Poly(alkylene carbonate) Isomerization for Primary Hydroxyl End Groups

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Solution Overview

Problem

Current methods for producing poly(alkylene carbonate) polymers with predominantly primary hydroxyl end groups are inefficient, often requiring additional reaction steps and resulting in polymers with a significant portion of secondary hydroxyl end groups, which complicates polyurethane synthesis.

Innovation Solution

A method involving isomerization, either through heating or the use of isomerization catalysts, to increase the ratio of primary to secondary hydroxyl end groups in poly(alkylene carbonate) polymers, thereby enhancing the polymer's regioregularity and reactivity with isocyanates.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional polymerization catalysts (e.g., double metal cyanide catalysts) are used to produce poly(alkylene carbonate) polymers, then the polymerization reaction proceeds efficiently, but the resulting polymers predominantly contain secondary hydroxyl end groups rather than primary hydroxyl end groups

Engineering Contradiction:
Improvepolymerization reaction efficiencyVSAvoidhydroxyl end group regiochemistry
Core Design Contradiction:
ProductivityVSManufacturing precision

Solution Approach 1:

The patent applies preliminary action by performing isomerization treatment on the polymer after conventional polymerization. The polymer is treated with an isomerization catalyst (such as boron compounds, aluminum compounds, or zinc compounds) under controlled conditions (temperature: 50-150°C, time: 1-48 hours) to convert secondary hydroxyl end groups into primary hydroxyl end groups before the polymer is used in polyurethane synthesis. This preliminary treatment ensures the desired primary hydroxyl content is achieved without compromising the efficiency of the original polymerization process.

Inventive Principle:
Principle #10Preliminary action

2Manufacturing precision

If additional reaction steps (such as reacting with cyclic carboxylic acid anhydride followed by ethylene oxide) are introduced to generate primary hydroxyl groups, then the primary hydroxyl end group content increases, but the process complexity and number of steps increase

Engineering Contradiction:
Improveprimary hydroxyl end group contentVSAvoidnumber of reaction steps
Core Design Contradiction:
Manufacturing precisionVSDevice complexity

Solution Approach 1:

The patent extracts the isomerization function from the complex multi-step process and implements it as a single, dedicated treatment step. Instead of using sequential reactions with anhydrides and ethylene oxide, the invention directly treats the polymer with isomerization catalysts under simplified conditions. This extraction of the essential function (converting secondary to primary hydroxyl groups) eliminates unnecessary intermediate steps and reagents, reducing process complexity while achieving the same or better results.

Inventive Principle:
Principle #2Taking out (Extraction)

Solution Approach 2:

The patent applies parameter changes by optimizing the isomerization treatment conditions (catalyst type, temperature, time, and catalyst-to-polymer ratio) to achieve high primary hydroxyl content in a single step. By carefully controlling these parameters, the process achieves efficient conversion without requiring multiple reaction steps, thus simplifying the overall manufacturing process while maintaining high precision in hydroxyl end group composition.

Inventive Principle:
Principle #35Parameter changes

3Productivity

If polymers with predominantly secondary hydroxyl end groups are used in polyurethane synthesis, then the reaction rate with isocyanates decreases, but the production process becomes more complex and less efficient

Engineering Contradiction:
Improvepolyurethane synthesis efficiencyVSAvoidreaction rate with isocyanate
Core Design Contradiction:
ProductivityVSEase of operation

Solution Approach 1:

The patent applies self-service by enabling the polymer to undergo self-isomerization when treated with appropriate catalysts. The isomerization process allows the polymer chains to spontaneously rearrange their hydroxyl end groups from secondary to primary configuration under controlled catalytic conditions. This self-service approach eliminates the need for complex external intervention or multiple processing steps, thereby improving both the ease of operation and the subsequent polyurethane synthesis efficiency.

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

This approach simplifies the production of poly(alkylene carbonate) polymers with a higher primary hydroxyl end group content, improving their reactivity and efficiency in polyurethane synthesis, allowing for more convenient and efficient polyurethane formation processes.

Implementation Method 1

contacting a starting poly(alkylene carbonate) polymer composition with an isomerization catalyst to provide a modified poly(alkylene carbonate) polymer composition wherein the modified poly(alkylene carbonate) polymer composition has a higher ratio of primary to secondary OH end groups

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

isomerizing (e.g., isomerization promoted by heating) a starting poly(alkylene carbonate) polymer composition to provide a modified poly(alkylene carbonate) polymer composition wherein the modified poly(alkylene carbonate) polymer composition has a higher ratio of primary to secondary —OH end groups

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentUS11230625B2End-group isomerization of poly(alkylene carbonate) polymers
Publication Date: 2022.01.25 SAUDI ARAMCO TECH CO
  • US11230625B2 patent drawing
  • US11230625B2 patent drawing
  • US11230625B2 patent drawing

AI summary

Described herein are methods of preparing poly(alkylene carbonate) polymers comprising an increased ratio of primary hydroxyl end groups to secondary hydroxyl end groups, and compositions thereof.