Copolymers including ultraviolet absorbing groups and fluoropolymer compositions including them

Patent metadata

Field	Value
Publication number	US-9670300-B2
Application number	US-201314654121-A
Country	US
Kind code	B2
Filing date	Dec 20, 2013
Priority date	Dec 20, 2012
Publication date	Jun 6, 2017
Grant date	Jun 6, 2017

Abstract

A thermoplastic copolymer that includes a first divalent unit having a pendent ultraviolet absorbing group and a second divalent unit that is fluorinated. A fluoropolymer composition including the thermoplastic copolymer is also disclosed.

First claim

What is claimed is:

1. A copolymer comprising:
a first divalent unit comprising a pendent ultraviolet absorbing group comprising a triazine; and
a second divalent unit represented by formula:

wherein
Rf represents a fluoroalkyl group having from 1 to 6 carbon atoms optionally interrupted by one —O— group, or Rf represents a polyfluoropolyether group;
R 1 is hydrogen or methyl;
Q is a bond, —SO 2 —N(R)—, or —C(O)—N(R)—, wherein R is alkyl having from 1 to 4 carbon atoms or hydrogen; and
m is an integer from 0 to 11,

wherein the copolymer is a thermoplastic copolymer.

2. The copolymer of claim 1 , wherein the first divalent unit is represented by formula:

wherein
R 1 is hydrogen or methyl;
V is O or NH;
X is alkylene or alkyleneoxy group having from 1 to 10 carbon atoms and optionally interrupted by one or more —O— groups and optionally substituted by a hydroxyl group;
R is alkyl having from one to four carbon atoms;
n is 0 or 1; and
Z is a 4,6-bisphenyl[1,3,5]triazin-2-yl group, wherein the 4,6-bisphenyl[1,3,5]triazin-2yl group, is optionally substituted by one or more alkyl, aryl, alkoxy, hydroxyl, or halogen substituents, or a combination of these substituents.

3. The copolymer of claim 1 , wherein Rf represents a perfluoroalkyl group having up to 4 carbon atoms.

4. The copolymer of claim 1 , further comprising a third divalent unit represented by formula:

wherein
R 6 is hydrogen or methyl; and
R 5 is alkyl having from 1 to 4 carbon atoms.

5. The copolymer of claim 1 , wherein the second divalent unit is present in the copolymer in an amount of up to 50 percent by weight, based on the total weight of the copolymer.

6. A composition comprising a fluoropolymer and the copolymer of claim 1 .

7. The composition of claim 6 , further comprising poly(methyl methacrylate).

8. The composition of claim 6 , wherein the fluoropolymer is present in the composition in an amount of at least 50 percent by weight, based on the total weight of the composition.

9. The composition of claim 6 , further comprising a second copolymer comprising the first divalent unit and at least one of the second divalent unit or a third divalent unit represented by formula:

wherein
R 6 is hydrogen or methyl; and
R 5 is alkyl having from 1 to 4 carbon atoms.

10. The composition of claim 9 , wherein the copolymer and the second copolymer are present in the composition in an amount up to 20 percent combined weight, based on the total weight of the composition.

11. The composition of claim 6 , wherein the composition is essentially free of volatile organic solvent.

12. The composition of claim 6 , wherein the fluoropolymer is selected from the group consisting of ethylene-tetrafluoroethylene copolymer, a tetrafluoroethylene-hexafluoropropylene copolymer, a tetrafluoroethylene-hexafluoropropylene-vinylidene fluoride copolymer, or polyvinylidene fluoride.

13. The composition of claim 6 in the form of a film.

14. A photovoltaic device comprising the composition of claim 6 .

15. The composition of claim 13 , wherein the film is a multilayer film.

16. A composition comprising:
a fluoropolymer;
a copolymer comprising:
a first divalent unit comprising a pendent ultraviolent absorbing group; and
a second divalent unit represented by formula:

wherein
Rf represents a fluoroalkyl group having from 1 to 6 carbon atoms optionally interrupted by one —O— group, or Rf represents a polyfluoropolyether group;
R 1 is hydrogen or methyl;
Q is a bond, —SO 2 —N(R)—, or —C(O)—N(R)—, wherein R is alkyl having from 1 to 4 carbon atoms or hydrogen; and
m is an integer from 0 to 11,

wherein the copolymer is a thermoplastic copolymer; and

a second copolymer, wherein the second copolymer is a copolymer of methyl methacrylate and an acrylate- or methacrylate-functional ultraviolet absorbing group.

17. The copolymer of claim 1 , wherein the copolymer is an oligomer with a number average molecular weight of up to 50,000 grams per mole.

18. The copolymer of claim 17 , wherein the oligomer has a number average molecular weight greater than 5000 grams per mole.

19. The composition of claim 16 , wherein the pendent ultraviolet absorbing group comprises a triazine, a benzophenone, or a benzotriazole.

20. The composition of claim 16 , further comprising poly(methyl methacrylate).

Assignees

• 3M Innovative Properties Co

Inventors

• Olson David B
• Savu Patricia M
• Hebrink Timothy J

Classifications

• C08J2333/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08L33/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C08J2427/16

  Homopolymers or copolymers of vinylidene fluoride · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08F220/22

  Esters containing halogen · CPC title