Fluorinated Allyl Xanthate Monomers for Functional Polymer Copolymerization

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Solution Overview

Problem

Existing technologies face challenges in incorporating monomers with functional groups such as —CF2SO3H and —CF2SH into polymers, particularly for applications in fuel cells and electrolysis, due to difficulties in copolymerization and achieving desired functional group placement.

Innovation Solution

The development of a novel monomer comprising a fluorinated allyl xanthate group, which can be used to synthesize polymers with pendant functionalities that can be converted into various functional groups post-polymerization, thereby enabling the creation of polymers tailored for specific applications.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If monomers bearing —CF2SO3H and —CF2SH side chain functional groups are introduced directly into polymerization, then polymers with desired functionality can be obtained, but the copolymerization process becomes extremely difficult and may not proceed in the desired manner

Engineering Contradiction:
Improvefunctionality of polymerVSAvoidcopolymerization process
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies preliminary action by introducing a protecting group (xanthate) onto the functional monomer before polymerization. This allows the monomer to be incorporated into the polymer chain without the problematic functional groups interfering with copolymerization. The functional groups are then revealed after polymerization through removal of the protecting group, thus achieving the desired functionality without manufacturing difficulties.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

The xanthate group serves as an intermediary that temporarily masks the problematic —CF2SO3H and —CF2SH functional groups during polymerization. This intermediary protecting group enables successful copolymerization by preventing direct interaction of the functional groups with the polymerization process, while still allowing the monomer to be incorporated. After polymerization, the intermediary is removed to reveal the desired functional groups.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Manufacturing precision

If functional monomers are placed periodically along the polymer chain or functionality is introduced post-polymerization, then specific functionality can be achieved, but the process complexity increases

Engineering Contradiction:
Improvefunctionality placementVSAvoidpolymerization process
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent uses preliminary action by pre-equipping the monomer with the functional group masked by a protecting group. This allows the functionality to be incorporated into the polymer chain in a single polymerization step without requiring complex post-polymerization modifications or precise periodic placement strategies, thereby reducing process complexity while maintaining manufacturing precision.

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 approach allows for the production of polymers with enhanced electrochemical performance and mechanical properties, particularly suitable for fuel cell and electrolysis applications, by facilitating the incorporation of functional groups that improve system efficiency and durability.

Implementation Method 1

The Applicant has found a novel monomer, more specifically a monomer comprising a fluorinated allyl xanthate, which can be used for the synthesis of polymers bearing pendant functionalities

Methodology Applied
Scientific EffectPolymerization:

Implementation Method 2

Polymer (P) may suitably be subjected to chemical transformations in order to convert the —S(═S)ORb groups present in the recurring units deriving from compound (AX) into different functional groups

Methodology Applied
Scientific EffectChemical transformation:

Data Source

PatentUS20250154296A1Method for preparing functionalized polymers
Publication Date: 2025.05.15 SOLVAY SPECIALTY POLYMERS ITALY SPA
  • US20250154296A1 patent drawing
  • US20250154296A1 patent drawing
  • US20250154296A1 patent drawing

AI summary

The present invention provides compounds that include a fluorinated allyl xanthate group of formula (I). The invention also relates to a process for making these compounds and the use of said compounds as chain transfer agents or as monomers. The invention relates also to polymers, including copolymers, comprising units deriving from compounds of formula (I).