CH615937A5 - Process for the preparation of novel dyestuffs for synthetic textile material - Google Patents

Process for the preparation of novel dyestuffs for synthetic textile material Download PDF

Info

Publication number: CH615937A5
Authority: CH; Switzerland
Prior art keywords: formula; radical; alkyl; lower alkyl; groups
Prior art date: 1973-04-04

Application number

CH479873A

Other languages

German (de)

English (en)

Inventor

Stefan Dr Koller

Peter Aeschlimann

Original Assignee

Ciba Geigy Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-04-04

Filing date

1973-04-04

Publication date

1980-02-29

1973-04-04 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-04-04 Priority to CH479873A priority Critical patent/CH615937A5/de

1974-03-25 Priority to CA195,858A priority patent/CA1032537A/fr

1974-03-28 Priority to US05/455,779 priority patent/US3998805A/en

1974-04-01 Priority to CA196,542A priority patent/CA1051423A/fr

1974-04-01 Priority to GB1432774A priority patent/GB1471333A/en

1974-04-02 Priority to DE2416003A priority patent/DE2416003A1/de

1974-04-02 Priority to DE19742416002 priority patent/DE2416002A1/de

1974-04-02 Priority to AR25310974A priority patent/AR201685A1/es

1974-04-03 Priority to IT5001574A priority patent/IT1004075B/it

1974-04-03 Priority to FR7411762A priority patent/FR2224523B1/fr

1974-04-03 Priority to ES424894A priority patent/ES424894A1/es

1974-04-03 Priority to ZA00742134A priority patent/ZA742134B/xx

1974-04-03 Priority to IT50014/74A priority patent/IT1004074B/it

1974-04-03 Priority to FR7411763A priority patent/FR2224525B1/fr

1974-04-03 Priority to ZA00742133A priority patent/ZA742133B/xx

1974-04-03 Priority to BE142775A priority patent/BE813217A/fr

1974-04-03 Priority to BE142774A priority patent/BE813216A/fr

1974-04-03 Priority to ES424893A priority patent/ES424893A1/es

1974-04-04 Priority to JP3746674A priority patent/JPS49130920A/ja

1974-04-04 Priority to GB1503774A priority patent/GB1469453A/en

1974-04-04 Priority to JP49037465A priority patent/JPS49130919A/ja

1980-02-29 Publication of CH615937A5 publication Critical patent/CH615937A5/de

Links

239000000463 material Substances 0.000 title claims abstract description 14
238000000034 method Methods 0.000 title claims description 37
238000002360 preparation method Methods 0.000 title claims description 4
229920002994 synthetic fiber Polymers 0.000 title abstract description 3
239000004758 synthetic textile Substances 0.000 title abstract 2
230000008878 coupling Effects 0.000 claims abstract description 60
238000010168 coupling process Methods 0.000 claims abstract description 60
238000005859 coupling reaction Methods 0.000 claims abstract description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 47
238000004043 dyeing Methods 0.000 claims abstract description 20
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 7
125000001424 substituent group Chemical group 0.000 claims abstract description 6
150000001989 diazonium salts Chemical class 0.000 claims abstract description 5
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 4
-1 benzene radical Chemical class 0.000 claims description 176
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 44
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
125000003545 alkoxy group Chemical group 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 29
239000000460 chlorine Substances 0.000 claims description 25
239000000975 dye Substances 0.000 claims description 24
150000003254 radicals Chemical class 0.000 claims description 24
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 19
229920000728 polyester Polymers 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
125000004093 cyano group Chemical group *C#N 0.000 claims description 11
239000006185 dispersion Substances 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
239000000986 disperse dye Substances 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
239000002270 dispersing agent Substances 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
238000001914 filtration Methods 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
230000002209 hydrophobic effect Effects 0.000 claims description 3
239000011368 organic material Substances 0.000 claims description 3
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 3
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
125000001769 aryl amino group Chemical group 0.000 claims description 2
125000005110 aryl thio group Chemical group 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
239000003086 colorant Substances 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002894 organic compounds Chemical class 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
239000000835 fiber Substances 0.000 description 16
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 11
102100040996 Cochlin Human genes 0.000 description 11
101000748988 Homo sapiens Cochlin Proteins 0.000 description 11
125000000370 germanetriyl group Chemical group [H][Ge](*)(*)* 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
229920001577 copolymer Chemical class 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
239000004952 Polyamide Substances 0.000 description 3
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
229920002647 polyamide Polymers 0.000 description 3
239000001632 sodium acetate Substances 0.000 description 3
235000017281 sodium acetate Nutrition 0.000 description 3
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 2
239000012267 brine Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
125000006125 ethylsulfonyl group Chemical group 0.000 description 2
239000004744 fabric Substances 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
239000005457 ice water Substances 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
239000000203 mixture Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
MLVYOYVMOZFHIU-UHFFFAOYSA-M sodium;4-[(4-anilinophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].C1=CC(S(=O)(=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 MLVYOYVMOZFHIU-UHFFFAOYSA-M 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000000859 sublimation Methods 0.000 description 2
230000008022 sublimation Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000002351 wastewater Substances 0.000 description 2
ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
QQLILYBIARWEIF-UHFFFAOYSA-N 2-(2-hydroxyethylsulfonyl)ethanol Chemical compound OCCS(=O)(=O)CCO QQLILYBIARWEIF-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
BLMPRGKLRSGNAM-UHFFFAOYSA-N 2-chloro-1-[3-(diethylamino)phenyl]ethanone Chemical compound CCN(CC)C1=CC=CC(C(=O)CCl)=C1 BLMPRGKLRSGNAM-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
NKXPRYBNUGINBZ-UHFFFAOYSA-N 4,6-diamino-2-bromopyridine-3-carbonitrile Chemical compound NC1=CC(N)=C(C#N)C(Br)=N1 NKXPRYBNUGINBZ-UHFFFAOYSA-N 0.000 description 1
125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
VDBJCDWTNCKRTF-UHFFFAOYSA-N 6'-hydroxyspiro[2-benzofuran-3,9'-9ah-xanthene]-1,3'-dione Chemical compound O1C(=O)C2=CC=CC=C2C21C1C=CC(=O)C=C1OC1=CC(O)=CC=C21 VDBJCDWTNCKRTF-UHFFFAOYSA-N 0.000 description 1
GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
101100005001 Caenorhabditis elegans cah-5 gene Proteins 0.000 description 1
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
229920000571 Nylon 11 Polymers 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
150000003926 acrylamides Chemical class 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
LFZDEAVRTJKYAF-UHFFFAOYSA-L barium(2+) 2-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonate Chemical compound [Ba+2].C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21.C1=CC=CC2=C(S([O-])(=O)=O)C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C21 LFZDEAVRTJKYAF-UHFFFAOYSA-L 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
KYPOHTVBFVELTG-UHFFFAOYSA-N but-2-enedinitrile Chemical group N#CC=CC#N KYPOHTVBFVELTG-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
OIQPTROHQCGFEF-UHFFFAOYSA-L chembl1371409 Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 OIQPTROHQCGFEF-UHFFFAOYSA-L 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004040 coloring Methods 0.000 description 1
NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 description 1
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
125000001142 dicarboxylic acid group Chemical group 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
229940008406 diethyl sulfate Drugs 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000004044 disperse dyeing Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical group 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
QEGNUYASOUJEHD-UHFFFAOYSA-N gem-dimethylcyclohexane Natural products CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
UMRWDRULUZVLAY-UHFFFAOYSA-N hydroxymethylsulfonylmethanol Chemical compound OCS(=O)(=O)CO UMRWDRULUZVLAY-UHFFFAOYSA-N 0.000 description 1
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
LZBDHQJAHVRQDI-UHFFFAOYSA-N n-(3-acetamido-5-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC(N)=CC(NC(C)=O)=C1 LZBDHQJAHVRQDI-UHFFFAOYSA-N 0.000 description 1
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
HQLFTQUBRWAEGR-UHFFFAOYSA-N n-[3-(dibenzylamino)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 HQLFTQUBRWAEGR-UHFFFAOYSA-N 0.000 description 1
FPUKYOSOAAPHTN-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]acetamide Chemical compound CCN(CC)C1=CC=CC(NC(C)=O)=C1 FPUKYOSOAAPHTN-UHFFFAOYSA-N 0.000 description 1
SVIPVFDSQLTSKB-UHFFFAOYSA-N n-[3-(diethylamino)phenyl]formamide Chemical compound CCN(CC)C1=CC=CC(NC=O)=C1 SVIPVFDSQLTSKB-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
239000004753 textile Substances 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000002759 woven fabric Substances 0.000 description 1
239000001043 yellow dye Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH479873A 1973-04-04 1973-04-04 Process for the preparation of novel dyestuffs for synthetic textile material CH615937A5 (en)

Priority Applications (21)

Application Number	Priority Date	Filing Date	Title
CH479873A CH615937A5 (en)	1973-04-04	1973-04-04	Process for the preparation of novel dyestuffs for synthetic textile material
CA195,858A CA1032537A (fr)	1973-04-04	1974-03-25	Teintures pour tissus synthetiques
US05/455,779 US3998805A (en)	1973-04-04	1974-03-28	Sulphatoethylene (sulphonyl or sulphonylamino) phenyleneazo dyestuffs
CA196,542A CA1051423A (fr)	1973-04-04	1974-04-01	Teintures pour textiles synthetiques
GB1432774A GB1471333A (en)	1973-04-04	1974-04-01	Monoazo dyes containing a sulphato-ethyl group
DE2416003A DE2416003A1 (de)	1973-04-04	1974-04-02	Farbstoffe fuer synthetisches textilmaterial deren herstellung und verwendung
DE19742416002 DE2416002A1 (de)	1973-04-04	1974-04-02	Farbstoffe fuer synthetisches textilmaterial verfahren zu deren herstellung und ihre verwendung
AR25310974A AR201685A1 (es)	1973-04-04	1974-04-02	Nuevos colorantes monoazoicos para materiales textiles sinteticos
IT5001574A IT1004075B (it)	1973-04-04	1974-04-03	Coloranti a dispersione per materiali sintetici e procedimento per la loro produzione ed applicazione
FR7411762A FR2224523B1 (fr)	1973-04-04	1974-04-03
ES424894A ES424894A1 (es)	1973-04-04	1974-04-03	Procedimiento para la preparacion de colorantes de disper- sion acuosolubles.
ZA00742134A ZA742134B (en)	1973-04-04	1974-04-03	New dyestuffs for synthetic textile material their manufacture and their use
IT50014/74A IT1004074B (it)	1973-04-04	1974-04-03	Coloranti a dispersione per materiali sintetici e procedimento per la loro produzione ed applica zione
FR7411763A FR2224525B1 (fr)	1973-04-04	1974-04-03
ZA00742133A ZA742133B (en)	1973-04-04	1974-04-03	New dyestuffs for synthetic fibres, their manufacture and their use
BE142775A BE813217A (fr)	1973-04-04	1974-04-03	Nouveaux colorants pour matieres textiles synthetiques
BE142774A BE813216A (fr)	1973-04-04	1974-04-03	Nouveaux colorants pour matieres textiles synthetiques
ES424893A ES424893A1 (es)	1973-04-04	1974-04-03	Procedimiento para la preparacion de colorantes de disper- sion acuosolubles.
JP3746674A JPS49130920A (fr)	1973-04-04	1974-04-04
GB1503774A GB1469453A (en)	1973-04-04	1974-04-04	Monoazo dyes containing a sulphato-ethyl group
JP49037465A JPS49130919A (fr)	1973-04-04	1974-04-04

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH479873A CH615937A5 (en)	1973-04-04	1973-04-04	Process for the preparation of novel dyestuffs for synthetic textile material

Publications (1)

Publication Number	Publication Date
CH615937A5 true CH615937A5 (en)	1980-02-29

Family

ID=4282726

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH479873A CH615937A5 (en)	1973-04-04	1973-04-04	Process for the preparation of novel dyestuffs for synthetic textile material

Country Status (3)

Country	Link
BE (2)	BE813217A (fr)
CH (1)	CH615937A5 (fr)
ZA (2)	ZA742134B (fr)

1973
- 1973-04-04 CH CH479873A patent/CH615937A5/de not_active IP Right Cessation
1974
- 1974-04-03 ZA ZA00742134A patent/ZA742134B/xx unknown
- 1974-04-03 BE BE142775A patent/BE813217A/fr unknown
- 1974-04-03 BE BE142774A patent/BE813216A/fr unknown
- 1974-04-03 ZA ZA00742133A patent/ZA742133B/xx unknown

Also Published As

Publication number	Publication date
BE813217A (fr)	1974-10-03
ZA742133B (en)	1975-03-26
BE813216A (fr)	1974-10-03
ZA742134B (en)	1975-03-26

Legal Events

Date	Code	Title	Description
1983-12-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE1932806C3 (de)	1974-10-10	Wasserunlösliche Monoazofarbstoffe
DE2416003A1 (de)	1974-10-24	Farbstoffe fuer synthetisches textilmaterial deren herstellung und verwendung
CH634863A5 (de)	1983-02-28	Verfahren zur herstellung von von sulfonsauren gruppen freien azofarbstoffen.
DE2201112C2 (de)	1982-09-23	Disperse Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Textilmaterialien
DE2062717B2 (de)	1974-06-27	Azofarbstoffe aus 2,6-Diamino pyridin-derivaten, Verfahren zu deren Herstellung und Verwendung
DE2004488A1 (en)	1971-08-05	Water-soluble azo dyes for wool and poly-amide fibres
DE2460238A1 (de)	1975-07-03	Verfahren zur herstellung von azofarbstoffen und deren anwendung
CH616695A5 (en)	1980-04-15	Process for the preparation of azo dyestuffs
DE1932810B2 (de)	1979-06-07	Wasserunlösliche Monoazofarbstoffe und Verfahren zu deren Herstellung
DE2339010A1 (de)	1974-02-14	Neue farbstoffe fuer synthetisches textilmaterial
CH538528A (de)	1973-06-30	Verfahren zur Herstellung von faserreaktiven Farbstoffen
DE1901749A1 (de)	1969-07-31	Verfahren zur Herstellung von Azofarbstoffen
DE2050657C3 (de)	1974-06-20	Azofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung
DE19500228A1 (de)	1995-07-20	Dispersionsfarbstoffe
DE2309638A1 (de)	1974-09-12	Dispersionsfarbstoffe der 2,6diaminopyridinreihe
DE2801951A1 (de)	1979-07-19	Azofarbstoffe
DE1644052A1 (de)	1971-03-25	Verfahren zur Herstellung von neuen,wasserunloeslichen Azofarbstoffen
DE1912123A1 (de)	1969-10-23	Farbstoffe,Verfahren zu deren Herstellung und ihre Anwendung
DE2033253A1 (de)	1971-01-14	Farbstoffe. Verfahren zu deren Herstellung und ihre Anwendung
DE2416002A1 (de)	1974-10-24	Farbstoffe fuer synthetisches textilmaterial verfahren zu deren herstellung und ihre verwendung
DE2329133A1 (de)	1974-01-03	Disperse monoazofarbstoffe
DE2162179C3 (de)	1978-05-18	Azofarbstoffe und deren Verwendung
DE1644371A1 (de)	1972-03-16	Verfahren zur Herstellung in Wasser schwer loeslicher Farbstoffe
EP0362708A2 (fr)	1990-04-11	Colorants azo de la série du thiazole avec un composé diazoique de la série de l'isothiazole ou du thiadiazole
CH319237A (de)	1957-02-15	Verfahren zur Herstellung neuer kobalthaltiger Azofarbstoffe