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Preparation of copolymer of norbornene and maleic anhydride

A norbornene and maleic anhydride technology, which is applied in the field of preparation of norbornene and maleic anhydride copolymers, can solve the problems of less research on norbornene and maleic anhydride copolymerization, small molecular weight of copolymers, and alternating copolymers. low degree, etc., to achieve the effect of good catalytic effect, high degree of alternation, and good copolymerization reaction performance

Inactive Publication Date: 2008-12-24
NINGBO UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These free radical synthesis 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 there are few domestic researches on the copolymerization of norbornene and maleic anhydride.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Dissolve 0.01 mol of neodymium naphthenate in 20 ml of cyclohexane, add 0.005 mol of α, α'-bipyridyl and 0.30 mol of triethylaluminum to the above solution, keep the temperature in a water bath at 50°C for 30 minutes, and immediately after cooling A rare earth complex catalyst was obtained.

[0029] Add 0.024 mol of bicyclo[2,2,1]hept-2-ene and 0.024 mol of maleic anhydride into a 25 ml nitrogen-filled single-port polymerization bottle, and add 5 ml of toluene to dissolve. Take 1ml of rare earth complex catalyst and inject it into the above mixture with a syringe. Put it into a constant temperature water tank, and react at 80° C. for 6 hours. The product was poured into methanol solution containing 5% hydrochloric acid to precipitate norbornene and maleic anhydride copolymer, the precipitate was washed with methanol to neutrality, and vacuum-dried. The reaction yield (based on norbornene and maleic anhydride total amount) was 90.0 %.

Embodiment 2

[0031] Dissolve 0.03 mole of neodymium naphthenate in 30 ml of toluene, add 0.01 mole of α, α'-bipyridyl and 0.20 mole of diethylzinc to the above solution, keep the temperature in a water bath at 50°C for 15 minutes, and obtain rare earth after cooling complex catalyst.

[0032] Add 0.024 mol of 1-methylbicyclo[2,2,1]hept-2-ene and 0.024 mol of maleic anhydride into a 25 ml nitrogen-filled single-port polymerization bottle, and add 5 ml of toluene to dissolve. Take 1.5ml of catalyst and inject it into the above mixture with a syringe. Put it into a constant temperature water bath, and react at 70° C. for 7 hours. The product was poured into a methanol solution containing 5% hydrochloric acid to precipitate norbornene and maleic anhydride copolymer, the precipitate was washed with methanol to neutrality, and vacuum-dried. The reaction yield (based on the total amount of norbornene and maleic anhydride) was 92.1 %.

Embodiment 3

[0034] Dissolve 0.01 mol of neodymium naphthenate in 20 ml of toluene, add 0.01 mol of α, α'-bipyridyl and 2.50 mol of diethylzinc to the above solution, keep the temperature in a water bath at 50°C for 15 minutes, and obtain rare earth after cooling complex catalyst.

[0035] Add 0.024 mol of 5-methylbicyclo[2,2,1]hept-2-ene and 0.024 mol of maleic anhydride into a 25 ml nitrogen-filled single-port polymerization bottle, and add 5 ml of toluene to dissolve. Take 1ml of the catalyst and inject it into the above mixture with a syringe. Put it into a constant temperature water bath, and react at 70° C. for 7 hours. The product was poured into a methanol solution containing 5% hydrochloric acid to precipitate norbornene and maleic anhydride copolymer, the precipitate was washed with methanol to neutrality, and vacuum-dried. The reaction yield (based on the total amount of norbornene and maleic anhydride) was 75.3 %.

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Abstract

The invention relates to a method for preparing a norbornene and maleic anhydride copolymer. The method adopts a rare-earth complex as a catalyst to catalyze the alternating copolymerization of norbornene and maleic anhydride under normal pressure and at a temperature of between 4 and 100 DEG C; the reaction time is short, with only 5 to 9 hours required; the yield of copolymerization products is high and can reach over 67 percent; and the alternating degree of the copolymerization products is high.

Description

technical field [0001] The invention relates to the field of polymer synthesis, in particular to a preparation method of a norbornene-maleic anhydride copolymer. 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 inserting maleic anhydride into the main chain of polynorbornene, the cohesiveness and solubility of the polymer can be improved, and this copolymer can be used as a photoresist material in 193nm photolithography technology. 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, 193nm photolithography technology can be selected. These technologies involve all aspects of the photol...

Claims

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Application Information

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IPC IPC(8): C08F232/08C08F222/06C08F4/54
Inventor 房江华杨建平胡敏杰高浩其
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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