Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers

The method of preparing a radiation-curable polymer, said polymer being crosslinkable and having pendant ethylenically unsaturated peptide groups and the following structural formula ##STR16## wherein M is a unit from one or more free radically polymerizable ethylenically unsaturated monomers;

• R.sup.1 is hydrogen or methyl;
• R.sup.2 is selected from a single bond, --R.sup.3 -- and ##STR17## in which R.sup.3 is alkylene having 1 to 12 carbon atoms, preferably 1 to 6 carbon atoms, and W is --O--, --S-- or NH--;
• R.sup.4 and R.sup.7 are independently selected from a single bond and methylene, or substituted methylene having 1 to 12 carbon atoms;
• R.sup.5 and R.sup.6 are independently alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl or aralkyl having 6 to 12 carbon atoms or R.sup.5 and R.sup.6 taken together with the carbon to which they are joined form a 5- or 6-membered carbocyclic ring, or may be H when at least one of R.sup.4 and R.sup.7 is methylene;
• n is 1, 2 or 3;
• X is --O--, --NH-- or --S--;
• A is a polymerizable, ethylenically unsaturated group selected from
• (a) ##STR18## in which R.sup.8 is an alkylene group having 1 to 12 carbon atoms, an arylene group having 1 to 12 carbon atoms, an arylene group having 6 to 10 carbon atoms, or an oxyalkylene group, --OR--.sub.p in which R is a lower alkylene group having 2 to 4 carbon atoms and p is 1 to 4;
• R.sup.9 and R.sup.10 are independently hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms or
• (b) --R.sup.8 WY in which R.sup.8 is as defined under the definition for A, W as defined under the definition for R.sup.2, and Y is an ethylenically unsaturated acyl group selected from the group including acryloyl, methacryloyl, cinnamoyl, maleoyl, fumaroyl, itaconoyl and crotonoyl;
• a and b are independent whole integer numbers, and b is at least 1, sufficient to provide a polymer wherein the distribution of M units and ##STR19## units is random throughout the polymer, which method includes the steps of
• a. blending together in a non-nucleophilic solvent
• (1) an ethylenically unsaturated nucleophilic compound of the formula HXA wherein
• H is hydrogen;
• X is --O--, --NH-- or --S--;
• A is a polymerizable, ethylenically unsaturated group selected from
• (a) ##STR20## in which R.sup.8 is an alkylene group having 1 to 12 carbon atoms, an arylene group having 6 to 12 carbon atoms, or an oxyalkylene group, --OR--.sub.p in which R is a lower alkylene group having 2 to 4 carbon atoms and p is 1 to 3;
• R.sup.9 and R.sup.10 are independently hydrogen, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms or
• (b) --R.sup.8 --WY in which R.sup.8 is as defined under the definition for R.sup.2, and Y is an ethylenically unsaturated acryl group selected from the group including acryloyl, methacryloyl, cinnamoyl, maleoyl, fumaroyl, itaconoyl and crotonoyl, and
• (2) a polymer having pendant azlactone groups, said polymer resulting from interpolymerization of
• (a) 10 to 100 percent by weight of units from one or more ethylenically unsaturated azlactone monomers, and
• (b) 90 to 0 percent by weight of one or more vinyl monomers, and
• (3) 0 to 5 percent by weight of a Lewis acid catalyst and
• b. reacting components (1) and (2).