• Title/Summary/Keyword: quaternization

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Studies on the Quaternization of Tertiary Amines (Ⅳ). Kinetics and Mechanism for the Reaction of Substituted Phenacyl Tosylates with Substituted Pyridines

  • Lee, Oh-Seuk;Yoh, Soo-Dong
    • Bulletin of the Korean Chemical Society
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    • v.6 no.2
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    • pp.99-102
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    • 1985
  • Substituent effects of substrate and nucleophile for the reaction of substituted phenacyl tosylates with pyridines were determined conductometrically in acetonitrile. Activation parameters for these reactions were also calculated. The substituent effects in nucleophile were increased with electron-donating power of pyridines and Br${\o}$nsted linear relationship was shown. Rate constant was increased by both electron-donating and electron-attracting groups in the substrate. It seems that dissociative S$_{N}$2 ("loose" transition state) mechanism is operating in the case of electron-donating substituents while associative S$_{N}$2 ("tight" transition state) mechanism is operative in the case of electron-attracting substituents.

Influence of Quaternary Ammonium Anion Exchange Moieties onto Mechanical Properties of Radiation-grafting Anion Exchange Membranes (방사선그라프팅 음이온교환막의 기계적 물성에 대한 4차 암모늄 음이온교환기의 영향)

  • Ko, Beom-Seok;Sohn, Joon-Yong;Shin, Junhwa
    • Journal of Radiation Industry
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    • v.6 no.1
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    • pp.49-54
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    • 2012
  • Various anion exchange membranes were prepared by radiation graft copolymerization of vinylbenzyl chloride onto fluorinated films and subsequent quaternization with various tertiary amines such as trimethylamine, N,N-dimethylbuthylamine, N,N-dimethylaniline, and N-methylpiperidine. The quaternizations of the anion exchange membranes were confirmed by measuring of the ion exchange capacities of the membranes. The mechanical properties and the water uptakes were also measured. The elongation at break was found to be largely dependent on the fluorinated film, the quateranry ammonium, and the degree of grafting. The results indicate that the poly (ethylene-alt-tetrafluoroethylene) with quaternized trimethylamine moiety exhibits higher flexible property compared to the other prepared anion exchange membranes.

Antibacterial Activity by Chitosan Derivatives with Quaternary Ammonium Salt (4차 암모늄기를 가진 키토산 유도체의 항균성)

  • Kim, C.H.;Choi, Y.S.;Choi, K.S.
    • Applied Chemistry for Engineering
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    • v.7 no.5
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    • pp.1020-1026
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    • 1996
  • Chitosan is the deacetylation product of chitin. Chitosan was converted to N-alkyl chitosan derivatives using proper aldehyde having different alkyl chains, then chitosan derivatives with quaternary ammonium salt were producted by quaternization with methyl iodide. Their antibacterial activities aganst S. aureus(ATCC 6538P) and E. coli (ATCC 14339), gram-positive bacteria and gram-negative bacteria, respectively, as introduced alkyl length were evaluated by shake flask method using colony count. The antibacteiral activity was found to be increased as alkyl chains. hydrophobic goups. These antibacterial agents were more active against S. aureus than E. coli. It may be due to the different of structure of cytoplasmic membrane.

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Synthesis and Permeability of Cationic Polycarbonate-Polyurethane (양이온성 폴리카보네이트-폴리우레탄의 합성과 분리특성)

  • Lee, Snag-Woo;Oh, Boo-Keun;Lee, Young-Moo;Noh, Si Tae;Kim, Kea-Yong
    • Applied Chemistry for Engineering
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    • v.1 no.1
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    • pp.52-62
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    • 1990
  • Cationic polycarbonate type polyurethane was prepared from the quaternization reaction of N-methyldiethanolamine(MDEA) in urethane backbone which was obtained from the reaction of polycarbonate polyol, MDI and MDEA(chain exetender). Tensile strength and modulus of the cationic urethane resins were increased sharply with increasing the ionic content in urethane backbone. But hydrolysis resistance was decreased with increasing ionic contents. The selectivity of the cationic polycabonate urethane membrane for water/ethanol separation by pervaporation was about 20. The carrier mediated transport mechanism was considered the most probable separation mechanism for these membranes.

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Synthesis of Water Soluble Chitosan Derivatives with Quaternary Ammonium Salt and Their Flocculating Behavior (4차 Ammonium 기를 가진 새로운 수용성 Chitosan 유도체의 제조 및 이들의 응집거동에 관한 연구)

  • Kim, Chun-Ho;Jung, Byung-Ok;Choi, Kyu-Suk;Kim, Jae-Jin
    • Applied Chemistry for Engineering
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    • v.7 no.1
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    • pp.118-128
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    • 1996
  • N-methyl, N-butyl and N,N-dibutyl chitosan derivatives were prepared by Schiff's base formation and hydrogenation in aqueous media. Furthermore quaternization of the chitosan derivatives was performed in N-methyl-2-pyrrolidone using methyl iodide to obtain water soluble cationic polyelectrolytes. It was confirmed that O-alkylation was occured as well as selective N-alkylation in these reactions. Chitosan and chitosan derivatives with quaternary ammonium iodide showed high flocculation power as the cationic flocculant. When tested on paper mill waste water, they showed high flocculation power, independing of pH range. The flocculation power was increased as the N-alkyl chain length was increased. Among them, N-butyl dimethyl chitosan ammonium iodide showed better flocculation power than chitosan. But, N,N-dibutyl-N-methyl chitosan ammonium iodide showed less flocculation powre than chitosan itself.

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The Study on thickness uniformity of copper electrodeposits controlled by the degree of quaternization of imine functional group (구리 도금 평탄제의 imine 작용기 4차화에 의한 도금 두께 불균일도 제어에 관한 연구)

  • Jo, Yu-Geun;Kim, Seong-Min;Jin, Sang-Hun;Lee, Un-Yeong;Lee, Min-Hyeong
    • Proceedings of the Korean Institute of Surface Engineering Conference
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    • 2018.06a
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    • pp.77-77
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    • 2018
  • Panel level packaging (PLP) 공정은 차세대 반도체 패키징 기술로써 wafer level packaging 대비 net die 면적이 넓어 생산 단가 절감에 유리하다. PLP 공정에 적용되는 구리 재배선 층 (RDL, redistribution layer)은 두께 불균일도에 의해 전기 저항의 유동이 민감하게 변화하기 때문에 RDL의 두께를 균일하게 형성하는 것은 신뢰성 측면에서 매우 중요하다. 구리 RDL은 주로 도금 공정을 통해 형성되며, 균일한 도금막 형성을 위해 도금조에 평탄제를 첨가하여 도금 속도를 균일하게 한다. 도금막에 대한 흡착은 주로 평탄제의 imine 작용기에 포함된 질소 원자가 관여하며, imine 작용기의 4차화에 의한 평탄제의 흡착 정도를 제어하여 평탄제 성능을 개선할 수 있다. 본 연구에서는 도금 평탄제에 포함된 imine 작용기의 질소 원자를 4차화하여 구리 RDL의 도금 두께 불균일도를 제어하고자 하였다. 유기첨가제와 4차화 반응을 위해 알킬화제로써 dimethyl sulfate의 비율을 조절하여 각각 0, 50, 100 %로 4차화 반응을 진행하였다. 평탄제의 4차화 여부를 확인하기 위해 gel permeation chromatography (GPC) 분석을 실시하였다. 도금은 20 ~ 200 um의 다양한 배선 폭을 갖는 구리 RDL 미세패턴에서 진행하였으며, 4차화 평탄제를 첨가하여 광학 현미경과 공초점 레이저 현미경을 통해 도금막 표면과 두께에 대한 분석을 실시하였다. GPC 분석을 통해 4차화 반응 후 알킬화제에 의해 나타나는 GPC peak이 감소한 것을 확인하였다. 광학 현미경 및 공초점 레이저 현미경 분석 결과, 4차화된 질소 원자가 존재하지 않는 평탄제의 경우, 도금 시 도금막의 두께가 불균일하였으며 단면 분석 시 dome 형태가 관찰되었다. 또한 100 % 4차화를 실시한 평탄제를 첨가하여 도금 한 경우 마찬가지로 두께가 불균일한 dish 형태의 도금막이 형성되었다. 반면, 50 % 4차화를 적용한 평탄제를 첨가한 경우, 도금막 단면의 형태는 평평한 모습을 보였으며 매우 양호한 균일도를 가지는 것으로 확인되었다. 이로 인해 imine 작용기를 포함한 평탄제의 4차화 반응을 통해 구리 RDL의 단면 형상 및 불균일도가 제어되는 것을 확인하였으며, 4차화된 imine 작용기의 비율을 조절하여 높은 균일도를 갖는 구리 RDL 도금이 가능한 것으로 판단되었다.

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Humidity Sensitive Properties of Humidity Sensor using Quaternized Cross-linked Copolymers of Vinylbenzyl chloride (4차 염화 가교화된 Vinylbenzyl chloride 공중합체를 감습막으로 이용한 습도센서의 감습 특성)

  • Lee, Seong-Su;Gong, Myeong-Seon
    • Korean Journal of Materials Research
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    • v.10 no.12
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    • pp.825-830
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    • 2000
  • The copolymers with various composition of vinylbenzyl chloride (VBC), methyl methacrylate (MMA), and 2-hydroxyethyl methacrylate(HEMA) were synthesized as a humidity sensitive material and quaternized with N, N, N', N'-tetraethylene diamine.. Resistance versus relative humidity decreased with increase in the content of MMA in the copolymer. The introduction of HPMA increased the resistance of the humidity sensor as well as enhanced the adherence to the alumina substrate. In the case of VBC/MMA/HEMA=80/10/10, the hysteresis and temperature dependency coefficient were $\pm$2%RH and -0.46~0.42%RH/$^{\circ}C$. The average resistance at 30%RH, 60%RH and 90%RH were 3.0M$\Omega$ ,200k$\Omega$ and 9k$\Omega$, respectively.

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A Study on the Synthesis and Physical Properties of N-acyloxyethyl carboxybetaine Type Amphoteric Surfactants (N-acyloxyethylcarboxybetaine 형 양성계면활성제의 합성과 물성에 관한 연구)

  • Kim, Yong-In;Soh, Hie-Jeun;Oh, Yang-Hwan;Kim, Byung-Kie
    • Journal of the Korean Applied Science and Technology
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    • v.6 no.1
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    • pp.31-40
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    • 1989
  • Five novel amphoteric surfactants of N-acyloxyethylcarboxybetaine series were synthesized via Schotten-Baumman reaction between five acid chlorides containing 10, 12, 14, 16 and 18 carbon atoms in their N-alkyl groups and dimethylaminoethanol to give the intermediate products, 2-dimethylaminoethylalkanoates(2). Quaternization of these products(2) was permitted to from 2-(acyloxyethyldimethylammonic)- acetates(3), whose structures were identified by elemental analysis, IR spectrophotometry and $^1Hnmr$ spectrometry. The yield of the final products was shown in the range of 77-80% based on the intermediate products. The surface tension of the aqueous solution of (3) was measured, and the critical micelle concentrations (cmc) were shown in the range of $2.1\;{\times}\;10^{-3}\;-\;3.3\;{\times}\;10^{-4}mol/l$, and the surface tension at cmc was 28-36 dyne/cm. Cmc was lowered gradually by the increment of the length of N-alkyl ester containing group. The isoelectric point was shown in the range of 4.44-5.20. It showed a tendency to lean toward the acidic site and its range was broadened as increase of the hydrophobic group length. A linear relationship between log cmc and the number of carbon atoms(N) in the hydrophobic alkyl chain was shown in the relative equation of log cmc=-1.75-0.1N, and the contribution rate of N on the standard free energy change in micellization, ${\bigtriangleup}({\bigtriangleup}G^{\circ}m)/{\bigtriangleup}N$, was calculated as -0.23 RT.

Synthesis and Surface Activities of Betaine Amphoteric Surfactant Having Ether Bond (에테르 결합을 가진 베타인계 양성계면활성제(兩性界面活性濟) 합성(合成) 및 계면활성(界面活性))

  • Cha, Kyung-On;Lee, Hi-Jong;Kim, Yong-In
    • Journal of the Korean Applied Science and Technology
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    • v.9 no.1
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    • pp.63-71
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    • 1992
  • Four novel amphoteric surfactants of N-alkoxyethylcarboxybetaine series were synthesized via Schotten-Baurnman reaction between four alkyl chlorides contaning 10, 12, 14 and 16 carbon atoms in their N-alkyl group and dimethylaminoethanol to give the intermediate products, alkoxyethyldimethylamine, Quaternization of these intermediates was permitted to form 2-(alkoxyethyldimethylarnmonio) acetates, whose structures were identified by elemental analysis. IR spectrophotometry and $^1$Hnmr spectrometry. The yield of the final products was shown in the range of $74{\sim}77%$ based on the yield of the intermediate products, Surface tension of the aqueous solution of the final products was measured. and the critical micelle concentrations(cmc) were shown in the range of $2.82{\times}10^{-3}{\sim}2.67{\times}10^{-6}$mol/l, and the surface thension at erne was 35${\sim}$43dyne/cm. Cmc was lowered gradually by the increase of carbon numbers in N-alkyl ether containing group. The isoelectric point was shown in the range of 4.08${\sim}$6.03. It showed a tendency to lean toward the acidic site and its range was broadened as increase of the hydrophobic group length. A linear relationship between log erne and the number of carbon atoms(N) in the hydrophobic alkyl chain was shown in the relative equation of log cmc=2.49-0.50N.

Resistive Humidity Sensor Using New N-Methacryloyl-N'-ethyl-N'-propyl Piperazinium Bromide Monomer and Their Properties (새로운 N-Methacryloyl-N'-ethyl-N'-propyl Piperazinium Bromide 단량체를 사용한 습도센서 및 그들의 특성 조사)

  • Lee, In-Ho;Park, Chan-Kyo;Gong, Myoung-Seon
    • Polymer(Korea)
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    • v.33 no.4
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    • pp.326-332
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    • 2009
  • New humidity-sensitive monomer, N-methacryloyl-N'-ethyl-N'-propyl piperazinium bromide (MANEPPB) was prepared by the quaternization reaction of N-methacryloyl-N'-ethyl piperazine (MANEP) with 1-bromopropane. Polyelectrolytes derived from the copolymers composed of MANEPPB/MMN/AA=60/35/5, 70/25/5, 80/15/5, 90/5/5 and 95/0/5 were prepared for the humidity-sensitive membranes, which were fabricated on the gold electrode by dipping method and were crosslinked by reacting copolymers with aziridine crosslinker, trimethylolpropane tris(2-methyl-1-aziridinopropionate) (TTAP). When the resistance dependences on the relative humidity of the sensors were measured, it was found that the resistance varied three orders of magnitude between 20 and 90%RH, which was satisfied with the requirement for the common humidity sensor operating at ambient humidity. Their hysteresis, temperature dependence, frequency dependence, response and recovery time and water durability were measured and evaluated as a humidity-sensing membrane.