GB950140A - New azo dyes - Google Patents
New azo dyesInfo
- Publication number
- GB950140A GB950140A GB544062A GB544062A GB950140A GB 950140 A GB950140 A GB 950140A GB 544062 A GB544062 A GB 544062A GB 544062 A GB544062 A GB 544062A GB 950140 A GB950140 A GB 950140A
- Authority
- GB
- United Kingdom
- Prior art keywords
- denotes
- group
- isocyanate
- radical
- halogen atom
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
- C09B62/82—Azo dyes
- C09B62/825—Monoazo dyes
Abstract
The invention comprises azo dyes containing, attached by way of a nitrogen atom, the radical of the formula <FORM:0950140/C3/1> in which R1 denotes a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl group, R2 denotes a hydrogen atom or an alkyl, cycloalkyl, aralkyl or aryl group, E denotes a halogen atom, a quaternary ammonium group or an ester group the acid radical of which is derived from polybasic mineral acid or an organic derivative thereof and Y denotes a group of the general formula <FORM:0950140/C3/2> in which A denotes an alkylene radical or a substituted alkylene radical, Z1 denotes a hydrogen atom, a halogen atom or an alkyl group and Z2 denotes a hydrogen atom, a halogen atom or an alkyl group and processes for the preparation thereof wherein (a) an azo dye or an intermediate suitable for the production of an azo dye, which contains one or more reactive hydrogen atoms attached by way of nitrogen is reacted with an isocyanate of the general formula <FORM:0950140/C3/3> or with a corresponding compound capable of being converted into the isocyanate under the reaction conditions and, when a dye intermediate has been used completing the conversion of the reaction product to the azo dye, or (b) an azo dye or an intermediate suitable for the production of an azo dye, which contains one or more reactive hydrogen atoms attached by way of nitrogen, is reacted with an isocyanate of the general formula <FORM:0950140/C3/4> in which R1, R2 have the meanings given above, X denotes a halogen atom and X1 denotes a halogen atom or an OH group protected by an acyl radical capable of being split-off or with a corresponding compound capable of being converted into the isocyanate under the reaction conditions, the radical X1 in the reaction product is converted into a quaternary ammonium group when a halogen atom or into an ester group of which the acid radical is derived from a polybasic mineral acid or an organic derivative thereof when an OH group and, when a dye intermediate has been used the conversion of the reaction product to the azo dye is completed. Examples of compounds capable of being converted into isocyanates are carbamic acid halides, phenyl-carbamic acid esters and carboxylic acid azides. Among the isocyanates specified for use in the process are 1-chlorobut-2-ine-4-isocyanate and 1,2-dichloro-but-2-ene-4-isocyanate. The reactive hydrogen in the starting materials may be present in primary or secondary alkyl-amino, arylamino, alkyl- and arylhydrazino groups, hydroxyl-amino, carboxylic acid amide and amidine or hydrazide groups. Cyanamide, urethane, urea, guanidine or sulphonamide groupings may be present where suitable. Acylatable NH groups may also form part of a heterocyclic ring combined with the initial materials as e.g. in pyrrolidine, piperidine, piperazine, pyrrolidone, caprolactan and succinimide. The dyes are suitable for dyeing or printing wool, silk, polyamides, polyurethanes, cellulose or regenerated cellulose and leather with the addition of basic agents. Representative of specific dyes described are those obtained by coupling diazotized N-(41-aminophenyl)-N1 - (1 - chlorobut - 2 - inyl - 4) - urea or diazotized p - amino - sulphanilyl - N1 - dichlorobutenylurea with 1-naphthol-4-sulphonic acid or by reacting chlorobutinyl isocyanate with the dye obtained by coupling p-acetylamino-benzene diazonium chloride with p-cresol and splitting off the acetyl group.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEB61269A DE1211347B (en) | 1961-02-14 | 1961-02-14 | Process for the production of fiber-reactive azo dyes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB950140A true GB950140A (en) | 1964-02-19 |
Family
ID=6973140
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB544062A Expired GB950140A (en) | 1961-02-14 | 1962-02-13 | New azo dyes |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE613865A (en) |
DE (1) | DE1211347B (en) |
GB (1) | GB950140A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0433764A1 (en) * | 1989-12-15 | 1991-06-26 | BASF Aktiengesellschaft | Reactive dyestuffs with triazin- and chlorobutinyl anchor |
EP3009422A1 (en) * | 2014-10-14 | 2016-04-20 | Ludwig-Maximilians-Universität München | Photo-switchable sulfonylureas and their uses |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1217337A (en) * | 1957-12-23 | 1960-05-03 | Sandoz Ag | Water-soluble dyes containing reactive groups, method of manufacture and applications |
-
1961
- 1961-02-14 DE DEB61269A patent/DE1211347B/en active Pending
-
1962
- 1962-02-13 BE BE613865A patent/BE613865A/en unknown
- 1962-02-13 GB GB544062A patent/GB950140A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0433764A1 (en) * | 1989-12-15 | 1991-06-26 | BASF Aktiengesellschaft | Reactive dyestuffs with triazin- and chlorobutinyl anchor |
EP3009422A1 (en) * | 2014-10-14 | 2016-04-20 | Ludwig-Maximilians-Universität München | Photo-switchable sulfonylureas and their uses |
WO2016059093A1 (en) * | 2014-10-14 | 2016-04-21 | Ludwig-Maximilians-Universität München | Photo-switchable sulfonylureas and their uses |
Also Published As
Publication number | Publication date |
---|---|
BE613865A (en) | 1962-08-13 |
DE1211347B (en) | 1966-02-24 |
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