CH637677A5 - Reaktivfarbstoffe. - Google Patents
Reaktivfarbstoffe. Download PDFInfo
- Publication number
- CH637677A5 CH637677A5 CH361079A CH361079A CH637677A5 CH 637677 A5 CH637677 A5 CH 637677A5 CH 361079 A CH361079 A CH 361079A CH 361079 A CH361079 A CH 361079A CH 637677 A5 CH637677 A5 CH 637677A5
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- yellow
- methyl
- chloro
- carbonyl
- Prior art date
Links
- 239000000985 reactive dye Substances 0.000 title description 3
- -1 methoxy, ethoxy, phenoxy, chlorophenoxy, benzoyl Chemical group 0.000 description 79
- 239000000975 dye Substances 0.000 description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 239000001257 hydrogen Substances 0.000 description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 17
- 229910052801 chlorine Inorganic materials 0.000 description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 229920002678 cellulose Polymers 0.000 description 8
- 239000001913 cellulose Substances 0.000 description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000010985 leather Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- RXNKCIBVUNMMAD-UHFFFAOYSA-N 4-[9-(4-amino-3-fluorophenyl)fluoren-9-yl]-2-fluoroaniline Chemical compound C1=C(F)C(N)=CC=C1C1(C=2C=C(F)C(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 RXNKCIBVUNMMAD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000001488 sodium phosphate Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 229910018828 PO3H2 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 2
- 235000019801 trisodium phosphate Nutrition 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
- DYCSWJLEEYACLO-UHFFFAOYSA-N 1-(2-chloro-4-methylphenyl)-5-oxo-4H-pyrazole-3-carboxylic acid Chemical compound ClC1=C(C=CC(=C1)C)N1N=C(CC1=O)C(=O)O DYCSWJLEEYACLO-UHFFFAOYSA-N 0.000 description 1
- MEZOTFSAQNETCH-UHFFFAOYSA-N 1-(2-chloro-6-methylphenyl)-5-oxo-4H-pyrazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)C)N1N=C(CC1=O)C(=O)O MEZOTFSAQNETCH-UHFFFAOYSA-N 0.000 description 1
- GIKMWFAAEIACRF-UHFFFAOYSA-N 2,4,5-trichloropyrimidine Chemical compound ClC1=NC=C(Cl)C(Cl)=N1 GIKMWFAAEIACRF-UHFFFAOYSA-N 0.000 description 1
- LYBDHGMSPQBSNW-UHFFFAOYSA-N 2,4,5-trifluoropyrimidine Chemical compound FC1=NC=C(F)C(F)=N1 LYBDHGMSPQBSNW-UHFFFAOYSA-N 0.000 description 1
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- YADSWTKOIHUSDX-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(N)=C(S(O)(=O)=O)C=C1S(O)(=O)=O YADSWTKOIHUSDX-UHFFFAOYSA-N 0.000 description 1
- OLOLDTJCNAOMQJ-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=CC(Cl)=NC(S(C)(=O)=O)=N1 OLOLDTJCNAOMQJ-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- GHBWBMDGBCKAQU-OWOJBTEDSA-N 5-amino-2-[(e)-2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O GHBWBMDGBCKAQU-OWOJBTEDSA-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
- JAEBRIOOHLIKRB-UHFFFAOYSA-N 5-chloro-4-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC=C1Cl JAEBRIOOHLIKRB-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- AJFXNBUVIBKWBT-UHFFFAOYSA-N disodium;boric acid;hydrogen borate Chemical compound [Na+].[Na+].OB(O)O.OB(O)O.OB(O)O.OB([O-])[O-] AJFXNBUVIBKWBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 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
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
-
- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/007—Dyestuffs containing phosphonic or phosphinic acid groups and derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Luminescent Compositions (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2817033A DE2817033C2 (de) | 1978-04-19 | 1978-04-19 | Reaktivfarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH637677A5 true CH637677A5 (de) | 1983-08-15 |
Family
ID=6037442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH361079A CH637677A5 (de) | 1978-04-19 | 1979-04-17 | Reaktivfarbstoffe. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4544738A (en, 2012) |
| JP (1) | JPS54139934A (en, 2012) |
| BE (1) | BE875625A (en, 2012) |
| CH (1) | CH637677A5 (en, 2012) |
| DE (1) | DE2817033C2 (en, 2012) |
| FR (1) | FR2432540A1 (en, 2012) |
| GB (1) | GB2020681B (en, 2012) |
| IT (1) | IT1112958B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348318A (en) * | 1978-11-30 | 1982-09-07 | Ciba-Geigy Corporation | Azo-dyes, their preparation and use |
| DE3023920A1 (de) * | 1980-06-26 | 1982-01-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von azo-reaktivfarbstoffen |
| CH663028A5 (de) * | 1985-04-03 | 1987-11-13 | Ciba Geigy Ag | Monoazofarbstoffe und deren herstellung. |
| US5030701A (en) * | 1987-12-31 | 1991-07-09 | Minnesota Mining And Manufacturing Company | Fluorine- and chromophore-containing polymer |
| US4909806A (en) * | 1987-12-31 | 1990-03-20 | Minnesota Mining And Manufacturing Company | Fluorine- and chromophore-containing polymer |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US156115A (en) * | 1874-10-20 | Improvement in hay-wagons | ||
| US149837A (en) * | 1874-04-21 | Improvement in solar compasses | ||
| US2795576A (en) * | 1953-08-10 | 1957-06-11 | Ciba Ltd | New monoazo-dyestuffs |
| DE1066302B (de) * | 1955-11-25 | 1959-10-01 | Imperial Chemical Industries Limited, London | Verfahren zur Herstellung von Monoazofarbstoffe^ |
| FR1160909A (fr) * | 1955-11-25 | 1958-08-13 | Ici Ltd | Nouveaux colorants monoazoïques |
| CH348493A (de) * | 1956-07-05 | 1960-08-31 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
| US2945021A (en) * | 1956-09-14 | 1960-07-12 | Ciba Ltd | Monoazo and disazo triazine dyes |
| CH349014A (de) * | 1956-10-29 | 1960-09-30 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
| CH384747A (de) * | 1957-05-07 | 1965-02-26 | Ciba Geigy | Verfahren zur Herstellung neuer Farbstoffe |
| FR1246743A (fr) * | 1957-11-20 | 1960-11-25 | Sandoz Ag | Colorants cyanuriques hydrosolubles, leur procédé de fabrication et leurs applications |
| FR1223655A (fr) * | 1958-02-12 | 1960-06-20 | Ici Ltd | Nouveaux colorants azoïques |
| CH366611A (de) * | 1958-05-23 | 1963-01-15 | Geigy Ag J R | Verfahren zur Herstellung von Azofarbstoffen |
| GB948160A (en) * | 1960-08-04 | 1964-01-29 | Ici Ltd | New monoazo dyestuffs |
| FR1296942A (fr) * | 1961-08-04 | 1962-06-22 | Ici Ltd | Nouveaux colorants monoazoïques réactifs |
| GB984802A (en) * | 1962-01-10 | 1965-03-03 | Ici Ltd | New azo dyestuffs containing unsaturated carboxylic acid amide groups |
| DE1252824B (de) * | 1963-03-01 | 1967-10-26 | J. R. Geigy A.G., Basel (Schweiz) | Verfahren zur Herstellung von reaktiven Farbstoffen |
| DE1230152B (de) * | 1963-05-14 | 1966-12-08 | Hoechst Ag | Verfahren zur Herstellung von Azofarbstoffen |
| CH477529A (de) * | 1964-06-29 | 1969-08-31 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
| DE1283989B (de) * | 1964-08-06 | 1968-11-28 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen und deren Metallkomplexverbindungen |
| DE1276844B (de) * | 1964-11-06 | 1968-09-05 | Hoechst Ag | Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen |
| CH1371667A4 (de) * | 1966-10-12 | 1970-08-31 | Mitsubishi Chem Ind | Reaktivfarbstoffhaltige Klotz- oder Färbeflotte bzw. Druckpaste für Textilmaterialien |
| DE1644215B2 (de) * | 1967-05-27 | 1976-07-01 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche monoazofarbstoffe, ein verfahren zu ihrer herstellung und ihre verwendung |
| DE1795086C3 (de) * | 1968-08-07 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Cellulosefasern, Wolle, Seide, Polyamidfasern und Leder |
| BE757027A (fr) * | 1969-10-06 | 1971-04-05 | Agripat Sa | Fixage electrolytique de colorants reactifs |
| DE2009421C3 (de) * | 1970-02-28 | 1979-09-27 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Leder, Wolle, Seide, Polyamid-, Polyurethan- und/oder nativen oder regenerierten Cellulosefasermaterialien |
| JPS4873582A (en, 2012) * | 1972-01-11 | 1973-10-04 | ||
| US3993440A (en) * | 1972-01-30 | 1976-11-23 | Imperial Chemical Industries Limited | Coloration with azo carboxy pyrazolone |
| US4145340A (en) * | 1973-01-30 | 1979-03-20 | Imperial Chemical Industries Limited | Water-soluble reactive monoazo dye containing a nonylphenoxy, chlorotriazine group |
| GB1455995A (en) * | 1973-01-30 | 1976-11-17 | Ici Ltd | Colouration process |
| JPS502725A (en, 2012) * | 1973-05-11 | 1975-01-13 | ||
| JPS5064317A (en, 2012) * | 1973-10-08 | 1975-05-31 |
-
1978
- 1978-04-19 DE DE2817033A patent/DE2817033C2/de not_active Expired
-
1979
- 1979-03-16 FR FR7906695A patent/FR2432540A1/fr active Granted
- 1979-03-20 IT IT21161/79A patent/IT1112958B/it active
- 1979-04-16 JP JP4550979A patent/JPS54139934A/ja active Granted
- 1979-04-17 BE BE0/194642A patent/BE875625A/xx not_active IP Right Cessation
- 1979-04-17 CH CH361079A patent/CH637677A5/de not_active IP Right Cessation
- 1979-04-18 GB GB7913394A patent/GB2020681B/en not_active Expired
-
1980
- 1980-09-24 US US06/190,179 patent/US4544738A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE2817033C2 (de) | 1983-03-24 |
| JPS54139934A (en) | 1979-10-30 |
| GB2020681B (en) | 1982-11-10 |
| FR2432540B1 (en, 2012) | 1984-04-27 |
| DE2817033A1 (de) | 1979-10-25 |
| IT1112958B (it) | 1986-01-20 |
| FR2432540A1 (fr) | 1980-02-29 |
| BE875625A (fr) | 1979-10-17 |
| US4544738A (en) | 1985-10-01 |
| IT7921161A0 (it) | 1979-03-20 |
| JPS6325027B2 (en, 2012) | 1988-05-24 |
| GB2020681A (en) | 1979-11-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |