Synthesis of polyamides by active polycondensation. The structural and kinetical aspects of active esters aminolysis reactions

Katsarava, Ramaz; Kharadze, Darejan; Bendiashvili, T. M.; Urman, Ya.G.; Slonim, I.Ya.; Alekseeva, S. G.; Čefelín, P.; Janout, Václav

doi:10.1002/actp.1988.010390911

Cited by 9 publications

(7 citation statements)

References 38 publications

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“…However, this side reaction can be reduced like the industrial synthesis of the PA 46 (Stanyl®, DSM) reveals; or like it is also described by Pipper et al [55]. If the synthesis of high-molecular weight polysuccinamides runs over special esters of succinic acid, the chain growth stopping reaction of the aminolysis can almost be suppressed completely [59][60][61].…”

Section: Polymerizationmentioning

confidence: 86%

“…A technical synthesis of PA 44 has not been described in the literature yet. Publications can be found concerning polyamides, either on the basis of 1,4-butanediamine (PA 4n) [55][56][57][58] or on the basis of succinic acid (PA n4) [56,[59][60][61][62]. These polyamide types show interesting and unexpected properties.…”

Section: Polyamidesmentioning

confidence: 98%

“…Katsarava et al [59][60][61] suggested a new polycondensation method for the synthesis of high-molecular weight polysuccinamides on mild reaction conditions.…”

Section: Polyamidesmentioning

confidence: 99%

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Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources

et al. 2008

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Succinic acid is predicted to be one of the future platform chemicals that can be derived from renewable resources. The improvements in biotechnological succinic acid production are presented. Chemical conversion pathways to c-butyrolactone, tetrahydrofuran, 1,4-butanediole, and pyrrolidones are reviewed. An overview of possible new biopolymers (e. g. polyesters, polyamides, and poly(ester amide)s) based on succinic acid and its derivatives is given. Nevertheless, industrial processes using purified succinic acid from fermentation broths are not state of the art yet. Further improvements are needed until succinic acid-based chemical production will be economically favorable.

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Section: Polymerizationmentioning

confidence: 86%

Section: Polyamidesmentioning

confidence: 98%

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Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources

et al. 2008

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“…9 In the present work, we describe the synthesis and properties of a series of new polyamides obtained by polycondensation reaction of pentachlorophenyl 2,3,4,5tetra-O-methyl-D-mannarate (1Mn) or pentachlorophenyl 2,3,4,5-tetra-O-methylgalactarate (1Ga) with different diamines. This method [13][14][15] has been extensively used by us [5][6][7][8][9][10][11][12] and other authors 16 in previous works.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Poly(d-mannaramide)s and Poly(galactaramide)s

et al. 2004

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We describe a series of new aregic polyamides of the AABB-type by polycondensation reaction of pentachlorophenyl 2,3,4,5-tetra-O-methyl-D-mannarate or pentachlorophenyl 2,3,4,5-tetra-O-methylgalactarate with different diamines. Fully sugar-based polyamides have been prepared from the aldaric esters and the dihydrochlorides of 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-methyl-L-arabinitol or 1,5-diamino-1,5-dideoxy-2,3,4-tri-O-methylxylitol. Polyamides derived from the aldaric esters and non-carbohydrate alkylenediamines are also investigated. All the polyamides were soluble in the usual organic solvents, and slightly soluble in water. All of them were very hygroscopic, especially those that were fully sugarbased. DSC and X-ray powder diffraction studies showed that most of them are crystalline and that the thermal properties and crystal structure of these carbohydrate-based polyamides depend on their constitution and on the configuration of the carbohydrate-based moiety.

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“…In this connection, it was the purpose of the present work to study a third approach, namely polycondensations of free diamines with activated esters (here the 4‐chlorophenyl ester) of dicarboxylic acids. This approach was previously used by Katsarava and coworkers for syntheses of numerous polyamides,6–9 but at that time analytical methods allowing for the detection of cyclic oligo‐ and polyamides were not available. For the present work, oligoether diamines were used as nucleophilic monomers for two reasons.…”

Section: Introductionmentioning

confidence: 99%

New Polymer Syntheses, 112

Kricheldorf

Richter

Steinmann

et al. 2003

Macro Chemistry & Physics

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Bis(4‐chlorophenyl)sebacate (BCPS) was polycondensed with 1,12‐diamino‐4,9‐dioxadodecane or with its bistrimethylsilyl derivative in three different solvents with variation of time and temperature. The highest molecular weights were obtained in dimethylsulfoxide at 60 °C. The highest fraction of cyclic polyamides was detected by MALDI‐TOF mass spectrometry in the samples with the highest molecular weights. Numerous polycondensations of BCPS and 1,13‐diamino‐4,7,10‐trioxatridecane were performed with variation of solvent, time and temperature. Again the best results were obtained in dimethylsulfoxide at 60 °C. The fraction of cyclic polyamides increased with higher average molecular weights of the samples. The MALDI‐TOF mass spectrum of the sample with the highest molar mass (Mn ca. 30 000 Da) exclusively displayed mass peaks of cycles (detected up to 13 000 Da). No side reactions were observed.

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Synthesis of polyamides by active polycondensation. The structural and kinetical aspects of active esters aminolysis reactions

Abstract: &iTSAlCAVA, l

Cited by 9 publications

References 38 publications

Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources

Succinic Acid: A New Platform Chemical for Biobased Polymers from Renewable Resources

Synthesis and Properties of Poly(d-mannaramide)s and Poly(galactaramide)s

New Polymer Syntheses, 112

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