IP Library Granted Patent US 9,249,248
Granted Patent B1
US 9,249,248 · App. 14/457,477 · Granted Feb 2, 2016

Crosslinkable polymers

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Quick Facts
Patent No.
US 9,249,248
App. No.
14/457,477
Granted
Feb 2, 2016
Kind
B1
Abstract

Crosslinkable polymers comprise recurring units represented by: wherein R, R′, and R″ are independently hydrogen or an alkyl, cyano, or halo group; R 1 is hydrogen or a halo, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, cyano, hydroxy, alkoxy, carboxy, or ester group; L is an organic linking group; EWG represents an electron withdrawing group having a Hammett-sigma value greater than or equal to 0.35 such that the oxygen-carbon bond in O—C(EWG)(R 1 ) is cleavable in the presence of a cleaving acid having a pK a of 2 or less as measured in water; Ar is a substituted or unsubstituted arylene group; X is NR 2 or oxygen; R 2 is hydrogen or an alkyl group; t-alkyl represents a tertiary alkyl group having 4 to 6 carbon atoms, and m represents at least 1 mol % and up to and including 100 mol %, based on the total recurring units in the polymer.

Claims (21)

1. A polymer comprising (a) recurring units that are represented by the following Structure (A):

wherein:

R, R′, and R″ are independently hydrogen or an alkyl, cyano, or halo group,

R 1 is hydrogen or a halo, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, cyano, hydroxy, alkoxy, carboxy, or ester group,

L is an organic linking group,

EWG represents an electron withdrawing group having a Hammett-sigma value greater than or equal to 0.35 such that the oxygen-carbon bond in O—C(EWG)(R 1 ) is cleavable in the presence of a cleaving acid having a pK a of 2 or less as measured in water,

Ar is a substituted or unsubstituted arylene group,

X is NR 2 or oxygen,

R 2 is hydrogen or an alkyl group,

t-alkyl represents a tertiary alkyl group having 4 to 6 carbon atoms, and

m represents at least 1 mol % and up to and including 100 mol %, based on the total recurring units in the polymer.

2. The polymer of claim 1 , wherein R, R′, and R″ are independently hydrogen, methyl, ethyl, or chloro, R 1 is hydrogen, methyl, ethyl, or halo-substituted methyl, X is oxygen, EWG represents a trifluoroalkyl group having 1 to 3 carbon atoms, a trichloroalkyl group having 1 to 3 carbon atoms, cyano, nitro, carboxylic acid, or a carboxylic acid ester, Ar is substituted or unsubstituted phenylene, and t-alkyl represents a tertiary alkyl group having 4 or 5 carbon atoms.

3. The polymer of claim 1 , wherein EWG represents a trichloromethyl group or a trifluoromethyl group, Ar is unsubstituted phenylene, and t-alkyl represents a tertiary butyl group.

4. The polymer of claim 1 , wherein L is a carbonyloxyalkylene group having 1 to 10 carbon atoms in the alkylene chain or a substituted or unsubstituted arylene group.

5. The polymer of claim 1 , wherein m represents at least 10 mol % and up to and including 95 mol %, based on total recurring units in the polymer.

6. The polymer of claim 1 further comprising (b) recurring units comprising pendant groups that provide crosslinking in the presence of the cleaving acid having a pK a of 2 or less as measured in water.

7. The polymer of claim 6 , wherein the (b) recurring units are present in an amount of at least 1 mol % based on the total recurring units in the polymer.

8. The polymer of claim 6 , wherein the (b) recurring units comprise pendant glycidyl groups and are present in an amount of at least 1 mol % and up to and including 50 mol %, based on the total recurring units in the polymer.

9. The polymer of claim 6 further comprising additional (c) recurring units that are different from all (a) and (b) recurring units, wherein the additional (c) recurring units are present in an amount of at least 1 mol % and up to and including 50 mol %, based on the total recurring units in the polymer.

10. The polymer of claim 1 , wherein R, R′, and R″ are independently hydrogen or methyl, R 1 is hydrogen or methyl, L is a carbonyloxyalkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted arylene group, EWG represents a trichloromethyl or trifluoromethyl group, X is oxygen, Ar is a substituted or unsubstituted phenylene group, and t-alkyl represents a tertiary alkyl group having 4 or 5 carbon atoms.

11. The polymer of claim 10 , wherein EWG represents trifluoromethyl, Ar is an unsubstituted phenylene group, and t-alkyl represents a tertiary butyl group.

Assignments (14)
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Jul 24, 2023
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A.
Reel/Frame 064364/0847 →
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 056733/0681 →
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 056734/0233 →
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 Jan 13, 2017
From: EASTMAN KODAK COMPANY
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 041042/0877 →
SECURITY INTEREST Recorded Nov 7, 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 PHILIPPINES, LTD.; KODAK REALTY, INC.; LASER-PACIFIC MEDIA CORPORATION; QUALEX INC.; NPEC INC.
To: BANK OF AMERICA, N.A., AS AGENT
Reel/Frame 034183/0278 →
ASSIGNMENT SECURITY AGREEMENT Recorded Nov 7, 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.; KJODAK PHILIPPINES, LTD.; NEPC INC.
To: BANK OF AMERICA N.A., AS AGENT
Reel/Frame 034215/0071 →
SECURITY INTEREST Recorded Nov 6, 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 034179/0554 →
SECURITY INTEREST Recorded Nov 6, 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 034179/0733 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2014
From: BRUST, THOMAS B.; BENNETT, GRACE ANN; IRVING, MARK EDWARD
To: EASTMAN KODAK COMPANY
Reel/Frame 033514/0692 →