CH615693A5 - Process for preparing new trisazo dyes, the trisazo dyes and use thereof - Google Patents
Process for preparing new trisazo dyes, the trisazo dyes and use thereof Download PDFInfo
- Publication number
- CH615693A5 CH615693A5 CH1139574A CH1139574A CH615693A5 CH 615693 A5 CH615693 A5 CH 615693A5 CH 1139574 A CH1139574 A CH 1139574A CH 1139574 A CH1139574 A CH 1139574A CH 615693 A5 CH615693 A5 CH 615693A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- groups
- trisazo dyes
- carbon atoms
- hydroxydiphenylamine
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title 1
- 230000008878 coupling Effects 0.000 claims description 25
- 238000010168 coupling process Methods 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 20
- FMMQDMHSGNXJSQ-UHFFFAOYSA-N n,n-diphenylhydroxylamine Chemical compound C=1C=CC=CC=1N(O)C1=CC=CC=C1 FMMQDMHSGNXJSQ-UHFFFAOYSA-N 0.000 claims description 14
- 238000004043 dyeing Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000010985 leather Substances 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 150000001555 benzenes Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000004753 textile Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000004040 coloring Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- -1 polyazo Polymers 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SUHWXARLXCIBFK-UHFFFAOYSA-N 3-(2-methylanilino)phenol Chemical compound CC1=CC=CC=C1NC1=CC=CC(O)=C1 SUHWXARLXCIBFK-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 4
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical group C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 3
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 2
- TWYLNUMRYUFZIN-UHFFFAOYSA-N 3-(4-methylanilino)phenol Chemical compound C1=CC(C)=CC=C1NC1=CC=CC(O)=C1 TWYLNUMRYUFZIN-UHFFFAOYSA-N 0.000 description 2
- NDACNGSDAFKTGE-UHFFFAOYSA-N 3-hydroxydiphenylamine Chemical compound OC1=CC=CC(NC=2C=CC=CC=2)=C1 NDACNGSDAFKTGE-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920000742 Cotton Polymers 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000006598 aminocarbonylamino group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000001769 aryl amino group Chemical group 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical class OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 150000001733 carboxylic acid esters Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 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
- CHQNGSJEKNJUBX-UHFFFAOYSA-N 1-amino-8-hydroxy-2h-naphthalene-1,2-disulfonic acid Chemical compound C1=CC(O)=C2C(N)(S(O)(=O)=O)C(S(O)(=O)=O)C=CC2=C1 CHQNGSJEKNJUBX-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- JSQGOXTYKZBABW-UHFFFAOYSA-N 3-(3-hydroxyanilino)phenol Chemical compound OC1=CC=CC(NC=2C=C(O)C=CC=2)=C1 JSQGOXTYKZBABW-UHFFFAOYSA-N 0.000 description 1
- BCPQALWAROJVLE-UHFFFAOYSA-N 4-(2,4-dinitroanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O BCPQALWAROJVLE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 229940035422 diphenylamine Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XZSDLFHCPIUHJB-UHFFFAOYSA-N formamide;urea Chemical compound NC=O.NC(N)=O XZSDLFHCPIUHJB-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/20—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling compounds of different types
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/44—Trisazo dyes ot the type the component K being a hydroxy amine
- C09B35/46—Trisazo dyes ot the type the component K being a hydroxy amine the component K being an amino naphthol
- C09B35/463—D being derived from diaminodiphenyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712122166 DE2122166C3 (de) | 1971-05-05 | 1971-05-05 | Trisazofarbstoffe, deren Herstellung und Verwendung zum Färben vegetabilischer Fasern |
| DE19722208973 DE2208973A1 (de) | 1972-02-25 | 1972-02-25 | Polyazofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH615693A5 true CH615693A5 (en) | 1980-02-15 |
Family
ID=25761057
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1139574A CH615693A5 (en) | 1971-05-05 | 1972-05-03 | Process for preparing new trisazo dyes, the trisazo dyes and use thereof |
| CH654472A CH616174A5 (en) | 1971-05-05 | 1972-05-03 | Process for the preparation of novel polyazo dyestuffs, and their use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH654472A CH616174A5 (en) | 1971-05-05 | 1972-05-03 | Process for the preparation of novel polyazo dyestuffs, and their use |
Country Status (10)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2748719A1 (de) * | 1977-10-29 | 1979-05-03 | Bayer Ag | Azofarbstoffe |
| EP0169808A3 (en) * | 1984-07-24 | 1988-12-21 | Ciba-Geigy Ag | Uv-absorber compounds, method for their preparation and their use as image dyes in photographic materials for the silver dye-bleaching process |
| US5095100A (en) * | 1989-06-13 | 1992-03-10 | Orient Chemical Industries, Ltd. | Metal complex dyes and preparation thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE153557C (enrdf_load_stackoverflow) * | ||||
| DE93853C (enrdf_load_stackoverflow) * | ||||
| US2073000A (en) * | 1932-12-21 | 1937-03-09 | Gen Aniline Works Inc | Trisazodyestuffs |
| US2103778A (en) * | 1935-02-02 | 1937-12-28 | Gen Aniline Works Inc | Azodyestuffs |
-
1972
- 1972-04-04 ES ES402367A patent/ES402367A1/es not_active Expired
- 1972-05-03 DD DD16271772A patent/DD100277A5/xx unknown
- 1972-05-03 DD DD17236572A patent/DD104990A5/xx unknown
- 1972-05-03 CH CH1139574A patent/CH615693A5/de not_active IP Right Cessation
- 1972-05-03 CA CA141,173A patent/CA984836A/en not_active Expired
- 1972-05-03 NL NL7205964A patent/NL7205964A/xx not_active Application Discontinuation
- 1972-05-03 CH CH654472A patent/CH616174A5/de not_active IP Right Cessation
- 1972-05-03 IT IT2386772A patent/IT961158B/it active
- 1972-05-04 BE BE783019A patent/BE783019A/xx unknown
- 1972-05-05 GB GB2103372A patent/GB1395397A/en not_active Expired
- 1972-05-05 FR FR7216240A patent/FR2135349B1/fr not_active Expired
-
1975
- 1975-12-26 JP JP50155139A patent/JPS5198728A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT961158B (it) | 1973-12-10 |
| CH616174A5 (en) | 1980-03-14 |
| JPS5198728A (enrdf_load_stackoverflow) | 1976-08-31 |
| FR2135349A1 (enrdf_load_stackoverflow) | 1972-12-15 |
| DD100277A5 (enrdf_load_stackoverflow) | 1973-09-12 |
| BE783019A (fr) | 1972-11-06 |
| CA984836A (en) | 1976-03-02 |
| DD104990A5 (enrdf_load_stackoverflow) | 1974-04-05 |
| FR2135349B1 (enrdf_load_stackoverflow) | 1978-03-03 |
| GB1395397A (en) | 1975-05-29 |
| ES402367A1 (es) | 1975-03-16 |
| NL7205964A (enrdf_load_stackoverflow) | 1972-11-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE742517C (de) | Verfahren zur Herstellung von metallhaltigen Azofarbstoffen | |
| DE1215282B (de) | Verfahren zur Herstellung von wasserloeslichen Disazofarbstoffen | |
| DE942345C (de) | Verfahren zur Herstellung neuer direktziehender Azofarbstoffe | |
| CH615693A5 (en) | Process for preparing new trisazo dyes, the trisazo dyes and use thereof | |
| DE2154942A1 (de) | Neue monoazo-reaktivfarbstoffe, ihre verwendung und verfahren zu ihrer herstellung | |
| DE2355279A1 (de) | Auf der faser diazotierbare direktfarbstoffe | |
| DE2126299C3 (de) | Phenyl-naphthotrlazolmonoazofarbstoffe, deren Herstellung und Verwendung | |
| CH496069A (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| DE2140864A1 (de) | Disazofarbstoffe | |
| DE2034591A1 (de) | Neue wasserlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| DE1960895C3 (de) | Wasserlösliche, reaktive Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Leder oder Fasermaterialien aus Wolle, Seide, Polyamiden, Polyurethanen, regenerierten Proteinfasern oder nativen oder regenerierten Cellulosefasern | |
| DE1544541C3 (enrdf_load_stackoverflow) | ||
| DE925539C (de) | Verfahren zur Herstellung neuer Trisazofarbstoffe | |
| DE921225C (de) | Verfahren zur Herstellung von Disazofarbstoffen | |
| EP0073387A1 (de) | Wasserlösliche Polyazofarbstoffe, ihre Herstellung und ihre Verwendung | |
| DE849736C (de) | Verfahren zur Herstellung direktziehender Azofarbstoffe | |
| DE956710C (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1019025B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| EP0586339A1 (de) | Azofarbstoffe, Verfahren zu deren Herstellung und deren Verwendung | |
| DE952018C (de) | Verfahren zur Herstellung substantiver Disazofarbstoffe | |
| DE545625C (de) | Verfahren zur Darstellung von Disazofarbstoffen | |
| DE1644222C (de) | Orangenfarbige bis scharlachrote Mono azoreaktivfarbstoffe und Verfahren zu deren Herstellung | |
| DE1644200C3 (de) | Wasserlösliche Monoazofarbstoffe und Verfahren zu ihrer Herstellung | |
| CH314329A (de) | Verfahren zur Herstellung direktziehender Azofarbstoffe | |
| DE1644087C3 (de) | Verfahren zur Herstellung wasserlöslicher organischer Reaktivfarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |