Preparation of vegetable oil-based monomers for use in thermosetting resins
Inventors
Assignees
Washington State University WSU
Publication Number
US-10815186-B2
Publication Date
2020-10-27
Expiration Date
2037-09-07
Interested in licensing this patent?
MTEC can help explore whether this patent might be available for licensing for your application.
Abstract
The present embodiments herein generally relate to thermoset resins that are derived from vegetable oil based sources, including fibrous plant sources. The utilization of plant based oil as starting materials makes the technology a green alternative to currently available solutions. This, coupled with the novel synthetic methods that are utilized, results in a transformation of the plant based oils into useful, durable, and resilient thermoset resins.
Core Innovation
The invention relates to thermoset resins derived from vegetable oil-based sources, including fibrous plant sources such as hempseed oil, cottonseed oil, soybean oil, castor oil, tung oil, and linseed oil. The process utilizes plant-based oils as starting materials combined with synthetic methods that transform these oils into useful, durable, and resilient thermoset resins. Biobased monomer compounds are derived from fatty acids, produced by hydrolysis of vegetable oils, and further functionalized to become suitable for thermosetting resin formation.
The problem addressed is that vegetable oil-derived monomers, when used alone as base resin monomers, typically produce crosslinked polymer networks with insufficient modulus and strength. This deficiency is primarily due to the monomers’ triglyceride structure, which introduces a long flexible fatty chain and results in polymer materials with poor mechanical properties, making them unsuitable for applications such as composite matrix polymers and protective coatings. The aim is to provide synthetic routes that increase the crosslink density and introduce more polymerizable groups, thereby improving strength and modulus.
The invention discloses various types of fatty acid-derived monomers, including acrylates, methacrylates, thiol-containing, and silane-containing monomers. These are synthesized through specific sequences involving hydrolysis, functional group modification (acrylation, methacrylation, epoxidation), and, where necessary, silane or thio modifications. These monomers can be polymerized or copolymerized via thermal or photo initiation to form crosslinked network structures with tailored properties and improved performance compared to prior vegetable oil-derived resins.
Claims Coverage
There are two independent claims providing two main inventive features in this patent.
Compound with a structure of Formula II
The invention covers a compound having a structure of Formula II, wherein: - The structure includes variable functional groups R1, R2, and R3, which are specified in the dependent claims, - The linker L1 is defined as a C1-C9 alkylene, with specific mention of a C5 alkylene, - The structural descriptions for R1, R2, and R3 provide for variations, such as methyl or hydrogen substituents, with possible definitions for R4, R5, R6, R7, and integers m and q. This inventive feature focuses on a compositionally specific molecule with flexibility in its substituents and linkers, enabling a range of fatty acid-based monomer compounds.
Composition comprising the compound of Formula II and a second compound
The invention also covers compositions comprising the compound of Formula II (as described above) in combination with a second compound. - This feature allows for the incorporation of the Formula II compound into mixtures, broadening application possibilities, - The dependent claims specify further combinations where R1, R2 and the structure of the compound can vary among the alternatives described above. This inventive feature is distinct in protecting mixtures, enabling the incorporation of the innovative monomer into varied resin or polymer systems.
In conclusion, the claims protect both the specific structure and composition of fatty acid-derived monomers exhibiting variable functional groups and linkers, as well as their use in compositions with other compounds. This provides protection for both the novel monomers and their practical incorporation in resin systems.
Stated Advantages
Provides a green alternative to currently available thermosetting resins by using plant-based oils as starting materials.
Transforms plant-based oils into useful, durable, and resilient thermoset resins through novel synthetic methods.
Allows for thermosetting polymers with increased crosslink density, giving improved strength and modulus compared to previous vegetable oil-based monomers.
Offers vegetable oil-derived epoxies (such as FA-diepoxy and FA-triepoxy) that are liquid at room temperature, have lower viscosity than commercial bisphenol A epoxy resin, and exhibit higher reactivity.
FA-derived epoxies have thermal stability similar to commercial epoxy resins and can result in resins with well-balanced physical properties when mixed in appropriate ratios.
The products and processes offer a reduced carbon footprint compared to petroleum-based thermoset resins.
Documented Applications
Use in composite matrix polymers.
Use in protective coatings.
Epoxy applications where improved thermal and mechanical properties are desired, including areas requiring high flexural strength and modulus.
Interested in licensing this patent?