Lithographic printing plate precursor
A lithographic printing plate precursor is disclosed including a support and a coating comprising (i) a photopolymerisable layer including a polymerisable compound, a photoinitiator and an asymmetrically substituted infrared absorbing compound.
1 . A lithographic printing plate precursor including on a support a coating comprising a photopolymerisable layer including a polymerisable compound, a photoinitiator, and an infrared absorbing dye of Formula I:
wherein
Z and Z′ each independently represent —S—, —CR a R b —, or —CH═CH—, wherein R a and R b each independently represent an alkyl, aralkyl, or aryl group;
A represents a halogen, an optionally substituted aliphatic hydrocarbon group, an optionally substituted (hetero) aryl group, or —NR 1 R 2 , wherein R 1 and R 2 each independently represent hydrogen, an optionally substituted aliphatic hydrocarbon group, an optionally substituted (hetero) aryl group, or combinations thereof;
Q represents the necessary atoms to form a ring;
T and T′ each independently represent hydrogen, alkyl, halogen, alkoxy, cyano, —CO 2 R n , —CONR k R m , —SO 2 R n , —SO 2 NR o R p , or an optionally substituted annulated benzene ring, wherein R k and R m each independently represent hydrogen or an optionally substituted alkyl or aryl group, R n represents an optionally substituted alkyl or aryl group, and R o and R p each independently represent hydrogen or an optionally substituted alkyl or aryl group;
W − represents a counterion in order to obtain an electrically neutral compound; and
R z and R z′ each independently represent an optionally substituted alkyl group, characterized in that R z and R z′ are different.
2 . The printing plate precursor of claim 1 , wherein Q is represented by Formula II, III, or IV:
wherein
Ry and Ry′ each independently represent hydrogen, an optionally substituted alkyl, aralkyl, alkaryl, or aryl group, or the necessary atoms, when combined, to form a cyclic structure.
3 . The printing plate precursor of claim 1 , wherein Rz and Rz′ each independently represent a linear or branched alkyl group including C 1 to C 15 carbon atoms, provided that Rz and Rz′ are different.
4 . The printing plate precursor of claim 2 , wherein Rz and Rz′ each independently represent a linear or branched alkyl group including C 1 to C 15 carbon atoms, provided that Rz and Rz′ are different.
5 . The printing plate precursor of claim 1 , wherein Rz represents a methyl or ethyl group and Rz′ represents an octyl, nonyl, or decyl group.
6 . The printing plate precursor of claim 2 , wherein Rz represents a methyl or ethyl group and Rz′ represents an octyl, nonyl, or decyl group.
7 . The printing plate precursor of claim 1 , wherein the coating further includes a toplayer provided above the photopolymerisable layer.
8 . The printing plate precursor of claim 7 , wherein the toplayer includes a second infrared absorbing compound which includes a thermocleavable group which transforms into a group which is a stronger electron-donor upon exposure to heat and/or IR radiation, and is capable of forming a print-out image upon exposure to heat and/or IR radiation.
9 . The printing plate precursor of claim 8 , wherein the second infrared absorbing dye is represented by Formula VI
wherein
Ar 1 and Ar 2 each independently represent an optionally substituted aromatic hydrocarbon group or an aromatic hydrocarbon group with an annulated benzene ring which is optionally substituted,
W 1 and W 2 each independently represent a sulphur atom, an oxygen atom, NR*, NH, or a —CM 10 M 11 group, wherein R* represents an optionally substituted alkyl group and M 10 and M 11 each independently represent an optionally substituted aliphatic hydrocarbon group or an optionally substituted (hetero) aryl group;
M 1 and M 2 each independently represent hydrogen, an optionally substituted aliphatic hydrocarbon group or the necessary atoms, when combined, to form an optionally substituted cyclic structure which may comprise an optionally substituted annulated benzene ring;
M 3 and M 4 each independently represent an optionally substituted aliphatic hydrocarbon group;
M 5 , M 6 , M 7 , and M 8 each independently represent hydrogen, a halogen, or an optionally substituted aliphatic hydrocarbon group,
M 9 is a group which is transformed by a chemical reaction, induced by exposure to IR radiation or heat, into a group which is a stronger electron-donor than said M 9 ; and said transformation provides an increase of the integrated light absorption of said dye between 350 and 700 nm;
and optionally one or more counterions in order to obtain an electrically neutral compound.
10 . The printing plate precursor of claim 9 , wherein M 1 and M 2 represent the necessary atoms, when combined, to form an optionally substituted cyclic structure which may comprise an optionally substituted annulated benzene ring.
11 . The printing plate precursor of claim 9 , wherein M 1 and M 2 represent the necessary atoms, when combined, to form a 5- or 6-membered ring.
12 . The printing plate precursor of claim 9 , wherein M 1 and M 2 represent the necessary atoms, when combined, to form a 5-membered ring.
13 . The printing plate precursor of claim 9 , wherein M 1 and M 2 represent the necessary atoms, when combined, to form a 5-membered ring having a cyclic structure of 5 carbon atoms.
14 . The printing plate precursor of claim 1 , wherein R a and R b each independently represent an alkyl group.
15 . The printing plate precursor of claim 1 , wherein R a and R b each independently represent a methyl or ethyl group.
16 . A method for making a printing plate precursor, the method comprising:
coating on a support (i) a photopolymerisable layer including a polymerisable compound, a photoinitiator, and an infrared absorbing dye as defined in claim 11 , and
drying the precursor.
17 . A method for making a printing plate, the method comprising:
image-wise exposing the printing plate precursor as defined in claim 11 to heat and/or IR radiation whereby a lithographic image consisting of image areas and non-image areas is formed, and
developing the exposed precursor.
18 . The method for making a printing plate of claim 17 , wherein the precursor is developed by mounting the precursor on a plate cylinder of a lithographic printing press and rotating the plate cylinder while feeding dampening liquid and/or ink to the precursor.