Azide-terminated Fluoropolymer Synthesis via Mixed Solvent TRIZ Case

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Solution Overview

Problem

There is a lack of an effective method for terminal modification of fluoropolymers, particularly for large-size parts and heat-sensitive applications, as existing methods face challenges with solubility and side reactions when introducing azide groups at both ends of the molecular chain.

Innovation Solution

A method involving a fluoropolymer capped with a hydroxymethyl group, protected with a sulfonyl ester group, reacted with sodium azide in a mixture of non-fluorinated and partially or fully fluorinated organic solvents to achieve an azide group-containing fluoropolymer with a specific molecular structure, enhancing compatibility and reaction efficiency.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of manufacture

If a fluoropolymer is reacted with sodium azide in a non-fluorinated organic solvent to introduce azide groups, then the reaction can proceed, but the solubility of the fluoropolymer is poor and side reactions occur

Engineering Contradiction:
Improvereaction feasibilityVSAvoidsolubility and side reactions
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent changes the solvent parameter from pure non-fluorinated organic solvent to a mixed solvent system comprising non-fluorinated organic solvent and fluorinated organic solvent. This parameter change improves both solubility (reducing side reactions) and maintains reaction feasibility, resolving the technical contradiction between ease of manufacture and reliability.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If existing terminal modification methods are used for fluoropolymers, then some modifications are achievable, but they face challenges with solubility and side reactions when introducing azide groups

Engineering Contradiction:
Improvemodification capabilityVSAvoidsolubility and side reactions
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent modifies the solvent parameter by introducing a mixed solvent system with specific fluorinated and non-fluorinated organic solvents. This enables reliable azide group introduction while maintaining the versatility of terminal modification for fluoropolymers, resolving the contradiction between adaptability and reliability.

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If azide groups are introduced at both ends of the molecular chain, then the polymer can be used for crosslinking applications, but solubility problems and side reactions occur during the process

Engineering Contradiction:
Improvecrosslinking application potentialVSAvoidsolubility and side reactions
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The patent employs a mixed solvent system comprising fluorinated organic solvent and non-fluorinated organic solvent in specific proportions. This parameter change ensures the fluoropolymer remains soluble during azide group introduction at both ends of the molecular chain, enabling crosslinking applications while preventing side reactions, thus resolving the contradiction between versatility and reliability.

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 approach allows for the quantitative preparation of azide group-containing fluoropolymers with improved solubility and reaction rates, reducing side reactions and enabling their use in crosslinking applications requiring chemical and oil resistance.

Implementation Method 1

reacted with sodium azide in a mixture of non-fluorinated and partially or fully fluorinated organic solvents to achieve an azide group-containing fluoropolymer

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Data Source

PatentUS10822456B2Azide group-containing fluoropolymers and method for preparing the same
Publication Date: 2020.11.03 SHIN ETSU CHEMICAL CO LTD
  • US10822456B2 patent drawing
  • US10822456B2 patent drawing
  • US10822456B2 patent drawing

AI summary

An azide group-containing fluoropolymer of formula (1) having a perfluoropolyether group of specific molecular structure as the backbone and terminated with an azide group via methylene group is provided.N3—CH2—Rf1—CH2—N3  (1)