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Norbornene, octafluorocyclopentene and N-phenyl maleimide ternary copolymerization catalyst and ternary copolymerization method

A maleimide ternary copolymerization catalyst and maleimide ternary technology, applied in the field of polymers, can solve the problems of small molecular weight of copolymers, low degree of alternation of copolymers, and low yield of copolymers. Achieve the effects of low reaction temperature, improved solubility and toughness, and high copolymer yield

Active Publication Date: 2017-05-31
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

[0025] In a three-necked flask with a dry inert atmosphere, dissolve 0.001 mol of titanocene dichloride and 0.001 mol of 8-hydroxyquinoline in 10 ml of benzene, and drop 0.001 mol of triisobutyltrialuminum into the above solution at 150 rpm , and after the drop is completed, stir at the same temperature at 30° C. for 30 minutes at the same stirring rate to obtain a titanium-aluminum complex catalyst.

[0026] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of octafluorocyclopentene and 0.01 mole of N-phenylmaleimide to several vacuum-pumped, nitrogen-filled autoclaves, Add 20ml of benzene to dissolve. According to the amount of titanocene dichloride in the catalyst, it is taken as 0.01% of the total weight of bicyclo[2,2,1]hept-2-ene, octafluorocyclopentene and N-phenylmaleimide The above-mentioned titanium-aluminum complex catalyst is injected into the above-mentioned mixture with a syringe. React at a constant temperature of 80°C and a pressure of 0.1MPa for 6 hours. ...

Embodiment 2

[0029] In a dry three-necked flask with an inert atmosphere, dissolve 0.001 mol of titanocene dichloride and 0.006 mol of α, α'-bipyridine in 10 ml of toluene, and drop 0.008 mol of triisobutylaluminum into the above-mentioned In the solution, stir at the same temperature at 50° C. for 50 minutes at the same stirring rate after dropping, to obtain a titanium-aluminum complex catalyst.

[0030] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of octafluorocyclopentene and 0.01 mole of N-phenylmaleimide to several vacuum-pumped, nitrogen-filled autoclaves, Add 20ml of toluene to dissolve. According to the amount of titanocene dichloride in the catalyst, it is taken as 0.10% of the total weight of bicyclo[2,2,1]hept-2-ene, octafluorocyclopentene and N-phenylmaleimide The above-mentioned titanium-aluminum complex catalyst is injected into the above-mentioned mixture with a syringe. React at a constant temperature of 110° C. and a pressure of 4 MPa for 6 hours. The product i...

Embodiment 3

[0032] In a three-necked flask with a dry inert atmosphere, dissolve 0.001 moles of titanocene dichloride and 0.010 moles of phenanthrocene in 10 ml of tetrahydrofuran, and drop 0.004 moles of triethylaluminum into the above solution at 150 rpm. After completion, stir at the same temperature at 30° C. for 50 minutes at the same stirring rate to obtain a titanium-aluminum complex catalyst.

[0033] Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene, 0.01 mole of octafluorocyclopentene and 0.01 mole of N-phenylmaleimide to the In the autoclave, add 20ml THF to dissolve. According to the amount of titanium dichloride in the catalyst, it is the total weight of 1-methylbicyclo[2,2,1]hept-2-ene, octafluorocyclopentene and N-phenylmaleimide 0.07% of the above-mentioned titanium-aluminum complex catalyst was injected into the above-mentioned mixture with a syringe. The reaction was carried out at a constant temperature of 130° C. and a pressure of 6 MPa for 1 hour. The product is po...

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PUM

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Abstract

The invention relates to a norbornene, octafluorocyclopentene and N-phenyl maleimide ternary copolymerization catalyst and a ternary copolymerization method. The norbornene, octafluorocyclopentene and N-phenyl maleimide ternary copolymerization catalyst is characterized in that a preparation method for the norbornene, octafluorocyclopentene and N-phenyl maleimide ternary copolymerization catalyst comprises the steps of dissolving titanocene dichloride and a ligand in a first solvent in a 3-mouth flask in a dry inert atmosphere; dripping aluminum alkyl to the 3-mouth flask at 130-170 rpm; after the dripping is finished, stirring the materials at a constant temperature of 30-60 degrees centigrade for 30-60 minutes to obtain a titanium-aluminum complex catalyst; taking norbornene, octafluorocyclopentene and N-phenyl maleimide monomers according to a mole ratio of 1:1:1; adding the norbornene, octafluorocyclopentene and N-phenyl maleimide monomers to a nitrogen charged reaction kettle which is vacuumized for multiple times; adding a second solvent to the reaction kettle to dissolve the monomers; and then adding the titanium-aluminum complex catalyst to the reaction kettle and enabling the materials in the reaction kettle to react at a certain temperature and under a certain pressure; pouring a reaction product into ethanol solution containing 4-5wt% hydrochloric acid; washing obtained precipitates by using ethanol to be neutral; and drying the washed precipitates in a vacuum manner to obtain a norbornene, octafluorocyclopentene 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, octafluorocyclopentene 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 193nm ultraviolet lithography. The main disadvantages of this material are brittleness, poor viscosity and low molecular weight. After perfluoroolefin is inserted 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 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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F232/08C08F232/04C08F222/40C08F4/6592
CPCC08F4/65925C08F222/40C08F232/04C08F232/08
Inventor 周国权王江波胡敏杰房江华李正辉高浩其杨建平
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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