Tannic Acid Curing Agent for Epoxy Toughening

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Solution Overview

Problem

Current epoxy resin curing agents are primarily derived from petroleum resources and lack sustainability, and existing toughening methods face challenges such as poor compatibility between resin and toughening agents, leading to issues like demulsification and high viscosity requirements.

Innovation Solution

A tannic acid curing agent is developed using bio-based materials, specifically prepared through a method involving substitution and addition reactions with 10-undecenoyl chloride, mercapto compounds, and photoinitiators under ultraviolet irradiation, which introduces a long fatty chain and improves network mobility.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If traditional petroleum-based curing agents are used, then the curing performance is reliable, but the sustainability and renewability are poor

Engineering Contradiction:
Improvecuring performanceVSAvoidsustainability
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention changes the chemical composition parameters of the curing agent by replacing petroleum-based materials with tannic acid (a natural polyphenol) as the primary curing agent and incorporating long-chain fatty acid mercapto compounds as reactive toughening agents. This substitution maintains curing performance while achieving sustainability goals with 85-93% renewable carbon content.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite curing agent system combining tannic acid with long-chain fatty acid mercapto compounds (such as ricinoleic acid, linoleic acid, or oleic acid). This composite approach leverages the crosslinking capability of tannic acid and the toughening effect of the mercapto compounds, achieving both reliable curing performance and improved toughness while maintaining sustainability.

Inventive Principle:
Principle #40Composite materials

2Strength

If toughening agents are added to epoxy system, then the toughness is improved, but the compatibility problems arise leading to demulsification and shrinkage cavities

Engineering Contradiction:
ImprovetoughnessVSAvoidcompatibility
Core Design Contradiction:
StrengthVSStability of the object's composition

Solution Approach 1:

The invention merges the curing agent and toughening agent functions into a single integrated system. The long-chain fatty acid mercapto compounds serve dual purposes: they act as reactive toughening agents that incorporate into the crosslinking network and as compatibility promoters that ensure uniform mixing with epoxy resin, eliminating demulsification and shrinkage cavity issues.

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The long-chain fatty acid mercapto compounds act as intermediaries between the polar epoxy resin and the non-polar toughening agents. Their molecular structure contains both polar groups (mercapto and carboxyl) that can interact with epoxy and non-polar long chains that provide toughness, facilitating compatibility and preventing phase separation.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Ease of operation

If reactive toughening agents are used to introduce flexible segments, then the network mobility is increased, but the viscosity becomes excessively high

Engineering Contradiction:
Improvenetwork mobilityVSAvoidviscosity
Core Design Contradiction:
Ease of operationVSForce

Solution Approach 1:

The invention optimizes the molecular weight and chain length parameters of the mercapto compounds used. By selecting long-chain fatty acid mercapto compounds with specific carbon chain lengths (C18-C22), the invention achieves sufficient network mobility for toughness while controlling viscosity to remain manageable for processing, avoiding the excessively high viscosity problem.

Inventive Principle:
Principle #35Parameter changes

4Adaptability or versatility

If bio-based raw materials are used instead of petroleum materials, then the renewability is improved, but the performance consistency becomes challenging

Engineering Contradiction:
ImproverenewabilityVSAvoidperformance consistency
Core Design Contradiction:
Adaptability or versatilityVSReliability

Solution Approach 1:

The invention applies local quality control by selecting specific mercapto compounds from natural sources with well-defined molecular structures (ricinoleic acid, linoleic acid, oleic acid). Each component has controlled purity and composition, ensuring consistent performance while maintaining the renewable nature of the materials.

Inventive Principle:
Principle #3Local quality

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 tannic acid curing agent significantly enhances the toughness of epoxy resins, with deformation under stress reaching 60% at 5.5 MPa, and its renewable carbon content reaches 85-93%, facilitating mass production and improved compatibility.

Implementation Method 1

mixing tannic acid, 10-undecenoyl chloride, a catalyst and a solvent for a substitution reaction to obtain undecylenyl tannic acid

Methodology Applied
Scientific EffectSubstitution reaction: Chemical Bonding

Implementation Method 2

mixing the undecylenyl tannic acid, a mercapto compound, the solvent and a photoinitiator for an addition reaction under an ultraviolet irradiation to obtain the tannic acid curing agent

Methodology Applied
Scientific EffectAddition reaction: Chemical Bonding

Implementation Method 3

mixing the undecylenyl tannic acid, a mercapto compound, the solvent and a photoinitiator for an addition reaction under an ultraviolet irradiation

Methodology Applied
Scientific EffectPhotopolymerization: Photopolymerisation

Data Source

PatentUS11447458B2Tannic acid curing agent and preparation method and application thereof
Publication Date: 2022.09.20 JIANGXI SCI & TECH NORMAL UNIV
  • US11447458B2 patent drawing
  • US11447458B2 patent drawing
  • US11447458B2 patent drawing

AI summary

A tannic acid curing agent and a preparation method thereof are provided. The present invention uses tannic acid as a raw material and the long fatty chain of 10-undecenoyl chloride is introduced into the tannic acid structure to obtain the tannic acid curing agent. The preparation method includes the following steps: mixing tannic acid, 10-undecenoyl chloride, a catalyst and a solvent for a substitution reaction to obtain undecylenyl tannic acid, in which the catalyst includes an acid binding agent and 4-diaminopyridine, and the solvent includes ethyl acetate and N,N-dimethylformamide; mixing the undecylenyl tannic acid, a mercapto compound, a solvent and a photoinitiator for an addition reaction under an ultraviolet irradiation to obtain the tannic acid curing agent, in which the mercapto compound is a mercapto carboxylic acid compound or a mercapto alcohol compound.