GB1018987A - Improvements relating to ú´-hydroxyphenyl-ú¾-triazines and their use - Google Patents

Abstract

New o-hydroxyphenyl-s-triazines of general formula <FORM:1018987/C3/1> in which one of X and Y represents a radical of formula <FORM:1018987/C3/2> and the other represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and the benzene rings A and B can be further substituted in the 3-, 4- and 5-positions by alkyl, alkenyl, cycloalkyl, aralkyl, aryl and free, etherified or acylated hydroxyl groups or by halogens, are used for improving the stability of light-sensitive organic materials. They may be incorporated, for example, in thermoplastic or thermosetting addition or condensation polymers, e.g. (a) homopolymers and copolymers of vinyl and vinylidene compounds, epoxides, especially bisepoxides, lactams and lactones, and aldehydes; (b) reaction products of isocyanates with hydroxyl and/or amino compounds or with polyesters and/or polyethers; (c) linear condensation products derived from dicarboxylic acids and dihydroxy compounds; (d) cross-linked polycondensates obtained by the condensation of aldehydes with compounds such as ureas, phenols and melamines; and (e) condensation polymers subsequently cross-linked by addition polymerization, e.g. copolymers of polyesters of unsaturated carboxylic acids with polyhydric alcohols modified by dicarboxylic acids or vinyl or vinylidine monomers. They may also be incorporated in natural polysaccharides which may be modified, e.g. cellulose and cellulose esters. Examples are given of the use of the new compounds in stabilizing the following compositions; (a) cellulose acetate films (Example 16); (b) a polyester resin produced by adding a mixture of maleic anhydride and tetrachlorphthalic acid anhydride (or phthalic anhydride) to a mixture of ethylene glycol and diethylene glycol and treating the polyester so produced with styrene or methyl methacrylate (Example 17); (c) methyl methacrylate polymerized in the presence of lauroyl peroxide (Example 18); (d) a copolymer of polyvinyl chloride and dioctyl phthalate (Example 20); (e) polyethylene or polypropylene (Example 19); (f) polycaprolactam or polyhexamethylene adipamide (Example 21); and (g) a lacquer comprising cellulose acetobutyrate, dimethyl glycol phthalate, methyl alcohol and acetone (Example 22).ALSO:The invention comprises compounds of the formula <FORM:1018987/C2/1> in which one of X and Y represents a monovalent aromatic radical of formula <FORM:1018987/C2/2> and the other represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted, and the benzene rings A and B can be further substituted in the 3-, 4- and 5-positions by alkyl, alkenyl, cycloalkyl or aryl groups; free, etherified or esterified hydroxyl groups; and halogens. The new compounds may be prepared by heating equimolar amounts of an oxazine compound of formula <FORM:1018987/C2/3> and of a compound of formula <FORM:1018987/C2/4> In a modification of this process a compound of formula <FORM:1018987/C2/5> may be used instead of the oxazine compound. Any reactive substituents present in the new compounds may be altered e.g. an alkoxyalkyl group can be converted by treatment with hydrogen bromide into a bromoalkyl group; a halogen radical can be replaced by a hydroxy group, an ether group or an amino group by reaction with aqueous sodium hydroxide, alkali alcoholates or phenolates, or with ammonia or primary or secondary amines respectively; and if the compounds contain alcoholic or phenolic hydroxy groups (in addition to the o-hydroxy group) these may be esterified or etherified. Compounds in which X or Y is an alkenyl radical may conveniently be prepared by splitting off water, a hydrohalic acid, an alcohol or an amine from a compound containing a hydroxyalkyl, haloalkyl, alkoxyalkyl or aminoalkyl radical respectively. Examples are given of the preparation of compounds in which (a) the benzene nucleus A carries in addition to the o-hydroxy group no other substituent and alkoxy, alkyl, or alkyloxy, and chlorine substituents; (b) either X or Y is a benzene nucleus carrying in addition to the o-hydroxy group no other substituent or alkoxy, alkyl, aryl, cycloalkyl, aralkyl or chlorine substituents and (c) the other of X and Y is an alkyl, aryl, cycloalkyl, chlorphenylmethyl, alkyl mercaptoalkyl, dialkyl aminoethyl, styryl, methyl styryl, methoxystyryl chlorostyryl, alkoxyalkyl, carboxyalkyl, or haloalkyl group.