Lithographic printing plate precursor

1. A negative-working lithographic printing plate precursor comprising:

a support; and

a coating provided on the support and including vinylogous vitrimer particles including a resin having at least one moiety having Formula (I), (II), and/or (Ill):

wherein

R1 represents hydrogen; an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group; COR4; or CN;

R2 represents hydrogen; an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group; or COR4;

R1 and R2 may represent atoms necessary to form a five to eight membered ring;

R3 represents an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group;

R4 represents hydrogen; an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group; OR5; or NR6R7;

R5 represents an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group;

R6 and R7 independently represent hydrogen; an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group; or R6 and R7 may represent atoms necessary to form a five to eight membered ring;

X represents O , NR8, or CR9R10;

R8, R9, and R10 independently represent hydrogen; or an optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aralkyl, alkaryl, aryl, or heteroaryl group;

R8 and R3 may represent atoms necessary to form a five to eight membered ring; and

any of R3, R9, and R10 may represent atoms necessary to form a five to eight membered ring.

2. The printing plate precursor according to claim 1 , wherein X represents O.

3. The printing plate precursor according to claim 1 , wherein the resin has a moiety according to Formula I.

4. The printing plate precursor according to claim 1 , wherein R1 and R2 independently represent hydrogen or an optionally substituted alkyl, aryl, or heteroaryl group.

5. The printing plate precursor according to claim 1 , wherein the vinylogous vitrimer particles include a core and shell structure in which the shell includes the resin.

6. The printing plate precursor according to claim 5 , wherein the coating further includes an infrared absorbing dye.

7. The printing plate precursor according to claim 6 , wherein the infrared absorbing dye is provided in the core of the vinylogous vitrimer particles.

8. The printing plate precursor according to claim 6 , wherein the infrared absorbing dye is represented by Formula (A):

wherein

Ar 1 and Ar 2 are independently an optionally substituted aromatic hydrocarbon group or an aromatic hydrocarbon group including an annulated benzene ring that is optionally substituted;

W 1 and W 2 are independently a sulphur atom or a —CM 10 M 11 group in which M 10 and M 11 are independently an optionally substituted aliphatic hydrocarbon group or an optionally substituted (hetero)aryl group, or in which M 10 and M 11 together include atoms necessary to form a cyclic structure;

M 1 and M 2 together include atoms necessary to form an optionally substituted cyclic structure;

M 3 and M 4 independently represent an optionally substituted aliphatic hydrocarbon group;

M 5 , M 6 , M 7 , and M 8 independently represent hydrogen, a halogen, or an optionally substituted aliphatic hydrocarbon group;

M 9 represents a halogen, an optionally substituted aliphatic hydrocarbon group, an optionally substituted (hetero)aryl group, —NR 1 R 2 , —NR 1 —CO—R 6 , —NR 1 —S02-R 4 , or —NR 1 —SO—R 5 ;

R 1 and R 2 independently represent hydrogen, an optionally substituted aliphatic hydrocarbon group, or an optionally substituted (hetero)aryl group;

R 4 and R 6 independently represent 0R 7 , —NR 8 R 9 , or —CF 3 ;

R 7 represents an optionally substituted (hetero)aryl group or an optionally branched aliphatic hydrocarbon group;

R 8 and R 9 independently represent hydrogen, an optionally substituted aliphatic hydrocarbon group, or an optionally substituted (hetero)aryl group, or in which R 8 and R 9 together include atoms necessary to form a cyclic structure;

R 5 represents hydrogen, an optionally substituted aliphatic hydrocarbon group, SO 3 − , —COOR 10 , or an optionally substituted (hetero)aryl group, in which R 10 represents an optionally substituted (hetero)aryl group or an aliphatic hydrocarbon group; and

the infrared absorbing dye may include one or more counter ions to obtain an electrically neutral molecule.

9. The printing plate precursor according to claim 1 , wherein the coating further includes a compound capable of generating a visual print-out image.

10. A method for making a printing plate comprising;

image-wise exposing the printing plate precursor as defined in claim 1 to heat and/or IR radiation; and

developing the exposed printing plate precursor.

11. The method according to claim 10 , wherein the step of developing is performed off-press and includes treating the exposed printing plate precursor with a developing solution to remove non-exposed areas of the coating from the support.

12. The method according to claim 11 , wherein the developing solution includes water, or a gum solution that develops and gums the exposed printing plate precursor in one single step.

13. The method according to claim 10 , wherein the step of developing is performed on-press and includes mounting the exposed printing plate precursor on a plate cylinder of a lithographic printing press and rotating the plate cylinder while supplying dampening liquid and/or ink to the coating.

14. The method according to claim 10 , wherein the IR radiation has an energy density between 70 mJ/m 2 and 180 mJ/m 2 .