Synthesis and characterization of novel degradable photocrosslinked poly(ether-anhydride) networks

Kim, Beom Soo; Hrkach, Jeffrey S.; Langer, Robert

doi:10.1002/(sici)1099-0518(20000415)38:8<1277::aid-pola11>3.0.co;2-s

Cited by 41 publications

(26 citation statements)

References 12 publications

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“…The introduction of PEG into polyanhydrides can improve their hydrophilicity and thus adjust the degradation rate of obtained materials. 16,17 Kim and Langer synthesized degradable networks of poly(ether anhydride) from PEGbis(carboxymethyl)ethers by photopolymerization. The strong hydrophilicity of the networks made the degradation ways change from surface erosion to bulk hydrolysis.…”

Section: Introductionmentioning

confidence: 99%

“…The strong hydrophilicity of the networks made the degradation ways change from surface erosion to bulk hydrolysis. 16 Previously, 18 -21 we reported the polymerization of ⑀-caprolactone and lactide initiated by potassium poly(ethylene glycol)ate (PEGOK). As an extension of our past work, this study mainly dealt with the ring-opening polymerization of AA initiated by a PEGOK macroinitiator.…”

Section: Introductionmentioning

confidence: 99%

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Anionic ring‐opening polymerization of adipic anhydride initiated by potassium poly(ethylene glycol)ate

Deng

Yuan

et al. 2003

J of Applied Polymer Sci

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Poly(adipic anhydride) (PAA) was prepared by the ring-opening polymerization of adipic anhydride (AA) initiated by potassium poly(ethylene glycol)ate. The effects of various factors, such as the amount of initiator, concentration of the monomer, reaction time and temperature, and polarity of the solvent on the polymerization were investigated. The crude polymerized product was a mixture of PAA homopolymer and poly(ethylene glycol)-poly(adipic anhydride) block copolymer, as confirmed by 1 H-NMR and gel permeation chromatography. Chain-transfer reactions occurred intensively for the AA polymerization in both the nonpolar solvent toluene and the polar solvents CHCl 3 and tetrahydrofuran, which predominantly determined the molecular weight and the monomer conversion for the polymerized product. The lower monomer conversion in toluene was ascribed to a lower livingness for the initiator in the nonpolar solvent when compared with other two, polar solvents.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anionic ring‐opening polymerization of adipic anhydride initiated by potassium poly(ethylene glycol)ate

Deng

Yuan

et al. 2003

J of Applied Polymer Sci

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“…Besides environmental conditions, such as temperature, the degradation rate is strongly dependent on the film thickness, 1 additives such as monomer, 2 basic compounds, 3 acid drugs 4 or superoxide ion, 5 and catalyst such as SnOct 2 or zinc metal, 6-9 etc. The molecular architecture, 10-13 hydrophilicity, 14-16 reasonable crosslink, 17,18 and surface modification 19,20 have vital influence on the degradation properties, too.End-group effect is demonstrable on the degradation rate. 21 It was shown that poly(lactide-co-glicolide) (PLGA) with a free carboxyl group at the polymer terminus (uncapped PLGA) degrades faster than PLGA with a hydrophobic alkyl ester linkage at the polymer terminus (capped PLGA).…”

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confidence: 99%

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confidence: 99%

Synthesis, Characterization, and Degradation Behaviors of End-Group-Functionalized Poly(trimethylene carbonate)s

Zhuo

2003

Polym J

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KEY WORDSPolycarbonate / Biodegradable Material / End-Group Effect / Biodegradable polymers are under investigation for biomedical, pharmaceutical applications, etc. Degradability is one of their important characters. Many factors affect the degradation rate. Besides environmental conditions, such as temperature, the degradation rate is strongly dependent on the film thickness, 1 additives such as monomer, 2 basic compounds, 3 acid drugs 4 or superoxide ion, 5 and catalyst such as SnOct 2 or zinc metal, 6-9 etc. The molecular architecture, 10-13 hydrophilicity, 14-16 reasonable crosslink, 17,18 and surface modification 19,20 have vital influence on the degradation properties, too.End-group effect is demonstrable on the degradation rate. 21 It was shown that poly(lactide-co-glicolide) (PLGA) with a free carboxyl group at the polymer terminus (uncapped PLGA) degrades faster than PLGA with a hydrophobic alkyl ester linkage at the polymer terminus (capped PLGA). 22 Lee 21 synthesized various end-group-functionalized, such as OH-, NH 2 -, Cl-, or COOH-terminated polylactides (PLAs) and found that the COOH end group plays a crucial role in the hydrolysis degradation in both alkaline and acidic medium. Protection of OH end group results in a substantial retarded degradation. 23 Polyanhydrides capped with fatty terminals also show a significantly slow degradation and drug release rate. 24 Linear aliphatic polycarbonates, such as poly(1,3-trimethylene carbonate) (PTMC), have been shown to be potential for use as medical implants and for drugdelivery applications. 25 But they degrade unexpectedly slow. 10 Many efforts have been made to enhance their degradation rate. Copolymers of PTMC were synthesized for adapting to applications requiring different degradation rates and mechanical properties. 10,[26][27][28][29] Pendant hydroxyl groups have been introduced to improve the hydrophilicity and hence the degradability. 30 Since end groups have special effect on degradation rate, end-group functionalized polycarbonates will have different degradation rate. Because the polymers of multiarm architecture have a higher end-group concentration than linear polymers of the same molecular weights, the multiarm structure can strengthen the end group effect. Some researchers have synthesized the OH-terminated PTMC by ring-opening polymerization (ROP), but the degradability has not been involved up to now. 31 In the present study, we synthesize PTMC with different number of arms terminated by hydroxyl group or carboxylic group and study the degradability of such end-group-functionalized PTMCs preliminarily. EXPERIMENTAL 1,3-Trimethylene carbonate (TMC) was synthesized according to the reported method. 32 All other regents were treated just before use. Synthesis of OH-Terminated PTMC (OH-PTMC)The ring-opening polymerizations (ROP) of TMC initiated by alcohols are illustrated in Scheme 1. These polymerization reactions were carried out in the melt bulk. All reaction reagents were used just after treated. A known amount of TMC was charged ...

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“…Domb et al [7] prepared copolyanhydrides from sebacic acid (SA) and unsaturated dicarboxylic acids such as fumaric acid and stillbenedicarboxylic acid, which were radically crosslinked with styrene or methylmetacrylate. Recently, photocrosslinked poly(etheranhydride) networks were synthesized to develop rapidly degradable biomaterials [8].…”

Section: Introductionmentioning

confidence: 99%

Photocrosslinkable degradable copolyanhydries made from sebacic acid and 4-hydroxycinnamic acid

Nagata

Ioka

2005

Reactive and Functional Polymers

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Synthesis and characterization of novel degradable photocrosslinked poly(ether-anhydride) networks

Cited by 41 publications

References 12 publications

Anionic ring‐opening polymerization of adipic anhydride initiated by potassium poly(ethylene glycol)ate

Anionic ring‐opening polymerization of adipic anhydride initiated by potassium poly(ethylene glycol)ate

Synthesis, Characterization, and Degradation Behaviors of End-Group-Functionalized Poly(trimethylene carbonate)s

Photocrosslinkable degradable copolyanhydries made from sebacic acid and 4-hydroxycinnamic acid

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