IP Library Granted Patent US 10,040,957
Granted Patent B2
US 10,040,957 · App. 14/856,630 · Granted Aug 7, 2018

Ink jettable, UV-curable compositions

Inventors: Thomas B. Brust (Webster, NY); Anne Troxell Wyand (Victor, NY); Grace Ann Bennett (Scottsville, NY); Catherine A. Falkner (Rochester, NY)
Assignee: EASTMAN KODAK COMPANY
C09D11/101C09D11/00C09D11/10C09D11/102C09D11/30C09D125/04C09D133/02C09D133/14C09D133/26
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,040,957
App. No.
14/856,630
Granted
Aug 7, 2018
Kind
B2
Abstract

Ink jettable and UV-curable compositions include a reactive polymer comprising: (a1) at least 20 mol % of recurring units comprising pendant metal complexing water-solubilizing groups, and (b) at least 5 mol % of recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition. The compositions can optionally have a humectant, a dye or pigment colorant, an anionic or nonionic surfactant, a water-soluble or water-dispersible acrylic polymer, or a water-soluble or water-dispersible polyurethane. Such ink jettable and UV-curable compositions can include a complex of reducible metal ions or metal nanoparticles with the reactive polymer.

Claims (36)

1. An ink jettable and UV-curable composition comprising:

a reactive polymer comprising: (a1) at least 40 mol % of recurring units comprising pendant metal complexing water-solubilizing groups that include a sulfonic acid group or sulfonate group in combination with a carboxylic acid group or carboxylate group, (b) at least 5 mol % of recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition, and optionally (c) at least 1 mol % of recurring units comprising a pendant amide, hydroxyl, or lactam group, or a pendant precursor moiety for the pendant amide, hydroxyl, or lactam group, all amounts based on the total recurring units in the reactive polymer; and

optionally, one or more of the following components:

a humectant,

a dye or pigment colorant,

an anionic or nonionic surfactant,

a water-soluble or water-dispersible acrylic polymer, and

a water-soluble or water-dispersible polyurethane.

2. The ink jettable and UV-curable composition of claim 1 , wherein the reactive polymer comprises at least 40 mol % and up to and including 95 mol % of the (a1) recurring units, based on the total recurring units in the reactive polymer.

3. The ink jettable and UV-curable composition of claim 1 , wherein the reactive polymer comprises at least 5 mol % and up to and including 50 mol % of the (b) recurring units, based on the total recurring units in the reactive polymer.

4. The ink jettable and UV-curable composition of claim 1 , wherein the reactive polymer comprises at least 1 mole % and up to and including 55 mol % of (c) recurring units comprising pendant hydroxyl or amide groups, based on the total recurring units in the reactive polymer.

5. The ink jettable and UV-curable composition of claim 1 , wherein the (b) recurring units comprise:

(i) a photosensitive —C(═O)—CR═CR 1 —Y group wherein R and R 1 are independently hydrogen or an alkyl group having 1 to 7 carbon atoms, a 5- to 6-membered cycloalkyl group, an alkoxy group having 1 to 7 carbon atoms, a phenyl group, or a phenoxy group, and Y is an aryl or heteroaryl group;

(ii) a photosensitive, non-aromatic unsaturated carbocyclic group;

(iii) a photosensitive, aromatic or non-aromatic heterocyclic group comprising a carbon-carbon double bond that is conjugated with an electron withdrawing group;

(iv) a photosensitive non-aromatic unsaturated heterocyclic group comprising one or more amide groups that are conjugated with a carbon-carbon double bond, which photosensitive non-aromatic unsaturated heterocyclic group is linked to the water-soluble backbone at an amide nitrogen atom; or

(v) a photosensitive substituted or unsubstituted 1,2-diarylethylene group.

6. The ink jettable and UV-curable composition of claim 1 , further comprising a humectant that is chosen from at least one of the following groups of compounds:

(1) polyhydric alcohols;

(2) polyoxygenated polyols and their derivatives;

(3) sulfur-containing polyol compounds;

(4) cyclic lactams; and

(5) cyclic ureas.

7. The ink jettable and UV-curable composition of claim 1 , further comprising a pigment colorant.

8. The ink jettable and UV-curable composition of claim 1 further comprising a pigment colorant that has a median particle diameter of less than 150 nm, in an amount of at least 0.1 weight % and up to and including 30 weight %, based on the total weight of the ink jettable and UV-curable composition.

9. The ink jettable and UV-curable composition of claim 1 , further comprising a nonionic surfactant.

10. The ink jettable and UV-curable composition of claim 1 , further comprising a water-soluble or water-dispersible polyurethane.

11. The ink jettable and UV-curable composition of claim 1 having a viscosity of less than 3 centipoise as measured at 25° C.

12. The ink jettable and UV-curable composition of claim 1 , further comprising a photosensitizer.

13. The ink jettable and UV-curable composition of claim 5 further comprising a pigment colorant that has a median particle diameter of less than 150 nm, in an amount of at least 0.1 weight % and up to and including 30 weight %, based on the total weight of the ink jettable and UV-curable composition.

14. The ink jettable and UV-curable composition of claim 1 that comprises a complex of reducible silver ions or silver nanoparticles with the reactive polymer.

15. The ink jettable and UV-curable composition of claim 1 , comprising a complex of silver nanoparticles with the reactive polymer, wherein the silver nanoparticles have an average diameter of at least 2 nm and up to and including 500 nm.

16. The ink jettable and UV-curable composition of claim 1 , comprising a complex of silver nanoparticles with the reactive polymer, wherein the silver nanoparticles have an aspect ratio of less than 2.

17. The ink jettable and UV-curable composition of claim 1 , comprising a complex of silver nanoparticles with the reactive polymer, wherein the silver nanoparticles have an aspect ratio of greater than or equal to 2.

18. The ink jettable and UV-curable composition of claim 1 that comprises a complex of reducible palladium ions or palladium nanoparticles with the reactive polymer.

19. The ink jettable and UV-curable composition of claim 1 that comprises a complex of reducible metal ions or metal nanoparticles with the reactive polymer.

Assignments (11)
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 056734/0233 →
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 056733/0681 →
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: 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.; QUALEX, INC.; KODAK PHILIPPINES, LTD.; NPEC, INC.; CREO MANUFACTURING AMERICA LLC; KODAK AVIATION LEASING LLC
Reel/Frame 050239/0001 →
SECURITY INTEREST Recorded Oct 29, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 036912/0560 →
SECURITY INTEREST Recorded Oct 29, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 036912/0553 →
SECURITY INTEREST Recorded Oct 29, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER SPECIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA N.A.
Reel/Frame 036912/0167 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2015
From: BRUST, THOMAS B.; WYAND, ANNE TROXELL; BENNETT, GRACE ANN; FALKNER, CATHERINE A.
To: EASTMAN KODAK COMPANY
Reel/Frame 036587/0164 →
Continuity (1)
Related Publication 20170081532A1 · Mar 23, 2017