IP Library Granted Patent US 9,453,095
Granted Patent B2
US 9,453,095 · App. 14/301,375 · Granted Sep 27, 2016

Photocurable and thermally curable thiosulfate-containing polymers

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Quick Facts
Patent No.
US 9,453,095
App. No.
14/301,375
Granted
Sep 27, 2016
Kind
B2
Abstract

Photocurable or thermally curable thiosulfate-containing polymers have a T g of at least 50° C. and (a) recurring units comprising pendant thiosulfate groups, and (b) recurring units comprising organic charge balancing cations that are associated with the (a) recurring units sufficiently to provide a net neutral charge with the pendant thiosulfate groups. These polymers can be represented by the following Structure (III): wherein R represents the organic polymer backbone, G is a single bond or a divalent linking group, M + represents the organic charge balancing cation, and “a” represents at least 0.5 mol % and up to and including 50 mol % of (a) recurring units, and “b” represents the (b) recurring units and is at least equal to the “a” mol %, based on the total recurring units. These thiosulfate-containing polymers can be used to made dielectric compositions and gate dielectric layers in various devices.

Claims (19)

1. A photocurable or thermally curable thiosulfate-containing polymer that has a T g of at least 50° C. and comprises an organic polymer backbone comprising:

(a) recurring units comprising pendant thiosulfate groups, and

(b) recurring units comprising organic charge balancing cations that are associated with the (a) recurring units sufficiently to provide a net neutral charge with the pendant thiosulfate groups,

which photocurable or thermally curable thiosulfate-containing polymer is represented by the following Structure (III):

wherein R represents the organic polymer backbone, G is a single bond or a divalent linking group, M + represents the organic charge balancing cation, and “a” represents at least 0.5 mol % and up to and including 50 mol % of (a) recurring units, and “b” represents the (b) recurring units and is at least equal to the “a” mol %, based on the total recurring units in the photocurable or thermally curable thiosulfate-containing polymer.

2. The photocurable or thermally curable 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 or thermally curable thiosulfate polymer of claim 1 , wherein the (a) recurring units are represented by the following Structure (II) in place of or in addition to the (a) recurring units represented by Structure (III):

wherein R represents the organic polymer backbone, G is a single bond or divalent linking group, Q + is an organic charge balancing cation, and “a” is as defined above.

4. The photocurable or thermally curable 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 a electron-accepting photosensitizer component, 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 or thermally-curable thiosulfate-containing polymer.

5. The photocurable or thermally curable thiosulfate-containing polymer of claim 4 , further comprising (d) recurring units that are represented by the following Structure (V):

wherein 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 linear, branched, or carbocyclic non-aromatic hydrocarbon substituents, at least one of which linear, branched, or carbocyclic non-aromatic hydrocarbon substituents has at least 6 carbon atoms and up to and including 18 carbon atoms, and “d” represents at least 1 mol % and up to and including 40 mol % of (d) recurring units, based on the total recurring units in the photocurable or thermally-curable thiosulfate-containing polymer.

6. The photocurable or thermally curable thiosulfate-containing polymer of claim 1 , further comprising (d) recurring units that are represented by the following Structure (V):

wherein 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 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 1 mol % and up to and including 40 mol % of (d) recurring units, based on the total recurring units in the photocurable or thermally-curable thiosulfate-containing polymer.

7. The photocurable or thermally curable thiosulfate-containing polymer of claim 3 , further comprising (d) recurring units that are represented by the following Structure (V):

wherein 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 branched, or carbocyclic non-aromatic hydrocarbon substituents, at least one of which has at least 6 carbon atoms and up to and including 18 carbon atoms, and “d” represents at least 1 mol % and up to and including 40 mol % of (d) recurring units, based on the total recurring units in the photocurable or thermally-curable thio sulfate-containing polymer.

8. The photocurable or thermally curable thiosulfate-containing polymer of claim 1 , which comprises the (a) recurring units in an amount of at least 0.5 mol % and up to and including 50 mol %, and the (b) recurring units in an amount of at least 0.5 mol % and up to and including 50 mol %, all based on total recurring units in the photocurable or thermally curable thiosulfate-containing polymer.

9. The photocurable or thermally curable thiosulfate-containing polymer of claim 1 , further comprising (e) recurring units that are different from (a) recurring units, (b) recurring units, any (c) recurring units, and any (d) recurring units, which (e) recurring units are present in an amount of up to and including 50 mol %, based on the total recurring units in the photocurable or thermally curable thiosulfate-containing polymer.

10. The photocurable or thermally curable thiosulfate-containing polymer of claim 9 , wherein the (e) recurring units are derived from one or more alkyl acrylates, alkyl methacrylates, (meth)acrylamides, styrene and styrene derivatives, vinyl ethers, vinyl benzoates, vinylidene halides, vinyl halides, vinyl imides, and ethylenically unsaturated polymerizable monomers comprising an epoxy or epithiopropyl group.

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: QUALEX, INC.; 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.; 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.
To: EASTMAN KODAK COMPANY
Reel/Frame 033072/0662 →