Poly(ester amide)s derived from 1,4-butanediol, adipic acid and 1,6-aminohexanoic acid: characterization and degradation studies

Botines, Emma; Rodríguez‐Galán, Alfonso; Puiggalı́, Jordi

doi:10.1016/s0032-3861(02)00577-3

Cited by 32 publications

(13 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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. Wholly aromatic poly(ester amide)s are well known for their superior resistance to heat, outstanding mechanical resistance, poor biodegradability, and poor solubility in common solvents.…”

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

View full text Add to dashboard Cite

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.

show abstract

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

View full text Add to dashboard Cite

show abstract

“…Several poly(ester amide)s have been recently proposed and their promising performances are at present under evaluation 2–7. A commercial series of poly(ester amide)s is now circulated with the trade name BAK, based on adipic acid, caprolactone and hexamethylenediamine as the amide components and 1,4‐butanediol and ethylene glycol as the ester components 8–10. In general, polymeric systems with regular sequences possess high crystallinity but worse biodegradation rate, and vice versa 11–13.…”

mentioning

confidence: 99%

Sequence determination in aliphatic poly(ester amide)s by matrix‐assisted laser desorption/ionization time‐of‐flight and time‐of‐flight/time‐of‐flight tandem mass spectrometry

Rizzarelli

Puglisi²,

Montaudo

2005

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Poly(ester amide)s from dimethyl sebacate or sebacic acid and 2-aminoethanol or 4-amino-1-butanol were characterized by post-source decay matrix-assisted laser desorption/ionization time-of-flight (PSD-MALDI-TOF) and time-of-flight/time-of-flight tandem mass spectrometry (MALDI-TOF/TOF-MS/MS). Sodiated oligomers were selected as precursor ions for dissociation studies. PSD analysis was performed on dimethyl sebacate, dicarboxylic, carboxylic and amino alcohol, and diamino alcohol terminated oligomers. PSD-MALDI-TOF mass spectra yielded information on the fragmentation mechanisms of the poly(ester amide) chains, showing that the main cleavages proceed through a beta-hydrogen transfer rearrangement. MALDI-TOF/TOF-MS/MS provided structural information concerning ester/amide sequences in the polymer chains. As expected, together with the ions appearing in the PSD-MALDI mass spectrum, several new abundant fragment ions in the low-mass range are present in MALDI-TOF/TOF-MS/MS spectra. These new product ions proved to be diagnostic and made it possible to establish the presence of random sequences of ester and amide bonds in the poly(ester amide)s samples.

show abstract

“…Other types of preformed monomers were condensed with activated esters in solution [37,[42][43][44][45][46][47][48] or with dicarboxylic acid dichlorides or activated esters by interfacial polymerisation [49][50][51][52][53][54][55][56][57]. Polymerization of diamide-diesters with diols yields alternating PEAs which have a higher degree of crystallinity than the corresponding random PEAs [58][59][60]. α-Amino-acid-based sequential PEAs have been investigated by numerous research groups.…”

Section: Regular Peas With Aaee Sequencesmentioning

confidence: 99%

Concept and Synthesis of Poly(ester amide)s with One Isolated, Two or Three Consecutive Amide Bonds Randomly Distributed Along the Polyester Backbone

Garg

Keul

Klee

et al. 2009

Designed Monomers and Polymers

View full text Add to dashboard Cite

Poly(ester amide)s (PEAs) were prepared from diols, amino alcohols and diamines with an in-built amide group via polycondensation with 1,4-butanediol and dimethyl adipate. The tailor-made monomers were synthesized by ring opening of ε-caprolactone and ε-caprolactam using 1,4-diaminobutane, 4-aminobutanol and 2-aminoethanol. PEAs having an isolated amide bond or two or three consecutive amide bonds in the poly(butylene adipate) (PBA) backbone, respectively, were obtained via melt polycondensation. The concentration of the amide groups in the PEAs was varied by the amount of preformed α,ω-diamines, amino alcohols or diols introduced in the feed. A simple synthetic route to these preformed monomers and the corresponding PEAs is described. The products were obtained in high purity and high yields.

show abstract

Poly(ester amide)s derived from 1,4-butanediol, adipic acid and 1,6-aminohexanoic acid: characterization and degradation studies

Cited by 32 publications

References 7 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

Sequence determination in aliphatic poly(ester amide)s by matrix‐assisted laser desorption/ionization time‐of‐flight and time‐of‐flight/time‐of‐flight tandem mass spectrometry

Concept and Synthesis of Poly(ester amide)s with One Isolated, Two or Three Consecutive Amide Bonds Randomly Distributed Along the Polyester Backbone

Contact Info

Product

Resources

About