T. J. Micich

Nonionic Surfactant Amides As Soil Wetting Agents

Isomeric hydroxyethyl tertiary amides, RCONR′CH2CH2OH, where R and R′ are 7- 8 carbon linear or branched aliphatic groups, were oxyethylated to form polydisperse adducts containing 5- 20 moles of ethylene oxide. The adducts RCONR′(E.O.)xH were free of unreacted amide and contained minimum ester contaminant where R and R′ were branched. Ester content of the adducts does not change with time, but the monomer does revert to amide on standing. All series of adducts showed good wetting at intermediate chain lengths but instantaneous wetting only at short chain lengths where both R and R′ were branched. Good water solubility occurred at the intermediate chain length while maximum surface activity was found for short chain lengths corresponding to a hydrophile- lipophile balance of ~9. All adduct series were excellent wetting agents for cotton skeins and a burned over sandy loam. For this soil the adducts effectively promote wetting at 0.01% level.

Oxyethylated sulfonamides as nonionic soil wetting agents

Various N-alkylbenzenesulfonamides of the type RφSO2NHR′, where R is t-butyl, or hydrogen and R′ is decyl, octyl, t-octyl, 2-ethylhexyl, hexyl, and butyl, were treated with ethylene oxide (EO) to yield polydisperse adducts RφSO2 N(R′)(EO)xH where x is any integer from 2 to 20. Each series of adducts exhibited a range of properties and water solubility. Wetting ability, surface tension, cloud point, and hydrophilic-lipophilic balance (HLB) were related to structure and EO content to determine the most efficient wetting agent for peat moss and cotton skeins. Optimum wetting properties were found for adducts containing 5–10 EO units and in particular with t-C4 H9φSO2N(t-C8H17)(EO)xH. This EO chain-length region corresponded to cloud points of 25°, minimal surface tensions, and HLB values 10–12.

Polyhydric alcohol esters of α-sulfo fatty acids

Direct esterification of α-sulfopalmitic and α-sulfostearic acids with excess ethylene glycol, glycerol, pentaerythritol and 2-methoxyethanol was carried out in carbon tetrachloride to give products containing essentially monoesters. Surface active properties of these compounds were measured with emphasis on washing ability in combination with soap. The detergency of these esters was compared with those of hexitol and sucrose α-sulfo fatty acid esters. Although the esters had moderate lime soap dispersing ability, their detergency showed synergism when combined with soap.

Oxyethylated secondary amides as soil wetting agents

Polydisperse adducts, RCONR’ (CH2CH2O)xH, with attractive wetting properties were prepared by oxyethylating aliphatic and aromatic secondary amides to calculated x values of 5 to 20. Moderate wetting profiles were observed with adducts where R and R’ contained 15 to 18 carbon atoms and had short ethylene oxide chains. These products, however, contained unreacted amide and/or ester contaminants. Consequently, the products showed high water solubility, fairly flat surface tension curves and average wetting ability. In the transition of adducts derived from aliphatic amides to those from aromatic amides, unreacted amide concentration decreased and ester contaminant increased.

Soap-based detergent formulations: VIII. N-Alkylsulfosuccinamates as lime soap dispersants

A series of sodium methyl N-alkylsulfosuccinamates was prepared by the reaction of methyl N-alkylmaleamates with sodium bisulfite in aqueous ethanol. The surface-active properties and detergency of these derivatives were compared with those of a series of disodium N-alkylsulfosuccinamates prepared by the reaction of sodium sulfite with N-alkylmaleamic acid in water. The ester derivatives generally showed good lime soap dispersing requirement and washing ability in combination with soap, where-as the disodium salts were somewhat deficient in these properties and exhibited good washing ability only at 0.2% concentration with the surfactant as the sole component.

Cobaltothiocyanate colorimetric analysis for homologous polyoxyethylated alkyl amides

Cobaltothiocyanate colorimetry has been used for quantitative analysis of polyethoxylates in biodegradation and environmental studies. Usually, the calibration parameters (slope and intercept of a calibration line) for the cobaltothiocyanate colorimetry are dependent on ethylene oxide chain length. To make the colorimetric method useful for polyoxyethylated surfactant mixtures, where the average chain length is polydispersed, a condition was found yielding parameters independent of chain length in a homologous series of polyethoxylates within a limited chain length range. The dependency can be correlated to the thermodynamics of the ethylene oxide-cobaltothiocyanate complexation and the solvent extraction.

Soap-based detergent formulations: XXII. Sulfobetaine derivatives ofN-alkylglutaramides and adipamides

Abstract and SummaryThe acid chlorides of methyl hydrogen glutarate and methyl hydrogen adipate were allowed to react with various primary fatty amines. The resulting amido esters were converted into the corresponding amino diamides by sodium catalyzed reaction with N,N-dimethylaminoalkylamines. The desired sulfobetaines were obtained by reaction of the resulting N-alkyl-N′-(1,1-dimethylaminoalkyl) glutaramides and adipamides with 1,3-propanesultone. The compouds possess the same excellent lime soap dispersing ability, water solubility, calcium ion stability, and detergency properties as the analogous succinamide derivatives previous reported. This indicates that the spacing between the two amido groups or that between the quaternary nitrogen atom and the nearest amido group does not affect surface active properties.

Inhibition ofClostridium botulinum by aliphatic amines and long chain aliphatic aminodiamides

N-substituted aminodiamides of the general structure, RNHCO (CH2)x -CONH(CH2)yN(CH3)2, and the corresponding N-sulfopropyl derivatives were studied for their inhibiting effect on growth ofClostridium botulinum in culture media. With R = C16H33, more activity was observed with x = 2, 3, or 4 and y = 2, 3, or 4 than with R = C12H25 or C10H21 . There was little or no correlation of activity with the length of the x or y chains, but the addition of the sulfopropyl group resulted in decreased inhibitory activity. The C3 to C18 saturated aliphatic amines used for synthesizing the aminodiamides were effective inhibitors ofC. botulinum; tetradecyl-, pentadecyl-, and hexadecylamines were the most active with minimum inhibitory concentrations (MIC) of 0.8 μ/ml-The ratio of molecular weights of the diamides to the corresponding aliphatic amines indicated that most if not all of the inhibitory activity of the aminodiamides could be attributed to the amine moiety.

Soap-based detergent formulations: IV. The synthesis and surface active properties of sulfopropyl esters of N-substituted iminodiacetic acids

A series of di(potassium 3-sulfopropyl) N-alkyl and N-acyliminodiacetates were prepared by reacting 1,3-propanesultone with the corresponding dipotassium N-alkyl and N-acyliminodiacetates, respectively. The washing ability of these products was examined alone and in combination with soap. Whereas the surfactant properties of the precursor iminodiacetates were poor, the addition of two sulfopropyl groups resulted in products with excellent lime soap dispersing power, calcium ion stability and water solubility.

Synthesis and bacteriostatic properties of acylarylureas and alkylarylureas

Fatty substituted ureas (RNHCONHR’) were prepared where R is an aliphatic acyl or alkyl group and R’ is a substituted phenyl group or a thiazole group. The benzene ring was generally substituted with chlorine, nitro, hydroxy, or a combination of these groups. The compounds were ineffective against gram-negative microorganisms but a number of samples inhibited the growth ofStaphylococcus aureus at 1 ppm. Bacteriostatic activity was generally observed where the acyl or alkyl group contained 6–10 carbon atoms and where R’ is 4-nitrophenyl, 4-chloro-3-nitrophenyl or a thiazole group derived from 2-amino-5-nitrothiazole. Scattered activity at 1 ppm was observed where R’ is 3-nitrophenyl, 2,4- and 3,5-dichlorophenyl, 2-hydroxy-5-chlorophenyl, 2-hydroxy-5-nitrophenyl, 3-nitro-4-hydroxyphenyl, 3,5-dinitrophenyl and 2-nitro-4-chlorophenyl. The alkylureas appear to be more active than the acylureas.