DE1945053C3 - Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben, Bedrucken und Massefärben von Polyacrylnitril, sauer modifizierten Polyestern oder modifizierten Polyamiden - Google Patents
Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben, Bedrucken und Massefärben von Polyacrylnitril, sauer modifizierten Polyestern oder modifizierten PolyamidenInfo
- Publication number
- DE1945053C3 DE1945053C3 DE19691945053 DE1945053A DE1945053C3 DE 1945053 C3 DE1945053 C3 DE 1945053C3 DE 19691945053 DE19691945053 DE 19691945053 DE 1945053 A DE1945053 A DE 1945053A DE 1945053 C3 DE1945053 C3 DE 1945053C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- phenyl
- substituted
- pyrazoline
- basic dyes
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 239000000981 basic dye Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000004043 dyeing Methods 0.000 title description 12
- 229920000728 polyester Polymers 0.000 title description 7
- 239000004952 Polyamide Substances 0.000 title description 4
- 229920002239 polyacrylonitrile Polymers 0.000 title description 4
- 229920002647 polyamide Polymers 0.000 title description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 124
- 239000001257 hydrogen Substances 0.000 claims description 124
- 150000002431 hydrogen Chemical class 0.000 claims description 108
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- -1 phenoxy, Thienyl Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 150000001450 anions Chemical class 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 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 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004188 dichlorophenyl group Chemical group 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000003219 pyrazolines Chemical class 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- RXQQWLMUBOTBSO-UHFFFAOYSA-N 3,5-diphenyl-2,3-dihydro-1h-pyrazole Chemical compound N1NC(C=2C=CC=CC=2)=CC1C1=CC=CC=C1 RXQQWLMUBOTBSO-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FJRXVHBDFFLPJZ-UHFFFAOYSA-N 5-(2-ethylphenyl)-2,3-dihydro-1H-pyrazole Chemical compound C(C)C1=C(C=CC=C1)C=1NNCC1 FJRXVHBDFFLPJZ-UHFFFAOYSA-N 0.000 description 1
- IEUDHPNYDCLIBH-UHFFFAOYSA-N 5-(4-chlorophenyl)-2,3-dihydro-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=CCNN1 IEUDHPNYDCLIBH-UHFFFAOYSA-N 0.000 description 1
- ISGSGHXVZFZYSY-UHFFFAOYSA-N 5-(4-propan-2-ylphenyl)-2,3-dihydro-1H-pyrazole Chemical compound C1=CC(C(C)C)=CC=C1C1=CCNN1 ISGSGHXVZFZYSY-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 244000198134 Agave sisalana Species 0.000 description 1
- NXVOGIGPSRCJOI-UHFFFAOYSA-N BrC1=CC=C(C=C1)C=1NNCC1 Chemical compound BrC1=CC=C(C=C1)C=1NNCC1 NXVOGIGPSRCJOI-UHFFFAOYSA-N 0.000 description 1
- PVLPTQIQJZHNAE-UHFFFAOYSA-N C1(=CC=CC=C1)C=1NNCC1C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C=1NNCC1C1=CC=CC=C1 PVLPTQIQJZHNAE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- AJCHQLSBETWPLY-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C=1NNCC1 Chemical compound ClC1=C(C=CC(=C1)Cl)C=1NNCC1 AJCHQLSBETWPLY-UHFFFAOYSA-N 0.000 description 1
- CMEPHBQTYKKWEQ-UHFFFAOYSA-N ClC1=CC=C(C2NNC(C=CC(C=C3)=CC=C3Cl)=C2)C=C1 Chemical compound ClC1=CC=C(C2NNC(C=CC(C=C3)=CC=C3Cl)=C2)C=C1 CMEPHBQTYKKWEQ-UHFFFAOYSA-N 0.000 description 1
- XYPAVLJUPYCANU-UHFFFAOYSA-N ClC=1C=C(C=CC1)C=1NNCC1 Chemical compound ClC=1C=C(C=CC1)C=1NNCC1 XYPAVLJUPYCANU-UHFFFAOYSA-N 0.000 description 1
- KLENCTJOUUTNCN-UHFFFAOYSA-N ClC=1C=C(C=CC1Cl)C=1NNCC1 Chemical compound ClC=1C=C(C=CC1Cl)C=1NNCC1 KLENCTJOUUTNCN-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 240000004792 Corchorus capsularis Species 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- DDKMFOUTRRODRE-UHFFFAOYSA-N chloromethanone Chemical compound Cl[C]=O DDKMFOUTRRODRE-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000005528 methosulfate group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QYQVNWWXGMIROZ-UHFFFAOYSA-N oxalic acid perchloric acid Chemical compound Cl(=O)(=O)(=O)O.C(C(=O)O)(=O)O QYQVNWWXGMIROZ-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- ZUKJXYRXZAVUJV-UHFFFAOYSA-N phosphoryl trichloride trichlorophosphane Chemical compound ClP(Cl)Cl.ClP(Cl)(Cl)=O ZUKJXYRXZAVUJV-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
- C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
- C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
-
- 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/06—Naphtholactam dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE755757D BE755757A (fr) | 1969-09-05 | Colorants basiques et leur obtention | |
| DE19691945053 DE1945053C3 (de) | 1969-09-05 | 1969-09-05 | Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben, Bedrucken und Massefärben von Polyacrylnitril, sauer modifizierten Polyestern oder modifizierten Polyamiden |
| CH1864170A CH508693A (de) | 1969-09-05 | 1970-08-20 | Verfahren zur Herstellung basischer Farbstoffe |
| CH1248770A CH538008A (de) | 1969-09-05 | 1970-08-20 | Verfahren zum Färben oder Bedrucken von Textilmaterialien |
| CH1248770D CH1248770A4 (enrdf_load_stackoverflow) | 1969-09-05 | 1970-08-20 | |
| AT778070A AT295688B (de) | 1969-09-05 | 1970-08-27 | Verfahren zur Herstellung von neuen basischen Farbstoffen |
| CA091967A CA918156A (en) | 1969-09-05 | 1970-08-31 | Basic dyestuffs |
| US00068485A US3770727A (en) | 1969-09-05 | 1970-08-31 | Novel basic pyrazoline dyes |
| NL7013067A NL166967C (nl) | 1969-09-05 | 1970-09-03 | Werkwijze voor het bereiden van basische kleurstoffen, werkwijze voor het verven, bedrukken en/of in de massa verven van materialen, alsmede de uit deze behandelde materialen bestaande gevormde voortbrengsels. |
| JP7674970A JPS5338291B1 (enrdf_load_stackoverflow) | 1969-09-05 | 1970-09-03 | |
| JP45076750A JPS4817628B1 (enrdf_load_stackoverflow) | 1969-09-05 | 1970-09-03 | |
| FR7032322A FR2061008A5 (enrdf_load_stackoverflow) | 1969-09-05 | 1970-09-04 | |
| GB1301492D GB1301492A (enrdf_load_stackoverflow) | 1969-09-05 | 1970-09-04 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691945053 DE1945053C3 (de) | 1969-09-05 | 1969-09-05 | Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben, Bedrucken und Massefärben von Polyacrylnitril, sauer modifizierten Polyestern oder modifizierten Polyamiden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1945053A1 DE1945053A1 (de) | 1971-03-11 |
| DE1945053B2 DE1945053B2 (de) | 1978-02-09 |
| DE1945053C3 true DE1945053C3 (de) | 1978-10-12 |
Family
ID=5744693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691945053 Expired DE1945053C3 (de) | 1969-09-05 | 1969-09-05 | Basische Farbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben, Bedrucken und Massefärben von Polyacrylnitril, sauer modifizierten Polyestern oder modifizierten Polyamiden |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS5338291B1 (enrdf_load_stackoverflow) |
| AT (1) | AT295688B (enrdf_load_stackoverflow) |
| BE (1) | BE755757A (enrdf_load_stackoverflow) |
| CA (1) | CA918156A (enrdf_load_stackoverflow) |
| CH (2) | CH1248770A4 (enrdf_load_stackoverflow) |
| DE (1) | DE1945053C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2061008A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1301492A (enrdf_load_stackoverflow) |
| NL (1) | NL166967C (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2858553B1 (fr) * | 2003-08-05 | 2005-09-23 | Oreal | Composition de teinture des fibres keratiniques comprenant un derive 1h-pyrazolyl-ethenyl-indolium |
-
0
- BE BE755757D patent/BE755757A/xx unknown
-
1969
- 1969-09-05 DE DE19691945053 patent/DE1945053C3/de not_active Expired
-
1970
- 1970-08-20 CH CH1248770D patent/CH1248770A4/xx unknown
- 1970-08-20 CH CH1248770A patent/CH538008A/de unknown
- 1970-08-27 AT AT778070A patent/AT295688B/de not_active IP Right Cessation
- 1970-08-31 CA CA091967A patent/CA918156A/en not_active Expired
- 1970-09-03 JP JP7674970A patent/JPS5338291B1/ja active Pending
- 1970-09-03 NL NL7013067A patent/NL166967C/xx not_active IP Right Cessation
- 1970-09-03 JP JP45076750A patent/JPS4817628B1/ja active Pending
- 1970-09-04 GB GB1301492D patent/GB1301492A/en not_active Expired
- 1970-09-04 FR FR7032322A patent/FR2061008A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5338291B1 (enrdf_load_stackoverflow) | 1978-10-14 |
| GB1301492A (enrdf_load_stackoverflow) | 1972-12-29 |
| NL166967C (nl) | 1981-10-15 |
| NL7013067A (enrdf_load_stackoverflow) | 1971-03-09 |
| FR2061008A5 (enrdf_load_stackoverflow) | 1971-06-18 |
| CH538008A (de) | 1972-12-29 |
| DE1945053A1 (de) | 1971-03-11 |
| JPS4817628B1 (enrdf_load_stackoverflow) | 1973-05-30 |
| DE1945053B2 (de) | 1978-02-09 |
| CA918156A (en) | 1973-01-02 |
| CH1248770A4 (enrdf_load_stackoverflow) | 1972-12-29 |
| BE755757A (fr) | 1971-02-15 |
| AT295688B (de) | 1972-01-10 |
| NL166967B (nl) | 1981-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |