Selected Patents Relating to Oils and Fats 2014

The following list contains brief details of current patents, which appeared to the editor to be especially relevant. Inevitably, there is an element of subjectivity in the choice. Topics included in the list are based on the Divisions of the AOCS and the topical sessions held at the AOCS annual meetings. Patents are listed here at intervals as they are published in INFORM.

Enzymatic oil recuperation process (Kellens, M., and W. De Greyt, N.V. Desmet Ballestra Engineering SA, US8435766, May 7, 2013).

A process for the recuperation of acylglycerols or acylglycerols containing free fatty acids from gums, present as aqueous emulsions, said gums being obtained by subjecting triglyceride oil to one or more degumming processes, said recuperation process comprising the steps of: subjecting said gums to enzymatic hydrolysis catalyzed by one or more enzymes with phospholipase activity; allowing said gums to separate into two or more phases, said two or more phases including at least an oily phase and an aqueous phase; and recuperating said oily phase comprising acylglycerols or acylglycerols containing free fatty acids; wherein said enzymatic hydrolysis is accelerated by adding at least part of the one or more enzymes with phospholipase activity to at least part of the water used in the recuperation and/or at least one degumming process; and/or at least part of said triglyceride oils treated in said degumming process; and/or by facilitating mixing at least part of said one or more enzymes with phospholipase activity into said gums by increasing the triglyceride oil content of said gums; and an oil obtained by this process.

Reduced-odor thiol compositions (Medri, M.W., Consumer Products Corp., US8440219, May 14, 2013).

The present invention provides compositions for and methods of delivering a therapeutically effective dose of a mal-odorous sulfide or disulfide group-containing compound, for example glutathione (reduced) and/or glutathione disulfide, in a vehicle that is effective to reduce the unpleasant odor and/or taste of the compound. The invention further provides methods for reducing the amount of oxidation occurring when sulfide group-containing compounds, such as glutathione, are incorporated into sugar and or sugar-free hard candies without subjecting the glutathione to thermal and/or moisture degradation where degradation is expressed as oxidation. The invention further provides vehicle compositions including the protected sulfide group-containing compounds and their use as medicaments. The sulfide group-containing compounds are protected from degradation by their dispersion into fats, oil, and/or fractionated or partially hydrogenated oils prior to their blending into the vehicle.

Fat crystallization accelerator (Nakano, M., et al., Fuji Oil Co., Ltd., US8440250, May 14, 2013).

Provided is a crystallization accelerator capable of accelerating fat crystallization a short time during a production step of a product of margarine, shortening, chocolate, or hard butter to be used for confectionary production or bread production. A phenomenon that sorbitan fatty acid ester having an esterification ratio of from 28% to 60% and a sorbitol-type content of from 20% to 40% exhibits a remarkable effect on acceleration of fat crystallization in a short time was found, and thus, the invention was completed.

Method for reducing 1, 2-diglyceride content of an edible oil (Wassell, P., et al, DuPont Nutrition Biosciences ApS, US8440435, May 14, 2013).

The present application provides a method of reducing and/or removing diglyceride from an edible oil, comprising admixing an edible oil with an acyl acceptor substrate and a diglyceride:glycerol acyltransferase, wherein the diglyceride:glycerol acyltransferase is characterized as an enzyme which in an edible oil is capable of transferring an acyl group from a diglyceride to glycerol. The diglyceride:glycerol acyltransferase can comprise the amino acid sequence motif GDSX. The present invention also relates to the use of a diglyceride:glycerol acyltransferase in the manufacture of an edible oil, for reducing and/or removing diglyceride from said edible oil and to the use of said enzyme in the manufacture of a foodstuff comprising an edible oil for improving the crystallization properties of said foodstuff.

Molecular aggregate capable of undergoing phase transition by dehydrating condensation and method of phase transition thereof (Kunishima, M., Japan Science and Technology Agency, US8449979, May 28, 2013).

Provided is a bilayer membrane vesicle capable of under-going a phase transition. The bilayer membrane vesicle includes (i) a fatty acid salt having 6–20 carbon atoms; (ii) an alcohol or an amine compound having an aliphatic chain of 6–20 carbon atoms; and (iii) an artificial synthetic lipid or a phospholipid capable of forming a bilayer membrane. Preferably, this bilayer membrane vesicle further contains (iv) a tertiary amine as a component of the membrane. Also provided is a method of inducing a phase transition of a bilayer membrane vesicle, the method including the step of adding a dehydrating condensing agent or a dehydrating condensing agent precursor having the property of accumulating at an interface to the bilayer membrane vesicle. By causing the lipids that form a molecular aggregate to chemically change, it is possible to change the physical property and the morphology of the molecular aggregate and control the timing of phase transitions such as membrane fusion. In the membrane fusion, for example, fusion can occur without leakage of the con-tents of the bilayer membrane vesicle.

Low viscosity mono-unsaturated acid containing oil-based dielectric fluids (Amanullah, M., et al., Biolectric Pty. Ltd., US8440116, May 14, 2013).

Disclosed herein are a dielectric fluid composition and a method thereof. Also disclosed are viscosity modifiers and a method of lowering the viscosity of an oil-based dielectric fluid. The composition includes an oil with a high mono-unsaturated fatty acid content and one or more fatty acid alkyl esters, each having a fatty acid and an alkyl moiety, wherein the alkyl moiety of the fatty acid alkyl esters has 1–4 carbon atoms, and wherein both the oil and the fatty acid alkyl ester are in the range of 40–60% v/v of the dielectric fluid composition. The viscosity modifier includes one or more fatty acid alkyl esters with an alkyl moiety and a fatty acid moiety, wherein the alkyl moiety has 1–4 carbon atoms. The method of lowering the viscosity includes blending the viscosity modifier and a vegetable oil-based dielectric fluid in a ratio of 40:60–60:40.

Solubilizing composition (Ohkawa, Y., NOF Corp., US8440726, May 14, 2013).

A solubilizing composition containing (i) at least one oily component selected from esters of oleic acid with alcohols having 1–3 carbon atoms and triglycerides of fatty acids having 6–12 carbon atoms, (ii) a polyoxyethylenesorbitan fatty acid ester, (iii) a polyhydric alcohol which is liquid at 15–25°C, and (iv) one or more acidic phospholipids where the fatty acid constituting an acyl group thereof is selected from saturated fatty acids having 6–14 carbon atoms and unsaturated fatty acids have 16–18 carbon atoms, which contains 20–40% by weight of the component (i), 30–45% by weight of component (ii), 15–40% by weight of component (iii), and 0.5–4% by weight of the component (iv), based on 100% by weight of a total amount of the components (i) to (iv).

Lipid-treated particles and polymers containing the particles (El-Shoubary, M., Cristal USA Inc., US8436077, May 7, 2013).

A coated particulate solid composition includes a particulate inorganic solid having deposited on its surface a treatment oil comprising lipids. The particulate inorganic solid can include a base particle of titanium dioxide, zinc sulfide, zinc oxide, iron oxide, lead oxide, aluminum oxide, silicon dioxide, zirconium oxide, and/or chromium oxide. The treatment oil is optionally a vegetable oil. The treatment oil containing lipids optionally contains glycerides such as triglycerides and diglycerides, and can contain phospholipids. In one embodiment, the coated particulate solid composition includes particulate titanium dioxide, wherein the treatment oil provides increased bulk density and enhanced dispersibility in plastic as well as improved lacing resistance.

Lubricating composition containing borated phospholipid (Baker, M., and G.B. Rhoads, The Lubrizol Corp., US8445417, May 21, 2013).

The invention relates to a lubricating composition containing (i) a borated phospholipid, (ii) an amine salt of a phosphoric acid ester, and (iii) an oil of lubricating viscosity. The invention further provides for the use of the lubricating composition for lubricating a limited slip differential.

Microemulsion and sub-micron emulsion process and compositions (Larm, M.G., et al., Stiefel Research Australia Pty. Ltd., US8449867, May 28, 2013).

An oil-in-water microemulsion or sub-micron emulsion composition for dermal delivery of at least one pharmaceutically active ingredient is provided. The composition includes an oil phase dispersed throughout a water phase, the oil phase including at least one member selected from the group consisting of an animal oil, a mineral oil, a vegetable oil, a silane member, a siloxane, an ester, a fatty acid, a fat, a halogen compound, and an alkoxylated alcohol; and at least one lipophilic surfactant, the water phase including at least one hydrophilic surfactant, water, and optionally a non-surfactant amphiphilic compound, the weight ratio of the at least one hydrophilic surfactant to the at least one lipophilic surfactant being approximately 9.0:1.0 to 2.0:3.0.

Generation of triacylglycerols (Dayton, C., Bunge Oils, Inc., US8541211, September 24, 2013).

A method is disclosed for the generation of triacylglycerols from gums that have been separated from an oil product. The gums are treated with an enzyme having PLC [phospholipase C] activity, which results in the formation of diacylglycerols and phosphates, and treated with an enzyme having PLA [phospholipase A] activity, which results in the formation of lyso-phospholipids and free fatty acids (FFA). The diacylglycerols and FFA from these two separate reactions then combine in the presence of the enzymes to generate new triacylglycerol molecules.

Processes for the preparation of phosphatide salts (Rutenberg, D., Lipogen Ltd., US8546104, October 1, 2013).

The present invention discloses a process for the preparation of phosphatide-salt complexes, the process including the steps of: using at least one raw material lecithin as a substrate; and enzymatically processing at least one raw material lecithin with phospholipase-D, racemic or enantiomerically pure serine, and/or amine in an aqueous carboxylate-salt-complex solution, wherein the step of processing is performed in a single-phase reaction environment, to produce phosphatide-salt complexes having a structural fatty-acid chain derived from at least one raw material lecithin. Preferably, the step of processing is performed at a pH in the range of about 4.5–8.0 at a temperature in the range of about 25–60°C. Preferably, the aqueous carboxylate–salt-complex solution is formed from an aqueous solution of a carboxylic acid with a chain length of C2–C8 and a salt in an approximately 1:2 (weight per weight) acid-to-salt ratio.

Lipid depot formulations (Thuresson, K., et al., Camarus AB, US8545832, October 1, 2013).

The present invention relates to pre-formulations comprising low viscosity, non-liquid crystalline, mixtures of: (i) at least one neutral diacyl lipid and/or at least one tocopherol; (ii) at least one phospholipid; (iii) at least one biocompatible, oxygen-containing, low viscosity organic solvent; wherein at least one bioactive agent is dissolved or dispersed in the low viscosity mixture and wherein the pre-formulation forms, or is capable of forming, at least one liquid crystalline phase structure upon contact with an aqueous fluid. The preformulations are suitable for generating parenteral, non-parenteral, and topical depot compositions for sustained release of active agents. The invention additionally relates to a method of delivery of an active agent comprising administration of a preformulation of the invention, a method of treatment comprising administration of a preformulation of the invention and the use of a preformulation of the invention in a method for the manufacture of a medicament.

GLP-1 analogue formulations (Joabsson, F., et al, Camarus AB, US8546326, October 1, 2013).

The present invention relates to compositions forming a low viscosity mixture of: (i) at least one neutral diacyl lipid, such as a diacyl glycerol; (ii) at least one phospholipid, such as a phosphatidyl choline; (iii) at least one biotolerable solvent, such as an oxygen-containing solvent; (iv) at least one glucagon-like peptide-1 (GLP-1) analogue; wherein the preformulation forms, or is capable of forming, at least one liquid crystalline phase structure upon contact with an aqueous fluid. The invention further relates to methods of treatment comprising administration of such com-positions, especially in treating diabetes, and to pre-filled administration devices and kits containing the formulations. Prilled waxes comprising small particles and smooth-sided compression candles made therefrom Uptain, K., et al., Elevance Renewable Sciences, Inc., US8551194, October 8, 2013 A candle and process for making it are disclosed. The candle comprises prilled wax particles, comprising hydrogenated natural oil and wherein at least 75% of the prilled wax particles are less than 800 µm in diameter. The candle includes a compressed core and a thermally fused outer layer.

High modulus bio-based polymer formulations (Boyles, D., et al., South Dakota School of Mines and Technology, US8552081, October 8, 2013).

The present invention is a high modulus bio-based polymer plastic composition or mixture and methods of preparing the same. The composition is formed from the reaction of a bio-based epoxidized triglyceride oil, an energy-activated catalyst, and a bio-based non-aromatic cross-linking compound to form a structural polymer plastic. The bio-based epoxidized triglyceride oil is selected from a bio-based epoxidized triglyceride or a bio-based acrylated epoxidized triglyceride. The non-aromatic cross-linking compound is selected from itaconic acid or itaconic anhydride, and the energy-activated catalyst is activated by ultraviolet radiation or heat.

Preparation process of oil extended rubber for tire, oil extended rubber for tire, and rubber composition and tire using the same (Sakaki, T., et al., Sumitomo Rubber Industries, Ltd., US8563628, October 22, 2013).

The present invention provides an oil extended rubber for a tire, which is obtained by: (i) a step of preparing an oil-in-water type emulsion by emulsifying a vegetable oil having an iodine value of not less than 135 with a surfactant; (ii) a step of mixing said emulsion of vegetable oil and a modified natural rubber latex, and then maturing the mixture; and (iii) a step of coagulating the mixture obtained in step (ii) to obtain a lump of a rubber.

Preparation of soy protein isolate using calcium chloride extraction (“S703”) (Segall, K.I., et al., Burcon Nutrascience (MB) Corp., US8557321, October 15, 2013).

A soy protein product having a protein content of at least about 60 wt% (N × 6.25) dry basis, preferably an isolate, is formed by a procedure in which soy protein is extracted from a soy source material using an aqueous calcium chloride solution at low pH, generally about 1.5 to about 5, and separating the resulting aqueous soy protein solution from residual soy protein source. The resulting clarified aqueous soy protein solution may be diluted and the pH adjusted within the range of 1.5–5.0. The solution may be concentrated by ultrafiltration, diafiltered, and then dried to provide the soy protein product. The soy protein product is soluble in acidic medium and produces transparent, heat stable solutions and hence may be used for protein fortification of soft drinks and sports drinks.

Liquid preparation (Goto, N., and K. Shibusawa, Eisai R&D Management Co., Ltd., US8557259, October 15, 2013).

It is an object of the present invention to provide a liquid preparation that excels in stability with no occurrence of precipitates and lees even after long storage. The liquid preparation contains a lipophilic material, a sucrose fatty acid ester, a polyoxyethylene hydrogenated castor oil, a polyglycerin fatty acid ester, a polyol, and water. Also provided are a pharmaceutical preparation, cosmetic preparation, and food and drink that contain the liquid preparation.

Antimicrobial composition based on botanical extracts from oil palm vegetation liquor (Sambanthmurthi, R., and Y.A. Yew, Malaysian Palm Oil Board, US8557309, October 15, 2013).

The present invention provides an antimicrobial composition comprising compounds extracted from the vegetation liquor of the palm oil milling process. This composition is rich in antioxidants and exhibits enhanced antimicrobial activity and bactericidal effect against a number of micro-organisms.

High-strength, environmentally friendly corrugated board (Netravali, A., and P. Govang, Cornell University, US8557367, October 15, 2013).

The present invention includes a high-strength, lightweight corrugated board. The board comprises a first sheet made of a soy protein-based resin and one or more sheets of plant-based fibers. The first sheet is connected to a corrugated member. In one aspect of the present invention, there is a method of manufacturing a high-strength, corrugated board.

Compositions and methods for making and modifying oils (Lam, D., et al., DSM IP Assets B.V., US8557551, October 15, 2013).

The invention provides novel methods for making or modifying oils, for example, plant, animal or microbial oils, such as vegetable oils or related compounds, that are low in a particular fatty acid(s), for example, low linoleic oils, low linolenic oils, low palmitic oils, low stearic oils, or oils low in a combination thereof. Oils are incubated with a polypeptide that selectively hydrolyzes palmitic acid.

Oral composition (Casey, J., et al., Conopco, Inc., US8546445, October 1, 2013).

A composition that is adapted for oral consumption comprising daidzein and an anthocyanidin, wherein the weight ratio of daidzein to anthocyanidin is in the range of from 1:1 to 1:100, wherein the daidzein is in the form of a pre-prepared aqueous dispersion, and wherein the composition is free of soy protein, which can exhibit an anti-inflammatory effect in skin, the use of a composition containing daidzein and an anthocyanidin for obtaining an anti-inflammatory effect in the skin and a method of reducing skin inflammation through the oral consumption of the composition.

Antispattering agent (Garcia, R.E., and G.A. Viecco Castillo, Team Foods Colombia S.A., US8563068, October 22, 2013).

The invention relates to an agent comprising vegetable oil, a hydrophilic colloidal metal oxide, a hydrophobic treated metal oxide, and a mixture of polypropylene glycols, which, when added to pure edible fats or oils, provides same with a low spatter property when said oils and fats are used for frying foods. Said antispattering agent does not alter the organoleptic properties or appearance of the oil or fat, such as smell, taste, color, transparency, and stability at low temperatures, or produce any negative effects, such as the formation of scum during frying or the presence of particles.

Environment friendly base fluid to replace the toxic mineral oil-based base fluids (Amanullah, M., Saudi Arabian Oil Co., US8563482, October 22, 2013).

Processes for producing alkyl esters useful as base fluids in oil-based mud compositions. The alkyl esters are produced from raw material waste oil that includes vegetable oil. The raw material waste oil can be obtained from the food industry, such as from food chains. The raw material waste oil is purified by removing impurities from it. The raw material waste oil is then esterified with an alcohol in the presence of a catalyst. The resulting alkyl ester products are then separated from triglycerides. The alkyl ester products are then washed and dried.

Skin cleansing agent with particles containing hydrogenated castor oil (Stolz, H.J., et al., Peter Greven Hautschutz GmbH & Co., US8563492, October 22, 2013).

A skin cleaning agent containing from 2 to 25% by weight of a cleaning body having a mean grain size of from 100–1000 µm and containing at least 50% hydrogenated castor oil; from 2 to 30% by weight of surfactants; from 0.1 to 10% by weight of thickeners; water and optionally further auxiliaries.

Synthetic lung surfactant and use thereof (Notter, R.H., et al., University of Rochester, Los Angeles Bio-Medical Research Institute at Harbor-UCLA Medical Center N/A, University of Guelph, US8563683, October 22, 2013).

The present invention relates to synthetic lung surfactant compositions that contain one or more of phospholipase-resistant phosphoglycerol derivatives, phospholipase-resistant phosphocholine derivatives, and surface active proteins or peptides, more preferably a combination of at least two or all tharee of these materials. Novel phospholipase-resistant phosphoglycerol derivatives, phospholipase-resistant phosphocholine derivatives, and surface active peptides are also disclosed herein. Uses of the surfactant compositions of the present invention to treat endogenous surfactant dysfunctional or deficient lung tissue, to prepare synthetic peptides for use in the surfactant compositions, and to deliver therapeutic agents are also disclosed.

Process for extracting lipids from microalgaeo disclosed. (Hutton, M.W., and C.R. Lehr, Cal Poly Corp., US8563759, October 22, 2013).

A process for extracting lipids from microalgae; the process involves pretreating a quantity of non-homogenized microalgae with an aliphatic alcohol for a predetermined period of time. The pretreatment liberates a substantial portion of lipids from the microalgae without requiring energy intensive cell membrane disruptive technologies. The liberated lipids are then treated with a transesterification reagent to form fatty acid methyl esters. The fatty acid methyl esters are separated from the resulting mixture and may be further purified to remove remaining solvents or other impurities. The fatty acid methyl esters produced by the process are suitable as a green energy biodiesel product.

Glutathione-based delivery system (Wang, A.J., et al., Industrial Technology Research Institute, US8569239, October 29, 2013).

A delivery system that includes a carrier or an active com-pound and a glutathione or a glutathione derivative grafted thereon. The invention also provides a compound including a moiety comprising a vitamin E derivative or a phospholipid derivative, a polyethylene glycol (PEG), or a PEG derivative bonded thereto, and a glutathione (GSH) or a GSH derivative bonded to the polyethylene glycol or the polyethylene glycol derivative.

Plant-derived seed extract rich in essential fatty acids derived from Salvia hispanica L. seed: composition of matter, manufacturing process, and use (Minatelli, J., et al., U.S. Nutraceuticals LLC, US8574637, November 5, 2013).

A Salvia hispanica L. derived seed oil extract composition containing from 60–88% polyunsaturated fatty acids in a ratio of from 3.1:1–3.3:1 of α-linolenic acid to linoleic acid, 4–10% of C18 monounsaturated fatty acid, 1–5% of C18 saturated fatty acid, and 4–8% of C16 saturated fatty acid in a mixed triglyceride form that is stable at room temperature of 12–24 months containing a mixture of selected antioxidants.

Lipase powder, method for manufacture thereof, and use thereof (Suganuma, T., et al., The Nisshin OilliO Group, Ltd., US8580550, November 12, 2013).

There is provided a lipase powder that is a granulated material comprising a lipase and at least one member selected from the group consisting of fatty acids having 8–12 carbon atoms, alcohol esters thereof, and a mixture thereof. This lipase powder has an increased lipase activity.

Method of continuous in-situ triglyceride stabilization and sulfur reduction of FOG (fats, oil, and grease) to optimize fuel extraction (Lenger, M. J., amd G.H. Lenger, US8585901, November 19, 2013).

A method for continuous in-situ triglyceride stabilization in FOG (fats, oil, and grease) commonly referred to as trap grease. The stabilization is achieved by eliminating hydrolysis and thus preventing the BTU-rich triglycerides breaking down into free fatty acids (FFA) or the formation of mono- and diglycerides. A closed loop aeration and recirculation of the FOG ensures sufficient dissolved oxygen not only arresting hydrolysis but also eliminating the formation of hydrogen sulfide. The method furthermore employs the formation and continuing functioning of a biofilm for the microbiological reduction of the FOG’s sulfur content. A low FFA/high triglycerides concentration as well as sulfur reduction is highly desirable, allowing for easy biodiesel fuel conversion or biogasification. The resulting biofuel does not exhibit the typical hygroscopic property found in B100 biodiesel.

Method for reprocessing biodiesel sludge (Seidel, E., et al., Lurgi GmbH, US8580987, November 12, 2013).

A method for reprocessing a phase substantially consisting of steryl glycoside/fatty acid alkyl ester/water agglomerates, which was formed when fatty acid alkyl ester generated by transesterification of vegetable oils or animal fats was washed with water, wherein the water content is evaporated by heating the phase and subsequently the steryl glycosides are split into their sterol and sugar fractions in the presence of an acid catalyst.

Nutritional composition for infants (Mace, C., et al., Nestec S.A., US8586077, November 19, 2013).

A nutritional composition for infants comprises a protein source, a lipid source, and a carbohydrate source wherein the lipid source includes at least 16 wt% linoleic acid and at least 2 wt% α-linolenic acid expressed as a percentage of total fatty acid content in each case and in amounts such that the ratio of linoleic acid/α-linolenic acid is in the range from 1–10.

Composition suitable for use in baking (McNeill, G.P., et al., Loders Croklaan USA LLC, US8586122, November 19, 2013).

A composition comprising: (i) from about 20% to about 80% by weight of an interesterified palm oil olein; (ii) from about 5% to about 25% by weight of a liquid oil; (iii) from about 15% to about 75% by weight of a fat selected from the group consisting of palm oil stearins, interesterified palm oil stearins, palm oil oleins, fully hydrogenated oils, and mixtures thereof may be used as a bakery fat, particularly a laminating fat for products such as puff pastry.

Biobased penetrating oil (Westerman, T., et al., State Industrial Products Corp., US8586518, November 19, 2013).

A biobased penetrating oil for use to reduce friction between fittings. The penetrating oil composition preferably contains one or more long-chain, low-volatile esters specifically derived from a natural plant-based oil, such as a combination of methyl esters derived from soybean oil, and an unsulfurized terpene, such as a pine oil or limonene, and various orange terpenes as a solvent. The penetrating oil can be an aerosolized product and include a carbon dioxide propellant.

Composition for preventing and improving metabolic syndrome (Saito, S., et al., J-Oil Mills, Inc., US8586529, November 19, 2013).

A method for improving blood HDL/LDL [high density lipoprotein/low density lipoprotein] cholesterol ratio, reducing blood triglyceride level, reducing blood sugar level, and/or reducing body weight, that includes ingesting a composition containing a concentrated soybean germ product. The soybean germ product includes soybean germ protein; 1.0% by weight or less of saponin relative to the total weight of the soybean germ product; and 0.5% by weight or less of isoflavone relative to the total weight of the soybean germ product.

Plant-derived seed extract rich in essential fatty acids derived from Salvia hispanica L. seed: composition of matter, manufacturing process, and use (Minatelli, J., et al., U.S. Nutraceuticals LLC, US8586104, November 19, 2013).

A Salvia hispanica L. derived seed oil extract composition of matter containing from 60–88% polyunsaturated fatty acids in a ratio of from 3.1:1–3.3:1 of α-linolenic acid to linoleic acid, 4–10% of C18 monounsaturated fatty acid, 1–5% of C18 saturated fatty acid and 4–8% of C16 saturated fatty acid in a mixed triglyceride form that is stable at room temperature of 12–24 months containing a mixture of selected antioxidants.

Tailored oils produced from recombinant heterotrophic microorganisms (Franklin, S., et al., Solazyme, Inc., US8592188, November 26, 2013).

Methods and compositions for the production of oil, fuels, oleochemicals, and other compounds in recombinant microorganisms are provided, including oil-bearing microorganisms and methods of lowcost cultivation of such microorganisms. Micro-algal cells containing exogenous genes encoding, for example, a lipase, a sucrose transporter, a sucrose invertase, a fructokinase, a polysaccharide-degrading enzyme, a keto acyl-ACP [acyl carrier protein] synthase enzyme, a fatty acyl-ACP thioesterase, a fatty acyl-CoA/aldehyde reductase, a fatty acyl-CoA reductase, a fatty aldehyde reductase, a fatty aldehyde decarbonylase, and/or an acyl carrier protein, are useful in manufacturing transportation fuels such as renewable diesel, biodiesel, and renewable jet fuel, as well as oleochemicals such as functional fluids, surfactants, soaps, and lubricants.

Emulsion system derived from engkabang (illipe) fat esters (Basri, M., et al., Universiti Putra Malaysia, US8598236, December 3, 2013).

An isotropic or homogeneous emulsion system comprises an oil phase including fat esters of illipe fat and a solubilizer; a non-ionic surfactant; and deionized water; characterized in that the solubilizer is a mixture of polyethyleneglycol-40 hydrogenated castor oil, polysorbate-20, and octoxynol-12.

Method and compositions for production of transgenic plants (Ahmad, G.K.P., Malaysian Palm Oil Board, US8598410, December 3, 2013).

The present invention relates generally to a process of producing transgenic plants and more particularly transgenic palm oil plants carrying exogenous genetic material that confers on said plants or cells of said plants particular phenotypic traits. The present invention is further directed to oil, and particularly palm oil, having beneficial and desirable characteristics, produced by the transgenic plants made in accordance with the present invention.

Method for the removal of phosphorus (Havlik, P., et al., Syntroleum Corp., US8575409, November 5, 2013).

A process for producing a hydrocarbon from biomass. A feed stream containing biomass having fatty acids, mono-, di-, and/or triglycerides, and a phosphorus content of between about 1 wppm [weight parts per million] and about 1,000 wppm is provided. A heated hydrocarbon solvent and a hydrogen-rich gas are provided. The feed stream, the heated hydrocarbon solvent, and the hydrogen-rich gas are combined in the presence of a low activity hydrogenation catalyst. A spent low-activity hydrogenation catalyst is recovered at the end of a run wherein the spent low-activity hydrogenation catalyst contains at least 3% by weight phosphorus.

Composition of biodegradable gear oil (Singh, A.K., and A. Chamoli, Council of Scientific & Industrial Research, US8557754, October 15, 2013).

A composition of biodegradable gear oil that mainly contains modified non-edible vegetable oils. Mono-esters are hydrogenated, epoxidized, or aryl alkylated or mixture thereof, and C7–C12 primary alcohol. In addition to chemically modified non-edible vegetable oils, the composition also contains an additive pack, which comprises at least one: antioxidant, an extreme pressure additive, an anti-foaming agent, a pour point depressant, a corrosion inhibitor, and a detergent-dispersant additive. The product of this invention has utility as industrial and automotive gear oil GL 4 grade. The compositions are significantly biodegradable, eco-friendly, reduce use of petroleum, have lower cost than synthetic oil, are miscible in mineral and synthetic fluids, and are safe to use due to higher flash point.

Aqueous polymer compositions obtained from epoxidized natural oils (Pajerski, A.D., and S.N. Lerner, Lubrizol Advanced Materials, Inc., US8568889, October 29, 2013).

Aqueous polyurethane dispersions are made from urethane prepolymers comprising one or more polyhydroxy compounds from ketone functional molecules derived from an epoxidized natural oil. Addition of a hydrazine functional moiety to the pre-polymer dispersion can further provide a crosslinking mechanism resulting in the formation of azomethine linkages in the resulting polyurethane during drying. When the ketone functional molecule is derived from levulinic acid and epoxidized vegetable oil, the resulting urethane dispersion can also be converted into a hybrid polyurethane-vinyl dispersion by adding and polymerizing one or more vinyl monomers in the polyurethane prepolymer or polyurethane dispersion.

Production of soluble protein solutions from soy (“s701” CiP) (Schweizer, M., et al., Burcon Nutrascience (MB) Corp., US8563071, October 22, 2013).

A soy protein product, which may be an isolate, produces transparent heat-stable solutions at low pH values and is useful for the fortification of soft drinks and sports drinks without precipitation of protein. The soy protein product is obtained by extracting a soy protein source material with an aqueous calcium salt solution to form an aqueous soy protein solution, separating the aqueous soy protein solution from residual soy protein source, adjusting the pH of the aqueous soy protein solution to a pH of about 1.5 to about 4.4 to produce an acidified clear soy protein solution, which may be dried, following optional concentration and diafiltration, to provide the soy protein product.

Wax compositions and methods of preparing wax compositions (Lemke, D.W., and M.C. Thiede, Elevance Renewable Sciences, Inc., US8603197, December 10, 2013).

Described are morphology stable wax compositions comprising the (trans)esterification product of a wax-forming composition comprising: (i) a triglyceride stock, a fatty acid stock, or a mixture thereof; and (ii) a glycerol-based composition comprising glycerol, polyglycerol, or a mixture thereof. Methods of making the waxes are also described. The wax compositions may be used in candles, stack waxes, jell candles, cosmetics, food coatings, adhesives, board manufacturing (e.g., particle board and oriented strand board), urethane foams or coatings, alkyd coatings, coating formulation additives, printing additives, polymer processing agents, extrusion processing aids, polymer plasticizers, mold releases, polishes, and stick markers.

Stable whippable and whipped food products (Perks, C., et al., Rich Products Corp., US8603559, December 10, 2013).

The present invention provides stable whippable or pre-whipped food products comprising exudate gums in combination with proteins and optionally comprising cellulosic hydrocolloids; triglycerides; sweetener/bulking agents and water. The whippable liquid product is free of fat-based emulsifiers. The product is stable through processing and freeze/thaw and when whipped the resulting product can be used as icing, topping, and filling in a dessert. The prewhipped product further comprises non-hydrogenated fat-based emulsifiers but is free of other fat-based emulsifiers. This product can be stored frozen and when thawed, can be directly applied as icing, topping, and filling.

Coffee-derived surfactants (Gaonkar, A.G., et al., Intercontinental Great Brands LLC, US8603562, December 10, 2013).

Coffee-derived surfactants are provided by transesterification reactions of sugars and coffee oil. The coffee-derived surfactants are especially useful in the production of coffee oil emulsions for use with, or incorporation into, coffee products.

Photopolymerisable composition (Knocke, F., XETOS AG, US8603730, December 10, 2013).

There is described a photopolymerisable composition comprising: (i) 75–99% by weight of an ethylenically unsaturated monomer or a monomer mixture of different ethylenically unsaturated monomers, (ii) 0.5–25% by weight of a triglyceride or a mixture of different triglycerides, and (iii) 0.1–10% by weight of a photoinitiator system that activates the polymerisation of the ethylenically unsaturated monomer(s) upon exposure to actinic radiation, wherein the composition is a homogeneous, clear and, at 20°C, liquid mixture. Furthermore, there are described elements manufactured from such photo-polymerisable compositions and methods for the formation of lightresistant holograms therefrom. The photopolymerisable compositions are useful, in particular, as recording material for optical elements having refractive index modulation, in particular, holograms.

Method for purifying fatty acid alkyl ester greatly loaded with saponification products (Bonsch, R., et al., Lurgi GmbH, US8604228, December 10, 2013).

A method for the continuous extraction of impurities, in particular saponification products, from a fatty acid alkyl ester phase produced by transesterification of vegetable or animal oils or fats with a great tendency to form saponification products, by means of an aqueous, acid glycerol phase containing a complexing agent.

Method for preserving a microorganism (Higashiyama, K., Nippon Suisan Kaisha, Ltd., US8609397, December 17, 2013).

A method for preservation of a microorganism capable of microbial production of a polyunsaturated fatty acid or a compound comprising a polyunsaturated fatty acid as a constituent fatty acid, which method comprises: (i) forming spores in a spore-forming medium at pH 4–7 containing a nutrient source comprising an inorganic salt and a saccharide; (ii) suspending the spores obtained in (i) in sterilized water, or sterilized water containing a surfactant and/or an inorganic salt to prepare a spore suspension, and adding a cryoprotectant at 5–15% to prepare a cryopreserving spore suspension; and (iii) preserving the cryopreserving spore suspension obtained in (ii) at between –100°C and –20°C.

Selective biodegradation of free fatty acids in fat-containing waste (Reuter, C.J., et al., Osprey Biotechnics, Inc., US8609398, December 17, 2013).

A process of selectively degrading fatty acids in fat-containing waste materials without significant degradation of triglycerides, thereby converting otherwise economically burdensome waste materials into valuable products, involves contacting a fat-containing waste comprising triglycerides and fatty acids with a bacterial culture comprising Pseudomonas bacteria capable of degrading fatty acids into water and carbon dioxide, and wherein the bacterial culture is substantially free of microorganisms capable of producing extracellular lipase in an amount that would cause significant degradation of the triglycerides.

Gear oil composition (Okada, T., and S. Hara, Idemitsu Kosan Co., Ltd., US8609596, December 17, 2013).

To provide a gear oil composition containing a base oil, and compounded therein: (i) an ashless dithiocarbamate compound and (ii) an ester of pentaerythritol and a C12–C20 branched fatty acid, the ester having a hydroxyl value of 20–100 mg KOH/g. The gear oil composition has a high transmission efficiency and shows both of resistance to sludge formation and extreme pressure property.

Stabilized, antimicrobially effective composition with a content of bispyridinium alkane (Beilfuss, W., et al., Air Liquide Sante (International), US8609697, December 17, 2013).

An aqueous-based composition which includes (i) at least one bispyridinium alkane (for example, octenidine) and (ii) at least one stabilizer selected from antioxidants, complexing agents, reducing agents, UV filters and photoprotective agents, in particular α-tocopherol, and BHT [butylated hydroxytoluene]. The composition can also include (iii) one or more auxiliaries selected from, for example, nonionic surfactants, ethers, solvents and polymers, in particular fatty alcohol alkoxylates and alkoxylated fatty acid monoglycerides. The presence of the stabilizer reduces or prevents the appearance of decomposition products of bispyridinium alkanes and, in the case of the presence of auxiliaries, of decomposition products of the auxiliaries, such as ethers and peroxides.

Fatty acid composition for treatment of Alzheimer’s disease and cognitive dysfunction (Bryhn, M., Pronova Biopharma Norge AS, US8609726, December 17, 2013).

This invention relates to the use of a fatty acid composition comprising at least docosahexaenoic acid (DHA), or derivatives thereof, and eicosapentaenoic acid (EPA), or derivatives thereof for manufacturing of a medicinal product or a food stuff for the treatment and/or prevention of amyloidosis-related diseases, such as Alzheimer’s disease, as well as treatment/prevention of cognitive dysfunction.

Cosmetic particles that transform from hard to soft particles comprising hydrogenated long-chain triglyceride oils (Kleiman, R., et al., International Flora Technologies, Ltd., US8613956, December 24, 2013).

Cosmetic particle compositions are provided which are adapted to form hard cosmetic particles that transform to soft cosmetic particles after their incorporation into topical formulations, particularly surfactant-based topical formulations. The composition includes one or more partially or fully hydrogenated triglyceride oils, at least 50% of which have at least 15% by weight fatty acid moieties with carbon chain lengths of C18 or higher. Additives may be disposed in or on the hard cosmetic particles and delivered when the cosmetic particles are broken proximate a target such as the skin, hair, or nails of a mammalian subject or another target. The transformable hard cosmetic particles permit the storage and shipment of intact cosmetic particles yet transform in situ to achieve the benefits of soft cosmetic particles.

Process for production isomer-enriched conjugated linoleic acid compositions (Taran, V., et al., Stepan Specialty Products LLC, US8614074, December 24, 2013).

A process for the preparation of a composition comprising the cis-9, trans-11 and trans-10, cis-12 isomers of conjugated linoleic acid (CLA) comprises: providing a mixture comprising cis-9, trans-11 and trans-10, cis-12 isomers of conjugated linoleic acid (CLA) in which one of the cis-9, trans-11 and trans-10, cis-12 isomers is present in a first weight ratio X of at least 1.3:1 with respect to the other isomer; and subjecting the mixture to crystallization to form a composition comprising the cis-9, trans-11 and trans-10, cis-12 isomers in which one of the cis-9, trans-11 and trans-10, cis-12 isomers is present at a second weight ratio Y with respect to the other isomer, wherein Y is greater than X.

Users of long-chain fatty acids for treatment of autoimmune disease (Burstein, P., and A. Ben-Nun Yeda Research and Development Co., Ltd., US8614248, December 24, 2013).

Agents selected from: (i) a C1–C24 alkyl ester of a saturated or cis-unsaturated C10–C24 fatty acid; (ii) a monoester or polyester of a polyol having at least four hydroxy groups with a saturated or cis-unsaturated C10–C24 fatty acid or an anhydro derivative thereof; (iii) a monoester or polyester of a mono-, di- or polysaccharide with a saturated or cis-unsaturated C10–C24 fatty acid; (iv) an amide of a saturated or cis-unsaturated C10–C24 fatty acid with an aliphatic or aromatic amine or with an amino acid, peptide, protein or aminosaccharide; and (v) combinations of any of (i) to (iv), can be used for treatment of autoimmune diseases and other immune-associated inflammatory disorders. Preferred agents are ethyl oleate and mannide monooleate or a combination thereof.

Process for the production of a fatty acid/carnitine derivative (Smida, D., Lonza Ltd., US 8614343, December 24, 2013).

The present invention discloses a process for the production of a fatty acid/l-carnitine derivative, whereby the educts are reacted in the presence of monochloroacetic acid.

Sealing of a cap on a glass container (Grayer, A., and G. Boiron, Amcor Flexibles Selestat SAS, US8617674, December 31, 2013).

A multi-layer sheet designed for the sealing of a container made of glass by heat sealing on the sealing ring of the container treated by means of oxides and/or of metal salts comprises at least a support layer and a lower layer made of a polymeric heat-sealable material onto which is grafted an unsaturated carboxylic acid.

Non-dispersive process for insoluble oil recovery from aqueous slurries (Kipp, P.B., et al., Board of Regents, The University of Texas System; Organic Fuels Algae Technologies, US8617396, December 31, 2013).

The development and application of a novel non-polar oil recovery process utilizing a non-dispersive solvent extraction method to coalesce and recover oil from a bio-cellular aqueous slurry is described herein. The process could apply to recovery of algal oil from a lysed or non-lysed algae slurry, recovery of omega fatty acids from a bio-cellular aqueous feed, recovery of β-carotene from a bio-cellular aqueous feed, and for the removal from produced water in oil production and similar type applications. The technique of the present invention utilizes a microporous hollow fiber (MHF) membrane contactor. The non-polar oil recovery process described herein can be coupled to a collecting fluid (a non-polar solvent such as heptane, a biodiesel mixture or the previously extracted oil) that is circulated through the hollow fiber membrane.In cases where the biodiesel mixture or the previously extracted oil is used, the solvent recovery step (e.g., distillation) can be eliminated.

Robust multi-enzyme preparation for the synthesis of fatty acid alkyl esters (Basheer, S., et al., Transbiodiesel Ltd., US8617866, December 31, 2013).

Disclosed is an enzymatic process for the preparation of fatty acid alkyl esters, particularly fatty acid methyl esters (biodiesel), in a solvent-free microaqueous system, from a fatty acid source and an alcohol or alcohol donor, employing a robust lipase preparation that comprises at least two lipases separately or jointly immobilized on a suitable support, where one of the lipases has increased affinity to partial glycerides, another is sn-1,3 positional specific, and an optional third lipase has high selectivity toward the sn-2 position of the glycerol backbone of the fatty acid source.

Compositions for removing lead from metal surfaces (Hunt, D., and G. Kuhlmann, Stone Chemical Co., US8618038, December 31, 2013).

The invention provides an aqueous composition that includes a hydroxy-substituted mono-, di-, or tricarboxylic acid; phosphoric acid; a surfactant; and water. The invention further provides a method for removing lead from the surface of metal; the method includes contacting a metal surface with an aqueous composition that includes a hydroxyl-substituted mono-, di-, or tricarboxylic acid; phosphoric acid; a surfactant; and water; to provide a metal surface with a reduced amount of leachable lead. The leachable lead on the surface of the metal can be reduced to below 1 ppb by using the composition described herein.

Lipid preparation for enhancing mineral absorption (Shulman, A., et al., Enzymotec Ltd., US8618050, December 31, 2013).

Disclosed is a dietary ingredient comprising at least one edible lipid that does not inhibit mineral absorption, enhances mineral absorption and intake, particularly a chemically or enzymatically synthesized synthetic oil, particularly glyceride-based lipid with high levels of mono- or polyunsaturated fatty acids at positions sn-1 and sn-3 of the glycerol backbone, vegetable- and plant-derived oil, such as flax and canola oils, short- and medium-chain lipids, preferably medium-chain triglycerides, and an oil mimicking the triglyceride composition of human mother’s milk fat and its various uses. The dietary ingredient is particularly intended for use in enhancing calcium absorption and in the prevention and/or treatment of disorders associated with depletion of bone calcium and bone density, prevention and treatment of osteoporosis, for the enhancement of bone formation and bone mass maximization, and for the enhancement of bone formation in infants and young children.

Chocolate products containing amorphous solids and methods of producing same (Hanselmann, W., The Hershey Co., US8617635, December 31, 2013).

The invention relates to novel food, confectionery, and chocolate compositions and methods of producing them. In one embodiment, an amorphous sugar, such as a corn syrup solid, wholly or partially replaces crystalline sugar in the chocolate composition. In a second embodiment, an amorphous sugar is combined with cocoa solids, milk solids, and/or fruit purees and incorporated into a chocolate product or composition. In a further embodiment, the invention relates to a chocolate composition comprising amorphous sugar and crystallized sugar wherein the ratio of amorphous sugar to crystallized sugar is such that the combination of amorphous sugar and crystallized sugar has a glass transition temperature of at least room temperature and amorphous sugar is detectable in the final product or composition.

Charged lipoprotein complexes and their uses (Dasseux, J.-L., US8617615, December 31, 2013).

The present disclosure provides charged lipoprotein complexes that include as one component a negatively charged phospholipid that is expected to impart the complexes with improved therapeutic properties.

Catalyst for transesterification process (Banavali, R., and J. Trejo, Rohm and Haas Co., US8685881, April 1, 2014).

The present invention relates to a method for producing esters from triglycerides by using solid heterogeneous catalysts comprised of calcined calcium carbonate, particularly for obtaining biodiesel.

Polyurethane made from hydroxyl-methyl containing fatty acids or alkyl esters of such fatty acids (Van der Wal, H.R., and C.F. Camiel, Dow Global Technologies LLC, US8686057, April 1, 2014).

Polyurethane polymers are made from a reaction mixture that contains a polyisocyanate, a hydroxylmethyl-containing fatty acid or ester, and another polyol, polyamine, or aminoalcohol. The carboxylic acid or ester group on the hydroxymethyl-containing fatty acid or ester is capable of engaging in a variety of reactions with the polyisocyanate and/or amine or hydroxyl groups present in the reaction mixture. This allows for good-quality, high molecular weight polymers to be produced even though the hydroxymethyl-containing fatty acid or ester tends to be a low functionality material.

Process for preparing diesel fules using vegetable oils or fatty acid derivatives (Hanks, P.L., et al., ExxonMobil Research and Engineering Co., US8686203, April 1, 2014).

A process for preparing fuels, such as diesel fuels or jet fuels, by hydrotreating vegetable oils or fatty acid derivatives that may be applied to existing equipment for treating fossil fuels.
The process comprises feeding hydrotreating a combined oxgenate feed stream, such as fatty acid methyl esters, and a hydro-carbon feed stream until not more than 86 wt% of the esters in the oxygenate feed stream are converted to hydrocarbons, and optionally further hydrotreating the product stream within at least a second hydrotreatment reaction zone until at least 90 wt% of the esters in the oxygenate feed stream are converted to hydrocarbons, before removing and separating a hydrocarbon stream suitable for use as fuel.

Detergent for metal (Maeyama, S., et al., Lion Corp., US8685912, April 1, 2014).

A detergent composition for metal according to the present invention contains a specific nonionic surfactant, a specific nitro-gen-containing organic compound, a specific carboxylic acid or salt thereof, and a specific alkanol amine, and has a pH of at least 9 that is measured at 25°C when the detergent composition is diluted to 1% by mass of an aqueous solution. According to the present invention, the detergent composition for metal having excellent corrosion inhibition properties, excellent effluent treatment properties, excellent foaming suppressing properties, and excellent liquid stability in addition to high detergent properties for metal can be provided.

In-shower lotion compositions comprising up to 10% free fatty acids wherein ration of unsaturated to saturated fatty acids is at least 1:1 (Patel, R., and R.M. Paredes, Conopco, Inc., US8691197, April 8, 2014).

This invention relates to rinse-off skin-conditioning compositions comprising relatively low amounts of oil/emollient and relatively low amounts of aqueous phase stabilizer/structurant. Use of unsaturated fatty acid (or at least minimum amount of unsaturated fatty acid as percentage of total fatty acid) has been found to result in unexpectedly high hydration. In a second embodiment, use of branched fatty acid (at minimum amount branched as percentage of total) also results in superior hydration. Also mixtures of unsaturated and branched fatty acids can be used. In a second embodiment, the invention relates to method of enhancing hydration using compositions as noted.