IP Library Granted Patent US 9,250,521
Granted Patent B2
US 9,250,521 · App. 14/350,462 · Granted Feb 2, 2016

Lithographic printing plate precursor and a method for making a printing plate

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Quick Facts
Patent No.
US 9,250,521
App. No.
14/350,462
Granted
Feb 2, 2016
Kind
B2
Abstract

A positive-working lithographic printing plate precursor exhibits satisfactory developability and has long print run length, satisfactory scratch resistance, and exhibits improved ink receptivity. This precursor has an image forming layer comprising a water-insoluble and alkali-soluble or alkali-dispersible resin. The image forming layer comprises at least a lower layer and an upper layer. A resin in at least one of the lower layer and the upper layer is a polyurethane including a recurring unit comprising a substituent having an acidic hydrogen atom and a recurring unit represented by the following formula: wherein R f is an alkyl or polyether group in which at least 50% of hydrogen atoms have been fluorinated, R 1 is a hydrogen atom, or a substituted or non-substituted alkyl group, m is 0 or 1 to 10, n is 1 to 30, and x is 1 to 4.

Claims (44)

1. A positive-working lithographic printing plate precursor comprising a substrate having thereon an image forming layer comprising a water-insoluble and alkali-soluble or alkali-dispersible resin in an aqueous alkali solution,

wherein the image forming layer comprises at least a lower layer and an upper layer, and

the resin of one of the lower layer and the upper layer, or both of the lower layer and the upper layer comprises a polyurethane comprising:

a recurring unit comprising a substituent having an acidic hydrogen atom, which substituent is selected from the group consisting of a carboxyl group, a —SO 2 NHCOO— group, a —CONHSO 2 — group, a —CONHSO 2 NH— group, and a —NHCONHSO 2 — group, and

a recurring unit represented by the following general formula:

wherein

R f is an alkyl or polyether group in which at least 50% of hydrogen atoms have been fluorinated,

R 1 is a hydrogen atom, or a substituted or non-substituted alkyl group,

m is 0 or 1 to 10, n is 1 to 30, and

x is 1 to 4.

2. The positive-working lithographic printing plate precursor according to claim 1 , wherein the recurring unit represented by general formula is derived from a diol and the recurring unit comprising the acidic hydrogen atom is derived from another.

3. The positive-working lithographic printing plate precursor according to claim 1 , wherein

at least 75% of R f in the general formula is fluorinated, and R 1 is an alkyl group having 1 to 4 carbon atoms, m is 0, 1, 2, or 3, and x is 1 or 2.

4. The positive-working lithographic printing plate precursor according to claim 1 , wherein the upper layer comprises the polyurethane.

5. The positive-working lithographic printing plate precursor according to claim 4 , wherein the amount of the polyurethane contained in the upper layer is from 10% to 90% based on the total dry weight of the upper layer.

6. The positive-working lithographic printing plate precursor according to claim 1 , wherein one of the lower layer and the upper layer, or both of the lower layer and the upper layer comprise(s) a photothermal conversion material.

7. The positive-working lithographic printing plate precursor according to claim 6 , wherein the upper layer comprises a photothermal conversion material.

8. A positive-working lithographic printing plate precursor comprising a substrate having thereon an image forming layer comprising a water-insoluble and alkali-soluble or alkali-dispersible resin in an aqueous alkali solution,

wherein the positive-working lithographic printing plate precursor further comprises a photothermal conversion material, and

a resin, which is water-insoluble and alkali-soluble or alkali-dispersible in the aqueous alkali solution, and

comprises a polyurethane comprising:

a recurring unit comprising a substituent having an acidic hydrogen atom, which substituent is selected from the group consisting of a carboxyl group, a —SO 2 NHCOO— group, a —CONHSO 2 — group, a —CONHSO 2 NH— group, and a —NHCONHSO 2 — group, and

a recurring unit represented by the following general formula:

wherein

R f is a fluorinated alkyl or polyether group in which at least 50% of hydrogen atoms have been fluorinated,

R 1 is a hydrogen atom, or a substituted or non-substituted alkyl group,

m is 0 or 1 to 10, n is 1 to 30, and

x is 1 to 4.

9. A method for producing a lithographic printing plate, which comprises the steps of:

imagewisely exposing the positive-working lithographic printing plate precursor according to claim 1 using infrared rays to form exposed areas; and

developing the exposed positive-working lithographic printing plate precursor with an alkali developing solution to remove the image forming layer in the exposed areas, and thus forming image areas and non-image areas.

10. The method for producing a lithographic printing plate according to claim 9 , wherein the alkali developing solution has pH of 12 or less.

11. The method for producing a lithographic printing plate according to claim 9 , wherein the alkali developing solution comprises an organic solvent in the amount of 20% or less based on the total mass of the developing solution.

12. The method for producing a lithographic printing plate according to claim 9 , wherein the alkali developing solution substantially comprises no silicate.

13. The positive-working lithographic printing plate precursor of claim 1 , wherein the lower layer further comprises the water-insoluble and alkali-soluble or alkali-dispersible resin that can be produced by polymerizing a monomer mixture comprising one or more ethylenically unsaturated monomers having functional groups selected from a hydroxyl group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an imide groups, an amide group, and a combinations thereof.

14. The positive-working lithographic printing plate precursor of claim 1 , wherein the water-insoluble and alkali-soluble or alkali-dispersible resin comprises recurring units that are derived from at least one ethylenically unsaturated monomer represented by the following

wherein:

R 4 is a hydrogen atom, a C 1-22 linear, branched or cyclic alkyl group, a C 1-22 linear, branched or cyclic substituted alkyl group, a C 6-24 aryl group, or a substituted aryl group, and the substituent is selected from a C 1-4 alkyl group, an aryl group, a halogen atom, a keto group, an ester group, an alkoxy group, or a cyano group;

X is O, S, and NR 5 , in which R 5 is hydrogen, a C 1-22 linear, branched or cyclic alkyl group, a C 1-22 linear, branched or cyclic substituted alkyl group, a C 6-24 aryl group, or a substituted aryl group, and substituent is selected from a C 1-4 alkyl group, an aryl group, a halogen atom, a keto group, an ester group, an alkoxy group, or a cyano group;

Y is a single bond, or C 1-22 linear, branched or cyclic alkylene, alkyleneoxyalkylene, poly(alkyleneoxy)alkylene, or alkylene-NHCONH—; and

Z is a hydrogen atom, a hydroxy group, carboxylic acid, —C 6 H 4 —SO 2 NH 2 , —C 6 H 3 —SO 2 NH 2 (—OH), or a group represented by the following

or a mixture thereof.

15. The positive-working lithographic printing plate precursor of claim 1 , wherein the water-insoluble and alkali-soluble or alkali-dispersible resin comprises recurring units that are derived from a (meth)acrylic acid ester, (meth)acrylamide, maleimide, or (meth)acrylonitrile.

16. The positive-working lithographic printing plate precursor of claim 1 , wherein the polyurethane has a molecular weight of from 2,000 to 100,000.

Assignments (13)
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jul 24, 2023
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A.
Reel/Frame 064364/0847 →
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0001 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056734/0233 →
RELEASE OF SECURITY INTEREST Recorded Jan 24, 2020
From: BARCLAYS BANK PLC
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST) INC.; KODAK AMERICAS LTD.; KODAK REALTY INC.; LASER PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES LTD.; NPEC INC.
Reel/Frame 052773/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 30, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; PFC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 049901/0001 →
RELEASE OF SECURITY INTEREST Recorded Jul 22, 2019
From: JP MORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: QUALEX, INC.; EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC, INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER PACIFIC MEDIA CORPORATION; PAKON, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
SECURITY INTEREST Recorded Jan 13, 2017
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 041042/0877 →
SECURITY INTEREST Recorded May 13, 2014
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; KODAK AVIATION LEASING LLC
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 032874/0257 →
SECURITY INTEREST Recorded May 12, 2014
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; KODAK AVIATION LEASING LLC
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 032869/0181 →
SECURITY INTEREST Recorded May 12, 2014
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK IMAGING NETWORK, INC.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.; KODAK AVIATION LEASING LLC
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 032869/0226 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 8, 2014
From: KAMIYA, MASAMICHI; ASAWA, YASUHIRO; MIYAMOTO, YASUSHI; ABURANO, MARU; HAYAKAWA, EIJI
To: EASTMAN KODAK COMPANY
Reel/Frame 032627/0088 →