Fluorine-Containing Ether via Liquid-Phase Fluorination

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Solution Overview

Problem

Current methods for synthesizing fluorine-containing polymers, such as radical polymerization and direct fluorination with fluorine gas, face limitations in achieving homogeneous fluorination and high fluorine content, especially for high molecular weight polymers, due to low solubility issues and surface preferential fluorination.

Innovation Solution

A fluorine-containing ether compound with enhanced fluorine content is achieved by fluorinating a polymer with a repeating unit represented by Formula (I), using liquid-phase direct fluorination with diluted fluorine gas in a solvent saturated with fluorine, allowing for higher fluorine incorporation and improved solubility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Quantity of substance

If direct fluorination of solid polymer with fluorine gas is performed, then fluorine content is increased, but homogeneous fluorination is not achieved due to surface preferential fluorination

Engineering Contradiction:
Improvefluorine contentVSAvoidhomogeneity of fluorination
Core Design Contradiction:
Quantity of substanceVSManufacturing precision

Solution Approach 1:

The patent changes the physical state parameter of the polymer from solid to dissolved state in a fluorinated solvent. This parameter change allows fluorine gas to access and react with polymer chains throughout the bulk solution rather than only at the surface, achieving homogeneous fluorination while maintaining high fluorine content.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a fluorinated solvent as an intermediary medium. The solvent dissolves the polymer and saturates with fluorine gas, creating a fluorinated environment that mediates the fluorination reaction. This intermediary allows uniform distribution of fluorine throughout the polymer solution, preventing surface preferential reaction.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If liquid phase fluorination is performed with high molecular weight polymer, then reaction does not proceed sufficiently due to low solubility in fluorinated solvent

Engineering Contradiction:
Improvereaction extentVSAvoidsolubility
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent modifies the chemical composition parameters of the solvent by selecting specifically fluorinated solvents with appropriate molecular structures. These solvents have enhanced solvating power for high molecular weight polymers while maintaining high fluorine content, enabling both complete reaction and sufficient solubility.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent uses composite solvent systems comprising fluorinated solvents that combine appropriate molecular weight, fluorine content, and solvating properties. This composite approach creates a solvent environment that can dissolve high molecular weight polymers effectively while maintaining the fluorination reaction efficiency.

Inventive Principle:
Principle #40Composite materials

3Stability of the object's composition

If fluorine component is introduced into side chain to improve solubility, then solubility in fluorinated solvent is improved, but fluorine content of produced polymer is not satisfactorily high

Engineering Contradiction:
ImprovesolubilityVSAvoidfluorine content
Core Design Contradiction:
Stability of the object's compositionVSQuantity of substance

Solution Approach 1:

The patent performs preliminary dissolution of the polymer in the fluorinated solvent before conducting the fluorination reaction. This preliminary action ensures complete solvation and accessibility of all polymer chains to fluorine gas, enabling subsequent achievement of high fluorine content throughout the polymer structure without solubility limitations.

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

This method efficiently produces fluorine-containing ether compounds with high fluorine content, exhibiting properties like low refractive index, chemical resistance, and electrical insulation, applicable as transparent materials with improved physical properties.

Implementation Method 1

fluorinating a polymer including a repeating unit represented by the following Formula (I)

Methodology Applied
Scientific EffectFluorination reaction: Chemical Bonding

Data Source

PatentUS8106222B2Fluorine-containing ether compound
Publication Date: 2012.01.31 FUJIFILM CORP
  • US8106222B2 patent drawing
  • US8106222B2 patent drawing
  • US8106222B2 patent drawing

AI summary

A fluorine-containing ether compound with a fluorine content increased, the fluorine content being enhanced by fluorinating a polymer including a repeating unit represented by the following Formula (I):wherein Rh1 represents a divalent linkage group; Rf2 represents an perfluoroalkylene group; each of Rf3 and Rf4 independently represents a fluorine atom, a perfluoroalkyl group or a perfluoroalkoxy group, and any two of Rf2, Rf3 and Rf4 may be combined with each other to form a ring.