GB427803A - Process for the manufacture of water-soluble diazoimino compounds - Google Patents
Process for the manufacture of water-soluble diazoimino compoundsInfo
- Publication number
- GB427803A GB427803A GB30224/33A GB3022433A GB427803A GB 427803 A GB427803 A GB 427803A GB 30224/33 A GB30224/33 A GB 30224/33A GB 3022433 A GB3022433 A GB 3022433A GB 427803 A GB427803 A GB 427803A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- sulphonic acid
- diazotized
- compounds
- diazoimino
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Water soluble diazoamino compounds are made by causing a diazotized aromatic amine free from groups inducing solubility in water to react in the presence of an acid-binding agent on a secondary amine not capable of azo dyestuff formation in which the NH-group forms part of a ring system and which cyclic imine contains at least one sulphonic acid and/or carboxylic acid group with the exception of the compounds specified in Specification 407,840. They are useful in the manufacture of azodyestuffs and in dyeing or printing. In examples diazoimino compounds from the following are described: (1) diazotized 2 - chloro - 4 - benzoylamino - 5 - methoxyaniline and 2 : 2 : 4 : 6 - tetramethyl - 1 : 2 : 3 :-4-tetrahydroquinoline sulphonic acid; (2) diazotized m-chloraniline and 2-methyl-2 : 3-dihydroindole sulphonic acid; (3) diazotized 4-chlor-2-anisidine and carbazole-2-sulphonic acid; (4) diazotized 4-chloro-2-toluidine and hexahydrocarbazole sulphonic acid. 2-2 : 4 : 6 - Tetramethyl - 1 : 2 : 3 : 4 - tetrahydroquinoline sulphonic acid is made by dihydrogenating 2 : 2 : 4 : 6 - tetramethyl - 1 - 2-dihydroquinoline with tin and alcoholic hydrochloric acid and sulphonating. 2 - Methyl - 2 : 3 - dihydroindole sulphonic acid and hexahydrocarbazole sulphonic acid are obtained by sulphonation of the corresponding base. p The Specification as open to inspection under Sect. 91 comprises the following examples: (1) The diazoimino compound from diazotized m-chloraniline and 2-methyl-2 : 3-dihydroindole sulphonic acid is made into a printing paste with the o-toluidide of 2 : 3-oxynaphthoic acid and cotton printed therewith is steamed and the colour developed in an acetic acid, formic acid and Glauber's salt bath; (2) the diazoimino compound from diazotized 4-chloro-2-toluidine and hexahydro-carbazole sulphonic acid and diacetoacetyl - o - toluidine are used as above; (3) dry mixtures comprising the above components are described; (4) a solution of the o-toluidide of 2 : 3-oxynaphthoic acid and the diazoimino compound from diazotized 4-chloro-2-toluidine and hexahydrocarbazole sulphonic acid is treated with acetic acid to precipitate the dyestuff; (5) cotton is impregnated with the o-toluidide of 2 : 3-oxynaphthoic acid and treated with a solution obtained by adding acetic acid to the diazoimino compound from diazotized m-chloraniline and a -methyldihydroindole sulphonic acid. Diazoimino compounds from 6-substituted tetrahydroquinoline-8-sulphonic acid are specified. It is also stated that tetrahydroquinoline-8-sulphonic acid couples in the 6-position with diazo compounds to form azo dyes. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE427803X | 1933-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB427803A true GB427803A (en) | 1935-04-30 |
Family
ID=6477362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30224/33A Expired GB427803A (en) | 1933-02-15 | 1933-10-31 | Process for the manufacture of water-soluble diazoimino compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB427803A (en) |
-
1933
- 1933-10-31 GB GB30224/33A patent/GB427803A/en not_active Expired
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