Bio-based Linear Alkylphenyl Sulfonates for Cold Water Solubility

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Solution Overview

Problem

The surfactant industry faces challenges with linear alkylphenyl sulfonates due to their poor solubility in cold water and hard water conditions, limited biodegradability, and reliance on non-renewable petroleum-based resources, which are costly and environmentally unsustainable.

Innovation Solution

A method is developed to produce C10-C14 linear alkylphenyl sulfonates using a bio-based approach, involving the dehydration of plant-derived or bioengineered alcohol mixtures to form alkenes, which are then used to alkylate benzene and subsequently sulfonate, resulting in surfactants with a biobased content of at least 50%, improving solubility and biodegradability while reducing reliance on petroleum-based resources.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If linear alkylphenyl sulfonates are used as surfactants, then cleaning performance is improved, but solubility in cold water and hard water deteriorates

Engineering Contradiction:
Improvecleaning performanceVSAvoidsolubility in cold water and hard water
Core Design Contradiction:
ReliabilityVSEase of operation

Solution Approach 1:

The patent changes the molecular structure parameters of the surfactant by introducing ethoxylated groups and modifying the alkyl chain structure. This transforms the traditional linear alkylphenyl sulfonate into an ethoxylated linear alkylphenyl sulfonate, which maintains cleaning performance while improving solubility in cold and hard water through the hydrophilic ethoxylate groups.

Inventive Principle:
Principle #35Parameter changes

2Ease of manufacture

If conventional linear alkylphenyl sulfonates are used, then cost-effectiveness is maintained, but biodegradability deteriorates

Engineering Contradiction:
Improvecost-effectivenessVSAvoidbiodegradability
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent modifies the molecular structure by adding ethoxylated groups and controlling the alkyl chain length and branching. These structural parameter changes enhance biodegradability while maintaining cost-effectiveness through efficient synthesis processes and the use of readily available raw materials.

Inventive Principle:
Principle #35Parameter changes

3Ease of manufacture

If petroleum-based resources are used to produce surfactants, then manufacturing process is established, but environmental sustainability deteriorates

Engineering Contradiction:
Improvemanufacturing processVSAvoidenvironmental sustainability
Core Design Contradiction:
Ease of manufactureVSObject-generated harmful factors

Solution Approach 1:

The patent changes the source of raw materials from petroleum-based to renewable resources such as vegetable oils and animal fats. This substitution maintains manufacturing feasibility while significantly improving environmental sustainability and reducing dependence on non-renewable resources.

Inventive Principle:
Principle #35Parameter changes

4Ease of operation

If solubility of linear surfactants is increased by introducing cosurfactants, then solubility improves, but formulation flexibility deteriorates

Engineering Contradiction:
ImprovesolubilityVSAvoidformulation flexibility
Core Design Contradiction:
Ease of operationVSAdaptability or versatility

Solution Approach 1:

The patent combines the functions of solubility enhancement and surfactant activity into a single molecule by integrating ethoxylated groups directly into the linear alkylphenyl sulfonate structure. This eliminates the need for separate cosurfactants and preserves full formulation flexibility.

Inventive Principle:
Principle #5Merging (Combining)

5Ease of operation

If AES surfactants are used to improve solubility, then solubility improves, but surface activity and mass efficiency deteriorate

Engineering Contradiction:
ImprovesolubilityVSAvoidsurface activity and mass efficiency
Core Design Contradiction:
Ease of operationVSReliability

Solution Approach 1:

The patent merges the hydrophilic ethoxylated groups with the hydrophobic alkylphenyl sulfonate core into a single integrated molecule. This unified structure maintains high surface activity and mass efficiency while providing inherent solubility enhancement, avoiding the performance compromises associated with AES surfactants.

Inventive Principle:
Principle #5Merging (Combining)

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 method enhances the solubility and biodegradability of linear alkylphenyl sulfonates, making them more effective in cleaning products and reducing environmental impact by utilizing renewable resources, thereby addressing the limitations of traditional surfactants.

Implementation Method 1

a mixture of C 10 -C 14 alkenes produced by any convenient method known in the art, for example, by the Fischer-Tropsch synthesis

Methodology Applied
Scientific EffectFischer-Tropsch synthesis: Chemical Bonding

Implementation Method 2

dehydrating a C 10 -C 14 alcohol mixture derived either from plant matter or a bioengineered microorganism to form a mixture of C 10 -C 14 alkenes

Methodology Applied
Scientific EffectDehydration: Chemical Bonding

Data Source

PatentEP2675784B1Bio-based linear alkylphenyl sulfonates
Publication Date: 2017.09.13 PROCTER & GAMBLE CO
  • EP2675784B1 patent drawing
  • EP2675784B1 patent drawing
  • EP2675784B1 patent drawing

AI summary

The invention is directed to mixtures comprising C10-C14 linear alkylphenyl sulfonates with alkyl groups having a biobased content of at least 50%. These C10-C14 linear alkylphenyl sulfonates are used in consumer product cleaning and personal care compositions (e.g., dishcare, laundry, hard surface cleaners, shampoos, conditioners, and soaps). The invention is further directed to a method of making a mixture of partially or wholly bio-based C10-C14 linear alkylphenyl sulfonates with alkyl groups having a particular bio-based content.