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Norbornenes, vinyl ethyl ether and perfluoromethyl vinyl ether terpolymerization catalyst and terpolymerization method

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

Active Publication Date: 2019-02-15
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

[0024] In a three-necked flask with a dry inert gas atmosphere, 0.001 mole of bis(cyclopentadiene) vanadium and 0.001 mole of 8-hydroxyquinoline were dissolved in 10 milliliters of benzene to obtain a mixed solution; 0.006 mole of diethylzinc was dropped into the mixed solution, and then stirred at a constant temperature of 30° C. for 60 minutes to obtain a vanadium-zinc complex catalyst.

[0025] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of vinyl ethyl ether and 0.01 mole of perfluoromethyl vinyl ether into an autoclave that has been evacuated several times and filled with nitrogen, and add 20ml of benzene to dissolve . According to the amount of bis(cyclopentadienyl) vanadium in the catalyst, it is 0.07% of the total weight of bicyclo[2,2,1]hept-2-ene, vinyl ethyl ether and perfluoromethyl vinyl ether to get the above-mentioned The vanadium-zinc complex catalyst is injected into the above mixture with a syringe. The reaction was carried out at a constant tempera...

Embodiment 2

[0028] In a three-necked flask with a dry inert gas atmosphere, 0.001 mole of bis(cyclopentadiene) vanadium and 0.006 mole of α, α'-bipyridine were dissolved in 10 milliliters of toluene to obtain a mixed solution; 0.001 mole of diethyl zinc was dropped into the mixed solution at 350 rpm, and then stirred at a constant temperature of 40° C. for 40 minutes to obtain a vanadium-zinc complex catalyst.

[0029] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of vinyl ethyl ether and 0.01 mole of perfluoromethyl vinyl ether into an autoclave that has been evacuated several times and filled with nitrogen, and dissolved in 20ml of toluene . According to the amount of bis(cyclopentadienyl) vanadium in the catalyst, it is 1.00% of the total weight of bicyclo[2,2,1]hept-2-ene, vinyl ethyl ether and perfluoromethyl vinyl ether to get the above-mentioned The vanadium-zinc complex catalyst is injected into the above mixture with a syringe. React at a constant temperature of 90°C and...

Embodiment 3

[0031] In a three-necked flask with a dry inert gas atmosphere, 0.001 mole of bis(cyclopentadienyl) vanadium and 0.012 mole of phenanthrene were dissolved in 10 milliliters of tetrahydrofuran to obtain a mixed solution; 0.010 mole of diethylzinc was dropped into the mixed solution, and after the dropping was completed, it was stirred at a constant temperature of 60° C. for 60 minutes to obtain a vanadium-zinc complex catalyst.

[0032]Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene, 0.01 mole of vinyl ethyl ether and 0.01 mole of perfluoromethyl vinyl ether into an autoclave that has been evacuated several times and filled with nitrogen, Add 20ml tetrahydrofuran to dissolve. According to the amount of bis(cyclopentadienyl) vanadium in the catalyst, it is the total weight of 1-methylbicyclo[2,2,1]hept-2-ene, vinyl ethyl ether and perfluoromethyl vinyl ether 0.08% Take the above-mentioned vanadium-zinc complex catalyst and inject it into the above-mentioned mixture with a syr...

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PUM

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Abstract

The invention relates to a norbornene, vinyl ethyl ether and perfluoromethyl vinyl ether ternary copolymerized catalyst and a ternary copolymerizing method. The preparation method of the catalyst comprises the following steps: dissolving bis(cyclopentadiene) vanadium and ligand in a first solvent in a dried container at an inert gas atmosphere to obtain a mixed solution; dripping diethyl zinc into the mixed solution, and stirring for 30-60 minutes at 30-60 DEG C after dripping to obtain a vanadium-zinc complex catalyst; adding norbornene, vinyl ethyl ether and perfluoromethyl vinyl ether into an autoclave which is vacuumized for multiple times and inflated with nitrogen, adding a second solvent and dissolving; adding the vanadium-zinc complex catalyst, and reacting for 1-6 hours at certain temperature and pressure; and pouring the product obtain in reaction into a hydrochloric acid-containing alcohol solution, washing the precipitate to be neutral with alcohol, and drying in vacuum to obtain the norbornene, vinyl ethyl ether and perfluoromethyl vinyl ether ternary copolymerized catalyst.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a norbornene, vinyl ether and perfluoromethyl vinyl ether ternary copolymerization catalyst and a ternary 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 inserting fluorine-containing ethylene and oxyethylene into the main chain of polynorbornene, it can improve the cohesiveness and solubility of the polymer, and reduce the absorbance of the material itself. This copolymer can be used as a photoresist material for 157nm photocopying Technologies, such as A.E. Feiring and M.Toriumi, etc. use norbornene, tetrafluoroethylene and acrylate copolymers as photolithographic materials, and their...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F216/18C08F216/14C08F4/6592
CPCC08F4/65925C08F216/1408C08F216/18C08F232/08
Inventor 周国权胡敏杰高浩其房江华王江波杨建平王志强陈斌
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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