Rigid, bio-based polyamides from galactaric acid derivatives with elevated glass transition temperatures and their characterization

Wróblewska, Aleksandra A.; Bernaerts, Katrien V.; Wildeman, Stefaan M. A. De

doi:10.1016/j.polymer.2017.07.069

Cited by 14 publications

(30 citation statements)

References 20 publications

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“…For example, the common method for the synthesis of polyamides is the polymerization of polyamide salts but it cannot be used for the synthesis of polyamides from galactaric acid derivatives due to their rapid degradation occurring simultaneously with melting. 16 , 25 …”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, the alkylation of amine groups is a significant side reaction, which leads to the deactivation of reactive groups and ultimately has inhibiting effect on the polymerization. 16 , 25 , 51 If aliphatic esters are used during the aminolysis the reaction time needs to be elongated. Exposition of the polymerization mixture to elevated temperatures for elongated periods results in a higher cross-linking risk for GalX, more degradation and more alkylation of the amine functional groups.…”

Section: Introductionmentioning

confidence: 99%

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Solvent-Free Method for the Copolymerization of Labile Sugar-Derived Building Blocks into Polyamides

Wróblewska

Stevens

Garsten

et al. 2018

ACS Sustainable Chem. Eng.

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This research focuses on the preparation of biobased copolyamides containing biacetalized galactaric acid (GalX), namely, 2,3:4,5-di-O-isopropylidene-galactaric acid (GalXMe) and 2,3:4,5-di-O-methylene-galactaric acid (GalXH), in bulk by melt polycondensation of salt monomers. In order to allow the incorporation of temperature-sensitive sugar-derived building blocks into copolyamides at temperatures below the degradation temperature of the monomers and below their melting temperatures, a clever selection of salt monomers is required, such that the sugar-derived salt monomer dissolves in the other salt monomers. The polymerization was investigated by temperature dependent FT-IR and optical microscopy. The structure of the obtained copolyamides was elucidated by NMR and matrix-assisted laser desorption ionization-time-of-flight (MALDI-TOF) techniques. The positive outcome of this modified polycondensation method depends on the solubility of sugar-derived polyamide salts in polyamide salts of comonomers and the difference between their melting temperatures, however does not depend on the melting temperature of the used sugar-derived monomer. A variety of comonomers was screened in order to establish the underlying mechanisms of the process.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Solvent-Free Method for the Copolymerization of Labile Sugar-Derived Building Blocks into Polyamides

Wróblewska

Stevens

Garsten

et al. 2018

ACS Sustainable Chem. Eng.

Self Cite

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“…The monomer is subsequently polymerized via aminolysis with a primary diamine and finally, the hydroxy groups are de‐protected with the addition of trifluoroacetic acid ( Scheme A) . A similar protocol was used for the synthesis of rigid polyamides having elevated glass transition temperatures (Scheme B) and for the dibutyltin (IV) oxide‐catalyzed synthesis of acetalized galactarate polyesters (Scheme C) . The second strategy involves the conversion of GlcA to the glucaric acid chloride acetate and its polymerization with various diols (Scheme D) and diamines (Scheme E) in dimethylacetamide solution or by interfacial polymerization in water and chloroform solutions …”

Section: Methodsmentioning

confidence: 99%

“…[17] A similar protocol was used for the synthesis of rigid polyamides having elevated glass transition temperatures (Scheme 1B) and for the dibutyltin (IV) oxide-catalyzed synthesis of acetalized galactarate polyesters (Scheme 1C). [18,19] The second strategy involves the conversion of GlcA to the glucaric acid chloride acetate and its polymerization with various diols (Scheme 1D) and diamines (Scheme 1E) in dimethylacetamide solution or by interfacial polymerization in water and chloroform solutions. [20,21] In the present work, we describe a novel three step biocatalyzed strategy that involves: 1) the extraction of pectin from sugar beet pulp and the recovery of GalA; followed by 2) the laccase-catalyzed oxidation of the GalA aldehyde and the recovery of GA; and 3) the enzymatic polycondensation of GA to obtain fully bio-based functional polyesters carrying lateral hydroxy functionalities without the use of traditional protection chemistry (Scheme 2).…”

Section: Doi: 101002/marc201900361mentioning

confidence: 99%

Sustainable Galactarate‐Based Polymers: Multi‐Enzymatic Production of Pectin‐Derived Polyesters

Vastano

Pellis

Machado

et al. 2019

Macromol. Rapid Commun.

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Large amounts of agricultural wastes are rich in pectins that, in many cases, disrupt the processing of food residues due to gelation. Despite pectins being a promising sustainable feedstock for bio‐based chemical production, the current pathways to produce platform molecules from this polysaccharide are hazardous and entail the use of strong acids. The present work describes a sequence of biocatalyzed reactions that involves 1) the extraction of pectin from sugar beet pulp and enzymatic recovery of galacturonic acid (GalA), followed by 2) the enzymatic oxidation of the GalA aldehyde and the recovery of galactaric acid (GA), and 3) the biocatalyzed polycondensation of GA to obtain fully bio‐based polyesters carrying lateral hydroxy functionalities. The acid‐free pectin extraction is optimized using enzymes and microwave technology. The conditions for enzymatic oxidation of GalA allow the separation of the GA produced by a simple centrifugation step that leads to the enzyme‐catalyzed polycondensation reactions.

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“…In the last decade, a lot of research was devoted to bio‐based PAs . The strategy is to enhance the mechanical properties of classical bio‐based PAs like PA 11.…”

Section: Introductionmentioning

confidence: 99%

Dynamic relaxations in a bio‐based polyamide with enhanced mechanical modulus

Haddou

Roggero

Dandurand

et al. 2018

J of Applied Polymer Sci

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A new grade of bio-based polyamide (PA)-PA meta-xylylene diamine 10 (PA mXD 10)-was investigated. Its first interest is that it permits mild processing conditions at about 200 C. The calorimetric study shows the existence of two cold crystallizations indicative of slow crystallization rate. The glass transition stabilizes at 55 C. By combining calorimetry with dynamic mechanical analysis and dynamic dielectric spectroscopy, we found a perfect consistency between the set of data giving the molecular mobility. The localized relaxations follow Arrhenius equations while the viscoelastic transition follows a Vogel-Fulcher-Tammann law. The compilation of all the relaxation times determined by means of the different analyses highlights a good correlation. This result is perfectly explained by the polarity of the macromolecular chain. The dynamic mechanical behavior showed a storage modulus higher than for the corresponding aliphatic PA and nearly constant until room temperature.

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Rigid, bio-based polyamides from galactaric acid derivatives with elevated glass transition temperatures and their characterization

Cited by 14 publications

References 20 publications

Solvent-Free Method for the Copolymerization of Labile Sugar-Derived Building Blocks into Polyamides

Solvent-Free Method for the Copolymerization of Labile Sugar-Derived Building Blocks into Polyamides

Sustainable Galactarate‐Based Polymers: Multi‐Enzymatic Production of Pectin‐Derived Polyesters

Dynamic relaxations in a bio‐based polyamide with enhanced mechanical modulus

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