JPS603108B2 - 繊維反応性フタロシアニン−アゾ染料の製法 - Google Patents

繊維反応性フタロシアニン−アゾ染料の製法

Info

Publication number: JPS603108B2
Authority: JP; Japan
Prior art keywords: group; formula; carbon atoms; amine; substituted
Prior art date: 1976-04-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP52042734A

Other languages

English (en)

Japanese (ja)

Other versions

JPS52127925A (en

Inventor

ロルフ・ミユ−レル

ヨアヒム・リプカ

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

Sanofi Aventis Deutschland GmbH

Original Assignee

Cassella AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1976-04-17

Filing date

1977-04-15

Publication date

1985-01-25

1977-04-15 Application filed by Cassella AG filed Critical Cassella AG

1977-10-27 Publication of JPS52127925A publication Critical patent/JPS52127925A/ja

1985-01-25 Publication of JPS603108B2 publication Critical patent/JPS603108B2/ja

Status Expired legal-status Critical Current

Links

239000000987 azo dye Substances 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims description 7
-1 phthalocyanine amine Chemical class 0.000 claims description 168
125000004432 carbon atom Chemical group C* 0.000 claims description 150
150000001412 amines Chemical class 0.000 claims description 87
125000000217 alkyl group Chemical group 0.000 claims description 61
238000000034 method Methods 0.000 claims description 49
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
125000003545 alkoxy group Chemical group 0.000 claims description 35
125000001424 substituent group Chemical group 0.000 claims description 35
125000003118 aryl group Chemical group 0.000 claims description 32
238000005859 coupling reaction Methods 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
239000000975 dye Substances 0.000 claims description 27
230000008878 coupling Effects 0.000 claims description 26
238000010168 coupling process Methods 0.000 claims description 26
239000000126 substance Substances 0.000 claims description 24
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims description 22
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 20
150000001989 diazonium salts Chemical class 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000000547 substituted alkyl group Chemical group 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 15
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 14
125000005236 alkanoylamino group Chemical group 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000001931 aliphatic group Chemical group 0.000 claims description 12
239000003513 alkali Substances 0.000 claims description 12
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 9
125000004957 naphthylene group Chemical group 0.000 claims description 9
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
WDEQGLDWZMIMJM-UHFFFAOYSA-N benzyl 4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate Chemical group OCC1CC(O)CN1C(=O)OCC1=CC=CC=C1 WDEQGLDWZMIMJM-UHFFFAOYSA-N 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
230000007935 neutral effect Effects 0.000 claims description 6
125000005650 substituted phenylene group Chemical group 0.000 claims description 6
229910052751 metal Inorganic materials 0.000 claims description 5
239000002184 metal Substances 0.000 claims description 5
125000000542 sulfonic acid group Chemical group 0.000 claims description 5
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000005760 substituted naphthylene group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
239000012736 aqueous medium Substances 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
125000000129 anionic group Chemical group 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
150000003443 succinic acid derivatives Chemical class 0.000 claims 7
150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 4
125000001183 hydrocarbyl group Chemical group 0.000 claims 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
125000000623 heterocyclic group Chemical group 0.000 claims 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 description 56
239000000243 solution Substances 0.000 description 35
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
239000007859 condensation product Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
239000000203 mixture Substances 0.000 description 12
PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 11
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 10
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 10
238000007127 saponification reaction Methods 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 8
150000002430 hydrocarbons Chemical group 0.000 description 8
230000002378 acidificating effect Effects 0.000 description 7
229910052759 nickel Inorganic materials 0.000 description 7
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 6
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 6
150000004985 diamines Chemical class 0.000 description 6
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 6
235000010288 sodium nitrite Nutrition 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
239000001913 cellulose Substances 0.000 description 5
229920002678 cellulose Polymers 0.000 description 5
239000000463 material Substances 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000000985 reactive dye Substances 0.000 description 5
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 4
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 4
JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000002860 competitive effect Effects 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
229940018564 m-phenylenediamine Drugs 0.000 description 4
JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000047 product Substances 0.000 description 4
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
SENOENRYIMUSNW-UHFFFAOYSA-N 1,4-diaminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(N)=CC(S(O)(=O)=O)=C(N)C2=C1 SENOENRYIMUSNW-UHFFFAOYSA-N 0.000 description 3
QBOLYQPBEJEHQB-UHFFFAOYSA-N 1,5-diaminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1N QBOLYQPBEJEHQB-UHFFFAOYSA-N 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
RKWKDLKDFWIJMD-UHFFFAOYSA-N 3,7-diaminonaphthalene-1-sulfonic acid Chemical compound C1=C(N)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 RKWKDLKDFWIJMD-UHFFFAOYSA-N 0.000 description 3
YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 3
BFWYZZPDZZGSLJ-UHFFFAOYSA-N 4-(aminomethyl)aniline Chemical compound NCC1=CC=C(N)C=C1 BFWYZZPDZZGSLJ-UHFFFAOYSA-N 0.000 description 3
WVRFOWUCHMXFRU-UHFFFAOYSA-N 5-amino-2-(aminomethyl)benzenesulfonic acid Chemical compound NCC1=CC=C(N)C=C1S(O)(=O)=O WVRFOWUCHMXFRU-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
QKZIVVMOMKTVIK-UHFFFAOYSA-N anilinomethanesulfonic acid Chemical compound OS(=O)(=O)CNC1=CC=CC=C1 QKZIVVMOMKTVIK-UHFFFAOYSA-N 0.000 description 3
239000004305 biphenyl Substances 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
239000003431 cross linking reagent Substances 0.000 description 3
238000006193 diazotization reaction Methods 0.000 description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
229950008177 disulfamide Drugs 0.000 description 3
229960002449 glycine Drugs 0.000 description 3
235000013905 glycine and its sodium salt Nutrition 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000005185 salting out Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
BBDGNUHKKJPLRG-UHFFFAOYSA-N 1,4-diaminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=CC(C(O)=O)=C(N)C2=C1 BBDGNUHKKJPLRG-UHFFFAOYSA-N 0.000 description 2
CVXIRTCLVZZRKV-UHFFFAOYSA-N 1,4-dichlorophthalazine-6-carbonyl chloride Chemical compound ClC1=NN=C(Cl)C2=CC(C(=O)Cl)=CC=C21 CVXIRTCLVZZRKV-UHFFFAOYSA-N 0.000 description 2
BSZXAFXFTLXUFV-UHFFFAOYSA-N 1-phenylethylbenzene Chemical compound C=1C=CC=CC=1C(C)C1=CC=CC=C1 BSZXAFXFTLXUFV-UHFFFAOYSA-N 0.000 description 2
ODMHNISSKQSEFM-UHFFFAOYSA-N 2,3-dichloroquinoxaline-5-carbonyl chloride Chemical compound ClC1=C(Cl)N=C2C(C(=O)Cl)=CC=CC2=N1 ODMHNISSKQSEFM-UHFFFAOYSA-N 0.000 description 2
NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 2
VZLILCJJQCJIRS-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=C2N=C(Cl)C(Cl)=NC2=C1 VZLILCJJQCJIRS-UHFFFAOYSA-N 0.000 description 2
GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 2
BQWFGJYQYFBDFD-UHFFFAOYSA-N 2,4-diamino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC(S(O)(=O)=O)=C(N)C=C1N BQWFGJYQYFBDFD-UHFFFAOYSA-N 0.000 description 2
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 2
QGNJPFLIBOTDKU-UHFFFAOYSA-N 2,5-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C(S(O)(=O)=O)=C1 QGNJPFLIBOTDKU-UHFFFAOYSA-N 0.000 description 2
NUYJCMGJLNVOML-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NC(Cl)=N1 NUYJCMGJLNVOML-UHFFFAOYSA-N 0.000 description 2
KRAWOYVPVQRUAE-UHFFFAOYSA-N 2-(4-aminoanilino)acetic acid Chemical compound NC1=CC=C(NCC(O)=O)C=C1 KRAWOYVPVQRUAE-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
PKKGGWLTUCMSSD-UHFFFAOYSA-N 3,5-diamino-2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=C(N)C(C)=C(S(O)(=O)=O)C(C)=C1N PKKGGWLTUCMSSD-UHFFFAOYSA-N 0.000 description 2
BRAAWLKLYJBAPT-UHFFFAOYSA-N 3,5-diamino-2,4-diethylbenzenesulfonic acid Chemical compound CCC1=C(N)C=C(S(O)(=O)=O)C(CC)=C1N BRAAWLKLYJBAPT-UHFFFAOYSA-N 0.000 description 2
OCDSFJBMDKBLRJ-UHFFFAOYSA-N 3,5-diamino-2-chlorobenzenesulfonic acid Chemical compound NC1=CC(N)=C(Cl)C(S(O)(=O)=O)=C1 OCDSFJBMDKBLRJ-UHFFFAOYSA-N 0.000 description 2
AFUHLZJMSIKUOK-UHFFFAOYSA-N 3,5-diamino-2-methylbenzenesulfonic acid Chemical compound CC1=C(N)C=C(N)C=C1S(O)(=O)=O AFUHLZJMSIKUOK-UHFFFAOYSA-N 0.000 description 2
IPQWXJDRMKGSFI-UHFFFAOYSA-N 3,5-diamino-4-methylbenzenesulfonic acid Chemical compound CC1=C(N)C=C(S(O)(=O)=O)C=C1N IPQWXJDRMKGSFI-UHFFFAOYSA-N 0.000 description 2
UGKIAJNNQAMSHX-UHFFFAOYSA-N 3,6-dichloropyridazine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NN=C1Cl UGKIAJNNQAMSHX-UHFFFAOYSA-N 0.000 description 2
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
DKIDDWUQCDKOEN-UHFFFAOYSA-N 4,5-diaminonaphthalene-1-sulfonic acid Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1S(O)(=O)=O DKIDDWUQCDKOEN-UHFFFAOYSA-N 0.000 description 2
NKIMEOGXUQUZLR-UHFFFAOYSA-N 4,8-diaminonaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1N NKIMEOGXUQUZLR-UHFFFAOYSA-N 0.000 description 2
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MSDFMCHKCAUTSC-UHFFFAOYSA-N 4,7-diaminonaphthalene-1-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C2=CC(N)=CC=C21 MSDFMCHKCAUTSC-UHFFFAOYSA-N 0.000 description 1
KKSYUUWNMBUBQG-UHFFFAOYSA-N 4,8-diaminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1N KKSYUUWNMBUBQG-UHFFFAOYSA-N 0.000 description 1
ABSXMLODUTXQDJ-UHFFFAOYSA-N 4-(4-sulfophenyl)benzenesulfonic acid Chemical group C1=CC(S(=O)(=O)O)=CC=C1C1=CC=C(S(O)(=O)=O)C=C1 ABSXMLODUTXQDJ-UHFFFAOYSA-N 0.000 description 1
DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
HYKDWGUFDOYDGV-UHFFFAOYSA-N 4-anilinobenzenesulfonic acid Chemical compound C1=CC(S(=O)(=O)O)=CC=C1NC1=CC=CC=C1 HYKDWGUFDOYDGV-UHFFFAOYSA-N 0.000 description 1
ZRWALVBIVUPROW-UHFFFAOYSA-N 4-chloro-2,6-bis(methylsulfonyl)pyrimidine-5-carbonyl chloride Chemical compound CS(=O)(=O)C1=NC(Cl)=C(C(Cl)=O)C(S(C)(=O)=O)=N1 ZRWALVBIVUPROW-UHFFFAOYSA-N 0.000 description 1
POWFLCAWHSPOHP-UHFFFAOYSA-N 4-chloro-2-methylpyrimidine-5-carbonyl chloride Chemical compound CC1=NC=C(C(Cl)=O)C(Cl)=N1 POWFLCAWHSPOHP-UHFFFAOYSA-N 0.000 description 1
VXMQMLQIYFEILO-UHFFFAOYSA-N 4-chloro-2-methylsulfonylpyrimidine-5-carbonyl chloride Chemical compound CS(=O)(=O)C1=NC=C(C(Cl)=O)C(Cl)=N1 VXMQMLQIYFEILO-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
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VYHPXGUVWWAOAK-UHFFFAOYSA-N 4-n-(3-chlorobutyl)benzene-1,4-diamine Chemical compound CC(Cl)CCNC1=CC=C(N)C=C1 VYHPXGUVWWAOAK-UHFFFAOYSA-N 0.000 description 1
IELAVJDOWOPAMD-UHFFFAOYSA-N 4-n-hexylbenzene-1,4-diamine Chemical compound CCCCCCNC1=CC=C(N)C=C1 IELAVJDOWOPAMD-UHFFFAOYSA-N 0.000 description 1
SLGPNZKFEWLKAB-UHFFFAOYSA-N 5-amino-2-(3-aminopropyl)benzenesulfonic acid Chemical compound NCCCC1=CC=C(N)C=C1S(O)(=O)=O SLGPNZKFEWLKAB-UHFFFAOYSA-N 0.000 description 1
REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 description 1
BATOZQRGECFVTF-UHFFFAOYSA-N 5-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(C)=CC=CC2=C1S(O)(=O)=O BATOZQRGECFVTF-UHFFFAOYSA-N 0.000 description 1
BNDRECGBDISUAI-UHFFFAOYSA-N 6-(2-phenylethenyl)cyclohexa-2,4-diene-1,1-disulfonic acid Chemical compound OS(=O)(=O)C1(S(O)(=O)=O)C=CC=CC1C=CC1=CC=CC=C1 BNDRECGBDISUAI-UHFFFAOYSA-N 0.000 description 1
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BPSXAFIVZFIWQX-UHFFFAOYSA-N 6-chloro-2-methylsulfonylpyrimidine-4-carbonyl chloride Chemical compound CS(=O)(=O)C1=NC(Cl)=CC(C(Cl)=O)=N1 BPSXAFIVZFIWQX-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
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VUVIOJKNCGURFR-UHFFFAOYSA-N C(C)(C)OC=1C(=NN=NC=1Cl)Cl Chemical compound C(C)(C)OC=1C(=NN=NC=1Cl)Cl VUVIOJKNCGURFR-UHFFFAOYSA-N 0.000 description 1
DGXAKRVNQDBVMB-UHFFFAOYSA-N COC=1C(=NN=NC1Cl)Cl Chemical compound COC=1C(=NN=NC1Cl)Cl DGXAKRVNQDBVMB-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
241000219112 Cucumis Species 0.000 description 1
235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
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XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
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238000003436 Schotten-Baumann reaction Methods 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
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FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
208000029650 alcohol withdrawal Diseases 0.000 description 1
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150000004984 aromatic diamines Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
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HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
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239000000872 buffer Substances 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
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125000000950 dibromo group Chemical group Br* 0.000 description 1
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150000002170 ethers Chemical class 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000001046 green dye Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
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238000011534 incubation Methods 0.000 description 1
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239000000178 monomer Substances 0.000 description 1
KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 1
QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
BEPGHZIEOVULBU-UHFFFAOYSA-N n,n'-diethylpropane-1,3-diamine Chemical compound CCNCCCNCC BEPGHZIEOVULBU-UHFFFAOYSA-N 0.000 description 1
CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 1
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
OKBVMLGZPNDWJK-UHFFFAOYSA-N naphthalene-1,4-diamine Chemical compound C1=CC=C2C(N)=CC=C(N)C2=C1 OKBVMLGZPNDWJK-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000004304 potassium nitrite Substances 0.000 description 1
235000010289 potassium nitrite Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
210000001747 pupil Anatomy 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000009938 salting Methods 0.000 description 1
239000013535 sea water Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
235000011008 sodium phosphates Nutrition 0.000 description 1
QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 1
239000004071 soot Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
229910000406 trisodium phosphate Inorganic materials 0.000 description 1
235000019801 trisodium phosphate Nutrition 0.000 description 1
239000010981 turquoise Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/0068—Azodyes dyes containing in the molecule at least one azo group and at least one other chromophore group
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Coloring (AREA)

JP52042734A 1976-04-17 1977-04-15 繊維反応性フタロシアニン−アゾ染料の製法 Expired JPS603108B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE26171266		1976-04-17
DE2617126A DE2617126C2 (de)	1976-04-17	1976-04-17	Verfahren zur Herstellung faserreaktiver Phthalocyanin-Azofarbstoffe

Publications (2)

Publication Number	Publication Date
JPS52127925A JPS52127925A (en)	1977-10-27
JPS603108B2 true JPS603108B2 (ja)	1985-01-25

Family

ID=5975729

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP52042734A Expired JPS603108B2 (ja)	1976-04-17	1977-04-15	繊維反応性フタロシアニン−アゾ染料の製法

Country Status (12)

Country	Link
JP (1)	JPS603108B2 (fr)
BE (1)	BE853676A (fr)
BR (1)	BR7702433A (fr)
CA (1)	CA1095899A (fr)
CH (1)	CH626115A5 (fr)
DE (1)	DE2617126C2 (fr)
ES (1)	ES457850A1 (fr)
FR (1)	FR2348254A1 (fr)
GB (1)	GB1559724A (fr)
IN (1)	IN146093B (fr)
IT (1)	IT1143648B (fr)
NL (1)	NL7704037A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01202519A (ja) *	1988-02-08	1989-08-15	Kinugawa Rubber Ind Co Ltd	自動車用ウェザーストリップ構造

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB874355A (en) *	1958-08-07	1961-08-02	Cassella Farbwerke Mainkur Ag	New azo dyestuffs of the phthalocyanine series
FR1242908A (fr) *	1958-08-07	1960-10-07	Cassella Farbwerke Mainkur Ag	Nouveaux colorants azoïques de la série de la phtalocyanine et leur préparation
CH478211A (de) *	1966-04-05	1969-09-15	Bayer Ag	Verfahren zur Herstellung von Azophthalocyanin-Reaktivfarbstoffen

1976
- 1976-04-17 DE DE2617126A patent/DE2617126C2/de not_active Expired
1977
- 1977-04-11 IN IN541/CAL/77A patent/IN146093B/en unknown
- 1977-04-13 NL NL7704037A patent/NL7704037A/xx not_active Application Discontinuation
- 1977-04-15 BE BE176786A patent/BE853676A/fr unknown
- 1977-04-15 JP JP52042734A patent/JPS603108B2/ja not_active Expired
- 1977-04-15 CA CA276,280A patent/CA1095899A/fr not_active Expired
- 1977-04-15 IT IT22532/77A patent/IT1143648B/it active
- 1977-04-15 BR BR7702433A patent/BR7702433A/pt unknown
- 1977-04-15 GB GB15758/77A patent/GB1559724A/en not_active Expired
- 1977-04-15 ES ES457850A patent/ES457850A1/es not_active Expired
- 1977-04-18 FR FR7711588A patent/FR2348254A1/fr active Granted
- 1977-04-18 CH CH478077A patent/CH626115A5/de not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH01202519A (ja) *	1988-02-08	1989-08-15	Kinugawa Rubber Ind Co Ltd	自動車用ウェザーストリップ構造

Also Published As

Publication number	Publication date
IT1143648B (it)	1986-10-22
IN146093B (fr)	1979-02-17
FR2348254B1 (fr)	1980-02-01
JPS52127925A (en)	1977-10-27
BR7702433A (pt)	1978-05-09
DE2617126A1 (de)	1977-10-20
DE2617126C2 (de)	1982-05-27
GB1559724A (en)	1980-01-23
NL7704037A (nl)	1977-10-19
BE853676A (fr)	1977-10-17
CA1095899A (fr)	1981-02-17
CH626115A5 (en)	1981-10-30
FR2348254A1 (fr)	1977-11-10
ES457850A1 (es)	1978-08-01

Publication	Publication Date	Title
JPS603109B2 (ja)	1985-01-25	新規な反応性染料及びその製法
US4754023A (en)	1988-06-28	Reactive dyestuffs comprising a triazine moiety and a vinylsulfonyl moiety both being linked by a substituted alkylene bridge member
JPS5929620B2 (ja)	1984-07-21	新規染料の製法
JPS5855188B2 (ja)	1983-12-08	シンキセルロ−スハンノウセイセンリヨウノセイホウ
JPS602337B2 (ja)	1985-01-21	繊維反応性染料およびその製法
JPS6147177B2 (fr)	1986-10-17
JPH0611869B2 (ja)	1994-02-16	反応染料とその製造方法及び使用
JPS5929615B2 (ja)	1984-07-21	反応性染料の製法
JP2001510875A (ja)	2001-08-07	ピペラジンを含有する反応性染料
JP4012249B2 (ja)	2007-11-21	ネガティブ染料およびネガティブ染料を用いる着色法
US4283331A (en)	1981-08-11	Azo dyes, their preparation and use
US4801693A (en)	1989-01-31	Substituted sulfobenzene and triazine-containing reactive dyes
JPH0244862B2 (fr)	1990-10-05
CA1117938A (fr)	1982-02-09	Teintures reactives, leur preparation et leur emploi
JPS6353231B2 (fr)	1988-10-21
JPS603108B2 (ja)	1985-01-25	繊維反応性フタロシアニン−アゾ染料の製法
JPH02308864A (ja)	1990-12-21	多官能性の繊維―反応性染料
JPS6069164A (ja)	1985-04-19	反応性染料
JPS6058958A (ja)	1985-04-05	ナフトールスルホン酸、その製法およびアゾ染料の製法
JPS6248708B2 (fr)	1987-10-15
KR850001354B1 (ko)	1985-09-21	반응성 염료의 제조방법
EP0592105B1 (fr)	1999-04-14	Colorants réactifs
US6180765B1 (en)	2001-01-30	Reactive diamine-linked azo dyes
JPH0273867A (ja)	1990-03-13	新規な二重アンカー反応性染料及びその中間体としてのベンジル化合物
JPH03195776A (ja)	1991-08-27	反応性染料

JPS603108B2 - 繊維反応性フタロシアニン−アゾ染料の製法 - Google Patents

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