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Polyfluoroalkylphosphonic acid esters and processes for production of same

A technology of polyfluoroalkylphosphonate and its manufacturing method, which is applied in the field of polyfluoroalkylphosphonate and its preparation, and can solve the problems of durability influence, orientation reduction, and inability to obtain sufficient performance, etc.

Active Publication Date: 2014-09-03
UNIMATEC CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, for compounds with 6 or less carbon atoms in the perfluoroalkyl group, the orientation on the surface of the treated substrate is significantly reduced, and the melting point, glass transition temperature Tg, etc. are also significantly lower than those with 8 carbon atoms. Therefore, it will be greatly affected by environmental conditions such as temperature, humidity, stress, and contact with organic solvents.
Therefore, the required sufficient performance cannot be obtained, and it also has an influence on durability, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0078] The present invention will be described below with reference to examples.

reference example 1

[0080] In a 1200ml autoclave with a stirrer and a thermometer, charge

[0081] CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 I (99GC%)

[0082] 603g (0.99 moles) and 7g 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 adjust the internal pressure to 0.5 MPa. Once the internal pressure drops to 0.2MPa, ethylene is introduced again to make the internal pressure 0.5MPa, and so on. While maintaining the internal temperature at 80-115°C, 41 g (1.45 mol) of ethylene was introduced over about 3 hours. The content is recovered at an internal temperature below 50°C to obtain

[0083] CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 (CH 2 CH 2 )I (98GC%), namely

[0084] C 4 f 9 CH 2 (CF 2 ) 5 CH 2 CH 2 I

[0085] 637g (98.8% yield).

Embodiment 1

[0087] In a four-necked bottle with a capacity of 1 L, which has a thermometer and a receiver for removing low boilers, it is charged with the

[0088] CF 3 (CF 2 ) 3 (CH 2 CF 2 )(CF 2 CF 2 ) 2 (CH 2 CH 2 )I (98GC%)

[0089] 500g (0.78 mol) and triethyl phosphite P (OC 2 h 5 ) 3 181g (1.56 moles), stirred at 155°C. At this time, in order to remove ethyl iodide as a by-product from the reaction system, nitrogen gas was bubbled into the reaction liquid using a thin tube. A small amount of the reaction solution was collected and analyzed by gas chromatography. After confirming the residual amount of triethyl phosphite, triethyl phosphite was further added in 4 times, 91 g (0.78 mol) per time, and stirred for a total of 18 hours.

[0090] After the reaction, the reaction mixture was subjected to simple distillation under reduced pressure under the conditions of internal pressure 0.2kPa, internal temperature 160-170°C, and tower top temperature 150-155°C, and the dis...

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PUM

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Abstract

By the general formula CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OR)2 (wherein, R is an alkyl group with 1 to 4 carbon atoms, n is 1 to 6, and a is 1 ~4, b is 1~3, c is the polyfluoroalkyl phosphonate represented by 1~3), it is manufactured by the following method, namely, make by general formula CnF2n+1(CH2CF2)a(CF2CF2)b( CH2CH2)cI represents the method of polyfluoroalkyl iodide represented by the general formula P (OR) phosphite trialkyl ester reaction, or represented by the general formula CnF2n+1(CH2CF2)a(CF2CF2)bCH=CH2 A method of reacting a polyfluoro-1-alkene with a dialkyl phosphite represented by the general formula (RO)2P(O)H.

Description

technical field [0001] The present invention relates to polyfluoroalkyl phosphonates and processes for their preparation. More specifically, the present invention relates to a polyfluoroalkyl phosphonate that can be effectively used as a synthetic raw material for a mold release agent, an additive for lubricating oil, and the like, and a method for producing the same. Background technique [0002] Polyfluoroalkyl phosphonates are widely used as synthetic raw materials for mold release agents. The mold release performance when used as a mold release agent is most likely to be manifested in compounds with perfluoroalkyl carbon atoms of 8 to 12, especially as C 8 of telomer compounds [0003] CF 3 (CF 2 ) 7 CH 2 CH 2 P(O)(OC 2 h 5 ) 2 [0004] It is preferably used for such an application (see Patent Documents 1 to 4). [0005] However, it has been reported that telomer compounds having a perfluoroalkyl group with 8 to 12 carbon atoms are biodegraded in the environm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/40
CPCC07F9/4006C07B41/12C07F9/40
Inventor 村田清一郎佐藤胜之
Owner UNIMATEC CO LTD
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