GB459894A - Manufacture of intermediates and azo-dyestuffs derived therefrom - Google Patents

Manufacture of intermediates and azo-dyestuffs derived therefrom

Info

Publication number
GB459894A
GB459894A GB20513/35A GB2051335A GB459894A GB 459894 A GB459894 A GB 459894A GB 20513/35 A GB20513/35 A GB 20513/35A GB 2051335 A GB2051335 A GB 2051335A GB 459894 A GB459894 A GB 459894A
Authority
GB
United Kingdom
Prior art keywords
chloroformate
methyl
condensed
product
reduced
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
GB20513/35A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB459894A publication Critical patent/GB459894A/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
    • C09B29/10Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

Azo dyes, forming upon the material; printing.--Colouring matters are produced on cellulosic fibre by combining a diazotized 4-amino-2 : 5-diethoxyphenylurethane of the general formula <FORM:0459894/IV/1> where X is methyl or ethyl, with 2 : 3-hydroxynaphthoic anilide, o - toluidide, 5 - chloro - o - toluidide or b -naphthalide. The dyeing may be effected by the following methods: (a) the fibre is padded with the coupling component and immersed in a solution of the diazo-compound or printed with a paste containing it; (b) the material is printed with an alkaline paste containing a soluble derivative of the diazo-compound stable under alkaline conditions and the coupling component, and the print is developed by treatment with a mild acidic reagent. In examples: (1) cotton skeins are impregnated with 2 : 3 - hydroxynaphthoic anilide and developed with diazotized N-(4-amino - 2 : 5 - diethoxyphenyl) - methyl - carbamate, yielding a blue dyeing; (2) cotton piece goods are printed with a paste containing the diazoamino compound from diazotized N-(4-amino - 2 : 5 - diethoxyphenyl) - methyl - carbamate and piperidine-a -carboxylic acid, 2 : 3-hydroxynaphthoic anilide, turkey red oil, caustic soda and starch-tragacanth thickener and the print is developed by the action of steam containing acetic acid vapour; for the preparation of the diazoamino compound there may alternatively be used other secondary amines containing water-solubilizing groups, e.g. sarcosine, ethyltaurine, proline and methylglucamine. Specification 17279/13, [Class 15 (ii)], is referred to. Urethanes of the formula given above are obtainable by the following methods: (a) 4-nitro-2 : 5-diethoxyaniline is condensed with methyl or ethyl chloroformate and the product is reduced; (b) the diazo-salt of a water-soluble arylamine, e.g. a sulphonated aniline or naphthylamine derivative, is coupled to 2 : 5-diethoxyaniline and the product is condensed with methyl or ethyl chloroformate and reduced; (c) 2 : 5-diethoxyaniline is condensed with methyl or ethyl chloroformate and the product is nitrated and reduced. The Specification as open to inspection under Sect. 91 comprises the manufacture, by methods similar to those described above, of carbamates of the general formula <FORM:0459894/IV/2> where X is an alkyl, aralkyl, aryl or hydroaryl radicle which may carry substituents, e.g. alkyl or alkoxy groups or halogen, and each Y represents an alkoxy group, and also the production on the fibre of azo dyestuffs by diazotizing these compounds and coupling with ice-colour coupling components, e.g. the arylamides (e.g. anilides, toluidides, alkoxy- and aryloxyanilides, halogenated anilides, halogenated toluidides, halogenated alkoxy- and aryloxyarylides, trifluoromethylanilides, dianisidides, a - and b -naphthylamides) of hydroxyarylcarboxylic acids (e.g. 2 : 3-hydroxynaphthoic acid, and alkyl, alkoxy, alkylamino and arylamino derivatives thereof, 2-hydroxycarbazole-3-carboxylic acid and 2-hydroxyanthracene-3-carboxylic acid), also various acylaminonaphthols (e.g. 1-benzoylamino-7-naphthol, 2-toluylamino - 3 - naphthol and 1 - (2<1> - chlorobenzoylamino) - 5 - naphthol). In additional examples: (1) 2 : 5-dimethoxyaniline is condensed with methyl chloroformate and the product is nitrated and reduced; the methylchloroformate may be replaced by ethyl, butyl, or benzyl chloroformate; (2) 2 : 5-diethoxyaniline is condensed with b -methoxyethyl chloroformate and the product is nitrated and reduced; (3) 2 : 5-diethoxyaniline is condensed with n-butyl chloroformate and the product is nitrated and reduced; (4) the n-butyl chloroformate in (3) is replaced by isobutyl chloroformate; and (5) by benzyl chloroformate; (6) sulphanilic acid is diazotized and coupled with 2 : 5-diethoxyaniline and the product is condensed with methyl chloroformate and reduced; (7) and (8) 2 : 5-diethoxyaniline is condensed with methyl chloroformate and the product is nitrated and reduced; in (8), ethyl chloroformate may alternatively be used; (9) cotton is padded with 2 : 3 - hydroxynaphthoic o-toluidide and a blue dyeing is developed with diazotized N-(4-amino-2 : 5-diethoxyphenyl)-b -methoxyethyl urethane; (10) a reddish-blue dyeing is similarly obtained from 2 : 3-hydroxynaphthoic anilide and diazotized N-(4-amino-2 : 5-diethoxyphenyl)-n-butyl carbamate; (11) a navy blue dyeing is similarly obtained from 2 : 3-hydroxynaphthoic b -naphthylamide and diazotized N - (4-amino - 2 : 5-diethoxyphenyl)-benzyl carbamate. This subject-matter does not appear in the Specification as accepted.
GB20513/35A 1934-07-18 1935-07-18 Manufacture of intermediates and azo-dyestuffs derived therefrom Expired GB459894A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US459894XA 1934-07-18 1934-07-18

Publications (1)

Publication Number Publication Date
GB459894A true GB459894A (en) 1937-01-18

Family

ID=21940955

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20513/35A Expired GB459894A (en) 1934-07-18 1935-07-18 Manufacture of intermediates and azo-dyestuffs derived therefrom

Country Status (1)

Country Link
GB (1) GB459894A (en)

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