Fatty acids and unsaponifiable matters from the liver oils of Chionoecetes opilio, Lithodes turritus and Paralithodes camtschatica were examined. It was found that these liver oils were composed of C12C24 fatty acids, in which major component was oleic acid, by GLC analysis. Unsaponifiables were fractionated by low temperature fractional crystallization. The precipitate obtained from the unsaponifiables of Paralithodes camtschatica liver oil was further fractionated into two fractions. It was found that one of the fractions contained cholesterol and ergosterol and that the other consisted of C8C19 α-alkyl glyceryl ethers by comparing their IR and NMR spectra with those of the authentic samples and by GLC analyses. From the mother liquors obtained from these liver oils, four fractions were obtained, respectively, by means of column chromatography and preparative TLC, and they were confirmed to be C10C20 saturated hydrocarbons, C11C18 aliphatic alcohols, higher aliphatic aldehydes and methyl ketones.
Some chelate surfactants were synthesized which had one or two hydrophobic long chained N-alkyl groups and hydrophilic EDTA-metal chelate ions, and their properties were investigated. Some EDTA, N-alkyl substitution products and EDTA, N, N'-bisalkyl substitution products (alkyl group; decyl, dodecyl, tetradecyl, hexadecyl and octadecyl) were treated with salts of some transitional metals as the chelating agents, and many pure chelates were obtained. Some of those chelate surfactants thus obtained showed good surface activities.
Tetra-ethyleneglycol monoethers of butyl, pentyl, hexyl, heptyl and octyl resorcinols were prepared by the reaction of tetra-ethyleneglycol monochloride with alkyl resorcinols which had been obtained by acylation of resorcinol with fatty acid, followed by Clemmensen's reduction. The monochloride used had been produced from ethylene chlorohydrin and ethylene oxide. Surface tension of the aqueous solutions of these ethers was determined and it was found that as the number of carbon atoms in the alkyl group increased from four to eight, the surface tension lowered to about 30 dyne/cm. Antimicrobial activity of the monoethers was evaluated in terms of minimum inhibitory concentration (MIC) by agar streak method. Monoethers of butyl and pentyl resorcinols were as active as hexylresorcinol but other monoethers were more active than those although the number of OH group in the monoethers was less than that in alkylresorcinol. Of those ethers, that of heptylresorcinol gave the lowest MIC. Moreover, di-, tri- and tetra-ethylene-glycol monoethers of hexylresorcinol were prepared. The antimicrobial activity of tetra-ethyleneglycol monoether was found highest of the three.
The reactions of fluoroalcohols witn ethylene oxide (mole ratio 1 : 1) were examined in the presence of a small amount of sodium hydroxide catalyst at 8090°C in an autoclave. The products obtained were distilled in vacuo. The physical properties and surface tensions of fluoroalcohol-ethylene oxide (1 : 1) adducts were studied. The results were as follows : 1) The structure of fluoroalcohol-ethylene oxide (1 : 1) adducts was confirmed by means of mass, nuclear magnetic resonance and infrared spectroscopy, and by molecular refraction. 2) In aqueous solution, HCF2CF2CH2OC2H4OH, H (CF2CF2) 2CH2OC2H4OH, and CF3 (CF2) 2CH2OC2H4OH had low surface tension in comparison with their starting materials. 3) The surface tensions of fluoroalcohol-ethylene oxide (1 : 1) adducts and the starting alcohols in five organic solvents were measured. The adducts showed a high ability in reducing the surface tension in ethyleneglycol.
The velocity gradient dependence of flow birefringence has been investigated on highly concentrated aqueous solutions (10-25%) of polyoxyethylene dodecyl ether sodium sulfate (C12H25 (OCH2CH2) nOSO3Na, n=6 and 13) (I) and sodium dodecyl sulfate (II). In the concentration and temperature range experimented, every solution showed positive birefringence. This suggests that the solution structure mainly consists of lamellar micelle. In addition, in the solutions of I a network is likely to be formed by the interlinking of the polyoxyethylene chains situated outside the micelle. The solution of II showed larger velocity gradient dependency in flow birefringence than the solutions of I. This would be due to absence of the network formation. Flow birefringence was measured twice at every velocity gradient, in the course of raising the velocity gradient and in the returning course. In the case of 6 OE dodecyl ether sulfate, bire-fringence curves obtained on lowering the velocity gradient laid above those on raising, that is, hysteresis in velocity gradient dependence of the birefringence is present. Elevation of temperature and addition of electrolyte reduced the hysteresis. This supports the inference that in the case of 6 OE dodecyl ether sulfate the formation of the network, which is hindered, because of the relatively short chain length, by electrostatic effect of the ion group at the end of the polyoxyethylene chain, is promoted by the increase of the velocity gradient.