Fluoropolymer compositions comprising a curing agent with ethylenically unsaturated and electron donor groups, and substrates coated therewith

Patent metadata

Field	Value
Publication number	US-12291588-B2
Application number	US-202017766372-A
Country	US
Kind code	B2
Filing date	Oct 27, 2020
Priority date	Nov 4, 2019
Publication date	May 6, 2025
Grant date	May 6, 2025

Abstract

A method of making a crosslinked fluoropolymer is described. The method comprises applying a composition to a substrate, wherein the composition comprises fluoropolymer and a fluorinated solvent, one or more curing agents comprising an ethylenically unsaturated group and an electron donor group or precursor thereof. The method further comprises removing the solvent and curing the fluoropolymer with actinic (e.g. ultraviolet “UV”) radiation. Also described is a composition comprising a fluoropolymer dissolved in a fluorinated solvent, and one or more curing agents comprising an ethylenically unsaturated group and an electron donor group or precursor thereof; and article comprising the crosslinked fluoropolymer.

First claim

What is claimed is:

1. A method of making a crosslinked fluoropolymer comprising:
i) applying a composition to a substrate, wherein the composition comprises
a fluorinated solvent and a fluoropolymer, wherein the fluoropolymer comprises sufficient polymerized units derived from perfluorinated monomers such that the fluoropolymer dissolves in the fluorinated solvent; and cure sites comprising atoms selected from iodine, bromine, or chlorine; and
one or more curing agents comprising an ethylenically unsaturated group and an electron donor group or precursor thereof;

ii) removing the solvent;
iii) curing the fluoropolymer with actinic radiation.

2. The method of claim 1 wherein the actinic radiation comprises ultraviolet radiation.

3. The method of claim 1 wherein the fluoropolymer has less than 5, 4, 3, 2, or 1 wt. % of polymerized units of VDF.

4. The method of claim 1 wherein the fluoropolymer comprises at least 90% by weight of polymerizable units derived from perfluorinated monomers.

5. The method of claim 1 wherein the perfluorinated monomers are selected from tetrafluoroethene (TFE) and one or more unsaturated perfluorinated alkyl ethers.

6. The method of claim 5 wherein the unsaturated perfluorinated alkyl ether of the fluoropolymer has the general formula
R f —O—(CF 2 ) n —CF═CF 2

wherein n is 1 or 0 and R f is a perfluoroalkyl or perfluoroether group.

7. The method of claim 1 wherein the curing agent comprising the electron donor group is an amine compound.

8. The method of claim 7 wherein the amine compound is an amino organosilane ester compound or ester equivalent.

9. The method of claim 1 wherein the curing agent comprises at least two ethylenically unsaturated groups.

10. The method of claim 1 wherein the curing agent comprises at least one ethylenically unsaturated group and at least one alkoxy silane group.

11. The method of claim 1 wherein the composition further comprises an alkoxy silane compound that lacks one or more amine groups.

12. The method of claim 1 wherein the fluoropolymer comprises 0 to 5 wt.-% of polymerized units derived from non-fluorinated or partially fluorinated monomers.

13. The method of claim 1 wherein the fluorinated solvent has the formula:
C p F 2p+1 —O—C q H 2q+1

wherein q is an integer from 1 to 5 and p is an integer from 5 to 11.

14. The method of claim 13 wherein the C p F 2p+1 -unit is branched.

15. The method of claim 1 wherein the fluorinated solvent has a global warming potential GWP of less than 1000.

16. The method of claim 1 wherein the composition further comprises a second fluoropolymer.

17. The method of claim 16 wherein the second fluoropolymer does not dissolve in the fluorinated solvent.

18. The method of claim 17 wherein the second fluoropolymer comprises crystalline fluoropolymer particles.

19. The method of claim 1 wherein the substrate is a release liner, an organic substrate, or inorganic substrate.

Assignees

• 3M Innovative Properties Company

Inventors

• Jing Naiyong
• Gu Cheng
• Hintzer Klaus
• Nguyen Tho Q
• Scott Peter J

Classifications

• C08L2312/06

  by radiation · CPC title

• C08L27/04

  containing chlorine atoms · CPC title

• C08L27/10

  containing bromine or iodine atoms · CPC title

• C08L27/12

  containing fluorine atoms · CPC title

• C08L27/22

  modified by chemical after-treatment · CPC title