• Title/Summary/Keyword: quaternization

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Influence of Quaternization on UCST Properties of Hydroxyl-Derivatized Polymers

  • Lee, Hyung-Il
    • Bulletin of the Korean Chemical Society
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    • v.35 no.10
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    • pp.3001-3004
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    • 2014
  • A series of hydroxyl-derivatized quaternized polymers were successfully synthesized by atom transfer radical polymerization (ATRP) and Cu(I)-catalyzed 1,3-dipolar cycloaddition of azide and alkynes (click chemistry), followed by quaternization reactions. ATRP was employed to synthesize poly(2-hydroxyethyl methacrylate) (PHEMA), followed by introduction of alkyne groups using pentynoic acid, leading to HEMA-Alkyne. 2-Azido-1-ethanol and 3-azido-1-propanol were combined with the HEMA-Alkyne backbone via click reaction, resulting in triazole-ring containing hydroxyl-derivatized polymers. Quaternization reactions with methyl iodide were conducted on the triazole ring of each polymer. Molecular weight, molecular weight distribution, and the degree of quaternization (DQ) were determined by gel permeation chromatography (GPC) and $^1H$ NMR spectroscopy. The average molecular weight ($M_n$) of the resulting polymers ranged from $5.9{\times}10^4$ to $1.05{\times}10^5g/mol$ depending on the molecular architecture. The molecular weight distribution was low ($M_w/M_n$ = 1.26-1.38). The transmission spectra of the 0.1 wt % aqueous solutions of the resulting quaternized polymers at 650 nm were measured as a function of temperature. Results showed that the upper critical solution temperature (UCST) could be finely controlled by the level of DQ.

Study on the Synthesis of Polyurethane Cationomers and Their Mechanical Properties (양이온성 폴리우레탄의 합성 및 기계적 특성에 관한 연구)

  • Ann, Choun-Kee;Jin, Je-Yong;Choi, Sei-Yong
    • Elastomers and Composites
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    • v.33 no.3
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    • pp.177-184
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    • 1998
  • Polyurethane(PU) prepolymers were synthesized from polytetramethylene ether glycol(PTMG), with 4,4'-diphenylmethane diisocyanate(MDI), toluene 2,4-diisocyanate (TDI) and isophoron diisocyanate(IPDI). After chain extention using n-methyl-diethanol amine(n-MDEA), aqueous polyurethane cationomers were prepared by addition of glycolic acid(GA) as a quaternizer. The effect of the content of chain extender and the degree of neutralization on the stability of emulsion, adhesive strength, viscosity, glass transition temperature and physical properties of emulsion cast film were investigated using UTM, viscometer and DSC.

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Studies on the Quaternization of Tertiary Amine (V). The Quaternization of Pyridine with Phenacyl Arenesulfonates (3차 아민의 4차화 반응에 관한 연구 (제 5 보). 페나실 아렌술포네이트류에 의한 피리딘의 4차화반응)

  • Lee, Oh-Seuk
    • Journal of the Korean Chemical Society
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    • v.31 no.3
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    • pp.280-286
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    • 1987
  • The effect of substituent inleaving group on the rates of reactions of phenacyl substituted-benzenesulfonates with pyridine was determined conductometrically in acetonitrile and in methanol at 35, 45, and $55^{\circ}C$, respectively. The reaction rate became faster in proportion to electron-attracting ability of substituent, which indicates that the substituent in leaving group can directly control reaction rate. It was shown that the specific to the carbonyl carbon as the rate-determining step.

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Well-Defined Thermoresponsive Copolymers with Tunable LCST and UCST in Water

  • Jung, Seo-Hyun;Lee, Hyung-Il
    • Bulletin of the Korean Chemical Society
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    • v.35 no.2
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    • pp.501-504
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    • 2014
  • A thermoresponsive polymer, poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA), was successfully synthesized by atom transfer radical polymerization (ATRP). Different amounts of 1,3-propanesultone were used as quaternization agent to transit the PDMAEMA into partially modified poly(zwitterions), resulting in p[DMAEMA-co-3-dimethyl(methacryloyloxyethyl)ammonium propanesulfonate] (PDMAEMA-co-PDMAPS). Molecular weight, molecular weight distribution, and degree of quarternization were determined by gel permeation chromatography (GPC) and 1H NMR spectroscopy. The transmission spectra of the 1.0 wt % aqueous solutions of the resulting polymers at 650 nm were measured as a function of temperature. Results showed that the lower critical solution temperature (LCST) and the upper critical solution temperature (UCST) could be easily controlled by the different composition of dimethylamino and zwitterion groups. The effect of partial quaternization on thermoresponsive properties was also studied by dynamic light scattering (DLS) with the same aqueous concentration (1.0 wt %) as employed for turbidimetry studies. The LCST and UCST values measured by DLS correlated well with those determined by turbidimetry.

Quaternized Polyamidoamine Dendrimers as Novel Gene Delivery System: Relationship between Degree of Quaternization and Their Influences

  • Lee, Jung-Hoon;Lim, Yong-Beom;Choi, Joon-Sig;Choi, Myung-Un;Yang, Chul-Hak;Park, Jong-Sang
    • Bulletin of the Korean Chemical Society
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    • v.24 no.11
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    • pp.1637-1640
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    • 2003
  • Quaternary ammonium groups were introduced to Starburst polyamidoamine (PAMAM) dendrimers for a gene carrier. These quaternary dendritic carriers exhibited reduced cytotoxicity on 293T cells compared to parent dendrimers examined and their transfection efficiency were similar with parent dendrimers. Quaternization could be a promising tool to improve properties of dendrimers as a gene delivery carrier.

Synthesis and Functionalized Conditions of Quaternized Poly(vinylimidazole-co-trifluoroethylmethacrylate-co-divinylbenzene) Anion Exchange Membrane (질산성 질소 제거용 Quaternized Poly(vinylimidazole-co-trifluoroethylmethacrylate-co-divinylbenzene) 음이온교환막 제조와 관능화 조건)

  • Oh, Chang Min;Hwang, Taek Sung
    • Polymer(Korea)
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    • v.39 no.1
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    • pp.157-164
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    • 2015
  • In this study, we synthesized poly(vinylimidazole-co-trifluoroethylmethacrylate-co-divinylbenzene) (PVTD) copolymer and introduced functional group through quaternization reaction for removing nitrate from drinking water. Also, optimizing conditions (reaction time, reaction temperature and functionalized agents concentration) for introducing the functional group were confirmed. The basic properties such as water uptake, swelling ratio, electrical resistance, ion exchange capacity and anion permselectivity for removing nitrate from drinking water were measured. The optimal values of water uptake, electrical resistance and ion exchange capacity of synthesized anion exchange membrane were 51.2%, $5.4{\Omega}{\cdot}cm^2$, and 1.04 meq/g, respectively.

Platelet Anti-aggregating Activities of Higenamine Analogs (Higenamine 유도체들의 혈소판응집 억제작용)

  • 윤혜숙;백승환;이종란
    • YAKHAK HOEJI
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    • v.30 no.5
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    • pp.245-252
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    • 1986
  • Various structural analogs of higenamine, 1-(4'-hydroxylbenzyl)-6,7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline, were synthesized and their inhibitory activities against platelet aggregation induced by either arachidonic acid, ADP or collagen. Among the twenty-five compounds tested, inhibitory activity is favored by the 3, 4-dihydroisoquinoline system with the methyl bridge between the two aromatic rings replaced by either ethyl or ethenyl group. N-Methyl quaternization decreased the inhibitory activities. * 이논문의 내용중 편집상의 오류가 있습니다. 그에대한 정오표는 v.31, n.1의 45p.에 있습니다.

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1,2,4-Triazine III : Synthesis of 1-Methyl-1,2,4-triazinium Iodides and Their Ring Contraction Reaction to 1-Methyl-1,2,4-triazoles (1,2,4-Triazine III : 1,2,4-Triazine 유도체의 Methiodide 염 합성과 이들 염의 고리 축소화반응에 의한 1,2,4-Triazole 유도체 합성)

  • Jae Keun Lee;Ryu Hyang Sun;W. W. Paudler
    • Journal of the Korean Chemical Society
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    • v.33 no.4
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    • pp.419-425
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    • 1989
  • Various 1-methyl-1,2,4-triazinium iodides were easily synthesized by the reaction of various 1,2,4-triazines and methyl iodide in acetone. When methyl iodide salts of 1,2,4-triazine derivatives were treated with $K_3Fd(CN)_6$ in 10% NaOH solution, 1-methyl-1,2,4-triazole derivatives as the main products were obtained by ring contraction. In addition to 1-methyl-1,2,4-triazole derivatives, 1,6-dihydro-6-oxo-1,2,4-triazine derivatives as the minor products were also obtained when there were no substitutents in $C_6$-position of 1,2,4-triazines. The formation of pseudo base by $OH^-$ and then oxidation to either 1,6-dihydro-6-oxo-1,2,4-triazines or 1-methyl-1,2,4-triazoles were suggested as the mechanism of the ring contraction. This mechanism also verified that the position of quaternization was neither $N_2$ nor $N_4$ but 1-nitrogen of 1,2,4-triazine.

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Studies on the Preparation of Durable Softners using Alkyl Imidazoline and Fatty Carbamide (알킬이미다졸린과 지방산 카르바미드를 이용한 내구성 유연제의 제조에 관한 연구)

  • Jung, Choong-Ho;Park, Hong-Soo;Kim, Young-Keun
    • Applied Chemistry for Engineering
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    • v.4 no.1
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    • pp.54-63
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    • 1993
  • Some emulsified 1, 2-disubstituted imidazolinium salts were synthesized by quaternization of 1, 2-disubstituted imidazoline which had been prepared by the reaction of dodecanoic acid with tetraethylenepentamine. 2-Docosamido-2'-docosanoyloxydiethylamine was prepared by the reaction of docosanoic acid with hydroxylethylethylenediamine. Then, some emulsified fatty carbamide salts were also synthesized by quaternization of fatty carbamide which had been prepared by the reaction of urea with the 2-docosamido-2'-docosanoyloxydiethylamine. Some softners were prepared by blending of these salts mentioned above. These softners were treated on acrylic fiber, then several properties were measured. As the results, softening and lubricating properties are good and a little antistatic property was observed. The synthesized softners were also proved as a durable softner by means of the several experiments : bending resistance test and measurements of feeling change with washing according to the pH changes. The surface structure of acrylic fibers treated with the softner were characterized by SEM.

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Preparation of Amine-Containing Poly(amide-sulfone)s Using Vinylsulfone Reactive Monomers and Their Properties

  • Jeon, Young-Min;Lim, Tai-Ho;Kim, Soo-Han;Kim, Jong-Gyu;Gong, Myoung-Seon
    • Macromolecular Research
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    • v.15 no.1
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    • pp.17-21
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    • 2007
  • A series of new, vinyl sulfone-containing monomers was prepared by p-aminophenyl vinyl sulfone (1) with various acid chlorides such as adipoly chloride, terephthaloyl chloride and isophthaloyl chloride. Finally, tertiary amine-containing poly(amide-sulfone)s were prepared by the Michael-type addition polymerization using N,N-dimethylethylenediamine (DMEDA), p-phenylenediamine and piperazin. To evaluate the relevant properties for permselective membranes and enzyme substrate, various physical properties such as molecular weight, solubility, quaternization behavior and thermal properties were examined.