Disulfide Crosslinked Polyester Resin for Self-Healing Adhesion

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Solution Overview

Problem

Existing crosslinked polyester resins are difficult to recycle and reuse due to their heat-resistant and solvent-resistant properties, and lack self-healing and moldability, as well as effective adhesion to substrates like PET and polyimide films.

Innovation Solution

A crosslinked polyester resin with disulfide bonds is developed, allowing for dynamic covalent crosslinking that enables self-healing and moldability, with a relaxation modulus adjustment through ester and disulfide bond exchanges, and adhesion to substrates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a crosslinked polyester resin is used to achieve high heat resistance and chemical resistance, then the resin exhibits high strength and stability, but it becomes difficult to melt by heat or dissolve in solvents, making recycling and repeated use challenging

Engineering Contradiction:
Improveheat resistance and chemical resistanceVSAvoidrecyclability and reusability
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent introduces dynamic covalent bonds (disulfide bonds and ester bonds) into the crosslinked polyester resin network. These bonds can undergo reversible exchange reactions under specific conditions (heat, catalyst), allowing the resin to transition from a rigid crosslinked structure to a more flexible state that enables melting and reshaping, thus achieving recyclability while maintaining high temperature stability during service

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent utilizes bond exchange reactions that are activated by changing parameters such as temperature and catalyst presence. At service temperatures, the crosslinked structure provides high strength and heat resistance. At processing temperatures with catalyst activation, the bond exchange reactions enable the resin to soften and become processable, allowing for recycling and remolding

Inventive Principle:
Principle #35Parameter changes

2Strength

If a thermosetting resin is used to achieve high adhesion and durability, then the resin provides strong bonding, but it lacks self-healing properties and moldability

Engineering Contradiction:
Improveadhesion strengthVSAvoidself-healing capability and moldability
Core Design Contradiction:
StrengthVSAdaptability or versatility

Solution Approach 1:

The patent incorporates dynamic bond exchange mechanisms that allow the resin to adapt its structure in response to environmental conditions. The disulfide bond exchange and ester bond exchange reactions enable the resin to flow and reconfigure at elevated temperatures, providing moldability, while maintaining strong adhesion at service temperatures through the crosslinked network structure

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent exploits temperature-induced phase transitions and bond exchange reactions to enable self-healing and moldability. When heated to the activation temperature for bond exchange, the resin transitions from a rigid crosslinked state to a softer, more mobile state that allows for reshaping and healing of defects, then returns to the crosslinked state upon cooling, restoring strength and adhesion

Inventive Principle:
Principle #36Phase transitions

3Ease of manufacture

If the activation temperature for bond exchange is lowered to enable self-healing and moldability, then the resin becomes processable at lower temperatures, but the strength and stability at room temperature may be compromised

Engineering Contradiction:
Improveprocessing temperatureVSAvoidroom temperature strength
Core Design Contradiction:
Ease of manufactureVSStrength

Solution Approach 1:

The patent creates a composite crosslinked network containing both disulfide bonds and ester bonds, each contributing different properties. The disulfide bonds provide reversible crosslinking that enables self-healing and moldability at moderate temperatures, while the ester bonds contribute to the overall structural integrity and room temperature strength, creating a synergistic effect that balances processability and mechanical performance

Inventive Principle:
Principle #40Composite materials

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 resin exhibits high strength at room temperature, softens at lower temperatures for self-healing, and adjusts bond exchange temperatures through disulfide bond ratios, facilitating recyclability and effective bonding.

Implementation Method 1

a resin that possesses two types of reactive sites in one polymer chain, one for an ester bond exchange and the other for a disulfide exchange reaction

Methodology Applied
Scientific EffectDisulfide bond exchange: Chemical Bonding

Implementation Method 2

a resin that possesses two types of reactive sites in one polymer chain, one for an ester bond exchange and the other for a disulfide exchange reaction

Methodology Applied
Scientific EffectEster bond exchange: Chemical Bonding

Data Source

PatentEP4678678A1Crosslinked polyester resin having disulfide bond
Publication Date: 2026.01.14 TOYOBO CO LTD
  • EP4678678A1 patent drawing
  • EP4678678A1 patent drawing

AI summary

An object of the present invention is to provide a crosslinked polyester resin that exhibits high self-healing properties, high molding processability while exhibiting high adhesion to resin substrates such as a PET film and a polyimide film. A crosslinked polyester resin having a disulfide bond, obtained by crosslinking a polyester (A) having a carboxy group with an epoxy compound (B). A paint, a coating agent, and an adhesive containing the crosslinked polyester resin. An assembly including a layer containing the crosslinked polyester resin and adherend.