Coumarin-Modified Epoxy Adhesive for UV-Reversible Bonding

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Solution Overview

Problem

Epoxy adhesives are difficult to rework or recycle due to their irreversible cross-linking reactions, and adding fluorescent dyes to detect repair work can weaken the adhesive and leach out, compromising mechanical properties.

Innovation Solution

A coumarin-modified epoxy adhesive with a covalently attached fluorescent dye that remains strong and detectable under UV light, synthesized by glycidylation of 7-hydroxycoumarin and epichlorohydrin, which is curable under long-wave UV and reversible under short-wave UV, maintaining adhesive strength and allowing for easy detection.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Difficulty of detecting and measuring

If fluorescent dye is added to epoxy adhesive to enable detection, then detectability is improved, but adhesive strength deteriorates

Engineering Contradiction:
ImprovedetectabilityVSAvoidadhesive strength
Core Design Contradiction:
Difficulty of detecting and measuringVSStrength

Solution Approach 1:

The patent merges the fluorescent dye with the epoxy adhesive matrix by covalent bonding, integrating the detection function into the structural material itself. This eliminates the need for separate dye application and ensures the dye remains permanently embedded in the adhesive, preventing leaching while maintaining detection capability.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent creates a composite material system where fluorescent dye molecules are covalently bonded to epoxy resin chains. This composite structure allows the material to simultaneously exhibit the mechanical properties of epoxy and the optical properties of fluorescent dye, resolving the contradiction between strength and detectability.

Inventive Principle:
Principle #40Composite materials

2Difficulty of detecting and measuring

If fluorescent dye is added to epoxy adhesive to enable detection, then detectability is improved, but dye stability deteriorates

Engineering Contradiction:
ImprovedetectabilityVSAvoiddye stability
Core Design Contradiction:
Difficulty of detecting and measuringVSStability of the object's composition

Solution Approach 1:

The patent merges the fluorescent dye with the epoxy adhesive matrix by covalent bonding, integrating the detection function into the structural material itself. This eliminates the need for separate dye application and ensures the dye remains permanently embedded in the adhesive, preventing leaching while maintaining detection capability.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The patent uses covalent bonds as an intermediary mechanism to attach the fluorescent dye to the epoxy resin. This chemical bonding acts as a permanent anchor, preventing the dye from leaching or extracting from the adhesive matrix, thereby ensuring long-term stability while maintaining detection capability.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Strength

If epoxy adhesive is used for permanent bonding, then bond strength is improved, but reworkability deteriorates

Engineering Contradiction:
Improvebond strengthVSAvoidreworkability
Core Design Contradiction:
StrengthVSEase of repair

Solution Approach 1:

The patent introduces dynamic reworkability to the traditionally static epoxy adhesive system. The adhesive can transition between bonded and unbonded states through UV irradiation, allowing it to be permanently bonded during normal use but reversibly degraded for repair or recycling when needed, thus adding temporal flexibility to the material's properties.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent utilizes photochemical phase transitions to enable reworkability. The adhesive undergoes a reversible transformation between a bonded thermoset state and a degraded monomer state through UV irradiation, allowing the material to cycle between permanent bonding and removable states for repair or recycling applications.

Inventive Principle:
Principle #36Phase transitions

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 coumarin-modified epoxy adhesive exhibits increased adhesive bond strength and fluorescence without weakening the material, enabling easy detection and potential for reworkability, expanding applications in art conservation and consumer markets.

Implementation Method 1

the coumarin-modified epoxy adhesive fluoresces blue under shortwave ultraviolet (UV) radiation

Methodology Applied
Scientific EffectFluorescence: Fluorescence

Implementation Method 2

Epoxy resins are hardened or cured by a cross-linking reaction

Methodology Applied
Scientific EffectCross-linking reaction: Chemical Bonding

Implementation Method 3

the composition is photochemically degradable by UV irradiation at a second range of wavelengths, which causes the cured epoxy adhesive to undergo a reversible photoscission

Methodology Applied
Scientific EffectPhotoscission: Photodissociation

Data Source

PatentUS10723921B2Coumarin-modified epoxy adhesives
Publication Date: 2020.07.28 THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIV OF ARIZONA
  • US10723921B2 patent drawing
  • US10723921B2 patent drawing
  • US10723921B2 patent drawing

AI summary

Coumarin modification of epoxies provide for epoxy adhesives that fluoresce under short wave ultraviolet irradiation while remaining invisible under normal light. Furthermore, these modified epoxy adhesives can have increased adhesive bond strengths. In addition, photochemical curing of an epoxy modified coumarin and a hardening agent with UV irradiation at certain wavelengths affords an epoxy adhesive composition. Further UV irradiation of the composition at certain wavelengths causes photoscission, which breaks the crosslinks that make the cured epoxy adhesive insoluble and intractable.