Sulfonated Urethane Composition for Water Repellency and Stain Release

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Solution Overview

Problem

Current non-fluorinated water repellents for textiles and coatings lack effectiveness in stain release and surfactant properties compared to their fluorinated counterparts.

Innovation Solution

A sulfonated urethane composition is developed by reacting isocyanate group-containing compounds with fluorinated or sugar-substituted alcohols and ethylenically unsaturated compounds, followed by a bisulfate source, to enhance stain release and surfactant properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If non-fluorinated copolymers are used as water repellents, then water repellency is provided, but stain release effectiveness is reduced compared to fluorinated counterparts

Engineering Contradiction:
Improvestain release effectivenessVSAvoidlack of fluorine
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent applies parameter changes by introducing sulfonate groups (-SO3-) into the non-fluorinated copolymer structure. This chemical modification changes the polar and ionic parameters of the polymer, enabling it to achieve stain release effectiveness comparable to fluorinated compounds without requiring fluorine atoms. The sulfonated copolymer maintains water repellency while gaining enhanced stain release capability through the charged sulfonate functionality.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite material system by combining non-fluorinated copolymer chains with sulfonate functional groups. This composite structure integrates the hydrophobic backbone of the copolymer with the hydrophilic, charged sulfonate groups, resulting in a material that exhibits both water repellency and effective stain release properties, resolving the contradiction between avoiding fluorine and achieving high performance.

Inventive Principle:
Principle #40Composite materials

2Reliability

If fluorinated copolymers are used, then excellent water and oil repellency are achieved, but environmental and health concerns arise

Engineering Contradiction:
Improvewater and oil repellencyVSAvoidenvironmental and health concerns
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent extracts and removes the fluorinated components from the copolymer structure while retaining the essential water and oil repellency functions through the non-fluorinated copolymer backbone. By eliminating fluorine atoms entirely and replacing them with sulfonate functional groups, the invention achieves high-performance repellency without the environmental persistence and health concerns associated with fluorinated compounds.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The invention replaces expensive and environmentally problematic fluorinated materials with more benign, biodegradable non-fluorinated copolymers containing sulfonate groups. These alternative materials provide comparable performance but with reduced environmental impact and lower cost, aligning with sustainable chemistry principles.

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

3Reliability

If conventional non-fluorinated copolymers are used, then water repellency is provided, but surfactant properties are insufficient

Engineering Contradiction:
Improvesurfactant propertiesVSAvoidinsufficient surface tension reduction
Core Design Contradiction:
ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The patent dramatically changes the surface chemical parameters of the copolymer by incorporating sulfonate groups, which are highly polar and ionic. This transformation enables the material to function as an effective surfactant by significantly reducing surface tension of aqueous systems, a property that conventional non-fluorinated copolymers lack. The sulfonate groups provide the necessary amphiphilic character for surfactant activity.

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 resulting composition demonstrates improved water repellency and stain release performance comparable to fluorinated treatments, while reducing surface tension in aqueous media.

Implementation Method 1

Fluorinated and non-fluorinated surfactants are known to be useful as additives to aqueous systems including architectural coatings for reducing surface tension

Methodology Applied
Scientific EffectSurface tension reduction: Surfactant

Implementation Method 2

Various compositions are known to be useful as treating agents to provide water repellency or stain release to textile substrates

Methodology Applied
Scientific EffectWater repellency: Hydrophobe

Implementation Method 3

Many such treating agents are fluorinated polymers and copolymers, or non-fluorinated polymers and copolymers

Methodology Applied
Scientific EffectStain release: Surfactant

Data Source

PatentUS10208155B2Sulfonated fluorinated, non-fluorinated or partially fluorinated urethanes
Publication Date: 2019.02.19 THE CHEMOURS CO FC LLC
  • US10208155B2 patent drawing
  • US10208155B2 patent drawing
  • US10208155B2 patent drawing

AI summary

The invention relates to a compound prepared by (i) reacting (a) at least one compound selected from diisocyanate, polyisocyanate, or mixture thereof; (b) at least one isocyanate-reactive compound selected from a fluorinated alcohol; a cyclic or acyclic sugar alcohol which is substituted with at least one —R1, —C(O)R1, —(CH2CH2O)n(CH(CH3)CH2O)mR2, —(CH2CH2O)n(CH(CH3)CH2O)mC(O)R1, or mixtures thereof; or mixtures of a fluorinated alcohol and a substituted cyclic or acyclic sugar alcohol; and (c) at least one isocyanate-reactive ethylenically unsaturated compound; wherein each n is independently 0 to 20; each m is independently 0 to 20; m+n is greater than 0; each R1 is independently a linear or branched alkyl group having 5 to 29 carbons optionally comprising at least 1 unsaturated bond; each R2 is independently —H, or a linear or branched alkyl group having 6 to 30 carbons optionally comprising at least 1 unsaturated bond, or mixtures thereof; and (ii) reacting the reaction product of step (i) with a bisulfate source.