Functionalized Amide Polymers with Pendant Groups

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Solution Overview

Problem

Polymers produced through step growth condensation lack pendant functional groups, limiting their ability to modulate physical, chemical, and biological properties for biomedical applications where interaction with the biological environment is necessary.

Innovation Solution

Development of functionalized amide polymers with pendant functional groups, achieved by polymerizing end-functionalized amide compounds, allowing for the creation of polyesters and polyurethanes with amide units that include these groups, which can be further modified through post-polymerization functionalization.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If step growth condensation polymerization is used to produce polymers, then the polymers have good mechanical properties and structural stability, but they lack pendant functional groups that are necessary for biomedical applications

Engineering Contradiction:
Improveability to interact with biological environmentVSAvoidpolymer structure simplicity
Core Design Contradiction:
Adaptability or versatilityVSEase of manufacture

Solution Approach 1:

The polymer structure is segmented into distinct functional regions: the backbone provides mechanical stability while pendant functional groups attached at regular intervals provide biological interaction capabilities. This segmentation allows each part to fulfill its specific function without compromising the other.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

Pendant functional groups are introduced at specific locations along the polymer backbone rather than uniformly throughout. This local quality approach allows the polymer to maintain structural integrity in the backbone while providing targeted biological functionality at specific sites where pendant groups are attached.

Inventive Principle:
Principle #3Local quality

2Adaptability or versatility

If pendant functional groups are incorporated into the polymer backbone, then the polymers can modulate physical and chemical properties for biomedical applications, but the polymerization process becomes more complex

Engineering Contradiction:
Improvemodulation of physical and chemical propertiesVSAvoidpolymerization process complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

End-functionalized amide compounds are prepared in advance with protected pendant functional groups before polymerization. This preliminary action allows the complex functional groups to be pre-assembled and protected, simplifying the actual polymerization process while ensuring the desired functionality is incorporated into the final polymer.

Inventive Principle:
Principle #10Preliminary action

Solution Approach 2:

Protecting groups serve as intermediaries during the polymerization process, temporarily masking the reactivity of pendant functional groups. This allows the polymerization to proceed smoothly without unwanted side reactions, after which the protecting groups are removed to reveal the desired functionality.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Reliability

If poly(lactic acid) is used for biomedical applications, then the polymer is biodegradable with good mechanical properties, but it lacks functional groups to provide signaling cues in biological environments

Engineering Contradiction:
Improvebiodegradability and mechanical propertiesVSAvoidability to provide biological signaling cues
Core Design Contradiction:
ReliabilityVSAdaptability or versatility

Solution Approach 1:

The invention creates composite polymer structures where the poly(lactic acid) backbone provides biodegradability and mechanical properties, while attached pendant functional groups provide biological signaling capabilities. This composite approach combines the advantages of different functional components into a single polymer system.

Inventive Principle:
Principle #40Composite materials

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 incorporation of pendant functional groups enhances the polymers' ability to interact with biological environments, modulating their properties and providing desired functionalities, such as biodegradability and improved adhesion, while allowing for post-polymerization modifications to achieve specific biological or chemical outcomes.

Implementation Method 1

Polymers made from step growth condensation are used in numerous applications

Methodology Applied
Scientific EffectStep growth condensation: Chemical Bonding

Implementation Method 2

These functional groups modulate the physical, chemical and biological properties of the polymers

Methodology Applied
Scientific EffectChemical interaction: Chemical Bonding

Implementation Method 3

poly(lactic acid) is commonly used for several biomedical applications since it is biodegradable

Methodology Applied
Scientific EffectBiodegradation: Decomposition (biological)

Data Source

PatentEP2820067B1Biodegradable polymers with pendant functional groups attached through amide bonds
Publication Date: 2023.02.15 THE UNIVERSITY OF AKRON
  • EP2820067B1 patent drawingFigure 1
  • EP2820067B1 patent drawingFigure 2
  • EP2820067B1 patent drawing

AI summary

Amide compounds are defined and are polymerized to create polyesters and polyurethanes having amide units bearing a pendant functional group, where the nitrogen atom of the amide group is part of the polymer backbone. The pendant functional group of the functionalized amide polymer may be modified or added by post polymerization functionalization of the functionalized amide polymer. The pendant functional group of the functionalized amide polymer may include a protecting group that may be removed after polymerization. The pendant functional groups of the functionalized amide polymers may be used to modulate the physical, chemical and biological properties of the polymers.