• Title/Summary/Keyword: Nitrile group

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A Study on Chemical Modification Effect of Papermaking Fiber by Cyanoethylation (Cyanoethyl화에 의한 제지용 섬유의 화학적 개질효과에 관한 연구)

  • Yoon, Se-Young;Jo, Byoung-Muk;Oh, Jung-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.25 no.1
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    • pp.56-64
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    • 1997
  • Since there are three hydroxyl groups on each anhydroglucose ring of the cellulose, the renewable resources, we can get various functional papers by the chemical modification of cellulose. The reaction involving the introduction of the ${\beta}$-cyanoethyl ($-CH_2-CH_2$-CN) group into organic substances containing reactive hydrogen atoms is known as cyanoethylation. Cellulose reacts with acrylonitrile in the presence of strong alkalis in a typical manner of primary and secondary alcohols to form cyanoethyl ethers. In cyanoethylation, important factors of reaction are temperature, concentration of the NaOH, and addition rate of acrylronitrile. FT-IR spectra of cyanoethyl group was confirmed at $2250cm^{-1}$, which corresponds the introduction of aliphatic nitrile group. Effect of cyanoethyl DS(degree of substitution) on strength properties was resulted that cyanoethylated BKP of DS 0.04 appeared to be the best choice for overall strength properties. Also, excellent thermal stability in aging characteristics was obtained.

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Introduction of Heterocycles at the 2-Position of Indoline as Ester Bioisosteres

  • Lee, Sung-Kyung;Yi, Kyu-Yang;Yoo, Sung-Eun
    • Bulletin of the Korean Chemical Society
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    • v.25 no.2
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    • pp.207-212
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    • 2004
  • In this study, we attempted to prepare compounds with heterocyclic replacements for metabolically unstable esters of benzopyranyl indole-2-carboxylic esters, which showed good in vitro and in vivo cardioprotective efficacies possibly through the opening of mitochondrial ATP-sensitive potassium channel ($K_{ATP}$). Initially, we tried to construct indolin-2-yl-heterocycles using unprotected indoline-2-carboxylic acid, but the cyclization was proceeded with oxidation of the indoline ring to the indole, which didn't react with benzopyranyl epoxide. Thus we introduced N-Boc group to deplete the electron density of the indoline ring. We successfully prepared various indolin-2-yl-heterocycles by the cyclization of the building blocks including carboxamide, ${\beta}$-hydroxy amide, hydrazide, nitrile starting from N-Boc-indoline-2-carboxylic acid.

Crystal Structure Analysis of 3-(4-ethylphenyl)-3H-chromeno[4,3-c]isoxazole-3a(4H)-carbonitrile

  • Malathy, P.;Ganapathy, Jagadeesan;Srinivasan, J.;Manickam, Bakthadoss
    • Journal of Integrative Natural Science
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    • v.8 no.4
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    • pp.250-257
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    • 2015
  • The crystal structure of the potential active 3-(4-ethylphenyl)-3H-chromeno[4,3-c]isoxazole-3a(4H)-carbonitrile ($C_{19}H_{16}N_2O_2$) has been determined from single crystal X-ray diffraction data. In the title compound crystallizes in the monoclinic space group $P2_1/c$ with unit cell dimension a=6.6869 (8) ${\AA}$, b=15.8326 (19) ${\AA}$ and c= 15.237 (2) ${\AA}$ [${\alpha}=90^{\circ}$, ${\beta}=100.663^{\circ}$ and ${\gamma}=90^{\circ}$]. In the structure chromene, isoxazole and carboxylate are almost coplanar each other. All geometrical parameters revelled that chromene ring of pyran ring adopt sofa conformation. The crystal packing is stabilized by intermolecular C-H...N and C-H...O hydrogen bond interaction.

Synthesis and Catalytic Activity of Water-Soluble Iridium-Sulfonated Triphenylphosphine Com;lex. Hydration of Nitriles

  • 진종식;김상열;주광석;원경식;종대성
    • Bulletin of the Korean Chemical Society
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    • v.20 no.5
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    • pp.535-538
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    • 1999
  • Five coordinated water-soluble iridium(l) complex, IrH(CO)(TPPTS)3 (1) (TPPTS = P(m-C6H4SO3Na)3-xH2O) has been prepared from the reaction of IrCl3·3H2O with TPPTS and HCHO in H2O/EtOH solution. Complex 1 catalyzes the hydration of nitrites (RC ≡ N, R = CH3, CICH2, CH3(CH2)4, Ph) in aqueous solution to give the corresponding amides (RCONH2) at 100℃. The hydration of unsaturated nitrites (R'C ≡ N, R'=CH3CH=CH, CH3OCH=CH, trans-PhCH=CH, CH2=C(CH3)) takes place regioselectively on-C ≡ N group to give unsaturated amides (R'CONH2) leaving the olefinic group intact. The yields of the amides seem to be depending on the electrophilicity of the carbon of nitrile: The more the electron withdrawing ability of the substituents on nitrites, the more amides are obtained. The hydration of dinitriles (NC-R-CN, R=(CH2)4, (CH2)6) with complex 1 initially gives mono-hydration products (NC-R-CONH2) which are slowly hydrated further to give dihydration products (H2NCO-R-CONH2). The hydration of 1,4-dicyanobutane has been found to be somewhat faster than that of 1,6-dicyanohexane.

Revisit of Thermoplastic EPDM/PP Dynamic Vulcanizates

  • Lim, Jaehwa;Park, Jun Il;Park, Joon Chul;Jo, Mi Young;Bae, Jae Yeong;Choi, Seok Jin;Kim, Il
    • Elastomers and Composites
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    • v.52 no.1
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    • pp.35-47
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    • 2017
  • A comprehensive survey of the available literature showed that in the last few decades, there has been a growing interest in the use of thermoplastic vulcanizates (TPVs). TPVs are the second largest group of soft thermoplastic elastomers (TPEs) after styrene-based block copolymers, and offer a wide range of potential and proven applications, including in mechanical rubber goods, under-the-hood applications in the automotive field, industrial hose applications, electrical applications, consumer goods, and soft touch applications. Over the last two decades, TPVs have shown a strong and steady market growth (~12% per year). Commercialized TPVs are commonly based on blends of ethylene propylene diene monomer (EPDM) rubber and polypropylene (PP), and to a lesser extent on combinations of butyl or nitrile rubber with PP. EPDM/PP TPVs are characterized by finely dispersed crosslinked EPDM rubber particles (particles size varying between 0.5 and $2.0{\mu}m$) distributed in a continuous thermoplastic PP matrix. If the rubber particles of such a blend are small enough and if they are vulcanized well enough, then the properties of the blend are generally improved. This review article introduces various topics and aspects relevant to EPDM/PP TPVs. The development of TPVs, the use of various types of crosslinking systems and co-agents as crosslinking agents for PP/EPDM blends, the morphology and rheology of TPVs, and their typical end-use applications are also reviewed.

Eliminations from (E)-2,4-Dinitrobenzaldehyde O-Aryloximes Promoted by R3N/R3NH+ in 70 mol% MeCN(aq). Effects of Leaving Group and Base-Solvent on the Nitrile-Forming Transition-State

  • Cho, Bong Rae;Pyun, Sang Yong
    • Bulletin of the Korean Chemical Society
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    • v.34 no.4
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    • pp.1030-1034
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    • 2013
  • Elimination reactions of $(E)-2,4-(NO_2)_2C_6H_2CH=NOC_6H_3-2-X-4-NO_2$ (1a-e) promoted by $R_3N/R_3NH^+$ in 70 mol % MeCN(aq) have been studied kinetically. The reactions are second-order and exhibit Br$\ddot{o}$nsted ${\beta}$ = 0.80-0.84 and ${\mid}{\beta}_{lg}{\mid}$ = 0.39-0.42, respectively. For all leaving groups and bases employed in this study, the ${\beta}$ and ${\mid}{\beta}_{lg}{\mid}$ values remained almost the same. The results can be described by a negligible $p_{xy}$ interaction coefficient, $p_{xy}={\partial}{\beta}/pK_{lg}={\partial}{\beta}_{lg}/pK_{BH}{\approx}0$, which describes the interaction between the base catalyst and the leaving group. The negligible pxy interaction coefficient is consistent with the $(E1cb)_{irr}$ mechanism. Change of the base-solvent system from $R_3N$/MeCN to $R_3N/R_3NH^+$-70 mol % MeCN(aq) changed the reaction mechanism from E2 to $(E1cb)_{irr}$. Noteworthy was the relative insensitivity of the transition state structure to the reaction mechanism change.

Studies on Amidoximated Acrylic Fiber(I) -Amidoximation and Adsorption Capacity to Transition Metals - (아크릴 섬유의 아미도옥심화에 관한 연구(I) -아미도옥심 반응과 천이금속의 흡착능-)

  • Chin, Young Gil;Kim, Kyu Beom
    • Textile Coloration and Finishing
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    • v.8 no.6
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    • pp.40-46
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    • 1996
  • In order to investigate a practical application of fibrous absorbents to transition metals such as copper, nickel, cobalt, chrome, and iron, amidoximated fiber as a particular class of solid chelate agents were prepared from acrylic fibers treatment with hydroxylamine. The adsorption mechanisms of metal ions onto amidoximated acrylic fibers and their complexes were studied. Amidoximation of acrylic fiber with hydroxylamine is found to be first-order reaction, followed by the disappearance of infrared adsorption peaks due to nitrile groups of acrylic fibers. The uptake of metal ions onto amidoximated acrylic fiber is increased with temperature raising and the adsorption is also depended on pH of the soiutions. About 70% of metal ions can be recovered from aqueous solutions of Ni(II), Co(II), Cr(III), and Fe(II) on the concentration below 5x 10$^$^{-4}$ in the range of pH 2.1~10.0. Transition metals are adsorbed to form complex with amidoxime group by the ligand sites such as C=N, NH, NO, NHOH.OH.

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Stability of Mono- and Bis-pyridinium Oximes in Aqueous Systems (Monopyridinium Oxime과 Bispyridinium Oxime 화합물의 수용액 중 안정성 연구)

  • Jung, Chang-Hee;Choi, Seung-Ju;Seo, Won-Jun;Sok, Dai-Eun
    • Journal of Pharmaceutical Investigation
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    • v.24 no.4
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    • pp.273-279
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    • 1994
  • The stability of three oximes, Hl-6 [(4-carbamoyl-2'[(hydroxyimino)-methyl]- 1,1'-oxydimethylenedi-(pyridinium chloride)], Hl-CN [(4 cyano-2'-[(hydroxyimino)-methyl] -1,1'-oxydimethylene-di-(pyridinium chloride)], and 2-PAM [pralidoxime chloride] in aqueous solutions was evaluated by HPLC assay. The rate of degradation is dependent on the pH as well as the temperature at which the solution is stored. The optimum pH for the stability of these oximes was pH 2 to 3. The degradation rate constant for 2-PAM ($k\;at\;70^{\circ}C$, $2.07{\times}10^{-4}/hr;\;E_a\;value$, 27.2 kcal/mol) was smaller than those for bis-pyridiniumoximes, Hl-6 ($k\;at\;70^{\circ}C$, $3.38{\times}10^{-3}/hr$) and Hl-CN ($k\;at\;70^{\circ}C$, $8.66{\times}10^{-3}/hr;\;Ea\;value$, 20.7 kcal/mol). In mechanistic analyses, it was found that Hl-CN was decomposed through not only the hydrolysis of nitrile group but also the cleavage of methylene ether bridge, in contrast to Hl-6 which was degraded mainly through the cleavage of methylene ether bridge.

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Thin layer(Overcoat) for TFT-LCD color filter (LCD용 컬러필터 보호막)

  • Kim, Myeong-Koo;Park, Joo-Hyeon;Lim, Young-Taek
    • Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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    • 2006.11a
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    • pp.273-273
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    • 2006
  • Over the past years, a large number of acrylate polymers have been developed and the overcoat thin layer containing acrylate polymers have been used for TFT-LCD color filter. As forming thin layer using acrylate polymers, the existing acrylate polymers have some problems such as low hardness by low Tg temperature, coating uniformity and solubility in organic solvent. To solve these problems, we synthesized new polymer(Scheme.), containing olefin monomer, which has high Tg temperature, good coating uniformity and good solubility in organic solvent. The overcoat thin layer containing new polymer resulted in good coating uniformity, stain, spot, scratch, heat resistance, DOP(Degree Of Planarization) on RGB glass, transparency, hardness, adhesion, anti-chemicals(anti-acid, anti-base, anti-organic solvent), insulation and anti-humidity. Scheme. The structure of new polymer X = Olefin monomer contains ketone, ester, hydroxy, ether, halogen, nitrile, alkoxy, phenyl functional group $R_1$ and $R_2$= H or $CH_3$. Ratio=0<[1/(1+m+n)]<0.7,0.1[$\leq$[n/(1+m+n)]<0.5.

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A New Combined Source of "CN" from N,N-Dimethylformamide and Ammonia in the Palladium-Catalyzed Cyanation of Aryl C-H Bonds

  • Choi, Ji-Ho;Kim, Jin-Ho;Chang, Suk-Bok
    • Proceedings of the Korean Vacuum Society Conference
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    • 2011.08a
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    • pp.207-207
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    • 2011
  • Aromatic nitriles possess versatile utilities and are indispensible not only in organic synthesis but also in chemical industry. In fact, the nitrile group is an important precursor for various functional groups such as aldehydes, amines, amidines, tetrazoles, amides, and their carboxyl derivatives. Representative methods for the preparation of organonitriles with cyanide-containing reagents are the Sandmeyer and Rosenmund-von Braun reactions. Recently, a catalytic route to aryl nitriles has been reported on the basis of the chelation-assisted C-H bond activation or metal-catalyzed cyanation of haloarenes. In those cyanation protocols, the "CN" unit is provided from metal-bound precursors of MCN (M=Cu, K, Na, Zn), TMSCN, or K3Fe(CN)6. Additionally, it can be generated in situ from nitromethane or acetone cyanohydrin. Herein, we report the first example of generating "CN" from two different, readily available precursors, ammonia and N,N-dimethylformamide (DMF). In addition, its synthetic utility is demonstrated through the Pd-catalyzed cyanation of arene C-H bonds.

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