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Norbornenes, acrylonitrile and n-phenylmaleimide terpolymerization catalyst and terpolymerization method

A technology of maleimide ternary and norbornene, which is applied in the field of high polymers, can solve the problems of small molecular weight of copolymers, low degree of alternation of copolymers, and low yield of copolymers, and achieve low reaction temperature and easy Effect of washing separation and high copolymer yield

Active Publication Date: 2019-07-09
NINGBO UNIVERSITY OF TECHNOLOGY
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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

[0024] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 mol of zirconium naphthenate and 0.001 mol of 8-hydroxyquinoline in 10 ml of benzene, and drop 0.014 mol of triisobutylaluminum into the above solution at 200 rpm , after the dropwise stirring at the same temperature at 20° C. for 40 minutes, the zirconium-aluminum complex catalyst was obtained.

[0025] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of acrylonitrile and 0.01 mole of N-phenylmaleimide to several times vacuumed and nitrogen-filled autoclave, add 20ml of benzene dissolve. According to the amount of zirconium naphthenate in the catalyst, it is 0.10% of the total weight of bicyclo[2,2,1]hept-2-ene, acrylonitrile and N-phenylmaleimide to get the above zirconium-aluminum complex Compound catalyst, injected into the above mixture with a syringe. React at a constant temperature of 80°C and a pressure of 2MPa for 6 hours. The product is poured into an ethanol solution containing 5wt...

Embodiment 2

[0028] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 mol of zirconium naphthenate and 0.006 mol of α, α'-bipyridine in 10 ml of toluene, and drop 0.004 mol of triethylaluminum into the above solution at 150 rpm After dripping, stir at the same temperature at 40°C for 50 minutes at the same stirring rate to obtain a zirconium-aluminum complex catalyst.

[0029] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of acrylonitrile and 0.01 mole of N-phenylmaleimide to several vacuum-pumped, nitrogen-filled autoclaves, add 20ml of toluene dissolve. According to the amount of zirconium naphthenate in the catalyst, it is 0.08% of the total weight of bicyclo[2,2,1]hept-2-ene, acrylonitrile and N-phenylmaleimide to get the above-mentioned zirconium-aluminum complex Compound catalyst, injected into the above mixture with a syringe. React at a constant temperature of 90°C and a pressure of 1 MPa for 5 hours. The product is poured into an ethanol solution co...

Embodiment 3

[0031] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of zirconium naphthenate and 0.008 moles of phenanthroline were dissolved in 10 milliliters of tetrahydrofuran, and 0.008 moles of triisobutylaluminum was dropped into the above solution at 190 rpm, After the drop is completed, stir at a constant temperature of 40° C. for 40 minutes at the same stirring rate to obtain a zirconium-aluminum complex catalyst.

[0032] Add 0.01 mol of 1-methylbicyclo[2,2,1]hept-2-ene, 0.01 mol of acrylonitrile and 0.01 mol of N-phenylmaleimide into a vacuum-evacuated, nitrogen-filled autoclave , add 20ml tetrahydrofuran to dissolve. According to the amount of zirconium naphthenate in the catalyst, it is 0.07% of the total weight of 1-methylbicyclo[2,2,1]hept-2-ene, acrylonitrile and N-phenylmaleimide. Zirconium-aluminum complex catalyst is injected into the above mixture with a syringe. The reaction was carried out at a constant temperature of 80° C. and a pressure of 4 ...

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Abstract

The invention relates to a norbornene, acrylonitrile and N-phenyl maleimide ternary polymerization catalyst and a ternary polymerization method. The ternary polymerization catalyst is characterized in that the preparation method of the catalyst comprises the steps that in a three-necked flask in a dry inert gas atmosphere, zirconium naphthenate and a ligand are dissolved in a first solvent, and a mixed solution is obtained; aluminum alkyl is dropwise added into the mixed solution under stirring, after dropping addition is completed, reacting is conducted at the temperature of 20-50 DEG C for 20-50 min, and a zirconium-aluminum complex catalyst is obtained; a norbornene monomer, acrylonitrile and an N-phenyl maleimide monomer are obtained to be added into an autoclave which is vacuumized repeatedly and filled with nitrogen, and a second solvent is added for dissolving; then the zirconium-aluminum complex catalyst is added for reacting at a certain temperature and pressure for 1-6 hours; a product obtained from the reaction is poured into an alcohol solution, an obtained sediment is washed with alcohol to be neutral, and the norbornene, acrylonitrile and N-phenyl maleimide ternary copolymer is obtained after vacuum drying.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a ternary copolymerization catalyst of norbornene, acrylonitrile and N-phenylmaleimide 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 oxygen-containing N-phenylmaleimide into the main chain of polynorbornene, it can improve the adhesion and solubility of the polymer, and reduce the light absorption rate of the material itself. This copolymer can be used as a photoresist material Applied to 157nm photocopying technology, such as A.E. Feiring and M.Toriumi, etc., use norbornene, tetrafluoroethylene and acrylate copolymer as photolithographic materials, and the per...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F220/48C08F222/40C08F4/642
CPCC08F4/64C08F4/642C08F220/48C08F222/40C08F232/08
Inventor 李正辉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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