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Norbornene, pentene and vinylene carbonate ternary copolymerized catalyst and ternary copolymerizing method

A vinylene carbonate ternary copolymerization catalyst and vinylene carbonate ternary technology, applied in the field of high polymers, can solve the problems of low copolymer alternation, small copolymer molecular weight, low copolymer yield, etc., and achieve solubility and toughness improvement, low reaction temperature and high copolymer yield

Active Publication Date: 2017-06-13
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

[0026] In a three-necked flask with a dry inert gas atmosphere, dissolve 0.001 mole of bis(pentamethylcyclopentadienyl) hafnium dichloride (iv) and 0.006 mole of 8-hydroxyquinoline in 10 ml of benzene, at 200rpm , drop 0.010 moles of triisobutylaluminum into the above solution, and then stir at the same stirring rate at 60°C for 20 minutes at a constant temperature to obtain a hafnium-aluminum complex catalyst.

[0027] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of 1-pentene and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20ml of benzene to dissolve. Bicyclo[2,2,1]hept-2-ene, 1-pentene and vinylene carbonate based on the amount of bis(pentamethylcyclopentadienyl)hafnium(iv) dichloride Take 0.06% of the total weight of the above-mentioned hafnium-aluminum complex catalyst and inject it into the above-mentioned mixture with a syringe. React at a constant temperature of 90° C. and a pressure of 8 MPa for 6...

Embodiment 2

[0030] In a three-necked flask with a dry inert gas atmosphere, 0.001 mole of bis(pentamethylcyclopentadienyl) hafnium dichloride (iv) and 0.007 mole of α, α'-bipyridine were dissolved in 10 ml of toluene, At 400 rpm, 0.020 mol of triethylaluminum was dropped into the above solution, and then stirred at the same stirring rate at 20° C. for 50 minutes at a constant temperature to obtain a hafnium-aluminum complex catalyst.

[0031] Add 0.01 mole of bicyclo[2,2,1]hept-2-ene, 0.01 mole of 2-pentene and 0.01 mole of vinylene carbonate into an autoclave evacuated several times and filled with nitrogen, and add 20ml of toluene to dissolve. Bicyclo[2,2,1]hept-2-ene, 2-pentene and vinylene carbonate tri Take 0.01% of the total weight of the above-mentioned hafnium-aluminum complex catalyst and inject it into the above-mentioned mixture with a syringe. React at a constant temperature of 100°C and a pressure of 6 MPa for 6 hours. The product is poured into an ethanol solution containi...

Embodiment 3

[0033] In a three-necked flask with a dry inert gas atmosphere, 0.001 moles of bis(pentamethylcyclopentadienyl) hafnium dichloride (iv) and 0.012 moles of phenanthroline were dissolved in 10 milliliters of tetrahydrofuran, at 350rpm, 0.010 moles of triisobutylaluminum was dropped into the above solution, and then stirred at the same stirring rate at 60° C. for 50 minutes at a constant temperature to obtain a hafnium-aluminum complex catalyst.

[0034]Add 0.01 mole of 1-methylbicyclo[2,2,1]hept-2-ene, 0.01 mole of 3-methyl-1-pentene and 0.01 mole of vinylene carbonate to the Kettle, add 20ml tetrahydrofuran to dissolve. 1-methylbicyclo[2,2,1]hept-2-ene, 3-methyl-1 - 0.10% of the total weight of pentene and vinylene carbonate Take the above-mentioned hafnium-aluminum complex catalyst and inject it into the above-mentioned mixture with a syringe. React at a constant temperature of 90°C and a pressure of 7MPa for 5 hours. The product was poured into an ethanol solution containi...

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Abstract

The invention relates to a norbornene, pentene and vinylene carbonate ternary copolymerized catalyst and a ternary copolymerizing method. The method for preparing the catalyst comprises the following steps: dissolving bis(pentamethylcyclopentadienyl) hafnium dichloride (iV) and ligand in a first solvent in a dried three-mouth flask at an inert gas atmosphere, dripping aluminum alkyl under 200-400rpm, stirring at constant temperature at the same stirring speed at constant temperature of 20-60 DEG C for 20-60 minutes to obtain a hafnium-aluminum complex catalyst; adding norbornene, pentene and vinylene carbonate into a reaction kettle which is vacuumized for multiple times and inflated with nitrogen, adding a second solvent and dissolving; adding the hafnium-aluminum complex catalyst, and reacting for 1-6 hours at certain temperature and pressure; and pouring the product obtain in the reaction into a hydrochloric acid-containing alcohol solution, washing the precipitate to be neutral with alcohol, and drying in vacuum to obtain the norbornene, pentene and vinylene carbonate ternary copolymerized catalyst.

Description

technical field [0001] The invention relates to the field of high polymers, in particular to a norbornene, pentene and vinylene carbonate 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. After oxygen-containing compounds and olefins are 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 w...

Claims

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Application Information

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IPC IPC(8): C08F232/08C08F210/14C08F218/00C08F4/6592
CPCC08F4/65912C08F4/65925C08F210/14C08F218/00C08F218/24C08F232/08
Inventor 胡敏杰王江波房江华高浩其杨建平王志强陈斌
Owner NINGBO UNIVERSITY OF TECHNOLOGY
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