Photosensitive composition and lithographic printing plate precursor using the same
View Patent ↗A photosensitive composition comprising: (A) a polymerizable compound represented by the following formula (I): A—{O—[(CH(—R 1 )CH(—R 2 )) m —O] n —C(═O)—C(—R 3 )═CH 2 } p (I) wherein R 1 , R 2 and R 3 each represents a hydrogen atom or a methyl group, A represents a polyhydric alcohol residue or a polyhydric phenol residue, m represents an integer of from 1 to 6, n represents an integer of from 1 to 20, and p represents an integer of from 1 to 6; (B) an infrared absorber; and (C) an onium salt.
1. A photosensitive composition comprising;
(A) a polymerizable compound represented by the following formula (I):
A—{O—[(CH(—R 1 )CH(—R 2 )) m —O] n —C(═O)—C(—R 3 )═CH 2 } p (I)
wherein R 1 , R 2 and R 3 each represents a hydrogen atom or a methyl group, A represents a polyhydric phenol residue, m represents an integer of from 1 to 6, n represents an integer of from 2 to 10, and p represents an integer of from 1 to 6;
(B) an infrared absorber; and
(C) an onium salt,
wherein an amount of the polymerizable compound represented by formula (I) is from 75 to 100 wt % based on the total polymerizable compounds contained in the photosensitive composition.
2. The photosensitive composition as claimed in claim 1 ,
which further comprises a polymerizable compound having a urethane skeleton.
3. The photosensitive composition as claimed in claim 2 , wherein the amount of the polymerizable compound having a urethane skeleton is from 2 to 25 wt % based on the total polymerizable compounds contained in the photosensitive composition.
4. The photosensitive composition as claimed in claim 2 , wherein the amount of the polymerizable compound having a urethane skeleton is from 5 to 20 wt % based on the total polymerizable compounds contained in the photosensitive composition.
5. The photosensitive composition as claimed in claim 1 , wherein the onium salt is a compound represented by the following formula (1):
wherein, R 11 , R 12 and R 13 , which may be the same or different, each represents a hydrocarbon group having 20 or less carbon atoms which may have a substituent; and Z 11− represents a counter ion selected from the group consisting of a halogen ion, a perchlorate ion, a tetrafluoroborate ion, a hexafluorophosphate ion, a carboxylate ion and a sulfonate ion.
6. The photosensitive composition as claimed in claim 1 , which further comprises (D) a binder polymer having a crosslinkable group.
7. The photosensitive composition as claimed in claim 6 , wherein the binder polymer having a crosslinkable group contains an alkali-soluble group selected from the group consisting of
(1) a phenolic hydroxyl group (—Ar—OH)
(2) a sulfonamide group (—SO 2 NH—R)
(3) a substituted sulfonamide-based acid group (—SO 2 NHCOR, —SO 2 NHSO 2 R or —CONHSO 2 R)
(4) a carboxylic acid group (—CO 2 H)
(5) a sulfonic acid group (—SO 3 H), and
(6) a phosphoric acid group (—OPO 3 H 2 )
wherein Ar represents a divalent aryl linking group which may have a substituent; and R represents a hydrogen atom or a hydrocarbon group which may have a substituent.
8. The photosensitive composition as claimed in claim 6 ,
wherein the binder polymer having a crosslinkable group contains a structural unit represented by the following formula (i):
wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a linking group comprising one or more atoms selected from the group consisting of a carbon atom, a hydrogen atom, an oxygen atom, a nitrogen atom and a sulfur atom; A represents an oxygen atom or —NR 3 —; R 3 represents a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; and n represents an integer of from 1 to 5.
9. A lithographic printing plate precursor comprising a support having thereon a photosensitive layer containing the photosensitive composition as claimed in claim 1 .
10. The lithographic printing plate precursor as claimed in claim 9 , which further comprises a protective layer on the photosensitive layer.
11. The lithographic printing plate precursor as claimed in claim 10 , wherein the protective layer comprises a water-soluble polymer selected from polyvinyl alcohol, vinyl alcohol/vinyl phthalate copolymer, vinyl acetate/vinyl alcohol/vinyl phthalate copolymer, vinyl acetate/crotonic acid copolymer, polyvinyl pyrrolidone, acidic cellulose, gelatin, gum arabic, polyacrylic acid and polyacrylamide.
12. The photosensitive composition as claimed in claim 1 , wherein the amount of the polymerizable compound represented by formula (I) is from 80 to 100 wt % based on the total polymerizable compounds contained in the photosensitive composition.
13. A photosensitive composition comprising:
(A) a polymerizable compound represented by the following formula (I):
A—{O—[(CH(—R 1 )CH(—R 2 )) m —O] n —C(═O)—C(—R 3 )═CH 2 } p (I)
wherein R 1 , R 2 and R 3 each represents a hydrogen atom or a methyl group, A represents a polyhydric alcohol residue, m represents an integer of from 1 to 6, n represents an integer of from 2 to 10, and p represents an integer of from 1 to 6;
(B) an infrared absorber; and
(C) an onium salt,
wherein the amount of the polymerizable compound represented by formula (I) is from 75 to 100 wt % based on the total polymerizable compounds contained in the photosensitive composition.
14. The photosensitive composition as claimed in claim 13 , which further comprises a polymerizable compound having a urethane skeleton.
15. The photosensitive composition as claimed in claim 14 , wherein the amount of the polymerizable compound having a urethane skeleton is from 2 to 25 wt % based on the total polymerizable compounds contained in the photosensitive composition.
16. The photosensitive composition as claimed in claim 14 , wherein the amount of the polymerizable compound having a urethane skeleton is from 5 to 20 wt % based on the total polymerizable compounds contained in the photosensitive composition.
17. The photosensitive composition as claimed in claim 13 , wherein the onium salt is a compound represented by the following formula (1):
wherein R 11 , R 12 and R 13 , which may be the same or different, each represents a hydrocarbon group having 20 or less carbon atoms which may have a substituent; and Z 11− represents a counter ion selected from the group consisting of a halogen ion, a perchiorate ion, a tetrafluoroborate ion, a hexafluorophosphate ion, a carboxylate ion and a sulfonate ion.
18. The photosensitive composition as claimed in claim 13 , which further comprises (D) a binder polymer having a crosslinkable group.
19. The photosensitive composition as claimed in claim 18 , wherein the binder polymer having a crosslinkable group contains an alkali-soluble group selected from the group consisting of
(1) a phenolic hydroxyl group (—Ar—OH)
(2) a sulfonamide group (—SO 2 NH—R)
(3) a substituted sulfonamide-based acid group (—SO 2 NHCOR, —SO 2 NHSO 2 R or —CONHSO 2 R)
(4) a carboxylic acid group (—CO 2 H)
(5) a sulfonic acid group (—SO 3 H), and
(6) a phosphoric acid group (—OPO 3 H 2 )
wherein Ar represents a divalent aryl linking group which may have a substituent; and R represents a hydrogen atom or a hydrocarbon group which may have a substituent.
20. The photosensitive composition as claimed in claim 18 , wherein the binder polymer having a crosslinkable group contains a structural unit represented by the following formula (i):
wherein R 1 represents a hydrogen atom or a methyl group; R 2 represents a linking group comprising one or more atoms selected from the group consisting of a carbon atom, a hydrogen atom, an oxygen atom, a nitrogen atom and a sulfur atom; A represents an oxygen atom or —NR 3 —; R 3 represents a hydrogen atom or a monovalent hydrocarbon group having from 1 to 10 carbon atoms; and n represents an integer of from 1 to 5.
21. A lithographic printing plate precursor comprising a support having thereon a photosensitive layer containing the photosensitive composition as claimed in claim 13 .
22. The lithographic printing plate precursor as claimed in claim 21 , which further comprises a protective layer on the photosensitive layer.
23. The lithographic printing plate precursor as claimed in claim 22 , wherein the protective layer comprises a water-soluble polymer selected from polyvinyl alcohol, vinyl alcohol/vinyl phthalate copolymer, vinyl acetate/vinyl alcohol/vinyl phthalate copolymer, vinyl acetate/crotonic acid copolymer, polyvinyl pyrrolidone, acidic cellulose, gelatin, gum arabic, polyacrylic acid and polyacrylamide.
24. The photosensitive composition as claimed in claim 13 , wherein the amount of the polymerizable compound represented by formula (I) is from 80 to 100 wt % based on the total polymerizable compounds contained in the photosensitive composition.