• Archives of Pharmacal Research
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• v.20 no.3
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• pp.253-258
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• 1997

Ten, heretofore unreported, $ 5^I-methyl-5^I-[2-(5-substituted uracil-1-yl)ethyl)]-2^I-oxo-3^I$-methylenetetrahydrofurans (H, F, Cl, Br, I, $ CH_3$,$CF_3$,$CH_2CH_3$,$ CH=CH2$, SePh) (7a-j) were synthesized and evaluated against four cell lines (K-562, FM-3A, P-388 and U-937). For the preparation of ${\alpha}$-methylene-${\gamma}$-butyrolactone-linked to 5-substituted uracils (7a-j), the convenient Reformasky type reaction was employed which involves the treatment of ethyl ${\alpha}$-(bromomethyl)acrylate and zinc with the respective 1-(5-substituted uracil-1-yl)-3-butanone (6a-j). The 5-substituted uracil ketones (6a-j) were directly obtained by the respective Michael type reaction of vinyl methyl ketone with the $K_2CO_3$(or NaH)-treated 5-substituted uracils (5a-j) in the presence of acetic acid in the DMF solvent. The .alpha.-methylene-.gamma.-butyrolactone compounds showing the most significant antitumor activity are 7e, 7f, 7h and 7j (inhibitory concentration $(IC_50)$ ranging from 0.69 to $2.9 {\mu}g/ml$), while 7b, 7g and 7i have shown moderate to significant activity. The compounds 7a, 7c and 7d were found to be inactive. The synthetic intermediate compounds 6a-j were also screened and found marginal to moderate activity where compounds 6b and 6g showed significant activity $(IC_50:0.4~2.8 {\mu}g/ml)$.

• Corrosion Science and Technology
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• v.9 no.4
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• pp.147-152
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• 2010

Conventional paints for conversion coating applications in steel production derived mainly from water-based polymer dispersions containing several additives actually show good general performance, but suffer from poor scratch and abrasion resistance during use. The reason for this is because the relatively soft organic binder matrix dominates the mechanical surface properties. In order to maintain the high quality and decorative function of coated steel sheets, the mechanical performance of the surface needs to be improved significantly. In fact the wear resistance should be enhanced without affecting the optical appearance of the coatings by using appropriate nanoparticulate additives. In this direction, nanocomposite coating compositions (Nanomer$^{(R)}$) have been derived from water-based polymer dispersions with an increasing amount of surface-modified nanoparticles in aqueous dispersion in order to monitor the effect of degree of filling with rigid nanoparticles. The surface of nanoparticles has been modified for optimum compatibility with the polymer matrix in order to achieve homogeneous nanoparticle dispersion over the matrix. This approach has been extended in such a way that a more expanded hybrid network has been condensed on the nanoparticle surface by a hydrolytic condensation reaction in addition to the quasi-monolayer type small molecular surface modification. It was expected that this additional modification will lead to more intensive cross-linking in coating systems resulting in further improved scratch-resistance compared to simple addition of nanoparticles with quasi-monolayer surface modification. The resulting compositions have been coated on zinc-galvanized steel and cured. The wear resistance and the corrosion protection of the modified coating systems have been tested in dependence on the compositional change, the type of surface modification as well as the mixing conditions with different shear forces. It has been found out that for loading levels up to 50 wt.-% nanoparticles, the mechanical wear resistance remains almost unaffected compared to the unmodified resin. In addition, the corrosion resistance remained unaffected even after $180^{\circ}$ bending test showing that the flexibility of coating was not decreased by nanoparticle addition. Electron microscopy showed that the inorganic nanoparticles do not penetrate into the organic resin droplets during the mixing process but rather formed agglomerates outside the polymer droplet phase resulting in quite moderate cross linking while curing, because of viscosity. The proposed mechanisms of composite formation and cross linking could explain the poor effect regarding improvement of mechanical wear resistance and help to set up new synthesis strategies for improved nanocomposite morphologies, which should provide increased wear resistance.

• Polymer(Korea)
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• v.36 no.4
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• pp.427-433
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• 2012

A series of poly(imide-aramid-sulfone)s with alternatingly introduced imide/aramid groups were prepared by reacting divinyl sulfone (DVS) and $N^1,N^4$-bis(4-(vinylsulfonyl)phenyl)terephthalamide (2) with pyromellitic diimide. Three model compounds, N-[2-(p-aminophnenylsulfonyl)ethyl]phthalimide (3), 2,2'-(2,2'-sulfonylbis(ethane-2,1-diyl))diisoindoline-1,3-dione (4), and N,N-bis(4-(2-(1,3-dioxoisoindolin-2-yl)ethylsulfonyl)phenyl)terephthalamide (5), resembling polymers were prepared with good yields by reacting p-aminophenyl vinyl sulfone, DVS, and 2 with phthalimide. Condensation polymerization was carried out by Michael-type addition reaction of the difunctional phthalimide group with the DVS group in the presence of tetrabutylammonium hydroxide (TBAH), resulting in poly(imide-aramid-sulfone)s 6-12 with moderate molecular weights and good yields. They were highly soluble in polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, N-methylpyrrolidinone and tetrahydrofuran. The ratios of DVS/2 were 1/0, 3/1, 2/1, 1/1, 1/2, 1/3, and 0/1. Molecular weight and physical properties such as solubility, viscosity, and thermal properties of the polymers were examined.

• Korean Journal of Agricultural Science
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• v.10 no.2
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• pp.354-364
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• 1983

Confonmation of (Z)-cinnamonitrile have been studied by molecular orbital theoretically using extended Huckel theory(EHT) and CNDO/2 molecular orbital calculation methods. The results indicate that the stability of conformation is(Z)-gauch>(Z)-planar. The rate constants for alkalie hydrolysis of cinnamonitrile at pH 7.0-14.0 range have been determined by ultra-violet spectrophotometry in 50% methanol at $25^{\circ}C$ and the following rate equation which can be applied over wide pH range was obtained; $${\therefore}k=({\frac{1.41{\times}10^{-14}+1.21{\times}10^7/[H_3O^+]}{2.65{\times}10^{-7}+1.64/[H_3O^+]})+9.14{\times}10^9/[H_3O^+]$$ The rate equation reveals that, at pH 7.0-10.0, the reaction is initiated by the addition of water molecule to unsaturated cabon-carhon double bond of cinnamonitrile and ${\alpha}C-{\beta}C$ bond scission follow subsequently in neutral and alkalie media. At pH 12.0-14.0, in strong alkalie solution, that so-called Michael type nucleophilic addition that the over-all rate constants is only dependent upon the concentration of hydroxide ion occurs competitively and are very complicated. Hence, the reaction mechanism of alkalie hydrolysis of cinnamonitrile which did not carefully before can be fully explained.