Hydroxyl Vinyl Ether Polymerization via Water Solvent

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Solution Overview

Problem

Current methods for producing hydroxyl group-containing vinyl ether polymers face inefficiencies due to low monomer conversion rates, generation of polyacetal, and the need for removal steps for residual monomers and initiator residues, especially when using radical polymerization with non-nitrile azo initiators and alcoholic solvents.

Innovation Solution

Radical polymerization of vinyl ethers with a specific azo compound, such as dimethyl 2,2'-azobis(2-methylpropionate), in the presence of water as a solvent, which improves monomer conversion rates and reduces the amount of polymerization initiator required, while suppressing polyacetal formation.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If radical polymerization is performed using non-nitrile azo initiators and alcoholic solvents, then monomer conversion rate is improved, but polyacetal is generated and yield is reduced

Engineering Contradiction:
Improvemonomer conversion rateVSAvoidpolyacetal generation
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The harmful alcoholic solvent component is extracted and removed from the polymerization system, replacing it with water as the solvent. This eliminates the source of polyacetal generation while maintaining the benefits of radical polymerization with azo initiators.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The solvent parameter is changed from alcoholic solvent to water, fundamentally altering the polymerization environment. This parameter change eliminates polyacetal formation while allowing high monomer conversion rates to be achieved through optimized azo initiator selection and concentration.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If large amount of polymerization initiator is used to improve monomer conversion rate, then conversion rate increases, but residual initiator residues increase requiring removal steps

Engineering Contradiction:
Improvemonomer conversion rateVSAvoidresidual initiator residues
Core Design Contradiction:
ProductivityVSLoss of substance

Solution Approach 1:

The type of polymerization initiator is changed from conventional azo initiators to specific non-nitrile azo initiators with optimized molecular structure. This parameter change allows achieving high monomer conversion rates (90% or more) with lower initiator concentrations, thereby reducing residual initiator residues and eliminating the need for additional removal steps.

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If vinyl ether with many carbons and higher hydrophobicity is used, then polymer diversity is improved, but monomer conversion rate is reduced

Engineering Contradiction:
Improvepolymer diversityVSAvoidmonomer conversion rate
Core Design Contradiction:
Adaptability or versatilityVSProductivity

Solution Approach 1:

The solvent parameter is changed to water, which fundamentally alters the polymerization environment to accommodate hydrophobic monomers with many carbons. This enables efficient polymerization of diverse vinyl ether monomers including cycloaliphatic structures, achieving high conversion rates that were previously unattainable.

Inventive Principle:
Principle #35Parameter changes

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

This method allows for a high monomer conversion rate of 80% or more, minimizing residual monomers and initiator residues, and enables the production of hydroxyl group-containing vinyl ether polymers with a low content of low boiling point impurities, facilitating their use in various applications like paints and adhesives without additional purification steps.

Implementation Method 1

a step of radical polymerizing at least one vinyl ether selected from vinyl ether having a hydroxyl group

Methodology Applied
Scientific EffectRadical polymerization: Chemical Bonding

Data Source

PatentEP3318583B1Improved method for producing hydroxy group-containing vinyl ether polymer
Publication Date: 2020.06.17 MARUZEN PETROCHEMICAL CO LTD
  • EP3318583B1 patent drawing
  • EP3318583B1 patent drawing
  • EP3318583B1 patent drawing

AI summary

[Object] To provide a simple and efficient method for producing a hydroxyl group-containing vinyl ether polymer, without the need of a removal step of low boiling point impurities such as residual monomers and initiator residues and polyacetal, or the like, by improving the monomer conversion rate while reducing the amount of a polymerization initiator to be used, and suppressing generation of polyacetal. [Means for solving problem] A method for producing a hydroxyl group-containing vinyl ether polymer according to the present invention comprises: a step of radical polymerizing at least one vinyl ether selected from vinyl ether having a hydroxyl group represented by the following formula (2): wherein R7 represents an alkylene group which is straight-chained, branched or comprises an alicyclic structure, and p is 1, 2, or 3, in the presence of water as a polymerization solvent and an azo compound represented by the following formula (1) as a polymerization initiator: wherein R1 to R4 each independently represent a hydrogen atom or an alkyl group and R5 and R6 each independently represent an alkoxy group optionally having a substituent group or an alkyl amino group optionally having a substituent group.