IP Library Granted Patent US 10,351,720
Granted Patent B2
US 10,351,720 · App. 15/729,714 · Granted Jul 16, 2019

Non-crosslinked, crosslinkable polyurethane

Inventors: Peter John Ghyzel (Rochester, NY); Catherine A. Falkner (Rochester, NY); John Leonard Muehlbauer (Stafford, NY); Thomas B. Brust (Webster, NY)
Assignee: EASTMAN KODAK COMPANY
C09D11/30C08G18/3203C08G18/348C08G18/4854C08G18/6204C08G18/6692C08G18/7671C09D11/102C09D175/08
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Quick Facts
Patent No.
US 10,351,720
App. No.
15/729,714
Granted
Jul 16, 2019
Kind
B2
Abstract

A non-crosslinked, crosslinkable polyurethane has an acid number of 20-40 and a glass transition temperature of up to and including 40° C. It can be derived from an aromatic diisocyanate; and a diol mixture of at least D 1 , D 2 , D 3 , and D 4 diols. D 1 has a C 3 to C 7 aliphatic group and at least one pendant carboxy group or pendant neutralized carboxy group. D 2 has a chain of repeating C 2 to C 6 alkylene oxide groups and a molecular weight of 250-3000. D 3 is an alkoxylated bisphenol A or aliphatic cyclic diol present in an amount of at least 5 mol %. D 4 is a hydroxy-terminated polybutadiene having a molecular weight of at least 1000, and is present in an amount of at least 0.1-5 mol %.

Claims (24)

1. A non-crosslinked, crosslinkable polyurethane having an acid number of at least 20 and up to and including 40, and a glass transition temperature (T g ) of up to and including 40° C.,

the non-crosslinked, crosslinkable polyurethane derived from:

1) an aromatic diisocyanate; and

2) a diol mixture of at least D 1 , D 2 , D 3 , and D 4 diols,

wherein:

the D 1 diol comprises a C 3 to C 7 aliphatic group between two hydroxy groups, and at least one pendant carboxy group or pendant neutralized carboxy group,

the D 2 dial comprises a chain of one or more repeating C 2 to C 6 alkylene oxide groups and has a molecular weight of at least 250 and up to and including 3,000,

the D 3 diol is an alkoxylated bisphenol A or an aliphatic cyclic diol that is present in an amount of at least 5 mol %, based on the total molar amount of the at least D 1 through D 4 diols in the diol mixture, and

the D 4 diol is a hydroxy-terminated polybutadiene having a molecular weight of at least 1000, and is present in an amount of at least 0.1 mol % and up to and including 5 mol %, based on the total molar amount of the at least D 1 through D 4 diols in the diol mixture.

2. The non-crosslinked, crosslinkable polyurethane of claim 1 , having an acid number of at least 20 and up to and including 35.

3. The non-crosslinked, crosslinkable polyurethane of claim 1 , having a glass transition temperature (T g ) of at least 10° C. up to and including 40° C.

4. The non-crosslinked, crosslinkable polyurethane of claim 1 , having a weight average molecular weight (M w ) of at least 20,000 and up to and including 150,000.

5. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 1 diol comprises a C 3 to C 5 aliphatic group between the two hydroxy groups.

6. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 2 diol comprises a chain of repeating C 3 or C 4 alkylene oxide groups and has a molecular weight of at least 250 and up to and including 1,000.

7. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 3 diol comprises an alkoxylated bisphenol A.

8. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 3 diol is present in an amount of at least 5 mol % and up to and including 30 mol %, based on the total molar amount of the at least D 1 through D 4 diols in the diol mixture.

9. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 3 diol is present in an amount of at least 8 mol % and up to and including 25 mol %, based on the total molar amount of the at least D 1 through D 4 diols in the diol mixture.

10. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 4 diol has a molecular weight of at least 1,000 and up to and including 7,000.

11. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 4 diol is present in an amount of at least 0.2 mol % and up to and including 2 mol %, based on the total molar amount of the D 1 through D 4 diols in the dial mixture.

12. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 1 diol is present in an amount of at least 25 mol % and up to and including 40 mol %, the D 2 diol is present in an amount of at least 30 mol % and up to and including 75 mol %, the D 3 diol is present in an amount of at least 8 mol % and up to and including 25 mol %, and the D 4 diol is present in an amount of at least 0.3 mol % and up to and including 1.5 mol %, all based on the total molar amount of the at least D 1 through D 4 diols in the diol mixture.

13. The non-crosslinked, crosslinkable polyurethane of claim 1 , having an acid number of at least 25 and up to and including 35 and a glass transition temperature (T g ) of at least 10° C. up to and including 40° C., and wherein the aromatic diisocyanate is 4,4′-methylenebis(phenylisocyanate), the D 1 diol is 2,2′-bis(hydroxymethyl)propionic acid or a neutralized form thereof, the D 2 diol is poly(tetramethylene glycol) (M n of 650), the D 3 diol is bisphenol A bis(2-hydroxypropyl) ether, and the D 4 diol is hydroxyl terminated poly(butadiene).

14. The non-crosslinked, crosslinkable polyurethane of claim 1 , having a weight average molecular weight (M w ) of at least 35,000 and up to and including 120,000.

15. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 1 diol has an acyclic aliphatic group and a carboxy group that is attached to the acyclic aliphatic group at least one carbon atom removed from each hydroxy group.

16. The non-crosslinked, crosslinkable polyurethane of claim 1 , wherein the D 1 diol is at least partially neutralized using ammonium hydroxide, dimethylaminoethanol, or potassium hydroxide.

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 13, 2017
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 044100/0585 →
SECURITY INTEREST Recorded Nov 13, 2017
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 044099/0729 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 11, 2017
From: GHYZEL, PETER JOHN; FALKNER, CATHERINE A.; MUEHLBAUER, JOHN LEONARD; BRUST, THOMAS B.
To: EASTMAN KODAK COMPANY
Reel/Frame 043833/0833 →
Continuity (1)
Related Publication 20190106585A1 · Apr 11, 2019