IP Library Granted Patent US 11,037,692
Granted Patent B2
US 11,037,692 · App. 16/367,715 · Granted Jun 15, 2021

Articles having silver ion α-oxy carboxylate oxime complexes

Inventors: Deepak Shukla (Webster, NY); Kevin M. Donovan (Bergen, NY)
Assignee: EASTMAN KODAK COMPANY
H01B1/02C09D11/52H05K3/106H05K2203/1157H05K2203/121
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Quick Facts
Patent No.
US 11,037,692
App. No.
16/367,715
Granted
Jun 15, 2021
Kind
B2
Abstract

A product article is prepared from a precursor article that has a substrate and a photosensitive thin film or a photosensitive thin film pattern on a supporting side. The product article have an electrically-conductive silver metal-containing film or thin film patterns, each of which contains electrically-conductive metallicsilver obtained by reduction of silver ions in the precursor article, an α-oxy carboxylate, an oxime compound, and a photosensitizer that can either reduce reducible silver ions or oxidize the α-oxy carboxylate.

Claims (51)

1. A product article comprising a substrate having a first supporting side and a second opposing supporting side, and having on at least the first supporting side,

an electrically-conductive silver metal-containing thin film or one or more electrically-conductive silver metal-containing thin film patterns, comprising:

silver metal;

an α-oxy carboxylate;

an oxime compound; and

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

wherein:

the α-oxy carboxylate is represented by the following formula (II):

wherein R 1 is hydrogen, and R 2 , and R 3 are independently branched or linear alkyl groups having 1 to 8 carbon atoms,

the oxime compound is 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.

2. The product article of claim 1 , comprising two or more electrically-conductive silver metal-containing thin film patterns in different portions on the first supporting side of the substrate.

3. The product article of claim 1 , further comprising one or more electrically-conductive silver metal-containing thin film patterns in different portions on the second opposing supporting side of the substrate,

each of these one or more electrically-conductive silver metal-containing thin film patterns comprising:

silver metal;

an α-oxy carboxylate;

an oxime compound; and

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

wherein:

the α-oxy carboxylate is represented by the following formula (II):

wherein R 1 is hydrogen, and R 2 , and R 3 are independently branched or linear alkyl groups having 1 to 8 carbon atoms,

the oxime compound is 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 product article of claim 1 that is provided as a wound roll of a continuous material.

5. The product article of claim 4 , wherein the wound roll of a continuous material is a wound roll of a polyester.

6. A product article comprising a substrate having a first supporting side and a second opposing supporting side, and having on at least the first supporting side,

an electrically-conductive silver metal-containing thin film or one or more electrically-conductive silver metal-containing thin film patterns, comprising:

silver metal;

an α-oxy carboxylate;

an oxime compound; and

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

wherein the α-oxy carboxylate is derived from:

the group consisting of 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 and the oxime compound is 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 product article of claim 1 , 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.

8. The product article 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 product article of claim 1 , wherein the electrically-conductive silver metal-containing thin film or each of the one or more electrically-conductive silver metal-containing thin film patterns, has a resistivity of less than 10 6 ohms/□ as measured using a 4-point probe device.

10. The product article of claim 1 , wherein the electrically-conductive silver metal-containing thin film or each of the one or more electrically-conductive silver metal-containing thin film patterns, has a resistivity of less than 500 ohms/□ as measured using a 4-point probe device.

11. The product article of claim 1 , wherein R 2 and R 3 are different branched or linear alkyl groups.

12. The product article of claim 1 , wherein the α-oxy carboxylate is 2-hydroxyisobutyrate or 2-hydroxy-2-methylbutyrate.

13. A product article comprising a substrate having a first supporting side and a second opposing supporting side, and having on at least the first supporting side,

an electrically-conductive silver metal-containing thin film or one or more electrically-conductive silver metal-containing thin film patterns, comprising:

silver metal;

an α-oxy carboxylate;

an oxime compound; and

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

wherein:

the α-oxy carboxylate is represented by the following formula (H):

wherein R 1 is hydrogen or a branched or linear alkyl group having 1 to 3 carbon atoms, and R 2 , and R 3 are different branched or linear alkyl groups having 1 to 8 carbon atoms, and

the oxime compound is 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.

Assignments (5)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2019
From: SHUKLA, DEEPAK; DONOVAN, KEVIN M.
To: EASTMAN KODAK COMPANY
Reel/Frame 048727/0043 →
Continuity (2)
Division 15362907 · Nov 29, 2016
Related Publication 20190228873A1 · Jul 25, 2019