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Functional acrylic esters monomers containing perfluorocyclobutane aryl-ether unit, preparation method and application

A technology of perfluorocyclobutyl aryl ether and acrylate, which is applied in the field of functional acrylate monomers and can solve the problems of limited application scope, limited design and synthesis, few types of polymers, etc.

Active Publication Date: 2009-02-11
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the relatively high polymerization temperature (>150 °C) and unique polymerization mechanism, the design and synthesis of functional groups linked to trifluorovinyl groups in monomers are limited, and the types of PFCB-based polymers reported in the literature are limited. few
At the same time, it is difficult to introduce common commercial monomers into trifluorovinyl aryl ether monomers to obtain composite fluoropolymers, and the application range of PFCB-based polymers is limited.

Method used

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  • Functional acrylic esters monomers containing perfluorocyclobutane aryl-ether unit, preparation method and application
  • Functional acrylic esters monomers containing perfluorocyclobutane aryl-ether unit, preparation method and application
  • Functional acrylic esters monomers containing perfluorocyclobutane aryl-ether unit, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Synthesis of 4-methyl-(2-bromotetrafluoroethoxy)benzene 7

[0026]

[0027] Add p-cresol (108 g, 1 mol) and dimethyl sulfoxide (DMSO) (700 mL) into a 1000 mL three-necked flask equipped with a water separator and a reflux condenser, and stir to dissolve the phenol. After decompressing with an oil pump for 30 minutes, nitrogen was bubbled into the solution for 30 minutes to remove oxygen in the solution. Under nitrogen protection, potassium hydroxide (68 g, 1 mol, 82%) was added. After bubbling nitrogen through the solution for 30 min, freshly distilled toluene (200 mL) was added. Under the protection of nitrogen, the temperature was raised to reflux the system, and the water layer in the water separator was continuously separated. After about 24 hours of reflux, when there is no more water layer in the water separator, stop heating and cool at room temperature. After the system is cooled to room temperature, quickly remove the water separator and replace...

Embodiment 2

[0029] Example 2 Synthesis of trifluorovinyl (4-methylphenyl) ether 8

[0030]

[0031]Install a reflux condenser on the 1000mL three-necked bottle, and add zinc powder (40g, 0.72mol). After replacing the nitrogen with an oil pump, it is baked with a gas fire, and then filled with nitrogen. repeat three times. After cooling to room temperature, 600 mL of freshly distilled acetonitrile was added. Compound 7 (156 g, 0.55 mol) was added in the dropping funnel. The temperature of the oil bath was raised to 110°C to reflux the acetonitrile. Then compound 7 was slowly added dropwise, and the dropwise addition was completed within 4 h. During the dropwise addition, acetonitrile was refluxed vigorously. After the dropwise addition, react at 110°C for 10h. Stop heating, and let it cool down at room temperature. The generated salt precipitated in the lower part of the three-necked flask, and the supernatant was poured out; the remaining reactants were washed with water, extrac...

Embodiment 3

[0033] Synthesis of Example 3 Compound 9

[0034]

[0035] Add compound 8 (18.8g, 100mmol) and trifluorovinyl (4-methoxyphenyl) ether (20.4g, 100mmol) into a 250mL dry three-necked flask, replace the nitrogen three times and then bubble with nitrogen for 20min , Put into 180 ℃ oil bath and stir for 24h. After cooling at room temperature, flash column chromatography gave 18.82 g of a colorless transparent liquid with a yield of 48%.

[0036] 1 H NMR (300MHz, CDCl 3 ): δ 2.31(s, 3H), 3.79(s, 3H), 6.83(d, J=7.2Hz, 2H), 7.03-7.13(m, 6H). 19 F NMR (282MHz, CDCl 3 ): δ-131.83, -131.63, -131.30, -131.03, -130.39, -130.25, -129.81, -129.59, -129.46, -129.02, -128.78, -128.67, -127.51. 13 C NMR (75MHz, CDCl 3 ): δ 20.6, 55.6, 114.6, 117.3, 118.2, 119.9, 123.0, 130.1, 134.8, 135.1, 146.1, 150.4, 157.0.IR(KBr): 3006, 2956, 2840, 1611, 1507, 1466, 1319, 1249 1193, 1118, 1036, 962, 829cm -1 .MS(EI) m / z(% relative intensity): 65(26), 77(45), 91(60), 107(26), 123(50), 157(22), 204...

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PUM

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Abstract

The invention provides a function acrylic ester monomer containing perfluor cyclobutyl aryl ether unit, a preparation method and the application thereof. The preparation method comprises a three-step reactions: firstly, thermal cyclization reaction is carried out between trifluoro vinyl aryl ether and trifluoro vinyl (4-methoxyphenyl) ether to produce perfluor cyclobutyl aryl ether, and then methyl is removed to obtain phenol containing perfluor cyclobutyl aryl ether unit, finally, by esterification, acrylic ester monomer containing perfluor cyclobutyl aryl ether unit is obtained. The monomer can be used for preparing polyacrylate polymer containing perfluor cyclobutyl aryl ether unit.

Description

technical field [0001] The invention relates to a functional acrylate monomer containing a perfluorocyclobutyl (PFCB) aryl ether unit, a preparation method and an application. Background technique [0002] Perfluorocyclobutyl aryl ether aryl ether polymers are a new class of fluoropolymers developed by researchers at Dow Chemical Co. in 1993. This type of fluoropolymer is usually produced by [2π+2π] thermal cyclopolymerization of trifluorovinyl (trifluorovinyl, TFVE) aryl ether monomer at a temperature between 150°C and 250°C without any initiator or catalyst , and no small molecular compounds are released. As a new type of fluoropolymer, PFCB-based polymers not only have the traditional excellent properties of fluoropolymers, such as thermal / oxygen stability and chemical corrosion resistance, etc., but also have good solution processability. [0003] In recent years, the research on PFCB-based polymers has mainly focused on the synthesis of different homopolymers and rand...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/54C07C67/14C08F20/30
Inventor 黄晓宇张森李永军陆国林童亮
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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