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Patent

High modulus polymers and composites from plant oils

20 Oct 1998-
TL;DR: The liquid resins described in this article are derived from plant and animal oil triglycerides by suitably functionalizing the triglyceride with chemical groups that render it polymerizable, which is a combination of various triesters of fatty acids linked together with glycerol.
Abstract: The liquid resins described herein are derived from plant and animal oil triglycerides by suitably functionalizing the triglyceride with chemical groups that render it polymerizable. The triglyceride molecular structure is a combination of various triesters of fatty acids linked together with glycerol. The fatty acid residues are linear carboxylic acids containing from about 4 to about 30 carbon atoms, but preferably from about 14 to about 22 carbons and from about zero to about 4, or preferably from about 2 to 3 carbon-carbon double bonds. As obtained in nature, these double bonds are predominantly in the cis (Z) configuration and, in the case of polyunsaturated acids, not conjugated. The fatty acids derived from triglycerides include, but are not limited to the following: Lauric (C12:0), i.e., 12 carbon atoms long containing zero C=C double bonds, Myristic (C14:0), Palmitic (C16:0), Stearic (C18:0), Oleic (C18:1), Linoleic (C18:2), Linolenic (C18:3), Eicosanoic (C20:0), cis-11-Eicosanoic (C20:1), Docosanoic (C22:0) and cis-13-Docosanoic (C22:1). Typical plant oil triglycerides used for the purpose of this invention contain about 10-20 % saturated, about 20-30 % mono-unsaturated, about 40-60 % di-unsaturated, and about 5-15 % tri-unsaturated fatty acid residues, but other distributions, both narrow and broad, of fatty acid residues can also be used for the thermoset and plastic resins described in this invention.
Citations
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Journal ArticleDOI
TL;DR: In this paper, the composite panels made by room temperature cure with natural fiber reinforcement of about 10-50 wt% increased the flexural modulus to a range between 1.5 and 6 GPa depending on the nature of the fiber mat.

420 citations

Journal ArticleDOI
TL;DR: In this article, the ACRES (Affordable Composites from Renewable Sources) group at the University of Delaware has developed new chemistries to synthesize rigid polymers from plant oils.
Abstract: The goal of this project is to develop new composites using fibers and resins from renewable resources. The ACRES (Affordable Composites from Renewable Sources) group at the University of Delaware has developed new chemistries to synthesize rigid polymers from plant oils. The resins produced contain at least 50% plant triglycerides and have mechanical properties comparable to commercially available synthetic resins such as vinyl esters, polyesters and epoxies. This project explores the development of all-natural composites by using natural fibers such as hemp and flax as reinforcements in the ACRES resins. Replacing synthetic fibers with natural fibers has both environmental and economic advantages. Unlike carbon and glass fibers, natural fibers are abundantly available from renewable resources. In terms of cost, natural fibers are cheaper than the synthetic alternatives. The natural fibers and plant-based resins have been shown to combine to produce a low cost composite with good mechanical properties. Tensile strength in the 30 MPa range has been obtained for a composite containing about 30 wt% Durafibre Grade 2 flax. The tensile modulus was found to be 4.7 GPa for a 40 wt% flax composite. Similar numbers where obtained for the hemp composites obtained from Hemcore Inc. Composites from renewable resources offer significant potential for new high volume, low cost applications.

333 citations

Journal ArticleDOI
TL;DR: In this paper, structural panels and unit beams were manufactured out of soybean oil based resin and natural fibers (flax, cellulose, pulp, recycled paper, chicken feathers) using vacuum assisted resin transfer molding (VARTM) technology.

298 citations

Journal ArticleDOI
06 Jan 2005-Polymer
TL;DR: In this article, an acrylated epoxidized soybean oil (AESO), which has an average of 3.4 acrylates per triglyceride, was used as starting material.

235 citations

Journal ArticleDOI
TL;DR: In this article, the authors synthesize a monomer from a fatty acid methyl ester capable of forming high molecular weight polymers, which may be of considerable interest for pressure sensitive adhesive applications.
Abstract: The focus of this work is to synthesize a monomer from a fatty acid methyl ester capable of forming high molecular weight polymers. The mono-unsaturation in the starting material, methyl oleate, was first epoxidized using a peroxy acid. This intermediate material was further modified using acrylic acid. The acrylated molecule is able to participate in free-radical polymerization reactions to form high molecular weight polymers. The rate of polymerization was low because of the long aliphatic structure of the monomer. It is hypothesized that the polymerization reaction occurred in the interface between the particle and water, thereby slowing down the reaction. After 18 h of reaction, a monomer conversion of approximately 91% was achieved. A maximum weight-average molecular weight of approximately 106 g/mol was observed after 14 h of reaction. At early reaction times linear polymers were formed. However, as the reaction time increased, the amount of branching that occurred on the polymer molecule increased, as indicated by gel permeation chromatography and light scattering. This has been attributed to chain transfer to polymer via hydrogen abstraction from a tertiary backbone C–H bond. The resulting polymer may be of considerable interest for pressure-sensitive adhesive applications. © 2002 John Wiley & Sons, Inc. J Polym Sci Part A: Polym Chem 40: 451–458, 2002; DOI 10.1002/pola.10130

203 citations

References
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Patent
06 Mar 1989
TL;DR: A plastic surgical clip comprises a pair of arms having inturned opposing tips, the arms being joined by a bridge having a lesser cross-section to provide a locus for bending by drawing the ears in parallel directions against an intermediate support as mentioned in this paper.
Abstract: A plastic surgical clip comprises a pair of arms having inturned opposing tips, the arms being joined by a bridge having a lesser cross-section to provide a locus for bending by drawing the ears in parallel directions against an intermediate support.

255 citations

Journal ArticleDOI
TL;DR: A broad range of crosslinked polyesters were prepared by curing epoxidized soybean oil with various dicarboxylic acid anhydrides in the presence of cure catalysts such as tertiary amines, imidazoles, or aluminum acetylacetonate as discussed by the authors.
Abstract: A broad range of crosslinked polyesters were prepared by curing epoxidized soybean oil with various dicarboxylic acid anhydrides in the presence of cure catalysts such as tertiary amines, imidazoles, or aluminum acetylacetonate. The mechanical and thermal properties of the casting resins were dependent upon the type of anhydride. While the anhydrides of hexahydrophthalic acid, succinic acid, and norbornene dicarboxylic acid yielded highly flexible rubbery materials with glass transition temperatures below room temperature, the more rigid anhydrides of maleic and phthalic acid gave amorphous stiff polyesters with higher glass transition temperatures varying between 43 and 73°C. When the cure reaction was carried out in polypropylene melts, multiphase polymers were formed containing polyester phases dispersed in the continuous polyolefin matrix.

82 citations

Patent
19 Apr 1985
TL;DR: In this article, certain vegetable oil lipid adducts, either alone or in combination with disproportionated vegetable oils, are disclosed which provide persistent softening effects upon incorporation in skin and hair care preparations.
Abstract: Certain vegetable oil lipid adducts, either alone or in combination with disproportionated vegetable oils, are disclosed which provide persistent softening effects upon incorporation in skin and hair care preparations. The emollients of the invention include both the water-soluble and water-insoluble salts of the vegetable oil adducts. The certain vegetable oil adducts of the invention are the adducts prepared from vegetable oils containing nonconjugated polyunsaturated fatty acid esters which are conjugated and then modified via Diels-Alder addition with acrylic acid, fumaric acid, or maleic anhydride.

50 citations

Patent
10 Jul 1975
TL;DR: In this article, the reaction of an epoxide of a long chain (1) unsaturated fatty oil or ester thereof with a mixture of (a) acrylic acid or methacrylic acid, (b) a diepoxide, and (c) at least one other modifying compound.
Abstract: Polymerizable reaction product mixtures are prepared by the reaction of an epoxide of a long chain (1) unsaturated fatty oil or (ii) unsaturated fatty acid or ester thereof with a mixture of (a) acrylic acid or methacrylic acid, (b) a diepoxide, and (c) at least one other modifying compound. The modifying compounds contain a group that will react with the epoxidized fatty oil or with the epoxidized fatty acid or ester. The mixtures produced are useful per se and in formulations as inks or coatings that are curable by exposure to radiation or by heating.

37 citations

Patent
19 Jul 1994
TL;DR: In this article, the authors defined a group of membrane lipids which are comprised by the groups (I) lipids having the formula C13H27-CH=CH-CH(OH)-CH(NHCOR2)-CH2-OR4, C13 H27- is an unbranched alkyl chain, R4 is hydrogen or R3, where R3 is a sugar moiety, including glucose, fructose, galactose, saccharose, lactose and maltose residues.
Abstract: Triglyceride oil crystallisation modifying substance being membrane lipids which are comprised by the groups (I) lipids having the formula C13H27-CH=CH-CH(OH)-CH(NHCOR2)-CH2-OR4, C13H27- is an unbranched alkyl chain, R4 is hydrogen or R3; (II) lipids having formula (a) including the corresponding lysophosphatides where one of the ester groups have been hydrolysed; (III) lipids having formula (b) where R1 and R2 are unbranched (C1-C24)-hydrocarbon chains, provided at least one of R1 and R2 is a (C8-C24)-hydrocarbon chain, P is a phosphoryl moiety, which comprises phosphoryl serine, phosphoryl ethanolamine, phosphoryl choline, disphosphoryl glycerol and phosphoryl inositol according to figures (5 - 9) respectively and where R3 is a sugar moiety which comprises a monosaccharide residue, a disaccharide residue or an oligosaccharide residue, including glucose, fructose, galactose, saccharose, lactose and maltose residues; (IV) a sphingomyelin according to figure (1); (V) a cerebroside according to figure (3), where [S] is a sugar moiety chosen from the group comprising a monosaccharide residue, a disaccharide residue or an oligosaccharide residue, including glucose, fructose, galactose, saccharose, lactose and maltose residues; (VI) mixtures of lipids taken from groups (I - V). When in a crystallising oil a membrane lipid is present, a higher separation efficiency of the stearin phase from the crystallised oil can be accomplished.

36 citations