Bio-Based Surfactant Chemistry for Water-Miscible Cleaning

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Solution Overview

Problem

Existing surfactants face challenges in achieving high water solubility and miscibility, leading to unsuitable performance in various applications, and there are concerns about the sustainability and environmental impact of traditional materials like cocamide DEA.

Innovation Solution

Development of bio-based surfactants derived from functionalized epoxidized high oleic soybean oil (HOSO) through specific reaction pathways to create compounds with tailored functional groups, ensuring high water miscibility and biobased carbon content, including betaine, hydroxysultaine, and chelating surfactants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If traditional surfactants like cocamide DEA are used, then cleaning performance is achieved, but environmental toxicity and sustainability concerns arise

Engineering Contradiction:
Improveenvironmental toxicityVSAvoidcleaning performance
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent changes the chemical composition parameters by using bio-based fatty acid esters with specific chain lengths (C12-C18) and functional groups (carboxylate, sulfate, sulfonate, carboxylate amide, carboxylate ester) to create surfactants that are both effective and environmentally friendly, replacing traditional petroleum-based surfactants

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite surfactant molecules by combining bio-based fatty acid esters with various functional groups and structures (amphoteric, anionic, nonionic, zwitterionic) to achieve both cleaning effectiveness and environmental sustainability

Inventive Principle:
Principle #40Composite materials

2Productivity

If bio-based surfactants are developed, then sustainability is improved, but water solubility and miscibility challenges arise

Engineering Contradiction:
Improvebiobased carbon contentVSAvoidwater solubility and miscibility
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The patent applies local quality modification by introducing hydrophilic functional groups (carboxylate, sulfate, sulfonate, amide, ester) at specific positions in the molecular structure to enhance water solubility while maintaining the hydrophobic fatty acid chain for cleaning effectiveness

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent changes molecular parameters by selecting specific fatty acid chain lengths (C12-C18) and functional group configurations to optimize the balance between hydrophobicity and hydrophilicity, ensuring high water solubility and miscibility for bio-based surfactants

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If existing surfactant formulations are used, then cleaning applications are satisfied, but high non-biobased carbon content and environmental harm occur

Engineering Contradiction:
Improveenvironmental harmVSAvoidnon-biobased carbon content
Core Design Contradiction:
Object-affected harmful factorsVSQuantity of substance

Solution Approach 1:

The patent uses biodegradable fatty acid ester molecules that can be safely disposed of and broken down in the environment, replacing persistent petroleum-based surfactants with natural, renewable resources that decompose harmlessly

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

Solution Approach 2:

The patent changes the carbon source parameter from petroleum-based to bio-based (plant-derived) fatty acids, increasing biobased carbon content while maintaining effective cleaning performance through optimized molecular structures

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 bio-based surfactants demonstrate equivalent or superior performance in hard surface cleaning, laundry detergents, and oil recovery, while reducing environmental toxicity and reliance on non-renewable resources.

Implementation Method 1

The invention provides a composition, comprising one or more compounds selected from candidates 14-32, 34-48, and 50-55

Methodology Applied
Scientific EffectSurfactant: Surfactant

Implementation Method 2

reacting the epoxide with an alcohol to form an ether

Methodology Applied
Scientific EffectEpoxy ring-opening: Chemical Bonding

Implementation Method 3

reacting with an amide to form a C(O)N moiety

Methodology Applied
Scientific EffectAmide formation: Chemical Bonding

Implementation Method 4

reacting the oleic acid or other oleate in a hydroformylation reaction followed by hydrogenation to form a hydroxymethyl group

Methodology Applied
Scientific EffectHydroformylation: Chemical Bonding

Implementation Method 5

a chelating surfactant comprising a polyether sidechain connected via an ether linkage to the C18 carbon chain moiety or a polyamine sidechain connected via an amine linkage to the C18 carbon chain moiety

Methodology Applied
Scientific EffectChelation: Chemical Bonding

Data Source

PatentUS12351539B2Bio-based surfactants
Publication Date: 2025.07.08 BATTELLE MEMORIAL INST
  • US12351539B2 patent drawing
  • US12351539B2 patent drawing
  • US12351539B2 patent drawing

AI summary

Bio-based surfactants have great opportunity for use in a variety of applications such as laundry detergents, industrial cleaners, adjuvants, and oil & gas. Surfactants in these applications can be nonionic, anionic, cationic, or amphoteric. Utilizing high oleic soybean oil as a platform chemical, a variety of surfactants and properties can be produced. While early work focused solely on surfactant use in laundry cleaning and fracking, recent work has expanded functional groups and application evaluations in hard surface cleaning.The current invention expands on Battelle's high oleic soybean oil (HOSO) surfactant technology. Use of HOSO overcomes the limitations of regular soybean oil and significantly reduces or eliminates undesirable byproducts in most chemistries. However, with use of select reagents, a few candidates were achievable with regular epoxidized soybean oil (ESO). The HOSO surfactant platform offers several key advantages including: a highly water miscible (not typical of C18 surfactants) and water stable surfactant; ability to adjust and vary hydrophilic-lipophilic (HLB) values for stain removal performance; and increased biodegradability without toxic or persistent by-products.