GB437675A - Manufacture of arylides from 4-hydroxydiphenyl-3-carboxylic acid and of azo-dyestuffs therefrom - Google Patents

Manufacture of arylides from 4-hydroxydiphenyl-3-carboxylic acid and of azo-dyestuffs therefrom

Info

Publication number
GB437675A
GB437675A GB1374934A GB1374934A GB437675A GB 437675 A GB437675 A GB 437675A GB 1374934 A GB1374934 A GB 1374934A GB 1374934 A GB1374934 A GB 1374934A GB 437675 A GB437675 A GB 437675A
Authority
GB
United Kingdom
Prior art keywords
amino
hydroxydiphenyl
chlorobenzene
nitrobenzene
arylides
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
GB1374934A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB1374934A priority Critical patent/GB437675A/en
Publication of GB437675A publication Critical patent/GB437675A/en
Expired legal-status Critical Current

Links

Abstract

Arylides of 4-hydroxydiphenyl-3-carboxylic acid are manufactured by condensing the acid or its chloride with an arylamine which does not contain sulphonic or carboxylic acid groups, e.g. aniline or its homologues, polynuclear arylamines such as naphthylamines, alkoxyarylamines, halogen or nitro-substitution products of the said arylamines, diamines, such as those of the benzene, diphenyl or naphthalene series or diamines derived from a ring system having rings connected by an intermediate member, such as diaminodiphenylamine or diaminocarbazole. In examples, 4-hydroxydiphenyl-3-carboxylic is reacted in toluene solution, in the presence of phosphorus trichloride, with (1) aniline, (2) dianisidine. A table (I) gives the properties of the products obtained by condensation with 1-amino-2-methoxybenzene, 1-amino-2-, 3- and 4-methylbenzene, 1-amino2:4-dimethylbenzene, 1-amino-4-chlorobenzene, 2-aminonaphthalene, 3 : 6-diaminocarbazole, 1 : 4-diaminobenzene, 4 : 4<1>-diaminostilbene, 4 : 4<1>-diaminodiphenylmethane, 1 : 5-diaminonaphthalene, and 1-amino-4-nitrobenzene. Azo dyes; azo dyes, forming upon the material; lakes.--Azo dyes are manufactured by coupling an arylide of 4-hydroxydiphenyl-3-carboxylic acid in substance, on the fibre, or in the presence of a substratum, with a diazo-, tetrazo- or diazoazo-compound, neither component containing solubilizing groups. In examples: (3) cotton piece goods are impregnated with 4 - hydroxydiphenyl - 3 - carboylaminobenzene and developed with diazotized 1-amino-2-(4<1>-chlorophenoxy) - 5 - chlorobenzene yielding a green-olive dyeing; there is similarly obtained from diazotized 1-amino-2-phenoxy-5-chlorobenzene, a green-olive with 4-hydroxydiphenyl-3-carboyl-(1<1>-amino-4<1>-chlorobenzene) and a brown-olive with 4-hydroxydiphenyl-3-carboyl-(1<1>-amino-2<1> -methoxybenzene); (4) cotton yarn is impregnated with bis-(4-hydroxydiphenyl-3-carboyl) - 4<1> - 4<11> - diamino - 3<1>: 3<11> - dimethoxydiphenyl and developed with diazotized 1-amino-2 : 5-dichlorobenzene or 1-amino-2-(2<1> : 5<1>-dichlorophenoxy) - 5 - chlorobenzene, yielding yellowish brown dyeings; (5) the dyestuff 1-amino-2 : 5-dichlorobenzene --> 4-hydroxydiphenyl - 3 - carboyl - (1<1> - aminonaphthalene) is produced in substance. A table (II) gives the tints obtained with additional dyestuffs, employing as additional coupling components certain of the arylides described in table (I) and also the arylides from 1-amino-2 : 5-dimethoxybenzene and 1-amino-3-nitrobenzene, and employing the following additional diazo components : 4 - amino - 3 : 2<1> - dimethyl - 1 : 1<1>-azobenzene, 4 - amino - 4<1> - methoxydiphenylamine, 4 : 4<1> - diamino - 3 : 3<1> - dichlorodiphenyl, 4 : 4<1> - diamino - 3 : 3<1> - dimethoxydiphenyl, 1 - amino - 4 - benzoylamino - 2 : 5-dichlorobenzene, 1-amino-4-(2<1> : 5<1>-dichlorophenoxy)-3-chlorbenzene, 1-amino-2 : 4 : 5-trichlorobenzene, 1-amino-4-nitronaphthalene, 1-amino-2-methyl-4-nitrobenzene, 1-amino-4-benzoylamino - 3 - methoxy - 6 - chlorobenzene, 1-amino-2-chloro-4-nitrobenzene, 1-amino-4-methyl-2-nitrobenzene, 1-amino-2-methoxy-4-nitrobenzene, 1-amino-3-methyl-2 : 4-dichlorobenzene, 1-amino-2-phenylsulphonylbenzene, 1 - amino - 2 - chloro - 5 - trifluoromethylbenzene, 1 - aminoanthraquinone, 4 - amino - 2 : 5-dimethoxy - 4<1> - nitroazobenzene, 1 - amino - 4 - benzoylamino - 2 : 5 - diethoxybenzene and 1-amino-2-methyl-5-chlorobenzene. 1-Amino-2-(2<1> : 5<1>-dichlorophenoxy)-3-chlorobenzene are manufactured by condensing 1 : 4-dichloro-2-nitrobenzene and 3 : 4-dichloro-1-nitrobenzene respectively with a 2 : 5-dichlorophenolate and reducing the nitro-group.
GB1374934A 1934-05-07 1934-05-07 Manufacture of arylides from 4-hydroxydiphenyl-3-carboxylic acid and of azo-dyestuffs therefrom Expired GB437675A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1374934A GB437675A (en) 1934-05-07 1934-05-07 Manufacture of arylides from 4-hydroxydiphenyl-3-carboxylic acid and of azo-dyestuffs therefrom

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1374934A GB437675A (en) 1934-05-07 1934-05-07 Manufacture of arylides from 4-hydroxydiphenyl-3-carboxylic acid and of azo-dyestuffs therefrom

Publications (1)

Publication Number Publication Date
GB437675A true GB437675A (en) 1935-11-04

Family

ID=10028672

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1374934A Expired GB437675A (en) 1934-05-07 1934-05-07 Manufacture of arylides from 4-hydroxydiphenyl-3-carboxylic acid and of azo-dyestuffs therefrom

Country Status (1)

Country Link
GB (1) GB437675A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2744916A (en) * 1953-02-12 1956-05-08 Cutter Lab Phenyl-substituted salicylamides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2744916A (en) * 1953-02-12 1956-05-08 Cutter Lab Phenyl-substituted salicylamides

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