GB954140A - Azo dyes and their production - Google Patents

Azo dyes and their production

Info

Publication number
GB954140A
GB954140A GB25585/62A GB2558562A GB954140A GB 954140 A GB954140 A GB 954140A GB 25585/62 A GB25585/62 A GB 25585/62A GB 2558562 A GB2558562 A GB 2558562A GB 954140 A GB954140 A GB 954140A
Authority
GB
United Kingdom
Prior art keywords
acid
amino
radical
hydroxynaphthalene
anilide
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
Application number
GB25585/62A
Inventor
Rudolf Schroedel
Werner Rohland
Hermann Weissauer
Rudolf Waechter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB954140A publication Critical patent/GB954140A/en
Expired legal-status Critical Current

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
    • C09B62/4401—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 two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—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 two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • 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
    • C09B62/503—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 the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C09B62/507—Azo dyes
    • C09B62/513—Disazo or polyazo dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

3-Amino-b -phenoxypropionic anilide, the corresponding b - methoxy compound and 4-amino-b -phenylmercapto-propionic anilide are obtained by hydrogenating the corresponding nitro compounds using a Raney nickel catalyst. 2-amino-5-hydroxynaphthalene-7-sulphonic acid is amidated with b -phenoxypropionic chloride.ALSO:The invention comprises azo dyes of the formula <FORM:0954140/C3/1> in which A denotes the radical of an azo dye which may contain one or more sulphonic acid groups, R1 is a hydrogen atom or an alkyl radical having from 1 to 5 carbon atoms, R denotes an alkyl radical, a cycloalkyl radical or an aryl radical, X denotes an oxygen atom or a sulphur atom and n is the number 1 or a number greater than 1. The dyes are produced by reacting an acylating agent which yields a radical of the formula <FORM:0954140/C3/2> with an azo dye or an intermediate suitable for the production of an azo dye, which contains at least one acylatable amino group to form a b -(propionamide) ether or thioether derivative and, when an intermediate has been used, completing the preparation of the azo dye in a conventional manner. Acylating agents specified include acid halides or anhydrides of such compounds as b -methylmercapto- or b -methoxypropionic acid, b -phenoxy or b -phenyl thiopropionic acids optionally substituted in the phenyl group with substituents such as chloro, methyl, methoxy and nitro groups. The acylating agents are reacted with the dyes or intermediates in aqueous solution or suspension or in organic solvents and the usual inorganic and organic acid binding agents. Representative of the large number of dyes described in examples are those obtained by coupling diazotised 3-amino-b -phenoxypropionic acid anilide with 1 - hydroxynaphthalene - 4 - sulphonic acid, 1 - (3 - sulphophenyl) - 3 - methylpyrazolone, 1 - (6 - chloro - 2 - methyl - 4- sulphophenyl) - 3 - methyl pyrazolone, 1 - benzoyl or - acetylamino - 8 - hydroxynaphthalene - 3,6-disulphonic acid and by coupling diazotised 4-amino - b - phenylmercaptopropionic acid anilide with 1-(2-chloro-5-sulphophenyl)-3-methylpyrazolone or 1 - hydroxynaphthalene - 4 - sulphonic acid. The products are suitable for dyeing or printing wool, silk, synthetic linear polyamides or polyurethanes, paper and textiles of natural or regenerated cellulose.
GB25585/62A 1961-07-05 1962-07-04 Azo dyes and their production Expired GB954140A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB63139A DE1285642B (en) 1961-07-05 1961-07-05 Process for the production of azo dyes

Publications (1)

Publication Number Publication Date
GB954140A true GB954140A (en) 1964-04-02

Family

ID=6973860

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25585/62A Expired GB954140A (en) 1961-07-05 1962-07-04 Azo dyes and their production

Country Status (4)

Country Link
BE (1) BE619784A (en)
CH (1) CH425034A (en)
DE (1) DE1285642B (en)
GB (1) GB954140A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1198990A (en) * 1957-03-07 1959-12-10 Ciba Geigy New Azo Dyes, Their Preparation and Use

Also Published As

Publication number Publication date
CH425034A (en) 1966-11-30
DE1285642B (en) 1968-12-19
BE619784A (en) 1963-01-04

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