Esterquats, which are quaternary ammonium compounds having two long (C₁₆-C₁₈) fatty acid chains with 2 weak ester linkages, represent a new generation of fabric softening agents, having replaced the dialkyldimethylammonium salts (e.g. DTDMAC and DSDMAC).The inclusion of ester linkages into the aliphatic chains has significantly improved the kinetics of biodegradation of the cationic surfactants, lowering the environmental exposure levels. This new generation of fabric softening agents combines a good environmental profile with the structural features required for an effective fabric conditioner. The present paper reviews the synthesis, types, actives combines a good environmental profile with the structural features required for a properties and applications of esterquats.

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Novel four 2,3-dihydro-1H-imidazo[1,2-a]pyridine-4-ylium derivatives were obtained with increase of UV absorption at 350 nm and browning of the solution by heating paste lecithin from soybean (SL) in octane. These four derivatives were formed by reaction of one molar of any sugar except 2-deoxysugars with two molar of phosphatidylethanolamines (PE) in SL. To confirm the reaction mechanism, several ¹³C-labeled-sugars were reacted with 1,2-di-O-stearoyl-sn-glycero-3-phosphatidylethanolamine (DSPE), respectively. These reactants clearly showed that five carbons of the pyridinium ring and one carbon of the substituted group were based on those of a sugar and that the formation of the pyridinium derivatives was accompanied with cleaving between the carbons of 1- and 2-positions in the sugar and rearrangement. This reaction is a new rearrangement reaction and we named it “new pseudo Maillard rearrangement reaction”.

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This study investigated the effects of a liquid meal containing medium- and long-chain triacylglycerols (MLCT) on diet-induced thermogenesis (DIT) and was conducted in double-blind cross-over manner. Twenty subjects participated in this examination. The subjects consumed the liquid meal, which was made with 14g of canola oil (LCT, long-chain triacylglycerols) or MLCT containing about 12% medium-chain fatty acids (MCFA). Oxygen consumption and carbon dioxide production were measured by indirect calorimetry. Resting energy expenditure (REE) was determined based on there parameters, applying the equation of Weir. Increase in DIT after ingesting the liquid meal with MLCT during 6h was significantly greater than with LCT (P<0.05). The results suggest that the substitution of MLCT for cooking oil is useful to control body weigh and fat in subjects.

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In recent years, hair coloring gains popularity as a trend of consumer’s hair care. This coloring frequently damages hair. In response to this, a new shampoo-base was developed for repairing hair damaged by coloring. The new shampoo-base was prepared by dispersing cationic assembly in a solution of amphoteric surfactants. The mixture of behenyl trimethyl ammonium chloride (C22TAC) and behenyl alcohol (C22OH) was applied as the cationic assembly, which are dispersed in amido propyl betaine laurate (LPB) solution. LPB, which behaves as an amphoteric surfactant, was used as the wash-base. It was verified from the results on the measurements of DSC, calorimeter polarization, cryo-SEM and X-ray diffraction that the cationic assembly has a crystalline structure in the LPB solution. The new shampoo-base was highly efficient to change the color-damaged hair from hydrophilic to hydrophobic. The friction level of the hair washed with the new shampoo-base recovered to the same state as that of healthy hair. The exfoliation of cuticle was reduced after washing with the new shampoo-base.

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Micelle formation induced by disproportionation was attained for a diblock copolymer containing 2,2,6,6-tetramethylpyperidine-1-oxyl (TEMPO). Poly(4-vinylbenzyloxy-TEMPO)-block-polystyrene (PVTEMPO-b-PSt) showed no self-assembly in 1,4-dioxane, a nonselective solvent. Light scattering studies demonstrated that the copolymer self-assembled into micelles in this solvent with the addition of hydrochloric acid (HCl). The hydrodynamic diameter of the copolymer was estimated to be ca. 55 nm based on the cumulant analysis of the complete micellization. A UV analysis confirmed that the micellizarion proceeded through the disproportionation of the TEMPO into the oxoaminium chloride and the hydroxylamine by the reaction with HCl, because the absorption based on the oxoaminium chloride increased with an increase in the amount of HCl. ESR verified that the radical concentration of the TEMPO decreased with an increase in the HCl. Before the addition of HCl, the PVTEMPO-b-PSt copolymer showed broad signals based on the random orientation. As the amount of HCl increased, the broad signals changed to the typical triplet of TEMPO, accompanied by a decrease in the signal intensity. The g values had a negligible change throughout the micellization. Finally, 40% of the TEMPO remained unreacted when the micellization was completed. The micellization prevented the dispropotionation of the TEMPO, because the PVTEMPO blocks formed the micellar cores which were covered with the micellar coronas of the PSt blocks. TEM observations demonstrated that PVTEMPO-b-PSt formed spherical micelles through the dispropotionation-induced micellization.

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The synthesis and herbicidal activity of ureas and amides with carvone residues were examined. (S)-(+)-(1) and (R)-(-)-Carvone(2) were converted to the respectively, primary amines(3) and (4) by oximation and reduction with LiAlH₄. Primary amine derivatives were further converted into the urea and amide compounds (3a)∼(3e) and (4a)∼(4e). The herbicidal activity of products (3a)∼(3e) and (4a)∼(4e) towards weeds found in a paddy field and field was measured in the pot. Products (3a) showed a particularly strong inhibitory effect on the growth of Amaranthus retroflexus(AR) and Setaria viridis(SV).

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Lipase-catalyzed acetylation of 2-alkanol with vinyl acetate has been studied kinetically using Burkholderia cepacia lipase (BCL), enantiomerically pure (R)- and (S)-2-alkanols and different organic solvents. The rate equation was derived by the steady state method for the simplified mechanism. The second order rate constants (k_R and k_S) for (R)- and (S)-2-alkanols were evaluated from the slopes of the double reciprocal plots, v^-1 vs. [2-alkanol]^-1, where v is the initial rate of the reaction. The log k_R value increased with the solvent hydrophobicity log P, where P is a partition coefficient of a given solvent between octanol and water. The log k_S value also increased with log P except the bulky solvents such as 1,4-dioxane and cyclohexane, in which the rates were faster than those expected from the log k_S vs. log P plot. The slope of log k_S vs. log P plot was larger than that for (R)-2-alkanol. Thus, log E (E=k_R/k_S: enantioselectivity) decreased with log P except the bulky solvents. The rate constants and the enantioselectivity were different depending on the structure (carbon number CN) of 2-alkanol. The log E vs. CN plot was minimized at CN=8 and 10 and the log k_S vs. CN plot maximized at CN=8 and 10. In contrast the log k_R vs. CN plot showed a different feature from the log E vs. CN plot. These facts suggest that dependence of E on CN is more strongly affected by the reactivity of (S)-2-alkanol than that of (R) isomer in this acetylation.

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