Phase Transfer Catalyst for Dental Material Polymerization

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Solution Overview

Problem

Current polymerizable dental materials face challenges with insufficient polymerization at the interface between adhesives and dental materials, leading to reduced adhesion and prolonged treatment times, especially when used with all-in-one adhesives and Prime + Bond systems, due to interference from phosphoric acid groups and the need for multiple application steps.

Innovation Solution

A polymerizable dental material comprising a catalyst paste with an organic peroxide, filler, and phase transfer catalyst, and a base paste with a free-radically polymerizable monomer, amine co-initiator, and water-soluble reducing agent, which together facilitate rapid and complete curing under oral conditions without premature activation during storage.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If a polymerizable dental material is used with all-in-one adhesives or Prime + Bond systems containing phosphoric acid groups, then adhesion to tooth structure is improved, but polymerization at the interface is insufficient leading to reduced bond strength

Engineering Contradiction:
Improveadhesive bond strengthVSAvoidpolymerization completeness at interface
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent changes the chemical parameters of the initiator system by introducing a redox initiator system (organic peroxide and amine) that operates effectively in the presence of phosphoric acid groups, unlike traditional initiators that are inhibited by these groups. This parameter change enables complete polymerization at the adhesive-dental material interface even when all-in-one adhesives or Prime + Bond systems are used, thereby maintaining high adhesive bond strength without compromising polymerization completeness

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a phase transfer catalyst as an intermediary substance that facilitates the reaction between the organic peroxide and amine in the redox initiator system. This catalyst mediates the interaction between hydrophobic and hydrophilic phases, ensuring effective initiator activation at the interface between the adhesive and dental material, thus resolving the polymerization insufficiency problem while maintaining strong adhesion

Inventive Principle:
Principle #24Intermediary (Mediator)

2Reliability

If traditional initiator systems are used, then storage stability is maintained, but polymerization is incomplete at the interface with adhesives

Engineering Contradiction:
Improvepolymerization completenessVSAvoidstorage stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent segments the initiator system into two separate components: an organic peroxide component and an amine component, which are kept separate during storage to maintain stability. Upon application, these components mix and react through the redox mechanism catalyzed by the phase transfer catalyst, achieving complete polymerization at the interface without compromising storage stability of the individual components

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent creates a composite initiator system combining organic peroxide, amine, and phase transfer catalyst that exhibits both storage stability (due to the stability of individual components when separated) and complete polymerization capability (when mixed and activated). This composite approach resolves the contradiction between maintaining storage stability and achieving complete interfacial polymerization

Inventive Principle:
Principle #40Composite materials

3Strength

If multiple application steps (etching, primer, bonding agent) are used, then adhesion is improved, but treatment time is prolonged

Engineering Contradiction:
Improveadhesive bond strengthVSAvoidtreatment time
Core Design Contradiction:
StrengthVSLoss of time

Solution Approach 1:

The patent merges the functionality of multiple separate application steps (etching, primer, and bonding agent) into a single all-in-one adhesive or Prime + Bond system. The improved redox initiator system with phase transfer catalyst ensures complete polymerization at the interface with this combined adhesive, maintaining high bond strength while reducing treatment time by eliminating multiple separate application and polymerization steps

Inventive Principle:
Principle #5Merging (Combining)

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 ensures adequate curing and improved adhesive bond strength with high storage stability, allowing for efficient use with various adhesives, including Prime + Bond systems and all-in-one adhesives, while maintaining mechanical strength and reducing treatment time.

Implementation Method 1

A polymerizable dental material is disclosed, comprising a catalyst paste (A) and a base paste (B), which, when mixed, form a polymerizable dental material that cures rapidly under oral conditions. The catalyst paste comprises at least one organic per-oxygen compound, and the base paste comprises an amine as a co-initiator of the radical polymerization

Methodology Applied
Scientific EffectRedox reaction: Redox Reactions

Implementation Method 2

At least one catalyst paste and/or base paste contains at least one phase transfer catalyst, which is an ammonium, phosphonium and/or sulfonium salt containing an inorganic or organic anion

Methodology Applied
Scientific EffectPhase transfer catalysis: Catalysis

Implementation Method 3

at least one salt-like, water-soluble, and powdered reducing agent (hereinafter also referred to as: reducing agent) dispersed in the base paste (B). Furthermore, at least one catalyst paste and/or base paste contains at least one phase transfer catalyst

Methodology Applied
Scientific EffectRedox reaction: Redox Reactions

Data Source

PatentEP3267963B1Polymerizable dental material having a phase transfer catalyst
Publication Date: 2020.02.12 KETTENBACH GMBH & CO KG
  • EP3267963B1 patent drawing

AI summary

The invention relates to a polymerizable dental material, containing a catalyst paste (A) and a base paste (B), wherein the catalyst paste (A) contains at least one organic peroxide compound, at least one radically polymerizable organic (meth)acrylic monomer, and at least one filler, and wherein the base paste (B) contains at least one radically polymerizable organic (meth)acrylic monomer, an amine as co-initiator of the radical polymerization, at least one filler, and at least one salt-like, water-soluble, and powdery reducing agent dispersed therein, wherein the catalyst paste (A) and/or the base paste (B) contains at least one phase transfer catalyst, which is selected from the group comprising ammonium salts, phosphonium salts, and/or sulfonium salts, which contain an inorganic or organic anion, with the stipulation that, in the case of organic anions, the phase transfer catalyst has only organic anions having 1-4 carbon atoms and that anions of sulfonic acids are excluded.