PL60565B1 - - Google Patents

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Publication number: PL60565B1
Authority: PL; Poland
Prior art keywords: formula; halogen; hydrogen; alkoxy; alkyl
Prior art date: 1966-11-28

Application number

PL117626A

Other languages

English (en)

Polish (pl)

Original Assignee

Ciba Societe Anonyme

Filing date

1966-11-28

Publication date

1970-06-25

1966-11-28 Application filed by Ciba Societe Anonyme filed Critical Ciba Societe Anonyme

1970-06-25 Publication of PL60565B1 publication Critical patent/PL60565B1/pl

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-1 carboxylic acid halide Chemical class 0.000 claims description 21
239000000975 dye Substances 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
229910052736 halogen Chemical group 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
229910052796 boron Inorganic materials 0.000 claims 1
150000008049 diazo compounds Chemical class 0.000 claims 1
239000002253 acid Substances 0.000 description 13
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960004050 aminobenzoic acid Drugs 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
238000002156 mixing Methods 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
229920000915 polyvinyl chloride Polymers 0.000 description 5
239000004800 polyvinyl chloride Substances 0.000 description 5
CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
230000005012 migration Effects 0.000 description 3
238000013508 migration Methods 0.000 description 3
239000000049 pigment Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 2
CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
GBOUQGUQUUPGLO-UHFFFAOYSA-N 2-chloro-5-methoxyaniline Chemical compound COC1=CC=C(Cl)C(N)=C1 GBOUQGUQUUPGLO-UHFFFAOYSA-N 0.000 description 2
HPSCXFOQUFPEPE-UHFFFAOYSA-N 2-chloro-5-methylaniline Chemical compound CC1=CC=C(Cl)C(N)=C1 HPSCXFOQUFPEPE-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 2
WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
229920000297 Rayon Polymers 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000000987 azo dye Substances 0.000 description 2
POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000001054 red pigment Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
CEMAWMOMDPGJMB-CYBMUJFWSA-N (2r)-1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-CYBMUJFWSA-N 0.000 description 1
MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
YECYUHRFXUFJRV-UHFFFAOYSA-N 2,4-dichloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=C(Cl)C=C1Cl YECYUHRFXUFJRV-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
WRTAZRGRFBCKBU-UHFFFAOYSA-N 2,5-dibromoaniline Chemical compound NC1=CC(Br)=CC=C1Br WRTAZRGRFBCKBU-UHFFFAOYSA-N 0.000 description 1
LNEVUNYUJNORRV-UHFFFAOYSA-N 2-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1 LNEVUNYUJNORRV-UHFFFAOYSA-N 0.000 description 1
RQJRPJUZTWJZLA-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline;hydrochloride Chemical compound Cl.NC1=CC(C(F)(F)F)=CC=C1Cl RQJRPJUZTWJZLA-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
RKUSRLUGUVDNKP-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethyl)aniline Chemical compound COC1=CC=C(C(F)(F)F)C=C1N RKUSRLUGUVDNKP-UHFFFAOYSA-N 0.000 description 1
XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
FNDYIQSNURRMNP-UHFFFAOYSA-N 2-phenoxy-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1OC1=CC=CC=C1 FNDYIQSNURRMNP-UHFFFAOYSA-N 0.000 description 1
AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
QNAAQOLWUDNQFY-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1.NC1=CC=CC(Cl)=C1 QNAAQOLWUDNQFY-UHFFFAOYSA-N 0.000 description 1
XDTTUTIFWDAMIX-UHFFFAOYSA-N 3-methyl-4-nitrobenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1[N+]([O-])=O XDTTUTIFWDAMIX-UHFFFAOYSA-N 0.000 description 1
QHWDUJPWCGEBTH-UHFFFAOYSA-N 4-amino-n-phenylbenzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1 QHWDUJPWCGEBTH-UHFFFAOYSA-N 0.000 description 1
GFONYIXQVXCOIX-UHFFFAOYSA-N 4-aminobenzoic acid;methanamine Chemical compound NC.NC1=CC=C(C(O)=O)C=C1 GFONYIXQVXCOIX-UHFFFAOYSA-N 0.000 description 1
CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 1
XBAPOWUMJRIKAV-UHFFFAOYSA-N 4-chloro-2-methoxy-5-methylaniline Chemical compound COC1=CC(Cl)=C(C)C=C1N XBAPOWUMJRIKAV-UHFFFAOYSA-N 0.000 description 1
WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
RPJXLEZOFUNGNZ-UHFFFAOYSA-N 5-methoxy-2-methylaniline Chemical compound COC1=CC=C(C)C(N)=C1 RPJXLEZOFUNGNZ-UHFFFAOYSA-N 0.000 description 1
240000002319 Citrus sinensis Species 0.000 description 1
MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000007499 fusion processing Methods 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
CDGNLUSBENXDGG-UHFFFAOYSA-N meta-Cresidine Chemical compound COC1=CC=C(N)C(C)=C1 CDGNLUSBENXDGG-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
150000002763 monocarboxylic acids Chemical class 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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
LPEZIAPDJJLVHP-UHFFFAOYSA-N n-chloro-4-methylaniline Chemical compound CC1=CC=C(NCl)C=C1 LPEZIAPDJJLVHP-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
QRKVRHZNLKTPGF-UHFFFAOYSA-N phosphorus pentabromide Chemical compound BrP(Br)(Br)(Br)Br QRKVRHZNLKTPGF-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000002964 rayon Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
229960005369 scarlet red Drugs 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

PL117626A 1966-11-28 PL60565B1 (de)

Publications (1)

Publication Number	Publication Date
PL60565B1 true PL60565B1 (de)	1970-06-25

Publication	Publication Date	Title
AU641483B2 (en)	1993-09-23	Water-insoluble azo dyes, their manufacture and use
US3252964A (en)	1966-05-24	Water-soluble cationic azo-dyestuffs
US3872078A (en)	1975-03-18	Disazo pigments, processes for their manufacture and use
US3711461A (en)	1973-01-16	Monoazo dyestuffs containing an acetylamino 2,4-dioxo-1,2,3,4-tetrahydroquinazoline
US3113938A (en)	1963-12-10	Water-insoluble monoazo-dyestuffs and process for their manufacture
US3532683A (en)	1970-10-06	Cationic mono azo dyes for anionic fibers
US3609134A (en)	1971-09-28	Azo pigments containing a 4-carboxamido phenomorpholene-(3) group
US4229344A (en)	1980-10-21	Monazo pigments containing hydroxynaphthoylaminobenzimidazalone radical
US3549612A (en)	1970-12-22	Cationic aryl monoazo and disazo - 3 - substituted - 1 - aminomethylpyrazolone dyes
PL60565B1 (de)	1970-06-25
US3325470A (en)	1967-06-13	Water-insoluble monoazo dyestuffs
JPS62116669A (ja)	1987-05-28	ピペラジン残基を有する化合物及びその用途
US3402168A (en)	1968-09-17	Monoazo pigments containing 2, 3-hydroxynaphthoic acid amide
US3509125A (en)	1970-04-28	Monoazo dyestuff pigments
US3684792A (en)	1972-08-15	New water-insoluble azo-compounds containing a carboxamido-carbostyril group
US3257378A (en)	1966-06-21	Indazolium azo dyestuffs
US3849394A (en)	1974-11-19	Monoazo pigments containing a hydroxynaphthoylaminoacridone radical
US3336288A (en)	1967-08-15	Mono-azo pigments
US2221029A (en)	1940-11-12	Azo compounds and material colored therewith
US4055559A (en)	1977-10-25	Disazo pigment containing at least 2 chlorine atoms and process for their manufacture
US2468457A (en)	1949-04-26	Water-insoluble azo dyestuffs
US3366623A (en)	1968-01-30	Monoazo dyestuff pigments
US3642768A (en)	1972-02-15	Water-insoluble phenyl-azo-naphthol dyestuffs
US4100156A (en)	1978-07-11	Chlorine-containing disaza pigments
US2231707A (en)	1941-02-11	Azo compounds and material colored therewith

PL60565B1 - - Google Patents

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