Rapid Synthesis of Polyanhydrides by Microwave Polymerization

Vogel, Brandon M.; Mallapragada, Surya K.; Narasimhan, Balaji

doi:10.1002/marc.200300156

Cited by 39 publications

(26 citation statements)

References 19 publications

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“…Poly(anhydride)s are studied since long time as drug delivery systems with a tunable surface erosion: the synthesis of several poly(anhydride)s from aliphatic and aromatic diacids were conducted under microwave conditions to reduce reaction times from 3 h to 6-20 min at atmospheric pressure. Molecular weights were similar to the product of conventional heating; working under vacuum, as well as the isolation of an intermediate acetylated prepolymer, was not necessary, drastically simplifying the synthetic procedure (Vogel et al, 2003). With the aim of valorizing renewable feedstocks, interesting poly(ether)s were synthesized from isosorbide (1,4:3,6-dianhydrosorbitol) and 1,8-dibromoor 1,8-dimesyl-octane using phase transfer catalysis under microwave irradiation.…”

Section: Other Step Growth Polymerizationsmentioning

confidence: 99%

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Frediani¹,

Giachi²,

Rosi³

et al. 2011

Microwave Heating

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Section: Other Step Growth Polymerizationsmentioning

confidence: 99%

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Frediani¹,

Giachi²,

Rosi³

et al. 2011

Microwave Heating

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“…Mallapragada and co-workers showed that the polymerization can be carried out in a single step, admittedly with intermediate removal of unreacted acetic anhydride (Scheme 5b). [54] The dicarboxylic acid (like sebacic acid) and excessive acetic anhydride were placed in a high-pressure vial that was capped and irradiated for 2 min in a microwave oven (General Electrics, 1 100 W). Immediately after the reaction, the vial was decapped and the unreacted acetic anhydride was evaporated from the hot reaction solution by an inert gas flow.…”

Section: Polyethers and Polyestersmentioning

confidence: 99%

Microwave‐Assisted Polymer Synthesis: State‐of‐the‐Art and Future Perspectives

Wiesbrock

Hoogenboom

Schubert

2004

Macromol. Rapid Commun.

465

256

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Summary: Monomodal microwaves have overcome the safety uncertainties associated with the precedent domestic microwave ovens. After fast acceptance in inorganic and organic syntheses, polymer chemists have also recently discovered this new kind of microwave reactor. An almost exponential increase of the number of publications in this field reflects the steadily growing interest in the use of microwave irradiation for polymerizations. This review introduces the microwave systems and their applications in polymer syntheses, covering step‐growth and ring‐opening, as well as radical polymerization processes, in order to summarize the hitherto realized polymerizations. Special attention is paid to the differences between microwave‐assisted and conventional heating as well as the “microwave effects”.Results of search on number of publications on microwave‐assisted polymerizations, sorted by year.imageResults of search on number of publications on microwave‐assisted polymerizations, sorted by year.

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“…[12][13][14][15][16][17] However, none of these examples has addressed condensation polymerization reactions on a high-throughput level without the use of a catalyst, deep-well plates that require large solution volumes, or solution polymerizations that have concentration dependence. Additionally, characterization of these polymer libraries requires isolation of the product from the reaction solvent.…”

Section: Introductionmentioning

confidence: 99%

Parallel Synthesis and High Throughput Dissolution Testing of Biodegradable Polyanhydride Copolymers

et al. 2005

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We have demonstrated that polycondensation reactions can be carried out in a combinatorial fashion and that the polymer library can be screened at high throughput using a rapid prototyping technique to fabricate multiwell substrates. A linearly varying compositional library of 100 different biodegradable polyanhydride random copolymers that are promising carriers for controlled drug delivery was designed, fabricated, and characterized by IR microscopy within a few hours. The polyanhydride copolymer library was based on 1,6-bis(p-carboxyphenoxy)hexane (CPH) and sebacic anhydride (SA) and was characterized with infrared microspectroscopy to determine the composition within each well. Since degradation and release rates depend on copolymer composition, we also developed new high-throughput methods to investigate drug release from this library of copolymers by designing specific wells for each task. A subset of this library was chosen, and a substrate was designed and fabricated to enable the synthesis and monitoring of dye dissolution from a range of polyanhydride copolymers in a parallel fashion using a CCD camera. Multisample substrates were fabricated with a novel rapid prototyping method that consists of an organic solvent-resistant array of 10 x 10 microwells of 2-Î¼L volume each. The libraries were deposited with a custom-built liquid dispensing system consisting of a series of computer-controlled volume-dispensing pumps and XYZ motion stages. The parallel dye dissolution study displayed a decreasing rate of release with increasing CPH content. This result agrees with previously published data for dye release from poly(CPH-co-SA) copolymers. The methodology described in this work is amenable to numerous applications in the arenas of high-throughput polymer synthesis and characterization. We have demonstrated that polycondensation reactions can be carried out in a combinatorial fashion and that the polymer library can be screened at high throughput using a rapid prototyping technique to fabricate multiwell substrates. A linearly varying compositional library of 100 different biodegradable polyanhydride random copolymers that are promising carriers for controlled drug delivery was designed, fabricated, and characterized by IR microscopy within a few hours. The polyanhydride copolymer library was based on 1,6-bis(p-carboxyphenoxy)hexane (CPH) and sebacic anhydride (SA) and was characterized with infrared microspectroscopy to determine the composition within each well. Since degradation and release rates depend on copolymer composition, we also developed new high-throughput methods to investigate drug release from this library of copolymers by designing specific wells for each task. A subset of this library was chosen, and a substrate was designed and fabricated to enable the synthesis and monitoring of dye dissolution from a range of polyanhydride copolymers in a parallel fashion using a CCD camera. Multisample substrates were fabricated with a novel rapid prototyping method that consists of an organic s...

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Rapid Synthesis of Polyanhydrides by Microwave Polymerization

Cited by 39 publications

References 19 publications

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Synthesis and processing of biodegradable and bio-based polymers by microwave irradiation

Microwave‐Assisted Polymer Synthesis: State‐of‐the‐Art and Future Perspectives

Parallel Synthesis and High Throughput Dissolution Testing of Biodegradable Polyanhydride Copolymers

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