Three phase-transfer catalysis of insoluble poly (styrene) -bound poly (ethylene glycol monomethyl ether) (oxyethylene (EO) units; 3, 6, 8) (solid phase) was investigated in a halogen-exchange reaction between powdered metal iodides (solid phase) and 1-bromooctane (liquid phase) in benzene. The reaction rate showed a first-order dependency on the 1-bromooctane concentration and the rate was dependent on the number of EO units of poly (oxyethylene) linked to the polymer, the metal cation of the iodide employed, and the quantity of the resin catalyst. Sodium iodide reacted much faster with 1-bromooctane than any other metal iodides under anhydrous conditions, and the addition of water caused a sharp drop in the reaction rate. Use of potassium iodide made little difference in the rate between aqueous and nonaqueous reaction systems. The effect of the poly (oxyethylene) ring substitution on the rate was also examined. The cation complexing effect and amphipathic property of the catalysts were discussed.

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The effects of surfactants and substituents on the visible spectra and the values of pKa of twenty one substituted nitrophenols were studied in 3%, aqueous ethanol at 30°C by means of the spectrophotometric method. The used surfactants were CTAB, CPC, LBS, and B-35. The addition of the cationic surfactant over cmc caused marked effects on the spectra of the nitrophenolate ion (NPO^-), that is, the hyperchromic effect and the bathochromic shift were observed. Moreover, these spectral changes were more significant in o-nitro-isomers rather than p-nitro-isomers. LBS and B-35 had no effect on the spectra. These results were discussed mainly from both the changes in the apparent values of pKa of nitrophenols and the electrostatic interactions of NPO^- with micelles. In order to clarify this discussion, the measurements of pKa of substituted nitrophenols were carried out. The cationic surfactants caused the marked lowering of the apparent values of pKa, and the anionic one did a little increase. However, non-ionic one had no effect. It was found that these pKa changes depended on the extents of electrostatic, and hydrophobic interactions of the substituents (including the hydroxy and the nitro groups) with the micelles as well as the ionic properties of the surfactants. The extents of the hydrophobic interaction of the alkyl substituents with micelles were discussed by the thermodynamic parameter, -δΔG (Y-X) which implied that the substituent effect on the stabilization energy of NPOH (or NPO^-) due to the hydrophobic interaction with the micelles.
A significant deviation from Hammett relationship between pKa of p-substituted o-nitrophenols and σ^- was observed in the presence of CTAB, although this relationship showed a fairly straight line in the absence of the surfactant. This observation also suggested that the substituent present influenced the value of pKa of nitrophenol in the micelle solution not only by the electronic effects but also by above described interactions.

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Carps of about 10 g weight were grouped and treated as follows, 1) removing swimbladder, 2) loading with lead belt, 3) stressed with laparotomy and vinyl belt, 4) loading with float, and 5) un loaded control. They were fed the diets supplemented with 1-hexadecanol, palmitic acid, and hexadecyl palmitate for 10, 20, and 30 d. The concentration ratio of wax esters (WE) to triglycerides (TG) were increased significantly in the plus loaded group and decreased in the minus loaded group in comparison to the stress and control groups. In either case the tendencies of ratios were 1>2>3=5>4 with a few exceptions in the case of palmitic acid supplement.
The diabetic carps induced with alloxan donation were characterized by the liberation of free fatty acids and by the significant increase of WE against the reciprocal decrease of TG comparing to the controls. The higher incorporation of [1-¹⁴C] acetic acid into WE in the swimbladderectomized carp and that of [1-¹⁴C] 1-hexadecanol in the hepatopancreas homogenate of diabetic carp were obserbed, respectively. The relationship of the two lipid classes, namely WE and TG, seems to be regulated by the hydrostatic conditions concerning the buoyancy and through the metabolism of the ester counterparts of fatty acids.

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Commercial nonylphenyl poly (oxyethylene) ethers (n=3.811.0) were formylated at their benzene nucleus. The formyl derivatives (POE-CHO) obtained were then oxydized to the corresponding carboxylic acids (POE-COOH). Moreover, sodium salts (POE-COONa) and methyl esters (POE-COOCH₃) of those acids were prepared. The surface tension of the aqueous solutions of POE-CHO, POE-COOH, POE-COONa and POE-COOCH₃ were found to be almostly as low as those of their starting ethers. The antimicrobial and antifungal activities of those compounds were rearranged. POE-COONa and POE-COOCH₃ had little or no activity at the concentration of 100μg/ml. Although POE-CHO were nonionic surface active compouds and POE-COOH depended their surface activity on the nonionic moiety of their molecules, POE-CHO and POE-COOH showed considerably antimicrobial and antifungal on bacteria and notably on some fungi, respectively.

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Some p-nonylphenyl poly (oxyethylene) ether derivatives having one or two nitro groups or one or two amino groups in the aromatic nucleus were prepared. Antimicrobial activities and surface tensions of these derivatives were examined.
Surface tensions of water solutions of these derivatives were larger than that of the corresponding starting ether by 23 dyn/cm, but there was no difference in surface tension between the derivatives having one nitro or amino group and the derivatives bearing two nitro or amino groups.
Antimicrobial activity was not exhibited by the derivatives having one nitro or amino group, but that against some microorganisms was found in the derivatives bearing two nitro or amino groups. The effect of amino group on antimicrobial activity was stronger than that of nitro group.

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The removal of a small quantity of p-nonylphenyl poly (oxyethylene) ether (EO 10 moles) in water was studied by foam fractionation method.
Air was bubbled through water at a constant flow rate (150cm³/min), and the adsorption of the surfactant on the (generated) bubble surface and its removal (effect) were measured.
The results were as follows :
1) The adsorption of the surfactant on the bubble surface was found to come to an equilibrium in about two or three seconds, and the adsorption isotherm was confirmed to be in good agreement with Langmuir equation.
2) In the continuous foam fractionation at a constant air flow rate, the removal effect was better as the concentration of the fed liquid was lower and the feeding rate was smaller.

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