Cycloketene Acetal Bone Adhesive via Ring-Opening Polymerization

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Solution Overview

Problem

Traditional medical adhesives, such as cyanoacrylate, face issues with high hardness, poor toughness, toxicity, and refractory degradation, which hinder tissue healing and limit their application in bone adhesion due to lack of biodegradability and osteogenic activity.

Innovation Solution

A fast-curing and degradable strong bone adhesive is developed, comprising a cycloketene acetal compound and a vinyl monomer mixture with a cross-linking agent and reducing agent, which undergoes in-situ free radical ring-opening polymerization, forming a structure with ester bonds for biodegradability and osteogenic activity.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Speed

If traditional cyanoacrylate medical adhesive is used, then fast curing and good instant adhesion strength are achieved, but the polymer product becomes hard and brittle, releasing toxic substances and being difficult to degrade

Engineering Contradiction:
Improvecuring speedVSAvoidtoxicity and refractory degradation
Core Design Contradiction:
SpeedVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the adhesive by replacing cyanoacrylate with cycloketene acetal compounds, fundamentally altering the polymerization mechanism and degradation properties while maintaining fast curing characteristics

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite system by combining cycloketene acetal compound with vinyl monomer, cross-linking agent, and bioactive particles, achieving both fast curing and biodegradability through material composition optimization

Inventive Principle:
Principle #40Composite materials

2Strength

If formaldehyde inhibitor is added to cyanoacrylate medical adhesive, then toughness of adhesive film is improved, but refractory degradation problem still exists

Engineering Contradiction:
ImprovetoughnessVSAvoiddegradation time
Core Design Contradiction:
StrengthVSDuration of action of stationary object

Solution Approach 1:

The patent fundamentally changes the chemical structure from cyanoacrylate to cycloketene acetal, which inherently provides both improved toughness and biodegradability through the ester bond-containing polymer backbone

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent extracts and eliminates the refractory degradation property by removing the cyanoacrylate chemical structure and replacing it with biodegradable cycloketene acetal-based polymer structure

Inventive Principle:
Principle #2Taking out (Extraction)

3Duration of action of stationary object

If natural polymer such as gelatin-based hydrogel is introduced to improve degradability, then biodegradability is achieved, but adhesion and mechanical strength become far less than synthetic adhesives

Engineering Contradiction:
ImprovebiodegradabilityVSAvoidadhesion strength and mechanical strength
Core Design Contradiction:
Duration of action of stationary objectVSStrength

Solution Approach 1:

The patent creates a composite material system combining synthetic cycloketene acetal-based polymer with controlled biodegradability, achieving both high mechanical strength and biodegradability that neither pure natural nor pure synthetic materials can achieve alone

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent introduces local biodegradability through ester bonds in the polymer backbone while maintaining overall structural integrity and mechanical strength through cross-linking and bioactive particle reinforcement

Inventive Principle:
Principle #3Local quality

4Strength

If traditional medical adhesive is used for bone adhesion, then adhesion is achieved, but lack of osteogenic activity hinders bone tissue regeneration

Engineering Contradiction:
Improveadhesion strengthVSAvoidlack of osteogenic activity
Core Design Contradiction:
StrengthVSObject-affected harmful factors

Solution Approach 1:

The patent makes the adhesive multi-functional by incorporating bioactive particles that provide osteogenic activity, transforming it from a simple adhesive into a composite material that simultaneously adheres bone tissue and promotes regeneration

Inventive Principle:
Principle #6Universality (Multi-functionality)

Solution Approach 2:

The patent introduces bioactive particles as intermediary substances that mediate between the adhesive and bone tissue, facilitating osteogenic activity and tissue regeneration while the adhesive provides mechanical bonding

Inventive Principle:
Principle #24Intermediary (Mediator)

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 adhesive achieves rapid adhesion, high mechanical strength, and biodegradability, promoting bone tissue regeneration while avoiding tissue damage and infection, with a simple preparation method and clinical maneuverability.

Implementation Method 1

undergoes in-situ free radical ring-opening polymerization, forming a structure with ester bonds for biodegradability and osteogenic activity

Methodology Applied
Scientific EffectFree radical ring-opening polymerization: Photopolymerisation

Implementation Method 2

The component A comprises a cycloketene acetal compound and an oxidizing agent; The component B comprises a vinyl monomer, a cross-linking agent and a reducing agent

Methodology Applied
Scientific EffectRedox reaction: Redox Reactions

Data Source

PatentUS12194190B2Medical adhesive and preparation method thereof
Publication Date: 2025.01.14 CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY CHINESE ACADEMY OF SCIENCES
  • US12194190B2 patent drawing
  • US12194190B2 patent drawing
  • US12194190B2 patent drawing

AI summary

The present disclosure provides a medical adhesive and a preparation method thereof, comprising a component A and a component B: the component A comprises a cycloketene acetal compound and an oxidizing agent; the component B comprises a vinyl monomer, a cross-linking agent and a reducing agent, wherein the cycloketene acetal compound is selected from one or more of 2-methylene-1,3-dioxepane, 2-methylene-4-phenyl-1,3-dioxolane, 5,6-benzo-2-methylene-1,3-dioxepane and 4,7-dimethyl-2-methylene-1,3-dioxepane. The medical adhesive overcomes the disadvantages of conventional medical adhesives.