Alternating Copoly(ester amide)s derived from Amino Alcohols andL-Tartaric and Succinic Acids

Villuendas, Isabel; Bou, Jordi J.; Rodríguez‐Galán, Alfonso; Muñoz‐Guerra, Sebastián

doi:10.1002/1521-3935(20010101)202:2<236::aid-macp236>3.0.co;2-h

Cited by 25 publications

(15 citation statements)

References 5 publications

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“…Generally, these materials are biodegradable and are applicable in the biomedical field, for instance in the fabrication of controlled drug delivery devices. [9][10][11][12][13] In the present paper, the preparation of biodegradable poly(ether ester)s containing different hydrogen bonding units and PEG segments is reported. Symmetrical diesterterminated monomers, carrying amide, carbamate, or urea H-bonding units were synthesized and used as comonomers, and the influence of different H-bonding units on the ultimate properties of the materials was evaluated.…”

Section: Introductionmentioning

confidence: 99%

“…4H, OCH 2 CH 2 OCO), 4.1 (t, 4H, CH 2 OCO), 3.6 (t, 80H, CH 2 O) 3.2 (m, 8H, CH 2 NHCO), 2.3 (t, 8H, CH 2 COO), 2.2 (t, 8H, CH 2 CONH), 1.7 (m, 4H, CH 2 CH 2 OCO), 1.6 (b, 6H, CH 2 CH 2 NH and CH 2 CH 2 O), 1.5 (m, 16H, CH 2 CH 2 CONH), 1.3 (m, 8H, CH 2 ) 13. C NMR (CDCl 3 ): d ¼ 173.7 (CONH), 173.1 (COO), 70.5 (COOCH 2 CH 2 O), 69.1 (OCH 2 CH 2 O), 63.7 (CH 2 OCO), 63.3 (CH 2 OCO), 39.0 (CH 2 NHCO) 36.6 (CH 2 CONH), 34.1 (CH 2 COO), 29.4 (CH 2 CH 2 NH), 28.9 (CH 2 ), 26.0 (CH 2 ), 25.6 (CH 2 ), 25.3 (CH 2 CH 2 CONH), 24.7 (CH 2 CH 2 COO).Poly(diethyl 9,16-diaza-7,18-dioxa-8,17-dioxo-1,24-tetracosanedioate-alt-1,4-butandiol/PEG1000) (Run pC6-30)This polymer sample was prepared according to the procedure described above starting from E5C6 (5.0 g, 10 mmol), PEG1000 (1.5 g, 1.0 mmol), 1,4-butanediol (1.2 g, 13 mmol), Irganox 1330 (76 mg), and Ti(OBu) 4 (153 ml of 5% toluene solution).…”

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confidence: 97%

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Synthesis and Characterization of Segmented Poly(ether ester)s Containing H‐Bonding Units

Signori

Solaro

Chiellini

et al. 2003

Macro Chemistry & Physics

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A series of poly(ether ester)s containing different H‐bonding units (amide, carbamate, urea) was prepared by polycondensation in bulk, using Ti(OBu)4 as a catalyst. The copolymers were obtained starting from PEG1000, 1,4‐butanediol, and a symmetrical, bis‐ester terminated monomer carrying H‐bonding units. These materials were designed for biomedical applications, in which ultimate biodegradability of the materials is required. The influence of the nature of the H‐bonding unit and of the length of the methylene spacer between H‐bonding groups on the thermal and solubility properties of copolymers was investigated. Amide containing copolymers were more thermally stable than ones containing carbamate, consistent with the observed behavior of the corresponding monomers. In most cases, differential scanning calorimetry (DSC) traces were quite complex because of phase separation and dependent on the applied cooling rate. Copolymers containing urea bonds were less soluble in most organic solvents, but their thermal properties were not significantly different than their amide containing counterparts.

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Section: Introductionmentioning

confidence: 99%

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confidence: 97%

Synthesis and Characterization of Segmented Poly(ether ester)s Containing H‐Bonding Units

Signori

Solaro

Chiellini

et al. 2003

Macro Chemistry & Physics

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“…Regular PEAs with AAEE sequences can be synthesized by condensing preformed bisamide diols or bisester diamines with diacids or diacid chlorides in solution [37][38][39] or melt [37][38][39][40][41]. 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].…”

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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“…Readily available monosaccharides either produced by degrading polysaccharides or simply recovered from natural resources, are conveniently modified to afford aldaric acids, alditols and diaminoalditols suitable for polycondensation. A variety of polyamides, [4][5][6][7][8][9][10][11][12] polyesters, [13][14][15][16][17] and polyesteramides [18][19][20][21][22][23][24][25] as well as other polycondensates 26 derived from tetroses, pentoses and hexoses have been thus obtained and characterized, their structure examined, and some of their more relevant properties comparatively evaluated. We have been dedicated to the research of carbohydrate-based linear polycondensates for more than two decades so a pretty wide number of systems have been studied so far.…”

Section: Introductionmentioning

confidence: 99%

Carbohydrate-based polyamides and polyesters: an overview illustrated with two selected examples

Muñoz‐Guerra

2012

High Performance Polymers

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An overview on the synthesis, structure and properties of polyamides and aromatic copolyesters produced by using monomers derived from carbohydrates is provided. Two examples are selected for illustration: (a) aliphatic polyamides prepared from aldaric acids and (b) aromatic copolyesters containing alditols units. Polycondensation in solution of n-alkanediamines (n taking even values from 6 to 12) with activated pentaric (L-arabino and xylo) and hexaric (galacto and D-manno) acids bearing the secondary hydroxyl groups protected as methyl ether, afforded linear polyaldaramides PA-nSu with M w oscillating between 25 000 and 150 000 g mol À1 . They are stable above 300 C and are semicrystalline even so only PA-nMn are stereoregular. Melting temperatures of PA-nSu range between 140 and 230 C and most of them are able to crystallize from the melt at a rate that increases with the length of the polymethylene segment. Both melting and glass transition temperatures decrease with the content in sugar units. Spherulitic films, oriented fibers and lamellar single crystals could be obtained from PA-nSu. All these polyamides seem to adopt a common crystal structure made of hydrogen-bonded sheets with the sugar residue skewed to attain an efficient side-by-side packing of the polymer chains. Aromatic homopolyesters and copolyesters derived from terephthalic acid and mixtures of butylene glycol and O-methylated alditols were prepared by polycondensation in the melt with M w in the 20 000-50 000 g mol À1 range and a random microstructure. The thermal properties of PBT containing alditols units are very depending on the sugar constitution and copolyester composition. In general they are thermally stable above 300 C and display crystallinity for contents in alditols up to 30%. Melting temperatures decrease with the content in alditols whereas an opposite trend is observed for glass transition temperatures. The crystalline structure of PBT is preserved in the crystalline copolyesters whereas a different crystal lattice is adopted by homopolyesters entirely made of alditol units. In general, polyamides and polyesters containing sugar derived units are widely soluble in organic solvents, markedly hydrophilic and more susceptible to hydrolysis than their parent polymers.

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Alternating Copoly(ester amide)s derived from Amino Alcohols andL-Tartaric and Succinic Acids

Cited by 25 publications

References 5 publications

Synthesis and Characterization of Segmented Poly(ether ester)s Containing H‐Bonding Units

Synthesis and Characterization of Segmented Poly(ether ester)s Containing H‐Bonding Units

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

Carbohydrate-based polyamides and polyesters: an overview illustrated with two selected examples

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