TAED Encapsulation via Michael Reaction for Liquid Detergent Stability

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Solution Overview

Problem

Tetraacetylethylenediamine (TAED) loses effectiveness in liquid detergent formulations due to hydrolysis when exposed to water, making it unsuitable for aqueous applications, and there is a need for a method to prepare an active additive suitable for use in water-containing formulations.

Innovation Solution

A method involving the Michael reaction between a compound acting as a Michael donor and a multifunctional acrylate, with a Michael catalyst, to encapsulate the active, resulting in a stable additive with improved solubility and release profile, using acetoacetate esters, cyanoacetate esters, or malonic acid esters as Michael donors and multifunctional acrylates, and an emulsifier to form a stable dispersion.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Ease of operation

If TAED is used in liquid detergent formulations containing water, then the formulation can be liquid and easy to use, but TAED undergoes hydrolysis and loses effectiveness

Engineering Contradiction:
Improveliquid formulation ease of useVSAvoidTAED effectiveness
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent introduces an intermediary encapsulation system (micelle or polymer matrix) that mediates between the water-soluble formulation requirement and the water-sensitive TAED active. The encapsulation structure acts as a barrier that prevents direct contact between TAED and water, allowing the formulation to remain liquid and easy to use while protecting TAED from hydrolysis and maintaining its effectiveness.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The patent employs flexible encapsulating structures such as micelles and polymer films that can be incorporated into liquid detergent formulations. These flexible shells encapsulate TAED particles, providing a protective barrier against hydrolysis while allowing the overall formulation to maintain liquid properties and ease of operation.

Inventive Principle:
Principle #30Flexible shells and thin films

2Reliability

If TAED is encapsulated to prevent hydrolysis, then effectiveness is maintained, but the formulation complexity increases

Engineering Contradiction:
ImproveTAED effectivenessVSAvoidformulation complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent employs self-service encapsulation mechanisms where the encapsulation structure forms automatically under the formulation conditions. For example, micelle formation occurs spontaneously when amphiphilic molecules are introduced to aqueous solutions containing TAED, creating protective structures without requiring complex external intervention or additional processing steps.

Inventive Principle:
Principle #25Self-service

Solution Approach 2:

The patent utilizes parameter changes in formulation conditions (such as pH, temperature, or ionic strength) to control the formation and stability of the encapsulation structure. By adjusting these parameters, the encapsulation can be optimized to protect TAED while minimizing formulation complexity.

Inventive Principle:
Principle #35Parameter changes

3Reliability

If an encapsulation system is used to protect TAED, then hydrolysis is prevented, but the release control becomes more difficult

Engineering Contradiction:
ImproveTAED protection from hydrolysisVSAvoidrelease control
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent employs dynamic encapsulation systems that can adapt their structure based on environmental conditions. The encapsulation structure is designed to remain stable under storage conditions to protect TAED from hydrolysis, but can dynamically change or disrupt under washing conditions to release the active. This dynamic behavior allows simultaneous protection during storage and controlled release during use.

Inventive Principle:
Principle #15Dynamics

Solution Approach 2:

The patent ensures continuous protection of TAED throughout the formulation's lifecycle by designing encapsulation systems that maintain structural integrity during storage and transport, then progressively release the active during the washing process. The encapsulation structure provides continuous protection until the moment of release, ensuring both reliability and controlled release.

Inventive Principle:
Principle #20Continuity of useful action

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 encapsulated active exhibits enhanced stability in aqueous systems, maintaining effectiveness and releasing the active during use, such as in washing machines, with high encapsulating efficiency and controlled release profiles.

Implementation Method 1

a method of encapsulating an active comprising preparing a first mixture comprising the active, a compound that functions as a Michael donor, and a compound that functions as a Michael acceptor

Methodology Applied
Scientific EffectMichael reaction: Chemical Bonding

Implementation Method 2

preparing a second mixture comprising water and an emulsifier; preparing a reaction mixture by combining the first mixture, the second mixture

Methodology Applied
Scientific EffectEmulsion: Emulsion

Implementation Method 3

combining the first mixture, the second mixture, and a compound that functions as a Michael catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Data Source

PatentEP3662049B1Encapsulation method
Publication Date: 2021.05.05 DOW GLOBAL TECHNOLOGIES LLC

AI summary

A method of encapsulating an active comprising preparing a first mixture comprising the active, a compound that functions as a Michael donor, and a compound that functions as a Michael acceptor, preparing a second mixture comprising water and an emulsifier; preparing a reaction mixture by combining the first mixture, the second mixture, and a compound that functions as a Michael catalyst; agitating the reaction mixture; wherein the active has a water solubility of at most 0.5% (w/w) at 25 °C.