Fluorinated Ethoxylated Polyurethanes for Stable Surface Modification

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Solution Overview

Problem

Existing fluorinated ethoxylated surfactants with longer perfluoroalkyl chains are costly and inefficient, while those with shorter chains lack effective surface modification capabilities, and most surfactants are not stable in acidic, basic, or brine solutions, which limits their application in coatings, foaming, and oil field operations.

Innovation Solution

Development of fluorinated ethoxylated polyurethanes with C1 to C6 perfluoroalkyl chains, specifically compounds of Formula 1, which are synthesized by reacting perfluorinated alcohols with polyisocyanates, providing stability and effective surface modification in acidic, basic, and brine environments, and exhibiting fast foam disintegration.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If longer perfluoroalkyl chains are used in fluorinated ethoxylated surfactants, then effective surface modification properties are achieved, but production cost increases significantly

Engineering Contradiction:
Improvesurface modification capabilityVSAvoidproduction cost
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent changes the chemical structure parameters by introducing polyurethane linkages and specific ether groups into the surfactant molecule. This structural modification allows shorter perfluoroalkyl chains (C1-C6) to achieve the same surface modification effectiveness as longer chains, thereby reducing production cost while maintaining reliability.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite molecular structure combining perfluoroalkyl groups with polyurethane and ether segments. This composite architecture enables the shorter perfluoroalkyl chains to work synergistically with the polyurethane backbone, achieving effective surface modification without requiring long chain lengths, thus resolving the cost-effectiveness contradiction.

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If shorter perfluoroalkyl chains are used to reduce cost, then production cost decreases, but surface modification capability is insufficient

Engineering Contradiction:
Improveproduction costVSAvoidsurface modification capability
Core Design Contradiction:
Ease of manufactureVSReliability

Solution Approach 1:

The patent modifies the molecular parameters by incorporating polyurethane linkages and ether groups that enhance the surface activity of shorter perfluoroalkyl chains. These structural changes compensate for the reduced chain length, maintaining surface modification capability while enabling cost-effective production with C1-C6 chains.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The polyurethane and ether segments act as intermediary structures that bridge the perfluoroalkyl groups to the surfactant functionality. These intermediaries amplify the surface modification effect of shorter chains, allowing them to perform as effectively as longer chains would have, thus resolving the capability deficit.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Productivity

If conventional surfactants are used for low foaming applications, then foam disintegration speed improves, but stability in acidic, basic or brine solutions deteriorates

Engineering Contradiction:
Improvefoam disintegration speedVSAvoidstability in aggressive media
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The patent employs a composite molecular structure with polyurethane backbones and fluorinated side chains that combines the rapid foam disintegration properties of conventional surfactants with the chemical stability of fluorinated compounds. This composite architecture enables the surfactant to withstand acidic, basic, and brine environments while maintaining fast foam breakdown capability.

Inventive Principle:
Principle #40Composite materials

Solution Approach 2:

The invention applies local quality differentiation by positioning stable perfluoroalkyl groups at specific locations in the molecule while maintaining reactive polyurethane segments for foam disintegration. This spatial arrangement allows different parts of the molecule to perform specialized functions: the fluorinated portions provide stability in aggressive media, while the polyurethane segments enable rapid foam breakdown.

Inventive Principle:
Principle #3Local quality

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 compounds demonstrate improved surface tension lowering, leveling, and wetting properties, stability in aggressive media, and quick foam disintegration, offering comparable or superior performance to longer chain surfactants at reduced fluorine usage, making them suitable for various industrial applications.

Implementation Method 1

The compounds demonstrate improved surface tension lowering, leveling, and wetting properties

Methodology Applied
Scientific EffectSurface tension lowering: Surface Tension

Implementation Method 2

exhibiting fast foam disintegration

Methodology Applied
Scientific EffectFoam disintegration: Antifoam

Data Source

PatentUS9464160B2Fluorinated ethoxylated polyurethanes
Publication Date: 2016.10.11 THE CHEMOURS CO FC LLC
  • US9464160B2 patent drawing
  • US9464160B2 patent drawing
  • US9464160B2 patent drawing

AI summary

The present invention comprises fluorinated ethoxylated polyurethanes of formula [Rf—(X)n—(CH2CHR1—O)m—CH2CH2—O—C(O)—NH]p-A, wherein Rf is a C1 to C6 perfluoroalkyl; X is a divalent radical; n is 0 or 1; R1 is H or C1 to C4 alkyl; m is 1 to 20; p is a positive integer of at least 2; and A is the residue of a polyisocyanate, and methods for altering surface behavior of liquids using such compounds.