CA1041486A - Azo colorants - Google Patents
Azo colorantsInfo
- Publication number
- CA1041486A CA1041486A CA221,708A CA221708A CA1041486A CA 1041486 A CA1041486 A CA 1041486A CA 221708 A CA221708 A CA 221708A CA 1041486 A CA1041486 A CA 1041486A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- atoms
- denotes
- group
- alkyl
- 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
- 239000003086 colorant Substances 0.000 title claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 239000000306 component Substances 0.000 claims abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- -1 phenylcarbamoyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 238000004040 coloring Methods 0.000 abstract description 6
- 239000011368 organic material Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 description 19
- 238000010168 coupling process Methods 0.000 description 19
- 238000005859 coupling reaction Methods 0.000 description 19
- 239000002253 acid Substances 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- QOMNJPSRBRDQSU-UHFFFAOYSA-N 5-aminobenzimidazol-2-one Chemical compound C1=C(N)C=CC2=NC(=O)N=C21 QOMNJPSRBRDQSU-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-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
- 150000003839 salts Chemical class 0.000 description 4
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000001913 cellulose Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-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
- 150000007513 acids Chemical class 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-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
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 235000021388 linseed oil Nutrition 0.000 description 2
- 239000000944 linseed oil Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 description 1
- ZJWAGKRIOBSJHQ-NTSYASGDSA-N (z,12r)-1-butoxy-12-hydroxy-1-oxooctadec-9-ene-2-sulfonic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCC(S(O)(=O)=O)C(=O)OCCCC ZJWAGKRIOBSJHQ-NTSYASGDSA-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
- ZECUELAGGOAWOP-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)propan-2-one Chemical compound C1=CC=C2NC(CC(=O)C)=NC2=C1 ZECUELAGGOAWOP-UHFFFAOYSA-N 0.000 description 1
- GINUIEXFKFIZSF-UHFFFAOYSA-N 1-(methylamino)ethanesulfonic acid Chemical compound CNC(C)S(O)(=O)=O GINUIEXFKFIZSF-UHFFFAOYSA-N 0.000 description 1
- SDHMGKANHNMOSS-UHFFFAOYSA-N 1-aminoethanesulfonic acid Chemical compound CC(N)S(O)(=O)=O SDHMGKANHNMOSS-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- ULHUJEISMDMVSX-UHFFFAOYSA-N 1-oxo-1,3-benzothiazol-6-amine Chemical compound NC1=CC=C2N=CS(=O)C2=C1 ULHUJEISMDMVSX-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
- BWOVACANEIVHST-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1 BWOVACANEIVHST-UHFFFAOYSA-N 0.000 description 1
- HQBYPWYCPDCYMP-UHFFFAOYSA-N 2-(6-chloro-1h-benzimidazol-2-yl)acetonitrile Chemical compound ClC1=CC=C2N=C(CC#N)NC2=C1 HQBYPWYCPDCYMP-UHFFFAOYSA-N 0.000 description 1
- LOIWTVOSJIKEOW-UHFFFAOYSA-N 2-(6-ethoxy-1h-benzimidazol-2-yl)acetonitrile Chemical compound CCOC1=CC=C2NC(CC#N)=NC2=C1 LOIWTVOSJIKEOW-UHFFFAOYSA-N 0.000 description 1
- OYWGPHBMKLNVKU-UHFFFAOYSA-N 2-(6-methoxy-1h-benzimidazol-2-yl)acetonitrile Chemical compound COC1=CC=C2N=C(CC#N)NC2=C1 OYWGPHBMKLNVKU-UHFFFAOYSA-N 0.000 description 1
- PIGCSKVALLVWKU-UHFFFAOYSA-N 2-Aminoacridone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3NC2=C1 PIGCSKVALLVWKU-UHFFFAOYSA-N 0.000 description 1
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 1
- IFSWUJHOYKYNBX-UHFFFAOYSA-N 2-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]acetonitrile Chemical compound FC(F)(F)C1=CC=C2NC(CC#N)=NC2=C1 IFSWUJHOYKYNBX-UHFFFAOYSA-N 0.000 description 1
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 description 1
- DHAWWYIBJYMILF-UHFFFAOYSA-N 2-amino-7-ethoxy-10H-acridin-9-one Chemical compound C1=C(N)C=C2C(=O)C3=CC(OCC)=CC=C3NC2=C1 DHAWWYIBJYMILF-UHFFFAOYSA-N 0.000 description 1
- BELPTNJEEUPGQO-UHFFFAOYSA-N 2-amino-N-phenylnaphthalene-1-carboxamide Chemical compound NC1=C(C2=CC=CC=C2C=C1)C(=O)NC1=CC=CC=C1 BELPTNJEEUPGQO-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- QHCCOYAKYCWDOJ-UHFFFAOYSA-N 2-ethyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CC)=NC2=C1 QHCCOYAKYCWDOJ-UHFFFAOYSA-N 0.000 description 1
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 1
- SSILWUSDXOOUDQ-UHFFFAOYSA-N 3-(2-methoxyphenyl)-1h-benzimidazol-2-one Chemical compound COC1=CC=CC=C1N1C(=O)NC2=CC=CC=C21 SSILWUSDXOOUDQ-UHFFFAOYSA-N 0.000 description 1
- HAVMFSNJYOWIOE-UHFFFAOYSA-N 3-amino-6-chloro-10h-acridin-9-one Chemical compound ClC1=CC=C2C(=O)C3=CC=C(N)C=C3NC2=C1 HAVMFSNJYOWIOE-UHFFFAOYSA-N 0.000 description 1
- RAWUUYDTDLKVCW-UHFFFAOYSA-N 3-amino-n-methylnaphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(O)=NC)=CC(N)=CC2=C1 RAWUUYDTDLKVCW-UHFFFAOYSA-N 0.000 description 1
- HXUIDZOMTRMIOE-UHFFFAOYSA-N 3-oxo-3-phenylpropionic acid Chemical compound OC(=O)CC(=O)C1=CC=CC=C1 HXUIDZOMTRMIOE-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-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
- SWXFMMWYVSYQGF-UHFFFAOYSA-N 4-(ethylamino)benzoic acid Chemical compound CCNC1=CC=C(C(O)=O)C=C1 SWXFMMWYVSYQGF-UHFFFAOYSA-N 0.000 description 1
- NXBWFXMEJVOABP-UHFFFAOYSA-N 4-amino-1h-quinazolin-2-one Chemical compound C1=CC=C2C(N)=NC(=O)NC2=C1 NXBWFXMEJVOABP-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- CRXVBLLLPNWFBS-UHFFFAOYSA-N 4-aminobenzimidazol-2-one Chemical compound NC1=CC=CC2=NC(=O)N=C12 CRXVBLLLPNWFBS-UHFFFAOYSA-N 0.000 description 1
- HCSXGHIWQVZBJK-UHFFFAOYSA-N 4-aminobenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)C3=C2C1=CC=C3N HCSXGHIWQVZBJK-UHFFFAOYSA-N 0.000 description 1
- HVAXPRLYMAWEBL-UHFFFAOYSA-N 4-chlorobenzimidazol-2-one Chemical compound ClC1=CC=CC2=NC(=O)N=C12 HVAXPRLYMAWEBL-UHFFFAOYSA-N 0.000 description 1
- INZPKLIRWQFSQE-UHFFFAOYSA-N 5-amino-2-phenyl-1h-quinazolin-4-one Chemical compound N=1C(O)=C2C(N)=CC=CC2=NC=1C1=CC=CC=C1 INZPKLIRWQFSQE-UHFFFAOYSA-N 0.000 description 1
- OLQMJWBCGGBPOU-UHFFFAOYSA-N 5-amino-3-hydroxy-2h-quinazolin-2-ol Chemical compound OC1N(O)C=C2C(N)=CC=CC2=N1 OLQMJWBCGGBPOU-UHFFFAOYSA-N 0.000 description 1
- ACINCUZZZYSFLY-UHFFFAOYSA-N 5-amino-6-bromo-3h-1,3-benzoxazol-2-one Chemical compound C1=C(Br)C(N)=CC2=C1OC(=O)N2 ACINCUZZZYSFLY-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
- YNVHDYNZKQQWRB-UHFFFAOYSA-N 5-amino-6-methyl-3h-1,3-benzoxazol-2-one Chemical compound C1=C(N)C(C)=CC2=C1NC(=O)O2 YNVHDYNZKQQWRB-UHFFFAOYSA-N 0.000 description 1
- NJXKEICRIHQSEX-UHFFFAOYSA-N 5-amino-7-bromo-3h-1,3-benzoxazol-2-one Chemical compound NC1=CC(Br)=C2OC(=O)NC2=C1 NJXKEICRIHQSEX-UHFFFAOYSA-N 0.000 description 1
- CISSNNJOGJQORG-UHFFFAOYSA-N 5-amino-7-chloro-3-hydroxy-2h-quinazolin-2-ol Chemical compound OC1N(O)C=C2C(N)=CC(Cl)=CC2=N1 CISSNNJOGJQORG-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
- SVWKMEJWRQRPGJ-UHFFFAOYSA-N 5-amino-7-methoxy-3h-1,3-benzoxazol-2-one Chemical compound COC1=CC(N)=CC2=C1OC(=O)N2 SVWKMEJWRQRPGJ-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
- XSWMKHWNNALEMD-UHFFFAOYSA-N 5-aminobenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC2=CC(N)=CC(C(=O)NC3=O)=C2C3=C1 XSWMKHWNNALEMD-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
- CEJRCDKSGFPKGL-UHFFFAOYSA-N 6-amino-3-(4-chlorophenyl)-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC(N)=CC=C2N1C1=CC=C(Cl)C=C1 CEJRCDKSGFPKGL-UHFFFAOYSA-N 0.000 description 1
- XLWYFLUAYKPZSE-UHFFFAOYSA-N 6-amino-3-phenyl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC(N)=CC=C2N1C1=CC=CC=C1 XLWYFLUAYKPZSE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- XISPHYHTKGCYGL-UHFFFAOYSA-N 6-amino-4-chloro-3-phenyl-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC(N)=CC(Cl)=C2N1C1=CC=CC=C1 XISPHYHTKGCYGL-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
- DMXLKTXMZKZRGR-UHFFFAOYSA-N 6-amino-4-methoxybenzimidazol-2-one Chemical compound COC1=CC(N)=CC2=NC(=O)N=C12 DMXLKTXMZKZRGR-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
- 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 1
- MXXTUBQPWCZEDE-UHFFFAOYSA-N 7-amino-2-methyl-1h-quinolin-4-one Chemical compound C1=CC(N)=CC2=NC(C)=CC(O)=C21 MXXTUBQPWCZEDE-UHFFFAOYSA-N 0.000 description 1
- QZEOWPYTNFYDGY-UHFFFAOYSA-N 8-amino-6-methoxy-1h-quinolin-2-one Chemical compound N1=C(O)C=CC2=CC(OC)=CC(N)=C21 QZEOWPYTNFYDGY-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N Azide Chemical class [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical group COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- YTLQFZVCLXFFRK-UHFFFAOYSA-N bendazol Chemical compound N=1C2=CC=CC=C2NC=1CC1=CC=CC=C1 YTLQFZVCLXFFRK-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 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
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000004816 dichlorobenzenes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- JDXYSCUOABNLIR-UHFFFAOYSA-N diethyl 2-oxobutanedioate Chemical compound CCOC(=O)CC(=O)C(=O)OCC JDXYSCUOABNLIR-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([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 class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 238000007646 gravure printing Methods 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002900 methylcellulose Drugs 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- ZVIDMSBTYRSMAR-UHFFFAOYSA-N p-methylamino-benzoic acid Natural products CNC1=CC=C(C(O)=O)C=C1 ZVIDMSBTYRSMAR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 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
- 229920000728 polyester Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920000098 polyolefin 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000080 wetting agent 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH341774A CH591540A5 (en, 2012) | 1974-03-12 | 1974-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1041486A true CA1041486A (en) | 1978-10-31 |
Family
ID=4255526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,708A Expired CA1041486A (en) | 1974-03-12 | 1975-03-10 | Azo colorants |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4012371A (en, 2012) |
| JP (1) | JPS50126716A (en, 2012) |
| CA (1) | CA1041486A (en, 2012) |
| CH (1) | CH591540A5 (en, 2012) |
| DE (1) | DE2510373A1 (en, 2012) |
| FR (1) | FR2264062B1 (en, 2012) |
| GB (1) | GB1453023A (en, 2012) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1550401A (en) * | 1976-01-07 | 1979-08-15 | Hexachimie | Hydrazine derivatives their preparation and their use |
| US5686560A (en) * | 1995-06-06 | 1997-11-11 | Hitachi Chemical Co., Ltd. | Polyquinazolines and methods for their preparation |
| WO2004050768A2 (en) * | 2002-12-05 | 2004-06-17 | Ciba Specialty Chemicals Holding Inc. | Benzimidazole-pyridone-based azo dyes |
| CN1764699A (zh) * | 2003-03-25 | 2006-04-26 | 西巴特殊化学品控股有限公司 | 单偶氮喹诺酮颜料、其制备方法和应用 |
| EP1975205B1 (en) * | 2006-01-06 | 2012-05-02 | Nippon Kayaku Kabushiki Kaisha | Trisazo compound, ink composition, recording method and colored matter |
| WO2008096697A1 (ja) * | 2007-02-05 | 2008-08-14 | Nippon Kayaku Kabushiki Kaisha | トリスアゾ化合物、インク組成物、プリント方法及び着色体 |
| US7901498B2 (en) * | 2007-11-27 | 2011-03-08 | Nippon Kayaku Kabushiki Kaisha | Trisazo compound, ink composition, printing method and colored product |
| US8080100B2 (en) * | 2008-05-07 | 2011-12-20 | Nippon Kayaku Kabushiki Kaisha | Trisazo compound, ink composition, recording method and colored body |
| JP5456667B2 (ja) * | 2008-05-07 | 2014-04-02 | 日本化薬株式会社 | トリスアゾ化合物、インク組成物、記録方法及び着色体 |
| WO2010109843A1 (ja) * | 2009-03-27 | 2010-09-30 | 日本化薬株式会社 | アゾ化合物、インク組成物、記録方法及び着色体 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2742457A (en) * | 1954-07-07 | 1956-04-17 | Gen Aniline & Film Corp | Pyrido-benzimidazol azo dyes |
| CH427092A (de) * | 1964-02-06 | 1966-12-31 | Sandoz Ag | Verfahren zur Herstellung von Azofarbstoffen |
| DE2023295A1 (en) * | 1970-05-13 | 1971-11-25 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Water insoluble azo dyes for dyeing polyesters polyamides cellulose - esters and polypropylene |
-
1974
- 1974-03-12 CH CH341774A patent/CH591540A5/xx not_active IP Right Cessation
-
1975
- 1975-03-10 DE DE19752510373 patent/DE2510373A1/de active Pending
- 1975-03-10 US US05/556,744 patent/US4012371A/en not_active Expired - Lifetime
- 1975-03-10 CA CA221,708A patent/CA1041486A/en not_active Expired
- 1975-03-11 FR FR7507488A patent/FR2264062B1/fr not_active Expired
- 1975-03-11 GB GB1003175A patent/GB1453023A/en not_active Expired
- 1975-03-12 JP JP50029974A patent/JPS50126716A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1453023A (en) | 1976-10-20 |
| JPS50126716A (en, 2012) | 1975-10-06 |
| US4012371A (en) | 1977-03-15 |
| FR2264062A1 (en, 2012) | 1975-10-10 |
| DE2510373A1 (de) | 1975-09-18 |
| FR2264062B1 (en, 2012) | 1977-04-15 |
| CH591540A5 (en, 2012) | 1977-09-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1041486A (en) | Azo colorants | |
| US3956266A (en) | Bis-(benzimidazolone-azo-acetoacetylamino)-phenylene pigments | |
| US3658783A (en) | Monoazo dyestuffs containing a triazine in the coupling component | |
| US4220586A (en) | Hetero-aryl azo acylamino substituted aceto-acetarylide pigments | |
| US3963694A (en) | Hydroxyquinolyl- and quinazolonylazoacetoacetylbenzimidazolone pigments | |
| US3872078A (en) | Disazo pigments, processes for their manufacture and use | |
| US4003886A (en) | Tetracarboxylic acid ester substituted disazo pigments | |
| US4229344A (en) | Monazo pigments containing hydroxynaphthoylaminobenzimidazalone radical | |
| US3609134A (en) | Azo pigments containing a 4-carboxamido phenomorpholene-(3) group | |
| US4555568A (en) | Monoazo compounds derived from 3-nitro-4-amino-benzoates and 5-(2'-hydroxy-3'-naphthoylamino)-benzimidazolones | |
| CA1058165A (en) | Disazopigments | |
| US3978038A (en) | Disazo pigments containing at least one nitro group on the diazo component | |
| CA1135688A (en) | Disazo compounds, process for their manufacture and their use | |
| CA1045120A (en) | Disazo pigments and a process for their manufacture | |
| US3963693A (en) | Quinolone azo barbituric acid pigments | |
| CA1180325A (en) | Monoazo pigments containing heterocycles, processes for producing the pigments, and the use thereof | |
| US4070353A (en) | Dicarboxylic acid ester diazo pigments | |
| US4206114A (en) | Monoazo pigments from diazotized 5-acylaminoanthranilic acid derivatives and acetoacetylaminobenzimidazolones | |
| US3985725A (en) | Quinolino-azo-aceto-acetylaminobenzimidazolone pigments fast to heat | |
| CA1107274A (en) | Monoazo pigments and process for their production | |
| US3781266A (en) | Water-insoluble phenyl-azo-naphthyl-amido-benzimidazolone dyestuffs | |
| US3897411A (en) | Monoazo pigments containing a phenylamino-quinazoline radical | |
| US4081439A (en) | Aromatic disazo pigments | |
| US4065449A (en) | Tetrachloro substituted disazo pigments | |
| US4062838A (en) | Disazo pigments containing acylamino groups |