Patent GB-875274-A (GB)
Title: Stilbyl-triazole optical whitening agents
Inventor: ADAMS DENNIS ARTHUR WILLIAM
IPC: C07D487/04
Filed: 1957-03-01
Abstract: Plastics, e.g. polystyrene, contain as opitcal whitening agents compounds of formula: <FORM:0875274/IV (a)/1> where R is an unsubstituted or substituted phenyl group, Y is a substituted or unsubstituted aryloxy group, a mono- or di-substituted amino group, a group -NH,CO,NHZ (in which Z is hydrogen, alkyl or aryl or an alkyl, alkaryl or aryl group, and A is: <FORM:0875274/IV (a)/2> where R1 and R2 are hydrogen or hydrocarbyl groups which may be substituted (for preparation see Group IV(b)).ALSO:The invention comprises optical whitening agents of general formula <FORM:0875274/IV (b)/1> where R is an unsubstituted or substituted phenyl group, Y is a substituted or unsubstituted aryloxy group, any substituents being non-chromophoric, a mono- or disubstituted amino group, -NH.CO.NHZ (where Z is H or an alkyl or aryl group), an alkyl group, an alkaryl group or an aryl group, and A represents <FORM:0875274/IV (b)/2> <FORM:0875274/IV (b)/3> <FORM:0875274/IV (b)/4> <FORM:0875274/IV (b)/5> where R1 and R2 are H or a hydrocarbon radical which may be substituted, e.g. a hydroxyalkyl or polyethanoxy group, or, in residue 4, a chlorophenyl, sulphophenyl or alkaryl group. Residue 1 may be substituted with non-polar groups, e.g. alkyl, alkoxy or halogen.  Substituents on R are preferably nonpolar, e.g. chlorine or alkoxy, and preferably o- or pto the side chain.  They may be prepared by oxidising an o-amino azo dye of formula <FORM:0875274/IV (b)/6> or of formula <FORM:0875274/IV (b)/7> where B is <FORM:0875274/IV (b)/8> <FORM:0875274/IV (b)/9> <FORM:0875274/IV (b)/100> <FORM:0875274/IV (b)/111> followed by conversion of -SO3H to -SO2Y, e.g. via the acid chloride.  Mild oxidising agents are preferably used such as copper sulphate in diethanolamine, cuprammonium sulphate, copper sulphate/pyridine complex, sodium hypochlorite, thionyl chloride or sulphuryl chloride.  Compounds of formula II and III may be made in any convenient manner, e.g. by diazotising a compound of formula <FORM:0875274/IV (b)/122> where C is -SO3H or -SO2Y, and coupling the diazo compound with a compound HB. The intermediate diazo compound may be isolated.  The conversion of -SO3H to -SO2Y may be effected at any convenient stage preferably by first forming the sulphonyl chloride, e.g. with POCl3 or PCl5 in chlorobenzene or with thionyl chloride and then reacting with, e.g. an amine, an aromatic hydrocarbon in the presence of a Friedel-Crafts catalyst or with a phenol.  Specification 874,611 is referred to.ALSO:Washing compositions (synthetic and saponaceous) for synthetic fibres comprise as optical whitening agents compounds of the formula:-  <FORM:0875274/IV(c)/1> where R is an unsubstituted or substituted phenyl group, Y is a substituted or unsubstituted aryloxy group, a mono- or di-substituted amino group, a group NH,CO,NHZ (where Z is H, alkyl or aryl) or an alkyl, alkaryl or aryl group, and A is <FORM:0875274/IV(c)/2> where R1 and R2 are hydrogen or hydrocarbon radicals, which may be substituted (for preparation see Group IV(b)).  As intermediates in the preparation of the above there are prepared #s-aminoazo dyes of the formulae:- <FORM:0875274/IV(c)/3> and <FORM:0875274/IV(c)/4> where B is:- <FORM:0875274/IV(c)/5> by diazotizing a compound of formula:- <FORM:0875274/IV(c)/6> where C is SO3H or SO2Y and coupling the diazotized compound with a compound of formula HB.ALSO:Soap or detergent compositions contain, as optical whitening agents, compounds of the formula <FORM:0875274/III/1> where R is an unsubstituted or substituted phenyl group, Y is a substituted or unsubstituted aryloxy group, a mono- or di-substituted amino group, a group -NH.CO.NHZ (where Z is H, alkyl or aryl) or an alkyl alkaryl or aryl group, and A is <FORM:0875274/III/2> where R1 and R2 are hydrogen or hydrocarbon radicals, which may be substituted.  The products may be dispersed in soap solutions by adding a solution in diethylene glycol to the soap solution.