Fluorinated diene compound and fluoropolymer, and methods for their production

• US 20050182217A1
• Filed: 03/15/2005
• Published: 08/18/2005
• Est. Priority Date: 10/31/2001
• Status: Abandoned Application

• Current Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Original Assignee: Asahi Glass Company, Limited (AGC, Inc.)
• Inventors: Kashiwagi, Kimiaki, Watanabe, Kunio, Ogawa, Gen, Oharu, Kazuya, Okazoe, Takashi, Murotani, Eisuke
• Application Number:
  US11/079,276
• Publication Number:
  US 20050182217A1
• Time in Patent Office: Days
• US Class Current: 526/252
• CPC Class Codes: C07C 43/17 containing halogen
• CPC Class Codes: C08F 16/32 Monomers containing two or more unsaturated aliphatic radicals
• CPC Class Codes: C08F 214/18 Monomers containing fluorine
• CPC Class Codes: C08L 29/10 Homopolymers or copolymers of unsaturated ethers C08L35/08 takes precedence
• CPC Class Codes: G02B 1/046 characterised by the core material
• CPC Class Codes: G02B 6/02033 Core or cladding made from organic material, e.g. polymeric material G02B1/04 takes precedence
• CPC Class Codes: G02B 6/02038 with core or cladding having graded refractive index

Abstract

A novel fluoropolymer which can be an optical resin material having a low refractive index and excellent heat resistance, and a novel fluorinated diene compound having two unsaturated bonds, capable of presenting such a fluoropolymer, are presented. Further, by virtue of the low refractive index and excellent heat resistance, the polymer presents a high performance optical transmitter and a plastic optical fiber.

A fluorinated diene compound represented by CF₂═CFCF(OR^f)CF₂OCF═CF₂ (wherein R^f is a perfluoroalkyl group such as a trifluoromethyl group), and a fluoropolymer thereof. Further, an optical transmitter made by using such a fluoropolymer, and a plastic optical fiber having a core comprising such a fluoropolymer and a fluorinated low molecular compound contained therein as a refractive index-increasing agent.

Claims

1. A fluorinated diene compound represented by the following formula (1):

CF₂═

CFCF(OR^f)CF₂OCF═

CF₂ 

 

(1)

wherein R^f is a perfluoroalkyl group.

2. The fluorinated diene compound according to claim 1, wherein R^f is a trifluoromethyl group.

3. A method for producing a fluorinated diene compound represented by the following formula (1), characterized in that a dehalogenation reaction is carried out at halogen atoms other than fluorine atoms in at least one compound selected from a compound represented by the following formula (2) and a compound represented by the following formula (3):

CF₂═

CFCF(OR^f)CF₂OCF═

CF₂ 

 

(1)
CF₂Z¹CFZ²CF(OR^f)CF₂OCF═

CF₂ 

 

(2)
CF₂Z¹CFZ²CF(OR^f)CF₂OCFZ³CF₂Z⁴ 

 

(3)

wherein R^f is a perfluoroalkyl group, and each of Z¹, Z², Z³ and Z⁴ which are independent of one another, is a halogen atom other than a fluorine atom.

4. A fluoropolymer comprising monomer units formed by cyclopolymerization of a fluorinated diene compound represented by the formula (1), or monomer units formed by cyclopolymerization of a fluorinated diene compound represented by the formula (1) and monomer units formed by polymerization of other monomer polymerizable with the fluorinated diene compound represented by the formula (1):

CF₂═

CFCF(OR^f)CF₂OCF═

CF₂ 

 

(1)

wherein R^f is a perfluoroalkyl group.

5. The fluoropolymer according to claim 4, wherein R^f is a trifluoromethyl group.

6. The fluoropolymer according to claim 4, wherein the monomer units formed by the cyclopolymerization of the fluorinated diene monomer represented by the formula (1), are monomer units represented by any one of the following formulae, wherein R^f is as defined above:

7. The fluoropolymer according to claim 4, wherein the monomer units of other polymerizable monomer are monomer units formed by polymerization of at least one member selected from a fluorinated diene which is cyclopolymerizable, other than the fluorinated diene compound represented by the formula (1), a monomer having a fluorinated aliphatic cyclic structure, a fluorinated non-cyclic vinyl ether monomer and a fluoroolefin.

8. The fluoropolymer according to claim 4, wherein the other monomer units are monomer units formed by polymerization of at least one member selected from tetrafluoroethylene, perfluoro(butenyl vinyl ether) and perfluoro(2,2-dimethyl-1,3-dioxole).

9. A fluoropolymer solution having the fluoropolymer as defined in claim 4 dissolved in at least one fluorocarbon solvent selected from perfluoro(2-butyltetrahydrofuran), perfluorooctane, perfluorohexane, perfluoro(tributylamine), perfluoro(tripropylamine), perfluorobenzene and dichloropentafluoropropane.

10. An optical transmitter made by using the fluoropolymer as defined in claim 4.

11. A plastic optical fiber having a core formed of a mixture comprising the fluoropolymer as defined in claim 4 and a fluorinated low molecular compound as a refractive index-increasing agent.

12. The plastic optical fiber according to claim 11, wherein the fluorinated low molecular compound is at least one compound selected from perfluoro(triphenyltriazine), perfluoro(1,3,5-triphenylbenzene) and a chlorotrifluoroethylene oligomer.

13. The plastic optical fiber according to claim 11, wherein the plastic optical fiber is a refractive index distribution type optical fiber.