Synthesis of Renewable Copolyacetals with Tunable Degradation

Rajput, Bhausaheb S.; Chander, Umesh; Arole, Kailash; Stempfle, Florian; Menon, Shamal K.; Mecking, Stefan; Chikkali, Samir H.

doi:10.1002/macp.201600071

Cited by 20 publications

(12 citation statements)

References 51 publications

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“…The field of renewable and biodegradable polymers is rapidly growing and attracting significant attention due to pressing environmental concerns [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. Renewable feedstocks will play an important role in reducing greenhouse gas emissions and ensuring energy security in the 21st century [ 7 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

High Bio-Content Thermoplastic Polyurethanes from Azelaic Acid

2022

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To realize the commercialization of sustainable materials, new polymers must be generated and systematically evaluated for material characteristics and end-of-life treatment. Polyester polyols made from renewable monomers have found limited adoption in thermoplastic polyurethane (TPU) applications, and their broad adoption in manufacturing may be possible with a more detailed understanding of their structure and properties. To this end, we prepared a series of bio-based crystalline and amorphous polyester polyols utilizing azelaic acid and varying branched or non-branched diols. The prepared polyols showed viscosities in the range of 504–781 cP at 70 °C, with resulting TPUs that displayed excellent thermal and mechanical properties. TPUs prepared from crystalline azelate polyester polyol exhibited excellent mechanical properties compared to TPUs prepared from amorphous polyols. These were used to demonstrate prototype products, such as watch bands and cup-shaped forms. Importantly, the prepared TPUs had up to 85% bio-carbon content. Studies such as these will be important for the development of renewable materials that display mechanical properties suitable for commercially viable, sustainable products.

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Section: Introductionmentioning

confidence: 99%

High Bio-Content Thermoplastic Polyurethanes from Azelaic Acid

2022

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“…Hydrolysis can be accelerated with an acid, base, or enzyme . Unlike conventional polyesters, some degradable polyesters have a structure into which water molecules penetrate well because of the large free volume of the renewable monomers, such as derivatives of isosorbide and mannitol, and the wide spacing between polymer chains. ,, However, physically designing the molecules to facilitate water access has limitations for accelerating polymer degradation.…”

Section: Introductionmentioning

confidence: 99%

Fast Hydrolysis Polyesters with a Rigid Cyclic Diol from Camphor

et al. 2017

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2,2:3,3-Bis(4'-hydroxymethylethylenedioxy)-1,7,7-trimethylbicyclo[2.2.1]heptane, abbreviated as CaG, is a compound obtained by transforming a ketone group to a ketal group with camphorquinone and glycerol. The CaG diol has a complex and rigid structure and two primary hydroxyl groups. A polyester series was synthesized with the CaG diol, ethylene glycol, and dimethyl terephthalate. The polyesters exhibited adequate thermal stability up to nearly 330 °C and had a high T, which steadily increased from 78 to 129 °C as the content of CaG increased. A high proportion of the CaG moiety led to an amorphous region that is susceptible to hydrolysis and promoted degradation of the polyester in acidic conditions. Depending on the proportion of CaG in the polymer, the hydrolytic degradation of the polyesters was adjustable.

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“…The polymers based on acetals could be prepared via transacetalation with p -toluenesulfonic acid as the catalyst . Recently, the progress of syntheses of acetal-based polymers has been reviewed. , Based on the dissociation of the acetal structure catalyzed by acids, the acetal-based polymers can be degraded. − The dynamic covalent networks based on acetal exchange have been reported recently . The system contains two possible mechanisms, that is, transacetalation and acetal metathesis.…”

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confidence: 99%

Catalyst-Free Metathesis of Cyclic Acetals and Spirocyclic Acetal Covalent Adaptable Networks

Zhang

et al. 2020

ACS Macro Lett.

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Due to the exchangeability of dynamic covalent bonds in the covalent adaptable networks (CANs) at elevated temperature, they possess recyclability while still maintaining many of the superior properties of thermosets. The exploration of dynamic covalent chemistry is of great significance to the expansion of CANs library and hence the sustainable development of thermosets. In this work, we discovered that, in absence of catalyst, the direct metathesis of the cyclic acetals proceeds while the acyclic acetals cannot. The metathesis kinetics of the cyclic acetals were fully revealed with model compounds. For the CANs demonstration, a series of cross-linked spirocyclic acetal polymers with excellent reprocessability, high thermal stability, and high refractivity were prepared via thiol–ene click polymerization. We envisage that the uncovering of the catalyst-free metathesis of cyclic acetals will enrich the dynamic chemistry of acetals and greatly promote the development of acetal-based CANs and their potential applications in optical devices.

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Synthesis of Renewable Copolyacetals with Tunable Degradation

Cited by 20 publications

References 51 publications

High Bio-Content Thermoplastic Polyurethanes from Azelaic Acid

High Bio-Content Thermoplastic Polyurethanes from Azelaic Acid

Fast Hydrolysis Polyesters with a Rigid Cyclic Diol from Camphor

Catalyst-Free Metathesis of Cyclic Acetals and Spirocyclic Acetal Covalent Adaptable Networks

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