A synergist for tocopherol (Toc) was isolated from a culture broth of Penicillium commune. It was a phenolic compound and identified as gentisyl alcohol (2, 5-dihydroxybenzyl alcohol) on the basis of elementary analysis and spectral data. Under autoxidation conditions, this alcohol (0.025%) was found to be a potent antioxidant and synergist with Toc (0.04%) in lard, the AOM stabilities of which were 160 and 234h, respectively. It was also capable of stabilizing vegetable oils such as soybean, rapeseed, and palm oils. The addition of this alcohol to Toc in lard failed to retard its oxidation. However, the AOM stabilities of lard treated under the thermal oxidation conditions were always higher in the presence of this alcohol than in its absence.

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The ¹H NMR spectra of the acetyl derivatives of six types (lanostane, cycloartane, cucurbitane, dammarane, euphane, and tirucallane types) of tetracyclic and eleven types (ursane, ψ-taraxastane, oleanane, taraxerane, multiflorane, lupane, fernane, hopane, arborinane, adianane, and glutinane types) of pentacyclic 3β-monohydroxy triterpenes were examined in the presence of tris (dipivaloyl-methanato) europium [Eu (dpm)₃], a lanthanide shift reagent. Assignments of their methyl resonances were made. Furthermore, lanthanide-induced shifts, expressed in terms of relative ΔEu-values, of the methyl resonances of the 3β-monoacetoxy triterpenes determined in this study were found useful for characterizing and distinguishing these compounds from each other.

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6-Hexyl-3- [7- (methoxycarbonyl) heptyl] -1-cyclohexene-4, 5-dicarboxylic anhydride (1) obtained by the addition of maleic anhydride to methyl (E, E) -9, 11-octadecadienoate was treated with m-chloroperbenzoic acid in chloroform to give 4, 5-epoxy-6-hexyl-3- [7- (methoxycarbonyl) heptyl] -1, 2-cyclohexanedicarboxylic anhydride (2). The ¹H-NMR, ¹³C-NMR, IR, EI-MS, and CI-MS spectroscopies of (1) and (2) indicated (1) and (2) to each have predominantly the half-chair conformation structure.

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To use CWM as a fuel in large quantity, the feasibility of this must first be demonstrated by a larger scale experiment. For this purpose, the properties of CWM containing a nonionic dispersant [N-poly (oxyalkylene) polyethylenimine, abbreviated as POA-PEI] or anionic dispersant (sodium salt of formalin condensate of naphthalenesulfonic acid, NSF-Na) were examined by continuous production and storage tests.
The findings warranting attention are as follows :
1) CWM produced by the large-scale continuous and small-scale batch processes showed essentially the same properties. CWM produced by the batch process made it possible to examine the physical properties of that produced by the large scale continuous process.
2) CWM was obtained with a coal concentration and viscosity that was higher and lower, respectively, than that containing NSF-Na, using POA-PEI, regardless of the scale of production.
3) Older, or more carbonized coal could be made into CWM loaded to a greater extent. Analytical values (O/C and H/C values) of coal made possible estimation of the loading level of CWM.
4) POA-PEI showed higher pulverizing efficiency in CWM production than NSF-Na.
5) The viscosity of CWM using POA-PEI could be owered more effectively by stirring than using NSF-Na. The CWM showed storage stability exceeding a period of one month.

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Determination of the lipid productivity and composition of 33 strains of the genus Mortierella using glucose or decane as the carbon source was carried out. The maximum accumulation of lipids was 2.01g/400ml medium (total intracellular lipids/dry cell weight, 49.7%) in the M. isabellia IFO 8308 strain grown at 20°C using glucose as a carbon source. The lipids extracted from 10 day-cultured cells were fractionated into neutral and polar lipid fractions by silicic acid column chromatography. The fatty acid and lipid compositions of both fractions were determined. The content of γ-linolenic acid (all cis-6, 9, 12-octatrienoic acid) in the M. ramanniana var. angulispora IFO 8187 strain was high under each cultural condition using either glucose or decane as the carbon source.

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Poly (β-DL-malic acid) sodium salt (PMLA) with a number average molecular weight (Mn) of 30006000 was prepared by the ring-opening polymerization of benzyl malolactonate. Poly (DL-malic acid) sodium salt with both α and β ester linkages of malic acid (PMLA-D) was prepared by the direct polymerization of DL-malic acid in dimethylsulfoxide under reduced pressure at 90°C. The biodegradability of the polymer was studied under aerobic conditions using activated sludge, soil bacteria and poly (malic acid) assimilable bacteria obtained by enrichment culture techniques. The enzymatic degradation of poly (malic acid) was carried out so as to elucidate the mechanism of the biodegradation. The sequestration capacity for Ca (II) ions and dispersion capacity for MnO₂ of both these salts were determined and compared in these respects with sodium tripolyphosphste (STPP), disodium 3-oxapentanedioate (ODA) and trisodium citrate. Their building performance in detergents was also examined.
Poly (malic acid) s obtained both by ring-opening and direct polymerization showed excellent biodegradability with activated sludge and soil bacteria. The biodegradation of poly (malic acid) appeared to occur first by the enzymatic hydrolysis of the terminal ester group of the polymer by bacteria, giving monomeric malic acid. The malic acid was metabolized in an usual manner. The polymers examined in this report showed the comparable detergency building performance to that of trisodium citrate and ODA.

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Maleinized liquid polybutadiene (LPM) and its derivatives (half-esterified, LPME) were neutralized by alkaline solution to obtain an aqueous solution. The effects of these oligomer surfactants as dispersing agents on aqueous dispersion systems of inorganic pigments (TiO₂, ZnO and CaCO₃) and organic pigments (Hanza Yellow and Phthalocianine Blue) were examined.
Their dispersing action was more effective than common dispersants on the market. A series of evaluation tests on the effects of the surfactants as dispersant on various water-based paints was carried out to find the best dispersing action and good water-resistency of film obtained from these paints.
The order of the solubilizing power (the number of moles of dimethylaminoazobenzene, DMAB, solubilized per moles of dispersant monomer) of LPM and LPME was found to be as follos :
LPME (h) *1>LPM (L) *2>LPME (l) *3>LPM (H) *4
*1 esterified LPM (H) by higher alcohol
*2 low Acid Value (AV) LPM, AV=100mg KOH/g LPM
*3 esterified LPM (H) by lower alcohol
*4 high Acid Value LPM, AV=200mg KOH/g LPM
This order is essentially the same as that for the conversion of the emulsion polymerization of styrene, using the above dispersants as emulsifiers.
The data presented above suggest the formation of aggregated micells of the dispersants and/or quasi-micells.

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The optically active and racemic forms of N-dodecyl and N-dodecyl-N-methylamino acids were synthesized by reductive N-alkylation of α-alanine and valine. The structures of these compounds were confirmed by NMR, IR and elementary analyses. N-dodecylamino acids are not soluble in water but N-dodecyl-N-methylamino acids are readily soluble. The L- and D-isomers of N-dodecyl N-methylamino acids were confirmed to be optically pure by HPLC using a chiral column. Surface tension and spectral change of a dye were used to determine the critical micelle concentration (cmc) of N-dodecyl-N-methylamino acids. The cmc values were the same, whether between optically active isomers or optical and racemic isomers. These phenomena suggest that the mechanism of micelle formation of N, N-dialkylated amino acids differs from that of N-acylamino acids.

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The lipase (EC 3.1.1.3) was found to be active in various organic solvents on esterification of cholesterol and fatty acid. The recovered lipase could be used again several times for esterification. Its enzymatic activity was much higher in repeated use than in the first use.

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The effects of the crystal structure of a surfactant on the coloration of azo oil dyes were studied and found to depend on the kinds of auxochrome in the dye molecule and hydrophilic groups and alkyl chain length in the surfactant molecule.
In particular, when crystals of sodium alkyl (tetradecyl, hexadecyl and octadecyl) sulfates were precipitated at room temperature, they interacted with the azo oil dye having an amino group at the 4-position of naphthalene. The maximal absorption of the crystals had a specific wavelength (610nm), possibly due to the polymorphism of the sodium alkyl sulfates.

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A synthesis and properties of the polyalkylene oxide adducts of carbazole as nonionic surfactants have been studied.
The adducts have the following properties;
1) Extremely low foaming, 2) Excellent electro-conductivity, 3) High resistant toward thermal decompostion.
The oxide adducts should find application not only as water-soluble surfactants but also as oil-soluble and useful additives for the modification of resin properties.

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