Etheric Sophorolipid Composition for pH and Heat Stability

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Solution Overview

Problem

Lactonic sophorolipids are susceptible to pH and temperature instability, limiting their use in environments outside a narrow range, which affects the predictability and control of their functional properties.

Innovation Solution

Development of modified sophorolipids with a cyclic ether structure, derived from lactonic sophorolipids, which are more pH- and temperature-stable, reducing HLB values, and enhancing wetting, solubilization, and antimicrobial activities.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If lactonic sophorolipids are used, then surface tension-reducing properties and emulsion stability are improved, but pH and temperature stability deteriorate

Engineering Contradiction:

Improvesurface tension-reducing propertiesVSAvoidpH and temperature stability

Core Design Contradiction:

ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent modifies the chemical structure of lactonic sophorolipids by changing the functional group parameters - specifically replacing the ester linkage with an ether linkage in the cyclic structure. This structural parameter change transforms the molecule from being susceptible to hydrolysis (ester bond cleavage) to being stable against pH and temperature variations, while preserving the cyclic ether structure that provides the desired surface active properties

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining the sophorose head group with a modified cyclic ether-fatty acid tail. This composite structure integrates the hydrophilic carbohydrate portion with a stabilized hydrophobic portion, achieving both the surface activity of lactonic forms and the stability of ether-linked structures

Inventive Principle:

Principle #40Composite materials

2Adaptability or versatility

If the pH range is expanded beyond 4-7, then applicability to diverse industries is improved, but hydrolysis of ester bond increases

Engineering Contradiction:

Improveapplicability to diverse industriesVSAvoidhydrolysis of ester bond

Core Design Contradiction:

Adaptability or versatilityVSObject-generated harmful factors

Solution Approach 1:

The patent converts the harmful ester linkage (prone to hydrolysis) into a beneficial ether linkage that is inherently resistant to hydrolysis. The ether bond replaces the chemically vulnerable ester bond, transforming a structural weakness into a stability advantage, enabling the sophorolipid to function across extreme pH ranges (3-14) without degradation

Inventive Principle:

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

3Adaptability or versatility

If temperature is increased to expand application range, then functional versatility is improved, but ring opening transformation increases

Engineering Contradiction:

Improvefunctional versatilityVSAvoidcyclic structure stability

Core Design Contradiction:

Adaptability or versatilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical bonding parameters within the cyclic structure, replacing the temperature-sensitive ester bond with a thermally stable ether bond. This parameter modification raises the thermal stability threshold of the molecule, preventing ring-opening transformations at elevated temperatures and enabling applications in high-temperature environments

Inventive Principle:

Principle #35Parameter changes

Data Source

PatentUS12516360B2PH- and temperature-stable etheric sophorolipids and their use

Publication Date: 2026.01.06 LOCUS SOLUTIONS IPCO LLC

AI summary

The present invention provides modified sophorolipids of formula (I) that are more pH-and temperature-stable than its lactonic counterparts. Moreover, the compound has reduced HLB parameters, as well as improved wetting and solubilization parameters, water-in-oil emulsification ability, surface tension-lowering activity, and/or antimicrobial activity compared to their acidic or even lactonic counterparts.