- Novel long chain unsaturated diisocyanate from fatty acid: Synthesis, characterization, and application in bio-based polyurethane
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A novel long chain linear unsaturated terminal diisocyanate, 1,16-diisocyanatohexadec-8-ene (HDEDI) was synthesized from oleic acid via Curtius rearrangement. Its chemical structure was identified by FTIR, 1H NMR, 13C NMR, and HRMS. This diisocyanate was used as a starting material for the preparation of entirely bio-based polyurethanes (PUs) by reacting it with canola diol and canola polyol, respectively. The physical properties and crystalline structure of the PUs prepared from this diisocyanate were compared to their counterparts prepared from similar fatty acid-derived diisocyanate, 1,7-heptamethylene diisocyanate (HPMDI). The HDEDI based PUs demonstrated various different properties compared to those of HPMDI based PUs. For example, HDEDI based PUs exhibited a triclinic crystal form; whereas HPMDI based PUs exhibited a hexagonal crystal lattice. In addition, canola polyol-HDEDI PU demonstrated a higher tensile strength at break than that of canola polyolHPMDI, attributed to the higher degree of hydrogen bonding associated with the former sample. Nevertheless, lower Young's modulus and higher elongation in canola polyol-HDEDI PU were obtained because of the flexibility of the long chain introduced by the HDEDI diisocyanate.
- Hojabri, Leila,Kong, Xiaohua,Narine, Suresh S.
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- METHOD FOR SYNTHESISING BIOBASED UNSATURATED ACIDS
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The invention relates to a method for preparing a compound of formula (I), wherein n is an integer from 1 to 21,said method comprises reacting a light olefin fraction, in the presence of a metathesis catalyst, with a compound having from 10 to 24 carbon atoms, of the following formula (II): wherein, n is an integer from 1 to 21,R corresponds to a hydrogen atom or an alkyl or alkenyl chain from 1 to20 carbon atoms optionally substituted by at least one hydroxyl group, said compound of formula (II) being used alone or in a mixture of compounds of formula (II).
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Paragraph 0093-0099
(2015/12/07)
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- ESTERAMINES AND DERIVATIVES FROM NATURAL OIL METATHESIS
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Esteramine compositions and their derivatives are disclosed. The esteramines comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a tertiary alkanolamine. Derivatives made by quaternizing, sulfonating, alkoxylating, sulfating, and/or sulfitating the esteramines are also disclosed. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The esteramines and derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.
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Page/Page column 22; 32
(2012/05/20)
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- Functional thermoplastics from linear diols and diisocyanates produced entirely from renewable lipid sources
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An unsaturated terminal diol, 1,18-octadec-9-endiol (ODEDO), and a saturated terminal diol, 1,9-nonanediol (NDO), were synthesized from oleic acid. The feasibility of utilizing these new diols for the production of thermoplastic polyurethanes (TPUs) was demonstrated by reacting them with a fatty acid-derived diisocyanate, 1,7-heptamethylene diisocyanate (HPMDI), and a commercially available petroleum-derived diisocyanate, 1,6-hexamethylene diisocyanate (HDI). One type of phase structure was obtained for both TPUs in this study, owing to the similarity between the ODEDO and NDO molecular structure. In addition, double yielding behavior (observed for the first time in polyurethanes) was observed in the stress-strain curves for both TPU systems. Compared to the TPUs prepared from HDI, the totally biobased TPUs (ODEDO-NDO-HPDMI) demonstrated comparable properties within acceptable tolerances, considering the impacts on physical properties due to the odd-even effect introduced by the HPDMI. This work is the first that establishes the production of linear thermoplastic polyurethanes entirely from lipid feedstock.
- Hojabri, Leila,Kong, Xiaohua,Narine, Suresh S.
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experimental part
p. 911 - 918
(2011/01/03)
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- Synthesis and characterization of highly functionalized symmetric aromatic hexa-ol intermediates from oleic acid
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A novel highly functionalized aromatic hexa-ol was synthesized by palladium-catalyzed cyclotrimerization of an alkyne fatty acid ester followed by LAH reduction. This polyol product is a novel monomer made from a renewable lipid raw material for the production of polyurethanes, polyesters and polyamides.
- Song, Dong,Narine, Suresh S.
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experimental part
p. 43 - 47
(2009/12/31)
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- Restricting the flexibility of crosslinked, interfacial peptide inhibitors of HIV-1 protease
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Interfacial peptides of HIV-1 protease were crosslinked with varying length alkyl-chains containing either a single cis or trans double bond, or a triple bond to remove degrees of freedom within the tethers. The synthesis of these compounds and their effects on the activity of HIV-1 protease are described.
- Ulysse, Luckner G.,Chmielewski, Jean
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p. 3281 - 3286
(2007/10/03)
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- Aleuritic acid in the preparation of (Z)-9-octadecene-1,18-dioic acid (intermediate in civetone synthesis) and queen substance of honey-bee utilizing phosphonate carbanions
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Wittig-Horner-Emmons olefination on aldehydes derived from aleuritic acid leading to the formation of both pure Z and E isomers of 9-octadecene-1,18 dioic acid, in good yield (valuable intermediate for musk perfume civetone) and a synthesis of 9-oxo-(E)-2-decenoic acid (queen bee substance) are reported.
- Subramanian,Ahuja, Seema
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p. 1043 - 1046
(2007/10/03)
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- Tetracarboxylic acids
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A process for polymerizing unsaturated dicarboxylic acids comprises heating the acids in the presence of a catalytic proportion of an unactivated clay and water. The product dimer is distilled to separate unreacted monomer acids. The product dimers of 36, 40 and 44 content are useful as corrosion inhibitors, epoxy resin curing agents, lubricants and intermediates for synthetic polymeric resins and polymeric resin plasticizers.
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