IP Library Granted Patent US 9,676,950
Granted Patent B2
US 9,676,950 · App. 14/856,658 · Granted Jun 13, 2017

Articles prepared using ink jettable, UV-curable compositions

Inventors: Thomas B. Brust (Webster, NY); Anne Troxell Wyand (Victor, NY)
Assignee: EASTMAN KODAK COMPANY
C09D11/322C09D11/101C09D125/04C09D133/02C09D133/14C09D133/26
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Quick Facts
Patent No.
US 9,676,950
App. No.
14/856,658
Granted
Jun 13, 2017
Kind
B2
Abstract

Articles are prepared with a substrate and an ink jetted and UV-curable image some of which also include metal nanoparticles or reducible metal ions. The in jetted and UV-curable image can be obtained from an ink jettable and UV-curable composition comprising: a reactive polymer comprising: (a1) or (a2) recurring units comprising pendant metal complexing water-solubilizing groups, (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. Such articles can be used to provide electrically-conductive articles and devices after electrolessly plating a complex of the metal nanoparticles and the UV-cured reactive polymer.

Claims (48)

1. An article comprising a substrate and having thereon an ink jetted and UV-curable image that is derived from an ink jettable and UV-curable composition comprising:

a reactive polymer comprising: (a1) at least 5 mol % of recurring units comprising pendant metal complexing water-solubilizing groups, (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 amid; 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.

2. The article of claim 1 , wherein the reactive polymer comprises at least 40 mol % of the (a1) recurring units comprising sulfonic acid or sulfonate groups, based on the total recurring units in the reactive polymer.

3. The article 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 article 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.

5. The article of claim 1 , wherein the ink jetted and UV-curable image further comprises 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.

6. The article of claim 1 , wherein the ink jetted and UV-curable composition further comprises a pigment colorant that has a median particle diameter of less than 150 nm and more likely less than 100 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.

7. The article of claim 1 , wherein the ink jetted and UV-curable composition further comprises a water-soluble or water-dispersible polyurethane.

8. An article comprising a substrate and having thereon an ink jetted and UV-curable metallized image that is derived from an ink jettable and UV-curable composition comprising:

a complex of reducible metal ions or metal nanoparticles with a reactive polymer comprising: (a2) at least 5 mol % of recurring units comprising pendant metal complexing sulfonate groups, (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.

9. The article of claim 8 , comprising a complex of reducible silver ions or 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.

10. The article of claim 8 , comprising a complex of silver nanoparticles with the reactive polymer, wherein the silver nanoparticles have an aspect ratio of less than 2.

11. The article of claim 8 , 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.

12. The article of claim 8 , comprising a complex of reducible palladium ions or palladium nanoparticles with the reactive polymer.

13. The article of claim 8 , wherein the reactive polymer comprises at least 40 mol % of the (a1) recurring units comprising sulfonic acid or sulfonate groups, based on the total recurring units in the reactive polymer.

14. The article of claim 8 , 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.

15. The article of claim 8 , 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.

16. The article of claim 8 , wherein the UV-curable metallized image further comprises a pigment colorant that has a median particle diameter of less than 150 nm and more likely less than 100 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.

17. The article of claim 1 , wherein the UV-curable metallized image further comprises a water-soluble or water-dispersible polyurethane.

18. An article comprising a substrate and having thereon an ink jetted and UV-curable image that is derived from 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, (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.

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
To: EASTMAN KODAK COMPANY
Reel/Frame 036587/0637 →
Continuity (1)
Related Publication 20170081536A1 · Mar 23, 2017