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Catalyst for terpolymerization of norbornene, acrylate and vinylene carbonate, and method for ternary copolymerization

A vinylene carbonate ternary and vinylene carbonate technology, applied in the field of high polymers, can solve the problems of low copolymer alternation, low copolymer molecular weight, low copolymer yield, etc. Low reaction temperature and good corrosion resistance

Active Publication Date: 2019-05-07
宁波市大学科技园发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These synthetic methods currently used have disadvantages such as long reaction time, low yield of copolymers, small molecular weight of copolymers, and low degree of alternation of copolymers.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 moles of bis(cyclopentadiene)magnesium and 0.004 moles of 8-hydroxyquinoline in 10 ml of benzene, and drop 0.012 moles of triisobutylaluminum at 250rpm into the above solution, and then stirred at the same temperature at 40° C. for 40 minutes at the same stirring rate to obtain a magnesium-aluminum complex catalyst.

[0026] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of methyl acrylate and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20ml of benzene to dissolve. According to the amount of bis(cyclopentadiene)magnesium in the catalyst, it is 0.01% of the total weight of bicyclo[2,2,1]hept-2-ene, methyl acrylate and vinylene carbonate to get the above-mentioned magnesium-aluminum Complex catalyst, injected into the above mixture with a syringe. React at a constant temperature of 80° C. and a pressure of 4 MPa for 6 hours. The p...

Embodiment 2

[0029] In a three-necked flask with a dry inert gas atmosphere, 0.001 mol of bis(cyclopentadiene) magnesium and 0.006 mol of α, α'-bipyridine were dissolved in 10 ml of toluene, and at 200 rpm, 0.015 mol of triisobutyl Aluminum was dropped into the above solution, and after the drop was completed, the magnesium-aluminum complex catalyst was obtained by stirring at the same temperature at 50° C. for 60 minutes at the same stirring rate.

[0030] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of ethyl acrylate and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20ml of toluene to dissolve. According to the amount of bis(cyclopentadiene)magnesium in the catalyst, it is 0.05% of the total weight of bicyclo[2,2,1]hept-2-ene, ethyl acrylate and vinylene carbonate to get the above-mentioned magnesium-aluminum Complex catalyst, injected into the above mixture with a syringe. The reaction was carried out at a constant t...

Embodiment 3

[0032] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of bis(cyclopentadiene) magnesium and 0.010 moles of phenanthroline were dissolved in 10 milliliters of tetrahydrofuran, and at 500 rpm, 0.012 moles of triethylaluminum was dropped into the above In the solution, after dropping, stir at the same temperature at 60° C. for 30 minutes at the same stirring rate to obtain the magnesium-aluminum complex catalyst.

[0033]Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene, 0.01 mole of butyl acrylate and 0.01 mole of vinylene carbonate to several vacuum-evacuated and nitrogen-filled autoclaves, add 20ml of tetrahydrofuran dissolve. According to the amount of bis(cyclopentadiene)magnesium in the catalyst, it is 0.10% of the total weight of 1-methylbicyclo[2,2,1]hept-2-ene, butyl acrylate and vinylene carbonate The above-mentioned magnesium-aluminum complex catalyst is injected into the above-mentioned mixture with a syringe. React at a constant temperature of...

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Abstract

The invention relates to a norbornene, acrylate and vinylene carbonate ternary polymerization catalyst. The norbornene, acrylate and vinylene carbonate ternary polymerization catalyst is characterized in that a preparation method of the catalyst comprises the following steps of dissolving di(cyclopentadienyl)magnesium and a ligand into a first solvent in a dry inert gas container, so as to obtain a mixing solution; stirring, dripping aluminum alkyl into the mixing solution, and continuing to stir for 30 to 60min, so as to obtain a magnesium-aluminum complex catalyst; adding a norbornene monomer, an acrylate monomer and a vinylene carbonate monomer into a nitrogen high-pressure kettle with multiple times of vacuum suction according to a molar ratio of 1:1:1, and adding a second solvent to dissolve; adding a magnesium-aluminum complex catalyst, and reacting for 1 to 6h at certain temperature and pressure; pouring the reacted product into an ethyl alcohol solution with 4 to 5wt% of hydrochloric acid, washing the obtained precipitate by the ethyl alcohol to be at a neutral state, and drying under the vacuum atmosphere, so as to obtain the norbornene, acrylate and vinylene carbonate terpolymer.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a norbornene, acrylate and vinylene carbonate terpolymerization catalyst and a terpolymerization 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 193nm ultraviolet lithography. The main disadvantages of this material are brittleness, poor viscosity and low molecular weight. After the oxygen-containing olefin 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 in 193nm photolithography. Moreover, the development of the microelectronics industry requires components with smaller sizes. For the exposure technology suitable for line widths of 1.3 μm and below...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F218/00C08F220/14C08F220/12C08F4/52C08F4/44
CPCC08F4/44C08F4/52C08F218/00C08F218/24C08F220/12C08F220/14C08F232/08
Inventor 胡敏杰房江华王江波高浩其杨建平王志强陈斌
Owner 宁波市大学科技园发展有限公司