IP Library Granted Patent US 9,718,842
Granted Patent B1
US 9,718,842 · App. 15/231,837 · Granted Aug 1, 2017

Silver ion carboxylate primary alkylamine complexes

Inventor: Deepak Shukla (Webster, NY)
Assignee: EASTMAN KODAK COMPANY
C07F1/00G03F7/063
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,718,842
App. No.
15/231,837
Granted
Aug 1, 2017
Kind
B1
Abstract

A non-hydroxylic-solvent soluble silver complex has a reducible silver ion complexed with an α-oxy carboxylate and a primary alkylamine. This 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 primary alkylamine; 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 that are then used to provide photosensitive thin films or photosensitive thin film patterns. The reducible silver ions can be quickly and efficiently reduced to electrically-conductive silver metal upon exposure to UV-visible radiation in various methods.

Claims (29)

1. A non-hydroxylic-solvent soluble silver complex comprising: a reducible silver ion complexed with an α-oxy carboxylate and a primary alkylamine,

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 primary alkylamine; 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 linear or branched 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 any of the hydrogen atoms in the R 4 branched or linear alkyl group optionally 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

selected from 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 a primary alkylamine having a boiling point of less than or equal to 175° C.

8. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein P is a primary alkylamine having a boiling point of less than or equal to 125° C.

9. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the primary alkylamine has an oxidation potential of greater than 1.0 V vs. SCE; the α-oxy carboxylate has a first oxidation potential of at least 1.2 V vs. SCE; and upon decarboxylation of the α-oxy carboxylate, a second radical is generated that has an oxidation potential of less than 1.0 V vs. SCE.

10. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the primary alkylamine has an oxidation potential of greater than 1.4 V vs. SCE.

11. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the primary alkylamine has a pKa of at least 1 and up to and including 30 as measured in acetonitrile.

12. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the primary alkylamine has a pKa of at least 10 and up to and including 25 as measured in acetonitrile, and the primary alkylamine has an oxidation potential that is greater than 1.0 V vs. SCE.

13. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the primary alkylamine comprises a branched or linear alkyl group having 3 to 6 carbon atoms.

14. The non-hydroxylic-solvent soluble silver complex of claim 1 , wherein the primary alkylamine is selected from the group consisting of propylamine, n-butylamine, t-butylamine, isopropylamine, 2,2,2-trifluoroethylamine, 2,2,3-pentafluoropropylamine, 3,3,3-trifluoropropylamine, 1,2-dimethylpropylamine, t-amyl amine, isopentylamine, 2-amino-3-methylbutane, 3,3-dimethyl-2-butylamine, 2-aminohexane, and sec-butylamine.

15. The non-hydroxylic-solvent soluble silver complex of claim 1 , which meets a silver ion stability test such that 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.

16. 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 (H) 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 a primary alkylamine that is selected from the group consisting of propylamine, n-butylamine, t-butylamine, isopropylamine, 2,2,2-trifluoroethylamine, 2,2,3,3,3-pentafluoropropylamine, 3,3,3-trifluoropropylamine, 1,2-dimethylpropylamine, t-amyl amine, isopentylamine, 2-amino-3-methylbutane, 3,3-dimethyl-2-butylamine, 2-aminohexane, and sec-butylamine.

17. 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.

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 Nov 16, 2016
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 040340/0193 →
SECURITY INTEREST Recorded Nov 16, 2016
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 040340/0017 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 9, 2016
From: SHUKLA, DEEPAK
To: EASTMAN KODAK COMPANY
Reel/Frame 039378/0533 →