DE1907118A1 - Verfahren zur Herstellung sulfonsaeuregruppenhaltiger Azofarbstoffe - Google Patents
Verfahren zur Herstellung sulfonsaeuregruppenhaltiger AzofarbstoffeInfo
- Publication number
- DE1907118A1 DE1907118A1 DE19691907118 DE1907118A DE1907118A1 DE 1907118 A1 DE1907118 A1 DE 1907118A1 DE 19691907118 DE19691907118 DE 19691907118 DE 1907118 A DE1907118 A DE 1907118A DE 1907118 A1 DE1907118 A1 DE 1907118A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- sulfonic acid
- radical
- hydrogen
- meaning given
- 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.)
- Pending
Links
- 125000000542 sulfonic acid group Chemical group 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 12
- 239000000987 azo dye Substances 0.000 title claims description 8
- -1 aliphatic radical Chemical class 0.000 claims description 46
- 239000000975 dye Substances 0.000 claims description 26
- 238000005859 coupling reaction Methods 0.000 claims description 21
- 230000008878 coupling Effects 0.000 claims description 20
- 238000010168 coupling process Methods 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 150000003254 radicals Chemical class 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 210000002268 wool Anatomy 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000003217 pyrazoles Chemical class 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920006306 polyurethane fiber Polymers 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 14
- 150000001298 alcohols Chemical class 0.000 description 11
- 239000002253 acid Substances 0.000 description 8
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- 150000005415 aminobenzoic acids Chemical class 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
- HUIYGGQINIVDNW-UHFFFAOYSA-N butyl anthranilate Chemical compound CCCCOC(=O)C1=CC=CC=C1N HUIYGGQINIVDNW-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001044 red dye Substances 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- ILCLJQFCMRCPNM-UHFFFAOYSA-N 2-Methylpropyl 2-aminobenzoate Chemical compound CC(C)COC(=O)C1=CC=CC=C1N ILCLJQFCMRCPNM-UHFFFAOYSA-N 0.000 description 1
- NORJRQVQTYNLAO-UHFFFAOYSA-N 2-amino-3,5-difluorobenzoic acid Chemical compound NC1=C(F)C=C(F)C=C1C(O)=O NORJRQVQTYNLAO-UHFFFAOYSA-N 0.000 description 1
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical group NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- LGPVTNAJFDUWLF-UHFFFAOYSA-N 2-amino-4-fluorobenzoic acid Chemical compound NC1=CC(F)=CC=C1C(O)=O LGPVTNAJFDUWLF-UHFFFAOYSA-N 0.000 description 1
- CUKXRHLWPSBCTI-UHFFFAOYSA-N 2-amino-5-bromobenzoic acid Chemical group NC1=CC=C(Br)C=C1C(O)=O CUKXRHLWPSBCTI-UHFFFAOYSA-N 0.000 description 1
- BNQPROAXWQCNKO-UHFFFAOYSA-N 2-amino-6-bromobenzoic acid Chemical group NC1=CC=CC(Br)=C1C(O)=O BNQPROAXWQCNKO-UHFFFAOYSA-N 0.000 description 1
- SZCPTRGBOVXVCA-UHFFFAOYSA-N 2-amino-6-chlorobenzoic acid Chemical compound NC1=CC=CC(Cl)=C1C(O)=O SZCPTRGBOVXVCA-UHFFFAOYSA-N 0.000 description 1
- RWSFZKWMVWPDGZ-UHFFFAOYSA-N 2-amino-6-fluorobenzoic acid Chemical compound NC1=CC=CC(F)=C1C(O)=O RWSFZKWMVWPDGZ-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 1
- WFSPEVFSRUTRCN-UHFFFAOYSA-N 3-amino-4-fluorobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC=C1F WFSPEVFSRUTRCN-UHFFFAOYSA-N 0.000 description 1
- AQBXIOGPHBWBFP-UHFFFAOYSA-N 4-amino-2-bromobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(Br)=C1 AQBXIOGPHBWBFP-UHFFFAOYSA-N 0.000 description 1
- MBDUKNCPOPMRJQ-UHFFFAOYSA-N 4-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(Cl)=C1 MBDUKNCPOPMRJQ-UHFFFAOYSA-N 0.000 description 1
- QHERSCUZBKDVOC-UHFFFAOYSA-N 4-amino-2-fluorobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C(F)=C1 QHERSCUZBKDVOC-UHFFFAOYSA-N 0.000 description 1
- JSKXHTHMCCDEGD-UHFFFAOYSA-N 4-amino-3-fluorobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1F JSKXHTHMCCDEGD-UHFFFAOYSA-N 0.000 description 1
- NHFKECPTBZZFBC-UHFFFAOYSA-N 4-amino-3-methylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1N NHFKECPTBZZFBC-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- TZBROGJRQUABOK-UHFFFAOYSA-N 4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 TZBROGJRQUABOK-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- GVCFFVPEOLCYNN-UHFFFAOYSA-N 5-amino-2-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C(C(O)=O)=C1 GVCFFVPEOLCYNN-UHFFFAOYSA-N 0.000 description 1
- LWWPSEIFAKNPKQ-UHFFFAOYSA-N 5-amino-2-methoxybenzoic acid Chemical compound COC1=CC=C(N)C=C1C(O)=O LWWPSEIFAKNPKQ-UHFFFAOYSA-N 0.000 description 1
- FSXVZWAWYKMFMX-UHFFFAOYSA-N 5-amino-2-methylbenzoic acid Chemical compound CC1=CC=C(N)C=C1C(O)=O FSXVZWAWYKMFMX-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
- FPQMGQZTBWIHDN-UHFFFAOYSA-N 5-fluoroanthranilic acid Chemical compound NC1=CC=C(F)C=C1C(O)=O FPQMGQZTBWIHDN-UHFFFAOYSA-N 0.000 description 1
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 description 1
- NWGAZJKRHMBSCV-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(O)C2=CC(N)=CC=C21 NWGAZJKRHMBSCV-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 101100380295 Mus musculus Asah1 gene Proteins 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229940041616 menthol Drugs 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A47—FURNITURE; DOMESTIC ARTICLES OR APPLIANCES; COFFEE MILLS; SPICE MILLS; SUCTION CLEANERS IN GENERAL
- A47L—DOMESTIC WASHING OR CLEANING; SUCTION CLEANERS IN GENERAL
- A47L13/00—Implements for cleaning floors, carpets, furniture, walls, or wall coverings
- A47L13/10—Scrubbing; Scouring; Cleaning; Polishing
- A47L13/28—Polishing implements
- A47L13/30—Implements for polishing and waxing or oiling, with dispensers for wax or oil
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691907118 DE1907118A1 (de) | 1969-02-13 | 1969-02-13 | Verfahren zur Herstellung sulfonsaeuregruppenhaltiger Azofarbstoffe |
| CH1389970A CH543566A (de) | 1969-02-13 | 1970-01-29 | Verfahren zur Herstellung sulfonsäuregruppenhaltiger Azofarbstoffe |
| CA073793A CA919662A (en) | 1969-02-13 | 1970-02-03 | Process for the production of azo dyestuffs containing sulphonic acid groups |
| GB634070A GB1269887A (en) | 1969-02-13 | 1970-02-10 | Azo dyestuffs containing sulphonic acid groups |
| NL7001946A NL7001946A (enrdf_load_stackoverflow) | 1969-02-13 | 1970-02-11 | |
| BE745887D BE745887A (fr) | 1969-02-13 | 1970-02-12 | Procede de fabrication de colorants azoiques contenant des groupes acide sulfonique |
| AT128270A AT289982B (de) | 1969-02-13 | 1970-02-12 | Verfahren zur Herstellung von neuen sulfonsäuregruppenhaltigen Azofarbstoffen |
| FR7005283A FR2033332B1 (enrdf_load_stackoverflow) | 1969-02-13 | 1970-02-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691907118 DE1907118A1 (de) | 1969-02-13 | 1969-02-13 | Verfahren zur Herstellung sulfonsaeuregruppenhaltiger Azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1907118A1 true DE1907118A1 (de) | 1970-10-15 |
Family
ID=5725080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691907118 Pending DE1907118A1 (de) | 1969-02-13 | 1969-02-13 | Verfahren zur Herstellung sulfonsaeuregruppenhaltiger Azofarbstoffe |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT289982B (enrdf_load_stackoverflow) |
| BE (1) | BE745887A (enrdf_load_stackoverflow) |
| CA (1) | CA919662A (enrdf_load_stackoverflow) |
| DE (1) | DE1907118A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2033332B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1269887A (enrdf_load_stackoverflow) |
| NL (1) | NL7001946A (enrdf_load_stackoverflow) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE81152C (enrdf_load_stackoverflow) * | ||||
| FR1079084A (fr) * | 1952-03-05 | 1954-11-25 | Geigy Ag J R | Colorants mono-azoïques jaunes et leur procédé de préparation |
| CH330485A (de) * | 1955-01-21 | 1958-06-15 | Sandoz Ag | Verfahren zur Herstellung saurer Monoazofarbstoffe |
-
1969
- 1969-02-13 DE DE19691907118 patent/DE1907118A1/de active Pending
-
1970
- 1970-02-03 CA CA073793A patent/CA919662A/en not_active Expired
- 1970-02-10 GB GB634070A patent/GB1269887A/en not_active Expired
- 1970-02-11 NL NL7001946A patent/NL7001946A/xx unknown
- 1970-02-12 AT AT128270A patent/AT289982B/de active
- 1970-02-12 BE BE745887D patent/BE745887A/xx unknown
- 1970-02-13 FR FR7005283A patent/FR2033332B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2033332A1 (enrdf_load_stackoverflow) | 1970-12-04 |
| GB1269887A (en) | 1972-04-06 |
| FR2033332B1 (enrdf_load_stackoverflow) | 1974-05-03 |
| CA919662A (en) | 1973-01-23 |
| AT289982B (de) | 1971-05-10 |
| NL7001946A (enrdf_load_stackoverflow) | 1970-08-17 |
| BE745887A (fr) | 1970-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2004487A1 (de) | Neue wasserlösliche Azofarbstoffe | |
| DE1917278B2 (de) | Monoazofarbstoffe, Verfahren zu deren Herstellung und Farbstoffzubereitungen | |
| DE2115449C3 (de) | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben von Wolle oder synthetischen Polyamidtextilmaterialien | |
| DE1644189C3 (de) | Azofarbstoffe und deren Verwendung | |
| DE2154942C3 (de) | faserreaktive Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefasern, natürlichen oder synthetischen Polyamidfasern oder von Polyurethanfasern | |
| DE1012010B (de) | Verfahren zur Herstellung von kobalthaltigen Monoazofarbstoffen | |
| DE1907118A1 (de) | Verfahren zur Herstellung sulfonsaeuregruppenhaltiger Azofarbstoffe | |
| DE2714204A1 (de) | Monoazofarbstoffe | |
| DE2250083A1 (de) | Monoazofarbstoffe | |
| DE2533723A1 (de) | Monoazofarbstoffe | |
| DE1544587A1 (de) | Farbstoff-Eisen-Komplex sowie Verfahren zu seiner Herstellung | |
| DE909383C (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE863972C (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| AT220740B (de) | Verfahren zur Herstellung neuer wasserlöslicher Azofarbstoffe | |
| DE639253C (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE2504068A1 (de) | Triazo-farbstoff und verfahren zu seiner herstellung | |
| DE1644223C3 (de) | Wasserlösliche organische Farbstoffe und Verfahren zu ihrer Herstellung | |
| DE1644198C3 (de) | Metallfreie, wasserlösliche Disazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE652868C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE955884C (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE2012151C3 (de) | Wasserlösliche Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Fasermaterialien aus nativer oder regenerierter Cellulose, Wolle, Seide, Polyamiden oder Polyurethanen | |
| DE2362330A1 (de) | Polyfluorierte saure azofarbstoffe | |
| CH543566A (de) | Verfahren zur Herstellung sulfonsäuregruppenhaltiger Azofarbstoffe | |
| DE2035644A1 (de) | Disazofarbstoffe | |
| DE2065646C3 (de) | 1 zu 1-Kupferkomplexverbindungen von Monoazofarbstoffe^ Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Leder oder Fasern aus Wolle, Seide, Polyamiden und/oder regenerierter Cellulose |