GB1011576A - Improvements relating to ª¤-hydroxyphenyl-s-triazines and their use - Google Patents

Abstract

New o - hydroxyphenyl - s - triazines of the general formula <FORM:1011576/C3/1> in which X is an aryl group which may be substituted; Y is an alkyl, cycloalkyl, alkenyl or aryl group which may be substituted (any alkneyl group present being separated from Z by at least one carbon atom), Z is -o-, -s-, or -N(R)- in which R is H or an alkyl group, and in which the benzene nucleus A may be further substituted in ths 31, 41 or 51 position by, for example, alkyl, alkenyl, cycloalkyl, aralkyl or aralkyl groups; free, etherified or esterified hydroxy groups, or halogens, are used for the stabilization 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 monomers, epoxides, particularly bis-peroxides; lactams and lactones; and aldehydes; (b) reaction products of isocyanates with hydroxyl and/or amino compounds or with polyethers and/or polyesters; (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 phenols, ureas and melamines; and (e) condensation polymers subsequently cross-linked by addition polymerization. They may also be incorporated 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) a film containing acetyl cellulose (or cellulose triacetate, tripropionate or acetobutyrate) dibutyl phthalate and acetone (Example 34); (b) a polyester resin obtained by adding a mixture of maleic anhydride and tetrachlorphthalic acid anhydride or phthalic anhydride to a mixture of ethylene glycol and diethylene glycol and polymerizing with styrene or methyl methacrylate (Example 35); (c) a polymer obtained from methyl methacrylate in the presence of lauroyl peroxide (Example 36); (d) a polymer obtained from polyvinyl chloride and dioctyl phthalate (Example 37); (e) polyethylene and polypropylene (Example 38); (f) granulated polycaprolactam and polyhexamethylene adipamide (Example 39); and (g) a lacquer prepared from cellulose acetobutyrate dimethyl glycol phthalate methyl alcohol, toluene and ethyl acetate (Example 40).ALSO:The invention comprises compounds of the general formula <FORM:1011576/C2/1> in which X is an aryl group which may be substituted, Y is an alkyl, cycloalkyl, alkenyl or aryl group which may be substituted and having the double bond of any alkenyl group separated from Z by at least one carbon atom, Z is -O-, -S- or -N(R)- in which R represents hydrogen or an alkyl group, and in which the benzene nucleus A can be further substituted in the 31-, 41- and 51-position by, for example, alkyl, alkenyl, cycloalkyl, aralkyl or aryl groups, free, etherified or esterified hydroxyl groups and halogens. The group Y may be alkyl substituted, for example, by hydroxy, alkoxy, alkylmercapto, amino, halogen, carboxylic, carboxylic amide or cyano groups. The new compounds may be prepared by heating 1 mole of an oxazine compound of formula <FORM:1011576/C2/2> with 1 mole of <FORM:1011576/C2/3> The reaction is preferably carried out in boiling organic solvents such as methanol, ethanol, ethylene glycol monomethyl or monoethyl ether or dioxan. Substituents in the product may be subsequently altered, e.g. if Y is an alkoxyalkyl group it may be converted by HBr into a bromoalkyl group, or a halogen radical can be replaced by hydroxyl, an ether group or an amine group. Compounds of the above formula in which Y is an alkenyl radical may be obtained by removal of hydrohalic acid, water, alcohol or amine from the corresponding compound in which Y is halogeno alkyl, hydroxy alkyl, alkoxyalkyl or aminoalkyl respectively. The new compounds may also be prepared by reacting 1 mole of a compound of formula <FORM:1011576/C2/4> with 1 mole of <FORM:1011576/C2/5> under the same conditions as in the method of preparation metioned previously. The oxazines used as starting materials may be prepared by splitting off water from compounds of formula <FORM:1011576/C2/6> or <FORM:1011576/C2/7> Long lists of starting materials are given and detailed examples are given of the preparation of 2-21-hydroxyphenyl)-triazines of the above formula in which A carries no other substituents other than the hydroxy groups or carries one or more hydrocarbon, bromine, chlorine, alkoxy or benzyloxy substituents or hydrocarbon substituents containing an ether group, Y is an unsubstituted hydrocarbon group or a hydrocarbon group substituted by a cyano, alkoxy, carboxylic, esterified carboxylic, chlorine, amino or thioether group and X is a phenyl group which is an unsubstituted or carries one or more hydrocarbon, hydroxy, chloro, bromo-alkoxy or benzyloxy substituents.