Oxyethylated sulfonamides as nonionic soil wetting agents

Self Cite

Polydisperse adducts, RCONRr(CH~CH~O)x H, 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.

Section: Properties Of Oxyethylated Amidescontrasting

confidence: 52%

Section: Synthesismentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

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Oxyethylated secondary amides as soil wetting agents

Micich

Linfield

1985

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“…Materials. The phenylsulfonamide derivatives were prepared by a co-worker in our laboratory, and their synthesis and wetting properties were described in a previous publication (6). The derivatives were mixtures of polydisperse compounds where n = average ethoxylation (EO), and all were liquid at room temperature.…”

Section: Methodsmentioning

confidence: 99%

Surface‐tension properties of some polydispersed alkyl‐substituted polyoxyethylated phenylsulfonamides

Hampson

Cornell

1996

Twenty-nine laboratory-prepared polydisperse nonionic surfactants, derived from polyoxyethylated Nalkylphenylsulfonamides [R~SO2N(R') (EO)nH], have been characterized. EO is ethyoxylation; R is hydrogen, n-butyl or tbutyl; R" is hexyl, octyl, or decyl; and (EO) n is varied from (EO) 4 to (EO)20. Surface tension in aqueous solution was studied. The critical micelle concentration, surface excess, minimum area per molecule, effectiveness of surface-tension reduction, and free energy of micelle formation were calculated from the surface-tension measurements. The critical micelle concentrations for the derivatives in which R' = hexyl were considerably higher than the corresponding derivatives where R' is octyl or decyl. The greatest surface-tension reduction was found in the R" = n-octyl derivatives where R is t-butyl with (EO) 9 or n-butyl with (EO)11. JAOCS 73, 891-895 (1996).

“…These adducts were characterizcd by good wetting and low water solubility. Subsequent studies ofoxyethylated branched aromatic sulfonamides showed that polydisperse adducts are at least equally as good wetting agents as were homogeneous adducts (9). Aromatic sulfonamides add E.O.…”

mentioning

confidence: 99%

Soil wetting agents from fatty nonionic tertiary amides: “Aromatic adducts without aminoester”

Micich

1989

Tertiary amides RCONR'K, where K is a hydroxy function and R,R′ are aliphatic and/or aromatic groups, were oxyethylated to adducts containing 5, 10, 15, and 20 moles of ethylene oxide. The hydroxy function K was derived from CH2CHR″OH,‐(CH2)yOH, or (CH2CH2O)zH, where R″ is methyl, ethyl, or octyl, y is 4 or 6 methylenes, and z is 2 or 3 ethoxy groups. Structural variations in R,R′ and K permitted the oxyethylation of aromatic amides with minimal aminoester formation. When K was diethoxy and R,R′ were linear aliphatic groups, no aminoester accompanied oxyethylation. Minimal aminoester formed when R,R′ were mixed aliphatic/ aromatic or when R was phenethyl and R′ aromatic. For aromatic amides where K was dior triethoxy, large aminoester concentrations accompanied oxyethylation. For aromatic amides where K was (CH2)4OH or (CH2)6OH smaller aminoester concentrations were observed. For branched alphatic amides where R″ is methyl, ethyl, or octyl, aminoester concentration remained at the level found where R″ is hydrogen. The increasing size of R″ decreased solubility and Draves wetting times. The adducts of this study were wetting agents for Idylwild hydrophobic soil and cotton skeins. The availability of aromatic substrates should permit formulation of soil wetting agents with greater stability to biodegradation than would be expected with aliphatic substrates.