Patent GB-712037-A (GB)
Title: A process for producing fast dyeings and the manufacture of dyestuffs for use therein
IPC: C09B1/34
Filed: 1951-01-02
Abstract: 1 - Aminophenyl - 3(a  - bromovinylsulphone) is prepared by treating phenylvinylsulphone with bromine in carbon tetrachloride, splitting off hydrogen bromide with alkali, nitrating to give 1-nitrophenyl-3(a -bromovinylsulphone) and then reducing.ALSO:Fibrous materials are dyed by means of an acid dyestuff containing one or more vinyl sulphone groups -SO2,CR : CH2 in which R is hydrogen, a low molecular weight hydrocarbon radical or bromine.  The invention comprises also the dyestuffs themselves and methods for their preparation by introducing one or more groups -SO2CR : CH2 into an acid dyestuff or primary product thereof, using methods known for introducing the vinyl sulphone group into an organic molecule. Alternatively, the vinyl sulphone group or groups may be introduced into a neutral dyestuff and the product then sulphonated.  The dyestuffs may be e.g., azo-, nitro-, p  anthraquinone-, triphenylmethane- or phthalocyanine-dyestuffs, many of which are specified.  The following examples are given: (1) Wool is dyed from an acid bath with the dyestuff 1-amino-2-methoxyphenyl-5-vinylsulphone-->1-hydroxynaphthalene-5 -sulphonic acid, (2) Wool is dyed from an acid bath with the dyestuff 1-amino-2-methoxyphenyl-5-vinylsulphone-->2-phenylamino-8 -hydroxynaphthalene-6-sulphonic acid, (3) Wool is dyed with the dyestuff 1-aminophenyl-3-vinylsulphone-->1-(2\sv-chloro-5\sv-sulphophenyl) -3-methyl-5-pyrazolone or the dyestuff 1-aminophenyl-3(a-bromovinylsulphone)-->1-(2\sv-chloro-5\sv sulphophenyl)-3-methyl-5-pyrazolone, the 1-aminophenyl-3(a-bromovinylsulphone) being prepared from phenylvinylsulphone by reacting with bromine in carbon tetrachloride, splitting off hydrogen bromide with alkali, nitrating to give 1-nitrophenyl-3(a-bromovinylsulphone) and then reducing, (4) Wool is dyed with the acid dyestuff 1-aminonaphthyl-5-vinylsulphone-->2-hydroxynaphthalene-6 -sulphonic acid.  (5) Wool is dyed with the dyestuff 1-aminophenyl-4-vinylsulphone-->1-amino-8-hydroxynaphthalene-3, 6-disulphonic acid\sManiline, (6) Wool is printed with a thickened paste containing thiodiglycol and <FORM:0712037/IV(c)/1> which is made by condensing sodium 1-amino-4-bromoanthraquinone-2-sulphonate with 1-amino-2-methoxyphenyl-5-b -hydroxyethyl sulphone and introducing the product into strong sulphuric acid.  (7) Cotton is dyed from a neutral bath containing the dyestuff obtained by coupling tetrazotized 4, 4\sv-diamino-3, 3\sv-dimethoxydiphenyl with 2-hydroxynaphthalene-6-b -hyroxyethysulphone and then with 2 - (2\sv - nitro - 4\sv - b -hydroxyethylsulphonyl)-phenylamino - 5-hydroxynaphthalene - 7 - sulphonic acid and converting into a vinyl sulphone as in (6), (8) Wool is dyed with the dyestuff obtained by coupling the diazo-sulphuric acid ester of 1-aminophenyl-2-b -hydroxyethylsulphone with 1-amino-8-hydroxynaphthalene-3, 6-disulphonic acid and then with diazotized 2-amino-1-methoxyphenyl-4-vinylsulphone followed by treatment with alkali to convert the sulphuric acid ester to the vinyl sulphone group, (9) Acetate rayon is printed with a paste containing thiodiglycol, triethanolamine and the dyestuff <FORM:0712037/IV(c)/2> (10) Wool is dyed with the dyestuff 1-aminophenyl-2-b -hydroxyethylsulphone sulphuric acid ester--> 1-amino - 8 - hydroxynaphthalene-3, 6-disulphonic acid\sM1-aminophenyl-3-vinylsulphone.  Many other suitable dyestuffs are specified.