GB921532A - New disazo triazine dyestuffs - Google Patents
New disazo triazine dyestuffsInfo
- Publication number
- GB921532A GB921532A GB1368659A GB1368659A GB921532A GB 921532 A GB921532 A GB 921532A GB 1368659 A GB1368659 A GB 1368659A GB 1368659 A GB1368659 A GB 1368659A GB 921532 A GB921532 A GB 921532A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- acid
- dyes
- sulphonic
- naphthol
- 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention comprises dyes which, as free acids, are of formula <FORM:0921532/IV(a)/1> where A is phenyl or naphthyl and may be substituted by halogen atoms or alkyl or alkoxy groups of not more than 4 carbon atoms or by hydroxy or sulphonic or carboxylic acid groups, R1 is H or alkyl of not more than 6 carbon atoms, X is Cl or Br, Y is amino, aryl, aryloxy, alkylamino, arylamino, sulphoarylamino or carboxyarylamino where the aryl residue has not more than 12 carbon atoms, m is 1 or 2, n is 1, 2, 3, 4 or 5, p is 1 or 2 and B may contain further substituents. The dyes may be made in conventional fashion by diazotizing an appropriate amine A-N=N-B.NH2 and coupling with the required triazine component, by treating an appropriate disazo amino dye with the necessary dihalo-triazine, or by treating a dye corresponding to the above formula but with Y as halogen with an appropriate compound H.D. where D is any of the above specified values of Y except aryl. Representative of specified values for A are methyl, butyl and ethoxy and for R1 are ethyl and butyl. Amongst indicated values of Y are tolyl, phenoxy, di-(b -hydroxyethyl)amino, phenyl- and naphthylamino, hydroxyphenylamino, 2-carboxyphenyl-amino, 3-sulphophenylamino and 3,5-disulphophenylamino. Examples of substituents for B are sulpho, chloro, methyl, ethoxy and acetyl- and benzyl-amino. Representative of amines corresponding to A are aniline, metanilic acid, 5-amino-2-hydroxybenzoic acid, 2-naphthylamine-8-mono-, 3,6-di- and -3,6,8-trisulphonic acids, 1-naphthylamine-7-sulphonic acid, 1-amino-8-naphthol-3,6-disulphonic acid, 5-chloro-4-methylaniline-2-sulphonic acid, 4-methoxyaniline-2-sulphonic acid, anthranilic acid, 4-sulphoanthranilic acid, 2-ethoxy-1-naphthyl-amine-6-sulphonic acid and 4-sulpho-2-amino-anisole. Representative of amines corresponding to B are 2-methoxy-5-methylaniline, m-toluidine, m-aminoacetanilide, 4-benzoylamino-2-amino-anisole, 2-amino-4-methoxyphenoxyacetic acid, anthranilic acid, 2-methoxy-1-naphthylamine-6-sulphonic acid and 1-naphthylamine. Amongst components specified which correspond to the naphthol sulphonic acid component are 1-amino-8-naphthol-3,6-disulphonic acid and its 31- or 41-aminobenzoylamino derivatives, 1-N-butylamino-8-naphthol-4,6-disulphonic acid and 1-amino-8-naphthol-3- and -4-sulphonic acids. Specified triazines include 2-phenyl-, -amino-, diethylamino, -phenylamino-, 21-sulphophenylamino, 31-carboxyphenylamino-, -phenoxy- and -41-hydroxy-31-carboxyphenylamino-4,6-dichloro-1,3, 5-triazine and 2-amino-4,6-dibromo-1,3,5-triazine. Preferred dyes are those containing a metallizable group in B in the ortho position to the azo bond linking B with the naphthalene nucleus. Hydroxy, carboxy, methoxy and carboxymethoxy are specified metallizable groups. Copper, nickel, cobalt and chromium are specified metals, copper being preferred. The metal complexes are made in usual fashion by condensing appropriate disazo amino dyes, dihalo triazines and metallizing agents. Preferably the dye is metallized before reaction with the dihalotriazine. When Y is not to be aryl the metal complexes may also be made by treating appropriate complexes of dihalotriazine disazo dyes with a compound of formula H.D. where D is as above defined. The dyes and their metal complexes colour cellulosic textile materials and are preferably used in conjunction with a treatment with an acid-binding agent vide Specification 797,946. Reddish-blue to greenish-blue shades are obtained. A preferred class of dyes are the copper complexes of dyes of formula <FORM:0921532/IV(a)/2> where B, X, Y and n are as above defined, A1 is a phenyl or naphthyl residue having at least one sulphonic acid group, 21 is OH or OMe and one T is SO3H and the other H. Preferably X is Cl, Y is mono- or di-sulphoanilino residue and n is 1. Numerous examples are provided of the preparation of the dyes and their metal complexes and their use in colouring cellulosic materials. Specifications 838,728 and 847,635 also are referred to.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DENDAT1249423D DE1249423B (en) | 1959-04-22 | Process for the production of disazo dyes, which may be metallizable | |
GB1368659A GB921532A (en) | 1959-04-22 | 1959-04-22 | New disazo triazine dyestuffs |
CH576265A CH452752A (en) | 1959-04-22 | 1960-04-22 | Process for the production of new azo dyes |
CH576365A CH450593A (en) | 1959-04-22 | 1960-04-22 | Process for the production of new azo dyes |
CH453560A CH393593A (en) | 1959-04-22 | 1960-04-22 | Process for the production of new azo dyes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1368659A GB921532A (en) | 1959-04-22 | 1959-04-22 | New disazo triazine dyestuffs |
Publications (1)
Publication Number | Publication Date |
---|---|
GB921532A true GB921532A (en) | 1963-03-20 |
Family
ID=10027566
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1368659A Expired GB921532A (en) | 1959-04-22 | 1959-04-22 | New disazo triazine dyestuffs |
Country Status (3)
Country | Link |
---|---|
CH (3) | CH450593A (en) |
DE (1) | DE1249423B (en) |
GB (1) | GB921532A (en) |
-
0
- DE DENDAT1249423D patent/DE1249423B/en active Pending
-
1959
- 1959-04-22 GB GB1368659A patent/GB921532A/en not_active Expired
-
1960
- 1960-04-22 CH CH576365A patent/CH450593A/en unknown
- 1960-04-22 CH CH453560A patent/CH393593A/en unknown
- 1960-04-22 CH CH576265A patent/CH452752A/en unknown
Also Published As
Publication number | Publication date |
---|---|
CH450593A (en) | 1968-01-31 |
CH452752A (en) | 1968-03-15 |
CH393593A (en) | 1965-06-15 |
DE1249423B (en) | 1967-09-07 |
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