GB708681A - Process for the production of azo dyestuffs - Google Patents

Process for the production of azo dyestuffs

Info

Publication number
GB708681A
GB708681A GB3975/52A GB397552A GB708681A GB 708681 A GB708681 A GB 708681A GB 3975/52 A GB3975/52 A GB 3975/52A GB 397552 A GB397552 A GB 397552A GB 708681 A GB708681 A GB 708681A
Authority
GB
United Kingdom
Prior art keywords
acid
methyl
sulphonic
acids
amino
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
GB3975/52A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB708681A publication Critical patent/GB708681A/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
    • C09B39/00Other azo dyes prepared by diazotising and coupling

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

Abstract

Compounds of the general formula <FORM:0708681/IV (b)/1> (wherein X represents a radical which contains one or more benzene or naphthalene rings or both and may also contain one or more pyrazolone rings, one Y represents NH2 and the other a carboxylic acid group which may be esterified, Z represents hydrogen or an alkyl, aralkyl or aryl group, and n is 1 or 2) are manufactured by the action of acid chlorides of the general formula <FORM:0708681/IV (b)/2> (wherein one A represents NO2 and the other COO. alkyl) on primary or secondary mono- or di-amines of the benzene or naphthalene series, which may contain further substituents (e.g. alkyl, aryl, aralkyl, hydroxy, acylamino or carboxylic or sulphonic acid groups, or halogen atoms), followed by reduction of the nitro group and, if desired, saponification of the ester group before or after the reduction. Specified amines, some of which are reacted in examples with 3 - carbomethoxy - 4 - nitrobenzoyl chloride or 3 - nitro - 4 - carbomethoxybenzoyl chloride, are: aniline and its 3- and 4-sulphonic acids and 2-, 3- and 4-carboxylic acids, o-, m-and p-toluidine, 2 : 4- and 2 : 5-dimethylaniline, o-, m- and p-chloraniline, 2 : 5-dichloroaniline and its 4-sulphonic acid, m- and p-phenylenediamine, 1 : 3-diaminobenzene-4-sulphonic acid, 1 : 4 - diaminobenzene - 31 - sulphonic and -3-carboxylic acid, p-acetyl- and -benzoyl-aminoaniline, p-carbethoxyaminoaniline, 4- and 5-aminosalicylic acids, 1-amino-4-hydroxy-3-carboxybenzene-5-sulphonic acid, benzidine, o-tolidine, dianisidine, 3 : 31-dichlorobenzidine, benzidine - 3 - sulphonic, - 3 : 31 - disulphonic and - 3 : 31 - dicarboxylic acids, 1 - amino - 4-(41 - aminobenzoylamino1 - benzene, 4 : 41 - diaminodiphenylurea, 4 : 41 - diaminostilbene-2 : 21 - disulphonic acid, 4 : 41 - diaminodiphenylamine, 4 : 41 - diaminobenzophenone, 4 : 41 - diaminodiphenylmethane, 4 : 41 - diaminodiphenyl sulphone, 1 -(41 - or 31 - aminophenyl) - 3 - methyl - 5 - pyrazolone, 4 - amino-41 - (311 - methyl - 511 - pyrazolonyl - 111) - stilbene - 2 : 21 - disulphonic acid, a - and b -naphthylamine, 1 - naphthylamine - 5 -, - 6-and - 7 - sulphonic acids and - 3 : 6 -, - 3 : 8-and - 4 : 8 - disulphonic acids, 2 - naphthylamine - 6 - sulphonic acid and - 3 : 6 -, - 4 : 8-, -5 : 7- and -6 : 8-disulphonic acids, 1 : 8 : 4-, 2 : 5 : 7-, 2 : 8 : 6- and 1 : 8 : 6-aminonaphtholsulphonic acids, 1 : 8 : 2 : 4-, 1 : 8 : 3 : 6- and 2 : 8 : 3 : 6 - aminonaphtholdisulphonic acids, N-methyl-, N-ethyl- and N-benzyl-aniline, N-ethylaniline-3- and -4-sulphonic acids, N-ethyl-o- and p-toluidine, N-methyl-m-anisidine, and N-methyl-2 : 5 : 7- and 2 : 6 : 6-aminonaphtholsulphonic acids. Specifications 612,174, [Group IV (c)], and 630,452 are referred to.ALSO:Azo dyestuffs are manufactured by coupling a diazo or tetrazo compound of an amine of the general formula <FORM:0708681/IV(c)/1> (wherein X represents a radical which contains one or more benzene or naphthalene rings or both and may also contain one or more azo groups or one or more pyrazolone rings or both, one Y represents NH2 and the other a carboxylic acid group which may be esterified, Z represents hydrogen or an alkyl, aralkyl or aryl group, and n is 1 or 2) with a compound containing a methylene group capable of coupling or with a hydroxybenzene or hydroxynaphthalene derivative coupling in ortho position to the hydroxy group, and, if desired, treating the product, in substance or on the fibre, with an agent yielding metal (e.g. chromium, cobalt, nickel, lead, manganese or copper). The products dye cellulose fibres in yellow, red, violet, blue, grey or green tints. The diazo or tetrazo components are obtainable by the action of acid chlorides of the general formula <FORM:0708681/IV(c)/2> (wherein one A represents NO2 and the other COO. alkyl) on primary or secondary mono- or di-amines of the benzene and naphthalene series, which may contain further substituents (e.g. alkyl, aryl, aralkyl, hydroxy, acylamino, azo, or carboxylic or sulphonic acid groups, or halogen atoms), followed by reduction of the nitro group and, if desired, saponification of the ester group before or after the reduction. The ester group may also be saponified in the final dyestuffs, as a separate step or in the course of metallization. Examples describe the preparation of the following dyestuffs: (1) 4 : 4\sv-di-(4"-amino-3"-carboxybenzoylamino)-diphenyl \sQ 1 - (4\sv-sulphophenyl) - 3-methyl - 5 - pyrazolone (2 mols), and its copper, nickel, lead and chromium complexes; (2) 4 : 4\sv-di-(4"-amino-3"-carboxybenzoylamino) - stilbene - 2 : 2\sv - disulphonic acid \sQ 1 mol. each of 1-(4\sv-sulphophenyl)- and 1-phenyl-3-methyl-5-pyrazolone; (3) 1-aminobenzene-2-carboxylic acid or its 5-sulphonic acid or 4-sulpho-(2\sv-carboxyphenyl)-amide --> 4-amino-4\sv-(3"-methyl-5"-pyrazolonyl-1")-stilbene-2 : 2\sv-disulphonic acid (acylated with 3-carbomethoxy-4- nitrobenzoyl chloride, saponified and reduced) --> acetoacetyl-o-anisidide, and its copper, nickel and cobalt complexes; (4) as in (3) except that the first component is 1-amino-2-carboxybenzene-4-sulphonic acid and the end component is 2-(p-acetoacetylaminophenyl)-6-methylbenzthiazole - 7 - sulphonic acid; (5) 1-aminobenzene- 2-carboxylic acid or its 4 - sulpho - (2\sv-carboxyphenyl)-amide --> 1 - (4\sv-(4"-amino-3"-carboxybenzoyl)-aminophenyl) -3-methyl-5-pyrazolone --> the compound obtained by monosulphonation of acetoacetyl-o-anisidide; (6) 1-amino-2-carboxybenzene-4- or 5-sulphonic acid or 4 - sulpho - (2\sv-carboxyphenyl)-amide --> 1-(4\sv-(3"-carboxy-4"-aminobenzoyl)-aminophenyl) -3-methyl-5-pyrazolone --> acetoacetyl-o-anisidide; (7) 1 : 8-dihydroxynaphthalene 3 : 6-disulphonic acid \sM dianisidine --> (alkaline) 2-(3\sv-amino-4\sv-carbomethoxybenzoylamino) -5-naphthol-7-sulphonic acid --> acetoacetanilide; (8) dianisidine \sQ 2-(3\sv-carbomethoxy-4\sv-aminobenzoylamino) -5-naphthol-7-sulphonic acid (2 mols) \sQ 1 - (4\sv-sulphophenyl)-3-methyl-5-pyrazolone (2 mols); (9) 3-carboxy-4-aminobenzanilide (2 mols) \sQ 4 : 4\sv-bis-(3"-methyl-5"-pyrazolonyl-1")-stilbene-2 : 2\sv-disulphonic acid; (10) 3-carboxy-4-aminobenzanilide --> 4-benzoylamino-4\sv-(3"-methyl-5"-pyrazolonyl-1") -stilbene-2 : 2\sv-disulphonic acid. In example (11), cotton is dyed yellow with the product of (4) from a bath containing sodium sulphate, with after-coppering in a separate bath containing copper sulphate and acetic acid. Lists are given of additional components, including diamines in which X in the general formula contains two benzene nuclei linked by -CONH-, -NHCONH-, -NH-, -CO-, -CH2- and -SO2-. Specifications 612,174 and 630,452 are referred to.
GB3975/52A 1951-02-17 1952-02-14 Process for the production of azo dyestuffs Expired GB708681A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH708681X 1951-02-17

Publications (1)

Publication Number Publication Date
GB708681A true GB708681A (en) 1954-05-05

Family

ID=4530583

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3975/52A Expired GB708681A (en) 1951-02-17 1952-02-14 Process for the production of azo dyestuffs

Country Status (1)

Country Link
GB (1) GB708681A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4625017A (en) * 1981-11-16 1986-11-25 Ciba-Geigy Corporation Metal complexes of azo dyes containing a 2-(P-N-aceloacetylaminophenyl) benzothiozole moiety

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4625017A (en) * 1981-11-16 1986-11-25 Ciba-Geigy Corporation Metal complexes of azo dyes containing a 2-(P-N-aceloacetylaminophenyl) benzothiozole moiety

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