Granted Patent B2

US 12,436,459 · App. 17/685,592 · Granted Oct 7, 2025

Inventors: Christopher D. Simpson (Osterode, DE); Stefanie Hansmann (Osterode, DE); Saija Werner (Hattorf, DE); Jianbing Huang (Trumbull, CT)

Assignee: EASTMAN KODAK COMPANY

G03F7/0045B41C1/1008

Abstract

Claims (49)

1. A lithographie printing plate precursor comprising:

a substrate, and

an infrared radiation-sensitive image-recording layer disposed on the substrate, the infrared radiation-sensitive image-recording layer comprising the following components (1), (2), and (3):

(1) a free radical initiator composition that is capable of generating free radicals upon exposure to infrared radiation, and which comprises an electron-donating agent;

(2) a free radically polymerizable composition; and

(3) a color-changing compound that is represented by the following Structure (I)

wherein:

Ar1 and Ar2 independently represent the atoms necessary to complete substituted or unsubstituted aromatic rings or to complete substituted or unsubstituted heteroaromatic rings;

R is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl groups;

R 1 and R 2 are independently unsubstituted alkyl groups or a chain of carbon atoms interrupted by one or more ether or ester linkages;

R 3 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;

Y represents an oxygen atom, a sulfur atom, or a dialkylmethylene group represented by >C(R 4 R 5 ) wherein R 4 and R 5 are independently substituted or unsubstituted alkyl groups having 1 to 4 carbons;

A 1 and A 2 independently represent substituted or unsubstituted alkyl groups, or together they represent the two or three carbon atoms necessary to form a substituted or unsubstituted 5- or 6-membered non-aromatic carbocyclic ring; and

Za represents one or more counter ions to balance the electric charge in the rest of the color-changing compound according to Structure (I).

2. The lithographie printing plate precursor of claim 1 , wherein R 3 is a trifluoromethyl group.

3. The lithographic printing plate precursor of claim 1 , wherein Ar1 and Ar2 are the same atoms necessary to complete substituted or unsubstituted aromatic rings.

4. The lithographie printing plate precursor of claim 1 , wherein one or both of the aromatic rings completed by the atoms of Ar1 and Ar2 are substituted with one or two halo groups that can be the same or different.

5. The lithographic printing plate precursor of claim 1 , wherein A 1 and A 2 together represent the two carbon atoms needed to complete an unsubstituted 5-membered non-aromatic carbocyclic ring.

6. The lithographic printing plate precursor of claim 1 , wherein Za comprises a tetraaryl borate anion.

7. The lithographie printing plate precursor of claim 1 , wherein the electron donating agent is an organic borate salt represented by the following Structure (II):

(B(R 10 R 11 R 12 R 13 ) − ) n M n+    Structure (II)

wherein R 10 , R 11 , R 12 , and R 13 are independently substituted or unsubstituted alkyl groups or substituted or unsubstituted aryl groups, and at least three of R 10 , R 11 , R 12 , and R 13 are the same or different substituted or unsubstituted aryl groups, n is an integer equal to or larger than 1, and M n+ is an n-valent cation.

8. The lithographie printing plate precursor of claim 7 , wherein all of R 10 , R 11 , R 12 , and R 13 are substituted or unsubstituted aryl groups.

9. The lithographie printing plate precursor of claim 7 , wherein all of R 10 , R 11 , R 12 , and R 13 are same substituted or unsubstituted phenyl groups.

10. The lithographic printing plate precursor of claim 1 , wherein the infrared radiation-sensitive image-recording layer further comprises a component (4) infrared absorbing material that is different from the (3) color-changing compound.

11. The lithographie printing plate precursor of claim 1 , wherein the (1) free radical initiator composition comprises an sodonium cation.

12. The lithographic printing plate precursor of claim 1 , wherein the infrared radiation-sensitive image-recording layer further comprises a component (5) acid-sensitive dye precursor that is different from all of the (1), (2), and (3) components defined above.

13. The lithographie printing plate precursor of claim 1 , wherein the infrared radiation-sensitive image-recording layer further comprises a component (6) non-free radically polymerizable polymeric material that is different from all of the (1), (2), and (3) components defined above and is present in particulate form.

14. The lithographic printing plate precursor of claim 1 , wherein the (3) color-changing compound represented by Structure (I) is present in the infrared radiation-sensitive image-recording layer in an amount of at least 0.5 weight % and up to and including 15 weight %, based on the total weight of the infrared radiation-sensitive image-recording layer.

15. The lithographie printing plate precursor of claim 1 wherein the infrared radiation-sensitive image-recording layer is the outermost layer.

16. The lithographie printing plate precursor of claim 1 , wherein the substrate comprises an aluminum-containing substrate comprising at least an inner aluminum oxide layer, an outer aluminum oxide layer disposed on the inner aluminum oxide layer, and a hydrophilic polymer coating that is disposed on the outer aluminum oxide layer.

17. A method for providing a lithographie printing plate, comprising:

A) imagewise exposing the lithographic printing plate precursor according to claim 1 to infrared radiation, to provide exposed regions and non-exposed regions in the infrared radiation-sensitive image-recording layer, and B) removing the non-exposed regions in the infrared radiation-sensitive image-recording layer from the substrate.

18. The method of claim 16 , comprising removing the non-exposed regions in the infrared radiation-sensitive image-recording layer from the substrate on-press using a lithographie printing ink, a fountain solution, or a combination of a lithographic printing ink and a fountain solution.

19. A lithographic printing plate precursor comprising:

a substrate, and

an infrared radiation-sensitive image-recording layer disposed on the substrate, the infrared radiation-sensitive image-recording layer comprising the following components (1), (2), and (3):

(1) a free radical initiator composition that is capable of generating free radicals upon exposure to infrared radiation, and which comprises an electron-donating agent;

(2) a free radically polymerizable composition; and

(3) a color-changing compound that is represented by the following Structure (I)

wherein:

Ar1 and Ar2 independently represent the atoms necessary to complete substituted or unsubstituted aromatic rings or to complete substituted or unsubstituted heteroaromatic rings;

R is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl groups,

R 1 and R 2 are independently substituted or unsubstituted alkyl groups;

R 3 is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group;

Y represents an oxygen atom, a sulfur atom, or a dialkylmethylene group represented by >C(R 4 R 5 ) wherein R 4 and R 5 are independently substituted or unsubstituted alkyl groups having 1 to 4 carbons;

A 1 and A 2 independently represent substituted or unsubstituted alkyl groups, or together they represent the two or three carbon atoms necessary to form a substituted or unsubstituted 5- or 6-membered non-aromatic carbocyclic ring; and

Za represents one or more tetraaryl borate anions to balance the electric charge in the rest of the color changing compound according to Structure (I).

20. The lithographic printing plate precursor of claim 19 , wherein the infrared radiation-sensitive image-recording layer further comprises a component (4) infrared absorbing material that is different from the (3) color-changing compound.

Assignments (2)

Continuity (2)

References Cited (58)