Bio-derived Isoindoline Yellow Pigment via Diels-Alder Synthesis

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Solution Overview

Problem

Commercially available isoindoline-based yellow pigments are derived from toxic phthalonitrile, which is harmful to humans and the environment, and are not sustainable due to their petroleum-based origin.

Innovation Solution

A bio-derived isoindoline compound is produced using bio-derived furan and maleic anhydride through the Diels-Alder reaction, followed by dehydroaromatization and amination with urea, resulting in a radiocarbon-labeled bio-DII that can be coupled with building blocks to form a bio-derived isoindoline-based yellow pigment.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If phthalonitrile is used as a starting raw material to produce isoindoline-based yellow pigments, then the pigments can be manufactured with good performance, but the process becomes harmful to human health and the environment due to toxicity

Engineering Contradiction:

Improvepigment performanceVSAvoidhuman health and environmental harm

Core Design Contradiction:

ReliabilityVSObject-affected harmful factors

Solution Approach 1:

The invention changes the chemical composition parameters by replacing phthalonitrile with phthalic anhydride as the starting material. This substitution maintains the isoindoline core structure and pigment performance while eliminating the toxic cyanide group, thereby resolving the contradiction between pigment performance and environmental safety.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention converts the traditionally harmful phthalonitrile route into a beneficial process by using phthalic anhydride, which is less toxic and can be derived from renewable resources. This transformation maintains product quality while converting a harmful chemical pathway into an environmentally friendly one.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

2Productivity

If phthalonitrile is used as a starting raw material, then isoindoline-based yellow pigments can be produced efficiently, but the process becomes unsustainable due to petroleum-based origin

Engineering Contradiction:

Improveproduction efficiencyVSAvoidsustainability

Core Design Contradiction:

ProductivityVSAdaptability or versatility

Solution Approach 1:

The invention changes the source parameter of the starting material from petroleum-derived phthalonitrile to bio-based phthalic anhydride. This parameter change enables the production of sustainable, bio-derived isoindoline pigments while maintaining production efficiency through established chemical pathways.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention converts the limitation of petroleum dependency into an opportunity for sustainability by utilizing bio-based phthalic anhydride. This approach maintains efficient production while adding the benefit of renewable resource utilization and reduced carbon footprint.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

3Reliability

If conventional isoindoline-based yellow pigments are used, then good light and heat fastness is achieved, but environmental impact increases due to toxic synthesis process

Engineering Contradiction:

Improvelight and heat fastnessVSAvoidenvironmental impact

Core Design Contradiction:

ReliabilityVSObject-generated harmful factors

Solution Approach 1:

The invention converts the harmful environmental impact of the synthesis process into a beneficial outcome by using phthalic anhydride instead of phthalonitrile. The resulting isoindoline pigments maintain excellent light and heat fastness properties while the synthesis process generates minimal environmental harm, achieving both performance and sustainability.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

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 bio-derived isoindoline compound provides a safe, clean, and green, carbon-neutral alternative for isoindoline-based yellow pigments, offering high light and heat fastness while reducing environmental impact.

Implementation Method 1

bio-derived furan and bio-derived maleic anhydride are used as a raw material to obtain a DA intermediate by the Diels-Alder (DA) reaction

Methodology Applied

Scientific EffectDiels-Alder reaction: Chemical Bonding

Implementation Method 2

the DA intermediate is dehydroaromatized and aminated with urea to obtain bio-DII containing a radiocarbon atom 14C

Methodology Applied

Scientific EffectDehydroaromatization: Chemical Bonding

Data Source

PatentEP4538267A1Isoindoline compound

Publication Date: 2025.04.16 DIC CORP

Figure 1~2

AI summary

Provided are a bio-derived isoindoline compound that can be used as an isoindoline-based yellow pigment and obtained by a safe, clean and green, and carbon-neutral approach, and a composition containing the isoindoline compound. The isoindoline compound contains a radiocarbon atom 14C and has a group represented by the following formula (A) . (In the formula (A), R1 to R4 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a phenyl group that is optionally substituted with an alkyl group. Note that R2 and R3 are optionally ring-closed to form a 5- to 8-membered ring. R7 and R8 each independently represent a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, or a phenyl group that is optionally substituted with an alkyl group. * represents a bonding hand.)