GB595491A - Manufacture of azo dyestuffs - Google Patents
Manufacture of azo dyestuffsInfo
- Publication number
- GB595491A GB595491A GB17811/45A GB1781145A GB595491A GB 595491 A GB595491 A GB 595491A GB 17811/45 A GB17811/45 A GB 17811/45A GB 1781145 A GB1781145 A GB 1781145A GB 595491 A GB595491 A GB 595491A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- nitro
- carboxylic
- amino
- sulphonic
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 abstract 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 2
- 239000000975 dye Substances 0.000 abstract 2
- -1 nitro-monoazo Chemical group 0.000 abstract 2
- GNTARUIZNIWBCN-UHFFFAOYSA-N 2-chloro-5-nitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC([N+]([O-])=O)=CC=C1Cl GNTARUIZNIWBCN-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-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
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229910052742 iron Inorganic materials 0.000 abstract 1
- 239000010985 leather Substances 0.000 abstract 1
- KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/08—Preparation of azo dyes from other azo compounds by reduction
- C09B43/085—Preparation of azo dyes from other azo compounds by reduction by reacting nitro azo dyes with amine or amino azo dye with nitro compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Azo dyestuffs, probably containing an azoxy group, are manufactured by condensing a 4-nitro-41-hydroxy-1 : 11-azobenzene-31-carboxylic acid (which may carry further substituents) with an aminodiphenylamine containing at least one water-solubilizing group (e.g. a sulphonic or carboxylic acid group), in the presence of an alkali, if desired under increased pressure. The products are suitable for dyeing wool (by the after-chroming process) and leather, and particularly for chrome printing on cellulose fibres (yielding reddish brown to deep brown prints). In examples, the following pairs of components are heated together in dilute caustic soda solution under reflux, or, in (1), at 110-115 DEG C. in a pressure vessel: (1) 4 - nitro - 41 - hydroxy - 1 : 11 - azo - benzene-31-carboxylic-2-sulphonic acid and 4-aminodiphenylamine-2-sulphonic acid; (2) the same nitro-monoazo dyestuff and 4-amino-41 - hydroxydiphenylamine - 31 - carboxylic - 2 - sulphonic acid; (3) the same nitro-monoazo dyestuff, or its 21-methyl derivative, and 4-amino-41-hydroxydiphenylamine-31-carboxylic-2 : 51-disulphonic acid; (4) 4-nitro-2-methoxy-41 - hydroxy - 1 : 11 - azobenzene - 31 - carboxylic acid and 4 - aminodiphenylamine - 2 : 31 - disulphonic acid. A table gives the properties of further dyestuffs, the following additional components being specified: nitro-monazo dyestuffs: 4-nitro-21-methyl-41-hydroxy-1 : 11-azobenzene - 51 - carboxylic - 2 - sulphonic acid, 4-nitro-5-methyl-41-hydroxy-2-methoxy-1 : 11-azobenzene-31-carboxylic acid and 4-nitro-2 : 5-dimethoxy-41-hydroxy - 1 : 11-azobenzene-31-carboxylic acid; aminodiphenylamine derivatives: 4-amino-41-methoxydiphenylamine-2-sulphonic acid, 4 - amino - 21 : 41 - dimethyl - diphenylamine-2-sulphonic acid and 4-aminodiphenylamine-31-carboxylic-2-sulphonic acid. 4-Amino-41-hydroxydiphenylamine-31-carboxylic acid-2 : 51-disulphonic acid, 4-amino-diphenylamine-2 : 31-disulphonic acid, 4-amino-21 : 41-dimethyldiphenylamine-2-sulphonic acid and 4-aminodiphenylamine-31-carboxylic acid-2-sulphonic acid are obtainable by reduction (e.g. with iron or sodium sulphide) of the nitro groups in the products obtained by condensing 4-nitro-1 - chlorobenzene - 2 - sulphonic acid, in the presence of an acid-binding agent (e.g. sodium acetate) with, respectively, 1-amino-4-hydroxybenzene - 3 - carboxylic acid - 5 - sulphonic acid, metanilic acid, 2 : 4-dimethylaniline and 3-aminobenzoic acid.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH595491X | 1944-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB595491A true GB595491A (en) | 1947-12-05 |
Family
ID=4522402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17811/45A Expired GB595491A (en) | 1944-06-27 | 1945-07-12 | Manufacture of azo dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB595491A (en) |
-
1945
- 1945-07-12 GB GB17811/45A patent/GB595491A/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB197809A (en) | Improvements in the preparation of azo compounds | |
| GB358055A (en) | Process for the manufacture of azo dyestuffs | |
| GB595491A (en) | Manufacture of azo dyestuffs | |
| US2373926A (en) | Azo dyestuffs | |
| US1823946A (en) | Process of dyeing and printing vegetable fibers | |
| GB459949A (en) | Process for the manufacture of o-hydroxyazo dyestuffs | |
| US1610936A (en) | Manufacture of yellow azo-dyestuffs | |
| US1934727A (en) | Safranine dyestuff intermediates and process of preparing the same | |
| GB602419A (en) | Process for the preparation of new brilliant colours of the anthraquinone series | |
| GB891794A (en) | New anthraquinone vat dyestuffs and process for their manufacture | |
| GB851537A (en) | New monoazodyestuffs derived from cyanuric halides, their application and production | |
| GB371449A (en) | Manufacture of new chromiferous azo-dyestuffs | |
| GB922827A (en) | New phthalocyanine dyestuffs and their manufacture and use | |
| GB567217A (en) | Process for the preparation of monoazo dyestuffs | |
| GB863155A (en) | New azodyestuffs containing a triazine nucleus, their application and process for their manufacture | |
| GB615606A (en) | New azo dyestuffs | |
| GB580642A (en) | Manufacture of vat dyestuffs | |
| GB467183A (en) | Manufacture of anthraquinone derivatives | |
| GB369604A (en) | Manufacture of vat-dyestuffs | |
| GB708663A (en) | Manufacture of new trisazo dyestuffs | |
| GB182759A (en) | Production of vat dyestuff | |
| GB191792A (en) | Manufacture of mordant dyestuffs | |
| GB627078A (en) | Manufacture of vat dyestuffs | |
| GB584838A (en) | Process for the preparation of disazodyestuffs | |
| GB788689A (en) | Ice-colours in textile printing |