GB1019118A - Improvements relating to ú´-hydroxyphenyl-ú¾-triazines and their use - Google Patents

Abstract

New o-hydroxyphenyl-s-triazines of formula <FORM:1019118/C3/1> in which one of X and Y represents a monovalent aromatic radical of formula <FORM:1019118/C3/2> in which R1 and R2 represent hydrogen or halogen or an alkyl, aralkyl, alkoxy or acyloxy group and the other of X and Y represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and in which the benzene rings A and B may be further substituted in the 3, 4 and 5 positions by alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups, halogens, or free etherified or esterified hydroxyl groups, 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 vinylidine compounds, epoxides, particularly 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 incorated in natural polysaccharides which may be modified, such as cellulose and cellulose esters. Examples are given of the use of the new compounds in stabilizing the following compositions: (a) cellulose acetate films (Example 9); (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 10); (c) methyl methacrylate polymerized in the presence of lauroyl peroxide (Example 11); (d) a copolymer of polyvinyl chloride and dioctyl phthalate (Example 12); (e) polyethylene or polypropylene (Example 13); (f) polycaprolactam or polyhexamethylene adipamide (Example 14); and (g) a lacquer comprising cellulose acetobutyrate, dimethyl glycol phthalate, methyl alcohol and acetone (Example 15).ALSO:The invention comprises o-hydroxyphenyl-s-triazines of formula <FORM:1019118/C2/1> in which one of X and Y represents a monovalent aromatic radical of formula <FORM:1019118/C2/2> in which R1 and R2 represent hydrogen, halogen or an alkyl, aralkyl, alkoxy or acyloxy group and the other of X and Y represents hydrogen or an alkyl, alkenyl, cycloalkyl or aralkyl group, the benzene rings A and B being optionally further substituted in the 3-, 4- and 5-positions by alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups, free, etherified or acylated hydroxyl groups, or by halogens. When X or Y is alkyl it may be substituted by halogen or have the formula -alkylene-E-D1 in which the alkylene group has 1-12 carbon atoms and E is -O-, -S-, or -N(D2)-. D1 and D2 represen alkyl radicals and if E is oxygen or nitrogen D1 or D2 can also be hydrogen. If X or Y is alkenyl it may be substituted by aryl groups. The new compounds may be prepared by heating 1 mole of an oxazine compound of formula <FORM:1019118/C2/3> with one mole of an amidine of formula <FORM:1019118/C2/4> Preferably the reaction is carried out in boiling organic solvents, for example methanol, ethanol, ethylene glycol monomethyl or monoethyl ether and dioxan. Reactive substituents in the new compounds may be replaced by other groups. For example if X or Y is an alkoxyalkyl group it may be converted by treatment with HBr into the corresponding bromoalkyl group. A halogen radical may be replaced by a hydroxyl group, an ether group or an amino group by reaction with aqueous sodium hydroxide, alkali alcoholates or phenates, or with primary or secondary amines respectively. Compounds which have alcoholic or phenolic hydroxyl groups may be esterified or etherified. Compounds containing alkenyl groups may be produced by splitting off hydrogen halide, water, alcohol or an amine from a halogenoalkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl derivative respectively. Examples are given of the preparation of compounds of the above general formula in which A carries only an OH substituent and also in which it is additionally substituted by alkyl, chlorine, alkoxy or aralkoxy and X and Y are H, phenyl; phenyl-substituted by alkoxy, chlorine, bromine or alkyl; alkyl; an alkyl group interrupted by sulphur; dialkylaminoalkyl; benzyl; alkoxyalkyl; alkyl substituted by free or esterified carboxyl groups; or cycloalkyl; at least one of the groups X and Y being a group <FORM:1019118/C2/5> as defined above. The oxazimes used as starting materials may be prepared by splitting off water from compounds of formula <FORM:1019118/C2/6> or <FORM:1019118/C2/7> in which the benzene rings may carry additional substituents as specified above for the benzene nucleus A.