Triazine-Based Polymerizable Resins for Dental Compositions

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Solution Overview

Problem

Dental resins are susceptible to hydrolytic degradation, especially in water and acidic conditions, which affects their long-term performance and durability, leading to a demand for hydrolytic stable and water-soluble polymerizable resins.

Innovation Solution

Development of hydrolytic stable and water-soluble polymerizable resins containing a 1,3,5-hexahydro-1,3,5-triazine moiety, specifically through selective Michael addition reactions to form mono- and di-substituted derivatives, which are then incorporated into dental compositions to enhance stability and solubility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If ester-based (meth)acrylate resin is used for dental applications, then the resin can be processed and applied, but it is susceptible to hydrolytic degradation in water and acidic conditions, reducing long-term performance and durability

Engineering Contradiction:
Improvehydrolytic stabilityVSAvoidlong-term performance
Core Design Contradiction:
ReliabilityVSDuration of action of stationary object

Solution Approach 1:

The patent changes the chemical structure parameter of the resin from ester-based to amide-based (acrylamide) chemistry. This fundamental parameter change transforms the chemical stability profile, making the resin resistant to hydrolytic degradation while maintaining polymerizability and dental application functionality

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite resin systems combining acrylamide-based polymerizable resins with traditional dental resin components. This composite approach integrates the hydrolytic stability of amide bonds with the established performance characteristics of dental resins, achieving both durability and clinical effectiveness

Inventive Principle:
Principle #40Composite materials

2Adaptability or versatility

If N-substituted acrylamide resins are used to improve water solubility, then water solubility increases, but the complexity of synthesis and formulation increases

Engineering Contradiction:
Improvewater solubilityVSAvoidsynthesis complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent modifies the N-substituent parameters of the acrylamide resin to optimize water solubility. By selecting specific hydrophilic groups for N-substitution and controlling the degree of substitution, the resin achieves enhanced water solubility while maintaining manageable synthesis complexity through systematic variation of chemical parameters

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 resulting resins demonstrate improved hydrolytic stability and water solubility, with the ability to form durable dental compositions that maintain performance in challenging conditions, including antimicrobial properties and adjustable refractive index.

Implementation Method 1

selective Michael addition reactions to form mono- and di-substituted derivatives

Methodology Applied
Scientific EffectMichael addition: Chemical Bonding

Data Source

PatentEP3063131B1Methods of making polymerizable resins containing a 1,3,5-hexahydro-1,3,5-triazine moiety
Publication Date: 2018.05.23 DENTSPLY SIRONA INC
  • EP3063131B1 patent drawing
  • EP3063131B1 patent drawing
  • EP3063131B1 patent drawing

AI summary

Disclosed herein are methods of making polymerizable resins containing a 1,3,5-hexahydro-1,3,5-triazine moiety and dental compositions comprising such novel hydrolytic stable, polymerizable resins derived from 1,3,5-triacryloyl-hexahydro-1,3,5-triazine (TAT).