DE2139148C3 - Telrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben vonpflanzlichen und tierischen Fasermaterialien, sowie von Leder - Google Patents
Telrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben vonpflanzlichen und tierischen Fasermaterialien, sowie von LederInfo
- Publication number
- DE2139148C3 DE2139148C3 DE2139148A DE2139148A DE2139148C3 DE 2139148 C3 DE2139148 C3 DE 2139148C3 DE 2139148 A DE2139148 A DE 2139148A DE 2139148 A DE2139148 A DE 2139148A DE 2139148 C3 DE2139148 C3 DE 2139148C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- acid
- naphthalene
- sulfonic acid
- formula
- 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
- 239000000975 dye Substances 0.000 title claims description 29
- 238000004043 dyeing Methods 0.000 title claims description 9
- 239000010985 leather Substances 0.000 title claims description 5
- 235000013311 vegetables Nutrition 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims 4
- 239000002657 fibrous material Substances 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 27
- -1 Amino monoazo Chemical group 0.000 claims description 13
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- LBQAJLBSGOBDQF-UHFFFAOYSA-N nitro azanylidynemethanesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C#N LBQAJLBSGOBDQF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 240000007817 Olea europaea Species 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical compound NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 4
- XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 4
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 4
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 4
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 3
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 3
- NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 3
- DQNAQOYOSRJXFZ-UHFFFAOYSA-N 5-Amino-1-naphthalenesulfonic acid Chemical compound C1=CC=C2C(N)=CC=CC2=C1S(O)(=O)=O DQNAQOYOSRJXFZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 2
- ZFRBZRZEKIOGQI-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound C1=CC(O)=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 ZFRBZRZEKIOGQI-UHFFFAOYSA-N 0.000 description 2
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 2
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 1
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- QNAAQOLWUDNQFY-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1.NC1=CC=CC(Cl)=C1 QNAAQOLWUDNQFY-UHFFFAOYSA-N 0.000 description 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000008233 hard water Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/18—Trisazo or higher polyazo dyes
- C09B33/26—Tetrazo dyes of the type A->B->C->K<-D
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/32—Material containing basic nitrogen containing amide groups leather skins
- D06P3/3206—Material containing basic nitrogen containing amide groups leather skins using acid dyes
- D06P3/3226—Material containing basic nitrogen containing amide groups leather skins using acid dyes dis-polyazo
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2139148A DE2139148C3 (de) | 1971-08-05 | 1971-08-05 | Telrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben vonpflanzlichen und tierischen Fasermaterialien, sowie von Leder |
| NL7210601A NL7210601A (OSRAM) | 1971-08-05 | 1972-08-02 | |
| DD164841A DD101177A5 (OSRAM) | 1971-08-05 | 1972-08-03 | |
| IT27862/72A IT963714B (it) | 1971-08-05 | 1972-08-03 | Tetrakis azocoloranti |
| CH1151572A CH556372A (de) | 1971-08-05 | 1972-08-03 | Verfahren zur herstellung von tetrakisazofarbstoffen. |
| US278089A US3862118A (en) | 1971-08-05 | 1972-08-04 | Tetrakisazo compounds |
| ES405542A ES405542A1 (es) | 1971-08-05 | 1972-08-04 | Procedimiento para la preparacion de colorantes tetraquisa-zoicos. |
| FR7228219A FR2155224A5 (OSRAM) | 1971-08-05 | 1972-08-04 | |
| JP47077736A JPS5122496B2 (OSRAM) | 1971-08-05 | 1972-08-04 | |
| GB3657272A GB1341646A (en) | 1971-08-05 | 1972-08-04 | Tetrakisazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2139148A DE2139148C3 (de) | 1971-08-05 | 1971-08-05 | Telrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben vonpflanzlichen und tierischen Fasermaterialien, sowie von Leder |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2139148A1 DE2139148A1 (de) | 1973-02-15 |
| DE2139148B2 DE2139148B2 (de) | 1975-02-20 |
| DE2139148C3 true DE2139148C3 (de) | 1975-10-02 |
Family
ID=5815824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2139148A Expired DE2139148C3 (de) | 1971-08-05 | 1971-08-05 | Telrakisazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben vonpflanzlichen und tierischen Fasermaterialien, sowie von Leder |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3862118A (OSRAM) |
| JP (1) | JPS5122496B2 (OSRAM) |
| CH (1) | CH556372A (OSRAM) |
| DD (1) | DD101177A5 (OSRAM) |
| DE (1) | DE2139148C3 (OSRAM) |
| ES (1) | ES405542A1 (OSRAM) |
| FR (1) | FR2155224A5 (OSRAM) |
| GB (1) | GB1341646A (OSRAM) |
| IT (1) | IT963714B (OSRAM) |
| NL (1) | NL7210601A (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH623346A5 (OSRAM) * | 1975-09-05 | 1981-05-29 | Sandoz Ag | |
| EP0322357B1 (de) * | 1987-12-16 | 1993-08-18 | Ciba-Geigy Ag | Verfahren zur Herstellung von Polyazofarbstoffen |
| JP6265973B2 (ja) * | 2013-03-28 | 2018-01-24 | 日本化薬株式会社 | 黒色用テトラキスアゾ化合物、それを含む染料組成物およびそれを用いる染色方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2106876A (en) * | 1935-04-04 | 1938-02-01 | Gen Aniline Works Inc | Azo dyestuffs |
| US2263894A (en) * | 1940-01-04 | 1941-11-25 | Du Pont | Tetrakisazo dye |
-
1971
- 1971-08-05 DE DE2139148A patent/DE2139148C3/de not_active Expired
-
1972
- 1972-08-02 NL NL7210601A patent/NL7210601A/xx not_active Application Discontinuation
- 1972-08-03 CH CH1151572A patent/CH556372A/xx not_active IP Right Cessation
- 1972-08-03 IT IT27862/72A patent/IT963714B/it active
- 1972-08-03 DD DD164841A patent/DD101177A5/xx unknown
- 1972-08-04 JP JP47077736A patent/JPS5122496B2/ja not_active Expired
- 1972-08-04 FR FR7228219A patent/FR2155224A5/fr not_active Expired
- 1972-08-04 GB GB3657272A patent/GB1341646A/en not_active Expired
- 1972-08-04 US US278089A patent/US3862118A/en not_active Expired - Lifetime
- 1972-08-04 ES ES405542A patent/ES405542A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES405542A1 (es) | 1975-07-01 |
| DE2139148B2 (de) | 1975-02-20 |
| US3862118A (en) | 1975-01-21 |
| JPS5122496B2 (OSRAM) | 1976-07-10 |
| DE2139148A1 (de) | 1973-02-15 |
| JPS4825729A (OSRAM) | 1973-04-04 |
| FR2155224A5 (OSRAM) | 1973-05-18 |
| CH556372A (de) | 1974-11-29 |
| NL7210601A (OSRAM) | 1973-02-07 |
| DD101177A5 (OSRAM) | 1973-10-20 |
| IT963714B (it) | 1974-01-21 |
| GB1341646A (en) | 1973-12-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |