DE2105935C3 - Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Textilfasermaterialien - Google Patents
Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen TextilfasermaterialienInfo
- Publication number
- DE2105935C3 DE2105935C3 DE19712105935 DE2105935A DE2105935C3 DE 2105935 C3 DE2105935 C3 DE 2105935C3 DE 19712105935 DE19712105935 DE 19712105935 DE 2105935 A DE2105935 A DE 2105935A DE 2105935 C3 DE2105935 C3 DE 2105935C3
- Authority
- DE
- Germany
- Prior art keywords
- indole
- methyl
- phenyl
- phenol
- acid
- 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
- 239000000975 dye Substances 0.000 title claims description 37
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 9
- 238000004043 dyeing Methods 0.000 title claims description 7
- 229920002994 synthetic fiber Polymers 0.000 title claims description 4
- 239000004758 synthetic textile Substances 0.000 title claims description 3
- 239000002657 fibrous material Substances 0.000 title 1
- -1 phenoxyacetyl Chemical group 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 2
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- NGRHHTODLFNUHB-UHFFFAOYSA-N CCN(CC)S(=O)=O Chemical compound CCN(CC)S(=O)=O NGRHHTODLFNUHB-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 230000008878 coupling Effects 0.000 description 30
- 238000010168 coupling process Methods 0.000 description 30
- 238000005859 coupling reaction Methods 0.000 description 30
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 18
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 16
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000004952 Polyamide Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 8
- 230000007935 neutral effect Effects 0.000 description 8
- 229920002647 polyamide Polymers 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 238000007127 saponification reaction Methods 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- IZNVWIXUMIMNSP-UHFFFAOYSA-N 2-phenyl-1h-indole-5-sulfonic acid Chemical compound C=1C2=CC(S(=O)(=O)O)=CC=C2NC=1C1=CC=CC=C1 IZNVWIXUMIMNSP-UHFFFAOYSA-N 0.000 description 5
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 150000001989 diazonium salts Chemical class 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- BJMUOUXGBFNLSN-UHFFFAOYSA-N 1,2-dimethylindole Chemical compound C1=CC=C2N(C)C(C)=CC2=C1 BJMUOUXGBFNLSN-UHFFFAOYSA-N 0.000 description 4
- SFWZZSXCWQTORH-UHFFFAOYSA-N 1-methyl-2-phenylindole Chemical compound C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 SFWZZSXCWQTORH-UHFFFAOYSA-N 0.000 description 4
- ZFLFWZRPMDXJCW-UHFFFAOYSA-N 2,5-dimethyl-1h-indole Chemical compound CC1=CC=C2NC(C)=CC2=C1 ZFLFWZRPMDXJCW-UHFFFAOYSA-N 0.000 description 4
- WUVWAXJXPRYUME-UHFFFAOYSA-N 5-chloro-2-methyl-1h-indole Chemical compound ClC1=CC=C2NC(C)=CC2=C1 WUVWAXJXPRYUME-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YZKUEVLTJBFTCA-UHFFFAOYSA-N 2-methyl-1H-indole 2-phenyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1.N1C2=CC=CC=C2C=C1C1=CC=CC=C1 YZKUEVLTJBFTCA-UHFFFAOYSA-N 0.000 description 3
- UNJRQDPTLDVHOR-UHFFFAOYSA-N 5-nitro-2-phenyl-1h-indole Chemical compound C=1C2=CC([N+](=O)[O-])=CC=C2NC=1C1=CC=CC=C1 UNJRQDPTLDVHOR-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000002475 indoles Chemical class 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- LMWMTSCFTPQVCJ-UHFFFAOYSA-N 2-methylphenol;phenol Chemical compound OC1=CC=CC=C1.CC1=CC=CC=C1O LMWMTSCFTPQVCJ-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052979 sodium sulfide Inorganic materials 0.000 description 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- JVTFGPFQEYYTQQ-UHFFFAOYSA-N 2-(aminodiazenyl)-3-hydroxybenzenesulfonic acid Chemical compound NN=NC1=C(O)C=CC=C1S(O)(=O)=O JVTFGPFQEYYTQQ-UHFFFAOYSA-N 0.000 description 1
- PYTYPCVWWHOWFP-UHFFFAOYSA-N 2-(aminodiazenyl)-3-methoxybenzenesulfonic acid Chemical compound COC1=CC=CC(S(O)(=O)=O)=C1N=NN PYTYPCVWWHOWFP-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
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- CTUAXDSKEHXGDT-UHFFFAOYSA-N 3-ethyl-1,2-dimethylindole Chemical compound C1=CC=C2C(CC)=C(C)N(C)C2=C1 CTUAXDSKEHXGDT-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- NNJZGKJLPCDYQB-UHFFFAOYSA-N 6-chloro-2-methyl-1h-indole Chemical compound C1=C(Cl)C=C2NC(C)=CC2=C1 NNJZGKJLPCDYQB-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 229910014276 N-Li Inorganic materials 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- RYOXRUCETIDZFH-UHFFFAOYSA-N N1C2=CC=CC=C2C=C1C1=CC=CC=C1.C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1.C=1C2=CC=CC=C2N(C)C=1C1=CC=CC=C1 RYOXRUCETIDZFH-UHFFFAOYSA-N 0.000 description 1
- 229910014326 N—Li Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- QKZIVVMOMKTVIK-UHFFFAOYSA-N anilinomethanesulfonic acid Chemical compound OS(=O)(=O)CNC1=CC=CC=C1 QKZIVVMOMKTVIK-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- CQUCHFCHKDWFHR-UHFFFAOYSA-N bromoethane;chloroethane Chemical compound CCCl.CCBr CQUCHFCHKDWFHR-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005056 compaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 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 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- UGGRVGVKANAYDM-UHFFFAOYSA-N nitrous hydrazide Chemical group NN=NO UGGRVGVKANAYDM-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 125000003111 oxaloamino group Chemical group C(=O)(C(=O)O)N* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000006207 propylation Effects 0.000 description 1
- 125000006239 protecting group Chemical class 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/12—Disazo dyes from other coupling components "C"
- C09B31/14—Heterocyclic components
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/28—Preparation of azo dyes from other azo compounds by etherification of hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712105935 DE2105935C3 (de) | 1971-02-09 | 1971-02-09 | Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Textilfasermaterialien |
| CH1282074A CH601434A5 (enrdf_load_stackoverflow) | 1971-02-09 | 1972-02-03 | |
| NL7201576A NL7201576A (enrdf_load_stackoverflow) | 1971-02-09 | 1972-02-07 | |
| IT2029672A IT954883B (it) | 1971-02-09 | 1972-02-07 | Disazocoloranti |
| GB581372A GB1328774A (en) | 1971-02-09 | 1972-02-08 | Disazo dyestuffs |
| FR7204376A FR2124606B1 (enrdf_load_stackoverflow) | 1971-02-09 | 1972-02-09 | |
| BE779131A BE779131A (fr) | 1971-02-09 | 1972-02-09 | Colorants disazoiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712105935 DE2105935C3 (de) | 1971-02-09 | 1971-02-09 | Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Textilfasermaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2105935A1 DE2105935A1 (de) | 1972-08-24 |
| DE2105935B2 DE2105935B2 (de) | 1978-04-13 |
| DE2105935C3 true DE2105935C3 (de) | 1978-12-21 |
Family
ID=5798172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712105935 Expired DE2105935C3 (de) | 1971-02-09 | 1971-02-09 | Disazofarbstoffe und ihre Verwendung zum Färben und Bedrucken von natürlichen und synthetischen Textilfasermaterialien |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE779131A (enrdf_load_stackoverflow) |
| CH (1) | CH601434A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2105935C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2124606B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1328774A (enrdf_load_stackoverflow) |
| IT (1) | IT954883B (enrdf_load_stackoverflow) |
| NL (1) | NL7201576A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2708188C2 (de) | 1977-02-25 | 1979-02-08 | Bayer Ag, 5090 Leverkusen | Stabilisierung anionischer Indolfarbstoffe |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1360578A (fr) * | 1963-06-14 | 1964-05-08 | Basf Ag | Bains de teinture et couleurs d'impression pour la teinture et l'impression d'objets de polyamides synthétiques et de polyuréthanes |
-
1971
- 1971-02-09 DE DE19712105935 patent/DE2105935C3/de not_active Expired
-
1972
- 1972-02-03 CH CH1282074A patent/CH601434A5/xx not_active IP Right Cessation
- 1972-02-07 NL NL7201576A patent/NL7201576A/xx unknown
- 1972-02-07 IT IT2029672A patent/IT954883B/it active
- 1972-02-08 GB GB581372A patent/GB1328774A/en not_active Expired
- 1972-02-09 FR FR7204376A patent/FR2124606B1/fr not_active Expired
- 1972-02-09 BE BE779131A patent/BE779131A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT954883B (it) | 1973-09-15 |
| DE2105935B2 (de) | 1978-04-13 |
| FR2124606A1 (enrdf_load_stackoverflow) | 1972-09-22 |
| GB1328774A (en) | 1973-09-05 |
| CH601434A5 (enrdf_load_stackoverflow) | 1978-07-14 |
| FR2124606B1 (enrdf_load_stackoverflow) | 1975-10-24 |
| NL7201576A (enrdf_load_stackoverflow) | 1972-08-11 |
| BE779131A (fr) | 1972-08-09 |
| DE2105935A1 (de) | 1972-08-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |