Reverse Acrylate Monomers for Hydrolysis-Resistant Crosslinked Polymers

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Solution Overview

Problem

Current crosslinked acrylate and methacrylate polymers are susceptible to hydrolytic degradation due to internal ester bonds, leading to polymer breakdown and loss of crosslinking, which limits their longevity and mechanical properties in applications such as adhesives, optical lenses, and biomaterials.

Innovation Solution

The development of 'reverse acrylate' monomers with ester bonds flipped relative to the internal crosslinking segment, allowing only pendant side chains to be lost during hydrolysis, thereby maintaining crosslinking integrity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional acrylate or methacrylate monomers are used to form crosslinked polymer networks, then the polymers can be synthesized through standard polymerization mechanisms, but the ester bonds in the crosslinks are susceptible to hydrolytic cleavage, leading to loss of crosslinking and polymer breakdown

Engineering Contradiction:

Improvehydrolytic resistanceVSAvoidcrosslinking integrity

Core Design Contradiction:

ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent inverts the conventional acrylate/methacrylate structure by placing the ester bond externally rather than internally within the crosslink. This structural inversion creates 'reverse acrylate' monomers where the polymerizable double bond is adjacent to the crosslinking segment, while the ester bond is positioned on the pendant side chain. This inversion protects the crosslinking integrity from hydrolytic cleavage while maintaining polymerizability through standard mechanisms.

Inventive Principle:

Principle #13The other way round (Inversion)

2Duration of action of stationary object

If crosslinked polymers are used in applications requiring longevity, then mechanical properties can be achieved, but the presence of internal ester bonds causes progressive hydrolytic degradation that accelerates over time due to acid-catalyzed mechanisms

Engineering Contradiction:

Improvepolymer longevityVSAvoidresistance to hydrolytic degradation

Core Design Contradiction:

Duration of action of stationary objectVSReliability

Solution Approach 1:

The patent extracts the hydrolytically vulnerable ester bond from the internal crosslinking position and relocates it to the external pendant side chain. This extraction removes the source of progressive hydrolytic degradation from the critical crosslinking network, thereby extending polymer longevity while maintaining mechanical properties. The ester bond remains present but is no longer positioned to cause chain scission.

Inventive Principle:

Principle #2Taking out (Extraction)

3Reliability

If conventional crosslinking monomers are used, then crosslinked polymer networks can be formed, but biological agents can enzymatically hydrolyze the ester bonds, accelerating degradation

Engineering Contradiction:

Improveresistance to enzymatic hydrolysisVSAvoidpolymer stability in biological environments

Core Design Contradiction:

ReliabilityVSDuration of action of stationary object

Solution Approach 1:

By inverting the monomer structure to place ester bonds externally, the patent protects the crosslinking network from enzymatic attack. Biological enzymes that target ester bonds in crosslinked polymers can no longer access or cleave the crosslinking esters, as these are replaced by carbon-carbon bonds. The inverted structure thereby confers resistance to enzymatic hydrolysis while maintaining biocompatibility.

Inventive Principle:

Principle #13The other way round (Inversion)

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 reverse acrylate monomers form hydrolytically resistant crosslinked polymer networks that retain mechanical properties and do not lose crosslinking groups during hydrolysis, enhancing the longevity and stability of polymer materials.

Implementation Method 1

crosslinking monomers that form crosslinked polymer networks via a free radical polymerization, an anionic polymerization, a cationic polymerization or other addition polymerization mechanism propagated through carbon-carbon double bonds

Methodology Applied

Scientific EffectFree radical polymerization:

Implementation Method 2

Methodology Applied

Scientific EffectAnionic polymerization:

Implementation Method 3

Methodology Applied

Scientific EffectCationic polymerization:

Data Source

PatentUS11897983B2Hydrolysis-tolerant crosslinked polymers from reverse-acrylate multifunctional monomers

Publication Date: 2024.02.13 TDA RESEARCH INC

AI summary

Crosslink-forming monomers, comprising reverse-acrylate groups, and crosslinked polymer networks formed by the polymerization of monomers that comprise said reverse-acrylate crosslink-forming monomers. Crosslink-forming monomers, comprising reverse-acrylate groups, comprising an alkyl, an aryl, an alkoxyl, and an alkylamino group bridging one or more reverse-acrylate groups. Crosslink-forming monomers, comprising reverse-acrylate groups, comprising an alkyl, an aryl, an alkoxyl, and an alkylamino ester groups. Crosslink-forming monomers, comprising reverse-acrylate groups, comprising alkyl groups where the group is selected from the group consisting of a methyl, an ethyl, a propyl, an n-butyl and a t-butyl. Reverse-acrylate crosslink-forming monomers comprise a chemical structure where the two or more polymerizable carbon-carbon double bonds are connected by a crosslinking group on the opposite side of the hydrolysable ester groups relative to normal crosslinking acrylate monomers. The crosslink-forming monomers herein form crosslinked polymer networks that do not lose their crosslinking upon hydrolysis of the ester linkages.