Stabilizing Perfluoro(2-methylene-4-methyl-1,3-dioxolane) Monomer

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Solution Overview

Problem

Perfluoro(2-methylene-4-methyl-1,3-dioxolane) is prone to polymerization and coloring during storage, which affects its quality and stability, particularly in optical applications like optical fibers, where controlling molecular weight and polymer properties is crucial.

Innovation Solution

Incorporating a hydroxy group-containing fluoroaromatic compound, such as perfluoro hydroquinone, into the composition to suppress polymerization reactions and maintain the temperature at 0° C. or lower, effectively stabilizing perfluoro(2-methylene-4-methyl-1,3-dioxolane and preventing quality changes.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If perfluoro(2-methylene-4-methyl-1,3-dioxolane) is stored for extended periods, then polymerization reactions occur, but storage stability is compromised

Engineering Contradiction:

Improvestorage periodVSAvoidmonomer stability

Core Design Contradiction:

Duration of action of stationary objectVSStability of the object's composition

Solution Approach 1:

A phenolic compound is introduced as an intermediary substance to inhibit polymerization reactions during storage. The phenolic compound acts as a polymerization inhibitor, selectively suppressing unwanted polymerization while allowing controlled polymerization to proceed when needed for production.

Inventive Principle:

Principle #24Intermediary (Mediator)

Solution Approach 2:

The storage temperature is reduced to -30°C or lower, changing the thermal parameter to suppress polymerization reactions. This low-temperature storage condition slows down the polymerization kinetics, maintaining monomer stability during extended storage periods.

Inventive Principle:

Principle #35Parameter changes

2Ease of operation

If perfluoro(2-methylene-4-methyl-1,3-dioxolane) is stored at room temperature, then ease of operation is improved, but coloring occurs during storage

Engineering Contradiction:

Improvehandling convenienceVSAvoidcoloring

Core Design Contradiction:

Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The phenolic compound serves as a protective intermediary that prevents coloring reactions during storage. It acts as an antioxidant or stabilizer that inhibits the chemical reactions causing discoloration, allowing the monomer to be stored and handled without quality degradation.

Inventive Principle:

Principle #24Intermediary (Mediator)

3Manufacturing precision

If controlled polymerization is performed to achieve specific molecular weights, then manufacturing precision is improved, but storage stability deteriorates

Engineering Contradiction:

Improvemolecular weight controlVSAvoidmonomer stability

Core Design Contradiction:

Manufacturing precisionVSStability of the object's composition

Solution Approach 1:

The phenolic compound is used as a selective inhibitor that suppresses unwanted polymerization during storage but can be removed or deactivated during the controlled polymerization process, allowing precise molecular weight control when production is required.

Inventive Principle:

Principle #24Intermediary (Mediator)

Solution Approach 2:

The monomer is pre-stabilized with the phenolic compound inhibitor during storage, and this stabilization is removed or overridden during the controlled polymerization process, enabling precise molecular weight control at the time of production.

Inventive Principle:

Principle #10Preliminary action

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

The method effectively stabilizes perfluoro(2-methylene-4-methyl-1,3-dioxolane, preventing polymerization and coloring during storage, ensuring high-quality preservation for applications in gas separation membranes and optical fibers.

Implementation Method 1

incorporating at least one selected from the group consisting of a hydroxy group-containing fluoroaromatic compound represented by General Formula (1) below and a hydroxy group-containing fluoroaromatic compound represented by General Formula (2) below into a composition containing perfluoro(2-methylene-4-methyl-1,3-dioxolane)

Methodology Applied

Scientific EffectPolymerization inhibition:

Implementation Method 2

maintaining the temperature at 0° C. or lower

Methodology Applied

Scientific EffectThermal stabilization:

Data Source

PatentUS11840522B2Method of stabilizing perfluoro(2-methylene-4-methyl-1,3-dioxolane) and composition containing stabilized perfluoro(2-methylene-4-methyl-1,3-dioxolane)

Publication Date: 2023.12.12 TOSOH CORP

AI summary

A method of stabilizing perfluoro(2-methylene-4-methyl-1,3-dioxolane) (hereinafter simply referred to as a “stabilization method”), including incorporating at least one selected from the group consisting of a hydroxy group-containing fluoroaromatic compound represented by General Formula (1) below and a hydroxy group-containing fluoroaromatic compound represented by General Formula (2) below into a composition containing perfluoro(2-methylene-4-methyl-1,3-dioxolane):(in the formula, R1 to R6 each independently represent one selected from the group consisting of a fluorine atom, a perfluoroalkyl group and a hydroxy group, and at least one of R1 to R6 is a hydroxy group);(in the formula, R7 to R14 each independently represent one selected from the group consisting of a fluorine atom, a perfluoroalkyl group and a hydroxy group, and at least one of R7 to R14 is a hydroxy group).