DE2620981A1 - Neue chromkomplexfarbstoffe, deren herstellung und verwendung - Google Patents
Neue chromkomplexfarbstoffe, deren herstellung und verwendungInfo
- Publication number
- DE2620981A1 DE2620981A1 DE19762620981 DE2620981A DE2620981A1 DE 2620981 A1 DE2620981 A1 DE 2620981A1 DE 19762620981 DE19762620981 DE 19762620981 DE 2620981 A DE2620981 A DE 2620981A DE 2620981 A1 DE2620981 A1 DE 2620981A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- radical
- sulfo
- alkyl
- 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.)
- Granted
Links
- 239000000975 dye Substances 0.000 title claims description 61
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 102
- -1 aliphatic radical Chemical class 0.000 claims description 70
- 229910052804 chromium Inorganic materials 0.000 claims description 57
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 56
- 239000011651 chromium Substances 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000000987 azo dye Substances 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 150000001413 amino acids Chemical class 0.000 claims description 14
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 12
- 238000010168 coupling process Methods 0.000 claims description 12
- 238000005859 coupling reaction Methods 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 239000004952 Polyamide Substances 0.000 claims description 10
- 229920002647 polyamide Polymers 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 9
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 8
- 150000002790 naphthalenes Chemical class 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004442 acylamino group Chemical group 0.000 claims description 7
- 238000004043 dyeing Methods 0.000 claims description 7
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003931 anilides Chemical class 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- PENGHVVNPVWBMD-UHFFFAOYSA-N OS(=O)(=O)Cl[N+]([O-])=O Chemical compound OS(=O)(=O)Cl[N+]([O-])=O PENGHVVNPVWBMD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 150000001576 beta-amino acids Chemical class 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 2
- 238000004532 chromating Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 240000007817 Olea europaea Species 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 12
- 150000001299 aldehydes Chemical class 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000010985 leather Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- DOPJTDJKZNWLRB-UHFFFAOYSA-N 2-Amino-5-nitrophenol Chemical compound NC1=CC=C([N+]([O-])=O)C=C1O DOPJTDJKZNWLRB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001845 chromium compounds Chemical class 0.000 description 3
- LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 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
- 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
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- DSTPUJAJSXTJHM-UHFFFAOYSA-N 4-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(C)=CC=C1O DSTPUJAJSXTJHM-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
- SEMRCUIXRUXGJX-UHFFFAOYSA-N 6-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=CC(N)=CC=C21 SEMRCUIXRUXGJX-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N Acetylene Chemical compound C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical group 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 229940000635 beta-alanine Drugs 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 150000001844 chromium Chemical class 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-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
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000565 sulfonamide group Chemical group 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- JWQYZECMEPOAPF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-ol Chemical compound C1=CC=C2CC(O)CCC2=C1 JWQYZECMEPOAPF-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- LLSNTRRAZWBTCK-UHFFFAOYSA-N 1-(3-hydroxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CC(O)=CC2=C1 LLSNTRRAZWBTCK-UHFFFAOYSA-N 0.000 description 1
- SAPGSAHOBOEJDV-UHFFFAOYSA-N 1-(4-hydroxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=C(O)C2=C1 SAPGSAHOBOEJDV-UHFFFAOYSA-N 0.000 description 1
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 description 1
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
- JXPVQFCUIAKFLT-UHFFFAOYSA-N 2,5-dimethyl-1h-pyrazol-3-one Chemical compound CC1=CC(=O)N(C)N1 JXPVQFCUIAKFLT-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- BCESCHGDVIYYPC-UHFFFAOYSA-N 2-(ethylamino)phenol Chemical compound CCNC1=CC=CC=C1O BCESCHGDVIYYPC-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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- UFDFFEMHDKXMBG-UHFFFAOYSA-N 2-acetamidoprop-2-enoic acid Chemical compound CC(=O)NC(=C)C(O)=O UFDFFEMHDKXMBG-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
- JSHJJLQJRLNBBA-UHFFFAOYSA-N 2-amino-3-chlorophenol Chemical compound NC1=C(O)C=CC=C1Cl JSHJJLQJRLNBBA-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
- TUADYTFWZPZZTP-UHFFFAOYSA-N 2-amino-4-methoxyphenol Chemical compound COC1=CC=C(O)C(N)=C1 TUADYTFWZPZZTP-UHFFFAOYSA-N 0.000 description 1
- RDFIUQJNELYXKG-UHFFFAOYSA-N 2-amino-5-chloro-4-methoxyphenol Chemical compound COC1=CC(N)=C(O)C=C1Cl RDFIUQJNELYXKG-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
- ZMXYNJXDULEQCK-UHFFFAOYSA-N 2-amino-p-cresol Chemical compound CC1=CC=C(O)C(N)=C1 ZMXYNJXDULEQCK-UHFFFAOYSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- USQHEVWOPJDAAX-UHFFFAOYSA-N 2-azaniumylcyclohexane-1-carboxylate Chemical compound NC1CCCCC1C(O)=O USQHEVWOPJDAAX-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-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
- DSXKMMAQDSAZAC-UHFFFAOYSA-N 2-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C)=C(O)C(C=O)=C1 DSXKMMAQDSAZAC-UHFFFAOYSA-N 0.000 description 1
- YRGYYQCOWUULNF-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CC(=O)NC(O)=C1C#N YRGYYQCOWUULNF-UHFFFAOYSA-N 0.000 description 1
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- VZLLZDZTQPBHAZ-UHFFFAOYSA-N 2-nitroaniline-4-sulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1[N+]([O-])=O VZLLZDZTQPBHAZ-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
- ANVZQEASRUZEQM-UHFFFAOYSA-N 3-(2-acetamidophenyl)prop-2-enoic acid Chemical compound CC(=O)NC1=CC=CC=C1C=CC(O)=O ANVZQEASRUZEQM-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
- ZEWCASRNRWXXSO-UHFFFAOYSA-N 3-amino-4-hydroxybenzonitrile Chemical compound NC1=CC(C#N)=CC=C1O ZEWCASRNRWXXSO-UHFFFAOYSA-N 0.000 description 1
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- 150000004992 toluidines Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 125000001874 trioxidanyl group Chemical group [*]OOO[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 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
- C09B55/001—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
-
- 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
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH619375A CH624979A5 (en, 2012) | 1975-05-14 | 1975-05-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2620981A1 true DE2620981A1 (de) | 1976-11-25 |
| DE2620981C2 DE2620981C2 (en, 2012) | 1988-02-25 |
Family
ID=4305727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762620981 Granted DE2620981A1 (de) | 1975-05-14 | 1976-05-12 | Neue chromkomplexfarbstoffe, deren herstellung und verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4033942A (en, 2012) |
| JP (1) | JPS51139826A (en, 2012) |
| AU (1) | AU508949B2 (en, 2012) |
| BE (1) | BE841773A (en, 2012) |
| CH (1) | CH624979A5 (en, 2012) |
| DE (1) | DE2620981A1 (en, 2012) |
| FR (1) | FR2311063A1 (en, 2012) |
| GB (1) | GB1540447A (en, 2012) |
| NL (1) | NL7604638A (en, 2012) |
| ZA (1) | ZA762865B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264494A (en) * | 1977-08-05 | 1981-04-28 | Basf Aktiengesellschaft | Chromium complex dyestuffs for natural polyamides and synthetic nylons |
| EP0017114A3 (de) * | 1979-04-05 | 1981-07-01 | Bayer Ag | Verfahren zur Herstellung von konzentrierten Lösungen von 1:2-Metallkomplex-Farbstoffen und deren Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Polyamiden |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4116952A (en) * | 1975-05-14 | 1978-09-26 | Ciba-Geigy Corporation | Unsymmetrical azo - azo methine 1:2 chromium complex dyes |
| DE2614201A1 (de) * | 1976-04-02 | 1977-10-20 | Basf Ag | Unsymmetrische, eine azo- und eine azomethinverbindung enthaltende 1 zu 2- chromkomplexe |
| DE2735287C2 (de) * | 1977-08-05 | 1985-03-28 | Basf Ag, 6700 Ludwigshafen | 1:2-Chromkomplexfarbstoffe, deren Herstellung und Verwendung |
| IT1096366B (it) * | 1977-05-23 | 1985-08-26 | Basf Ag | Coloranti complessi del cromo 1:2" |
| US4256633A (en) * | 1978-04-25 | 1981-03-17 | Ciba-Geigy Corporation | Chromium complex compounds, process for their manufacture and use thereof |
| PT70155A (en) * | 1978-09-20 | 1979-10-01 | Ciba Geigy Ag | Process for the preparation of chromium complex dyes |
| US4265811A (en) * | 1979-01-08 | 1981-05-05 | Polaroid Corporation | Novel azo dyes |
| US4267253A (en) * | 1979-01-08 | 1981-05-12 | Polaroid Corporation | Chrome complexed magenta dye developers |
| US4267252A (en) * | 1979-01-08 | 1981-05-12 | Polaroid Corporation | Chrome complexed magenta dye developers |
| US4340536A (en) * | 1979-05-23 | 1982-07-20 | Ciba-Geigy Corporation | Chrome-complex dyes and the production and use thereof |
| DE3034002A1 (de) | 1980-09-10 | 1982-04-22 | Basf Ag, 6700 Ludwigshafen | Sulfonsaeuregruppenhaltige 1 zu 2-chromkomplexfarbstoffe |
| JPS5757485A (en) * | 1980-09-25 | 1982-04-06 | Nippon Koei Co Ltd | Rail point freezing preventing device |
| US4507124A (en) * | 1982-07-02 | 1985-03-26 | Ciba-Geigy Corporation | 1:2 Metal complexes of azomethine dyes having arylazo groups |
| JPS59141554A (ja) * | 1983-02-01 | 1984-08-14 | Sogo Yatsukou Kk | 新規錯体形成化合物及びそれを有効成分として含有する血圧降下剤 |
| DE3433980A1 (de) * | 1984-09-15 | 1986-03-27 | Bayer Ag, 5090 Leverkusen | Unsymmetrische 1:2-chromkomplexfarbstoffe |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB947607A (en) * | 1961-05-03 | 1964-01-22 | Ici Ltd | Chromium-containing azomethine dyestuffs |
| DE2123453A1 (de) * | 1971-05-12 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Metallkomplex-Farbstoffe |
| DE2461481B2 (de) | 1974-12-24 | 1978-10-26 | Basf Ag, 6700 Ludwigshafen | Unsymmetrische, eine Azo- und eine Azomethinverbindung enthaltende 1 zu 2-Chromkomplexe, Verfahren zu deren Herstellung und ihre Verwendung |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1116491A (fr) * | 1953-11-26 | 1956-05-08 | Geigy Ag J R | Colorants métallifières et leur procédé de préparation |
| US2985646A (en) * | 1957-03-14 | 1961-05-23 | Geigy Ag J R | Chromium-containing dyestuffs |
| DE1444655C3 (de) * | 1963-02-19 | 1974-08-08 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2:1-Chrommischkomplex-Azofarbstoffen |
| CH443518A (de) * | 1964-07-31 | 1967-09-15 | Geigy Ag J R | Verfahren zur Herstellung wasserlöslicher chromhaltiger Farbstoffe |
| FR1442837A (fr) * | 1964-07-31 | 1966-06-17 | Geigy Ag J R | Nouveaux colorants azoïques, leur préparation et leurs applications |
| NL129233C (en, 2012) * | 1965-01-15 | |||
| DE1770959A1 (de) * | 1968-07-24 | 1971-06-03 | Basf Ag | Metallhaltige Farbstoffe |
| 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 |
| CH599307A5 (en, 2012) * | 1974-05-09 | 1978-05-31 | Ciba Geigy Ag |
-
1975
- 1975-05-14 CH CH619375A patent/CH624979A5/de not_active IP Right Cessation
-
1976
- 1976-04-27 US US05/680,640 patent/US4033942A/en not_active Expired - Lifetime
- 1976-04-29 NL NL7604638A patent/NL7604638A/xx not_active Application Discontinuation
- 1976-05-10 FR FR7613944A patent/FR2311063A1/fr active Granted
- 1976-05-12 DE DE19762620981 patent/DE2620981A1/de active Granted
- 1976-05-13 GB GB19834/76A patent/GB1540447A/en not_active Expired
- 1976-05-13 ZA ZA762865A patent/ZA762865B/xx unknown
- 1976-05-13 BE BE166978A patent/BE841773A/xx not_active IP Right Cessation
- 1976-05-13 AU AU13920/76A patent/AU508949B2/en not_active Expired
- 1976-05-14 JP JP51054440A patent/JPS51139826A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB947607A (en) * | 1961-05-03 | 1964-01-22 | Ici Ltd | Chromium-containing azomethine dyestuffs |
| DE2123453A1 (de) * | 1971-05-12 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Metallkomplex-Farbstoffe |
| DE2461481B2 (de) | 1974-12-24 | 1978-10-26 | Basf Ag, 6700 Ludwigshafen | Unsymmetrische, eine Azo- und eine Azomethinverbindung enthaltende 1 zu 2-Chromkomplexe, Verfahren zu deren Herstellung und ihre Verwendung |
Non-Patent Citations (2)
| Title |
|---|
| DE-AS 24 61 481 * |
| In Betracht gezogene ältere Anmeldungen: DE-AS 25 01 469 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4264494A (en) * | 1977-08-05 | 1981-04-28 | Basf Aktiengesellschaft | Chromium complex dyestuffs for natural polyamides and synthetic nylons |
| EP0017114A3 (de) * | 1979-04-05 | 1981-07-01 | Bayer Ag | Verfahren zur Herstellung von konzentrierten Lösungen von 1:2-Metallkomplex-Farbstoffen und deren Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Polyamiden |
Also Published As
| Publication number | Publication date |
|---|---|
| CH624979A5 (en, 2012) | 1981-08-31 |
| DE2620981C2 (en, 2012) | 1988-02-25 |
| BE841773A (fr) | 1976-11-16 |
| JPS6114177B2 (en, 2012) | 1986-04-17 |
| JPS51139826A (en) | 1976-12-02 |
| FR2311063B1 (en, 2012) | 1978-05-19 |
| FR2311063A1 (fr) | 1976-12-10 |
| AU508949B2 (en) | 1980-04-17 |
| NL7604638A (nl) | 1976-11-16 |
| AU1392076A (en) | 1977-11-17 |
| US4033942A (en) | 1977-07-05 |
| GB1540447A (en) | 1979-02-14 |
| ZA762865B (en) | 1977-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |