High speed aqueous solvent developable photopolymer compositions
First Claim
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1. An energy sensitive polymer having the formula:
- ##STR11## wherein R1 independently is hydrogen or methyl;
R2 is given by ##STR12## wherein n is 0 or 1;
R5, R6, R7, and R8 are independently an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms, an aryl or aralkyl group having 6 to 12 carbon atoms or at least one of the pairs R5 and R6, and R7 and R8, taken together with the carbon to which it is joined forms a 5- or 6-membered carbocyclic ring, or any of R5, R6, R7, and R8 may be H when n is 1;
W is --NH--, -NR20, --S-- or --O--;
wherein R20 is alkyl of 1 to 12 carbon atoms; and
Z represents ##STR13## wherein R5, R6, R7, R8, and n are as previously described;
R3 is a polymerizable, ethylenically unsaturated group selected from(a) ##STR14## in which R9 is an alkylene group having 1 to 12 carbon atoms, an arylene group having 6 to 10 carbon atoms, an oxyalkylene group or a poly(oxyalkylene) in which said alkylene group has 2 to 4 carbon atoms, the number of oxygen atoms is a positive integer less than or equal to four;
R10 is hydrogen, cyano, a carboxyl group, or a --C(═
O)NH2 group; and
R11 is hydrogen, an alkyl group having 1 to 12 carbon atoms, or a phenyl group or naphthyl group;
or(b) -R9 -W-T in which R9 is as defined as in (a), W is as previously defined, and T is an ethylenically unsaturated group selected from the group consisting of acryloyl, methacryloyl, cinnamoyl, maleoyl, fumaroyl, itaconoyl, and crotonoyl, and is preferably acryloyl or methacryloyl;
a, b, c, and d are independently integers, wherein a and b are at least 1, and the sum of a+b+c+d is sufficient to provide a polymer having a number average molecular weight in the range of 2,000 to 1,000,000;
G is given by -R9 -N+ R12 R13 R14 X-, wherein R9 is as previously defined, and R12 -R14 are independently an alkyl group having 1 to 16 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms, an aryl or aralkyl group having 6 to 12 carbon atoms or any two or all three of R12 -R14 taken together with the nitrogen to which they are joined can form a 5- to 8-membered heterocyclic ring, and X- represents any non-interfering anion including anions located elsewhere on the polymeric backbone or side chains;
R represents an aryl group having from 6 to 30 carbon atoms, cyano, --CO2 H, carboalkoxy group having from 2 to 40 carbon atoms, or a mono- or dialkylcarbamoyl group having from 2 to 40 carbon atoms;
R4 represents hydrogen, a solubilizing cation, or -E-A wherein E represents an organic divalent connecting group having up to a total of about 18 C, N, S, and nonperoxidic O atoms, and A is an acid selected from carboxylic acids, sulfonic acids, phosphonic acids, and salts thereof.
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Abstract
Novel photosensitive compositions based on azlactone derived polymers are described. The polymers have a hydrocarbyl backbone and pendant peptide groups with free-radically polymerizable functionality attached thereto, said polymer further comprising at least one oxyacid group or salt thereof, and optionally quaternary ammonium salt groups. A high speed durable printing plate having a mild pH aqueous developability is disclosed which incorporates these polymers in combination with a photoinitiator. The polymers are also useful as proofing films in graphic arts applications.
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Citations
12 Claims
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1. An energy sensitive polymer having the formula:
- ##STR11## wherein R1 independently is hydrogen or methyl;
R2 is given by ##STR12## wherein n is 0 or 1;
R5, R6, R7, and R8 are independently an alkyl group having 1 to 12 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms, an aryl or aralkyl group having 6 to 12 carbon atoms or at least one of the pairs R5 and R6, and R7 and R8, taken together with the carbon to which it is joined forms a 5- or 6-membered carbocyclic ring, or any of R5, R6, R7, and R8 may be H when n is 1;W is --NH--, -NR20, --S-- or --O--;
wherein R20 is alkyl of 1 to 12 carbon atoms; andZ represents ##STR13## wherein R5, R6, R7, R8, and n are as previously described; R3 is a polymerizable, ethylenically unsaturated group selected from (a) ##STR14## in which R9 is an alkylene group having 1 to 12 carbon atoms, an arylene group having 6 to 10 carbon atoms, an oxyalkylene group or a poly(oxyalkylene) in which said alkylene group has 2 to 4 carbon atoms, the number of oxygen atoms is a positive integer less than or equal to four;
R10 is hydrogen, cyano, a carboxyl group, or a --C(═
O)NH2 group; and
R11 is hydrogen, an alkyl group having 1 to 12 carbon atoms, or a phenyl group or naphthyl group;
or(b) -R9 -W-T in which R9 is as defined as in (a), W is as previously defined, and T is an ethylenically unsaturated group selected from the group consisting of acryloyl, methacryloyl, cinnamoyl, maleoyl, fumaroyl, itaconoyl, and crotonoyl, and is preferably acryloyl or methacryloyl; a, b, c, and d are independently integers, wherein a and b are at least 1, and the sum of a+b+c+d is sufficient to provide a polymer having a number average molecular weight in the range of 2,000 to 1,000,000; G is given by -R9 -N+ R12 R13 R14 X-, wherein R9 is as previously defined, and R12 -R14 are independently an alkyl group having 1 to 16 carbon atoms or a cycloalkyl group having 5 to 12 carbon atoms, an aryl or aralkyl group having 6 to 12 carbon atoms or any two or all three of R12 -R14 taken together with the nitrogen to which they are joined can form a 5- to 8-membered heterocyclic ring, and X- represents any non-interfering anion including anions located elsewhere on the polymeric backbone or side chains; R represents an aryl group having from 6 to 30 carbon atoms, cyano, --CO2 H, carboalkoxy group having from 2 to 40 carbon atoms, or a mono- or dialkylcarbamoyl group having from 2 to 40 carbon atoms; R4 represents hydrogen, a solubilizing cation, or -E-A wherein E represents an organic divalent connecting group having up to a total of about 18 C, N, S, and nonperoxidic O atoms, and A is an acid selected from carboxylic acids, sulfonic acids, phosphonic acids, and salts thereof. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
- ##STR11## wherein R1 independently is hydrogen or methyl;
Specification