CBDO-Based Resin Monomers for Low-Viscosity Dental Composites

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Solution Overview

Problem

Current dental and composite materials based on bis-GMA and bisphenol A derivatives are highly viscous and contain endocrine-disrupting phenolic compounds, requiring reactive diluents like styrene, which are hazardous and pose health concerns.

Innovation Solution

Development of unsaturated mono- or difunctional resin monomers based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol (CBDO), which form curable compositions with lower viscosities and are free from bisphenol A, reducing the need for styrene and minimizing endocrine disruption.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If phenolic compounds (bisphenol A derivatives) are used in cured compositions, then mechanical strength and durability are improved, but health safety deteriorates due to endocrine disruption

Engineering Contradiction:
Improvemechanical strengthVSAvoidendocrine disruption
Core Design Contradiction:
StrengthVSObject-affected harmful factors

Solution Approach 1:

The patent extracts and removes the harmful phenolic compounds (bisphenol A derivatives) from the cured composition while maintaining the beneficial mechanical properties through alternative non-phenolic monomer structures

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the harmful phenolic structure into a beneficial non-phenolic structure that eliminates endocrine disruption while preserving or enhancing mechanical strength and durability properties

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

2Strength

If high viscosity resins are used to achieve proper material properties, then mechanical performance is improved, but ease of operation deteriorates due to poor flowability

Engineering Contradiction:
Improvemechanical performanceVSAvoidflowability
Core Design Contradiction:
StrengthVSEase of operation

Solution Approach 1:

The patent changes the molecular structure parameters of the resin monomers to achieve an optimal balance between viscosity and mechanical performance, creating materials with lower viscosity that maintain proper strength and durability

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If reactive diluents (styrene) are added to reduce viscosity, then ease of operation is improved, but health safety deteriorates due to hazardous emissions

Engineering Contradiction:
ImproveviscosityVSAvoidstyrene emissions
Core Design Contradiction:
Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and eliminates the need for hazardous reactive diluents like styrene by designing monomer systems that achieve proper viscosity and flowability without additional harmful additives

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the harmful styrene diluent system into a beneficial alternative using non-hazardous monomer structures that provide similar or superior flow properties without toxic emissions

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

4Strength

If aromatic rings are included in resin structure for mechanical strength, then strength is improved, but UV transparency deteriorates

Engineering Contradiction:
Improvemechanical strengthVSAvoidUV transparency
Core Design Contradiction:
StrengthVSIllumination intensity

Solution Approach 1:

The patent changes the structural parameters by replacing aromatic rings with non-aromatic alternative structures that maintain mechanical strength while improving UV transparency for better light curing performance

Inventive Principle:
Principle #35Parameter changes

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 CBDO-based resins offer lower viscosity, improved flowability, reduced health risks, enhanced mechanical performance, and UV transparency, enabling better penetration and durability in dental applications and simplified composite formation with reduced styrene emissions.

Implementation Method 1

unsaturated mono- or difunctional resin monomers based on 2,2,4,4-tetramethyl-1,3-cyclobutanediol (CBDO), which form curable compositions

Methodology Applied
Scientific EffectPolymerization:

Data Source

PatentUS11584813B2Unsaturated monomers and oligomers free of phenolics
Publication Date: 2023.02.21 UNIV OF MASSACHUSETTS
  • US11584813B2 patent drawing
  • US11584813B2 patent drawing
  • US11584813B2 patent drawing

AI summary

Various embodiments disclosed relate to a resin having a structure of at least one of Formula I and Formula II: In Formula I or Formula II R1, R3, R4, R5, and R6 can each be independently selected from the group consisting of hydrogen and substituted or unsubstituted (C1-C10)alkyl. R2 is (C1-C10) alkylene. L is a substituted or unsubstituted (C1-C10)alkylene or (C3-C10)cycloalkylene. In Formula I or Formula II, n or m is greater than or equal to 0, and wherein the resin has an average molecular weight of less than 10,000 g/mol.