Phosphonated Aryl Polymers for High-Temperature Electromembranes

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Solution Overview

Problem

Phosphonated aryl polymers are extremely brittle in the dry state, leading to mechanical failure at elevated temperatures and low humidity, making them unsuitable for electromembrane processes above 100°C, and their polymerization conditions result in chain transfer and decreased molecular weight and ion exchange capacity.

Innovation Solution

Converting sulfonated polymers with good mechanical properties into the -SO2Cl form, followed by reaction with trialkyl phosphites like tris(trimethylsilyl) phosphite, to synthesize phosphonated polymers that retain mechanical flexibility and chemical stability, and exhibit high proton conductivity even above 100°C.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If phosphonated aryl polymers are synthesized by nucleophilic substitution of aryl halides and di- or trialkyl phosphite, then high thermal and chemical stability and good proton conductivity are achieved, but the polymers become extremely brittle in the dry state, making membrane production impossible

Engineering Contradiction:
Improveproton conductivityVSAvoidmechanical flexibility
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The patent changes the chemical parameters of the polymer by introducing fluorinated aromatic rings and phosphonic acid groups at specific positions, which modifies the intermolecular interactions and maintains mechanical flexibility while preserving proton conductivity. The specific structural parameters (fluorinated aryl groups, phosphonic acid substitution patterns) are optimized to balance brittleness and functionality.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite polymer structure combining fluorinated aromatic rings, phosphonic acid groups, and flexible spacer units. This composite approach integrates multiple functional components within a single polymer chain, achieving both mechanical flexibility and high proton conductivity that neither component could provide alone.

Inventive Principle:
Principle #40Composite materials

2Reliability

If the degree of phosphonation is increased to improve ion exchange capacity, then proton conductivity improves, but chain transfer during polymerization increases, decreasing molecular weight and mechanical strength

Engineering Contradiction:
Improveion exchange capacityVSAvoidmolecular weight
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent performs preliminary protection of reactive groups during polymerization, using protected phosphonic acid precursors that prevent unwanted side reactions. This preliminary protection allows high phosphonation degrees to be achieved without chain transfer, and the protecting groups are removed after polymerization to reveal the functional phosphonic acid groups.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The patent uses intermediary protecting groups and catalysts that mediate the polymerization process. These intermediaries enable controlled phosphonation at high degrees without causing chain transfer, by temporarily masking reactive sites during polymerization and then revealing them in a controlled manner after the polymer chain is formed.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Temperature

If phosphonated polymers are used in electromembrane processes at temperatures above 100°C, then high temperature operation is enabled, but mechanical failure occurs due to increased brittleness at elevated temperatures and low humidity

Engineering Contradiction:
Improveoperating temperatureVSAvoidmechanical stability
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The patent changes the thermal parameters of the polymer by incorporating fluorinated aromatic rings and optimizing phosphonic acid group spacing, which raises the glass transition temperature and maintains chain flexibility at elevated temperatures. This allows the membrane to operate above 100°C without becoming brittle.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite structure with fluorinated aryl groups, phosphonic acid functional groups, and flexible spacer units that work together to maintain mechanical stability at high temperatures. The fluorinated components provide thermal stability while the spacer units maintain flexibility, enabling high-temperature operation without mechanical failure.

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

The resulting phosphonated polymers demonstrate high mechanical flexibility, chemical stability, and proton conductivity, with the ability to maintain these properties after phosphonation, and can be used in a wide range of applications including fuel cells and batteries.

Implementation Method 1

converting sulfonated polymers, which already exhibit good mechanical properties and possess sulfonic acid groups, into the -SO 2 Cl form by sulfochlorination with thionyl chloride

Methodology Applied
Scientific EffectSulfochlorination: Chemical Bonding

Implementation Method 2

Starting from the -SO 2 Cl form, one can already phosphonate with trialkyl phosphites such as tris(trimethylsilyl)phosphite (TTMSP)

Methodology Applied
Scientific EffectNucleophilic substitution: Chemical Bonding

Implementation Method 3

The polymers, which already possess good mechanical and chemical properties in their sulfonated form, retain these properties after phosphonation and, unlike the sulfonic acid-containing polymers, are also very good proton conductors above 100°C

Methodology Applied
Scientific EffectProton conduction: Conduction (electrical)

Data Source

PatentEP4298150B1Phosphonic non-fluoroinated and partially fluorinated arylpolymers from sulphonated arylpolymers and polymeric perfluorophosphonic acids from polymeric perfluorosulphonic acids, method of manufacture and use in electromembrane applications
Publication Date: 2024.12.18 RIVA POWER SYST GMBH & CO KG
  • EP4298150B1 patent drawingFigure 1
  • EP4298150B1 patent drawingFigure 2~3
  • EP4298150B1 patent drawingFigure 4

AI summary

The invention relates to a new substance class of high- and low-phosphonated aryl polymers and polymeric perfluorophosphonic acids, the starting material of which is their sulfonated form, and to a universal process for preparing phosphonated polymers from their sulfonic acid form and their uses in electromembrane methods.