Alkali soluble resin
View Patent ↗An alkali soluble resin is disclosed comprising a first monomeric unit including at least one sulfonamide group and a second monomeric unit derived from the monomer according to the following structure (I) wherein R 1 represents a structural moiety comprising an ethylenically unsaturated polymerizable group; R 2 , R 3 and R 4 independently represent hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, alkaryl, aralkyl, aryl or heteroaryl group or, the necessary atoms to form a five to eight membered ring.
1. An alkali soluble resin comprising a first monomeric unit including at least one sulfonamide group and a second monomeric unit derived from the monomer according to the following structure:
wherein
R 1 represents a structural moiety comprising an ethylenically unsatured polymerisable group;
R 2 , R 3 and R 4 independently represent hydrogen, an optionally substituted alkyl group, cycloalkyl group, alkenyl, alkynyl, alkaryl or aralkyl group, an optionally substituted aryl or heteroaryl aryl group; or the necessary atoms to form a five to eight membered ring.
2. An alkali soluble resin according to claim 1 wherein the ethylenically unsaturated polymerisable group represents an acrylate, a methacrylate, a styrene, a maleimide, an acrylamide or a methacrylamide group.
3. An alkali soluble resin according to claim 1 wherein the second monomeric unit is derived from the monomer according to the following structure:
wherein
R 5 represents hydrogen or an optionally substituted alkyl group;
R 6 represents an optionally substituted alkyl, aryl or heteroaryl group, and
L 1 represents a divalent linking group.
4. An alkali soluble resin according to claim 1 wherein the second monomeric unit is derived from the monomers selected from the following list:
5. An alkali soluble resin according to claim 1 wherein the first monomeric unit comprises a sulphonamide group represented by —NR j —SO 2 —, —SO 2 —NR k — wherein R j and R k each independently represent hydrogen, an optionally substituted alkyl, alkanoyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl, heteroaralkyl group or combinations thereof.
6. An alkali soluble resin according to claim 1 wherein the first monomeric unit comprising a sulfonamide group is derived from the monomer according to the following structure:
wherein
R 7 , R 8 and R 9 independently represent hydrogen or an optionally substituted alkyl or aryl group;
L 2 represents a divalent linking group;
R 10 and R 11 represent hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, alkaryl, aralkyl, aryl, or heteroaryl group.
7. An alkali soluble resin according to claim 1 wherein the first monomeric unit comprising a sulfonamide group is derived from the monomer according to the following structure:
wherein
R 12 , R 13 and R 14 independently represent hydrogen or an optionally substituted alkyl group;
L 3 represents a divalent linking group;
t represents 0, 1 or an integer greater than 1;
R 15 and R 16 represent hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, alkaryl, aralkyl, aryl or heteroaryl group; and
R 18 , R 19 , R 20 and R 21 independently represent an alkyl, cycloalkyl, alkenyl or cyclo alkenyl group, an alkoxy group, a thio alkyl group, a hydroxyl group, —SH, a carboxylic acid group or an alkyl ester thereof, a sulphonic acid group or an alkyl ester thereof, a phosphonic acid group or an alkyl ester thereof, a phosphoric acid group or an alkyl ester thereof, an amino group, a sulphonamide group, an amide group, a nitro group, a nitrile group or a halogen.
8. An alkali soluble resin according to claim 1 wherein the first monomeric unit comprising a sulfonamide group is derived from the monomer according to the following structure:
wherein
R 12 , R 13 and R 14 independently represent hydrogen or an optionally substituted alkyl group;
L 3 represents a divalent linking group;
t represents 0, 1 or an integer greater than 1;
R 17 represent an optionally substituted alkyl, alkenyl, alkynyl, alkaryl, aralkyl group, an optionally substituted cycloalkyl group such as a cyclopentyl, cyclohexyl, 1,3-dimethylcyclohexyl group, an optionally substituted aryl group such as benzene, naphthalene or antracene or an optionally substituted heteroaryl aryl group such as furan, thiophene, pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, thiadiazole, oxadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine or 1,2,3-triazine, benzofuran, benzothiophene, indole, indazole, benzoxazole, quinoline, quinazoline, benzimidazole or benztriazole;
R 18 , R 19 , R 20 and R 21 independently represent an alkyl, cycloalkyl, alkenyl or cyclo alkenyl group, an alkoxy group, a thio alkyl group, a hydroxyl group, —SH, a carboxylic acid group or an alkyl ester thereof, a sulphonic acid group or an alkyl ester thereof, a phosphonic acid group or an alkyl ester thereof, a phosphoric acid group or an alkyl ester thereof, an amino group, a sulphonamide group, an amide group, a nitro group, a nitrile group or a halogen.
9. An alkali soluble resin according to claim 3 wherein the first monomeric unit comprising a sulfonamide group is derived from the monomer according to the following structure:
wherein
R 12 , R 13 and R 14 independently represent hydrogen or an optionally substituted alkyl group;
L 3 represents a divalent linking group;
t represents 0, 1 or an integer greater than 1;
R 17 represent an optionally substituted alkyl, alkenyl, alkynyl, alkaryl, aralkyl group, an optionally substituted cycloalkyl group such as a cyclopentyl, cyclohexyl, 1,3-dimethylcyclohexyl group, an optionally substituted aryl group such as benzene, naphthalene or antracene or an optionally substituted heteroaryl aryl group such as furan, thiophene, pyrrole, pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, thiadiazole, oxadiazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,2,4-triazine or 1,2,3-triazine, benzofuran, benzothiophene, indole, indazole, benzoxazole, quinoline, quinazoline, benzimidazole or benztriazole;
R 18 , R 19 , R 20 and R 21 independently represent an alkyl, cycloalkyl, alkenyl or cyclo alkenyl group, an alkoxy group, a thio alkyl group, a hydroxyl group, —SH, a carboxylic acid group or an alkyl ester thereof, a sulphonic acid group or an alkyl ester thereof, a phosphonic acid group or an alkyl ester thereof, a phosphoric acid group or an alkyl ester thereof, an amino group, a sulphonamide group, an amide group, a nitro group, a nitrile group or a halogen.
10. An alkali soluble resin according to claim 1 wherein the first monomeric unit comprising a sulfonamide group is derived from the monomers selected from the following monomers:
11. An alkali soluble resin according to claim 1 further comprising one or more monomeric unit(s) derived from the monomers selected from an alkyl or aryl (meth)acrylate, (meth)acrylic acid, (meth)acrylamide, a N-alkyl or N-aryl (meth)acrylamide, (meth)acrylonitrile, styrene, vinylpyridine, vinyl acetate, vinyl alcohol, vinyl acetal, vinyl butyral, a vinyl ether, vinyl amide, caprolactame, vinyl pyrrolydone or maleimide.
12. A method comprising the step of utilizing an alkali soluble resin according to claim 1 to make a lithographic printing plate.
13. A positive-working lithographic printing plate precursor which comprises on a support having a hydrophilic surface or which is provided with a hydrophilic layer, a heat and/or light-sensitive coating including an infrared absorbing agent and a first layer comprising an alkaline soluble resin according to claim 1 .
14. A positive-working lithographic printing plate precursor which comprises on a support having a hydrophilic surface or which is provided with a hydrophilic layer, a heat and/or light-sensitive coating including an infrared absorbing agent and a first layer comprising an alkaline soluble resin according to claim 3 .
15. A positive-working lithographic printing plate precursor which comprises on a support having a hydrophilic surface or which is provided with a hydrophilic layer, a heat and/or light-sensitive coating including an infrared absorbing agent and a first layer comprising an alkaline soluble resin according to claim 9 .
16. A positive-working lithographic printing plate precursor according to claim 13 wherein the coating comprises on top of the first layer a second layer comprising a phenolic resin.
17. A positive-working lithographic printing plate precursor according to claim 15 wherein the coating comprises on top of the first layer a second layer comprising a phenolic resin.
18. A method for making a positive-working lithographic printing plate comprising the steps of:
providing a heat-sensitive lithographic printing plate precursor according to claim 16 ;
imagewise exposing the heat-sensitive lithographic printing plate precursor to heat and/or infrared light;
developing said imagewise exposed precursor with an aqueous alkaline developer so that the exposed areas are dissolved.
19. A method for making a positive-working lithographic printing plate comprising the steps of:
providing a heat-sensitive lithographic printing plate precursor according to claim 17 ;
imagewise exposing the heat-sensitive lithographic printing plate precursor to heat and/or infrared light;
developing said imagewise exposed precursor with an aqueous alkaline developer so that the exposed areas are dissolved.
20. A method of lithographic printing comprising the steps of:
(i) providing a printing plate according to claim 18 ;
(ii) mounting the obtained printing plate on a press and start printing by applying ink and/or dampening liquid.