IP Library Granted Patent US 9,444,084
Granted Patent B2
US 9,444,084 · App. 13/995,100 · Granted Sep 13, 2016

Fluoropolymer compositions

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,444,084
App. No.
13/995,100
Granted
Sep 13, 2016
Kind
B2
Abstract

A composition for solubilizing a fluoropolymer is described. Further described, is how the fluoropolymer composition is obtained, as well as the process for its preparation and its use as a coating applicant. The composition can include a solubilized fluoropolymer and a solvent blend of a diester and dimethylsulfoxyde.

Claims (57)

1. A fluoropolymer composition comprising:

a solvent blend comprising:

a diester of formula (I):

R 1 —OOC-A-COO—R 2   (I),

wherein R 1 and R 2 , identical or different, are C 1 -C 20 alkyl, aryl, alkylaryl, or arylalkyl groups, linear or branched, cyclic or non cyclic, and

A is a linear or branched divalent alkylene group, and

dimethylsulfoxide (DMSO); and

a fluoropolymer solubilized in the solvent blend.

2. The composition as defined by claim 1 , wherein R 1 and R 2 , identical or different are selected from the group consisting of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, isooctyl, 2-ethylhexyl, cyclohexyl, phenyl and benzyl.

3. The composition as defined by claim 1 , wherein the diester is a mixture of different diesters of formula (I).

4. The composition as defined by claim 1 , wherein A is C 3 -C 10 branched divalent alkylene.

5. The composition as defined by claim 1 , wherein A is selected from the group consisting of the following:

A MG of formula —CH(CH 3 )—CH 2 —CH 2 —,

A ES of formula —CH(C 2 H 5 )—CH 2 —, and their mixtures.

6. The composition as defined by claim 1 , wherein the diester has the following formula:

CH 3 —OOC—CH(CH 3 )—CH 2 —CH 2 —COO—CH 3 .

7. The composition as defined by claim 1 , wherein the diester is a mixture comprising diesters of the following formula (I′), (I″) and optionally (II):

R 1 —OOC-A MG -COO—R 2   (I′)

R 1 —OOC-A ES -COO—R 2   (I″), and

optionally R 1 —OOC—(CH 2 ) 4 —COO—R 2   (II),

wherein:

A MG is —CH(CH 3 )—CH 2 —CH 2 —,

A ES is —CH(C 2 H 5 )—CH 2 —.

8. The composition as defined by claim 7 , wherein R 1 and R 2 are methyl groups.

9. The composition as defined by claim 7 , wherein the mixture of diesters comprises:

from 70% to 95% by weight of diester of formula (I′),

from 5% to 30% by weight of diester of formula (I″), and

from 0% to 10% by weight of diester of formula (II).

10. The composition as defined by claim 1 , wherein A is a divalent alkylene group of formula (CH 2 ) r , wherein r is an average number of from 2 to 4.

11. The composition as defined by claim 10 , wherein the diester is a mixture of dimethyladipate (r=4), dimethylglutarate (r=3) and diméthylsuccinate (r=2), or a mixture of diethyladipate (r=4), diethylglutarate (r=3) and diethylsuccinate (r=2), or a mixture of diisobutyladipate (r=4), diisobutylglutarate (r=3) and diisobutylsuccinate (r=2).

12. The composition as defined by claim 11 , wherein the diester is a mixture comprising:

from 9% to 17% by weight of dimethyladipate,

from 59% to 67% by weight of dimethylglutarate, and

from 20% to 28% by weight of dimethylsuccinate.

13. The composition as defined by claim 1 , wherein the weight ratio between the diester and DMSO is of from 1/99 to 99/1.

14. The composition as defined by claim 13 , wherein the weight ratio between the diester and DMSO is from 20/80 to 80/20.

15. The composition as defined by claim 13 , wherein the weight ratio between the diester and DMSO is from 70/30 to 30/70.

16. The composition as defined by claim 1 , wherein the diester is dimethylsuccinate.

17. The composition as defined by claim 1 , wherein the fluoropolymer is polyvinylidene_fluoride (PDVF) and copolymer of vinylidene fluoride with comonomers hexafluoropropylene (HFP) and/or chlorotrifluoroethylene (CTFE).

18. The composition as defined by claim 1 , wherein the amount of fluoropolymer is of from 1% to 15% by weight.

19. The composition as defined by claim 1 , wherein the composition comprises an odor masking agent.

20. The composition as defined by claim 1 , wherein the composition comprises an anti freezing agent.

21. A process of preparing the composition as defined by claim 1 , wherein the process comprises the steps of:

preparing the solvent blend by mixing a diester of formula (I) and dimethylsulfoxide,

introducing the solvent blend into the fluoropolymer, under stirring, and

heating the mixture at a temperature form room temperature to a temperature equal to or below 100° C., thereby solubilizing the fluoropolymer and forming the fluoropolymer composition of claim 1 .

22. The process as defined by claim 21 , further comprising cooling down the mixture.

23. The process as defined by claim 21 , wherein the solvent blend is heated at a temperature from 30° C. to 80° C.

24. A process of preparing the composition as defined by claim 1 , wherein the process of preparation comprises the steps of:

preparing the solvent blend by mixing a diester of formula (I) and dimethylsulfoxide,

heating the solvent blend at a temperature from room temperature to a temperature equal to or below 100° C., and

introducing the fluoropolymer into the solvent blend, thereby solubilizing the fluoropolymer and forming the fluoropolymer composition of claim 1 .

25. The process as defined by claim 24 , wherein the solvents blend is heated to a temperature from 30° C. to 80° C.

26. A method of preparing a membrane, a foam or a substrate coating, the method comprising preparing the membrane foam or coating using the fluoropolymer composition as defined by claim 1 as a raw material for the membrane, foam or coating.

27. A process for coating a substrate, the process comprising applying the fluoropolymer composition as defined by claim 1 onto one or two sides of the substrate or parts thereof and removing the solvent.

28. The process as defined by claim 27 , wherein the substrate is a battery separator material.

29. A method of recycling fluoropolymer, the method comprising using the solvent blend as defined by claim 1 in the recovery of PVDF from a backing of a photovoltaic panel or a wire coating, thereby forming the fluoropolymer composition of claim 1 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2024
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 066374/0642 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 7, 2023
From: RHODIA OPERATIONS
To: SPECIALTY OPERATIONS FRANCE
Reel/Frame 065488/0365 →
CHANGE OF NAME Recorded Jan 28, 2014
From: RHODIA (CHINA) CO., LTD
To: SOLVAY (CHINA) CO., LTD
Reel/Frame 032131/0301 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 30, 2013
From: CHENG, SHUJING; MU, ANN; DEROO, SOPHIE; LASNET DE LANTY, PATRICK
To: RHODIA (CHINA) CO., LTD; RHODIA OPERATIONS
Reel/Frame 031118/0564 →