Sulfonated Block Copolymer Membrane Sulfonation Process

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Solution Overview

Problem

Existing methods for sulfonating aromatic-containing block copolymers in non-halogenated solvents face challenges such as polymer precipitation and gelation, especially when using C2 to C8 acyl sulfates, which result in residual carboxylic acids that cause internal stresses and offensive odors in membranes.

Innovation Solution

A process involving sulfonation of precursor block polymers with C2 to C8 acyl sulfates in non-halogenated aliphatic solvents, followed by conversion of residual carboxylic acids to C1 to C4 alkyl esters, reducing their concentration to less than 2.0 wt%, thereby preventing membrane defects and odors.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If sulfonation is performed using C2 to C8 acyl sulfates in non-halogenated solvents, then high sulfonation levels can be achieved without halogenated solvents, but residual carboxylic acids are formed that cause internal stresses and offensive odors in membranes

Engineering Contradiction:
Improveresidual carboxylic acid contentVSAvoidsulfonation process complexity
Core Design Contradiction:
Object-affected harmful factorsVSEase of manufacture

Solution Approach 1:

The patent converts the harmful residual carboxylic acid byproducts into beneficial alkyl esters by reacting them with alcohols. This transformation eliminates the offensive odor and internal stress problems caused by free acids while maintaining the sulfonation benefits of using C2 to C8 acyl sulfates in non-halogenated solvents.

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

Solution Approach 2:

The patent changes the chemical form of the carboxylic acid byproduct from free acid to alkyl ester through esterification reaction. This parameter change in molecular structure fundamentally alters the properties of the byproduct, transforming it from harmful to benign or desirable.

Inventive Principle:
Principle #35Parameter changes

2Productivity

If polymer concentration is increased to improve productivity, then membrane production efficiency increases, but polymer precipitation and gelation occur

Engineering Contradiction:
Improvemembrane production efficiencyVSAvoidpolymer solution stability
Core Design Contradiction:
ProductivityVSReliability

Solution Approach 1:

The patent introduces an intermediary substance (alcohol) that mediates between the polymer and the carboxylic acid byproduct. The alcohol reacts with the acid to form ester, preventing the acid from causing precipitation or gelation at high polymer concentrations, thus enabling improved productivity without sacrificing solution stability.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Stability of the object's composition

If halogenated solvents are used to prevent polymer precipitation, then polymer solubility is maintained, but environmental and safety concerns arise

Engineering Contradiction:
Improvepolymer solubilityVSAvoidenvironmental and safety hazards
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The patent converts the harmful effect of carboxylic acid byproducts (which would normally require halogenated solvents to manage) into a beneficial esterification process. This allows the use of safe non-halogenated solvents while maintaining polymer solubility and preventing precipitation through the ester formation mechanism.

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

This approach enables high sulfonation levels without polymer precipitation or gelation, producing membranes with improved wet strength, dimensional stability, and reduced residual acid-related issues, such as internal stresses and odors.

Implementation Method 1

reacting the precursor block polymer with a C2 to C8 acyl sulfate in a reaction mixture further comprising at least one non-halogenated aliphatic solvent to form a sulfonated block polymer

Methodology Applied
Scientific EffectSulfonation: Chemical Bonding

Implementation Method 2

reacting the residual carboxylic acid with a C1 to C4 alcohol or mixture thereof in a molar ratio of alcohol to residual carboxylic acid of at least 0.9:1 to form the corresponding alkyl esters of the carboxylic acid

Methodology Applied
Scientific EffectEsterification: Chemical Bonding

Data Source

PatentEP2274351B1Improved method for making sulfonated block copolymers, method for making membranes from such block copolymers and membrane structures
Publication Date: 2015.07.08 KRATON POLYMERS US LLC
  • EP2274351B1 patent drawingFigure 1
  • EP2274351B1 patent drawingFigure 2
  • EP2274351B1 patent drawingFigure 3

AI summary

The present invention relates to an improved method for making sulfonated block copolymers and to methods for making membranes from such block copolymers. In particular, the present invention relates to an improved method for making sulfonated block copolymers having at least two polymer end blocks that are resistant to sulfonation and at least one polymer interior block that is susceptible to sulfonation where the sulfonation agent is C2 to C8 acyl sulfate. In the improved process the residual carboxylic acid formed from the C2 to C8 acyl sulfate is converted to C1 to C4 alkyl esters by contacting the residual carboxylic acid with at least a 0.9: 1 molar ratio of a C1 to C4 alcohol to residual carboxylic acid, resulting in an improved sulfonated block copolymer solution. The present invention further relates to the use of such sulfonated block copolymer solutions to prepare various membranes and other articles.