New Polyanhydrides Made from a Bile Acid Dimer and Sebacic Acid:  Synthesis, Characterization, and Degradation

Gouin, Sébastien G.; Zhu, Xiaoxia; Lehnert, Shirley

doi:10.1021/ma991364i

Cited by 56 publications

(49 citation statements)

References 33 publications

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“…The polymers have been subjected to degradation and release studies, using p-nitroaniline as the model drug. The degradation and release rates are found to be dependent on the copolymer composition, and no apparent toxicity is observed in vivo [110].…”

Section: Step-growth Polymerizationsmentioning

confidence: 91%

Synthesis of Terpene-Based Polymers

Zhao¹,

Schlaad²

2012

Advances in Polymer Science

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Terpenes or terpenoids are a large class of diverse biological compounds derived from isoprene. Due to their abundance in nature and desirable properties, there has been great interest in producing polymers with terpenes as either functional entities or as the main constituent. Terpene-based polymers have found applications as biomedical or liquid crystalline materials and, more importantly, have greatly contributed to the concept of sustainable polymer chemistry. The design and preparation of terpene-based polymers have involved different chemical strategies and a wide variety of polymerization techniques, making use of the chemical functionalities in terpene molecules, e.g. (conjugated) double bonds, hydroxyl and carboxyl groups. This review describes the synthetic methodologies for terpene-based polymers, classified by the position of terpene entities in the polymer chains, i.e., main chain, terminal or central group, and pendant group.

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Section: Step-growth Polymerizationsmentioning

confidence: 91%

Synthesis of Terpene-Based Polymers

Zhao¹,

Schlaad²

2012

Advances in Polymer Science

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“…[2][3][4] This easily available and low-cost chemical, thanks to its intrinsic biodegradability, biocompatibility and renewability combined with the easy modifiability of the hydroxyl and carboxyl groups and the stability of steroid skeleton, was chosen by many researchers to design and synthesize new cholic acid-containing oligomeric or polymeric materials. [5,6] Various types of such polymers were produced in the last two decades: in several of these, the CAs were part of the main chain, [7][8][9][10] while in others, the CAs were connected as pendants [11][12][13] or, more recently, as the core of star-shaped polymers. [14][15][16][17][18][19] New star-shaped polymers have attracted the attention of scientists for many years in virtue of their unique physicochemical properties.…”

Section: Introductionmentioning

confidence: 99%

Novel tri- and tetrafunctional cholic acid-based initiators for the synthesis of star-shaped poly(L-lactide)s

Donvito

Fantin

Fogagnolo

et al. 2016

Designed Monomers and Polymers

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In this investigation, two novel multifunctional initiators for ring-opening polymerization were synthesized in three steps starting from cholic acid. Thus, cholic acid (1a) and its methyl ester (1b) were quantitatively transformed, via solvent-free reaction with succinic anhydride, to the corresponding 3, 7, 12-tri-hemisuccinate derivatives (3a-b). The polyacidic compounds (3a-b) were treated with thionyl chloride affording the corresponding acyl chlorides 4a-b which, in turn, were reacted with ethylene glycol to give the derivatives 2a-b having three and four primary alcohol end groups. These compounds, fully characterized by 1 H, 13C NMR and mass spectrometry, have been assessed as initiators in the ring-opening polymerization of L-lactide using stannous octanoate as catalyst. The resulting three-and four-armed star-shaped poly(L-lactide)s, which were characterized by 1 H NMR, SEC, DSC and TGA analysis, were amorphous, and their glass transition temperatures ranged from 13.7 to 36.5 °C. Additionally, some cholic acid-based star-shaped polylactic structures recently published have been critically reconsidered showing that these molecules, described as star polymers, were actually linear polymers.

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“…Polyanhydrides have been synthesized from dimer and trimer unsaturated fatty acids [3][4][5] and other fatty acids [6][7][8] . The dimers of oleic acid and erucic acid are liquid oils containing two carboxylic acids available for anhydride polymerization.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Properties of Copolyanhydrides Based on 2-Hexadecylsuccinic Acid and Sebacic Acid

Hamdan¹,

Xiangmei²,

Huang³

et al. 2007

American J. of Applied Sciences

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Poly(2-hexadecylsuccinic acid-sebacic acid) (P(HSA-SA)) copolymers have been prepared by melt polycondensation. The copolymers were characterized by FT-IR, 1 HNMR, gel permeation chromatography (GPC), differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). In vitro studies showed that all our prepared copolymers are degradable in phosphate buffer at 37 °C. The release profiles of hydrophilic model drug, ciprofloxcin hydrochloride, from the copolymers, follow first order release kinetics. All the preliminary results suggested that the copolymer might be potentially used as drug delivery devices.

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New Polyanhydrides Made from a Bile Acid Dimer and Sebacic Acid: Synthesis, Characterization, and Degradation

Cited by 56 publications

References 33 publications

Synthesis of Terpene-Based Polymers

Synthesis of Terpene-Based Polymers

Novel tri- and tetrafunctional cholic acid-based initiators for the synthesis of star-shaped poly(L-lactide)s

Preparation and Properties of Copolyanhydrides Based on 2-Hexadecylsuccinic Acid and Sebacic Acid

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