Heat-sensitive lithographic printing plate precursor
View Patent ↗A heat-sensitive lithographic printing plate precursor is disclosed which comprises a hydrophilic support and an oleophilic coating comprising an infrared absorbing agent and a polymer, which comprises a phenolic monomeric unit wherein the phenyl group of the phenolic monomeric unit is substituted by a group having the structure —N═N-Q wherein the —N═N— group is covalently bound to a carbon atom of the phenyl group and wherein Q is an aromatic group and wherein the substitution increases the chemical resistance of the coating.
1. A heat-sensitive lithographic printing plate precursor comprising a support having a hydrophilic surface and an oleophilic coating provided on the hydrophilic surface, said coating comprising
an infrared light absorbing agent, and
a polymer which comprises a phenolic monomeric unit, wherein the phenyl group of the phenolic monomeric unit is substituted by a group having the structure —N═N-Q, wherein the —N═N— group is covalently bound to a carbon atom of the phenyl group, and wherein Q is an aromatic group.
2. The lithographic printing plate precursor according to claim 1 wherein Q is a group comprising at least one heteroatom.
3. The lithographic printing plate precursor according to claim 2 wherein said heteroatom is a nitrogen, an oxygen or a sulfur atom.
4. The lithographic printing plate precursor according to claim 1 wherein Q has the structure -A-(T) n
wherein A is a mono-cyclic 5- or 6-membered aromatic group or a 5- or 6-membered aromatic ring annelated with another ring system,
wherein n is an integer selected between 0 and the maximum available positions on the aromatic group A,
wherein each T group is selected from —SO 2 —NH—R 1 , —NH—SO 2 —R 4 , —CO—NR 1 —R 2 , —NR 1 —CO—R 4 , —NR 1 —CO—NR 2 —R 3 , —NR 1 —CS—NR 2 —R 3 , —NR 1 —CO—O—R 1 , —O—CO—NR 1 —R 2 , —O—CO—R 4 , —CO—O—R 4 , —CO—R 3 , —SO 3 —R 1 , —O—SO 2 —R 4 , —SO 2 —R 1 , —SO—R 4 , —P(═O)(—O—R 1 )(—O—R 2 ), —O—P(═O)(—O—R 1 )(—O—R 2 ), —NR 1 —R 2 , —O—R 2 , —S—R 2 , —N═N—R 4 , —CN, —NO 2 , a halogenide and -M-R 1 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 1 , R 2 and R 3 are each independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 and R 5 are selected from optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl and heteroaralkyl groups,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
5. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein X is CR 3 , NR 4 or N,
wherein Y denotes the necessary atoms to form a 5- or 6-membered aromatic ring, said atoms being selected from the group consisting of CR 3 , NR 4 , N, S and O,
wherein each R 1 , R 2 and R 3 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 5 , —NH—SO 2 —R 7 , —CO—NR 5 —R 6 , —NR 5 —CO—R 7 , —O—CO—R 7 , —CO—O—R 5 , —CO—R 5 , —SO 3 —R 5 , —SO 2 —R 5 , —SO—R 7 , —P(═O)(—O—R 5 )(—O—R 6 ), —NR 5 —R 6 , —O—R 5 , —S—R 5 , —CN, —NO 2 , halogen and -M-R 5 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 4 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, wherein R 7 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 7 together represent the necessary atoms to form a cyclic structure.
6. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein Z 1 and Z 2 are independently selected from CR 1 and N, wherein R 1 is selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein n is 0, 1, 2, 3 or 4,
wherein m is 0, 1, 2 or 3,
wherein R 2 and R 3 are independently selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 4 , —NH—SO 2 —R 6 , —CO—NR 4 —R 5 , —NR 4 —CO—R 6 , —O—CO—R 6 , —CO—O—R 4 , —CO—R 4 , —SO 3 —R 4 , —SO 2 —R 4 , —SO—R 6 , —P(═O)(—O—R 4 )(—O—R 5 ), —NR 4 —R 5 , —O—R 4 , —S—R 4 , —CN, —NO 2 , halogen and -M-R 4 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 4 and R 5 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, wherein R 6 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 6 together represent the necessary atoms to form a cyclic structure.
7. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2, 3, 4, or 5,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO-4, —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms, wherein R 2 and R 3 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 4 together represent the necessary atoms to form a cyclic structure.
8. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2, 3 or 4,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein X is O, S or NR 5 ,
wherein R 2 , R 3 and R 5 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
9. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms, wherein R 2 , R 3 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, or wherein at least two groups selected from each R 1 to R 4 together represent the necessary atoms to form a cyclic structure,
or wherein R 5 and R 6 together represent the necessary atoms to form a cyclic structure.
10. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein m is 0, 1, 2, 3 or 4, 3 wherein each R 1 and R 2 are independently selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 3 , —NH—SO 2 —R 5 , —CO—NR 3 —R 4 , —NR 3 —CO—R 5 , —O—CO—R 5 , —CO—O—R 3 , —CO—R 3 , —SO 3 —R 3 , —SO 2 —R 3 , —SO—R 5 , —P(═O)(—O—R 3 )(—O—R 4 ), —NR 3 —R 4 , —O—R 3 , —S—R 3 , —CN, —NO 2 , a halogen and -M-R 3 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 3 and R 4 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 5 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
11. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms, wherein R 2 , R 3 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 6 together represent the necessary atoms to form a cyclic structure.
12. The lithographic printing plate precursor according to claim 1 wherein the —N═N-Q group comprises one of the following formulae:
13. The lithographic printing plate precursor according to claim 1 , wherein said polymer comprising a phenolic monomeric unit is a novolac, resol or polyvinylphenol.
14. The lithographic printing plate precursor according to claim 1 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
15. The lithographic printing plate precursor according to claim 14 , wherein said dissolution inhibitor is selected from the group consisting of
an organic compound which comprises at least one aromatic group and a hydrogen bonding site,
a polymer or surfactant comprising siloxane or perfluoroalkyl units, and mixtures thereof.
16. The lithographic printing plate precursor according to claim 1 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
17. The lithographic printing plate precursor according to claim 2 wherein Q has the structure -A-(T) n
wherein A is a mono-cyclic 5- or 6-membered aromatic group or a 5- or 6-membered aromatic ring annelated with another ring system,
wherein n is an integer selected between 0 and the maximum available positions on the aromatic group A,
wherein each T group is selected from —SO 2 —NH—R 1 , —NH—SO 2 —R 4 , —CO—NR 1 —R 2 , —NR 1 —CO—R 4 , —NR 1 —CO—NR 2 —R 3 , —NR 1 —CS—NR 1 —R 3 , —NR 1 —CO—O—R 1 , —O—CO—NR 1 —R 2 , —O—CO—R 4 , —CO—O—R 4 , —CO—R 4 , —SO 3 —R 1 , —O—SO 2 —R 4 , —SO 2 —R 1 , —SO—R 4 , —P(═O)(—O—R 1 )(—O—R 2 ), —O—P(═O)(—O—R 1 )(—O—R 2 ), —NR 1 —R 2 , —O—R 2 , —S—R 2 , —N═N—R 4 , —CN, —NO 2 , a halogenide and -M-R 1 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 1 , R 2 and R 3 are each independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 and R 5 are selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
18. The lithographic printing plate precursor according to claim 3 wherein Q has the structure -A-(T) n
wherein A is a mono-cyclic 5- or 6-membered aromatic group or a 5- or 6-membered aromatic ring annelated with another ring system,
wherein n is an integer selected between 0 and the maximum available positions on the aromatic group A,
wherein each T group is selected from —SO 2 —NH—R 1 , —NH—SO 2 —R 4 , —CO—NR 1 —R 2 , —NR 1 —CO—R 4 , —NR 1 —CO—NR 2 —R 3 , —NR 1 —CS—NR 2 —R 3 , —NR 1 —CO—O—R 1 , —O—CO—NR 1 —R 2 , —O—CO—R 4 , —CO—O—R 4 , —CO—R 4 , —SO 3 —R 1 , —O—SO 2 —R 1 , —SO 2 —R 4 , —SO—R 4 , —P(═O)(—O—R 1 )(—O—R 2 ), —O—P(═O)(—O—R 1 )(—O—R 2 ), —NR 1 —R 2 , —O—R 2 , —S—R 2 , —N═N—R 4 , —CN, —NO 2 , a halogenide and -M-R 1 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 1 , R 2 and R 3 are each independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 and R 5 are selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
19. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein X is CR 3 , NR 4 or N,
wherein Y denotes the necessary atoms to form a 5- or 6-membered aromatic ring, said atoms being selected from the group consisting of CR 3 , NR 4 , N, S and O,
wherein each R 1 , R 2 and R 3 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 5 , —NH—SO 2 —R 7 , —CO—NR 5 —R 6 , —NR 5 —CO—R 7 , —O—CO—R 7 , —CO—O—R 5 , —CO—R 5 , —SO 3 —R 5 , —SO 2 —R 5 , —SO—R 7 , —P(═O)(—O—R 5 )(—O—R 6 ), —NR 5 —R 6 , —O—R 5 , —S—R 5 , —CN, —NO 2 , halogen and -M-R 5 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 4 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 7 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 7 together represent the necessary atoms to form a cyclic structure.
20. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein X is CR 3 , NR 4 or N,
wherein Y denotes the necessary atoms to form a 5- or 6-membered aromatic ring, said atoms being selected from the group consisting of CR 3 , NR 4 , N, S and O,
wherein each R 1 , R 2 and R 3 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 5 , —NH—SO 2 —R 7 , —CO—NR 5 —R 6 , —NR 5 —CO—R 7 , —O—CO—R 7 , —CO—O—R 5 , —CO—R 5 , —SO 3 —R 5 , —SO 2 —R 5 , —SO—R 7 , —P(═O)(—O—R 5 )(—O—R 6 ), —NR 5 —R 6 , —O—R 5 , —S—R 5 , —CN, —NO 2 , halogen and -M-R 5 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 4 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 7 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 7 together represent the necessary atoms to form a cyclic structure.
21. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein Z 1 and Z 2 are independently selected from CR 1 or N,
wherein R 1 is selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein n is 0, 1, 2, 3 or 4,
wherein m is 0, 1, 2 or 3,
wherein R 2 and R 3 are independently selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 4 , —NH—SO 2 —R 6 , —CO—NR 4 —R 5 , —NR 4 —CO—R 6 , —O—CO—R 6 , —CO—O—R 4 , —CO—R 4 , —SO 3 —R 4 , —SO 2 —R 4 , —SO—R 6 , —P(═O)(—O—R 4 )(—O—R 5 ), —NR 4 —R 5 , —O—R 4 , —S—R 4 , —CN, —NO 2 , halogen, and -M-R 4 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 4 and R 5 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 6 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 6 together represent the necessary atoms to form a cyclic structure.
22. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein Z 1 and Z 2 are independently selected from CR 1 and N,
wherein R 1 is selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein n is 0, 1, 2, 3 or 4,
wherein m is 0, 1, 2 or 3,
wherein R 2 and R 3 are independently selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 4 , —NH—SO 2 —R 6 , —CO—NR 4 —R 5 , —NR 4 —CO—R 6 , —O—CO—R 6 , —CO—O—R 4 , —CO—R 4 , —SO 3 —R 4 , —SO 2 —R 4 , —SO—R 6 , —P(═O)(—O—R 4 )(—O—R 5 ), —NR 4 —R 5 , —O—R 4 , —S—R 4 , —CN, —NO 2 , halogen and -M-R 4 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 4 and R 5 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 6 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 6 together represent the necessary atoms to form a cyclic structure.
23. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2, 3, 4, or 5,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 2 and R 3 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 4 together represent the necessary atoms to form a cyclic structure.
24. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2, 3, 4, or 5,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 2 and R 3 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 4 together represent the necessary atoms to form a cyclic structure.
25. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2, 3 or 4,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein X is O, S or NR 5 ,
wherein R 2 , R 3 and R 5 are independently selected from hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
26. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2, 3 or 4,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein X is O, S or NR 5 ,
wherein R 2 , R 3 and R 5 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
27. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 2 , R 3 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, or wherein at least two groups selected from each R 1 to R 4 together represent the necessary atoms to form a cyclic structure, or wherein R 5 and R 6 together represent the necessary atoms to form a cyclic structure.
28. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 2 , R 3 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 4 together represent the necessary atoms to form a cyclic structure,
or wherein R 5 and R 6 together represent the necessary atoms to form a cyclic structure.
29. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein m is 0, 1, 2, 3 or 4,
wherein each R 1 and R 2 are independently selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 3 , —NH—SO 2 —R 5 , —CO—NR 3 —R 4 , —NR 3 —CO—R 5 , —O—CO—R 5 , —CO—O—R 3 , —CO—R 3 , —SO 3 —R 3 , —SO 2 —R 3 , —SO—R 5 , —P(═O)(—O—R 3 )(—O—R 4 ), —NR 3 —R 4 , —O—R 3 , —S—R 3 , —CN, —NO 2 , a halogen and -M-R 3 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms, wherein R 3 and R 4 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 5 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
30. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein m is 0, 1, 2, 3 or 4,
wherein each R 1 and R 2 are independently selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 3 , —NH—SO 2 —R 5 , —CO—NR 3 —R 4 , —NR 3 —CO—R 5 , —O—CO—R 5 , —CO—O—R 3 , —CO—R 3 , —SO 3 —R 3 , —SO 2 —R 3 , —SO—R 5 , —P(═O)(—O—R 3 )(—O—R 4 ), —NR 3 —R 4 , —O—R 3 , —S—R 3 , —CN, —NO 2 , a halogen and -M-R 3 , wherein M represents a divalent linking group containing 1 to 8 carbon atoms, wherein R 3 and R 4 are independently selected from hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 5 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 5 together represent the necessary atoms to form a cyclic structure.
31. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 3 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 2 , R 3 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, or wherein at least two groups selected from each R 1 to R 6 together represent the necessary atoms to form a cyclic structure.
32. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises the following formula
wherein n is 0, 1, 2 or 3,
wherein each R 1 is selected from hydrogen, an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group, —SO 2 —NH—R 2 , —NH—SO 2 —R 4 , —CO—NR 2 —R 4 , —NR 2 —CO—R 4 , —O—CO—R 4 , —CO—O—R 2 , —CO—R 2 , —SO 3 —R 2 , —SO 2 —R 2 , —SO—R 4 , —P(═O)(—O—R 2 )(—O—R 3 ), —NR 2 —R 3 , —O—R 2 , —S—R 2 , —CN, —NO 2 , a halogen and -M-R 2 ,
wherein M represents a divalent linking group containing 1 to 8 carbon atoms,
wherein R 2 , R 3 , R 5 and R 6 are independently selected from hydrogen and an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
wherein R 4 is selected from an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, heterocyclic, aryl, heteroaryl, aralkyl or heteroaralkyl group,
or wherein at least two groups selected from each R 1 to R 6 together represent the necessary atoms to form a cyclic structure.
33. The lithographic printing plate precursor according to claim 2 wherein the —N═N-Q group comprises one of the following formulae:
34. The lithographic printing plate precursor according to claim 3 wherein the —N═N-Q group comprises one of the following formulae:
35. The lithographic printing plate precursor according to claim 2 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
36. The lithographic printing plate precursor according to claim 3 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
37. The lithographic printing plate precursor according to claim 4 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
38. The lithographic printing plate precursor as amended in claim 5 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
39. The lithographic printing plate precursor according to claim 6 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
40. The lithographic printing plate precursor according to claim 7 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
41. The lithographic printing plate precursor according to claim 8 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
42. The lithographic printing plate precursor according to claim 9 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
43. The lithographic printing plate precursor according to claim 10 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
44. The lithographic printing plate precursor according to claim 11 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
45. The lithographic printing plate precursor according to claim 12 , wherein said coating further comprises a dissolution inhibitor and wherein said precursor is a positive working lithographic printing plate precursor.
46. The lithographic printing plate precursor according to claim 2 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
47. The lithographic printing plate precursor according to claim 3 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
48. The lithographic printing plate precursor according to claim 4 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
49. The lithographic printing plate precursor according to claim 5 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
50. The lithographic printing plate precursor according to claim 6 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
51. The lithographic printing plate precursor according to claim 7 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
52. The lithographic printing plate precursor according to claim 8 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
53. The lithographic printing plate precursor according to claim 9 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
54. The lithographic printing plate precursor according to claim 10 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
55. The lithographic printing plate precursor according to claim 11 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
56. The lithographic printing plate precursor according to claim 12 , wherein said coating further comprising a latent Brönsted acid and an acid-crosslinkable compound and wherein said precursor is a negative working lithographic printing plate precursor.
57. A method for increasing the chemical resistance of a coating of a positive working heat-sensitive lithographic printing plate precursor, the method comprising providing a coating comprising:
a polymer which comprises a phenolic monomeric unit wherein the phenyl group of the phenolic monomeric unit is substituted by a group having the structure —N═N-Q wherein the —N═N— group is covalently bound to a carbon atom of the phenyl group and wherein Q is an aromatic group,
an infrared absorbing agent, and
a dissolution inhibitor.
58. A method for increasing the chemical resistance of a coating of a negative working heat-sensitive lithographic printing plate, the method comprising providing a coating comprising:
a polymer which comprises a phenolic monomeric unit wherein the phenyl group of the phenolic monomeric unit is substituted by a group having the structure —N═N-Q wherein the —N═N— group is covalently bound is a carbon atom of the phenyl group and wherein Q is an aromatic group,
a latent Brönsted acid, and
an acid-crosslinkable compound.