CH515315A - Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen - Google Patents
Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen FormazanfarbstoffenInfo
- Publication number
- CH515315A CH515315A CH287070A CH287070A CH515315A CH 515315 A CH515315 A CH 515315A CH 287070 A CH287070 A CH 287070A CH 287070 A CH287070 A CH 287070A CH 515315 A CH515315 A CH 515315A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- group
- formula
- heavy metal
- difluoro
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims abstract description 25
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 title claims description 14
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 title claims description 14
- 238000004043 dyeing Methods 0.000 title abstract description 7
- 239000004952 Polyamide Substances 0.000 title abstract description 4
- 229920002647 polyamide Polymers 0.000 title abstract description 4
- 239000001913 cellulose Substances 0.000 title description 4
- 229920002678 cellulose Polymers 0.000 title description 4
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 150000002790 naphthalenes Chemical class 0.000 claims 2
- 230000008878 coupling Effects 0.000 abstract description 6
- 238000010168 coupling process Methods 0.000 abstract description 6
- 238000005859 coupling reaction Methods 0.000 abstract description 6
- 239000011368 organic material Substances 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 239000004627 regenerated cellulose Substances 0.000 abstract description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- -1 heterocyclic radical Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- NTSYSQNAPGMSIH-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine Chemical compound FC1=CC(F)=NC(F)=N1 NTSYSQNAPGMSIH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BIMGULMREAFXSC-UHFFFAOYSA-N 2,4,5-trifluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1F BIMGULMREAFXSC-UHFFFAOYSA-N 0.000 description 1
- LUOWQRCVEYJUJS-UHFFFAOYSA-N 2,4,6-trifluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(C(F)(F)F)C(F)=N1 LUOWQRCVEYJUJS-UHFFFAOYSA-N 0.000 description 1
- AZVALKSFVWAVOL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1F AZVALKSFVWAVOL-UHFFFAOYSA-N 0.000 description 1
- CZHWBISSOIPPNL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=C(F)N=C(F)N=C1F CZHWBISSOIPPNL-UHFFFAOYSA-N 0.000 description 1
- SLCPPBRBHAMWLK-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine-5-carboxamide Chemical compound NC(=O)C1=C(F)N=C(F)N=C1F SLCPPBRBHAMWLK-UHFFFAOYSA-N 0.000 description 1
- YXYCPKOAGWDZKX-UHFFFAOYSA-N 2,4-difluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC=C(C(F)(F)F)C(F)=N1 YXYCPKOAGWDZKX-UHFFFAOYSA-N 0.000 description 1
- NIAMELKDNLLWRH-UHFFFAOYSA-N 2,4-difluoro-5-methylpyrimidine Chemical compound CC1=CN=C(F)N=C1F NIAMELKDNLLWRH-UHFFFAOYSA-N 0.000 description 1
- QYJOBZGPEJHODY-UHFFFAOYSA-N 2,4-difluoro-5-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=CN=C(F)N=C1F QYJOBZGPEJHODY-UHFFFAOYSA-N 0.000 description 1
- GIBOHPZCGYRPBS-UHFFFAOYSA-N 2,4-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=C(F)N=C1F GIBOHPZCGYRPBS-UHFFFAOYSA-N 0.000 description 1
- GJOGRJUICNPNSV-UHFFFAOYSA-N 2,4-difluoro-5-phenylpyrimidine Chemical compound FC1=NC(F)=NC=C1C1=CC=CC=C1 GJOGRJUICNPNSV-UHFFFAOYSA-N 0.000 description 1
- FKSSZHRRUUZKCM-UHFFFAOYSA-N 2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=CC(C(F)(F)F)=NC(F)=N1 FKSSZHRRUUZKCM-UHFFFAOYSA-N 0.000 description 1
- YKLOPWRWWFKUBX-UHFFFAOYSA-N 2,4-difluoro-6-methylpyrimidine Chemical compound CC1=CC(F)=NC(F)=N1 YKLOPWRWWFKUBX-UHFFFAOYSA-N 0.000 description 1
- ZCHHTEOFXSGDMW-UHFFFAOYSA-N 2,4-difluoro-6-phenylpyrimidine Chemical compound FC1=NC(F)=CC(C=2C=CC=CC=2)=N1 ZCHHTEOFXSGDMW-UHFFFAOYSA-N 0.000 description 1
- JZSYSXZDIQUOGP-UHFFFAOYSA-N 2,4-difluoropyrimidine Chemical compound FC1=CC=NC(F)=N1 JZSYSXZDIQUOGP-UHFFFAOYSA-N 0.000 description 1
- AOSHQVWIJNXEMB-UHFFFAOYSA-N 2,4-difluoropyrimidine-5-carbonitrile Chemical compound FC1=NC=C(C#N)C(F)=N1 AOSHQVWIJNXEMB-UHFFFAOYSA-N 0.000 description 1
- KRJYAVYJNNWRSQ-UHFFFAOYSA-N 2,4-difluoropyrimidine-5-sulfonamide Chemical compound NS(=O)(=O)C1=CN=C(F)N=C1F KRJYAVYJNNWRSQ-UHFFFAOYSA-N 0.000 description 1
- YEVZRRNYSGBIAU-UHFFFAOYSA-N 2,5-dibromo-4,6-difluoropyrimidine Chemical compound FC1=NC(Br)=NC(F)=C1Br YEVZRRNYSGBIAU-UHFFFAOYSA-N 0.000 description 1
- LRTVASZRVUNBAP-UHFFFAOYSA-N 2,5-dichloro-4,6-difluoropyrimidine Chemical compound FC1=NC(Cl)=NC(F)=C1Cl LRTVASZRVUNBAP-UHFFFAOYSA-N 0.000 description 1
- WFJGZGDYFGUMCA-UHFFFAOYSA-N 2,6-difluoropyrimidine-4-carbonitrile Chemical compound FC1=CC(C#N)=NC(F)=N1 WFJGZGDYFGUMCA-UHFFFAOYSA-N 0.000 description 1
- NJHDTSOAXCBXTA-UHFFFAOYSA-N 2,6-difluoropyrimidine-4-carboxamide Chemical compound NC(=O)C1=CC(F)=NC(F)=N1 NJHDTSOAXCBXTA-UHFFFAOYSA-N 0.000 description 1
- JXFGMKYBHVBLCH-UHFFFAOYSA-N 4,5-dibromo-2,6-difluoropyrimidine Chemical compound FC1=NC(F)=C(Br)C(Br)=N1 JXFGMKYBHVBLCH-UHFFFAOYSA-N 0.000 description 1
- BAIJUHNFHQYGHR-UHFFFAOYSA-N 4,5-dichloro-2,6-difluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(Cl)=N1 BAIJUHNFHQYGHR-UHFFFAOYSA-N 0.000 description 1
- SLCUSSPKUGKMGA-UHFFFAOYSA-N 4-bromo-2,6-difluoropyrimidine Chemical compound FC1=CC(Br)=NC(F)=N1 SLCUSSPKUGKMGA-UHFFFAOYSA-N 0.000 description 1
- VJMKIDUNVPFBOB-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1Cl VJMKIDUNVPFBOB-UHFFFAOYSA-N 0.000 description 1
- WOQIMJVYLVUMGO-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1Cl WOQIMJVYLVUMGO-UHFFFAOYSA-N 0.000 description 1
- ACYSJALOFWHUEX-UHFFFAOYSA-N 4-chloro-2,6-difluoropyrimidine Chemical compound FC1=CC(Cl)=NC(F)=N1 ACYSJALOFWHUEX-UHFFFAOYSA-N 0.000 description 1
- FRSCGYMSBBDAKE-UHFFFAOYSA-N 5-(chloromethyl)-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(CCl)C(F)=N1 FRSCGYMSBBDAKE-UHFFFAOYSA-N 0.000 description 1
- KSMWCDRMAKHSKP-UHFFFAOYSA-N 5-(difluoromethyl)-2,4,6-trifluoropyrimidine Chemical compound FC(F)C1=C(F)N=C(F)N=C1F KSMWCDRMAKHSKP-UHFFFAOYSA-N 0.000 description 1
- HTYRTGGIOAMLRR-UHFFFAOYSA-N 5-amino-4-hydroxybenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC(S(O)(=O)=O)=C1O HTYRTGGIOAMLRR-UHFFFAOYSA-N 0.000 description 1
- BOLIYMRNXVAWIJ-UHFFFAOYSA-N 5-bromo-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Br)C(F)=N1 BOLIYMRNXVAWIJ-UHFFFAOYSA-N 0.000 description 1
- DTRZSACSYOVLAN-UHFFFAOYSA-N 5-bromo-2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(Br)C(C(F)(F)F)=N1 DTRZSACSYOVLAN-UHFFFAOYSA-N 0.000 description 1
- ZBTCTILYGQNVOJ-UHFFFAOYSA-N 5-bromo-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Br ZBTCTILYGQNVOJ-UHFFFAOYSA-N 0.000 description 1
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 description 1
- LTRDQYKIIGULAQ-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=NC(F)=C(Cl)C(C(F)(F)F)=N1 LTRDQYKIIGULAQ-UHFFFAOYSA-N 0.000 description 1
- RMULVUFPLMJWOK-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Cl RMULVUFPLMJWOK-UHFFFAOYSA-N 0.000 description 1
- OJZLZLUROPDDOH-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-phenylpyrimidine Chemical compound FC1=NC(F)=C(Cl)C(C=2C=CC=CC=2)=N1 OJZLZLUROPDDOH-UHFFFAOYSA-N 0.000 description 1
- XZSZSTCLQANXKU-UHFFFAOYSA-N 5-chloro-2,4-difluoropyrimidine Chemical compound FC1=NC=C(Cl)C(F)=N1 XZSZSTCLQANXKU-UHFFFAOYSA-N 0.000 description 1
- RRGDBELLJTVUDW-UHFFFAOYSA-N 5-chloro-4-(difluoromethyl)-2,6-difluoropyrimidine Chemical compound FC(F)C1=NC(F)=NC(F)=C1Cl RRGDBELLJTVUDW-UHFFFAOYSA-N 0.000 description 1
- QNKBTVYFMYGMLH-UHFFFAOYSA-N 5-ethylsulfonyl-2,4-difluoropyrimidine Chemical compound CCS(=O)(=O)C1=CN=C(F)N=C1F QNKBTVYFMYGMLH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003165 hydrotropic effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/20—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a pyrimidine ring
- C09B62/205—Specific dyes not provided for in groups C09B62/22 - C09B62/26
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH287070A CH515315A (de) | 1968-01-29 | 1968-01-29 | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH132768A CH501713A (de) | 1968-01-29 | 1968-01-29 | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen |
| CH287070A CH515315A (de) | 1968-01-29 | 1968-01-29 | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH515315A true CH515315A (de) | 1971-11-15 |
Family
ID=4207856
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287070A CH515315A (de) | 1968-01-29 | 1968-01-29 | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen |
| CH132768A CH501713A (de) | 1966-07-21 | 1968-01-29 | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH132768A CH501713A (de) | 1966-07-21 | 1968-01-29 | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE727610A (en]) |
| CH (2) | CH515315A (en]) |
| DE (1) | DE1904112C3 (en]) |
| ES (1) | ES363024A1 (en]) |
| FR (1) | FR2000892A1 (en]) |
| GB (1) | GB1243873A (en]) |
| NL (1) | NL6901374A (en]) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2817780C2 (de) * | 1978-04-22 | 1984-09-20 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe |
| DE3406232A1 (de) * | 1984-02-21 | 1985-08-29 | Bayer Ag, 5090 Leverkusen | Faserreaktive formazanfarbstoffe |
| DE4122100A1 (de) * | 1991-07-04 | 1993-01-07 | Bayer Ag | Formazan-farbstoffe |
| DE4241918A1 (en]) * | 1991-12-20 | 1993-06-24 | Sandoz Ag |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE578932A (fr) * | 1958-05-23 | 1959-11-23 | Geigy Ag J R | Colorants azoïques réactifs, leur procédé de préparation et leurs applications. |
| DE1152774B (de) * | 1959-11-13 | 1963-08-14 | Geigy Ag J R | Verfahren zur Herstellung von metallhaltigen, reaktiven Farbstoffen |
| DE1155872B (de) * | 1960-01-15 | 1963-10-17 | Geigy Ag J R | Verfahren zur Herstellung von metallhaltigen, reaktiven Farbstoffen |
| DE1186963B (de) * | 1960-05-30 | 1965-02-11 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| DE1198469B (de) * | 1961-02-27 | 1965-08-12 | Basf Ag | Verfahren zur Herstellung von wasserloeslichen Reaktivfarbstoffen der Anthrachinonreihe |
| NL128069C (en]) * | 1963-03-01 | |||
| CH431758A (de) * | 1963-07-10 | 1967-03-15 | Geigy Ag J R | Verfahren zur Herstellung neuer reaktiver Farbstoffe |
| CH484996A (de) * | 1966-07-21 | 1970-01-31 | Geigy Ag J R | Verfahren zur Herstellung von schwermetallhaltigen Formazanfarbstoffen |
| DE1644171A1 (de) * | 1966-09-10 | 1970-07-30 | Bayer Ag | Reaktivfarbstoffe und Verfahren zu deren Herstellung |
| DE1644203B2 (de) * | 1967-03-25 | 1977-11-17 | Bayer Ag, 5090 Leverkusen | Reaktivfarbstoffe |
-
1968
- 1968-01-29 CH CH287070A patent/CH515315A/de not_active IP Right Cessation
- 1968-01-29 CH CH132768A patent/CH501713A/de not_active IP Right Cessation
-
1969
- 1969-01-28 GB GB468169A patent/GB1243873A/en not_active Expired
- 1969-01-28 FR FR6901646A patent/FR2000892A1/fr active Pending
- 1969-01-28 NL NL6901374A patent/NL6901374A/xx unknown
- 1969-01-28 ES ES363024A patent/ES363024A1/es not_active Expired
- 1969-01-28 DE DE1904112A patent/DE1904112C3/de not_active Expired
- 1969-01-29 BE BE727610D patent/BE727610A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE727610A (en]) | 1969-07-29 |
| NL6901374A (en]) | 1969-07-31 |
| FR2000892A1 (en]) | 1969-09-19 |
| GB1243873A (en) | 1971-08-25 |
| DE1904112C3 (de) | 1981-05-21 |
| ES363024A1 (es) | 1970-12-01 |
| DE1904112B2 (de) | 1980-07-17 |
| CH501713A (de) | 1971-01-15 |
| DE1904112A1 (de) | 1971-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0070808B1 (de) | Reaktivfarbstoffe, deren Herstellung und Verwendung | |
| DE1644203B2 (de) | Reaktivfarbstoffe | |
| DE1106897B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE1795175A1 (de) | Verfahren zur Herstellung von wasserloeslichen Disazofarbstoffen | |
| CH515315A (de) | Verfahren zur Herstellung von faserreaktiven, schwermetallhaltigen Formazanfarbstoffen | |
| DE1644366B1 (de) | Verfahren zur Herstellung von metallhaltigen wasserloeslichen Pyrimidinreaktiv-Azofarbstoffen | |
| CH515316A (de) | Verfahren zur Herstellung von faserreaktiven schwermetallhaltigen Formazanfarbstoffen | |
| DE2852037A1 (de) | Neue verbindungen, verfahren zu deren herstellung und deren verwendung | |
| DE2520123A1 (de) | Verfahren zur herstellung von formazanmetallkomplexfarbstoffen | |
| DE1444719A1 (de) | Verfahren zur Herstellung von metallhaltigen Formazanfarbstoffen | |
| DE2017873C3 (de) | Blaue Diazofarbstoffe | |
| DE1419837C3 (de) | Reaktive Monoazokupferkomplexfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1245515B (de) | Verfahren zur Herstellung wasserloeslicher reaktiver Disazofarbstoffe | |
| AT214545B (de) | Verfahren zur Herstellung von mindestens einen dihalogenierten Pyrimidinring enthaltenden wasserlöslichen Farbstoffen der Azo-, Anthrachinon- und Phthalocyaninreihe | |
| AT200686B (de) | Verfahren zur Herstellung neuer, wasserlöslicher Disazofarbstoffe | |
| AT235432B (de) | Verfahren zur Herstellung von neuen, schwermetallhaltigen, reaktiven Azofarbstoffen | |
| CH492767A (de) | Verfahren zur Herstellung von Reaktivfarbstoffen | |
| DE1419840C (de) | Verfahren zur Herstellung von reaktiven Färb stoffen | |
| DE3443962A1 (de) | Reaktive disazoverbindungen | |
| DE1152774B (de) | Verfahren zur Herstellung von metallhaltigen, reaktiven Farbstoffen | |
| DE1091677B (de) | Verfahren zur Herstellung von wasserloeslichen, Cellulose echt faerbenden Farbstoffen | |
| DE1644206B2 (de) | Wasserloesliche reaktivfarbstoffe, deren herstellung und verwendung zum faerben von cellulosematerialien, wolle, seide, polyamid- und polyurethanfasern | |
| DE1045575B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| CH472479A (de) | Verfahren zur Herstellung chromhaltiger Reaktivfarbstoffe | |
| CH387838A (de) | Verfahren zur Herstellung von reaktiven Farbstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |