Epoxy-Functional Polyester Manufacture via Phase Transfer Catalyst

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Solution Overview

Problem

Existing processes for manufacturing epoxy-functional polyesters often result in significant hydrolysis of the polymer backbone, leading to reduced molecular weight and glass transition temperatures (Tg) that are not suitable for applications like powder coatings.

Innovation Solution

A process involving the reaction of polyesters with epihaloalkanes in a liquid phase, followed by precipitation and solid-liquid separation, which maintains high conversion rates and glass transition temperatures, preventing molecular weight decrease and ensuring Tg remains above 35°C.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If conventional two-step processes with base catalysts and water are used for manufacturing epoxy-functional polyester, then the dehydrohalogenation reaction can proceed, but hydrolysis of the polyester backbone occurs leading to reduced molecular weight and reduced glass transition temperature

Engineering Contradiction:
Improveconversion rate of carboxyl groups to epoxy groupsVSAvoidmolecular weight of polyester
Core Design Contradiction:
ProductivityVSStability of the object's composition

Solution Approach 1:

The invention changes the reaction parameters by using a phase transfer catalyst instead of a base catalyst, and by conducting the reaction in a non-aqueous environment. This parameter change allows high conversion of carboxyl groups to epoxy groups while preventing hydrolysis of the polyester backbone, thus maintaining molecular weight.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The invention introduces a phase transfer catalyst as an intermediary substance that enables the dehydrohalogenation reaction to proceed efficiently without requiring base catalysts and water. The phase transfer catalyst mediates between the organic and aqueous phases, allowing the reaction to occur while protecting the polyester from hydrolysis.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Productivity

If conventional processes with base catalysts and water are used, then dehydrohalogenation can occur, but significant hydrolysis of the polymer backbone results leading to reduced glass transition temperature below suitable levels for powder coatings

Engineering Contradiction:
Improveconversion rate of carboxyl groups to epoxy groupsVSAvoidglass transition temperature
Core Design Contradiction:
ProductivityVSTemperature

Solution Approach 1:

The invention changes the reaction parameters by using a phase transfer catalyst and non-aqueous environment, which prevents hydrolysis and maintains the glass transition temperature above 35°C, making the polyester suitable for powder coating applications.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The phase transfer catalyst acts as an intermediary that enables high conversion rates while preventing hydrolysis, thus preserving the glass transition temperature at levels suitable for powder coatings.

Inventive Principle:
Principle #24Intermediary (Mediator)

3Manufacturing precision

If conventional processes are used to achieve high conversion of carboxyl groups, then epoxy functional groups are formed, but the process requires base catalysts and water that cause hydrolysis and molecular weight reduction

Engineering Contradiction:
Improveconversion rate of carboxyl-functional groups to epoxy-functional groupsVSAvoidhydrolysis of polyester backbone
Core Design Contradiction:
Manufacturing precisionVSObject-generated harmful factors

Solution Approach 1:

The phase transfer catalyst serves as an intermediary that enables high conversion of carboxyl groups to epoxy groups without requiring base catalysts and water, thereby preventing hydrolysis of the polyester backbone.

Inventive Principle:
Principle #24Intermediary (Mediator)

Solution Approach 2:

The invention changes the reaction conditions by using a phase transfer catalyst in a non-aqueous environment, which achieves high manufacturing precision in terms of conversion rate while eliminating the harmful hydrolysis effect.

Inventive Principle:
Principle #35Parameter changes

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 process achieves high conversion of carboxyl-functional groups to epoxy-functional groups with minimal molecular weight reduction, enabling the production of epoxy-functional polyesters suitable for powder coatings with maintained or elevated glass transition temperatures.

Implementation Method 1

b) reacting the functional groups of the polyester with an epihaloalkane to obtain an epoxy-functional polyester dissolved in a liquid phase

Methodology Applied
Scientific EffectChemical reaction: Chemical Bonding

Implementation Method 2

d) precipitating the epoxy-functional polyester from the liquid phase obtained in step b) or in step c)

Methodology Applied
Scientific EffectPrecipitation: Precipitation

Data Source

PatentUS11203661B2Process for the manufacture of an epoxy-functional polyester, epoxy-functional polyester obtained by such process and coating composition comprising such epoxy-functional polyester
Publication Date: 2021.12.21 AKZO NOBEL COATINGS INT BV

AI summary

The present invention relates to a process for the manufacture of an epoxy-functional polyester, and to solid epoxy-functional polyesters made by such process and to a coating composition, in particular a powder coating composition, comprising such solid epoxy-functional polyester. The polyester made as disclosed herein is particularly useful in powder coatings.