GB961088A - New water-soluble monoazo dyes containing haloquinazoline residues - Google Patents

New water-soluble monoazo dyes containing haloquinazoline residues

Info

Publication number
GB961088A
GB961088A GB23102/62A GB2310262A GB961088A GB 961088 A GB961088 A GB 961088A GB 23102/62 A GB23102/62 A GB 23102/62A GB 2310262 A GB2310262 A GB 2310262A GB 961088 A GB961088 A GB 961088A
Authority
GB
United Kingdom
Prior art keywords
quinazoline
dyes
chloro
give
aryl
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
GB23102/62A
Inventor
Hans Weidinger
Guenter Lange
Gerhard Wellenreuther
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 GB961088A publication Critical patent/GB961088A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0072—Preparations with anionic dyes or reactive dyes
    • C09B67/0073—Preparations of acid or reactive dyes in liquid form
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Paper (AREA)

Abstract

2-Aryl-4-haloquinazolines containing a primary amino group in the aryl residue or in the carbocyclic ring of the quinazoline residue are prepared as set forth in the following reaction schemes:- <FORM:0961088/C1/1> The amines are used as diazo components in the preparation of azo dyes. In examples: (1) 2-aminobenzamide is condensed with 4-nitrobenzoyl chloride to give 2-(p-nitrobenzoylamino)-benzamide which is cyclised by boiling in aqueous sodium hydroxide solution containing pyridine to give 2-(4-nitrophenyl)-4-hydroxy-1, 3-quinazoline which is treated with phosgene to give 2-(4-nitrophenyl)-4-chloro-1, 3-quinazoline which is reduced to 2-(4-aminophenyl)-4-chloro-1, 3-quinazoline; (8) as in (1) but using 3-nitrobenzoyl chloride as a starting material the corresponding 3-nitro- and 3-amino-compounds are prepared; (13) 2-amino-5-nitro-benzamide is condensed with benzoyl chloride to yield 2-benzoylamino-5-nitrobenzamide which is cyclised with aqueous sodium hydroxide solution to 2-phenyl-4-hydroxy-6-nitro-quinazolin which is treated with phosgene to give 2-phenyl-4-chloro-6-nitro-quinazoline which is reduced to 2-phenyl-4-chloro-6-aminoquinazoline. Specification 858,562 is referred to.ALSO:The invention comprises water-soluble monoazo dyes, containing at least one sulphonic acid group, of formula A-N = N-B, wherein A is a radical of a 2-aryl-4-haloquinazoline of formula <FORM:0961088/C4-C5/1> wherein Z is an aromatic radical and X is a halogen and B is a coupling component of the naphthalene or pyrazolone series. The dyes are prepared by coupling a diazotized 2-aryl-4-haloquinazoline which has a diazotizable amino group in the aryl radical (Z) or in the carbocyclic part of the quinazoline ring (see Division C2), with a naphthalene or pyrazolone coupling component, the components together containing at least one sulphonic acid group. The dyes may be used to colour cellulose materials by the usual methods for reactive dyes in yellow, red and blue shades. They may also be used to colour leather, paper, silk, wool, polyvinyl alcohol films and synthetic polyamide fibres. In an example 2-(4-aminophenyl)-4-chloroquinazoline is diazotized and coupled in a buffered acid medium with 1-(2-chloro-5-sulphophenyl)-3 - methyl - 5 - pyrazolone to give a dye of formula <FORM:0961088/C4-C5/2> Many further dyes are described in examples. Specification 858,562 is referred to.
GB23102/62A 1961-06-16 1962-06-15 New water-soluble monoazo dyes containing haloquinazoline residues Expired GB961088A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB62924A DE1223970B (en) 1961-06-16 1961-06-16 Process for the preparation of water-soluble azo dyes

Publications (1)

Publication Number Publication Date
GB961088A true GB961088A (en) 1964-06-17

Family

ID=6973779

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23102/62A Expired GB961088A (en) 1961-06-16 1962-06-15 New water-soluble monoazo dyes containing haloquinazoline residues

Country Status (4)

Country Link
BE (1) BE618973A (en)
CH (1) CH411174A (en)
DE (1) DE1223970B (en)
GB (1) GB961088A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3923774A (en) * 1972-04-20 1975-12-02 Basf Ag Quinazolone containing phenyl-azo-pyridine compounds
CN103467388A (en) * 2013-09-02 2013-12-25 温州大学 Method for synthesizing aryl or heteroaryl substituted quinazoline compound
CN103772296A (en) * 2013-12-19 2014-05-07 安徽师范大学 Synthesis method for quinazoline derivative

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR668862A (en) * 1928-02-03 1929-11-07 Ig Farbenindustrie Ag Process for the preparation of azo dyestuffs

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3923774A (en) * 1972-04-20 1975-12-02 Basf Ag Quinazolone containing phenyl-azo-pyridine compounds
CN103467388A (en) * 2013-09-02 2013-12-25 温州大学 Method for synthesizing aryl or heteroaryl substituted quinazoline compound
CN103772296A (en) * 2013-12-19 2014-05-07 安徽师范大学 Synthesis method for quinazoline derivative
CN103772296B (en) * 2013-12-19 2015-06-17 安徽师范大学 Synthesis method for quinazoline derivative

Also Published As

Publication number Publication date
DE1223970B (en) 1966-09-01
CH411174A (en) 1966-04-15
BE618973A (en) 1962-12-14

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