Fatty Acids, Esters and Amides

These are the classic lubricants, derived from natural oils and fats and acting by migrating to the surface. A wide range of fatty acid esters of polyols and other compounds is used as internal lubricants, especially in PVC. Good flow, surface finish and improved clarity can be achieved in most processes, using either compounded or dry blend formulations. According to type, they can improve mould release, melt flow, lubricity, and scratch/scuff resistance and reduce static build-up and wear. 

Compounds of adipates, palmitates. sebacates. and stearates are used as lubricants and plasticizers for many types of plastics, including PVC and engineering plastics. Cetyl palmitate can be used in place of natural wax and can act as a lubricant for engineering plastics. Octyl and iso-octyl palmitate are clear oily liquids with anti-blocking properties and additional heat stability that are also used as plasticizers for PVC and as a viscosity modifier for plastisols. The stearates are used, broadly, as viscosity stabilizers in PVC and lubricant/flow promoters in PS and ABS, particularly where low-temperature properties are required. Cetyl stearate is used as a lubricant for engineering plastics. 

Description high molecular weight acrylic copolymers, as white free-flowing powders, to improve processability of PVC compounds lubricant grades reduce adherence of melt to processing equipment  

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Saturated hydrocarbons (waxes), fatty acids, metal soaps, fatty acid amides and esters (primarily Cig-Cis) act as internal lubricants, fluoro elastomers as external lubricants. Many other polymer additives, e.g. antistatic agents, antifogs, antioxidants, UV stabilisers, etc., act as lubricants in the barrel of the extruder once they are in the liquid form. 

Sulfated Acids, Amides, and Esters. Reaction with sulfuric acid may be carried out on fatty acids, alkanolamides, and short-chain esters of fatty acids. The disodium salt of sulfated oleic acid is a textile additive and an effective lime soap dispersant. A typical sulfated alkanolamide stmcture is CiiH23C0NHCH2CH20S03Na. Others include the sulfates of mono and diethanolamides of fatty acids in the detergent range. The presence of... 

A variety of waxy hydrophobic hydrocarbon-based soHd phases are used including fatty acid amides and sulfonamides, hydrocarbon waxes such as montan wax [8002-53-7], and soHd fatty acids and esters. The amides are particularly important commercially. One example is the use of ethylenediamine distearamide [110-30-5] as a component of latex paint and paper pulp blackHquor defoamer (11). Hydrocarbon-based polymers are also used as the soHd components of antifoaming compositions (5) examples include polyethylene [9002-88-4], poly(vinyl chloride) [9002-86-2], and polymeric ion-exchange resins. 

There are over 150 different producers and some 2 million tonnes of commercial nonionic surfactants manufactured worldwide of which at least 50% are alkoxylated alcohols. Ethoxylated nonylphenol production is falling and accounts for 20% of the market while alkoxylated fatty acids account for some 15%. Fatty acid amides and sugar esters account for another 10% and there are a large number of specialities making up the balance. In general, non-ionic surfactants are easy to make, relatively inexpensive and derived from a variety of feedstocks. 

Extracellular anandamide, after it serves its function, is rapidly taken up by neuronal and non-neuronal cells by a high-affinity carrier-mediated transport mechanism. This mechanism meets key criteria of carrier-mediated transport, such as fast rate (t, of approximately 4 min), temperature dependence, satura-bility, and substrate selectivity (Beltramo et ah, 1997 Hillard et al., 1997). Furthermore, the transportation of anandamide is independent of sodium ions and is not affected by metabolic inhibitors. The second endogenous camiabinoid, 2-AG, competes for uptake with anandamide. It has been variously reported to exhibit a 2-fold higher affinity for the anandamide transporter than anandamide (Jarrahian et al, 2000), or equal affinity (Piomelli et al, 1999). The molecular structure of this hypothetical anandamide transporter remains unknown. However, it is selective for fatty acid amides or esters, and it is not a fatty acid transporter (Piomelli et al, 1999 Jarrahian et al, 2000). Very recent results indicate that anandamide uptake is a process driven by metabolism and other downstream events, rather than by a specific membrane-associated anandamide carrier (Glaser et al, 2003). 

Classification Monosubstituted fatty acid amide Definition Ester of erucyi aicohoi and stearic acid Properties Gardner 6 iow soi. in water m.p. 76-80 C iodine no. 46 Uses Lubricant, siip agent, antibiocking agent, and moid reiease agent for piastics, crayons, petroi. prods., asphaits, inks, metais, textiies moid release agent for thermoplastic resins in inj. molding defoamer and water repellent in industrial/ household applic. 

A. for fibers ( textile auxiliaries) are sulfonates and phosphates, - fatty amines, - fatty acid amides and their ethoxylates, - quaternary ammonium compounds as well as - fatty alcohol ethoxylates, fatty acid esters and their derivatives. For more durable finishes, polyamine resins cross-linked on the fiber are used. 

Epoxidized oils (- epoxides) are used as plasticizers, stabilizers and antioxidants for some coatings. Other plasticizers are - fatty acid esters, stand oils (- drying oils) and - castor oil. - Fatty acid amides and - metallic soaps (Zn and Ca) are used as matting or flattening agent and as hydro-phobic additive. Fatty acid derivatives, such as - glyceryl monostearate, chlorides and ammonium salts, improve the electric conductivity while - fatty amine ethoxylates, fatty acid amides and ammonium sulfates function as antistatic additives. Lit UUmann (5.) A18,465... 

Additives acting on the pour point also modify the crystal size and, in addition, decrease the cohesive forces between crystals, allowing flow at lower temperatures. These additives are also copolymers containing vinyl esters, alkyl acrylates, or alkyl fumarates. In addition, formulations containing surfactants, such as the amides or fatty acid salts and long-chain dialkyl-amines, have an effect both on the cold filter plugging point and the pour point. 

Fatty acid chlorides are very reactive and can be used instead of conventional methods to faciUtate production of amides and esters. lmida2oles are effective recyclable catalysts for the reaction with phosgene (qv) (24). 

Based on ether carboxylic acids it is possible in principle to make the same derivatives as with fatty acids, such as esters, amides, and acid chlorides. The hydrophilic chain in the molecule may confer special properties in comparison with the fatty acid derivatives. 

A number of amide- and ester-linked fatty acids and (/ )-3-hydroxy acids are components of the lipid A part in the LPS from Gram-negative bacteria. The acids have been tabulatedand the chemistry of lipid A summarized. The most common acids in lipid A from Enterobacteriaceae are the saturated 12 0,14 0, and 16 0, and the (/ )-3-hydroxy-14 0, The last is linked to N-2 and 0-3 of the 2-amino-2-deoxy-D-glucopyranosyl residues, and the others are ester-linked to the hydroxy acid, as in the lipid A (44) of Salmonella minnesota. Other linear and branched fatty acids, unsaturated acids, S)-2- and (/ )-3-hydroxy acids, and 3-oxotetradecanoic acid are components of lipid A from certain different species. In the lipid A from Rhizobium trifolii, 2,7-dihydroxyoctanoic acid is linked as amide to a 2-amino-2-deoxy-D-gl ucopy ranosy 1 residue. ... 

A wide range of anionic surfactants (Fig. 23) has been classified into groups, including alkyl benzene sulfonates (ABS), linear alkyl benzene sulfonates (LAS), alcohol sulfates (AS), alcohol ether sulfates (AES), alkyl phenol ether sulfates (APES), fatty acid amide ether sulfates (FAES), alpha-olefin sulfates (AOS), paraffin sulfonates, alpha sulfonated fatty acids and esters, sulfonated fatty acids and esters, mono- and di-ester sulfosuccinates, sulfosuccinamates, petroleum sulfonates, phosphate esters, and ligno-sulfonates. Of the anionic surfactants, ABS and LAS continue to be the major products of anionic surfactants [314, 324]. Anionic surfactants have been extensively monitored and characterized in various environmental matrices [34,35,45,325-329]. 

The compositions consist of a heat-plastified mixture of an ethylene homopolymer or copolymer, about 3 to 30 pbw of an elastomer, a stability control agent, which is a partial ester of a long chain fatty acid with a polyol, higher allyl amine, fatty acid amide or olefinically unsaturated carboxylic acid copolymer, and a hydrocarbon blowing agent having from 1 to 6 carbon atoms and a boiling point between -175 and 50C. 

Valproic acid is one of a series of fatty carboxylic acids that have antiseizure activity this activity appears to be greatest for carbon chain lengths of five to eight atoms. The amides and esters of valproic acid are also active antiseizure agents. 

The derivatization of fatty acids, and of acidic substances in general, has been a problem in analytical-organic chemistry for many years. The classically used derivatives have been amides and esters. The main problem in using methyl esters of fatty acid in HPLC is that one cannot then use the UV detector, because of inadequate absorption. Thus a search for an alternate method of forming UV-sensitive derivatives has been initiated in several laboratories. 

N-Benzylamides are recommended when the corresponding acid is liquid and/or water-soluble so that it cannot itself serve as a derivative. The benzyl-amides derived from the simple fatty acids or their esters are not altogether satisfactory since they are often low melting those derived from most hydroxy acids and from polybasic acids or their esters are formed in good yield and are easily purified. The esters of aromatic acids yield satisfactory derivatives but the method must compete with the equally simple process of hydrolysis and precipitation of the free acid, an obvious derivative when the acid is a solid. The procedure fails with esters of keto acids, sulphonic acids and inorganic acids and some halogenated aliphatic esters. 

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