Fluorinated Aryl Epoxide Synthesis for Water Oil Repellents

Solution Overview

Problem

Current methods for producing water and oil repellents and soil resists rely on expensive linear perfluorinated alcohols, necessitating the development of new starting materials that do not utilize these compounds.

Innovation Solution

A fluorinated aryl compound with a pendant epoxy group is synthesized, allowing for the production of polymers suitable for water and oil repellents and soil resists, using a method involving the reaction of perfluorovinyl ethers with functionalized aryl rings in the presence of a base and solvent, followed by epichlorohydrin to create the desired epoxy polymer.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If linear perfluorinated alcohols are used as starting materials, then water and oil repellent properties are achieved, but production cost increases and manufacturing complexity increases

Engineering Contradiction:

Improvewater and oil repellent propertiesVSAvoidproduction cost

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent replaces expensive linear perfluorinated alcohols with cheaper non-linear perfluorinated compounds (branched or cyclic structures) that provide equivalent water and oil repellent properties. This substitution directly addresses the cost issue while maintaining the desired functional performance through alternative molecular geometries

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The invention changes the structural parameters of the perfluorinated compounds from linear to non-linear configurations (branched or cyclic). This parameter change in molecular structure allows achievement of the same repellent properties through different structural arrangements, thereby reducing manufacturing cost and complexity

Inventive Principle:

Principle #35Parameter changes

2Reliability

If linear perfluorinated alcohols are used as starting materials, then water and oil repellent properties are achieved, but synthesis steps increase

Engineering Contradiction:

Improvewater and oil repellent propertiesVSAvoidsynthesis steps

Core Design Contradiction:

ReliabilityVSDevice complexity

Solution Approach 1:

The patent replaces expensive linear perfluorinated alcohols with cheaper non-linear perfluorinated compounds (branched or cyclic structures) that provide equivalent water and oil repellent properties. This substitution directly addresses the cost issue while maintaining the desired functional performance through alternative molecular geometries

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The invention changes the structural parameters of the perfluorinated compounds from linear to non-linear configurations (branched or cyclic). This parameter change in molecular structure allows achievement of the same repellent properties through different structural arrangements, thereby reducing manufacturing cost and complexity

Inventive Principle:

Principle #35Parameter changes

3Ease of manufacture

If new starting materials (non-linear compounds) are used, then production cost decreases, but product performance may be compromised

Engineering Contradiction:

Improveproduction costVSAvoidproduct performance

Core Design Contradiction:

Ease of manufactureVSReliability

Solution Approach 1:

The invention changes the structural parameters of the perfluorinated compounds from linear to non-linear configurations (branched or cyclic). This parameter change in molecular structure allows achievement of the same repellent properties through different structural arrangements, thereby reducing manufacturing cost and complexity

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent employs composite molecular structures combining perfluorinated groups with various hydrocarbon chains and cyclic or branched configurations. These composite structures maintain the essential perfluorinated functionality for repellent properties while incorporating cost-effective non-linear architectural elements

Inventive Principle:

Principle #40Composite materials

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 approach provides a cost-effective and efficient method for producing polymers with water and oil repellent properties, eliminating the need for linear perfluorinated alcohols and enabling the use of non-linear compounds as starting materials for these applications.

Implementation Method 1

contacting a compound of Formula (XV) with one or more compounds of formula (XVI) in the presence of a base and a solvent

Methodology Applied

Scientific EffectCatalysis: Catalysis

Implementation Method 2

The resulting polymers are useful for producing various water and oil repellents

Methodology Applied

Scientific EffectHydrophobe: Hydrophobe

Implementation Method 3

an aryl compound having a fluorinated ether group and a pendant epoxy group

Methodology Applied

Scientific EffectFluorophobic: Hydrophobe

Data Source

PatentUS9193702B2Fluorinated aryl epoxide compounds

Publication Date: 2015.11.24 DUPONT ELECTRONICS INC

AI summary

A fluorinated aromatic epoxy compound having a fluorinated ether tail and a pendant epoxy functional group. These compounds are particularly useful as starting materials for producing various water and oil repellents and soil resists.