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

Abstract

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.

Synthesis and thermal behavior of poly(ethylene oxide) poly(N‐substituted urethane)

“…Phenols, alcohols, carboxylic acids, and amines are among the active compounds mostly used. Primary amides are also frequently ethoxylated in industrial processes, whereas only a few reports on ethoxylation or alkylation of urethane are found in the literature 17–19…”