DE1808017A1 - New water-insoluble monoazo pigments and processes for their production - Google Patents
New water-insoluble monoazo pigments and processes for their productionInfo
- Publication number
- DE1808017A1 DE1808017A1 DE19681808017 DE1808017A DE1808017A1 DE 1808017 A1 DE1808017 A1 DE 1808017A1 DE 19681808017 DE19681808017 DE 19681808017 DE 1808017 A DE1808017 A DE 1808017A DE 1808017 A1 DE1808017 A1 DE 1808017A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- acid
- hydrogen
- water
- 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.)
- Granted
Links
- 239000000049 pigment Substances 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title claims description 4
- 239000000975 dye Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000004753 textile Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000000025 natural resin Substances 0.000 claims description 2
- 239000005060 rubber Substances 0.000 claims description 2
- 229920003002 synthetic resin Polymers 0.000 claims description 2
- 239000000057 synthetic resin Substances 0.000 claims description 2
- 239000002966 varnish Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 5
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 150000003857 carboxamides Chemical class 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 239000000839 emulsion Substances 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000000976 ink Substances 0.000 claims 1
- 239000004033 plastic Substances 0.000 claims 1
- 229920003023 plastic Polymers 0.000 claims 1
- 239000002253 acid Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000004800 polyvinyl chloride Substances 0.000 description 9
- -1 carboxylic acid alkyl amide Chemical class 0.000 description 8
- 229920000915 polyvinyl chloride Polymers 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 125000000664 diazo group Chemical class [N-]=[N+]=[*] 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000001052 yellow pigment Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 2
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- HUIYGGQINIVDNW-UHFFFAOYSA-N butyl anthranilate Chemical compound CCCCOC(=O)C1=CC=CC=C1N HUIYGGQINIVDNW-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- 239000004744 fabric Substances 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
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000007762 w/o emulsion Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- QYRDWARBHMCOAG-UHFFFAOYSA-N 2-amino-5-chlorobenzonitrile Chemical compound NC1=CC=C(Cl)C=C1C#N QYRDWARBHMCOAG-UHFFFAOYSA-N 0.000 description 1
- LNEVUNYUJNORRV-UHFFFAOYSA-N 2-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1 LNEVUNYUJNORRV-UHFFFAOYSA-N 0.000 description 1
- HPSCXFOQUFPEPE-UHFFFAOYSA-N 2-chloro-5-methylaniline Chemical compound CC1=CC=C(Cl)C(N)=C1 HPSCXFOQUFPEPE-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- MNURPFVONZPVLA-UHFFFAOYSA-N 2-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1Cl MNURPFVONZPVLA-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- CUYCWXMJPCLAHS-UHFFFAOYSA-N 3-amino-4-butoxybenzamide Chemical compound CCCCOC1=CC=C(C(N)=O)C=C1N CUYCWXMJPCLAHS-UHFFFAOYSA-N 0.000 description 1
- HDUINBMMWMTTLC-UHFFFAOYSA-N 3-amino-4-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(O)=O)C=C1N HDUINBMMWMTTLC-UHFFFAOYSA-N 0.000 description 1
- DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 1
- XKFIFYROMAAUDL-UHFFFAOYSA-N 3-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N XKFIFYROMAAUDL-UHFFFAOYSA-N 0.000 description 1
- OEEJOGRTURXKDF-UHFFFAOYSA-N 3-oxo-n-(2-oxobenzimidazol-4-yl)butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC2=NC(=O)N=C12 OEEJOGRTURXKDF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VVYGZYIYZOYELH-UHFFFAOYSA-N 4-amino-2,5-dimethoxy-N-propan-2-ylbenzenesulfonamide Chemical compound COC1=CC(S(=O)(=O)NC(C)C)=C(OC)C=C1N VVYGZYIYZOYELH-UHFFFAOYSA-N 0.000 description 1
- ZRSXRBFTNBKPKH-UHFFFAOYSA-N 4-amino-2,5-dimethoxy-n-phenylbenzamide Chemical compound C1=C(N)C(OC)=CC(C(=O)NC=2C=CC=CC=2)=C1OC ZRSXRBFTNBKPKH-UHFFFAOYSA-N 0.000 description 1
- MICDVUDJBHIFHA-UHFFFAOYSA-N 4-amino-2,5-dimethoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(OC)C=C1N MICDVUDJBHIFHA-UHFFFAOYSA-N 0.000 description 1
- GWSQAGVGSHXRJK-UHFFFAOYSA-N 4-amino-5-methoxy-n,2-dimethylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC(OC)=C(N)C=C1C GWSQAGVGSHXRJK-UHFFFAOYSA-N 0.000 description 1
- ORVMLAVZLCEJKL-UHFFFAOYSA-N 4-amino-N-ethyl-2,5-dimethoxybenzenesulfonamide Chemical compound C(C)NS(=O)(=O)C1=CC(=C(C=C1OC)N)OC ORVMLAVZLCEJKL-UHFFFAOYSA-N 0.000 description 1
- CVINWVPRKDIGLL-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)aniline Chemical compound NC1=CC=C(Cl)C=C1C(F)(F)F CVINWVPRKDIGLL-UHFFFAOYSA-N 0.000 description 1
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 description 1
- AHPWTJSAEDUARL-UHFFFAOYSA-N 4-chloro-2-nitroaniline;4-methyl-2-nitroaniline Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1.NC1=CC=C(Cl)C=C1[N+]([O-])=O AHPWTJSAEDUARL-UHFFFAOYSA-N 0.000 description 1
- KMIFZILWRRENBO-UHFFFAOYSA-N 4-nitrobenzimidazol-2-one Chemical compound [O-][N+](=O)C1=CC=CC2=NC(=O)N=C12 KMIFZILWRRENBO-UHFFFAOYSA-N 0.000 description 1
- APRTXLXKTLCGKJ-UHFFFAOYSA-N 5-amino-2,4-dichlorobenzamide Chemical compound NC(=O)C1=CC(N)=C(Cl)C=C1Cl APRTXLXKTLCGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical class [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-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
- 229920001756 Polyvinyl chloride acetate Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DZICUHOFOOPVFM-UHFFFAOYSA-N methyl 2-amino-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)C=C1N DZICUHOFOOPVFM-UHFFFAOYSA-N 0.000 description 1
- IGHVUURTQGBABT-UHFFFAOYSA-N methyl 2-amino-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1N IGHVUURTQGBABT-UHFFFAOYSA-N 0.000 description 1
- LOCJPOYKBUUVKU-UHFFFAOYSA-N methyl 3-amino-4-chlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(N)=C1 LOCJPOYKBUUVKU-UHFFFAOYSA-N 0.000 description 1
- QVDWKLDUBSJEOG-UHFFFAOYSA-N methyl 3-amino-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(N)=C1 QVDWKLDUBSJEOG-UHFFFAOYSA-N 0.000 description 1
- WKVJBYKFGNVWLM-UHFFFAOYSA-N methyl 4-amino-3-chlorobenzoate Chemical compound COC(=O)C1=CC=C(N)C(Cl)=C1 WKVJBYKFGNVWLM-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- MGVDUDAXURKVCE-UHFFFAOYSA-N n-(4-amino-3-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C([N+]([O-])=O)=C1 MGVDUDAXURKVCE-UHFFFAOYSA-N 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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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
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
FARBYTERKE HOECHST AG. vormals Heister Lucius & BrüningFARBYTERKE HOECHST AG. formerly Heister Lucius & Brüning
Aktenzeichen: Fw 5920File number: Fw 5920
Datum: 6. November 1968/Dr.B/BltDate: November 6, 1968 / Dr.B / Blt
Neue wasserunlösliche Monoazopigraente und Verfahren zu ihrer Herstellung New water-insoluble monoazopigraents and processes for their production
Die vorliegende Erfindung betrifft neue, wertvolle, wasserunlösliche Monoazopigmente der allgemeinen FormelThe present invention relates to new, valuable, water-insoluble Monoazo pigments of the general formula
COCHL HCOCHL H
COCH3 COCH 3
N-CHN-CH
CO-NH^~Vw ' (1>CO-NH ^ ~ Vw ' (1 >
worin X ein TTasserstoff- oder Halogenatom, Y und Z Wasserstoff-, Halogenatome, Nitro-, Alkoxy-, Aryloxy-, Alkyl-, Trifluomethyl-, Cyan-, Carbonsäurealkylester-, Carbonsäureamid-, Carbonsäurealkylamid-, Carbonsäurearylamid-, Acylamino-ι Sulfonsäureamide, Sulfonsäurealkylanid- oder SuIfonsäurearylamidgruppen, R eine Alkylgruppe mit 1-6 Kohlenstoffatomen und R1 ein Wasserstoff- oder Halogenatoa oder eine Methyl- oder Methoxygruppe bedeuten und ein Verfahren zu ihrer Herstellung, beidem man diazotlerte Amine der allgemeinen Formel wherein X is a T hydrogen or halogen atom, Y and Z hydrogen, halogen atoms, nitro, alkoxy, aryloxy, alkyl, trifluomethyl, cyano, carboxylic acid alkyl ester, carboxylic acid amide, carboxylic acid alkyl amide, carboxylic acid aryl amide, acylamino-ι Sulfonic acid amides, sulfonic acid alkylanide or sulfonic acid aryl amide groups, R is an alkyl group with 1-6 carbon atoms and R 1 is a hydrogen or halogen atom or a methyl or methoxy group and a process for their preparation, both of which are diazotized amines of the general formula
009824/1S51009824 / 1S51
in welcher X, Y und Z die vorstehend genannten Bedeutungen haben, mit Azokomponenten der allgemeinen Formelin which X, Y and Z have the meanings given above, with azo components of the general formula
CH3CO-CH2-CO-NH-T Vn^ (3)CH 3 CO-CH 2 -CO-NH-T Vn ^ (3)
in welcher R und JL die vorstehend genannten Bedeutungen haben, kuppelt.in which R and JL have the meanings given above have coupled.
Besonders vorteilhafte Eigenschaften haben diejenigen lionoazopigmente der obigen Formel (1), in denen Y eine Gruppe der Formel R-HNOC-, B3HNQ2S- oder R4OOC- bedeutet, in welchen Rg und .R3 ein Wasserstoffatom, eine niedere Alkylgruppe oder einen Arylrest und R. eine niedere Alkylgruppe darstellt.Those lionoazo pigments of the above formula (1), in which Y is a group of the formula R-HNOC-, B 3 HNQ 2 S- or R 4 OOC-, in which R g and R 3 are a hydrogen atom, have particularly advantageous properties lower alkyl group or an aryl radical and R. represents a lower alkyl group.
Als geeignete Amine der genannten Formel (2) seien beispielsweise genannt:Suitable amines of the formula (2) mentioned are, for example called:
Chloraniline, wie 2-Chlor-anilin, 2,4-Dichloranilin, 2,5-Dichloranilin, 2-Chlor-5-methylanilin, 2-Chlor-4-methoxyanilin, 4-Chlor--2-trifliiQrmethylanilinJ Nitraniline, wie 2-Nitro-anilin, 2-Nitro~4-chlor-anilin, 2-Nitro-4-methylanilin, 2-Nitro-4-ftcetyiiimino%nilin, weiterhin Aninobenzoeefturester, wie 2-Aminoben£oes%tsremethylester, 2-Amlnobenzoeeäurebutyleeter, l-Aminobenssol^,S-diuarbonsäuredimetliylester, l-Aninobenzol-S^-diearbomsäure-dimethylester, 4-Anißobenzoesäureiaethylesterj ferner Aminobenzoesäureanidej -ftlkyiardde ader -arylamide^ wie beispielsweise 4-Aminobenzoesäui-earaid, ^Chlor-S-arainobenzoösäureanidj 4,6-Dichlor-3-fciiirio'benzoesäureanid, 3-Anino-4-.:5thoKybenzo©sSui'ephenyl-HUBiCl1 3-Aaino-4-m©thyl-benzoesäureraethylar.iicl, 3-Anino-4-ctrbonethoxybenzoesäure-(2' >5*-dichlor)-phenylajnid, schliex^lich Äiainobeiizolsulfonsäureamide, -alkylanide oder -arylaislde,Chloroanilines, such as 2-chloro-aniline, 2,4-dichloroaniline, 2,5-dichloroaniline, 2-chloro-5-methylaniline, 2-chloro-4-methoxyaniline, 4-chloro-2-trifluoromethylaniline J Nitranilines, such as 2 -Nitro-aniline, 2-nitro-4-chloro-aniline, 2-nitro-4-methylaniline, 2-nitro-4-ftcetyiiimino% niline, further aninobenzoic acid ester, such as 2-aminobenzoic acid butyl ester, 2-aminobenzoic acid butyl ester, l -Aminobenssol ^, S-diuarboxylic acid dimetliyl ester, l-aninobenzene-S ^ -diearbomic acid dimethyl ester, 4-anisobenzoic acid ethyl esterj also aminobenzoic acid anidej -ftlkyiardde ader -arylamide ^ such as 4-aminobenzoic acid-earaid-, ^ chloro-dichloro-earaid-, ^ chloro-dichloro 3-fciiirio'benzoic anide, 3-Anino-4-.:5thoKybenzonahmsSui'ephenyl-HUBiCl 1 3-Aaino-4-m © thyl-benzoic acid ethylar.iicl, 3-Anino-4-carbonethoxybenzoic acid- (2 '> 5 * -dichlor) -phenylajnid, finally Äiainobeiizolsulfonsäureamide, -alkylanide or -arylaislde,
009824/1IS!009824 / 1IS!
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Fw 5920Fw 5920
wie beispielsweise 3-Araino~4-nethoxy-benzolsulfonsäurebutylaraid, 3-Amino-4-methylbenzolsulfonsäure:niethylaniid, S-Amino-^chlorbenzolsulfonsäure-isopropylanid, 2,5-Diraethoxy-4-aminobenzoi-sulfonsMuremethylaiaid und 2,5-Dimethoxy-4-arainobenzol-sulfonsäurephenylanid. such as 3-Araino ~ 4-nethoxy-benzenesulphonic acid butylaraid, 3-Amino-4-methylbenzenesulfonic acid: niethylaniid, S-Amino- ^ chlorobenzenesulfonic acid isopropylanide, 2,5-diraethoxy-4-aminobenzoi-sulfone, Muremethylaiaid and 2,5-dimethoxy-4-arainobenzene-sulfonic acid phenylanide.
Die als Azokomponenten verwendeten Verbindungen lassen sich nach bekannten Verfahren herstellen, beispielsweise durch Umsetzung von 2,4-Dinitrochlorbenzolen nit einen Amin der Formel R-HIL, in den R die τ/eiter oben angegebene Bedeutung iiat, zum entsprechenden 2,4-Dinitranilin, dessen partielle Reduktion, beispielsweise^it SuIfhydratlauge, zum entsprechenden 4-Nitro-o-phenylalanin, Umsetzung mit Harnstoff oder Phosgen zua entsprechenden Nitrobenzimidazolon, Reduktion zua entsprechenden Aminobenzinidazolon und Anlagerung von Diketen zua entsprechenden 5-Acetoacetylaminobenzimidazolon gemäß nachstehendem Schema, wobei JL die vorstehend genannte Bedeutung hat:The compounds used as azo components can be prepared by known processes, for example by reacting 2,4-dinitrochlorobenzenes with an amine of the formula R-HIL, in which R has the meaning given above, to give the corresponding 2,4-dinitraniline, its partial reduction, for example it sufhydrate liquor, to the corresponding 4-nitro-o-phenylalanine, reaction with urea or phosgene to a corresponding nitrobenzimidazolone, reduction to a corresponding aminobenzinidazolone and addition of diketene to a corresponding 5-acetoacetylaminobenzimidazolone according to the scheme below, the above-mentioned JL Has meaning:
CH3COCH2CONH-CH 3 COCH 2 CONH-
009824/1*51009824/1 * 51
Als geeignete Amine R-NH2 seien beispielsweise Methylamin, Ä'thylamin, n-Propylamin, iso-Propylamin, n-Butylamin oder iso-Butylamin genannt.Examples of suitable amines R-NH 2 are methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine or isobutylamine.
Als geeignete Azokomponenten der genannten Formel (3) seien beispielsweise genannt:As suitable azo components of the formula (3) mentioned are for example:
l-Methyl-S-Cacetoacetylarainoy-benzimidazolon l-Äthyl-S-Cacetoacetylaminoy-benzimidazolon l-n-Propyl-ö-Cacetoacetylaminoy-benzimidazolon l-iso-Propyl-S-Cacetoacetylaminoy-benzimidazolon l-iso-Butyl-S-Cacetoaeetylaminoy-benzimidazolon l-n-Butyl-5-(acetoacetylamino)-benziraidazolon !,G-Dimethyl-ö-Cacetoacetylaininoy-benzimidkzolon l-Hethyl-6~chlor-6-(acetoacetylamino)-benzimidazolon l-Methyl-T-brom-ö-(acetoacetylamino)-benzimidazolon l-llethyl-7-chlor-5-(acetoacetylamino)-benzimidazolon l-Methyl-e-methoxy-S-Cacetoacetylarainoy-benziraidazolon.1-methyl-S-cacetoacetylarainoy-benzimidazolone l-ethyl-S-cacetoacetylaminoy-benzimidazolone 1-n-propyl-6-cacetoacetylaminoy-benzimidazolone l-iso-propyl-S-cacetoacetylaminoy-benzimidazolone l-iso-butyl-S-cacetoaeetylaminoy-benzimidazolone l-n-butyl-5- (acetoacetylamino) benziraidazolone !, G-Dimethyl-ö-Cacetoacetylaininoy-benzimidkzolon 1-methyl-6-chloro-6- (acetoacetylamino) -benzimidazolone 1-methyl-T-bromo-δ- (acetoacetylamino) benzimidazolone l-llethyl-7-chloro-5- (acetoacetylamino) benzimidazolone 1-methyl-e-methoxy-S-cacetoacetylarainoy-benziraidazolone.
Die Herstellung der Diazoniumverbindungen erfolgt in bekannter Weise. In eiitigen Füllen sind die Diazoniumsalze in wässrigem Medium schwer löslich und scheiden sich ab. Man kann sie isolieren und als feuchte Paste zur Kupplung bringen. Man kann die Diazotierung jedoch auch in einem geeigneten organischen Medium durchführen, beispielsweise in Eisessig, Alkohol, Dioxan, Tetrahydrofuran, Formamid, Dimethylformamid oder Dimethylsulfoxyd, und die so erhaltene Losung der Diazoniumverbindung mit der Azokonponente vereinigen.The diazonium compounds are produced in known way. The diazonium salts are in full fill Slightly soluble in an aqueous medium and separate out. They can be isolated and used as a moist paste for coupling bring. However, the diazotization can also be carried out in a suitable organic medium, for example in glacial acetic acid, alcohol, dioxane, tetrahydrofuran, formamide, dimethylformamide or dimethyl sulfoxide, and the resulting Solution of the diazonium compound with the azo component unite.
Die Farbstoffe lassen sich in Substanz oder auf einem Substrat, z.B. Schwerspat, herstellen.The dyes can be produced in bulk or on a substrate, e.g. barite.
Die Herstellung in Substanz erfolgt nach an sich bekannten Methoden, beispielsweise durch Vereinigung der Diazoniumverbindungen mit den Azokomponenten in wässrigen Mediuni, vorteilhaft in Gegenwart eines anionaktiven, kationalrtivenThe preparation in bulk is carried out by methods known per se, for example by combining the diazonium compounds with the azo components in aqueous media, advantageously in the presence of an anion-active, kationalrtiven
009824/1651009824/1651
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p " Ν, » I pi lip Nr f w p "Ν,» I pi lip no fw
III ipIII ip
oder nichtionogenen Dispergiermittels oder in Gegenwart eines organischen Lösungsmittels.or nonionic dispersant or in the presence an organic solvent.
Die so erhaltenen Farbstoffe sind häufig von hartem Korn und müssen dann zur Erzielung der vollen Farbstärke und der optimalen Echtheiten einer Nachbehandlung unterworfen werden. Beispielsweise erhitzt man die getrockneten und gemahlenen oder feuchten Farbstoffe in Pyridin, Dimethyl« formamid oder anderen organischen Lösungsmitteln, wie Dime thylsulfoxyd, Alkohol oder Chlorbenzol einige Zeit unter Rückfluß oder auf höhere Temperaturen unter Druck. In einigen Fällen gelingt die Überführung in eine kornv/eiche Form auch durch Erhitzen mit Yiasser unter Druck, gegebenenfalls unter Zusatz von Dispergiermitteln.The dyes obtained in this way are often of hard grain and must then be subjected to an aftertreatment in order to achieve full color strength and optimum fastness properties will. For example, the dried and ground or moist dyes are heated in pyridine, dimethyl « formamide or other organic solvents such as dime methyl sulfoxide, alcohol or chlorobenzene for some time Reflux or at higher temperatures under pressure. In some cases, it can also be converted into a grainy / oak form by heating with water under pressure, if necessary under Addition of dispersants.
Die nach dem vorliegenden Verfahren erhältlichen Farbstoffe stellen wasserunlösliche Pigmente dar. Sie eignen sich zur Herstellung von gefärbten Lacken, Lackbildnern, Lösungen und Produkten aus Acetylzellulose, natürlichen Harzen oder Kunstharzen wie Polymerisations- oder Kondensationsharzen, wie beispielsweise Aminoplasten oder Phenoplasten, sowie aus Polystyrol, Polyolefinen, wie beispielsweise Polyäthylen oder Polypropylen, Polyacrylverbindungen, Polyvinylverbindungen, beispielsweise Polyvinylchlorid oder Polyvinylacetat, Polyestern, Gummi, Casein- oder Siliconharzen,The dyes obtainable by the present process represent water-insoluble pigments. They are suitable for the production of colored lacquers, lacquer formers, solutions and products made from acetyl cellulose, natural resins or synthetic resins such as polymerization or condensation resins, such as aminoplasts or phenoplasts, as well as from polystyrene, polyolefins, such as polyethylene or polypropylene, polyacrylic compounds, polyvinyl compounds, for example polyvinyl chloride or polyvinyl acetate, polyesters, rubber, casein or silicone resins,
Die neuen Farbstoffe eignen sich ferner für den Pigmentdruck auf einem Substrat, insbesondere auf Textilfasern sowie auch auf anderen flächenförmigen Gebilden, wie beispielsweise auf Papier· Sie können auch für andere Verwendungszwecke, z.B. in feinverteilter Fora zum Färben von Kunstseide aus Viskose oder Zelluloseätherη bzw, -estern, Polyamiden oder Polyurethanen in der Spinnmasse oder zum Färben von Papier verwendet werden.The new dyes are also suitable for pigment printing on a substrate, in particular on textile fibers as well on other sheet-like structures, such as for example on paper. They can also be used for other purposes, e.g. in finely divided form for dyeing rayon or cellulose ether or esters, polyamides or polyurethanes can be used in textile pulp or for dyeing paper.
009824/1651009824/1651
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Aufgrund ihrer günstigen Theologischen Eigenschaften lassen sich die Farbstoffe in den genannten Medien gut verarbeiten. Sie weisen dann gute Licht-, Tfetter- und Migrationsechtheiten auf. Sie sind v/eiterhin hitzebeständig, farbstark und zeigen in vielen Fällen reine, brillante Farbtöne. Gegen Einfluß von Chemikalien, z.B. von Lösungsmitteln, sind sie beständig, insbesondere gegen saure und alkalische Einwirkungen.Because of their favorable theological properties, the dyes can be used in the media mentioned to process. They then have good light, oil and migration fastness properties. They are still heat-resistant, strong in color and in many cases show pure, brilliant shades. Against the influence of chemicals, e.g. of solvents, they are resistant, especially to acidic and alkaline effects.
20,9 Gewichtsteile 5-Aiaino-isophthalsäuredimethylester werden mit SO Volurienteilen 5n Salzsäure etwa eine· Stunde verrührt und anschließend mit 300 Voluraenteilen Wasser verdünnt. Man diazotiert bei 10°C mit 20 Volumenteilen 5n Natriumnitritlösung, klärt mit Kieselgur und beseitigt einen eventuellen Überschuß an salpetriger Säure mit etwas Anidosulfosäure. 20.9 parts by weight of 5-alino-isophthalic acid dimethyl ester Stirred with 50 parts by volume of 5N hydrochloric acid for about an hour and then diluted with 300 parts by volume of water. It is diazotized at 10 ° C with 20 parts by volume of 5N sodium nitrite solution, clears with kieselguhr and removes any excess nitrous acid with a little anidosulfonic acid.
Diese Diftzolösung laßt man bei etwa 2O°C unter gutein Rühren zu einer essigsauren Suspension der Azokomponente fließen, die auf folgendem Wege hergestellt wurde:This Diftzo solution is left at about 20 ° C. with thorough stirring flow to an acetic acid suspension of the azo component, which was prepared in the following way:
25,5 Gewichtsteile l-Methyl-S-acetoacetylamino-benzimidazolon werden bei Raumtemperatur mit 200 Voluraenteilen Wasser verrührt und durch Zugabe von 60 Volumenteilen 5n Natronlauge gelöst« Diese Lösung wird mit Aktivkohle geklärt und die geklärte Lösung im Verlauf von etwa 30 Minuten unter Rühren in eine Lösung aus 300 Voluinenteilen Wasser, 41 Volumenteilen Eisessig und 80 Volumenteilen 5n Natronlauge bei Raumtemperatur eingetropft.25.5 parts by weight of 1-methyl-S-acetoacetylamino-benzimidazolone are stirred with 200 parts by volume of water at room temperature and dissolved by adding 60 parts by volume of 5N sodium hydroxide solution «This solution is clarified with activated charcoal and the Clarified solution in the course of about 30 minutes while stirring into a solution of 300 parts by volume of water, 41 parts by volume Glacial acetic acid and 80 parts by volume of 5N sodium hydroxide solution were added dropwise at room temperature.
Die Kupplung ist sofort beendet. Man bringt das Kupplungsgemisch zum Kochenι saugt ab, wäscht gründlich nit Wasser und trocknet bei 600C. Das erhaltene- gelbe Pigment wird gepulvert und in 450 Volumenteilen Dimethylformamid 4 StundenThe coupling is ended immediately. Bringing the coupling mixture to Kochenι filtered off, washed thoroughly and dried at 60 nit water 0 C. The erhaltene- yellow pigment is pulverized and in 450 parts by volume of dimethylformamide 4 hours
009124/1*61009124/1 * 61
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18080Π18080Π
auf 13O0C erhitzt. Anschließend -wird abgesaugt, das Dimethylformamid mit Methanol ausgewaschen und der Farbstoff getrocknet. Man erhält ein gelbes Pigment von weichem Korn, guter Farbstärke und reinem Farbton. In Polyvinylchlorid, einen Lack, eine Druckfarbe oder eine Dispersionsanstrichfarbe eingearbeitet, erhält man gelbe Färbungen hoher Lichtechtheit, einwandfreier Uberlackierechtheit und Hitzebeständigkeit und sehr guter Ausblutechtheit in Polyvinylchlorid. heated to 13O 0 C. Then it is filtered off with suction, the dimethylformamide is washed out with methanol and the dye is dried. A yellow pigment with a soft grain, good color strength and a pure shade is obtained. When incorporated into polyvinyl chloride, a lacquer, a printing ink or a dispersion paint, yellow colorations of high lightfastness, perfect overcoating fastness and heat resistance and very good fastness to bleeding in polyvinyl chloride are obtained.
Statt Dimethylformamid kann man die gleichen Gewichtsmengen Pyridin oder Eisessig einsetzen. In diesem Fall erhitzt man 4 Stunden unter Rückfluß.Instead of dimethylformamide, you can use the same weight amounts Use pyridine or glacial acetic acid. In this case, the mixture is refluxed for 4 hours.
Verwendet man im obigen Beispiel statt l-lIethyl-5-acetoacetylamino-benzlmidazolon die äquivalenten Mengen l-IIethyl-6-chlor-5-acetoacetylaraino-benzimidazolon, l-Methyl-7-chlor-5-acetoacetylaminobenzimidazolon, l-Methyl-7-bron-5-acetoacetylamino-benzinidazolon, l-llethyl-e-methoxy-ö-acetoacetylamino-benzimidazolon oder l,6~Dimethyl-5-acetoacetylaminobenzimidazolon, so erhält man gleichfalls gelbe Pigmente mit guten Echtheitseigenschaften.Is used in the above example instead of l-ethyl-5-acetoacetylamino-benzimidazolone the equivalent amounts of l-IIethyl-6-chloro-5-acetoacetylarainobenzimidazolone, l-methyl-7-chloro-5-acetoacetylaminobenzimidazolone, l-methyl-7-bron-5-acetoacetylamino-benzinidazolone, l-llethyl-e-methoxy-ö-acetoacetylamino-benzimidazolone or l, 6 ~ dimethyl-5-acetoacetylaminobenzimidazolone, yellow pigments with good fastness properties are likewise obtained in this way.
Die Verarbeitung in Polyvinylchlorid erfolgt beispielsweise nach folgendem Verfahren: 16,5 Gewichtsteile eines tfeichmachergemisches, bestehend aus gleichen Teilen Dioctyl- |Processing in polyvinyl chloride takes place, for example according to the following procedure: 16.5 parts by weight of a softener mixture, consisting of equal parts dioctyl- |
phthalat und Dibutylphthalat, werden mit 0,05 Gewichtsteilen Farbstoff und 0,25 Gewichtsteilen Titandioxyd vermischt. Dann werden 33,5 Gewichtsteile Polyvinylchlorid zugegeben. Das Gemisch wird 10 Minuten auf einem Zv/e !walzenstuhl mit Friktion gewalzt, wobei das sich bildende Fell nit einen Spatel fortlaufend zerschnitten und zusammengerollt wird. Dabei wird die eine tfalze auf einer Temperatur von 40°C, die andere auf einer Temperatur von 1400C gehalten. Anschließend wird das Genisch als Fell abgezogen und 5 Minuten bei 160°C zwischen zvei polierten Metallplatten gepreßt.phthalate and dibutyl phthalate are mixed with 0.05 part by weight of dye and 0.25 part by weight of titanium dioxide. Then 33.5 parts by weight of polyvinyl chloride are added. The mixture is rolled for 10 minutes on a Zv / e! Roller chair with friction, the skin that is formed being continuously cut up and rolled up with a spatula. In this case, the one tfalze at a temperature of 40 ° C, the other kept at a temperature of 140 0 C. Then the genic is peeled off as fur and pressed between two polished metal plates at 160 ° C for 5 minutes.
009824/1*51009824/1 * 51
gADgAD
24,6 Gewichtsteile l-Amino-2,5-diraethoxybenzol-4-sulfonsäuremethylamid werden mit einer Mischung aus 50 Volumenteilen Wasser und 45 Volumenteilen 5n Salzsäure mehrere Stunden verrührt, wobei sich das Hydrochlorid des einge- *■ setzten Amins bildet. Danach wird mit 100 Volumenteilen Wasser verdünnt, bei 15°C mit 20 Volumenteilen 5n Natriumnitritlösung diazotiert, ein eventueller Überschuß an salpetriger Säure durch Zugabe von etwas Amidosulfosäure beseitigt und zuletzt mit Kieselgur geklärt.24.6 parts by weight are stirred for several hours with a mixture of 50 parts by volume water and 45 parts by volume of 5N hydrochloric acid l-amino-2,5-4-sulfonic acid methylamide diraethoxybenzol-, whereby the hydrochloride of the amine added einge- * ■ forms. It is then diluted with 100 parts by volume of water, diazotized at 15 ° C. with 20 parts by volume of 5N sodium nitrite solution, any excess of nitrous acid is eliminated by adding a little sulfamic acid and finally clarified with kieselguhr.
Diese Diazolösung läßt man bei 20°C unter gutem Rühren zu einer essigsauren Suspension aus 25,5 Gewichtsteilen l-Methyl-5-acetoacetylamino-benzimidazolon, hergestellt entsprechend Beispiel 1, zulaufen. Nach beendeter Kupplung wird der Farbstoff abgesaugt, gewaschen und getrocknet. Der gemahlene Farbstoff wird mit 600 Volumenteilen Eisessig 3 Stunden unter Rückfluß erhitzt, anschließend wird abgesaugt, zunächst mit !!ethanol, dann mit T/asser gev/aschen und getrocknet, llan erhält ein gelbes Pigment, das, in Polyvinylchlorid, einen Lack, eine Druckfarbe oder eine Dispersionsanstrichfarbe eingearbeitet, rotstichige Gelbfärbungen hoher Lichtechtheit, einwandfreier Überlackierechtteit. und sehr guter Ausblutechtheit in Polyvinylchlorid gibt. Arbeitet man das Pigment in eine Oel-in-Wasser Emulsion oder eine Yfasser-in-Oel Emulsion ein, so erhält man Druckpasten, mit denen man Textilgewebe, zum Beispiel aus Baumwolle oder Polyesterfasern, in gelben Farbtönen mit guter Lichtechtheit und guter Trockenreinigungsechtheit färben kann.This diazo solution is left at 20 ° C. with thorough stirring to an acetic acid suspension of 25.5 parts by weight of l-methyl-5-acetoacetylamino-benzimidazolone according to example 1. After the coupling has ended, the dye is filtered off with suction, washed and dried. The ground dye becomes glacial acetic acid with 600 parts by volume Heated under reflux for 3 hours, then suctioned off, first with ethanol, then with water / ash and dried, llan receives a yellow pigment, which, in polyvinyl chloride, a varnish, a printing ink or a dispersion paint incorporated, reddish yellow coloring high lightfastness, perfect overcoating fastness. and very good resistance to bleeding in polyvinyl chloride. If you work the pigment in an oil-in-water emulsion or a water-in-oil emulsion, printing pastes are obtained with which one textile fabrics, for example made of cotton or polyester fibers, in yellow shades with good lightfastness and can dye with good dry cleaning fastness.
17,1 Gewichtsteile l-Araino-^-chlorbenzol-S-carbonsäureamid werden mit 50 Volumenteilen 5n Salzsäure und 175 Volunenteilen Wasser heiß gelöst und nach Zugabe von Eis bei 5° mit 20 Volumenteilen 5n Natriumnitritlösung diazotiert.17.1 parts by weight of 1-araino - ^ - chlorobenzene-S-carboxamide are dissolved hot with 50 parts by volume of 5N hydrochloric acid and 175 parts by volume of water and after adding ice 5 ° diazotized with 20 parts by volume of 5N sodium nitrite solution.
009824/1651009824/1651
0^O QHlQlHAL 0 ^ O QHlQlHAL
Die Diazolösung wird geklärt und mit einer entsprechend Beispiel 1 hergestellten Suspension aus 25,5 Gewichtsteilen l-Methyl-S-acetoacetylamino-benziraidazolon gekuppelt. Nach beendeter Kupplung wird der Farbstoff abgesaugt, gewaschen und getrocknet. Der gemahlene Farbstoff wird iait 600 '' Volumenteilen Eisessig 3 Stunden unter Rückfluß erhitzt, anschließend abgesaugt, zunächst mit Methanol, dann mit Wasser gewaschen und getrocknet.The diazo solution is clarified and coupled with a suspension prepared according to Example 1 of 25.5 parts by weight of 1-methyl-S-acetoacetylamino-benziraidazolone. After the coupling has ended, the dye is filtered off with suction, washed and dried. The ground dye is refluxed for 3 hours with 600 ″ parts by volume of glacial acetic acid, then filtered off with suction, washed first with methanol and then with water and dried.
Han erhält ein gelbes Pigment, das, in Polyvinylchlorid, einen Lack, 'eine Druckfarbe oder eine Dispersionsanstrichfarbe eingearbeitet, rotstichige Gelbfärbungen hoher Licht- ä echtheit, einwandfreier Uberlackierechtheit und sehr guter Ausblutechtheit in Polyvinylchlorid gibt. Arbeitet man das Pigment in eine OeI-in-Wasser Emulsion oder eine Wasser-in-Oel Emulsion ein, so erhält man Druckpasten, mit denen man Textilgewebe, zum Beispiel aus Baumwolle oder Polyesterfasern, in gelben Farbtönen mit guter Lichtechtheit und guten Trockenreinigungsechtheiten färben kann.Han A yellow pigment which, in polyvinyl chloride, a lacquer, 'a printing ink or a dispersion paint incorporated reddish yellow dyeings of high light fastness, etc., are perfect Uberlackierechtheit and very good resistance to bleeding in polyvinyl chloride. If the pigment is worked into an oil-in-water emulsion or a water-in-oil emulsion, printing pastes are obtained with which textile fabrics, for example made of cotton or polyester fibers, can be dyed in yellow shades with good lightfastness and good fastness to dry cleaning .
Verwendet man im obigen Beispiel statt 25,5 Gev/ichtsteilen l-Methyl-5-acetoacetylamino-benzimidazolon die äquivalente ilenge l-Xthyl-S-acetoacetylamino-benzimidazolon oder 1-Isopropyl-S-acetoacetylaaino-benzimidazolon oder l-Isobutyl-5- j acetoacetylamino-benzlmidazolon, so erhält man gleichfalls gelbe Pigmente mit ähnlich guten Eigenschaften.Is used in the above example instead of 25.5 weight parts l-methyl-5-acetoacetylamino-benzimidazolone the equivalent ilenge l-ethyl-S-acetoacetylamino-benzimidazolone or 1-isopropyl-S-acetoacetylaaino-benzimidazolone or l-isobutyl-5- j acetoacetylamino-benzimidazolone is also obtained yellow pigments with similarly good properties.
Entsprechend den Beispielen 1 bis 3 lassen sich die in der nachfolgenden Tabelle angeführten Diazo- und Azokoraponenten einsetzen· Der Farbton der auf diese Weise hergestellten Pigmente im graphischen Druck wird in der rechten Spalte angegeben:According to Examples 1 to 3, the diazo and azo-coraponents listed in the table below can be used insert · The hue of the produced in this way Pigments in graphic printing are indicated in the right column:
009824/1851009824/1851
BAD ORIGINALBATH ORIGINAL
DiazokomponenteDiazo component
AzokomponenteAzo component
Farbtonhue
2,5-Dichloranilin2,5-dichloroaniline
4-Chlor-2-nitroanilin 4-Methyl-2-nitroanilin4-chloro-2-nitroaniline 4-methyl-2-nitroaniline
4-Acetylamino-2-nitroanilin 2f5-Dichlor-4-nitroanilin4-acetylamino-2-nitroaniline 2 f 5-dichloro-4-nitroaniline
2-Hethoxy-5-acetylaminoanilin 2-Hethoxy-5-acetylaminoaniline
5~Methyl-2-chloranilin 2-Trifluormethyl-anilin5 ~ methyl-2-chloroaniline 2-trifluoromethyl aniline
4-Chlor-2-trifluormethylanllin 4-chloro-2-trifluoromethylanlline
l-Methyl-5-acetoacetylaraino-benziniclazolon l-methyl-5-acetoacetylaraino-benziniclazolone
IlIl
2-Amino-5-chlorbenzonitril "2-amino-5-chlorobenzonitrile "
gelb orangeyellow orange
rotstichiges Gelbreddish yellow
IlIl
gelbyellow
2-Aralnobenzoesäuremethylester 2-aralnobenzoic acid methyl ester
4-Chlor~2-aminobenzoesäuremethylester 4-chloro ~ 2-aminobenzoic acid methyl ester
4-Bron-2-aminobenzoesäure~ methylester4-bron-2-aminobenzoic acid ~ methyl ester
5-Chlor-2-aminobenzoesäuremethylester 5-chloro-2-aminobenzoic acid methyl ester
3-Chlor-4-aminobenzoesäuremethylester 3-chloro-4-aminobenzoic acid methyl ester
2,4-DiChIOr-O-aminobenzoesäuremethylester 2,4-DiChIOr-O-aminobenzoic acid methyl ester
5-Nitro-2-arainobenzoesKuremethylester 5-nitro-2-arainobenzoe cure methyl ester
4-Trifluormethyl-2-aminobenzoesäuremethylester 4-trifluoromethyl-2-aminobenzoic acid methyl ester
l-Arainobenzol-2,5-dicarbonßäure-dimethylester L-arobenzene-2,5-dicarboxylic acid dimethyl ester
l-Aminobenzol-2-carbonsäure-l-aminobenzene-2-carboxylic acid
methylester-5-carbonsäure-methyl ester-5-carboxylic acid
amidamide
l-Aminobenzol-2-carbonsäyre-l-aminobenzene-2-carboxylic acid
ftthylester-5-carbonsäure-ethyl ester-5-carboxylic acid
amidamide
l-Aminobenzol-2-carbonsäureisobutylester-5-carbonsäurearaid "Isobutyl l-aminobenzene-2-carboxylate-5-carboxylic acid araid "
l-Aninobenzol-2-carbonsäure- 1-Isobutyl-5-acetoraethylester-5-carbonsäureacetylanino-benzimidaamid zolon1-aninobenzene-2-carboxylic acid 1-isobutyl-5-acetoraethyl ester-5-carboxylic acid acetylanino-benzimidaamide zolon
009824/1C51 .009824 / 1C51.
ItIt
IlIl
IlIl
titi
IlIl
IlIl
IlIl
rotstichiges Gelbreddish yellow
gelbyellow
titi
ttdd
•ι• ι
IlIl
IlIl
BADBATH
DiazokomponenteDiazo component
AzokomponenteAzo component
Farbtonhue
il-Aminobenzol-2-caxtl)onsäure- !iaethylester-5-carbonsäurejmethylajnid il-aminobenzene-2-cax t l) onic acid- ! ethyl ester-5-carboxylic acid methyl ester
l-Aminobenzol-2-carbonsäuremethylester-5-carbonsäure-2',S'-dichlorphenylamid 1-aminobenzene-2-carboxylic acid methyl ester-5-carboxylic acid-2 ', S'-dichlorophenylamide
l-Amino-benzol-2-carbonsäuremethylester-5~carbonsäure-3'-trifluormethylphenylaraid 1-Amino-benzene-2-carboxylic acid methyl ester-5-carboxylic acid-3'-trifluoromethylphenyl aramid
4-llethyl-3-aminobenzoesäurenethylester Ethyl 4-llethyl-3-aminobenzoate
4-Methoxy-3-aminobenzoesäuremethylester : 4-Methoxy-3-aminobenzoic acid methyl ester :
4-Chlor-3-aminobenzoesäuremethylester 4-chloro-3-aminobenzoic acid methyl ester
4-Aminobenzoesäurearaid4-aminobenzoic acid arraid
4-Methyl-3-arainobenzoesäuremethylamid 4-methyl-3-arainobenzoic acid methylamide
4-iIethoxy-3-amlnobenzoesaureamid 4-iethoxy-3-aminobenzoic acid amide
4-Xthoxy-3-Rminobenzoesäureamid 4-Xthoxy-3-rminobenzoic acid amide
4-n-Butoxy-3-aminobenzoesäure amid4-n-butoxy-3-aminobenzoic acid amide
4-Methyl-3-aminobenzoesäurearaid 4-methyl-3-aminobenzoic acid avaid
4,6-Dichlor-3-aminobenzoesäureamid 4,6-dichloro-3-aminobenzoic acid amide
2-Amino-2·,4'-dichlor-diphenyläther-4-carbonsäure- arnid2-Amino-2, 4'-dichloro-diphenylether-4-carboxylic acid arnid
2-Amino-4·-methyl-diphenyläther-4-carbonsäureaiaid 2-Amino-4-methyl-diphenylether-4-carboxylic acid amide
2-Amino-4'-chlor-diphenyläther-4-carbonsaure-methyl- amid2-amino-4'-chloro-diphenyl ether-4-carboxylic acid methyl amide
4-Chlor-3-aminobenzoesäure-2 *,5-dichlorphenylamid4-chloro-3-aminobenzoic acid-2 *, 5-dichlorophenylamide
4-l,Iethoxy-3~aninobenzoesäure-3'-trifluormethylphenylamid l-Methyl-5-aceto-4-l, ethoxy-3-aninobenzoic acid-3'-trifluoromethylphenylamide l-methyl-5-aceto-
acetylamino-acetylamino
benzimidazolonbenzimidazolone
l-Methyl-5-aceto-l-methyl-5-aceto-
acetylaraino-acetylaraino-
benzimidazolonbenzimidazolone
gelbyellow
1111th
titi
IlIl
_ Il Il_ Il Il
IlIl
IlIl
IlIl
ItIt
IlIl
ttdd
ItIt
titi
l-Methyl-6-chlor-l-methyl-6-chloro
5-acetoacetylamino-5-acetoacetylamino
benzimidazolonbenzimidazolone
1-Isopropyl-6-chlor-1-isopropyl-6-chloro
5-acetoacetylamino-5-acetoacetylamino
benzimidazolonbenzimidazolone
l-lIethyl-5-acetoacetylaminobenz inidazolonl-l-ethyl-5-acetoacetylaminobenz inidazolone
titi
tt Il Iltt Il Il
009824/1651 BAD ORIGINAL 009824/1651 ORIGINAL BATHROOM
DiazokomponenteDiazo component
- 12 Azokonponente - 12 azo components
Farbtonhue
4-Methyl-3-aninobenzoesäureisopropylanid 4-methyl-3-aninobenzoic acid isopropylanide
4-Chlor-3-aninobenzoesäureäthylanid 4-chloro-3-aninobenzoic acid ethylanide
4-Chlor-3-a-iinobenzoesäure-2'-raethyl-3'-chlorphenylarnid 4-Chloro-3-α-iinobenzoic acid-2'-raethyl-3'-chlorophenyl amide
4-Methyl-3-aninobenzoesäure-2'-chlor-S'-trifluornethylphenylanid 4-methyl-3-aninobenzoic acid-2'-chloro-S'-trifluoromethylphenylanide
4-Chlor-3-aninobenzoesäuren-butylanid 4-chloro-3-aninobenzoic acid butyl anide
l-Aminobenzol-3,5-dicarbonsäuredlamid l-aminobenzene-3,5-dicarboxylic acid amide
l-Aminobenzol-3,5-dicarbonsäure-di-mononethylamid l-aminobenzene-3,5-dicarboxylic acid-di-mononethylamide
4-lIethoxy-3-aminobenzoesäuren '-methoxy-5 '-chlorphenylanid 4-ethoxy-3-aminobenzoic acid 'methoxy-5' chlorophenylanide
4-Chlor-3-aninobenzolsulfonsäureanid 4-chloro-3-aninobenzenesulfonic acid anide
4-Amino-2,5-dimethoxybenzol-sulfonsäureanid 4-Amino-2,5-dimethoxybenzenesulfonic acid anide
4-Amino-2,5-diraethoxybenzol-sulfonsäureanid 4-Amino-2,5-diraethoxybenzenesulfonic acid anide
4-Amino-2,5-dinethoxybenzolsulfonsäurenethyl- uaid4-amino-2,5-dinethoxybenzenesulfonic acid ethyl uaid
l-I.iethyl-5-acetoacetylanino- benzimidazolonl-I.iethyl-5-acetoacetylanino- benzimidazolone
gelbyellow
IlIl
IlIl
l-Methyl-6-brora-5-acetoacetylaninor benzimidazolonl-methyl-6-brora-5-acetoacetylaninor benzimidazolone
l-Athyl-5-acetoacetylaraino- benzimidazolonl-ethyl-5-acetoacetylaraino- benzimidazolone
l-n-Propyl-5-acetoacetylara5.no- benzimidazolonl-n-propyl-5-acetoacetylara5.no- benzimidazolone
l-Methyl-e-iaethoxy-öacetoacetylaraino- benzimidazolonl-methyl-e-iaethoxy-öacetoacetylaraino- benzimidazolone
1-Methyl-5-acet oacetylanino- benzimidazolon1-methyl-5-acet oacetylanino- benzimidazolone
l-Methyl-5-acetoacetylanino- benzimidazolonl-methyl-5-acetoacetylanino- benzimidazolone
l-Methyl-e-chlor-öacetoacetylamino- benzinidazolonl-methyl-e-chloro-acetoacetylamino- benzinidazolone
1,6-Diraethyl-S-acetoacetylamino- benzimidazolon1,6-diraethyl-S-acetoacetylamino- benzimidazolone
l-Methyl-eiaethoxy-5-acetoacetylaninobenzimidaz ölon1-methyl-eiaethoxy-5-acetoacetylaninobenzimidaz olon
l-n-Propyl-5-acetoacetylaiairio- benzinidazolonl-n-propyl-5-acetoacetylaiairio- benzinidazolone
IlIl
IlIl
• I Il• I Il
ItIt
009824/1651009824/1651
ORIGINALORIGINAL
DiazokomponenteDiazo component
AzokonponenteAzo component
Farbtonhue
4-Amino-2,5-dimethoxybenzolsulfonsäureraethylaraid 4-Amino-2,5-dimethoxybenzenesulfonic acid ethyl araid
4-Amino-5-methoxy-2-methylbenzol-sulfonsäuremethyl- amid4-Amino-5-methoxy-2-methylbenzene-sulfonic acid methyl amide
4-Amino-2,5~dimethoxybenzol sulfonsäureäthylamid4-amino-2,5-dimethoxybenzene sulfonic acid ethylamide
4-Amino-2,5-dimethoxybenzolsulfonsäure-isopropylamid 4-Amino-2,5-dimethoxybenzenesulfonic acid isopropylamide
4-Amino-2,5- diine thoxybenzol-8ulfonsäurern-butylamid 4-Amino-2,5-diine thoxybenzenesulfonic acid r n-butylamide
4-Amino-2,5-dimethoxybenzolsäurephenylamid 4-Amino-2,5-dimethoxybenzenic acid phenylamide
l-n-Butyl-5-aceto-l-n-butyl-5-aceto-
acetylaraino-acetylaraino-
benzinidazolonbenzinidazolone
l-Methyl-5-aceto-l-methyl-5-aceto-
acetylanino-acetylanino
benzimidazolonbenzimidazolone
gelbyellow
_ ti_ ti
titi
titi
4-Amino-2,5-dimethoxybenzol- „ Bulf onsäure-2',5 ^dimethoxy-4'-chlorphenylamid 4-Amino- 2,5-dimethoxybenzene- "sulfonic acid-2 ', 5 ^ dimethoxy-4'-chlorophenylamide
4~Aiaino-2,5- dimethoxy-benzol- " sulfonsäure-2'-methylphenylamid 4-Alino-2,5-dimethoxy-benzene- "sulfonic acid-2'-methylphenyl amide
It /It /
titi
IlIl
ttdd
titi
säuremethylamidacid methylamide
4-Methoxy-3-araino-benzolsulfonsäuremethylamid 4-methoxy-3-arainobenzenesulfonic acid methylamide
tt Iltt Il
IlIl
009824/1651009824/1651
BAD ORIGINALBATH ORIGINAL
Claims (1)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681808017 DE1808017C3 (en) | 1968-11-09 | Water-insoluble monoazo compounds, process for their preparation and their use as pigments | |
| CH1648569A CH510085A (en) | 1968-11-09 | 1969-11-05 | Process for the production of new water-soluble monoazo pigments |
| GB1266615D GB1266615A (en) | 1968-11-09 | 1969-11-10 | |
| FR6938739A FR2022980B1 (en) | 1968-11-09 | 1969-11-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681808017 DE1808017C3 (en) | 1968-11-09 | Water-insoluble monoazo compounds, process for their preparation and their use as pigments |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1808017A1 true DE1808017A1 (en) | 1970-06-11 |
| DE1808017B2 DE1808017B2 (en) | 1977-02-03 |
| DE1808017C3 DE1808017C3 (en) | 1977-09-22 |
Family
ID=
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956266A (en) * | 1973-10-30 | 1976-05-11 | Ciba-Geigy Corporation | Bis-(benzimidazolone-azo-acetoacetylamino)-phenylene pigments |
| US4080321A (en) * | 1973-08-01 | 1978-03-21 | Hoechst Aktiengesellschaft | Monoazo pigments from diazotized acylamino-anilines and acetoacetylamino benzimidazolones |
| DE2800765A1 (en) * | 1977-01-11 | 1978-07-13 | Ciba Geigy Ag | NEW MONOAZO PIGMENTS AND PROCESS FOR THEIR PRODUCTION |
| FR2398784A1 (en) * | 1977-07-27 | 1979-02-23 | Ciba Geigy Ag | MONOAZOIC PIGMENTS AND THEIR USES |
| US4169830A (en) * | 1976-11-13 | 1979-10-02 | Hoechst Aktiengesellschaft | Diamino-benzanilide disazo coloring agents |
| US4195020A (en) * | 1973-09-21 | 1980-03-25 | Hoechst Aktiengesellschaft | Dichloro-phenyl-azo-acetoacetylamino-benzimidazolone pigments |
| EP0010272A1 (en) * | 1978-10-21 | 1980-04-30 | Hoechst Aktiengesellschaft | Azo-compounds, process for their preparation and their use |
| EP0010273A1 (en) * | 1978-10-21 | 1980-04-30 | Hoechst Aktiengesellschaft | Monoazo-compounds of the acetoacetylaminobenzimidazolone series, their preparation and use |
| EP0029558A1 (en) * | 1979-11-24 | 1981-06-03 | Hoechst Aktiengesellschaft | Azo compounds, process for their preparation and their use |
| US4277397A (en) * | 1978-10-31 | 1981-07-07 | Hoechst Aktiengesellschaft | Monoazo compounds deriving from 5-amino-benzimidazole-2-one-6-carboxylic acid |
| EP0061728A1 (en) * | 1981-03-31 | 1982-10-06 | Hoechst Aktiengesellschaft | Monoazo compounds, their preparation and their use |
| DE3604488A1 (en) * | 1986-02-13 | 1987-08-27 | Halbach & Braun Ind Anlagen | DRIVE STATION FOR A CHAIN CONVEYOR, IN PARTICULAR STRAIGHT CONVEYOR |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080321A (en) * | 1973-08-01 | 1978-03-21 | Hoechst Aktiengesellschaft | Monoazo pigments from diazotized acylamino-anilines and acetoacetylamino benzimidazolones |
| US4195020A (en) * | 1973-09-21 | 1980-03-25 | Hoechst Aktiengesellschaft | Dichloro-phenyl-azo-acetoacetylamino-benzimidazolone pigments |
| US3956266A (en) * | 1973-10-30 | 1976-05-11 | Ciba-Geigy Corporation | Bis-(benzimidazolone-azo-acetoacetylamino)-phenylene pigments |
| US4169830A (en) * | 1976-11-13 | 1979-10-02 | Hoechst Aktiengesellschaft | Diamino-benzanilide disazo coloring agents |
| DE2800765A1 (en) * | 1977-01-11 | 1978-07-13 | Ciba Geigy Ag | NEW MONOAZO PIGMENTS AND PROCESS FOR THEIR PRODUCTION |
| US4206114A (en) * | 1977-07-27 | 1980-06-03 | Ciba-Geigy Corporation | Monoazo pigments from diazotized 5-acylaminoanthranilic acid derivatives and acetoacetylaminobenzimidazolones |
| FR2398784A1 (en) * | 1977-07-27 | 1979-02-23 | Ciba Geigy Ag | MONOAZOIC PIGMENTS AND THEIR USES |
| EP0010272A1 (en) * | 1978-10-21 | 1980-04-30 | Hoechst Aktiengesellschaft | Azo-compounds, process for their preparation and their use |
| EP0010273A1 (en) * | 1978-10-21 | 1980-04-30 | Hoechst Aktiengesellschaft | Monoazo-compounds of the acetoacetylaminobenzimidazolone series, their preparation and use |
| US4302388A (en) * | 1978-10-21 | 1981-11-24 | Hoechst Aktiengesellschaft | Monoazo compounds deriving from meta-amino-benzoic acid anilides and acetoacetyl amino-benzimidazolone |
| US4302389A (en) * | 1978-10-21 | 1981-11-24 | Hoechst Aktiengesellschaft | Azo compounds deriving from amino benzoic acid anilides and acetoacetylamino-benzimidazolone |
| US4368155A (en) * | 1978-10-21 | 1983-01-11 | Hoechst Aktiengesellschaft | Monoazo compounds derived from meta-amino-benzoic acid anilides and acetoacetylamino-benzimidazolone |
| US4504416A (en) * | 1978-10-21 | 1985-03-12 | Hoechst Aktiengesellschaft | Azo compounds deriving from amino benzoic acid anilides and acetoacetylamino-benzimidazolone |
| US4277397A (en) * | 1978-10-31 | 1981-07-07 | Hoechst Aktiengesellschaft | Monoazo compounds deriving from 5-amino-benzimidazole-2-one-6-carboxylic acid |
| EP0029558A1 (en) * | 1979-11-24 | 1981-06-03 | Hoechst Aktiengesellschaft | Azo compounds, process for their preparation and their use |
| EP0061728A1 (en) * | 1981-03-31 | 1982-10-06 | Hoechst Aktiengesellschaft | Monoazo compounds, their preparation and their use |
| DE3604488A1 (en) * | 1986-02-13 | 1987-08-27 | Halbach & Braun Ind Anlagen | DRIVE STATION FOR A CHAIN CONVEYOR, IN PARTICULAR STRAIGHT CONVEYOR |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2022980B1 (en) | 1974-02-22 |
| CH510085A (en) | 1971-07-15 |
| DE1808017B2 (en) | 1977-02-03 |
| GB1266615A (en) | 1972-03-15 |
| FR2022980A1 (en) | 1970-08-07 |
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