CA1087173A - Azo pigments and processes for producing them - Google Patents

Azo pigments and processes for producing them

Info

Publication number: CA1087173A
Authority: CA; Canada
Prior art keywords: formula; alkyl; group; atoms; hydrogen
Prior art date: 1977-08-04
Legal status (The legal status 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 status listed.): Expired

Application number

CA308,577A

Other languages

English (en)

French (fr)

Inventor

Rolf Muller

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

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.)

1977-08-04

Filing date

1978-08-02

Publication date

1980-10-07

1978-08-02 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1980-10-07 Application granted granted Critical

1980-10-07 Publication of CA1087173A publication Critical patent/CA1087173A/en

Status Expired legal-status Critical Current

Links

239000000049 pigment Substances 0.000 title claims description 28
238000000034 method Methods 0.000 title description 4
230000008569 process Effects 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 13
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Chemical group 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
239000004033 plastic Substances 0.000 abstract description 2
229920003023 plastic Polymers 0.000 abstract description 2
238000004040 coloring Methods 0.000 abstract 1
FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 abstract 1
235000019233 fast yellow AB Nutrition 0.000 abstract 1
238000005859 coupling reaction Methods 0.000 description 15
230000008878 coupling Effects 0.000 description 14
238000010168 coupling process Methods 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
239000000975 dye Substances 0.000 description 6
-1 5-amino-6-chloroquinazolin Chemical compound 0.000 description 5
239000004800 polyvinyl chloride Substances 0.000 description 5
229920000915 polyvinyl chloride Polymers 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YVDQZFKTMIYDOK-UHFFFAOYSA-N 6-amino-5-methyl-3h-1,3-benzoxazol-2-one Chemical compound C1=C(N)C(C)=CC2=C1OC(=O)N2 YVDQZFKTMIYDOK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000012670 alkaline solution Substances 0.000 description 3
238000000227 grinding Methods 0.000 description 3
230000005012 migration Effects 0.000 description 3
238000013508 migration Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
KQNZKBRSEJLVEO-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-5-yl)butanamide Chemical compound C1=C(NC(=O)CC(=O)C)C=CC2=NC(=O)N=C21 KQNZKBRSEJLVEO-UHFFFAOYSA-N 0.000 description 2
CRXVBLLLPNWFBS-UHFFFAOYSA-N 4-aminobenzimidazol-2-one Chemical class NC1=CC=CC2=NC(=O)N=C12 CRXVBLLLPNWFBS-UHFFFAOYSA-N 0.000 description 2
ZCXIPVIGYBHUTQ-UHFFFAOYSA-N 5-amino-6-methyl-1,3-dihydrobenzimidazol-2-one Chemical compound C1=C(N)C(C)=CC2=C1NC(=O)N2 ZCXIPVIGYBHUTQ-UHFFFAOYSA-N 0.000 description 2
STLPJYGZOIEDAJ-UHFFFAOYSA-N 6-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=C2NC(=O)OC2=C1 STLPJYGZOIEDAJ-UHFFFAOYSA-N 0.000 description 2
TZCLXZMPJPMDDL-UHFFFAOYSA-N 6-aminoquinoxaline-2,3-dione Chemical compound O=C1C(=O)N=C2C=C(N)C=CC2=N1 TZCLXZMPJPMDDL-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
150000008049 diazo compounds Chemical class 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-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
PKJBRKTYYNRVSN-UHFFFAOYSA-N 10-(aminomethyl)-9,10-dihydroanthracene-1,2-diol Chemical compound OC1=CC=C2C(CN)C3=CC=CC=C3CC2=C1O PKJBRKTYYNRVSN-UHFFFAOYSA-N 0.000 description 1
MDRBCQOOJMXHOC-UHFFFAOYSA-N 2-(2-aminophenyl)-1h-quinazolin-4-one Chemical class NC1=CC=CC=C1C1=NC(=O)C2=CC=CC=C2N1 MDRBCQOOJMXHOC-UHFFFAOYSA-N 0.000 description 1
GFPYWRAKDBTCKF-UHFFFAOYSA-N 2-(3-amino-4-chlorophenyl)-1h-quinazolin-4-one Chemical compound C1=C(Cl)C(N)=CC(C=2NC(=O)C3=CC=CC=C3N=2)=C1 GFPYWRAKDBTCKF-UHFFFAOYSA-N 0.000 description 1
GXQIQJXRQMKQLA-UHFFFAOYSA-N 2-(3-amino-4-chlorophenyl)-6-chloro-1h-quinazolin-4-one Chemical compound C1=C(Cl)C(N)=CC(C=2NC3=CC=C(Cl)C=C3C(=O)N=2)=C1 GXQIQJXRQMKQLA-UHFFFAOYSA-N 0.000 description 1
FADCGTNRYVBUOM-UHFFFAOYSA-N 2-(3-amino-4-methylphenyl)-1h-quinazolin-4-one Chemical compound C1=C(N)C(C)=CC=C1C1=NC2=CC=CC=C2C(=O)N1 FADCGTNRYVBUOM-UHFFFAOYSA-N 0.000 description 1
MBSRJSOAGGRAHX-UHFFFAOYSA-N 2-(4-amino-3-methylphenyl)-1h-quinazolin-4-one Chemical compound C1=C(N)C(C)=CC(C=2NC3=CC=CC=C3C(=O)N=2)=C1 MBSRJSOAGGRAHX-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
SDTFBAXSPXZDKC-UHFFFAOYSA-N 2-imino-1,2,3,4-tetrahydroquinazolin-4-one Chemical class C1=CC=C2C(=O)NC(N)=NC2=C1 SDTFBAXSPXZDKC-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
VGLGTAGWVRMFQF-UHFFFAOYSA-N 4-amino-3h-1,3-benzoxazol-2-one Chemical class NC1=CC=CC2=C1NC(=O)O2 VGLGTAGWVRMFQF-UHFFFAOYSA-N 0.000 description 1
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
ISAVYTVYFVQUDY-UHFFFAOYSA-N 4-tert-Octylphenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 ISAVYTVYFVQUDY-UHFFFAOYSA-N 0.000 description 1
NDFCFTOWEKYFMV-UHFFFAOYSA-N 5-amino-1h-quinazoline-2,4-dione Chemical class N1C(=O)NC(=O)C2=C1C=CC=C2N NDFCFTOWEKYFMV-UHFFFAOYSA-N 0.000 description 1
GJXXUHGUCBUXSL-UHFFFAOYSA-N 5-amino-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC=C2OC(=O)NC2=C1 GJXXUHGUCBUXSL-UHFFFAOYSA-N 0.000 description 1
GWMSBABWKBFZCF-UHFFFAOYSA-N 5-amino-6-chloro-3h-1,3-benzoxazol-2-one Chemical compound C1=C(Cl)C(N)=CC2=C1OC(=O)N2 GWMSBABWKBFZCF-UHFFFAOYSA-N 0.000 description 1
DSCFIYWTQBJIDM-UHFFFAOYSA-N 5-amino-6-chlorobenzimidazol-2-one Chemical compound C1=C(Cl)C(N)=CC2=NC(=O)N=C21 DSCFIYWTQBJIDM-UHFFFAOYSA-N 0.000 description 1
XSIRKEBRWGMNSO-UHFFFAOYSA-N 5-amino-6-ethoxybenzimidazol-2-one Chemical compound C1=C(N)C(OCC)=CC2=NC(=O)N=C21 XSIRKEBRWGMNSO-UHFFFAOYSA-N 0.000 description 1
BIJADNBQOKYCAT-UHFFFAOYSA-N 5-amino-6-methoxy-3h-1,3-benzoxazol-2-one Chemical compound C1=C(N)C(OC)=CC2=C1NC(=O)O2 BIJADNBQOKYCAT-UHFFFAOYSA-N 0.000 description 1
GLNHLEPOIVXMQF-UHFFFAOYSA-N 5-amino-7-chloro-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC(Cl)=C2OC(=O)NC2=C1 GLNHLEPOIVXMQF-UHFFFAOYSA-N 0.000 description 1
HNIOENKXYQWUDN-UHFFFAOYSA-N 5-amino-7-methyl-3h-1,3-benzoxazol-2-one Chemical compound CC1=CC(N)=CC2=C1OC(=O)N2 HNIOENKXYQWUDN-UHFFFAOYSA-N 0.000 description 1
QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 description 1
MAIZCACENPZNCN-UHFFFAOYSA-N 6-amino-1h-quinazolin-4-one Chemical compound N1=CNC(=O)C2=CC(N)=CC=C21 MAIZCACENPZNCN-UHFFFAOYSA-N 0.000 description 1
SDUUYVWJDAEWSE-UHFFFAOYSA-N 6-amino-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=CC(N)=CC=C21 SDUUYVWJDAEWSE-UHFFFAOYSA-N 0.000 description 1
HAVSRAMAYFTTFU-UHFFFAOYSA-N 6-amino-4-chlorobenzimidazol-2-one Chemical compound C1=C(N)C=C(Cl)C2=NC(=O)N=C21 HAVSRAMAYFTTFU-UHFFFAOYSA-N 0.000 description 1
LANVQVULFZTCQR-UHFFFAOYSA-N 6-amino-4-methylbenzimidazol-2-one Chemical compound CC1=CC(N)=CC2=NC(=O)N=C12 LANVQVULFZTCQR-UHFFFAOYSA-N 0.000 description 1
XGYICSXQOIEICF-UHFFFAOYSA-N 6-amino-5-chloro-3h-1,3-benzoxazol-2-one Chemical compound C1=C(Cl)C(N)=CC2=C1NC(=O)O2 XGYICSXQOIEICF-UHFFFAOYSA-N 0.000 description 1
WQXFFJUUIIGPRY-UHFFFAOYSA-N 7-amino-1h-quinazolin-4-one Chemical compound N1C=NC(=O)C=2C1=CC(N)=CC=2 WQXFFJUUIIGPRY-UHFFFAOYSA-N 0.000 description 1
YJVIGCMCVAFCCB-UHFFFAOYSA-N 7-amino-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C=2C1=CC(N)=CC=2 YJVIGCMCVAFCCB-UHFFFAOYSA-N 0.000 description 1
JQJPBYFTQAANLE-UHFFFAOYSA-N Butyl nitrite Chemical compound CCCCON=O JQJPBYFTQAANLE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000575946 Ione Species 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
229920001807 Urea-formaldehyde Polymers 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
229960003116 amyl nitrite Drugs 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
150000008641 benzimidazolones Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 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
229920003086 cellulose ether Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000002270 dispersing agent 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
229920001971 elastomer Polymers 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
CSDTZUBPSYWZDX-UHFFFAOYSA-N n-pentyl nitrite Chemical compound CCCCCON=O CSDTZUBPSYWZDX-UHFFFAOYSA-N 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
230000000485 pigmenting effect Effects 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
238000006068 polycondensation reaction Methods 0.000 description 1
229920000728 polyester 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
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000007864 suspending Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
- C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
- 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- 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
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
- 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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Compositions Of Macromolecular Compounds (AREA)
Coloring (AREA)

CA308,577A 1977-08-04 1978-08-02 Azo pigments and processes for producing them Expired CA1087173A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH958177		1977-08-04
CH9581/77		1977-08-04

Publications (1)

Publication Number	Publication Date
CA1087173A true CA1087173A (en)	1980-10-07

Family

ID=4353476

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA308,577A Expired CA1087173A (en)	1977-08-04	1978-08-02	Azo pigments and processes for producing them

Country Status (6)

Country	Link
EP (1)	EP0000737B1 (da)
JP (1)	JPS5429334A (da)
BR (1)	BR7804978A (da)
CA (1)	CA1087173A (da)
DE (1)	DE2860649D1 (da)
DK (1)	DK344678A (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2847285A1 (de) *	1978-10-31	1980-05-14	Hoechst Ag	Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung
DE4007535A1 (de) *	1990-03-09	1991-09-12	Hoechst Ag	Wasserunloesliche azofarbmittel, ihre herstellung und verwendung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH552034A (de) *	1971-03-03	1974-07-31	Ciba Geigy Ag	Verfahren zur herstellung von neuen azopigmenten.
BE793635A (fr) *	1972-01-03	1973-07-03	Hoechst Ag	Colorants azoiques solides a la chaleur
DE2329781C2 (de) *	1973-06-12	1986-06-05	Hoechst Ag, 6230 Frankfurt	Benzoxazindion-Azopigmente, Verfahren zu ihrer Herstellung und ihre Verwendung als Farbmittel
CH611642A5 (da) *	1976-11-09	1979-06-15	Ciba Geigy Ag

1978
- 1978-07-27 EP EP19780100516 patent/EP0000737B1/de not_active Expired
- 1978-07-27 DE DE7878100516T patent/DE2860649D1/de not_active Expired
- 1978-08-02 CA CA308,577A patent/CA1087173A/en not_active Expired
- 1978-08-03 BR BR7804978A patent/BR7804978A/pt unknown
- 1978-08-03 DK DK344678A patent/DK344678A/da unknown
- 1978-08-04 JP JP9516678A patent/JPS5429334A/ja active Granted

Also Published As

Publication number	Publication date
EP0000737B1 (de)	1981-04-29
DE2860649D1 (en)	1981-08-06
JPS5429334A (en)	1979-03-05
EP0000737A1 (de)	1979-02-21
DK344678A (da)	1979-02-05
JPS6143387B2 (da)	1986-09-27
BR7804978A (pt)	1979-04-10

Legal Events

Date	Code	Title	Description
1997-10-07	MKEX	Expiry

Publication	Publication Date	Title
CA1303026C (en)	1992-06-09	Mixed crystals of laked azo dyes
US3963694A (en)	1976-06-15	Hydroxyquinolyl- and quinazolonylazoacetoacetylbenzimidazolone pigments
US3609134A (en)	1971-09-28	Azo pigments containing a 4-carboxamido phenomorpholene-(3) group
CA1087173A (en)	1980-10-07	Azo pigments and processes for producing them
US4229344A (en)	1980-10-21	Monazo pigments containing hydroxynaphthoylaminobenzimidazalone radical
US4555568A (en)	1985-11-26	Monoazo compounds derived from 3-nitro-4-amino-benzoates and 5-(2'-hydroxy-3'-naphthoylamino)-benzimidazolones
CA1135688A (en)	1982-11-16	Disazo compounds, process for their manufacture and their use
US4302389A (en)	1981-11-24	Azo compounds deriving from amino benzoic acid anilides and acetoacetylamino-benzimidazolone
DE2457687A1 (de)	1976-06-16	Neue azofarbstoffe
US4206114A (en)	1980-06-03	Monoazo pigments from diazotized 5-acylaminoanthranilic acid derivatives and acetoacetylaminobenzimidazolones
US3923774A (en)	1975-12-02	Quinazolone containing phenyl-azo-pyridine compounds
US5484901A (en)	1996-01-16	Isoindolineazo pigments
US4602961A (en)	1986-07-29	Process for pigmenting high molecular weight organic material
US6872245B2 (en)	2005-03-29	Azo pigments
US4088641A (en)	1978-05-09	4-Methyl-5-(benzimidazolonylazo)-6-hydroxypyridone-2 pigment
US4302388A (en)	1981-11-24	Monoazo compounds deriving from meta-amino-benzoic acid anilides and acetoacetyl amino-benzimidazolone
US4055559A (en)	1977-10-25	Disazo pigment containing at least 2 chlorine atoms and process for their manufacture
US3402168A (en)	1968-09-17	Monoazo pigments containing 2, 3-hydroxynaphthoic acid amide
CA1169053A (en)	1984-06-12	Azo pigments
US4491544A (en)	1985-01-01	Dyes having a diazo component and an isoquinoline coupling component
US4100156A (en)	1978-07-11	Chlorine-containing disaza pigments
US4053464A (en)	1977-10-11	Disazo pigments containing ether substituted alkoxy carbonyl groups
CA1054607A (en)	1979-05-15	Iminoisoindolinone pigments
JPH0239541B2 (da)	1990-09-06
US3498966A (en)	1970-03-03	Monoazo pigments containing a benztriazole radical