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Improved method for producing hydroxy group-containing vinyl ether polymer

A technology of vinyl ether and manufacturing method, applied in the direction of unsaturated ether copolymer adhesive, adhesive type, application, etc., can solve the problem of lower monomer conversion rate, inability to perform efficient polymerization, vinyl ether polymer Yield decline and other problems, to achieve the effect of inhibiting the formation of polyacetal and improving the conversion rate of monomer

Active Publication Date: 2018-03-23
MARUZEN PETROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, it has been found that even when a non-nitrile-azo-based initiator and an alcohol-based solvent are used, depending on the type of alcohol used as a solvent, polyacetal is sometimes produced, and the target hydroxyl-containing vinyl ether is polymerized The yield of the product decreased significantly
[0007] In addition, in the method of Patent Document 1, for monomers having a large number of carbon atoms and high hydrophobicity, such as vinyl ether having an alkylene group containing an alicyclic structure, the conversion rate of the monomer is further reduced, and efficient polymerization

Method used

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  • Improved method for producing hydroxy group-containing vinyl ether polymer
  • Improved method for producing hydroxy group-containing vinyl ether polymer
  • Improved method for producing hydroxy group-containing vinyl ether polymer

Examples

Experimental program
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Effect test

Embodiment 1

[0094] Embodiment 1: the manufacture of poly(2-hydroxyethyl vinyl ether) (1)

[0095] A stirrer, and 2-hydroxyethyl vinyl ether (hereinafter referred to as "HEVE") as a monomer, 500 mole parts, MAIB (Wako Pure Chemical Industries, Ltd.) as a radical polymerization initiator were put into the test tube ) product, trade name V-601) 1 mole part (0.2 mole % with respect to the monomer), further adding water as a polymerization solvent so that the HEVE concentration becomes 50 mass %, and fully dissolved it. Next, nitrogen gas was blown into the test tube to remove oxygen. After removing the oxygen, the test tube was sealed, and the polymerization reaction was started in an oil bath at 70°C. After 48 hours, the polymerization was terminated by cooling and exposure to air, and 1 H NMR analysis and GPC analysis. As a result, the monomer conversion after 48 hours had passed was 99% or more, the number average molecular weight Mn of the obtained polymer was 33900, and the molecula...

Embodiment 2

[0096] Embodiment 2: the manufacture of poly(2-hydroxyethyl vinyl ether) (2)

[0097] The polymerization reaction was performed in the same manner as in Example 1 except that water was added so that the HEVE concentration became 20% by mass. As a result, the monomer conversion after 48 hours had passed was 99% or more, the number average molecular weight Mn of the obtained polymer was 10700, and the molecular weight distribution Mw / Mn was 1.59.

Embodiment 3

[0098] Embodiment 3: the manufacture of poly(2-hydroxyethyl vinyl ether) (3)

[0099] 2,2'-Azobis[2-methyl-N-(2-hydroxyethyl)propionamide] (manufactured by Wako Pure Chemical Industries, Ltd., trade name V-086) was used as a radical polymerization initiator , except that, the polymerization reaction was carried out by the same operation as in Example 1. As a result, the monomer conversion after 93 hours had passed was 99% or more, the number average molecular weight Mn of the obtained polymer was 11400, and the molecular weight distribution Mw / Mn was 1.94.

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Abstract

The invention provides a simple and efficient method for producing a hydroxy group-containing vinyl ether polymer, which does not require a step for removing low-boiling-point impurities such as residual monomers and initiator residues, polyacetals and the like by suppressing the production of polyacetals by improving the monomer conversion rate, while reducing the amount of a polymerization initiator used therefor. A vinyl ether having a hydroxy group represented by formula (2) is radically polymerized in the presence of water, which serves as a polymerization solvent, and an azo compound represented by formula (1), which serves as a polymerization initiator. (In formula (1), each of R1-R4 independently represents a hydrogen atom or an alkyl group; and each of R5 and R6 independently represents an optionally substituted alkoxy group or an optionally substituted alkylamino group.) (In formula (2), R7 represents a linear, branched or alicyclic structure-containing alkylene group; and prepresents 1, 2 or 3.).

Description

technical field [0001] The present invention relates to a simple and efficient method for producing a hydroxyl group-containing vinyl ether polymer. Furthermore, the present invention relates to a simple and efficient method for producing an aqueous solution of a vinyl ether polymer having a hydroxyl group. Background technique [0002] Hydroxyl-containing vinyl ether polymers are excellent in adhesion to substrates and processability based on cross-linking reactions with various resins, and are used as paints, inks, adhesives, resin modifiers, metal recovery resins, compatibilizers It is useful as a main ingredient or a compounding component of an agent, a surfactant, a dispersant, a binder, and the like. [0003] It is known that vinyl ether generally has an electron-donating substituent and is a cationically polymerizable monomer, and thus undergoes cation polymerization. However, since the hydroxyl group initiates a termination reaction against the cationic polymerizat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F16/26C08F4/04C08K3/18C08L29/10C09D11/00C09D129/10C09J129/10
CPCC08F4/04C08F16/26C08F116/14C09D129/10C09J129/10C08K3/18C09D11/00C08L29/10C09D11/106C08F2/10C08F16/04
Inventor 杉原伸治吉田宪弘
Owner MARUZEN PETROCHEMICAL CO LTD
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