IP Library Granted Patent US 9,637,581
Granted Patent B2
US 9,637,581 · App. 14/301,380 · Granted May 2, 2017

Thiosulfate-containing polymers associated with photosensitizer component

Inventors: Deepak Shukla (Webster, NY); Kevin M. Donovan (Bergen, NY); Mark R. Mis (Rush, NY)
Assignee: Eastman Kodak Company
C08F228/02C08F220/14C08F222/02C08F222/10C08F222/40H01B3/447C08F2222/404
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Quick Facts
Patent No.
US 9,637,581
App. No.
14/301,380
Filed
Jun 11, 2014
Granted
May 2, 2017
Kind
B2
Examiner
HU, HENRY S
Art Unit
1764
USPC
526/240
Abstract

A photocurable or thermally curable thiosulfate-containing polymer has (a) recurring units and (d) recurring units, shown as either Structure (I) or (II) and Structure (V) below: R represents the organic polymer backbone, G is a single bond or divalent linking group, Q + is an organic charge balancing cation, M represents a charge balancing cation, and “a” represents at least 0.5 mol % and to 99.5 mol % of (a) recurring units; R″ represents the organic polymer backbone, G″ is a carbonyloxy group, R 3 comprises a monovalent linear, branched, or carbocyclic non-aromatic hydrocarbon group having 1 to 18 carbon atoms, or it comprises a phenyl group having one or more such substituents, and “d” represents at least 0.5 mol % and to 99.5 mol % of (d) recurring units. These thiosulfate-containing polymers can be used to made dielectric compositions and gate dielectric layers in various devices.

Claims (10)

1. A photocurable thiosulfate-containing polymer that has a T g of at least 50° C. and comprises: (a) recurring units comprising pendant thiosulfate groups, and (d) recurring units, wherein the photocurable thiosulfate-containing polymer has sensitivity to irradiation at a wavelength of from 150 nm to 700 nm to cause the pendant thiosulfate groups to form disulfide bonds,

which (a) recurring units are represented by Structure (II) below, and the (d) recurring units are represented by Structure (V) below:

wherein R represents an organic polymer backbone, G is a single bond or divalent linking group, Q + is an organic charge balancing cation, and “a” represents at least 0.5 mol % and up to and including 99.5 mol % of (a) recurring units, based on the total recurring units in the photocurable thiosulfate-containing polymer;

wherein R″ represents an organic polymer backbone, G″ is a carbonyloxy group, R 3 comprises a monovalent linear, branched, or carbocyclic non-aromatic hydrocarbon group having 1 to 18 carbon atoms, or R 3 comprises a phenyl group having one or more linear, branched, or carbocyclic non-aromatic hydrocarbon substituents, at least one of which linear, branched, or carbocyclic non-aromatic hydrocarbon substituent has at least 6 carbon atoms and up to and including 18 carbon atoms, and “d” represents at least 0.5 mol % and up to and including 99.5 mol % of (d) recurring units, based on the total recurring units in the photocurable thiosulfate-containing polymer.

2. The photocurable thiosulfate-containing polymer of claim 1 , wherein the organic charge balancing cations are selected from quaternary ammonium, pyridinium, morpholinium, benzolium, imidazolium, alkoxypyridinium, thiazolium, and quinolinium monovalent cations.

3. The photocurable thiosulfate polymer of claim 1 , further comprising (c) recurring units that are represented by the following Structure (IV):

wherein R′ represents the organic polymer backbone, G′ is a single bond or a divalent linking group, R 2 is an electron-accepting photosensitizer component derived from a cyano-substituted carbocyclic aromatic compound, an aromatic anhydride, an aromatic imide, a condensed pyridinium salt, a pyrylium salt, a quinone, or a ketocoumarin, and

“c” represents at least 1 mol % and up to and including 10 mol % of (c) recurring units, based on the total recurring units in the photocurable thiosulfate-containing polymer.

4. The photocurable thiosulfate-containing polymer of claim 1 , which comprises the (a) recurring units in an amount of at least 5 mol % and up to and including 30 mol %, and the (d) recurring units in an amount of at least 1 mol % and up to and including 30 mol %, all based on total recurring units in the photocurable thiosulfate-containing polymer.

5. The photocurable thiosulfate-containing polymer of claim 1 that has sensitivity to irradiation at a wavelength of from 150 nm to 450 nm to cause the pendant thiosulfate groups to form disulfide bonds.

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 Aug 20, 2014
From: 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; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 033570/0143 →
SECURITY INTEREST Recorded Aug 18, 2014
From: 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; QUALEX INC.; KODAK PHILIPPINES, LTD; NPEC INC.
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 033557/0276 →
SECURITY INTEREST Recorded Aug 18, 2014
From: 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; QUALEX INC.; KODAK PHILIPPINES, LTD.; NPEC INC.
To: BARCLAYS BANK PLC, AS ADMINISTRATIVE AGENT
Reel/Frame 033552/0979 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 11, 2014
From: SHUKLA, DEEPAK; DONOVAN, KEVIN M.; MIS, MARK R.
To: EASTMAN KODAK COMPANY
Reel/Frame 033072/0734 →
Continuity (1)
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