CA1060000A - Azo pigments - Google Patents
Azo pigmentsInfo
- Publication number
- CA1060000A CA1060000A CA211,136A CA211136A CA1060000A CA 1060000 A CA1060000 A CA 1060000A CA 211136 A CA211136 A CA 211136A CA 1060000 A CA1060000 A CA 1060000A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- formula
- alkoxy
- denotes
- methyl
- Prior art date
- 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
Links
- 239000000049 pigment Substances 0.000 title claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 4
- -1 acetylamino, guanidino Chemical group 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000005521 carbonamide group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000002825 nitriles Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000007639 printing Methods 0.000 abstract description 9
- 239000000976 ink Substances 0.000 abstract description 5
- 239000004922 lacquer Substances 0.000 abstract description 5
- 238000004043 dyeing Methods 0.000 abstract description 4
- 239000003973 paint Substances 0.000 abstract description 4
- 230000000485 pigmenting effect Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 208000000655 Distemper Diseases 0.000 abstract description 2
- 239000011230 binding agent Substances 0.000 abstract description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- JQZJMILBKZUKLV-UHFFFAOYSA-N (6-amino-4-oxo-1h-pyrimidin-2-yl)cyanamide Chemical compound NC1=CC(=O)N=C(NC#N)N1 JQZJMILBKZUKLV-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000306 component Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- YPSSCICDVDOEAI-UHFFFAOYSA-N methyl-2-amino-4-chlorobenzoate Natural products COC(=O)C1=CC=C(Cl)C=C1N YPSSCICDVDOEAI-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000001052 yellow pigment Substances 0.000 description 3
- UZHALXIAWJOLLR-UHFFFAOYSA-N 2-amino-4-chlorobenzonitrile Chemical compound NC1=CC(Cl)=CC=C1C#N UZHALXIAWJOLLR-UHFFFAOYSA-N 0.000 description 2
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- CXNVOWPRHWWCQR-UHFFFAOYSA-N 4-Chloro-ortho-toluidine Chemical compound CC1=CC(Cl)=CC=C1N CXNVOWPRHWWCQR-UHFFFAOYSA-N 0.000 description 2
- CISVVDNATRQDNU-UHFFFAOYSA-N 4-amino-2,5-dimethoxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(OC)=C(N)C=C1OC CISVVDNATRQDNU-UHFFFAOYSA-N 0.000 description 2
- WOXLPNAOCCIZGP-UHFFFAOYSA-N 4-chloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=CC=C1N WOXLPNAOCCIZGP-UHFFFAOYSA-N 0.000 description 2
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 2
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 2
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 229920001220 nitrocellulos Polymers 0.000 description 2
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- ZTPAUBJZUBGGEY-UHFFFAOYSA-N (2,4-dichlorophenyl)hydrazine Chemical compound NNC1=CC=C(Cl)C=C1Cl ZTPAUBJZUBGGEY-UHFFFAOYSA-N 0.000 description 1
- OXYZQTOFWJLWDE-UHFFFAOYSA-N (4,6-diamino-4-hydroxy-1h-pyrimidin-2-yl)urea Chemical compound NC(=O)NC1=NC(N)(O)C=C(N)N1 OXYZQTOFWJLWDE-UHFFFAOYSA-N 0.000 description 1
- KHCCJWUQBFVECB-UHFFFAOYSA-N (4,6-diaminopyrimidin-2-yl)cyanamide Chemical compound NC1=CC(N)=NC(NC#N)=N1 KHCCJWUQBFVECB-UHFFFAOYSA-N 0.000 description 1
- GNEVRRGHIFAWTJ-UHFFFAOYSA-N (4-amino-4-hydroxy-1h-pyrimidin-2-yl)urea Chemical compound NC(=O)NC1=NC(N)(O)C=CN1 GNEVRRGHIFAWTJ-UHFFFAOYSA-N 0.000 description 1
- SPAJGBOXQITFMS-UHFFFAOYSA-N (4-hydroxy-6-oxo-1h-pyrimidin-2-yl)cyanamide Chemical compound OC1=CC(=O)NC(NC#N)=N1 SPAJGBOXQITFMS-UHFFFAOYSA-N 0.000 description 1
- MANYVBUGTRHKES-UHFFFAOYSA-N (4-hydroxy-6-oxo-1h-pyrimidin-2-yl)urea Chemical compound NC(=O)NC1=NC(O)=CC(O)=N1 MANYVBUGTRHKES-UHFFFAOYSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- QQOBTPNGSQEDAS-UHFFFAOYSA-N 1-amino-2-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC(Cl)=C2N QQOBTPNGSQEDAS-UHFFFAOYSA-N 0.000 description 1
- BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 description 1
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 description 1
- KMWDXUMOFMAQRI-UHFFFAOYSA-N 2,4-dichloro-5-ethylaniline Chemical compound CCC1=CC(N)=C(Cl)C=C1Cl KMWDXUMOFMAQRI-UHFFFAOYSA-N 0.000 description 1
- AJROJTARXSATEB-UHFFFAOYSA-N 2,4-dichloro-5-methoxyaniline Chemical compound COC1=CC(N)=C(Cl)C=C1Cl AJROJTARXSATEB-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
- GEQNZVKIDIPGCO-UHFFFAOYSA-N 2,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C(OC)=C1 GEQNZVKIDIPGCO-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- PLVBBUUBVVJOIB-UHFFFAOYSA-N 2,5-dichloro-4-methylaniline Chemical compound CC1=CC(Cl)=C(N)C=C1Cl PLVBBUUBVVJOIB-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- XPKFTIYOZUJAGA-UHFFFAOYSA-N 2,5-diethoxyaniline Chemical compound CCOC1=CC=C(OCC)C(N)=C1 XPKFTIYOZUJAGA-UHFFFAOYSA-N 0.000 description 1
- ZTQGTYFYOODGOQ-UHFFFAOYSA-N 2,5-dimethoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=C(OC)C=C1N ZTQGTYFYOODGOQ-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- HBDOIAFHLHZMCF-UHFFFAOYSA-N 2-(4,6-diaminopyrimidin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(N)=CC(N)=N1 HBDOIAFHLHZMCF-UHFFFAOYSA-N 0.000 description 1
- NHKQFLAKTUCGQX-UHFFFAOYSA-N 2-(4-hydroxy-6-oxo-1h-pyrimidin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(O)=CC(O)=N1 NHKQFLAKTUCGQX-UHFFFAOYSA-N 0.000 description 1
- SGCCOSHUSKMIKV-UHFFFAOYSA-N 2-(6-amino-4-oxo-1h-pyrimidin-2-yl)guanidine Chemical compound NC(=N)NC1=NC(N)=CC(O)=N1 SGCCOSHUSKMIKV-UHFFFAOYSA-N 0.000 description 1
- AUFJTVGCSJNQIF-UHFFFAOYSA-N 2-Amino-4,6-dihydroxypyrimidine Chemical compound NC1=NC(O)=CC(=O)N1 AUFJTVGCSJNQIF-UHFFFAOYSA-N 0.000 description 1
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
- VMOJFUJVEWWUAV-UHFFFAOYSA-N 2-amino-3-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(N)C(Cl)=C2 VMOJFUJVEWWUAV-UHFFFAOYSA-N 0.000 description 1
- SIBBTUOKTWHCLA-UHFFFAOYSA-N 2-amino-4-[(2,5-dichlorobenzoyl)amino]benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(NC(=O)C=2C(=CC=C(Cl)C=2)Cl)=C1 SIBBTUOKTWHCLA-UHFFFAOYSA-N 0.000 description 1
- BNXBCSVIKODDEE-UHFFFAOYSA-N 2-amino-4-benzamidobenzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC(NC(=O)C=2C=CC=CC=2)=C1 BNXBCSVIKODDEE-UHFFFAOYSA-N 0.000 description 1
- GTAXMXNQWKHRMA-UHFFFAOYSA-N 2-amino-4-methyl-1,3-thiazole-5-carboxamide Chemical compound CC=1N=C(N)SC=1C(N)=O GTAXMXNQWKHRMA-UHFFFAOYSA-N 0.000 description 1
- QCVFVGONDMKXEE-UHFFFAOYSA-N 2-amino-4-methyl-1,3-thiazole-5-carboxylic acid Chemical compound CC=1N=C(N)SC=1C(O)=O QCVFVGONDMKXEE-UHFFFAOYSA-N 0.000 description 1
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- CGPPWNTVTNCHDO-UHFFFAOYSA-N 2-bromo-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Br CGPPWNTVTNCHDO-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- VLMRGLCBIFWPGL-UHFFFAOYSA-N 2-chloro-4-methylsulfonylaniline Chemical compound CS(=O)(=O)C1=CC=C(N)C(Cl)=C1 VLMRGLCBIFWPGL-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- KWIXNFOTNVKIGM-UHFFFAOYSA-N 2-chloro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1Cl KWIXNFOTNVKIGM-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
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- OEQGMPSQZNJJBM-UHFFFAOYSA-N n-(4-hydroxy-6-oxo-1h-pyrimidin-2-yl)acetamide Chemical compound CC(=O)NC1=NC(O)=CC(O)=N1 OEQGMPSQZNJJBM-UHFFFAOYSA-N 0.000 description 1
- ZAKMOHYYFMKCTR-UHFFFAOYSA-N n-(4-hydroxy-6-oxo-1h-pyrimidin-2-yl)benzenesulfonamide Chemical compound OC1=CC(O)=NC(NS(=O)(=O)C=2C=CC=CC=2)=N1 ZAKMOHYYFMKCTR-UHFFFAOYSA-N 0.000 description 1
- ZKCUZHITSHCPES-UHFFFAOYSA-N n-(4-hydroxy-6-oxo-1h-pyrimidin-2-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=NC(O)=CC(O)=N1 ZKCUZHITSHCPES-UHFFFAOYSA-N 0.000 description 1
- OITOSTVMHWDZDZ-UHFFFAOYSA-N n-(6-amino-4-oxo-1h-pyrimidin-2-yl)acetamide Chemical compound CC(=O)NC1=NC(N)=CC(O)=N1 OITOSTVMHWDZDZ-UHFFFAOYSA-N 0.000 description 1
- GMSLLLSAHFXIDD-UHFFFAOYSA-N n-(6-amino-4-oxo-1h-pyrimidin-2-yl)benzamide Chemical compound NC1=CC(O)=NC(NC(=O)C=2C=CC=CC=2)=N1 GMSLLLSAHFXIDD-UHFFFAOYSA-N 0.000 description 1
- CLUYXMSQAANAAG-UHFFFAOYSA-N n-(6-amino-4-oxo-1h-pyrimidin-2-yl)benzenesulfonamide Chemical compound N1C(N)=CC(=O)N=C1NS(=O)(=O)C1=CC=CC=C1 CLUYXMSQAANAAG-UHFFFAOYSA-N 0.000 description 1
- XUFWZWDPFYUBQG-UHFFFAOYSA-N n-(6-amino-4-oxo-1h-pyrimidin-2-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=NC(N)=CC(O)=N1 XUFWZWDPFYUBQG-UHFFFAOYSA-N 0.000 description 1
- MPNZRDLYXIEUSQ-UHFFFAOYSA-N n-chloro-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC=CC(NCl)=C1 MPNZRDLYXIEUSQ-UHFFFAOYSA-N 0.000 description 1
- PJTUIHLPKZXQNK-UHFFFAOYSA-N n-chloro-3-methoxyaniline Chemical compound COC1=CC=CC(NCl)=C1 PJTUIHLPKZXQNK-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000005609 naphthenate group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 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
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VNBATQCVJRLUOW-UHFFFAOYSA-N phenyl 3-amino-4-methoxybenzoate Chemical compound C1=C(N)C(OC)=CC=C1C(=O)OC1=CC=CC=C1 VNBATQCVJRLUOW-UHFFFAOYSA-N 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate 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
- 229920002223 polystyrene Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004408 titanium dioxide 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
- 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
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3665—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms
- C09B29/3669—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic ring with two nitrogen atoms from a pyrimidine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732351294 DE2351294A1 (de) | 1973-10-12 | 1973-10-12 | Azopigmente |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1060000A true CA1060000A (en) | 1979-08-07 |
Family
ID=5895263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA211,136A Expired CA1060000A (en) | 1973-10-12 | 1974-10-10 | Azo pigments |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US4014863A (enExample) |
| JP (1) | JPS5067324A (enExample) |
| BE (1) | BE820842A (enExample) |
| BR (1) | BR7408503D0 (enExample) |
| CA (1) | CA1060000A (enExample) |
| CH (1) | CH606299A5 (enExample) |
| DE (1) | DE2351294A1 (enExample) |
| DK (1) | DK143944C (enExample) |
| ES (1) | ES430944A1 (enExample) |
| FR (1) | FR2247511B1 (enExample) |
| GB (1) | GB1430905A (enExample) |
| IN (1) | IN142399B (enExample) |
| IT (1) | IT1022772B (enExample) |
| NL (1) | NL7413295A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3106358A1 (de) * | 1981-02-20 | 1982-09-09 | Bayer Ag, 5090 Leverkusen | Anthrachinonazoverbindungen, verfahren zu ihrer herstellung sowie ihre verwendung |
| US4536184A (en) * | 1983-12-12 | 1985-08-20 | Formulabs Industrial Inks, Inc. | Overprinting of dye colored poly(vinyl chloride) resins |
| DE4417718A1 (de) * | 1994-05-20 | 1995-11-23 | Hoechst Ag | Reaktivfarbstoffe für den Tintenstrahldruck |
| DE19529262A1 (de) * | 1995-08-09 | 1997-02-13 | Hoechst Ag | Wasserunlösliche Azofarbmittel auf Basis von Aminochinazolindionen |
| US5891231A (en) * | 1997-05-13 | 1999-04-06 | Lexmark International Inc. | Process for preparing pigment dispersions used in inks |
| JP5551441B2 (ja) * | 2006-10-25 | 2014-07-16 | チバ ホールディング インコーポレーテッド | ポリマーの原液着色用のモノアゾ着色剤 |
| US8013045B2 (en) | 2006-10-25 | 2011-09-06 | BASF SE Ludwigshafen | Monoazo colorants for mass-colouring of polymers |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2140536A (en) * | 1936-08-20 | 1938-12-20 | Eastman Kodak Co | Azo compounds and process for dyeing therewith |
| US2140537A (en) * | 1937-01-14 | 1938-12-20 | Eastman Kodak Co | Azo compounds and process for coloring therewith |
| US2140538A (en) * | 1937-01-14 | 1938-12-20 | Eastman Kodak Co | Coloration of organic derivatives of cellulose |
| US2140539A (en) * | 1937-01-23 | 1938-12-20 | Eastman Kodak Co | Azo compounds and process for coloring therewith |
| US2746951A (en) * | 1951-05-07 | 1956-05-22 | Bayer Ag | Pyrimidine azo dyestuffs |
| US2692263A (en) * | 1951-07-06 | 1954-10-19 | Bayer Ag | Yellow substantive azo and azoxy dyestuffs |
| US2675375A (en) * | 1951-07-14 | 1954-04-13 | American Cyanamid Co | Arylazopyrimidine compounds and methods of making the same |
| GB837338A (en) * | 1957-10-15 | 1960-06-09 | Takeda Pharmaceutical | Pyrimidinylazobenzene derivatives and their production |
| DE1445982A1 (de) * | 1963-10-08 | 1969-03-20 | Kyowa Hakko Kogyo Kk | Verfahren fuer die Herstellung von 4-Amin-5-Arylazopyrimidin-Derivaten |
| JPS4826037B1 (enExample) * | 1963-11-26 | 1973-08-03 | ||
| DE1544372B1 (de) * | 1965-02-23 | 1970-05-14 | Basf Ag | Verfahren zur Herstellung von Pigmentfarbstoffen der Anthrachinonazoreihe |
| DE1644259C3 (de) * | 1965-08-02 | 1978-03-23 | Ciba-Geigy Ag, Basel (Schweiz) | In Wasser schwerlösliche Azofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben |
| US3481918A (en) * | 1967-02-16 | 1969-12-02 | Eastman Kodak Co | Quaternized phenylazo-pyrimidine dyes |
| CH481986A (de) * | 1967-05-24 | 1969-11-30 | Geigy Ag J R | Verfahren zur Herstellung von wasserlöslichen Farbsalzen von Azopyrimidinfarbstoffen |
| DE1644239A1 (de) * | 1967-12-16 | 1971-04-15 | Hoechst Ag | Basische Azofarbstoffe und Verfahren zu ihrer Herstellung |
| US3726851A (en) * | 1970-09-23 | 1973-04-10 | Allied Chem | Water-soluble benzothiazolylphenylazo-barbituric acid dyestuffs |
| CA918643A (en) * | 1970-10-19 | 1973-01-09 | Blackwell John | Green-yellow monazo paper dyes derived from barbituric acid |
| US3862116A (en) * | 1972-01-03 | 1975-01-21 | Du Pont | Dehydrothio-p-toluidinesulfonic acid azo-hexahydro-4,6-dioxopyrimidineurea or cyanamide direct dyes for paper |
| BE794270A (fr) * | 1972-01-21 | 1973-07-19 | Basf Ag | Pigments organosolubles derives de la pyrimidine |
| US4028322A (en) * | 1972-07-13 | 1977-06-07 | Ciba-Geigy Corporation | 6-Methylbenzimidazolonylazobarbituric acid pigment |
| US4113720A (en) * | 1972-11-13 | 1978-09-12 | Basf Aktiengesellschaft | Disperse azo dye with diaminopyrimidine coupling component |
| CH580141A5 (enExample) * | 1973-05-03 | 1976-09-30 | Ciba Geigy Ag | |
| US4031073A (en) * | 1973-07-27 | 1977-06-21 | Ciba-Geigy Corporation | Monoazo pigments containing barbituric acid or thio- or imino-derivatives thereof |
| DE2424538A1 (de) * | 1974-05-21 | 1975-12-11 | Basf Ag | Azofarbstoffe mit einem phthalazonrest |
| US4062836A (en) * | 1975-02-03 | 1977-12-13 | Ciba-Geigy Corporation | Disperse phenylazophenylazobarbituric acid dyestuffs |
| US4092314A (en) * | 1975-07-07 | 1978-05-30 | Merck & Co., Inc. | Preparation of 4,6-diamino-5-arylazopyrimidines and adenine compounds |
| US4083841A (en) * | 1976-10-13 | 1978-04-11 | Shaw University | 2,4-Diamino-6-methyl-5-(halophenylazo) pyrimidines |
-
1973
- 1973-10-12 DE DE19732351294 patent/DE2351294A1/de not_active Withdrawn
-
1974
- 1974-09-20 IN IN2093/CAL/74A patent/IN142399B/en unknown
- 1974-10-09 NL NL7413295A patent/NL7413295A/xx not_active Application Discontinuation
- 1974-10-09 BE BE149333A patent/BE820842A/xx unknown
- 1974-10-09 JP JP49115736A patent/JPS5067324A/ja active Pending
- 1974-10-09 US US05/513,486 patent/US4014863A/en not_active Expired - Lifetime
- 1974-10-10 IT IT28296/74A patent/IT1022772B/it active
- 1974-10-10 CA CA211,136A patent/CA1060000A/en not_active Expired
- 1974-10-10 CH CH1366774A patent/CH606299A5/xx not_active IP Right Cessation
- 1974-10-11 ES ES430944A patent/ES430944A1/es not_active Expired
- 1974-10-11 FR FR7434315A patent/FR2247511B1/fr not_active Expired
- 1974-10-11 BR BR8503/74A patent/BR7408503D0/pt unknown
- 1974-10-11 GB GB4417174A patent/GB1430905A/en not_active Expired
- 1974-10-11 DK DK535174A patent/DK143944C/da active
-
1978
- 1978-01-03 US US05/866,538 patent/US4421601A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2247511B1 (enExample) | 1978-07-07 |
| BR7408503D0 (pt) | 1975-07-29 |
| DK143944B (da) | 1981-11-02 |
| FR2247511A1 (enExample) | 1975-05-09 |
| DE2351294A1 (de) | 1975-04-24 |
| IN142399B (enExample) | 1977-07-02 |
| BE820842A (fr) | 1975-04-09 |
| CH606299A5 (enExample) | 1978-10-31 |
| DK535174A (enExample) | 1975-06-09 |
| JPS5067324A (enExample) | 1975-06-06 |
| US4421601A (en) | 1983-12-20 |
| US4014863A (en) | 1977-03-29 |
| GB1430905A (en) | 1976-04-07 |
| ES430944A1 (es) | 1976-10-16 |
| IT1022772B (it) | 1978-04-20 |
| DK143944C (da) | 1982-04-19 |
| NL7413295A (nl) | 1975-04-15 |
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