Penicillium herquei IFO 7904菌株を, 麦芽培地で液体培養して, 菌体及び培養濾液から抗酸化活性及びトコフェロール (Toc) と顕著な相乗効果を示す赤色物質 (PHR) を得た。元素分析及びスペクトルデータによって, PHRの分子式はC₂₀H₂₀O₈ (MW=388.38) と決定されたが, 正確な構造を決定するには至らなかった。ラード及びリノール酸メチルを基質とした自動酸化条件において, PHRの抗酸化活性は天然d-Tocの抗酸化活性の半分であったが, PHRはTocと顕著な相乗効果を示した。また, PHRは市販植物油を安定化させた, 特に0.05%PHR添加パーム油のAOM値は440hに達した。また, PHRはラード中で比較的熱安定性があり, さらに, 熱酸化条件及び類似のフライ条件処理下で, ラード中のTocの熱酸化を効果的に防止した。このため, TocとPHRを添加したラードのAoM値は, Tocだけを添加したラードのAOM値より常に大きかった。

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DSCを用いたN-スクシンイミジルカルボネート (種々の脂肪酸, 置換安息香酸, 脂肪族ジカルボン酸のN-スクシンイミジルエステル) の簡易合成法について検討した。ピリジン存在下で酸とDSCとをアセトニトリル中で反応させると好収率で目的のエステルが得られた。反応に伴って生ずるN-ヒドロキシスクシンイミドと反応に加えたピリジンは反応物を水で処理することにより容易に除去できた。HPLC, TLC分析から副生成物は認められなかった。本報の方法はDCCを用いる合成法に比べて生成物の収率, 純度が高く, 更に, 精製が極めて簡単であることに利点がある。

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油脂の光酸化促進性及び油脂の酸化時の安定性がクロロフィル (Chl) より高いフェオフィチン (Phy) が精製食用植物中になぜChlより高比率で存在するかについて検討した。なたね種子 (カノーラ種) に含まれる油脂を6種の溶媒で抽出し, 色素量とその組成を蛍光定量によって分析した。その結果, ヘキサンを用いた際にPhyが97%も占めたが, 溶媒の極性をあげるとChl抽出量が増えることがわかった。このことは, ヘキサン抽出ではChlとタンパク質の結合が切れないためにPhyが優先的に抽出されたものと推定された。
なたね粉砕物を加熱あるいはなたね抽出油を酸処理した際の色素組成の変化を検討したところ, Chlの一部がPhyに変化していることが認められたが, 実際の製油工程では始めからPhyの比率が圧倒的に高いので, この変化はあまり問題にはならないと考えられる。

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To study surface adsorption of cationic surfactants on a hydrophilic polymer latex, ζ-potential of styrene/2-hydroxyethyl methacrylate [P (St/HEMA)] copolymer latex was measured in aqueous solutions of alkyl pyridinium bromides (abbr. APB, C_nH_2n+1NC₅H₅Br; n=12 : DPB, n=14 : TPB and n=16 : HPB). Hydrophobic polystyrene (PS) latex was used as the reference sample. The amount of surfactant adsorbed per unit area of the latex was calculated from the ζ-potential value. With increasing concentration of surfactant, the sign of the ζ-potential of the latex changed from negative to positive and the amount of surfactant adsorbed increased. The surfactant adsorption increased with the hydrocarbon chain length of APB in the order HPB > TPB > DPB. These results can be explained by electrostatic bonds and the van der Waals force between the latex and surfactant. The amount of surfactant adsorbed on the P (St/HEMA) latex was less than that on the PS latex. The free energy of adsorption ΔG for a surfactant on a latex was calculated from parameters such as the slope of the ζ-log C_s (C_s : the concentration of surfactant) curve. The negative value of ΔG increased with chain length of the surfactant. Also this value on the P (St/HEMA) latex was less than that on the PS latex. The large positive value of the entropy of adsorption ΔG indicates the importance of entropic interactions and the formation of hydrophobic bonds as driving forces for adsorption of the surfactant on the latex surface. The ΔG for P (St/HEMA) latex had a smaller positive value than that for PS latex. It is concluded that the adsorbability of surfactant on P (St/HEMA) latex is lower than that on the PS latex, since hydrophilic poly-HEMA layer is present on the surface of the P (St/HEMA) latex.

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New type polycarboxylates containing either ether linkages or ether and hydroxyl groups were prepared by the reaction of methyl α-D-glucopyranoside with ethyl diazoacetate (acetate-type) or diethyl diazomalonate (malonate-type), or by the air oxidation of ethoxylated methyl α-D-glucopyranoside with 5% platinum catalyst on carbon (acetate-type). Their building performance in detergents, sequestration capacity for Ca (II), dispersion capacity for MnO₂ and biodegradabilities were determined and compared in these respects with sodium tripolyphosphate (STPP), disodium 3-oxapentanedioate (ODA) and trisodium citrate (CA). O-carboxymethylated methyl α-D-glucopyranoside was found to have better detergency building performance than that of ODA, but was slightly inferior to that of STPP. Malonate-type ether polycarboxylate showed building performance far superior to that of the corresponding acetate type ether polycarboxylates. Of the acetate-type builders tested in this report, tribasic acid was the most effective. These polycarboxylates derived from methyl α-D-glucopyranoside were found to be biodegradable under aerobic conditions. Binary mixtures of zeolite with these polycarboxylates showed synergistic properties in detergency powers.

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Many studies have been carried out on the mechanism of the adsorption of anionic and cationic surfactants on textiles. The case of cationic and anionic surfactants used in combination has also been reported. In such a case, the cationic surfactant is treated as a dispersion and when used with excess anionic surfactant solution, it is not adsorbed on textiles. In the present research, it was found that if a cationic surfactant is used as a corpuscle (fine solid, over 10 μm) in the presence of excess anionics, adsorption on to various textiles becomes possible.
For an understanding of this phenomenon, the work of adhesion (W_a) between an anionic/cationic surfactant complex and the surface of a textile was calculated, measuring the contact angle of 2 liquids with the complex by Wu's equation. W_a and the amount of adsorbed cationic surfactant on textiles were found to show a very close correlation.
Thus, in an excess anionic surfactant solution, an anionic/cationic surfactant complex is apparently formed on the surface of a corpuscle of a cationic surfactant, and the work of adhession between this complex and each textile is related to the adsorption (or deposition) of a cationic surfactant on textiles.

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The relationship between the surface tension change with time and the foam volume was investigated for a system containing anionic AOS, LAS and/or nonionic alkyl or s-alkyl poly (oxyethylene) ether with alkyl chains of the same length. Dynamic and equilibrium surface tension was measured by the vibrating jet and Wilhelmy's plate methods, respectively. The anionics showed similar foam volume and surface tension change with time. In regard to the nonionics, on increase in the number of moles of ethylene oxide per molecule was found to make the equilibrium surface tension higher and foam volume smaller. As for dynamic surface tension change, some difference was noted between the alkyl and s-alkyl poly (oxyethylene) ethers. That is, the dynamic surface tension of the s-alkyl poly (oxyethylene) ethers decreased with an increase in the number of moles of ethylene oxide per molecule (abbrev. “EO_p”), but that of the alkyl poly (oxyethylene) ethers remained constant regardless of EO_p. In AOS/nonionics mixed systems, a s-alkyl poly (oxyethylene) ethers having a high EO_p gave lower dynamic surface tension and smaller foam volume.

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To determine if solid wax esters are hydrolyzed by enzymes (lipase or esterase) they were dissolved in organic solvents followed by incubation with aqueous solutions of commercial enzymes at 45°C, 500 rpm.
Among the commercial preparations of several microbial enzymes tested, lipases from Candida cylindracea and Rhizopus chinensis were found to act on vegetable wax esters such as rice bran wax, candelilla wax and esparto wax. The carnauba wax ester hardly underwent any hydrolysis by any lipase. There was virtually no reaction of the lipases with the above wax esters in aqueous reaction systems. The time courses of hydrolysis of the wax esters was noted to vary according to the particular lipase used. The amount of each lipase required to bring about the same extent of hydrolysis on the same wax ester differed significantly. These findings may be accounted for primarily on the basis of the substrate specificity of each lipase for the carbon chain length of alcohols and fatty acids which are constituents of the vegetable wax esters. The data of the present study demonstrate the enzymatical hydrolysis of solid wax esters. This is at variance with the generally held notion that solid waxes are not attacked by enzymes.

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3-Methyl-4-octanolide (1), (Whisky lactone or Quercus lactone), was synthesized from crotonic acid and pentanal. The reaction of pentanal (3) with crotonic acid (4) provided 3-methyl-4-oxooctanoic acid (5) in a 66% yield, which was reduced by NaBH₄ to give whisky lactone (1) in a 88% yield. Similarly, trans-3-methyl-4-nonanolide (2), one of the component of cognac, was prepared from crotonic acid and hexanal.

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