GB1602936A - 1:2 chromium complex dyes - Google Patents
1:2 chromium complex dyes Download PDFInfo
- Publication number
- GB1602936A GB1602936A GB21058/78A GB2105878A GB1602936A GB 1602936 A GB1602936 A GB 1602936A GB 21058/78 A GB21058/78 A GB 21058/78A GB 2105878 A GB2105878 A GB 2105878A GB 1602936 A GB1602936 A GB 1602936A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- dye
- nitro
- chlorine
- substituted
- Prior art date
- 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
Links
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052804 chromium Inorganic materials 0.000 title claims abstract description 21
- 239000011651 chromium Substances 0.000 title claims abstract description 21
- 239000000975 dye Substances 0.000 title abstract description 19
- -1 carbocyclic amine Chemical class 0.000 claims abstract description 49
- 239000000460 chlorine Chemical group 0.000 claims abstract description 39
- 239000001257 hydrogen Substances 0.000 claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 29
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 10
- 238000004043 dyeing Methods 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 210000002268 wool Anatomy 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000005605 benzo group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920001778 nylon Polymers 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000010985 leather Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 229920006306 polyurethane fiber Polymers 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 2
- 229920002994 synthetic fiber Polymers 0.000 claims 2
- 239000012209 synthetic fiber Substances 0.000 claims 2
- 239000000835 fiber Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 3
- 239000004952 Polyamide Substances 0.000 abstract 1
- 229920002647 polyamide Polymers 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 6
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 150000001844 chromium Chemical class 0.000 description 6
- 229910006069 SO3H Inorganic materials 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XPVBLJIHHYLHOE-UHFFFAOYSA-N 2-hydroxy-5-phenyldiazenylbenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1N=NC1=CC=CC=C1 XPVBLJIHHYLHOE-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 4
- YCTAOQGPWNTYJE-UHFFFAOYSA-N 3-amino-5-chloro-2-hydroxybenzenesulfonic acid Chemical compound NC1=CC(Cl)=CC(S(O)(=O)=O)=C1O YCTAOQGPWNTYJE-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 3
- ULUIMLJNTCECJU-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonate;hydron Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1O ULUIMLJNTCECJU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N 3,4-xylenol Chemical compound CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- RXCMFQDTWCCLBL-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(N)=C(O)C=C(S(O)(=O)=O)C2=C1 RXCMFQDTWCCLBL-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
- 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 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 2
- 240000007817 Olea europaea Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 230000009918 complex formation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-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
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- AZUXKVXMJOIAOF-UHFFFAOYSA-N 1-(2-hydroxypropoxy)propan-2-ol Chemical compound CC(O)COCC(C)O AZUXKVXMJOIAOF-UHFFFAOYSA-N 0.000 description 1
- MGUKDIACVRELBY-UHFFFAOYSA-N 1-amino-6-nitronaphthalen-2-ol Chemical compound [O-][N+](=O)C1=CC=C2C(N)=C(O)C=CC2=C1 MGUKDIACVRELBY-UHFFFAOYSA-N 0.000 description 1
- VBYYKJJOHHHSME-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)[CH]N VBYYKJJOHHHSME-UHFFFAOYSA-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
- FCWUFSJRTXLBTH-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC(Cl)=CC=C1Cl FCWUFSJRTXLBTH-UHFFFAOYSA-N 0.000 description 1
- CWESERWNUIUBJU-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1Cl CWESERWNUIUBJU-UHFFFAOYSA-N 0.000 description 1
- HVAINFDIRWAPQM-UHFFFAOYSA-N 2-(4-aminoanilino)-2-oxoacetic acid Chemical compound NC1=CC=C(NC(=O)C(O)=O)C=C1 HVAINFDIRWAPQM-UHFFFAOYSA-N 0.000 description 1
- WHIXQFSPEDIMGL-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-methyl-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=C(Cl)C=C1 WHIXQFSPEDIMGL-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
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- ZARYBZGMUVAJMK-UHFFFAOYSA-N 2-amino-4-chloro-5-nitrophenol Chemical compound NC1=CC(Cl)=C([N+]([O-])=O)C=C1O ZARYBZGMUVAJMK-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
- AJWIWEGQLDDWQC-UHFFFAOYSA-N 2-amino-4-methyl-6-nitrophenol Chemical compound CC1=CC(N)=C(O)C([N+]([O-])=O)=C1 AJWIWEGQLDDWQC-UHFFFAOYSA-N 0.000 description 1
- VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 1
- KTFUNVBAGAPLLC-UHFFFAOYSA-N 2-amino-5-ethoxybenzenesulfonic acid Chemical compound CCOC1=CC=C(N)C(S(O)(=O)=O)=C1 KTFUNVBAGAPLLC-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
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- LOCWBQIWHWIRGN-UHFFFAOYSA-N 2-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1Cl LOCWBQIWHWIRGN-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 1
- JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical compound NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 description 1
- GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 description 1
- TWYLNUMRYUFZIN-UHFFFAOYSA-N 3-(4-methylanilino)phenol Chemical compound C1=CC(C)=CC=C1NC1=CC=CC(O)=C1 TWYLNUMRYUFZIN-UHFFFAOYSA-N 0.000 description 1
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 description 1
- CTGSQPRDMHCIMM-UHFFFAOYSA-N 3-(ethylamino)-4-methylphenol Chemical compound CCNC1=CC(O)=CC=C1C CTGSQPRDMHCIMM-UHFFFAOYSA-N 0.000 description 1
- MVRGLMCHDCMPKD-UHFFFAOYSA-N 3-amino-1h-1,2,4-triazole-5-carboxylic acid Chemical compound NC1=NNC(C(O)=O)=N1 MVRGLMCHDCMPKD-UHFFFAOYSA-N 0.000 description 1
- PHRHXTTZZWUGNN-UHFFFAOYSA-N 3-amino-3-methylbutan-1-ol Chemical compound CC(C)(N)CCO PHRHXTTZZWUGNN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AVQFHKYAVVQYQO-UHFFFAOYSA-N 3-amino-4-hydroxybenzenesulfonamide Chemical compound NC1=CC(S(N)(=O)=O)=CC=C1O AVQFHKYAVVQYQO-UHFFFAOYSA-N 0.000 description 1
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 1
- SOZFVONLAQIHRF-UHFFFAOYSA-N 3-amino-n-phenylbenzenesulfonamide Chemical compound NC1=CC=CC(S(=O)(=O)NC=2C=CC=CC=2)=C1 SOZFVONLAQIHRF-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
- QNAAQOLWUDNQFY-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1.NC1=CC=CC(Cl)=C1 QNAAQOLWUDNQFY-UHFFFAOYSA-N 0.000 description 1
- NHLAPJMCARJFOG-UHFFFAOYSA-N 3-methyl-1,4-dihydropyrazol-5-one Chemical compound CC1=NNC(=O)C1 NHLAPJMCARJFOG-UHFFFAOYSA-N 0.000 description 1
- FRKPCXYPIHAOFI-UHFFFAOYSA-N 3-methylaniline Chemical compound [CH2]C1=CC=CC(N)=C1 FRKPCXYPIHAOFI-UHFFFAOYSA-N 0.000 description 1
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 1
- SJCTXIKOXTUQHC-UHFFFAOYSA-N 4-amino-2,5-dichlorobenzenesulfonic acid Chemical compound NC1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl SJCTXIKOXTUQHC-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- UEALKTCRMBVTFN-UHFFFAOYSA-N 4-nitroanthranilic acid Chemical compound NC1=CC([N+]([O-])=O)=CC=C1C(O)=O UEALKTCRMBVTFN-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
- WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
- GENSTRUCMIZOCD-UHFFFAOYSA-N 5-methyl-2-(2-methylphenyl)-4h-pyrazol-3-one Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1C GENSTRUCMIZOCD-UHFFFAOYSA-N 0.000 description 1
- IMZSHPUSPMOODC-UHFFFAOYSA-N 5-oxo-1-phenyl-4h-pyrazole-3-carboxylic acid Chemical compound O=C1CC(C(=O)O)=NN1C1=CC=CC=C1 IMZSHPUSPMOODC-UHFFFAOYSA-N 0.000 description 1
- HQWKOJIWYQRIAT-UHFFFAOYSA-N 6-anilinonaphthalen-1-ol Chemical compound C=1C=C2C(O)=CC=CC2=CC=1NC1=CC=CC=C1 HQWKOJIWYQRIAT-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- VVPHSMHEYVOVLH-UHFFFAOYSA-N 6-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(O)=CC=C21 VVPHSMHEYVOVLH-UHFFFAOYSA-N 0.000 description 1
- ZPLBZGGKAUXTRT-UHFFFAOYSA-N 8-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC=CC2=C1 ZPLBZGGKAUXTRT-UHFFFAOYSA-N 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
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- RZSYLLSAWYUBPE-UHFFFAOYSA-L Fast green FCF Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC(O)=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 RZSYLLSAWYUBPE-UHFFFAOYSA-L 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000006231 alkoxy propyl group Chemical group 0.000 description 1
- 125000004848 alkoxyethyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000006149 azo coupling reaction Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010014 continuous dyeing Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-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
- GTTFJYUWPUKXJH-UHFFFAOYSA-N n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=CC=C1 GTTFJYUWPUKXJH-UHFFFAOYSA-N 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
- ALNWQAFPXMGLTJ-UHFFFAOYSA-N n-(7-hydroxynaphthalen-1-yl)acetamide Chemical compound C1=C(O)C=C2C(NC(=O)C)=CC=CC2=C1 ALNWQAFPXMGLTJ-UHFFFAOYSA-N 0.000 description 1
- FLCPERRDPXWFDK-UHFFFAOYSA-N n-cyclohexyl-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1CCCCC1 FLCPERRDPXWFDK-UHFFFAOYSA-N 0.000 description 1
- 229950004864 olamine Drugs 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001694 spray drying Methods 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
- 239000000725 suspension Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- 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
-
- 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
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/14—Monoazo compounds
- C09B45/16—Monoazo compounds containing chromium
-
- 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
- C09B45/48—Preparation from other complex metal compounds of azo dyes
- C09B45/482—Chromium complexes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
1:2 Chromium complex dyes conform in the form of the free acids to the formula I <IMAGE> where A is the radical of the aliphatic or carbocyclic amine component, D is the radical of a diazo component, Z is an aliphatic radical, which may be substituted by an R2-substituted phenyl group, or is a carbocyclic or heterocyclic radical, X is -O- or -COO-, B is X or <IMAGE> , E is -O- or <IMAGE> , L is hydrogen or optionally substituted alkyl, cycloalkyl, aralkyl or aryl, R1 is hydrogen, chlorine, bromine, alkyl, alkoxy, nitro, acylamino, carboxyl or optionally N-substituted carbamoyl or sulphamoyl, R2 is hydrogen, chlorine, bromine, alkyl or nitro, or R1 and R2 together are a fused-on benzene ring, or where R1 or R2 are each one of the necessary three hydroxysulphonyl groups. The compounds of the formula (I) are highly suitable for dyeing nitrogen-containing fibres, such as wool, silk or polyamides, the dyeings obtained having good fastness properties.
Description
(54) 1:2 CHROMIUM COMPLEX DYES
(71) We, BASF AKTIENGESELLSCHAFT, a German Joint Stock
Company of 6700 Ludwigshafen, Federal Republic of Germany, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- The present invention relates to 1:2 chromium complex dyes.
According to the invention there are provided 1:2 chromium complex dyes which in the form of the free acids correspond to the general formula I
where A is the radical of an aliphatic or carbocyclic amine component, D is the radical of a diazo component, Z is an aliphatic, carbocyclic or heterocyclic radical,
X is -0- or -COO-, B is X or -N-L and E is -0- or -N-L, L is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, R1 is hydrogen, chlorine, bromine, alkyl, alkoxy, nitro, acylamino, carboxyl or unsubstituted or N-substituted carbamoyl or sulfamoyl, and R2 is hydrogen, chlorine, bromine, alkyl or nitro, or R1 and R2 together are a fused benzo ring, provided that the dye contains at most 2 azo groups, i.e. that none of A, D, Z, X, B, E, L, R1 and R2 contains an azo group.
The SO,H groups of the compounds of the formula I may be present in any of the radicals D, A and Z and/or in the ring which is substituted by R1 and R2.
The radicals of the diazo components D are in the main derived from the benzene or naphthalene series; however, they may also be derived from heterocyclic compounds, e.g. 3 - amino - 1,2,4 - triazole - 5 - carboxylic acid, 8 - amino - 2 - methylquinoline and 2 - (4' - aminophenyl) - 6 - methylbenzothiazole.
Examples of substituents of the radicals D, where these are of the benzene or naphthalene series, are those mentioned in defining R1 and R2.
The amines of the formula H2N-A-BH, where they are carbocyclic amines, are in general derived from the benzene or naphthalene series and may be substituted by Rl and/or R2; where they are aliphatic amines, they are in general 1,2- or 1,3diamines, -hydroxyamines or aminocarboxylic acids
Specific examples of compounds of the formula H2N-A-BH are: 2 - aminophenol, 4 - chloro - 2 - aminophenol, 4- or 5 - nitro - 2 - aminophenol, 4,6 - dichloro 2 - aminophenol, 4 - methyl - 6 - nitro - 2 - aminophenol, 4 - chloro - 5 - nitro - 2- aminophenol, 2 - aminobenzoic acid, 4 -nitro - 2 - aminobenzoic acid, 2 - aminobenzoic acid - 5 - sulfonic acid, 2 - aminophenol - 4 - sulfonic acid, 2 - aminophenol 4 - sulfonamide, 2 - aminophenol - 4 - sulfonic acid phenylamide, 2 - aminophenol5 - sulfonic acid dimethylamide, 2 - aminophenol - 4 - sulfonic acid y - methoxy propylamide, 4 - chloro - 2 - aminophenol - 6 - sulfonic acid, 4 - nitro - 2 - aminophenol - 6 - sulfonic acid, 5- or 6 - nitro - 2 - aminophenol - 4 - sulfonic acid, l- amino - 2 - naphthol - 4 - sulfonic acid, 2 - amino - 1 - naphthol - 5 - sulfonic acid,
1 - amino - 6 - nitro - 2 - naphthol - 4 - sulfonic acid, 1 - aminoethan - 2 - ol, 1
aminopropan - 2 - ol, 1 - aminopropan - 3 - ol, 3 - amino - 3 - methylbutan - I - ol,
2 - aminoacetic acid, 2 - aminopropionic acid, 3 - aminopropionic acid, 2 - amino
3 - hydroxypropionic acid, 2 - amino - 3 - phenylpropionic acid, 2 - aminobuty;ic acid, aminosuccinic acid and 2 - aminoglutaric acid, as well as ethylenediamine, 1,2
and 1,3 - propylenediamine, N - phenylethylenediamine, N - phenyl -1,2 - propylene
diamine and N - methylethylenediamine.
Radicals Z are radicals of azo coupling components (H-Z-EH) containing a
complex-forming hydroxyl or amino group adjacent to the coupling position and are
derived, for example, from the acetoacetarylide, pyrazole, benzene, napththalene, pyridine, pyrimidine or quinoline series; they may contain the conventional sub
stituents for such components, e.g. alkyl, aryl, halogen, unsubstituted or substitut.ed amino, hydroxyl, alkoxy or nitro.
As specific examples, the radicals of the coupling components may have the
formula
where
R3 is hydrogen, methyl, phenyl, carboxyl or carbamoyl,
R4 is hydrogen or is phenyl which is unsubstituted or substituted by methyl,
carboxyl or chlorine,
R5 is methyl, methoxy, acetylamino, propionylamino, benzoylamino, N-phenyl
amino, dimethylamino or diethylamino,
R6 is hydrogen or methyl and
R7 is hydrogen or, together with R8, a fused benzo ring which may or may not be
substituted by hydroxysulfonyl.
Specific examples of compounds of the formula H-Z-EH are: 4 - methylphenol, 3,4 - dimethylphenol, 4 - acetylaminophenol, 4 - methyl - 3 - acetylaminophenol, 4 - methoxyphenol, 3 - diethylaminophenol, 4 - methyl - 3 - ethylaminophenol, 3 - (4 - tolylamino) - phenol, 2 - naphthylamine, 2 - naphthol, 6 - bromo -2 - naphthol, 8 - acetylamino - 2 - naphthol, 5,8 - dichloro - 1 - naphthol, 1 - naphthol sulfonic acid, 2 - naphthol - 6 - sulfonic acid, 1 - naphthylamine - 4- and -5 - sulfonic acid, 2 - naphthylamine - 5- and -6 - sulfonic acid, 8 - acetylamino - 1 - naphthol5 - sulfonic acid, 6 - phenylamino - 1 - naphthol - 3 - sulfonic acid, 7 - amino - 1- naphthol - 3 - sulfonic acid, 3 - methyl - 5 - pyrazolone, 1 - phenyl - 3 - methyl pyrazolone, 1 - phenyl - 5 - aminopyrazole, 1,3 - diphenyl - 5 - pyrazolone, 1phenyl - 5 - pyrazolone - 3 - carboxylic acid, 1 - (2' - methylphenyl) - 3 - methyl- 5 - pyrazolone, 1 - (4' -chlorophenyl) - 3 - methyl - 5 - pyrazolone, 1 - (2',S' - di- chlorophenyl) - 3 - methyl - 5 - pyrazolone, 1 - phenyl - 3 - methyl - 5 - pyrazolonc4' - carboxylic acid, 1 - phenyl - 3 - methyl - 5 - pyrazolone - 3'- and -4' - sulfonic acid, 1,3 - diphenyl - 5 - pyrazolone - 2' - sulfonic acid, 1- (2' - chlorophenyl) - 3methyl - 5 - pyrazolone - 5' - sulfonic acid, 1 - (2',5' - dichlorophenyl) - 3 - methyl5 - pyrazolone - 4' - sulfonic acid, 2,4 - dihydroxyquinoline, N - acetoacetvlnhenylamide, N - acetoacetylcyclohexylamide and N - acetoacetyl - (4 - methylphenyl) - 2sulfonic acid.
The benzene ring, substituted by Rl and R2, which is present in the general formula I is the radical of an aniline derivative which carries a complexforming hydroxyl or carboxyl group in the o-position to the diazotizable amino group; these aniline derivatives accordingly are of the same type as the carbocyclic com- pounds HN--AA-BH, and may be identical to, or different from, these.
Specific examples of diazo components which contain the radical D are aniline, 2-, 3- and 4 - methylaniline, 2,5 - dimethylaniline, 2-, 3- and 4 - chloroaniline, 4bromoaniline, 2,5 - dichloroaniline, 5 - chloro - 2 - methoxyaniline, 4 - chloro - 2,5 - dimethoxyaniline, 4 - acetylaminoaniline, 4 - benzoylaminoaniline, N - (4 - aminophenyl) - oxamic acid, 2-, 3- and 4 - nitroaniline, 2 - chloro - 4 - nitroaniline, 4methyl - 2 - nitroaniline, 2 - methoxy - 5 - nitroaniline, aniline - 4 - sulfonamide, aniline - 3 - sulfonic acid N - phenylamide, 2 - aminobenzoic acid, aniline - 3- and -4 - sulfonic acid, 4 - methylaniline - 2 - sulfonic acid, 4 -ethoxyaniline - 2 - sulfonic acid, 2 - methoxyaniline - 5 - sulfonic acid, 2,5 - dichloroaniline - 4 - sulfonic acid, 4 - chloro - 5 - methylaniline - 2 - sulfonic acid, 4 - nitroaniline - 2 - sulfonic acid, 1 - aminonaphthalene, 1 - aminonaphthalene - 4- and -5 - sulfonic acid, 2 - aminonaphthalene - 5- and -6 - sulfonic acid and 2 - aminonaphthalene - 4,8 - disulfonic acid.
Examples of radicals L, in addition to hydrogen, are alkyl of 1 to 6 carbon atoms, hydroxyalkyl of 2 or 3 carbon atoms, (3-cyanoethyl, alkoxyethyl and alkoxypropyl, where alkoxy is of 1 to 4 carbon atoms, phenoxyethyl and phenoxypropyl, alkanoyloxyethyl and alkanoyloxypropyl, where alkanoyloxy is of-2 to 4 carbon atoms, benzoyloxyethyl and benzoyloxypropyl, phenylsulfonyloxyethyl and phenylsulfonyloxypropyl, tolylsulfonyloxyethyl and tolylsulfonyloxypropyl, cyclohexyl, benzyl, phenylethyl and phenvl which is unsubstituted or substituted by chlorine, bromine, methyl, ethyl, methoxy, ethoxy or hydroxysulfonyl.
Examples of preferred radicals L are alkyl of 1 to 4 carbon atoms, fi-hydroxy- ethyl and ss-hydroxypropyl, methoxyethyl, phenylsulfonyloxyethyl, tolylsulfonyloxyethyl, cyclohexyl or phenyl which is unsubstituted or substituted by chlorine, methyl, methoxy or hydroxysulfonyl.
Specific examples of radicals R1 and R2, in addition to those already mentioned, are alkyl of 1 to 4 carbon atoms, especially methyl, and for R1 alone methoxy, ethoxy, alkanoylamino of 1 to 4 carbon atoms, especially acetylamino and propionylamino, benzoylamino which is unsubstituted or substituted by methyl or chlorine, or carbamoyl or sulfamoyl which are N-monosubstituted or N,N-disubstituted by alkyl of 1 to 4 carbon atoms or are N-phenyl-substituted.
The 1:2 chromium complexes are prepared stepwise via the 1:1 complexes; advantageously, a 1:1 chromium complex of the general formula II
is prepared and reacted with an arylazo-azomethine compound of the general formula
III
to give the 1:2 chromium complex compounds of the general formula I.
In the formulae II and III, m and n are numbers from 0 to 3, where m+n=3; the remaining symbols have the meanings given in connection with formula I.
The 1:1 chromium complexes may be prepared in accordance with conventional methods; in the case of the o,o'-dihydroxyazo complexes, it is also possible to start from the corresponding o-alkoxy-o'-hydroxyazo compounds.
The reaction of the 1:1 chromium complexes of the formula II with the arylazoazomethines of the formula III or with their individual components is suitably carried out in aqueous solution or suspension; the addition of an organic solvent, e.g. an alcohol, glycol, carboxylic acid amide or urea derivative may be advantageous. The formation of the 1:2 complex takes place in a weakly acid to alkaline medium, preferably at pH 6^9, and at an elevated temperature, e.g. at from 50 to the boil.
The resulting 1:2 complexes may be isolated by acidifying, salting out with alkali metal salts, evaporating or spray-drying.
If suitable solvents or solvent mixtures are selected, the 1:2 chromium complexes can also be prepared in the form of stable, concentrated solutions which tan then be used directly, in this form, for preparing dyebaths or print pastes. To prepare these dye solutions, the compounds of the formulas II and III are advantageously used in the form of the free dye-sulfonic acids and the solvent is brought to the appropriate pH with alkanolamines.
The 1:2 chromium complex dyes of the general formula I may be used for dyeing and printing natural or synthetic nitrogen-containing materials, e.g. wool, leather, nylon fibers or polyurethane fibers. The dyeings obtained are distinguished by good fastness, for example to light, and especially by very good wetfastness, e.g.
fastness to washing, fulling, perspiration and potting, in respect of which they are frequently superior to comparable conventional dyes with only one or two sulfonic acid groups. It is surprising that the dyes according to the invention, in spite of their molecular size and large number of anionic charges, exhibit good migrating capacity and thus give level dyeings. Because of their high solubility, the dyes are particularly suitable for continuous dyeing processes, for example carpet dyeing.
Preferred compounds according to the invention are those which in the form of the free acids correspond to the formula
A is a radical of the formula
a is 1, 2 or 3, bisO, 1 our2, B' is hydrogen, chlorine, bromine, nitro, methyl, methoxy, acetylamino, sulfamoyl,
N - phenylsulfamoyl, N,N - dimethyl - N,N - diethyl- or N - y - methoxy
propyl - sulfamoyl or hydroxysulfonyl, and
B2 is hydrogen, chlorine, nitro or hydroxysulfonyl, or
B1 and B2 together are a fused benzo ring which is unsubstituted or substituted
by nitro, chorine or hydroxysulfonyl,
B3 iS -ICH20H, -CH2NH2 or(CH2)COOH, X is -0- or -COO-
L is hydrogen or alkyl of 1 to 15 carbon atoms which is unsubstituted or
substituted by hydroxyl or alkoxy of 1 to 4 carbon atoms, or is phenyl
sulfonyloxyethyl, tolylsulfonyloxyethyl, cyclohexyl or phenylalkyl, where alkyl
is of 1 to 4 carbon atoms, or is phenyl which is unsubstituted or substituted
by chlorine, methyl, methoxy or ethoxy,
D is phenyl which is unsubstituted or substituted by chlorine, bromine, nitro,
methyl, methoxy, ethoxy or hydroxysulfonyl, or is naphthyl substituted by
hydroxysulfonyl, or is 2- (4'-aminophenyl) -6-methylbenzthiazolyl, R1 is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4
carbon atoms, nitro, alkanoylamino of 1 to 4 carbon atoms, benzoylamino
or carboxyl, or is carbamoyl or sulfamoyl which are unsubstituted or are
monosubstituted or disubstituted by alkyl of 1 to 4 carbon atoms or phenyl,
or is hydroxysulfonyl, and
R2 is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, nitro or hydroxy
sulfonyl, or
R1 and R2 together are a fused benzo ring which is unsubstituted or substituted
by nitro or hydroxysulfonyl, and
Z is a radical of the formula
where R3 is hydrogen, methyl, phenyl, carboxyl or carbamoyl, R4 is hydrogen or is phenyl which is unsubstituted or substituted by methyl,
carboxyl or chlorine,
R5 is methyl, methoxy, acetylamino, propionylamino, benzoylamino, N-phenyl
amino, dimethylamino or diethylamino, R5 is hydrogen or methyl and R' is hydrogen or together with Rss is a fused benzo ring, which may or may
not be substituted by hydroxysulfonyl, and the molecule contains three
hydroxysulfonyl groups and two azo groups in all.
1:2 Chromium complexes which are obtained from 1:1 chromium complexes of azo compounds of the formula IV
together with arylazo-azomethines of the formula V
are of particular industrial importance.
In the formulae IV and V, A, B, E, R1, R2, X and Z have the above meanings, R8 and R9, independently of one another, are hydrogen, chlorine, bromine, nitro or acetylamino, or R8 and R9 together are a fused benz ring and p, q and r are 0, 1 or 2, the total number of sulfonic acid groups in the resulting 1:2 complexes being three.
In the Examples which follow, parts are by weight
EXAMPLE 1.
A suspension of 15.3 parts of 5 - phenylazo - 2 - hydroxybenzaldehyde - 4'sulfonic acid in 150 parts of water is heated with 11.4 parts of 4 - chloro - 2 - aminophenol - 6 - sulfonic acid and 12 parts of sodium acetate to 50 . After the azo-azomethine compound has formed, an equimolar amount (about 26 parts) of the 1:1 chromium complex of the azo dye obtained from diazotized 4 - nitro - 2 - aminophenol - 6 - sulfonic acid and 1 - phenyl - 3 - methyl - 5 - pyrazolone is added and the mixture is heated at 70--80", whilst stirring. At the same time the pH is kept at 7-8 by adding sodium hydroxide solution until the formation of the 1:2 complex has ended; the solution is then evaporated or spray-dried.
62 parts of the dye of the formula
are obtained; on wool and nylon fibers this dye gives level, yellowish orange dyeings having very good lightfastness and wetfastness.
The following dyes are obtained by a similar method: Ex1:1 chromium complex of Azomethine Hue ample
6 m 6 m C d ro 2 NSO3 HO HO H HO SO H reddish h > 8 h O St > h Cl Cil3 NO SO o X 3 a o N ,\Cl$NH=N red 3 NO / ON ff0 3 3 yellowish NO3 N=N NO2 H NOOC NO2 4 /\Cl 1, olive -- - SO3H NO2 SO3H NO3S OH NO NO2 COON HO Cl/\ g CH=N - reddish 5 NSO3/\N=N/Cl NO S \N=N SO N yellow x 3 OH HOOCi NSO3 OH HO Cl Cl Cl/\cH=NCH2 yellowish 6 NO3S /\N=N orange 503N C NO2 C113 EXAMPLE 7.
15.3 parts of 5 - phenylazo - 2 - hydroxybenzaldehyde - 4' - sulfonic acid, 11.8 parts of 4 - chloro - 2 - aminophenol - 6 - sulfonic acid and 35.5 parts of the 1:1 chromium complex of the azo dye obtained from diazotized 1 - amino - 2 - naphthol4 - sulphonic acid and 1 - phenyl - 3 - methyl - 5 - pyrazolone are suspended in 200 parts of water. The mixture is heated to 80 , whilst stirring, and the pH is brought to 7.5 with potassium hydroxide solution. After completion of the formation of the 1:2 complex, 180 parts of potassium chloride are added and the dye which has precipitated is isolated.
79 parts of the complex compound of the formula
are obtained. This gives yellowish red hues on wool; the dyeings have good fastnesses, especially very good fastness to wet treatments.
The following dyes were obtained by a similar method: Example 1:1 chromium complex of Azomethine Hue
c > o = o O i g ri t h o f ad ; Ns%/\N=N/- h n O h C O ke 0113 O O red OH HO NO2 X II N1=N CH=N JW H red 3 W H HO Cl OH HO NO2 CH=N brown 10 /\N=N/- I: N=N -- SO3H NO2. Cit3 OH OH HO SO3H c 11 II O3H/\N=NCl t; o X 12 t o o n Z+ > x 4 = Z EX < E | O ~l N Example 1:1 chromium complex of Azomethine Hue
EXAMPLE 14.
11.2 parts of 4 - chloro - 2 - aminophenol - 6 - sulfonic acid and 15.5 parts of 5 - phenylazo - salicylaldehyde - 4' - sulfonic acid in 30 parts of di - (2 - hydroxypropyl) ether and 40 parts of water are heated for 30 minutes at 50 ; 22.6 parts of the 1:1 chromium complex of the azo dye obtained from diazotized 1 - amino - 2naphthol - 4 - sulfonic acid and 2-naphthol are added to the azo-azomethine compound obtained, and 26.6 parts of 2 - (dimethylamino) - ethanol are introduced dropwise whilst stirring at 70 . When the 1:2 complex formation has ended, the reaction mixture is diluted with water to a total weight of 165 parts.
A solution, of about 45 per cent strength, of the complex salt of the formula
is thus obtained; the solution is stable on storage and when used to print textile floor coverings consisting of wool and/or nylons, gives olive patterns.
The solutions of the dyes shown in the Table which follows were obtained by a similar method: Example 1:1 chromium complex of Azomethine + Alkanolamine Hue
d ss OH 2 k 6 z NN=N / \ OH H!-C H -OH green 8 2: o re a, 6 k H803 / > 8 h Cit=N-C2H4 SO N iN SO H OH HOOC 16 8%\H=O3/ f/\N1=N CH=N bluish green SO3H + N(C21140H)3 OH HO OH NO W J . E i V 17 -N SO H \/H3 SOCH :n OH HO \fC3 X C > UO) UO) o ç F C) H < H Example 1:1 chromium complex of Azomethine + @@@@@olamine Hue
EXAMPLE 20.
15 parts of 5 - phenylazosalicylaldehyde - 4' - sulfonic acid are suspended in 300 parts of water and stirred with 8 parts of N-phenylethylenediamine for 30 minutes at 50 C. After adding 30 parts of the 1:1 chromium complex of the azo dye obtained from diazotized 1 - amino - 2 - hydroxy - naphthalene - 4 - sulfonic acid and 1hydroxynaphthalene - 8 - sulfonic acid, the mixture is heated at 80 and is kept at pH 7.5 until the complex formation has ended. After salting out with sodium chloride, 60 parts of the complex dye of the formula
are obtained; this gives fast green dyeings on wool and nylons.
The following dyes were obtained by a similar method: Example 1:1 chromium complex of Azomethine Hue
a a cu cu a, e fa o o o O O -C 2H4 21 HSO OH Xo Cs CH3 a-u 3 ON 7 X 22 1' SO H 5\N1=N CN=N-C2H4 red 35 e t X 0n U\T= green OH HN-CH 24 II HSO3- ${1N=NCH=NCI2H645 green Cl 25 H=N)6l3Hl7 green Us us H U n Ct CY Example 1: :1 chromium complex of Azomethine Hue
m H t o o s a d ak O :2 en P 0@ S03H u 3= 0 ON HSO HHO OH OoC 3 'H=N-CH-CH3 reddish 27 N=N;; c brown V on xM S d O GQ X es GO OJ N CU
Claims (19)
1. A 1:2 chromium complex dye which in the form of the free acid corresponds to the general formula I:
where A is the radical of an aliphatic or carbocyclic amine component, D is the radical of a diazo component, Z is an aliphatic, carbocyclic or heterocyclic radical,
X is -0- or -COO-, B is X or -N-L and E is -0- or -N-L, L is hydrogen or unsubstituted or substituted alkyl, cycloalkyl, aralkyl or aryl, R1 Is hydrogen, chlorine, bromine, alkyl, alkoxy, nitro, acylamino, carboxyl or unsubstituted or N-substituted carbamoyl or sulfamoyl, and R2 is hydrogen, chlorine, bromine, alkyl or nitro, or R1 and R2 together are a fused benzo ring, provided that the dye contains at most 2 azo groups.
2. A dye as claimed in claim 1 which in the form of the free acid corresponds
to the general formula
where
A is a radical of the formula
a is 1, 2 or 3, bis0,1 or2, Bl is hydrogen, chlorine, bromine, nitro, methyl, methoxy, acetylamino, sulfamoyl,
N - phenylsulfamoyl, N,N - dimethyl-, N,N - diethyl- or N - y - methoxy
propyl-sulfamoyl or hydroxysulfonyl, and
B2 is hydrogen, chlorine, nitro or hydroxysulfonyl, or Bl and B2 together are a fused benzo ring which is unsubstituted or substituted
by nitro, chlorine or hydroxysulfonyl,
B3 is -CH,OH, -CH2NH2 or (CH2)aCOOH, X is -0- or -COO
L is hydrogen or alkyl of 1 to 15 carbon atoms which is unsubstituted or substituted
by hydroxyl or alkoxy of 1 to 4 carbon atoms, or is phenylsulfonyloxyethyl,
tolylsulfonyloxyethyl, cyclohexyl or phenylalkyl, where alkyl is of 1 to 4
carbon atoms, or is phenyl which is unsubstituted or substituted by chlorine,
methyl, methoxy or ethoxy,
D is phenyl which is unsubstituted or substituted by chlorine, bromine, nitro,
methyl, methoxy, ethoxy or hydroxysulfonyl, or is naphthyl substituted by
hydroxysulfonyl, or is 2-(4'-aminophenyl) -6-methylbenzthiazolyl, R1 is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4
carbon atoms, nitro, alkanoylamino of 1 to 4 carbon atoms, benzoylamino
or carboxyl, or is carbamoyl or sulfamoyl which are unsubstituted or are
monosubstituted or disubstituted by alkyl of 1 to 4 carbon atoms or phenyl,
or is hydroxysulfonyl, and
R2 is hydrogen, chlorine, bromine, alkyl of 1 to 4 carbon atoms, nitro or hydroxy salfonyl, or
R1 and R2 together are a fused benzo ring which is unsubstituted or substituted
by nitro or hydroxysulfonyl, and
Z is a radical of the formula
where
R3 is hydrogen, methyl, phenyl, carboxyl or carbamoyl,
R4 is hydrogen or is phenyl which is unsubstituted or substituted by methyl,
carboxyl or chlorine, R is methyl, methoxy, acetylamino, propionylamino, benzoylamino, N-phenyl
amino, dimethylamino or diethylamino, R" is hydrogen or methyl and
R7 is hydrogen or together with R3 is a fused benzo ring, which may or may not
be substituted by hydroxysulfonyl, and the molecule contains three hydroxy
sulfonyl groups and two azo groups in all.
3. A dye as claimed in claim 2, wherein B1 is hydrogen, chlorine, nitro, methyl, sulfamoyl or hydroxysulfonyl and B2 is hydrogen, chlorine, nitro or hydroxysulfonyl.
4. A dye as claimed in claim 2 or claim 3 wherein L is hydrogen, fi-hydroxy- ethyl, alkyl of 1 to 4 carbon atoms or phenyl.
5. A dye as claimed in any of claims 2 to 4, wherein R1 is hydrogen, chlorine, methyl, methoxy, nitro, acetylamino, benzoylamino, carboxyl, carbamoyl, sulfamoyl or hydroxysulfonyl, R2 is hydrogen, chlorine, nitro or hydroxysulfonyl or R1 and RX together are a fused benzo ring which is unsubstituted or substituted by nitro or hydroxy suiphonyl.
6. A dye as claimed in any of claims 2 to 5 wherein Z is
R2 and R7 are each as defined in claim 2.
7. A dye as claimed in claim 1 and hereinbefore specifically identified.
8. A dye as claimed in claim 1, having the formula
9. A dye as claimed in claim 1, having the formula
10. A dye as claimed in claim 1, having the formula
11. A dye as claimed in claim 1, having the formula
12. A process for the manufacture of a compound as claimed in claim 1, wherein an arylazo-azomethine compound of the general formula III
is adducted with a 1:1 chromium complex of the general formula II
where m and n are 0, 1, 2 or 3, m+n is 3 and A, B, D, E, R1, R", X and Z have the meanings given in claim 1.
13. A process as claimed in claim 12 carried out substantially as described in any one of the foregoing specific Exampels.
14. A dye as claimed in claim 1 whenever obtained by a process as claimed in claim 12 or claim 13.
15. A dye formulation for dyeing nitrogen-containing, natural or synthetic fibers in which formulation a dye as claimed in any of claims 1 to 11 and 14 is present as dye.
16. Nitrogen-containing natural or synthetic fibers dyed by a dye as claimed in any of claims 1 to 11 and 14.
17. Wool, leather, nylon fibers or polyurethane fibers dyed by a dye as claimed in any of claims 1 to 11 and 14.
18. A textile finished product dyed by a dye as claimed in any of claims 1 to 11 and 14.
19. A carpet made of textile material comprised of fibers dyed by a dye as claimed in any of claims 1 to 11 and 14.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772723155 DE2723155A1 (en) | 1977-05-23 | 1977-05-23 | (1:2)-Chromium complex dyes contg. three sulphonic acid groups - with good migration power, giving level, light and wet fast dyeings on wool and nylon |
| DE19772735287 DE2735287C2 (en) | 1977-08-05 | 1977-08-05 | 1: 2 chromium complex dyes, their production and use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1602936A true GB1602936A (en) | 1981-11-18 |
Family
ID=25772051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21058/78A Expired GB1602936A (en) | 1977-05-23 | 1978-05-22 | 1:2 chromium complex dyes |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS53144930A (en) |
| CH (1) | CH649568A5 (en) |
| FR (1) | FR2392087A1 (en) |
| GB (1) | GB1602936A (en) |
| IT (1) | IT1096366B (en) |
| NL (1) | NL7805579A (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443370A (en) * | 1980-06-05 | 1984-04-17 | Ciba-Geigy Corporation | Chrome-complex dyes |
| DE3121923A1 (en) * | 1981-06-02 | 1982-12-16 | Bayer Ag, 5090 Leverkusen | ASYMMETRIC 1: 2 CHROME COMPLEX DYES |
| DE3132334A1 (en) * | 1981-08-17 | 1983-03-03 | Bayer Ag, 5090 Leverkusen | ASYMMETRICAL 1: 2 CHROME COMPLEX DYES |
| CH656890A5 (en) * | 1983-12-15 | 1986-07-31 | Ciba Geigy Ag | UNBALANCED 1: 2 CHROME COMPLEX DYES. |
| CH656891A5 (en) * | 1983-12-15 | 1986-07-31 | Ciba Geigy Ag | UNBALANCED 1: 2 CHROME COMPLEX DYES. |
| CH660196A5 (en) * | 1984-01-19 | 1987-03-31 | Ciba Geigy Ag | UNSYMMETRICAL 1: 2 CHROME COMPLEX, CONTAINING AN AZO AND AZOMETHINE COMPOUND. |
| DE3433980A1 (en) * | 1984-09-15 | 1986-03-27 | Bayer Ag, 5090 Leverkusen | UNBALANCED 1: 2 CHROME COMPLEX DYES |
| CH667465A5 (en) * | 1985-12-18 | 1988-10-14 | Ciba Geigy Ag | UNBALANCED 1: 2 chromium complex dyes. |
| DE4224558A1 (en) * | 1992-07-24 | 1994-01-27 | Bayer Ag | Unsymmetrical 1: 2 chromium complex dyes |
| JP7496873B2 (en) * | 2020-07-08 | 2024-06-07 | 富士フイルム株式会社 | Coloring composition, film, optical filter, solid-state imaging device, image display device, and compound |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH284873A4 (en) * | 1972-03-03 | 1975-10-15 | ||
| CH599307A5 (en) * | 1974-05-09 | 1978-05-31 | Ciba Geigy Ag | |
| DE2461481C3 (en) * | 1974-12-24 | 1979-06-13 | Basf Ag, 6700 Ludwigshafen | Unsymmetrical 1 to 2 chromium complexes containing an azo and an azomethine compound, process for their preparation and their use |
| CH624979A5 (en) * | 1975-05-14 | 1981-08-31 | Ciba Geigy Ag |
-
1978
- 1978-05-17 IT IT23528/78A patent/IT1096366B/en active
- 1978-05-19 CH CH5471/78A patent/CH649568A5/en not_active IP Right Cessation
- 1978-05-22 GB GB21058/78A patent/GB1602936A/en not_active Expired
- 1978-05-23 FR FR7815306A patent/FR2392087A1/en active Granted
- 1978-05-23 JP JP6067678A patent/JPS53144930A/en active Granted
- 1978-05-23 NL NL7805579A patent/NL7805579A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6138216B2 (en) | 1986-08-28 |
| JPS53144930A (en) | 1978-12-16 |
| NL7805579A (en) | 1978-11-27 |
| CH649568A5 (en) | 1985-05-31 |
| IT1096366B (en) | 1985-08-26 |
| FR2392087A1 (en) | 1978-12-22 |
| FR2392087B1 (en) | 1983-01-28 |
| IT7823528A0 (en) | 1978-05-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |