Patent GB-915263-A (GB)
Title: Substituted 1:3-oxazoles and process for their manufacture
Filed: 1959-03-13
Abstract: Light-screening and optical brightening agents of formula <FORM:0915263/IV(a)/1> where R1 is an aromatic radical substituted by at least one alkoxy or hydroxyalkoxy group, R2 is hydrogen, alkyl, aryl, or a group <FORM:0915263/IV(a)/2> where x is 1-6, and R3 is an aromatic residue or an heterocyclic residue of aromatic character, an aromatic residue attached via a -CH=CH-group, or a phenyl ring substituted in the 3-position, the 4-position, or the 3,5-positions by <FORM:0915263/IV(a)/3> (see Group IV(b)) are incorporated into plastics such as polyamides, polyurethanes, polyureas, high-melting linear polyesters, polyvinyl and polyacrylic compounds, and polyolefines. Specified polymers are polycaprolactam, the polyamide of adipic acid and hexamethylene diamine, co-polyamides of caprolactam with adipic acid hexamethylene diamine, the polyurethane of hexamethylene diisocyanate with 1,4-butanediol, mixtures of polyesters and polyvalent isocyanates or substances yielding them or heating, linear polyesters of terephthalic acid with glycols, polyvinyl formal, polyvinyl butyral, polyvinyl chloride and its copolymers, polyvinylidene chloride and its copolymers, polystyrene, and polymethyl methacrylate.ALSO:The invention comprises compounds of the formula <FORM:0915263/IV (b)/1> where R1 is an aromatic radical substituted by at least one alkoxy or hydroxyalkoxy group, R2 is hydrogen, alkyl or aryl or a group <FORM:0915263/IV (b)/2> where x is 1-6, and R3 is an aromatic residue or a heterocyclic residue of aromatic character, an aromatic residue attached via a -CH=CH- group, or a phenyl ring substituted in the 3-position, the 4-position, or the 3,5-positions by <FORM:0915263/IV (b)/3> and their preparation by reacting a compound R11H, where R11 is an aromatic radical substituted by at least one alkoxy or hydroxyalkoxy group, in a polyphosphoric acid at elevated temperature with a compound R13CONHCHR12COOH or the corresponding azlactone; <FORM:0915263/IV (b)/4> where R12 is hydrogen, alkyl, aryl, or a group -(CH2)xCH(COOH).NHCOR13 or the corresponding azlactone, and R13 is an aromatic residue, a heterocyclic residue of aromatic character, an aromatic residue attached via a -CH=CH-group, or a phenyl ring substituted in the 3-position, the 4-position, or the 3,5-positions by -CONHCHR12COOH or the corresponding azlactone.  Many examples and reactants are given.  The compounds of the invention may be further treated as follows: (1) by sulphonation; (2) amino groups (obtained by reduction of nitro groups) may be reacted to form N-sulphonic acid groups; or (3) amino groups may be chloracetylated and the halogen exchanged for solubilizing groups, such as quarternary ammonium groups, sulphuric acid groups, or thiosulphuric acid groups.  The compounds of the invention and their further reaction products are lightscreening and optical brightening agents (see Groups IV(a) and IV(c)).ALSO:Light-screening and optical brightening agents of the formula <FORM:0915263/IV (b)/1> where R1 is an aromatic radical substituted by at least one alkoxy or hydroxyalkyl group, R2 is hydrogen, alkyl, aryl, or a group <FORM:0915263/IV (b)/2> where x is 1-6, and R3 is an aromatic residue or a heterocyclic residue of aromatic character, an aromatic residue attached via a -CH=CH- group, or a phenyl ring substituted in the 3-position, the 4-position, or the 3,5-positions by <FORM:0915263/IV (b)/3> or their further reaction products (see Group IV(b)), are applied to fibrous substances (e.g. polyamide fibres and wool), foils or paper, e.g. from dispersions such as aqueous dispersions prepared with soap.