• Title/Summary/Keyword: Phthalic anhydride

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Synthesis and Curing Behaviors of Polyisoimide Oligomers with Ethynyl End Groups (Ethynyl 말단기를 갖는 Polyisoimide 올리고머의 합성 및 이들의 경화거동에 관한 연구)

  • Choi, Seok Woo;Kim, Bo Ock;Kim, Ji-Heung;Nam, Sung Woo;Jeon, Boong Soo;Kim, Young Jun
    • Polymer(Korea)
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    • v.38 no.6
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    • pp.774-781
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    • 2014
  • Acetylenic or phenylethynyl end-capped polyisoimide oligomers ($M_w$ 2500 g/mol, 5000 g/mol) based upon 4,4'-diamino diphenyl ether (4,4'-ODA)/4,4'-oxydiphthalic anhydride (ODPA) and 4,4'-ODA/3,3',4,4'-benzophenone tetracarboxylic acid dianhydride (BTDA) were synthesized by using 4-ethynylaniline (4-EA) or 4-phenylethynyl phthalic anhydride (4-PEPA) as an end capper. The incorporation of ethynyl groups were confirmed by FTIR spectroscopy. The isomerization temperature was influenced by molecular weight as well as the backbone structure of polyisoimides oligomers. Thus, polyisoimide oligomers with molecular weight of 2500 g/mol was found to be imidized at temperature $10^{\circ}C$ lower than that for the oligomers with molecular weight of 5000 g/mol. The crosslinking reaction of ethynyl groups occurred at a higher temperature than that for the isoimide/imide isomerization reaction. These two reactions were totally or partially overlapped on the DSC thermograms for the polyisoimide oligomer end-capped with 4-EA. Kinetics of thermal imidization and crosslinking reactions for the 4,4'-ODA/ODPA polyisoimide oligomers end-capped with 4-PEPA were investigated by performing dynamic DSC experiments at heating rate of $10^{\circ}C/min$. The activation energy and pre-exponential factors were 141 kJ/mol and $1.45{\times}10^{13}min^{-1}$ for the imidization reaction and 177 kJ/mol and $2.90{\times}10^{13}min^{-1}$ for the crosslinking reaction, respectively.

Synthesis and Properties of New Phthaloperinone Dyes (신규 Phthaloperinone 색소의 합성과 특성에 대한 연구)

  • Jun, Kun;Gwon, Seon Yeong;Kim, Sung Hoon
    • Textile Coloration and Finishing
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    • v.27 no.4
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    • pp.275-280
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    • 2015
  • New series of phthaloperinone dyes were synthesized by the condensation reaction between tetrachloro-phthalic anhydride, 2,3-naphthalene dicarboxylic anhydride and o-phenylenediamine, 1,8-diaminonaphthalene, 1,2-diaminoanthraquinone. These dyes absorb at around 370-490nm. It was found that introduction of naphthalene and anthraquinone moiety on the perinone system produces a large bathochromic shift of 100nm. The synthesized dye 7 containing anthraquinone moiety in perinone chromophoric system exhibited superior heat stability and bright color as yellow chromophore. New dye 7 have been investigated in terms of interacting with volatile organic compound(VOC) $EtNH_2$. The sensing behaviour of the dye 7 toward $EtNH_2$ was studied by UV-vis absorption spectroscopy. Sensing mechanism of dye 7 to $EtNH_2$ was supported by theoretical calculations based on DFT method.

Thermal Properties of Cured Epoxy Resin Filled with Rubber Complex-Treated Silica (고무상 복합물로 표면처리 한 실리카를 충전한 에폭시 수지 경화물의 열적 특성)

  • Choi, Sang-Goo;Suh, Won-Dong
    • Elastomers and Composites
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    • v.32 no.1
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    • pp.11-19
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    • 1997
  • [ ${\gamm}-Glycidoxy$ ] propyl trimethoxy silane, CTBN rubber(carboxyl terminated butadiene acrylonitrile rubber) and GMA(glycidyl methacrylate) were reacted on the surface of silica one by one in existence of TEA(triethylamine) or BPO(benzoyl peroxide). The amount of reactant was $2.5{\sim}5.8%$ of treated silica weight. The treated silica was mixed with epoxy resin and MTHPA(methyl tetrahydro phthalic anhydride) in the range of $0{\sim}60%$(wt.%) of total component. The thermal properties were tested for cured products. By using silica treated with silane/rubber or silane/rubber/vinyl, comparing with 3% of rubber mixed directly, it had 13% higher $T_g$ and 10% lower thermal expansion coefficient at $35{\sim}55%$ of silica contents.

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Synthesis of Aminophosphonate Derivatives Containing 7-Aminocephalosporanic acid (7-Aminocephalosporanic acid를 포함하는 Aminophosphonate유도체의 합성)

  • Kim, Sang Bum
    • Applied Chemistry for Engineering
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    • v.8 no.4
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    • pp.700-703
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    • 1997
  • 7-Aminocephalosporanic acid(7-ACA) was reacted with diphenyldiazomethane(DPM) to get diphenylmethyl 7-$\beta$-(O-ethylphthalimidomethylphosphony1)-3-acetoxymethyl-3-cephem-4-carboxylate. Diethyl phthalimidomethylphosphonate was chloridated with a slight excess of phosphorus pentachloride to the O-ethyl phthalimidoalkylphosphonochloridate. Previously unreported two compounds, diphenylmethy1 -7-$\beta$-(O-ethylphthalimidomethylphosphony1)-3-acetoxymethyl-3-cephem-4-carboxylate and diphenylmethyl-7-$\beta$-[O-ethylphthalimidoethylphosphonyl]-3-acetoxymethyl-3-cephem-4-carboxylate were synthesized by cupling reaction of DPM 7-ACA and O-ethyl phthalimidoalkylphosphonochloridate. All of the compounds including starting materials and reaction intermediates were characterized by $^1H$ NMR and FT-IR spectroscopy.

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Polyhydroxyamic Acid from 3,3′ - Dihydroxybenzidine and Pyromellitic Dianhydride as a Fire-safe Polymer

  • Park, Seung Koo;Farris, Richard J.;Kantor, Simon W.
    • Fibers and Polymers
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    • v.5 no.2
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    • pp.83-88
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    • 2004
  • In order to assess the potential of the hydroxy-containing polyamic acid (PHAA) synthesized from 3,3'-dihydroxy benzidine and pyromellitic dianhydride for a fire-safe polymer, the cyclization pathway of PHAA has been investigated using a model compound prepared from 2-aminophenol and phthalic anhydride. The reaction was monitored. by $^1{H-nuclear}$ magnetic resonance. N-(2-hydroxyphenyl) phthalamic acid is converted to N-(2-hydroxyphenyl) phthalimide at ca. 175$^{\circ}C$, showing endothermic reaction. The imide structure is rearranged to the benzoxazole structure over ca. $400^{\circ}C$. These results are similar with that of PHAA. According to pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) data, water and carbon dioxide are released during the cyclization and rearrangement reaction. One DMAc molecule is complexed with one carboxyl acid group in PHAA, which accelerates the imidization process to release more easily the flame retardant, water.

Kinetics of the Formation of Nickel-Phthalocyanine (Nickel-Phthalocyanine 생성의 반응속도론적 연구)

  • Bae, Kook-Jin;Hahn, Chi-Sun
    • Journal of the Korean Chemical Society
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    • v.16 no.2
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    • pp.84-92
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    • 1972
  • A mechanism for the ring formation of nickel phthalocyanine (Ni-Pc) has been proposed based on chemical kinetics. The effect of the catalyst on the rate was examined, and ammonium molybdate has been found to be the most effective. The reaction order of the ring formation was determined to be of the 1st order over all, with only the concentration of urea affecting the rate of the ring formation. All the results including thermodynamic parameters support a conclusion that the rate-determining step seems to be the enolization of the urea-catalyst transition complex, followed by fast decomposition of the tautomeric enolized urea into ammonia and isocyanic acid. These intermediates then reacted with the phthalic anhydride to form imino and diimino-phthalimide, which condense to form nickel phthalocyanine in the presence of the nickel cation.

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Facile Synthesis of $(\pm)$-2-[p-(1-Oxo-2-isoindolinyl)phenyl]butyric acid (Indobufen) ($(\pm)$-2-[p-(1-Oxo-2-isoindolinyl)phenyl]butyric acid(인도부펜)의 합성)

  • 최홍대;강병원;마정주;윤호상
    • YAKHAK HOEJI
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    • v.35 no.5
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    • pp.389-393
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    • 1991
  • A convenient method for the synthesis of indobufen, which is a potent antiinflammatory agent, was described. Ethyl 2-phenylbutyrate(4) was prepared by Friedel-Crafts reaction of benzene with ethyl $\alpha$-chloro-$\alpha$-(methylthio)acetate(l) followed by ethylation and desulfurization of the resultant ethyl 2-(methylthio)phenylacetate(2). Ethyl 2-(p-aminophenyl)butyrate(6) was prepared by nitration of (4) and successive reduction of ethyl 2-(p-nitrophenyl) butyrate(5). Indobufen was obtained by condensation reaction of (6) with phthalic anhydride followed by reduction and hydrolysis of the resultant ethyl 2-[p-(1, 3-dioxo-2-isoindolinyl)phenyl]butyrate(7).

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Synthesis of Novel Allylthio Heterocyclo(or aryl)alkylaminopyridazines and Their Anticancer Activity against SK-Hep-1 Cells

  • Lee, Myung-Sook;Kim, Eun-Sook;Moon, A-Ree;Park, Myung-Sook
    • Bulletin of the Korean Chemical Society
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    • v.30 no.1
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    • pp.83-91
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    • 2009
  • To develop new anticancer agents, 3-allylthio-6-aminopyridazine derivatives were synthesized from maleic anhydrides or phthalic anhydrides by formation of a pyridazine nucleus, dichlorination, allylthiolation and amination. The pyridazine nuclei were obtained by condensing a hydrazine monohydrate with maleic anhydride. An allylthio group as a pharmacologically active group was introduced into one side of a pyridazine ring. Arylalkylamines with benzene or pyridine moieties or heterocycloalkylamines with heterocycle moieties such as morpholine, piperidine, or pyrrolidine were also introduced into the para-position of allylthio pyridazine. These new compounds showed antiproliferative activities against SK-Hep-1 human liver cancer cells in MTT assays. These compounds are thus promising candidates for chemotherapy of hepatocellular carcinomas. Two compounds, 20c and 22a, showed higher potencies for inhibiting growth of hepatocellular carcinoma cells than did K6 ($ID_50$=1.08 mM). This suggests the potential anticancer activity of these two compounds.

Redox Property of Vanadium Oxide and Its Behavior in Cataltic Oxidation

  • 김영호;이호인
    • Bulletin of the Korean Chemical Society
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    • v.20 no.12
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    • pp.1457-1463
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    • 1999
  • Structure and their redox property of the vanadium oxides prepared by decomposing NH₄VO₃ at various temperatures were studied by XRD, SEM, XPS, and temperature programmed reduction/temperature programmed oxidation (TPR/TPO) experiment. All TPR profiles have two sharp peaks in the temperature range 650-750℃, and the area ratio of the two sharp peaks changed from sample to sample. There were three redox steps in TPR/TPO profiles. The oxidation proceeded in the reverse order of the reduction process, and both the reactions proceeded via quite a stable intermediates. The changes of the morphological factor $(I_{(101)}/I_{(010)})$, the ratio of $O_{1S}$ peak area (O$_{1S}$( α)/O$_{1S}$( β)) in the XPS results, and the ratio of hydrogen consumption in TPR profiles with various vanadium oxides showed the distinct relationship between the structural property and their redox property of vanadium oxides. The change of the specific yield of phthalic anhydride with various vanadium oxides showed a very similar trend to those of the peak area ratio in TPR profiles, which meant that the first reduction step related to the partial oxidation of o-xylene on the vanadium oxide catalyst.

Screening of Biologically Active Essential Oils from Ligusticum tenuissimum (고본(藁本)내 정유성분의 생리활성 탐색)

  • 김민희;김영길;이진하;홍거표;홍정기;공영준;이현용
    • Microbiology and Biotechnology Letters
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    • v.28 no.2
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    • pp.97-104
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    • 2000
  • Screening of Biologically Active Essential Oils from Ligusticum tenuissimum. Kim, Min-Hae, Young-Gil Kim, Jin-Ha Lee, Keo-Pyo Hong, Jung-Ki Hong, Young-Joon Kong, and Hyeon-Yong Lee*. Division of Food and Biotechnology, Kangwon National University, Chunchon 200-701, Korea, 1 Regional Crop Development Station, Kangwon Agricultural Research & Extension Services, Chunchon 200-150, Korea-The biological activities of the crude essential oils from Ligusticum tenuissimum and the control(phthalic anhydride) were compared. About 60% of the growth of MCF7, A549, and Rep3B cells were inhibited by adding 1.0 mg/ml of the crude essential oils and below 40% was observed by the control. Cytotoxicity on human normal lung cell(IMR90) was scored as 34.4% for the crude oil and 26.4% for control, respectively. It was found that the crude essential oils were more effective than the control in anti mutagenecity tested by both Rec-assay and CRG V79 cells. The growth of human T-cell(Jurkat) was enhanced up to 1.21 times by adding the crude essential oil compared with the control. 50% of a-glucosidase activity was inhibited by both the crude essential oil and the control. ACE activities were inhibited 80.1 % and 65.3% by adding 1.0 mg/ml of the crude oil and the control, respectively. The higher enhancement of glutathione-S-transferase activity was observed in the crude oil than those in the control: 301 % v.s 234% at 1.0 mg/ml of the treatment. Thrombolytic activity was measured as 42.9% and 28.6% for the crude oil and the standard, respectively. The effect of the oil on the nerve cells PCI2, was observed as follows: the neurite of PCl2 cells was lengthened up to 255 /-lm longer than 205 /-lm of control. The number of neurite-bearing cells were about two times higher than control. The survival ratio of the crude essential oil was also increased up to 56.4% which was about two fold higher than in control.

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