Triptycene-Based Polyimide Membranes for Gas Separation

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Solution Overview

Problem

Current polyimides for gas separation applications lack improved compositions and efficient synthesis methods, limiting their performance in membrane-based technologies for air separations, hydrogen recovery, natural gas sweetening, and carbon capture.

Innovation Solution

Development of ortho-dimethyl-substituted and tetramethyl-substituted triptycene-containing diamine monomers and microporous triptycene-based polyimides and polyamides, synthesized through specific chemical routes involving Friedel-Crafts alkylation, Diels-Alder reactions, and palladium-catalyzed hydrazine reduction, which are then polymerized with tetracarboxylic dianhydrides or dicarboxylic acids to form high molecular weight polymers with enhanced microporosity and thermal stability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional polyimide synthesis methods are used, then the polymerization process is simple, but the microporosity and gas separation performance are insufficient

Engineering Contradiction:
Improvegas separation performanceVSAvoidsynthesis process complexity
Core Design Contradiction:
ReliabilityVSDevice complexity

Solution Approach 1:

The patent modifies the chemical structure parameters of the polyimide by incorporating triptycene-based diamine monomers with specific substituent patterns (ortho-dimethyl and tetramethyl substitutions). This structural parameter change creates intrinsic microporosity within the polymer matrix, enabling gas separation performance without requiring complex post-synthesis processing or specialized equipment.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite polyimide structures by combining triptycene-based diamine monomers with various tetracarboxylic dianhydride monomers. This composite approach allows the polymer to exhibit both the structural stability of conventional polyimides and the microporosity needed for gas separation, achieving improved performance through material composition rather than process complexity.

Inventive Principle:
Principle #40Composite materials

2Stability of the object's composition

If triptycene-based diamine monomers are synthesized through multiple steps, then the microporosity and thermal stability are improved, but the synthesis time and cost increase

Engineering Contradiction:
Improvethermal stabilityVSAvoidsynthesis time
Core Design Contradiction:
Stability of the object's compositionVSLoss of time

Solution Approach 1:

The patent performs preliminary structural design and selection of triptycene-based diamine monomers with pre-established microporous characteristics. By preparing the monomers with the desired structural features before polymerization, the synthesis process avoids time-consuming post-synthesis modifications or characterization steps, achieving thermal stability and microporosity through careful monomer selection and pre-synthesis planning.

Inventive Principle:
Principle #10Preliminary action

3Productivity

If polyimides are used for membrane-based gas separation, then the gas separation efficiency is improved, but the membrane fabrication complexity increases

Engineering Contradiction:
Improvegas separation efficiencyVSAvoidmembrane fabrication complexity
Core Design Contradiction:
ProductivityVSDevice complexity

Solution Approach 1:

The triptycene-based polyimide monomers are designed to self-assemble into microporous structures during polymerization without requiring external templating, porogen additives, or complex fabrication equipment. The intrinsic microporosity emerges from the monomer structure itself, allowing the polymer to fabricate its own separation-active structure and eliminating the need for complex post-fabrication processing steps.

Inventive Principle:
Principle #25Self-service

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 polymers exhibit improved thermal stability, solubility, and microporosity, leading to enhanced performance in gas separation technologies, including increased surface area and efficiency in separating gases such as O2/N2, H2/N2, H2/CH4, CO2/CH4, and CO2/N2, making them suitable for various industrial applications.

Implementation Method 1

Gas separation is an emerging technology with a rapidly developing market, as such there exists an urgent need for improved compositions and methods of synthesizing compounds that can be used for such applications

Methodology Applied
Scientific EffectPermeation: Permeation

Implementation Method 2

polyimides of intrinsic microporosity (PIM-PIs) demonstrated promising properties for membrane-based gas separation applications

Methodology Applied
Scientific EffectMicroporosity: Porosity

Data Source

PatentUS10619009B2Ortho-substituted triptycene-based diamines, monomers, and polymers, methods of making and uses thereof
Publication Date: 2020.04.14 KING ABDULLAH UNIV OF SCI & TECH
  • US10619009B2 patent drawing
  • US10619009B2 patent drawing
  • US10619009B2 patent drawing

AI summary

Described herein are ortho-dimethyl-substituted and tetramethyi-substituted triptycene-containing diamine monomers and microporous triptycene-based poiyimides and poiyamides, and methods of making the monomers and polymers.