- Synthesis and characterization of allyl fatty acid derivatives as reactive coalescing agents for latexes
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This work evaluated the use of allyl fatty acid esters derived from vegetable oil (palmitic acid, soybean and sunflower oils) as reactive coalescing agents in a waterborne latex system. Allyl fatty acid derivatives (AFAD) from vegetable oils were synthesized by two different processes. The synthesis was monitored by IR-spectroscopy and the final product characterized by FT-IR, GC-MS, 1H and 13C NMR. The presence of conjugated double bonds in the aliphatic chain was confirmed, which is a determinant for the proposed autoxidative latexes drying mechanism. Each of the AFAD were subsequently added to a standard acrylic emulsion, in order to study its potential as reactive coalescing agent. The minimum film-forming temperature (MFT), glass transition temperature (Tg), drying time and rubbing resistance to solvents were evaluated. The results showed that, when added to water-borne acrylic resins, an AFAD acts as a non-volatile plasticizer capable of autoxidative crosslinking with itself. AOCS 2012.
- Barbosa, Joana V.,Oliveira, Fernanda,Moniz, Jorge,Magalhaes, Fernao D.,Bastos, Margarida M. S. M.
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p. 2215 - 2226
(2013/01/15)
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- Total synthesis of three natural products: Decyl 8-hydroxyheptadecanoate, undecyl hexadecanoate and 2,3-dihydroxypropyl hexadecanoate
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First syntheses of decyl 8-hydroxyheptadecanoate 1 and undecyl hexadecanoate 2 via utilization of microwave energy and a new improved synthesis of 2,3-dihydroxypropyl hexadecanoate 3 have been accomplished from readily available starting compounds.
- Singh, Ashima,Sharma,Singh, Jasvinder
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experimental part
p. 1648 - 1652
(2011/03/17)
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- Synthesis of allyl esters of fatty acids and their ovicidal effect on Cydia pomonella (L.)
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Eight allyl esters of fatty acids were synthesized in moderate to high yields with a novel two-step procedure using glycerol as a starting material. The two-step methodology avoids the use of allyl alcohol. The first step consisted of heating at 80 °C for 48 h a 2:1:5 mmol mixture of glycerol, a fatty acid, and chlorotrimethylsilane in a solvent-free medium. The crude compound was then dissolved in butanone and heated at 115 °C in the presence of Nal. A tandem Finkelstein rearrangement-elimination reaction occurs, producing the corresponding allyl ester. The activity of these esters against Cydia pomonella (L.) (Lepidoptera: Tortricidae) eggs was tested in the laboratory by topical application of one 0.1 μL drop. All of the compounds showed a concentration-mortality response and caused 100% mortality at the highest concentration tested (10 mg/mL). There was an inverse relationship between the alkyl chain length and the ovicidal activity of the allyl ester; the LC50 and the LC90 of the two compounds that have the longer alkyl chains were significantly higher than those of the rest of the compounds. The ovicidal and IGR activities of this kind of compound appear to be unprecedented.
- Escriba, Marc,Barbut, Montserrat,Eras, Jordi,Canela, Ramon,Avilla, Jesus,Balcells, Merge
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experimental part
p. 4849 - 4853
(2010/06/14)
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- A tandem Finkelstein-rearrangement-elimination reaction: a straightforward synthetic route to allyl esters
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Allyl esters can be obtained by a Finkelstein-rearrangement-elimination reaction of 2-chloro-1-(chloromethyl)ethyl esters induced by NaI. Sodium iodide can be used below equivalence using a reductive agent as sodium thiosulfate. High yields are obtained with most of the diverse esters studied. The method described avoids the use of allyl alcohol as a reagent. 2-Chloro-1-(chloromethyl)ethyl esters are prepared from glycerol, the main by-product of biodiesel industry. The effectiveness of iodine as reagent to hydrolyze allyl esters is also confirmed.
- Eras, Jordi,Escribà, Marc,Villorbina, Gemma,Oromí-Farrús, Mireia,Balcells, Mercè,Canela, Ramon
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experimental part
p. 4866 - 4870
(2009/10/02)
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- Esters, retroesters, and a retroamide of palmitic acid: Pool for the first selective inhibitors of N-palmitoylethanolamine-selective acid amidase
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Cyclohexyl hexadecanoate, hexadecyl propionate, and N-(3-hydroxypropionyl)pentadecanamide, respectively ester, retroester, and retroamide derivatives of N-palmitoylethanolamine, represent the first selective inhibitors of "N-palmitoylethanolamine hydrolase" described so far. These compounds are devoid of affinity for CB1 and CB 2 receptors and characterized by high percentages of inhibition of N-palmitoylethanolamine-selective acid amidase (84.0, 70.5, and 76.7% inhibition at 100 μM, respectively) with much lower inhibitory effect on either fatty acid amide hydrolase or the uptake of anandamide.
- Vandevoorde, Séverine,Tsuboi, Kazuhito,Ueda, Natsuo,Jonsson, Kent-Olov,Fowler, Christopher J.,Lambert, Didier M.
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p. 4373 - 4376
(2007/10/03)
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- Convenient synthesis of benzyl and allyl esters using benzyl and allyl 2,2,2-trichloro-acetimidate
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Benzyl and allyl 2,2,2-trichloroacetimidate are efficient reagents for the preparation of benzyl and allyl esters of carboxylic acids in the presence of a catalytic amount of boron trifluoride-diethyl ether complex.
- Kokotos, George,Chiou, Antonia
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p. 168 - 170
(2007/10/03)
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- A FACILE SYNTHESIS OF 1(3)-ACYLGLYCEROLS
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A facile route is described for the synthesis of 1(3)-acylglycerols for the first time through hydroxylation of allyl esters of fatty acids with the novel reagent cetyltrimethylammonium permanganate in a non-aqueous medium.
- Gangadhar, A.,Subbarao, R.,Lakshminarayana, G.
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p. 2505 - 2514
(2007/10/02)
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