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Norbornene and perfluoromethyl vinyl ether binary copolymerization catalyst and binary copolymerization method

A technology of perfluoromethyl vinyl ether and norbornene, which is applied in the field of high polymers, can solve the problems of small molecular weight of copolymers, low copolymer alternations, low copolymer yields, etc., and achieves low absorbance and reaction. Low temperature and good corrosion resistance

Active Publication Date: 2019-05-07
NINGBO UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A.E.Feiring and M.Toriumi et al. used norbornene, tetrafluoroethylene and acrylate free radical ternary copolymerization, etc., which generally have the disadvantages of long reaction time, low yield of copolymer, small molecular weight of copolymer, and low degree of alternation of copolymer.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 moles of antimony pentachloride and 0.001 moles of 8-hydroxyquinoline in 10 milliliters of benzene to obtain a mixed solution; Titanium isopropoxide is dropped into the mixed solution, and after the drop is completed, it is stirred at a constant temperature of 30° C. for 30 minutes to obtain an antimony-titanium complex catalyst.

[0024] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene and 0.01 mole of perfluoromethyl vinyl ether into an autoclave evacuated several times and filled with nitrogen, and add 20 ml of benzene to dissolve. According to the amount of antimony pentachloride in the catalyst, it is 0.01% of the two gross weights of bicyclo[2,2,1]hept-2-ene and perfluoromethyl vinyl ether to get the above-mentioned antimony-titanium complex catalyst, Inject the above mixture with a syringe. React at a constant temperature of 90°C and a pressure of 0.1MPa for 5 hours. The product is poured into an ...

Embodiment 2

[0027] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 mol of antimony pentachloride and 0.014 mol of α, α'-bipyridine in 10 ml of toluene to obtain a mixed solution; install an electric stirrer to stir, and mix 0.010 mol of One mole of titanium tetraisopropoxide is dropped into the mixed solution, and after the drop is completed, it is stirred at a constant temperature of 50° C. for 40 minutes to obtain an antimony-titanium complex catalyst.

[0028] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene and 0.01 mole of perfluoromethyl vinyl ether into an autoclave evacuated several times and filled with nitrogen, and add 20 ml of toluene to dissolve. According to the amount of antimony pentachloride in the catalyst, it is 0.06% of the two gross weights of bicyclo[2,2,1]hept-2-ene and perfluoromethyl vinyl ether to get the above-mentioned antimony-titanium complex catalyst, Inject the above mixture with a syringe. React at a constant temperature of 100°C and a pr...

Embodiment 3

[0030] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 moles of antimony pentachloride and 0.020 moles of phenanthroline in 10 milliliters of tetrahydrofuran to obtain a mixed solution; install an electric stirrer to stir, and mix 0.014 moles of tetraisocyanurate at 300 rpm Titanium propoxide was dropped into the mixed solution, and after the drop was completed, it was stirred at a constant temperature of 30° C. for 40 minutes to obtain an antimony-titanium complex catalyst.

[0031] Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene and 0.01 mole of perfluoromethyl vinyl ether into an autoclave evacuated several times and filled with nitrogen, and add 20 ml of tetrahydrofuran to dissolve. According to the amount of antimony pentachloride in the catalyst, it is 1.50% of the total weight of 1-methylbicyclo[2,2,1]hept-2-ene and perfluoromethyl vinyl ether to get the above antimony-titanium complex Compound catalyst, injected into the above mixture with a s...

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PUM

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Abstract

The invention relates to a norbornene-perfluoromethyl vinyl ether binary copolymer catalyst and a binary copolymerization method. The preparation method of the catalyst is characterized by comprising the following steps: in a container of dry inert gas atmosphere, dissolving antimony pentachloride and ligand in a first solvent; dropwise adding tetra-isopropoxy titanium at 200-300rpm, and then continuously stirring for 30-50 minutes at 30-50 DEG C to obtain an antimony-titanium complex catalyst; adding a norbornene monomer and a perfluoromethyl vinyl ether monomer in a molar ratio of 1:1 into an autoclave after repeated vacuumizing and nitrogen charge; adding a second solvent and dissolving; adding the antimony-titanium complex catalyst, and reacting for 1-6 hours at 30-120 DEG C and under the pressure of 0.1-8MPa; pouring the reaction product into an ethanol solution containing 4-5wt% of hydrochloric acid; washing the obtained precipitate with ethanol to neutrality; and performing vacuum drying to obtain a norbornene-perfluoromethyl vinyl ether binary copolymer.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a norbornene-perfluoromethyl vinyl ether binary copolymerization catalyst and a binary copolymerization method. Background technique [0002] Polynorbornene is a special polymer with excellent mechanical properties, heat resistance, solubility in organic solvents and transparency, and can be used for 157nm ultraviolet lithography. The main disadvantages of this material are brittleness, poor viscosity and low molecular weight. After fluorine-containing vinyl is inserted into the main chain of polynorbornene, the cohesiveness and solubility of the polymer can be improved, and the light absorption rate of the material itself can be reduced. This copolymer can be used as a photoresist material for 157nm printing technology, such as A.E. Feiring and M.Toriumi used norbornene, tetrafluoroethylene and acrylate copolymers as photolithographic materials, and their performance was greatly im...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F4/76C08F4/20C08F232/08C08F216/14
CPCC08F4/20C08F4/76C08F216/1408C08F232/08
Inventor 周国权王江波胡敏杰高浩其房江华杨建平王志强陈斌
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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