• Title/Summary/Keyword: phthalic acid

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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.

Analysis of Degradation Products in Madder Dyed Fabrics in Selective Degradation Conditions (퇴화조건에 따른 꼭두서니 염색물의 퇴화물 연구)

  • Ahn, Cheun-Soon;Obendorf, S.-Kay
    • Journal of the Korean Society of Clothing and Textiles
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    • v.29 no.12 s.148
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    • pp.1608-1618
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    • 2005
  • The purpose of this investigation was to investigate the degradation products of the dye component extracted from madder dyed fabrics using the GC-MS analysis and to evaluate the change of color due to degradation treatment. Four different degradation protocols were used in this study,; refrigeration at $7^{\circ}C$ (LT), room temperature (RT), oven treatment at $100^{\circ}C$ (OV), and $H_2O_2/UV(PER)$ method. Degradation times for each thermal system were 6 hour, 24 hour, 48 hour, 1 week, 2 week, 4 week. Alizarin was detected from the control and degraded samples of both alizarin dyed and madder dyed fabrics. Benzoic acid, 2, 4-di-tert-butylphenol, phthalic anhydride were detected as the degradation products for both alizarin dyed and madder dyed fabrics. The result suggest that these products can be used as the fingerprints of GC-MS analysis for the identification of madder dye in archaeological textiles. Both alizarin dyed and madder dyed samples became less red and less yellow after degradation. In the PER degradation system madder dyed sample showed the greatest color difference even after 1 week of degradation treatment. Further research is necessary for investigating the color change in the exhumed textiles, which is caused by the dual action of dye fading and the staining of organic matters in the soil.

Studies on the effect of phthalimido methyl-O,O-dimethyl-phosphorodithioate (Imidan) and its possible metabolites on the growth of rice plant (Phthalimido methyl-O,O-dimethyl phosphorodithioate (Imidan)과 그의 대사물질(代謝物質)이 수도(水稻) 생육(生育)에 미치는 영향(影響)에 관(關)한 연구(硏究))

  • Lee, Sung-Hwan;Lee, Dong-Suk;Lee, Jae-Koo
    • Applied Biological Chemistry
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    • v.7
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    • pp.105-117
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    • 1966
  • This experiment was conducted to investigate the effet of phthalimido-methyl-O,O-dimethyl-phosphorodithioate (Imidan) known as an acaricide and its possible metabolic products on the growth of plant, when sprayed on the leaves of rice plant. The results are summarized as follows. 1) Possible metabolic products of Imidan, the following compounds were synthesized or recrystallized for the present experiment a) N-Hydroxymethyl phthalimidem b) Phthalimide c) Phthalamidic acid d) Phthalic acid e) Anthranilic acid f) p-Amino benzoic acid g) p-Hydroxy benzoic acid h) Benzoic acid 2) Among the above materials, a), c), d), e), and Imidan were dissolved in a buffer solution respectively to be 10 and 20 p.p.m. and tested with the wheat coleoptile straight growth method. According to the results, Imidan inhibited the growth of coleoptile in both 10 and 20 p.p.m., whereas the others showed much better growth than the control, especially phthalamidic acid in 10 p.p.m. It appears that Imidan itself inhibits the coleoptile growth, whereas the metabolites derived from Imidan through various metabolisms, including hydrolysis in plant tissues show growth-regulating activity. (refer: Table 1, Fig. 1) 3) 20, 100 and 200 p.p.m. solutions of Imidall emulsion in xylene f·ere prepared. The lengths of shoot and root of rice seeds germinated on the re-respective media were measured after 12 days. The data showed that root was much more elongated in Imidan 20 p.p.m., whereas shoot in Imidan 100 p.p.m., respectively, than in the xylene control. An interesting finding was that xylene used as solvent had a tendency to inhibit seriously the root growth of rice seed. (refer: Table 2,5). 4) The emulsions of concentrations in 10, 25, 50 and 100 p.p.m's of control, Imidan, N-hydroxy methyl phthalimide, anthranilic acid, and phthalmide, respectively, were sprayed twice on the rice plant on pot. After a certain period of time lengths of rice culms were measured, showing that plots treated with Imidan and N-hydroxy methyl phthalimide exhibited much more growth than those of control and the others. 5) Loaves and stems of rice plant were sampled and extracted with dried acetone at the intervals of 3-, 5-, 7-, and 14 days after treated with Imidan 250 p.p.m. emulsion. This sample extracted with acetone was purified by means of prechromatographic purification method with acetonitrile and paperchromatographed to detect the following metabolic products. Imidan (Rf: 0.97-0,98), N-hydroxy-methyl phthalimide (Rf: 0.87) phthalimide (Rf: 0.86-0.87), phthalamidic acid (Rf: 0.13-0.14), phthalic acid (Rf: 0.02-0.03), benzoic acid (Rf: 0.42-0.43), p-amino benzoic acid or p-hydroxy benzoic acid (Rf: 0.08-0.09), and unidentified compounds (Rf: 0.73, 0.59, 0.33, 0.23. 0.07). In addition, in the early stages, such as 3- and 5 days nonhydrolyzed Imidan and its first hydrolytic product, N-hydroxymethyl phthalimide were detected in relatively large amounts, whereas in the last stages of 7- and 14 days due to further decomposition, the afore-mentioned two materials were reduced in the amount and p-hthalic, phthalamidic, benzoic, and p-Hydroxy benzoic, or p-Amino benzoic acids were detected in a considerably large amount. It is, therefore, believed that most of Imidan applied to the leaves of rice plant may be decomposed within almost 14 days. In the light of above observations it is considered that Imidan itself is not involved in plant growth regulating activity, whereas various phthaloyl derivatives produced in the course of metabolism (namelr, enzymic action) in plant tissues may have such effect.

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New Antibacterial Peptide Analogs of 5-Aminobenzimidazoles (새로운 펩티드 유사체인 5-aminobenzimidazoles의 합성)

  • Gondal, Humaira Y.;Mashooda, H.;Ali, Muhammad
    • Journal of the Korean Chemical Society
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    • v.55 no.4
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    • pp.650-655
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    • 2011
  • Three new peptide analogs 5a-c were obtained through coupling of 5-Amino benzimidazoles 2a-c with L-phenylalanine. For the purpose ${\alpha}$-amino group was blocked with phthalic anhydride and activation of ${\alpha}$-carboxy group of phenylalanine was carried out by preparing phthaloyl-L-phenylalanyl chloride 4. After developing a successful peptide linkage, the phthaloyl group was removed by treating 5a-c with hydrazine hydrate to get free peptides 6a-c, purified through a column of Amberlite (IR-4B). All of these compounds 2a-c and 5,6a-c have been characterized on the basis of their IR, 1H NMR and EIMS analyses. Antibacterial activity of these compounds is also been reported.

In vitro approach to investigating the free radical generation of endocrine disruptor

  • Kim HJ;Kim BH;An KH
    • Proceedings of the Korea Society of Environmental Toocicology Conference
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    • 2001.05a
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    • pp.117-117
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    • 2001
  • We investigated Free radical generation of endocrine disrupter, bisphenol A and alkyl esters of phthalic acid (DEP, DBP) using lipid peroxidation, enzyme assay (SOD, Catalase, Gpx-px), Cell viability and phototoxicity. Bisphenol A are monomers of various plastics including polycarbonates and epoxy resins which are used in numerous consumer products. The release of BPA from some of these materials has recently been reported. (omitted)

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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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Studies on the Heavy Metal Removal Characteristics of $FeS_(S)$ in the Presence of Organic Ligand (유기 리간드 존재하에서 $FeS_{(S)}$의 중금속 제거 특성 연구)

  • 박상원;박병주
    • Journal of Environmental Science International
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    • v.8 no.3
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    • pp.411-417
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    • 1999
  • The interfacial chemical behavior, lattice exchange and dissolution, of $FeS_{(S)}$ as one of the important sulfide minerals was studied. Emphases were made on the surface characterization of hydrous $FeS_{(S)}$, the lattice exchange of Cu(II) and $FeS_{(S)}$, and its effect on the dissolution of $FeS_{(S)}$, and also affect some organic ligands on that of both Cu(II) and $FeS_{(S)}$. Cu(II) which has lower sulfide solubility in water than $FeS_{(S)}$ undergoes the lattice exchange reaction when Cu(II) ion contacts $FeS_{(S)}$ in the aqueous phase. For heavy metals which have higher sulfide solubilities in water than $FeS_{(S)}$, these metal ions were adsorbed on the surface of $FeS_{(S)}$. Such a reaction was interpreted by the solid solution formation theory. Phthalic acid(a weak chelate agent) and EDTA(a strong chelate agent) were used to demonstrate the effect of organic lignads on the lattice exchange reaction between Cu(II) and $FeS_{(S)}$. The $pH_{zpc}$ of $FeS_{(S)}$ is 7 and the effect of ionic strength is not showed. It can be expected that phthalic acid has little effect on the lattice exchange reaction between Cu(II) and $FeS_{(S)}$. whereas EDTA has very decreased the removal of Cu(II) and $FeS_{(S)}$. This study shows that stability of sulfide sediments was predicted by its solubility. The pH control of the alkaline-neutralization process to treat heavy metal in wastewater treatment process did not needed. Thereby, it was regarded as an optimal process which could apply to examine a long term stability of marshland closely in the treatment of heavy metal in wastewater released from a disussed mine.

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Characterization of Colorless and Transparent Polyimide Films Synthesized with Various Amine Monomers (다양한 아민 단량체로 합성한 무색투명 폴리이미드 필름 특성)

  • Choi, Il-Hwan;Chang, Jin-Hae
    • Polymer(Korea)
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    • v.34 no.5
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    • pp.480-484
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    • 2010
  • A series of poly(amic acid)s(PAAs) was prepared by reacting 4,4'-(4,4'-isopropylidenediphenoxy) bis(phthalic anhydride)(BPADA) as the anhydride monomer and 2,2'-bis(trifluoromethyl) benzidine (TFB), bis(3-aminophenyl)sulfone (APS), 4,4'-methylenebis-(2-methylcyclohexylamine) (MMCA), or bis[4-(3-aminophenoxy) phenyl] sulfone (BAPS) as the amine monomer with 5 mol% melamine in N,N-dimethylacetamide (DMAc). Colorless and transparent polyimide (PI) films were obtained by casting the PAAs at various heat treatment temperatures. The thermo-mechanical properties and optical transparency of the PI films were investigated. The thermal properties of the PI films were examined using differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and thermomechanical analysis (TMA), and their optical transparency were measured by spectrophotometry. The coefficient of thermal expansion (CTE) and yellow index (YI) values of all samples were in the range of $48.53-64.24ppm/^{\circ}C$ and < 3.0, respectively.

Residue levels of phthalic acid esters (PAEs) and diethylhexyl adipate(DEHA) in various industrial wastewaters (업종별 산업폐수 중 프탈산에스테르와 디에틸헥실아디페이트의 잔류수준)

  • Kim, Hyesung;Park, Sangah;Lee, Hyeri;Lee, Jinseon;Lee, Suyeong;Kim, Jaehoon;Im, Jongkwon;Choi, Jongwoo;Lee, Wonseok
    • Analytical Science and Technology
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    • v.29 no.2
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    • pp.57-64
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    • 2016
  • Many phthalic acid esters (PAEs), including DMP, DEP, DBP, BBP, and DEHP, as well as DEHA are widely used as plasticizers in plastics. An analytical method was developed and used to analyze these compounds at 41 industrial facilities. The coefficient of determination (R2) for each constructed curve was higher than 0.98. The method detection limit (MDL) values were 0.4–0.7 μg/L for PAEs and 0.6 μg/L for DEHA. In addition, the recovery rate was shown to be 77.0–92.3%, while the relative standard deviation was shown to be in the range of 5.8-10.5%. DMP (n = 3), DEP (n = 2), DBP (n = 2), BBP (n = 2), and DEHA (n = 3) were detected in the range of 2.2-11.1% in the influent. DEHP was a predominant compound and was detected at > MDL in both the influent (n = 16, 35.6%) and the effluent (n = 4, 10.0%) at a high removal efficiency (92–100%). The highest levels of residue in industrial wastewater influent were 137.4 μg/L of DEHP at plastic products manufacturing facility, 12.5 μg/L of DEHA at a chemical manufacturing facility, and 14.0 μg/L of DEP at an electronics facility. The highest concentration of effluent was 12.5 μg/L of DEHP at a chemical manufacturing facility, which indicated that the effluent was below the allowable concentration (800 μg/L). Therefore, the levels of PAEs and DEHA that are discharged into nearby streams could not influence the health of the ecosystem.

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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