Polyrotaxane with Polyalkylene Oxide Substituent for Hydrolysis Resistance

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Solution Overview

Problem

Existing polyrotaxanes face issues with durability due to poor hydrolysis resistance and compatibility with materials other than polyrotaxane, particularly when they lack graft chains, leading to poor affinity and compatibility.

Innovation Solution

A polyrotaxane with a pseudopolyrotaxane structure featuring a linear molecule included in the cavity of a cyclic molecule and capping groups, where the cyclic molecule has a substituent represented by a specific formula, enhancing hydrolysis resistance and compatibility through a polyalkylene oxide chain or derivative, and a method involving reaction with a compound to introduce this substituent.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If a polyrotaxane has a polyester structure or polyamide structure in its cyclic molecule, then it can provide some functional properties, but it suffers from poor hydrolysis resistance and reduced durability

Engineering Contradiction:
Improvehydrolysis resistanceVSAvoidchemical stability
Core Design Contradiction:
ReliabilityVSStability of the object's composition

Solution Approach 1:

The patent changes the chemical composition parameter of the cyclic molecule by replacing ester or amide bonds with ether bonds in the polyalkylene oxide chain. This fundamental chemical parameter change transforms the molecular structure from one susceptible to hydrolysis (ester/amide groups) to one with superior hydrolysis resistance (ether groups), while maintaining the desired functional properties through the flexible polyalkylene oxide structure.

Inventive Principle:
Principle #35Parameter changes

2Adaptability or versatility

If a polyrotaxane lacks a graft chain, then it has simpler structure, but it exhibits poor compatibility and affinity with materials other than polyrotaxane

Engineering Contradiction:
Improvecompatibility with other materialsVSAvoidmolecular structure complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent applies local quality by introducing polyalkylene oxide chains at specific locations on the cyclic molecule (as substituents) rather than modifying the entire structure. This localized modification provides the necessary compatibility and affinity with other materials through the polar ether groups and flexible chains, while keeping the rest of the polyrotaxane structure simple and maintaining its characteristic properties.

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent creates a composite molecular structure by combining the polyrotaxane framework with polyalkylene oxide chains as graft substituents. This composite approach integrates the mechanical strength and structural integrity of the polyrotaxane with the compatibility and flexibility of the polyalkylene oxide chains, achieving enhanced overall performance.

Inventive Principle:
Principle #40Composite materials

3Reliability

If the cyclic molecule has a substituent with polyalkylene oxide chain, then it achieves improved hydrolysis resistance and compatibility, but the synthesis process becomes more complex

Engineering Contradiction:
ImprovedurabilityVSAvoidsynthesis process simplicity
Core Design Contradiction:
ReliabilityVSEase of manufacture

Solution Approach 1:

The patent employs preliminary action by first introducing a hydroxyl group substituent on the cyclic molecule, which then serves as a pre-prepared site for subsequent reaction with alkylene oxide monomers. This two-stage approach simplifies the overall synthesis by breaking down the complex grafting process into manageable steps, where the first stage prepares the substrate and the second stage builds the desired polyalkylene oxide chains.

Inventive Principle:
Principle #10Preliminary action

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 polyrotaxane exhibits improved durability, hydrolysis resistance, and compatibility with polymer materials, allowing for enhanced solubility, mechanical properties, and compatibility with various materials, including polymers.

Implementation Method 1

a pseudopolyrotaxane, which has a linear molecule and a cyclic molecule(s) in which the linear molecule is included in a cavity (cavities) of the cyclic molecule(s)

Methodology Applied
Scientific EffectHost-guest inclusion:

Implementation Method 2

the cyclic molecule has a substituent having a polyalkylene oxide chain or a derivative thereof... improved durability, in particular hydrolysis resistance

Methodology Applied
Scientific EffectHydrolysis resistance: Hydrolysis

Implementation Method 3

possessing compatibility with desired materials, for example polymer materials other than a polyrotaxane

Methodology Applied
Scientific EffectPolymer compatibility:

Data Source

PatentUS11072667B2Polyrotaxane having substituent having polyalkylene oxide chain or derivative thereof in cyclic molecule, and method for producing said polyrotaxane
Publication Date: 2021.07.27 ASM
  • US11072667B2 patent drawing
  • US11072667B2 patent drawing
  • US11072667B2 patent drawing

AI summary

The present invention provides a polyrotaxane having high durability and in particular, high hydrolysis resistance, and a method for producing said polyrotaxane. The present invention provides a polyrotaxane obtained by disposing blocking groups on both ends of a pseudopolyrotaxane so that an annular molecule cannot be displaced, said pseudopolyrotaxane being obtained by forming a clathrate by piercing the opening of the cyclic molecule with a linear molecule, said polyrotaxane being characterized in that the cyclic molecule has a substituent represented by formula I (in formula I, R1 represents a group such as —CH3 and —CH2—CH3, R2 represents H or a group such as —CH3, and n is the apparent degree of polymerization of a polyalkylene oxide chain or a derivative thereof added to the cyclic molecule, the value of n being 1.1 to 10.0).