Polycyclic Amide Dental Composition for Low-Shrinkage Restorations

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Solution Overview

Problem

Dental composite restoration procedures face issues such as enamel fractures, compromised bonding, and post-operative sensitivity due to polymerization shrinkage stress from composite resin polymerization, which existing monomers like (meth)acrylates fail to adequately address.

Innovation Solution

Incorporation of a polymerizable hydrolysis stable polycyclic amide monomer in dental compositions to reduce polymerization stress, using a compound of Formula (I) with specific substituents and structures that enhance polymerization kinetics and stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If (meth)acrylates are used as monomers in dental composite resin, then polymerization kinetics and bonding are improved, but polymerization shrinkage stress increases causing enamel fractures and compromised bonding

Engineering Contradiction:
Improvepolymerization kineticsVSAvoidpolymerization shrinkage stress
Core Design Contradiction:
ProductivityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the chemical structure parameters of the monomer by introducing a polycyclic amide core with specific substituents (R1-R6, X, n, m, Z) to modify polymerization behavior. This structural parameter change reduces polymerization shrinkage stress while maintaining acceptable polymerization kinetics, resolving the contradiction between productivity and harmful factors.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite monomer system combining polycyclic amide structure with polymerizable groups (vinyl, allyl, or (meth)acrylate). This composite approach integrates the low shrinkage advantage of cyclic structures with the kinetic benefits of reactive groups, achieving both reduced shrinkage stress and acceptable polymerization rate.

Inventive Principle:
Principle #40Composite materials

2Object-generated harmful factors

If monofunctional vinylcyclopropane derivatives are used to reduce polymerization stress, then shrinkage stress is reduced, but polymerization kinetic becomes slow

Engineering Contradiction:
Improvepolymerization shrinkage stressVSAvoidpolymerization kinetic
Core Design Contradiction:
Object-generated harmful factorsVSProductivity

Solution Approach 1:

The patent modifies the vinylcyclopropane structure by introducing amide functional groups and specific substituents (R1-R6, X, n, m, Z) to change the chemical parameters. This creates a balance where the cyclic structure provides low shrinkage stress while the amide and substituent parameters enhance polymerization kinetic, resolving the contradiction between reduced stress and slow polymerization.

Inventive Principle:
Principle #35Parameter changes

3Ease of operation

If bulk-fill restorations are implemented to improve ease of operation, then handling is simplified, but polymerization stress management becomes more challenging

Engineering Contradiction:
Improveease of handlingVSAvoidpolymerization stress
Core Design Contradiction:
Ease of operationVSObject-generated harmful factors

Solution Approach 1:

The patent changes the monomer structure parameters (polycyclic amide core with specific substituents) to reduce polymerization shrinkage stress specifically for bulk-fill applications. This allows larger restoration sizes to be placed and cured in single visits without excessive stress, improving ease of operation while managing polymerization stress through chemical modification.

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 use of the hydrolysis stable polycyclic amide monomer significantly reduces polymerization stress, enabling bulk-fill restorations with improved bonding and handling while maintaining esthetic properties.

Implementation Method 1

During polymerization, monofunctional vinylcyclopropane derivatives polymerize with a ring-opening mechanism

Methodology Applied
Scientific EffectPolymerization: Photopolymerisation

Implementation Method 2

the polymerization mechanism is based on intramolecular cyclopropanantion accompanied by a ring opening process

Methodology Applied
Scientific EffectRing-opening:

Implementation Method 3

high radical polymerization reactivity, in particular on photopolymerization

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS12396929B2Dental composition
Publication Date: 2025.08.26 DENTSPLY SIRONA INC
  • US12396929B2 patent drawing
  • US12396929B2 patent drawing
  • US12396929B2 patent drawing

AI summary

Disclosed herein is a dental material containing a polymerizable hydrolysis stable polycyclic amide monomer. The present disclosure relates to methods of making and use of the polymerizable hydrolysis stable polycyclic amide monomer for the preparation of a dental polymerizable hydrolysis stable polycyclic amide monomer composition. The present disclosure further relates to a cured dental material obtained by polymerizing the dental material.