DE2202419C3 - Sulfonsäuregruppenhaltige Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von natürlichen oder synthetischen Polyamiden sowie von Leder und Papier - Google Patents
Sulfonsäuregruppenhaltige Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von natürlichen oder synthetischen Polyamiden sowie von Leder und PapierInfo
- Publication number
- DE2202419C3 DE2202419C3 DE2202419A DE2202419A DE2202419C3 DE 2202419 C3 DE2202419 C3 DE 2202419C3 DE 2202419 A DE2202419 A DE 2202419A DE 2202419 A DE2202419 A DE 2202419A DE 2202419 C3 DE2202419 C3 DE 2202419C3
- Authority
- DE
- Germany
- Prior art keywords
- formula
- parts
- dyeing
- leather
- sulfonic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000542 sulfonic acid group Chemical group 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 title claims 2
- 239000004952 Polyamide Substances 0.000 title description 16
- 238000004043 dyeing Methods 0.000 title description 16
- 229920002647 polyamide Polymers 0.000 title description 16
- 239000010985 leather Substances 0.000 title description 3
- 239000000123 paper Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 10
- -1 aminomonoazo compound Chemical class 0.000 description 31
- 239000000975 dye Substances 0.000 description 22
- 238000000034 method Methods 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 229910052736 halogen Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000001000 anthraquinone dye Substances 0.000 description 3
- 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 3
- 125000002704 decyl group Chemical group [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])* 0.000 description 3
- 150000008049 diazo compounds Chemical class 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001400 nonyl 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])[H] 0.000 description 3
- 125000002889 tridecyl 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])[H] 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 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
- 229920001778 nylon Polymers 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl 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])[H] 0.000 description 2
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-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
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- AFPOMDNRTZLRMD-UHFFFAOYSA-N dodecyl carbonochloridate Chemical compound CCCCCCCCCCCCOC(Cl)=O AFPOMDNRTZLRMD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
- C09B43/1245—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters with formation of NHCOOR, NHCOSR or NHCSOR groups by acylation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/917—Wool or silk
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH78171A CH551471A (de) | 1971-01-20 | 1971-01-20 | Verfahren zur herstellung von sulfonsaeuregruppenhaltigen azofarbstoffen. |
| CH98671 | 1971-01-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2202419A1 DE2202419A1 (de) | 1972-08-31 |
| DE2202419B2 DE2202419B2 (de) | 1978-04-20 |
| DE2202419C3 true DE2202419C3 (de) | 1979-01-04 |
Family
ID=25685668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2202419A Expired DE2202419C3 (de) | 1971-01-20 | 1972-01-19 | Sulfonsäuregruppenhaltige Azofarbstoffe, ihre Herstellung und Verwendung zum Färben und Bedrucken von natürlichen oder synthetischen Polyamiden sowie von Leder und Papier |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3839316A (enExample) |
| JP (1) | JPS5742659B1 (enExample) |
| AU (1) | AU466879B2 (enExample) |
| BE (1) | BE778143A (enExample) |
| CA (1) | CA940124A (enExample) |
| CY (1) | CY907A (enExample) |
| DD (1) | DD95638A5 (enExample) |
| DE (1) | DE2202419C3 (enExample) |
| ES (2) | ES398969A1 (enExample) |
| FR (1) | FR2122538B1 (enExample) |
| GB (1) | GB1377422A (enExample) |
| HK (1) | HK29677A (enExample) |
| IT (1) | IT946724B (enExample) |
| NL (1) | NL162683C (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3133404A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Sulfonsaeuregruppenhaltige verlackte azofarbstoffe |
| DE3844771C2 (en) * | 1988-10-10 | 1992-04-23 | Geha-Werke Gmbh, 3000 Hannover, De | Application of correction medium to paper |
| DE59408909D1 (de) * | 1993-10-13 | 1999-12-16 | Ciba Sc Holding Ag | Neue Fluoreszenzfarbstoffe |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1758385A (en) * | 1926-11-15 | 1930-05-13 | Gen Aniline Works Inc | Azo dyestuffs and process of making same |
| FR644153A (fr) * | 1926-12-04 | 1928-10-03 | Ste Ind Chim Bale | Production de nouvelles matières colorantes azoïques |
| US1731150A (en) * | 1926-12-04 | 1929-10-08 | Chem Ind Basel | Monoazo dyestuffs |
| US2015225A (en) * | 1933-12-01 | 1935-09-24 | Gen Aniline Works Inc | Azo-dyestuffs |
| FR796465A (fr) * | 1934-10-17 | 1936-04-07 | Ig Farbenindustrie Ag | Nouveaux colorants azoïques et leur procédé de préparation |
| US2773055A (en) * | 1952-03-05 | 1956-12-04 | Geigy Ag J R | Yellow monoazo dyestuffs |
| FR1099740A (fr) * | 1953-05-06 | 1955-09-08 | Kodak Pathe | Nouveaux composés monoazoïques solubles dans l'eau et leurs applications |
| CH341586A (de) * | 1956-02-01 | 1959-10-15 | Sandoz Ag | Verfahren zur Herstellung walkechter Monoazofarbstoffe |
| CH386028A (de) * | 1960-05-12 | 1964-12-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen schwermetallhaltigen Formazanfarbstoffen |
| CH442567A (de) * | 1962-03-17 | 1967-08-31 | Basf Ag | Verfahren zur Herstellung neuer wasserlöslicher, reaktiver Azofarbstoffe |
| GB1175666A (en) * | 1966-03-14 | 1969-12-23 | Ici Ltd | Monoazo Dyestuffs |
-
1972
- 1972-01-12 AU AU37856/72A patent/AU466879B2/en not_active Expired
- 1972-01-14 US US00217946A patent/US3839316A/en not_active Expired - Lifetime
- 1972-01-17 GB GB208572A patent/GB1377422A/en not_active Expired
- 1972-01-17 BE BE778143A patent/BE778143A/xx not_active IP Right Cessation
- 1972-01-17 CY CY907A patent/CY907A/xx unknown
- 1972-01-18 ES ES398969A patent/ES398969A1/es not_active Expired
- 1972-01-19 DD DD160418A patent/DD95638A5/xx unknown
- 1972-01-19 CA CA132,745A patent/CA940124A/en not_active Expired
- 1972-01-19 IT IT19567/72A patent/IT946724B/it active
- 1972-01-19 DE DE2202419A patent/DE2202419C3/de not_active Expired
- 1972-01-20 JP JP47008000A patent/JPS5742659B1/ja active Pending
- 1972-01-20 NL NL7200782.A patent/NL162683C/xx not_active IP Right Cessation
- 1972-01-20 FR FR7201835A patent/FR2122538B1/fr not_active Expired
- 1972-04-12 ES ES401678A patent/ES401678A1/es not_active Expired
-
1977
- 1977-06-09 HK HK296/77A patent/HK29677A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3839316A (en) | 1974-10-01 |
| AU3785672A (en) | 1973-07-19 |
| NL7200782A (enExample) | 1972-07-24 |
| BE778143A (fr) | 1972-07-17 |
| NL162683C (nl) | 1980-06-16 |
| DD95638A5 (enExample) | 1973-02-12 |
| ES398969A1 (es) | 1975-05-16 |
| NL162683B (nl) | 1980-01-15 |
| IT946724B (it) | 1973-05-21 |
| CA940124A (en) | 1974-01-15 |
| AU466879B2 (en) | 1975-11-13 |
| CY907A (en) | 1977-10-07 |
| HK29677A (en) | 1977-06-17 |
| DE2202419A1 (de) | 1972-08-31 |
| FR2122538B1 (enExample) | 1975-10-24 |
| FR2122538A1 (enExample) | 1972-09-01 |
| GB1377422A (en) | 1974-12-18 |
| ES401678A1 (es) | 1976-02-01 |
| JPS5742659B1 (enExample) | 1982-09-09 |
| DE2202419B2 (de) | 1978-04-20 |
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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 |