —O — CH3 —CH2 — CH2 — O — COCHa — COCH3 —CH2 — CH2 — OCOCH3 —CH2 — CH2 — CH2O — COCH3 —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH3 —CH2 — CH2 — CH2 — O — C2H5 —CH2 — CH2 — O — CH2 — CH2 — OCHO —CH2 — CH2--0 — CH2 — CH2-4OH ^ CH2 ^ CH2 ^ O ^ CH2 ^ CH2 - ^^ COCH3 —IC ^^ CH ^ - ^ O ^ CHa- ^ CHgr ^ O ^ COCH, ^ Coloring 4 Red > » > » 99 red with a blue tint | and red-violet in Pi • 9 M. »L blue • » * » * vol »» »> IN »» in blue with a green tint | Table 6 Coupling component of formula 191 Example no 1 DCLXIII DCLXIV DCLXV DCLXVI DCLXVII DCLXVIII DCLXIX DCLXX DCLXXI DCLXXII DCLXXIII DCLXXIV DCLXXV DCLXXVI DCLXXVII DCLXXVIII DCLXXIX DCLXXX DCLXXXI DCLXXXII DCLXXXIII Ingredient two-phase 2 pattern 120 »> loam pattern 98 pattern 97 pattern 123 pattern 127 11 11 pattern 91 B2 3 H. —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 ^ O — CH2 — CH2 ^ OH H. —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2--0 — CH2 — CH2 — OH H. —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 ^ OH H. —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH H. —CHa — CH2 — OH —CH2 — CH2 — CH2 — OH H. —CH2 — CH2 — OH Coloring 4 scarlet; fiery red Red red with a tinge of yellow scarlet ¦ M ¦ 99 (Orange 19 19 99 red with a tinge of blue ruby 11 Red 11 99 yellow 19 l91820 37 38 Table 1 Coupling component of formula 194 (Example 1 no 1 1 : dclxxxv DCLXXXVI 1 DCLXXXVII DCLXXXVIII DCLXXXIX DCXC DCXCI DCXCII DCXCIII DCXCIV DCXCV DCXCVI DCXCVII And DCXCVIII DCXCIX DCC DCCI DCCII DCCIII DCCIV DCCV DCCVI DCCVII DCCVIII DCCIX DCCX DCCXI DOCXII DCCXIII DCCXIV DCCXV DCCXVI DCCXVII DCCXVIII DCCXIX DCCXX DCCXXI DCCXXII DCCXXIII DCCXXIV DCCXXV DCCXXVI DCCXXVII DCCXXVIII 1 DCCXXIX DCCXXX DCCXXXI DCCXXXII DCCXXXIII DCCXXXIV DCCXXXV | DCCXXXVI DOCXXXVII DOCXXXVIII DCCXXXIX DCCXL, 1 DCCXLI DCCXLII * DCCXLIII DCCXLIV DCCXLV DCCXLVI DCCXLVII DCCXLVlll 1 DCCXLIX 1 Ingredient two-phase 2 model 90 " »> ii pattern 911 »» »> pattern & 2 »» » j> ii pattern 93 9i and and et pattern 95 and *> and pattern 96 'ii pattern 97 in ii M. pattern 98 »> pattern 99 pattern 100 pattern 101 pattern 102 »» pattern 103 »» pattern 104 pattern 105 pattern 106 pattern 107 > pattern 108 »J ' R2 3 H. - ^ CH2 ^ CH2 — OH —CH2r2CH2-Cu2-^ OH pattern 94 H. —CH2 ^ CH2 — OH —CH2 —- ^ CH2 — CH2 — OH pattern 42 pattern 44 -hH —CH2 — CH2 — OH —CH2 — CH2 — CH2—> OH pattern 43 pattern 45 —H ^ CHo — CH2 — OH -1CH2 ^ CH2-CH2-OH pattern 94 pattern 46 H. --CH2-CHa-OH —CH2 — CH2 —- ^ CH2 — OH pattern 94 H. —CH2 ^ CH2 — OH —CH2 — CH2 — CH2 — OH H, pattern 42 —CH2-CH2- ^ CH2-OCOCH3 pattern 94 —CH2 — CH2 ^ O — CH3 —CH2-CH2 "-CH2-O-CH3 ^ CH2 ^ CH2OCHO ^ (CH2) —H ^ CH2 — CH2 - OH —CH2-CHa-CHr-OH pattern 94 —CH2 — CH2 - CH2 — O — CH3 -CH2 "-CH2-OH —-CH2 ~ -CH2- ^ CH2-OH —CH2 - CH2 — OH ^ CH2 — CHa — CH2 — OH ^ CH ^ CH ^ OH —CH2 ^ CH2 - CH2 — OH —CH2 ^ CH2- ^ OH —CH2 — CH2 — CH2 — OH —CH ^ CHa — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 ^ CH2 — CH2 — OH H. —CH2 — CH2 — OH —CH ^ —CH2 — CH2 — OH —CHa — CHa — CH2 — O — CH3 ^ CH2 ^ CH2 — OH —CH2 ^ —CH2 — CH2 ^ —OH —H —CH2 — CH2 — OH —CH2 — CH2 — OH (CH2) 5COOH ^ CHa — CH2 — O — CH3 —RCH2 — CH2 — CH2 — OH - ^ CHa — CH2 — OH Coloring | 4 yellow >> 1 »> 1 »1 yellow "1 in i . »» '.' ] yellow > and 1 j> 1 "1 yellow " » « a \, Orange ** 1 "1 »? 1 Orange »1 »| Orange »1 »» 1 9 * 1 "1 99 1 99 1 ii [ 99 | scarlet ** 1 »'I n 1 »F scarlet 1 .. *> 1 red with a tinge of yellow »1 Orange ** L. yellow I # f Orange t »1 yellow ii 1 golden yellow ii 1 99 1 99 L. yellow 1 »1 yellow a 1 ii zlottóólte (polyamide) yellow red with a tinge of yellow a ¦ 191820 1 ¦ ¦ 1 1 DCCL DCCLI DCCLII DCCLIII DCCLIV DCCLV DCCLVI ¦ DCCLVII DOCLVIII DCCLIX DCCLX DCCLXI " | DCCLXII 39 2 I formula 109 pattern 110 ** pattern 111 pattern 112 pattern 113 pattern 114 ^ 3 1 - ^ CH2 ^ CH2 — CH2 OH ' —CHy-CHz — OH —CH2 — CH2 — CH2 — OH ^ CHs- ^ CHa ^ OH —CH2 — CH2 — CH2 — OH model 94 l —CH2-ch; 2-oh —¦CH2- ^ CH ^ -CH2-OH (CH2) sCOOH —CH2 — CH2 — OH —CH2 — CH ^ —CHa — OH —CH2 — CH2 — OH 1H -CH2-CH2-CH2-OH 40 cont. table 1 4 l Orange [ yellow [ Hf I golden yellow 1 * »1 yellow I yellow-yellow (polyamide) 1 yellow yellow 1 in ' Array | 2 Coupling components of formula 195 Example inr 1 DCCLXIII DCCLXIV DCCLXV DCCLXVI [DCCLXVII DCCLXVIII DCCLXIX DCCLXX DCCLXXI DCCLXXII DCCLXXIII DCCLXXIV DCCLXXV DOCLXXVI | ' DCCLXXVII Ingredient two-phase 2 pattern 196 pattern 91 pattern 92 pattern 97 pattern 95 pattern 98 pattern 106 pattern 107 Fi 3 '-CH2-CH2 ^ OH —CH2 ^ CH2— * CH2 — OH —H —GH2 ^ CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CHa — OH —CHs — CH2 ^ OH —CH2 ^ CH2 ^ CH2 — OH —CH2 — CH2 — CH2 — OH ^ CH2 — CH2 — OH —CHj — CH2 ^ CH2 ^ OH _ ^ CH2 ^ CH2 - CH2 — OH —CH2 — CH2 — OP _CH2 — CH2 ^ CH2 — OH | —CH2 — CH2 — CH2 — CH3 Coloring 4 yellow yellow * t j, > » yellow 1 orange 1 and orange | scarlet yellow yellow 1 99 1 high-quality 23% sodium nitrite solution. He mixes for 2 more hours, remove any remaining excess nitric acid, in a known manner, and suck off.

(The sliver is added to the fusion mixture, then gradually introducing as much sodium acetate or soda lye to get the pH value of the mixture the coupling was 2–3. As long as stirring is agitated nina presents difficulties, then one can add ice water *. After you are done bonding The shash is heated to 70-80 ° C, sat or, washed with water and dried. You get about parts of brown powder, probably Fr. formula 193 (the dye contains a small amount of the isomer 2,6HdwTualkilbaminopyridine). The dye dissolves in dimethylformamide with a tinted color orange and the fabric made of polyethylene terephthalate bacwi to a strong, pure orange color high durability.

Characteristic dyes are obtained analogously rice with two-phase ingredients and ingredients coupling, given in tables 1 and 2. example DCCLXXVIII. 19.5 pieces 3-ami- 65 NO-S, Nitro-1 H-benzisothiazole is added portionwise with stirring at 15-25 ° C to about 75-85 parts of 96% sulfuric acid and a mixture of Shanine is cooled to 0-4 ° C. Then it drips up at this temperature, 32.5 parts of 23% nitro sulfide. Bicase after * 3-4 hours mixing at 0-5 ° C is complete and the diazonium mixture is added until cooled to 0 ° C of the solution or suspension 34.9 parts of the coupling component, with the formula 197 in 50 parts, 30% hydrochloric acid, 500 parts water and 160 parts of glacial hydrochloric acid.

During coupling, ice and heat are gradually added the sodium tan so that the temperature of the mixture is gania did not exceed 5 ° C. Finally the pH value is around 2. Lost dye of formula 198 is drained, washed with hot water and dried.

About 53.6 parts of black powder are obtained, dissolving in dimethylformamide z blue with a red tint, tinted.

Example of DOCLXXIX. 21.6 parts 2-amino- N -nitrabenzenemethylsulfone is mixed with 10091 820 41 43 Table 3 Coupling components of formula 194 1 Example no 1_ DCCLXXX DCCLXXXI DCCLXXXII DCCLXXXIII DCCLXXXIV DCCLXXXV DCCLXXXVI DCCLXXXVII DCCLXXXVIII DCCLXXXIX DCCXC DCCXCI DCCXCII DCCXCIII DCCXCIV DCCXCV DCCXCVI DCCXCVII DCCXCVIII DCCXCIX DCCC DCCCI "DCCCII DCCCIII DCCCIV DCCCV DCCCVI DCCCVII DCCCVIII DCCCIX DCCCX DCCCXI DCCCXII DCCCXIII DCCCXIV DCCCXV DCCCXVI DCCCXVII DCCCXVIII DCCCXIX DCCCXX DCCCXXI DCCCXXII DCCCXXIII DCCCXXIV DCCCXXV DCCCXXVI DCCCXXVII DCCCXXVIII • DCCCXXIX 1 "DCCCXXX iDCCCXXXT Dcccxxxn DCCCXXXIII | DCCCXXXIV 1 DCCCXXXV DCCCXXXVI DCCCXXXVII DCCCXXXVIII DCCCXXXIX DCCCXL DCCCXLI I DCCCXLII I Ingredient two-phase 2 pattern 120 » 11 pattern 121 pattern 122 11 91 91 11 pattern 123 s » 11 11 pattern 124 pattern 125 pattern 126 pattern 127 pattern 128 pattern 129 Si pattern 130 pattern 131 Xi pattern 132 pattern 133 pattern 202 pattern 136 pattern 136 > »1 a i pattern 91 9 * 1 ti ^ 2 3 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 - ^ CH2- ^ CH2-CHo ^ OCHO H. HCH2) c-OH —CH2 — CHa — O — COCH3 —CH> —CH2 — OH —CH2-CH2- ^ CH2-OH pattern 94 H. -H " —CHj — CH2 — OH —CH2 — CH2 - CH2 — OH pattern 94 —CH2 — CHo —- O — CH3 —CH2 — CH2 — CHo — O — CH3 ^ CHa — CH2 — O — COCH3 —H —CH ^ —CH2 — OH '—CH2 ^ —CH2 — CH ^ —OH pattern 94 —CH2 — CH2 — O — CH3 —C2H5 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CHo — OH —CH2 — CH2CH2 — OH —CH2 — CH2 — OH —CHs — CH2 — CH2 — OH —H —CH2 — CHo — OH —CHo — CHo — CH2 — OH —CH2- ^ CH2 — O — CH3 —CH2 — CHo — OH —CHo — CHo — CHo — OH —CH2 — CHo — O — COCH3 —CH2 — CHo — OH —CHo — CHo — CH2 — OH pattern 94 ^ CH2 — CH2 - OH —CHo — CHo ^ CHo — OH —CH2 — CH2 — CHs — O — CH3 CH2 — CH2 — O — H —CH2 — CH2 — CHo — OH —CH ^^ CHo-CHjr-O — CH3 —CH2 — CH2 ^ OH —CHo — CH2 — CH2 — OH —CH2 — CHo — OH —CHo — CH2 — CH2 — OH —CH2- ^ CH2-OH —CH2 — CH2 — CH2 — OH | - r - ^ CH2 — CH2 — OH —CH2 — CHs — CH2 — OH —H 1 —CH2 — CH2 — OH —CH ^ —CH2 — CH2 — OH pattern 94 —CH2 — CH2 — OH 1 —CH2 — CH2 — CH2 — OH pattern 94 • - ^ CH2) 6-OH - ^ CHa — CH2 — CH2 — O — CO ^ CH3 | Coloring 4 1 red with a tinge of yellow . no.I 1 " 1 »1 scarlet | red with a tinge of yellow 99 1 1 scarlet | a 1 »1 ruby 1 > »1 1 "1 M 1 ** 1 »L \ n 1 1 ruby f »1 \ n 1 99 1 »1 Red ** 1 Red Red Red » scarlet with a brown tinge 1 yi in 1 scarlet with a brown tinge ¦91 scarlet with a brown tinge "1 red with a blue tint 19 11 1 Red Red a l yellow 91 yellow Red and> 91 1 blue with a red tinge 91 11 1191820 43 44 c. d. table 3 1 DCCCXLIII DCCCXLIV DGCCXLV DCCCXLVI DCCCXLVtl DCCCXLVIII DCCCXLIX DCCCL, DOCCLI DCCCLII DCCCLIII DCCCLIV DCCCLV DCCCLVI DCCCLVII DCCCLVIII DCCCLIX DCOCLX DCCCLXI DCCCLXII DCCCLXIII DCCCLXIV DCCCLXV DCCCLXVI DCCCLXVII DCCCLXVIII DCCCLXIX DCCCLXX DCCCLXXI DCCCLXXII | DCCCLXXIII DCCCLXXIV DCCCLXXV DCCCLXXVI DCCCLXXVII DCCCLXXVIII DCOCLXXIX DCCCLXXX DCCCLXXXI | DCCCLXXXII 2 and 3 pattern 139 pattern 140 pattern 141 pattern 142 pattern 1.43. pattern 144 pattern 145 pattern 147 pattern 148 pattern 150 pattern 151 pattern 152 pattern 203 pattern 154 and pattern 61 1 y ' pattern 156 1 " pattern 157 1 " | pattern 158 pattern 159 1 " pattern 160 1 » | pattern 188 —CH2 — CH2 — CH2 ^ OH —Ca-ch2 — ch2 ^ oh - (CH2) 3-O-H —CH2 — CH2 — OH —CHi2-CH2-CH2 ^ OH H. - ^ (CH2) 3-OH H. —CH2 ^ —OH2 — OH • —CH2 — OH2 — CH2 —OH —CH2 — CH2 ^ OH H. ^ CH2 ^ CH2 ^ OH —CH2 ^ CH2 — CHa — OH —CH ^ p-CH2— | CH2 — OH h: —CH ^ —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH ^ CH2 — CH2- ^ CH2 — OH —H —CH2 — CH2 ^ OH —CH2 — OH2 —'CH2 —'OH —CH2 — CH2 — OH —CH2-CH2- ^ CH2-OH pattern 94 —H ^ CH2 — CH2 ^ OH - ^ CH2 ^ CH2 ^ CH2r — OCH3 —CH2 ^ CH2 ^ OH —CH2 - CH2 ^ CH2 — OH pattern 94 —CH2-CHr-OH —CH2 — CH2 ^ CH2 - OH —CH2 — CH2 — CH2 — OH —CH2 —'CH2 — OH - H. —CH2 — CH2 — OH —CH2 —'CH2 —'CH2 — OH ^ CH2 ^ CH2 — CH2- ^ OH 4 1 yellow colors | yellow '| yellow | red with a blue tint red with a blue tint scarlet scarlet ** 1 red with a blue tint j> l n i Violet violet • violet ruby Orange » Orange Violet red with a blue tint red with a blue tint 9> red with a shade of yellow, red with a blue tint Violet 9> blue Table 4 Coupling components of formula 195 Example no 1 DCCCLXXXIII DCCCLXXXIV DCCCLXXXV DCCCLXXXVI DCCCLXXXVII DCCCLXXXVIII DCCCLXXXIX DCCCXC DCCCXCI DCCCXCII Ingredient two-phase 2 pattern 121 pattern 120 > » pattern 136 9l / ^ 2 3 - '\ - xH2 — Ln2- ^ On —CH2 ^ CH2 — CH2 — OH —H —'CH2 — CH2 ^^ OH —CH2 ^ CH2 ^ O ^ COCH3 ^ CH2 — CH2 — CH2 — OH ^ CH2 — CHa- ^ O — CH2 — CH2 - OCHO - (CH2) 6OH ^ CH2 — CH2 — CH2 — OH —CH2 ^ CH2- Coloring 4 scarlet scarlet red with a tinge of yellow * » »» Vi red 91 820 45 46 c. D. Table 4 1 1 DCCCXCIII DCCCXCIV DCCCXCV DCCCXCVI DCCCXCVII DCCCXCVIII DCCCXCIX CM CMI CMII CMIII CMIV CMV CMVI CMVII CMYIII 2 and 3 pattern 122 Vi pattern 123 9) Oh pattern 162 pattern 147 pattern 150 pattern 163 pattern 127 pattern 142 pattern 159 pattern 124 —H —CH2 — CH2 ^ OH —CH2 ^ CH2 — CH2 — OH ^ H. —CH2 — CH2 ^ OH —CHo — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH ^ CH2 — CH2 — CH2 — OH —CH2 — CH2 — CH2 ^ OH H. —CH2 — CHo ^ OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OTI —CH2 — CHo — CH2 — OH —CH2 — CH2 — CH2 — OH 4 ruby Red ruby 99 Violet ruby. Violet blue with a red tinge Red red with a blue tint red with a blue tint red 1 Table 5 Coupling components of formula 182 1 Example no 1 CMIX CMX CMXI | CMXII CMXIII CMXIV CMXV CMXVI | CMXVII CMXVIII CMXIX CMXX | CMXXI CMXXII CMXXIII CMXXIV CMXXV 1 CMXXVI CMXXVII CMXXVIII CMXXIX CMXXX CMXXXI CMXXXII CMXXXIII CMXXXIV Ingredient two-phase 2 pattern 98 pattern 120 Bi pattern 123 pattern 136 pattern 163 pattern 153 ti pattern 97 Vi pattern 92 ».J R2 3 —CHo — CHo — OH —CHo — CHo — CH2 — O — CH —CHo — CHo — CH2 — OH —CH2 ^ CH2 — O — CH3 —CHo — CHo-OH —CH2 — CH2 — CH2 — OH —CHo — CH2 — C8H5 —CHo — CHo — CHo — O ^ CH3 —C3H5 1 —CHo — CHo — OH ^ (CH2) 3-OH —C0H4 — OCH3 —C2H5 —CHo — CHo — OH _ (CHo) 3 ^ 0 "H —C2h; - (CHo) 3 ^OH —C3H6 ^ OCH3 - (CH2) 3-OH —CH2 ^ CH2 — CH> —OCH —C3H7 (n) —CH2 — CHo — OH - (CH2) 3-0 ~ H —C6H5 —CH2 — CHo — OH —CH2 — CH2 — CH2 — OH Coloring 4 Red red with a blue tint b » red-violet red-violet » blue scarlet j> scarlet Red orange 47 91 820 Table 6 Coupling Components - Formula 183 48 Example no 1 * CMXXXV CMXXXVI CMxxxvn CMXXXVIII CMXXXIX CMXL CMXLI CMXLII CMXLIII • CMXUV CMXLV CMXLVI CMXLVII CMXLVIII CMXLIX OML CMLI l CMLII Ingredient two-phase 2 pattern 120 »» pattern 98 this pattern 97 pattern 123 pattern 136 pattern 91 1 (R2 3 - ^ CH2-CH2-C8Hs —CH2 — CH2 — OH —CH2 — CH2 — CH2 ^ -OH. pattern 94 —CH2 ^^ CH2 — CsHs - ^ CH2- ^ CH2-OH —CH2- ^ CH2-CH2-OH —CH2 — CH2 — CgHs —CH2 — CH2 — QH —CH> ^ CH2 — CH2 — OH —C4H ^ (n) —CH2 ^ CH2 — OH —CHr-CH2-CH2-4OH —C ^ n) ^ CHa — CH2 — OH - ^ CH2 ^ CH2-CHa-OH —CHo — CH2- ^ C6H5 ^ | —CH2 ^ CH2 - OH __ Coloring 4 scarlet fiery red red | red with a shade of yellow | scarlet l "r Orange "•» '1 ** 1 red with a blue tint 1 ruby Red ** yellow • »1 40 with 96% sulfuric acid at temperature -10 ° C, then added at 0 ° -5 ° C August 32.5 parts 23% nitrosyl sulfuric acid and the mixture was stirred for 4 hours at 30 - * Jt) ° C. The resulting diazonium salt solution tours take about 20 minutes to 35.5 a portion of the suspension cooled to 0 ° C the coupling component of formula 199 in the mixture 100 parts of glacial acetic acid, 1 part acimidosulfonic acid, 30 parts by volume concentrated hydrochloric acid and 500 parts of water. Pod the coupling time is kept in the mixture until giving sodium acetate, a pH value of 0-2 and for easy While mixing, water and ice are added.

Upon completion of the coupling, that at the value of pH> 2 is very fast and the mixture is drained shades of dyes of formula 200 and 201, washed water and dried.

'A dark powder is obtained, dissolving 45 in dimethylformamide with red-violet tinted and dyed terephthalic fabric polyethylene lamellae to a red-violet color.

[Example OMUIII. 20 parts of the dye o formula 193 is mixed with 100 parts of 50 acid formic for 10 hours at temperature 80 ° C to 1 ° C, then distilled off to a decrease about 50 parts of form acid under high pressure and dilute the residue after cooling 500 parts by volume of water. Executed 55 the dye Formula 184 is filtered off, washed with water gives and dries. The obtained product dissolves in d-methylformamide with an orange color and dyes polyethylene terephthalate fabric flax to orange with an unusual 60 power and light resistance.

(Valuable dyes are also: example CMLIV, dye formula 62, gives orange color, example CMLV dye formula 63 color 65 scarlet wreath, Example CMLVI Dye Formula 64 Color golden yellow, Example CMLVH Dye Formula 65 Color orange wreaths, Example CMLVIII dye Formula 66, color red-violet crowns, Example CMLIX dye formula 67, color yellow fruit, Example CMLX dye formula 68, color scarlet crown, * * ¦ example CMLXI dye formula 69, color yellow wreath.

Example CMLXIL ¦ Mixture of 56 parts 2,6-dichloro-3-cyano-4-methylpyridine, 160 jun volume of N-methylpyrrolidone and 50 parts of volumetric triethylamine, 50 parts are asked cut the amine of Formula 71 and mix for approx. hours at 55-60 ° C and then gives about 1000 parts of water and acidifies concentrated [with hydrochloric acid. The reddish brown separates an oil which, after decanting the aqueous phase, washing the water becomes clear. Then adds up otttfblo 60 parts of 2-hydroxyethylaimine and mixed for 3-1 hours at 105-130 ° C. After When cold, it is diluted with about 300 parts of ice high acetic acid and acidifies 50 parts m of volumetric concentrated hydrochloric acid. Down ice is added to the mixture until the temperature is reached temperature 0 ° C, then treated with a salt solution diazo, obtained as follows: 49 parts of 2-amino-5-initrobenzonitrile are added in portions at 0-4 ° C while vigorously mixing to a mixture of 240 concentrated parts sulfuric acid and 98 parts of 23% ni- troyl sulfide. The mixture is stirred for 4-5 hours at 0-4 ° C, and added por to the above-described coupling mixture.

By simultaneous addition of ice and ice water easy to mix niny and temperature 0 ° C. Then within 20 mi-91,820 * »50 Table 1 Coupling components of formula 74 Example 1 no 1 CMLXIII CMLXIV CMLXV CMLXVI CMLXVII CMLXVIII CMLXIX CMLXX CMLXXI CMLXXII CMLXXIII CMLXXIV CMLXXV CMLXXVI CMLXXVII CMLXXVIII CMLXXIX CMLXXX CMLXXXI CMLXXXII CMLXXXIII CMLXXXIII CMLXXXIV CMLXXXV CMLXXXVI CMLXXXVII CMLXXXVIII CMLXXXIX CMXC CMXCI CMXCII CMXCIII CMXCIV CMXCV CMXCVI CMXCVII CMXCVIII CMXCIX M. TO ME MII MIII MIV MV MVI MVII MVIII MIX MX MXI MXII MXIII MXIV MXV MXVI MXVII MXVIII MXIX MXX MXXI MXXII MXXIII 1 MXXIV 1 Ingredient two-phase 1 2 pattern 90 and »» ** and * » pattern 91 pattern 92 1) 9 this » pattern 93 91 pattern 95 pattern 96 01 11 pattern 97 31 91 l » 11 pattern 98 91 M> ii fi ii pattern 99 ii pattern 100 »9 pattern 101 pattern 102 11 1 pattern 103 91 pattern 104 is 1 ^ 2 j 1 3 H. —CH2 — CH2 — OH —CH ^ Clis — CH2 ^ OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH ^ CH2- ^ CH2-O-CH3 1H —CH9 — CH2 — OH —CH2 ^ CH2 — CH2 ^ OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —H —CH, -CHo ^ OH —CH2 — CH2 — CH2 ^ OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —H —CH, —CH2 — OH —CH2 ^ CH2 — CH2 - OH pattern 94 —CH2 — CH2 — O — CH2 — Clla — OH H. —CH2 — CH2 — OH —CH2 ^ CH2 — CH2 ^ OH pattern 94 —CH2 ^ CH2 — O — CH2 — CH2 - OH H. —CH2 ^ CH9 — OH —CH2 — CH ^ CHo — OH —CH2 — CH2 — O — CH2 — CH2 — OH H. —CH2 — CH9 ^ OH —CH2 — CH2 — CH2 — OCOCH3 pattern 94 —CH2- ^ CH2 — O — CH2 — CH2 — OH —CH2 — CH9 —'O — CH3 —CHo — CH2 — CH2 — O — CH3 —CH9 — CH2OCHO —I (iCH2) k — OH —H —CH2 — CH2 — OH —CH <> ^ CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH pattern 94 —CH9 — CH2 — CH ^ —O — CH3 ^ CH2 — CH9 — CH ^ OCOCHa —CH2 — CHo — OH —CH2 ^ CH ^ CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2OH —CH ^ CH ^ CH ^ OH —CH2 — CHz — O — CH2 — CHg- ^ OH —CH2 — CH2 — OH —CH ^ CH? —CH2 — OH —CH2-CH2- ^ OH —CH2 — CH2 — CH2 — rOH —CH2 — CH2 ^ O — CH2 — CH3 - OH —CH2 — CH2 — OH —CH2 ^ GH2 — CH2 ^ OH —CH2 — CH2 — O — CHs — CHs — OH —CH2 — CHa — OH ^ CH2- ^ CH2 — CH2 ^ OH —CH2 — CH2 — O — CH2 — CH3 ^ OH | Coloring 4 yellow 99 1 W. 1 ** ** yellow »1 • in 1 M 1 yellow 91 11 1 11 I 11 yellow I '* 1 »I a 1 » Orange * "1 ».» 1 99 1 99 1 Orange in* 11 ti; Orange 91 11 1 * 1 1 "L. n V '* ¦ 1 r> 1 scarlet 11 and> 11 3 * 1 13 1 1 * scarlet 99 red with a tinge of yellow 11 11, 1 Orange 11, -, yellow " »1 Orange at ii yellow "1 5L 191820 5l 52 continued table 1 | _ u MXXV MXXVI DVEXXVII MXXVIII MXXIX MXXX MXXXI MXXXH iMXXXIII IMXXXIV MXXXVI (MXXXVII MXXXVIII MXXXIX 1 MXL MXLI MXLII MXUII MXLIV MXLV MXLVI MXLVII MXLVIII MXLIX * • ¦¦ • ML MLI MLII MLIII MLIV | | a | 3 pattern 105 1 JJ 1 * " pattern 106 09 pattern 107 ho pattern 108 no pattern 109 pattern 110 pattern 111 pattern 112 this pattern 113 »J 1 pattern 114 a 1 H. -CHa-CH2-OH —CH2 — CH2 ^ CH2 ^ OH - ^ CH2-CH2-CHa-O ^ CH3 1 ^ CHa — CH2 — OH f —-CH2 ^ -CHa —— CH2-OH - 2 CH 2 2 CH 2 -O- 1 CH 3 -HCH 2 OH —H —CH2 — CH2 — OH —CH2 -— OIL — CH2 — OH '- ^ Ha ^ HCHs ^ O- ^ CH ^ CHa- ^ OH ^ CHa — CH2 — O ^ CH3 —CHa — CHa — CHa — OH.

—CH2 — CHa — OH - ^ CHa — CHa — CH2 — OH H 2 CH 2 CH 2 O 2 CH 2 → CH 2 4 OH —CHa- ^ Ha- ^ OH - ^ CHr-CH2-CH2-OH ^ CH2- ^ CH2 ^ O-CHa-^ CH ^ OH, —CH ^ -CHa — OH —CHa — CHa — CH2 — OH pattern 94 —CHa ^ CHa — O ^ CHa ^ CHa ^ OH —CHa — CH2 - OH —CHap — CH3 —'CHa — OH ^ CHa ^ CHa — O ^ CH2- ^ CHa ^ OH - ^ CH2 — CH2 ^ OH ^ CHa ^ CHa — CH2 — OH —CH2 — CHa- ^ OH —CHa — CH2 — CHa — OH 1 4 yellow l » ** 1 yellow »1 yellow * »¦.¦" f «1 red with a tinge of yellow (orange l yellow golden yellow "1 9i V yellow M. yellow yellow Table 2 Coupling component of formula 75 Example (no 1 1 MLV MLVI MLVII MLVIII MLIX iMLX 1 ^ MLXI MLXII MLXIII MLXIV MLXV MLXVI MLXVn MLXVIII MLXlk MLXX MLXXI .MLXXII | MLXXIII MLXXIV 1 MLXXV I Ingredient two-phase 2 pattern 90 pattern 91 ha pattern 92 99 '*> pattern 97 pattern 95 99 pattern 98 9 and 1 pattern 106 pattern 107 99 I »1 Bi 3 —CHa — CHa — OH —CHa - "CHa — CHa — OH —H —CH2 — CH2 ^ OH —'CHa — CHa — CHa — OH —CHa — CH2 — CHa ^ O ^ (CH2) 2OH —CH2 — CH2 — OH —CHa — CH2 — CH2 ^ OH —CHa- ^ CHa — O — CH2 — CH3 — OH —CH2 — CH2 ^ OH —CHa — CH2 — CH2 — OH ^ CH2 — CH2 ^ O ^ (CH2) 2 OH —CHa — CHa — CH2 — OH —CHa — CH2 — O — CH2 — CH3 — OH —CH2 — CH2 — OH - ^ CHa — CH2 — CH2 — OH —CHa — CH2 — CHa — OH - ^ CH2 — CH2 — O— (CH2) 2OH | —CHa — CHz — OH —CHa — CHa — CH2 — OH —CHa — CH2 — CH2 — CH 1 Coloring 4 yellow 1 > <> yellow yellow golden yellow yellow Orange "[ 99 1 Orange 99 ¦ V scarlet 99 I yellow > 9 1 yellow »> > »¦ '53 91820 Coupling components of formula 74 Example no 1 MLXXVIII MLXXIX MLXXX MLXXXI MLXXXII MLXXXIII MLXXXIV MLXXXV MLXXXVI MLXXXVII MLXXXVIII MLXXXIX MXC MXCI MXCII MXCHI MXCIV MXCV MXCVI MXCVII MXCVIII MXCIX MC MCI MCII MCIII MCIV MCV MCVI MCVII MCVIII MCIX MCX MCXI MCXII M & XIII MCXIV MCXV MCXVI MCXVII MCXVIII MCXIX MCXX 1 MCXXI MCXXII MCXXIII MCXXIV MCXXV MCXXVI MCXXVII MCXXVIII MCXXIX MCXXX MCXXXI MCXXXII MCXXXIII MCXXXIV MCXXXV MCXXXVI MCXXXVII MCXXXIII MCXXXIX MCXL 1 MCXLI | Ingredient two-phase 1 2 pattern 120 1 B> 1 " 'Formula 112: 1 h M. Vi pattern 122 ii \) 3 pattern 123 hi pattern 124 pattern 125 IW pattern 120 pattern 127 » ii »» pattern 128 iii Vi pattern 129 pattern 130 *> "and pattern 131 hi and* pattern 132 pattern 133 and* 99 pattern 149 in 1 H2 1 3 —CHq — CH3 —CH2 — CH2 ^ —CH2 — OH pattern 94 —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OCH3 H. ^ (CH ^ OH —CH2 — CHs- ^ O — COCH3 —CH2-CH2 -OH —'CH2 — CH2 ^ —CH2 — OH pattern 94 * —CH2 — CH2 — O — CH2 - CH2 — OH H. H. —CH2 — CH2 — OH —CHsr-CHs-CH2-4OH pattern 94 —CH2 — CH2 — u — ctf ^ CHa — OH —ICH2 — CH2 — O — CH3 —CH2 — CH2 — CH2 — O — CH3 —CH2 — CH2 ^ O — COCH3 —H —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2-CH2- ^ O-CH2-CHa-^ OH —CH2 — CH2O — CH3 C2H5 —CH2 — CH2 - OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHs — CH2 — OH —CH2 — CH2 ^ OH —CHj — CH2 — CH2 — OH —CH2 — CH2 — O — CHa — CH2 — OH —CH2 — CH2 - OH —CH2 — CH2 — CH2 — OH ^ H. —CH2 — CH2 — OH —OH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 - CH2- ^ OH —CH2 — CH2 — p-O — CH3 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2—0 — CHa ^ CHa ^ OH —CH ^ —CH2 ^ O — CH3 ^ CH2 ^ CH2 — OH —CH2 — CH2 — CH2 — OH pattern 94 —CH2 — CH2 — O — CHa — CHa — OH —CH2 — CH2 - OH —CH2 — CH2 — CH2 — OH —CH2-CH2-CH2- ^ O-CH3 —CH2 — CH2AO — H —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — CH2 — O — CH3 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — CH2OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH ^ —CHj — OH , —CH2—, CH2 — CH2 — OH 1 —CHa — CH2 ^ -O — CH2 — CH2 — OH | Coloring 1 - 4. red with a tinge of yellow * » ii. 1 "* scarlet red with a tinge of yellow ii scarlet "^ 1 \ ii, i Ir) | ruby ii 1 M 1 1 "1 "1 "1 "[ 99 ruby "1 ** • 1 99 1 fi 1 »1 Red M 1 "1 Red «1 in 1 Red in 1 red 1 »| 99 I * i i 9 and 1 scarlet with a brown tinge "1 scarlet with a brown tinge scarlet with a brown tinge M 1 "1 "f scarlet with a brown tinge 0) 1 "1 red with a blue tint ** hi Red Vi and 1 Red yellow «1 V91820 55 56 c. D. Table 3 1 1 MCXLII MCXLIII MCXLIV MCXLV MCXLVI MCXLVII MCXLVIII MCXLIX MCL MCLI MCUI MCLIII MCLIV MCLV MCLVI MCLVII MCLWII MCLIX MCLX MCLXI MCLXII MCLXIII MCLXIV MCLXV MCLXVI MCLXVII MCLXViri MCLXIX MCLXX MCLXXI MCLXXII MCLXXIII MCLXXIV MCLXXV MCLXXVI MCLXXVII MCLXXVIII MCLXXIX MCLXXX and MCLXXXI MCLXXXII MCLXXXIII J MCLXXXIV MCLXXXV MCLXXXVI MCLXXXVII MCLXXXVIII MCLXXXIX M £ XC MCXCI • MCXCII MCXCIII MCXCIV MCXCV MCXCVI MCXCVII MCXCVIII MCXCIX 1 MCC MCCI MCCII MCCIII MCCIV MCCV MCCVI MCCVII MCCVIII MCCIX MCCX MCCXI MCCXII 1 MCCXIII 2 I 3 | '4 | pattern 135 pattern 136 (91) pattern 137 »» and" * » ki pattern 138 pattern 139 pattern 140 pattern 141 pattern 142 visor 143 pattern 144 pattern 145 pattern 146 pattern 147 pattern 148 pattern 150 pattern 151 pattern 152 pattern 153 Of the Jagiellonian University pattern 154 pattern 61 pattern 156 and.} pattern 157 91 pattern 158 pattern 159 pattern 160 pattern 188 —CH2 — CH2 — OH —CH2 — CHa — CHa — OH —CH2 — CH2 — O — CH2 — CHa — OH —H —CH2 — CH2 — OH —CH2 — CH2 — CHa — OH pattern 94 ^ (CH2) 3-0- (CH2) 4-OH —CH2 — CH2 — OH —CH2 — CH2 — CHz — OH pattern 94 ^ CH2 — CH2 — O — CHa — CH2 — OH ^ CCH2) 6-OH - (CH2) 3-O- (CH2) 4-OH ^ CHs — CHj — CH2 — O — CO — CH3 —CH2 — CH2-0 — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH —CHa — CH2 — CHa- ^ OH —CH2 — CH2 — O — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH ^ CH2) 3- ^ O-H —CH2-CH2-OH —CH2 — CH2 — CH2 — OH H. —CH2 — CH2 ^ O — CHa — CH2 — OH - (CH2) 3 ^OH —CH2 — CH2 — O — CH2 — CHo — OH H. —CH2 — CH2 ^ OH —CHa — CH2 — CHa- ^ OH —CHa — CH2 — OH —CH2 — CH2 —'OH H. —CH2-CH2- ^ OH —CH2 -! - CH2 — CHa — OH —CHy-CH2 — O — CHa — CH2 — OH ^ (CH2) 3- ^ 0- (CH2) 4-OH —CH2 — CH2 — CHa — OH —CH2 — CH2 — O — CHa — CH2 — OH —H —CHa — CH2 — CH2 — OH —CH2 — CH2 — O — CHa — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHj — CHa — OH.

—CHa- ^ CHa — CH2- ^ OH —H ^ CHa — CH2- ^ OH —CH2 — CH2 — CH2 — OH —CHa — CH2 — O — CHa — CH2 — OH —CH2 — CH3 —CHj — CH2 — CHa — OH pattern 94 —CH2 — CH2 — O — CHa — CH2 — OH —H —CH2-CHa-OH —CH2 — CH2 — CHa — OH —CH2 — CH2 — O — CHa — CH2 ^ OH - * CH2 — CHa - OH —CHa — CH2 — CH2 — OH —CH2 — CH2 — O — CHa — CH2 - OH pattern 94 —CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHa — CH2 — OH —CH2 — CH2 — CH2 — OH —CHa — CH2 ^ OH —CH2 — CH2 — CH2 — OH H. —CHa — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH yellow »» 1 M 1 red 1 n 1 *and blue with a red tint \ "'i by "\ blue (blue) 1 yellow picture I. *> _ »: F yellow *> yellow f in red with a blue tint 99 91 Si red with a blue tint »| S'zkarlatne scarlet ». scarlet 1 red with a blue tint 1 them *and Violet red with a blue tint Violet - * » Violet » ruby Orange * f; 1 Orange M. 99 91 vi Violet i2 • red with a blue tint ii red with a blue tint ** ri ^ _ red with a tinge of yellow red with a blue tint .91 Violet ¦ r ¦ blue with a tint of red91820 57 58 Table 4 Coupling components of formula 185 1 Example j 1 MCCXIV MCCXV MCCXVI MCCXVII MCCXVIII MCCXIX MCCXX MCCXXI MCCXXII MCCXXIII ] MCCXXIV MCCXXV MGCXXVI MCCXXVII MCCXXVIII MCCXXIX MCCXXX MCCXXXI MCCXXXII MCCXXXIII MCCXXXIV MCCXXXV MCCXXXVI MCCXXXVII MCCXXXVIII * MCCXXXIX MCCXL MCCXLI 'MCCXLII MCCXLIII MCCXLIV MCCXLV MCCXLVI MCCXLVII MCCXLVIII MCCXUX MCCL MCCLI 1 MCCLII | Ingredient two-phase 1 2 pattern 121 pattern 120 •> pattern 136 pattern 122 ii ii and pattern 123 pattern 162 pattern 147 pattern 150 ' pattern 163 9J pattern 164 pattern 127 » pattern 142 pattern 159 pattern 124 Hi 1 3 —CH2-CH2- ^ OH ——CH2 CH2 ^^ CH2 OH —CH2 — CHj — O — CHy-CH2 — OH —H —CHa — CH2 — OH —CH2 — CHa- ^ O — COCH3 —CHa — CH2 — CH2 — OH - ^ CHa — CH2 — O — CH2 — CH2 — OE —CH2CH2r-O ^ CH2 ^ CH.> OCHiO | - (CH ^ H —CH, ^ CH2 — CH2 — OH —CHa — CH2 — OH —H —CH2-CH2-OH —CH2 — CH2 — CH2 — OH —CHa — CH2 — O — CHa — CH2- ^ OH —H —CHa — CH2 — OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CHa — CHa — OH - (CH2) 3-O- (CH2) 4-OH —CHs — CH2 — CH2 — OH —CH2 — CH2 — CH2 — OH —CHa — CH2 — O — CH * —CH2 — OH —CH ^ —CH2 — CH2 — OH —CHa — CH2 — O — CHa — CHa- ^ OH —CH2 — CH2 — CH2 — OH —CHr-CH2 ^ O-CH2-CHa-^ OH —CHa — CHa — O — CH2 — CH2 - OH H. —CH2 — CH2 — OH —CHj— ^ Cxi2 — CH2 — OH 1 —CHa — CHa — O ^ CH2 — CH2 — OH —CH2 — CHa — CH2 — OH —CH ^ —CH2 — O — CH2 — CH2 — OH —CH2 — CHa — CHa — OH —CHa — CH2 — O— (CH2 aOH —CH> —CHa — CH2 — OH —CH2 — CHa — O — CH2 — CH2- ^ OH | Coloring 1 4 scarlet 19 1 "1 scarlet red with a shade of yellow J l and 1 > »1 »> 1 1 in 1 Red * t 1 Red "1 »» 1 »> L red j * »I ruby »1 n 1 Violet ruibinowe 1 Violet blue with a red tinge. *> 1 blue Red here 1 Hi 1 red with a blue tint t red with a blue tint Red Table 5 Dyes of formula 186 Example 1 MCCLIII MCCLIV MCCLV MCCLVI MCCLVII MCCLVIII MCCLIX MCCLX MCCLXI MCCLXII MCCLXIII MCCLXIV MCCLXV MCCLXVI MCCLXVII 1 MCCLXVIII] Y 2 —H —Cl —CN —CH3 —Br —CN ^ CN —CN —N02 —SO 2 CH 3 —SO 2 CH 3 —SO 2 CH 3 —SO 2 CH 3 - ^ CN - ^ CN - ^ CN 1 Ti 3 ^ N02 ^ N02 ^ N02 ^ N02 ^ NOa —N02 —N02 —N02 ^ N02 --N02 —N02 —NOa ^ NOa —N02 ^ Cl —H Y2 4 —H —H —H —H —H —H —Cl -and —H —H —H —H —H —H —H —H J X —H —H —CN —CN —CN —H —CN —CN —CN —CN —H —CN —CN —CN —CN —CN R2 6 —CIV-CH2 — OH —CH2 — CH2 — OH —CH2 — CH2OH —CH2 — CH2 — OH —CH2 — CH2OH —CH2 — CH2 — CHa-OH —CHa — CH2 — CHa- ^ OH —CH2-CH2-OH —CH2 — CH2 — OH —CHa — CH2 — OH —CH2 — CH2 — OH —CH2 — CHa — OH ^ (CH2) ^ OH —CH2 — CHa — OH —CH2 — CHa — OH —CH2 — CH2 - OH Coloring 7 Red vo IN Orange scarlet red with a tinge it is blue ruby in i " dark red Violet Red golden yellow yellow '91 59 Aqueous sodium acetate solution is added to the note until the pH of the mixture is 1.5 - 1.00 After the coupling is completed, the mixture is heated to at a temperature of 60-80 ° C, the color disappears nickel, washed with water and dried. You get about . 162 parts of red brown powder, dissolve lurking in dimethylifbnmaimide with red tinting and dyeing the fabric polyethylene phthalate for extremely resistant to . light, moisture and temperature red color.

This dye corresponds to pattern 72 and contains he has a small amount of the 2y6-dialkylamnopyridine isomer formula 73.

Scharak dyes are obtained analogously terrified with two-phase components and with component- / coupling, listed in tables 1 and 2.

Example MLXXVI. 19.5 parts 3-aminp- * 5 ^ yttrium-2,1-ibenzisothiazole is added in portions, with stirring, at a temperature of 15-25 ° C to about 75-85 parts of 96% sulfuric acid and a mixture of The shanine is cooled to 0-4 ° C and then added dropwise at this temperature, 33.5 parts of 23% nitro sulfuric acid. Two-phase operation is not complete after about 3 to 4 hours of stirring at temperature 0- 5 ° C. Then a mixture of dio-salt is added azonium to a cooled to 0 ° C solution or suspension of 34 parts of the coupling component with a pattern 7tf in 50 parts of 30% hydrochloric acid, 500 parts of water and 150 parts of glacial acetic acid wego. When coupling, it is added gradually ice and sodium acetate so that the temperature is mixed the coupling did not exceed 5 ° C and the pH value it was finally about 2. Lost dye formula 77 is filtered off, washed with hot water t dries. You get about 53 parts of black a powder that dissolves in dimethylform- blue with a red tint dyed and dyed poly-terephthalate fabric ethylene blue with a red tinge nym, with very good durability.

Example MLXXVII. 11 parts of a metho ester 2-amino-5-yl-nitrobenzoic acid xyethyl It is consumed with 180 volumetric ice cold it acetic acid, 15 parts by volume hydrochloric acid and 10 parts of ice, after cooling to 0 ° C - 5 ° C, 13.5 parts by volume are added high quality 23% sodium nitrite solution. After about 2-3 hours of mixing it decomposes an emerging slight excess of nitrous acid v known method, dilutes diazonium salt solution input 1000 parts by volume of ice cold water and adds a solution of 11.0 parts of the coupling component formula 78 in 100 parts of glacial acid acetic acid and 10 parts of concentrated hydrochloric acid, then it is stirred for 1/2 hour and 50% of salt is added until the pH of the mixture is reached 2. After the coupling is finished the precipitated dye of formula 79 is removed and washed water and dried. A red powder is obtained, dissolving in dimethylformamide z ?. red tint and fabric dyeing with polyethylene terephthalate to strongly scarlet red color, very high durability.

Example MGCGLVI. 93 parts 2-amino-5- ^ nitrobenzonitrile is added in portions at 820 60 0-4 ° C with vigorous stirring to a mixture of 48 parts of concentrated sulfuric acid and 19.6 parts of 23% nitrosyl sulfuric acid. Chap the two-phase product is stirred for 4-5 hours in teimpe- temperature 0-4 ° C and a mixture of diazotones to a cooled to 0 ° C solution lulb of the suspension of 28.5 parts of the coupling component o formula 211, containing a small amount of an ingredient coupling of formula 212, to a mixture of 150 parts i ° volumetric glacial acetic acid, 20 volumetric parts of concentrated hydrochloric acid, 1 part sulphamic acid I 500 parts vol qualitative water. When joining, it is added sodium acetate and ice, so that the pH value of the mixture was constantly 0-2, the temperature was maintained at about 0 ° C and the mixture was easy for mixing. After the final coupling which it runs very quickly at a pH value of 1 ^ 2, the precipitated dye mixture is filtered off * of formula 213 containing a small amount of the isomer The 2,6-dialkylaminopyridines are washed with water and dried s. A reddish brown powder is obtained, a solution flashing in dimethylformamad with red tinted and tinted fabric with ter- , polyethylene phthalate to a red color extremely light resistant.

Example MCCGLVII. 8.8 parts ingredient of the diazo of formula 214 is stirred at temperature 10-15 bC with 24 g of concentrated sulfuric acid it, then cooled to 8-10 ° C and to the bottom gives 70 parts by volume of glacial acid acetic acid and 12 parts by volume of propio-acid new. After further cooling to temperature At 0-4 ° C, 13 parts of nitrosylsulfur acid are added dropwise and stirred for 3 hours at temperature 0-4 ° C. The obtained diazonium salt is added to 13.1 parts of a cooled to 0 ° C solution or the suspension of the coupling component of formula 215, with what a small part of the coupling component consists of of the 2, 6-) dialkyliminopyridine isomers, with stirring There is no 150 parts by volume of concentrated acid acetic acid, 15 parts by volume of concentrated acid salt, 500 parts by volume of water and 1 part aimidosulphionic acid.

Ice and sodium acetate are added during coupling, so that the temperature remains the pH was 2-0. As far as the mixture is difficult, no need to stir, you can add a little ice water hate. 50 Bonding at a pH value of 2 occurs quickly to end. The lost dye of formula 216 as well 217 is drained, washed with water and dried. Received I have a brown powder that dissolves in 55 dimethylformimide with red border tinting and dyeing polyester terephthalate fabric orange polyethylene with an unusual color persistence in light.

Example MOOCLVIII. 5.5 parts p-nitroani- 60 ropes are mixed with 40 volumetric steels hydrochloric acid and then diluted with ice and hydrochloric acid up to a volume of 200 parts by volume partial, adds 15 parts by volume 23% sodium nitrite solution and stirred for 2 hours. 65 After filtering the diazonium salt solution, solution 91 820 61 62 Table 6 Coupling components of formula 187 Example 1 mr 1 1 MCCLXIX MCCLXX MCCLXXI MCCLXXII MCCLXXIII MCCLXXIV MCCLXXV MCCLXXVI MCCLXXVII MCCLXXVIII MCCLXXIX MCCLXXX MCCLXXXI 1 MCCLXXXII Ingredient two-phase 2 pattern 61 pattern 61 pattern 61 pattern 156 pattern 81 pattern 81 pattern 01 pattern 91 pattern 91 pattern 91 pattern 120 pattern 120 pattern 98 pattern 97 R2 3 —CH2 — CH2 — OH —CH2- ^ CH2 - OH CHa — CH2 OH —CH2 — CH2 ^ OH —CH2- ^ CH2 ^ OH —CH2 — CH2 ^ OH —CHj — CHa- ^ OH ^ CH2 — CH2 — OH —CH2 — CH2 — OH —CHs — CHa — CHa- ^ OH —CH2-CH2-CH1- ^ OH ^ CHa- ^ Hjj — OH —CH2 — CH2 — OH —CH2- ^ CH2-OH B 4 —CH3 —H —H —CH3 —CHs —H —H ^ C (CH3) 3 —H —H —H —H —H —H Bi —H ^ CH3 ^ a —H —H —CH3 ^ CH3 —H ^ OCH3 —CH3 —CH3 —CH3 —CH3 —CH3 Coloring 6 red-purple red-violet red-violet red with a shade 1 blue | orange | Orange yellow yellow yellow f yellow Red Red scarlet orange | Table 7 Coupling components of formula 204 Example no 1 fl MCCLXXXIII MCCLXXXIV MCCLXXXV MCCLXXXVI MCCLXXXVII MCCLXXXVIII MCCLXXXIX MCCXC MCCXCI MCCXCII MCCXCIII MCCXCIV MCCXCV MCCXCVI MCCXCVII MCCXCVIII MCCXCIX MCCC MCCCI MCCCII 'MCCCIII Ingredient two-phase 2 pattern 120 > i »» ii pattern 98 you \ ii model 97 j pattern 123 and pattern 127 pattern 91 »> 3 H. —CH2 — CH2 — OH —CH2-CH2-CH2- ^ OH pattern 94 —CH 2 CH 2 —O — CH 2 —CH 2 - OH H. —CH2 — CH2 ^ OH —CH2 — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH H. —CHa — CH2 — OH —CHa — CH2 — CH2 — OH —CH2 — CH2 — O — CH2 — CH2 — OH H. —CHa — CH2 ^ OH —CH2 — CH2 — CH2 — OH H. —CH2-2CH2-OH —CHa — CH2 — CHz — OH H. ^ CHa ^ CHa ^ OH Coloring 1 4 scarlet Red » red with a tinge of yellow scarlet ij Orange ** > i red with a blue tint ruby Red yellow 9 and 163 91820 Table 8 Dye formula 205 64 Example no .1 MCCCIV MCCCV MCCCYI MCCCYII MCCCYIII MCCCIX MCCCX MCCCXI MCCCXII MCCCXIII MCCCXIV MCCCXV MCCCXVI MCCCXVII MCCCXVIII MCCCXIX MCCCXX | MCCCXXI 1 MCCCXXII Y 2 -CN ^ CN —CN ^ CN —H ^ Cl --C1 —CN —CH3 —OCH3 —SOaCHg —CF3 —CFa —CN ¦ —CN - ^ a —Br —H: —H | Yt 3 —H —N02 —NC2 ^ a .—. No2 ^ N02 -and -nBr —NC2 —N02 —NC2 —H - ^ a —CN —NO2 -JTO2 - ^ NOa -nNOa —NC2 I. Y2 4 —H —1H Cl —H —H —H —CN —H —H ^ H. —H ^ H. —H —H —Br —H —H —H —H X 6 —H —CN —CN —H —CN —H —CN —CN —CN ^ CN —CN —CN —CN —CN —CN. 1 —CN —CN —H —CONH2 1 1 Coloring 6 [ golden yellow red -1 ruby f Orange »> L Red Orange • golden yellow (Orange iszikarlatne [ red with a tinge of blue f yellow r »1 (orange ~ [ ruibin-red [ scarlet [ * »L red 1 scarlet "[ Dyes with the following patterns are especially valuable dyes: Example no 1 IMOOCXXIII MCCCXXIV MCCCXXV MCCCXXVt 1 MCCCXXVII MCCCXXVIII MCCCXXIX MCCCXXX MCCCXXXI MCCCXXXII MCCCXXXIII Pattern Q pattern 82 pattern 83 pattern 84 pattern 86 pattern 86 pattern 87 pattern 88 pattern 89 pattern 206 pattern 207 pattern 208 Coloring "3 red with a blue tint red-violet Red "1 »L Orange yellow scarlet | Table 9 Dyes of formula 209 Example no MCCCXXXIV MCCCXXXV MCCCXXXVI MCCCXXXVII MCCCXXXVIII MCCCXXXIX Y ^ SOjCHs —SO ^ CH * —SO2CH3 ^ CN —CN —CN Vt ^ N02 ^ sro2 —N02 —N02 —Cl —H Y2 \ kkkkkk E. —CHg —C3H7 (in) —CsHuiCn) —CH3 —CH3.

—CH3 R2 —CH2 — CH2 ^ OH —CH2 — CH2 ^ OH —CH2 — CH2 ^ OH —CH2 — CH2 ^ OH —CH2 — CH2 — OH —CH2-CH2- ^ OH Coloring Red Red Red Red golden yellow yellow | any excess acid is deposited nitrous acid in the known manner, and the diazot The dust is added to cooled to temperature ° C of a solution or suspension of 10 parts of the ingredient coupling of formula 218 in 250 parts of water and 20 parts of concentrated hydrochloric acid. By the introduction of sodium acetate increases the value the pH of the coupling mixture to 2-3, so that the coupling the chase ends quickly. Disappointed dye of formula 219, washed with water and dried. 65 You get about 15 parts scarlet red- it is a powder that dissolves in dimethyl phosphor mummy with an orange tint and foar- Binding fabric with polyethylene terephthalates for strength well, the orange color is very good. exposure to light and thermal conditions, method Carrier, and HT.

Similar to those described in the examples MOCCLVI — MOCCLYIIiI methods are produced dyes given in the following tables. 91820 65 6 * Translation no MCCCXL MCCCXLI MCCCXLII MCCCXLin MCCCXLIV MCCCXLV MCCCXLVI MCCCXLVII MCCCXLVIII MCCCXLIX MCCCL MCCCLI MCCCLII MCCCLIII MCCCLIV 1 MCCCLV y —CN —CN —CN —CN —H —Cl —Cl —CN —CH3 ^ OCH3 —SO4 Hz —CF3 ^ CFs —CN —H —H Table 10 Dyes of formula 210 Yi —H —N02 —N02 —Cl ^ N02 —N02 —Cl —Br -WELL* ^ NOa ^ N02 —H —Cl —CN - ^ N02 ^ NOa ya —H ^ H. —Cl —H —H —H —CN —H —H —H —IH —H —H —H —H —H E. —CH3 —CH3 —CH3 —CHt —CH3 —CH3 —CH3 —CH3 -CH3 —CH3 —CH3 —CH3 -r-CH3 —CH3 -QH5 CaHyfn) Coloring yellow red A l ruby golden yellow " Orange scarlet Orange golden yellow | (Orange scarlet red with a blue tint 1 yellow »1 Orange 99 l f »; j When coupling the coupling components with a pattern 232 in Table 4 result in mixtures because the coupling can take place either in position 3 and position 5 of the pyridine ring.

The dyes entered in the table 5 are also especially valuable. They show high efficiency associated with high thermal preservation long durability.

When used in the production of dyes with e.g. clades MDLIV- ^ MDLX and 2-cyano-4-chloroanil- Compounds which give a color to the gold are obtained yellow. ¦! Example MDLXXXVIII. A mixture of 187 2,6 parts of chioro-3-cyano-4-ethylpyridine, 500 parts of methanol and 135 parts of 2-phenylpropylami- ny-1 is stirred for 1 hour at temperature from about 25 ° C to a maximum of 55 ° C, adds 105 parts of triethylamine within 15 minutes and mixed for 6 hours at a temperature of about 45 ° up to 55 ° C. Then it distilled off at temperature 50-56 ° C under reduced pressure of approx 250 parts by volume of methanol and an excess of three Ethylamine cooled slightly and the remainder added when mixing to a mixture of about 1500 parts water, 500 parts of ice and 50 parts of concentrated acid salt, then stirs for another hour, the precipitate is filtered off and dried. I get about 265 parts of a colorless melting powder at 85-90 ° C. 27.5 parts of this powder is mixed with about 60 parts' / fnhydroxyethylamine 4-5 hours in temperature of 130 ° C 155 ° C, cooling and stirring nine 200 parts by volume of glacial acid 40 45 50 vol acetic acid and 30 parts concentrated hydrochloric acid.

A solution of the coupling component is obtained * possibly of formula 251 containing mala the amount of the coupling component), probably of the pattern on 262.

The mixture of coupling components is suitable about '50 parts of ice and cooled to temperature around 0 ° C. It is added in portions simultaneously about 100 parts of ice and a solution of the diazotized 2-amiino- -5- Nitriqbenzonitrile, prepared as follows way: 1116 ^ 3 parts of 2-amino-5-nitrobenzonitrile are added with stirring at 0-4 ° C mixture, 50 parts of concentrated reticular acid and 13 parts of 23% nitrosyl sulfuric acid. Yes that the temperature does not exceed 4 ° C. It mixes up for 4 hours at 0-5 ° C. and fuses as described above. For a faster end mating: which should run at around 0 ° C, the pH of the mixture is adjusted to 1.5-5 by adding sodium acetate. For the fugitives mixing can be done during the mixing process give loflow water.

The mixture is stirred for another hour, heats the steam to a temperature of 60-80 ° C, drain, rinse with water and dry. I get about 47 parts of red-brown powder, right likewise formula 253 containing a small amount a dye which is a 2,6-alkylaminopdry- isomer. dyin, dissolving in two-methylformaimi- day with a red tint and dyed fabric nine from polyethylene tereEftaflate to deep red highly durable color 67 91820 Blackboard pattern 220 68 Example ^ no 1 MCCCLIX / MCCCLX MCCCLXI MCCCLXH MOCCLXIH 'MCCCLXIV MCCCLXV MCCCLXVI | MCCCLXVII D — NH2 2 pattern 91 pattern 91 pattern 91 pattern 121 pattern 156 pattern 97 pattern 97 pattern 91 pattern 120 z1 .3 _ ^ (CH2) 3 — O ^ CHa — CH2— —Q) ^ - CH3 and* —H —H pattern 7 formula 8 formula 8 formula 8.

WITH* 4 ^ (CH2) 30 (CH2) 4-OH - (CH2) 30 (CH4) 6-OH -, (CH2 ^ O (CH2CH2O) 2C2H5 < ^ (CH2) 3 — O— (CH2Xr — OH ^ (CH2) 3 — O— (CH2) 6 — OH —CHa — CH2 — OH —OH, —CH2 ^ OH —CH ^ —CH2 — OH —CH2 — CH2 ^ OH Coloring yellow "1 ».» and scarlet Red Orange »» 1 yellow red 1 Blackboard pattern 220 Example no 1 D — NH2 Z1 v> iZ * Colors MCCCLXVIII MOCCLXIX . MCCCLXX mccclxxi mocclxxii mccclxxiii mccclxxiv mocclxxv mcoclxxvi mccclxxvii MCCCLXXVni MCCCLXXIX MOCCLXXX MOCCLXXXl MC5CCLXXXn MCCCLXXXIII MCCCLXXXIV MCCCLXXXV MCX2CLXXXVI MOCCLXXXVn MOCCLXXXVTII MCCCLXXXIX MCCCXC MCCCXCI MCCCXCTI MCCCXCIII MCCCXCIV MCCCXCV MCCCXCVI MCOCXCVTI Mcccxcvm MCCCXCIX MD MDI MDII MDIII MDIV MDV MDVI MDVII MDVni MDIX MDX MDXI MDXII pattern 91 pattern 97 MDXIII pattern 99 pattern 98 pattern 121 pattern 100 pattern 106 ^ (CH2) 3-O-C2H4- ^ O-C2H5 _ (CH2> 3 — O — C2H4 — O — C6H5 pattern 13 pattern 20 —LCHsfe — O — CH2 — CH2 — C8H5 1- (CH2) 3-O-CH2-C6H5 —H —H pattern 16 —H pattern 221 - (CH2) 2-O-C6H5 pattern 20 - ^ CH ^ - ^ O ^ CCH ^ OH pattern 7 visor 20 ^ (CH2) 3 - ^ (O-C2H4) 2- ^ OCH3 ^ (CH2) 3— (003114) 3-0-0 ^ 5 pattern 222 —H —H ^ -H —H —H —F (CH2) tT- ^ O — e> H4) 2 ^ OCOH5 pattern 225 MCH2) 3 — O — C2H4--0— —CH2 ^^ C6H5 - (CH2) s-0 — QEfi — O— —CH21 — CgHs - (CH2) r-O-C2H4- ^ O- —CH (CH3) 2 - (CH2) 3-O-C2H4-C8Hs - ^ (CH2) 3- ^ O-C2H4-C6H5 - (CH2) 3-O-C2H4-C8Hs ^ (CHjjJg- ^ O — CA) 2- ^ 0— —C6H5 pattern 226 —H -H •? ^ (CH2) 3-0-CH2-C6H5 - ^ (CH2) 3-O-CH2-C8H5 pattern 13 -H ^ .. * pattern 13 - (CH2 - ^ O-CH2-C6H5 -h (CH2) HO-C2H4) 3--0— and (1CH2) 3-H (O ^ C2H4) ^ 0- ft ^ (CH2) r-OH - (CH2) 3-OH HCH2) 3-OH ¦ —CH2 — CH2 — OH —CH2 — CH2 — OH —CI $ 2 — CH2 - OH ^ (CH ^ a — O — CHa — CeHg ^ CH2) 3-O- (C ^ OaCeH6 —CH2 — CHr ^ OH ^ CCH2) 3-0- (C2H40) 3C6H5 —CH2 — CHa — OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 - OH —CH2 — CH2 ^ OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — OH '—CH2 — CH2 ^ OH —CH2 — CH2 ^ OH —CH2 — CH2 — OH - ^ CH ^ a- ^ O — CWaOCHj pattern 223 pattern 20 ^ (CH2) 3— (O — CH2CH2) 2 OC6H5 pattern 224 ^ CH2 — CH2 ^ OH —CH2 — CHa- ^ OH —CH2 — CH2OH —CH2 — CH2 ^ OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — OH - (CH2) 3-OH —CH2 — CH2 ^ OH —CH2 — CH2 ^ OH - (CH2) 3-O-CH2-OgH5 _ (CH2) 3-O-C2H4OC6H5 —CH2 — CH2 ^ OH —CH2 — CH2 ^ OH —CH2 — CHs- ^ OH - (CH ^^ OCHsCH ^ aOCgHs —CH2-CH2- ^ OH —CH2-CHj- ^ OH —CH2 — CH2 ^ OH yellow golden yellow yellow golden yellow .Orange scarlet Red with a shade yellow yellow 91 820 60 70 continued table 2 1 MDXIV MDXV MDXVI MDXVn 1 MDXVIII MDXIX MDXX MDXXI MDXXII MDXXIII MDXXIV MDXXV MDXXVI MDXXVTI MDXXVIII MDXXIX MDXXX MDXXXI MDXXXII MDXXXIII MDXXXEV MDXXXV MDXXXVI MDXXXVII MDXXXVIII MDXXXIX MDXL MDXLI MDXLII MDXLin MDXLIV MDXLV MDXLVI MDXLVII MDXLVIII MDXLIX 1 MDL 2 pattern 106 pattern 227 »» pattern 228 " pattern 96 > » pattern 124 »> j » n »> pattern 99 »» »» '» and ai V 11 pattern 128 »5 pattern 136 »Vol » »» »» pattern 133 V, ii ai pattern 108 pattern 163 »» pattern 230 _3 HCH2) r-o-CaHs) * - O- ^ C2H5 » —H —H - {CH2) 3-O-CH2-CeHs ^ (CH2) 3--0-Cft2-C6H5 pattern 229 pattern 229 - (CHJs-O- (CH2) 6-OH —H —CH2 — C (CH3) R ^ O — C6H5 —CH2 — CH2 — O — Cgli5 —H ^ -H —H - (CHj) 3-0-CHa-CeHg - (GH2) 3-O-CH2-CeH5 ^ (CH2) 3-OC2H4-O-C2H5 pattern 14. « pattern 222 ^ (CH2) 3-0 ^ (CH2CH2O) 2CH3 - - (CH2) 3-O-CH, -C6H5 —H - (CH2fcO — C2H40C4H9 -> (CH2) 3 — O-5 — C2H4 — O— —CH. (CH.3) 2 2 CH 2) 3-O 2 (CH 2) 2 - C 6 H 5 ^ (0 ^) 3- ^ 0 ^ (0 ^ 40) 2-C6H5 - (GH2) 3-O- (C-ftO) * - C6H5 - (CH2) 3-0-CH2-C6H5 ^ (CH2) 3-O-CH2-C6H5 ^ (CH2) 3 — O— (C2H40) a — C6H5 —H - ^ (CH2) ^ O- (CH2) 2 — ÓH ^ (CH2) 3-O-CH2-C6H5 - (CH2) 3-O-CH2-C6H5 • ^ (OH2) 3- ^ O-CH2 — C6H5 . ' 4 HiCH2) r-OH ^ (CH2) 3-OH - (CH2) 3-O-CH, -C6H5 - (CH2) 3-O-CH2-C6H5 —CHs — CH2 — OH —CH2 — CH2 ^ OH —CH2 — CH2OH —CH2 — CHa — OH —H ^ (CH2) 3--0- —CH2 — CH * —OH —CH2 — CH2 — OH _ (CH2) 3-O- (CH2) dOH - (0 ^) 3 ^ 0 ^ (0 ^ 40) 2—0 ^ 5 - (CH2) 3-O-CH2-C6H5 ^ H. —CH2 — CH2 — OH —CHs — CH2 - OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CHa — CH2 — OH —CH ^ CHa — OH —CH2 — CH2 — OH -h (CH2) 3-0-CH2-CeHg —CHa — CHa — OH —CH2 — CHa — OH —CH2 — CHa — OH —CH2 — CHa — OH —CH2 — CH2 — OH. —CHo — CH2 — OH - (CH2) 3-OH —CH2-CH2- ^ OH ^ (CH2) 3- ^ O-CHa-CflHg —H - (CH2) 3-OH —CH2 — CH2 ^ OH —CH2 — CH2 — OH, AND yellow * »1 * '1 golden yellow. Orange "1 Red scarlet to me Red ** \ *> 1 ** * Orange * »And • 'and scarlet ':' » n Red ruby »» « ? ' > » » »» Red Orange blue with a shade red violet | Table 3 Pattern 231 Example no ¦1 MDLI MDLII MDLIII D ^ NH2 2 pattern 123 pattern 120 pattern 98 Z1 3 ^ (CH2) 3 — O — CH2 — C6H5 / - (CH2) 3-O-CH2-C6H5 - (CH2) 3 R 2 -CH 2 -C 6 H 5 Z2 4 —CH2 — CHa — OH —CH2 — CHa — OH —CH2 — CHa — OH Coloring • red- Violet Red with a shade blue red | Table4 j Coupling components of formula 232 Example no MDLIV MDLV MDLVI MDLVII MDLVIII MDLIX . MDLX .MDLXI MDLXII Ingredient two-phase pattern 163 Sl pattern 136 pattern 122 pattern 123 <»» pattern 98 Z1 l - (CH2) 3 R 2 -CH 2 -C 6 H 5 ,, ^ CH2) r-O-C2H4-OGjHg - {CH2) 3-O-CH2-C8H5 pattern 20 pattern 20 - (CH2) 3-O-CH2-C8H5 l> Z2 —CH2 — CH * —OH ^ (CH2) 3-OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CHa — CHa — OH —CH2 — CHa — OH —CH2 — CHa — OH —CH2 — CHa — OH ^ (iCH2) 2-hOH Coloring blue with a shade green red- Violet V) in Red with a shade blue | 71 91 820 Talblica 5 Coupling components of formula 233 72 Example no 1 MCDLXin MCDLXIV MCDLXV MCDLXVI MCDLXVII MCDLXVHI MCDLXIX MCDLXX MCDLXXI MCDLXXII MCDLXXIII MCDLXXIV MCDLXXV MCDLXXVI MCDLXXVII MCDLXXVIII MCDLXXIX MCDLXXX MCDLXXXI MCDLXXXII MCDLXXXIII 1 MCDLXXXIV Ingredient two-phase 2 pattern 120 • pattern 127 pattern 98 pattern 1.23 pattern 122 » pattern 156 pattern 92 " pattern 61 pattern 153 ,, pattern 124 3> Pattern 234 ?? n 3 2 8 2 3 2 3 2 3 2 3 2 3 2 13 ' 2 3 | 2 3 2 3 2 3 Coloring 4 Red red with a blue tint scarlet » red with a blue tint »¦ » J} golden yellow red-violet » Orange ** Red a and orange M; ! Table 6 Coupling components of formula 235 Example no MCDLXXXV MCDLXXXVI MCDLXXXVII MCDLXXXVIII MCDLXXXIX MCDXC MCDXCI MCDXCII MCDXCIII MCDXCIV MCDXCV MCDXCVI D — NH2 pattern 91 pattern 97 pattern 98 3) pattern 127 pattern 91 pattern 92 n 2 3 6 2 6 2 3 2 3 2 2 Z1 ^ (CH2) 3-O- (CH2) 20H - (CH2) 3-O- (CH2) 2OH - (CH2) 3-O (CH2) 2pH 2 (CH 2) 3 - O (CH 2) 20H - (CH2) 3-O-tCHa ^ H ^ (CH2) S-O- (CH2) 2 OH ^ (CH9) 3-0 ^ (CH2) 2PH -h (CH2) 3-0 [theta] (CH9), OH -. (CH2) 3-O— (CH2) ibH - '(CH2) 3-O-CH2-CeHs ^ (CH2) 3 - O ^ CH2 — C6H5 Dyes of formula 236 Coloring yellow . and orange shikarlatne red with a blue tint yellow golden yellow Red Table 7 Coupling components of formula 237 Example \ no 1 and MCDXCVII : MCDXCVIII MCDXCIX and MD | MDI ; mdii j MDIII MDIV 'MDV MDVI MDVII MDVIII MDIX MDX MDXI MDXII MDXIII 1 MDXIV Ingredient two-phase 2 pattern 90 ._ pattern 91 »> pattern 92 ,. pattern 93 pattern 95 pattern 96 pattern 97 ,, pattern 93 pattern 99 pattern 100 pattern 102 pattern 103 pattern 238 WITH* 3 C2H30C2H4 C2H4OC2H4OCH3 pattern 20 C2H40C2H4OH C2H4OC2H4OH pattern 20 C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH (CH2) dO (CH2) 6OH C2H4OC2H4OH (CH2) 3 (OC2H4) 2OCH3 CsHPCsI ^ OH C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH Coloring 4 yellow AT" • » Sr> t » *> * y Orange M. ii ii scarlet 99 » red with a tint yellow Orange yellow yellow 91 S20 73 74 c. D. Table 7 1 MDXV MDXVI MDXVII MDXVIII MDXIX MDXX MDXXI MDXXII MDXXIII MDXXIV MDXXV MDXXVI MDXXVII MDXXVIII MDXXIX MDXXX MDXXXI MDXXXII MDXXXIII MDXXXIV MDXXXV MDXXXVI MDXXXVII MDXXXVTII MDXXXIX MDXL MDXLI MDXLII MDXLIII MDXLIV MDXLV MDXLVI MDXLVII MDXLVIII MDXLIX MDL MDLI MDLII MDLIII MDLIV MDLV MDLVI MDLVII MDLVIII MDLIX MDLX MDLXI MDLXII And MDLXIII 2 pattern 108 pattern 107. pattern 109 pattern 239 formula 1.11 pattern 240 pattern 120 pattern 121 pattern 122 pattern 123 pattern 124 pattern 125 pattern 127 pattern 128 pattern 129 pattern 131 pattern 133 pattern 241 pattern 242 pattern 136 pattern 243 " pattern 244 pattern 245 pattern 139 pattern 140 pattern 246 pattern 142 pattern 143 pattern 147 pattern 247 " pattern 153 pattern 248 pattern 61 pattern 156 pattern 157 pattern 97 8 C2H4OC2H4OH C2H4OC2H4OH C2H4OCoH4OH CAOCAOH C2H4OC2H4OH CAOCAOH CAOCAOH CH / .OCoH4OH CAOCAOH CAOCAOH CAOCAOH caocaoH CAOCAOH CAOCEiOH CAOCAOH CEpcaOH C, H4OC> H, (OH CAOC2H4OH CAOCoH / .OH (CH1, CKCH,) 4OH (CH2) oQ (CH2) /, OH CAÓCAOH CAOCH / iOH CAOCAOH CAOCAOH CoH / sOCoHyOH CAOCAOH CAOCAOH C2H, OC2H4OH ,, (CH1), O (CH1), OH C, H, OG, H, ÓH • C, H, OC-.H, 10H ,, pattern 7 (CH1).} O (CH2) 2OH formula 8 pattern 14 pattern 222 (CH1) 3OCriH5 (CH.,) 3OCH, CfiH5 (CH2) 3OCoH4CfiH5 (CH.) 1OC2H4OCflH5 CH, CHOHCnHr> 4 yellow (Orange yellow golden yellow yellow red with a tint scarlet ruby »> Red ,, ,, scarlet with a tinge " red with a tint Red yellow ", Red blue with a tint »L . ,, b, » yellow-brown yellow . »» red with a tint 1> J -V ,, Violet Violet sky [Orange « . » red with a tint r » .Orange ,, » « », ,, J> ,, ,., " yellow brown blue red blue blue J. Table 8 Coupling components of formula 249 Example mr MDLXIV MDLXV MDLXVI MDLXVII MDLXVIII MDLXIX MDLXX MDLXXI MDLXXII MDLXXIII MDLXXIV MDLXXV MDLXXVI MDLXXVII MDLXXVIII MDLXXIX MDLXXX MDLXXXI 1 MDLXXXII Ingredient two-phase pattern 91 pattern 92 yi pattern 97 pattern 95 pattern 106 pattern 121 pattern 120 pattern 122 pattern 123 ", pattern 147 pattern 150 pattern 243 pattern 245 pattern 127 pattern 142 pattern 159 pattern 124 'Z1 (CH1) ;; O (CIL) 2 OH pattern 7 CH ^ OCHaOH C2H, OC9H4OH CAOCoH / jOH C, H4OC, H, OH CoH4OC2H, OH CH / PCzH / iOH G, H, 10OCoH, 1OH CAOCoH ^ .OH (CH.) OO (CH9) 4 OH CAOCAOH C2H4OC0H4OH C> H4OC2H, 1OH C2H, 1OC2H4OH CoH / hOC2H4OH C2H * OC2HyOH CoH / .OCoHr.OH C, H, OC2H4OH Coloring yellow golden yellow yellow Orange »1 yellow scarlet red with a tinge of yellow ruby » " ,, Violet blue with a red tinge blue Red Red with a blue tinge » red75 91830 Table 9 Components! coupling with formula 250 [Example no MDXXXIII MDXXXIV MDXXXV MOLXXXVI l MD (LXXXVII Ingredient two-phase pattern 120 pattern 08 pattern 97 pattern 120 pattern 123 X H. H. H. CONH2 * » WITH* C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH C2H4OC2H4OH Coloring red with a shade of yellow s ^ carlalt Orange red reddish phyllene 1 / Table 1 pattern 054 Example no MDLXXXIX R —C2H5 X —CH2 — CH2OH Y -CeH5 Coloring red with a tint blue | T a fo 1 i c a 2 Pattern 256 Example no MDXC MDXCI R —C3H7 —C3H7 X —CH2-CH2- ^ OH —H Y -H (CH2) 3- ^ O — CH2— —CfiH5 —C6H5 1 ruby color red with a tint blue 1 Table 3 'Pattern 256 ! Example no MDXCII ! MDXCIII R | X —C3H7 —C3H7 —CH2 ^ CH2- ^ OH —H —T Y ^ (CH2) 3- ^ 0 — CH2— "—CgH7." —C6H5 Coloring ruby red with a tint blue | IT ablic a 4 pattern 2157 | Example no | R MDXCIV MDXCV —C3H7 —C3H7 X | Y —CHa — CH2- ^ OH —CH2-CHj- ^ OH ^ C6H5 Pattern 258 Coloring red with a tint blue dark red 1 IT a fol i c a 5 • pattern 259 Example no MDXCVI 1 MDXCVII r —C2H5 —C2H5 X —CH2 — CH2 — O— —CH2 ^ CH2- ^ OH —CH2 — CHs- ^ OH Y —C6H5 —C6H5 Coloring red with a tint yellow 99 1 Table 6 aeo formula Example no MDXCVIII 1 MDXCIX R —C2H5 —C2H5 X ^ CH2- ^ CH2- ^ OH —CH2 — CH2 - OH Y —CeHg —C6H5 Coloring red with a tint yellow in 191 820 77 78 Table 7 pattern 261 Example no MDC MDCI MDCII MDCIII R —CaHrfn) —C ^ Cn) —C2H5 —C2H5 X ^ CHa — CHz — OH —CHa — CHa — OH --CHa — CH2 — OH —CH2 ^ CH2- ^ OH 1 Y ¦. pattern 20 —CeHs —CeH5 -C6H5 Coloring orange with - red shadow scarlet " and Table 8 Style 282 (Example no MDCIV MDCV MDGVI MDCVII QVCDCVIII MDCIX | MDCX R —C2H5 —C3H7 (n) —C2H5 —CaH ^ n) —C2H5 —CaH ^ n) —CjH ^ n) X —H —CHa — CHj — OH —CHz — CH2 — OH —CHa — CH2 — OH —CH * —CHa — OH —CHa — CH2 — OH —CHa — CHa — OH Y ^ (CH2) 3- ^ 0 - ^ (CHa) 6— —OH Pattern 258 Pattern 258 —Z ^ 6 ^ 5 —C6H5 Pattern 263 pattern 264 Coloring Red ruby-^ red "1 9> »> M. > t \ Table 9 pattern 265 Example no MDCXI MDCXII MDCXin MDCXIV | MDCXV B —C2H5 —C2H5 —C3H7 (n) —C3H7 (n) ^ C3H7 (n) * —CH2 — CH2 — CH2 ^ OH —CHa — CH2 — OH —H Pattern 258 Pattern 258 Y —C6H5 —C6H5 Pattern 258 —H —CHa — CHa — OH Color 1 islot yellow to orange ranch M. yellow > and 1 Table, 10 pattern 266 Example no MDCXVI 1 MDCXVII R —C3H7 (n) —C3H7 (n) X —CHa — CHa — OH —CHa- ^ CHa — CHa — OH Y Colors —CfiHs —C6H5 golden yellow »__! Table 11 pattern 267 Example no MDCXVIII MDCXIX MDCXX MDCXXI MDCXXII MDCXXIII 1 MDCXXIV R —C2H5 —C3H7 (n) —C2H5 —C3H7 (n) —C2H5 —CsH7 (n) —C3H7 (n) X —H —CHa — CHa — OH —CHa — CHa — OH —CHa — CH2 ^ OH —CHa — CHa — OH —CHa — CHa — OH —CHa — CHa — OH Y ^ (CHa ^ - ^ O ^ CHJe— —OH Pattern 258 Pattern 258 —C6H5 —C6H5 Pattern 263 pattern 264 Coloring red with undefined yellow Red »1 »1 »1 »1 Table 12 pattern 268 Example no | * R MDCXXV —C2H5 X —CH2 — CHa ^ OH Y —C6H5 Coloring red __J Table 13 pattern 269 [Example no | R | X 1 ¦ 1 MDCXXVI —C2H5 —CHa — CHa — OH Y Colors —C6H5 'ruby 91820 79 80 Example no MDCXXVII MDCXXVIII MDCXXIX MDCXXX \_with B —C2Hs —C2H5 —C2H5 ^ C3H7 (n) T a.iblic a Pattern 270 X —CH2 ^ CH2-rOH —CH2 — CH2 — CH2 — OH —CH2 — CH2 ^ OH ^ (CH2) 3 — O— (CH2) 6- —OH 14 Y ^ CfiH5 —CfiH.ij -C6H5 —H Coloring blue " * ' Violet Table 15 Pattern 271 [Example no MDCXXXI MDCXXXII MDCXXXIII MDCXXXIV R —C3H7 (n) —C3H7 (n) —C, H7 (n) —C3H7 (n) X —CH2 — CH2 - OH —H —CH2 — CH2 — OH Y ^ (CH2) 3—0 ^ (CH2) 2— —O— (CH2) 2 — OCH3 —CfiHs Pattern 258 Pattern 258 Coloring red-purple « •> " Table 16 visor 272 Example no MDCXXXV MDCXXXVI MDCXXXVII 1 MDCXXXVIII AND formula 273 formula 273 formula 273 CH, OCOCH2CH2 E. —C2H5 —C3H7 (m) —C3H7 (in) ^ C3H7 (n) X —CHs — CH2 — OH —CHa — CH2 — OH —CH2 — CH2 — CHa — OH —CH2-CH2 -OH Y —C6H5 —C6HR —C6H5 Pattern 258 Coloring Orange »1 Example no MDCXXXIX MDCXL MDCXLI MDCXLII R —C3H7 (n) —C3H7 (n) —C2H5 —C2H5 Table 17 pattern 274 X and Y —CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — OH —CH2 — CH2 — OH pattern 20 -CfiH, —CbH5 —CfiHs Coloring orange with odor a shadow of red scarlet »» " Example no MDCXLIII MDCXLIV MDCXLV MDCXLVI R -C3H7 (n) —C3H7 (n) —C2H5 —C2H5 Blackboard pattern 275 X —CH2-CH2-OH ^ —CH2 — CHa — OH —CH2 — CH2 — OH —CH2 — CHj — O— —CH2 — CH2 — OH 18 Y Pattern 258 -CeH5 —CeH5 -C6H5 Coloring Orange scarlet 9J Example no MDCXLVII MDCXLVIII MDCXLIX MDCL R —C ^ H7 (n) -C3H7 (n) —C2H5 —Q, HB Blackboard pattern 276 X —CH2 — CH2. — dk --CH2 — CH2 — OH ^ CH2 — CH2 — OH —CH2 ^ CH2 — O— —CH2 — CH2 — OH 19 Y pattern 20 —C6H5 —CfiH5 —CfiH5 - Coloring Orange (scarlet 91 Example no MDCLI MDCLII MDCLIII MDCLIV R -C3H7 (n) —C3H7 (n) —C2H5 -C2H5 Blackboard pattern 277 X —CHj — CH2 — OH —CHa — CHj — OH —CH2 — CH2 — OH —CH2 ^ GH2 — O— —CH2 - CH2 — OH Y pattern 20 —CfiHs —CfiH5 —C6HS Colors « yellow Orange "1SI 91820 Table 21 pattern 278 82 Example no. R X Coloring MDCLV MDCLVI MDCLVII MDCLVIII MDCLIX —C2H5 —C2H5 —Cyw-n) —C3H7 (n) —CH2 — CH2 — CH2 — OH —CH ^ CH ^ OH —H Pattern 258 Pattern 258 —CfiHf; Pattern 258 —H —CHs — CH2 ^ OH golden yellow to orange yellow Table 32 pattern 279 Example no. Coloring MDCLX MDCLXI MDCLXII MDCLXIII MDCLXIV —C2H5 —CaH ^ Cn) —C3H7 (n) —C3H7 (n) —CH2 — CH2 — CHb2OH —CH2 — CH2 — OH —H Pattern 258 Pattern 258 —CfiH3 CfiHr; Pattern 258 —H —CH2 — CH2 — OH golden yellow to orange yellow Board '23 model 280 Example no. Coloring MDCLXV MDCLXVT .3H7 C3H7 (n) -CH2-CH2-OH -H . (CH2) 3- ^ 0 — CH2— —CfiH5 -CfiHs red with a tint blue This is the face 24 pattern 281 Example no X Colors MDCLXVTI MDCLXVIII —C3H7 (n) 'OlHy -CH2 — CH2 ^ OH -H ¦4 (CH2) r-O — CH2— ¦ — CrH5 red with a tint blue Table 25 pattern 282 Example no. R X Coloring MDCLXIX MDCLXX -CaHTdi) -C3H7 (n) -CH2-CH2-OH -H u (CH2) 3-0-CHj— —CeH5 red with a tint blue Table, 26 formula 283 Example no MDCLXXI MDCLXXII MDCLXXIII MDCLXXIV MDCLXXV MDCLXXVI MDCLXXWI MDCLXXVin MOCLXXIX MDCLXXX MPCLXXXI MDCLXXXII MDCLXXXIII MDCLXXXIV MDCLXXXV MDCLXXXVI | MDCLXXXVII R1 H. H. H. H. H. H. H. iCCH ^ ÓCHAHfi . (CHaJiOCHjCeHB and (CH2) 3OCH2C6H5 and (CH2) 3OCH2C6H5 (CH2) 30CH2Cf; H5 pattern 17 pattern 17 pattern 17 pattern 17 jR2 (CH2) 3Oi (CH2) 2OH (CH2) 30 (CH2) riOH (CH2) 30 (CH2) &lt; 4 &gt; OH pattern 264 (CH2) 30i (CH2) 2OH (CH2) 30-CH2C6H5 pattern 284 CH2CH2OH (CH2) 30H (CH2) 30H CH2CH2OH CH2CH2OH (CH2) &lt; 4 &gt; OH (CH ^ OH CH2CH2OH CH2CH2OH (CH2) iOH iR3 C2HS C3H7 CH3 CH3 CH3 CH, CH3 C2H5 C2H5 CH3 CH3 CH3 CH3 CH ^ CH3 CH3 C2H5 R4 | CHa CH, CH, CH3 CH3 CH, CH ^. CH3 CH, CH3 CH3 C2H5 C <^ H ^ 0 ^ 5 C2H5 CHq CH3 Coloring pink ** 1 »> 3> red with a tint blue '' a * "* " ** »» " »• and — L - * - 191820 83 84

Claims (1)

1. Claim *. The preparation of 2,6-divalinopyridine azo dyes of formula I, in which D represents the rest of the active ingredient, R represents an optionally substituted alkyl group or an optionally substituted phenyl group, X represents a hydrogen group, cyano or optionally substituted carbanoyl, R 1 is (C 6 H 5, 4, 5, 6, (CH 2) 4 (CH 2) 2 OH, (CH 2) (CH 2) tfOH, 7 or 8 , of formula (CHaaCO ^OR7, (CH2) ^ (iOC2H4) qOR8, (CH2) ^ OR9, of formula 9, of formula C2H40C6H5, 52H40C6H5CH3, of formula 10 or 11 or containing hydroxyl groups of formula 12, R2 is hydrogen, the group given for R1, or an alkyl group of 1-8 carbon atoms, optionally containing an oxygen atom in the chain and optionally substituted hydroxy, alkoxy, acyloxy, carboxyl, carboxyester, cycloalkoxy, arylalkoxy or aryloxy groups or R2 "represents a cycloalkyl group - ~ 8 carbon atoms, optionally substituted hydroxy, chlorine, hydroxyalkyl, tMoroalkyl or alkyl groups, 7- to 15-atom arylalkyl groups, carbon or phenyl group, alkenyl, pyrrolidinylalkyl, or carboxyalkyl groups, which can be substituted by chlorine, hydroxy, alkoxy , alkyl, hydroxyalkoxy, or hydroxyalkyl; R3 is an alkyl group of 1-3 carbon atoms or a hydroxyalkyl group * R4 is hydrogen, an alkyl group of 1-3 carbon atoms or a hydroxyalkyl group * R5 is a hydrogen or a hydroxy group, R6 is a hydrogen, an allkyl group with 1-4 C atoms, methoxyl, ethoxy or chlorine group, and R7 is ethyl, propyl, butyl, cyclohexyl, benzyl, phenylethyl or methylphenyl group, R8 is hydrogen, alkyl group of 1-4 C atoms, cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl, R9 is cyclohexyl, phenyl, methylphenyl, benzyl or phenylethyl, m is 1 or 2, n is 0, 1 or 2, q is 3, 3 or 4, p is the number 1, 2 or 4, characterized in that the two% compound of the amine of formula 2 is reacted with the reactive component of formula 3, where the symbols D, R, R1, R2 and X have the above-mentioned importance. 15 20dl 820 RJ) -NN X R2HN N NHR1 Formula 4 (CH2) 3fOCH-CH ^ CH3 pVr8 Formula 9 YY y2Al_HNANANH_A1 Formula 4a R .. D-NH2 R2 HN N ^ \ NHR1 ^ H, H (CH-CH3-OC6H5 fCH-CH) OC6H4CH3 XCH3 \ h3 Formula 40 r CH- CH- fCH2) n R4 Formula M _ / ^ _ p5 Formulai> Formula 3 Formula \ 1 (CH2) m CH-C6H5 - (CH2) m CHC6U4CH3 CH3 CH3 (CH2) 3 0CH-CU2-OC6% (CW2) 3 0CHCH20CH3 CW3 CH3 Formula 4 Wór5 Formula 13 Formula M CH3 CH-rCH2) 3 ~ C -OH ^ CH2) 3 O ^ H) Ch3 Ch3 (C ^ 3-OChi-CH2- OCAHg CH3 Formula 6 Formula? Formula 15 • fCH2) 3-0CH2- (H) -CH2 0W fCH2) 3-OCH-CH2-OCH2C6W5 CH3 Formula 8 Formula \ b91820 • C ^ 3 (CH2) 3-0CH2 CH-0CGH5 Formula WI CH3 Formula 18 Formula 20 -0CH2CH- Formula 19 M2M-OC6H5 -CH-CH2-0C6H5 1 L CH3 CH3 Formula 21 rcH2} 3 0CH2CHC4U9 C2H5 Formula 27 ¦CHCH2OCH3 -CHCW20C4H9 CH3 CH3 Formula 28 Formula 29 ¦CMCH2OCH2C6H5 -CU2CHOCMo II CH3 W / zór 30 l4 / ztór3f CH3 ¦CH- (CH2h- \ / - ° H Formula 22 ¦CH2CH-OC2H5 -CH2CM-OC4H9 CH3 CH3 iA / ztfr 32 lA / Zdr 33 • CH2-CH-C4Hg C2H5 Formula 23 - CH2CH0H CH3 Formula 24 -CH2CH-OC2H4C6H5 -CH2-CH-0-4cyL CW3 Formula 34 CH3 Formula 35 • CH-CH20H _CH2 ^ h> Ch20M CH3 -C0-CH- (CH2) 3-CH3 -C0-CH = C H-l \ C2H5 Formula 25 Formula 26 Formula 36 Formula 3791820 C0-CH2-0 - {^ \ CO "(~) OH H - (H Formula 38 Formula 39 Formula bO Formula 51 CO- / \ ..». uu / \ HJ - <H CH2CW2OH - 'XOCH2CH2OH Formula 40 6 Formula 42 WzsrAi (CH2b- <moor 52 CH3 I CH (CH2) 2- Pattern6r53 -OH Wair43 Formula 54 (CH2IrO Formula 44 H Formula 46 - © (CH2 ^ - 0 Formula 45 -a; Formula 47 <3 CH * CH2 CH-C6H5 CH (CW2> 3 CfCH3) 2 CH3 CH3 OH Formula 55 (CH2) 3 0- (h Formula 57 H3C CN Formula 56 R1HN N ~ NH2 \ Nz6r 58 NH> = M / a moor48 moor 49 moor 5991820 H3CNCN j3-o NH-CH2-CH2-CH2-OH Formula 60 02H \ N = N CH3 CN,> = <: CH3 CH3 v / rNH-CH- (CH2) 3 -C-OH NH-CH- (CH2) 3-C-rCH3) 2 J CH3 OH Formula 62 -N O2N As- NH2 Formula 61 CH3 CN Cl CH3 y CH3 CH3 NH-CH- (CH2) 3-C-OH CH3 CH3 NH-CH-CCH2) 3-C-OH CH3 CH3 Formula 63 Ci- / CU CH3 CN CH3 CH3 VN = fH \ 7) -NH-CH-rCH2) 3-C-OH -N CH3 CH3 N'H -CH-fCH2) 3-C-OH CW3 CH3 Formula 64 O2K O CH3 .CN N- -N \ rm * cu3 MH-CH- (CH2b-C-OH C% CH3 Formula 65 02N-1A /> = < CH3 XH NH2 CH3 NH-CH- (CH2) 3-C-OH CH3, Ch3 Formula 66 CN CHq CN CH3 NH-CH- (CH2) 3-C-OH CH3 CH3 Formula 6791820 CH3 CN N = HO "^ VN CH3 | / h-CH- (CH2) 3-C- ° H CH3 cH3 y formula 69 L_ / yN = N- N ^ -CH- (CH2) 3-C- ° H CH3 CH3 Formula 69 H3C, CN 02H-1) -H4) -NH- (. / NH-CH2-CH2-CH2-OW Cal > r 70, CH3 H2N-CH-CH2-CH2 / OH Formula 71 CN H3CCN? H3 02NJT ^ N = N / ~ V NH-CH-CH2-CH2 NH-CH2-CH2-OH Formula 71 / OH CN H3C CN qzn - (~ \ n = n \) -nh-ch2-ch2-oh XX -N, CH3 -CH'-CH2-CH2-r ^ - OK Formula 7391820 H3C, CN CH3 nh-ch-ch2-ch2 OH NHR2 Formula 74 H 3 C CN 1 f 1 1 1 H -CH-CH 2 -CH 2 - {/ "CH 3 mor 75 OM HsC. , CN - <P *) —NH-CH-CH2-CH2 ^ (_) - OH 4 ^ H-CH2-CH2-CH2-OH Formula 76 H3C CH CH3 ¦r * r ^ • H / h NH-CH-CH2 -CH2 xx N NH-CH2-CH2-CH2-OH Formula 77 OH H3C CN U NH2 NH-CH-CH2-CH2 CH3 / \ OH Ext 78 * feN:, C00CH2-CH2-0CH3 H3C CN N = N (j- NHo NH-CH-CH2-CH2-f Yc-H CH3 Formula 79 NHf ≤ 2 W * Jr80 and CH3S- ^ VnH2 NS Formula 8191 820 p2N CN H3C C0NH2 NH-CH2-CH2-OH Formula 82 OH CfcN- /, S % CH3 CH3CONH2 N- N -f) -NH-CH-CH2-CH2 NH-CH2-CH2-OH Formula 83 OH 02N XN and N = H3C H rl, COHH2 rC \ <\ r ^ H-CH-CH2-CH2 -fVOH NH-CH2-CH2-0H Formula 84 02N- f CN N - - N- E) -NH-CH-CH-CH2- (V NH-CH2-CH2-OH Formula 85 OH O2N Cl H3C CN ",, . J \ _ / CH3 / Vm_mV) - \ m-ch-zh-chJ A 'l -NN CH3 NH-CH2-CH2-OH Wals 86 OH 02N // N H3C CN N- NJA / - NH- CH- CH2-CHX V-0CHO NH-CH2-CH2 OCHO Formula 8791820 .CH N <~ \ / ~ m2 W = C- / ~ ^ VnH2 HO Formula 102 C00C2H5 NH2 C00C2H5 Formula 10A 9h Cl \ NH2 Formula 106 Formula 103 CL -, S03CH3 r ^ NH2 0 Formula 105 CH2-CHz-OH NO / r-NH2 moor 107 Formula 113 C4 Hg-NC - ^ - NH2 HO Formula 114 H3C CM ^ J-NH-R, O NH Formula 115 Q ^ N_N ^ -y NH2 Formula 108 COOCH3 BrY ~ "VNH2 CH3-N - | - / ~~ \ -NH2 Br Formula 109 Br C2H5-0C ^^ NH2 ^ H 0 in 0 Formula 1fO Cfy-CHg-O-CrA CH2 W, = 0 / V MH2 Formula W Formula 112 H3CC0NH2 NH-CH2-CH2-CH2 -0-CH3 Formula 116 NOr H3C / C0NH2 / \ IH-CH2-CH2-CH2-0-CH3 Formula li7% C .CN // ~ m ¦H / NH2 Formula 11891820 H3C CU CH20H NH-CH2-CH2-OH Wztfr88 .a CkN ~ \ / N H3C CN CH2 OH ML> N ~ \ // - NH-CH-CH2 NH-CH2-CH2-OH Formula 89 \ NH- COOCH3 a-TyNlfe 'D2N ^^ NH2 Tl Formula 30 Formula 91 Formula 96 Formula 97 CN Cl - / 7-NH2 / CN Br - ^^ - NH2 a O ^ t-Cj- ^ 2 02N- CH3 i - / ^ JhNH2 Formula 92 Formula 93 Formula 98 Formula 99 \ cw3 BM CN fy- NH9 xBr OCH3 Q2N - /> - NH2 \ = / N02 CL- / yNH2 V 'Formula 94 Formula © Formula iOO Formula W91820 NH2 Formula H9 Formula 124 Formula i25 CN L * r, n / ^ J-nh2 o2n ^ J-nh2 o2n- / ~ \ <& 9 Formula 120 .N - (_ VnH2 Formula 122 V Formula 121 02N ^ 3 ~ NH2 Xl Formula 123 Br nar 129 CN CN Formula m no2 WC "\ _ / ~ NH2 Cl Formula \ 33 \> t / MQ2 o2n ^ / ~ ^ Vnh2 \ ¦ Formula <27 Al ozN-Cymz Br Formula (30 W \ VnH2 Formula 32 C4Hgfr) HHCoC \ tti2 Formula 134 COOCH2-CH2-OCH3 ar * 26 Cl 02N- / Vnh2 CL Formula - (2891 820 ( .n) C4H9NH-CO \ -Br -NH2 'Br Formula \ 2> b SO2C6W5 Wzcr W0 / NO2 Br (Cl) O 1 s- I o Wa & rWf "Nfcfc NH2 a Formula 137 mdr in NH2 Wzdr 143 rryNH2 Rein 138 Formula 139 Formula 139 Formula 144 CH30-c4 N: NH2 NC J \ JH2 02N Exfir 145 ^ -NH2 Formula ^ 146 -CL 02 ^ -NH2 ^ ¦N * ^ Formula 147 C4% n) NHSO2 \ CL CL 02ff ^ V NHz -NH WzdrH9 WzóMSO91820 - £ S * o fi CM to S to -o cM V = o S § -o o 2— <I! O tO § CNI R 0 = 0 "RI CN 00 v» 1 a co r <to ^ 2 n: OO o to -o £ -LO zc CN ci1 & <0. C \ i X 2 2: "CNI CNI CM ^ O CO 3H o cS1 / co. im) -, SO m JO JM "91820 K s ^ o 1 £ • o CN: r every 1 O 1 CN and CM every 1 00 • o £ ^ 1 u ^ ° \ J ^ \ 1 1 ^^ T ii ^ ^ z ^ LO 1 CNJ r. ej ii CN XO 1 O! CM ZT every 1 CM CO ^ -Z CT) CD i— 15 ^ cS4 I91820 O- o 1 o 1 CNI xox \ z? 1 o i1 1 i4 o 1 8 X ooo 1 CO "? 4 X o 1 en lxx o- ^ 00 i_ -o 5: what ooo I CM 00 -r 5-5 0Q -o NI J = f> what X -o ss s lty X ' O cO 1 x zr oo CM X o 1 i: z Z [o JL \ ^^^ »o ^ en 1 TL ^ 4P zr O 1 oi CM 3: O it CN rr of CNI X ^ J ^ 2 ^ l> - k_ ¦p ^ ^: what are ki CM XO i X "Z-. JL"> z X o cvi 1C o 1 CNI X Ci <£> t ^ ^ "x_ ¦o to Of o— I CNI X o I what 1? rkl X91820 what I Oo CM CNI XO * 'OXOX ix jn CNI X sif -o jcri CM • X. O. every 1 s = c 0- ^^ o> k. "O ^ l S 00 co £ csl : n ^ o co er m UT) X UD O 1 XO i '"1 CM X every 1 X ^ 1 j Vs ^^ XO: J_ ^^ en co CM X; / / ^ OO § o every cS491 820 m < 2? 'Csi O N- ^ o— <_>. Ze 5 I yS JU1- O ro o: o 1 oii CN zz ol CNI ZL O 1 CN | o "^ Z t * - o> -o NI ^ _ £ D OO-CJ co * cxl nz o coT o-every 1 rO ZE, O rr what every I cvi I Ol s / £ s 00 en IE -r- w ^ V oo < - ^ »CN4 ZE O ^ s * m i = C X o-o 1 I 1 r ^ r 3? by 1 CN | o 1 oo CM ¦p £ # 91820 o * CS] CM CO i—> - ^ 91820 X (OOIOI co x: r oo i cvi o ix o I CM X os CM X o IX iO CM ON iO X th OIO oo i CM £ O CO 1 \ Q = 0 ii O CO X o 5 O -SN XO 1 CM XO l X "Z IO CM s <= zo \ ox; £» O kix: OIO i X en x oo o:? CM O fooo O ri * K ^ O ^ J en ^ X 1 I oi rf ^ CNI X oau JL li UL X o \ Ol 3 CNJ XI O II O a JP * ^ CM X yi cm ¦o> ^ * 91 820 H3C CN Wy / CU f ~ ym2 j) -n = n / JVnh-z1 NH-fCH2) 3-0-CH2-CH2-0H NH-Z2 Formula2W Formula 220 H3C XN (fcN- / VN = N- / Vnh2 NH -fCH2) 3-O-fCH2) 2-0H (CH2) 3-0- (CH2-CH-0) 2 C4H9 _ (CH2) 3 _ roCH2 CH) 20C6H5 CH3 CH3 Wdr 22/1 Formula 224 • (CH2) 3- (09HCH2) 2-O-CH3 - (CH2) 3- (O-C2H4) 2-O ^^ CH3 Formula 222 Mor 225. (CH2) 3- (O-CHCH2) 3 0CH3 - (CH2) 3- ( 0-CH-CH2) 2-0-C6H5 CH3 CH3 Vomit 223 Formula 22691820 Formula 227 -CH2-CH- CH3 Formula 229 Cl- COOCH3 NH2 Formula 228 / CN CH3 MC- / VNH2 Formula 230 H3C CC NH-Z2 Formula 231 C "3 H3C /: 0NH2 JD-NN - ^ / VNH-Zf jTj | Z2-HW NH-Z4 CH3, CN ¦ ¦m- (CU2> 3-0-CUzC6U5 NH- (CH2) n-OH Formula 233 CH3 / CN NH- (CH2; n-NM Formula 232 0 Formula 235 CN CH3 CN O2N - {/ - N = NA> ~ NH- CH2- CH2-0H / MH- (CH2 / 3-O-fCH2-CH20) 2-C6H5 Formula 236 H3C CN N = <- "CH3 CH3 NHCHrCH2i3 C-OH CH3 Formula 237 CH3S02 -Q-NH2 Formula 23491820 X00C2H5 H5C2Q0C-l VnH2 CH3HN02 $ - (/ ~ NH2 Formula 238 C3M7OCH3 Formula 240 HgC4HN (# Formula 239 a Br / rNH2 H9C4HN0C- () -NH2 Cl Formula 241 with Br NH2 Formula 247 02M I NH2 Formula 244 cy ^ -C} - 'w2 Formula 246 C ^ 3Q0CH2CU2C5 HV \ s Formula 248 NHZ1 / CH3 NHCH— (CH2) 3-C-OH ch3 \ h3 Formula 249 C \ _VX CH3 CH3 ( yNHCHCCH2) 3C-OH) = N CH3 NHZ 'C2H5 CN Formula 250 CH3 (^) —NH-CH2-CH-C6H5 NH-CH2-CH2-0H Wr ^ r 25 101 820 C2H5 CN K NH-CH2-CH2-0H NH -CH2-CH-C6H5 Formula 252 CN C2H5 CN CH3 02M ^ y N = (U / VNH-CHrCH-C6H5 NH-CH2-CH2-OH Formula 253 CN CN p2N-f \ -N = fU ^ -NH-Y - CH2-CH-c5H5 CHa Formula 2 "55 o2H- ^ j ^^ Nt-ym_y y— / n NH-X Formula 255 yBr flyCN o2N- {JyN = NJ- \ NH_y> = N NH-X Wzc5r 260 CN R ' \ 02N N = N 'XN N CN> -NH-Y Ci HN-X Formula 255 CN R ° 2N ~ Q ^ N = N v ^ CN NH-Y Br HN-X lA / zór 256 RC H PzN ^ JN = N- / ~ VnH-Y NH Formula 261 H3CO2S A Vycn 02N-Q- N = N ^ yNH-Y NH-X Formula 262 yN02 R CN ° 2N ~ f Vn-N- / VNH_Y NH-X Formula 257 p3 ^ CHs -CH2-CH2-p-C6H5 -CH-rCH2) 3-C-OH C ^ 3 \ u3 Formula 263 IrYznr 26491 820 CN R CN CL - /) - N-.N - () - NH -Y \ A / N NH-X Formula 265 R .CN Xl "W" NH-X Formula 271 CN R CN /) _ n - N- / ~~} -NH-Y NH-X Formula 266 H3C02C R CH NH -X Formula 267 a "Vn rwcn N 3-N = NHfVNH-Y NH-X Formula 272 0 CH30C2U4 OC-CU2-CH2- Formula 273 O2N H3CO R .CN ¦NN NH-Y = N NH-X Formula 268" la ; iv / Vn-n- (Vnh-y NH-X Formula 274 02 \ NO2 R CN NC- / Vn-N - /) - NH-Y a / NH-X Formula 269 R CN 1 "NNf Vnh-y NH -X Formula 270 NH-Y CN R CN - ^ J ^ N = N ^} - NH-Y Cl NH-X Formula 27691820 Br CN R, cn »-NH-Y aC NH-X Formula 277 COOCH3 R / CN N = | \ lY) -MH-Y NH-X Pattern6r 278 H3C CN CH3OC 0 As \ _NJ ^ / n MN-X Formula 280 M02 RxCN n / u HN-X Formula 281 Cl CDOCH3 RN = N NH-Y Q2N NO02 Br , CN \ ~ Ui) -NH-Y HN-X Formula 282 CH3 CN R4-0-C CN • 5 ^ \ N_N_ / Vmh-R1 N 0 M-R2 Wzfir 283 (CH2> 3QCH2CH20CH2 CH3 C6H5 Wzc> r 284 WZGraf ., Zd. No. 2, sam. 831/77, A4, 110 Price PLN 10