Novel Biodegradable Polyamides Based on Tartaric Acid: Preparation and Properties

Mathakiya, Ismail; Rakshit, Animesh Kumar; Iyer, Bragadish D; Shah, Avinash K.

doi:10.1080/00914030490429915

Cited by 6 publications

(5 citation statements)

References 15 publications

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“…Polycarbonates have attracted much attention due to their biodegradability, biocompatibility, and non toxicity. Moreover, the presence of hydrophilic functional groups enhances their biodegradability [213][214][215][216][217][218].…”

Section: Ring Opening Polymerization Of Carbonatesmentioning

confidence: 99%

“…In particular, L-tartaric acid has been extensively used in organic synthesis as a source of chirality, but its application in polymers has been somewhat limited to the synthesis of polyamides [217,218], polyesters [219], polyurethanes [220,221] and polycarbonates [222][223][224]. Degradable tartaric acid-based polymers have been prepared by condensation polymerization, which is limited by the removal of the condensate.…”

Section: Ring Opening Polymerization Of Carbonatesmentioning

confidence: 99%

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Lipases as Efficient Catalysts in the Synthesis of Monomers and Polymers with Biomedical Applications

Liñares¹,

Baldessari

2013

COC

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Enzymatic polymerization shows to be an advantageous approach in polymer chemistry, particularly in the case of obtaining polymers required for biomedical applications, which are intented for human consumption. Enzymes apply procedures that are environmentally friendly involving waste minimization, hazard reduction, the efficient use of energy and the use of renewable sources. This paper reviews selected examples of the recent progress in lipase-catalyzed polymerization. The application of this hydrolase in the synthesis of polyesters, polycarbonates and polyamides following traditional mechanisms is covered. Moreover, lipase-catalyzed synthesis of novel vinyl copolymers and monomers is described.

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Section: Ring Opening Polymerization Of Carbonatesmentioning

confidence: 99%

Section: Ring Opening Polymerization Of Carbonatesmentioning

confidence: 99%

Lipases as Efficient Catalysts in the Synthesis of Monomers and Polymers with Biomedical Applications

Liñares¹,

Baldessari

2013

COC

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“…In this paper we wish to report on triblock copolyesters made of L-tartaric and L-lactic acids. L-tartaric acid is the common name of (2S,3S)-2,3-dihydroxy succinic acid, a naturaloccurring aldaric acid that is widely available, relatively inexpensive, and that has been extensively used in the synthesis of polyamides [26][27][28], polyesters [29], polyesteramides [30,31], and polycarbonates [32,33]. In this work dimethyl 2,3-di-O-isopropylidene-L-tartrate (iThxCOOMe) was polycondensated with 1,4-butanediol to obtain an OH-(PBiThx) x -OH telechelic homopolyester.…”

Section: Introductionmentioning

confidence: 99%

Hydroxyl-functionalized amphiphilic triblock copolyesters made of tartaric and lactic acids: Synthesis and nanoparticle formation

Захарова

Ilarduya

León

et al. 2018

Reactive and Functional Polymers

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Bio-based triblock copolyesters were synthesized by ring-opening polymerization of Llactide in solution using a hydroxyl-ended polytartrate as di-functional macroinitiator. This telechelic polyester with a M n about 3000 g•mol-1 was obtained by non-stoichiometric melt polycondensation of dimethyl 2,3-di-O-isopropylidene-L-tartrate and 1,4-butanediol. Two symmetrical triblock copolyesters with M n in the 5,000-7,000 g•mol-1 range and differing in the length of the polylactide blocks were prepared. The protecting isopropylidene group was removed in trifluoracetic acid to generate amphiphilic triblock copolyesters bearing free hydroxyl groups in the central block. All copolyesters started to decompose approximately at 260-280 ºC, were semicrystalline, and readily degraded by hydrolysis of the main chain under both acid and basic conditions. The acetalized copolyesters had a single T g , whereas free-hydroxyl bearing copolyesters showed two T g indicative of blocks phase separation. All copolyesters were able to form nanoparticles with average diameters within the ~200-450 nm range. The influence of the block lengths and protection/deprotection of the hydroxyl groups on size and ζ-potential of the nanoparticles was evaluated.

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“…l -Tartaric acid, which is mainly obtained from a large variety of fruits, has been employed in polymer synthesis. Different classes of polymers have made based on l -tartaric acid, for example, polyamide, poly(ester−amide), polyesters, and polycarbonate. , However, the incorporation of tartaric acid or its derivative in degradable polymers has been through condensation polymerization, which is limited by the removal of the condensate, i.e., water or alcohol; efficient removal of the condensate is required to shift the equilibrium to the polymerization. The ring-opening polymerization (ROP) of cyclic monomers is more efficient as no leaving group is involved and, unlike condensation polymerization, can be performed at much lower temperature and is hence energy-efficient.…”

Section: Introductionmentioning

confidence: 99%

One-Shot Block Copolymerization of a Functional Seven-Membered Cyclic Carbonate Derived from l-Tartaric Acid with ε-Caprolactone

Al‐Azemi

Bisht

2009

Macromolecules

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Block copolymerization of a seven-membered cyclic carbonate (5S,6S)-dimethyl-5,6-isopropylidene-1,3-dioxepin-2-one (ITC) with ε-caprolactone in “one-shot feeding” is reported. The cyclic carbonate monomer ITC was synthesized from naturally occurring l-tartaric acid in three steps. Three catalystsstannous octanoate, Sn(Oct)2, triisopropoxide aluminum, Al(O i Pr)3, and diethylzinc monohydrate, ZnEt2−H2Owere tested for the homopolymerization of ITC monomer at 120 °C for 12 h in bulk. The results show that Sn(Oct)2 was the most effective catalyst to carry out the polymerization (M n = 24 000 g/mol; PDI = 1.6; [α]D 20 = +77.8). The copolymerization of ITC with ε-caprolactone (CL) in various feed ratios was also investigated. The detailed spectral and thermal analysis of the copolymers catalyzed by Sn(Oct)2 revealed formation of the block copolymer (poly[44%ITC-block-56%CL], M n = 24 000 g/mol; PDI = 1.6; [α]D 20 = +33.8). Two glass transition temperatures (T g) were observed for poly(44%ITC)-block-poly(56% ε-CL) at −59.1 and −37.2 °C for the poly(CL) and the poly(ITC) block, respectively, confirming the diblock nature of the copolymer. It is the first report of “one-shot” block copolymerization of ε-caprolactone with a cyclic carbonate monomer. The deprotection of the ketal groups resulted in copolymers containing free hydroxy groups in the polymer backbone.

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Novel Biodegradable Polyamides Based on Tartaric Acid: Preparation and Properties

Cited by 6 publications

References 15 publications

Lipases as Efficient Catalysts in the Synthesis of Monomers and Polymers with Biomedical Applications

Lipases as Efficient Catalysts in the Synthesis of Monomers and Polymers with Biomedical Applications

Hydroxyl-functionalized amphiphilic triblock copolyesters made of tartaric and lactic acids: Synthesis and nanoparticle formation

One-Shot Block Copolymerization of a Functional Seven-Membered Cyclic Carbonate Derived from l-Tartaric Acid with ε-Caprolactone

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