Fluorinated ether polymer, the preparation method therefore and use thereof

Patent metadata

Field	Value
Publication number	US-11299586-B2
Application number	US-201816955666-A
Country	US
Kind code	B2
Filing date	Dec 21, 2018
Priority date	Dec 26, 2017
Publication date	Apr 12, 2022
Grant date	Apr 12, 2022

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.

First claim

The invention claimed is:

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;
R f 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.

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

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

4. The fluorinated ether polymer of claim 1 , wherein R f is derived from
F(CFCF 3 CF 2 O) n CFCF 3 COOH,
F(CFCF 3 CF 2 O) n CFCF 3 CH 2 OH,
HO(CH 2 CH 2 O) m CH 2 CF 2 O(CF 2 CF 2 O) p (CF 2 O) q CF 2 CH 2 (OCH 2 CH 2 ) m OH
HOCH 2 CF 2 O(CF 2 CF 2 O) p (CF 2 O) n CF 2 CH 2 OH
HOOCCF 3 FC(CFCF 3 CF 2 O) n CFCF 3 COOH
F(CF 2 CF 2 O) n CFCF 3 COOH
HOOCCFCF 3 (CF 2 CF 2 O) n CFCF 3 COOH
F(CF 2 CF 2 O) n CF 2 COOH
HOOCCF 2 (CF 2 CF 2 O) n CF 2 COOH
F(CF 2 CF 2 OCF 2 CF 2 CF 2 O) n CF 2 COOH
HOOCCF 2 (CF 2 CF 2 OCF 2 CF 2 CF 2 O) n CF 2 COOH
HOOCCH 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 COOH
CF 3 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 COOH
HOOC(OCH 2 CH 2 ) n CH 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 (OCH 2 CH 2 ) n COOH
CF 3 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 (OCH 2 CH 2 ) n COOH
F(CFCF 3 CF 2 O) n CFCF 3 CH 2 OH
HOCH 2 CF 3 FC(CFCF 3 CF 2 O) n CFCF 3 CH 2 OH
F(CF 2 CF 2 O) n CFCF 3 CH 2 OH
HOCH 2 CFCF 3 (CF 2 CF 2 O) n CFCF 3 CH 2 OH
F(CF 2 CF 2 O) n CF 2 CH 2 OH
HOCH 2 CF 2 (CF 2 CF 2 O) n CF 2 CH 2 OH
F(CF 2 CF 2 OCF 2 CF 2 CF 2 O) n CF 2 CH 2 OH
HOCH 2 CF 2 (CF 2 CF 2 OCF 2 CF 2 CF 2 O) n CF 2 CH 2 OH
HOCH 2 CH 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 CH 2 OH
CF 3 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 CH 2 OH
HOCH 2 (OCH 2 CH 2 ) n CH 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 (OCH 2 CH 2 ) n CH 2 OH, or
CF 3 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CH 2 (OCH 2 CH 2 ) n CH 2 OH
wherein m, n, p, q are integers, and on average, independently ranging from 1 to 50.

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

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

7. A method for preparing the fluorinated ether polymer of claim 1 , comprising:
a) mixing a perfluoropolyether containing R f , 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.

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

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

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.

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

Assignees

• Akzo Nobel Coatings Int Bv

Inventors

• Wang Jianhui
• Lu Junbiao
• Xu Zhenglin
• Shi Zheng
• Xing Shili

Classifications

• C08G65/007 Primary

  containing fluorine · CPC title

• C08G65/3322

  acyclic · CPC title

• C08G63/682 Primary

  containing halogens · CPC title

• C09D167/06

  Unsaturated polyesters having carbon-to-carbon unsaturation · CPC title

• C08G2650/48

  containing fluorine, e.g. perfluropolyethers · CPC title