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Norbornene, tetrafluoroethylene and n-phenylmaleimide ternary copolymerization catalyst and ternary copolymerization 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 Washing separation, high catalytic efficiency

Active Publication Date: 2019-03-29
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

[0022] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of bis(tricyclohexylphosphine)palladium dichloride and 0.001 moles of 8-hydroxyquinoline were dissolved in 10 milliliters of benzene to obtain a mixed solution; At 200 rpm, 0.001 mole of tetraisopropoxytitanium was dropped into the mixed solution, and then stirred at 30° C. for 30 minutes at a constant temperature to obtain a palladium-titanium complex catalyst.

[0023] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of tetrafluoroethylene and 0.01 mole of N-phenylmaleimide to several vacuum-pumped, nitrogen-filled autoclaves, add 20ml Benzene dissolves. According to the amount of bis(tricyclohexylphosphine)palladium dichloride in the catalyst, it is 0.01% of the total weight of norbornene, tetrafluoroethylene and N-phenylmaleimide to get the above-mentioned palladium-titanium complex Catalyst, injected into the above mixture with a syringe. React at a constant temperature of 90°C and a pressur...

Embodiment 2

[0026] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of bis(tricyclohexylphosphine)palladium dichloride and 0.006 moles of α,α'-bipyridine were dissolved in 10 milliliters of toluene to obtain a mixed solution; After stirring, 0.004 mole of titanium tetraisopropoxide was dropped into the mixed solution at 250 rpm, and then stirred at 40°C for 40 minutes at a constant temperature to obtain a palladium-titanium complex catalyst.

[0027] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of tetrafluoroethylene and 0.01 mole of N-phenylmaleimide to several vacuum-pumped, nitrogen-filled autoclaves, add 20ml Toluene dissolves. According to the amount of bis(tricyclohexylphosphine)palladium dichloride in the catalyst, it is 0.09% of the total weight of norbornene, tetrafluoroethylene and N-phenylmaleimide to get the above-mentioned palladium-titanium complex Catalyst, injected into the above mixture with a syringe. React at a constant temperature of 100°C...

Embodiment 3

[0029] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of bis(tricyclohexylphosphine)palladium dichloride and 0.012 moles of phenanthroline were dissolved in 10 milliliters of tetrahydrofuran to obtain a mixed solution; 0.004 mol tetraisopropoxytitanium was dropped into the mixed solution at 220 rpm, and then stirred at a constant temperature of 30° C. for 50 minutes to obtain a palladium-titanium complex catalyst.

[0030] Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene, 0.01 mole of tetrafluoroethylene and 0.01 mole of N-phenylmaleimide to several vacuum-evacuated, nitrogen-filled autoclaves In, add 20ml tetrahydrofuran to dissolve. According to the amount of bis(tricyclohexylphosphine)palladium dichloride in the catalyst, it is 2.00% of the total weight of norbornene, tetrafluoroethylene and N-phenylmaleimide to get the above-mentioned palladium-titanium complex Catalyst, injected into the above mixture with a syringe. The reaction was carried out a...

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Abstract

The invention relates to a norbornene, tetrafluoroethylene and N-phenyl maleimide ternary copolymerization catalyst and a ternary copolymerization method. The ternary copolymerization method is characterized by comprising the steps of dissolving bis(tricyclohexylphosphine)palladium dichloride and a ligand in a first solvent in a 3-mouth flask in a dry inert atmosphere so as to obtain a mixed solution; dripping titanium iso-propylate to the mixed solution at 150-250 rpm; after the dripping is finished, continuing to stir the materials at a temperature of 30-50 degrees centigrade for 30-50 minutes to obtain a palladium-titanium complex catalyst; taking and adding the norbornene, tetrafluoroethylene and N-phenyl maleimide monomers to a nitrogen charged high pressure kettle which is vacuumized for multiple times; adding a second solvent to the high pressure kettle to dissolve the monomers; and then adding the palladium-titanium complex catalyst to the high pressure kettle and enabling the materials in the high pressure kettle to react at a certain temperature and under a certain pressure; pouring a reaction product into ethanol solution containing hydrochloric acid; washing obtained precipitates by using ethanol to be neutral; and drying the washed precipitates in a vacuum manner to obtain a norbornene, tetrafluoroethylene and N-phenyl maleimide ternary copolymer.

Description

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

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F214/26C08F222/40C08F4/76C08F4/80
CPCC08F4/76C08F4/80C08F214/265C08F222/40C08F232/08
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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