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Doll K.M.,U.S. Department of Agriculture | Heise G.L.,Anderson Development Company | Myslinska M.,Anderson Development Company | Sharma B.K.,University of Illinois at Urbana - Champaign
American Society of Mechanical Engineers, Tribology Division, TRIB | Year: 2012

A new additive was produced from a natural oil and boron. The synthesis involves the use of the epoxidized form of soybean oil which then undergoes a catalytic ring opening to produce the additive material. Due to their remaining triacylglycerol structure, the products are highly compatible with bio-based lubricants and due to their covalent boron attachments, show effective properties for the reduction of wear. Some performance examples: Using a traditional Falex 4-ball wear test, the scar diameter observed in a soybean oil lubricant could be reduced from 0.61 mm to 0.41 mm by the inclusion of 1% or the additive. A second generation additive, while not as effective at reducing wear, was able to increase the oxidation onset temperature of soybean oil under pressurized oxygen by 14°C. Next, these additives were tested in a formulation of biobased gear oil composed of heat treated soybean oil and synthetic esters. In the best formulation, these additives were able to surpass the oxidation onset of a gear oil that was formulated with commercially available additives, while giving nearly as good of performance by wear scar analysis. This oxidation onset value, of 258°C, approaches that of off-the-shelf gear oils. Overall, these new additives are strong performers which can be made using simple chemistry. Their properties combined with their high biobased content are valuable assets in the search for biobased lubricants and gear oils. Copyright © 2012 by ASME.


Sharma B.K.,Anderson Development Company | Doll K.M.,University of Illinois at Urbana - Champaign | Doll K.M.,1815 North University Street | Heise G.L.,Anderson Development Company | And 2 more authors.
Industrial and Engineering Chemistry Research | Year: 2012

The synthesis of lubricant additives based on boron and epoxidized soybean oil are presented. These additives are made from a simple patent pending method involving a ring-opening reaction of the epoxidized oil. A couple of these borates were tested in soybean oil, polyalpha olefin basestock, group III basestock, and hexadecane. An aromatic additive was able to increase the oxidation onset of the basestocks by 14, 52, 48, and 49 °C, respectively, when used at 2% wt. The other additive was shown to reduce the wear scar diameter in a friction test when used in soybean oil basestock, from 0.61 mm down to 0.41 mm. These additives were also tested in a gear oil blend, and shown to reduce both wear and oxidation. They were also compatible with a popular additive, additive zinc dialkyl dithiophosphate. © 2012 American Chemical Society.


Myslinska M.,Anderson Development Company | Heise G.L.,Anderson Development Company | Walsh D.J.,Anderson Development Company
Tetrahedron Letters | Year: 2012

The syntheses of boronates derived from the reaction of dioxaborolanes and dioxaborinanes with either organolithium or organomagnesium reagents are investigated along with their subsequent use in the palladium cross coupling reaction. The intrinsic stability of these cyclic esters contributes to their facile reaction with both lithium and magnesium nucleophiles at mild and safe conditions. We have found that many of the reactions proceed at room temperature which is a significant improvement over the traditional routes which require cryogenic temperatures. The scope of these reactions and their practical application to large scale process synthesis is described. © 2012 Elsevier Ltd. All rights reserved.


Some historical PMA literature can be found on polyurethane degradation pertaining to hydrolytic stability, although not very much. In this paper, a comprehensive study is presented comparing multiple backbones, isocyanates, and durometers using not only tensile strength as an indicator of degradation, but also other physical properties. Looking at the trends of the data can give direction of what type of urethane to use in aqueous applications.


Ranges of glycidyl methacrylate containing acrylic resin monomer compositions and polymer properties which are suitable to be used in chain extension processes for Poly(lactic acid) or Polylactide (PLA). The selection of monomer compositions and molecular weight ranges of the acrylic chain extender resins, and the examples of chain extension reaction between the acrylic chain extender and PLA are also provided.


Polyurethane/urea elastomer compositions which retain their dimensions at elevated temperatures. These polyurethane/urea elastomers surprisingly have improved green strength or dimensional stability upon demolding at typical mold temperatures of 80 to 130 C and remain dimensionally stable throughout the post cure process which is typically overnight at about 100 C. They are useful in indirect food contact or dry food contact applications since the compositions use trimethylene glycol di(p-aminobenzoate) as a chain extender or curative. The polyurethane/urea elastomers may be prepared by reacting toluene diisocyanate prepolymers with trimethylene glycol di(p-aminobenzoate). The toluene diisocyanate prepolymers are reaction products of toluene diisocyanate containing at least 25% by weight of the 2,6-isomer, preferentially at least 35%, more preferentially at least 45%, and most preferentially 60% with polyols such as polyoxyalkylene polyether polyols like polytetramethylene glycol, polypropylene glycol and polyethylene glycol, polyester polyols, polycaprolactone polyols, polycarbonate polyols, polybutadiene polyols or mixtures thereof.


Patent
Anderson Development Company | Date: 2012-05-11

Borates, compositions comprising chiral (cyclic and acyclic) and achiral (cyclic and acyclic) borates; chiral (cyclic and acyclic) and achiral (cyclic and acyclic) biborates; and methods for their synthesis. Additionally, a significantly improved synthetic protocol for the synthesis of wide range of boronates starting from borates or biborates and Grignard or organolithium reagents that can be used for kilo lab and commercial scale production.

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