• Title/Summary/Keyword: Cyclic imide

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Synthesis and characterization of star-shaped imide compounds

  • Jeon, Eunju;Yoon, Tae-Ho
    • Rapid Communication in Photoscience
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    • v.1 no.1
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    • pp.19-20
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    • 2012
  • Novel star-shaped imide compounds containing electron-donating triphenylamine and/or electron-withdrawing bis(trifluoromethyl)phenyl side groups were synthesized via a two-step process. First, 3,6-dibromo-benzene-1,2,4,5-tetracarboxylic acid (2B4BA) was reacted with 4-aminophenyl (diphenylamine) (ATPA) or 3,5-bis(trifluoromethyl)aniline (6FA) by imide reaction. Then, Suzuki coupling reaction was carried out on these compounds with 4-(N,N-diphenylamino)-1-phenyl boronic acid (BTPA) or 3,5-bis(trifluoromethyl)phenyl boronic acid (6FBB), resulting in 3,6-bis[4-(diphenylamino)phenyl]-N,N'-bis[4-(diphenylamino) phenyl]-pyromellitimide (TPTPPI), 3,6-bis[3,5-bis(trifluoro methyl) phenyl]-N,N'-bis[3,5-bis(trifluoromethyl) phenyl]-pyro mellitimide (6F6FPI) or 3,6-bis[4-(diphenylamino)phenyl]-N,N'-bis[3,5-bistrifluoromethyl)phenyl]-pyromellitimide (6FTPPI). The imide compounds obtained were characterized by NMR, FT-IR, DSC, TGA, melting point analyzer, EA, and solubility measurements. In addition, their optical and electrical properties were evaluated by fluorescence spectroscopy, UV-vis spectroscopy, and cyclic voltammetry (CV). 6F6FPI exhibited deep blue emission (443 nm), along with high $T_m$ ($382^{\circ}C$) and relatively high $T_g$ ($148^{\circ}C$).

Zinc Mediated Barbier Type Allylation of Cyclic Imides and Subsequent Coupling Reactions with Carbon Nucleophiles

  • Kang, Seok-Won;Heo, Eun-Young;Jun, Jong-Gab;Kim, Sung-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.25 no.12
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    • pp.1924-1928
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    • 2004
  • Allylations of N-benzyl and N-methyl cyclic imides were accomplished successfully under mild Barbier type conditions using zinc metal, allyl bromide and catalytic amount of $PbBr_2$. Subsequent coupling reactions with some carbon nucleophiles afforded 1,2- and 1,4-addition products in moderate to high yields.

Suppression of Aluminum Corrosion in Lithium Bis(trifluoromethanesulfonyl)imide-based Electrolytes by the Addition of Fumed Silica

  • Louis, Hamenu;Lee, Young-Gi;Kim, Kwang Man;Cho, Won Il;Ko, Jang Myoun
    • Bulletin of the Korean Chemical Society
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    • v.34 no.6
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    • pp.1795-1799
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    • 2013
  • The corrosion property of aluminum by lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) salt is investigated in liquid and gel electrolytes consisting of ethylene carbonate/propylene carbonate/ethylmethyl carbonate/diethyl carbonate (20:5:55:20, vol %) with vinylene carbonate (2 wt %) and fluoroethylene carbonate (5 wt %) using conductivity measurement, cyclic voltammetry, scanning electron microscopy, and energy dispersive X-ray spectroscopy. All corrosion behaviors are attenuated remarkably by using three gel electrolytes containing 3 wt % of hydrophilic and hydrophobic fumed silica. The addition of silica particles contributes to the increase in the ionic conductivity of the electrolyte, indicating temporarily formed physical crosslinking among the silica particles to produce a gel state. Cyclic voltammetry also gives lower anodic current responses at higher potentials for repeating cycles, confirming further corrosion attenuation or electrochemical stability. In addition, the degree of corrosion attenuation can be affected mainly by the electrolytic constituents, not by the hydrophilicity or hydrophobicity of silica particles.

Herbicidal Activity and Molecular Similarity of 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-thiourea Derivatives (1-(4-chloro-2-fluoro-5-propargyloxyphenyl)-3-thiourea 유도체의 제초활성과 분자 유사성)

  • Soung, Min-Gyu;Park, Kwan-Yong;Song, Jong-Hwan;Sung, Nack-Do
    • Applied Biological Chemistry
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    • v.51 no.3
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    • pp.219-222
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    • 2008
  • In the search for third generation herbicidal cyclic imide derivatives, the average values of herbicidal activity ($pI_{50}$) in vivo (pre-emergence) of 40 new peroxidizing herbicides, 1-(4-chloro-2-fluoro-5-propargyloxyphenyl)thiourea derivatives (1-40) against rice plant (Orysa sativa) and barnyard grass (Echinochlor crus-galli) were studied. The molecular similarity between protoporphyrinogen IX (protogen) as the substrate of protox enzyme and Urea derivatives (1-40) was discussed quantitatively. The diallyl (20) and 3-nitro substituent (33) showed the selective herbicidal activity against barnyard grass. Allyl substituent (8) and their molecular similarity in dice (S=0.81) showed the highest levels of herbicidal activity ($pI_{50}$=4.71). Also, similarity indices (S) and superimposed volume (C) of protogen and aryl-substituents (21-40) showed good correlation.

Synthesis and herbicidal activities of 2-(5-Propargyloxyphenyl)-4,5,6,7-tetrahydro-2H-indazole and their related derivatives (새로운 2-(5-Propargyloxyphenyl)-4,5,6,7-tetrahydro-2H-indazole의 합성과 제초활성)

  • Jeon, Dong-Ju;Park, Kwaun-Yong;Kim, Young-Mi;Kim, Hyoung-Rae;Song, Jong-Hwan;Hwang, In-Taek;Ryu, Eung-K.
    • The Korean Journal of Pesticide Science
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    • v.5 no.4
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    • pp.68-71
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    • 2001
  • Of the cyclic imide type compounds, S-275 was known to exhibit a potent herbicidal effects. We have designed and synthesized the compounds having diverse subsutuents in place of the chlorine group of bicyclic 4,5,6,7-tetrahydroindazole part of S-275. Their herbicidal activities were studied under flooded paddy conditions. The results showed that the most compounds gave relatively weak herbicidal activities, whereas tile compound substituted with methylthio group showed potent herbicidal effects against paddy weeds at a rate of 0.015 kg/ha and improved tolerance on rice compared to S-275.

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Synthesis and herbicidal activities of 9-(5-isoxazolemethoxy-phenyl)imino-8-thia-1,6-diazabicyclo[4.3.0]nonan-7-one and their related derivatives (새로운 9-(5-isoxazolemethoxyphenyl)imino-8-thia-1,6-diazabicycio [4.3.0]nonan-7-one 유도체의 합성과 제초활성)

  • Jeon, Dong-Ju;Park, Kwaun-Yong;Chung, Soon-Min;Kim, Hyoung-Rae;Song, Jong-Hwan;No, Zae-Sung;Hwang, In-Taek
    • The Korean Journal of Pesticide Science
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    • v.7 no.4
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    • pp.310-313
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    • 2003
  • New series of 9-(5-Isoxazolemethoxyphenyl)imino-8-thia-l,6-diazabicyclo[4.3.0]nonan-7-one which are the cyclic imide type compounds were designed and synthesized. The herbicidal activities of main dominant weeds to these compounds were evaluated under rice field condition. There is the possibility for a new herbicide since the most of compounds were excellent to main dominant weeds occurring in rice field without the serious rice injury.

New method for the synthesis of 3-chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole (3-Chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole의 제조방법에 관한 연구)

  • Park, Chang-Min;Park, Kwan-Young;Kim, Hyoung-Rae;Song, Jong-Hwan;Hwang, In-Taek;Jeon, Dong-Ju
    • The Korean Journal of Pesticide Science
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    • v.9 no.1
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    • pp.23-25
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    • 2005
  • 3-Chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole, which is the key intermediate of cyclic imide type compounds such as EK 5439 and S-275 series, were practically synthesized by the procedure of hydrolysis of by-products and were produced in the reaction of 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahydroindazol-3-one with phosgene.

Synthesis and Film Properties of Cross-linked Polysulfone with Imide Side Chain (이미드 곁가지로 가교되는 폴리설폰의 합성 및 필름 특성)

  • Lee Eun-Sang;Hong Sung-Kwon;Kim Yong-Seok;Lee Jae-Heung;Kim In-Sun;Won Jong-Chan
    • Polymer(Korea)
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    • v.30 no.2
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    • pp.140-145
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    • 2006
  • The mort commonly available substrate material is glass in the display fibrication process. However, glass is not desirable due to its heaviness and fragility. Recently, plastics such polysulfone (PSF), polyethesulfone (PES), polycarbonate (PC), polyethylene terephthalate (PET) and cyclic olefin polymers (COP) have been investigated to replace glass as a substrate material for display fibrication. Plastic substrates are advantageous in that they are lightweight, huh impart resistance, flexibility, and ability for roll to roll manufacturing process. But many plastics have poor chemical resistance in organic solvent. The chemica resistance is also lequired because they are exposed to solvents for various chemical treatments din the manufacturing process. So, we have an interest in the chemical modification of PSF to improve chemical resistance. We introduced crosslinkable imide moieties using chloromethylation method for the modification of PSF which could be overcome above shortcomings for display substrate based on plastic film. We prepared the cross-linked polysulfone films which were represented chemical resistance in HeOH, THF, DMSO and NMP. The thermal properties were measured by TGA, DSC and TMA. As the results, we have confirmed to enhance of the thermal property. They had low coefficient of thermal expansion (CTE) which decreased to 15% and had increased $T_g\;from\;180^{\circ}C\;to\;252^{\circ}C$. Cross-linked polysulfone films with imide side-chain had good optical properties and chemical resistance so that they could be used as flexible display substrate.

Preparation and Curing Studies of Maleimide Bisphenol-A Based Epoxy Resins

  • Nanjunda Gowda, Shivananda Kammasandra;Mahendra, Kadidal Nagappa
    • Bulletin of the Korean Chemical Society
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    • v.27 no.10
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    • pp.1542-1548
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    • 2006
  • Maleimide modified epoxy compounds were prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with diglycidylether of bisphenol-A. Triphenylphosphine was used as catalyst and methylethylketone as solvent. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of the maleimide epoxy compound with amine curing agents such as 1-(2-aminoethyl) piperazine (AEP) and 5-amino-1,3,3-trimethylcyclohexane methylamine isophorone diamine, IPDA) were studied. Incorporation of maleimide groups in the epoxy resin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples were found to have good thermal stability, chemical resistance (acid/alkali/solvent) and water absorption resistance.

Synthesis, Characterization and Curing Studies of Thermosetting Epoxy Resin with Amines

  • Lakshmi, B.;Shivananda, K.N.;Mahendra, K.N.
    • Bulletin of the Korean Chemical Society
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    • v.31 no.8
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    • pp.2272-2278
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    • 2010
  • A new hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) is prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with Epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possesses both the oxirane ring and maleimide group. The curing reaction of these maleimidophenyl glycidylether epoxy compound (N-MPGE) with amines as curing agents such as ethylendiamine (EDA), diethylentriamine (DETA) and triethylenetetramine (TETA), aminoethylpiperazine (AEP) and isophoronediamine, IPDA), are studied. Incorporation of maleimide groups in the epichlorohydrin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples exhibited good thermal stability, excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.