Fluorinated Tensides with Short Chains for Biodegradable Surfactants

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Solution Overview

Problem

Conventional fluorosurfactants are bioaccumulative and toxic, degrading into persistent compounds that accumulate in the food chain and pose health risks, while their alternatives with shorter fluorinated chains often have poorer application properties.

Innovation Solution

Development of new surface-active compounds with specific fluorinated end groups that do not degrade into long-chain persistent compounds, featuring a formula (I) or (I') with a fluorinated alkyl chain attached to a hydrocarbon unit, providing improved surface activity without the environmental and health concerns of traditional fluorosurfactants.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional fluorosurfactants with long perfluorinated alkyl chains (C6-C8) are used, then surface activity and application properties are improved, but bioaccumulation and toxicity increase, and persistent degradation products are formed

Engineering Contradiction:
Improvesurface activityVSAvoidbioaccumulation and toxicity
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chain length parameter of the fluorinated alkyl group from long-chain (C6-C8) to short-chain (C1-C4), which fundamentally alters the degradation behavior and environmental persistence while maintaining surface-active properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces specific structural features (alpha-alkyl substitution and cyclic carboxylate core) at critical positions of the surfactant molecule, creating localized structural qualities that prevent degradation into persistent compounds while preserving surface activity

Inventive Principle:
Principle #3Local quality

2Object-affected harmful factors

If fluorosurfactants with shorter fluorinated chains are used, then environmental properties are improved, but application properties deteriorate

Engineering Contradiction:
Improveenvironmental persistenceVSAvoidapplication properties
Core Design Contradiction:
Object-affected harmful factorsVSReliability

Solution Approach 1:

The patent creates a composite molecular structure combining a short fluorinated alkyl chain (for environmental compatibility) with a cyclic carboxylate core and hydrophilic groups (for surfactant functionality), achieving both environmental safety and application performance

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The patent optimizes the fluorinated chain length to C1-C4 and introduces alpha-alkyl substitution, changing structural parameters that enable short-chain molecules to achieve surface activity comparable to long-chain counterparts

Inventive Principle:
Principle #35Parameter changes

3Reliability

If perfluoroalkyl substituents are used, then surface activity is improved, but degradation into persistent perfluoroalkane carboxylic and sulfonic acids occurs

Engineering Contradiction:
Improvesurface activityVSAvoidenvironmental persistence of degradation products
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent extracts the problematic perfluoroalkyl substituent structure and replaces it with a fluorinated alkyl group attached to a cyclic carboxylate core, eliminating the source of persistent degradation products while retaining fluorine-based surface activity

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent converts the potential harm of fluorinated compounds degrading into persistent substances by designing a structure where fluorinated groups are terminally positioned and sterically protected, transforming them into stable, non-degradable end-groups that provide surface activity without environmental persistence

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

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

These compounds exhibit surface activity comparable to or superior to conventional hydrocarbon surfactants, are biodegradable, and do not form persistent perfluorinated degradation products, offering enhanced environmental properties and improved application efficiency.

Implementation Method 1

Fluorinated surfactants, which have a very low static surface tension (16-20 mN/m), can be used in a wide variety of applications and contribute, for example, to improved surface wetting

Methodology Applied
Scientific EffectSurface tension reduction: Surface Tension

Data Source

PatentEP3107894B1Fluorinated tensides
Publication Date: 2020.02.12 MERCK PATENT GMBH
  • EP3107894B1 patent drawingFigure 1
  • EP3107894B1 patent drawing
  • EP3107894B1 patent drawing

AI summary

The invention relates to novel compounds having fluoridated terminal groups, to the use thereof as surface-active substances, and to agents containing said compounds.