IP Library Granted Patent US 9,586,200
Granted Patent B2
US 9,586,200 · App. 14/571,354 · Granted Mar 7, 2017

Forming catalytic sites from reducible silver complexes

Inventors: Deepak Shukla (Webster, NY); Kevin M. Donovan (Bergen, NY)
Assignee: EASTMAN KODAK COMPANY
B01J37/344B01J23/50B01J31/06B01J37/0219B01J37/16C23C18/1637C23C18/1834C23C18/34C23C18/40C23C18/405
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Quick Facts
Patent No.
US 9,586,200
App. No.
14/571,354
Granted
Mar 7, 2017
Kind
B2
Abstract

A non-aqueous metal catalytic composition includes (a) a silver complex comprising reducible silver ions, (b) an organic phosphite, (c) an oxyazinium salt silver ion photoreducing agent, (d) a hindered pyridine, (e) a photocurable component, a non-curable polymer, or combination of a photocurable component and a non-curable polymer, and (f) a photosensitizer different from all components (a) through (e) in the non-aqueous metal catalytic composition, in an amount of at least 1 weight %. This non-aqueous metal catalytic composition can be used to form silver metal particles in situ during suitable reducing conditions. The silver metal can be provided in a suitable layer or pattern on a substrate, which can then be subsequently subjected to electroless plating to form electrically-conductive layers or patterns for use in various articles or as touch screen displays in electronic devices.

Claims (40)

1. A method for providing an article, comprising:

providing a metal catalytic pattern composed of a non-aqueous metal catalytic composition on a substrate, the non-aqueous metal catalytic composition comprising, in admixture:

(a) a silver complex comprising reducible silver ions, in an amount of at least 2 weight % and up to and including 25 weight %, wherein the silver complex is silver acetate, silver benzoate, silver nitrite, silver oxide, silver sulfate, silver thiocyanate, silver carbonate, silver myristate, silver citrate, silver phenylacetate, silver malonate, silver succinate, silver adipate, silver phosphate, silver perchlorate, silver tetrafluoroborate, silver acetylacetonate, silver lactate, silver oxalate, silver 2-phenylpyridine; a silver fluoride complex; a β-carbonyl ketone silver (I) complex; a silver protein; or a combination thereof,

(b) an organic phosphite in an amount of at least 2 weight % and up to and including 10 weight %, wherein the organic phosphite is tri-iso-propyl phosphite, tri n-butyl phosphite, tri-iso-propyl phosphite, tri-iso-butyl phosphite, triamyl phosphite, tri-n-hexyl phosphite, tri-n-octyl phosphite, tri-n-nonyl phosphite, tri(ethylene glycol) phosphite, tri(propylene glycol) phosphite, tri(iso-propylene glycol) phosphite, tri(n-butylene glycol) phosphite, tri(iso-butylene glycol) phosphite, tri(n-pentylene glycol) phosphite, tri(n-hexylene glycol) phosphite, tri(n-nonylene glycol) phosphite, tri(diethylene glycol) phosphite, tri(triethylene glycol) phosphite, tri(polyethylene glycol) phosphite, tri(polypropylene glycol) phosphite, or tri(polybutylene glycol) phosphite, or a mixture thereof,

(c) an oxyazinium salt silver ion photoreducing agent in an amount of at least 2 weight % and up to and including 25 weight %,

(d) a hindered pyridine in an amount of at least 5 weight % and up to and including 20 weight %, wherein the hindered pyridine in a compound having an alkyl group having 1 to 18 carbon atoms, a phenyl group or a naphthyl group in an ortho position on the pyridine ring

(e) a photocurable component, non-curable polymer, or combination of a photocurable component and a non-curable polymer in an amount of at least 10 weight % and up to and including 88 weight %, and

(f) a photosensitizer different from all components (a) through (e) in the non-aqueous metal catalytic composition, in an amount of at least 1 weight % and up to and including 10 weight %,

all amounts being based on the total amount of components (a) through (f) in the non-aqueous metal catalytic composition,

to provide a precursor article comprising the metal catalytic pattern composed of the non-aqueous metal catalytic composition;

photoreducing the reducible silver ions to silver particles in the metal catalytic pattern by imagewise exposure of the precursor article to radiation having a wavelength of at least 150 nm and up to and including 700 nm;

the method further comprising:

electrolessly plating a metal other than silver onto the silver particles in the metal catalytic pattern, or

removing organic phosphite from metal catalytic pattern, and electrolessly plating a metal other than silver onto the silver particles in the metal catalytic pattern,

wherein the oxyazinium salt silver ion photoreducing agent is one or more of the oxyazinium salt compounds OZ-1 through OZ-16 in the following TABLE I:

TABLE I

OZ-1

OZ-2

OZ-3

OZ-4

OZ-5

OZ-6

OZ-7

OZ-8

OZ-9

OZ-10

OZ-11

OZ-12

OZ-13

OZ-14

OZ-15

OZ-16

2. The method of claim 1 , comprising:

photoreducing the reducible silver ions to silver particles in the metal catalytic pattern in the presence of oxygen.

3. The method of claim 1 , wherein the photosensitizer is a ketocoumarin, xanthone, thioxanthone, arylketone, polycyclic aromatic hydrocarbon, or combination thereof.

4. The method of claim 1 , comprising:

photoreducing the reducible silver ions to silver particles having an average particle size of at least 10 nm and up to and including 1000 nm and at least 80% of the number of the silver particles have a particle size of at least 10 nm and up to and including 100 nm.

5. The method of claim 1 , wherein the non-aqueous metal catalytic composition further comprises an organic solvent that is acetone, dichloromethane, isopropanol, dipropylene glycol methyl ether, ethylene glycol, chloroform, methanol, ethanol, isopropanol, 1-methoxy-2-propanol, methylene chloride, or a mixture thereof.

6. The method of claim 1 , wherein the photocurable component or non-curable polymer acts as an organic solvent medium.

7. The method of claim 1 , wherein the metal catalytic pattern is provided on the substrate by inkjet printing or flexographic printing.

Assignments (11)
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 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 4, 2021
From: EASTMAN KODAK COMPANY
To: ALTER DOMUS (US) LLC
Reel/Frame 056733/0681 →
RELEASE OF SECURITY INTEREST Recorded Jan 24, 2020
From: BARCLAYS BANK PLC
To: 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.
Reel/Frame 052773/0001 →
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 24, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 035272/0372 →
SECURITY INTEREST Recorded Mar 23, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 035258/0321 →
SECURITY INTEREST Recorded Mar 23, 2015
From: EASTMAN KODAK COMPANY; FAR EAST DEVELOPMENT LTD.; FPC INC.; KODAK (NEAR EAST), INC.; KODAK AMERICAS, LTD.; KODAK PORTUGUESA LIMITED; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 035247/0116 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 16, 2014
From: SHUKLA, DEEPAK; DONOVAN, KEVIN M
To: EASTMAN KODAK COMPANY
Reel/Frame 034512/0612 →
Continuity (1)
Related Publication 20160167036A1 · Jun 16, 2016