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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.
Worldwide efforts have been devoted to converting biomass into chemicals due to the high abundance, low cost, and renewability. Carbohydrates are of particular interest as one of its derivatives, FDCA, is one of the top 14 bio-based chemicals that can be used as a replacement in the synthesis of polyethylene terephthalate (PET). Though made from renewable resources, recyclability of the polymers has remained an issue. Sivaguru et al addressed this through the use of a nitrobenzyl phototrigger unit backbone which allows for controlled photodegradation, via UV irradiation, of biomass-derived polymers.
Scientists from North Dakota State University have utilized the vanillin that was derived from lignin as a bio-based cross-linker in melamine-formaldehyde coatings. Vanillin is first reacted with any acetoacetylated polyol via a Knoevenagel Condensation, allowing production of a wide range of intermediates that are suitable for crosslinking with MF resins. The resulting products would have numerous potential applications, including laminate flooring, cabinetry, surface coatings, textile finishes, and paper processing. The use of vanillin not only provides a bio-based alternative, but the resulting coatings were shown to provide increased impact resistance, hardness, and solvent resistance.
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 hav ing low surface energy as well as reduce the hazards of isocyanates.
There has been growing commercial and industrial interest in biodegradable and renewable materials over petroleum-based materials. Particularly, soybean oil is widely used due to its availability and low cost. Chisholm et al have determined that appropriate modification of soybean oil results in materials for use as a processing oil for rubber compounds. They show, through numerous examples, that the use of unmodified soybean oil reduces key mechanical properties, such as moduli and tensile strength when compared to conventional petroleum-based processing oils. However, rheological and mechanical properties can be substantially improved by 1) styrenating the soybean oil or 2) producing a higher molecular weight liquid from soybean oil (ex: sucrose soyate and soy-based oligomer). Thus, soybean oil can be used as the basis for a bio-based and green alternative to petroleum-based oils for rubber compounds.
Though corrosion is well understood in terms of mechanisms and methods of control, it still accounts for a notable number of failures in pipelines buried or on the ground. This is due to a large number of potential complications such as varying soil properties along the pipeline and over time, local cracks on the soft coating surface, separation of coating from the pipeline surface, and corrosive environments. To address this, Azarmi et al developed smart coatings which can both prevent and monitor corrosion of steel through the use of a hard coating deposited by thermal spraying with embedded Fiber Bragg Grating (FBG) sensors.
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.
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.
NDSU Researchers have developed a process to modify lignin, so as to produce acetoacetylated (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.
There has been growing interest in bio-based resins due to the foreseeable limit of fossil feedstocks and increasing environmental concern. Additionally, polyurethanes are widely used commercially but rely on petroleum-based materials and utilize isocyanate, which is hazardous. Webster et al. have developed a novel bio-based material that can be reacted with amines to form polyurethanes using a non-isocyanate route, and thus are safer than current systems. Specifically, the resins contain a high number of cyclic carbonate groups synthesized from the reaction of epoxidized sucrose fatty acid ester resin with carbon dioxide. Further, these resins are prepared from epoxidized sucrose fatty acid esters from different vegetable oils and can be fully or partially carbonylated.
Thermosetting Thermosetting polymers and composites are widely used in industry due to their low density, good mechanical properties, low cost, and dimensional stability. However, most resins are synthesized primarily using petroleum-based chemicals. Researchers at NDSU have developed vanillin-based epoxy resins synthesized from the reaction between vanillin and diamines to form a Schiff base (I), which is then glycidated to form an epoxy resin (II). The resin may then be crosslinked using amines to form a thermoset coating (the example showing reaction with a diamine that leads to a crosslinked coating). Vanillin from any source may be used, including from lignin, which could expand the opportunity for value-added uses of lignin.
Scientists at NDSU have developed a one-step method to convert plant oil 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.
Thermosetting polymers and composites are widely used in industry due to their many desirable characteristics, such as low density and cost, dimensional stability, and good mechanical properties. However, most of these resins are petroleum-based raising environmental concerns and potentially increasing cost and regulations. Thus, there is a demand for novel resins and composites synthesized from renewable materials, such as plant oils. Webster et al. answer that need with a novel bio-based resin containing a large number of unsaturated vinyl groups. Specifically, they have developed a polyfunctional bio-based oligomer synthesized from an epoxidized sucrose fatty acid ester resin and an ethylenically unsaturated ester (RFT-459). More recent modifications by the group (RFT-489) have added an acid anhydride leading to a vinyl functionalized resin with a lower viscosity. The resins can then be cured using free radical initiators to form highly crosslinked thermosets with numerous applications. These systems use significantly lower amounts of styrene than petrochemical vinyl ester resins.
The use of bio-based resins and/or natural fibers in composites has emerged due to the need for improved chemical sustainability and environmental impact. There is growing interest in polyurethanes as they are durable and cost effective. However, they are traditionally made from petroleum based polyols and isocyanates. Ulven et al answer the need for sustainable materials with the development of structural biocomposites comprising cellulose-based bast natural fibers and/or glass fibers and bio-based polyurethanes. Specifically, bio-based polyols are reacted with polyisocyanates to generate bio-based polyurethanes. These materials have a higher modulus, hardness, and Tg than other bio-based and petroleum-based polyols.
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.
Due to the finite supply of fossil resources and the growing environmental concern, there is a major need for chemicals and materials derived from renewable resources. Aromatic building blocks, such as phenols, are particularly important and can be derived from renewable sources. Chisholm et al are the first to convert eugenol and iso-eugenol into vinyl ether monomers via reaction of the hydroxyl group. The result is soluble, processable linear polymers that retain the allyl group for crosslinking reactions and incorporation of other functional groups.
Scientists working at NDSU have discovered a way to make vinyl-block bio-based carboxylic acid crosslinkers for epoxy resins that are particularly useful for vegetable oil based epoxy resins. The resulting coatings have an excellent combination of hardness, flexibility, adhesion, and solvent resistance.
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.
Surfaces having non-fouling characteristics are of great interest for the development of advanced materials in many different applications. In medical device applications, protein attachment can cause any number of unwanted immune reactions when exogenous materials are implanted into biological systems. Materials developed with polyethylene glycols, often referred to as PEGylated materials, are of great interest due to their protein resistance and nontoxic properties.
Scientists working at NDSU have developed branched and hyperbranched oligomers derived from a combination of soybean and cashew nutshell oils (CNSL). These oligomers can be either UV-cured (for coatings) or thermally cured (to produce thermoset polymers). Coatings incorporating this hyperbranched material had improved adhesion and impact resistance, because the coatings were both strong and flexible. This material can be used in anti-corrosion and coatings and sealants, composites, inks, and adhesives, as well as directly in thermoset polymers. These oligomers impart improved material properties compared to current bio-based materials, and in some cases exhibit properties superior to even their petroleum-based counterparts.
NDSU Scientists have developed a UV-curable anti-corrosive coating for metal and wood substrates. The coating is curable in 30 to 60 seconds at room temperature under UV light. Coating components include well-known materials, including a UV-responsive photoinitiators, acrylated plant oil (providing hydrophobicity and contributing to physical barrier), and hyperbranched polyester (providing physical barrier to moisture). Variations on this basic formula can be developed and optimized for specific substrates and environmental conditions to create highly functional anti-corrosion coatings with a high bio-based content.
Scientists at NDSU have synthesized monomer-grafted sucrose ester resins by polymerizing styrene in the presence of the sucrose ester resins. At a composition of 50% styrene-50% sucrose ester, coatings had extremely fast tack free drying times, similar to a commercial styrenated alkyd resin. However, the styrenated sucrose ester resin had a much lower viscosity than the commercial resin, meaning that higher solids coatings can be prepared. In addition, water dispersible resins were prepared by grafting a mixture of styrene and acrylic acid with the sucrose ester resin. These could be cross-linked with a melamine-formaldehyde resin to yield coatings that had good hardness, adhesion, and flexibility.
NDSU Scientists have found that incorporating oligo (ethylene glyol) segments and perfluorinated siloxane segments into moisture-curable polysiloxane coatings results in a synergist enhancement in fouling-release properties toward a suite of marine organisms. Also, the addition of the oieties does not negatively affect the mechanical properties of the coating after immersion in water. This invention has lead to the development of novel amphiphilic fouling release coatings that exhibit superior fouling release properties.
This proprietary technology platform involves the conversion of plant oil triglycerides to polymerizable monomers that are subsequently used to produce a wide variety of bio-based polymers, tailored for specific applications in multiple industries. There are four major attributes of the proprietary polymerization process that set this technology apart from all other previously developed plant oil-based technologies developed to date. These key features also allow major material performance advantages that enable this renewable polymer technology to successfully compete with petroleum-based polymer materials.
NDSU Scientists have synthesized a highly functional epoxy resins from the epoxidation of vegetable oil esters of polyols having 4 hydroxyl groups per molecule. These epoxy resins can be cured using UV photo-initiators into hard coatings. The novel epoxy resins can also be incorporated into formulations containing oxetanes, cycloaliphatic epoxies, and polyols. The photo-polymerization rate is significantly higher for these novel epoxy resins when compared to conventional epoxidized vegetable oil.
Researchers in the NDSU Department of Coatings and Polymeric Materials (CPM) have discovered enamine resins which are the reaction products of an acetoacetatylated resin, and a C1-C20 alkyl amine or a mixture of C1-C20 alkyl amines. The acetoacetylated resin is the reaction product of a polyol having 4 or more hydroxyl groups; and at least one acetoacetate. The invention also relates to an acetoacetylated resin which is the reaction product of a polyol having 4 or more hydroxyl groups and at least one acetoacetate, where a portion of the hydroxyl groups of the polyol are replaced by acetoacetate groups and the remaining hydroxyl groups are replaced by a saturated monofunctional carboxylic acid ester, unsaturated monofunctional carboxylic acid ester, or a mixture thereof; as well as to enamine resins prepared from these acetoacetylated resins.
Scientists at North Dakota State University have invented a Low-VOC, chromate-free, solventborne, low viscosity, highly flexible coating resin system. This resin system has the functionality of an epoxy resin while providing the performance of a polyurethane coating without exposing the end-user to isocyanates. When crosslinked with amines, these GC coatings have excellent adhesion, hardness, solvent resistance, gloss, and flexibility on cold-rolled steel and aluminum substrates. This polymer technology was specifically developed to be used to obtain highly flexible coatings while maintaining good solvent and chemical resistance.
Scientists at North Dakota State University have invented a unique ‘dual action’ anti-microbial polysiloxane coating that has the capability of exhibiting long-term antimicrobial activity on implantable medical devices. The coatings have a leachable silver-based antimicrobial domain in conjunction with a surface-bound contact active microbial agent - Quaternary Ammonium salt (QAS) that exhibits the two levels of antimicrobial protection. While the covalently bound QAS groups inhibits bio-film formation by microorganisms that come into contact with the coating prior to insertion of the devices into the body, the leachable antimicrobial agent inhibits bio-film formation by microorganisms in the vicinity of the device.
A new type of UV-curable PDMS coating was formulated and characterized in this invention. Preliminary investigations have shown that the surface is hydrophobic and films are softer than that obtained from unmodified polyester. The basis of this invention is in the synthesis of novel unsaturated polyester compositions containing poly-dimethyl-siloxane (PDMS) by mixing these polyesters with co-reactants and photoinitiators, and curing the compounds using either visible or UV light to form coatings having low surface energy. Applications include marine, packaging materials, protective wood coatings, anti-graffiti coatings, easy clean coatings and release coatings. The uniqueness and importance of this invention pertains to its novel siloxane-modied unsaturated polyesters, UV curable technology (so no oxygen inhibition), low siloxane (cost effective), and solvent free nature.
This invention pertains to the development of a polymer material that exhibits superior sustained release of therapeutic levels of the active antibiotic when compared to simple physical bending or doping technologies. The material is prepared by combining a powerful, broad spectrum antibiotic (Levofloxacin), tethered to a siloxane polymer. This invention can potentially be used to coat a variety of biomedically implanted devices for prevention of microbial infection.
This invention pertains to novel siloxane-urethane coatings that were developed from unique single-end-functional siloxane polymers. These reaction siloxanes are incorporated into polyurethane coatings and result in coatings having low surface energy but good adhesion and mechanical properties.
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.
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.
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.
This invention pertains to the development of stable polymeric anti-fouling surface coating formulation that contains Quaternary Ammonium Salts (QAS) as the primary disinfectant.
Scientists at NDSU have invented a novel non-toxic, crosslinked thermoset polysiloxane-polyurethane coating that exhibits properties as foul release (FR) coating and allows organisms to be sloughed off by shear forces obtained at a ship's cruising speed. In addition to exhibiting its fouling release behavior, these coatings have been demonstrated to provide improved durability to its coating surface.
Scientists at North Dakota State University have combined biocidal and fouling release activities into a single polymeric formulation to develop a unique environmentally friendly coating that holds promise in both marine and medical applications. This novel formulation consists of biocidal moieties that are tethered to its polymer matrix, which in turn prevent them from leaching into the environment.
NDSU inventors have developed polymer films and additives that can be used in polymer films such as polyol photosensitizers, carrier gas UV laser ablation sensitizers and other additives that can be used in preparation of such carrier films.
This invention pertains to novel coating compositions that spontaneously phase separate to form uniform micro-domains on the coating surface, providing a multiphase topographical surface structure with textured surface that inhibits adhesion.
Scientists at North Dakota State University have invented a group of novel polymeric coating formulations that have been found to demonstratae its effectiveness in preventing marine-life fouling on surfaces exposed to salt and fresh water. The invention encompasses novel poly-siloxane-polylactone block copolymer compositions that contain carbamate linking groups that provide superior compatibility with polyurethante coating compositions.
This invention pertains to novel water dispersible compositions (and methods of making same) having epoxy urethane functional groups. These compounds can be dispersed in water with an added surfactant to form a dispersion containing no volatile organic solvent. The dispersed polymer can self-crosslink and can also crosslink with multifunctional amine compounds into a hard, glossy, solvent resistant coating.
These inventions pertain to unsaturated polyester polymer compositions containing monomer molecules that sensitize the resulting polymer coating/film to ablation (i.e., removal of film material) by exposure to laser radiation. This technology is of potential value to parties in the semi-conductor and electronic manufacturing industries.
Since the early 1980’s, the use of chromates and other chromium-containing compounds have been subject to stringent regulations due to their recognized carcinogenic properties. In an attempt to find a substitute for widely used chromium-based primer coating products, scientists at North Dakota State University have invented a novel, chrome–free primer coating with proven anti-corrosive properties on metal substrates The use of this primer eliminates risks associated with handling toxic and carcinogenic chromium metallic compounds, and alleviates waste disposal hazards. This invention has been proven to be the only technology that protects high strength Aluminum alloys from corrosion, without the need of any chromate pretreatment or pigmentation.
Proprietary and novel, silicone-based compounds (and methods for synthesis), some of which incorporate tethered biocide moieties (for marine applications), have been developed that can be used in coating formulations to prevent or reduce fouling by marine life and related substances on ship surfaces.
This technology package consists of two different disclosures. One is a protective primer coating for two different aluminum alloys used in the construction of aircraft. The second is the application and optimization of that coating to structures of different alloys such as aircraft skin, rivets and struts. This technology protects aluminum from corrosion while eliminating toxic and carcinogenic materials such as chromium, that are currently used for corrosion protection.
Linear and cyclic polysiloxanes functionalized with amine moieties have been synthesized utilizing aminoalcohols. The reaction is cost effective and a one-pot process with minimal purification of end product required. A diverse and versatile array of amino-silicone products are possible due to the variety of aminoalcohols commercially available.
This NDSU invention is a ceramer precursor coating composition which can be used to form ceramer coatings having high tensile modulus and tensile strength while exhibiting a relatively moderate strain-at-break value. The coating composition includes an unsaturated oil stock and a sol-gel precursor which includes a mixture of at least two different sol-gel precursor species. The use of two sol-gel precursors has resulted in superior film properties over the use of a single sol-gel precursor. Examples of suitable mixed metal sol-gel precursors include mixtures which contain at least one titanium and one zirconium sol-gel precursors.