Thiol-Ene Click Chemistry for Antimicrobial Material Functionalization

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Solution Overview

Problem

Current methods for imparting desirable functionalities to materials, such as antimicrobial properties, face challenges including complex reaction processes, high costs, and environmental concerns, with limited efficacy duration and compatibility with harsh conditions.

Innovation Solution

The process employs thiol-ene click chemistry to react unsaturated compounds with thiol reactants, using environmentally friendly initiators like hydrogen peroxide, to functionalize materials with pendant amino, amido, imino, or hydroxyl groups, enabling the incorporation of functionality imparting groups like antimicrobial agents, under mild conditions.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Duration of action of stationary object

If chemical bonding techniques are used to improve efficacy duration, then the duration of action is improved, but the process complexity and cost increase

Engineering Contradiction:
Improveefficacy durationVSAvoidprocess complexity
Core Design Contradiction:
Duration of action of stationary objectVSDevice complexity

Solution Approach 1:

The patent changes the chemical parameters by using thiol-ene click chemistry with environmentally friendly initiators like hydrogen peroxide instead of traditional complex multi-step bonding processes. This simplifies the procedure while maintaining durable chemical bonding for long-lasting efficacy

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent applies functionalization at specific local sites on material surfaces through thiol-ene reactions, creating localized functional groups that provide sustained efficacy without requiring complex overall process changes

Inventive Principle:
Principle #3Local quality

2Duration of action of stationary object

If traditional chemical bonding processes are used to improve efficacy duration, then the duration of action is improved, but environmental harm increases due to harsh solvents

Engineering Contradiction:
Improveefficacy durationVSAvoidenvironmental harm
Core Design Contradiction:
Duration of action of stationary objectVSObject-generated harmful factors

Solution Approach 1:

The patent converts potentially harmful traditional chemical processes into environmentally benign reactions by using thiol-ene click chemistry with green initiators like hydrogen peroxide, which decomposes into water and oxygen, eliminating harmful solvent waste while maintaining durable bonding

Inventive Principle:
Principle #22Blessing in disguise (Convert harm into benefit)

Solution Approach 2:

The patent uses environmentally friendly, biodegradable initiators and reagents that are inexpensive and break down harmlessly, replacing persistent harmful solvents with short-lived benign substances that decompose into harmless products

Inventive Principle:
Principle #27Cheap short-living objects (Disposable)

3Duration of action of stationary object

If chemical bonding of functional compounds is used to improve efficacy duration, then the duration of action is improved, but the manufacturing cost increases

Engineering Contradiction:
Improveefficacy durationVSAvoidmanufacturing cost
Core Design Contradiction:
Duration of action of stationary objectVSEase of manufacture

Solution Approach 1:

The patent changes the manufacturing parameters by using simple one-step thiol-ene click chemistry reactions that proceed under mild conditions without requiring complex equipment or multiple processing steps, reducing manufacturing costs while achieving durable functionalization

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The thiol-ene click chemistry reactions are self-catalyzing and proceed spontaneously under ambient conditions without requiring expensive catalysts or complex process control, making the manufacturing process more economical and easier to implement

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

This approach results in materials with enhanced and sustained antimicrobial efficacy, suitable for demanding applications, while reducing costs and environmental impact by using low-cost, environmentally preferable reaction conditions and initiators.

Implementation Method 1

The process employs thiol-ene click chemistry to react unsaturated compounds with thiol reactants

Methodology Applied
Scientific EffectThiol-ene click chemistry: Chemical Bonding

Implementation Method 2

using environmentally friendly initiators like hydrogen peroxide

Methodology Applied
Scientific EffectHydrogen peroxide initiation: Hydrogen Peroxide

Data Source

PatentUS20240208946A1Functionalized materials and compounds
Publication Date: 2024.06.27 UNIV OF SOUTH ALABAMA
  • US20240208946A1 patent drawing
  • US20240208946A1 patent drawing
  • US20240208946A1 patent drawing

AI summary

Processes for chemical functionalization of materials are described. The processes generally include chemical reaction between a thiol group of a first compound or material and an alkene group or alkyne group of a second compound or material. Also disclosed are functionalized materials and compounds suitable for functionalizing a material.