Nitrile Oxide Compound with Fluoroalkyl Linker

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Solution Overview

Problem

Conventional nitrile oxide compounds are limited in structure due to synthesis difficulties, and there is no reported method for synthesizing compounds with a fluoroalkyl or fluoropolyether group bonded via a heteroatom to the carbon atom with the nitrile oxide group, which is effective for imparting oil-repellency to base materials.

Innovation Solution

A nitrile oxide compound is developed, represented by formula (I), where a fluoroalkyl or fluoropolyether group is bonded via a heteroatom to the carbon atom with the nitrile oxide group, enabling oil-repellency on base materials.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a nitrile oxide compound with a fluoroalkyl or fluoropolyether group is synthesized to impart oil-repellency, then oil-repellency is improved, but synthesis difficulty increases due to structural complexity

Engineering Contradiction:

Improveoil-repellencyVSAvoidsynthesis difficulty

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The molecule is divided into distinct functional segments: a nitrile oxide group for reactivity, a heteroatom linker for structural flexibility, and a fluoroalkyl or fluoropolyether group for oil-repellency. This segmentation allows each component to be optimized independently while maintaining overall functionality.

Inventive Principle:

Principle #1Segmentation

Solution Approach 2:

The compound combines multiple functional groups with different properties (nitrile oxide for chemical reactivity, heteroatom for structural mediation, fluoroalkyl/fluoropolyether for surface properties) into a single composite molecular structure, achieving multifunctionality that resolves the contradiction between performance and synthesizability.

Inventive Principle:

Principle #40Composite materials

2Reliability

If a substituent containing fluoroalkyl or fluoropolyether group is bonded via heteroatom to the carbon atom with nitrile oxide group, then oil-repellency is enhanced, but molecular stability decreases due to increased reactivity

Engineering Contradiction:

Improveoil-repellencyVSAvoidmolecular stability

Core Design Contradiction:

ReliabilityVSStability of the object's composition

Solution Approach 1:

The heteroatom (oxygen, sulfur, or nitrogen) serves as an intermediary between the highly reactive nitrile oxide group and the fluoroalkyl/fluoropolyether group. This mediator modulates the electronic distribution and steric environment, allowing the nitrile oxide to maintain its reactivity for oil-repellency while the heteroatom provides structural buffering that enhances overall molecular stability.

Inventive Principle:

Principle #24Intermediary (Mediator)

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 compound provides effective oil-repellency to base materials by incorporating a fluoroalkyl or fluoropolyether group bonded via a heteroatom, addressing the structural limitations of conventional nitrile oxide compounds.

Implementation Method 1

Compounds having a nitrile oxide group readily undergo a click reaction ([2+3] addition cyclization reaction) with an unsaturated bond in another compound

Methodology Applied

Scientific EffectClick reaction ([2+3] addition cyclization reaction): Chemical Bonding

Data Source

PatentUS12209062B2Nitrile oxide compound

Publication Date: 2025.01.28 DAIKIN INDUSTRIES LTD

AI summary

The present invention provides a compound represented by formula (I) wherein symbols in the formula are as defined in the specification.