Reversible-Bond Glycidyl Ether Resin for Repair and Remolding

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Solution Overview

Problem

Existing epoxy resin-based cured products face issues with low long-term reliability, poor recyclability, and environmental waste due to their insolubility and lack of repairability and remoldability, with existing solutions like reversible bonds being limited to gel-like substances with poor mechanical strength.

Innovation Solution

A glycidyl ether group-containing compound with specific structural units linked by reversible bonds having a dissociation temperature of 120°C or higher, such as Diels-Alder reactions and disulfide bonds, is used in a curable resin composition to enable repairability and remoldability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If epoxy resin is used to achieve excellent heat resistance and mechanical strength, then the cured product has good performance, but it becomes insoluble and unmeltable, resulting in poor recyclability and waste

Engineering Contradiction:
Improvemechanical strengthVSAvoidrecyclability
Core Design Contradiction:
StrengthVSReliability

Solution Approach 1:

The patent introduces reversible bonds with specific dissociation temperatures into the cured product structure. By controlling the dissociation temperature parameter (set at 120°C or higher), the material transitions from permanently crosslinked to dynamically reversible, enabling recyclability while maintaining strength at operating temperatures.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent transforms the static, permanent crosslinks of traditional epoxy into dynamic reversible bonds that can break and reform. This dynamic characteristic allows the cured product to be remolded and recycled while maintaining mechanical integrity during service life.

Inventive Principle:
Principle #15Dynamics

2Reliability

If reversible bonds are introduced to achieve repairability and remoldability, then the cured product can be reused, but the raw materials are limited to gel-like substances with poor mechanical strength

Engineering Contradiction:
ImproverepairabilityVSAvoidmechanical strength
Core Design Contradiction:
ReliabilityVSStrength

Solution Approach 1:

The patent creates a composite structure combining traditional epoxy resin with reversible bond-containing compounds. This composite approach allows the system to exhibit both the mechanical strength of epoxy and the repairability of reversible bonds, overcoming the limitation of gel-like substances alone.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent introduces reversible bonds at specific locations within the cured product network rather than throughout the entire structure. This localized approach allows different regions to have different properties: high strength where epoxy dominates and reversibility where the reversible bonds are present, enabling both strength and repairability.

Inventive Principle:
Principle #3Local quality

3Ease of repair

If a compound with thermal degradability is blended to enable disassembly by heating, then the adhesive strength is reduced for disassembly, but the overall recyclability of the adhesive remains insufficient

Engineering Contradiction:
ImprovedisassemblyVSAvoidrecyclability
Core Design Contradiction:
Ease of repairVSReliability

Solution Approach 1:

The patent enables the cured product to self-disassemble through the inherent reversibility of the bonds when heated. The reversible bonds automatically break at their dissociation temperature, eliminating the need for external degradation compounds and enabling direct recycling of the adhesive material.

Inventive Principle:
Principle #25Self-service

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 cured product achieves extended service life and reduced waste through repairability and remoldability, maintaining mechanical strength and flexibility.

Implementation Method 1

the reversible bond is any one of an addition-type structure by a Diels-Alder reaction

Methodology Applied
Scientific EffectDiels-Alder reaction: Chemical Bonding

Implementation Method 2

the reversible bond is any one of an addition-type structure by a Diels-Alder reaction, all of which have a dissociation temperature of 120°C or higher

Methodology Applied
Scientific EffectRetro-Diels-Alder reaction: Chemical Bonding

Implementation Method 3

the reversible bond is a disulfide bond sandwiched between aromatic rings

Methodology Applied
Scientific EffectThermal decomposition: Thermolysis

Data Source

PatentUS20250277081A1Glycidyl ether group-containing compound, curable resin composition, cured object, and laminate
Publication Date: 2025.09.04 DIC CORP
  • US20250277081A1 patent drawing
  • US20250277081A1 patent drawing
  • US20250277081A1 patent drawing

AI summary

There is provided a compound which, while being a curable resin, can easily exhibit repairability and remoldability when being in the form of a cured product, a curable resin composition obtained using the same, and a cured product thereof. A glycidyl ether group-containing compound is used, in which a structural unit A having one or more glycidyl ether groups and a structural unit B different from the structural unit A are linked in A-B-A, and the structural unit A and the structural unit B are bonded by a reversible bond having a dissociation temperature of 120° C. or higher. This reversible bond is preferably an anthracene-type addition-type structure formed by a Diels-Alder reaction or a disulfide bond sandwiched between aromatic rings.