Synthesis and properties of stereoregular poly(ester amides) derived from carbohydrates

Pinilla, Inmaculada Molina; Martı́nez, Manuel Bueno; Mata, Francisca Zamora; Galbis, Juan A.

doi:10.1002/(sici)1099-0518(19980115)36:1<67::aid-pola10>3.3.co;2-q

Cited by 5 publications

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“…Polyesteramides were synthesized by the polycondensation of monomers I and II with DMF as a solvent and triethylamine as an acid acceptor to produce free amino groups in II 9, 23, 24. To obtain high molecular weight polymers, polycondensation using this kind of active ester has been generally conducted at room temperature, often for up to 10 days.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Fan

Kobayashi

Kise

2001

J. Polym. Sci. A Polym. Chem.

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Novel polyesteramides were synthesized from p‐nitrophenyl esters of sebacic or adipic acids and diamines containing α‐amino acid ester groups. The optimal polymerization condition was 60 °C in N,N‐dimethylformamide. The structures of these polymers were confirmed by IR and NMR. The number‐average molecular weights of these polyesteramides ranged from 2280 to 23,600 (except for the polymers containing glycine residues), depending on the nature of the amino acid used. The biodegradability of the polyesteramides was investigated by in vitro hydrolysis with proteases and a lipase as catalysts in borate buffer solutions. The results indicated that the polymers containing L‐phenylalanine were hydrolyzed most effectively by α‐chymotrypsin, subtilisin Carlsberg, and subtilisin BPN′. The polyesteramides containing other amino acid residues also underwent hydrolysis to different extents, reflecting the substrate specificity of the proteases. Lipase had almost no effect on the hydrolytic degradation of these polyesteramides. The polymers containing glycine residues were hardly decomposed by any of the enzymes used. © 2001 John Wiley & Sons, Inc. J Polym Sci A: Polym Chem 39: 1318–1328, 2001

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Section: Resultsmentioning

confidence: 99%

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Fan

Kobayashi

Kise

2001

J. Polym. Sci. A Polym. Chem.

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“…Three polymerization methods are usually used to prepare PEAs: melt polycondensation,14–16 interfacial polycondensation,8 and solution polycondensation 3, 11, 13, 17–19. In comparison with the other two methods, solution polycondensation can be carried out under milder conditions, such as lower temperatures, and is easy to operate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel biodegradable unsaturated poly(ester amide)s

Guo

Chu

Chkhaidze

et al. 2005

J. Polym. Sci. A Polym. Chem.

113

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A series of novel biodegradable unsaturated poly(ester amide)s (UPEAs) were synthesized through the solution polycondensation of two unsaturated monomers, di-p-nitrophenyl fumarate and L-phenylalanine 2-butene-1,4-diol diester p-toluene sulfonate, and four other saturated monomers in different combinations. The UPEAs were obtained in fairly good yields with N,N-dimethylacetamide (DMA) as the solvent. The number-average and weight-average molecular weights of the UPEAs, measured by gel permeation chromatography, ranged from 10 to 30 kg/mol, they had a rather narrow molecular weight distribution of 1.40. The chemical structures of the novel biodegradable UPEAs were confirmed by both IR and NMR spectra. The UPEAs had higher glass-transition temperatures than saturated PEAs of similar structures, and their glass-transition temperatures were affected more by the CAC double bond located in the diamide part than by those in the diester part. The solubility of the polymers was poor in water but better in DMA and dimethyl sulfoxide. With the availability of these inherent CAC double bonds in the UPEA backbones, these UPEAs have the functionality of CAC bonds, such as photochemical reactivity or the ability to react with or be modified by other bioactive or other environmentally sensitive compounds, and this can easily extend their applications to biomedical and pharmaceutical areas.

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“…Naturally occurring sugars such as L-arabinose and D-xylose have been incorporated in the polymer backbone to yield stereoregular PEAs [101][102][103]. The starting materials, which are sugars, come from renewable resources and are easily available and cost effective.…”

Section: Monomers/building Blocks From Natural (Origin) Sourcesmentioning

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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Synthesis and properties of stereoregular poly(ester amides) derived from carbohydrates

Cited by 5 publications

References 0 publications

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Synthesis and specific biodegradation of novel polyesteramides containing amino acid residues

Synthesis and characterization of novel biodegradable unsaturated poly(ester amide)s

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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