Chlorine-Resistant Polyamide Membranes via Fluorinated Monomers

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Solution Overview

Problem

Current polyamide desalting membranes are susceptible to degradation by chlorine, requiring dechlorination and reducing their lifespan, which increases operational costs and biofouling issues in water treatment systems.

Innovation Solution

Modification of acid chloride monomers with electron-withdrawing groups to create a chlorine-resistant polyamide membrane that minimizes chlorination and N-chlorination, using monomers like monofluorotrimesoyl chloride, perfluorotrimesoyl chloride, and nitrotrimesoyl chloride, combined with amines such as m-phenylenediamine, to enhance chemical stability and transport properties.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If standard polyamide membranes are used for desalting, then salt rejection and water flux are achieved, but the membranes are susceptible to chlorine degradation and have short lifespan

Engineering Contradiction:
Improvemembrane lifespanVSAvoidchlorine susceptibility
Core Design Contradiction:
ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The patent modifies the chemical parameters of the polyamide membrane by incorporating fluorinated aromatic rings into the polymer structure. This changes the electron density distribution and chemical reactivity of the membrane, making it resistant to chlorine oxidation while maintaining its desalination function. The fluorinated structure alters the membrane's chemical properties without compromising its physical separation performance.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention creates a composite polyamide structure by combining standard polyamide chains with fluorinated aromatic ring units. This composite approach integrates the beneficial properties of both components: the polyamide provides the necessary membrane structure and separation function, while the fluorinated aromatic rings provide chlorine resistance through their electron-withdrawing effect that protects against oxidative degradation.

Inventive Principle:
Principle #40Composite materials

2Reliability

If dechlorination is performed before membrane treatment, then chlorine degradation is prevented, but additional costs are incurred and disinfection effectiveness is reduced

Engineering Contradiction:
Improvemembrane protectionVSAvoidprocess complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent extracts the vulnerability to chlorine from the membrane system by incorporating chlorine-resistant fluorinated aromatic rings directly into the polyamide structure. This eliminates the need for separate dechlorination process steps, as the membrane itself becomes inherently resistant to chlorine degradation while allowing the disinfection function to remain effective.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The fluorinated aromatic rings act as intermediary protective groups within the membrane structure. These groups serve as a chemical barrier that intercepts and neutralizes chlorine's oxidative effect before it can damage the polyamide chains, thereby protecting the membrane without requiring external dechlorination processes.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If electron-withdrawing groups are added to acid chloride monomer, then chlorine resistance is improved, but manufacturing complexity increases

Engineering Contradiction:
Improvechemical stabilityVSAvoidmonomer synthesis
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by selecting specific fluorinated aromatic carboxylic acids as monomers that can be polymerized using modified versions of existing polycondensation processes. While the monomer structure is more complex than standard terephthalic acid, the use of well-established polymerization techniques and the availability of fluorinated aromatic acids from industrial chemistry reduces the overall manufacturing complexity burden.

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 chlorine-resistant membranes exhibit improved durability, preventing biofouling and reducing operational costs by maintaining effective disinfection while extending membrane life and maintaining high salt rejection and water flux performance.

Implementation Method 1

modifying the acid side, i.e., the acid chloride, with electron-withdrawing groups that are active enough to minimize ring chlorination on both the amine and acid and to also minimize N-chlorination

Methodology Applied
Scientific EffectElectron-withdrawing effect:

Implementation Method 2

Such improvement is critical for Reverse Osmosis (RO) plants operating on wastewaters, surface waters and open seawater intakes wherein disinfection by chlorination is required to control the growth of microorganisms

Methodology Applied
Scientific EffectOxidation resistance: Oxidation

Implementation Method 3

desalting membranes for water treatment systems

Methodology Applied
Scientific EffectReverse osmosis: Reverse Osmosis

Data Source

PatentUS7806275B2Chlorine resistant polyamides and membranes made from the same
Publication Date: 2010.10.05 SEPARATION SYST TECH
  • US7806275B2 patent drawing
  • US7806275B2 patent drawing
  • US7806275B2 patent drawing

AI summary

A chlorine resistant polyamide is formed from the reaction product of an amine and an acid chloride monomer wherein the acid chloride monomer is modified with electron-withdrawing groups that exhibit sufficient activity to (i) minimize any chlorination on both the amine and acid chloride side and (ii) minimize N-chlorination. A membrane is made from the polyamide and, in one application, the membrane is used in a desalination unit.