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Polyfluoroalkadiene mixture and method of manufacture therefor

A technology of polyfluorinated alkadiene and manufacturing method, which is applied in the fields of dehydrohalogenation preparation, organic chemistry, etc., can solve the problems of large influence, reduced surface orientation of treated substrate, unable to obtain sufficient performance, etc., and achieves bioaccumulation. low sex effect

Active Publication Date: 2011-05-18
UNIMATEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] As a result, companies making such telomer compounds are exiting their manufacture, or moving toward 6 Substitution of the following perfluoroalkyl compounds, etc., but for compounds with a perfluoroalkyl group of 6 or less carbon atoms, the orientation on the surface of the treated substrate is significantly reduced, and the melting point, glass transition temperature, etc. are different from C 8 Compared with the compound, it is significantly lower, so it is greatly affected by the environmental conditions of use such as temperature, humidity, stress, and organic solvents, so that the required sufficient performance cannot be obtained, and it also has an impact on durability, etc.

Method used

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  • Polyfluoroalkadiene mixture and method of manufacture therefor

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Embodiment

[0108] Next, the present invention will be described by way of examples.

reference example 1

[0110] In an autoclave with a capacity of 1200ml equipped with a stirrer and a thermometer, put

[0111] CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 I (99GC%)

[0112] 603 g (0.99 mol) and 7 g (0.05 mol) of di-tert-butyl peroxide, and the autoclave was degassed with a vacuum pump. After heating the internal temperature to 80°C, ethylene was sequentially introduced to make the internal pressure 0.5 MPa. After the internal pressure was reduced to 0.2 MPa, ethylene was introduced again to be 0.5 MPa, and this operation was repeated. While maintaining the internal temperature at 80 to 115°C, 41 g (1.45 mol) of ethylene was introduced over about 3 hours. The contents are recovered under the condition that the internal temperature is 50°C or lower to obtain

[0113] CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 (CH 2 CH 2 )I (98GC%)

[0114] which is

[0115] C 4 F 9 CH 2 (CF 2 ) 5 CH 2 CH 2 I

[0116] 637g (98.8% yield).

Embodiment 1

[0118] The 3, 3, 4, 4, 5, 5, 6, 6, 3, 3, 4, 4, 5, 5, 6, 6, 7,7,9,9,10,10,11,11,12,12,12-Nadetafluoro-1-iodododecane C 4 F 9 CH 2 (CF 2 ) 5 CH 2 CH 2 I 5 g (7.8 mmol) was dissolved in 15 ml of a fluorinated organic solvent (Asahi Glass Co., Ltd. AK-225). After cooling with ice, 1,8 - Diazabicyclo[5.4.0]-7-undecene [DBU] 2.6 g (17.2 mmol). After the dropwise addition was completed, stirring was carried out at about 0° C. for about 1 hour, and then stirring was continued at room temperature for about 23 hours (total reaction time was 24 hours).

[0119] After the completion of the reaction, washing with 20 ml of water was performed twice, and then washing with saturated brine was performed once, and the resulting reaction product solution was dehydrated and dried with anhydrous magnesium sulfate. After the reaction solvent was distilled off under reduced pressure, the residue was purified by reduced pressure distillation to obtain 2.8 g (yield: 77%) of a fraction having a...

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Abstract

A polyfluoroalkadiene mixture represented by a general formula CF3(CF2)nCF=CH(CF2)m+1CH=CH2 [Ia] and a general formula CF3(CF2)n+1CH=CF(CF2)mCH=CH2 [Ib] (wherein n is an integer from 0 to 5 and m is an integer from 0 to 6) is obtained and manufactured as a mixed fraction of products [Ia] and [Ib] by causing an organic basic compound to react with a polyfluoroalkayl iodide represented by the general formula CF3(CF2)n+1CH2(CF2)m+1(CH2CH2)I [II]. This polyfluoroalkadiene mixture is a compound in which the number of CF2 groups linked to a perfluoroalkyl group is 5 or less, and is effectively used as a copolymeric monomer in the manufacture of resinoid- or elastomer-inclusive fluorine-based copolymers that are the active ingredient in finishing agents, such as a water repellants and mold release agents, etc.

Description

technical field [0001] The present invention relates to polyfluorinated alkadiene mixtures and methods for their manufacture. In further detail, it relates to a polyfluorinated alkadiene mixture and a method for producing the same, the polyfluorinated alkadiene mixture having a C 6 The following perfluoroalkyl compounds are used as comonomers when producing fluorinated copolymers as active ingredients of water and oil repellents. Background technique [0002] Acrylic derivatives of perfluoroalkyl alcohols such as CF 3 (CF 2 ) 7 CH 2 CH 2 OCOCH=CH 2 , which is widely used as a synthetic monomer of water and oil repellent for fibers. Moreover, the perfluoroalkyl alcohol which is a raw material of this acrylate is widely used as surfactant etc. (refer patent document 1). [0003] In this way, compounds having a perfluoroalkyl group as a structural unit are generally known, and by applying them to the surfaces of fibers, metals, glass, rubber, resins, etc., they have imp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C21/19C07C17/25C08F214/18C08F236/20
CPCC08F214/182C08F236/20C07C17/25C08F214/18C07C21/19
Inventor 佐藤胜之村田清一郎池田昭彦村井大介前田满
Owner UNIMATEC CO LTD
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