SU893138A3 - Способ крашени полиамидных материалов металлокомплексным азо- или азометиновым красителем - Google Patents
Способ крашени полиамидных материалов металлокомплексным азо- или азометиновым красителем Download PDFInfo
- Publication number
- SU893138A3 SU893138A3 SU752155211A SU2155211A SU893138A3 SU 893138 A3 SU893138 A3 SU 893138A3 SU 752155211 A SU752155211 A SU 752155211A SU 2155211 A SU2155211 A SU 2155211A SU 893138 A3 SU893138 A3 SU 893138A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- residue
- methyl
- dye
- azo
- Prior art date
Links
- 239000004952 Polyamide Substances 0.000 title claims abstract description 20
- 229920002647 polyamide Polymers 0.000 title claims abstract description 20
- 239000000463 material Substances 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 13
- 238000004043 dyeing Methods 0.000 title claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011651 chromium Substances 0.000 claims abstract description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 6
- 239000010941 cobalt Substances 0.000 claims abstract description 4
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- -1 sulfo- Chemical class 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 229950011260 betanaphthol Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 claims 1
- 229960001413 acetanilide Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 34
- 239000010949 copper Substances 0.000 abstract description 15
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- 229910052802 copper Inorganic materials 0.000 abstract description 7
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract description 4
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 abstract description 4
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001868 cobalt Chemical class 0.000 abstract description 2
- 238000004040 coloring Methods 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 abstract 2
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 229910052727 yttrium Inorganic materials 0.000 abstract 2
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical compound OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 abstract 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical class OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 6
- 125000004442 acylamino group Chemical group 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- UAJUXJSXCLUTNU-UHFFFAOYSA-N pranlukast Chemical compound C=1C=C(OCCCCC=2C=CC=CC=2)C=CC=1C(=O)NC(C=1)=CC=C(C(C=2)=O)C=1OC=2C=1N=NNN=1 UAJUXJSXCLUTNU-UHFFFAOYSA-N 0.000 description 4
- 229960004583 pranlukast Drugs 0.000 description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 3
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910000365 copper sulfate Inorganic materials 0.000 description 3
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- OITQDWKMIPXGFL-UHFFFAOYSA-N 1-hydroxy-2-naphthaldehyde Chemical compound C1=CC=C2C(O)=C(C=O)C=CC2=C1 OITQDWKMIPXGFL-UHFFFAOYSA-N 0.000 description 1
- 150000004782 1-naphthols Chemical class 0.000 description 1
- AOFRNZNXMCOXHP-UHFFFAOYSA-N 2-(2-carboxyphenyl)sulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1C(O)=O AOFRNZNXMCOXHP-UHFFFAOYSA-N 0.000 description 1
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 1
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 1
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- LWUAMROXVQLJKA-UHFFFAOYSA-N 2-amino-3-chlorobenzoic acid Chemical compound NC1=C(Cl)C=CC=C1C(O)=O LWUAMROXVQLJKA-UHFFFAOYSA-N 0.000 description 1
- TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 description 1
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 1
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 description 1
- XPHRTKOIPMJCAR-UHFFFAOYSA-N 2-hydroxybenzaldehyde;3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1.OC1=CC=CC=C1C=O XPHRTKOIPMJCAR-UHFFFAOYSA-N 0.000 description 1
- 150000004786 2-naphthols Chemical class 0.000 description 1
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical class N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
- MQVFKNRZTODPQQ-UHFFFAOYSA-N 4,6-diamino-2-piperidin-1-ylpyridine-3-carbonitrile Chemical compound NC1=CC(N)=C(C#N)C(N2CCCCC2)=N1 MQVFKNRZTODPQQ-UHFFFAOYSA-N 0.000 description 1
- KEGNUIZNBCHWLZ-UHFFFAOYSA-N 5,8-dichloronaphthalen-1-ol Chemical compound C1=CC(Cl)=C2C(O)=CC=CC2=C1Cl KEGNUIZNBCHWLZ-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- IPZJPYHEVWLBNH-UHFFFAOYSA-N 5-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=CC2=C1Cl IPZJPYHEVWLBNH-UHFFFAOYSA-N 0.000 description 1
- FVCBEMCHOGFXKE-UHFFFAOYSA-N C(CC(=O)C)(=O)O.C(CC(=O)C)(=O)NC1=CC=CC=C1 Chemical compound C(CC(=O)C)(=O)O.C(CC(=O)C)(=O)NC1=CC=CC=C1 FVCBEMCHOGFXKE-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- 235000001543 Corylus americana Nutrition 0.000 description 1
- 240000007582 Corylus avellana Species 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 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 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 239000011324 bead Substances 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000012730 carminic acid Nutrition 0.000 description 1
- 239000004106 carminic acid Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910000361 cobalt sulfate Inorganic materials 0.000 description 1
- 229940044175 cobalt sulfate Drugs 0.000 description 1
- KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
- 229940080423 cochineal Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- KJADDPWIRVBKPZ-UHFFFAOYSA-N ethyl n-(7-hydroxynaphthalen-1-yl)carbamate Chemical compound C1=C(O)C=C2C(NC(=O)OCC)=CC=CC2=C1 KJADDPWIRVBKPZ-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- DZNFLGGCJZUMEM-UHFFFAOYSA-N methyl n-(7-hydroxynaphthalen-1-yl)carbamate Chemical compound C1=C(O)C=C2C(NC(=O)OC)=CC=CC2=C1 DZNFLGGCJZUMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- MHQYNOHBRKPLGX-UHFFFAOYSA-N n-(5-hydroxy-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC(O)=CC=C1C MHQYNOHBRKPLGX-UHFFFAOYSA-N 0.000 description 1
- DFPNOBYKTMZUIK-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)propanamide Chemical compound C1=C(O)C=C2C(NC(=O)CC)=CC=CC2=C1 DFPNOBYKTMZUIK-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- KQTXINGLCJCFJE-UHFFFAOYSA-N propyl n-(7-hydroxynaphthalen-1-yl)carbamate Chemical compound C1=C(O)C=C2C(NC(=O)OCCC)=CC=CC2=C1 KQTXINGLCJCFJE-UHFFFAOYSA-N 0.000 description 1
- PTHOQHHSYVYATB-UHFFFAOYSA-N pyrazol-3-imine Chemical compound N=C1C=CN=N1 PTHOQHHSYVYATB-UHFFFAOYSA-N 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
-
- 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
- C09B55/00—Azomethine dyes
- C09B55/002—Monoazomethine dyes
-
- 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
- D06P1/02—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 azo dyes
- D06P1/10—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 azo dyes containing metal
-
- 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
- D06P1/13—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 azomethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH976474A CH603758A5 (en) | 1974-07-16 | 1974-07-16 | Metallised azo or axomethine dyes |
| CH675075 | 1975-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU893138A3 true SU893138A3 (ru) | 1981-12-23 |
Family
ID=25700111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752155211A SU893138A3 (ru) | 1974-07-16 | 1975-07-15 | Способ крашени полиамидных материалов металлокомплексным азо- или азометиновым красителем |
Country Status (12)
| Country | Link |
|---|---|
| US (3) | US4215042A (enExample) |
| JP (1) | JPS5921904B2 (enExample) |
| AR (1) | AR207988A1 (enExample) |
| CA (1) | CA1055019A (enExample) |
| DD (1) | DD120462A5 (enExample) |
| DE (1) | DE2531443C2 (enExample) |
| ES (1) | ES439414A1 (enExample) |
| FR (1) | FR2278738A1 (enExample) |
| GB (1) | GB1520308A (enExample) |
| IT (1) | IT1040931B (enExample) |
| NL (1) | NL7507204A (enExample) |
| SU (1) | SU893138A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2288243C2 (ru) * | 2001-01-26 | 2006-11-27 | Циба Спешиалти Кемикэлз Холдинг Инк. | Азокрасители, способ их получения и их применение при окрашивании гидрофобных волокнистых материалов или печатании на них |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4507124A (en) * | 1982-07-02 | 1985-03-26 | Ciba-Geigy Corporation | 1:2 Metal complexes of azomethine dyes having arylazo groups |
| CH660016A5 (de) * | 1983-11-09 | 1987-03-13 | Ciba Geigy Ag | Reaktivfarbstoffe und deren herstellung. |
| EP0183651B1 (de) * | 1984-11-30 | 1990-05-23 | Ciba-Geigy Ag | Neue Metallkomplexe, Verfahren zu deren Herstellung und Verwendung |
| US4760134A (en) * | 1985-08-28 | 1988-07-26 | Hoechst Celanese Corporation | Process for the preparation of the copper complex disazo compounds from disazo compounds containing an O'-alkoxyaniline group by coppering dimethylation at a pH at about 3-6 |
| US5821356A (en) | 1996-08-12 | 1998-10-13 | The Perkin Elmer Corporation | Propargylethoxyamino nucleotides |
| GB9921928D0 (en) * | 1999-09-16 | 1999-11-17 | Avecia Ltd | Compound |
| DE10206564A1 (de) * | 2002-02-18 | 2003-09-04 | Bayer Ag | Inkjet-Farbstoffe |
| GB0413557D0 (en) * | 2004-06-17 | 2004-07-21 | Avecia Ltd | Compounds |
| JP2013091723A (ja) * | 2011-10-26 | 2013-05-16 | Sumitomo Chemical Co Ltd | 化合物 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3040019A (en) * | 1962-06-19 | Metal-complex dyestuffs | ||
| US2317733A (en) * | 1940-06-20 | 1943-04-27 | Geigy Ag J R | Dyestuffs becoming green when chromed and their manufacture |
| US2602080A (en) * | 1947-10-22 | 1952-07-01 | Gen Aniline & Film Corp | Metallized ortho-hydroxy monoazo dyestuffs |
| US2897190A (en) * | 1951-12-21 | 1959-07-28 | Ciba Ltd | Metalliferous azo-dyestuffs |
| DE934905C (de) * | 1951-12-21 | 1955-11-10 | Ciba Geigy | Verfahren zur Herstellung neuer metallhaltiger Azofarbstoffe |
| US2897189A (en) * | 1951-12-21 | 1959-07-28 | Ciba Ltd | Metalliferous azo-dyestuffs |
| CH340284A (de) * | 1955-12-20 | 1959-08-15 | Sandoz Ag | Verfahren zur Herstellung metallisierbarer Monoazofarbstoffe |
| US2970137A (en) * | 1958-09-09 | 1961-01-31 | Verona Pharma Chemical Corp | Metallized mixed azo-dyestuffs |
| DE1275706B (de) * | 1958-12-12 | 1968-08-22 | Sandoz Ag | Verfahren zur Herstellung von Metallkomplexfarbstoffen |
| CH384108A (de) * | 1959-05-28 | 1964-11-15 | Sandoz Ag | Verfahren zur Herstellung metallhaltiger Azofarbstoffe |
| DE1233518B (de) * | 1961-12-14 | 1967-02-02 | Bayer Ag | Verfahren zur Herstellung metallhaltiger Azofarbstoffe |
| CH442574A (de) * | 1962-03-21 | 1967-08-31 | Acna | Verfahren zur Herstellung von neuen metallisierten Farbstoffen |
| CH473871A (de) * | 1965-02-19 | 1969-06-15 | Sandoz Ag | Verfahren zur Herstellung wasserlöslicher, kupferhaltiger Reaktivfarbstoffe |
| CH503781A (de) | 1968-05-15 | 1971-02-28 | Sandoz Ag | Verfahren zur Herstellung von basischen Farbstoffen |
| CH544138A (de) | 1968-07-15 | 1973-11-15 | Ciba Geigy Ag | Verfahren zur Herstellung metallhaltiger Azofarbstoffe |
| CH552035A (de) | 1968-07-15 | 1974-07-31 | Ciba Geigy Ag | Verfahren zur herstellung von azofarbstoffen. |
| CH552661A (de) | 1968-11-12 | 1974-08-15 | Ciba Geigy Ag | Verfahren zur herstellung neuer azofarbstoffe. |
| US3936436A (en) | 1969-12-22 | 1976-02-03 | Imperial Chemical Industries Limited | Water-soluble azo dyestuffs containing triazine and 3-azo-2,6-dihydroxypyrid-6-one radicals |
| US4067864A (en) | 1970-05-15 | 1978-01-10 | Ciba-Geigy Ag | Fiber-reactive 2-hydroxy-pyrid-6-on-(3)-yl azo dyestuffs |
| US3723490A (en) * | 1970-05-20 | 1973-03-27 | Ciba Geigy Ag | Production of azomethine pigments |
| US3700709A (en) * | 1970-05-20 | 1972-10-24 | Ciba Geigy Ag | Azomethine pigments |
| GB1350602A (en) | 1970-07-10 | 1974-04-18 | Ici Ltd | Azo dyestuffs |
| US4017477A (en) | 1970-08-19 | 1977-04-12 | Ciba-Geigy Ag | 3-Halogeno-6-hydroxy-pyridone-(2) azo dyestuffs |
| CH562301A5 (enExample) * | 1971-12-13 | 1975-05-30 | Ciba Geigy Ag | |
| US4058515A (en) * | 1972-05-30 | 1977-11-15 | Toms River Chemical Corporation | Metallized phenyl-azo-naphthol compounds |
| US4092308A (en) | 1972-10-05 | 1978-05-30 | Ciba-Geigy Corporation | 4-Sulphomethyl substituted hydroxypyridone azo dyestuffs |
| DE2307341A1 (de) * | 1973-02-15 | 1974-08-29 | Hoechst Ag | Wasserunloesliche monoazomethinfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| US4066637A (en) | 1974-06-18 | 1978-01-03 | Ciba-Geigy Corporation | Basic diaminopyridine-(3)-azo dyestuffs |
| US4096157A (en) * | 1974-08-28 | 1978-06-20 | Hoechst Aktiengesellschaft | Azamethine metal complex compounds |
| US4116952A (en) | 1975-05-14 | 1978-09-26 | Ciba-Geigy Corporation | Unsymmetrical azo - azo methine 1:2 chromium complex dyes |
| CH636632A5 (de) | 1976-10-08 | 1983-06-15 | Ciba Geigy Ag | Neues verfahren zur herstellung von schwermetallkomplexen. |
| CH627201A5 (enExample) | 1977-03-14 | 1981-12-31 | Sandoz Ag | |
| GB1555423A (en) | 1977-05-27 | 1979-11-07 | Ici Ltd | Reactive dyestuffs containing a halogeno-pyridine residue |
-
1975
- 1975-01-01 AR AR259567A patent/AR207988A1/es active
- 1975-06-17 NL NL7507204A patent/NL7507204A/xx not_active Application Discontinuation
- 1975-06-23 JP JP50075795A patent/JPS5921904B2/ja not_active Expired
- 1975-07-10 FR FR7521712A patent/FR2278738A1/fr active Granted
- 1975-07-14 CA CA231,396A patent/CA1055019A/en not_active Expired
- 1975-07-14 IT IT50505/75A patent/IT1040931B/it active
- 1975-07-14 DE DE2531443A patent/DE2531443C2/de not_active Expired
- 1975-07-15 ES ES439414A patent/ES439414A1/es not_active Expired
- 1975-07-15 SU SU752155211A patent/SU893138A3/ru active
- 1975-07-15 GB GB29634/75A patent/GB1520308A/en not_active Expired
- 1975-07-15 DD DD187307A patent/DD120462A5/xx unknown
-
1978
- 1978-05-09 US US05/904,358 patent/US4215042A/en not_active Expired - Lifetime
-
1980
- 1980-05-05 US US06/146,973 patent/US4318849A/en not_active Expired - Lifetime
-
1981
- 1981-11-09 US US06/319,533 patent/US4436659A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2288243C2 (ru) * | 2001-01-26 | 2006-11-27 | Циба Спешиалти Кемикэлз Холдинг Инк. | Азокрасители, способ их получения и их применение при окрашивании гидрофобных волокнистых материалов или печатании на них |
Also Published As
| Publication number | Publication date |
|---|---|
| US4436659A (en) | 1984-03-13 |
| ES439414A1 (es) | 1977-02-01 |
| US4318849A (en) | 1982-03-09 |
| GB1520308A (en) | 1978-08-09 |
| JPS5921904B2 (ja) | 1984-05-23 |
| DE2531443C2 (de) | 1985-02-14 |
| AR207988A1 (es) | 1976-11-22 |
| AU8304675A (en) | 1977-01-20 |
| FR2278738A1 (fr) | 1976-02-13 |
| FR2278738B1 (enExample) | 1977-12-16 |
| CA1055019A (en) | 1979-05-22 |
| US4215042A (en) | 1980-07-29 |
| IT1040931B (it) | 1979-12-20 |
| NL7507204A (nl) | 1976-01-20 |
| DD120462A5 (enExample) | 1976-06-12 |
| JPS5117220A (enExample) | 1976-02-12 |
| DE2531443A1 (de) | 1976-01-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4704133A (en) | Process for the photochemical stabilization of synthetic polyamide fibre materials with water-soluble copper complex dye | |
| SU893138A3 (ru) | Способ крашени полиамидных материалов металлокомплексным азо- или азометиновым красителем | |
| JPS60252790A (ja) | 未染色および染色されたポリアミド繊維材料およびポリアミド混合繊維材料の光化学的安定化方法 | |
| JPS6114177B2 (enExample) | ||
| JPS5839185B2 (ja) | シンキクロムサクタイセンリヨウノセイホウ | |
| DE2361837A1 (de) | Neue chromkomplexe, verfahren zu ihrer herstellung und ihre verwendung | |
| CH637676A5 (de) | Metallkomplexfarbstoffe. | |
| CA1070296A (en) | Chromium complexes, their manufacture and use | |
| GB778262A (en) | Improvements relating to monoazo dyestuffs containing heavy metal and their use | |
| US4996303A (en) | Preparation of 1:2 metal complex dyes by coupling in the presence of a metal donor in an inert gas atmosphere | |
| US4560744A (en) | Azo dye 2:1-chromium complexes | |
| DE3123969A1 (de) | "unsymmetrische 1:2-azo-azomethin-chromkomplexe | |
| CA1168654A (en) | Chrome-complex dyes and the production and use thereof | |
| US3933785A (en) | Azo compounds | |
| CA1290104C (en) | Process for the trichromatic dyeing of leather | |
| US5229502A (en) | Preparation of 1:2 chromium complexes one sulfo substituted and one sulfonamido or the like substituted azo dyes | |
| US2897190A (en) | Metalliferous azo-dyestuffs | |
| US3169951A (en) | Chromhjm-containing azo dyestuffs | |
| US3978037A (en) | Azo, azo methine 1:2 chromium complex dyes | |
| JPH0245569A (ja) | アゾ染料 | |
| GB2170213A (en) | Asymmetric 1:2 chromium complex dyes | |
| GB2186282A (en) | Asymmetric 1:2-chromium complex dyes | |
| US4116624A (en) | New heavy metal complex dyes, process for their manufacture and use thereof | |
| EP0141416B1 (de) | Faserreaktive Chromkomplexe, deren Herstellung und Verwendung | |
| JPS5889657A (ja) | アゾ染料またはこれを含む金属錯体染料およびそれらの製造方法 |