Biobased plastics and elastomers from renewable rosin via "living" ring-opening metathesis polymerization

Mitra S. Ganewatta; Wenyue Ding; Md Anisur Rahman; Liang Yuan; Zhongkai Wang; Nasrollah Hamidi; Megan L. Robertson; Chuanbing Tang

doi:10.1021/acs.macromol.6b01496

Biobased plastics and elastomers from renewable rosin via "living" ring-opening metathesis polymerization

Mitra S. Ganewatta, Wenyue Ding, Md Anisur Rahman, Liang Yuan, Zhongkai Wang, Nasrollah Hamidi, Megan L. Robertson, Chuanbing Tang

Research output: Contribution to journal › Article › peer-review

63 Scopus citations

Abstract

Utilization of biomass for commodity polymers has gained tremendous interest. We report a method to prepare high molecular weight renewable homopolymers and block copolymers derived from natural rosin. Monomers with high renewable content (70 wt %) were prepared via a simple esterification reaction between dehydroabietic alcohol and 5-exo-norbornenecarboxylic acid. Living and controlled polymerization of these monomers were achieved by ring-opening metathesis polymerization to obtain polymers with molecular weight up to ∼500 kg/mol. These homopolymers exhibit structure-dependent glass transition temperatures, excellent thermal stabilities, and thermoplastic properties. Chain entanglement molecular weight was determined via rheological assessments for such polymers with bulky side moieties. Using the living ROMP, dehydroabietic-based homopolymer was chain-extended with a soybean oil-derived norbornene monomer to yield triblock copolymers, which showed behaviors of thermoplastic elastomers.

Original language	English
Pages (from-to)	7155-7164
Number of pages	10
Journal	Macromolecules
Volume	49
Issue number	19
DOIs	https://doi.org/10.1021/acs.macromol.6b01496
State	Published - Oct 11 2016
Externally published	Yes

Funding

The authors acknowledge the support from National Science Foundation (DMR-1252611). X-ray work was carried out at South Carolina SAXS Collaborative supported by the NSF Major Research Instrumentation program (DMR-1428620). We thank H. N. Lokupitiya for the assistance with the SAXS measurements. M.LR. and W.D. acknowledge financial support by the National Science Foundation through Grant DMR-1351788.

Funders	Funder number
National Science Foundation	1351788, DMR-1351788, DMR-1428620, DMR-1252611, 1252611

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abstract = "Utilization of biomass for commodity polymers has gained tremendous interest. We report a method to prepare high molecular weight renewable homopolymers and block copolymers derived from natural rosin. Monomers with high renewable content (70 wt %) were prepared via a simple esterification reaction between dehydroabietic alcohol and 5-exo-norbornenecarboxylic acid. Living and controlled polymerization of these monomers were achieved by ring-opening metathesis polymerization to obtain polymers with molecular weight up to ∼500 kg/mol. These homopolymers exhibit structure-dependent glass transition temperatures, excellent thermal stabilities, and thermoplastic properties. Chain entanglement molecular weight was determined via rheological assessments for such polymers with bulky side moieties. Using the living ROMP, dehydroabietic-based homopolymer was chain-extended with a soybean oil-derived norbornene monomer to yield triblock copolymers, which showed behaviors of thermoplastic elastomers.",

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AU - Ganewatta, Mitra S.

AU - Ding, Wenyue

AU - Rahman, Md Anisur

AU - Yuan, Liang

AU - Wang, Zhongkai

AU - Hamidi, Nasrollah

AU - Robertson, Megan L.

AU - Tang, Chuanbing

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AB - Utilization of biomass for commodity polymers has gained tremendous interest. We report a method to prepare high molecular weight renewable homopolymers and block copolymers derived from natural rosin. Monomers with high renewable content (70 wt %) were prepared via a simple esterification reaction between dehydroabietic alcohol and 5-exo-norbornenecarboxylic acid. Living and controlled polymerization of these monomers were achieved by ring-opening metathesis polymerization to obtain polymers with molecular weight up to ∼500 kg/mol. These homopolymers exhibit structure-dependent glass transition temperatures, excellent thermal stabilities, and thermoplastic properties. Chain entanglement molecular weight was determined via rheological assessments for such polymers with bulky side moieties. Using the living ROMP, dehydroabietic-based homopolymer was chain-extended with a soybean oil-derived norbornene monomer to yield triblock copolymers, which showed behaviors of thermoplastic elastomers.

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Biobased plastics and elastomers from renewable rosin via "living" ring-opening metathesis polymerization

Abstract

Funding

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