GB768999A - New disazo-dyestuffs and process for making them - Google Patents

New disazo-dyestuffs and process for making them

Info

Publication number
GB768999A
GB768999A GB25215/53A GB2521553A GB768999A GB 768999 A GB768999 A GB 768999A GB 25215/53 A GB25215/53 A GB 25215/53A GB 2521553 A GB2521553 A GB 2521553A GB 768999 A GB768999 A GB 768999A
Authority
GB
United Kingdom
Prior art keywords
chloro
carboxylic acid
methyl
methoxy
azo
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
GB25215/53A
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 Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB768999A publication Critical patent/GB768999A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B35/00Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • C09B35/02Disazo dyes
    • C09B35/021Disazo dyes characterised by two coupling components of the same type
    • C09B35/033Disazo dyes characterised by two coupling components of the same type in which the coupling component is an arylamide of an o-hydroxy-carboxylic acid or of a beta-keto-carboxylic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Vinyl polymers, e.g. polyvinyl chloride, are coloured with pigment dyestuffs of formula R2-N=N-R1-N=N-R2, where R1 is an anthraquinone residue free of sulphonic and carboxylic acid groups and in which the two carbon atoms to which the azo linkages are bound are separated from one another by at least three carbon atoms of the anthraquinone nucleus and R2 is a residue of an azo component free of sulphonic and carboxylic acid groups and bound to the azo linkage in a position vicinal to a hydroxyl group. The preparation of the dyestuffs and lists of components from which they are obtained is in Group IV (c). Yellow, red, brown and blue shades are obtained. In examples, polyvinyl chloride is coloured by rolling in pigments made from 1,5-diaminoanthraquinone and (1) 1-acetoacetylamino-2-chloro- and -methoxy-, -2-chloro-5-trifluoromethyl, -4-methyl-, -2,5-dichloro-, 2,4-dimethyl-5-chloro-, -2-chloro-4-acetylamino-5-methoxy-, -2,5-dimethoxy-4-chloro-, -3-sulphonamido- and -2-methoxy-5-methyl-benzenes, 2-acetoacetylamino-6-ethoxybenzthiazole, acetoacetylaminobenzene, 1 - benzoylacetylamino - 2 - methoxy - 5 - methylbenzene and 1-phenyl- and -(21-chlorophenyl)-3-methyl-5-pyrazolone; (2) 1-(21-oxy-31 - naphthoylamino) - benzene and -2-methoxybenzene and (4) 2 - oxycarbazole - 3 - carboxylic acid -(41-chlor)-anilide and 2-oxydiphenylene oxide -3-carboxylic acid -(21,51-dimethoxy)-anilide from 2,6-diaminoanthraquinone and (3) 1 - acetoacetylamino - 2 - chloro- and -methoxy-, -2,5-dichloro-, -4-methyl- and 2,5-dimethoxy-4-chloro - benzenes, 1 - acetoacetylamino - benzene, 1-(21-chlorophenyl)-3-methyl-5-pyrazolone and 21 - oxy - 31 - naphthoylamino - benzene and -2-methoxybenzene, from 2,5- and 2,6-diaminoanthraquinones and (5) 5,8-dichloro-1-naphthol and from 2,6-diamino-3,7-dibrom-, 1,5-dichloro-and -1,3,5,7-tetrabrom-anthraquinones and (6) 1-acetoacetylamino-2-chlorobenzene.ALSO:The invention comprises dyestuffs of formula R2-N=N-R1-N=N-R2 where R1 is an anthraquinone residue free of sulphonic and carboxylic acid groups and in which the two carbon atoms to which the azo linkages are bound are separated from one another by at least three carbon atoms of the antraquinone nucleus and R2 is a residue of an azo component free of sulphonic and carboxylic acid groups and bound to the azo linkage in a position vicinal to a hydroxyl group. They are made by coupling appropriate tetrazotized diamino anthraquinones with coupling components. Advantageously the diamine is tetrazotized in concentrated sulphuric acid and the tetrazo compound isolated before coupling. Coupling is advantageously effected in a weakly acid medium in the presence of a wetting or dispersing agent. Specified diaminoanthraquinones are: 1, 5-, 1, 6-, 1, 7-, 2, 6-, and 2, 7-diamino-, 4, 8-dichlor-, 2, 4, 6, 8-tetrachlor-, 2, 6-dibromo- and 2, 4, 6, 8-tetrabromo-1, 5-diamino-, 1, 5-dichloro-, 1, 5- and 3, 7-dibromo- and 1, 3, 5, 7-tetrabromo-2, 6-diamino- and 3, 6-dibromo-2, 7-diamino-anthraquinone. Azo components specified are 4-methyl- and 5, 8-dichloro-1-naphthol, 2-naphthol, 6-bromo-2-naphthol, 2-naphthol-3-carboxylic acid naphthyl-(1)-amide, -phenylamide and -21-methoxyphenylamide. 2-oxycarbazole-3-carboxylic acid anilide and -41-chloranilide, 2-oxydiphenylene oxide-3-carboxylic acid anilide or -21, 51dimethoxy-anilide, 1-benzoylacetylamino-2-methoxy-5-methylbenzene and acetylamino compounds derived from the following amines: aniline, 1-amino-2-chloro, -methyl- and -methoxy-, -4-methyl, -2, - 5-dichloro-, -2, - 4-dimethyl-5-chloro-, 2-chloro-4-acetylamino-5-methoxy-2-chloro-5-trifluoromethyl-, -2, - 5-dimethoxy-4-chloro-, -2-methoxy-5-methyl- and -2, 6-dimethylbenzene and 1-aminobenzene-3-sulphonic acid amide and 2-acetoacetylamino-6-methoxybenzthiazole, barbuturic acid, 1-naphthyl-(2)-, -phenyl-, ,-(21-chlorophenyl)- and (21methoxy-51 methylphenyl)-3-methyl-5-pyrazoline. The products are used in the dyeing or printing of a wide variety of materials and especially in pigment printing. The following materials may be dyed, paper, glass fibres, artificial silks, rubber, lacquers, natural and synthetic resins, coloured pencils, cosmetic preparations and laminated plates, yellow, red, brown and blue shades are obtained. Examples and tables specified components an additional of dyestuffs from certain of the above are provided illustrating the preparation coupling component being 2-acetoacetylamino-6-ethoxy-benzthiazole.ALSO:Pigment dyestuffs of formula R2 - N = N - R1 - N = N - R2 where R1 is an anthraquinone residue free of sulphuric and carboxylic acid groups and in which the two carbon atoms to which the azo linkages are bound are separated from one another by at least three carbon atoms of the anthraquinone nucleus and R2 is a residue of an azo component free of sulphuric and carboxylic acid groups and bound to the azo linkage in a position vicinal to a hydroxyl group are used for colouring rubber. The preparation of the dyestuffs and lists of components used therein is in Group IV(c). The pigments are in yellow, red, brown, and blue shades.
GB25215/53A 1952-09-12 1953-09-11 New disazo-dyestuffs and process for making them Expired GB768999A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH768999X 1952-09-12

Publications (1)

Publication Number Publication Date
GB768999A true GB768999A (en) 1957-02-27

Family

ID=4535244

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25215/53A Expired GB768999A (en) 1952-09-12 1953-09-11 New disazo-dyestuffs and process for making them

Country Status (1)

Country Link
GB (1) GB768999A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343882A (en) * 1980-04-11 1982-08-10 Ricoh Company, Ltd. Electrophotographic bisazo photoconductor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4343882A (en) * 1980-04-11 1982-08-10 Ricoh Company, Ltd. Electrophotographic bisazo photoconductor

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