Radically Polymerizable Compound for Self-Etching Dental Adhesion
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Solution Overview
Problem
Current dental materials lack effective adhesion promoters that provide long-term adhesive strength to tooth surfaces without the need for separate etching or priming steps, and existing compounds may not be hydrolysis-stable or easily adaptable for specific dental applications.
Innovation Solution
Development of radically polymerizable compounds with a specific formula (SG)x A((PEI)TG)m, incorporating phosphonic acid groups and polyethyleneimine derivatives, which are hydrolysis-stable and contain multiple radically polymerizable groups for enhanced adhesion and stability, allowing for self-etching and self-priming dental materials.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of operation
If conventional adhesion promoters are used, then adhesion to tooth surfaces is achieved, but separate etching and priming steps are required, increasing treatment time and complexity
Solution Approach 1:
The patent combines etching and adhesion promoter functions into a single compound (Formula I) that contains both phosphonic acid groups for mineral surface bonding and radically polymerizable groups for resin integration. This merging eliminates the need for separate etching and priming steps, allowing one-step application that reduces treatment time and procedural complexity while maintaining effective adhesion to dentin and enamel.
Solution Approach 2:
The adhesion promoter compound of Formula I performs multiple functions simultaneously: it acts as an etching agent through phosphonic acid groups that bond to mineral surfaces, serves as a primer through its spacer group structure, and provides polymerization capability through radically polymerizable groups. This multi-functionality allows a single compound to replace multiple traditional materials and steps in the adhesive protocol.
2Reliability
If existing polymerizable compounds are used, then polymerization is achieved, but hydrolysis stability is insufficient, leading to reduced long-term adhesion
Solution Approach 1:
The patent creates a composite molecular structure (Formula I) that integrates phosphonic acid groups known for their hydrolysis stability and strong mineral surface affinity with radically polymerizable groups and polyethyleneimine spacer groups. This composite structure combines the beneficial properties of different functional groups to achieve both long-term adhesion reliability and resistance to hydrolysis in the oral environment.
Solution Approach 2:
The patent modifies the chemical structure by selecting specific parameters: phosphonic acid groups instead of weaker acid groups for enhanced stability, spacer groups A with specific carbon chain lengths (1-20 carbons) for optimal balance between flexibility and stability, and controlled degrees of polymerization for the polyethyleneimine groups. These parameter optimizations ensure hydrolysis stability while maintaining adhesion performance.
3Adaptability or versatility
If simple adhesion promoters are used, then ease of manufacture is achieved, but adaptability for specific dental applications is limited
Solution Approach 1:
The patent segments the adhesion promoter into distinct functional modules in Formula I: acid groups (SG) for mineral bonding, spacer groups (A) for structural flexibility, polyethyleneimine derivative groups (PEI) for polymerization control, and terminal groups (TG) for customization. This segmentation allows independent optimization of each module and facilitates adaptation to specific dental applications by modifying individual segments without redesigning the entire molecule.
Solution Approach 2:
The patent applies local quality by allowing different regions of the molecule to have specialized functions: phosphonic acid groups specifically for calcium phosphate bonding in enamel and dentin, polyethyleneimine groups with controlled polymerization characteristics for resin integration, and customizable terminal groups for specific application requirements. This localized functional differentiation enhances adaptability while maintaining a systematic manufacturing approach.
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 compounds demonstrate high adhesive strength, maintaining stability during storage and in oral environments, enabling the creation of one-component dental materials that do not require mixing multiple components and can be used in self-etching and self-priming applications.
Implementation Method 1
SG is an acid group or its ester or salt, preferably an acid group that has the ability to adhere to a mineral surface. Preferred acid groups are phosphonic acid groups.
Implementation Method 2
radically polymerizable compounds with a specific formula (SG)x A((PEI)TG)m, incorporating phosphonic acid groups and polyethyleneimine derivatives, which are hydrolysis-stable and contain multiple radically polymerizable groups
Implementation Method 3
The compounds demonstrate high adhesive strength, maintaining stability during storage and in oral environments
Data Source
AI summary
The invention relates to a radically polymerizable compound in which an acid group is linked to a polyethyleneimine group via a spacer group. The polyethyleneimine group has at least one radically polymerizable group in the side chain and/or at the end. The invention further relates to a process for producing such compounds by cationic polymerization of oxazolines, the use of such compounds as a component of a dental material, and a dental material containing the compounds according to the invention.