Dioxanone-Modified Vegetable Oil Derivatives for Sustainable Coatings
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Solution Overview
Problem
Current efforts to expand the functionality of vegetable oil products using petrochemical feedstocks, such as phenol, are limited, and there is a need for more sustainable industrial chemicals derived from biobased components.
Innovation Solution
Development of compounds and compositions containing carboxylic acid and/or ester moieties attached to a carbon chain with a dioxanone ring system, which can be used to create dioxanone-containing fatty acid derivatives, coatings, and polymers, enhancing their physical and chemical properties for various applications.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If petrochemical feedstocks are used to functionalize vegetable oil products, then the functionality of vegetable oil products is expanded, but the sustainability and biobased content of the chemicals are reduced
Solution Approach 1:
The invention changes the chemical parameters by using different feedstocks (biobased gamma-butyrolactone and ethyl lactate instead of petrochemical phenol) to achieve functionalization of vegetable oils while maintaining high biobased content. This resolves the contradiction by altering the source material parameter rather than the functionalization approach.
Solution Approach 2:
The invention creates composite chemical structures by combining biobased components (vegetable oil, gamma-butyrolactone, ethyl lactate) to form new derivatives with enhanced functionality. These composite biobased materials replace petrochemical-based products while maintaining or improving functional performance.
2Loss of substance
If dioxanone ring systems are formed from biobased components, then the sustainability is improved, but the complexity of synthesis increases
Solution Approach 1:
The synthesis is segmented into distinct stages: first forming the dioxanone ring system from biobased gamma-butyrolactone or ethyl lactate, then subsequently functionalizing with vegetable oil derivatives. This segmentation allows each step to be optimized independently, managing overall synthesis complexity while maintaining biobased content.
Solution Approach 2:
The invention uses intermediate compounds (such as hydroxy esters and epoxidized intermediates) as mediators in the synthesis pathway. These intermediates facilitate the transformation from simple biobased starting materials to complex dioxanone-containing derivatives, making the overall synthesis more manageable and efficient.
3Productivity
If vegetable oil products are functionalized to create new industrial derivatives, then the productivity of biobased chemicals is increased, but the reliance on petrochemicals persists
Solution Approach 1:
The invention extracts and eliminates the petrochemical component from the functionalization process by replacing phenol-based reagents with biobased alternatives (gamma-butyrolactone and ethyl lactate). This extraction of the harmful dependency maintains productivity while achieving full biobased content in the final derivatives.
Data Source
AI summary
The present invention is directed to carboxylic acid and ester moieties that are attached to a carbon chain that is between 2 and 24 carbons in length wherein, the chain contains at least one dioxanone ring system, said dioxanone being formed from two adjacent carbons in the chain and/or at least one carbon in the chain is substituted with a pendant dioxanone ring system. In preferred embodiments, the carbon chain is a fatty acid residue. The carbons of said chain can be optionally substituted, saturated or unsaturated. When two or more said ester moieties are present, the invention is directed to a polyester such as a triglyceride, that contains multiple carbon chains wherein each chain is independently derivatized such that the triglyceride contains at least one dioxanone ring system, said dioxanone being formed from two adjacent carbons in at least one of said chains. The present invention is also directed to a method of preparing a dioxanone containing composition or fatty acid derivative. The present invention is also directed to coating formulations and polymers that utilize a dioxanone containing composition or fatty acid derivative, and methods of making such coatings and polymers.