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Novel triarylphosphine or triarylarsine compounds, alpha-olefin polymerization catalysts using same, terpolymer, and process for production of copolymer of alpha-olefin and (meth)acrylic comonomer

A technology for olefin polymerization and catalyst, which is applied in nickel organic compounds, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. It can solve the problem of sticky components and improve the balance between mechanical properties and adhesion Problems such as insufficient mechanical properties of ethylene-based copolymers

Active Publication Date: 2014-12-10
JAPAN POLYETHYLENE CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] On the other hand, terpolymers of ethylene and α-olefins and polar group-containing monomers are also known. For example, Patent Document 9 discloses that the content of ethyl acrylate prepared by using a specific chromium-based catalyst is 12.1 to 35.5 mol% ethylene / 1-octene / ethyl acrylate terpolymer, but this copolymer is still insufficient in terms of improving the balance of mechanical properties and adhesiveness, and there are many sticky components, and eye dropsy during molding Objects, film adhesion and other problems
In addition, Patent Document 10 discloses an ethylene-propylene-methyl acrylate terpolymer with a propylene content of 13.5 to 18.5 mol% and a methyl acrylate content of 8 to 27.2 mol%, prepared using a specific vanadium-based catalyst. According to research by the inventors of the application, as a material, its strength is not as strong as expected for polyethylene
In this way, when compared with vinyl polymers (copolymers) not containing polar groups, a significant reduction in the mechanical properties of vinyl copolymers containing polar groups is unavoidable.

Method used

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  • Novel triarylphosphine or triarylarsine compounds, alpha-olefin polymerization catalysts using same, terpolymer, and process for production of copolymer of alpha-olefin and (meth)acrylic comonomer
  • Novel triarylphosphine or triarylarsine compounds, alpha-olefin polymerization catalysts using same, terpolymer, and process for production of copolymer of alpha-olefin and (meth)acrylic comonomer
  • Novel triarylphosphine or triarylarsine compounds, alpha-olefin polymerization catalysts using same, terpolymer, and process for production of copolymer of alpha-olefin and (meth)acrylic comonomer

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0151] Examples of the monomer used for the preparation of the copolymer include α-olefins, (meth)acrylic olefins, and other olefins described below.

[0152] (a) α-Olefins

[0153] One of the monomers used in the present invention is the general formula CH 2 =CHR 17 The shown α-olefin (hereinafter may be referred to as "(a) component"). Here, R 17 is hydrogen or an alkyl group having 1 to 20 carbon atoms.

[0154] Among them, R having 1 to 10 carbon atoms is exemplified as a preferable component (a). 17 of α-olefins. As more preferable (a) component, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, 1-decene, 3-methyl-1-butene are mentioned , 4-methyl-1-pentene, more preferably propylene, 1-butene, 1-pentene, 1-hexene, 1-octene, particularly preferably 1-hexene. Moreover, (a) component may be used individually, and multiple types (a) component may be used in combination.

[0155] (b) (meth)acrylic olefins

[0156] Another monomer used in the present inven...

Embodiment

[0219] The present invention will be specifically described below by the examples and comparative examples, and by the data of each suitable example and the contrast of each example and each comparative example, the rationality and significance of the technical solution of the present invention and the comparison with existing ones are confirmed. There is technical excellence. In addition, the structures of ligands used in Examples and Comparative Examples are shown in Table 1.

[0220] [Table 1]

[0221]

[0222] In addition, the following abbreviations are used in the examples.

[0223] Pd(dba)2: Bis(dibenzylideneacetone)palladium

[0224] Ni(cod)2: bis(cyclooctadiene) nickel

[0225] MA: methyl acrylate

[0226] EA: ethyl acrylate

[0227] tBA: tert-butyl acrylate

[0228] MMA: methyl methacrylate

[0229] AA: Acrylic

[0230] VA: vinyl acetate

[0231] LUA: lauryl acrylate

[0232] HEA: 2-Hydroxyethyl Acrylate

[0233] EUA: ethyl undecylenate

[0234] NBMOH:...

Synthetic example 1

[0317] (Synthesis Example 1) Synthesis of Ligand (I)

[0318] Slowly add n-butyllithium hexane solution (2.5M, 2mL, 5mmol) dropwise to a solution of benzenesulfonic anhydride (400mg, 2.5mmol) in tetrahydrofuran (20mL) at 0°C and stir while raising the temperature to room temperature 1 hour. The reaction solution was cooled to -70°C, phosphorus trichloride (340 mg, 2.5 mmol) was added, and the mixture was stirred for 2 hours while raising the temperature to room temperature (reaction solution A).

[0319] Slowly add n-butyllithium hexane solution (2.5M, 2mL, 5mmol) dropwise into a solution of 1-bromo-2-isopropylbenzene (1g, 5mmol) in diethyl ether (20mL) at -30°C. The mixture was stirred for 3 hours while allowing the temperature to rise to room temperature. This solution was added dropwise to the previous reaction solution A at room temperature, and stirred overnight. After the reaction, water (20 mL) was added, extracted with ether (20 mL×2), washed with 1N hydrochloric ac...

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Abstract

To provide an industrially useful α-olefin.((meth)acrylic acid)-based olefin copolymer having both a high molecular weight and a high comonomer content, a catalyst component capable of realizing a production of two different kinds of α-olefin.((meth)acrylic acid)-based olefin copolymers, and a production process using the catalyst. An α-olefin.((meth)acrylic acid)-based olefin copolymer is produced by using a metal complex complexed with a ligand represented by the following formula (Y is phosphorus or arsenic) for a catalyst composition.

Description

technical field [0001] The present invention relates to novel triarylphosphine or triarylarsine compounds, α-olefin polymerization catalysts using them, and methods for producing α-olefin / (meth)acrylic copolymers, and more particularly to α-olefin-based copolymers produced by using these novel compounds. An alpha-olefin / (meth)acrylic acid terpolymer with high molecular weight and high comonomer content prepared by polymerizing a catalyst, and a preparation method thereof. Background technique [0002] Conventionally, among resin materials, ethylene-based polymers such as ethylene polymers and copolymers of ethylene and α-olefins have excellent physical properties, moldability, and other properties, and are also high in economical efficiency and adaptability to environmental problems. Commonly used and important industrial materials. However, vinyl polymers do not have a polar group, and applications requiring physical properties such as adhesion to other materials, printabi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/50C07F9/655C07F9/74C08F4/80C08F10/00C07F15/00C07F15/04
CPCC07F9/65515C07F15/04C08F10/00C08F210/16C07F9/74C07F9/5022C08F4/80C08F210/06C08F2500/03C08F210/14C08F210/02C08F2/00
Inventor 小林稔内野英史山本和弘江头俊昭清水浩之森冈哲哉
Owner JAPAN POLYETHYLENE CORP
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