Patent GB-820173-A (GB)
Title: Improvements in light-sensitive linear polymers
IPC: G03F7/038
Filed: 1956-05-25
Abstract: Linear polymers containing recurring units of the form <FORM:0820173/IV (a)/1> where m is 1 or 2, k is 0 or 1, R represents a styrene, vinyl acetate, isopropenyl acetate, alkyl acrylate, alkyl methacrylate, vinyl alkyl ether or ethylene unit, R1 represents an alkylene group containing 2 or 3 carbon atoms and R2 represents a hydrogen or halogen atom, or a hydroxy, methylenedioxy, alkyl, alkoxy, carboxymethoxy, acetamino, -COOR3 or -SO3R3 group, where R3 is hydrogen or an alkali metal, or <FORM:0820173/IV (a)/2> group, where R4 is an alkyl group, the alkyl and alkoxy groups containing 1 to 4 carbon atoms, may be prepared by esterifying maleic anhydride copolymers with chalcones of the form <FORM:0820173/IV (a)/3> in an anhydrous nitrogen base solvent, e.g. pyridine.  Lists of acetophenones and aldehydes suitable for the preparation of chalcones are given and examples describe the esterification of styrene-maleic anhydride copolymers with 41-(b -hydroxy)-chalcone; 4-methoxy-41-(b -hydroxyethoxy)-chalcone; 3,4-methylenedioxy - 41 - (b  - hydroxyethoxy) - chalcone; 4 - carboxymethoxy - 41 - (b  - hydroxyethoxy) - chalcone; 4 - dimethylamino - 41 - (b  - hydroxyethoxy) - chalcone; 2 - sodium sulpho - 41 - (b  - hydroxyethoxy)-chalcone and 41-(a -hydroxyethyl)-chalcone.  The polymers may be dissolved in acetone, dioxane, methyl ethyl ketone, pyridine, methyl "Cellosolve," ethyl "Cellosolve" and "Cellosolve" esters ("Cellosolve" is a Registered Trade Mark) and chlorinated hydrocarbons, and the solutions used in sizing, impregnating and coating and, optionally with sensitizers, e.g. 2-benzoyl methylene-1-methyl-b -naphthothiazoline, in photomechanical printing for forming resist images which may be developed by moist 2-butanone and dilute ammonium hydroxide.ALSO:Chalcones of the form <FORM:0820173/IV (a)/1> where k is 0 or 1, m is 1 or 2, R1 is an alkylene group containing 2 or 3 carbon atoms and RS is hydrogen, halogen, hydroxy, methylenedioxy, alkyl, alkoxy, carboxymethoxy, acetamino, -COOR3 or -SO3R3, where R3 is hydrogen o alkali metal, or <FORM:0820173/IV (a)/2> where R4 is alkyl, the alkyl and alkoxy groups having 1 to 4 carbon atoms, may be prepared by reacting the corresponding acetophenones and benzaldehydes, dissolved in ethyl alcohol, in the presence of aqueous sodium hydroxide solution.  Lists of suitable acetophenones and benzaldehydes are given and examples describe the reaction of 4-(b -hydroxyethoxy) acetophenone with (2) benzaldehyde to give 41-(b -hydroxyethoxy) chalcone; (3) 4-methoxy benzaldehyde to give 4-methoxy-41-(b -hydroxyethoxy) chalcone; (4) 3,4 methylenedioxybenzaldehyde to to give 4-dimethylamino-41-(b -hydroxyethoxy) chalcone; (5) 4-carboxymethoxybenzaldehyde to give 4-carboxymethoxy-41-(b -hydroxyethoxy) chalcone; (6) 4-dimethylaminobenzaldehyde to give 4-dimethylamino-41-(b -hydroxyethoxy) chalcone; (7) 2-sodium sulpho benzaldehyde to give 2-sodium sulpho-41-(b -hydroxyethoxy) chalcone and 1-(p-acetophenyl) ethanol with benzaldehyde to give 41-(a -hydroxyethyl) chalcone. Light-sensitive linear polymers may be prepared by reacting the chalcones with maleic anhydride copolymers (see Group IV (a)).  4 - (b  - hydroxyethoxy) acetophenone may be prepared by reacting p-hydroxyacetophenone with (1(a)) ethylene chlorohydrin in the presence of aqueous sodium hydroxide solution or (1(b)) ethylene oxide.  1-(p-Acetophenyl) ethanol may be prepared by reacting 1-(p-acetophenyl) ethyl acetate with methanol in the presence of sodium methoxide, and acidifying with hydrogen chloride in methanol.