Bio-renewable Polythiol Compounds via Click Reaction Synthesis
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
The chemical industry relies on non-sustainable petroleum-based carbon feedstocks, and there is a need for bio-renewable sources of thiol functional compounds for use in click reactions, which are currently derived from petrochemical sources.
Innovation Solution
Development of polythiol compounds derived from bio-renewable resources such as phenols, polyphenols, or phenolic acids, specifically through processes involving allylation, thiol-ene reactions, and deprotection steps to create compounds with general formulas VIA, VIB, or VIC, which can be used in curable compositions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If petroleum-based carbon feedstocks are used, then chemical products can be manufactured efficiently, but sustainability deteriorates due to consumption of feedstock requiring millions of years to form
Solution Approach 1:
The patent changes the source parameter of carbon feedstock from petroleum-based to biomass-based, transforming the temporal scale of feedstock formation from millions of years to recent biological cycles, thereby resolving the sustainability contradiction while maintaining chemical manufacturing efficiency
Solution Approach 2:
The patent creates bio-renewable thiol functional compounds that copy the functional properties of petrochemical thiol compounds, allowing substitution in the same chemical applications while using sustainably sourced biomass instead of depleting petroleum resources
2Reliability
If biomass feedstock is used, then sustainability improves, but processing efficiency and cost disruption worsen without an efficient production paradigm
Solution Approach 1:
The patent segments the biomass processing into distinct functional steps: (1) derivation of platform chemicals from biomass, (2) conversion to thiol-containing compounds via click reactions, and (3) application in coatings, adhesives, and sealants. This segmentation enables efficient processing by treating each stage independently with optimized conditions
Solution Approach 2:
The patent introduces thiol-containing compounds as intermediary products that bridge biomass-derived platform chemicals and final chemical products. These intermediaries enable efficient conversion from biomass to end-products through well-established thiol-ene and thiol-epoxy chemistry, resolving the processing efficiency challenge
3Quantity of substance
If traditional petrochemical sources are used for thiol-containing compounds, then availability is ensured, but environmental impact worsens due to non-sustainable resource consumption
Solution Approach 1:
The patent changes the source parameter of thiol compounds from non-renewable petrochemicals to bio-renewable biomass, transforming the environmental impact profile while maintaining compound availability through established biomass conversion pathways and click reaction chemistry
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 polythiol compounds offer a sustainable alternative for use in coatings, adhesives, and sealants, with high biocarbon content and efficient processing, reducing environmental impact and production costs.
Implementation Method 1
the use of so-called 'click reactions' in the synthesis of these materials provides an ecologically-friendly technology on account of the limited amount of waste originated, the low energy consumption, the completeness of the reaction process and the high yield without the formation of by-products
Implementation Method 2
WO2010/136725A1 (Centre National de la Recherche Scientifique (C.N.R.S.) et al.) describes a process for preparing epoxy resins from a mixture of epoxidized phenolic compounds, wherein said epoxidized phenolic compounds are obtained by epoxidation of natural phenolic compounds
Implementation Method 3
U.S. Pat. No. 8,513,374 B2 (Dasgupta) describes-ene compounds which are derivatives of a plant polyphenol and which are selected from the group consisting of curcumin diallyl carbonate, tetrahydrocurcumin diallyl carbonate, resveratrol triallyl carbonate
Data Source
AI summary
The present application is directed to a polythiol compound obtainable independently from a) eugenol, b) gallic acid, c) the adduct of guaiacol and vanillin or d) resveratrol and, respectively, having the general Formula VIA, VIB, VIC or VID, wherein: R1 is a C1-C18 alkylene group, C2-C18 oxyalkylene group, C2-C18 thioalkylene group, C6-C18 arylene or C7-C18 aralkylene group; and R2 is H or methyl.