Moisture-curable composition, method of using, and composite article

Patent metadata

Field	Value
Publication number	US-9725546-B2
Application number	US-201414901261-A
Country	US
Kind code	B2
Filing date	Jun 6, 2014
Priority date	Jun 25, 2013
Publication date	Aug 8, 2017
Grant date	Aug 8, 2017

Abstract

A moisture-curable composition includes a polymer preparable by free-radical copolymerization of monomers comprising at least one monomer A and at least one monomer B. Monomer(s) A comprise free-radically polymerizable hydrolyzable silane. Monomer(s) B include a divalent group selected from the group consisting of —(CF 2 O) a —, —(CF 2 CF 2 O) b —, —(CF 2 CF 2 CF 2 O) c —, —(CF 2 CF 2 CF 2 CF 2 O) d —, —(CF 2 CF(CF3)O) e —, and combinations thereof, wherein a, b, c, d, and e represent integers in the range of from 0 to 130, and wherein 1≦<a+b+c+d+e≦130. A composite article includes a layer of a composition on a substrate. The composition comprises a cross-linked reaction product of components including the moisture-curable composition. Methods of making the composite article are also disclosed.

First claim

What is claimed is:

1. A moisture-curable composition comprising a polymer prepared by free-radical copolymerization of monomers comprising at least one monomer A, at least one monomer B, and at least one monomer C, wherein:
each monomer A is independently represented by the formula

wherein
R 1 represents H or methyl,
L 1 is a covalent bond or a divalent aliphatic group having from 1 to 10 carbon atoms,
each Y 1 independently represents a hydrocarbyl group having from 1 to 6 carbon atoms,
each Y 2 independently represents a hydrolyzable group, and
g is 0, 1, or 2;

each monomer B is independently represented by the formula

wherein
R 2 , R 3 , and R 4 represent H, methyl, trifluoromethyl, or F, wherein at least one of R 2 , R 3 , and R 4 is F,
R f 1 represents a covalent bond or a divalent group selected from the group consisting of —(CF 2 O) a —, —(CF 2 CF 2 O) b —, —(CF 2 CF 2 CF 2 O) c —, —(CF 2 CF 2 CF 2 CF 2 O) d —, —(CF 2 CF(CF 3 )O) e —, and combinations thereof, wherein a, b, c, d, and e represent integers in the range of from 0 to 130, and wherein 1≦a+b+c+d+e≦130,
R f 2 is a perfluoroalkyl group; and

each C is independently represented by the formula

wherein
L 2 represents a covalent bond or divalent aliphatic group comprising from 1 to 6 carbon atoms, and
R 5 represents a photocrosslinking group containing a benzophenone or substituted benzophenone moiety, and

further wherein the polymer contains less than or equal to 0.49 percent by weight of fluorinated alkene.

2. The moisture-curable composition of claim 1 , wherein the weight ratio of said at least one monomeric unit B to said at least one monomeric unit A is at least 0.8.

3. The moisture-curable composition of claim 1 , wherein L 1 is a covalent bond.

4. The moisture-curable composition of claim 1 , wherein Y 2 is selected from the group consisting of alkoxy groups having from 1 to 4 carbon atoms, alkanoyloxy groups having from 2 to 4 carbon atoms, a hydroxyl group, and Cl.

5. The moisture-curable composition of claim 1 , wherein said at least one monomer B has an average sum of a+b+c+d+e in the range of from 30 to 40.

6. The moisture-curable composition of claim 1 , wherein said at least one monomer B has an average sum of a+b+c+d+e in the range of from 4 to 8.

7. A composite article comprising a composition disposed on a substrate, wherein the composition comprises a cross-linked reaction product of components comprising the moisture-curable composition of claim 1 .

8. A moisture-curable composition comprising a polymer prepared by free-radical copolymerization of monomers comprising at least one monomer A, at least one monomer B, and at least one monomer C, wherein:
each monomer A is independently represented by the formula

wherein
R 1 represents H or methyl,
L 1 is a covalent bond or a divalent aliphatic group having from 1 to 10 carbon atoms,
each Y 1 independently represents a hydrocarbyl group having from 1 to 6 carbon atoms,
each Y 2 independently represents a hydrolyzable group, and
g is 0, 1, or 2;

each monomer B is independently represented by the formula

wherein
R 2 , R 3 , and R 4 represent H, methyl, trifluoromethyl, or F, wherein at least one of R 2 , R 3 , and R 4 is F,
R f 1 represents a covalent bond or a divalent group selected from the group consisting of —(CF 2 O) a —, —(CF 2 CF 2 O) b —, —(CF 2 CF 2 CF 2 O) c —, —(CF 2 CF 2 CF 2 CF 2 O) d —, —(CF 2 CF(CF 3 )O) e —, and combinations thereof, wherein a, b, c, d, and e represent integers in the range of from 0 to 130, and wherein 2≦a+b+c+d+e≦130, and
R f 2 is a perfluoroalkyl group; and

each monomer C is independently represented by the formula

wherein
L 2 represents a covalent bond or divalent aliphatic group comprising from 1 to 6 carbon atoms, and
R 5 represents a photocrosslinking group containing a benzophenone or substituted benzophenone moiety.

9. The moisture-curable composition of claim 8 , wherein the weight ratio of said at least one monomeric unit B to said at least one monomeric unit A is at least 0.8.

10. The moisture-curable composition of claim 8 , wherein L 1 is a covalent bond.

11. The moisture-curable composition of claim 8 , wherein Y 2 is selected from the group consisting of alkoxy groups having from 1 to 4 carbon atoms, alkanoyloxy groups having from 2 to 4 carbon atoms, a hydroxyl group, and Cl.

12. The moisture-curable composition of claim 8 , wherein said at least one monomer B has an average sum of a+b+c+d+e in the range of from 30 to 40.

13. The moisture-curable composition of claim 8 , wherein said at least one monomer B has an average sum of a+b+c+d+e in the range of from 4 to 8.

14. A composite article comprising a composition disposed on a substrate, wherein the composition comprises a cross-linked reaction product of components comprising the moisture-curable composition of claim 8 .

Assignees

• 3M Innovative Properties Co

Inventors

• Yang Yu
• Iyer Suresh S
• Guerra Miguel A
• Chen-Ho Kui
• Vitcak Daniel R

Classifications

• C08F214/08

  Vinylidene chloride · CPC title

• C08F210/14

  Monomers containing five or more carbon atoms · CPC title

• C08F214/182

  Monomers containing fluorine not covered by the groups C08F214/20 - C08F214/28 · CPC title

• C08F220/36

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C08F220/06

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title