Bio-based Oligomers via Esterification for Low Viscosity
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Solution Overview
Problem
Current bio-based resins derived from plant oils face limitations due to low glass transition temperature and mechanical properties, requiring the introduction of petroleum-based monomers to achieve desired material properties, which compromises their renewable content.
Innovation Solution
Development of novel biobased resins with a large number of unsaturated ester groups by esterifying epoxidized sucrose fatty acid esters with ethylenically unsaturated acids and acid anhydrides, reducing resin viscosity and enhancing processing capabilities without the need for styrene diluents.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Object-affected harmful factors
If plant oils are used as bio-renewable feedstocks, then environmental friendliness and sustainability are improved, but the glass transition temperature and mechanical properties deteriorate
Solution Approach 1:
The patent applies parameter changes by modifying the chemical structure of plant oil derivatives through esterification reactions. Specifically, epoxidized plant oils are reacted with unsaturated acids to introduce ester groups, which changes the molecular parameters (functionality, crosslink density) while maintaining the bio-based nature. This resolves the contradiction by improving mechanical properties through chemical modification without sacrificing environmental friendliness.
Solution Approach 2:
The patent creates composite molecular structures by combining epoxidized plant oil derivatives with unsaturated acid components. The resulting oligomers contain multiple functional groups (ester, carboxyl, hydroxyl) that work synergistically to provide both the environmental benefits of bio-based materials and the enhanced mechanical properties needed for practical applications.
2Speed
If epoxidized plant oils are modified to improve reactivity, then polymerization speed is improved, but the internal epoxy groups become less reactive
Solution Approach 1:
The patent changes the chemical parameters of epoxidized plant oils by introducing ester groups through reaction with unsaturated acids. This modification transforms the less reactive internal epoxy groups into more reactive ester-functionalized structures, thereby improving both reactivity and polymerization speed while maintaining the crosslinked network structure.
Solution Approach 2:
The patent uses unsaturated acids as intermediary compounds to bridge the reactivity gap. These acids react with epoxidized plant oils to create intermediate structures (ester-functionalized oligomers) that possess higher reactivity than the original epoxy groups, enabling faster polymerization while maintaining crosslinking capability.
3Ease of operation
If styrene diluents are added to reduce viscosity, then processing capability is improved, but the renewable content deteriorates
Solution Approach 1:
The patent changes the molecular weight and functionality parameters of the bio-based oligomers to achieve lower viscosity without adding petroleum-based diluents. By controlling the degree of esterification and selecting appropriate unsaturated acid components, the resin viscosity is reduced to processing-friendly levels while maintaining 100% renewable content.
Solution Approach 2:
The patent enables the bio-based system to self-regulate its viscosity through controlled oligomerization and esterification reactions. The molecular architecture of the oligomers (chain length, branching, functionality) is optimized to provide inherent flow properties suitable for processing, eliminating the need for external petroleum-based viscosity modifiers.
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 resins exhibit improved mechanical properties and reduced viscosity, allowing for the creation of thermosetting compositions with enhanced functionality and reduced styrene requirements, thus expanding the utility of bio-based materials in coatings, composites, and adhesives.
Implementation Method 1
esterifying epoxidized sucrose fatty acid esters with ethylenically unsaturated acids and acid anhydrides
Implementation Method 2
taking advantage of the autoxidation crosslinking of the double bonds in the fatty acid chains
Implementation Method 3
a variety of plant oil-based polymers have been developed via free radical or cationic homo-polymerization
Data Source
AI summary
The invention relates to a polyfunctional bio-based oligomer which is the reaction product of a) at least one epoxidized sucrose fatty acid ester resin; b) at least one ethylenically unsaturated acid selected from methacrylic acid, acrylic acid, crotonic acid, and mixtures thereof; c) at least one acid anhydride selected from acetic acid anhydride, acrylic acid anhydride, methacrylic acid anhydride, crotonic acid anhydride, and mixtures thereof; d) optionally, at least one catalyst; and e) optionally, at least one inhibitor. In a polyfunctional bio-based oligomer of the invention, the ratio of ethylenically unsaturated acid to acid anhydride ranges from 90:1 to 1:90; at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one ethylenically unsaturated acid; and at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one acid anhydride. Other embodiments of the invention relate to methods of making the polyfunctional bio-based oligomers of the invention and to curable coating compositions containing them.