Silver ion α-oxy carboxylate-oxime complexes

Patent metadata

Field	Value
Publication number	US-9783553-B1
Application number	US-201615362868-A
Country	US
Kind code	B1
Filing date	Nov 29, 2016
Priority date	Nov 29, 2016
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

A non-hydroxylic-solvent soluble silver complex comprises a reducible silver ion complexed with an α-oxy carboxylate and an oxime compound. The non-hydroxylic-solvent soluble silver complex can be 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. Such complexes can be incorporated into photosensitive compositions in method to provide thin films or patterns in various articles to provide electrically-conductive silver metal.

First claim

The invention claimed is:

1. A non-hydroxylic-solvent soluble silver complex consisting of a reducible silver ion complexed with an α-oxy carboxylate and an oxime compound,
the non-hydroxylic-solvent soluble silver complex being represented by the following formula (I):
(Ag + ) a (L) b (P) c    (1)

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.

2. The non-hydroxylic-solvent soluble silver complex 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.

3. The non-hydroxylic-solvent soluble silver complex of claim 2 , 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 independently branched or linear alkyl groups having 1 to 8 carbon atoms, wherein any of the hydrogen atoms in the R 1 , R 2 , and R 3 branched or linear alkyl groups optionally can be replaced with a fluorine atom.

4. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the α-oxy carboxylate has a molecular weight of 250 or less.

5. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein L is represented by the following formula (III):

wherein R 4 is a branched or linear alkyl group having 1 to 8 carbon atoms and optionally, any of the hydrogen atoms in the R 4 branched or linear alkyl group can be substituted with a fluorine atom.

6. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the α-oxy carboxylate is selected from:
the group consisting of lactate, 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 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.

7. The non-hydroxylic-solvent soluble silver complex 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.

8. The non-hydroxylic-solvent soluble silver complex of claim 7 , 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.

9. The non-hydroxylic-solvent soluble silver complex of claim 7 , wherein R 7 is hydrogen or an alkyl group having 1 to 3 carbon atoms.

10. The non-hydroxylic-solvent soluble silver complex 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.

11. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the oxime compound has an oxidation potential of at least 1.5 V vs. saturated calomel electrode (SCE); the α-oxy carboxylate has a first oxidation potential of at least 1 V vs. SCE; and upon decarboxylation of the α-oxy carboxylate, a second radical is generated that has an oxidation potential of less than 1 V vs. SCE.

12. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the oxime compound has an oxidation potential of at least 1.5 V vs. SCE.

13. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the oxime compound has a molecular weight of 200 or less.

14. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the oxime compound has a boiling point of less than 150° C. at 760 mm atmospheric pressure.

15. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the oxime compound has a boiling point of less than 100° C. at 760 mm atmospheric pressure.

16. The non-hydroxylic-solvent soluble silver complex of claim 1 , which meets a silver ion stability test wherein, when the non-hydroxylic-solvent soluble silver complex is held for 24 hours at ambient temperature and under yellow safelight, less than 0.1 mol % of its original silver ion content is reduced to silver metal.

17. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein:
L has a molecular weight of 250 or less, and L is represented by either the following formula (II) or (III):

wherein R 1 is hydrogen or an alkyl group having 1 or 2 carbon atoms, R 2 and R 3 are independently branched or linear alkyl groups having 1 to 8 carbon atoms, wherein any of the hydrogen atoms in the R 1 , R 2 , and R 3 branched or linear alkyl groups optionally can be replaced with a fluorine atom, and R 4 is a branched or linear alkyl group having 1 to 8 carbon atoms wherein any of the hydrogen atoms optionally can be replaced with a fluorine atom; and
P is represented by the following Structure (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, an acyl group, 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.

18. The non-hydroxylic-solvent soluble silver complex 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.

Assignees

• Eastman Kodak Co

Inventors

• Shukla Deepak
• Welter Thomas Robert

Classifications

• C07F1/005 Primary

  without C-Metal linkages · CPC title