CH658252A5 - Verfahren zur herstellung von 1:2-chromkomplexfarbstoffen. - Google Patents
Verfahren zur herstellung von 1:2-chromkomplexfarbstoffen. Download PDFInfo
- Publication number
- CH658252A5 CH658252A5 CH1146/84A CH114684A CH658252A5 CH 658252 A5 CH658252 A5 CH 658252A5 CH 1146/84 A CH1146/84 A CH 1146/84A CH 114684 A CH114684 A CH 114684A CH 658252 A5 CH658252 A5 CH 658252A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dyes
- azo
- chromium
- chromium complex
- complex
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 49
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims description 52
- 239000000987 azo dye Substances 0.000 claims description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 40
- 239000011651 chromium Substances 0.000 claims description 34
- 229910052804 chromium Inorganic materials 0.000 claims description 32
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 25
- -1 phenylazo Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 9
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 150000001844 chromium Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005580 one pot reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000004532 chromating Methods 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims 2
- BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical class [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims 1
- 239000002657 fibrous material Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 210000002268 wool Anatomy 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229950011260 betanaphthol Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052801 chlorine Chemical group 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000001174 sulfone group Chemical group 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- RHPXYZMDLOJTFF-UHFFFAOYSA-N 3-amino-4-hydroxy-5-nitrobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC([N+]([O-])=O)=C1O RHPXYZMDLOJTFF-UHFFFAOYSA-N 0.000 description 2
- HDHQZCHIXUUSMK-UHFFFAOYSA-N 4-hydroxy-2-quinolone Chemical compound C1=CC=C2C(O)=CC(=O)NC2=C1 HDHQZCHIXUUSMK-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 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
- MZKALFCNIJHTJG-UHFFFAOYSA-N 2,5-diphenyl-4h-pyrazol-3-one Chemical compound O=C1CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 MZKALFCNIJHTJG-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
- QQDKXJSYZGJGKJ-UHFFFAOYSA-N 2-amino-3,4,6-trichlorophenol Chemical compound NC1=C(O)C(Cl)=CC(Cl)=C1Cl QQDKXJSYZGJGKJ-UHFFFAOYSA-N 0.000 description 1
- WASQBNCGNUTVNI-UHFFFAOYSA-N 2-amino-4,6-dichlorophenol Chemical compound NC1=CC(Cl)=CC(Cl)=C1O WASQBNCGNUTVNI-UHFFFAOYSA-N 0.000 description 1
- SWFNPENEBHAHEB-UHFFFAOYSA-N 2-amino-4-chlorophenol Chemical compound NC1=CC(Cl)=CC=C1O SWFNPENEBHAHEB-UHFFFAOYSA-N 0.000 description 1
- FZCQMIRJCGWWCL-UHFFFAOYSA-N 2-amino-5-chlorophenol Chemical compound NC1=CC=C(Cl)C=C1O FZCQMIRJCGWWCL-UHFFFAOYSA-N 0.000 description 1
- AACMNEWXGKOJJK-UHFFFAOYSA-N 2-amino-6-nitrophenol Chemical compound NC1=CC=CC([N+]([O-])=O)=C1O AACMNEWXGKOJJK-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
- WTHUWXPBPNTSHJ-UHFFFAOYSA-N 2-hydroxy-3,6-dimethylbenzaldehyde Chemical compound CC1=CC=C(C)C(C=O)=C1O WTHUWXPBPNTSHJ-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
- IHFRMUGEILMHNU-UHFFFAOYSA-N 2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C=C1C=O IHFRMUGEILMHNU-UHFFFAOYSA-N 0.000 description 1
- NNZXDXMEXBYSRF-UHFFFAOYSA-N 2-methyl-4h-pyrazol-3-one Chemical compound CN1N=CCC1=O NNZXDXMEXBYSRF-UHFFFAOYSA-N 0.000 description 1
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 description 1
- KJDPLFMXUGEZSU-UHFFFAOYSA-N 3-butyl-2-hydroxybenzaldehyde Chemical compound CCCCC1=CC=CC(C=O)=C1O KJDPLFMXUGEZSU-UHFFFAOYSA-N 0.000 description 1
- DOHOPUBZLWVZMZ-UHFFFAOYSA-N 3-chloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=CC=C1C=O DOHOPUBZLWVZMZ-UHFFFAOYSA-N 0.000 description 1
- IPPQNXSAJZOTJZ-UHFFFAOYSA-N 3-methylsalicylaldehyde Chemical compound CC1=CC=CC(C=O)=C1O IPPQNXSAJZOTJZ-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical group C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- UQKAOPWZAUTFPK-UHFFFAOYSA-N 4-amino-2-chloro-5-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1O UQKAOPWZAUTFPK-UHFFFAOYSA-N 0.000 description 1
- DHXPRBHRJQAXHK-UHFFFAOYSA-N 4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 DHXPRBHRJQAXHK-UHFFFAOYSA-N 0.000 description 1
- WJASNMAUXFNVNB-UHFFFAOYSA-N 4-chloro-2-hydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(Cl)=C([N+]([O-])=O)C=C1C=O WJASNMAUXFNVNB-UHFFFAOYSA-N 0.000 description 1
- QNZWAJZEJAOVPN-UHFFFAOYSA-N 4-chloro-2-hydroxybenzaldehyde Chemical compound OC1=CC(Cl)=CC=C1C=O QNZWAJZEJAOVPN-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- ACNOLCYSQPFXFF-UHFFFAOYSA-N 5,8-dichloronaphthalen-2-ol Chemical compound ClC1=CC=C(Cl)C2=CC(O)=CC=C21 ACNOLCYSQPFXFF-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
- NSKZAOKQZDLHGO-UHFFFAOYSA-N 5-chloro-2-hydroxy-3-methylbenzaldehyde Chemical compound CC1=CC(Cl)=CC(C=O)=C1O NSKZAOKQZDLHGO-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
- WWPKRXOOVICNJY-UHFFFAOYSA-N 6-methoxynaphthalen-2-ol Chemical compound C1=C(O)C=CC2=CC(OC)=CC=C21 WWPKRXOOVICNJY-UHFFFAOYSA-N 0.000 description 1
- TWLMSPNQBKSXOP-UHFFFAOYSA-N 6358-09-4 Chemical compound NC1=CC([N+]([O-])=O)=CC(Cl)=C1O TWLMSPNQBKSXOP-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- QVKBELCKHUHPRW-UHFFFAOYSA-N 8-chloronaphthalen-1-ol Chemical compound C1=CC(Cl)=C2C(O)=CC=CC2=C1 QVKBELCKHUHPRW-UHFFFAOYSA-N 0.000 description 1
- DQIVFTJHYKDOMZ-UHFFFAOYSA-N 96-67-3 Chemical compound NC1=CC([N+]([O-])=O)=CC(S(O)(=O)=O)=C1O DQIVFTJHYKDOMZ-UHFFFAOYSA-N 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910021556 Chromium(III) chloride Inorganic materials 0.000 description 1
- 229910021564 Chromium(III) fluoride Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- XHFVDZNDZCNTLT-UHFFFAOYSA-H chromium(3+);tricarbonate Chemical compound [Cr+3].[Cr+3].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O XHFVDZNDZCNTLT-UHFFFAOYSA-H 0.000 description 1
- 239000011636 chromium(III) chloride Substances 0.000 description 1
- 235000007831 chromium(III) chloride Nutrition 0.000 description 1
- GRWVQDDAKZFPFI-UHFFFAOYSA-H chromium(III) sulfate Chemical compound [Cr+3].[Cr+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRWVQDDAKZFPFI-UHFFFAOYSA-H 0.000 description 1
- 229910000356 chromium(III) sulfate Inorganic materials 0.000 description 1
- 239000011696 chromium(III) sulphate Substances 0.000 description 1
- 235000015217 chromium(III) sulphate Nutrition 0.000 description 1
- CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 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
- 239000010985 leather Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- QXYMVUZOGFVPGH-UHFFFAOYSA-N picramic acid Chemical compound NC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O QXYMVUZOGFVPGH-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- ZRRGOUHITGRLBA-UHFFFAOYSA-N stattic Chemical compound [O-][N+](=O)C1=CC=C2C=CS(=O)(=O)C2=C1 ZRRGOUHITGRLBA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber 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
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic 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
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/01—Complex metal compounds of azo dyes characterised by the method of metallisation
-
- 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
- C09B55/001—Azomethine dyes forming a 1,2 complex metal compound, e.g. with Co or Cr, with an other dye, e.g. with an azo or azomethine dye
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1146/84A CH658252A5 (de) | 1984-03-08 | 1984-03-08 | Verfahren zur herstellung von 1:2-chromkomplexfarbstoffen. |
| EP85810089A EP0156768B1 (de) | 1984-03-08 | 1985-03-04 | Verfahren zur Herstellung von 1:2-Chromkomplexfarbstoffen |
| US06/707,924 US4997917A (en) | 1984-03-08 | 1985-03-04 | Preparation of 1:2 chromium complex azo dyes asymmetrically substituted with solubilizing |
| DE8585810089T DE3566125D1 (en) | 1984-03-08 | 1985-03-04 | Process for the preparation of 1:2 chromium complex dyes |
| KR1019850001468A KR850006437A (ko) | 1984-03-08 | 1985-03-07 | 1:2형 크롬 착염 염료의 제조방법 |
| JP60046328A JPS60208363A (ja) | 1984-03-08 | 1985-03-08 | １：２‐クロム錯塩染料の製造方法 |
| HK479/91A HK47991A (en) | 1984-03-08 | 1991-06-20 | Process for the preparation of 1:2 chromium complex dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1146/84A CH658252A5 (de) | 1984-03-08 | 1984-03-08 | Verfahren zur herstellung von 1:2-chromkomplexfarbstoffen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH658252A5 true CH658252A5 (de) | 1986-10-31 |
Family
ID=4203558
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1146/84A CH658252A5 (de) | 1984-03-08 | 1984-03-08 | Verfahren zur herstellung von 1:2-chromkomplexfarbstoffen. |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4997917A (en, 2012) |
| EP (1) | EP0156768B1 (en, 2012) |
| JP (1) | JPS60208363A (en, 2012) |
| KR (1) | KR850006437A (en, 2012) |
| CH (1) | CH658252A5 (en, 2012) |
| DE (1) | DE3566125D1 (en, 2012) |
| HK (1) | HK47991A (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0384893B1 (de) * | 1989-02-23 | 1994-09-07 | Ciba-Geigy Ag | Verfahren zur Herstellung von asymmetrischen 1:2-Metallkomplexfarbstoffen |
| KR970061918A (ko) * | 1996-02-22 | 1997-09-12 | 성재갑 | 대장균에서 발현된 유전자 재조합 닭 성장 호르몬의 정제방법 |
| GB2372750B (en) * | 2001-01-18 | 2004-09-08 | Avecia Ltd | Hexa co-ordinated metal complexes of monoazo dyes for use in inks suitable for ink jet printing |
| CN101387836B (zh) * | 2008-10-23 | 2011-05-25 | 湖北鼎龙化学股份有限公司 | 电荷调节剂的制造方法 |
| JP7408915B2 (ja) * | 2019-01-31 | 2024-01-09 | セイコーエプソン株式会社 | インクジェット捺染インク組成物及び記録方法 |
| JP7283249B2 (ja) * | 2019-06-19 | 2023-05-30 | セイコーエプソン株式会社 | 水系インクジェット捺染インク組成物及び捺染方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2906746A (en) * | 1959-09-29 | Metalliferous azo dyestuffs | ||
| DE151003C (en, 2012) * | ||||
| FR1040664A (fr) * | 1950-04-06 | 1953-10-16 | Ciba Geigy | Colorants azoïques métallifères, leur préparation et leur ? |
| US2985646A (en) * | 1957-03-14 | 1961-05-23 | Geigy Ag J R | Chromium-containing dyestuffs |
| GB967011A (en) * | 1962-04-12 | 1964-08-19 | Wolfen Filmfab Veb | New chromium complex azo dyestuff |
| GB1143643A (en, 2012) * | 1965-07-23 | |||
| GB1163713A (en) * | 1966-02-10 | 1969-09-10 | Ici Ltd | Chromium-Containing Azo Dyestuffs |
| US3939140A (en) * | 1971-04-23 | 1976-02-17 | Hoechst Aktiengesellschaft | Process for the preparation of a dyestuff consisting substantially of only unsymmetrical 1:2-chromium complex azo dyestuffs |
| NL7205191A (en, 2012) * | 1971-04-23 | 1972-10-25 | ||
| DE2313722C3 (de) * | 1973-03-20 | 1987-04-16 | Bayer Ag, 5090 Leverkusen | Chromischkomplex-Farbstoff und dessen Verwendung zum Färben und Bedrucken von stickstoffhaltigen Fasermaterialien |
| CH649773A5 (de) * | 1979-09-24 | 1985-06-14 | Sandoz Ag | Asymmetrische 1:2-chromkomplexe aromatischer azoverbindungen, verfahren zu ihrer herstellung und diese enthaltende praeparate. |
| DE3023664A1 (de) * | 1980-06-25 | 1982-01-21 | Hoechst Ag, 6000 Frankfurt | 1:2-chrom-mischkomplexfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
-
1984
- 1984-03-08 CH CH1146/84A patent/CH658252A5/de not_active IP Right Cessation
-
1985
- 1985-03-04 DE DE8585810089T patent/DE3566125D1/de not_active Expired
- 1985-03-04 EP EP85810089A patent/EP0156768B1/de not_active Expired
- 1985-03-04 US US06/707,924 patent/US4997917A/en not_active Expired - Fee Related
- 1985-03-07 KR KR1019850001468A patent/KR850006437A/ko not_active Withdrawn
- 1985-03-08 JP JP60046328A patent/JPS60208363A/ja active Granted
-
1991
- 1991-06-20 HK HK479/91A patent/HK47991A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HK47991A (en) | 1991-06-28 |
| JPH0521152B2 (en, 2012) | 1993-03-23 |
| EP0156768A3 (en) | 1986-03-19 |
| EP0156768B1 (de) | 1988-11-09 |
| DE3566125D1 (en) | 1988-12-15 |
| US4997917A (en) | 1991-03-05 |
| KR850006437A (ko) | 1985-10-05 |
| EP0156768A2 (de) | 1985-10-02 |
| JPS60208363A (ja) | 1985-10-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: CIBA-GEIGY AG TRANSFER- CIBA SC HOLDING AG |
|
| PFA | Name/firm changed |
Owner name: CIBA SC HOLDING AG TRANSFER- CIBA SPECIALTY CHEMIC |
|
| PL | Patent ceased |