JP2598065B2 - ホルマザン―銅錯化合物および該化合物を染料として使用する方法 - Google Patents
ホルマザン―銅錯化合物および該化合物を染料として使用する方法Info
- Publication number
- JP2598065B2 JP2598065B2 JP63038790A JP3879088A JP2598065B2 JP 2598065 B2 JP2598065 B2 JP 2598065B2 JP 63038790 A JP63038790 A JP 63038790A JP 3879088 A JP3879088 A JP 3879088A JP 2598065 B2 JP2598065 B2 JP 2598065B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- amino
- atom
- zero
- substituted
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 82
- 238000000034 method Methods 0.000 title claims description 40
- 239000000975 dye Substances 0.000 title description 30
- 238000004043 dyeing Methods 0.000 claims description 62
- -1 hydroxy, phenyl Chemical group 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 125000003277 amino group Chemical group 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 239000002657 fibrous material Substances 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 239000000835 fiber Substances 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 239000003513 alkali Substances 0.000 claims description 11
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 2
- 229920001577 copolymer Chemical group 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 125000005521 carbonamide group Chemical group 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 239000000243 solution Substances 0.000 description 45
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000004744 fabric Substances 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 17
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 17
- 239000000985 reactive dye Substances 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- 229910000029 sodium carbonate Inorganic materials 0.000 description 14
- 235000017550 sodium carbonate Nutrition 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
- 229920000742 Cotton Polymers 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920003043 Cellulose fiber Polymers 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- PIAMYXAFTDDKMQ-UHFFFAOYSA-N n'-amino-n-hydrazinylidenemethanimidamide;copper Chemical compound [Cu].NN=CN=NN PIAMYXAFTDDKMQ-UHFFFAOYSA-N 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- 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 8
- 159000000000 sodium salts Chemical class 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000003792 electrolyte Substances 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 210000004243 sweat Anatomy 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 description 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000004061 bleaching Methods 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000001431 2-methylbenzaldehyde Substances 0.000 description 3
- SFUJTLIHMWZDTL-UHFFFAOYSA-N 3-acetamido-5-amino-4-hydroxybenzenesulfonic acid Chemical compound CC(=O)NC1=CC(S(O)(=O)=O)=CC(N)=C1O SFUJTLIHMWZDTL-UHFFFAOYSA-N 0.000 description 3
- HIMMCCJEMMCUJS-UHFFFAOYSA-N 4-fluorotriazine Chemical class FC1=CC=NN=N1 HIMMCCJEMMCUJS-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000005236 alkanoylamino group Chemical group 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000001694 spray drying Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 description 2
- DVJOCGDWMPJDIH-UHFFFAOYSA-N 2-amino-4-butylsulfonylphenol Chemical compound CCCCS(=O)(=O)C1=CC=C(O)C(N)=C1 DVJOCGDWMPJDIH-UHFFFAOYSA-N 0.000 description 2
- UPJVUFCLBYQKFH-UHFFFAOYSA-N 2-amino-4-ethylsulfonylphenol Chemical compound CCS(=O)(=O)C1=CC=C(O)C(N)=C1 UPJVUFCLBYQKFH-UHFFFAOYSA-N 0.000 description 2
- TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 description 2
- SFLMBHYNCSYPOO-UHFFFAOYSA-N 2-amino-4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C(N)=C1 SFLMBHYNCSYPOO-UHFFFAOYSA-N 0.000 description 2
- HCPJEHJGFKWRFM-UHFFFAOYSA-N 2-amino-5-methylphenol Chemical compound CC1=CC=C(N)C(O)=C1 HCPJEHJGFKWRFM-UHFFFAOYSA-N 0.000 description 2
- IXGURTAEYOZRDF-UHFFFAOYSA-N 2-amino-5-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(N)C(O)=C1 IXGURTAEYOZRDF-UHFFFAOYSA-N 0.000 description 2
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 2
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 2
- OYDYLEBWNAYHMY-UHFFFAOYSA-N 2-hydrazinyl-4-sulfobenzoic acid Chemical compound NNC1=CC(S(O)(=O)=O)=CC=C1C(O)=O OYDYLEBWNAYHMY-UHFFFAOYSA-N 0.000 description 2
- WYVGYYIZXPXHAZ-UHFFFAOYSA-N 3-Chlor-4-methoxy-benzaldehyd Natural products COC1=CC=C(C=O)C=C1Cl WYVGYYIZXPXHAZ-UHFFFAOYSA-N 0.000 description 2
- GXINVVNDQWECJP-UHFFFAOYSA-N 3-amino-2-hydroxy-5-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(O)C(S(O)(=O)=O)=C1 GXINVVNDQWECJP-UHFFFAOYSA-N 0.000 description 2
- ZLTOYIGWKLTQBJ-UHFFFAOYSA-N 3-amino-2-hydroxy-5-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(C(O)=O)=C1O ZLTOYIGWKLTQBJ-UHFFFAOYSA-N 0.000 description 2
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 2
- BLKRLPPJSAMUNN-UHFFFAOYSA-N 3-amino-4-hydroxy-n,n-dimethylbenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(O)C(N)=C1 BLKRLPPJSAMUNN-UHFFFAOYSA-N 0.000 description 2
- NFNLMGYLSDEJKS-UHFFFAOYSA-N 3-amino-4-hydroxy-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(O)C(N)=C1 NFNLMGYLSDEJKS-UHFFFAOYSA-N 0.000 description 2
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 2
- YCTAOQGPWNTYJE-UHFFFAOYSA-N 3-amino-5-chloro-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC(S(O)(=O)=O)=C1O YCTAOQGPWNTYJE-UHFFFAOYSA-N 0.000 description 2
- QGTXBWMKRGHPDD-UHFFFAOYSA-N 3-amino-5-chloro-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(Cl)=C1O QGTXBWMKRGHPDD-UHFFFAOYSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 2
- HCEYSAVOFADVMD-UHFFFAOYSA-N 4-amino-3-hydroxybenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1O HCEYSAVOFADVMD-UHFFFAOYSA-N 0.000 description 2
- JLMVULREWBLCCD-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 JLMVULREWBLCCD-UHFFFAOYSA-N 0.000 description 2
- HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 2
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 230000001180 sulfating effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4407—Formazane dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3705789.8 | 1987-02-24 | ||
| DE19873705789 DE3705789A1 (de) | 1987-02-24 | 1987-02-24 | Kupferkomplex-formazan-verbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63225663A JPS63225663A (ja) | 1988-09-20 |
| JP2598065B2 true JP2598065B2 (ja) | 1997-04-09 |
Family
ID=6321594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63038790A Expired - Lifetime JP2598065B2 (ja) | 1987-02-24 | 1988-02-23 | ホルマザン―銅錯化合物および該化合物を染料として使用する方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4906736A (en, 2012) |
| EP (1) | EP0280139B1 (en, 2012) |
| JP (1) | JP2598065B2 (en, 2012) |
| KR (1) | KR960003082B1 (en, 2012) |
| BR (1) | BR8800752A (en, 2012) |
| DE (2) | DE3705789A1 (en, 2012) |
| ES (1) | ES2032309T3 (en, 2012) |
| IN (1) | IN168388B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0333656B1 (de) * | 1988-03-17 | 1993-04-28 | Ciba-Geigy Ag | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| DE3903455A1 (de) * | 1989-02-06 | 1990-08-09 | Hoechst Ag | Kupferkomplex-formazanverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| EP0402318B1 (de) | 1989-06-08 | 1994-04-20 | Ciba-Geigy Ag | Verfahren zur Herstellung von faserreaktiven Formazanverbindungen |
| ES2071076T3 (es) * | 1989-07-24 | 1995-06-16 | Ciba Geigy Ag | Colorantes formazano reactivos con las fibras, procedimiento para su obtencion y uso de los mismos. |
| ES2054316T3 (es) * | 1989-07-24 | 1994-08-01 | Ciba Geigy Ag | Colorantes de formazano reactivos con las fibras, procedimiento para su obtencion, y su empleo. |
| DE4219421A1 (de) * | 1992-06-13 | 1993-12-16 | Basf Ag | Verfahren zur Herstellung von faserreaktiven Formazanfarbstoffen sowie Aminophenole |
| DE4221543C1 (en, 2012) * | 1992-07-01 | 1993-08-26 | Basf Ag, 6700 Ludwigshafen, De | |
| DE102006003864A1 (de) * | 2006-01-27 | 2007-08-02 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Wasserlösliche faserreaktive Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung |
| WO2017129297A1 (en) | 2016-01-29 | 2017-08-03 | Huntsman Advanced Materials (Switzerland) Gmbh | Fibre reactive formazan dyes, their preparation and their use |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH627206A5 (en, 2012) * | 1978-07-06 | 1981-12-31 | Ciba Geigy Ag | |
| JPS6018357B2 (ja) * | 1979-06-20 | 1985-05-09 | 住友化学工業株式会社 | セルロ−ズ系繊維の染色法 |
| JPS5915451A (ja) * | 1982-07-19 | 1984-01-26 | Sumitomo Chem Co Ltd | 金属ホルマザン化合物、その製造法およびそれを用いる繊維材料の染色方法 |
| EP0214093B1 (de) * | 1985-08-14 | 1990-01-03 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
-
1987
- 1987-02-24 DE DE19873705789 patent/DE3705789A1/de not_active Withdrawn
-
1988
- 1988-02-01 IN IN86/CAL/88A patent/IN168388B/en unknown
- 1988-02-15 DE DE8888102164T patent/DE3867864D1/de not_active Expired - Fee Related
- 1988-02-15 ES ES198888102164T patent/ES2032309T3/es not_active Expired - Lifetime
- 1988-02-15 EP EP88102164A patent/EP0280139B1/de not_active Expired - Lifetime
- 1988-02-23 US US07/159,188 patent/US4906736A/en not_active Expired - Lifetime
- 1988-02-23 BR BR8800752A patent/BR8800752A/pt not_active Application Discontinuation
- 1988-02-23 JP JP63038790A patent/JP2598065B2/ja not_active Expired - Lifetime
- 1988-02-24 KR KR1019880001896A patent/KR960003082B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3867864D1 (de) | 1992-03-05 |
| DE3705789A1 (de) | 1988-09-01 |
| JPS63225663A (ja) | 1988-09-20 |
| KR880009974A (ko) | 1988-10-06 |
| EP0280139A2 (de) | 1988-08-31 |
| EP0280139A3 (en) | 1989-02-08 |
| BR8800752A (pt) | 1988-10-04 |
| US4906736A (en) | 1990-03-06 |
| EP0280139B1 (de) | 1992-01-22 |
| ES2032309T3 (es) | 1993-02-01 |
| KR960003082B1 (ko) | 1996-03-04 |
| IN168388B (en, 2012) | 1991-03-23 |
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