IP Library Granted Patent US 10,745,570
Granted Patent B2
US 10,745,570 · App. 15/880,830 · Granted Aug 18, 2020

Copper-containing articles

Inventors: Thomas B. Brust (Webster, NY); Grace Ann Bennett (Scottsville, NY); Catherine A. Falkner (Rochester, NY); Anne Troxell Wyand (Victor, NY)
Assignee: EASTMAN RODACK COMPANY
C09D5/1618C08F2/60C08F212/14C08F220/06C08F220/36C08F220/58C09D5/14C09D5/1662C09D125/16C09D133/14C09D133/26C23C18/40C08F220/365C08F220/585C08F2800/10C08K2003/085C08K2201/011
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Quick Facts
Patent No.
US 10,745,570
App. No.
15/880,830
Granted
Aug 18, 2020
Kind
B2
Abstract

A water-soluble composition includes reducible copper ions or copper nanoparticles complexed with a reactive polymer. The reactive polymer can be crosslinked using suitable irradiation to provide copper-containing water-insoluble complexes. The water-soluble composition can be used to provide various articles and electrically-conductive materials that can be assembled in electronic devices. The reactive polymer has greater than 1 mol % of recurring units comprising sulfonic acid or sulfonate groups, at least 5 mol % of recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition, and optionally at least 1 mol % of recurring units comprising a pendant amide, amine, hydroxyl, lactam, phosphonic acid, or carboxylic acid group.

Claims (27)

1. A copper-containing article comprising a substrate and having disposed thereon a copper-containing composition comprising a water-soluble complex of a reactive polymer with reducible copper ions or copper nanoparticles, the reactive polymer comprising: (a) greater than 1 mol % of recurring units comprising sulfonic acid or 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, amine, hydroxyl, lactam, phosphonic acid, or carboxylic acid group, all amounts based on the total recurring units in the reactive polymer.

2. The copper-containing article of claim 1 , wherein the reactive polymer comprises:

(i-a) at least 5 mol % and up to and including 50 mol % of the recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition, based on the total recurring units in the reactive polymer,

(i-b) at least 1 mol % and up to and including 93 mol % of recurring units comprising a pendant hydroxyl, amide, or carboxylic acid group, based on the total recurring units in the reactive polymer, or

both (i-a) and (i-b).

3. The copper-containing article of claim 1 , wherein the recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition comprise:

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.

4. The copper-containing article of claim 1 , wherein the substrate has a first supporting side and an opposing second supporting side, and the copper-containing composition is disposed on one or both the first supporting side and the opposing second supporting of the substrate.

5. The copper-containing article of claim 1 , wherein the copper-containing composition is disposed on the substrate in a patternwise fashion.

6. A copper-containing article comprising a substrate and having disposed thereon a water-insoluble composition comprising a crosslinked water-insoluble complex of a crosslinked reacted polymer with reducible copper ions or copper nanoparticles, the crosslinked reacted polymer derived from photoexposure of a reactive polymer comprising: (a) greater than 1 mol % of recurring units comprising sulfonic acid or 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, amine, hydroxyl, lactam, phosphonic acid, or carboxylic acid group, all amounts based on the total recurring units in the reactive polymer.

7. The copper-containing article of claim 6 , wherein the water-insoluble composition comprises copper nanoparticles that have an average diameter of at least 2 nm and up to and including 500 nm.

8. The copper-containing article of claim 6 , wherein the same or different crosslinked water-insoluble complex is disposed on both the first supporting side and the opposing second supporting side of the substrate in the same or different patternwise fashion.

9. The copper-containing article of claim 6 , wherein the substrate is a continuous polymeric web.

10. The copper-containing article of claim 6 , wherein the reactive polymer comprises:

(i-a) at least 5 mol % and up to and including 50 mol % of the recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition, based on the total recurring units in the reactive polymer,

(i-b) at least 1 mol % and up to and including 93 mol % of recurring units comprising a pendant hydroxyl, amide, or carboxylic acid group, based on the total recurring units in the reactive polymer, or

both (i-a) and (i-b).

11. The copper-containing article of claim 6 , wherein the recurring units comprising a pendant group capable of crosslinking via [2+2] photocycloaddition comprise:

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.

Assignments (9)
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
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 →
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 Apr 4, 2018
From: 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.
To: BANK OF AMERICA N.A.
Reel/Frame 045433/0108 →
SECURITY INTEREST Recorded Apr 4, 2018
From: 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.
To: JP MORGAN CHASE BANK N.A.
Reel/Frame 045433/0010 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2018
From: BRUST, THOMAS B.; BENNETT, GRACE ANN; FALKNER, CATHERINE A.; WYAND, ANNE TROXELL
To: EASTMAN KODAK COMPANY
Reel/Frame 044739/0252 →
Continuity (2)
Division 14714422 · May 18, 2015
Related Publication 20190233660A1 · Aug 1, 2019