Both monohydroperoxides (MHP) and more polar secondary oxidation products (SP) formed by autoxidation of methyl linolenate were separated by high performance liquid chromatography (HPLC) into their corresponding four major components. The isomeric compositions of these components were determined by mass chromatographic analysis. All components were positive to the thiobarbituric acid (TBA) test. The reactivities of MHP to TBA did not vary with their isomeric compositions, when iron (II) ion was added in the test reaction. It was concluded that all hydroperoxide isomers present in autoxidized methyl linolenate yielded TBA reacting materials.

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When the solution of bovine serum albumin (BSA) at pH 9 was heated at 65°C, new components (1'), (2), (3), ......were formed. Here the components (1'), (2), and (3) are modified monomer, dimer, and probably trimer, respectively. The component (1') was formed by the intramolecular sulf hydryl disulfide exchange reaction. Components (2) and (3) were formed by the intermolecular sulfhydryl disulfide exchange reaction. If appropriate amounts of anionic surfactant were added to BSA solution, the formation of component (1'), or the intramolecular exchange reaction, was prevented. It is known since earlier data that fatty acid anions prevent the denaturation of BSA. The cause found in this study was that the anionic surf actant prevented the formation of component (1').
The minimum amounts of various surfactants to prevent the formation of component (1') were determined. The minimum molar ratio of surfactant/BSA was as follows : 5 for sodium tetradecyl sulfate and sodium palmitate, 6 for sodium tridecyl sulfate and sodium laurate, 7 for sodium dodecyl sulfate and sodium undecyl sulfate, 10 for sodium decyl sulfate, about 40 for sodium nonyl sulfate, and 28 for sodium hydrogen N-lauroyl-L-glutamate (LS-11). These values are conventional measures of a relative affinity of surfactant to BSA, indicating that the affinity of LS-11 is between that of sodium decyl sulfate and sodium nonyl sulfate. The present method is useful in determining the relative affinity of any anionic surfactant to BSA.

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Stearic-9, 10-d₂, stearic-9, 9, 10, 10-d₄, oleic-9, 10-d₂, decanoic-3, 3-d₂, lauric-3, 3-d₂, myristic-3, 3-d₂, palmitic-3, 3-d₂, and stearic-3, 3-d₂ acids were synthesized, and ¹H NMR spectra of the methyl esters of these deuterated acids were measured. The signals due to the protons which were substituted by deuterons disappeared on the ¹H NMR spectra of the deuterated acid methyl esters. Estimation of the deuterium-labeled acid content in unlabeled acids was possible by measuring the relative decrease in the integrated areas of the signals for the corresponding methylene or olefinic protons which were replaced with deuterons in the deuterated acids. The shift reagents, Eu (fod) ₃ and Pr (fod) ₃, were effective for the NMR determination of deuterium-labeled fatty acids. Oleic-9, 10-d₂ acid and saturated 3, 3-dideutero acids seem to be useful as nonradioactive tracers in the NMR analysis.

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The interaction in an oil-water system between an anionic surfactant and oily materials has been studied by the observation with a polarizing microscope and by the measurement of the interfacial tension at oil/water interface. When dodecane, a non-polar oily material, was gently in contact with SDS solution, no change occurred at the interface. On the other hand, in the case of 1-dodecanol, a polar oily material, spontaneous emulsification occurred in the water phase or liquid crystal formed at the oil/water interface. These were affected by the concentration of SDS in water. In the case of oleic acid, a polar oily material, spontaneous emulsification occurred in the water and/or oil phases, and the liquid crystal formed only at high concentration of SDS in water. The interfacial tension was 3.3 dyn/cm when the liquid crystal formed at the 1-dodecanol/water interface, and that in case of oleic acid was 1.1 dyn/cm. Further, in the case of 1-dodecanol, the composition of the liquid crystal formed at the interface was the same as that of the liquid crystal region in a phase diagram of the ternary system.

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Some of the malonate-type ether polycarboxylates including trisodium 2-oxa-1, 1, 3-propanetricarboxylate (CMT) and trisodium 2-oxa-1, 3, 4-butane-tricarboxylate (CMOS) were prepared from the corresponding alcohols and ethyl diazomalonate, then their building performances were compared with those of the acetate-type ether polycarboxylates, sodium tripolyphosphate (STPP) and disodium 3-oxapentanedioate (ODA).
The detergency building action of the aqueous solutions of binary systems consisting of those ether polycarboxylate builders were also discussed. The detergency were tested on naturally soiled cotton patches and the detergency powers were evaluated by Scheff e's method in a detergent system formulating sodium alkylbenzenesulf ovate (LAS).
From the results summarized in Fig.-1, it was evident that malonate-type ether polycarboxylates showed the building performances much superior to those of the corresponding acetate-type ether polycarboxylates. Above all malonate-type ether carboxylate with methyl group on the carbon neighboring dicarboxymethoxyl group, i.e., tetrasodium 3-methyl-2, 5-dioxa-1, 1, 6, 6-hexane tetracarboxylate (MEGDM) showed a building performance superior to that of STPP. From Fig.-2, it was found that some mixtures of these acids exhibited synergistic effects on their building performances.

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As emulsion is non-equilibrium state, the technique of emulsification greatly affects the droplet size and its distribution of emulsion. When it is tried to form stable O/W emulsion by nonionic surfactants, the agent-in-oil method dissolving the surfactants in the oil phase is generally adopted.
In this paper, the reasons, which this method is desirable for forming homogeneous O/W emulsion, were investigated from the soluble state of surfactants-water-oil system.
As the results, it was shown that homogeneous O/W emulsions were formed under the conditions appearing oil-continuous phase-liquid crystalline phase-white gel emulsion-O/W emulsion in the process of emulsification. And it was indicated the possibility to decrease the difference of quality due to manufacturers by utilizing this emulsification method.
The structures of the liquid crystal and the gel which exsist in the process of emulsification were determined by X-ray low angle diff ractometer and electron microscope. And the mechanism forming a homogeneous O/W emulsion was elucidated.

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Builder effects of hydroxy carboxylates, amino acids and N-acylamino acid were studied and compared with those of sodium tripolyphosphate (STP). Chelating capacities of the builders for individual and binery systems as a function of pH were examined using calcium ion selective electrode at 30°C. On the other hand, builder effects of the compounds on detergency with 0.05% anionic surfactant [sodium dodecylbenzensulfonate (DBS) or α-olefinsulfonate (AOS)] were tested for cotton and polyester fabrics soiled with dust, in 100 ppm hard water at pH 9.5, 30°C.
It was demonstrated that chelating capacity (mg CaCO₃ / g) and detergency of STP were superior than the others, but hydroxy carboxylates were more effective on detergency performance at fairly high concentration than STP at ordinary level, and also more effective consisting with DBS than AOS. Moreover, it was found that AOS was an excellent surfactant for low phosphate detergent formulations because of its high performance in hard water.

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A gas chromatography, using water-vapor as a carrier gas, was investigated for the determination of water-soluble solvents in liquid detergents.
These solvents were separated and determined on porous polymer beads columns, Porapak Q or Tenax GC, and quantitatively recovered from standard detergent in the range of useful formulation.
The recoveries of these solvents were as follows ;
Methyl alcohol : 102.3% Butyl carbitol : 103.3%
Ethyl alcohol : 101.7% Monoethanolamine : 101.3%
Isopropyl alcohol : 100.2% Diethanolamine : 100.9%
Propylene glycol : 100.6% Triethanolamine : 102.4%
Butyl cellosolve : 98.3%
These results were obtained with good accuracy.
This method is applicable to a rapid determination of water-soluble solvent in liquid detergent.

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The amounts of water dissolved in safflower oil were measured by GLC, which was connected a sample-heater.
The peak area of gas chromatogram increased in proportion to the amount of water in the range of 1.2 to 9.8g.
This method is better than the Karl Fischer method on these points of the reduction of measuring time and the precision.

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