CA1108127A - Fibre-reactive azo dyes, processes for their production and use thereof - Google Patents

Fibre-reactive azo dyes, processes for their production and use thereof

Info

Publication number: CA1108127A
Authority: CA; Canada
Prior art keywords: formula; hydrogen; carbon atoms; carbamoyl; alkyl
Prior art date: 1977-11-04
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

CA315,198A

Other languages

English (en)

French (fr)

Inventor

Rainer Begrich

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.)

BASF Schweiz AG

Original Assignee

Individual

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.)

1977-11-04

Filing date

1978-10-31

Publication date

1981-09-01

1978-10-31 Application filed by Individual filed Critical Individual

1981-09-01 Application granted granted Critical

1981-09-01 Publication of CA1108127A publication Critical patent/CA1108127A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 19
230000008569 process Effects 0.000 title claims description 14
239000000987 azo dye Substances 0.000 title claims description 9
238000004519 manufacturing process Methods 0.000 title claims description 5
-1 sulfo, carboxyl Chemical group 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
239000000985 reactive dye Substances 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
125000001424 substituent group Chemical group 0.000 claims abstract description 7
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
235000013350 formula milk Nutrition 0.000 claims description 71
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 18
230000008878 coupling Effects 0.000 claims description 17
238000010168 coupling process Methods 0.000 claims description 17
238000005859 coupling reaction Methods 0.000 claims description 17
238000004043 dyeing Methods 0.000 claims description 11
238000009833 condensation Methods 0.000 claims description 9
230000005494 condensation Effects 0.000 claims description 9
UGEHFOSBNBEWMP-UHFFFAOYSA-N 2,3-diaminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1N UGEHFOSBNBEWMP-UHFFFAOYSA-N 0.000 claims description 7
239000007859 condensation product Substances 0.000 claims description 7
150000008049 diazo compounds Chemical class 0.000 claims description 7
SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 claims description 6
JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical group NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 claims description 5
238000007127 saponification reaction Methods 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 5
GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical group C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
229940076134 benzene Drugs 0.000 abstract description 4
239000002253 acid Substances 0.000 description 31
239000000243 solution Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
239000000975 dye Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
229920000742 Cotton Polymers 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
230000007935 neutral effect Effects 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
229940083608 sodium hydroxide Drugs 0.000 description 10
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000725 suspension Substances 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000003513 alkali Substances 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000004744 fabric Substances 0.000 description 3
235000019233 fast yellow AB Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
LKUPJDFPVKUQFF-UHFFFAOYSA-N 2-[(2-aminoacetyl)amino]benzenesulfonic acid Chemical compound NCC(=O)NC1=CC=CC=C1S(O)(=O)=O LKUPJDFPVKUQFF-UHFFFAOYSA-N 0.000 description 2
JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
YUNBHHWDQDGWHC-UHFFFAOYSA-N 6-aminonaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=CC(N)=CC=C21 YUNBHHWDQDGWHC-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000003599 detergent Substances 0.000 description 2
150000004985 diamines Chemical class 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
229960000443 hydrochloric acid Drugs 0.000 description 2
235000011167 hydrochloric acid Nutrition 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
PQSTUAGLUWYWEW-UHFFFAOYSA-N (2-hydroxy-4-methyl-6-oxo-1h-pyridin-3-yl)methanesulfonic acid Chemical compound CC1=CC(O)=NC(O)=C1CS(O)(=O)=O PQSTUAGLUWYWEW-UHFFFAOYSA-N 0.000 description 1
LITZXSLYAKVNBM-UHFFFAOYSA-N (5-carbamoyl-2-hydroxy-4-methyl-6-oxo-1h-pyridin-3-yl)methanesulfonic acid Chemical compound CC1=C(CS(O)(=O)=O)C(O)=NC(O)=C1C(N)=O LITZXSLYAKVNBM-UHFFFAOYSA-N 0.000 description 1
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
CYCGXYKRUBKWHT-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)piperazine;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=C(Cl)C(N2CCNCC2)=C1 CYCGXYKRUBKWHT-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
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 1
VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-N 0.000 description 1
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 1
YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 1
YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
OTEBTSPEXWSPLD-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC(=O)NC(O)=C1C(N)=O OTEBTSPEXWSPLD-UHFFFAOYSA-N 0.000 description 1
MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
UCTREIIEJSFTDI-UHFFFAOYSA-N 3-aminonaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1 UCTREIIEJSFTDI-UHFFFAOYSA-N 0.000 description 1
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 1
RKDUVPVDHFMLPC-UHFFFAOYSA-N 4,6-difluorotriazine Chemical class FC1=CC(F)=NN=N1 RKDUVPVDHFMLPC-UHFFFAOYSA-N 0.000 description 1
RXNKCIBVUNMMAD-UHFFFAOYSA-N 4-[9-(4-amino-3-fluorophenyl)fluoren-9-yl]-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1(C=2C=C(F)C(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RXNKCIBVUNMMAD-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
KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 1
GFPQSWFFPRQEHH-UHFFFAOYSA-N 7-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(N)=CC2=C1S(O)(=O)=O GFPQSWFFPRQEHH-UHFFFAOYSA-N 0.000 description 1
CMOLPZZVECHXKN-UHFFFAOYSA-N 7-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC=C21 CMOLPZZVECHXKN-UHFFFAOYSA-N 0.000 description 1
OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 description 1
101100338892 Arabidopsis thaliana HHO3 gene Proteins 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
229910006069 SO3H Inorganic materials 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
FPVGTPBMTFTMRT-UHFFFAOYSA-L disodium;2-amino-5-[(4-sulfonatophenyl)diazenyl]benzenesulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-UHFFFAOYSA-L 0.000 description 1
239000002270 dispersing agent Substances 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
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 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
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000010985 leather Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000009980 pad dyeing Methods 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- C09B62/08—Azo dyes
- C09B62/085—Monoazo dyes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CA315,198A 1977-11-04 1978-10-31 Fibre-reactive azo dyes, processes for their production and use thereof Expired CA1108127A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
LU78455A LU78455A1 (de)	1977-11-04	1977-11-04	Faserreaktive azofarbstoffe,deren herstellung und verwendung
LU78455		1977-11-04

Publications (1)

Publication Number	Publication Date
CA1108127A true CA1108127A (en)	1981-09-01

Family

ID=19728753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA315,198A Expired CA1108127A (en)	1977-11-04	1978-10-31	Fibre-reactive azo dyes, processes for their production and use thereof

Country Status (12)

Country	Link
JP (1)	JPS5473829A (cs)
BE (1)	BE871750A (cs)
BR (1)	BR7807215A (cs)
CA (1)	CA1108127A (cs)
CH (1)	CH637986A5 (cs)
CS (1)	CS197331B2 (cs)
DE (1)	DE2847658A1 (cs)
ES (1)	ES474787A1 (cs)
FR (1)	FR2407965A1 (cs)
GB (1)	GB2009775B (cs)
IT (1)	IT7851742A0 (cs)
LU (1)	LU78455A1 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0122881B1 (de) *	1983-04-15	1986-08-13	Ciba-Geigy Ag	Reaktivfarbstoffe, deren Herstellung und Verwendung
DE3542001A1 (de) *	1985-11-28	1987-06-04	Bayer Ag	Reaktivfarbstoffe

1977
- 1977-11-04 LU LU78455A patent/LU78455A1/de unknown
1978
- 1978-10-11 CH CH1055078A patent/CH637986A5/de not_active IP Right Cessation
- 1978-10-31 CA CA315,198A patent/CA1108127A/en not_active Expired
- 1978-11-01 BR BR7807215A patent/BR7807215A/pt unknown
- 1978-11-02 JP JP13568878A patent/JPS5473829A/ja active Pending
- 1978-11-02 FR FR7831087A patent/FR2407965A1/fr active Granted
- 1978-11-02 DE DE19782847658 patent/DE2847658A1/de not_active Withdrawn
- 1978-11-02 IT IT7851742A patent/IT7851742A0/it unknown
- 1978-11-03 ES ES474787A patent/ES474787A1/es not_active Expired
- 1978-11-03 CS CS787191A patent/CS197331B2/cs unknown
- 1978-11-03 GB GB7843092A patent/GB2009775B/en not_active Expired
- 1978-11-03 BE BE191523A patent/BE871750A/xx unknown

Also Published As

Publication number	Publication date
BE871750A (fr)	1979-05-03
CH637986A5 (de)	1983-08-31
FR2407965A1 (fr)	1979-06-01
ES474787A1 (es)	1979-09-01
GB2009775B (en)	1982-06-09
JPS5473829A (en)	1979-06-13
GB2009775A (en)	1979-06-20
LU78455A1 (de)	1979-06-13
DE2847658A1 (de)	1979-05-10
CS197331B2 (en)	1980-04-30
IT7851742A0 (it)	1978-11-02
FR2407965B1 (cs)	1983-04-01
BR7807215A (pt)	1979-06-12

Legal Events

Date	Code	Title	Description
1998-09-01	MKEX	Expiry

Publication	Publication Date	Title
US4754023A (en)	1988-06-28	Reactive dyestuffs comprising a triazine moiety and a vinylsulfonyl moiety both being linked by a substituted alkylene bridge member
US4649193A (en)	1987-03-10	Water-soluble dyestuffs containing fibre-reactive groups of the vinylsulfone series and the fluoro-s-triazinyl-amino series
CA1161034A (en)	1984-01-24	Reactive dyes, processes for their manufacture and use thereof
JPS603109B2 (ja)	1985-01-25	新規な反応性染料及びその製法
KR910002517B1 (ko)	1991-04-23	실크 또는 함실크 혼방물의 염색방법
JPS6048546B2 (ja)	1985-10-28	繊維反応性染料およびその製法
JPH02132160A (ja)	1990-05-21	反応染料、その製造方法、及びその使用
US4912244A (en)	1990-03-27	Vinylsulfonylalkylamino-alkylamines as intermediates for the preparation of fiber-reactive dyes
US3966705A (en)	1976-06-29	Disulfo naphthalene containing fiber-reactive tetrazo dyes
US5747657A (en)	1998-05-05	Reactive monoazo dyestuffs and the processes in which they are produced
US3518245A (en)	1970-06-30	Azo dyestuffs and their metal complex compounds
KR100293044B1 (ko)	2001-11-22	반응성염료,이들의제조방법및이들을사용한염색또는날염방법_
JPS58164650A (ja)	1983-09-29	反応染料とその製造法および用法
CS198103B2 (en)	1980-05-30	Process for preparing dyes reactive with fiber
US4128544A (en)	1978-12-05	Copper complexes of substituted sulfophenyl-azo-phenyl-azo-naphthalene sulfonic acids containing a heterocyclic fiber-reactive group
CA1108127A (en)	1981-09-01	Fibre-reactive azo dyes, processes for their production and use thereof
JPS6136367A (ja)	1986-02-21	反応性染料
US5847111A (en)	1998-12-08	Aluminum phthalocyanine reactive dyes
JPS6375067A (ja)	1988-04-05	反応染料とその製造方法と使用
GB1566814A (en)	1980-05-08	Fibrereactive azo dyestuffs containing a fluorotriazine residue their manufacture and use
CA1111025A (en)	1981-10-20	Azo dyes, processes for their production and use thereof
JPH0711158A (ja)	1995-01-13	反応性染料
US4129736A (en)	1978-12-12	Triazinyl-antraquinone dyestuffs
US4929719A (en)	1990-05-29	Fiber-reactive dyes containing an aniline radical which carries two different vinylsulfonyl moieties
JPH01158076A (ja)	1989-06-21	反応染料、その製造方法および使用