Organoborane Stabilizer for Polymerizable Composition Storage Stability

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Solution Overview

Problem

Existing polymerizable compositions containing organoborane-amine complexes suffer from premature polymerization due to dissociation, leading to reduced storage stability and adverse effects on bonding durability and color of the cured product, particularly when used with biological hard tissues like teeth.

Innovation Solution

A polymerizable composition comprising an organoborane, an acidic group-free polymerizable monomer, and a stabilizer, such as a Lewis base or a compound with a conjugated electron system, that maintains viscosity below 100 after 48 hours at 45°C, ensuring long-term storage stability and high adhesion to biological hard tissues.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If an organoborane-amine complex is used as a polymerization initiator system, then polymerization can be initiated, but the complex dissociates over time causing premature polymerization and reduced storage stability

Engineering Contradiction:

Improvestorage stabilityVSAvoidcomplex stability

Core Design Contradiction:

ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical parameters of the stabilizer component, specifically using compounds with conjugated electron systems (such as quinone derivatives, phenolic compounds, or carboxylic acid derivatives) that can form stable complexes with organoborane through electron donation, thereby preventing premature dissociation while maintaining可控 polymerization initiation capability

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent introduces a stabilizer as an intermediary substance that mediates between the organoborane and the amine components. This stabilizer forms a protective complex with the organoborane, preventing direct interaction that would lead to premature polymerization, while still allowing controlled initiation when desired

Inventive Principle:

Principle #24Intermediary (Mediator)

2Reliability

If the organoborane-amine complex is used, then polymerization initiation is achieved, but free amine exudes on the cured product surface causing discoloration and reduced bonding durability

Engineering Contradiction:

Improvebonding durabilityVSAvoidfree amine exusion

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent converts the potentially harmful free amine by using a stabilizer that binds to it or prevents its release. The stabilizer components (such as quinone derivatives or phenolic compounds) react with or complex the free amine, transforming it from a harmful exuding substance into a stable complex that remains in the bulk material, thereby preventing surface discoloration and maintaining bonding durability

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

3Productivity

If organoborane is used without sufficient stabilization, then polymerization can proceed, but the composition shows poor long-term storage stability at elevated temperatures

Engineering Contradiction:

Improvepolymerization efficiencyVSAvoidstorage duration

Core Design Contradiction:

ProductivityVSDuration of action of stationary object

Solution Approach 1:

The patent optimizes the concentration ratio between organoborane and stabilizer components, typically maintaining a stabilizer to organoborane ratio that ensures complete stabilization during storage while allowing sufficient active organoborane to remain for effective polymerization initiation. This parameter optimization maintains both long-term storage stability and polymerization efficiency

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 composition achieves superior storage stability and excellent adhesion to biological hard tissues, making it suitable for medical and dental applications without premature polymerization or discoloration.

Implementation Method 1

the stabilizer (C) includes at least one selected from (C1) Lewis bases capable of forming a complex with the organoborane (A)

Methodology Applied

Scientific EffectLewis base complexation:

Implementation Method 2

compounds which have a conjugated electron system, have a diketone structure, and have a hydrogen atom belonging to the conjugated electron system

Methodology Applied

Scientific EffectConjugated electron system stabilization:

Data Source

PatentUS11130864B2Polymerizable composition and kit, and polymerization initiator

Publication Date: 2021.09.28 SUN MEDICAL CO LTD

AI summary

The present invention improves the long-term storage stability of a polymerizable composition including an organoborane and a polymerizable monomer. A polymerizable composition includes (A) an organoborane, (B) an acidic group-free polymerizable monomer, and (C) a stabilizer for the organoborane (A), the composition being such that when the composition, after being allowed to stand at 45° C. for 48 hours, is analyzed with an E-type viscometer at a temperature of 25° C. and a rotational speed of 50 rpm, the ratio of the viscosity after the standing to the viscosity before the standing (viscosity after standing/viscosity before standing) is less than 100.