Masafumi Moriya

New amphoteric surfactants containing a 2-hydroxyalkyl group: II. the dependence of physicochemical properties on the pH value for N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines

The dependence of physicochemical properties on the pH of micellar solutions for N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β alanines (HAA) was studied by means of a differential titration method (DTM), Fourier transform infrared (FTIR) spectra, and measurements of critical micelle concentration, surface tension, and foaming power. The aspect of the dissociation of HAA was pursued by DTM. The mutual transformation among cationic, zwitterionic, and anionic forms with the change of pH range was confirmed by FTIR spectroscopy. The micelle formation energy was determined at each pH value. Further, the dependence of surface active properties on the pH value for the adducts of ethylene oxide to Na-HAA was also investigated.

New amphoteric surfactants containing a 2-hydroxyalkyl group: I preparation and properties of N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines

A series of new amphoteric surfactants, sodium salts of N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines (Na-HAA) was prepared by adding methyl acrylate to N-(2-hydroxyalkyl)-ethanolamine and subsequent saponification. Neutralization with HCl gave N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines, and the addition of ethylene oxide to Na-HAA gave oxyethylated drivatives. The structures of these compounds prepared were confirmed by infrared spectra, proton magnetic resonance spectra, elementary analyses, etc. Solubility in water, surface tension, foaming power, and critical micelle concentration were determined.

New amphoteric surfactants containing a 2-hydroxyalkyl group: IV. Performance of amphoteric surfactant/soap blends

The performance of new amphoteric surfactants,N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines (HAA) and their oxyethylated derivatives (HAA-nEO) was studied in blends with a fatty acid soap. The solubility, foaming power and fabric detergency were measured for blends of (Na-HAA or Na-HAA-nEO)/soap. Furthermore, lime soap dispersing power, toxicity to fish and biodegradability for HAA or HAA-nEO homologs were examined and evaluated. The blend of tallow soap and not less than 10% of C12–14-Na-HAA exhibited better solubility behavior than tallow soap or tallow/coconut oil soap alone. Fabric detergency was improved by blending Na-HAA with soap. Soil deposition in Na-HAA/soap or Na-HAA/soap/Na2CO3 solution was measured. On the basis of the results for: (a) the measurements of redeposition; (b) interfacial tension between oil and water and (c) contact angle between oil and fabric in water, it was presumed that since Na-HAA adsorbed more or less in preference to soap on the surface of fabric in water, soil redeposition would be prevented in the Na-HAA/soap detergent solution.

New amphoteric surfactant containing a 2-hydroxyalkyl group: III. Performance of binary systems of amphoteric/anionic surfactants

The performance of new amphoteric surfactants, N-(2-hydroxyethyl)-N-(2-hydroxyalkyl)-β-alanines (HAA), and their oxyethylated derivatives (HAA-nEO) was studied in blends with conventional anionic surfactants. Viscosity, ultraviolet (UV) spectroscopy, surface tension, foaming power, dye solubilization and detergency were measured for the blends of various compositions. The interaction between HAA and sodium linear alkylbenzene sulfonate (LAS) was discussed with respect to the deviation of molar extinction coefficient in the UV spectra. A complex formation was assumed. A notable change in viscosity of 1.0% aqueous solutions was observed at pH 8.0 for the compositions of HAA/LAS (3:1) and HAA/sodium lauryl sulfate (4:1). The binary systems exhibited excellent detergency and other surface active properties, and indicated synergistic effects at a certain weight ratio. Human and rabbit skin irritation also was evaluated.

Surface-active properties and thermal behavior of S-alkylthio-carboxylic acids and their potassium salts

S-Alkylthiocarboxylic acids and their potassium salts were prepared by photoaddition of α-olefins (C10, C12, and C14) with mercapto carboxylic acids such as thiomalic acid, thiopropionic acid, and thioglycolic acid. The physicochemical solution properties and thermal stabilities for three series of thiosurfactants were evaluated. S-Alkylthiocarboxylic acids that contain bridged S-bonds provide excellent thermally stable surfactants, and their alkaline salts exhibit good surface activity.

New amphoteric surfactants containing a 2-hydroxyalkyl group VIII. Synthesis and surface activities for amphoteric oligomeric or polymeric surfactants of β-alanine type

A series of amphoteric oligomeric and polymeric surfactants of poly(iminoethylene) (PIE) containing both a 2-hydroxyalkyl group (C12-HA or C14-HA) and a 2-carboxyethyl (CE) group as N-substituents was studied as follows: PIE having 1,000 or 20,000 molecular weight was treated with 1,2-epoxydodecane or 1,2-epoxytetradecane and subsequently methyl acrylate. The adducts were saponified to obtain amphoteric oligomeric surfactants (AO) or amphoteric polymeric surfactants (AP), poly{[N-(2-carboxyethyl)-N′-(2-hydroxyalkyl)]iminoethylene}. Various adducts of which the ratios of CE/HA for one unit of iminoethylene group are 2, 3.5, 8, 17 and 89 were synthesized.Surface activities such as surface tension, solubilization of orange OT, and foaming power, and physicochemical properties such as turbidity, isoelectric point, and the dissociation constant, were studied. Particular attention was paid to the dependence of solubilization, viscosity and turbidity on pH value.

New amphoteric surfactants containing a 2-hydroxyalkyl group. IX: The pH dependence of micellar assemblies composed of amphoteric oligomeric and polymeric surfactants

Abstract A series of amphoteric oligomeric surfactants (AO) and amphoteric polymeric surfactants (AP) containing both a 2-carboxyethyl (CE) group and a 2-hydroxyalkyl (C12-HA or C14-HA) group has been studied. The bobbin-like molecular structure of the micelle formed by these surfactants poly{[N-(2-carboxyethyl)-N′-(2-hydroxyalkyl)]aminoethylene} and the local movements of the molecular chain therein have been examined for pH dependence of 1H NMR spectroscopy on the CE HA ratio. From an analysis of chemical shifts and half-linewidths, the presence of micellar aggregates in a particular configuration has been inferred. The peaks of both and −CH2COO groups shift to a higher field with increasing pH (alkaline side). The half-linewidth is broad on the acidic side and narrow on the alkaline side. The dissociation occurs and the bobbin structure becomes loose. The dissociation constant and bulk behavior are also discussed using the Henderson-Hasselbach equation.