Urethane Methacrylate Monomer Stability via Amine Catalyst

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Solution Overview

Problem

There is a need for alternative catalysts to Sn-based catalysts for forming urethane (meth)acrylates to reduce heavy metal usage and improve the stability of these compounds, which are commonly used in curable compositions like dental materials.

Innovation Solution

A monomer composition comprising an acidic phosphoric acid ester, an amine-based catalyst, and a (meth)acrylate with a urethane bond or a —NHC(═S)O— bond, where the (meth)acrylate is a reaction product of an iso(thio)cyanate with a (meth)acrylate having a hydroxy group, is used, along with a curable composition that includes this monomer and a polymerization initiator, to enhance stability and reduce Sn-based catalyst content.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If Sn-based catalysts are used for forming urethane (meth)acrylates, then the synthesis reaction proceeds efficiently, but heavy metal content increases and stability deteriorates

Engineering Contradiction:
Improvestability of urethane (meth)acrylateVSAvoidheavy metal content
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention extracts and removes the harmful Sn-based catalyst from the synthesis system, replacing it with an amine-based catalyst. This eliminates the heavy metal content while maintaining the synthesis functionality, directly resolving the contradiction between stability improvement and heavy metal reduction.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention changes the catalyst type parameter from Sn-based to amine-based, and introduces an acidic phosphoric acid ester to modify the reaction conditions. This parameter change enables the use of non-heavy metal catalysts while improving the stability of the urethane (meth)acrylate product.

Inventive Principle:
Principle #35Parameter changes

2Object-affected harmful factors

If alternative catalysts to Sn-based catalysts are used, then heavy metal content is reduced, but the stability of urethane (meth)acrylate may deteriorate

Engineering Contradiction:
Improveheavy metal contentVSAvoidstability of urethane (meth)acrylate
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The invention uses a composite catalyst system combining amine-based catalyst and acidic phosphoric acid ester together. This composite approach compensates for the potential stability issues of alternative catalysts by creating a synergistic system that maintains both low heavy metal content and high product stability.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The acidic phosphoric acid ester acts as an intermediary substance that facilitates the reaction between the amine-based catalyst and the reactants. This intermediary enables the amine-based catalyst to function effectively while improving the stability of the urethane (meth)acrylate product without introducing heavy metals.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If amine-based catalyst and acidic phosphoric acid ester are used together, then stability is improved, but device complexity increases

Engineering Contradiction:
Improvestability of urethane (meth)acrylateVSAvoidcatalyst system complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The invention merges the amine-based catalyst and acidic phosphoric acid ester into a unified catalytic system. By combining these two components, the system achieves improved stability while the merged nature of the system allows for simplified process control compared to using multiple separate catalyst systems.

Inventive Principle:
Principle #5Merging (Combining)

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 proposed solution provides a stable monomer composition with improved mechanical properties and reduced heavy metal content, suitable for use in dental materials and other applications, by suppressing decomposition and polymerization of the (meth)acrylate, thereby enhancing the performance and safety of the cured products.

Implementation Method 1

an amine-based catalyst (B)

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

an acidic phosphoric acid ester (A)... suppressing decomposition and polymerization of the (meth)acrylate

Methodology Applied
Scientific EffectChemical inhibition:

Data Source

PatentUS12098236B2Monomer composition and production method thereof, raw material composition, curable composition, and molded body
Publication Date: 2024.09.24 MITSUI CHEMICALS INC
  • US12098236B2 patent drawing
  • US12098236B2 patent drawing
  • US12098236B2 patent drawing

AI summary

A monomer composition, including: an acidic phosphoric acid ester (A); an amine-based catalyst (B); and a (meth)acrylate (E) having at least one of a urethane bond or a —NHC(═S)O— bond.