GB431661A - The manufacture of indigoid vat dyestuffs - Google Patents
The manufacture of indigoid vat dyestuffsInfo
- Publication number
- GB431661A GB431661A GB17067/34A GB1706734A GB431661A GB 431661 A GB431661 A GB 431661A GB 17067/34 A GB17067/34 A GB 17067/34A GB 1706734 A GB1706734 A GB 1706734A GB 431661 A GB431661 A GB 431661A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxythionaphthene
- dichloro
- methoxy
- chloride
- acid
- 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
- 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
- C09B7/00—Indigoid dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Thioindigoid vat dyestuffs are manufactured by condensing an alkoxydichlorohydroxythionaphthene, in which the alkoxy group is in the 5, 6 or 7 position and one o-position thereto is free, with an isatin of the benzene or naphthalene series or a reactive 2-derivative thereof or with a reactive 2-derivative of a hydroxythionaphthene of the benzene or naphthalene series, or by condensing a reactive 2-derivative of the said alkoxydichlorohydroxythionaphthene with a hydroxythionaphthene of the benzene or naphthalene series. Some of the products may be improved by after - halogenation. In examples: (1) 5 - methoxy - 6 : 7 - dichloro-3-hydroxythionaphthene is condensed with 9-chloro-1 : 2-naphthisatin; the product dyes cotton grey shades; (2) 5-bromisatin is converted into its chloride by means of phosphorus pentachloride and condensed with 5-methoxy-4 : 7 - dichloro - 3 - hydroxythionaphthene; the product dyes cotton navy blue shades; (3) 6-ethoxy-4 : 7-dichloro-3-hydroxythionaphthene is condensed with 6-methoxy-2 : 3-diketodidihydrothionaphthene-2-(p-dimethylaminoanil) (obtainable by reacting 6-methoxy-3-hydroxythionaphthene with nitrosodimethylaniline); the product dyes cotton orange shades; (4) 5-methoxy-6 : 7-dichloro-2 : 3-diketodihydrothionaphthene - p - dimethylaminoanil (obtained by reacting 5 - methoxy - 6 : 7 - dichloro-3-hydroxythionaphthene with nitrosodimethylaniline) is condensed with 2 : 1-naphthoxythiophene; the product dyes cotton brown shades; (5) 5 : 7-dichlorisatin is converted by means of p phosphorus pentachloride into its chloride, which is condensed with 7 - methoxy - 4 : 5 - dichloro - 3-hydroxythionaphthene; the product dyes cotton blue shades. A table gives the properties of further dyestuffs, the following additional second components being specified: 5 : 7-dibromisatin chloride, 4 - methyl - 5 - chloro - 7-methoxyisatin chloride, 4-methyl-6-chloro-3-hydroxythionaphthene-anil, 6-ethoxy-3-hydroxythionaphthene-anil and 3-hydroxythionaphthene-anil. Specification 222,094, [Class 2 (iii)], is referred to. The Specification as open to inspection under Sect. 91 contains also a reference in the table to the use of 8-chloro-1 : 2-naphthisatin chloride. This subject-matter does not appear in the Specification as accepted. The alkoxydichlorohydroxythionaphthenes employed as starting materials are manufactured by converting the corresponding alkoxydichlorobenzenesulphonic acids by way of the sulphochlorides and mercaptans into the thioglycollic acids and effecting ring closure thereof, or by introducing a sulphur-containing radicle into the o-position to the amino group of a corresponding alkoxydichloroaminobenzene. In examples: (1) 5-methoxy-6 : 7-dichloro-3-hydroxythionaphthene is prepared by acting with phosphorus pentachloride on the sodium salt of 2 : 3 - dichloranisole - 4 - sulphonic acid (obtainable by sulphonation and alkylation of 2 : 3-dichlorophenol), or with chlorosulphonic acid on 2 : 3-dichloranisole, reducing the resulting sulphochloride to the mercaptan, converting this by means of chloracetic acid into the thioglycollic acid and effecting ring closure; (2) 5 - methoxy - 4 : 7 - dichloro - 3 - hydroxythionaphthene is similarly prepared from the sodium salt of 2 : 5-dichloramisole-4-sulphonic acid obtainable from 2 : 5-dichlorophenol as in (1); (3) 6-ethoxy-4 : 7-dichloro-3-hydroxythionaphthene is prepared from 2 : 5-dichloro-4-ethoxyaniline hydrochloride by way of the sulphur chloride compound, 1-amino-2 : 5-dichloro-4-ethoxybenzene - 6 - thioglycollic acid, the cyanogen compound and the aminothionaphthenecarboxylic acid; (5) 7-methoxy-4 : 5-dichloro-3-hydroxythionaphthene is produced from 3 : 4 - dichloranisole - 6 - sulphonic acid (obtainable by sulphonation and alkylation of 3 : 4-dichlorophenol) by a method analogous to that of (1).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE431661X | 1933-06-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB431661A true GB431661A (en) | 1935-07-12 |
Family
ID=6488385
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB17067/34A Expired GB431661A (en) | 1933-06-08 | 1934-06-08 | The manufacture of indigoid vat dyestuffs |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB431661A (en) |
-
1934
- 1934-06-08 GB GB17067/34A patent/GB431661A/en not_active Expired
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