Radiation-curable coating compositions containing amide acrylate compounds

Claim 2

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of one or more amide acrylate compounds having one nitrogen atom and being of the formula: ##STR6## wherein X, Y and Z may each independently be H, alkyl, aryl, acrylyloxyalkyl, acrylyloxy aliphatic ester formed by reaction of acrylating material with hydroxyl terminated aliphatic ester-containing intermediate resulting from the reaction of inner ester of hydroxy carboxylic acid and amino alcohol, or acrylyloxy aliphatic ether, provided that X, Y and Z together have two, three of four acrylyloxy groups.

Claim 3

The composition of claim 1 wherein X is hydrogen, Y and Z are each ##STR7##

Claim 4

The composition of claim 1 wherein X is ##STR8## Y and Z are each ##STR9##

Claim 5

The composition of claim 1 wherein X is ##STR10## Y and Z are each ##STR11##

Claim 6

The composition of claim 1 wherein X is ##STR12## Y and Z are each ##STR13##

Claim 7

The composition of claim 1 wherein X is ##STR14## Y and Z are each ##STR15##

Claim 8

The composition of claim 1 wherein X is ##STR16## Y and Z are each ##STR17##

Claim 9

The composition of claim 1 wherein X is ##STR18## Y and Z are each ##STR19##

Claim 10

The composition of claim 1 wherein X is ##STR20## Y is --CH 3 Z is ##STR21##

Claim 11

The composition of claim 1 wherein X is ##STR22## Y and Z are each ##STR23##

Claim 12

The composition of claim 1 comprising esterified or partially esterified reaction product of a lower alkyl polyhydric alcohol or an alkyl or aryl polyfunctional epoxide and acrylic acid or methacrylic acid.

Claim 13

The composition of claim 11 wherein said lower alkyl polyhydric alcohol is selected from the group consisting of diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, hexane diol, glycerol, neopentyl glycol, pentaerythritol, trimethylolethane, trimethylolpropane and 2,2-dimethyl-3-hydroxypropyl 2,2-dimethyl-3-hydroxypropionate.

Claim 14

The composition of claim 11 wherein said alkyl or aryl polyfunctional epoxide is selected from the group consisting of butane diol diglycidyl ether, neopentyl glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether and bisphenol A diglycidyl ether.

Claim 15

The composition of claim 1 comprising a reactive compound copolymerizable with said amide acrylate compound selected from the group consisting of styrenes, vinyl amides, esters of vinyl alcohols, acrylate esters, maleate esters and fumarate esters.

Claim 16

The composition of claim 1 comprising a substantially non-reactive solvent selected from the group consisting of xylene, toluene, 2-methoxyethanol, methyl isobutyl ketone and isopropyl alcohol.

Claim 17

The composition of claim 1 comprising a viscosity modifying agent selected from the group consisting of cellulose acetate butyrate, carboxymethyl cellulose, microcrystalline cellulose, fumed silica, castor oil based compositions, 12-hydroxystearic acid, alkyd polymers, acrylic polymers, and modified clays.

Claim 18

The composition of claim 1 comprising a surface tension reducing agent selected from the group consisting of branched lower alkyl acrylate polymers, fluorocarbon polymers and non-ionic alkyl ester surfactants, ethoxylated alkyl ester surfactants and ethoxylated phenol surfactants.

Claim 19

The composition of claim 17 wherein said branched lower alkyl acrylate polymer is poly(2-ethylhexylacrylate).

Claim 20

The composition of claim 1 comprising a slip-aid agent selected from the group consisting of polysiloxanes, fatty acids, fatty acid esters and waxes comprised of esters of long chain monohydric alcohols and long chain fatty acids.

Claim 21

The composition of claim 19 wherein said wax comprises a mixture of cetyl palmitate and related fatty acid esters.

Claim 22

The composition of claim 20 wherein said wax is spermaceti wax.

Claim 23

The composition of claim 1 comprising a photocatalyst system comprising one or more of a photosensitizer, a photopromoter or a photoinitiator, said photocatalyst system being present in an amount in the range of about 0.01 to about 20 percent by weight of polymerizable compound in said composition.

Claim 24

The composition of claim 22 wherein said photosensitizer is selected from the group consisting of benzil, anthraquinone, benzophenone, 3-methoxybenzophenone, anthrone, thioxanthone and chlorothioxanthone.

Claim 25

The composition of claim 22 wherein said photopromoter is selected from the group consisting of tertiary alkyl amines, tertiary alkanol amines and diamines.

Claim 26

The composition of claim 22 wherein said photoinitiator is selected from the group consisting of benzoin, methyl benzoin ether, butyl benzoin ether, isobutyl benzoin ether, α,α-diethoxyacetophenone, α,α-dimethoxy-α-phenyl-acetophenone, α-chloroacetophenone and methyl phenylglyoxylate.

Claim 27

The composition of claim 3 wherein (a) said prepolymer moiety is selected from the group consisting of a polyester polyol, a polyether polyol and a poly(hydrocarbyl siloxane) containing hydroxy functional groups pendent to the siloxane backbone; (b) said isocyanato-containing compound is selected from the group consisting of aliphatic polyisocyanates and aromatic polyisocyanates; and (c) said polyfunctional compound is acrylic acid or a hydroxyl-containing acrylic ester.

Claim 28

The composition of claim 1 comprising extender or hiding pigment.

Claim 29

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of amide acrylate compound of the formula: ##STR24##

Claim 30

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of amide acrylate compound of the formula: ##STR24##

Claim 31

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of amide acrylate compound of the formula: ##STR25##

Claim 32

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising from about one to 99 percent by weight of amide acrylate compound of the formula: ##STR25##

Claim 33

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising (A) from about one to 99 percent by weight of one or more amide acrylate compounds having one nitrogen atom and being of the formula: ##STR26## wherein X, Y and Z may each independently be H, alkyl, aryl, acrylyloxyalkyl, acrylyloxy aliphatic ester formed by reaction of acrylating material with hydroxyl terminated aliphatic ester-containing intermediate resulting from the reaction of inner ester of hydroxy carboxylic acid and amino alcohol, or acrylyloxy aliphatic ether, provided that X, Y and X together have two, three or four acrylyloxy groups; and (B) a urethane acrylate co-curing agent derived from the stepwise reaction of: (a) a prepolymer moiety of molecular weight 300 to 3,000 having a plurality of hydroxyl functional groups, (b) a compound having a plurality of isocyanato groups, a portion of said isocyanato groups reactive with said prepolymer moiety hydroxyl functional groups, and (c) a polyfunctional compound containing at least one functional group which is reactive with an isocyanato group and which polyfunctional compound after reaction with said isocyanato group provides at least one ethylenic functional group in said reaction product.

Claim 34

Radiation polymerizable, highly radiation-sensitive composition curable to form a film comprising (A) from about one to 99 percent by weight of one or more amide acrylate compounds having one nitrogen atom and being of the formula: ##STR26## wherein X, Y and Z may each independently be H, alkyl, aryl, acrylyloxyalkyl, acrylyloxy aliphatic ester formed by reaction of acrylating material with hydroxyl terminated aliphatic ester-containing intermediate resulting from the reaction of inner ester of hydroxy carboxylic acid and amino alcohol, or acrylyloxy aliphatic ether, provided that X, Y and X together have two, three or four acrylyloxy groups; and (B) a urethane acrylate co-curing agent derived from the stepwise reaction of: (a) a prepolymer moiety of molecular weight 300 to 3,000 having a plurality of hydroxyl functional groups, (b) a compound having a plurality of isocyanato groups, a portion of said isocyanato groups reactive with said prepolymer moiety hydroxyl functional groups, and (c) a polyfunctional compound containing at least one functional group which is reactive with an isocyanato group and which polyfunctional compound after reaction with said isocyanato group provides at least one ethylenic functional group in said reaction product.