# US 11,299,586 B2 · Fluorinated ether polymer, the preparation method therefore and use thereof

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- Number: US 11,299,586 B2
- Document ID: US11299586B2
- Status: Granted
- Kind: B2
- Application number: 16/955,666
- Filed: 2018-12-21
- Published: 2020-12-10
- Granted: 2022-04-12
- Earliest claimed: 2017-12-26
- Assignees: Akzo Nobel Coatings International B.V.
- Applicants: Akzo Nobel Coatings International B.V.
- Inventors: Jianhui Wang; Junbiao Lu; Zhenglin Xu; Zheng Shi; Shili Xing
- Web page: https://patentgrep.com/patent/US11299586B2

## CPC

- C08G 65/007: {containing fluorine}
- C08G 63/682: containing halogens
- C08G 65/3322: {acyclic}
- C08L 51/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
- C09D 151/08: grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09D 167/06: Unsaturated polyesters having carbon-to-carbon unsaturation
- C08G 2650/48: containing fluorine, e.g. perfluropolyethers
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

The embodiments herein relate to a fluorinated ether polymer which is capable of forming coatings with stain resistance, anti-fingerprint and anti-scratching properties. The polymer may be cured with multiple measures, therefore it has a variety of applications in coating and ink industry. The fluorinated ether polymers of the embodiments herein may be added into coating formulations to decrease the surface energy of resulting coatings. It is also feasible that the fluorinated ether polymers of the embodiments herein are used as the main resin component in coating formulations. The embodiments herein also relates to a method for manufacturing the polyester resin, and the use of the polyester resin in industries.

## Claims

### Claim 1

A fluorinated ether polymer comprising one of the following structures (I) to (VIII),
wherein A is a functional group comprising the following structure:
B is a functional group comprising one of the following structures:
n is an integer, on average, ranging from 1 to 50;
Rf is a functional group derived from a perfluoropolyether containing a carboxyl group at one end of its molecular chain, a perfluoropolyether containing carboxyl groups at both ends of its molecular chain, a perfluoropolyether containing a hydroxyl group at one end of its molecular chain, or a perfluoropolyether containing hydroxyl groups at both ends of its molecular chain, the average molecular weight of perfluoropolyether being from 500 to 4000.

### Claim 2 (depends on 1)

The fluorinated ether polymer of claim 1, wherein n is an integer, on average, ranging from 10 to 30.

### Claim 3 (depends on 1)

The fluorinated ether polymer of claim 1, wherein the number average molecular weight of Rf is from 1000 to 3000.

### Claim 4 (depends on 1)

The fluorinated ether polymer of claim 1, wherein Rf is derived from
F(CFCF3CF2O)nCFCF3COOH,
F(CFCF3CF2O)nCFCF3CH2OH,
HO(CH2CH2O)mCH2CF2O(CF2CF2O)p(CF2O)qCF2CH2(OCH2CH2)mOH
HOCH2CF2O(CF2CF2O)p(CF2O)nCF2CH2OH
HOOCCF3FC(CFCF3CF2O)nCFCF3COOH
F(CF2CF2O)nCFCF3COOH
HOOCCFCF3(CF2CF2O)nCFCF3COOH
F(CF2CF2O)nCF2COOH
HOOCCF2(CF2CF2O)nCF2COOH
F(CF2CF2OCF2CF2CF2O)nCF2COOH
HOOCCF2(CF2CF2OCF2CF2CF2O)nCF2COOH
HOOCCH2CF2O(CF2CF2O)m(CF2O)nCF2CH2COOH
CF3O(CF2CF2O)m(CF2O)nCF2CH2COOH
HOOC(OCH2CH2)nCH2CF2O(CF2CF2O)m(CF2O)nCF2CH2(OCH2CH2)nCOOH
CF3O(CF2CF2O)m(CF2O)nCF2CH2(OCH2CH2)nCOOH
F(CFCF3CF2O)nCFCF3CH2OH
HOCH2CF3FC(CFCF3CF2O)nCFCF3CH2OH
F(CF2CF2O)nCFCF3CH2OH
HOCH2CFCF3(CF2CF2O)nCFCF3CH2OH
F(CF2CF2O)nCF2CH2OH
HOCH2CF2(CF2CF2O)nCF2CH2OH
F(CF2CF2OCF2CF2CF2O)nCF2CH2OH
HOCH2CF2(CF2CF2OCF2CF2CF2O)nCF2CH2OH
HOCH2CH2CF2O(CF2CF2O)m(CF2O)nCF2CH2CH2OH
CF3O(CF2CF2O)m(CF2O)nCF2CH2CH2OH
HOCH2(OCH2CH2)nCH2CF2O(CF2CF2O)m(CF2O)nCF2CH2(OCH2CH2)nCH2OH, or
CF3O(CF2CF2O)m(CF2O)nCF2CH2(OCH2CH2)nCH2OH
wherein m, n, p, q are integers, and on average, independently ranging from 1 to 50.

### Claim 5 (depends on 1)

The fluorinated ether polymer of claim 1, wherein the number average molecular weight of the fluorinated ether polymer is from 1000 to 100000.

### Claim 6 (depends on 1)

The fluorinated ether polymer of claim 1, wherein the number average molecular weight of the fluorinated ether polymer is from 2000 to 5000.

### Claim 7 (depends on 1)

A method for preparing the fluorinated ether polymer of claim 1, comprising:
a) mixing a perfluoropolyether containing Rf, monomers that are capable of forming structures A and B according to claim 1, and an inhibitor that stabilizes carbon double bonds;
b) heating the mixture to a temperature ranging from 90 to 120° C., and
c) maintaining the temperature for 2 to 5 hours.

### Claim 8 (depends on 7)

The method of claim 7, wherein the molar ratio of perfluoropolyether containing Rf, monomer that is capable of forming structure A, and monomer that is capable of forming structure B is 1:1-15:1-15.

### Claim 9 (depends on 8)

The method of claim 8, wherein the molar ratio of perfluoropolyether containing Rf, monomer that is capable of forming structure A, and monomer that is capable of forming structure B is 1:5-10:5-10.

### Claim 10

A method of using a fluorinated ether polymer to form a coating onto a substrate, comprising applying and then curing the fluorinated ether polymer on the substrate.

### Claim 11 (depends on 1, 7)

A coating composition which contains a fluorinated ether polymer according to claim 1 or prepared by the method of claim 7.