GB533060A - Manufacture of hexakisazo dyestuffs, more especially suitable for dyeing leather - Google Patents
Manufacture of hexakisazo dyestuffs, more especially suitable for dyeing leatherInfo
- Publication number
- GB533060A GB533060A GB27180/39A GB2718039A GB533060A GB 533060 A GB533060 A GB 533060A GB 27180/39 A GB27180/39 A GB 27180/39A GB 2718039 A GB2718039 A GB 2718039A GB 533060 A GB533060 A GB 533060A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- nitro
- sulphonic acid
- resorcinol
- aminodiphenylamine
- 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
- 239000010985 leather Substances 0.000 title abstract 8
- 238000004043 dyeing Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 18
- 239000002253 acid Substances 0.000 abstract 16
- 239000000975 dye Substances 0.000 abstract 10
- 239000000203 mixture Substances 0.000 abstract 7
- 238000000034 method Methods 0.000 abstract 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 1
- 229940044174 4-phenylenediamine Drugs 0.000 abstract 1
- ZBZGGZGVFCIXDE-UHFFFAOYSA-N 5-amino-2-(4-aminophenyl)benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1S(O)(=O)=O ZBZGGZGVFCIXDE-UHFFFAOYSA-N 0.000 abstract 1
- HYLOSPCJTPLXSF-UHFFFAOYSA-N 5-amino-2-anilinobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1NC1=CC=CC=C1 HYLOSPCJTPLXSF-UHFFFAOYSA-N 0.000 abstract 1
- CAYLYXRCMNCWDM-UHFFFAOYSA-N 5-chloro-2-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(Cl)=CC=C1[N+]([O-])=O CAYLYXRCMNCWDM-UHFFFAOYSA-N 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 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
- C09B35/64—Higher polyazo dyes, e.g. of the types
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
533,060. Dyes. GEIGY AKT.-GES., J. R. Oct. 4, 1939, No. 27180. Convention date, Oct. 5, 1938. [Classes 2 (iii) and 15 (ii)] Hexakisazo dyes, suitable for dyeing leather, strong shades of reddish to yellowish brown, of the general formula wherein A represents the residue of resorcinol, B represents a naphthalene residue C represents a diphenylamine residue and D represents a radicle comprising two benzene nuclei connected directly or through an atom or group such as - O- ,-S-, -NH-, -CH<SP>2</SP>-, -SO 2 -, -CH 2 -CH 2 -, - CH = CH- or -HN.CO-, and in which the whole dyestuff contains at least four sulphonic acid groups, are obtained by (a) diazotizing the monazo dyestuff C-N = N-B-NH 2 (2 mols.) and coupling in alkaline solution with the disazo dyestuff (1 mol.) or (b) tetrazotizing the diamine H 2 N-D-NH 2 (1 mol.) and coupling with the disazo Examples relate to the preparation of the following dyestuffs, (1)4<SP>1</SP>-nitro-4-aminodiphenylamine - 2<SP>1</SP> - sulphonic acid # 1:6 - aminonaphthalenesulphonic acid (with or without the 1:7 - isomer) - resorcinol # benzidine - 2 - sulphonic acid or N, 3<SP>1</SP> - aminobenzoyl - 1:4 - diaminobenzene - 3 - sulphonic acid # resorcinol # 1:6 - aminonaphthalenesulphonic acid as above # 4<SP>1</SP> - nitro - 4 - aminodiphenylamine - 2<SP>1</SP> - sulphonic acid, by either of methods (a) or (b) above ; the products dye leather deep reddish brown ; (2) 4<SP>1</SP> - nitro - 4 - aminodiphenylamine - 2<SP>1</SP> - sulphonic acid # 1:6 - and 1:7 - aminonaphthalenesulphonic acids in admixture # resorcinol # 4:4<SP>1</SP> - diaminostilbene - 2:2<SP>1</SP> - disulpbonic acid or 4:4<SP>1</SP> - diaminodiphenylsulphide - 2:2<SP>1</SP> - disulphonic acid or 4:4<SP>1</SP>-diaminodibenzyl-2:21- disulphonic acid or 4:4<SP>1</SP>-diamino-3:3<SP>1</SP>-dimethyldiphenylmethane disulphonic acid or 4:4<SP>1</SP>- diaminodiphenylether - 3:3<SP>1</SP> - disulphonic acid # resorcinol # the 1:6 - and 1:7 - acid mixture as above # 4<SP>1</SP> - nitio - 4 - aminodiphenylamine - 2<SP>1</SP> - sulphonic acid, by method (a) above ; the products dye leather deep reddish brown; (3) 4-aminodiphenylamine-2-sulphonic acid # the 1:6- and 1:7-acid mixture as above - resorcinol # benzidine - 2:2<SP>1</SP> - disulphonic acid - resorcinol # the 1:6 - and 1:7 - acid mixture as above - 4 - aminodiphenylamine - 2 - sulphonic acid, by method (a) above ; the product dyes leather deep brown ; (4) 4<SP>1</SP>-nitro - 4 - aminodiphenylamine - 2<SP>1</SP> - sulphonic acid or the 2<SP>1</SP>-nitro-4<SP>1</SP>-sulpho isomer # the 1:6- and 1:7 - acid mixture as above or 1 - aminonaphthalene # resorcinol # benzidine - or tolidine - 2:2<SP>1</SP> - disulphonic acid or 4:4<SP>1</SP> - diaminodiphenylamine - 2 - sulphonic or 2:3<SP>1</SP> - disulphonic acid # resorcinol # the 1:6 - and 1:7 - acid mixture as above or 1 - aminonaphthalene # 4<SP>1</SP> - nitro - 4 - aminodiphenyl - amine - 2<SP>1</SP> - sulphonic acid or its 2<SP>1</SP> - nitro- 4' - sulpho isomer, by method (a) above the product dyes leather deep brown ; (5) 2<SP>1</SP>-nitro- 4 - aminodiphenylamine - 4<SP>1</SP> - phenylsulphone - 3<SP>11</SP> - sulphonic acid # the 1:6- and 1:7-acid mixture as above # resorcinol # benzidine - 2:2<SP>1</SP> - disulphonic acid - resorcinol - the 1:6 - and 1:7-acid mixture as above # 2<SP>1</SP> - nitro - 4 - aminodiphenylamine - 4<SP>1</SP> - phenylsulphone - 3<SP>11</SP> - sulphonic acid, by method (a) above ; the product dyes leather deep yellow-brown. An example of the process of dyeing leather is given. N, 3<SP>1</SP> - - Aminobenzoyl - 1:4 - - diaminobenzene-3 - sulphonic acid is obtained by reducing the nitro group in the product of reaction of 3-nitrobenzoyl chloride with 1:4-phenylenediamine sulphonic acid. 4:4<SP>1</SP>-Diaminodiphenyl ether-3:3<SP>1</SP>-disulphonicacid is obtained by reducing the nitro groups in the product of reaction of 1-chloro-4-nitrobenzene-3-sulphonic acid with 4-nitrophenol-3- sulphonic acid. 2<SP>1</SP>- Nitro - 4 - amiazodiphenylamine 4<SP>1</SP> - phenylsulphone-3<SP>11</SP>-sulphonic acid is obtained by saponifying the product of reaction of 4-chloro- 3-nitro-diphenylsulphone-3<SP>1</SP>-sulphonic acid with 4 -acetylaminoaniline.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH533060X | 1938-10-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB533060A true GB533060A (en) | 1941-02-05 |
Family
ID=4518585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB27180/39A Expired GB533060A (en) | 1938-10-05 | 1939-10-04 | Manufacture of hexakisazo dyestuffs, more especially suitable for dyeing leather |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB533060A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998041581A1 (en) * | 1997-03-18 | 1998-09-24 | Basf Aktiengesellschaft | Oligomeric azo dyes |
-
1939
- 1939-10-04 GB GB27180/39A patent/GB533060A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998041581A1 (en) * | 1997-03-18 | 1998-09-24 | Basf Aktiengesellschaft | Oligomeric azo dyes |
| US6114512A (en) * | 1997-03-18 | 2000-09-05 | Basf Aktiengesellschaft | Oligomeric azo dyes |
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