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US5235015A Expired / Lapsed US ⏱️ 0.0 years remaining

High speed aqueous solvent developable photopolymer compositions

Assignee: 3M Innovative Properties Co
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Filing: 1991-02-21
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Granted: 1993-08-10
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Expires: 2011-02-21
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Abstract

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.

Inventors

  • 👤 M. Zaki Ali
  • 👤 Mahfuza B. Ali
  • 👤 Dean M. Moren

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 05:35
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/038; G03F7/0388; C; C08; C08F; C08F8/00; C08F8/30; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31692; Y10T428/31696

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 556 words
An energy sensitive polymer having the formula: ##STR11## wherein R 1 independently is hydrogen or methyl; R 2 is given by ##STR12## wherein n is 0 or 1; R 5 , R 6 , R 7 , and R 8 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 R 5 and R 6 , and R 7 and R 8 , taken together with the carbon to which it is joined forms a 5- or 6-membered carbocyclic ring, or any of R 5 , R 6 , R 7 , and R 8 may be H when n is 1; W is --NH--, -NR 20 , --S-- or --O--; wherein R 20 is alkyl of 1 to 12 carbon atoms; and Z represents ##STR13## wherein R 5 , R 6 , R 7 , R 8 , and n are as previously described; R 3 is a polymerizable, ethylenically unsaturated group selected from (a) ##STR14## in which R 9 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; R 10 is hydrogen, cyano, a carboxyl group, or a --C(═O)NH 2 group; and R 11 is hydrogen, an alkyl group having 1 to 12 carbon atoms, or a phenyl group or naphthyl group; or (b) -R 9 -W-T in which R 9 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 -R 9 -N + R 12 R 13 R 14 X - , wherein R 9 is as previously defined, and R 12 -R 14 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 R 12 -R 14 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, --CO 2 H, carboalkoxy group having from 2 to 40 carbon atoms, or a mono- or dialkylcarbamoyl group having from 2 to 40 carbon atoms; R 4 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.
Claim 2
Dependent Claim 556 words
An energy sensitive polymer having the formula: ##STR11## wherein R 1 independently is hydrogen or methyl; R 2 is given by ##STR12## wherein n is 0 or 1; R 5 , R 6 , R 7 , and R 8 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 R 5 and R 6 , and R 7 and R 8 , taken together with the carbon to which it is joined forms a 5- or 6-membered carbocyclic ring, or any of R 5 , R 6 , R 7 , and R 8 may be H when n is 1; W is --NH--, -NR 20 , --S-- or --O--; wherein R 20 is alkyl of 1 to 12 carbon atoms; and Z represents ##STR13## wherein R 5 , R 6 , R 7 , R 8 , and n are as previously described; R 3 is a polymerizable, ethylenically unsaturated group selected from (a) ##STR14## in which R 9 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; R 10 is hydrogen, cyano, a carboxyl group, or a --C(═O)NH 2 group; and R 11 is hydrogen, an alkyl group having 1 to 12 carbon atoms, or a phenyl group or naphthyl group; or (b) -R 9 -W-T in which R 9 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 -R 9 -N + R 12 R 13 R 14 X - , wherein R 9 is as previously defined, and R 12 -R 14 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 R 12 -R 14 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, --CO 2 H, carboalkoxy group having from 2 to 40 carbon atoms, or a mono- or dialkylcarbamoyl group having from 2 to 40 carbon atoms; R 4 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.
Claim 3
Dependent Claim 23 words
The polymer according to claim 1 wherein R 1 is H, and R 5 and R 6 are methyl, and n is 0.
Claim 4
Dependent Claim 11 words
The polymer according to claim 1 which has a homopolymeric backbone.
Claim 5
Dependent Claim 11 words
The polymer according to claim 1 which has a copolymeric backbone.
Claim 6
Dependent Claim 29 words
The polymer according to claim 1 wherein the A group of R 4 is an alkali metal or a tetra-substituted ammonium salt of a carboxyl, sulfo, or phospho group.
Claim 7
Dependent Claim 26 words
The polymer according to claim 1 wherein the A group of R 4 is PO 3 H 2 , SO 3 H, or CO 2 H.
Claim 8
Dependent Claim 10 words
The polymer according to claim 1 wherein R is --COOH.
Claim 9
Dependent Claim 13 words
The polymer according to claim 1 which is derived from an alkenylazlactone monomer.
Claim 10
Dependent Claim 21 words
The polymer according to claim 1 which is derived from an alkenylazlactone monomer and at least one additional free-radically polymerizable comonomer.
Claim 11
Dependent Claim 12 words
The polymer according to claim 9 wherein said comonomer is a diacid.
Claim 12
Dependent Claim 39 words
The polymer according to claim 9 wherein said alkenylazlactone is present in the range of 10 to 100 weight percent and said at least one comonomer is present in the range of more than 0 to 90 weight percent.
Claim 13
Dependent Claim 19 words
The polymer according to claim 1 having a number average molecular weight in the range of 2,000 to 1,000,000.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-08-09 1997-02-08 1997-08-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-08-09 2001-02-08 2001-08-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-08-09 2005-02-08 2005-08-10 $7700.00 Window Closed / Lapsed

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