IP Library Granted Patent US 10,487,221
Granted Patent B2
US 10,487,221 · App. 15/362,879 · Granted Nov 26, 2019

Photosensitive compositions containing silver ion α-oxy carboxylate-oxime complexes

Inventors: Deepak Shukla (Webster, NY); Thomas Robert Welter (Webster, NY)
Assignee: EASTMAN KODAK COMPANY
C09D5/24C09D11/033C09D11/52H01B1/02
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Quick Facts
Patent No.
US 10,487,221
App. No.
15/362,879
Granted
Nov 26, 2019
Kind
B2
Abstract

A photosensitive reducible silver ion-containing composition can be used to provide electrically-conductive silver metal in thin films or patterns. This composition comprises: a) a non-hydroxylic-solvent soluble silver complex represented by the following formula (I): (Ag + ) a (L) b (P) c    (I) wherein L represents an α-oxy carboxylate; P represents an oxime compound; a is 1 or 2; b is 1 or 2; and c is 1, 2, 3, or 4, provided that when a is 1, b is 1, and when a is 2, b is 2; b) optionally, a photosensitizer that can either reduce the reducible silver ion or oxidize the α-oxy carboxylate; and c) a solvent medium comprising at least one non-hydroxylic solvent. Electrically-conductive silver can be provided by photochemical conversion of the reducible silver ions in the complex.

Claims (22)

1. A photosensitive reducible silver ion-containing composition consisting essentially of:

a) a non-hydroxylic-solvent soluble silver complex consisting of one or more reducible silver ions, each reducible silver ion being complexed with one or more α-oxy carboxylates via one or two oxygen atoms and the same reducible silver ion being complexed with one or more oxime compounds via a nitrogen atom,

the non-hydroxylic-solvent soluble silver complex being represented by the following formula (I):

(Ag + ) a (L) b (P) c    (I)

wherein L represents the α-oxy carboxylate; P represents the oxime compound; a is 1 or 2; b is 1 or 2; and c is 1, 2, 3, or 4, provided that when a is 1, b is 1, and when a is 2, b is 2;

b) a solvent medium comprising propylene carbonate; and

c) optionally, a photosensitizer that can either reduce the reducible silver ion or oxidize the α-oxy carboxylate.

2. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the non-hydroxylic-solvent soluble silver complex is silver lactate acetoxime, silver lactate acetaldoxime, silver lactate butanal O-methyloxime, silver 2-hydroxyisobutyrate acetoxime, silver 2-hydroxy-2-methylbutyrate acetaldoxime, or silver 2-hydroxy-2-methylbutyrate acetaldoxime.

3. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the solvent medium further comprises one or more non-hydroxylic solvents selected from the group consisting of acetonitrile, benzonitrile, butyronitrile, propionitrile, isovaleronitrile, valeronitrile, and a mixture of two or more of these organic solvents.

4. The photosensitive reducible silver ion-containing composition of claim 1 , wherein L is represented by the following formula (II):

wherein R 1 , R 2 , and R 3 are independently hydrogen or branched or linear alkyl groups.

5. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the α-oxy carboxylate is derived from:

the group of conjugate acids consisting of lactic acid, 2-hydroxybutyric acid, 2-hydroxy-3-methylbutyric acid, 2-hydroxy-3,3-dimethylbutyric acid, 2-hydroxy-isobutyric acid, 2-hydroxy-2-methylbutyric acid, 2-ethyl-2-hydroxybutyric acid, 2-hydroxy-2,3-dimethylbutyric acid, 2-ethyl-2-methoxybutyric acid, 2-methoxy-2-methylpropanoic acid, 1-hydroxycyclopentane-1-carboxylic acid, 2,3-dihydroxy-2,3-dimethylsuccinic acid, and 2,4-dihydroxy-2,4-dimethylpentanedioic acid; or

the group of conjugate acids consisting of pyruvic acid, 3-methylpyruvic acid, 3,3-dimethylpyruvic acid, 3,3-dimethyl-2-oxobutanoic acid, 3,3-dimethyl-2-oxopentanoic acid, and 2,3-dioxosuccinic acid.

6. The photosensitive reducible silver ion-containing composition of claim 1 , wherein P is an oxime compound represented by the following formula (IV):

wherein R 5 and R 6 are independently hydrogen or an alkyl group having 1 to 6 carbon atoms, provided that at least one of R 5 and R 6 is the alkyl group, or R 5 and R 6 can together represent the carbon atoms sufficient to provide a 5- or 6-membered carbocyclic ring; and R 7 is hydrogen, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, a —C(═O)R 8 group, or a carbonyloxyalkyl group [—C(═O)OR 8 ], wherein R 8 is hydrogen or an alkyl having 1 to 6 carbon atoms.

7. The photosensitive reducible silver ion-containing compositions of claim 6 , wherein R 7 is hydrogen or an alkyl group having 1 to 3 carbon atoms.

8. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the oxime compound is selected from the group consisting of acetoxime, acetaldoxime, Aldicarb, dimethylglyoxime, methylethyl ketone oxime, propionaldehyde oxime, cyclohexanone oxime, cyclopentanone oxime, heptanal oxime, acetone-O-methyl oxime, acetaldehyde-O-methyl oxime, propionaldehyde-O-methyl oxime, butanaldehyde-O-methyl oxime, 2-butanone-O-methyl oxime, cyclopentanone-O-methyl oxime, and 2-butanone-O-ethyl oxime.

9. The photosensitive reducible silver ion-containing composition of claim 1 , wherein:

(i) a and b are both 1 and c is 1 or 2;

(ii) a and b are both 2 and c is 2; or

(iii) a and b are both 2 and c is 4.

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 Mar 23, 2017
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 041696/0145 →
SECURITY INTEREST Recorded Mar 23, 2017
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: JPMORGAN CHASE BANK, N.A.
Reel/Frame 041695/0364 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 29, 2016
From: SHUKLA, DEEPAK; WELTER, THOMAS ROBERT
To: EASTMAN KODAK COMPANY
Reel/Frame 040440/0131 →
Continuity (1)
Related Publication 20180148583A1 · May 31, 2018