Patent GB-833396-A (GB)
Title: New water-insoluble monoazo triazine dyestuffs
Inventor: BAKER RONALD
IPC: C09B62/08
Filed: 1956-06-15
Abstract: Triazines of formula <FORM:0833396/IV (b)/1> where R is an alkyl radicle which may be substituted, R1 is H or an alkyl radicle which may be substituted or an aryl radicle, X is Hly, Y is a substituted or unsubstituted alkyl or aryl group, a chlorine atom or a hydroxyl or amino group or an organic radicle linked to the triazine nucleus via N, O or S, Z is an alkylene radicle and Q may be substituted provided that R, R1, Y and Q are free from sulpho, sulphato and carboxy groups are made in conventional fashion, by reacting appropriate Z- and Y-containing reagents with trihalo-triazines or Z-containing components with a dihalo-triazine containing Y. Specified for R are ethyl and hydroxyethyl and for R1 are methyl, ethyl and phenyl. Substituents specified for R1 and Y, when alkyl, are hydroxyl, methoxy, cyano and fluorine and, when aryl, are methyl, methoxy, chlorine and bromine.  X is specified as Cl and Br.  Y, when linked via O, N and S, is specified as methoxy, ethoxy, phenoxy, thiophenoxy, b  - hydroxyethyl -, di - b  - hydroxyethyl -, methyl-, ethyl-, dimethyl-, phenyl-, cyclohexyl-, N-methylphenyl-, b -cyanoethyl- and b -carbethoxyethyl-amino and methylmercapto.  Z is specified as ethylene and propylene and substituents specified for Q are methyl, methoxy, chlorine, bromine, nitro, cyano, methyl-, aminoand methylamino-sulphonyl, trifluoromethyl, amino and acetylamino.  The products are coupling components for azo dyes (see Group IV (c)).  The preparation of N-b -(4-chloro-6-b -hydroxyethylamino - 1,3,5 - triazin - 2 - ylamino) - ethyl - N - ethyl - and - b  - hydroxyethyl-anilines and N-b -(4-chloro-6-N-methylglucamyl - 1,3,5 - triazin - 2 - ylamino/ethylN-ethylaniline is described. The first of the above methods is used, the reactions being effected in acetone or aqueous acetone and if necessary, in the presence of an acid-binding agent. In each case the Z component is reacted first and the triazine intermediate isolated before reaction with the Y component.ALSO:The invention comprises dyes of formula <FORM:0833396/IV(c)/1> where R is a substituted or unsubstituted alkyl radicle, R1 is H or a substituted or unsubstituted hydrocarbon radicle, X is Hlg, Y is a substituted or unsubstituted alkyl or aryl radicle or an hydroxyl or amino group or an organic radicle containing N, O or S linkings to the triazine ring, Z is an alkylene radicle and P and Q may be substituted provided that R, R1, Y, P and Q are free from sulpho, sulphato or carboxy groups.  They may be made, in conventional fashion, by diazotizing an amine corresponding to P and coupling with the heterocyclic component corresponding to Q or, when Y is a hydroxy or amino group or the said organic radicle, by treating an appropriate dihalo triazine dye with the compound H-Y.  Specified for R are ethyl and hydroxyethyl and for R1 are methyl, ethyl and phenyl. Specified substituents for R1 and Y, when alkyl, are hydroxyl, methoxy, cyano and fluorine and, when aryl, are methyl, methoxy, chlorine and bromine.  X is specified as Cl and Br.  Y, when the radicle linked via O, N and S, is specified as methoxy, ethoxy, phenoxy, thiophenoxy, b -hydroxyethyl - di - b  - hydroxyethyl -, methyl -, ethyl-, dimethyl -, phenyl -, cyclohexyl -, N - methyl-phenyl -, b  - cyanoethyl - and b  - carbethoxyethyl-amino and methylmercapto.  Z is specified as ethylene and propylene and specified substituents for P and Q are methyl, methoxy, chlorine, bromine, nitro, cyano, methyl-, amino-and methylamino-sulphonyl, trifluoromethyl, amino and acetylamino.  Specified amines corresponding to P are 2-chloro-4-nitro- and -ethane-sulphonyl -, 4 - cyano - 2 - trifluoromethyl - and 6 - chloro - 2,4 - dinitro - anilines.  Specified for the preparation of coupling components Q by mutual interaction are the amines N-ethyl- and b  - hydroxyethyl - N - b  - aminoethylanilines and N - b  - hydroxyethyl - N - [b  - (b  - hydroxyethylamino)-ethyl] aniline and the triazines 2,4-dichloro - 6 - methoxy -, - phenoxy - dimethylamino -, - phenylamino -, phenyl - and - methyl - 1,3,5 - triazines.  The dyes are used in aqueous dispersion for animal fibres such as wool and silk, cellulose esters such as the acetate and triacetate and synthetic polyamide and polyurethane fibres. Yellow to red shades are obtained.  If amino groups are present in the dyes they may be diazotized on the fibre and coupled with components such as 2-hydroxy-3-naphthoic acid to give navy and black shades.  Examples are provided of the preparation of the dyes and their use in dyeing nylon and cellulose acetate the reactants used being chosen from those indicated above with the addition of 2-amino-5-cyano- and -ethylsulphonyl - benzotrifluoride, 2,5 - dichloro - 4-aminobenzene - sulphon - N - methylamide and 2,4 - bis - methylsulphonylaniline as diazotizable amines and N - b  - (4 - chloro - 6 - N-methylglucamyl - 1,3,5 - triazin - 2 - ylamino]-ethyl-N-ethylaniline as a coupling component.  Additional matter described in the Provisional Specification is given in Specification 825,377.