Amine-Containing Polymer Compositions Using ADAMS and ACAMP Monomers

Resolve Bottlenecks,
Find Innovative SolutionsGenerate Solutions

Solution Overview

Problem

Existing methods face challenges in reliably synthesizing and polymerizing styrenic monomers with nitrogen-containing groups pendant to the phenyl ring, leading to propagation issues and inefficiencies in polymerization reactions.

Innovation Solution

Anionic polymerization of addition-polymerizable monomer compositions, specifically focusing on alpha-substituted functional monomers with nitrogen-containing moieties, such as amine-derivatized alpha-methyl styrene (ADAMS) and aminated conjugated aliphatic methylated polyene (ACAMP), to achieve nitrogen-containing functionality without being pendant to the phenyl ring.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If styrenic monomers with nitrogen-containing groups pendant to the phenyl ring are synthesized and polymerized, then nitrogen-containing functional polymers can be produced, but propagation issues occur and synthesis reliability deteriorates

Engineering Contradiction:

Improvesynthesis reliabilityVSAvoidpolymerization propagation efficiency

Core Design Contradiction:

ReliabilityVSProductivity

Solution Approach 1:

The patent extracts the nitrogen-containing functional group from the conventional styrenic monomer structure and relocates it to an allylic position in the side chain, separating the nitrogen functionality from the phenyl ring. This structural extraction eliminates the propagation issues caused by amine groups directly attached to the phenyl ring while preserving the desired nitrogen-containing functional polymer product.

Inventive Principle:

Principle #2Taking out (Extraction)

Solution Approach 2:

Instead of attaching nitrogen-containing groups to the phenyl ring of styrenic monomers (conventional approach), the patent inverts the structural arrangement by placing the nitrogen-containing group in the allylic position of the side chain. This inversion resolves the propagation problems while maintaining polymerization functionality.

Inventive Principle:

Principle #13The other way round (Inversion)

2Productivity

If post-polymerization chemical reactions are used to add amine groups, then propagation issues are avoided, but manufacturing complexity and reaction reliability deteriorate

Engineering Contradiction:

Improvepolymerization propagation efficiencyVSAvoidsynthesis process complexity

Core Design Contradiction:

ProductivityVSDevice complexity

Solution Approach 1:

The patent incorporates the nitrogen-containing functional group into the monomer structure before polymerization occurs. By pre-installing the allylic amine group in the monomer synthesis step, the patent eliminates the need for subsequent post-polymerization chemical reactions, thereby reducing manufacturing complexity while maintaining propagation efficiency.

Inventive Principle:

Principle #10Preliminary action

3Reliability

If conventional styrenic monomers with pendant amine groups are used, then nitrogen-containing polymers can be formed, but synthesis and polymerization reliability deteriorate

Engineering Contradiction:

Improvepolymerization reliabilityVSAvoidmonomer synthesis ease

Core Design Contradiction:

ReliabilityVSEase of manufacture

Solution Approach 1:

The patent extracts the nitrogen-containing group from the phenyl ring position and relocates it to the allylic position of the side chain. This structural extraction simplifies both monomer synthesis and polymerization processes, improving overall manufacturing ease while maintaining polymer reliability.

Inventive Principle:

Principle #2Taking out (Extraction)

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 efficient polymerization of functional polymers with nitrogen-containing groups, overcoming propagation issues and providing a simpler, more reliable synthesis method.

Implementation Method 1

Anionic polymerization of addition-polymerizable monomer compositions, specifically focusing on alpha-substituted functional monomers with nitrogen-containing moieties

Methodology Applied

Scientific EffectAnionic polymerization:

Data Source

PatentEP4596661A1Amine containing polymer compositions and uses thereof

Publication Date: 2025.08.06 INFINEUM INT LTD

AI summary

Disclosed herein are amine containing polymer compositions based on anionic polymerization of monomer compositions including an amine-derivatized alpha-methyl styrene (ADAMS) monomer according to structure (I) and/or an aminated conjugated aliphatic methylated polyene (ACAMP) monomer according to structure (II): with k, R, R1, R2, R3, and R4 defined herein. Also provided are amine containing polymer compositions based on anionic polymerization of difunctional monomers of these types with two polymerizable loci and/or two amine loci. Further disclosed herein are methods for using such polymer compositions.