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Production method of copolymer of allyl monomer containing polar group

A technology of polar groups and copolymers, which is applied in the field of preparing copolymers of allyl monomers containing polar groups, can solve the problems of reduced polymerization activity, high catalyst cost, and difficulty in use, so as to achieve improved activity, Effect of improving catalyst life and reducing catalyst cost

Active Publication Date: 2012-06-13
THE UNIV OF TOKYO +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, usually when using a late transition metal catalyst system, not only the activity is low, but also the polymerization activity will decrease during long-time polymerization, so the cost of using an expensive late transition metal complex catalyst is very high. Difficulty using on

Method used

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  • Production method of copolymer of allyl monomer containing polar group
  • Production method of copolymer of allyl monomer containing polar group
  • Production method of copolymer of allyl monomer containing polar group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0229] Embodiment 1: Copolymerization of allyl acetate and ethylene (preparation of copolymer 1)

[0230] Under argon atmosphere, dichloromethane (3.75ml), toluene (3.75ml) and allyl acetate (7.5ml, 7.0g, 70mmol) were added to a solution containing metal complex catalyst 1 (58.2g, 0.10mmol). 50ml volume autoclave. After filling the autoclave with ethylene (3.0 MPa), the contents of the autoclave were stirred at 80° C. for 3 hours. After the autoclave was cooled to room temperature, methanol (about 20 ml) was added thereto. The resulting copolymer was recovered by filtration, washed with methanol and dried under reduced pressure to obtain Copolymer 1. Yield 754 mg. By size exclusion chromatography, the number average molecular weight and weight average molecular weight of the copolymer were calculated to be 8,100 and 16,200, respectively, and Mw / Mn was 2.0. By using the inverse gating decoupling method of the 13 The allyl acetate content of the copolymer was determined by ...

Embodiment 2

[0235] Embodiment 2: the copolymerization of allyl acetate and ethylene (preparation copolymer 2)

[0236] Toluene (7.5 ml) and allyl acetate (7.5 ml, 7.0 g, 70 mmol) were added to a 50 ml volume autoclave containing metal complex catalyst 1 (58.2 g, 0.10 mmol) under an argon atmosphere. After filling the autoclave with ethylene (3.0 MPa), the contents of the autoclave were stirred at 80° C. for 3 hours. After the autoclave was cooled to room temperature, methanol (about 20 ml) was added thereto. The resulting copolymer was recovered by filtration, washed with methanol and dried under reduced pressure to obtain Copolymer 2. Yield was 585 mg. By size exclusion chromatography, the number average molecular weight and weight average molecular weight of the copolymer were calculated to be 7,900 and 15,500, respectively, and Mw / Mn was 2.0. By using the inverse gating decoupling method of the 13 The allyl acetate content of the copolymer was determined by C-NMR spectrum, and the ...

Embodiment 3

[0237] Embodiment 3: the copolymerization of allyl acetate and ethylene (preparation copolymer 3)

[0238] Metal complex catalyst 2 was synthesized in the same manner as metal complex catalyst 1 using 2-(dicyclopentylphosphino)benzenesulfonic acid as a starting material.

[0239]

[0240] Cyp = cyclopentyl

[0241] Using the obtained metal complex catalyst 2, the copolymerization of allyl acetate and ethylene was carried out in the same manner as in Example 2. That is, under an argon atmosphere, toluene (7.5 ml) and allyl acetate (7.5 ml, 7.0 g, 70 mmol) were added to a 50 ml volume autoclave containing metal complex catalyst 2 (0.10 mmol). After filling the autoclave with ethylene (3.0 MPa), the contents of the autoclave were stirred at 80° C. for 3 hours. After the autoclave was cooled to room temperature, methanol (about 20 ml) was added thereto. The resulting copolymer was recovered by filtration, washed with methanol and dried under reduced pressure to obtain copoly...

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Abstract

The present invention relates to a method for producing a high-molecular-weight copolymer of polar group- containing allyl monomers comprising monomer units represented by formulae (3) and (4) (in the formulae, R1 represents a hydrogen atom (H) or hydrocarbon group having 1 to 6 carbon atoms; R2 represents -OH, -OCOR3 (R3 represents hydrocarbon group having 1 to 5 carbon atoms), -N(R4)2 (R4 represents a hydrogen atom or hydrocarbon group having 1 to 5 carbon atoms); and n and m are a value representing the molar ratio of each of the monomer units), which has few branches and unsaturated group at the molecular end, by copolymerizing olefin and an allyl compound using a metal complex of group 10 elements in the periodic system represented by a specific formula as a catalyst.

Description

technical field [0001] The present invention relates to a preparation method of a copolymer of an allyl monomer containing a polar group and a copolymer obtained by the method. Background technique [0002] Copolymers of non-polar monomeric olefins such as ethylene and propylene with polar group-containing vinyl monomers are well known. In particular, ethylene-vinyl alcohol copolymer (EVOH) is a random copolymer comprising ethylene and vinyl alcohol, which is synthesized by saponifying ethylene-vinyl acetate copolymer obtained by radical copolymerization of ethylene and vinyl acetate . Due to excellent gas barrier properties, EVOH is widely used in fields such as food packaging applications. [0003] It is widely known that copolymers obtained by copolymerization of ethylene by radical polymerization generate short-chain branches and long-chain branches due to back biting reactions. For example, in the case of EVOH, it is reported that there are about 1 mol% of alkyl bran...

Claims

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Application Information

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IPC IPC(8): C08F210/02C08F4/80
CPCC08F110/02C08F210/02C08F4/80C08F2500/03C08F216/08C08F214/02C08F218/02C08F226/02C08F214/00C08F220/10C08F210/06C08F18/02
Inventor 野崎京子伊藤慎库奥村吉邦黑田润一
Owner THE UNIV OF TOKYO
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