Patent GB-858183-A (GB)
Title: Water-soluble azo dyestuffs containing acryloylamino groups
Inventor: EISELE JULIUS
IPC: C08F2/44
Filed: 1958-12-12
Abstract: The invention comprises azo dyes which contain; besides at least one water-solubilising group, at least one group of formula: <FORM:0858183/IV (c)/1> where R1 and R2 are H, alkyl, hydroxyalkyl or halogen and R3 is H, alkyl, hydroxyalkyl, halogen or carboxy the group being linked to the dye molecule via an imino group. Preferred are dyes which are free from SO3H groups in the diazo component part of the molecule but which contain at least once, combined by an imino group, a group of formula:  <FORM:0858183/IV (c)/2> where R4 is H, alkyl or halogen and R5 is H or COOH, particularly preferred being those compounds where R4 and R5 are both H.  Water-solubilising groups indicated are sulphonic and carboxylic acid groups, which are preferred, and sulphonamide, alkylsulphone and alcoholic hydroxyl groups.  The dyes are made by treating appropriate dyes containing a primary or secondary acylatable amino group with the required acylating agent or by conventional diazotisation and coupling processes.  Cl p  and Br are specified halogen atoms.  Methyl, ethyl, isopropyl, hydroxyethyl, hydroxyisobutyl are specified alkyl and hydroxyalkyl groups.  Indicated diazo components are derived from benzene, diphenylsulphide, -sulphone, -methane and -amine and naphthalene and they may contain as substituents, additional to those indicated above, further groups such as alkyl, alkoxy, aralkyl- and aryl-sulphone, nitro and halo groups.  Indicated coupling components are pyrazolones, which advantageously contain residues such as -CH3 <FORM:0858183/IV (c)/3> and benzene and naphthalene compounds containing, besides phenolic or enolic hydroxy or amino groups, water-solubilising groups as indicated above.  Other substituents mentioned for the coupling components are -CO-C(R4)= C(R5)H, combined via an imino group, acylated amino groups, alkyl groups or an azo group.  The dyes are used for dyeing and printing-foils, films and textile materials of natural and/or synthetic materials containing carboxylic acid amide groups e.g. wool, silk, polyamides, polyurethanes and leather.  Examples are provided of the preparation of monazo dyes from such diazo components as 1- amino -4- acryloyl-aminobenzene, 1- amino -4-(a chloroacryloyl)-aminobenzene -2- sulphonic acid, 1- amino-benzene -4- sulphonic acid, 2- aminobenzoic acid, 2- methyl -5- nitroaniline, 4- acetylaminoaniline, aniline -4- sulphonamide, 4- acyloyl-amino -2- chloroaniline and 4- amino -41-acryloylaminodiphenyl - sulphide, - sulphone, -methane and -amine and coupling components such as 2- naphthol -6- mono- and 3, 6-disulphonic acids, 1-(phenyl -3- sulphonic acid) -3-methyl -5- pyrazolone, N- acryloyl and -benzoyl-1- amino -8- naphthol -4, 6- disulphonic acids and 1- acryloylaminobenzene -3- hydroxy -6-methylbenzene and the disazo dyes 2- amino -5-nitrophenyl-methylsulphone \sQ and 1- amino -4-acryloylaminobenzene \sQ 1, 8- dihydroxynaphthalene -3, 6- disulphonic acid, the former disazo dye being treated with acryloyl chloride, and the dyes prepared are used in processes to provide dyeings of red, orange and violet shades.  Specification 857,445 is referred to.