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Siloxane-polyurethane hybrid coatings were assessed for biofouling control caused by freshwater mussels. Invasive species such as zebra (

Combining amphiphilic fouling-release (FR) coatings with the surface-active nature of amphiphilic additives can improve the antifouling/fouling-release (AF/FR) properties needed to offer broad-spectrum resistance to marine biofoulants. This work is focused on further tuning the amphiphilic character of a previously developed amphiphilic siloxane-polyurethane (SiPU) coating by varying the amount of PDMS and PEG in the base system. Furthermore, surface-modifying amphiphilic additives (SMAAs) were incorporated into these amphiphilic FR SiPU coatings in varying amounts. ATR-FTIR, contact angle and surface energy measurements, and AFM were performed to assess changes in surface composition, wettability, and morphology. AF/FR properties were evaluated using laboratory biological assays involving

Grooming may be an effective technique to control marine biofouling without damaging the coating or discharging active ingredients into the environment. This study assessed the grooming performance of three experimental biocide-free siloxane polyurethane (SiPU) fouling-release coatings. Coatings were statically immersed in Port Canaveral, Florida, and groomed every two weeks for five months using three different brush types. The ungroomed panels became heavily fouled with biofilm, tubeworms, barnacles, and bryozoans. Two of the brushes were able to control the fouling with a coverage of via grooming without damage or changing the surface properties.

In this work, surface-modifying amphiphilic additives (SMAAs) were synthesized via hydrosilylation using various polymethylhydrosiloxanes (PMHS) and allyl-terminated polyethylene glycol monomethyl ethers (APEG) of varying molecular weights. The additives synthesized were incorporated into a hydrophobic, self-stratifying siloxane-polyurethane (SiPU) coating system to produce an amphiphilic surface. Contact angle experiments and atomic force microscopy (AFM), in a dry and hydrated state, were performed to assess changes in surface wettability and morphology. The antifouling and fouling-release (AF/FR) performances were evaluated by performing laboratory biological assays using the marine bacterium Cellulophaga lytica, the microalga Navicula incerta, the macroalga Ulva linza, the barnacle Amphibalanus amphitrite, and the marine mussel, Geukensia demissa. Several of the formulations showed improved AF/FR performance vs the base SiPU and performed better than some of the commercial standard marine coatings. Formulations containing SMAAs with a low grafting density of relatively high molecular weight PEG chains showed the best performance overall.

Amphiphilic surfaces, containing both hydrophilic and hydrophobic domains, offer desirable performance for many applications such as marine coatings or anti-icing purposes. This work explores the effect of the concentration of amphiphilic moieties on converting a polyurethane (PU) system to a coating having fouling-release properties. A novel amphiphilic compound is synthesized and added at increasing amounts to a PU system, where the amount of the additive is the only variable in the study. The additive-modified surfaces are characterized by a variety of techniques including ATR-FTIR, XPS, contact angle measurements, and AFM. Surface characterizations indicate the presence of amphiphilic domains on the surface due to the introduction of the self-stratifying amphiphilic additive. The fouling-release properties of the surfaces are assessed with three biological assays using Ulva linza, Cellulophaga lytica, and Navicula Incerta as the test organisms. A change in the fouling-release performance is observed and plateaued once a certain amount of amphiphilicity is attained in the coating system, which we call the critical amphiphilic concentration (CAC).

Although soybean oil (SBO) has been used as a bio-based processing oil (PO) for rubber compounds, direct replacement of a conventional petroleum-based PO with SBO often results in a reduction of some important properties. As a result, it was of interest to investigate two higher molecular weight SBO-derived materials as POs, namely, sucrose octasoyate (SS) and poly(2-vinyloxyethyl)soyate (P2VOES). When these compounds were used in carbon black (CB)-filled SBR, mechanical properties were significantly improved. This result was mainly attributed to higher crosslink densities resulting from their higher degree of unsaturation per molecule as compared with SBO. Higher unsaturation per molecule increases the probability that the PO will be incorporated into the crosslinked network as elastically effective crosslinks as opposed to dangling chain ends. With regard to tire tread performance, both SS and P2VOES-based vulcanizates showed a lower predicted rolling resistance than the SBO-based control, and the P2VOES vulcanizate showed a better balance between rolling resistance and wet traction. Vulcanizates derived from SS and P2VOES showed a small tangent delta peak between −13 and 35 °C that might be associated with relatively highly crosslinked domains rich in SS or P2VOES.

A series of asymmetric and symmetric diols were prepared in high yields from biomass-derived feedstocks 5-hydroxymethyl furfural (HMF) and 2,5-diformyl furan (DFF) as potential replacements for bis...

Photodegradable, recyclable, and renewable, crosslinked polymers from bioresources show promise towards developing a sustainable strategy to address the issue of plastics degradability and recyclability. Photo processes are not widely exploited for upcycling polymers in spite of the potential to have spatial and temporal control of the degradation in addition to being a green process. In this report we highlight a methodology in which biomass-derived crosslinked polymers can be programmed to degrade at ≈300 nm with ≈60 % recovery of the monomer. The recovered monomer was recycled back to the crosslinked polymer.

Icephobic coatings have applications in many industries to protect surfaces from deterioration and avoid catastrophic incidents. In this work, we report a new strategy to prepare amphiphilic siloxane-glycidyl carbamate coatings (AmpSiGC) coatings with anti-icing property. Polydimethyl siloxane (PDMS) and poly(ethylene glycol) (PEG) provided amphiphilicity for the AmpSiGC coatings. The designed experiment considered several factors: molecular weight of the surface-modifying polymers and their amount in the coating system. Although amphiphilic coatings have demonstrated promising results as marine coatings, investigations on their icephobic applications have been limited. This work discusses three aspects of the developed AmpSiGC systems: (1) preparation of the incorporated ingredients and their characterization by Fourier transform infrared spectroscopy (FTIR); (2) surface characterization of coatings via ATR (attenuated total reflectance)-FTIR, X-ray photoelectron spectroscopy (XPS), and atomic force microscopy (AFM); and (3) ice-adhesion, electrochemical impedance spectroscopy (EIS), and mechanical property evaluations. Overall, the surface analysis indicated the presence of both hydrophobic and hydrophilic domains and most of the coatings demonstrated promising performance for anti-icing applications with desirable barrier and mechanical properties in comparison to controls.

Highly functional bio-based methacrylate and acrylate resins were synthesized from epoxidized sucrose soyate (ESS) and incorporated into formulations for stereolithographic (SLA) printing. These fo...

Carboxylic acids are widely used as building blocks in several types of coating systems, including as hardeners for epoxy resins. The chemical structure of the acid significantly impacts the coatin...

Frontal polymerization has been explored as a technique to form two-dimensional thin films (0.5 mm) on wood. We used trimethylolpropane triacrylate with a thermal free-radical initiator. The viscosity of the resin was adjusted by incorporating fumed silica within the formulation. As filler materials, either calcium carbonate or graphene nanoplatelets was used to evaluate the effect of filler type and content on front propagation. We observed that resin viscosity and film thickness critically affected the qualitative and quantitative propagation of the thermal front resulting in the formation of the coating. A workable coating was formed at a viscosity of 0.6 Pa·s, which was obtained when 3 phr (parts per hundred resin) of fumed silica was used in the resin formulation. Wet film thickness for this resin system was also found to have a limiting value, and full propagation of the front to result in a conformal coating required at least 15 mil (1 mil = 25 μm) of wet film thickness. Filler materials affected film propagation as a function of particle size and thermal properties. While 15 phr calcium carbonate could be incorporated with the resin, only 5 phr graphene nanoplatelets could be loaded within the matrix to ensure complete propagation of the front. Interestingly, for graphene fronts, velocity and temperature reduced systematically as a function of filler content. Filler type and content affected porosity and roughness of the coating, which was quantified by computerized tomography to understand the relationship between porosity and adhesion of the coated film with the wood substrate.

The invention relates to curable non-isocyanate polyurethane coating compositions which is the reaction product of a polycarbamate resin and a dialdehyde. The invention also relates to methods of making and using the curable coating compositions of the invention. The invention also relates to objects coated with the curable coating composition of the invention

Soybean oil (SBO) was modified with polystyrene via a radical graft polymerization reaction for use as a processing oil in tire tread compounds. Poly(styrene-butadiene)/polybutadiene rubber compounds with silica and carbon black, containing different processing oils including naphthenic oil (NO), aromatic oil (AO), SBO, and polystyrene-modified SBO (SBO-PS), were formulated, vulcanized, and tested. The curing behavior, mechanical properties, and dynamic properties were investigated. The cure test results showed that all SBO-based rubbers had a shorter scorch time and cure window than the NO- and AO-based rubbers. The tensile tests demonstrated that partial and complete replacement of NO with SBO led to reduced tensile modulus but increased elongation of rubber. For the rubbers compounded with SBO-PS and with a 50/50 mixture of NO/SBO-PS, tensile strength and elongation were higher than for the NO-based rubber. The same tendency was observed when SBO-PS–based rubbers were compared with SBO- and AO-based rubbers. SBO-PS–based rubbers demonstrated better tensile properties than AO-based rubbers and far better properties than SBO-based rubbers. In the tear resistance test and durometer hardness test, SBO-PS contained rubbers that showed similar properties to NO-containing rubber. The dynamic mechanical analysis of SBO-PS–containing rubbers demonstrated that use of this compound in tire treads is expected to improve both rolling resistance and wet traction when compared with an AO-based rubber. The modification of SBO with grafted PS is a promising method of making processing oil, which can replace petroleum-based processing oils with bio-based renewable oils in tire tread compounds while improving their properties.

A series of novel plant oil (PO)-based poly(vinyl ether)s were produced that varied with respect to PO composition and molecular weight (MW). The POs investigated were soybean oil, linseed oil, and camelina oil. All of the polymers were liquids at room temperature and were used to produce crosslinked networks, both as free-standing films and as surface coatings on steel substrates. Crosslinking was achieved at ambient conditions through the process of autoxidation. Viscosity of the neat polymers as well as the viscoelastic and mechanical properties of crosslinked networks were highly dependent on parent PO composition. At a given polymer MW, viscosity decreased with increasing PO unsaturation, while glass transition temperature, Young’s modulus, and tensile strength of crosslinked networks increased with increasing PO unsaturation. For polymers derived from the most highly unsaturated PO, i.e. linseed oil, impact resistance of coatings was significantly compromised, due to the relatively high crosslink density of these coatings. Overall, these results demonstrated that viscosity and the properties of crosslinked films based on these novel PO-based poly(vinyl ether)s could be tailored through selection of the parent PO and control of polymer MW. This class of highly bio-based polymers appears to have particular utility for the production of one-component, ambient-cured coatings. One component, ambient-cured thermoset coatings are highly desired because of their ease of use, lower waste production, and energy cost savings compared to other thermoset coating systems.

Biocomposites can be both environmentally and economically beneficial: during their life cycle they generally use and generate less petroleum-based carbon, and when produced from the byproduct of another industry or recycled back to the manufacturing process, they will bring additional economic benefits through contributing to a circular economy. Here we investigate and compare the environmental performance of a biocomposite composed of a soybean oil-based resin (epoxidized sucrose soyate) and flax-based reinforcement using life cycle assessment (LCA) methodology. We evaluate the main environmental impacts that are generated during the production of the bio-based resin used in the biocomposite, as well as the biocomposite itself. We compare the life cycle impacts of the proposed biocomposite to a functionally similar petroleum-based resin and flax fiber reinforced composite, to identify tradeoffs between the environmental performance of the two products. We demonstrate that the bio-based resin (epoxidized sucrose soyate) compared to a conventional (bisphenol A-based) resin shows lower negative environmental impacts in most studied categories. When comparing the biocomposite to the fossil fuel derived composite, it is demonstrated that using epoxidized sucrose soyate versus a bisphenol A (BPA)-based epoxy resin can improve the environmental performance of the composite in most categories except eutrophication and ozone layer depletion. For future designs, considering an alternative cross-linker to facilitate the bond between the bio-based resin and the flax fiber, may help improve the overall environmental performance of the biocomposite. An uncertainty analysis was also performed to evaluate the effect of variation in LCA model inputs on the environmental results for both the biocomposite and composite. The findings show a better overall carbon footprint for the biocomposite compared to the BPA-based composite at almost all times, demonstrating a good potential for marketability especially in the presence of incentives or regulations that address reducing the carbon intensity of products. This analysis allowed us to pinpoint hotspots in the biocomposite&rsquo, s supply chain and recommend future modifications to improve the product&rsquo, s sustainability.

A series of plant oil based polyvinyl ethers were synthesized and evaluated as potential replacements for linseed oil in artists' paints. For hundreds of years, plant oils have been used as binders for artist paints, but due to their slow drying, yellowing, and cracking on aging the binder market has shifted to petroleum-based acrylics. In this study, plant oil vinyl ether (POVE) monomers were synthesized from linseed, soybean, and palm oils and then polymerized using cationic polymerization. The synthesized POVE monomers had color impurities that were successfully removed via distillation resulting in essentially colorless monomers. The synthesized poly(POVE)s, showed drying behavior faster than linseed oil. A similar trend was observed in the presence of drying catalysts or pigments. Drying time and viscosity were tailored by varying the molecular weight of the poly(POVE)s. Compared to linseed oil, purified poly(POVE) binders resulted in significantly lower “yellowness” when films were produced with TiO2 pigment. Pigmented films from poly(POVE)s also resulted in better mechanical properties compared to those made using linseed oil as the binder.

A new class of biobased nanocarriers, soysomes, has been discovered and investigated. These nanocarriers are derived from a synthetically accessible, scalable macromolecule, methoxylated sucrose soyate polyol (MSSP), derived from chemical building blocks obtained from soybean oil and sucrose. We observed for the first time that MSSP, when dissolved in an organic solvent of different polarity and slowly added to an aqueous phase at a predetermined rate under "nanoprecipitation" conditions, will form a stable, self-assembled structure with a size range from 100 to 200 nm depending on the polarity difference between the precipitating solvent pairs. Without the aid of poly(ethylene glycol) or any surfactants, these soysomes were found to be stable in water for an extended period and can withstand the destabilizing effect of time, temperature, and pH. We also found that the soysomes were able to encapsulate and release a hydrophobic bioactive compound, such as curcumin. Both MSSP and their self-assembled structures were highly biocompatible and did not trigger cellular toxicity to mammalian cell lines. Our experiments showed that such 100% biobased, noncytotoxic material as MSSP and a related class of products have the potential for use toward the sustainable manufacturing of drug nanocarriers for biomedical applications.

A concise series of renewable vinyl compounds has been prepared from benign biosourced precursors, vanillin and eugenol, in fair overall yield. These were evaluated against styrene as reactive diluents in a renewable high-performance vinyl ester resin thermoset: dimethacrylated-epoxidized-sucrose-soyate (DMESS). Each diluent contained a 1,2-dimethoxybenzene or veratrole core structure that connotes a decreased vapor pressure and thereby reduced exposure hazard. Viscosities for formulations (10, 20, and 30% by weight of diluents) with styrene and all three veratrole-diluents were evaluated. Veratrole-diluents were comparable to styrene at similar molar concentration. Thermosets formulated with 30% by weight of diluents were prepared and characterized by thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and dynamic mechanical thermal analysis (DMTA); the most promising thermoset was prepared using 3-allyl-1,2-dimethoxy-5-vinylbenzene-diluted-DMESS and closely matched the performance...

Formulations of bio-based poly(cyclic carbonates) and amines using cooperative catalysis were studied to produce non-isocyanate polyurethanes (NIPUs). Concerns on the use of isocyanates as starting materials for polyurethanes (PUs) have risen due to their effects on human health after exposure and also because their synthesis involves the use of phosgene. Polyurethanes are highly versatile materials used in widespread industries such as automotive, building, construction, and packaging. They have also been used as flexible and rigid foams, adhesives, coatings, thermoplastic, or thermoset materials. Traditionally, PUs are synthesized from polyols and polyisocyanates. In order to circumvent the concerns, much research has been devoted to exploring alternative approaches to the synthesis of PUs. NIPU synthesis using cyclic carbonates and amines has gained popularity as one of the new approaches. In this study, novel bio-based resins were synthesized by converting epoxidized sucrose soyate into carbonated sucrose soyate (CSS) under supercritical conditions. Initial studies have shown promise in systems where CSS is crosslinked with multifunctional amines generating coatings with good solvent resistance. This work focused on studying the effect of catalysts and developing formulations of bio-based non-isocyanate polyurethane coatings.

A series of highly functional methacrylated bio-based resins were synthesized and used in the formulation of UV curable coatings systems. Methacrylated epoxidized sucrose soyate (MESS) and dimethacrylated epoxidized sucrose soyate (DMESS) were synthesized from epoxidized sucrose soyate (ESS). The resins were combined with multifunctional reactive diluents and a photoinitiator and cured under UV light. A commercially available bisphenol A glycerolate dimethacrylate (BisGMA) resin was used as the control. The curing kinetics was studied using real-time infrared spectroscopy equipped with a UV light. Shrinkage of the coatings was measured by the volume change before and after the curing process. The extent of cure was determined using Attenuated Total Reflectance-Fourier transform infrared spectroscopy (ATR-FTIR). Thermal and mechanical properties were evaluated using thermogravimetric analysis (TGA), thermomechanical analysis (TMA), and atomic force microscopy (AFM). Performance of the coatings was also assessed by measuring the moisture uptake and abrasion resistance. Coatings made from these formulations displayed good solvent resistance and hardness due to the high crosslink density achieved due to the high number of functional groups on the bio-based resin system.

A study was carried out to evaluate the impact of modification of epoxidized sucrose soyate using a combination of methacrylate and inert esters (acetate propionate, butyrate) on the properties of the resins as well as the thermosets. Previous studies have shown that methacrylated epoxidized sucrose soyate (MESS) can yield thermosets having high glass transition temperature (Tg) and good mechanical properties, but had high resin viscosity due to hydrogen bonding of the hydroxyl groups. Further functionalization to yield dimethacrylated epoxidized sucrose soyate (DMESS) resulted in reduced resin viscosity, but some of the thermosets were brittle. In this study, to maintain low resin viscosity and improve thermoset ductility, replacement of some methacrylate groups with various ester groups was explored. The synthesis of these resins was carried out in a one-pot process involving the sequential slow addition of anhydrides of the acids mixed prior to addition. The synthesized resins were characterized for their viscosity with and without styrene diluent. Formulations were made using varying amounts of styrene and free-radically cured using peroxyesters as initiators. The bio-based resins with 30% styrene gave much lower viscosities compared to commercial resins containing higher amounts of styrene (33% and 45%). The thermosets produced had improved flexibility and toughness with only a slight reduction in the glass transition temperature. The inclusion of the non-functional esters in the resin structure acted as internal plasticizers for the polymer system. The new sets of thermomechanical properties demonstrated the tunability of the bio-based resin system and opens up different avenues for end-use applications.

A cis-3,4-di(furan-2-yl)cyclobutane-1,2-dicarboxylic acid (CBDA-2) is readily prepared stereospecifically from trans-3-(2-furyl)acrylic acid, a furfural-derived compound, through a solid-state [2 + 2] photocycloaddition in 95% isolated yield. The cyclobutane ring in CBDA-2 shows desired stabilities during thermal, sunlight, and chemical tests. The single crystal structure of CBDA-2 revealed the geometry of this molecule and orientation of the two dicarboxylic acid groups displaying its potential to serve as a unique, semirigid diacid building block in material science. A preliminary study showed that condensation of this diacid with glycerol yielded a green polymer with good stability. The diacid could also be used as a cross-linker for a biobased epoxy to yield an exceptionally hard and solvent-resistant thermoset.

Epoxidized sucrose soyate (ESS) is a biobased, reactive substrate useful in the production of a range of new materials. Several readily available metal catalysts for the synthesis of ESS by epoxidation of sucrose soyate (SS) with various oxidants have been surveyed, with the consideration of environmental sustainability. Among them, a methyltrioxorhenium(MTO)/H2O2 system in 2-methyltetrahydrofuran solvent is identified as the most effective method with mild reaction conditions, high activity and high selectivity.

Biobased photoacids were synthesized from naturally occurring vanillin analogues and evaluated for their photoacidity. It was determined that substituted ortho-vanillin possessed the strongest acidity in the excited state.

To tune the properties and reduce the viscosity of methacrylate functional epoxidized sucrose soyate (MESS), the use of a dual functionalization strategy was explored. Bio-based thermosets have previously been produced from free-radical curing of MESS having a large number of functional groups and have demonstrated a high glass transition temperature (Tg) and good mechanical properties. However, the MESS viscosity was high. To reduce the MESS viscosity, further functionalization of MESS was carried out by sequential addition of methacrylic anhydride. The synthesis was optimized and the resulting dimethacrylated epoxidized sucrose soyate (DMESS) was characterized using Fourier transform infrared spectroscopy (FTIR), proton nuclear magnetic resonance spectroscopy (1H NMR), gel permeation chromatography (GPC), and viscosity measurements. A series of DMESS with varying range of degrees of methacrylation was synthesized. The synthesized DMESS series were combined with varying amounts of styrene diluent and cured using a free radical process with peroxyesters as initiators. The extent of cure was determined by gel content using Soxhlet extraction and confirmed using FTIR. The thermal and mechanical properties were evaluated using thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), dynamic mechanical thermal analysis (DMTA), and tensile testing.

Compared with thermoplastic polymers, thermoset polymers are difficult to recycle because they can not be remolded once cured and often do not decompose under mild conditions. Thermosets designed to be degradable afford a useful route to obtain thermoset recyclability and enable the recycling of valuable components that may be encapsulated in thermoset materials. In this review, the need for degradable thermosets as well as a summary of research progress is presented. Degradable thermosets are divided into different categories based on the different labile bonds or linkages studied such as esters, sulfur containing linkages (disulfide, sulfonate, 5-membered cyclic dithiocarbonate, trithiocarbonate, sulfite), nitrogen containing structures (acylhydrazone, alkoxyamine, azlactones, Schiff base, hindered ureas, aminal, carbamate), orthoester structures, carbonates, acetals, hemiacetals, olefinic bonds, D-A addition structures, vicinal tricarbonyl structures, peroxide bonds, phosphorus containing structures, tertiary ether bonds, and so on. The synthetic route, recycling methods, degradation mechanisms and progress in research of each approach to degradable thermosets is described. The efforts of the applicability of some degradable thermosets are also summarized. Finally, conclusions and trends of future work are highlighted.

Indulin AT Kraft lignin has been chemically modified without a catalyst by reaction with t-butyl acetoacetate. Elucidation and quantification of the modified lignin structure has been facilitated by employing a series of readily prepared model compounds which isolate three of the major hydroxyl containing moieties characteristic of lignin.

A novel vinyl ether monomer from eugenol, 2-eugenoloxyvinyl ether (EEVE), was synthesized and used as a building block for polymeric epoxy resins. The EEVE monomer was polymerized via cationic polymerization of the vinyl ether group leaving the allylic functionality of eugenol available for further epoxidation. Epoxidized poly(EEVE) resins varying in levels of epoxidation (epoxy equivalent weights from 360 to 870 g/eq) were produced and cured with twelve amine curatives at ambient and elevated temperatures for different time intervals to evaluate and optimize the curing regime. The cured coatings were screened with high throughput dye extraction and “conventional” coating testing methods and compared to coatings produced from diglycidyl ether of bisphenol-A (DGEBA). Results showed that coatings derived from epoxidized poly(EEVE) [Epoly(EEVE)] can be tuned from soft and elastic with hardness 500 GPa and Tgs > 60 °C by varying the extent of epoxidation and the nature of curative, whereas DGEBA resulted in hard and brittle coatings irrespective of the type of curative used in the study. Compared to DGEBA resin, coatings with similar or higher crosslink densities and hardness were obtained from Epoly(EEVE) resins with >50% epoxidation of EEVE moieties using the same curative and curing regime. These partially biobased epoxy compounds derived from eugenol have the potential to be competitive with petroleum-based DGEBA resins in coatings applications.

A series of amphiphilic siloxane polyurethane (AmSiPU) coatings were investigated for their icephobic properties. The use of coatings having amphiphilic surfaces for anti-icing applications has not been studied to a large extent although these types of coatings have more recently been studied for anti-fouling (AF)/foul release (FR) applications. Several polyurethane based amphiphilic coatings were prepared having variations in the composition as well as molecular weight of hydrophobic polydimethyl siloxane (PDMS), and hydrophilic polyethylene glycol (PEG). Surface characterizations of the coatings revealed the presence of both PDMS and PEG moieties, implying amphiphilic surface characteristics. The icephobic properties of these coatings were evaluated to investigate if amphiphilic formulations can deter ice adhesion. Water absorption and barrier behaviors of these coatings and their correlation to anti-icing properties were also studied.

A study was conducted to evaluate the mechanical properties of low density fiberboard produced with combinations of two fibers soybean straw ( Glycine max ), and wheat straw ( Triticum aestivum ) and two resins methylene diphenyl diisocyanate (MDI) and epoxidized sucrose soyate (ESS) resin as binders. ESS is a high performance, soybean oil based epoxy that has shown promise as a highly biobased adhesive. Six formulations of panels were produced using various combinations of straw and resin binder. Mechanical testing of sample boards was conducted using ASTM standard D1037-12. Test results showed that type of resin did not influence soy straw or wheat straw board’s stiffness and strength properties but had a major impact on water resistance, screw withdrawal strength and internal bond strength. The study demonstrated the potential of ESS as a novel binder for fiberboard system if a suitable crosslinker and catalyst is utilized. It also showed that increasing ESS content over 50% in a MDI blend lowered the performance characteristics of boards. However, analytical testing of the resin systems showed limited reactivity between ESS soyate and MDI, indicating other compatible resin chemistries should be explored for achieving superior board properties. Overall, a resin blend with 25–50% ESS in MDI appears favorable for low density fiberboards. ESS can be a promising bio-based resin as it has the potential to meet California Air and Resources Board (CARB) standards while providing acceptable properties as an adhesive.

The kinetics of curing of epoxidized sucrose soyate with a cycloaliphatic anhydride was studied using differential scanning calorimetry. Epoxidized sucrose soyate (ESS), a novel bio-based resin with high epoxy functionality, can be used to produce thermoset polymers for structural applications. ESS was cross-linked with methyl hexahydrophthalic anhydride using a zinc-based catalyst. Differential scanning calorimetry studies indicated that the reaction kinetics was influenced by the formulation variables, i.e., anhydride-to-epoxy molar ratio and catalyst amount. Multiple exothermic peaks suggest the presence of several different reaction mechanisms of the epoxy-anhydride reaction using metal complex catalyst, based on the formulation variables. All of the reaction rate data can be fitted into both n-th order and autocatalytic kinetic models. Based on the value of reaction order in the n-th order and autocatalytic kinetic model, the curing process is more dominated by non-autocatalytic reaction and less controlled by the autocatalytic process. This kinetic model observation suggested that the presence of hydroxyl groups or carboxylic acid pendant chains in the ESS molecule or as the product of side reactions did not autocatalyze the reaction, and the reaction is initiated solely from the metal complex.

Using Michael addition crosslinking technology, thermoset coatings were prepared from acrylated epoxidized sucrose soyate (AESS) and amine crosslinkers. AESS was synthesized from sucrose soyate, which is the sucrose ester of soybean oil fatty acids and has an average of about 12 functionalities per molecule. Due to the high functionality of AESS and fast reactivity of the amine crosslinkers, the coatings can be cured at ambient temperature (21 °C) in a relatively short period of time yielding good coatings properties. When AESS was reacted with 4′4′-methylene bis(cyclohexylamine), the acrylate group conversion was determined by FTIR to be up to 90%. It was also found that the type of solvent used in the coatings formulation affected the film formation and thus the coatings properties. The addition of 1,6-hexanediol diacrylate diluent in the formulations resulted in softer and lower T g coatings. Using a trifunctional amine such as diethylene triamine, coatings could be prepared without the addition of any catalyst. Overall, thermosets made from AESS Michael crosslinking technology provide a highly bio-based coating system with good hardness and chemical resistance.

The popularity and variety of bio-based polymers are increasing as the chemical industry identifies and develops commercial biomass alternatives for traditional petroleum-based products. Environmental impacts and renewability of novel biochemical processes or materials must be determined in a quantitative manner to support sustainable development. A life cycle assessment (LCA) model was constructed for programmed photodegradation of polymeric/oligomeric materials derived from renewable bioresources. This research evaluates the sustainability for the production of 2,5-furandicarboxylic acid (FDCA), a polymer building block, from 5-hydroxymethylfurfural (HMF), an intermediate derived from renewable resource fructose. A phototrigger is attached to the monomers during the polymerization process, resulting in a polymer that degrades in the presence of UV light. The LCA results indicate that 38–49% of environmental impacts were attributed to the conversion of FDCA to polymer, where electricity consumption and use of non-renewable chemicals such as dichloromethane and other solvents were significant contributors. The process of recycling of polymeric material reduced all environmental impacts, suggesting that recycling outweighs the impacts caused by the production of phototriggers.