IP Library Granted Patent US 11,453,731
Granted Patent B2
US 11,453,731 · App. 16/220,189 · Granted Sep 27, 2022

Curable fluorocopolymer formed from tetrafluoropropene

Inventors: Wanchao Jiang (Shanghai, CN); Shijun Feng (Shanghai, CN); Siyuan Zhang (Shanghai, CN); Yun Lin (Shanghai, CN); Andrew J. Poss (Kenmore, NY)
Assignee: HONEYWELL INTERNATIONAL INC.
C08F14/185C08F4/76C08F14/18C08F214/18C08F214/186C08F214/188C09D127/12
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Quick Facts
Patent No.
US 11,453,731
App. No.
16/220,189
Granted
Sep 27, 2022
Kind
B2
Abstract

The present invention is directed to partially fluorinated copolymers and the production thereof. More specifically, the copolymers, which are preferably produced by a solution polymerization process, preferably have at least three units, the first unit selected from 2,3,3,3-tetrafluoropropene and 1,3,3,3-tetrafluoropropene, the second unit having a polymerized monomer selected from the vinyl esters and vinyl ethers, and the third unit having a polymerized monomer derived from a hydroxyl group-containing vinyl ether. The resulting copolymer is environmentally friendly, has favorable molecular weight characteristics, and may be shipped economically in high concentration.

Claims (20)

1. A copolymer composition comprising a copolymer and a solvent or solvents, wherein said copolymer consists of:

(a) from 40 mol % to 60 mol % of polymerized monomers of 1,3,3,3-tetrafluoropropene;

(b) from 5 mol % to 45 mol % of polymerized monomers of vinyl ester(s) or vinyl ether(s); and

(c) from 3 mol % to 30 mol % of polymerized monomers of hydroxyl group-containing vinyl ether(s);

wherein said solvent or solvents comprise from 15-50 wt % of said copolymer composition.

2. The copolymer composition of claim 1 wherein said composition comprises at least 70 wt. % of said copolymer.

3. The copolymer composition of claim 1 wherein said copolymer has hydroxyl groups.

4. The copolymer composition of claim 3 , wherein said hydroxyl group-containing vinyl ether(s) is a compound of formula CH 2 ═CR 5 —OR 6 , wherein R 5 is hydrogen or a methyl group, and R 6 is an unsubstituted straight-chain, branched-chain or alicyclic alkyl group having a hydroxyl groups.

5. The copolymer composition of claim 4 , wherein said hydroxyl group-containing vinyl ether is hydroxyalkyl vinyl ether.

6. The copolymer composition of claim 1 , wherein the copolymer comprises a vinyl ester and wherein said vinyl ester is a compound of formula CH 2 ═CR 1 —O(C═O)R 2 , wherein R 1 is hydrogen or a methyl group, and wherein R 2 is an unsubstituted straight-chain, branched-chain or alicyclic alkyl group having 1 to 12 carbon atoms.

7. The copolymer composition of claim 6 , wherein said vinyl ester is a vinyl versatate ester formed from a C 9 carboxylic acid or a vinyl versatate ester formed from a C 10 carboxylic acid.

8. The copolymer composition of claim 1 , wherein said copolymer consists of said polymerized 1,3,3,3-tetrafluoropropene, vinyl esters and hydroxyl group-containing vinyl ether(s).

9. The copolymer composition of claim 1 , wherein the copolymer has a number average molecular weight of between 5000 and 50000.

10. The copolymer composition of claim 1 , wherein the copolymer has a number average molecular weight of between 5000 and 10000.

11. The copolymer composition of claim 1 wherein the copolymer comprises from 45 mol % to 55 mol % of said polymerized monomers of 1,3,3,3-tetrafluoropropene; from 25 mol % to 45 mol % of said polymerized monomers of vinyl esters or vinyl ethers; and from 5 mol % to 20 mol % of said polymerized monomers of hydroxyl group-containing vinyl ether(s).

12. The copolymer composition of claim 1 , wherein said copolymer consists of said polymerized 1,3,3,3-tetrafluoropropene, ethyl vinyl ether, and hydroxyl butyl vinyl ether.

13. The copolymer composition of claim 1 , wherein said copolymer consists of said polymerized 1,3,3,3-tetrafluoropropene, a vinyl versatate ester formed from a C 10 carboxylic acid and hydroxyl butyl vinyl ether.

14. The copolymer composition of claim 1 , wherein the component (b) is the vinyl ether and wherein said vinyl ether is a compound of formula CH 2 ═CR 3 —OR 4 wherein R 3 is hydrogen or a methyl group, and wherein R 4 is an unsubstituted straight-chain, branched-chain or alicyclic alkyl group having 1 to 12 carbon atoms.

15. The copolymer composition of claim 1 , wherein said copolymer consists of said polymerized 1,3,3,3-tetrafluoropropene, vinyl ethers and hydroxyl group-containing vinyl ether(s).

16. The copolymer composition of claim 1 , wherein the composition comprises 15-25 wt % solvent.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 17, 2020
From: FENG, SHIJUN; JIANG, WANCHAO; LIN, YUN; POSS, ANDREW JOSEPH; ZHANG, SIYUAN
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 054396/0176 →