Mechanochemical synthesis of poly(lactic acid) block copolymers: overcoming the miscibility of the macroinitiator, monomer and catalyst under solvent-free conditions

Lee, Gue Seon; Moon, Bo Reum; Jeong, Haemin; Shin, Jihoon; Kim, Jeung Gon

doi:10.1039/c8py01520a

Cited by 33 publications

(33 citation statements)

References 32 publications

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“…However, the relatively slow propagation rate of DBU-mediated trimethyl carbonate polymerization allowed for well-controlled chain lengths. The previous examples on mechanochemical poly(lactic acid) synthesis resulted in broader molecular weight distributions due to the fast propagation rate [13–14].…”

Section: Resultsmentioning

confidence: 99%

“…In our previous study on poly(lactic acid) synthesis, liquid-assisted grinding (LAG), the addition of a very small amount of a liquid, prevented chain-degradation from high impact collisions, and afforded PLA with over 100,000 g/mol. Thus, LAG was also tested in the PTMC synthesis [13–14] with toluene and THF as liquids. A catalytic amount of liquid (10 or 20 µL to 100 mg TMC), however, failed to protect the poly(trimethylene carbonate) chain from mechanical degradation and similar molecular weights were obtained, regardless of LAG.…”

Section: Resultsmentioning

confidence: 99%

“…The Borchardt research team reported the efficient mechanochemical synthesis of poly(azomethine) and poly(phenylene) [11–12]. Our group also contributed to this area by developing a ball-milling promoted high-molecular weight poly(lactic acid) synthesis [13–14] and a solvent-free post-polymerization modification of functional polystyrenes [15]. The Friščić team also showed that poly(ethylene oxide) end group modification is facile under ball-mill conditions [16].…”

Section: Introductionmentioning

confidence: 99%

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Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

Park

Kim

2019

Beilstein J. Org. Chem.

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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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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

Park

Kim

2019

Beilstein J. Org. Chem.

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“…Block co-polymerization of PLA with poly(ethylene glycol) (PEG) is another common technique used to enhance the biodegradability of polylactide [ 34 , 75 , 76 , 77 ]. A study revealed a solvent-free synthesis of a PLA–PEG block copolymer with enhanced biodegradability [ 78 ].…”

Section: Bio-based Materials For Packaging Applicationsmentioning

confidence: 99%

Bio-Based Packaging: Materials, Modifications, Industrial Applications and Sustainability

et al. 2020

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Environmental impacts and consumer concerns have necessitated the study of bio-based materials as alternatives to petrochemicals for packaging applications. The purpose of this review is to summarize synthetic and non-synthetic materials feasible for packaging and textile applications, routes of upscaling, (industrial) applications, evaluation of sustainability, and end-of-life options. The outlined bio-based materials include polylactic acid, polyethylene furanoate, polybutylene succinate, and non-synthetically produced polymers such as polyhydrodyalkanoate, cellulose, starch, proteins, lipids, and waxes. Further emphasis is placed on modification techniques (coating and surface modification), biocomposites, multilayers, and additives used to adjust properties especially for barriers to gas and moisture and to tune their biodegradability. Overall, this review provides a holistic view of bio-based packaging material including processing, and an evaluation of the sustainability of and options for recycling. Thus, this review contributes to increasing the knowledge of available sustainable bio-based packaging material and enhancing the transfer of scientific results into applications.

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“…In the realm of polymer science, mechanochemistry has often been used as a tool for the controlled chain scission of macromolecules containing mechanophores . However, there are examples that describe the use of mechanochemistry to facilitate polymer synthesis . An idea that has been investigated to a lesser extent is the use of mechanochemistry to facilitate post‐polymerization modification reactions.…”

Section: Introductionmentioning

confidence: 99%

Post‐Polymerization Thiol Substitutions Facilitated by Mechanochemistry

Ashlin

Hobbs

2019

Macro Chemistry & Physics

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The use of mechanical force to facilitate post‐polymerization, solvent‐free thiol substitution reactions is described. These reactions are amenable to halogen‐containing materials prepared using ring opening metathesis polymerization and free radical polymerization reactions. Reactions of these polymers with various thiols can be carried out in a ball mill and are complete in a matter of minutes. Further, 1H NMR and GPC analysis show no significant decomposition of the polymer chain.

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Mechanochemical synthesis of poly(lactic acid) block copolymers: overcoming the miscibility of the macroinitiator, monomer and catalyst under solvent-free conditions

Abstract: Efficient mixing and energy delivery by ball-milling promoted the lactide polymer growth from macroinitiators without the use of a solvent.

Cited by 33 publications

References 32 publications

Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

Bio-Based Packaging: Materials, Modifications, Industrial Applications and Sustainability

Post‐Polymerization Thiol Substitutions Facilitated by Mechanochemistry

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