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Norbornene-based and vinylene carbonate binary copolymerization catalyst and binary copolymerization method

A technology of vinylene carbonate 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, improved solubility and toughness , The effect of high copolymer yield

Active Publication Date: 2019-05-07
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 mole of tris(butylcyclopentadiene)scandium and 0.001 mole of 8-hydroxyquinoline in 10 ml of benzene, and drop 0.015 mole of diethylzinc at 150 rpm Add it into the above solution, and stir at the same stirring rate at 30°C for 30 minutes at a constant temperature after dropping to obtain a scandium-zinc complex catalyst.

[0025] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20 ml of benzene to dissolve. According to the amount of scandium tri(butylcyclopentadiene) in the catalyst, it is 0.01% of the total weight of bicyclo[2,2,1]hept-2-ene and vinylene carbonate, and the above-mentioned scandium-zinc complex Catalyst, injected into the above mixture with a syringe. React at a constant temperature of 80°C and a pressure of 5MPa for 6 hours. The product was poured into an ethanol solution cont...

Embodiment 2

[0028] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of tris(butylcyclopentadiene)scandium and 0.015 moles of α, α'-bipyridine were dissolved in 10 ml of toluene, and 0.008 moles of diethyl Zinc is dropped into the above solution, and after the drop is completed, it is stirred at a constant temperature at the same stirring rate of 50° C. for 50 minutes to obtain a scandium-zinc complex catalyst.

[0029] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20 ml of toluene to dissolve. According to the amount of scandium tri(butylcyclopentadiene) in the catalyst, it is 0.09% of the total weight of bicyclo[2,2,1]hept-2-ene and vinylene carbonate, and the above-mentioned scandium-zinc complex Catalyst, injected into the above mixture with a syringe. The reaction was carried out at a constant temperature of 100° C. and a pressure of 4 MPa for 6 hours. The ...

Embodiment 3

[0031] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of tris(butylcyclopentadiene) scandium and 0.006 moles of phenanthroline were dissolved in 10 ml of tetrahydrofuran, and 0.010 moles of diethylzinc was dropped into In the above solution, stir at the same temperature at 45° C. for 50 minutes at the same stirring rate after dropping to obtain the scandium-zinc complex catalyst.

[0032] Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20 ml of tetrahydrofuran to dissolve. According to the amount of scandium tri(butylcyclopentadiene) in the catalyst, it is 0.08% of the total weight of 1-methylbicyclo[2,2,1]hept-2-ene and vinylene carbonate, and the above-mentioned scandium- Zinc complex catalyst, injected into the above mixture with a syringe. React at a constant temperature of 120° C. and a pressure of 6 MPa for 5 hours. The product is pour...

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Abstract

The invention relates to a norbornene and vinylene carbonate binary copolymerized catalyst, and is characterized in that a preparation method of the catalyst comprises the following steps: in a dry three-neck flask with an inert gas atmosphere, dissolving tri(butylcyclopentadienyl)scandium and a ligand in a first solvent, dropping diethyl zinc at a speed rate of 150-300 rpm, and after the dropping is completed, carrying out isothermal stirring for 30-60 minutes at the temperature of 30-60 DEG C at the same stirring speed rate, to obtain a scandium-zinc complex catalyst; taking norbornene and vinylene carbonate monomers according to the molar ratio of 1:1, adding the components into a reaction kettle vacuumized for multiple times and filled with nitrogen, adding a second solvent, and dissolving; then adding the scandium-zinc complex catalyst, and carrying out a reaction for 1-6 hours at the temperature of 20-130 DEG C and the pressure of 0.1-8 MPa; and pouring the product obtained from the reaction into an ethanol solution containing 4.5-5.5 wt% of hydrochloric acid, washing an obtained precipitate with ethanol to be neutral, and vacuum-drying to obtain the norbornene and vinylene carbonate binary copolymerized catalyst.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a norbornene and vinylene carbonate binary copolymerization catalyst and a binary 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 the oxygen-containing olefin is inserted into the main chain of polynorbornene, the cohesiveness and solubility of the polymer can be improved, and the light absorption rate of the material itself can be reduced. 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 and bel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F218/00C08F4/54C08F4/52
CPCC08F4/52C08F4/545C08F218/00C08F218/24C08F232/08
Inventor 周国权房江华王江波胡敏杰高浩其杨建平王志强陈斌
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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