Lubricants and lubricant additives: II. Performance characteristics of some substituted fatty acid esters

Sixty-one compounds, principally substituted fatty esters of mono- and polyhydric alcohols, but including some amides and two imidazolidines, were prepared and evaluated as lubricants and lubricant additives for paraffin and diester base oils. The effects of chloro, phosphato, phosphorodithio, thio, epithio, mercapto, and sulfuryl substituents, alone and in certain combinations, on the performances of the compounds as antiwear and extreme pressure lubricants were investigated. The epithio (thiirane) group was the most effective and consistent in enhancing extreme pressure and antiwear performances of the compounds as additives. Sulfurized and chloro-sulfone derivatives also were effective, but perhaps somewhat less predictably so, than the epithio derivatives. The phosphato and phosphorodithio derivatives were good, consistent, antiwear additives, but only the latter seemed potentially useful for improving extreme pressure lubrication. Structure-performance correlations favor use of the esters over the amides.     

Lubricants and lubricant additives: III. Performance characteristics of some thioacetate,phosphorodithioate, and hexachlorocyclopentadiene derivatives of stearic acid amides and esters

A number of N-mono, N,N-disubstitured amides, and esters of substituted fatty acids have been prepared and evaluated as base lubricants and lubricant additives for paraffin (S-105) or diester (DOS) base oils. The effect of acetylthio, phosphorodithio, thio, chloro, and bromotrichloromethyl substituents, as well as hexachlorocyclopentadiene adducts upon performance as antiwear and extreme-pressure lubricants was investigated. Sulfurized 1,4-bis(pentachlorostearoyloxy)-2-butene was most effective in extreme-pressure (EP) tests, both neat and as an additive for S-105 and DOS base oils. Several of the phosphorodithio derivatives have good antiwear properties when formulated in one or both of the base oils, and were also fair EP additives. Of the addition compounds evaluated in this study, the phosphorodithio derivatives offer the most promise for development as antiwear additives for both paraffin and diester base oils. The sulfurized products offer the most promise as EP additives.     

Sulfur derivatives of N,N-Disubstituted amides of long chain fatty acids and their antimicrobial activities

Mercaptoacetic acid was added to the internal double bond of N,N-disubstituted oleamides and the terminal double bond of 11-undecenoylmorpholine. Unreacted starting materials were removed by distillation and as urea complexes. The internal carboxyl group of N,N-disubstituted-9(10)-(carboxymethylthio)stearamides and the terminal carboxyl group of 11-(carboxymethylthio)undecanamide were esterified. Screening for broad range antimicrobial activity againstCandida albicans, Staphylococcus aureus, Escherichia coli, andAspergillus species indicated that all compounds tested were active. However, 9(10)-(carbomethoxymethylthio)stearoylmorpholine and 9(10)-carbethoxymethylthio)stearoyl-4-methylpiperidine were the most effective and strongly inhibited the growth of all organisms tested.     

Antimicrobial activity and physical characteristics of some N,N-Disubstituted decanamides

A number of N,N-disubstituted decanamides have been prepared, characterized and screened for their antimicrobial activity against a number of pathogenic organisms including bacteria both gram positive and negative, yeasts and molds. Several of these compounds exhibited a broad spectrum and high level of activity against all or most of the test organisms. The antimicrobial activity of these compounds has been shown to correlate with their dispersibility and surface tension in an aqueous systems. So. Utiliz. Res. Dev. Div., ARS, USDA.     

Preparation and plasticizing characteristics of a series of symmetrical and unsymmetrical N,N-Disubstituted oleamides

Thirty-five N,N-disubstituted oleamides, mostly dialkyl oleamides, have been prepared and evaluated as plasticizers for vinyl chloride-vinyl acetate copolymer to investigate the relative effect upon plasticizer performance of N,N-symmetrical and unsymmetrical substitution; groups such as alkyl, cycloalkyl, benzyl, 2-alkoxyethyl, 2-acetoxyethyl, 2-(3-carbobutoxypropionlyoxy)ethyl, 2-(3-carbohexanoxypropionyloxy)ethyl, and cyanoethyl have been investigated in systematic combinations. The compatibility of symmetrical or unsymmetrical N,N-dialkyl oleamides, involving normal, branched, or cyclic alkyls, is controlled by the total carbon count of the combined substituent groups rather than that of the larger group. For retention of compatibility the total carbon count must not exceed about 13 atoms. Symmetrical and unsymmetrical dialkyl oleamides of the same total alkyl carbon count do not differ significantly in their plasticizing characteristics. Acyclic N,N-dialkyl oleamides are, with few exceptions, highly efficient plasticizers, which impart good, sebacate-like, low-temperature impact performance to the plastic composition. A substituent attached to the nitrogen through a secondary carbon severely impairs plasticizer efficiency and cyclic or cycloalkyl substituents are detrimental to low-temperature performance. Substitution of an alkyl group for one of the N,N-disymmetrical substituents has little or no effect upon low-temperature impact performance. Many of the disubstituted oleamides impart antistatic properties to the plastic composition.     

N，N-二取代苯磺酰亚胺类化合物的合成研究进展

N,N-二取代苯磺酰亚胺类化合物是一类具有脒结构的化合物。该类化合物不仅是重要的有机合成中间体,而且具有消炎、抗茵、抗肿瘤等多种生物活性,在医用和合成方面都具有广泛的应用。本文以不同的底物出发概述了一些N,N-二取代苯磺酰亚胺类化合物的合成方法。     

N,N-Bis(2-Acyloxyethyl) amides of long chain fatty acids as plasticizers

A series of N,N-bis-(2-acyloxyethyl) amides and a few related derivatives have been prepared wherein a long chain fatty acid or fatty acid mixture comprises 33 mole percent of the total acyl groups present: the other 66 mole percent being either a short chain aliphatic or aromatic acyl group. Both ordered and random diesteramides have been prepared. All have been tested as plasticizers for vinyl chloride copolymers. Some are acceptable as nitrile rubber softeners and cellulose acetate plasticizers. The ordered diesteramides give the best overall performance as plasticizers, but it is possible to achieve acceptable performance levels in semi-ordered diesteramides. Presented at the AOCS meeting in New Orleans, La., 1962. A laboratory of the So. Utiliz. Res. & Dev. Div., ARS, U.S.D.A.     

减摩抗磨类新型润滑油添加剂的研究进展

减摩抗磨类润滑油添加剂能提高基础润滑油的摩擦学性能使其在润滑领域具有广阔的应用前景,但是商用润滑油添加剂大多含有P、S等有害元素,因此,寻找更加环保、经济的润滑油添加剂具有重要意义。本文根据润滑油添加剂结构种类和润滑机理的不同,以及国内外各种润滑油添加剂在润滑方面的相关成果,综述了近年来纳米颗粒(纳米单质及其复合颗粒、纳米氧化物、纳米硫化物、纳米氮化物)、含氮杂环化合物及其衍生物、硼酸酯及其衍生物、离子液体等添加剂的合成方法以及在减摩抗磨方面的应用,并对其发展状况和减摩抗磨机理进行了探究。指出了其润滑机理主要为吸附膜机理、摩擦反应膜机理和滚珠机理。最后对其存在的问题进行分析,提出了当前润滑领域研究的热点和方向依然是复合添加剂的制备和机理探究。     

Cuticular lipids of the booklouse,Liposcelis bostrychophila: hydrocarbons,aldehydes, fatty acids,and fatty acid amides

The booklouse, Liposcelis bostrychophila, is an increasingly common pest of stored food products worldwide. We report here the cuticular lipid composition of this pest (the first report of the hydrocarbons of any member of the Order Psocoptera and the first report of fatty acid amides as cuticular components for any insect). No unsaturated hydrocarbons were present. A homologous series of n-alkanes (C₂₁–C₃₄), monomethyl alkanes (3-, 4-, 5-, 7-, 9-, 11-, 12-, 13- and 15-methyl-) with a carbon chain range of C₂₈–C₄₂, and dimethyl alkanes (3, 7-; 9, 13-; 11, 15-; 13, 17-; 9, 21-; 11, 19-; and 13, 21-); with a carbon number range of C₃₁–C₄₃ were identified. The relative abundances of these hydrocarbons were low, comprising approximately 0.0125% of total biomass. The amides were a homologous series (C₁₆–C₂₂ in chain length), with the major amide being stearoyl amide. In addition to the amides, free fatty acids (C_16:1, C_16:0, C_18:2, C_18:1, and C_18:0 in chain length) and three straight chain aldehydes (C₁₅, C₁₆, and C_17:1 in chain length) also occurred as cuticular components. These findings are discussed in terms of the chemical and physiological ecology of this species.     

Vinyl ester resin modified with silicone‐based additives. I. Mechanical properties

Silicone‐based additives have been used as fire retardants for thermoplastics and present the advantages of improving the processing and impact resistance of the polymers. In this study, we used three different silicone‐based additives as modifiers of a vinyl ester resin. The additives were fine powders made up of about 50 wt % polydimethylsiloxane and 50 wt % silica. The differences among them were the functional groups inserted in the polymer chains and the size and size distribution of the particles. The additives were dispersed in resin containing 35 wt % styrene. To cure the mixture, a conventional catalyst and initiator were used, and the reaction was carried out in three ways, which differed in the curing temperature, postcuring temperature, time, and addition of dimethylaniline (DMA) as a promoter of the polyaddition reaction. Dynamic mechanical analysis showed that the phase behavior of the resulting composites depended strongly on the curing conditions. The flexural modulus of composites containing 5 wt % additive was lower than that for the cured resin. The impact resistance of the composites also depended on the curing conditions but not on the composition or size of the particle of the additive. The fracture morphologies of specimens subjected to impact resistance tests were different for samples cured in the presence or in the absence of DMA, which suggested that it influenced the mechanism of network formation. © 2005 Wiley Periodicals, Inc. J Appl Polym Sci, 2006     

Soap based detergent formulation: XXIV. Sulfobetaine derivatives of fatty amides

Sulfobetaines were prepared from the reaction of fatty acids, fatty acid methyl esters or fatty glycerides with N,N-dimethyl-1,3-propanediamine to form an aminoamide which could be allowed to react further with either sodium 3-chloro-2-hydroxy-1-propanesulfonate (from epichlorohydrin and sodium bisulfite) or with allyl chloride followed by addition of sodium bisulfite to form sulfobetaines. The conditions for the reaction between aminoamide and sodium 3-chloro-2-hydroxyl-1-propanesulfonate were studied in an effort to minimize the extent of hydrolysis of the 3-chloro-compound and thus increase the yield of desired compound. Investigation of the quaternization of the aminoamide with allyl chloride showed that this reaction proceeded readily at pressures above atmospheric. The addition of sodium bisulfite to the resulting allyl quaternary ammonium compound took place readily in the presence of certain free radical initiators. Solution properties and detergency performance of the compounds are reported. Detergency of ternary formulations of soap, glassy silicate builder, and the above sulfobetaines was the same as that obtained with ternary formulations containing the analogous sulfobetaines obtained from the reaction of propanesultone with the aminoamide. We have developed a synthetic scheme for fatty amino sulfobetaines that requires no purification, avoids the use of carcinogenic 1,3-propanesultone and expensive fatty tertiary amines, and produces detergents that perform as well as the previously described purified sulfobetaines [Parris et al., JAOCS 50:509 (1973); Paris et al., Ibid. 53:60 (1976)]. Presented at the AOCS Meeting, Chicago, September 1976.     

Partially imidized,water-soluble polymeric amides. I. Partially imidized polyacrylamide and polymethacrylamide

Five to six million molecular weight polyacrylamide and polymethacrylamides of comparable post-alkaline hydrolysis viscosities were imidized by dissolution and heating in 6N HCl. After alkaline hydrolysis, the imidized polymers demonstrated significantly better retention of viscosity to 2% NaCl than did similar partially hydrolyzed polymers. Viscosities in 0.01% NaCl and resistance to shear were not markedly affected by this modification. It is assumed that this improved performance in brine is the result of chain stiffening due to intrachain imide rings.     

Separation of cholesterol,and fatty acylglycerols,acids and amides by thin-layer chromatography

A rapid unidimensional thin-layer chromatographic (TLC) method for the separation of neutral lipids is described, using two sequential solvent systems of different polarity. Excellent separations of mono-, di- and triglycerides, fatty acids, fatty amides, and cholesterol are thereby achieved. Separation is accomplished at room temperature and requires 25 min. Reference to brand of firm name does not constitute endorsement by the United States Department of Agriculture over others of a similar nature not mentioned.     

Soap-based detergent formulations: XXI. Amphoteric derivatives of fatty amides of aminoethylethanolamine1

Amides and 2-alkyl-N-(2-hydroxyethyl)-imidazolines were converted into various types of sulfated or sulfonated amphoteric lime soap dispersants. The alkylimidazolines could be readily hydrolyzed to give amidoamines. The cyclized amphoteric surfactants were generally superior in detergency and lime soap dispersing ability to analogous surfactants derived from amidoamines. Some of the cyclized surfactants, when formulated with soap and silicate builder, washed about as well under the test conditions as a control containing 50% sodium tripolyphosphate.     

Performance and exhaust emission characteristics of a CI engine fueled with diesel-nitrogenated additives

In present work the effects of nitromethane (NM) and nitroethane (NE) as nitrogenated additives on physical properties, combustion performance, and emission of diesel fuel, were studied. Nitrogenated additives have high oxygen content and are considered as oxygenated additives. These additives were blended with diesel fuel, in 1/9 volume ratio. The experimental study was carried out on ECE R-96 8-modes cycle. The result showed that the use of additives reduces viscosity but increases cetane index. In addition, nitrogenated additives increased brake thermal efficiency (BTE) while reduced certain exhaust emissions. Results of AVL SPC 472_MCE97 analysis showed that the addition of NE can reduce the overall smoke value by 44%. The smoke emission decreased at the maximum torque speed (1500 rpm) rather than at the rated power speed (2200 rpm).     

Soap-based detergent formulations: II. Oxyethylated fatty amides as lime soap dispersing agents

Nonionic surface active agents with two oxyalkyl chains were prepared from the triethylamine catalyzed reaction of ethylene oxide with diethanolamides of palmitic, stearic and tallow fatty acids. The addition of 4 moles of ethylene oxide was required to render these diethanolamides water soluble, whereas 9 moles were required to make the corresponding monoethanolamide soluble. Efficiency of lime soap dispersion increased as oxyethyl chain length was increased. Best detergency of soap-nonionic combinations was achieved when the oxyethyl chain length was at the minimum required for water solubility. Theγ-hydroxyethanolamides and -diethanolamides were prepared by the uncatalyzed reaction of the corresponding amines withγ-stearolactone. These compounds became water soluble at lower levels of oxyethylation, but the lime soap dispersing power and detergency were not improved over those of corresponding compounds derived from stearic acid. Presented at the AOCS Meeting, Los Angeles, April 1972. E. Market. Nutr. Res. Div., ARS, USDA.     

Free radical addition of dialkyl phosphites to N,N-disubstituted amides of unsaturated fatty acids and screening of the products for antimicrobial activity

Free radical addition of dibutyl phosphites to terminal and internal double bonds of monounsaturated amides was attained in high yield. The reaction was initiated by irradiation using Cobalt-60. Attempts to add diphenyl phosphite to the unsaturated amides failed with the amides being recovered unchanged. Similar attempts to add dialkyl phosphites to N-linoleoylmorpholine resulted in products that were deficient in phosphorus. Screening for antimicrobial activity againstEscherichia coli, Trichosporon capitatum, Trichoderma viride andCandida lipolytica indicated that terminal addition products may be more active than the internal addition products, with the former strongly inhibiting the growth of all four test organisms. Presented at the AOCS Meeting, Los Angeles, April 1972. ARS, USDA.     

Lubricants. I. Preparation and properties of benzyl and substituted benzyl esters of dilinoleic acid

Benzyl and substituted benzyl esters of dilinoleic acid and of hydrogenated dilinoleic acid have been prepared in good yield. Some of the chemical characteristics and physical properties of the resulting products have been measured including a study of their thermal stability by thermogravimetry. Also, they have been examined by several of the bench tests used in laboratory evaluation of lubricants. Several of them compare favorably with control materials used in the study. E. Utiliz. Res. Devel. Div., ARS, USDA.