Synthesis and characterization of amino-functionalized poly(propylene carbonate)

Song, Pengfei; Shang, Yingqi; Chong, Siying; Zhu, Xiaogang; Xu, Haidong

doi:10.1039/c5ra02854j

Cited by 12 publications

(11 citation statements)

References 21 publications

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“…Such aminofunctional polymers are a general precursor for postfunctionalized polycarbonates and for the attachment of proteins or drugs. They exhibit potential for medical devices, drug delivery systems, and in tissue engineering …”

Section: Functional Ethylene‐oxide‐based and Terminal Epoxide Monomersmentioning

confidence: 99%

“…In the following, a brief summary of the classes of functional monomers that have been employed, will be given: (i) cyclohexene oxide derivatives; (ii) ethylene oxide derivatives; (iii) glycidyl ethers. In order to prevent side reactions, the functional groups in the monomers are often protected prior to polymerization, and the protective groups should be conveniently removed after polymerization, with no impact on the polycarbonate chains . Besides the use of functionalized monomers, the properties and functionality of aliphatic polycarbonates can also be controlled by the polymer architecture.…”

Section: Introductionmentioning

confidence: 99%

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Functional Polycarbonates from Carbon Dioxide and Tailored Epoxide Monomers: Degradable Materials and Their Application Potential

Scharfenberg

Hilf

Frey

2018

Adv Funct Materials

178

109

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Aliphatic polycarbonates synthesized from carbon dioxide (CO 2 ) and epoxides are resource-saving, highly biocompatible and biodegradable polymers. Since the discovery of the copolymerization of epoxides and CO 2 in 1969 by Inoue et al., this has become an important and useful technology for the large-scale utilization of CO 2 in chemical synthesis, employing mainly propylene oxide, and cyclohexene oxide (CHO). Only in recent years, functionalized polycarbonates have become an emerging topic with a broad scope of potential applications. This review summarizes synthetic routes and properties of numerous functionalized polycarbonates synthesized from CO 2 and functional epoxide monomers. Implications for new materials and possible applications, for instance for pharmaceutical purposes and membranes are reviewed. Besides polycarbonates based on oxirane and CHO derivatives, particular emphasis is placed on the manifold synthetic approaches and postpolymerization modifications of glycidyl ether based polycarbonates. Not only functionalized linear polycarbonates are presented but also a variety of novel polycarbonate architectures, e.g., star and hyperbranched polymers.

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Section: Functional Ethylene‐oxide‐based and Terminal Epoxide Monomersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Functional Polycarbonates from Carbon Dioxide and Tailored Epoxide Monomers: Degradable Materials and Their Application Potential

Scharfenberg

Hilf

Frey

2018

Adv Funct Materials

178

109

View full text Add to dashboard Cite

show abstract

“…Besides, when functional groups are incorporated into the polymer backbones; the potential applications will be further broadened. For example, the introduction of hydroxyl, 6–9 carboxyl, 10,11 and amino groups 12–19 can effectively tunning the hydrophilic properties. Pendant functional groups may also provide active sites for further modification such as crosslinking, attaching bioactive substances to satisfy more specific applications 3,4,20,21 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new aliphatic poly(ester‐carbonate)s bearing amino groups based on photolabile protecting group and evaluation of antibacterial property

Gao

Chen

et al. 2021

Polymers for Advanced Techs

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Amino‐functionalized six‐membered cyclic carbonate 5‐((2‐nitrobenzyl) amino)‐1,3‐dioxan‐2‐one (NBAC) was synthesized with 2‐nitrobenzyl group as photolabile protecting group. The following copolymerization was carried out by using l‐lactide as comonomer and Sn (Oct)2 as catalyst. The amino‐functionalized polymer P(LA‐co‐AC) was obtained by ultraviolet irradiation of P(LA‐co‐NBAC) to remove the protecting group. The structures of products were confirmed by 1H nuclear magnetic resonance (NMR) and 13C NMR analysis. The pendant amino groups not only resulted in an enhancement of the hydrophilicity, but also played a role of antibacterial effect due to the positive charge imparted to the material.

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“…Recently, numerous chemists have been looking for effective ways to improve PPC performance and enlarge its application fields. For example, different third monomer, such as lactone, N , N ‐dibenzyl amino glycidol, and lactide, has been introduced into the copolymerization of CO 2 and PO to produce block polymer. Wang et al reported a triblock copolymer of poly(allylglycidylether carbonate) (PAGEC)‐b‐PPC‐b‐PAGEC.…”

Section: Introductionmentioning

confidence: 99%

Amphiphilic block poly(propylene carbonate)‐block‐allyloxypolyethyleneglycol copolymer based shell cross‐linked micelles for controlled release of drug

Niu

2019

Polymers for Advanced Techs

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Amphiphilic block poly(propylene carbonate)‐block‐allyloxypolyethyleneglycol (PPC‐b‐APEG) copolymer was synthesized by the click chemistry, and its structure were characterized. PPC‐b‐APEG can self‐assemble into micelles without emulsifier in water. Shell cross‐linked micelles were obtained by the reaction of the allyloxy groups, which were exposed on the outer of the PPC‐b‐APEG micelles, and N‐vinylpyrrolidone (NVP). The morphology and size of the micelles before and after cross‐link reactions were characterized. The research result shows that the shell cross‐linking could improve the stability of micelles. The particle size of uncross‐linked micelle was about 800 nm. The size of cross‐linked micelles increased with increasing amount of cross‐linking degree. To better evaluate the release behavior of PPC‐b‐PEG copolymer, doxorubicin (DOX)‐loaded micelles were synthesized using DOX as the model drug. Results showed that the DOX releasing rate decreased with increasing of NVP. The shell cross‐linking do decrease the burst release behaviours of DOX and reduce the DOX release rate.

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Synthesis and characterization of amino-functionalized poly(propylene carbonate)

Abstract: The first synthesis of amino-functionalized poly(propylene carbonate) (PPC) by terpolymerization of carbon dioxide (CO2), propylene oxide (PO), and N,N-dibenzyl amino glycidol (DBAG) following the removal of benzyl protecting groups.

Cited by 12 publications

References 21 publications

Functional Polycarbonates from Carbon Dioxide and Tailored Epoxide Monomers: Degradable Materials and Their Application Potential

Functional Polycarbonates from Carbon Dioxide and Tailored Epoxide Monomers: Degradable Materials and Their Application Potential

Synthesis of new aliphatic poly(ester‐carbonate)s bearing amino groups based on photolabile protecting group and evaluation of antibacterial property

Amphiphilic block poly(propylene carbonate)‐block‐allyloxypolyethyleneglycol copolymer based shell cross‐linked micelles for controlled release of drug

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