Multi-Aziridine Compound for Polymer Crosslinking with Reduced Genotoxicity

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Solution Overview

Problem

Existing aziridine crosslinkers, such as trimethylolpropane tris(2-methyl-1-aziridinepropionate), have an unfavourable genotoxic profile, necessitating the development of compounds with reduced genotoxicity and good crosslinking efficiency for applications like coatings and adhesives.

Innovation Solution

A multi-aziridine compound with 2 to 6 structural units, linked by chains and a molecular weight of 840 to 5000 Daltons, featuring reduced genotoxicity and improved crosslinking efficiency, achieved through specific structural units and linking chains.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If trimethylolpropane tris(2-methyl-1-aziridinepropionate) is used as a crosslinking agent, then crosslinking efficiency is improved, but genotoxicity increases

Engineering Contradiction:
Improvecrosslinking efficiencyVSAvoidgenotoxicity
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the molecular weight parameter of the aziridine crosslinker from low (trimethylolpropane tris(2-methyl-1-aziridinepropionate) with MW ~374 g/mol) to a controlled range of 840-5000 Daltons. This parameter change reduces genotoxicity while preserving crosslinking efficiency through multi-aziridine structural units (2-6 aziridinyl groups per molecule).

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining multiple aziridine functional units (2-6 structural units A) connected by linking chains. This composite approach distributes the crosslinking function across multiple units while the overall molecular weight control reduces harmful genotoxic effects, achieving both efficiency and safety.

Inventive Principle:
Principle #40Composite materials

2Object-affected harmful factors

If molecular weight of aziridine compound is increased to reduce genotoxicity, then safety is improved, but crosslinking efficiency may deteriorate

Engineering Contradiction:
ImprovegenotoxicityVSAvoidcrosslinking efficiency
Core Design Contradiction:
Object-affected harmful factorsVSProductivity

Solution Approach 1:

The patent optimizes the molecular weight parameter to a specific range (840-5000 Daltons) that balances two competing requirements: high enough to reduce genotoxicity compared to low molecular weight crosslinkers, but low enough to maintain adequate reactivity and crosslinking efficiency. This precise parameter control resolves the contradiction between safety and performance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention concentrates multiple aziridine reactive units (2-6 structural units A) within a controlled molecular weight range, creating local high reactivity zones while the overall molecular size remains manageable. This local quality approach ensures sufficient crosslinking activity despite the increased molecular weight compared to conventional crosslinkers.

Inventive Principle:
Principle #3Local quality

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 multi-aziridine compound exhibits either weakly positive or no genotoxicity, comparable to natural background levels, while maintaining effective crosslinking performance, thus enhancing safety and efficacy in coatings and adhesives.

Implementation Method 1

compounds with at least two aziridinyl groups which can be used for example for crosslinking of for example carboxylic acid functional polymers

Methodology Applied
Scientific EffectCrosslinking reaction: Chemical Bonding

Data Source

PatentUS12378189B2Multi-aziridine compound
Publication Date: 2025.08.05 COVESTRO NETHERLANDS BV
  • US12378189B2 patent drawing
  • US12378189B2 patent drawing
  • US12378189B2 patent drawing

AI summary

The present invention relates to a multi-aziridine compound having: a) from 2 to 6 of the following structural units (A): whereby R′, R″ are as defined herein m is an integer from 1 to 6; b) one or more linking chains wherein each one of these linking chains links two of the structural units A; and c) a molecular weight in the range from 840 Daltons to 5000 Daltons. The multi-aziridine compound can be used for example for crosslinking of for example carboxylic acid functional polymers dissolved and/or dispersed in an aqueous medium.