Synthesis, properties, and biodegradation of poly(1,3-trimethylene carbonate)

Zhu, Kan; Hendren, R W; Jensen, Kasper Løvborg; Pitt, Colin G.

doi:10.1021/ma00008a008

Cited by 482 publications

(469 citation statements)

References 9 publications

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“…From 3-h hydrolysis time showing M n decreases, the kinetics study of the hydrolytic surface degradation can be established. The kinetic expression, Eq 4, is applied for non-catalytic chain scission mechanism [25,29] in pH 7.4 ISOTON II buffered condition. In both data reduction practices, good linearity can be obtained from the data and rate constants can be calculated from the slope showing the decrease in linear relationship.…”

Section: Resultsmentioning

confidence: 99%

“…Hence, the hydrolytic degradation rate in non-catalytic system is proportional to water and ester concentrations at the solid matrix/ surrounding aqueous buffer interface. It can be expressed to a pseudo first-order reaction [25,29] as follows:…”

Section: Hydrolytic Degradation Kineticsmentioning

confidence: 99%

“…In the quantitative degradation studies of biodegradable polymers, a conventional bulk characterization technique like GPC [23][24][25][26] has been widely employed for the determination of decrease in MW average of polymer matrices retrieved at various time intervals. However, the bulk properties do not always represent the surface characteristics of degraded biodegradable polymer matrices and do not provide any information about chemical structure and MWD of degradation products, degradation reaction mechanism, and chemical structural change that may occur at the surface during degradation process.…”

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confidence: 99%

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Quantitative TOF-SIMS analysis of oligomeric degradation products at the surface of biodegradable poly(α-hydroxy acid)s

Lee

Gardella

2002

J. Am. Soc. Mass Spectrom.

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This paper reports the development of a new method for quantification of the hydrolytic surface degradation kinetics of biodegradable poly(␣-hydroxy acid)s using time-of-flight secondary ion mass spectrometry (TOF-SIMS). We report results from static SIMS spectra of a series of poly(␣-hydroxy acid)s including poly(glycolic acid), poly( L -lactic acid), and random poly( D,L -lactic acid-co-glycolic acid) hydrolyzed in various buffer systems. The distribution of the most intense peak intensities of ions generated in high mass range of the spectrum reflects the intact degradation products (oligomeric hydrolysis products) of each biodegradable polymer. First, a detailed analysis of the oligomeric ions is given based on rearrangement of the intact hydrolysis products. The pattern of ions can distinguish both degradation-generated intact oligomers and their fragment ion peaks with a variety of combinations of each repeat unit. Then, the integration and summation of the area of all ion peaks with the same number of repeat units is proposed as a measurement that provides a more accurate MW average than the typically used method which counts only the most intense peak. The multiple ion summation method described in this paper would be practical in the improvement of quantitative TOF-SIMS studies as a better data reduction method, especially in the surface degradation kinetics of biodegradable polymers. , additives in a polymer [13], and detailed structural characterization [14,15] and quantitative analysis [16 -20] of polymers. Most TOF-SIMS spectra of polymers have been obtained in the mass range m/z Ͻ10,000 [5, 18 -20].Two main processes are observed in the TOF-SIMS spectra of polymers; these are the fragmentation of polymer chains and the desorption of intact oligomers. Fragmentation under ion bombardment in ultra-high vacuum (UHV) environment generates distinct fragmentation patterns that are unique to a given polymer. From the fragmentation patterns the mass of the repeat unit, terminal groups, side groups, and functional groups in a repeat unit can be determined [14,15]. Desorption of intact oligomers provides a direct measure of molecular weight distribution (MWD) from which a molecular weight average can be evaluated. According to the recent reports [21,22] on the comparison of mass spectrometric techniques, TOF-SIMS produced a result similar to electrospray ionization (ESI) and fast atom bombardment (FAB). They consistently showed lower MW averages compared with gel permeation chromatography (GPC)-deduced results, whereas

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Section: Resultsmentioning

confidence: 99%

Section: Hydrolytic Degradation Kineticsmentioning

confidence: 99%

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confidence: 99%

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Quantitative TOF-SIMS analysis of oligomeric degradation products at the surface of biodegradable poly(α-hydroxy acid)s

Lee

Gardella

2002

J. Am. Soc. Mass Spectrom.

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“…The length of terephthalate block has decisive influence on copolymer biodegradation. When the number average block length is 3 or higher degradation rate is small and it is difficult to achieve complete biodegradation of aliphatic-aromatic polyester [29].…”

Section: Synthesis Of Poly(tetramethylene Carbonate)mentioning

confidence: 99%

“…Furthermore, polycarbonates have lower degradation rate than polyesters [28,29], which would be advantageous in the applications where relatively higher stability is desired.…”

Section: Introductionmentioning

confidence: 99%

Aliphatic-aromatic poly(ester-carbonate)s obtained from simple carbonate esters, α,ω-aliphatic diols and dimethyl terephthalate

et al. 2015

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Two reaction pathways for synthesis of high molar mass (M w above 50 000 g/mol) aliphatic-aromatic poly(estercarbonate)s were elaborated. Simple organic carbonates such as dimethyl carbonate or propylene carbonate were used as carbonate linkage sources and dimethyl terephthalate as the precursor of ester linkages. 1,4-Butanediol, 1,5-pentanediol, 1,6-hexanediol and 1,10-decanediol were used as diol monomers. To adjust the carbonate units content in the copolymer, solid alkylene bis(methylcarbonate) was used as a semiproduct instead of volatile dimethyl carbonate. In case of usage propylene carbonate as a starting material the process can be carried out in one pot without the need for isolation of the semiproduct. The obtained copolymers based on 1,4-butanediol, containing ca. 50 mol.% of carbonate units exhibited better mechanical strength (37 MPa) than commercially available aliphatic-aromatic copolyester Ecoflex ® keeping the thermal properties at the same level.

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Copolymerization and polymer blending of trimethylene carbonate and adipic anhydride for tailored drug delivery

Edlund

Albertsson

1999

J. Appl. Polym. Sci.

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The copolymerization in bulk and solution of trimethylene carbonate (TMC) with adipic anhydride (AA) as well as the blending of homopolymers are described. We show experimentally that the components are not copolymerizable but partially miscible, forming a microscopic dispersion without any visible signs of phase separation. Poly(adipic anhydride) (PAA) functions as a plasticizer, permitting an increase in the erosion rate by increasing the porosity and hydration. Drug delivery from the blends was evaluated. A statistical factorial model was designed to explore the influence of three important blend parameters and their interactions, making it possible to predict the erosion and drug‐release behavior of the blend matrices. The PAA:poly(trimethylene carbonate) (PTMC) ratio and molecular weight of the polycarbonate component significantly influence the drug‐release performance, mass loss, and degree of plasticization. The interaction among these factors also influences the blend properties. Plasticization of PTMC enhances the drug release to an extent that is dependent on the amount of PAA used. We demonstrate that blending offers a convenient alternative to copolymerization for the preparation of polymer matrices with predictable drug delivery. © 1999 John Wiley & Sons, Inc. J Appl Polym Sci 72: 227–239, 1999

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Synthesis, properties, and biodegradation of poly(1,3-trimethylene carbonate)

Cited by 482 publications

References 9 publications

Quantitative TOF-SIMS analysis of oligomeric degradation products at the surface of biodegradable poly(α-hydroxy acid)s

Quantitative TOF-SIMS analysis of oligomeric degradation products at the surface of biodegradable poly(α-hydroxy acid)s

Aliphatic-aromatic poly(ester-carbonate)s obtained from simple carbonate esters, α,ω-aliphatic diols and dimethyl terephthalate

Copolymerization and polymer blending of trimethylene carbonate and adipic anhydride for tailored drug delivery

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