Alkyd Resin Drying and Yellowing via Diels-Alder Adducts

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Solution Overview

Problem

Current biorenewable alkyd resins for coatings face issues with yellowing and slow drying, particularly when using biobased building blocks like rosin and fatty acids, while also needing to reduce volatile organic compounds (VOC) emissions and minimize the use of non-renewable monomers like phthalic anhydride without compromising coating performance.

Innovation Solution

The development of alkyd resins using Diels-Alder adducts derived from citraconic acid, citraconic anhydride, itaconic acid, and itaconic anhydride with C4-C14 conjugated dienes, such as isoprene or terpenes, which can replace phthalic acid in paint formulations, enhancing drying rates and hardness while reducing yellowing.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Object-affected harmful factors

If biobased building blocks like rosin and fatty acids are used to increase biobased content, then environmental sustainability is improved, but yellowing and slow drying occur

Engineering Contradiction:
ImproveyellowingVSAvoidbiobased content
Core Design Contradiction:
Object-affected harmful factorsVSArea of moving object

Solution Approach 1:

The patent changes the chemical parameters of the resin by incorporating Diels-Alder adducts with specific functional groups that modify the oxidation behavior and molecular structure, thereby reducing yellowing while preserving biobased content

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite resin system combining biobased components (fatty acids, rosin) with Diels-Alder adducts that have improved stability properties, achieving a balance between sustainability and performance

Inventive Principle:
Principle #40Composite materials

2Ease of operation

If resin viscosity is lowered to improve coating application, then ease of operation is improved, but drying time increases and coating properties deteriorate

Engineering Contradiction:
Improvecoating applicationVSAvoiddrying time
Core Design Contradiction:
Ease of operationVSDuration of action of moving object

Solution Approach 1:

The patent modifies the resin's molecular parameters by using Diels-Alder adducts that provide appropriate viscosity characteristics, enabling good flow and application properties while maintaining sufficient crosslinking density for proper drying rate

Inventive Principle:
Principle #35Parameter changes

3Object-affected harmful factors

If phthalic anhydride is replaced with biobased monomers to reduce VOC and increase sustainability, then environmental impact is improved, but coating performance such as hardness and drying rate decreases

Engineering Contradiction:
ImproveVOC emissionsVSAvoidcoating hardness
Core Design Contradiction:
Object-affected harmful factorsVSStrength

Solution Approach 1:

The patent changes the chemical structure parameters by using Diels-Alder adducts with specific functional groups that enable proper crosslinking and film formation, achieving hardness comparable to phthalic anhydride-based resins while using biobased materials

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent substitutes the traditional phthalic anhydride chemistry with Diels-Alder adduct chemistry, replacing a non-biobased monomer system with a biobased alternative that achieves similar performance through different chemical mechanisms

Inventive Principle:
Principle #28Mechanics substitution (Replace mechanical system)

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 alkyd resins exhibit improved drying rates, higher hardness, and reduced yellowing compared to prior art biorenewable alkyd resins, while maintaining a high biobased content and minimizing the use of non-renewable monomers, thus addressing ecological and performance concerns.

Implementation Method 1

an alkyd resin comprising the condensation product of at least the following components (A) a polybasic acid, (B) a polyhydric alcohol, and (C) a linear C12-C60 hydrocarbo carboxylic acid

Methodology Applied
Scientific EffectCondensation polymerization: Chemical Bonding

Implementation Method 2

unsaturated alkyd resin denotes a polyester comprising one or more unsaturated fatty acid moieties which is autoxidisable under air at ambient conditions

Methodology Applied
Scientific EffectAutoxidation: Oxidation

Data Source

PatentEP3158017B1Resin, composition and use
Publication Date: 2018.01.03 DSM IP ASSETS BV
  • EP3158017B1 patent drawing
  • EP3158017B1 patent drawing
  • EP3158017B1 patent drawing

AI summary

The present invention relates to an alkyd resin comprising the condensation product of at least the following components (A) a polybasic acid, (B) a polyhydric alcohol, and (C) a linear C12-C60 hydrocarbo monocarboxylic acid, and optionally (D) at least one component other than any of components A to C characterized in that at least a part of the polybasic acid (A) is a (optionally hydrogenated) Diels Alder adduct of citraconic acid with C4-C14 conjugated diene, a (optionally hydrogenated) Diels Alder adduct of citraconic anhydride with C4-C14 conjugated diene, a half ester of such a Diels Alder adduct and/or a diester of such a Diels Alder adduct.