GB589145A - Manufacture of monoazo-dyestuffs - Google Patents

Manufacture of monoazo-dyestuffs

Info

Publication number
GB589145A
GB589145A GB23206/44A GB2320644A GB589145A GB 589145 A GB589145 A GB 589145A GB 23206/44 A GB23206/44 A GB 23206/44A GB 2320644 A GB2320644 A GB 2320644A GB 589145 A GB589145 A GB 589145A
Authority
GB
United Kingdom
Prior art keywords
amino
acid
methyl
hydroxybenzoic
sulphobenzoyl
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
GB23206/44A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB589145A publication Critical patent/GB589145A/en
Expired legal-status Critical Current

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Abstract

Monoazo dyes are manufactured by diazotizing an amine of the general formula <FORM:0589145/IV/1> in which X represents an -SO3H or -SO2- aryl group, and Y a mono- or poly-nuclear residue of the benzene series comprising an o-hydroxycarboxyphenyl residue, and in which the benzene ring having the substituent X may contain further substituents, and coupling the resulting diazo compound in an acid medium with 2 : 8 : 6-aminonaphtholsulphonic acid or an N-monoalkyl (e.g. the N-monomethyl) derivative thereof. The products dye wool from an acid bath bright red shades which are only slightly changed by after-chroming. In an example 2 : 8 : 6-acid is coupled with diazotized 3 - (31 - amino - 41 - sulphobenzoyl)-amino - 2 - hydroxybenzoic acid, 5 - (31 - amino-41 - sulphobenzoyl) - amino - 2 - hydroxybenzoic acid or its 3-methyl-derivative, 5-(61-chloro-31-amino - 41 - sulphobenzoyl) - amino - 2 - hydroxybenzoic acid, 41 - (311 - amino - 411 - sulphobenzoyl) - amino - 3 - methyl - 4 - hydroxydiphenylmethane - 5 - carboxylic acid, 311-(3111-amino - 4111 - sulphobenzoyl) - amino - 2 : 21 - dihydroxy - 5 : 51 - dimethyltriphenylmethane - 3 : 31 - dicarboxylic acid or 5-[31 - amino - 41 - (p - tolylsulphone) - benzoyl] - amino - 2 - hydroxybenzoic acid. Specification 10168/13, [Class 2 (iii)], is referred to. Amines of the general formula given above are obtainable by condensing an o-hydroxycarboxy compound of the benzene series, containing an amino group, with a 4-halogen-3-nitrobenzoyl halide in the presence of an acid-binding agent, exchanging the halogen atom for a sulphonic acid group by the means of sodium sulphite, or for an aryl-sulphone residue by means of a salt of an arylsulphinic acid, and reducing the nitro group. o-Hydroxycarboxy compounds specified are 3- and 5-amino-, 3 - amino - 5 - methyl-, 5 - amino - 3- and -4-methyl-, 3-amino-5-sulpho- and 5-amino-3-sulpho-2-hydroxybenzoic acids, 41-amino-3-methyl - 4 - hydroxydiphenylmethane - 5 - carboxylic acid and 311-amino-2 : 21-dihydroxy-5 : 51-dimethyltriphenylmethane-3 : 31-dicarboxylic acid. 41 - Amino - 3 - methyl - 4 - hydroxydiphenylmethane - 5 - carboxylic acid is obtainable by heating 5-chloromethyl-3-methyl-2-hydroxybenzoic acid with aniline in water for several hours. 311 - Amino - 2 : 21 - dihydroxy - 5 : 51 - dimethyltriphenylmethane-3 : 31-dicarboxylic acid is obtainable by condensing one molecular proportion of m-nitrobenzaldehyde with two of p-cresotic acid and reducing the nitro group. The Specification as open to inspection under Sect. 91 comprises also the use of diazo components of the general formula above in which X represents halogen, which compounds are obtainable as described above except that the step of exchanging the halogen atom for a sulphonic acid or arylsulphone group is omitted. In an additional example, N-methyl-2 : 8 : 6-acid is coupled with diazotized 5-(41-chloro-31-aminobenzoyl) - amino - 2 - hydroxybenzoic acid or its 3-sulpho-derivative, 3-(41-chloro-31-aminobenzoyl) - amino - 5 - methyl - 2 - hydroxybenzoic acid or 5-(21 : 41-dichloro-31-aminobenzoyl) - amino - 2 - hydroxybenzoic acid. This subject-matter does not appear in the Specification as accepted.
GB23206/44A 1943-11-23 1944-11-22 Manufacture of monoazo-dyestuffs Expired GB589145A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH589145X 1943-11-23

Publications (1)

Publication Number Publication Date
GB589145A true GB589145A (en) 1947-06-12

Family

ID=4522019

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23206/44A Expired GB589145A (en) 1943-11-23 1944-11-22 Manufacture of monoazo-dyestuffs

Country Status (1)

Country Link
GB (1) GB589145A (en)

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