IP Library Granted Patent US 11,041,078
Granted Patent B2
US 11,041,078 · App. 16/597,995 · Granted Jun 22, 2021

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

Inventor: Deepak Shukla (Webster, NY)
Assignee: EASTMAN KODAK COMPANY
C09D5/24C07C59/08C07C251/38C09D11/033C09D11/52H01B1/02
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Quick Facts
Patent No.
US 11,041,078
App. No.
16/597,995
Granted
Jun 22, 2021
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) 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 (19)

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

a) a non-hydroxylic-solvent soluble silver complex consisting of one or two reducible silver ions, each reducible silver ion being complexed with an α-oxy carboxylate 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 that is derived from 2-hydroxybutyric acid, 2-hydroxyisobutyric acid, or 2-hydroxy-2-methylbutyric acid; 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, bis 2;

b) a solvent medium comprising at least one non-hydroxylic solvent that is selected from the group consisting of acetonitrile, benzonitrile, methyl ethyl ketone, butyronitrile, propionitrile, isovaleronitrile, valeronitrile, and a mixture of two or more of these non-hydroxylic solvents, and the solvent medium does not contain water or if water is present, it is present in an amount of less than 5 weight % based on the total weight of the solvent medium; and

c) 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 one or more non-hydroxylic-solvent soluble silver complexes are present in an amount of at least 5 weight % and up to and including 90 weight % based on the total weight of the photosensitive reducible silver ion-containing composition; and the photosensitizer is present in an amount of at least 0.5 weight % and up to and including 4 weight %, based on the total weight of the one or more non-hydroxylic-solvent soluble silver complexes.

3. 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.

4. The photosensitive reducible silver ion-containing composition of claim 3 , wherein one of R 5 and R 6 is hydrogen and the other is an alkyl having 1 to 3 carbon atoms, or both R 5 and R 6 are independently alkyl groups each having 1 to 3 carbon atoms.

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

6. 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.

7. 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.

8. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the h) solvent medium contains only one or more of acetonitrile, benzonitrile, butyronitrile, propionitrile, isovaleronitrile, valeronitrile, or a mixture of two or more of these non-hydroxylic solvents.

9. The photosensitive reducible silver ion-containing composition of claim 1 , wherein the solvent medium does not contain water or if water is present, it is present in an amount of less than 1 weight % based on the total weight of the solvent medium.

Assignments (6)
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 →
NOTICE OF SECURITY INTERESTS Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 056984/0001 →
SECURITY INTEREST Recorded Nov 13, 2019
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 050991/0573 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 10, 2019
From: SHUKLA, DEEPAK
To: EASTMAN KODAK COMPANY
Reel/Frame 050675/0377 →
Continuity (2)
Continuation In Part 15362879 · Nov 29, 2016
Related Publication 20200048479A1 · Feb 13, 2020