CA1063600A - Fibre-reactive dyes, their manufacture and use - Google Patents

Fibre-reactive dyes, their manufacture and use

Info

Publication number: CA1063600A
Authority: CA; Canada
Prior art keywords: formula; fibre; dye; radical; acid
Prior art date: 1975-03-20
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

CA248,220A

Other languages

English (en)

French (fr)

Inventor

Gert Hegar

Herbert Seiler

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.)

Novartis AG

Original Assignee

Ciba Geigy 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.)

1975-03-20

Filing date

1976-03-19

Publication date

1979-10-02

1975-03-20 Priority claimed from CH357075A external-priority patent/CH615450A5/de

1976-03-19 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-10-02 Application granted granted Critical

1979-10-02 Publication of CA1063600A publication Critical patent/CA1063600A/en

Status Expired legal-status Critical Current

Links

239000000985 reactive dye Substances 0.000 title claims abstract description 31
238000004519 manufacturing process Methods 0.000 title claims description 9
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
125000000217 alkyl group Chemical group 0.000 claims abstract description 19
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
150000004056 anthraquinones Chemical class 0.000 claims abstract description 16
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 abstract description 15
125000004999 nitroaryl group Chemical group 0.000 claims abstract description 13
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
-1 sulpho groups Chemical group 0.000 claims description 80
239000000975 dye Substances 0.000 claims description 69
150000001875 compounds Chemical class 0.000 claims description 38
150000003254 radicals Chemical class 0.000 claims description 36
238000000034 method Methods 0.000 claims description 32
230000008569 process Effects 0.000 claims description 29
238000004043 dyeing Methods 0.000 claims description 19
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 19
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 15
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 15
125000003277 amino group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000005263 alkylenediamine group Chemical group 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 7
239000000047 product Substances 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
239000007864 aqueous solution Substances 0.000 claims description 5
239000000835 fiber Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 4
239000000463 material Substances 0.000 claims description 3
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
BXWKHWCXQWEOBL-UHFFFAOYSA-N 4,6-difluoro-n-phenyl-1,3,5-triazin-2-amine Chemical compound FC1=NC(F)=NC(NC=2C=CC=CC=2)=N1 BXWKHWCXQWEOBL-UHFFFAOYSA-N 0.000 claims 2
229920003043 Cellulose fiber Polymers 0.000 claims 1
239000007859 condensation product Substances 0.000 claims 1
QZGIWPZCWHMVQL-UIYAJPBUSA-N neocarzinostatin chromophore Chemical compound O1[C@H](C)[C@H](O)[C@H](O)[C@@H](NC)[C@H]1O[C@@H]1C/2=C/C#C[C@H]3O[C@@]3([C@@H]3OC(=O)OC3)C#CC\2=C[C@H]1OC(=O)C1=C(O)C=CC2=C(C)C=C(OC)C=C12 QZGIWPZCWHMVQL-UIYAJPBUSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 8
239000002253 acid Substances 0.000 description 87
239000000243 solution Substances 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
229920000742 Cotton Polymers 0.000 description 13
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 12
229910052802 copper Inorganic materials 0.000 description 12
239000010949 copper Substances 0.000 description 12
238000009833 condensation Methods 0.000 description 11
230000005494 condensation Effects 0.000 description 11
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000008878 coupling Effects 0.000 description 9
238000010168 coupling process Methods 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
239000011780 sodium chloride Substances 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
239000004744 fabric Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
230000000875 corresponding effect Effects 0.000 description 6
229940075566 naphthalene Drugs 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 5
125000004442 acylamino group Chemical group 0.000 description 5
239000003513 alkali Substances 0.000 description 5
150000004699 copper complex Chemical class 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
239000011734 sodium Substances 0.000 description 5
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 4
VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
125000004433 nitrogen atom Chemical group N* 0.000 description 4
RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 3
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 3
241001024304 Mino Species 0.000 description 3
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000000732 arylene group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
150000001555 benzenes Chemical class 0.000 description 3
239000000337 buffer salt Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000002843 carboxylic acid group Chemical group 0.000 description 3
229920002678 cellulose Polymers 0.000 description 3
239000001913 cellulose Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052804 chromium Inorganic materials 0.000 description 3
239000011651 chromium Substances 0.000 description 3
150000004985 diamines Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
150000003142 primary aromatic amines Chemical class 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
235000021286 stilbenes Nutrition 0.000 description 3
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical group CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
240000008881 Oenanthe javanica Species 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
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
150000004982 aromatic amines Chemical class 0.000 description 2
150000004984 aromatic diamines Chemical class 0.000 description 2
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
ICIDZHMCYAIUIJ-UHFFFAOYSA-N dinaphthalen-1-yldiazene Chemical compound C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ICIDZHMCYAIUIJ-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000001046 green dye Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
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 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
239000001488 sodium phosphate Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
238000010792 warming Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
210000002268 wool Anatomy 0.000 description 2
FNZSVEHJZREFPF-SSDOTTSWSA-N (2r)-2-pentylbutanedioic acid Chemical compound CCCCC[C@@H](C(O)=O)CC(O)=O FNZSVEHJZREFPF-SSDOTTSWSA-N 0.000 description 1
ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
DVXMQZHDVBYYEQ-UHFFFAOYSA-N 2,4,6-triaminopyridine-3-carbonitrile Chemical compound NC1=CC(N)=C(C#N)C(N)=N1 DVXMQZHDVBYYEQ-UHFFFAOYSA-N 0.000 description 1
NUMXHEUHHRTBQT-AATRIKPKSA-N 2,4-dimethoxy-1-[(e)-2-nitroethenyl]benzene Chemical compound COC1=CC=C(\C=C\[N+]([O-])=O)C(OC)=C1 NUMXHEUHHRTBQT-AATRIKPKSA-N 0.000 description 1
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
OLBAMNTVQSDZQI-UHFFFAOYSA-N 2-(sulfoamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NS(O)(=O)=O OLBAMNTVQSDZQI-UHFFFAOYSA-N 0.000 description 1
WBBFBHOZKCHJHN-UHFFFAOYSA-N 2-amino-1-hydroxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(O)C(N)=CC=C3C(=O)C2=C1 WBBFBHOZKCHJHN-UHFFFAOYSA-N 0.000 description 1
CFCXQQUQLZIZPI-UHFFFAOYSA-N 2-amino-3,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(N)C(S(O)(=O)=O)=C1 CFCXQQUQLZIZPI-UHFFFAOYSA-N 0.000 description 1
OBSIQMZKFXFYLV-UHFFFAOYSA-N 2-amino-3-phenylpropanamide Chemical compound NC(=O)C(N)CC1=CC=CC=C1 OBSIQMZKFXFYLV-UHFFFAOYSA-N 0.000 description 1
VRLPHBSFRWMMPW-UHFFFAOYSA-N 2-amino-4-chloro-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1Cl VRLPHBSFRWMMPW-UHFFFAOYSA-N 0.000 description 1
BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
IIQLVLWFQUUZII-UHFFFAOYSA-N 2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1=CC=C(N)C(C(O)=O)=C1 IIQLVLWFQUUZII-UHFFFAOYSA-N 0.000 description 1
LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 1
LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-UHFFFAOYSA-N 0.000 description 1
MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 1
CMOQNSVFSKVGJA-UHFFFAOYSA-N 2-methoxy-n,5-dimethylaniline Chemical compound CNC1=CC(C)=CC=C1OC CMOQNSVFSKVGJA-UHFFFAOYSA-N 0.000 description 1
NMFFUUFPJJOWHK-UHFFFAOYSA-N 2-phenoxyaniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1 NMFFUUFPJJOWHK-UHFFFAOYSA-N 0.000 description 1
ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
ZFMZSZMUFWRAOG-UHFFFAOYSA-N 3-methoxy-n-methylaniline Chemical compound CNC1=CC=CC(OC)=C1 ZFMZSZMUFWRAOG-UHFFFAOYSA-N 0.000 description 1
ASFAFOSQXBRFMV-LJQANCHMSA-N 3-n-(2-benzyl-1,3-dihydroxypropan-2-yl)-1-n-[(1r)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzene-1,3-dicarboxamide Chemical compound N([C@H](C)C=1C=CC(F)=CC=1)C(=O)C(C=1)=CC(N(C)S(C)(=O)=O)=CC=1C(=O)NC(CO)(CO)CC1=CC=CC=C1 ASFAFOSQXBRFMV-LJQANCHMSA-N 0.000 description 1
PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 1
KOGDFDWINXIWHI-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1 KOGDFDWINXIWHI-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
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical class NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
QUXLCYFNVNNRBE-UHFFFAOYSA-N 6-methylpyridin-2-amine Chemical compound CC1=CC=CC(N)=N1 QUXLCYFNVNNRBE-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
101150034533 ATIC gene Proteins 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000238366 Cephalopoda Species 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
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
241000896693 Disa Species 0.000 description 1
101100536354 Drosophila melanogaster tant gene Proteins 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
241000530268 Lycaena heteronea Species 0.000 description 1
DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
239000011609 ammonium molybdate Substances 0.000 description 1
235000018660 ammonium molybdate Nutrition 0.000 description 1
229940010552 ammonium molybdate Drugs 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
239000001045 blue dye Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004956 cyclohexylene group Chemical group 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000010985 leather Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910000403 monosodium phosphate Inorganic materials 0.000 description 1
235000019799 monosodium phosphate Nutrition 0.000 description 1
PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-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
AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
FDWBUGCBGXWJLC-UHFFFAOYSA-N naphthalen-1-yl(phenyl)diazene Chemical compound C1=CC=CC=C1N=NC1=CC=CC2=CC=CC=C12 FDWBUGCBGXWJLC-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
150000004995 p-toluidines Chemical class 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000010025 steaming Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
239000001043 yellow dye 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CA248,220A 1975-03-20 1976-03-19 Fibre-reactive dyes, their manufacture and use Expired CA1063600A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH357075A CH615450A5 (en)	1975-03-20	1975-03-20	Process for preparing fibre-reactive dyes
CH277876		1976-03-05

Publications (1)

Publication Number	Publication Date
CA1063600A true CA1063600A (en)	1979-10-02

Family

ID=25691377

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,220A Expired CA1063600A (en)	1975-03-20	1976-03-19	Fibre-reactive dyes, their manufacture and use

Country Status (8)

Country	Link
JP (1)	JPS602337B2 (cs)
BR (1)	BR7601712A (cs)
CA (1)	CA1063600A (cs)
CS (1)	CS190527B2 (cs)
DE (1)	DE2611550C2 (cs)
ES (1)	ES446171A1 (cs)
GB (1)	GB1529645A (cs)
IT (1)	IT1061627B (cs)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5984978A (en) *	1997-02-07	1999-11-16	Ciba Specialty Chemicals Corporation	Reactive dyes, their preparation and use
US5989297A (en) *	1995-07-19	1999-11-23	Ciba Specialty Chemicals Corporation	Dye mixtures processes for their preparation and their use

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH617929A5 (cs) *	1976-10-15	1980-06-30	Ciba Geigy Ag
DE2729240C2 (de) *	1977-06-29	1982-07-29	Bayer Ag, 5090 Leverkusen	Azo-Reaktivfarbstoffe
LU78082A1 (de) *	1977-09-06	1979-05-23	Ciba Geigy Ag	Farbstoffe,deren herstellung und verwendung
DE2800147C2 (de) *	1978-01-03	1982-05-06	Basf Ag, 6700 Ludwigshafen	Reaktivfarbstoffe
DE3043915A1 (de) *	1979-12-06	1981-06-11	Sandoz-Patent-GmbH, 7850 Lörrach	Halo-triazinyl verbindungen
US5395925A (en) *	1980-10-07	1995-03-07	Sandoz Ltd.	Asymmetric sulfo group-containing disazo compounds containing two 6-halo-1,3,5-triazinyl groups
CH656629A5 (de) *	1981-08-08	1986-07-15	Sandoz Ag	Tetrakisazoverbindungen mit brueckenglied, verfahren zur herstellung und verwendung.
FR2518106B1 (fr) *	1981-12-11	1986-12-05	Sandoz Sa	Procede de teinture et d'impression de substrats organiques a l'aide de colorants directs bisazoiques
EP0096659B1 (de) *	1982-06-09	1987-04-01	Ciba-Geigy Ag	Verfahren zum Färben oder Bedrucken von textilen Fasermaterialien mit Reaktivfarbstoffen
GB8619914D0 (en) *	1986-08-15	1986-09-24	Ici Plc	Reactive dyes
US5196033A (en) *	1986-08-15	1993-03-23	Imperial Chemical Industries Plc	BIS-azotriazinyl reactive dyes having an N-alkyl-phenylenediamine link for cellulose textiles
EP0302006B1 (de) *	1987-07-03	1992-02-05	Ciba-Geigy Ag	Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
EP0458743A3 (en) *	1990-05-21	1992-10-21	Ciba-Geigy Ag	Reactive dyestuffs, methods of their preparation and use
ES2106070T3 (es) *	1990-09-25	1997-11-01	Ciba Geigy Ag	Colorantes y mezclas de colorantes reactivos con las fibras y utilizacion de los mismos.
EP0495753B1 (de) *	1991-01-16	1997-07-16	Ciba SC Holding AG	Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung
CA2129750C (en) *	1992-03-06	2003-05-06	Jean-Francois Landre	Process for the dyeing of cellulose-containing fibre materials with reactive dyes
DE59408632D1 (de) *	1993-05-24	1999-09-23	Ciba Sc Holding Ag	Verfahren zum Waschen von Drucken oder Färbungen auf cellulosehaltigen Textilmaterialien
TW415961B (en) *	1994-10-14	2000-12-21	Ciba Sc Holding Ag	Fibre-reactive anthraquinone dyes, process for their preparation, and their use
PT832940E (pt) *	1996-09-26	2002-02-28	Ciba Sc Holding Ag	Misturas de corantes, processos para a sua preparacao e sua utilizacao
ATE260955T1 (de)	1999-02-05	2004-03-15	Ciba Sc Holding Ag	Schwarzfärbende tinten und ihre verwendung
US6068667A (en) *	1999-05-05	2000-05-30	Everlight Usa, Inc.	Mixtures of symmetrical and unsymmetrical red reactive dyes
TWI548704B (zh)	2015-05-08	2016-09-11	臺灣永光化學工業股份有限公司	高固著數位紡織印花墨水組成物
DE112017000346T5 (de)	2017-12-28	2019-08-29	Nippon Micrometal Corporation	Bonddraht für Halbleiterbauelement

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1283771A (en) *	1969-01-16	1972-08-02	Ici Ltd	New reactive disazo dyestuffs
GB1288079A (cs) *	1969-07-04	1972-09-06
BE787122A (fr) *	1971-08-04	1973-02-05	Ciba Geigy	Composes azoiques, leur preparation et leur utilisation
GB1439801A (en) *	1973-05-10	1976-06-16	Ici Ltd	Reactive azo dyestuffs

1976
- 1976-03-18 ES ES446171A patent/ES446171A1/es not_active Expired
- 1976-03-18 IT IT4863776A patent/IT1061627B/it active
- 1976-03-18 DE DE19762611550 patent/DE2611550C2/de not_active Expired
- 1976-03-19 CS CS180276A patent/CS190527B2/cs unknown
- 1976-03-19 JP JP3076576A patent/JPS602337B2/ja not_active Expired
- 1976-03-19 GB GB1127276A patent/GB1529645A/en not_active Expired
- 1976-03-19 CA CA248,220A patent/CA1063600A/en not_active Expired
- 1976-03-19 BR BR7601712A patent/BR7601712A/pt unknown

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5989297A (en) *	1995-07-19	1999-11-23	Ciba Specialty Chemicals Corporation	Dye mixtures processes for their preparation and their use
US5984978A (en) *	1997-02-07	1999-11-16	Ciba Specialty Chemicals Corporation	Reactive dyes, their preparation and use

Also Published As

Publication number	Publication date
BR7601712A (pt)	1976-09-21
ES446171A1 (es)	1977-10-16
DE2611550A1 (de)	1976-09-30
DE2611550C2 (de)	1987-03-26
GB1529645A (en)	1978-10-25
CS190527B2 (en)	1979-05-31
IT1061627B (it)	1983-04-30
JPS51119033A (en)	1976-10-19
JPS602337B2 (ja)	1985-01-21

Publication	Publication Date	Title
CA1063600A (en)	1979-10-02	Fibre-reactive dyes, their manufacture and use
CA1077469A (en)	1980-05-13	Reactive dyestuffs, their manufacture and use
CA1087172A (en)	1980-10-07	Dyestuffs, their preparation and use
CA1161034A (en)	1984-01-24	Reactive dyes, processes for their manufacture and use thereof
CA1067894A (en)	1979-12-11	Fibre-reactive dyes, process for their manufacture and use thereof
US4507236A (en)	1985-03-26	Fibre-reactive dyes, containing both chloro and fluoro triazine radicals
US3120507A (en)	1964-02-04	Dyestuffs having a pyrimidine ring substituted by two halogen atoms and by a cyano group in the 5-position
US5149790A (en)	1992-09-22	Bis chlorotriazine reactive dyes containing a benzylamine linking group
CA1099704A (en)	1981-04-21	Dyes, processes for their production and use thereof
CS195257B2 (en)	1980-01-31	Process for preparing azodyes reactive with fibres
CA1052777A (en)	1979-04-17	Tetrareactive disazo dyestuffs, their manufacture and their use
US5410041A (en)	1995-04-25	Bisreactive dyes having a disulfophenylene bridging member
US4082739A (en)	1978-04-04	Fibre-reactive dyestuff containing a bis-triazinylamino
US6365719B1 (en)	2002-04-02	Bridged disazo compounds
US4129736A (en)	1978-12-12	Triazinyl-antraquinone dyestuffs
US6319290B1 (en)	2001-11-20	Fiber-reactive disazo dyestuffs
JPS62283159A (ja)	1987-12-09	水溶性アゾ化合物、その製法及び該化合物を染料として使用する方法
US3666747A (en)	1972-05-30	Azo dyestuffs
KR20010032016A (ko)	2001-04-16	할로벤젠 핵을 함유하는 반응성 염료
EP1380621B1 (en)	2007-08-22	Fibre reactive azo dyes
GB2057479A (en)	1981-04-01	Reactive Dyes
US3639662A (en)	1972-02-01	Azo dyes of the triazine series
US3123594A (en)	1964-03-03	-sojnh-
US4033944A (en)	1977-07-05	Fibre-reactive hydroxycycloalkenyl-halo triazinyl containing dyestuffs
IE57997B1 (en)	1993-06-02	Reactive dyes,process for their preparation and use thereof

CA1063600A - Fibre-reactive dyes, their manufacture and use - Google Patents

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