Radical crosslinking of polyether carbonate polyols that have electron-poor and electron-rich double bonds

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Solution Overview

Problem

Current processes for producing polyethercarbonate polyols face challenges in achieving efficient crosslinking and processing due to high curing temperatures and long curing times, as well as the limitations of existing functionalization methods.

Innovation Solution

A process involving the use of a catalyst and a suspension medium without H-functional groups, metering in carbon dioxide and two unsaturated compounds, one with an electron-rich double bond and the other with an electron-poor double bond, to produce polyethercarbonate polyols with favorable properties for crosslinking.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If conventional crosslinking processes are used for polyethercarbonate polyols, then crosslinking can be achieved, but high curing temperatures and long curing times are required

Engineering Contradiction:
Improvecrosslinking efficiencyVSAvoidcuring temperature
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent changes the chemical structure parameters of the polyethercarbonate polyol by incorporating unsaturated groups with different electron densities (electron-rich and electron-poor double bonds) during copolymerization. This structural modification enables the material to undergo crosslinking at lower temperatures and shorter times compared to conventional saturated polyethercarbonates, directly resolving the contradiction between crosslinking efficiency and curing temperature requirements

Inventive Principle:
Principle #35Parameter changes

2Reliability

If conventional crosslinking processes are used for polyethercarbonate polyols, then crosslinking can be achieved, but long curing times are required

Engineering Contradiction:
Improvecrosslinking efficiencyVSAvoidcuring time
Core Design Contradiction:
ReliabilityVSLoss of time

Solution Approach 1:

By modifying the chemical composition parameters through copolymerization with unsaturated compounds, the patent creates polyethercarbonate polyols with reactive unsaturated groups that facilitate faster crosslinking reactions. The presence of both electron-rich and electron-poor double bonds creates favorable electronic conditions for rapid crosslinking, significantly reducing curing time while maintaining crosslinking efficiency

Inventive Principle:
Principle #35Parameter changes

3Adaptability or versatility

If polyethercarbonate polyols are functionalized with unsaturated groups, then subsequent crosslinking reactions become possible, but the processing complexity increases

Engineering Contradiction:
Improvefunctionalization capabilityVSAvoidprocess complexity
Core Design Contradiction:
Adaptability or versatilityVSDevice complexity

Solution Approach 1:

The patent combines the copolymerization step and the introduction of unsaturated groups into a single integrated process step. By incorporating unsaturated compounds (such as vinyl-containing monomers) directly during the CO2 copolymerization reaction, the patent achieves functionalization without requiring separate post-polymerization modification steps, thereby maintaining process simplicity while enabling crosslinking capability

Inventive Principle:
Principle #5Merging (Combining)

Solution Approach 2:

The copolymerization catalyst system serves multiple functions: it catalyzes both the insertion of CO2 and the incorporation of unsaturated monomers into the polymer chain. This multi-functionality eliminates the need for separate functionalization steps and simplifies the overall process while providing versatile crosslinking-capable polyethercarbonate polyols

Inventive Principle:
Principle #6Universality (Multi-functionality)

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 results in polyethercarbonate polyols with unsaturated groups that can be reproducibly crosslinked at lower temperatures and faster times, offering improved processing and mechanical properties.

Implementation Method 1

A process is described for the preparation of polyethercarbonate polyols (2) containing unsaturated groups (C=C) by copolymerization of carbon dioxide (I) and unsaturated compounds (III) in the presence of a DMC catalyst

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

Radical crosslinking of polyether carbonate polyols that have electron-poor and electron-rich double bonds

Methodology Applied
Scientific EffectRadical crosslinking: Chemical Bonding

Data Source

PatentUS10179835B2Radical crosslinking of polyether carbonate polyols that have electron-poor and electron-rich double bonds
Publication Date: 2019.01.15 COVESTRO DEUTSCHLAND AG
  • US10179835B2 patent drawing
  • US10179835B2 patent drawing
  • US10179835B2 patent drawing

AI summary

The present invention relates to a method for producing polyether carbonate polyols, the polyether carbonate polyols having electron-poor and electron-rich double bonds, said method preferably comprising the steps of (a) providing a suspending agent and/or an H-functional starter compound and a DMC catalyst, 03) adding at least one epoxide and (y) adding carbon dioxide, an epoxide that does not contain an unsaturated group, and at least two unsaturated compounds, the unsaturated compounds in method step (y) being selected from the group comprising unsaturated epoxides and unsaturated cyclic anhydrides, and one of the unsaturated compounds having an electron-rich double bond and one of the unsaturated compounds having an electron-poor double bond. The invention also relates to the crosslinking of polyether carbonate polyols, the polyether carbonate polyols having electronpoor and electron-rich double bonds, and to the crosslinked polyether carbonates obtainable therefrom.