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Polymer containing phospho-fluoro monomer

A technology of polymers and compounds, applied in phosphorus organic compounds, compounds of group 5/15 elements of the periodic table, devices for coating liquids on surfaces, etc., can solve problems such as impractical, inconvenient to use, and unsatisfied

Inactive Publication Date: 2003-07-02
EI DU PONT DE NEMOURS & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it is usually inconvenient and impractical to directly utilize this functionalized monomer in fluoroplastics.
[0005] Therefore, there is a hitherto unmet need in the field of fluoropolymers for functionalized monomers that are easy to use

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0054] CF 2 =CFO-CF 2 CF(CF 3 )O-CF 2 CF 2 -CH 2 -OP(O)-Cl 2

[0055] as well as

[0056] CF 2 =CF-CF 2 CF 2 -CH 2 CH 2 -OP(O)-Cl 2

[0057] In a pre-dried flask was added: 9,9-dihydro-9-hydroxy-perfluoro(3,6-dioxa-5-methyl-1-nonene) (EVE-OH, US Patent 5,059,720) ( 257g, 0.652mol), phosphorus oxychloride (500g, 3.257mol) and anhydrous calcium chloride (3.6g, 0.0324mol). The reaction mixture was heated at 110 °C for 6-8 h or until the EVE-OH starting material was consumed. Excess phosphorus oxychloride is recovered by atmospheric distillation (boiling point 105°C-108°C). Subsequently, the remaining liquid was distilled under reduced pressure, as a result of which 9-phosphoryl chloride-9,9-dihydro-perfluoro(3,6-dioxa-5-methyl-1-nonene) (EVE-P - chloride, see the above formula) product, which is a transparent, colorless liquid with a boiling point of 85°C to 90°C at 5mmHg (or 67°C to 72°C at 2mmHg). Yield: 200 g (60%).

example 2

[0060] CF 2 =CFO-CF 2 CF(CF 3 )O-CF 2 CF 2 -CH 2 -OP(O)-(OH) 2

[0061] as well as

[0062] CF 2 =CF-CF 2 CF 2 -CH 2 CH 2 -OP(O)-(OH) 2

[0063] Into a round bottom flask was charged 700 g (1.37 mol) of EVE-P-chloride (Example 1) followed by slow addition of water (49.4 g, 2.75 mol). After all the water was added, the reaction mixture was stirred vigorously at room temperature overnight. Subsequently, the product was placed under high vacuum at 60°C to drive off any remaining moisture, resulting in 9-phosphoryl-9,9-dihydro-perfluoro(3,6-dioxa-5-methyl-1 -nonene) (EVE-P, see formula above) as a clear, viscous liquid (640 g, 98.6% yield).

[0064] Using CF in the above program 2 =CF-CF 2 CF 2 -CH 2 CH 2 -OP(O)-Cl 2 When used as a substitute for EVE-P-chloride, the obtained phosphorus-containing compound (I) is then phosphoryl compound CF 2 =CF-CF 2 CF 2 -CH 2 CH 2 -OP(O)-(OH) 2 .

example 3

[0066] Copolymerization of EVE-P and TFE

[0067] In a 400mL stainless steel shaker test tube (tuble), add: deionized water (280mL), ammonium perfluorononanoate surfactant (C-9, 2.0g), disodium phosphate (2.0g), EVE-P (4.0g , Example 2) and ammonium persulfate (APS, 0.6 g). The tube was sealed, cold-evacuated, and TFE (45 g, 0.45 mol) was transferred to the tube. The tube was sealed and heated at 70 °C for 4 h. After cooling, the obtained polymer latex was coagulated with dilute nitric acid. The resulting polymer was collected by filtration, and then washed well with warm water. After drying in a vacuum oven (150 mmHg) at 100°C overnight, a white polymer powder (44.0 g) was obtained. The polymer exhibited, as determined by DSC: Tm, 344.6°C (first heat curve) and Tm, 329.2°C (second heat curve). The volume molar composition of the polymer, according to the molten state of the polymer 19 As determined by F nuclear magnetic resonance, it was TFE / EVE-P=99.1 / 0.9.

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Abstract

Fluorinated vinyl ethers having phosphorus-containing groups are useful as monomers in making fluoropolymers having functional sites.

Description

[0001] This application is a divisional application of a Chinese patent application with a filing date of September 11, 1997 and an application number of 97197869.7 (PCT / US97 / 16070). related application [0002] This application claims priority to Provisional Application Serial No. 60 / 026,023 filed 1996-09-13. technical field [0003] The present invention belongs to the field of fluoropolymers. Background technique [0004] Currently, there is an increasing demand for functionalized fluoromonomers and polymers for adhesion, curing coatings, interfacial compatibilizers for compounding / blending, and more. Used in perfluoroelastomers such as CF 2 = CFOCF 2 CF(CF 3 )OCF 2 CF 2 Known cure site monomers, such as -CN (US Patent 4,281,091), require high temperature and the presence of a catalyst to complete cure. Therefore, it is usually inconvenient and impractical to directly utilize this functionalized monomer in fluoroplastics. [0005] Thus, there remains a hitherto un...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/09C07F9/113C07F9/14C07F9/143C07F9/146C08F30/02C08F214/18C08F214/26C08F230/02C08J7/043C09D4/00
CPCY10T428/31692Y10T428/31667C07F9/113C07F9/14Y10T428/31663C07F9/091C08F214/184C08J2443/00Y10T428/31544C08F30/02Y10T428/31855C08J7/047Y10T428/31678C09D4/00Y10T428/3154C07F9/1403C08F214/262C08J7/0427C08J7/043C08F214/18
Inventor P·D·布罗特尔斯M·-H·温M·J·米查尔斯塞克T·塔卡哈施
Owner EI DU PONT DE NEMOURS & CO