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The American Coatings Association (ACA) represents paint and coatings manufacturers, raw materials suppliers, distributors, and technical professionals.

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Academic Research: Fundamental to Advancing Sustainable Coating Technologies

[…] boom, biobased materials currently have difficulty competing on a cost basis, even with government incentive programs. Ghasideh Pourhashem, assistant professor in the Department of Coatings and Polymeric Materials at NDSU believes that a lack of standards for green or sustainable coatings is also hindering their development. “Better regulations and policies, including the establishment of specific standards or mandatory regulations for green and biobased coatings that have to be followed would benefit everyone,” she says. In particular, she would like to see standards that address the entire supply chain and not just the environmental and health benefits of the final coating formulations. “The impact of coatings begins long before they are made with the basic raw materials that are extracted from the earth or biomass. We, therefore, need standards that account for the entire supply chain when determining the greenness or sustainability of paints and coatings,” she explains. The conservative nature of the coatings industry is yet another challenge, according to Voronov. “While interest in more sustainable materials for use in coating formulations is definitely growing, there are only a few companies willing to take on the significant risk associated with using novel ingredients. The situation is changing, and there are numerous companies with stated plans to expand their portfolios with greener products over the next 10 years.” Only a Matter of Time The question, according to Sergiy Minko, Georgia power professor of Fiber and Polymer Science in the Department of Textiles, Merchandising and Interiors and the Department of Chemistry at the University of Georgia, is not if more sustainable technologies will be adopted, but how long it will take. “The future direction of the coatings sector is to be more sustainable. It will take time to address the technical, economic, and political aspects, but the time will come when sustainable materials and green chemistry are the norm,” he asserts. The role of academic researchers, Webster adds, is to perform the basic research needed to understand the chemistry and properties of various new polymers and what needs to be done to develop sustainable alternatives that meet the cost and performance requirements of industrial applications. “There is always a combination of technical push and market pull, and today we are still at the technical push stage. Scientists are looking at what materials are available from biomass and how they can be functionalized, transformed, or even directly used in coatings. We are completing the essential basic research in order to develop new materials that can then be evaluated for their benefits by actual users,” he concludes. Manipulation of Soybean Oil Seed/vegetable oils have long been used by the coatings industry—alkyds are a prime example. Many academic researchers are exploring a wider range of plant-based oils, novel derivatives, and the use of different comonomers with the goal of improving the performance characteristics of biobased resins in paint and coating formulations. Webster has been developing epoxidized sucrose soyates, 100% biobased materials generated from the reaction of soybean fatty acid with sucrose followed by epoxidation using hydrogen peroxide. The epoxidized sucrose soyates possess larger numbers of epoxy groups that can be used in curing processes to generate thermosets, which have applications in the construction, automotive, appliance, and furniture industries. “We view these epoxidized sucrose esters as a platform technology that can be converted via multiple mechanisms to many different types of resins with wide ranging properties,” states Webster. For instance, they can undergo photopolymerization, thermal crosslinking with anhydrides or blocked acids, or water-assisted acid crosslinking. They can be converted to polyols that can then be used to generate polyurethanes (PUs) with unique properties. The sucrose soyates can also be derivatized into carbonates, acrylates, or methacrylates, which also have a wide range of curing options and afford resins with interesting properties. “One major advantage we are realizing with this technology relates to the high functionality of the sucrose soyates. They provide high crosslink densities, yielding coatings that are hard and tough. One of the traditional challenges with vegetable oil-based coatings has been achieving the necessary physical and mechanical properties. We have overcome that issue with these materials,” Webster notes. He has even explored their use in composites with natural fibers. In many cases, the new coatings and composites that Webster has developed using the epoxidized sucrose soyates have properties competitive to those obtained using petrochemical-based materials. Some of this work is being done through the Center for Sustainable Material Science, a National Science Foundation-funded collaboration between researchers at NDSU and several other universities with a focus on investigating chemicals derived from biomass for the preparation of polymers and composites. Mannari’s group at Eastern Michigan University is also investigating coatings based on resins made from soybean oil derivatives. In one example, the soybean oil is reacted with biobased itaconic acid to form a polyester that is used as a major component in UV-curable green UV-LED gel nail polishes. “Nail polishes are one of the most widely used products in the U.S. cosmetic industry,” Mannari observes. He notes that by 2020, 122 million Americans alone are expected to use them. Gel nail polishes are attractive because, once crosslinked under UV radiation, they have much greater durability than conventional nail polishes. The gel nail polishes his group has recently developed are green for several reasons: they are cured using UV-LED radiation and are either zero-VOC solventborne or water-based formulations, including polyurethane dispersions, comprising approximately 50% biorenewable content. Mannari is not satisfied, though. “We are working to increase the biobased content by incorporating other biobased materials such as derivatives of gum/wood rosin, cardanol, and sorbitol, to name a few, as components in the formulations,” he comments. In a separate project, Mannari is exploring the development of bisphenol-A-free (BPA-free) epoxy resins predominantly from biobased resources. “There is good demand for BPA-free products due to the increasing concerns regarding the use of BPA, especially in food packaging and consumer products,” he notes.  Mannari is also developing waterborne UV-curable polyurethane wood coatings based on epoxidized soybean oil polyols with varying chemical structures and hard to soft properties. These formulations also include rosin. He intends to investigate this biobased approach for the development of packaging coatings given that this market is very much interested in renewable and recyclable materials.  Biobased Latexes One of the challenges in developing waterborne latex coatings using resins based on plant and vegetable is that these oils are very hydrophobic, and it is difficult to achieve an acceptable solids content (~40%) and high molecular weight during emulsion polymerization via a free radical mechanism, according to Voronov. For commercial applications, he notes that 99% conversion with no residual monomers is needed. To tackle this challenge, Voronov’s group has established a library of vinyl monomers prepared in one step from soybean, canola, sunflower, high-oleic soybean, hydrogenated soybean, and corn oils. The researchers have been exploring how these monomers act during free radical emulsion polymerization, both for the formation of homopolymers and copolymers (with commercially available monomers such as methyl methacrylate, styrene acrylate, etc.). High-oleic soybean oil is an attractive option because it has high heat stability, improved shelf life due to enhanced resistance to oxidation, and a better controlled composition because it is monounsaturated. “We anticipated that there would be fundamental challenges, including insufficient conversion due to the hydrophobicity of the monomers. The first step was to investigate the kinetics, reactivity, and other fundamental characteristics to identify opportunities for optimizing the polymerization to achieve better properties and performance,” Voronov observes. One approach employed to increase the conversion was to perform the reaction as a mini-emulsion. This method is more suited for hydrophobic monomers because the initiator is not soluble in water but soluble in oil, which potentially causes the polymerization to take place in oil droplets rather than in micelles, as is the case with traditional emulsions. His group has been able to easily achieve 95–97% conversion, which is not sufficient for commercial products, but is good enough for initial proof of concept testing. Vinyl monomers are indeed polymerizable with a broad variety of vinyl counterparts, providing a versatile platform with different properties achievable depending on the choice of oil from which the monomer was derived. “We have been able to show that the vinyl monomers are indeed polymerizable with a broad variety of vinyl counterparts, providing a versatile platform with different properties achievable depending on the choice of oil from which the monomer was derived,” says Voronov. He notes that one of the advantages of these resins is that unsaturated fragments are present that allow for crosslinking. “We can realize a broad range of properties, which allows for optimization of the desired combination of strength, flexibility, and toughness,” Voronov asserts. So far, the solids content has been sufficient too, but while close, 99% yields have not yet been obtainable. In addition to working on that goal, Voronov is exploring comonomers from the same seed/plant oils but with different chemistry to enable the production of 100% biobased resins. He is collaborating with a French group that has synthesized a biobased monomer containing a benzene ring that when copolymerized with the oil-based vinyl monomers provides resins that impart some strength to coatings. Voronov has also investigated acrylic monomers prepared from cardinol, which is obtained from cashew nut shell liquid. It contains an aromatic ring functionality and has the added advantage of being commercially available (annual production volume of one million tons). Isocyanate-free Polyurethanes In both military and industrial applications, there is a need to replace commonly used ingredients that are now recognized to pose a health and/or safety hazard to plant personnel and end users. The use of bisphenol A in can coatings, chromates in protective coatings, and isocyanates as curing agents for PUs are perhaps the three most pertinent examples. Biobased materials have potential utility in the development of alternatives in some cases. Webster, Mannari, and Soucek have all focused on the development of nonisocyanate curing agents. Webster has been exploring the use of cyclic carbonate derivatives of epoxidized sucrose soyates, which can be cured with amines. The reaction takes place at room temperature, but can also be accelerated with low levels of heat. The rate is dependent on the amine structure, with primary and less- hindered amines reacting more rapidly than secondary and bulky amines. Mannari’s solutions involve the use of cyclic carbonates and diamines. “Carbonate-diamine chemistry isn’t new for making polyurethanes, but our approach using cyclic carbonates is customized to ensure that the resultant resins have desirable properties,” he comments. The PUs formed in the reaction are slightly different from conventional PUs in that they possess a b-hydroxy group. The presence of a large number of such polar groups in the cured coating has the potential to impact chemical and alkali resistance and result in higher viscosities due to hydrogen bonding, according to Mannari. While higher viscosities were observed, he did not, however, see as large an impact on coating performance as expected. His group, therefore, investigated the use of different reactive diluents as a means for locking the hydroxyl groups via secondary crosslinking. Mannari proposed two types of nonisocyanate PUs for aerospace applications—high-solids (> 60% at time of application) and single-component UV-curable solventborne systems with zero HAPs. A total […]