Patent GB-1025060-A (GB)
Title: Improvements relating to ªÊ-hydroxyphenyl-úË-triazines and their use
IPC: C08K5/3492
Filed: 1964-01-23
Abstract: The invention comprises compounds of formula <FORM:1025060/C2/1> in which X and Y represent H or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and the benzene ring A may be substituted in the 31, 41 and 51 positions by halogen, alkyl, alkenyl or acyloxy groups or by cycloalkyl, aralkyl or aryl groups which may be further substituted.  If X and/or Y are alkyl, the carbon chain may be interrupted by the groups-O-and-S-and may be substituted by hydroxyl amino, aryl or cycloalkyl groups or halogen atoms.  The benzene ring A may be substituted by cycloalkyl, aralkyl or aryl groups further substituted by chlorine or bromine atoms; an acyloxy group derived from an aliphatic, cycloaliphatic or aromatic carboxylic acid which may carry a further carboxy, carbo-alkoxy or alkoxy group; or may carry a fused ring such as a tetramethylene group.  The new compounds may be prepared by heating 1 mole of an amidine of formula <FORM:1025060/C2/2> and one mole of an amidine of formula <FORM:1025060/C2/3> with one mole of an o-hydroxybenzene carboxyic acid ester of formula <FORM:1025060/C2/4> in which R is a hydrocarbon radical which may be substituted.  If desired, any reactive substituents in the new o-hydroxyphenyl-s-triazines can subsequently be altered as follows: if X or Y is an alkoxyalkyl group it can be converted by HBr to a bromoalkyl group; exchangeable halogen can be converted to hydroxy by treatment with sodium hydroxide, to ether groups by treatment with alkali alcoholates or phenolates, to amino groups by treatment with ammonia or a primary or secondary amine; and alcoholic or phenolic hydroxy groups can be esterified or etherified.  The acyloxy groups in the benzene ring A may be introduced by acylation of the corresponding hydroxy compounds. Examples are given of the preparation of the following compounds: (a) 2-(21-hydroxyphenyl) - 4,6 - dimethyl - s - triazine unsubstituted carrying the following substituents on the benzene ring:  51-methyl; 51-cyclohexyl; 51 - 111,111,311,311 - tetramethylbutyl; 31,51-dimethyl; 4,51-dimethyl; 51-benzyl; 51-phenyl; 31-phenyl; 51-chloro; 51-tert.-butyl; 31,51-dichloro; 31-chloro-51-methyl; 31-allyl-51-methyl; 41-acetoxy; 41-butyroyl; 41-methoxycarboxy; 41-cyclohexyloxycarboxy; 41-lauroyloxy; 41-b -carboxy - acryloyloxy; and #z - carbethoxy-valeroyl; and 2-(21-hydroxyphenyl)-s-triazin unsubstituted and carrying the following substituents on the triazine ring: 4,6-didecyl; 4,6-diethyl; 4,6-dimonyl; 4,6-diheptadecyl; 4,6-dipropyl; 4,6-dichloromethyl; 4,6-dibutyl; 4,6-bis - b  - methoxyethyl; 4,6 - bis - b  - methylmer-captoethyl; 4,6 - bis - b  - dimethylaminoethyl; 4,6 - bis - (211 - phenyl - D 111 - propenyl); 4,6-bis - b  - phenylvinyl and 4,6 - bis - b  - phenylethyl.ALSO:New 0-hydroxyphenyl-s-triazines of formula <FORM:1025060/C3/1> in which X and Y represent H or an alkyl, alkenyl, cycloalkyl or aralkyl group which may be substituted and the benzene ring A may be substituted in the 31, 41 and 51 position by halogen, alkyl, alkenyl or acyloxy groups or by cycloalkyl, aralkyl or aryl groups which may be further substituted 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 lactanes, 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; (e) condensation polymers subsequently cross-linked by addition polymerization, e.g. co-polymers of polyesters of unsaturated carbooxylic acids with polyhydric alcohols modified by dicarboxylic acids or vinyl or vinylidene monomers.  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) cellulose acetate films made from a composition comprising also dibutyl phthalate and acetone (Ex. 11); (b) a polyester resin produced by adding a mixture of maleic anhydride and tetrachlorophthalic 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 (Ex. 12); (c) methyl methacrylate polymerized in the presence of lauroyl peroxide (Ex. 13); (d) a copolymer of polyvinyl chloride and dioctyl phthalate (Ex. 14); (e) polyethylene or polypropylene (Ex. 15); (f) polycaprolactam or polyhexamethylene adipamide (Ex. 16); and (g) a lacquer comprising cellulose acetobutyrate, dimethyl glycol phthalate, methyl alcohol, toluene, a triazine derivative and acetone (Ex. 17).