各種のフェノール誘導体を合成し, エステル潤滑油に対するそれらの酸化防止能を示差熱分析装置を用いて研究した。トリフェニルメタン型フェノールの酸化防止能は, フェニル環上の置換基の性質に密接な関係があることが見いだされた。一般的に電子供与基は酸化防止能を向上させた。また, 赤外スペクトルにおけるフェノールのOH伸縮振動帯の振動数と酸化防止能の間に相関関係が認められた。すなわち, 強い水素結合は酸化防止能を低下させると考えられる。4, 4'-ジヒドロキシジフェニルスルフィド及びエーテルは, 相当するビスフェノールと比較してかなり強い酸化防止能を示した。さらに, スルフィドとフェノール類の混合物における協同効果についてものべる。

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二相系 (水-有機溶媒) において酵素反応を行うことを目的とした。モデル酵素として, ダイズより得られたリポキシゲナーゼ (LG) を用い, N-スクシンイミジルベンゾエート (1) でアミノ基を修飾し二相系 (水-ヘキサン) での酵素反応を試みた。
基質 (リノール酸) を溶かしたヘキサン溶液に, 酵素を溶かした水溶液を加えた二相系においては, 未修飾のLGは, 不安定でヘキサン中のリノール酸はほとんど酸化されなかった。しかし, (1) で修飾したLGはある程度ヘキサンに対し安定であり, またヘキサン中のリノール酸の酸化が観察された。また安定性及び反応性は, 修飾率が高い程大きく, すなわち酵素の疎水性を上げる程安定性及び反応性は, 増大することがわかった。また, このような二相系での反応性は (1) で修飾したBSAを加えることによっても見られるということから, (1) により修飾されたタンパク質が, この系での安定性及び反応性に寄与するものと考えられた。
以上の結果から (1) が酵素のヘキサンに対する安定性を高める修飾試薬として使用できるものと推論できる。

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To examine the nutritional and physiological effects of dietary hardened fish oil (HFO), three groups of weanling male rats were fed diets containing 20 % HFO, soybean oil (SO) or hardened soybean oil (HSO) for 5 days and 8 weeks. The effects of these fats on weight gain, serum lipids and fatty acid profiles of the liver, heart and adipose tissue were compared.
1) No rats showed abnormal external appearances or heart and liver condition at autopsy. Body weight gain was highest in the SO group and lowest in the HFO group, the HSO group showing intermediate gain. The relative liver weight of the HFO group increased temporarily after 5 days but became comparable to those of the other groups with prolonged feeding. Triglyceride and cholesterol serum levels were higher in the SO group than in the other groups.
2) In the livers of rats fed HFO and HSO, trans fatty acids, comprised primarily of monounsaturated acids, were detected, but their amounts decreased after a prolonged period of feeding. Trans isomers of 20 : 1 and 22 : 1, both characteristic of HFO, could hardly be detected in the HFO group. Although percentages of n-6 polyunsaturated fatty acids were very low and remained unchanged in the HFO group, they increased in the HSO group as the time of the feeding period progressed. Essentially the same was noted for heart lipid content.
3) In the SO group, detectable amounts of traps acids, absent from the dietary fat, were detected in liver and heart lipids, and also in adipose tissue but to a lesser degree.
4) These observations indicate long chain traps monoene fatty acids in HFO to apparently have no particularly unfavorable effects on rats.

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To elucidate the mechanism by which silicone oil (SO) surpresses the thermal deterioration of frying oil, the following experiments were carried out.
1) Soybean and linseed oils with 1 ppm or without SO were heated in a beaker for 4, 8 h at 180°C, and the same oils (12.5g, 25g, 50g) with 0.1100 ppm or without SO were also heated on an iron plate (23×30 cm) for 10 to 50 min at the same temperature. The degree of deterioration of the heated oil was estimated in terms of viscosity and the acid and carbonyl values of each oil.
The results from the beaker and iron plate experiments indicated the efffectiveness of the SO to be independent of the amount of SO until this amount became less than 1 ppm. Below this amount, the effectiveness of the SO was reduced.
2) The effects of various SOs in preventing thermal deterioration of soybean oil were compared. To determine the effects of SO, soybean oil was heated on an iron plate with various SO at 1 ppm and 10 ppm at 180°C for 10 and 15 min. Effective SOs, such as dimethylpolysiloxane (DMPS) were heat resistant and rather insoluble in glyceride. Fat-soluble SO, such as higher fatty acid modified SO, showed no protective effects.
The finding that effective SO such as DMPS becomes concentrated on the oil surface appears in agreement with the above results.

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The title compounds (4) (alkyl=n-C₁₀H₂₁, n-C₁₂H₂₅, n-C₁₄H₂₉ and n-C₁₆H₃₃), were prepared by reactions of N-alkyltaurines (3) with carbon disulfide, followed by ethylation with bromoethane (Scheme-1, Table-1). The critical micelle concentrations of their aqueous solutions were determined by surface tension and electric conductivity (Table-2, Fig.-1 and 2).Dispersion, emulsifying, and solubilization powers were also measured using calcium carbonate, liquid paraffin, and Orange OT, respectively (Fig.-4, 5, and 6). The results indicated good surface-active properties of (4), which became better with increasing alkyl chain length except for emulsifying power. Although the compounds (4) were inactive against the gram-negative bacterium, Escherichia coli, good inhibitory effects were observed against the gram-positive bacterium, Staphylococcus aureus and the fungus, Aspergillus oryzae, particularly in the cases of R 10- (4) and R 12- (4) (Table-3 and 4, Fig.-7).

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Five ionene polymers (A-A, A-O O-O, Am-A and Am-O), each having one or more groups in the polymer chain among alkylene (A), poly (oxyethylene) (O) and poly (N-methyl-aminoethylene) (Am), and branched (PEImB) polyethyleneimine were prepared. The ability of this polymers to break the dodecane/water emulsion stabilized by p-nonylphenyl poly (oxyethylene) ether (n=10) was evaluated on the basis of the final concentration of dodecane in the waterlayer. The effects of these polymers on demulsification increased in the order of A-A<O-O<A-O<Am-O<Am-A=PEImA=PEImB. Many A-O, Am-A, PEImA and PEImB, containing tertiary amino groups or ether linkages in the main chains, caused reduction in the concentration of dodecane from 2 000 ppm to a trace at their respective optimum dosages. This effect of the ionene polymer is discussed in terms of charge neutralization, polymer bridging effects, and polymer chain structure.

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