US 12,222,645 B2
Lithographic printing plate precursor and method of use
Christopher D. Simpson, Osterode (DE); Stefanie Hansmann, Osterode (DE); Saija Werner, HattorF (DE); and Jianbing Huang, Trumbull, CT (US)
Assigned to EASTMAN KODAK COMPANY, Rochester, NY (US)
Filed by Eastman Kodak Company, Rochester, NY (US)
Filed on Jun. 21, 2022, as Appl. No. 17/844,953.
Application 17/844,953 is a continuation in part of application No. 17/685,570, filed on Mar. 3, 2022, abandoned.
Prior Publication US 2023/0314935 A1, Oct. 5, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. G03F 7/004 (2006.01); B41C 1/10 (2006.01); G03F 7/029 (2006.01)
CPC G03F 7/0045 (2013.01) [B41C 1/1008 (2013.01); G03F 7/0295 (2013.01)] 22 Claims
 
1. 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 and one or more iodonium cations;
(2) a free radically polymerizable composition; and
(3) a color-changing compound that is represented by the following Structure (I)

OG Complex Work Unit Chemistry
wherein:
Ar1, Ar2, and Ar3 independently represent the atoms necessary to complete substituted or unsubstituted aromatic rings or to complete substituted or unsubstituted heteroaromatic rings;
Y represents an oxygen atom, a sulfur atom, or a dialkylmethylene group represented by >C(R4R5) wherein R4 and R5 are independently substituted or unsubstituted alkyl groups having 1 to 4 carbons;
R1 and R2 are independently substituted or unsubstituted alkyl groups;
X represents a single bond or a divalent linking group selected from —S—, —O—, and >N(R6) wherein R6 is hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or L;
L represents a —C(═O)—OR7 group, —SO2—R3 group, or —SO2NR8R9 group, wherein R7 represents a substituted or unsubstituted alkyl group that has a secondary or tertiary connecting carbon that connects to the remainder of the —C(═O)OR7 group; and R3, R8, and R9 independently represent substituted or unsubstituted alkyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups; 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),
wherein the infrared radiation-sensitive image-recording layer comprises one or more borate anions in an amount such that the molar ratio of the one or more borate anions to the one or more iodonium cations is at least 0.8:1 and up to and including 4:1, and the borate anions are represented by following Structure (IIIa):
B(R10R11R12R13)−   Structure (IIIa)
wherein R10, R11, R12, and R13 are independently substituted or unsubstituted alkyl groups or substituted or unsubstituted aryl groups, provided that at least three of R10, R11, R12, and R13 are the same or different substituted or unsubstituted aryl groups, and the substituted aryl groups each have no more than two halo substituents.