US 5,328,805 AGranted

Aqueous developable photosensitive polyurethane-(meth)acrylate

AssigneeW. R. Grace & Co.-Conn.

InventorsTruc-Chi T. Huynh-Tran, Ronald J. Kumpfmiller

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Abstract

A photopolymer useful in preparing water-developable, solid printing plates is prepared by preparing a urethane prepolymer by reacting polyoxyalkylene diols or polyester diols, or a mixture thereof, with an excess of diisocyanate, followed by chain extending the resulting prepolymer mixture with an alkyldialkanolamine, then reacting the chain-extended product with a hydroxyalkyl(meth)acrylate. The resulting photopolymer is suitably formulated with additional photoactive (meth)acrylate monomers or oligomers and photoinitiator for casting or extrusion on a substrate to form a flexographic printing plate. Following UV exposure of the plate through a negative, unexposed areas can be removed by washing with a slightly acidic aqueous medium, to give a plate with a desirable relief image. The use of the aqueous washout solution as opposed to organic solvents minimizes pollution problems.

Claims15

Dependent claims

Printing plate comprising a substrate and a layer of UV-curable composition thereon, where the composition comprises, in parts by weight,

Photopolymer, about 50-100;
Reactive diluent, 0 to about 25;
Photoinitiator, about 0.1-10;
wherein the photopolymer comprises G--R--R.sup.1 --G, where
R comprises B or E, or mixtures thereof;
and F;
A is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, or --CH.sub.2 CH(CH.sub.3)CH.sub.2 --;
B is;
,
D is, or --R--O--and has a number average molecular weight of about 600-6000;
E is,
F is,
G is CH.sub.2 .dbd.C(R.sup.9)--C(:O)--O--R.sup.8 --O--C(:O)--NH--;
R.sup.1 is a divalent aromatic, aliphatic, or cycloaliphatic group containing 2-20 carbons;
R.sup.2 is a divalent aliphatic, cycloaliphatic, or alpharyl group of 2-20 carbons;
R.sup.3 is a divalent aliphatic, cycloaliphatic, aryl, or alpharyl group of 1-20 carbons;
R.sup.4 and R.sup.6 are the same or different alkylene groups with 1-6 carbons;
or R.sup.4 can be --(CH.sub.2 CH.sub.2 O).sub.d CH.sub.2 CH.sub.2 --, provided R.sup.6 is --(CH.sub.2 CH.sub.2 O).sub.e CH.sub.2 CH.sub.2 --, where d and e are each 0-9 and d+e=3-15;
R.sup.5 is --N(R.sup.7)--, --N N--, or --(Ph)--;
R.sup.7 is an alkyl group with 1-6 carbons;
R.sup.8 is 1-7 carbon alkylene;
R.sup.9 is H or methyl;
A--O).sub.b has a number average molecular weight of about 650.degree.-7000.degree..

20 more elements

A printing plate made by making a mixture, comprising in parts by weight,

Photopolymer, about 50-100;
Reactive diluent, 0 to about 0.1-10;
Photoinitiator, about 0.1-10;
Organic solvent, 0 to about 200;
casting the mixture on a plate substrate;
and drying the plate to remove solvent;
wherein the photopolymer comprises a composition of the structure G--R--R.sup.1 --G, where
R comprises B or E or mixtures thereof;
and F;
A is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, or --CH.sub.2 CH(CH.sub.3)CH.sub.2 --;
B is;
,
D is, or --R--O--[C(:O)--(CH.sub.2).sub.5 --O--] and has a
molecular weight of about 600-6000;
E is,
F is,
G is CH.sub.2 .dbd.C(R.sup.9)--C(:O)--O--R.sup.8 --O--C(:O)--NH--;
R.sup.1 is a divalent aromatic, aliphatic, or cycloaliphatic group containing 2-20 carbons;
R.sup.2 is a divalent aliphatic, cycloaliphatic, or alpharyl group of 2-20 carbons;
R.sup.3 is a divalent aliphatic, cycloaliphatic, aryl, or alpharyl group of 1-20 carbons;
R.sup.4 and R.sup.6 are the same or different alkylene groups with 1-6 carbons;
or R.sup.4 can be --(CH.sub.2 CH.sub.2 O).sub.d CH.sub.2 CH.sub.2 --, provided R.sup.6 is --(CH.sub.2 CH.sub.2 O).sub.e CH.sub.2 CH.sub.2 --, where d and e are each 0-9 and d+e=3-15;
R.sup.5 is --N(R.sup.7)--, --N--, or --N(Ph)--;
R.sup.7 is an alkyl group with 1-6 carbons;
R.sup.8 is 1-7 carbon alkylene;
R.sup.9 is H or methyl;
(A--O).sub.b has a number average molecular weight of about 650-7000.

24 more elements

A printing plate made by a method comprising exposing a printing plate comprising a layer of a photopolymer composition on a substrate with UV radiation through a negative, thereby providing exposed and non-exposed areas of photopolymer composition on the plate, and developing the plate by removing the non-exposed areas by washing the plate with an aqueous acidic solution;

characterized in that the photopolymer composition comprises G--R--R.sup.1 --G, where
R comprises B or E or mixtures thereof and F;
A is --CH.sub.2 CH.sub.2 --, --CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, or --CH.sub.2 CH(CH.sub.3)CH.sub.2 --;
B is;,
D is, or --R--O--and has a molecular weight of about 600-6000;
E is,
F is,
G is CH.sub.2 .dbd.C(R.sup.9)--C(:O)--O--R.sup.8 --O--C(:O)--NH--;
R.sup.1 is a divalent aromatic, aliphatic, or cycloaliphatic group containing 2-20 carbons;
R.sup.2 is a divalent aliphatic, cycloaliphatic, or alpharyl group of 2-20 carbons;
R.sup.3 is a divalent aliphatic, cycloaliphatic, aryl, or alpharyl group of 1-20 carbons;
R.sup.4 and R.sup.6 are the same or different alkylene groups with 1-6 carbons;
or R.sup.4 can be --(CH.sub.2 CH.sub.2 O).sub.d CH.sub.2 CH.sub.2 --, provided R.sup.6 is --(CH.sub.2 CH.sub.2 O).sub.e CH.sub.2 CH.sub.2 --, where d and e are each 0-9 and d+e=3-15.
R.sup.5 is --N(R.sup.7)--, --N N--, or --N(Ph)--;
R.sup.7 is an alkyl group with 1-6 carbons;
R.sup.8 is 1-7 carbon alkylene;
R.sup.9 is H or methyl;
(A--O).sub.b has a number average molecular weight of about 650-7000.

15 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/924,264Filed 28 Aug 1992
Granted: 12 Jul 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

G03F 7/035
With binders: the binders being polyurethanes
C08G 18/12
Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step: using…
C08G 18/4018
Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64: mixtures of compounds of group…
C08G 18/4808
Two or more polyethers of different physical or chemical nature: mixtures of two or more polyetherdiols