Diisocyanate Silane Coupling Agent for Dental Resins

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Solution Overview

Problem

Conventional silane coupling agents used in medical and dental composite resins suffer from low mechanical strength, durability, and water resistance, and require expensive precious metal catalysts, leading to yellowing of the cured material and color stability issues.

Innovation Solution

A novel silane coupling agent with a chemical structure that imparts high affinity to radical polymerizable monomers, featuring urethane bonds and an aliphatic diisocyanate backbone, is used to treat inorganic fillers, eliminating the need for hydrosilylation reactions and allowing for higher temperature urethane reactions in more suitable solvents.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If conventional silane coupling agents (e.g., KBM-503) are used to treat inorganic fillers, then wettability is improved to some extent, but mechanical strength and durability are insufficient due to low hydrophobicity and low filling ratio

Engineering Contradiction:
Improvemechanical strengthVSAvoiddurability
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent changes the chemical parameters of the silane coupling agent by introducing a urethane bond-containing polymerizable monomer structure. This structural modification increases hydrophobicity and improves both mechanical strength and durability simultaneously, resolving the contradiction between strength and reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite structure by combining silane coupling agent with urethane bond-containing polymerizable monomer. This composite molecular structure integrates the adhesion benefits of silane with the hydrophobicity and mechanical properties of urethane polymers, achieving both high strength and durability.

Inventive Principle:
Principle #40Composite materials

2Productivity

If hydrosilylation reaction is used for synthesis of silane coupling agents, then the reaction proceeds efficiently, but expensive precious metal catalysts are required causing yellowing of cured material and color stability issues

Engineering Contradiction:
Improvesynthesis efficiencyVSAvoidyellowing and color instability
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent extracts and eliminates the problematic element (precious metal catalyst) from the synthesis process. By using alternative chemistry that does not require platinum or palladium catalysts, the invention prevents yellowing and color instability while maintaining synthesis efficiency.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces expensive precious metal catalysts with cheaper, non-catalytic or alternative catalytic systems. This substitution eliminates the harmful effects of residual precious metals while keeping the process economically viable.

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Reliability

If long alkyl chain silane coupling agents are used to improve durability and filling rate, then material durability improves, but mechanical strength has room for improvement

Engineering Contradiction:
ImprovedurabilityVSAvoidmechanical strength
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

Instead of merely extending the alkyl chain, the patent changes the fundamental chemical structure by incorporating urethane bonds and polymerizable monomer groups. This structural parameter change provides both durability through hydrophobicity and enhanced mechanical strength through polymer network formation.

Inventive Principle:
Principle #35Parameter changes

4Strength

If fluoroalkylene group silane coupling agents are used to improve wettability, then wettability improves, but water resistance is low and material durability is insufficient

Engineering Contradiction:
ImprovewettabilityVSAvoidwater resistance
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent changes the hydrophobicity parameter by using urethane bond-containing structures with appropriate alkyl chains instead of fluoroalkylene groups. This provides both good wettability and high water resistance, resolving the contradiction between these two properties.

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 solution provides high mechanical strength, flexibility, and pressure-sensitive adhesion to medical and dental curable compositions while ensuring excellent color stability and improved durability without the use of precious metal catalysts.

Implementation Method 1

the urethane reaction between the isocyanate group and the hydroxy group

Methodology Applied
Scientific EffectUrethane reaction: Chemical Bonding

Implementation Method 2

external energy such as photoirradiation is imparted, thus obtaining a radical polymerization cured body

Methodology Applied
Scientific EffectRadical polymerization: Photopolymerisation

Implementation Method 3

there were problems that hydrolysis tends to progress due to low hydrophobicity

Methodology Applied
Scientific EffectHydrolysis: Hydrolysis

Data Source

PatentUS11866590B2Diisocyanate-based radical polymerizable silane coupling compound having an urethane bond
Publication Date: 2024.01.09 SHOFU INC
  • US11866590B2 patent drawing
  • US11866590B2 patent drawing
  • US11866590B2 patent drawing

AI summary

The present invention relates to a novel diisocyanate-based radical polymerizable silane coupling compound having an urethane bond and a medical and/or dental curable composition comprising the same. The present invention provides a novel silane coupling agent that imparts high affinity to a radical polymerizable monomer, thereby imparting high mechanical strength and durability when used for a medical and/or dental curable composition, and an inorganic filler surface-treated with the novel silane coupling agent and a novel medical and/or dental curable composition.