Phenolic Fatty Acid Epoxy Curing Agents for Antimicrobial Coatings

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Solution Overview

Problem

Conventional antimicrobial agents face issues with residual toxicity, volatility, and environmental impact, while existing antimicrobial epoxy polymers lack water resistance and are often derived from petroleum-based materials, necessitating the development of bio-based, non-volatile, and effective antimicrobial solutions.

Innovation Solution

The synthesis of phenolic-branched chain fatty acid (PBC-FA) based epoxy curing agents by reacting PBC-FA methyl ester with polyamines, such as ethylenediamine, to create antimicrobial epoxy polymers that can be used in coatings, providing both antimicrobial activity and environmental sustainability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional antimicrobial agents are used, then antimicrobial activity is achieved, but residual toxicity and environmental harm occur

Engineering Contradiction:
Improveantimicrobial activityVSAvoidresidual toxicity
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the molecular weight parameter of antimicrobial agents by incorporating them into polymeric structures. This transformation maintains antimicrobial activity while eliminating residual toxicity issues associated with low molecular weight biocides, as the polymeric form prevents leaching and residual contamination.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite antimicrobial polymers by combining antimicrobial moieties with polymeric backbones. This composite structure integrates the antimicrobial function into the polymer matrix, providing sustained activity without the harmful residual effects of conventional small-molecule biocides.

Inventive Principle:
Principle #40Composite materials

2Reliability

If low molecular weight biocides are used, then antimicrobial effect is achieved, but volatility and chemical instability occur

Engineering Contradiction:
Improveantimicrobial effectVSAvoidchemical stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the physical state and molecular weight parameters by converting small-molecule biocides into polymeric forms. This eliminates volatility while maintaining antimicrobial effectiveness, as the polymeric structure prevents evaporation and enhances chemical stability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent segments the antimicrobial function from the carrier by incorporating antimicrobial moieties into polymeric chains. This segmentation allows the antimicrobial activity to be distributed throughout the polymer structure, providing stable, non-volatile protection.

Inventive Principle:
Principle #1Segmentation

3Reliability

If quaternary ammonium salt-functional epoxy compounds are used, then antimicrobial activity is achieved, but water resistance is lost

Engineering Contradiction:
Improveantimicrobial activityVSAvoidwater resistance
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent applies local quality by incorporating hydrophobic phenolic-branched chain fatty acid structures into the polymer backbone at specific locations. This local hydrophobicity compensates for the hydrophilic nature of curing agents, maintaining overall water resistance while providing antimicrobial activity through the phenolic groups.

Inventive Principle:
Principle #3Local quality

4Reliability

If petroleum-based antimicrobial polymers are used, then antimicrobial performance is achieved, but environmental sustainability is reduced

Engineering Contradiction:
Improveantimicrobial performanceVSAvoidenvironmental impact
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent changes the origin parameter of the polymer materials by replacing petroleum-based feedstocks with renewable plant-derived resources. This substitution maintains antimicrobial performance while improving environmental sustainability through biodegradability and reduced fossil fuel dependency.

Inventive Principle:
Principle #35Parameter changes

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 resulting PBC-FA-based epoxy polymers demonstrate significant antimicrobial activity against both Gram-positive and Gram-negative bacteria, with the phenolic group playing a crucial role in bacterial inactivation, and exhibit improved stability and water resistance, making them suitable for various applications.

Implementation Method 1

The resulting PBC-FA-based epoxy polymers demonstrate significant antimicrobial activity against both Gram-positive and Gram-negative bacteria, with the phenolic group playing a crucial role in bacterial inactivation

Methodology Applied
Scientific EffectAntimicrobial activity:

Implementation Method 2

The synthesis of phenolic-branched chain fatty acid (PBC-FA) based epoxy curing agents by reacting PBC-FA methyl ester with polyamines

Methodology Applied
Scientific EffectChemical bonding: Chemical Bonding

Data Source

PatentUS12012369B2Antimicrobial phenolic fatty acid-based epoxy curing agents for epoxies
Publication Date: 2024.06.18 THE GOVERNMENT OF THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY DEPARTMENT OF HEALTH & HUMAN SERVICES
  • US12012369B2 patent drawing
  • US12012369B2 patent drawing
  • US12012369B2 patent drawing

AI summary

Compositions containing at least one compound of formula Iwhere R1 is a phenolic compound (e.g., simple phenol, creosote, thymol, or carvacrol), and where R2 is a polyamine (e.g., ethylenediamine (EDA), diethylenetriamine (DETA), triethylenetetramine (TETA), tetraethylenepentamine (TEPA), hexamethylenediamine (HDA)); and optionally a carrier; the compositions may additionally contain at least one epoxy resin. Methods for killing microorganisms involving contacting the microorganisms with an effective microorganism killing amount of the above composition. Compositions containing at least one compound produced by a method involving reacting phenolic-branched chain fatty acid methyl ester with at least one polyamine.