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Fluoroolefin/vinyl alcohol copolymer and process for its production

Inactive Publication Date: 2012-11-22
ASAHI GLASS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0017]According to the process of the present invention, it is possible to produce a fluoroolefin / vinyl alcohol copolymer excellent in heat resistance with sufficiently high productivity, whereby a quality loss due to coloration is prevented.
[0018]Further, the fluoroolefin / vinyl alcohol copolymer of the present invention has a quality loss due to coloration prevented and has excellent heat resistance.

Problems solved by technology

However, in the method of hydrolyzing the fluoroolefin / vinyl acetate copolymer under a basic condition, although the reaction rate is high, the obtainable copolymer is likely to be colored yellow, whereby the product quality tends to be low.
Whereas, in the method of hydrolyzing the fluoroolefin / vinyl acetate copolymer under an acidic condition, the reaction rate is low, and the productivity is low.
Further, the obtained fluoroolefin / vinyl alcohol copolymer usually has a low thermal decomposition starting temperature and thus has a problem in thermal stability.

Method used

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  • Fluoroolefin/vinyl alcohol copolymer and process for its production
  • Fluoroolefin/vinyl alcohol copolymer and process for its production

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0080]Polymerization Step:

[0081]Into a stainless steel autoclave having an internal capacity of 200 mL and equipped with a stirrer (pressure resistance: 3 MPa), 79.0 g of t-butyl alcohol, 26.7 g of t-butyl vinyl ether (hereinafter referred to as “TBVE”) as the vinyl ether (b), 0.48 g of potassium carbonate and 0.46 g of an isooctane solution containing 70% of perbutyl perpivarate (hereinafter referred to as “PBPV”) were charged, and the oxygen in the system was removed by repeating pressure purging with N2 gas. Then, 26.7 g of tetrafluoroethylene (hereinafter referred to as “TFE”) as the fluoroolefin (a) was introduced into the autoclave, followed by heating to 55° C. The pressure at that time was 1.56 MPa. Then, polymerization was continued for 7 hours, and when the pressure decreased to 1.12 MPa, the autoclave was cooled with water, and non-reacted TFE was purged to terminate the polymerization. The obtained polymer solution was put into methanol to precipitate the formed copolyme...

example 2

[0086]The copolymer B1 obtained in Example 1 was used.

[0087]Deprotection Step:

[0088]2.0 g of the copolymer B1, 50 mL of 4N hydrochloric acid and 1 mL of 1,4-dioxane were put into a 100 mL flask, heated and stirred at 90° C. to carry out a deprotection reaction. This reaction system gradually became a uniform solution. The reaction was continued for a total of 12 hours, and then, the reaction solution was dropped into water to precipitate copolymer A2, which was washed with water and then vacuum-dried at 40° C. to isolate 1.49 g of the copolymer A2.

[0089]By the measurements of the 1H-NMR spectrum and the IR spectrum, it was confirmed that in the copolymer A2, at least 97% of protective groups (t-butyl groups) were eliminated.

example 3

[0090]The copolymer B1 obtained in Example 1 was used.

[0091]Deprotection Step:

[0092]2.0 g of the copolymer B1, 50 mL of trifluoroacetic acid and 1 mL of methylene chloride were put into a 100 mL flask and then stirred at room temperature. The reaction was continued for a total of 48 hours, and then, the precipitated copolymer was washed with water and then vacuum-dried at 40° C. to isolate 1.33 g of the copolymer A3.

[0093]By the measurements of the 1H-NMR spectrum and the IR spectrum, it was confirmed that in the copolymer A3, at least 97% of protective groups (t-butyl groups) were detached.

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Abstract

To provide a process for producing a fluoroolefin / vinyl alcohol copolymer with sufficiently high productivity and excellent heat resistance, whereby a quality loss by coloration is prevented, and a fluoroolefin / vinyl alcohol copolymer obtainable by such a process. A process for producing a fluoroolefin / vinyl alcohol copolymer, which comprises a polymerization step of copolymerizing a specific fluoroolefin and a vinyl ether having a hydrogen atom of a hydroxy group of a vinyl alcohol substituted with a protective group which can be deprotected, and a deprotection step of substituting the protective group in polymerized units based on the vinyl ether in the copolymer obtained in the polymerization step, with a hydrogen atom to form a hydroxyl group, and the fluoroolefin / vinyl alcohol copolymer obtainable by such a process.

Description

TECHNICAL FIELD[0001]The present invention relates to a fluoroolefin / vinyl alcohol copolymer and a process for its production.BACKGROUND ART[0002]A fluoroolefin / vinyl alcohol copolymer, i.e. a copolymer of a fluoroolefin and vinyl alcohol, is used as a raw material for coating resins, a material for gas / liquid separation membranes, a gas barrier material, a sealing material for solar cells, a material for various surface protective sheets, a hydrophilic porous material, etc. (Patent documents 1 and 2).[0003]As a method for producing a fluoroolefin / vinyl alcohol copolymer, a method has already been known wherein a fluoroolefin and vinyl acetate are copolymerized, followed by hydrolysis under an acidic or basic condition (Patent Documents 1 and 2, and Non-Patent Document 3). In such a method, a fluoroolefin and vinyl acetate are used as raw materials, and they are copolymerized to obtain a fluoroolefin / vinyl acetate copolymer, and in such a copolymer, an ester moiety in polymerized un...

Claims

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Application Information

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IPC IPC(8): C08F216/06C08F8/00
CPCC08F214/247C08F2810/50C08F214/267C08F216/1416C08F216/18C08F214/262C08F2800/10C08F216/06C08F8/12C08F214/26C08F216/165C08F216/14C08F214/24
Inventor KODAMA, SHUNICHI
Owner ASAHI GLASS CO LTD
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