Sequential poly(ester amide)s based on glycine, diols, and dicarboxylic acids: Thermal polyesterification versus interfacial polyamidation. Characterization of polymers containing stiff units

Asín, L.; Armelín, Elaine; Montané, J.; Rodríguez‐Galán, Alfonso; Puiggalı́, Jordi

doi:10.1002/pola.10082

Cited by 89 publications

(66 citation statements)

References 17 publications

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“…This procedure has been successfully applied to prepare poly(ester amide)s containing -amino acid units by reaction of a diol with a diamide-diester previously obtained by condensation of a diacid chloride with an -amino acid methyl ester [23,24] (Figure 3). Secondary reactions derived from the required high temperatures constitute the main disadvantage of this method that may limit the final molecular weight and cause problems when monomers have functional side groups highly susceptible to undertake these undesirable reactions.…”

Section: Melt Polycondensationmentioning

confidence: 99%

Degradable Poly(ester amide)s for Biomedical Applications

2010

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Poly(ester amide)s are an emerging group of biodegradable polymers that may cover both commodity and speciality applications. These polymers have ester and amide groups on their chemical structure which are of a degradable character and provide good thermal and mechanical properties. In this sense, the strong hydrogen-bonding interactions between amide groups may counter some typical weaknesses of aliphatic polyesters like for example poly(-caprolactone). Poly(ester amide)s can be prepared from different monomers and following different synthetic methodologies which lead to polymers with random, blocky and ordered microstructures. Properties like hydrophilic/hydrophobic ratio and biodegradability can easily be tuned. During the last decade a great effort has been made to get functionalized poly(ester amide)s by incorporation of -amino acids with hydroxyl, carboxyl and amine pendant groups and also by incorporation of carbon-carbon double bonds in both the polymer main chain and the side groups. Specific applications of these materials in the biomedical field are just being developed and are reviewed in this work (e.g., controlled drug delivery systems, hydrogels, tissue engineering and other uses like adhesives and smart materials) together with the main families of functionalized poly(ester amide)s that have been developed to date.

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Section: Melt Polycondensationmentioning

confidence: 99%

Degradable Poly(ester amide)s for Biomedical Applications

2010

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“…The resulting polymers showed T g between 100 and 190°C and were stable up to 400°C. Asín et al [199] synthesized sequential chiral PEAs derived from glycine by a two-steps method, involving a final thermal polyesterification. They compared this method in detail with their previous reported on the basis of interfacial polymerization.…”

Section: Poly(ester-amide)smentioning

confidence: 99%

Advances in synthetic optically active condensation polymers - A review

Mallakpour

Zadehnazari²,

Iran³

2011

Express Polym. Lett.

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Abstract. The study of optically active polymers is a very active research field, and these materials have exhibited a number of interesting properties. Much of the attention in chiral polymers results from the potential of these materials for several specialized utilizations that are chiral matrices for asymmetric synthesis, chiral stationary phases for the separation of racemic mixtures, synthetic molecular receptors and chiral liquid crystals for ferroelectric and nonlinear optical applications. Recently, highly efficient methodologies and catalysts have been developed to synthesize various kinds of optically active compounds. Some of them can be applied to chiral polymer synthesis. In a few synthetic approaches for optically active polymers, chiral monomer polymerization has essential advantages in applicability of monomer, apart from both asymmetric polymerization of achiral or prochiral monomers and enantioselective polymerization of a racemic monomer mixture. The following are the up to date successful approaches to the chiral synthetic polymers by condensation polymerization reaction of chiral monomers.

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“…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].…”

Section: Regular Peas With Aaee Sequencesmentioning

confidence: 99%

“…The incorporation of amino acids makes the polymer biocompatible. Preformed monomers can be synthesized by condensing amino acids such as alanine or glycine with diols to form diester-diamine salts which are then reacted with dicarboxylic acids or their dichlorides to form alternating PEAs [41,43,47,48,[51][52][53][54][55][61][62][63]. α,ω-Amino-alcohols-based alternating PEAs can also be obtained by condensing dicarboxylic acids with linear aliphatic amino alcohols with varying numbers of methylene groups [41,64].…”

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

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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.

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Sequential poly(ester amide)s based on glycine, diols, and dicarboxylic acids: Thermal polyesterification versus interfacial polyamidation. Characterization of polymers containing stiff units

Cited by 89 publications

References 17 publications

Degradable Poly(ester amide)s for Biomedical Applications

Degradable Poly(ester amide)s for Biomedical Applications

Advances in synthetic optically active condensation polymers - A review

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

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