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The Synthesis of Two-arm PEO with a Functional End Group and Its Derivatives

Author: CaiJiaBin
Tutor: HuangJunLian
School: Fudan University
Course: Chemical Engineering
Keywords: PEO End group Polyethylene oxide Segment Macroinitiator Groups Branched Hydroxy Polyfunctional Hydrodynamic volume Functional Copolymer Proton displacement Coupling reaction Ring-opening polymerization Styrene Polymerization polyethylene ATRP Main chain Bromo
CLC: O631.3
Type: Master's thesis
Year: 2010
Downloads: 72
Quote: 0
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Abstract


Poly(ethylene oxide) (PEO) is one of the most widely used biocompatible polymer due to its safety and non-toxicity for human body. PEO with low molecular weight used as drug carriers still had some disadvantages such as short circulation half-life in vivo. Recently, the research on the PEGylation of drugs had focused on the synthesis and modification of branched PEO, synthesis and modification of high molecular weight PEO, site-specific and releasable PEGylation. Among these, much attention had paid to the study of branched PEO, which shows smaller hydrodynamic volume and longer circulation half-life in vivo comparing to linear PEO with the same molecular weight. At present, branched PEO was usually synthesized by coupling linear PEOs with functional end group to a multi-functional core molecule. However, this coupling approach showed some shortages as long reaction period and complicated purification and separation procedures, that is the cause for the expensive price of this kind of PEOs and difficult production on large scale.In this thesis, a small molecular compound with two hydroxyl groups 3-[(1’-Ethoxyethyl)-ethoxyethyl]-1,2-propanediol (EEPD) was firstly synthesized with high purity. It was used as co-initiator with diphenylmethyl potassium (DPMK) to initiate the ring opening polymerization (ROP) of ethylene oxide (EO) to synthesize two arms PEO with a protected hydroxyl group at the conjunction point. After the end hydroxyl groups on PEO arms were end-capped by benzyl groups, the protected hydroxyl group was hydrolyzed to get PEO2-OH.Afterwards, PEO2-OH was reacted with acrylonitrile in the presence of sodium hydroxide to get PEO2-CN, Then the cyano group was converted into carboxyl group and N-chlorosuccinimide for PEO2-COOH and PEO2-SC, and the latter can be used for protein modification. The functional products were characterized by GPC and 1H NMR in detail.The active hydroxyl at the conjunction point of PEO2-OH was reacted with 2-bromoisobutyryl bromide to synthesize PEO2-Br, which can initiate atom transfer radical polymerization (ATRP) of styrene. Thus the star-shaped polymers (starPEO2PS) were obtained with two hydrophilic PEO arms and one hydrophobic PS arm. The three-arm amphiphilic starPEO2PS was characterized by GPC and 1H NMR in detail.

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CLC: > Mathematical sciences and chemical > Chemistry > Polymer chemistry ( polymer ) > Polymer physics and physical chemistry of polymers > The chemical nature of polymers
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