Robert R. Mod

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.

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.

Binary freezing-point diagrams for alpha- and beta-eleostearic acids with each other and with acetamide

SummaryComplete binary freezing-point data have been obtained for each of the polymorphic modifications of acetamide with alpha-eleostearic acid and beta-eleostearic acid and for alpha-eleostearic acid with beta-eleostearic acid. In the light of previously published data the fact that all of these systems are of the simple eutectic type suggests that the tendency of the long-chain fatty acids to form 1∶1 molecular compounds with acetamide and with each other decreases as the degree of unsaturation increases.The fact that the heat of fusion of beta-eleostearic acid, 13.2 kcal. per mole, calculated from the freezing-point data is greater than that for the alpha acid, 10.5 kcal. per mole, corroborates the conclusion that the beta acid is the trans-trans-trans modification. Calculations of heats of fusion have been made, based upon all the available freezing-point data in the literature for binary systems between pairs of C18 fatty acids of different degrees of unsaturation, and certain trends have been dsicussed.

Lubricants and lubricant additives: I. Performance characteristics of N-mono and N,N-Disubstituted fatty amides and modified fatty amides

A number of N-mono and N,N-disubstituted amides of substituted and unsubstituted C18 fatty acids have been prepared and evaluated as base lubricants and lubricant additives. The neat epithioamides possess extreme pressure lubricant characteristics and are noncorrosive at normal temperatures. The epithioamides also frequently function as extreme pressure additives and antiwear agents for paraffinic or diester base oils, sometimes in both capacities for both base oils. The intensiveness of these properties correlated directly with the degree of thiirane substitution in the compound. Performance in both these capacities at the same levels of epithioation was dependent upon the N- or N,N-substituent groups present.

Antimicrobial activity of some fatty acid derivatives

Petroselinic and ricinoleic acids and a number of their derivatives, together with stearic acid and two oleic acid derivatives which were in-cluded for the purpose of comparison, have been screened for antimycotic activity against 22 pathogenic yeasts and molds. A number of the compounds exhibited a wide spectrum of activity, testing either fair or good against all or most of the yeasts and molds, and almost all were fairly active against at least one of the organisms.

N,N-dialkylamides of long chain fatty acids as plasticizers

A number of N,N-dialkylamides have been prepared, characterized and evaluated as plasticizers for poly (vinyl chloride-vinyl acetate) copolymer. Among these are the N-oleoyl derivatives of diisopropyl, dibutyl, diisobutyl, diamyl, dihexyl, diheptyl, dioctyl, di-2-ethylhexyl and didecylamines. Also included are the N,N-dibutylamides of 2-ethylhexanoic, neodecanoic, neotridecanoic, palmitic, stearic, linoleic, erucic, ricinoleic, naphthenic, dimer, pinic, epoxystearic, animal, cottonseed, hydrogenated cottonseed, rapeseed,Limnanthes douglasii seed and parsley seed acids. Optimum low-temperature plasticizing properties are achieved for the N-oleoyl derivatives of dibutyl, diamyl and dihexyl amines. These low-temperature properties are comparable to those of the adipate and sebacate plasticizers without the adverse volatility characteristics of the adipates. Compatibility of the N,N-dialkyloleamides extends through the dihexyl derivative. A brief heat stability study of some selected plasticized polylvinyl chloride copolymer compositions indicates that the thermal stabilization of amide plasticizers is not an insurmountable problem.

Fatty acid morpholides as plasticizers for vinyl chloride resins. II. The morpholides of selectively hydrogenated and of epoxidized cottonseed fatty acids

The morpholides of selectively hydrogenated cottonseed acids and of epoxidized cottonseed acids have been prepared and shown to be good primary plasticizers for vinyl chloride homopolymer and copolymer resins. They are also acceptable plasticizers for cellulose triacetate and possibly also as Buna A softeners. The degree of hydrogenation or partial epoxidation was approximately that equivalent to the conversion of all the polyunsaturated acyls to monounsaturated acyls.

1,3-Diacyl derivatives of imidazolidine and hexahydropyrimidine: I. Preparation by novel method and characterization

The reaction of formaldehyde and diamides of 1,2-diamines in acetic acid containing a trace of hydrochloric acid was found to give 1,3-diacyl derivatives of imidazolidine in high yield. The similar reaction of formaldehyde and diamides of 1,3-propylenediamine gave high yields of 1,3-diacylhexahydropyrimidines. Attempts to extend this reaction to other aldehydes than formaldehyde failed, as did attempts to condense formaldehyde with a diamide which would give a four-membered or seven-membered ring system, the diamide being recovered unchanged in each instance. Twenty-two new compounds were prepared and characterized.

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.

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.