Chemistry & Materials

Biodegradable Soy-Based Plastics (RFT-597)
Soy Protein Isolate (SPI) has garnered the interest of the bio-plastics community due to its low cost, desirable transparency and film forming ability. However, poor mechanical strength, flexibility and water resistance have hindered the commercialization of SPI bioplastics. To overcome these fundamental limitations, researchers at NDSU have developed novel SPI based bioplastic formulations reinforced with cellulose nanofibers.
Improved Insulation Properties in Older Windows by Coating with Tightly Packed Aerogel Resin (RFT-590)
Researchers at NDSU have developed a method to produce aerogel coatings that provide thermal insulation and sound dampening.
Bio-Based Alternative to Bisphenol-A Diols and Epoxy Resins from 5-Hydroxymethyl Furfural and Diformyl Furan (RFT-583/584)
Scientists at NDSU have developed bio-based diols that are produced from 5-carbon compounds that can be extracted from cellulosic biomass. These diols may be used to produce epoxy resins without using bisphenol-A, as well as polyesters and polyurethanes. The epoxy resins can be used to produce a range of coatings, composites, and adhesives, including food and beverage container coatings. The 5-carbon compounds that are used to produce these diols are 5-hydroxymethyl furfural (HMF), diformyl furan (DFF), or derivatives of these compounds. The figure shows examples of the paths that can be utilized, but the are only a small sampling of the range of possibilities.
Lignin-Based Thermosets (RFT-542)
NDSU Researchers have developed a process to modify lignin, so as to produce aceto-acetylated (AA-lignin) and methacrylated (MA-lignin) derivatives that are well suited for production of thermosets. This technology enables modification of full sized lignin molecules, and depolymerized lignin subunits, by attaching reactive groups to some or all of the hydroxy groups. The derivatized lignin has lower viscosity than (for example) kraft lignin. This makes it easy to handle and to control crosslinking reactions and can be readily crosslinked to form thermosets through several different mechanisms, including reaction with amines, polyisocyanates, or melamine-formaldehyde resins.
Block-Scaffolds for Bone Regeneration using Nanoclay-Polycaprolactone Scaffolds with Supplements (RFT-533)
Scientists at NDSU have developed a flexible, modular, bone scaffold for filling large bone gaps and accelerating bone growth with various additives, such as nutrients, cytokines, therapeutics and minerals incorporated into the scaffold.  The scaffold is made of a clay and a polymer.
Photoinitiators that Trigger Extremely Rapid and Efficient Polymer Synthesis using UV or Visible Light (RFT-530)
NDSU researchers have developed a range of Type I, Type II, and acidic photoinitiators, which provide polymerization of polyacrylate with good efficiency at low concentrations.  The synthesis of photoinitiators is efficient using routine chemistry, and their structures are easily manipulated to tune for low energy (including visible) light wavelengths.  These photoinitiators are each triggered by a very narrow and easily defined wavelength, making timing of polymerization easy to control (and avoiding inadvertent triggering of the reaction).  The photoinitiators may be produced from either bio-based or petroleum-based starting materials, including such readily available materials as vanillin.
Photodegradable Polymers Enable Recovery of High Value Components from Electronics and Composites (RFT-529)
Only about 10% of post-consumer plastic is recycled in the U.S., leading to waste of plastic and valuable materials embedded in plastic. NDSU researchers have developed a technology to make many plastics photodegradable, enabling recovery of materials from plastics while broadly enhancing plastics recycling.  With respect to recovery of embedded materials, electronic devices and carbon fiber composites being two examples.  More than 30% of carbon fiber ends up discarded.  Electronics have an even worse recycling story.  Almost 90% of electronic waste is disposed without recycling, even though it is a gold mine … one ton of circuit boards contains 40 – 800 times more gold than a ton of ore.  There is also a tremendous amount of copper, silver, and palladium that is discarded rather than recovered.  The NDSU technology enables recovery of these valuable components, which is accomplished by including built-in photocleavable units into the plastic polymers. The resulting photodegradable polymers can be designed for degradation with specific wavelengths of UV and/or visible light by selecting the appropriate photocleavable unit(s).
Novel Non-Isocyanate Siloxane-Polyurethane Coatings (RFT-517)
Glycidyl carbamate (GC) functional resins are used due to their high mechanical strength, toughness and abrasion and chemical resistance associated with polyurethanes as well as the convenience of epoxy-amine chemistry. Webster et al. have combined these resins with polydimethylsiloxane to develop self-stratified coatings that yield coatings having low surface energy as well as reduce the hazards of isocyanates.
Metal-Free Synthesis of N-Containing Compounds Using Stabilized Photoreactive Hydrazide Scaffolds (RFT-514)
NDSU Scientists have developed highly stable hydrazide-based scaffolds that use visible light and a metal-free process to produce molecules and polymers that contain nitrogen (positioned singly or as a pair of adjacent nitrogen atoms).  This scaffold begins with a N-N bond that can be used as a catalyst to make anything from drug and specialty molecules to complex polymers.  The N-N moiety allows creation of unique N-containing molecules, using visible light rather than higher energy UV.  The unique approach is possible because the NDSU team as developed handling procedures that stabilize the hydrazide scaffold until a light sensitizer (such as thioxanthone) is added.  The scaffold utilizes photoinduced excited state chemistry rather than ground state redox chemistry, providing substantially different end products and performance attributes as compared with compounds derived from redox chemistry.
Styrenated Soybean Oil Derivatives as a Replacement for Naphthenic and Aromatic Rubber Processing Oils (RFT-512/513)
Scientists at NDSU have developed styrenated soybean oil derivatives that can be used as a direct replacement for naphthenic and aromatic oils in rubber processing. A particularly promising derivative is soybean oil (SBO) modified with polystyrene (SBO-PS). Tests using this bio-based rubber processing oil produced rubber with improved wet and ice traction with preserved low rolling resistance, while also providing better tensile properties, and similar durometer hardness and tear resistance, as compared with naphthenic and aromatic oils. These results demonstrate that non-toxic soybean oil derivatives can provide high performing alternatives to the more toxic naphthenic and aromatic oils that are currently used for rubber processing. See for example the figure below, comparing naphthenic oil (NO), SBO-PS, and a 50/50 mixture of the two.
Hard and Flexible, Degradable Thermosets from Renewable Bioresources with the Assistance of Water and Ethanol (RFT-502/521)
Thermosets are widely used in industry due to their superior dimensional stability, good processing ability, and high formulation flexibility for tailoring the desired properties such as high modulus, strength, durability, and thermal and chemical resistance. However, they may release VOCs, cannot be reprocessed by heat or solvent, and depend on non-renewable resources. To address these issues, Webster et al. developed degradable bio-based thermosets. These novel thermosets achieve high hardness while maintaining excellent flexibility as well as outstanding adhesion and solvent resistance, which is unprecedented in the field. Further, they degrade rapidly in aqueous base conditions in addition to being thermally degradable.
Polymers Derived from Bio-Diesel Waste for Road Dust Control (RFT-499)
Scientists at NDSU have developed a new material that can be applied to gravel roads for suppression of road dust. The material is made from the huge waste stream that is generated during the production of biodiesel which is primarily glycerol and biodegradable or bio-derived fatty acid esters. The new material is made up of mono- and di-gylcerides that are synthesized from a combination of waste glycerol and soybean oil triglycerides. Upon application to the road surface, the glycerides undergo crosslinking reactions to form a larger, more stable molecule.
Epoxidized Sucrose Esters of Fatty Acids (RFT-314, 422, 459, 488, 489, 502)
Scientists at North Dakota State University have developed a method to produce epoxidized sucrose esters of fatty acids (ESEFAs).  These are macromolecules with a rigid sucrose core from which 8 arms extend, the arms derived from fatty acids.  ESEFAs have extraordinary versatility with respect to potential uses and manufacturing processes.
Bio-Based Monomers for Polymers and Plastics (RFT-478)
Scientists at NDSU have developed bio-based monomers, derived from lignin or cellulose, that have promise for high quality polymers and plastics.  Use of lignin is made more reliable and less expensive by using the diverse core compounds that are intermixed in lignin polymers in whatever combinations and ratios they are found.  These compounds can be disassembled to form a pool of monomers, which are then modified en masse to form dicarboxylic acid derivatives, and then polymerized again to form linear polymers with surprisingly consistent and predictable properties.  Among the valuable end products that can be obtained from cellulose are several derived from hydroxymethylfurfural (HMF).  These include many di-alcohols, di-carboxylic acids, and diamines.  These monomers can be polymerized using standard Perkin condensation and other widely used chemical processes.  They may be used individually or together to produce polyesters and polyamides using the same types of processes and facilities that are currently used for production of PET and other petroleum-based polymers.
Acrylic Monomers Derived from Plant Oils - Synthesis and Use in High Value Polymers (RFT-462)
Scientists at NDSU have developed an efficient and cost-effective one-step method to convert plant oils into acrylic monomers that substitute for petroleum-based monomers in the production of acrylic polymers.  This method can use essentially any plant oil, animal fat, or other fatty esters as the raw material.  The output is a combination of (meth) acrylic fatty monomers that can be used directly in the production of latexes, adhesives, surfactants, sizing agents, resins, binders, and other products that utilize acrylic polymers.  Additionally, the NDSU monomers contain two types of double bonds.  The one within the acrylic group is reactive in conventional addition free radical polymerization, which allows formation of linear polymers.  The double bonds within the fatty chain remain unaffected during free radical polymerization, so remain available for oxidative cross-linking and additional tuning of the polymer performance characteristics.  This is in contrast to existing plant oil based monomers, which produce non-linear branched and cross-linked polymers (because their fatty chain double bonds may react during the polymerization reaction).
Epoxidized Sucrose Esters of Fatty Acids (RFT-314, 422, 459, 488, 489, 502)
Scientists at North Dakota State University have developed a method to produce epoxidized sucrose esters of fatty acids (ESEFAs).  These are macromolecules with a rigid sucrose core from which 8 arms extend, the arms derived from fatty acids.  ESEFAs have extraordinary versatility with respect to potential uses and manufacturing processes.
High Performance, Bio-based Polyamides for Injection Moldable Products (RFT-452)
Scientists working at NDSU have discovered a method for making thermoplastics for injection molding that are based, in part, on renewable resources. Unlike other bio-based polyamides, these possess the high melting temperatures, fast crystallization rates, low moisture uptake, and good mechanical properties associated with engineering thermoplastics. These polymers can be used to replace the petroleum-based nylon 6,6 and nylon 6 for high end injection molding applications such as the electronic and automotive parts.
Roll-to-Roll Synthesis of Silicon Thin Films from Liquid Silanes (RFT-447)
Silicon thin films are fundamental in solar and microelectronic industries, and are presently obtained using expensive low-pressure plasma enhanced chemical vapor deposition (PECVD) using gaseous silanes despite of its low precursor utilization efficiency. Instability and low vapor-pressure of liquid hydrosilanes have limited their use in the semiconductor industries for longtime. Researchers at NDSU have developed a process to synthesis silicon thin films from liquid hydrosilane (Si6H12) at ambient pressure in a roll-to-roll method using atmospheric pressure aerosol assisted chemical vapor deposition (AA-APCVD) that has higher deposition rates compared to the state-of-the-art PECVD. Solubility of solid dopants in the liquid hydrosilane facilitate the deposition of degenerately doped (n & p –type) Si thin films opposed to compressed toxic phosphine and borane gases used in other techniques. Low decomposition temperature (higher activation energy) of cyclohexasilane (Si6H12), a liquid hydrosilane, benefits for a new plasma-free process for the synthesis of silicon nitride films and Si nanowires (with suitable catalyst) at temperatures as low as 350 oC using the AA-APCVD, readily adoptable for large-scale roll-to-roll continuous manufacturing. Liquid hydrosilane compositions consisting of nanomaterials enable hybrid Si films with embedded nanomaterials that have applications in energy harvesting and light emitting devices.
Plant Oil-Based Reactive Diluents for Coating and Composite Applications (RFT-438)
NDSU scientists have developed plant oil-based reactive diluents for coating and composite applications that possess both low viscosity and high reactive functionality. With these improved characteristics, these plant oil-based materials eliminate or reduce the need to be blended with petrochemicals thereby increasing the bio-based content of the product, which is environmentally more desirable. The fundamental aspect of the invention involves transesterification of a plant oil triglyceride with an alcohol that also contains at least one double bond. By completely replacing the glycerol component of the plant oil triglyceride with three equivalents of the unsaturated alcohol, fatty acids esters are produced containing at least one double bond that is not derived from the parent plant oil. Depending on the application requirements, a low-cost, bio-based unsaturated alcohol can be used to produce the reactive diluents of the invention.
Vegetable Oil-Based Polymers for Nanoparticle Surface Modification (RFT-413)
The extremely high surface area of nanoparticles provides many advantages over conventional particles with dimensions in the micron scale. For a variety of applications, it is necessary to suspend the nanoparticles in a liquid medium. Researchers at NDSU have developed a new plant-oil-based polymer technology focused on the application of nanoparticle suspension in water.
Amphiphilic Siloxane-Modified Polyurethanes, Cosmetics, and Surfactants, Having Anti-Fouling/Anti-Biofilm Properties (RFT-380)
Scientists at NDSU have developed a graft co-polymer that confers amphiphilic properties to many materials, including polyurethanes, cosmetics, and surfactants. In the case of polyurethanes, this technology enables inclusion of resistance to biofouling and biofilm formation to be incorporated into the polyurethane structure.
Efficient Processes to Produce Polyalkylated Oligo-ethyl-polyamines (RFT-324)
Certain Polyalkylated Oligo-ethyl-polyamines such as TMEDA, TEEDA and PEDETA are useful intermediates in organic synthesis and analytical chemistry and used extensively in inorganic chemistry as ligands for a variety of metal complexes. In spite of high demands, PEDETA (penta-ethyl-di-ethylene-triamne) has not been available in industrial scales due to the difficulty in the realization of complete alkylation of the starting material using conventional methods. This novel method describes a process of obtaining PEDETA that is pure and without any side or incomplete alkylated product. The process involves no work-up and is thus environmentally friendly. In addition, the reaction time and work-up process is drastically reduced from the conventional synthesis method.
Electrospinning Process for Continuous High-Volume Silicon Micro- and Nano-Wire Production (RFT-311)
Scientists at North Dakota State University (NDSU) have developed a process for continuous high-volume production of silicon micro- and nano-wires based on electrospinning. The technology is based on the ability to use liquid silane as a starting material, so the length of the wires is essentially unlimited. The wires can be produced with a variety of polymers, metal particles, and silane variations to generate a range of properties and capabilities. Potential applications include composite materials, electronic devices, sensors, photodetectors, batteries, ultracapacitors, and photosensitive substrates.
The Use of Fibers From Agricultural Waste Streams as a Reinforcing Agent in Commodity Thermoplastics (RFT-278)
This invention describes a process wherein lignocellulosic fibers recovered from various agricultural waste streams (such as crop waste otherwise discarded by ethanol plants) are combined with commodity thermoplastics as a means of reinforcing and strengthening the plastics. This method works with commodity thermoplastics and recycled plastics where other fiber reinforcing processes have not succeeded.
Composition and Method of Forming Functionalized Cyclohexasiloxane (RFT-265)
This invention pertains to a composition of matter derived from cyclohexasilane. The compound has unique physical properties and can exist in a liquid state at standard temperature and pressure - a characteristic that renders them appropriate for applications in novel deposition routes including high-speed printing and direct-write. The invention has applications in the manufacture of silicon-based solar cell in the photovoltaic industry.
Modified Glycidyl Carbamate Resins Exhibiting Superior Mechanical Properties (RFT-226)
This invention pertains to novel glycidyl carbamate resins that have been modified with alkyl or ether alkyl groups. These resins have improved properties such as lower viscosity, which makes them good candidates for commercialization in the paint industry. In particular, it has potential for application as a coating on aircrafts.
Unique Sol-Gel Hybrid Coatings with Superior Properties for a Wide Range of Industrial Applications (RFT-225/240)
This invention pertains to the preparation of two-component polyurethane coating formulation comprising: an epoxy functional binder, and a blended curing component (having one sol-gel and one amine cross-linker.
Novel Polyurethane/Epoxy Hybrid Coatings (RFT-219)
This invention involves the preparation of a novel coating composition comprising a glycidyl carbamate functional resin, an aromatic epoxy resin, and a polyamine cross-linker. This coating formulation with the aromatic epoxy resin has improved corrosion resistance over coatings that do not contain the aromatic epoxy resin.