Copolymers of halogenated olefins and halogenated co-monomers

Patent metadata

Field	Value
Publication number	US-11725071-B2
Application number	US-201816651391-A
Country	US
Kind code	B2
Filing date	Sep 25, 2018
Priority date	Sep 27, 2017
Publication date	Aug 15, 2023
Grant date	Aug 15, 2023

Abstract

Copolymers of one or more halogenated olefins and one or more halogenated co-monomers selected from the group consisting of halogenated alkenyl ethers, halogenated alkenyl esters, and halogenated (meth)acrylates are useful in various end-use applications wherein the presence of halogen (e.g., fluorine) in the copolymer imparts one or more desirable properties, as compared to analogous copolymers not containing halogen.

First claim

What is claimed is:

1. A copolymer of a) at least one halogenated olefin represented by the formula
CX 1 X 2 ═CX 3 X 4

wherein the halogenated olefin comprises at least one halogen atom and X 1 , X 2 , X 3 and X 4 are independently selected from a hydrogen atom, a chlorine atom, a fluorine atom, or a halogenated or non-halogenated alkyl group having 1 to 8 carbon atoms, and b) at least one halogenated alkenyl ethers represented by the formula
CX 5 X 6 ═CX 7 —OR 1

wherein X 5 , X 6 and X 7 are independently selected from a hydrogen atom, a chlorine atom, a fluorine atom, or a halogenated or non-halogenated alkyl group having 1 to 8 carbon atoms and at least one of X 5 , X 6 and X 7 is halogen or fluoralkyl and at least one of X 5 , X 6 and X 7 is hydrogen, and R 1 is a non-halogenated alkyl group having 1 to 8 carbon atoms and substituted by at least one hydroxyl group, which may optionally contain one or more functional groups selected from carbonyl or ether functional groups and which may be substituted or unsubstituted wherein said halogenated alkenyl ether comprise at least one halogenated hydroxy alkenyl ether.

2. The copolymer of claim 1 , wherein the halogenated olefin comprises at least one fluorine atom.

3. The copolymer of claim 1 , wherein the halogenated olefin comprises at least one halogen atom which is selected from the group consisting of a fluorine atom and a chlorine atom and which is bonded to at least one carbon atom participating in a carbon-carbon double bond in the halogenated olefin.

4. The copolymer of claim 1 , wherein the at least one halogenated olefin comprises a halogenated olefin selected from the group consisting of CClF═CF 2 , CH 2 ═CF 2 , CFH═CH 2 , CF 2 ═CHF, CF 2 ═CF 2 , CHF═CHF, CF 3 CF═CH 2 , CF 2 ═CHCl, CF 3 CH═CHF, CClF═CH 2 , CF 3 CCl ═CH 2 , CF 3 CH═CHCl, CF 3 CF═CFH, CF 3 CH═CF 2 , CF 3 CF═CFCF 3 , CF 3 CF 2 CF═CF 2 , CF 3 CH═CHCF 3 , CF 2 HCH 2 CF═CH 2 , CF 2 HCH 2 CF═CClH, CF 2 HCH═CFCH 2 Cl and CF 3 —CF═CF 2 .

5. The copolymer of claim 1 , wherein the at least one co-monomer comprises at least one halogenated alkenyl ether comprised of at least one fluorine atom.

6. The copolymer of claim 1 , wherein the at least one co-monomer comprises a halogenated alkenyl ether selected from the group consisting of CF 3 —C(OR 1 )═CH 2 , CF 3 C(OR 1 )═CFH, CF 3 —CH═CH(OR 1 ), CF 3 CF═CH(OR 1 ), CF 3 CH═CF(OR 1 ), CF(OR 1 )═CHCl, CF(OR 1 )═CH 2 , CF(OR 1 )═CFH, CF 3 CH═C(OR 1 )CH 3 , CF 3 CH 2 C(OR 1 )═CH 2 , CF 3 C(OR 1 )═CHCF 3 , CF 3 CF 2 C(OR 1 )═CH 2 , CF 3 CF 2 CF(CF 3 )C(OR 1 )═CH, CH 3 CH 2 CH═CF(OR 1 ), (CF 3 ) 2 CFC(OR 1 )═CH 2 , and CF 3 CF 2 CF 2 CF 2 C(OR 1 )═CH 2 .

7. The copolymer of claim 1 , wherein the at least one halogenated hydroxy alkenyl ether comprises a halogenated hydroxy alkenyl ether represented by formula (4):
CX 8 X 9 ═CX 10 —O—R 2 —OH  (4)

wherein X 8 , X 9 and X 10 are independently selected from a hydrogen atom, a chlorine atom, a fluorine atom, or a halogenated or non-halogenated alkyl group having 1 to 8 carbon atoms, provided that at least one of X 8 , X 9 or X 10 is a halogen or a halogenated alkyl group, and R 2 is a non-halogenated alkyl group having 1 to 8 carbon atoms.

8. The copolymer of claim 7 , wherein —R 2 —OH is selected from the group consisting of hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, hydroxyoctyl, hydroxycyclobutyl, hydroxycyclopentyl, hydroxycyclohexyl, a polyethylene glycol residue, a polypropylene glycol residue, a polyethylene/polypropylene glycol residue, a glycerol residue, an alkoxylated glycerol residue, a sugar residue, an alkoxylated sugar residue, a trimethylolpropane residue, an alkoxylated trimethylolpropane residue, a pentaerythritol residue, an alkoxylated pentaerythritol residue, a dipentaerythritol residue, an alkoxylated dipentaerythritol residue, an alpha-glucoside residue, an alkoxylated alpha-glucoside residue, a trimethylolethane residue, an alkoxylated trimethylolethane residue, a sugar alcohol residue, an alkoxylated sugar alcohol residue, an alkanol amine residue, and an alkoxylated amine residue.

9. The copolymer of claim 1 , having a number average molecular weight of from 5000 to 1,00,000 daltons as measured by gel permeation chromatography using polystyrene standards.

10. The copolymer of claim 1 , wherein the copolymer is a random, alternating, gradient or block copolymer.

11. The copolymer of claim 1 , wherein the copolymer is comprised of from 1 to 99% by weight halogenated olefin and from 99 to 1% by weight halogenated alkenyl ether co-monomer in polymerized form.

12. An article, comprising a substrate having a surface and a coating comprised of a copolymer in accordance with claim 1 on at least a portion of the surface of the substrate.

13. A battery electrode binder, comprising a copolymer in accordance with claim 1 and at least one nonaqueous solvent.

14. A battery, comprising at least one electrode comprising an electrode active material and a copolymer in accordance with claim 1 .

15. A polymeric product obtained by reacting a copolymer in accordance with claim 1 , wherein the copolymer comprises one or more halogenated hydroxy alkenyl ethers in polymerized form, with at least one hydroxyl-reactive substance.

16. An article of manufacture comprising at least one copolymer in accordance with claim 1 , wherein the article of manufacture is selected from the group consisting of coatings, paints, adhesives, sealants, fibers, molded articles, films, sheets, composites and laminates.

Assignees

• Arkema Inc

Inventors

• Chen Benjamin Bin
• Lin Caiping
• Polsz Craig A
• Wood Kurt A
• Wood Brian T
• Clarkson Lucy

Classifications

• C08F214/184 Primary

  with fluorinated vinyl ethers · CPC title

• C08F214/202

  with fluorinated vinyl ethers · CPC title

• C08F214/222

  with fluorinated vinyl ethers · CPC title

• C08F214/242

  with fluorinated vinyl ethers · CPC title

• C08F214/262

  with fluorinated vinyl ethers · CPC title