• 제목/요약/키워드: lactide

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Synthesis of Lactide from Oligomeric PLA: Effects of Temperature, Pressure, and Catalyst

  • Yoo, Dong-Keun;Kim, Duk-Joon;Lee, Doo-Sung
    • Macromolecular Research
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    • v.14 no.5
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    • pp.510-516
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    • 2006
  • Lactide was produced from oligomeric PLA by back-biting reaction of the OH end groups. For optimization of the reaction conditions, the effects of temperature, pressure, PLA molecular weight, and catalyst type on the lactide synthesis were examined. The fraction of D,L-lactide decreased with increasing temperature. Among the various Sn-based catalysts, the D,L-lactide fraction was maximized when SnO was used. A higher yield with lower racemization was observed at lower pressure. The conversion of PLA was maximized at an oligomeric PLA molecular weight of ca. 1380. The yield of lactide increased but the fraction of D,L-lactide decreased with increasing molecular weight. The highest conversion with the lowest racemization degree was obtained at a catalyst concentration of 0.1 wt%. The lactide was more sensitive to racemization because of the entropic effect.

Ring-Opening Polymerization of L-lactide with Glycidol as Initiator (Glycidol을 개시제로 이용한 L-lactide 개환중합)

  • Yim, Jin-Heong;Kim, Da Hee;Ko, Young Soo
    • Polymer(Korea)
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    • v.37 no.5
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    • pp.606-612
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    • 2013
  • Glycidol-poly(lactide) (Gly-PLA) were synthesized via L-lactide ring opening polymerization with glycidol as an initiator and $Al(O-i-Pr)_3$ catalyst. The structure of Gly-PLA was analyzed and successfully confirmed by 1H NMR. The OH group of glycidol in Gly-PLA was absent according to the $^1H$ NMR analysis, indicating that the terminal OH group of glycidol successfully served as an initiator in the L-lactide polymerization. The solution and bulk polymerizations of L-lactide with glycidol were performed to examine the effect of L-lactide/glycidol molar ratio, polymerization temperature and time on the molecular characteristics of Gly-PLA. The conversion and molecular weight increased with an increase in L-lactide/glycidol molar ratio. Gly-PLA showed the bimodal type DSC curve. The low $T_m$ peak of low molecular weight reduced but the high $T_m$ peak of high molecular weight increased as L-lactide/glycidol molar ratio increased.

Studies of Degradation Behavior of Stereochemical Poly(lactide) Blend Fibers Prepared by Electrospinning (전기방사에 의한 이성질 폴리락타이드 블렌드의 섬유제조와 분해거동에 관한 연구)

  • Jang, Ei-Sup;Lee, Won-Ki
    • Journal of Environmental Science International
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    • v.23 no.3
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    • pp.473-481
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    • 2014
  • Poly(lactide)s(PLA) is an attractive material to solve the problem of waste plastic accumulation in nature because of its biodegradability. The lactide exists in three stereoisomeric configurations: L-lactide, D-lactide, and meso-lactide. PLA stereocomplexes, formed by the mixing of two enantiomers, poly(L-lactide)(PLLA) and poly(D-lactide)(PDLA), have many favorable characteristics because the stereocomplex showed $50^{\circ}C$ higher melting point than each enantiomeric polymer and the resistance toward degradation increased. In this study, we investigated the influence of the composition and the optical purity of each component on the formation of stereocomplexes. Also, the nanofibers of stereochemical PLA and their blends were prepared by electrospinning method. The properties of the obtained fibers were analyzed by differential scanning calorimetry and scanning electron microscopy. The results showed that a degree of stereocomplex was controlled by change of optical purity of each component. The enzymatic degradation of the fibers were strongly dependent on the stereocomplex.

Non-isothermal Crystallization Behavior of Poly(glycolide-co-ε-caprolactone-co-L-lactide) Block Copolymer (생체분해성 Poly(glycolide-co-ε-caprolactone-co-L-lactide) 블록 공중합물의 비등온 결정화 거동에 관한 연구)

  • Choi, Sei-Young;Song, Seung-Ho
    • Elastomers and Composites
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    • v.49 no.1
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    • pp.13-23
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    • 2014
  • In this work, glycolide, L-lactide and ${\varepsilon}$-caprolactone monomers were polymerized into the triblock copolymers by two step polymerization method and their non-isothermal crystallization behaviors were studied by combination of modified Avrami and Ozawa formula for further analysis of their behaviors. The result showed that PGCLA21 gave the highest value for supercooling analysis and super cooling degree increased with L-lactide content. Crystallization velocity constant, however, showed no significant change. The result of cooling function in specific relative crystallization degree showed that the increase of L-lactide content made an effect on the more enhancement of crystallization velocity of the PGCLA than PGCL. The result of big logF(T) value with the L-lactide content above critical point for PGCLA41 and PGCLA21 showed that bigger cooling velocity needed to gain same crystal size compared with PGCL. This means that it gives negative effect in the increase of crystallization velocity.

Studies on Synthesis of Block Copolymers Containing Polyester and Polypeptide for Drug Delivery System Ⅰ. Synthesis and Characterization of Copolymer of L-Lactic Acid and L-Glutamic Acid (폴리펩티드-의약 전달체 및 폴리펩티드 공중합체의 합성 및 물성에 관한 연구 (Ⅰ) L-Lactic Acid 와 L-Glutamic Acid 공중합체의 합성 및 그의 물성)

  • Kim, Hong Beom;Seong, Yong Gil;Jeong, Jae Hui;Baek, Hyeong Ge;Min, Tae Jin;Kim, Yeong Sun
    • Journal of the Korean Chemical Society
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    • v.34 no.2
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    • pp.203-210
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    • 1990
  • As a possible biocompatible and biodegrable polymer skeleton for drug delivery system, block copolymers of L-lactic acid and L-glutamic acid with different composition were synthesized and characterized. Poly (L-lactide) was prepared by polymerization of L-lactide with zine oxide at $130^{\circ}C$ for 72 hrs. 3-Amino-l-propanol was introduced to poly (L-lactide) by an ester linkage in order to initiate polymerization. Polymerization of $\gamma-benzyl-L-glutamate-N-carboxyanhydride(\gamma-BLG-NCA)$ utiliizing the amino group of modified poly (L-lactide) as an initiator gave rise to the block copoly $(L-lactide-\gamma-benzyl-L-glutamate).$ The NMR study of resulting block copolymers showed that the composition of L-lactic acid and $\gamma-benzyl-L-glutamate$ in block copolymers was depended on the weight ratio of poly (L-lactide) and $\gamma-BLG-NCA.$ The thermal properties of the resulting block copolymers were determined by the differential scanning calorimetry and by the thermogravimetry.

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Synthesis of Lactide/Hyaluronic Acid Polymer Membrane for the Application of Drug Delivery System (약물방출시스템 적용을 위한 락타이드/히아루론산 고분자 막의 제조)

  • Kim, Min-Su;Kwon, Ji-Young;Cheong, Seong-Ihl
    • Membrane Journal
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    • v.15 no.4
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    • pp.281-288
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    • 2005
  • The hyaluronic acid (HA) with excellent biocompatibility can be combined with lactide, the ester dimer of polylactide, with good biodegradability to produce biocompatible materials applicable to drug delivery system. By freeze drying method, HA and lactide were crosslinked with crosslinking agent, 1-ethyl-3-(3-dimethyl aminopropyl) carbodiimide. Degree of lactide and EDC reaction was determined by the analysis of nuclear magnetic resonance (NMR) spectroscopy. The degree of lactide and EDC reaction increased and swelling ratio decreased as the mole ratio of lactide to HA or crosslinking agent concentration increased or reaction temperature decreased. The drug release experiment result from membranes having different degree of lactide reaction showed that drug release rate reduced in proportion to the degree of lactide reaction. The drug release experiment result from drugs having different hyrodphobicity showed that the more hydrophobic drug was released more slowly.

poly(D,L-lactide-co-glycolide) nanoparticles제조와 약물방출 거동 및 생분해도

  • Yu, Jeong-Jun;Jeong, Yeong-Il;O, Dong-Seok;Im, Gyun-Taek
    • 한국생물공학회:학술대회논문집
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    • 2000.04a
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    • pp.550-553
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    • 2000
  • The polymeric matrices made with poly(D,L-lactide-co-glycolide) were prepared using copolymer of poly(D,L-lactide) and poly(ethylene glycol) for application of drug delivery systems. Catalyst made use of stannous actoate. Particle size were differ greatly$(435.3{\pm}11.2{\sim}2284.1{\pm}188.5)$ that nanoparticle made use of according to solvent of various kinds. Polymer could a sharp distinction with copolymerized among LE-1, LE-2 and LE-3 of PLA and PEG of content that to examine $^1H-NMR$ of copolymer make refine and reprecipitation. Drug delivery effect at PLGA nanoparticle : PLA amount more then proved highly drug delivery amount that each LE-1, LE-2, LE-3, drug and solvent was 40mg, 20mg and 10mg. Drug delivery effect proved higher 20mg that change(10mg, 20mg, 40mg) at drug feeding amount with LE-2. The first a lot of drug proved delivery. LE-3 most lactide content proved much delivery since biodegradable on PLGA copolymer result from lactide. Also biodegradable rate was highest at LE-3 much of lactide content, because influence at biodegradable effect of lactide by inclusive of soft PEG.

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생분해성 고분자 합성을 위한 락티드 합성에서 열분해 공정의 개선

  • No, Won-Gyun;Ryu, Hwa-Won
    • 한국생물공학회:학술대회논문집
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    • 2003.04a
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    • pp.622-624
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    • 2003
  • Poly(lactic acid) is a biodegradable themoplastic based on the renewable resources to substitute for petrochemical plastics. Most of PLA is produced by ring opening polymerization from lactide. However, pyrolysis process in the lactide synthesis is expensive, we studied lactide synthetic process for more economical preparation of PLA. In this research was tried to minimize the pyrolysis time, and obtained L-lactide from lactic acid without any catalyst.

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Preparation of Microcapsules and Their Application (Poly (L-lactide) Microcapsule) (마이크로캡슐의 제조와 그 응용(폴리락티드 마이크로캡슐))

  • 홍기정;박수민
    • Textile Coloration and Finishing
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    • v.10 no.2
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    • pp.29-36
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    • 1998
  • Poly(L-lactide) microcapsules containing hydrophilic penetrate were prepared by interfacial precipitation method through solvent evaporation from w/o/w emulsion. Effect of four determinative process parameters on the particle size distributions, morphologies, and release properties of microcapsules coated with poly(L-lactide) was investigated. Moreover, susceptible functional cotton fabrics treated with the mentioned microcapsules were prepared and laundry test up to 15 times were done to determine fastness properties. As a result, the prepared poly(L-lactide) microcapsules with a more sharp-distributive, rounder, and more permeable membranes could be prepared by means of protective colloid concentration, solution volume and stirring rate.

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Synthesis and Properties of Triblock and Multiblock Copolymers Consisting of Poly(L-lactide) and Poly(oxyethylene-co-oxypropylene)

  • Lee, Chan-Woo;Kang, Young-Goo;Kun Jun
    • Macromolecular Research
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    • v.9 no.2
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    • pp.84-91
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    • 2001
  • Both A-B-A triblock and multiblock copoly(ester-ether)s consisting of poly(L-Lactide) and poly(oxyethylene-co-oxypropylene) were prepared and characterized. The preparation of the triblock copolymer was done by ring-opening copolymerization of L-lactide with a commercially available telechelic copolyether, Pluronic$\^$TM/(PN) by catalysis of stannous octanoate. The molecular weight and unit composition of the produced copolymers were successfully controlled by changing the L-lactide/PN ratio in feed. However, a high molecular weight copolymer incorporating PN in large amount was not obtained because the molecular weight of the resulting copolymer was limited at a high L-lactide/PN composition. The multiblock copolymer was synthesized by the copolycondensation of oligo(L-lactic acid) prepared by thermal dehydration of L-lactic acid, PN, and dodecanedioic acid as carboxyl/hydroxyl adjusting agent. This polycondensation proceeded by catalysis of stannous oxide to give multiblock copolymers with high molecular weight and wide range of compositions.

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