Fluorinated compound, fluorinated polymer and fluorinated copolymer

• US 8,748,549 B2
• Filed: 12/18/2012
• Issued: 06/10/2014
• Est. Priority Date: 11/02/2009
• Status: Active Grant

• Current Assignee: AGC, Inc.
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Hoshino, Taiki
• Primary Examiner(s): Buie-Hatcher, Nicole M
• Application Number:
  US13/718,194
• Publication Number:
  US 20130123447A1
• Time in Patent Office: 539 Days
• Field of Search: 526/242, 560/130, 560/145
• US Class Current: 526/242
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 69/90 with esterified hydroxyl and carboxyl groups
• CPC Class Codes: C08F 14/18 Monomers containing fluorine

Abstract

To provide a fluorinated compound having an R^F group with at most 6 carbon atoms, whereby a fluorinated polymer having a highly durable water/oil repellency can be produced, and an environmental load is little, and a fluorinated polymer and a fluorinated copolymer having a highly durable water/oil repellency and presenting little environmental load, obtainable by polymerizing such a fluorinated compound. A fluorinated compound represented by the following formula (I) and its polymer:
CH₂═C(M)COO(CH₂)_nPhCOO(CH₂)_mC_rF_2r+1  (I)
(in the formula (I), M is a hydrogen atom, a methyl group or a halogen atom, n is an integer of from 0 to 2, Ph is a phenylene group, m is an integer of from 1 to 4, and r is an integer of from 1 to 6).

Claims

1. A fluorinated polymer comprising, in polymerized form, a fluorinated compound of formula (I):

CH₂═

C(M)COO(CH₂)_nPhCOO(CH₂)_mC_rF_2r+1 

 

(I)

wherein;

M is a hydrogen atom, a methyl group or a halogen atom;

n is an integer of 0 to 2;

Ph is a phenylene group;

m is an integer of 1 to 4; and

r is an integer of 1 to 6.

2. The fluorinated polymer of claim 1, having a mass average molecular weight of 2,000 to 1,000,000.

3. The fluorinated polymer of claim 1, having a mass average molecular weight of 5,000 to 500,000.

4. The fluorinated polymer of claim 1, consisting of, in polymerized form, the fluorinated compound of formula (I).

5. The fluorinated polymer of claim 1, wherein Ph is a 1,4-phenylene group.

6. The fluorinated polymer of claim 1, wherein r is an integer of 2 to 6.

7. The fluorinated polymer of claim 1, wherein r is an integer of 4 to 6.

8. The fluorinated polymer of claim 1, wherein the fluorinated compound of the formula (I) is a compound represented by any one of the following formulae (I-1) to (I-7):

9. The fluorinated polymer of claim 1, wherein r is an integer of 4 to 6, and C_rF_2r+1 is linear.

10. The fluorinated polymer of claim 1, wherein M is a hydrogen atom.

11. The fluorinated polymer of claim 1, wherein M is a methyl group.

12. The fluorinated polymer of claim 1, wherein n is 0 or 1.

13. The fluorinated polymer of claim 1, wherein m is 1, 2 or 3.

14. The fluorinated polymer of claim 1, which is a copolymer comprising, in polymerized form,to 99 mass % of the fluorinated compound of formula (I), and

1 to 90 mass % of another monomer X.

15. The fluorinated polymer of claim 14, wherein the other monomer X is selected from the group consisting of (i) a halogenated olefin, and (ii) a monomer having a cross-linkable functional group and having no polyfluoroalkyl group.

16. The fluorinated polymer of claim 14, wherein the other monomer X is a halogenated olefin selected from the group consisting of vinyl chloride, vinylidene chloride, tetrafluoroethylene, and vinylidene fluoride.

17. The fluorinated polymer of claim 14, wherein the other monomer X is a monomer having a cross-linkable functional group and having no polyfluoroalkyl group, wherein the cross-linkable functional group is selected from the group consisting of an isocyanate group, a blocked isocyanate group, an alkoxysilyl group, an amino group, an alkoxymethylamide group, a silanol group, an ammonium group, an amide group, an epoxy group, a hydroxy group, an oxazoline group, a carboxy group, an alkenyl group and a sulfonic acid group.

18. The fluorinated polymer of claim 14, wherein the other monomer X is selected from the group consisting of a (meth)acrylate, an acrylamide, a vinyl ether and a vinyl ester.

19. The fluorinated polymer of claim 1, which is a copolymer comprising, in polymerized form,to 95 mass % of the fluorinated compound of formula (I), and

5 to 80 mass % of another monomer X.

20. The fluorinated polymer of claim 1, which is a copolymer comprising, in polymerized form,to 90 mass % of the fluorinated compound of formula (I), andto 40 mass % of another monomer X.