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GB753591A - Improvements in new diazoamino derivatives, in a process for making them and in their application - Google Patents

Improvements in new diazoamino derivatives, in a process for making them and in their application

Info

Publication number
GB753591A
GB753591A GB32821/53A GB3282153A GB753591A GB 753591 A GB753591 A GB 753591A GB 32821/53 A GB32821/53 A GB 32821/53A GB 3282153 A GB3282153 A GB 3282153A GB 753591 A GB753591 A GB 753591A
Authority
GB
United Kingdom
Prior art keywords
amino
diazoamino
dicarboxylic acid
acid
diazotized
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
GB32821/53A
Inventor
Pierre Petitcolas
Robert Frederic Michel Sureau
Andre Paul Richard
Rene Pierre Victor Roe
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.)
Compagnie Francaise des Matieres Colorantes SARL
Original Assignee
Compagnie Francaise des Matieres Colorantes SARL
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 Compagnie Francaise des Matieres Colorantes SARL filed Critical Compagnie Francaise des Matieres Colorantes SARL
Publication of GB753591A publication Critical patent/GB753591A/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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/0003Monoazo dyes prepared by diazotising and coupling from diazotized anilines

Landscapes

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

Abstract

Diazoamino derivatives are prepared by condensing a diazo compound, in non-acid medium, with a compound of formula: <FORM:0753591/IV(a)/1> or a salt thereof, in which X is a substituted or unsubstituted alkyl group. Specified substituents in X are -OH, -OCH3, -OC2H5, -COOH, -SO3H, -OSO3H, -OPO3H2, -OPO2H2, -COO alkyl and -CON<. Specified amines from which the diazo compounds are derived are aniline, toluidines, xylidines, cresidines, anisidines, halogen substituted anisidines, monochloroanilines, nitroanilines, nitrotoluidines, nitroanisidines, nitrocresidines, monoacylated paradiamines which may be substituted by halogen atoms or alkyl or alkoxy groups, aromatic monoamines containing sulphamido, sulphone, or trifluoromethyl groups, aminobenzothiazoles, aminoindazoles and aminoazo dyestuffs. The diazoamino derivatives can be mixed with coupling components and used to prepare azo dyes on textile fibres (see Group IV (c)). In examples: (1) 4 : 41-di-N-methylamino - diphenylmethane - 3 : 31 - dicarboxylic acid is dissolved in sodium carbonate solution sodium hyposulphite is added, and a solution of the diazo compound from 1-amino-4-benzoylamino - 2 : 5 - dimethoxy - or - diethoxybenzene is slowly added thereto, the mixture is made alkaline with sodium hydroxide, and the diazoamino derivative is precipitated by the addition of a mixture of sodium hydroxide and sodium chloride; (2) diazotized 5-chloro-2-amino-1-methylbenzene is reacted with 4 : 41-di - N - methylamino - diphenylmethane-3 : 31 - dicarboxylic acid; (3) diazotized 1-amino - 5 - diethylsulphonamido - 2 - methoxybenzene is reacted with 4 : 41-di-N-hydroxyethylamino - diphenylmethane - 3 : 3 - dicarboxylic acid; (4) and (5) diazotized 4-chloro-2-amino-1- methylbenzene or 1-amino-5-diethyl- or - dimethylsulphamido - 2 - methylbenzene is reacted with 4 : 41-di-N-carboxymethylaminodiphenylmethane-3 : 31-dicarboxylic acid. 4 : 41 - Di - N - methylamino - or hydroxyethylamino - or - carboxymethylaminodiphenylmethane - 3 : 31 - dicarboxylic acids. These compounds are prepared by reacting the corresponding N-substituted anthranilic acids with formaldehyde in the presence of hydrochloric acid.ALSO:Diazoamino derivatives, prepared by condensing a diazo compound with a compound of formula <FORM:0753591/IV(c)/1> in which X is a substituted or unsubstituted alkyl group, are mixed with coupling components and developed to give azo dyestuffs on textile fibres of natural or regenerated cellulose. In examples (6) the diazoamino compound obtained by reacting diazotized 5 - chloro - 2 - amino - 1 - methyl-benzene with 4:41-di-N-methylamino - diphenylmethane-3:31-dicarboxylic acid is mixed with the sodium salt of the o-toluidide of b -hydroxynaphthoic acid and sodium sulphate, the mixture so obtained is pasted with water. denatured alcohol. caustic soda, sodium chloride and starch-tragacanth thickener, the paste printed on a cotton fabric and steamed with neutral steam to give yellowsih-red prints (the o-phenetidide of b -hydroxy-naphthoic acid and diacetoacetyl tolidine may also be used as coupling components in the above process and give scarlet and yellow prints respectively) (7) the diazoamino derivative obtained by reacting diazotized 1-amino-5 - diethylsulphamido - 2 - methoxy-benzene with 4:41-di-N-hydroxyethylaminodiphenylmethane-3 : 31-dicarboxylic acid is mixed with the 51-chloro-21 : 41-dimethoxyanilide of b -hydroxy-naphthoic acid, the mixture pasted with water, caustic soda, "Solutene Cl," sodium chlorate and starch-tragacanth thickener, the paste printed on a cotton fabric and steamed in neutral steam to give bluish-red prints; (8) the diazoamino derivative prepared by reacting diazotized 1-amino-5-dimethylsulphamido-2-methyl-benzene with 4 : 41-di-N-carboxymethylamino - diphenylmethane - 3 : 31 - dicarboxylic acid is mixed with the 41-chloro-21 : 51-dimethoxy-anilide of b -hydroxynaphthoic acid and treated as in (7) to give yellowish red prints; (9) the diazoamino derivative prepared by reacting diazotized 1-amino - 4 - benzoylamino - 2:5 - dimethoxy-benzene with 4:41-di-N-methylaminodiphenylmethane-3:31 -dicarboxylic acid is mixed with the sodium salt of the anilide of b -hydroxynaphthoic acid and the mixture treated as in (7) to give blue prints.
GB32821/53A 1952-11-28 1953-11-26 Improvements in new diazoamino derivatives, in a process for making them and in their application Expired GB753591A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR753591X 1952-11-28

Publications (1)

Publication Number Publication Date
GB753591A true GB753591A (en) 1956-07-25

Family

ID=9162831

Family Applications (1)

Application Number Title Priority Date Filing Date
GB32821/53A Expired GB753591A (en) 1952-11-28 1953-11-26 Improvements in new diazoamino derivatives, in a process for making them and in their application

Country Status (1)

Country Link
GB (1) GB753591A (en)

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