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Effect of the Configuration of a Bulky Aluminum Initiator on the Structure of Copolymers of l,l-Lactide with Symmetric Comonomer Trimethylene Carbonate.

ABSTRACT: The effect of configuration of an asymmetric bulky initiator 2,2'-[1,1'-binaphtyl-2,2'-diyl- bis-(nitrylomethilidyne)]diphenoxy aluminum isopropoxide (Ini) on structure of copolymer of asymmetric monomer l,l-lactide (Lac) with symmetric comonomer trimethylene carbonate (Tmc) was studied using polarimetry, dilatometry, Size Exclusion Chromatography (SEC), and Carbon Nuclear Magnetic Resonance (¹³C NMR). When the S-enantiomer of Ini was used the distribution in copolymer chains at the beginning of polymerization is statistical, with alternacy tendency, changing next through a gradient region to homoblocks of Tmc. However, when R-Ini was used, the product formed was a gradient oligoblock one, with Tmc blocks prevailing at the beginning, changing to Lac blocks dominating at the end part of chains. Initiation of copolymerization with the mixture of both initiator enantiomers (S:R = 6:94) gave a multiblock copolymer of similar features but shorter blocks. Analysis of copolymerization progress required complex analysis of dilatometric data, assuming different molar volume contraction coefficients for units located in different triads. Comonomer reactivity ratios of studied copolymerizations were determined.

SUBMITTER: Socka M

PROVIDER: S-EPMC6414924 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Preparation of multiblock copolymers via step-wise addition of l-lactide and trimethylene carbonate.

Project description:Poly(l-lactide) (PLA) is a bioderived and biodegradable polymer that has limited applications due to its hard and brittle nature. Incorporation of 1,3-trimethylene carbonate into PLA, in a block copolymer fashion, improves the mechanical properties, while retaining the biodegradability of the polymer, and broadens its range of applications. However, the preparation of 1,3-trimethylene carbonate (TMC)/l-lactide (LA) copolymers beyond diblock and triblock structures has not been reported, with explanations focusing mostly on thermodynamic reasons that impede the copolymerization of TMC after lactide. We discuss the preparation of multiblock copolymers via the ring opening polymerization (ROP) of LA and TMC, in a step-wise addition, by a ferrocene-chelating heteroscorpionate zinc complex, {[fc(PPh2)(BH[(3,5-Me)2pz]2)]Zn(?-OCH2Ph)}2 ([(fcP,B)Zn(?-OCH2Ph)]2, fc = 1,1'-ferrocenediyl, pz = pyrazole). The synthesis of up to pentablock copolymers, from various combinations of LA and TMC, was accomplished and the physical, thermal, and mechanical properties of the resulting copolymers evaluated.

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Influence of Radiation Sterilization on Properties of Biodegradable Lactide/Glycolide/Trimethylene Carbonate and Lactide/Glycolide/?-caprolactone Porous Scaffolds with Shape Memory Behavior.

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Poly(trimethylene carbonate-<i>co</i>-valerolactone) copolymers are materials with tailorable properties: from soft to thermoplastic elastomers.

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Poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) Amphiphilic Copolymers for Long-Acting Injectables: Synthesis, Non-Acylating Performance and In Vivo Degradation.

Project description:This article presents the evaluation of diblock and triblock poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) amphiphilic copolymers (PEG-PTMCs) as excipients for the formulation of long-acting injectables (LAIs). Copolymers were successfully synthesised through bulk ring-opening polymerisation. The concomitant formation of PTMC homopolymer could not be avoided irrespective of the catalyst amount, but the by-product could easily be removed by gel chromatography. Pure PEG-PTMCs undergo faster erosion in vivo than their corresponding homopolymer. Furthermore, these copolymers show outstanding stability compared to their polyester analogues when formulated with amine-containing reactive drugs, which makes them particularly suitable as LAIs for the sustained release of drugs susceptible to acylation.

| S-EPMC7962012 | biostudies-literature

Poly(trimethylene carbonate-co-ε-caprolactone) promotes axonal growth.

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Project description:Carbon dioxide utilisation (CDU) is currently gaining increased interest due to the abundance of CO2 and its possible application as a C1 building block. We herein report the first example of atmospheric pressure carbon dioxide incorporation into oxetane to selectively form trimethylene carbonate (TMC), which is a significant challenge as TMC is thermodynamically less favoured than its corresponding co-polymer.

| S-EPMC4502766 | biostudies-literature

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Project description:Mechanochemical polymerization is a rapidly growing area and a number of polymeric materials can now be obtained through green mechanochemical synthesis. In addition to the general merits of mechanochemistry, such as being solvent-free and resulting in high conversions, we herein explore rate acceleration under ball-milling conditions while the conventional solution-state synthesis suffer from low reactivity. The solvent-free mechanochemical polymerization of trimethylene carbonate using the organocatalysts 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) are examined herein. The polymerizations under ball-milling conditions exhibited significant rate enhancements compared to polymerizations in solution. A number of milling parameters were evaluated for the ball-milling polymerization. Temperature increases due to ball collisions and exothermic energy output did not affect the polymerization rate significantly and the initial mixing speed was important for chain-length control. Liquid-assisted grinding was applied for the synthesis of high molecular weight polymers, but it failed to protect the polymer chain from mechanical degradation.

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