Investigation on lipase-catalyzed solution polymerization of cyclic carbonate

Feng, Jun; Wang, Huafen; Zhang, Xian‐Zheng; Zhuo, Ren‐Xi

doi:10.1016/j.eurpolymj.2008.11.006

Cited by 21 publications

(13 citation statements)

References 29 publications

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“…Such a phenomenon, similar to solid-phase polymerization, has previously been reported in the lipase-catalyzed polymerization of lactide and cyclobis (decamethylene carbonate), as well as in spontaneous thermal polymerization of macrocyclic aromatic carbonates. 23 all parallel experiments because of the lowered system viscosity. An evident declining trend in M n with increasing toluene/carbonate ratio was observed.…”

Section: Resultsmentioning

confidence: 99%

“…However, research thus far has been limited to PTeMC, PHMC and PDMC derived from 1,4-butanediol, 1,6-hexanediol and 1,10-decanediol, respectively. [22][23][24][25] Our group recently reported the preparation of poly(pentamethylene carbonate) (PPMC) by Sn(Oct) 2 -catalyzed ROP of cyclobis(pentamethylene carbonate) (PMC) 2 . 26 An interesting odd-even effect was observed in relation to the number of CH 2 groups per -(CH 2 ) n OCOO-repeat unit (Num c ) of polycarbonates.…”

Section: Introductionmentioning

confidence: 99%

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Highly efficient enzymatic catalysis for cyclocarbonate polymerization

Luo

Feng

Wang

et al. 2010

Polym J

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In this study, we developed a metal-free biosynthetic strategy of enzymatic polymerization to fabricate aliphatic poly(pentamethylene carbonate) (PPMC). Novozym-435 lipase showed considerably high catalytic efficiency, and high molecular weights (M n ) of up to 6.0Â10 4 g mol À1 were readily achieved through the ring-opening polymerization of cyclobis(pentamethylene carbonate). The reaction parameters, including monomer concentration and lipase concentration, were examined. It seemed that little polymer degradation occurred during the polymerization, which would happen in the case of organometallic catalysis. In vitro enzymatic degradation tests indicate that the carbonate groups may not be sensitive to catalysis from the lipases of porcine pancreas and Candida rugosa (AYS). PPMC was found to possess higher flexibility and tenacity, relative to poly(trimethylene carbonate). Thermogravimetrical analyses suggest that the chemical structure of poly(alkylene carbonate)s exerts a significant influence on their thermal stability and decomposition mechanism.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Highly efficient enzymatic catalysis for cyclocarbonate polymerization

Luo

Feng

Wang

et al. 2010

Polym J

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“…PTMC, PCL, PDLLA, PCDLLA and PTCL were synthesized as previously described (Yang et al, 2010, Zhang et al, 2012, Zhang et al, 2013a). Briefly, the polymerizations were conducted by ring opening polymerization in evacuated and sealed glass ampules using SnOct 2 as catalyst (Feng et al, 2009). Polymerization was carried out for 24 h at 130 ± 2 °C.…”

Section: Methodsmentioning

confidence: 99%

Permeation measurement of gestodene for some biodegradable materials using Franz diffusion cells

Liu

Zhang

et al. 2015

Saudi Pharmaceutical Journal

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Biodegradable poly(d,l-lactide) (PDLLA), Poly(trimethylene carbonate) (PTMC), polycaprolactone (PCL), poly(caprolactone-co-d,l-lactide) (PCDLLA) and poly(trimethylene carbonate-co-caprolactone) (PTCL) are recently used for clinical drug delivery system such as subcutaneous contraceptive implant capsule due to their biodegradable properties that they could possess long-term stable performance in vivo without removal, however their permeation rate is unknown. In the work, biodegradable material membranes were prepared by solvent evaporation using chloroform, and commercial silicone rubber membrane served as a control. Gestodene was used as a model drug. Gestodene has high biologic progestational activity which allows for high contraceptive reliability at very low-dose levels. The permeation rate of gestodene for several biodegradable materials was evaluated. In vitro diffusion studies were done using Franz diffusion cells with a diffusion area of 1.33 cm(2). Phosphate buffer solution (PBS, pH 7.4), 10% methanol solution and distilled water were taken in donor and receiver chambers at temperature of 37 °C respectively. The in vitro experiments were conducted over a period of 24 h during which samples were collected at regular intervals. The withdrawn samples were appropriately diluted and measured on UV-vis spectrophotometer at 247 nm. Conclusion data from our study showed that permeation rate of PCDLLA with CL ratio more than 70% could be more excellent than commercial silicone rubber membrane. They may be suitable as a candidate carrier for gestodene subcutaneous contraceptive implants in contraceptive fields.

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“…33,38 Lipase has showed the outstanding capacity for ROP of macrocyclic lactones and carbonates compared to metal and organic catalysts. 35,39 Owing to the high melting point of M Se (T m = 93 °C, Figure S6), the ROP was carried out by solution polymerization in toluene at 70 °C. The obtained PSe structure was verified by 1 H NMR and 77 Se NMR (Figures 2b and S7).…”

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confidence: 99%

Well-Defined Selenium-Containing Aliphatic Polycarbonates via Lipase-Catalyzed Ring-Opening Polymerization of Selenic Macrocyclic Carbonate Monomer

Wei

Yan

et al. 2018

ACS Macro Lett.

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The synthesis of well-defined, biodegradable selenium-containing polymers remains a formidable challenge in polymer chemistry. Herein, a selenic cyclic carbonate dimer monomer (M Se ) was developed to generate well-defined, biodegradable aliphatic polycarbonates with selenide functionality on the backbone. The monomer was synthesized via the intermolecular cyclization of di(1-hydroxyethylene) selenide and diphenyl carbonate with lipase CA as catalysts in a mass of anhydrous toluene with very dilute monomer concentration. Then living ring-opening polymerization (ROP) was executed by solution method using the same lipase CA as catalysts. Similarly, the copolymerizations with commercial trimethylene carbonate (TMC) generated random copolymers demonstrated by 13 C NMR, regulating the density of selenium functional groups. The resulting polymers exhibited a living polymerization characteristic, as evidenced by polymerization kinetics, predictable molecular weights, narrow molecular-weight distribution, and controlled copolymer compositions. Using hydrophilic macroinitiators (PEG), amphiphilic di/triblock copolymers could be obtained, suggesting their potential as controlled drug delivery system (DDS) and hydrogel scaffolds for tissue engineering.

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Investigation on lipase-catalyzed solution polymerization of cyclic carbonate

Cited by 21 publications

References 29 publications

Highly efficient enzymatic catalysis for cyclocarbonate polymerization

Highly efficient enzymatic catalysis for cyclocarbonate polymerization

Permeation measurement of gestodene for some biodegradable materials using Franz diffusion cells

Well-Defined Selenium-Containing Aliphatic Polycarbonates via Lipase-Catalyzed Ring-Opening Polymerization of Selenic Macrocyclic Carbonate Monomer

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