Patent GB-991931-A (GB)
Title: Improvements in or relating to stilbene-triazole optical whitening agents
Inventor: ADAMS DENNIS ARTHUR WILLIAM
IPC: C07D249/20
Filed: 1960-05-04
Abstract: The invention comprises compounds of formula <FORM:0991931/C2/1> where Y represents hydrogen or a non-auxochromic or non-chromophonic substituent; R is a straight or branched chain alkyl group containing at least one hydroxy, alkoxy, cyano, carboxy, carbalkoxy, polyoxyalkyl or sulphate group, or a hydroxy group esterified with a polycarboxylic acid, R not being a hydroxyethyl group; A is a mono- or polycyclic aromatic or nitrogen containing heterocyclic residue, two vicinal carbon atoms of which form part of the triazole ring; and Z is a hydrogen atom or an -SO3H or -COOH group which may be in salt form. Preferably R represents -CH2CH2COOR2, -CH2CH2CN, -CH2COOR2, -CH2CH2OCOCH =CH.COOR2, -CH2CH2\CH2COOR2, -CH2CH2OCOCH2CH2 COOR2, -(CH2CH2O)nR2 (excluding hydroxyethyl)-C3H6O)nR2, -CH2CH(OR2)CH2OR2 or -CH2CH(OH)CH2OCH2CH2OCH3 where R2 is hydrogen or an alkyl group, and n is an integer from 1-10.  Where Y is other than hydrogen, it can be e.g. a lower alkoxy group, or halogen atom, preferably in positions ortho or para to the side chain.  A is preferably a benzene, naphthalene or 5- or 6-indazole residue.  The compounds may be prepared by esterification of the corresponding sulphinic acid, suitable reagents being aliphatic compounds containing an epoxide group, compounds having double-bond unsaturation and a substituent R as defined above, or aliphatic halohydrine. Any substituent group R in the product of formula I may be modified to a different group R, e.g. by esterification if applicable. The compounds may also be prepared by condensing the appropriate R ester of 4-methylnitrobenzene -3-sulphinic acid with a Y-substituted benzaldehyde, the resultant nitro-stilbyl compound being reduced to convert -NO2 to -NH2, diazotized and the resulting diazonium compound coupled with a compound ANH2, the ortho-amino azo dye produced, on oxidation yields a compound of Formula I.  The compounds are used as optical-whitening agents (see Divisions C5 and D1).  Specification 991,932 is referred to.ALSO:Ortho-amino azo stilbene dyes of formula <FORM:0991931/C4-C5/1> where Y = H or a non-auxochromic or non-chromophoric group, R is H or a straight or branched-chain alkyl group containing at least one hydroxy, alkoxy, cyano, carboxy, carbalkoxy, polyoxyalkyl group or sulphate group, or an hydroxy group esterified with a polycarboxylic acid, A is a mono- or polycyclic aromatic or nitrogen-containing heterocyclic residue, and Z is a hydrogen atom or -SO3H or -COOH group which may be in salt form, are prepared by coupling a compound ANH2 with the required diazonium compound which is itself made by reduction of a nitro-stilbene compound, and diazotization of the resultant aminostilbene.  Soap compositions comprising sodium carbonate and grain soap, contain as optical whitening agent compounds of formula <FORM:0991931/C4-C5/2> where Y represents hydrogen, or a non-auxochromic or non-chromophoric substituent; R is a straight or branched-chain alkyl group containing at least one hydroxy, alkoxy, cyano, carboxy, carbalkoxy, polyoxyalkyl, or sulphate group, or a hydroxy group esterified with a polycarboxylic acid, R not being an hydroxyethyl group; A is a mono- or polycyclic aromatic or nitrogen-containing heterocyclic residue two vicinal carbon atoms of which form part of the triazole ring, and Z is a hydrogen atom or an -SO3H or -COOH group which may be in salt form. Specification 991,932 is referred to.ALSO:Textiles made from polyamide, polyester and cellulose acetate fibres, and wool, and cellulosic materials particularly paper, are treated with optical whitening agents of formula <FORM:0991931/D1-D2/1> where Y represents hydrogen or a non-auxochromic or non-chromophoric substituent; R is a straight or branched chain alkyl group containing at least one hydroxy, alkoxy, cyano, carboxy, carbalkoxy, polyoxyalkyl or sulphate group, or a hydroxy group esterified with a polycarboxylic acid, R not being a hydroxyethyl group; A is a mono- or polycyclic aromatic or nitrogen-containing heterocyclic residue, two iranal carbon atoms of which form part of the triazole ring; and Z is a hydrogen atom or an -SO3H or -COOH group which may be in salt form. Examples illustrate the treatment of synthetic polyamide fibres with a triazole compound in the presence of formic acid, and the washing of fabrics with a mixture of triazole compound grain soap and sodium carbonate.  Specification 991,932 is referred to.