Dental Curable Composition Urethane Hydroxyl Carboxyl Monomers

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Solution Overview

Problem

Dental composite resins used in restorative materials and dental crown prosthesis face limitations in mechanical strength and durability, particularly under high occlusion stress and in oral cavity environments, where they experience mechanical strength degradation and aged deterioration.

Innovation Solution

A dental curable composition comprising a specific blend of polyfunctional (meth)acrylate monomers with urethane bonds, hydroxyl groups, and carboxyl groups, along with an inorganic filler, optimized to enhance mechanical strength and durability by controlling the ratio of these components and their viscosities, ensuring a balanced crosslinked structure.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If polyfunctional radical polymerizable (meth)acrylates such as Bis-GMA, UDMA, and TEGDMA are used to ensure safety and basic mechanical properties, then the material can be used for general dental applications, but the mechanical strength is insufficient for high stress areas like molar teeth

Engineering Contradiction:
Improvemechanical strengthVSAvoidapplication range
Core Design Contradiction:
StrengthVSAdaptability or versatility

Solution Approach 1:

The patent changes the chemical composition parameters by introducing polymerizable monomers with urethane bonds and specific hydroxyl group ratios. The controlled ratio of hydroxyl groups (0.1 to 2.0 times the number of methacryloyl groups) creates a crosslinked structure that significantly improves mechanical strength while maintaining adaptability for various dental applications including high stress areas.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite material system combining polymerizable monomers with urethane bonds, specific hydroxyl group-containing monomers, and inorganic fillers. This composite approach synergistically enhances mechanical strength through the crosslinked network formed by urethane bonds while the inorganic fillers provide additional structural support for high stress applications.

Inventive Principle:
Principle #40Composite materials

2Strength

If polymerizable monomers with urethane bonds are used to enhance mechanical strength, then high strength is achieved, but aged deterioration in water immersion environment becomes intense, reducing durability in oral cavity

Engineering Contradiction:
Improvemechanical strengthVSAvoiddurability
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent precisely controls the parameter of hydroxyl group content, limiting it to 0.1 to 2.0 times the number of methacryloyl groups. This parameter optimization allows the material to achieve high mechanical strength through urethane bond crosslinking while preventing excessive water absorption that would cause intense aged deterioration, thereby improving long-term durability in the oral cavity environment.

Inventive Principle:
Principle #35Parameter changes

3Strength

If the number of hydroxyl groups is increased to enhance mechanical strength through hydrogen bonding, then strength is improved, but water absorption increases leading to intense aged deterioration

Engineering Contradiction:
Improvemechanical strengthVSAvoidwater absorption
Core Design Contradiction:
StrengthVSLoss of substance

Solution Approach 1:

The patent establishes an optimal parameter relationship where the number of hydroxyl groups is controlled to be 0.1 to 2.0 times the number of methacryloyl groups. This controlled ratio ensures sufficient hydrogen bonding for mechanical strength while preventing excessive hydrophilicity that would lead to high water absorption and aged deterioration.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies local quality by strategically positioning hydroxyl groups at specific locations within the polymer chain structure rather than uniformly distributing them. This localized arrangement optimizes hydrogen bonding for strength while minimizing overall hydrophilicity and water absorption tendency.

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 composition achieves superior mechanical strength and durability, maintaining high performance under high occlusion stress and in underwater environments, suitable for dental filling, crown, and CAD/CAM applications.

Implementation Method 1

a dental curable composition using polymerizable monomers, comprising (A) a polymerizable monomer, (B) an inorganic filler, and (C) a polymerization initiator

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Implementation Method 2

methods for considerably enhancing the mechanical strength of dental composite resins has been proposed by utilizing the hydrogen bonds between urethane bonds and hydroxyl groups included in polymerizable monomers

Methodology Applied
Scientific EffectHydrogen bonding: Van der Waals Force

Data Source

PatentEP3363424B1Dental curable composition having high mechanical strength
Publication Date: 2023.10.25 SHOFU INC
  • EP3363424B1 patent drawing
  • EP3363424B1 patent drawing

AI summary

The present invention provides a dental curable composition comprising (A) a polymerizable monomer, (B) an inorganic filler, and (C) a polymerization initiator, wherein the polymerizable monomer (A) comprises (a1) a polyfunctional (meth)acrylate monomer comprising urethane bonds, (a2) a polyfunctional (meth)acrylate monomer comprising hydroxyl groups, and (a3) a polyfunctional (meth)acrylate monomer comprising carboxyl groups, the ratio by weight of (a1):(a2)+(a3) ranges from 1:1 to 9:1, the number of hydroxyl groups is not more than 0.5 relative to the number of (meth)acryloyl groups in one molecule of the above-mentioned (a2), and the number of carboxyl groups is not more than 0.5 relative to the number of (meth)acryloyl groups in one molecule of the above-mentioned (a3).