Synthesis and Characterization of a New Degradable Poly(ester amide) Derived from 6-Amino-1-hexanol and Glutaric Acid

Vera, Montserrat; Almontassir, Ahmed; Rodríguez‐Galán, Alfonso; Puiggalı́, Jordi

doi:10.1021/ma0345652

Cited by 36 publications

(27 citation statements)

References 29 publications

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“…The intense CO stretch at 1712 cm −1 confirmed the formation of ester bonds. This was similar with reported results for other poly(ester amide)s 13, 27. The characteristic ethylene oxide stretching bands at 1118 cm −1 were observed as well.…”

Section: Resultssupporting

confidence: 92%

“…There has been growing interest in poly(ester amide)s because these polymers may offer an interesting combination of properties: a high degradability caused by the ester linkages and good mechanical properties caused by the establishment of hydrogen bonds between amide groups. A number of poly(ester amide)s varying either in chemical structure and/or microstructure have been described by various authors 1–13. Moreover, the product of BAK 1095, which corresponds to a random poly(ester amide) derived from 1,4‐butaediol, adipic acid, and caprolactame by Bayer, has recently been commercialized 14, 15.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of novel biodegradable aromatic–aliphatic poly(ester amide)s containing ethylene oxide moieties

Wang

2008

J of Applied Polymer Sci

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A series of novel biodegradable aromaticaliphatic poly(ester amide)s containing approximately equal amounts of amide and ester groups were successfully prepared through the interfacial polycondensation of 1,6-hexanediamine and aromatic diacylchlorides containing ethylene oxide moieties. The structure of the poly(ester amide)s was verified by Fourier transform infrared and NMR spectra. Differential scanning calorimetry and thermogravimetric analysis measurements demonstrated that the obtained polymers were amorphous and stable up to 3008C under nitrogen. The synthesized poly(ester amide)s showed good hydrophilicity and took up water in amounts up to 50% of their weights when exposed to a humid atmosphere. Under physiological conditions, the poly(ester amide)s were hydrolysable in a rapid and steady way.

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Section: Resultssupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel biodegradable aromatic–aliphatic poly(ester amide)s containing ethylene oxide moieties

Wang

2008

J of Applied Polymer Sci

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“…Amino acid‐based biodegradable poly(ester‐amide) (PEA) has been widely investigated due to their excellent biocompatibility, biodegradability, and designability . Ester and amide bonds in the polymer backbone provide PEAs with the properties of both polyester and polyamides.…”

Section: Introductionmentioning

confidence: 99%

In vitro and in vivo degradation of potential anti‐adhesion materials: Electrospun membranes of poly(ester‐amide) based on l‐phenylalanine and p‐(dioxanone)

et al. 2016

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Electrospun membranes of poly(p-dioxanone-co-l-phenylalanine) (PDPA) hold potential as an anti-adhesion material. Since adjustable degradation properties are important for anti-adhesion materials, in this study, the in vitro and in vivo degradation processes of PDPA electrospun membranes were investigated in detail. The morphological analysis of these membranes revealed the main degradation conditions of PDPA membranes. The weight remaining and molecular weight variation showed that the overall degradation rate of the membranes could be adjusted by modulating the molecular structure of the PDPAs. Especially, α-chymotrypsin could catalyze the degradation process of PDPAs. Based on these results, the in vitro degradation mechanism was demonstrated, and confirmed by H NMR of the hydrolysis products. Finally, the in vivo degradation and biocompatibility of different PDPAs were investigated. The kinetic study showed that the in vitro and in vivo molecular weight loss of PDPAs have the first-order characteristics. The in vivo degradation rate of the most Phe-containing PDPA-3 is the slowest, and this result relates to the biocompatibilities of PDPAs. © 2016 Wiley Periodicals, Inc. J Biomed Mater Res Part B: Appl Biomater, 105B: 1369-1378, 2017.

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“…Polyglycolide 3 and poly(tetramethylene succinate), 4 with melting temperatures of 235 and 114 8C respectively, are exceptions to this rule and are also examples of polyesters employed as specialities and commodities, respectively. Different poly(ester amide)s with a statistical, 5,6 blocky, 7,8 or sequential [9][10][11][12] nature have been synthesized and characterized. However, structural studies on polymers with a regular disposition of amide and ester groups are scarce since the structural resolution is hindered by their relatively large repeat units.…”

Section: Introductionmentioning

confidence: 99%

Alternating poly(ester amide)s of glycolic acid and ω‐amino acids: Crystalline morphology and main crystallographic data

Botines

Casas

Puiggalı́

2007

J Polym Sci B Polym Phys

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The unit cell parameters of two alternating poly(ester amide)s constituted by glycolic acid and x-amino acid units have been determined by interpretation of Xray and electron diffraction patterns. Orthorhombic unit cells containing two chain segments with a nonplanar conformation have been derived. The electron diffraction patterns were rather different from those characteristic of aliphatic polyamides and polyesters with a zig-zag conformation. Chain-folded lamellar crystals have been obtained by isothermal crystallization of dilute diol or glycerine solutions and the crystalline habit has been studied by means of real space electron microscopy. Polyethylene decoration techniques have been applied to evaluate the regularity of the folding surfaces. Diffraction and morphologic data suggest that hydrogen bonds between amide groups were established along a single direction, which coincides with the preferential crystal growth direction. Spherulites prepared from both evaporation of formic acid solutions and melt crystallization have been also studied. Diffraction data indicate that hydrogen bonds are aligned along the spherulite radius. V V C 2007 Wiley Periodicals, Inc. J Polym Sci Part B: Polym Phys 45: 815-825, 2007

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Synthesis and Characterization of a New Degradable Poly(ester amide) Derived from 6-Amino-1-hexanol and Glutaric Acid

Cited by 36 publications

References 29 publications

Synthesis and characterization of novel biodegradable aromatic–aliphatic poly(ester amide)s containing ethylene oxide moieties

Synthesis and characterization of novel biodegradable aromatic–aliphatic poly(ester amide)s containing ethylene oxide moieties

In vitro and in vivo degradation of potential anti‐adhesion materials: Electrospun membranes of poly(ester‐amide) based on l‐phenylalanine and p‐(dioxanone)

Alternating poly(ester amide)s of glycolic acid and ω‐amino acids: Crystalline morphology and main crystallographic data

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