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Linear (per)fluoropolyethers with -CF(CF3)cof end groups and derivatives thereof

A -COF, linear technology, applied in the field of fluoropolyether, can solve problems such as poor yield and poor yield

Inactive Publication Date: 2014-08-06
SOLVAY SOLEXIS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] It was also pointed out that functionalized (per)fluoropolyethers (wherein the functional end groups pass through -CF(CF 3 )-moiety attached to the (per)fluoropolyether chain) can be prepared by adding hexafluoropropylene oxide (HFPO) to a (per)fluoropolyether containing -COF end groups in the presence of a suitable initiator ; however, due to the fact that HFPO undergoes oligomerization, a mixture of mono- or polyaddition products (i.e. products containing one or more HFPO or units at each end of the polymer chain) is produced, and these mixtures are difficult to separate, resulting in rate is bad
For example, US2004116742 (3M Innovation Co., Ltd. (3M INNOVATIVE PROPERTIES CO)) on June 17, 2004 disclosed a method for preparing linear fluorinated compounds by reacting HFPO with a precursor having a -COF end group, including With a -CF (CF 3 ) COF-terminated (per)fluoropolyether compounds; however, this method is in the presence of a fluoride salt as catalyst and a polar solvent and uses an excess of at least 10% of the In addition to the product of one HFPO unit, this method also provided poor yields containing a mixture of products containing many more HFPO units and significant amounts of unreacted precursors

Method used

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  • Linear (per)fluoropolyethers with -CF(CF3)cof end groups and derivatives thereof
  • Linear (per)fluoropolyethers with -CF(CF3)cof end groups and derivatives thereof
  • Linear (per)fluoropolyethers with -CF(CF3)cof end groups and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

example 2

[0182] Example 2-Synthesis of FC(O)CF(CF 3 )OCF 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CF 2 OCF(CF 3 )COF(MW1080)

[0183] This compound was synthesized according to method 2, using 2.0g CsF (MW=152, 13mmol), 70g diglyme, 110g H PFPE (Grade A), 50g with formula FC(O)CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 Diacyl fluoride of COF (MW=750; Mw / Mn1.1m / n=1.8, 67 mmol) and 35 g HFPO (MW=166, 211 mmol).

[0184] After removing the low-boiling fluorinated by-products and solvent by distillation at room pressure, the distillation residue was subjected to thin-layer distillation to provide 67.8 g of a mixture containing the following ( 19 F-NMR analysis):

[0185] -96% (60.3 mmol) of the title compound;

[0186] -3% one contains -CF (CF 3 )CF 2 OCF(CF 3 )COF end group compound and

[0187] -1% of a compound with the following formula: FC(O)CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CF 2 OCF(CF 3 ) COF.

[0188] The thin-layer distillation residue (approximately 4.7 g) includes:

[0189] -83% of FC(O)CF(C...

example 3

[0194] Example 3-Synthesis of CH 3 CH 2 OC(O)CF(CF 3 )OCF 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CF 2 O-CF(CF 3 )COOCH 2 CH 3 (MW2060)

[0195] 1.78g CsF (MW=152, 11.7mmol), 70g diglyme, 140g bistrifluoromethylbenzene and 48.4g of formula FC(O)CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 The diacyl fluoride of COF (MW=1650, Mw / Mn=1.2, m / n=1.5, 29.3mmol) was added to a 0.51 AISI316 reactor equipped with a stirrer, sampling device, thermocouple and pressure gauge under nitrogen atmosphere in. The resulting mixture was heated to 40°C and left under stirring for two hours, and then cooled to -25°C. The nitrogen was removed by connecting the reactor to a vacuum pump.

[0196] 14 g of HFPO (MW=166, 84.3 mmol) was added over 2 hours and the resulting mixture was left under stirring for 4 hours. After this time, 30g ethanol and 6g triethylamine (59.4mmol) were added to the mixture, keeping the temperature at -25°C; after the addition was completed, the temperature was raised to 20°C and the r...

example 4

[0211] Example 4-Synthesis of CH 3 CH 2 OC(O)CF(CF 3 )OCF 2 CF 2 O(CF 2 CF 2 O) m (CF 2 O) n CF 2 CF 2 OCF(CF 3 )C(O)OCH 2 CH 3 (MW=1112)

[0212] The title compound was prepared from the compound of Example 2 following the procedure described in Example 3 above.

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Abstract

The present invention relates to mono- or bi-functional (per)fluoropolyethers comprising a linear (per)fluoropolyether chain having two ends, wherein one or two ends contain —CF(CF3)COF groups, to a process for preparing them and to their use as precursors in the preparation of further functionalised (per)fluoropolyethers. The invention also relates to these further functionalised (per)fluoropolyethers.

Description

[0001] This application claims priority to European Patent Application No. 111833716.7 filed on October 3, 2011, the entire content of which is incorporated herein by reference for all purposes. Technical field [0002] The present invention relates to fluoropolyethers, especially linear (per)fluoropolyethers with functionalized end groups, and a method for preparing them. Background technique [0003] Contains -CF randomly distributed along the polymer chain 2 O-, -CF 2 CF 2 O-, -CF 2 CF 2 CF 2 O- and -CF 2 CF 2 CF 2 CF 2 O-unit linear (per) fluoropolyether is characterized by more than branched -CF (CF 3 )-Or-CF 2 CF(CF 3 )-Unit, (per)fluoropolyether with perfluoroalkane side groups has a lower glass transition temperature (Tg). In particular, contains (or basically consists of) -CF 2 O- and -CF 2 CF 2 O-unit linear (per)fluoropolyether is particularly flexible, and due to -CF 2 The presence of O-units has been given a Tg usually lower than -90°C. [0004] Contains -CF 2 O- and -C...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/00
CPCC07C69/708C07C59/135C08G65/00C08G65/007C08G65/22C08G65/2639
Inventor S.A.方塔纳C.A.P.托内里P.加维佐蒂
Owner SOLVAY SOLEXIS