Cyclic Ether Sophorolipids for pH- and Heat-Stable Surfactants

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Solution Overview

Problem

Lactonic sophorolipids are sensitive to temperature and pH changes, leading to instability and unpredictable properties, limiting their use in environments outside a narrow pH range of about 4-7.

Innovation Solution

The 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 emulsification ability are improved, but stability under varying pH and temperature conditions deteriorates

Engineering Contradiction:

ImprovestabilityVSAvoidapplication range

Core Design Contradiction:

ReliabilityVSAdaptability or versatility

Solution Approach 1:

The patent applies parameter changes by modifying the chemical structure of lactonic sophorolipids through reduction of the lactone carbonyl group to a cyclic ether. This structural parameter change transforms the unstable lactone ring into a stable ether linkage, enabling the surfactant to maintain reliability across extended pH ranges (3-14) and temperatures (up to 100°C) while preserving adaptability for diverse applications.

Inventive Principle:

Principle #35Parameter changes

2Adaptability or versatility

If the pH range is extended beyond 4-7, then application versatility is improved, but chemical stability deteriorates due to hydrolysis

Engineering Contradiction:

ImprovepH rangeVSAvoidchemical stability

Core Design Contradiction:

Adaptability or versatilityVSStability of the object's composition

Solution Approach 1:

The patent converts the harmful susceptibility of the lactone ring to hydrolysis into a benefit by reducing the carbonyl group to form a cyclic ether. This transformation eliminates the hydrolysis vulnerability while maintaining the desired amphiphilic properties, allowing the surfactant to achieve extended pH range adaptability without compromising chemical stability.

Inventive Principle:

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

3Productivity

If temperature is increased, then processing capability is improved, but sophorolipid stability deteriorates

Engineering Contradiction:

Improveprocessing capabilityVSAvoidstability

Core Design Contradiction:

ProductivityVSReliability

Solution Approach 1:

The patent applies parameter changes by transforming the temperature-sensitive lactone structure into a thermally stable cyclic ether through reduction. This structural modification enables the surfactant to maintain reliability at elevated temperatures (up to 100°C), thereby improving processing capability without sacrificing stability.

Inventive Principle:

Principle #35Parameter changes

Data Source

PatentUS20260110011A1Ph- and temperature-stable etheric sophorolipids and their use

Publication Date: 2026.04.23 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.