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Catalyst for ternary polymerization of norbornene, maleic anhydride and pentene, and ternary polymerization method

A pentene-based ternary copolymerization catalyst and norbornene technology, applied in the field of high polymers, can solve the problems of low copolymer yield, long reaction time, and few researches, and achieve high copolymer yield and preparation Simple method and high catalytic efficiency

Inactive Publication Date: 2013-11-20
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, and domestic studies on the ternary copolymerization of norbornene, maleic anhydride, and pentene have been carried out a lot. few

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a single-necked glass bottle that has been evacuated several times and baked with nitrogen, add 20 ml of tetrahydrofuran, 0.10 mol of bis(cyclopentadienyl) zirconium dichloride, 0.10 mol of 8-hydroxyquinoline and 0.05 mol of triethyl Aluminum, kept in a water bath at 50°C for 15 minutes, and cooled to obtain a zirconium complex catalyst.

[0027] Add 0.03 mole of bicyclo[2,2,1]hept-2-ene, 0.03 mole of maleic anhydride, and 0.03 mole of 1-pentene into a nitrogen-filled autoclave, and add 20 ml of tetrahydrofuran to dissolve. Take 1% of the above-mentioned catalyst according to the total weight of norbornene, maleic anhydride and 1-pentene, and inject it into the above-mentioned mixture with a syringe. Constant temperature at 90°C, 0.5MP pressure, react for 0.5 hours. The product was poured into a methanol solution containing 5% hydrochloric acid to precipitate norbornene, maleic anhydride, and 1-pentene terpolymer. The precipitate was washed with methanol to neutrali...

Embodiment 2

[0030] In a single-necked glass bottle that has been evacuated several times and baked with nitrogen, add 20 ml of anisole, 0.10 mole of bis(cyclopentadienyl) zirconium dichloride, 0.01 mole of α,α,-bipyridine and 0.01 mole of triisobutylaluminum, kept in a water bath at 40°C for 5 minutes, and cooled to obtain a zirconium complex catalyst.

[0031] Add 0.03 moles of 1-methylbicyclo[2,2,1]hept-2-ene, 0.03 moles of maleic anhydride, and 0.03 moles of 3-methyl-1-pentene into an autoclave filled with nitrogen, and add 20ml Anisole dissolved. According to the total weight of norbornene, maleic anhydride, and 3-methyl-1-pentene, 0.3% of the above-mentioned catalyst was taken and injected into the above-mentioned mixture with a syringe. Constant temperature at 90°C, 5MP pressure, react for 6 hours. The product was poured into a methanol solution containing 5% hydrochloric acid to precipitate norbornene, maleic anhydride, and 3-methyl-1-pentene terpolymer. The precipitate was washe...

Embodiment 3

[0033] 20 ml of 1,4-dioxane, 0.10 mol of bis(cyclopentadienyl) zirconium dichloride, 0.07 mol of o-diazo Phenanthrene and 0.03 moles of triethylzinc were kept in a water bath at 45°C for 15 minutes, and the zirconium complex catalyst was obtained after cooling.

[0034] Add 0.03 moles of 5-methylbicyclo[2,2,1]hept-2-ene, 0.03 moles of maleic anhydride, and 0.03 moles of 2-pentene into a nitrogen-filled autoclave, add 20ml of 1,4-diox The hexacyclic dissolves. Take 0.05% of the above-mentioned catalyst according to the total weight of norbornene, maleic anhydride and 2-pentene, and inject it into the above-mentioned mixture with a syringe. Constant temperature at 100°C, 1MP pressure, react for 4 hours. The product was poured into methanol solution containing 5% hydrochloric acid to precipitate norbornene, maleic anhydride, and 2-pentene terpolymer. The precipitate was washed with methanol until neutral, and dried in vacuum. The reaction yield was 61.2%.

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Abstract

The invention relates to a catalyst for ternary polymerization of norbornene, maleic anhydride and pentene, and a ternary polymerization method. The catalyst is prepared by following steps: dissolving bis(cyclopentadienyl) zirconium dichloride, a ligand and an alkyl metal compound to a first solvent in a dry single-opening glass bottle in which inert gas is filled; sealing the bottle opening by an emulsion tube, keeping the bottle at a constant temperature for 5 to 15min in a water bath of 40 to 50 DEC C; and cooling so as to obtain the zirconium complex catalyst. Preparation method of the catalyst is simple. The catalyst can produce catalytic activity under a certain pressure, at a temperature and in nitrogen protection system; the norbornene, maleic anhydride and pentene are catalyzed and are subjected to ternary polymerization; and products are easy to wash and separate after being soaked by methanol. The yield of copolymer is high; the reaction temperature is low; the catalyst is low in cost and is easy to obtain; and the catalytic efficiency is high.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a norbornene, maleic anhydride and pentene 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 193nm ultraviolet lithography. The main disadvantages of this material are brittleness, poor viscosity and low molecular weight. Inserting maleic anhydride into the main chain of polynorbornene can improve the cohesiveness and solubility of the polymer, and the incorporation of pentene can increase the toughness of the copolymer photoresist material. This terpolymer can be used as a photoresist material in 193nm photocopying technology. Moreover, the development of the microelectronics industry requires components with smaller sizes. For the exposure technology suitable for line wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F232/08C08F222/06C08F210/14C08F4/6592
Inventor 房江华高浩其杨建平胡敏杰方烨汶肖勋文丛杨王志强
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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