Stereomicrostructure-regulated biodegradable adhesives

Zhang, Zhen; Quinn, Ethan C.; Kenny, Jacob K.; Grigoropoulos, Alexandra; DesVeaux, Jason S.; Chen, Tiffany; Zhou, Li; Xu, Ting; Beckham, Gregg T.; Chen, Eugene Y.-X.

doi:10.1126/science.adr7175

Title: Stereomicrostructure-regulated biodegradable adhesives

Journal Article · 17 January 2025 · Science

DOI: https://doi.org/10.1126/science.adr7175 · OSTI ID:2522820

^[1];

^[2];

^[3];

^[2];

^[4];

^[1];

^[4];

^[2];

^[1]

Colorado State University, Fort Collins, CO (United States)
National Renewable Energy Laboratory (NREL), Golden, CO (United States); BOTTLE Consortium, Golden, CO (United States)
University of California, Berkeley, CA (United States)
University of California, Berkeley, CA (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Kavli Energy NanoScience Institute, Berkeley, CA (United States)

Commercial adhesives are petroleum-based thermoset networks or nonbiodegradable thermoplastic hot melts, making them ideal targets for replacement by biodegradable alternatives. Poly(3-hydroxybutyrate) (P3HB) is a biorenewable and biodegradable alternative to conventional plastics, but microbial P3HB, which has a stereoperfect stereomicrostructure, exhibits no adhesion. Here, in this study, by elucidating the fundamental relationship between chemocatalytically engineered P3HB stereomicrostructures and adhesion properties, we found that biodegradable syndio-rich P3HB exhibits high adhesion strength and outperforms common commercial adhesives, whereas syndiotactic, isotactic, or iso-rich P3HB shows no measurable adhesion. The syndio-rich stereomicrostructure brings about desired thermomechanical and viscoelastic properties of P3HB that enable strong adhesion to a range of substrates tested, including aluminum, steel, glass, and wood, and its performance is insensitive to molar mass and reprocessing or reuse.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); National Renewable Energy Laboratory (NREL), Golden, CO (United States)

Sponsoring Organization:: National Science Foundation (NSF); US Department of Energy; USDOE Office of Energy Efficiency and Renewable Energy (EERE), Energy Efficiency Office. Advanced Materials & Manufacturing Technologies Office (AMMTO); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Office of Sustainable Transportation. Bioenergy Technologies Office (BETO); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Materials Sciences & Engineering Division (SC-22.2); USDOE Office of Science (SC), Basic Energy Sciences (BES). Materials Sciences & Engineering Division (MSE); USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities (SUF)

Grant/Contract Number:: AC02-05CH11231; AC36-08GO28308; SC0012704

OSTI ID:: 2522820

Report Number(s):: NREL/JA--2A00-90493; MainId:92271; UUID:9a62669e-22df-4381-9f10-66b953d26bc1; MainAdminId:76099

Journal Information:: Science, Journal Name: Science Journal Issue: 6731 Vol. 387; ISSN 0036-8075

Publisher:: AAASCopyright Statement

Country of Publication:: United States

Language:: English

References (54)

Poly(hydroxyalkanoates): A Fifth Class of Physiologically Important Organic Biopolymers? Müller, Hans-Martin; Seebach, Dieter Angewandte Chemie International Edition in English, Vol. 32, Issue 4 https://doi.org/10.1002/anie.199304771	journal	April 1993
Toughening Brittle Bio‐P3HB with Synthetic P3HB of Engineered Stereomicrostructures Zhang, Zhen; Quinn, Ethan C.; Olmedo‐Martínez, Jorge L. Angewandte Chemie International Edition, Vol. 62, Issue 49 https://doi.org/10.1002/anie.202311264	journal	November 2023
Bio‐based propylene production in a sugarcane biorefinery: A techno‐economic evaluation for Brazilian conditions Machado, Pedro Gerber; Walter, Arnaldo; Cunha, Marcelo Biofuels, Bioproducts and Biorefining, Vol. 10, Issue 5 https://doi.org/10.1002/bbb.1674	journal	August 2016
Techno‐economic and greenhouse gas analyses of lignin valorization to eugenol and phenolic products in integrated ethanol biorefineries Martinez‐Hernandez, Elias; Cui, Xinguang; Scown, Corinne D. Biofuels, Bioproducts and Biorefining, Vol. 13, Issue 4 https://doi.org/10.1002/bbb.1989	journal	March 2019
Humidity control in the laboratory using salt solutions-a review Young, J. F. Journal of Applied Chemistry, Vol. 17, Issue 9 https://doi.org/10.1002/jctb.5010170901	journal	September 1967
Organocatalysis applied to the ring‐opening polymerization of β‐lactones: A brief overview Khalil, Ali; Cammas‐Marion, Sandrine; Coulembier, Olivier Journal of Polymer Science Part A: Polymer Chemistry, Vol. 57, Issue 6 https://doi.org/10.1002/pola.29322	journal	January 2019
Structural studies of polyesters: 5. Molecular and crystal structures of optically active and racemic poly (β-hydroxybutyrate) Yokouchi, M.; Chatani, Y.; Tadokoro, H. Polymer, Vol. 14, Issue 6 https://doi.org/10.1016/0032-3861(73)90087-6	journal	June 1973
Synthesis, structure and properties of polyhydroxyalkanoates: biological polyesters Sudesh, K.; Abe, H.; Doi, Y. Progress in Polymer Science, Vol. 25, Issue 10, p. 1503-1555 https://doi.org/10.1016/S0079-6700(00)00035-6	journal	December 2000
Lactic acid based polymers as hot melt adhesives for packaging applications Viljanmaa, M.; Södergård, A.; Törmälä, P. International Journal of Adhesion and Adhesives, Vol. 22, Issue 3 https://doi.org/10.1016/S0143-7496(01)00057-4	journal	January 2002
A comparative techno-economic analysis of renewable methanol synthesis from biomass and CO2: Opportunities and barriers to commercialization Harris, Kylee; Grim, R. Gary; Huang, Zhe Applied Energy, Vol. 303 https://doi.org/10.1016/j.apenergy.2021.117637	journal	December 2021
Polyhydroxyalkanoates: Characteristics, production, recent developments and applications Raza, Zulfiqar Ali; Abid, Sharjeel; Banat, Ibrahim M. International Biodeterioration & Biodegradation, Vol. 126 https://doi.org/10.1016/j.ibiod.2017.10.001	journal	January 2018
Demonstration of the adhesive properties of the medium-chain-length polyhydroxyalkanoate produced by Pseudomonas chlororaphis subsp. aurantiaca from glycerol Pereira, João R.; Araújo, Diana; Marques, Ana C. International Journal of Biological Macromolecules, Vol. 122 https://doi.org/10.1016/j.ijbiomac.2018.09.064	journal	February 2019
(Bio)Propylene production processes: A critical review Phung, Thanh Khoa; Pham, Thong Le Minh; Vu, Khanh B. Journal of Environmental Chemical Engineering, Vol. 9, Issue 4 https://doi.org/10.1016/j.jece.2021.105673	journal	August 2021
An economic analysis of twenty light olefin production pathways Zhao, Zhitong; Jiang, Jingyang; Wang, Feng Journal of Energy Chemistry, Vol. 56 https://doi.org/10.1016/j.jechem.2020.04.021	journal	May 2021
Techno-economic, life-cycle, and socioeconomic impact analysis of enzymatic recycling of poly(ethylene terephthalate) Singh, Avantika; Rorrer, Nicholas A.; Nicholson, Scott R. Joule, Vol. 5, Issue 9 https://doi.org/10.1016/j.joule.2021.06.015	journal	September 2021
Environmentally benign process for bulk ring opening polymerization of lactones using iron and ruthenium chloride catalysts Gowda, Ravikumar R.; Chakraborty, Debashis Journal of Molecular Catalysis A: Chemical, Vol. 301, Issue 1-2 https://doi.org/10.1016/j.molcata.2008.11.010	journal	March 2009
Tensile study of melt-spun poly(3-hydroxybutyrate) P3HB fibers: Reversible transformation of a highly oriented phase Perret, Edith; Reifler, Felix A.; Gooneie, Ali Polymer, Vol. 180 https://doi.org/10.1016/j.polymer.2019.121668	journal	October 2019
Adhesion of polymers Awaja, Firas; Gilbert, Michael; Kelly, Georgina Progress in Polymer Science, Vol. 34, Issue 9 https://doi.org/10.1016/j.progpolymsci.2009.04.007	journal	September 2009
Synthetic biodegradable polyhydroxyalkanoates (PHAs): Recent advances and future challenges Westlie, Andrea H.; Quinn, Ethan C.; Parker, Celine R. Progress in Polymer Science, Vol. 134 https://doi.org/10.1016/j.progpolymsci.2022.101608	journal	November 2022
Recyclable and (Bio)degradable Polyesters in a Circular Plastics Economy Shi, Changxia; Quinn, Ethan C.; Diment, Wilfred T. Chemical Reviews, Vol. 124, Issue 7, p. 4393-4478 https://doi.org/10.1021/acs.chemrev.3c00848	journal	March 2024
Biodegradable Plastic Blends Create New Possibilities for End-of-Life Management of Plastics but They Are Not a Panacea for Plastic Pollution Narancic, Tanja; Verstichel, Steven; Reddy Chaganti, Srinivasa Environmental Science & Technology, Vol. 52, Issue 18 https://doi.org/10.1021/acs.est.8b02963	journal	August 2018
Rare-Earth Complexes Supported by Tripodal Tetradentate Bis(phenolate) Ligands: A Privileged Class of Catalysts for Ring-Opening Polymerization of Cyclic Esters Carpentier, Jean-François Organometallics, Vol. 34, Issue 17 https://doi.org/10.1021/acs.organomet.5b00540	journal	August 2015
High-Value Propylene Glycol from Low-Value Biodiesel Glycerol: A Techno-Economic and Environmental Assessment under Uncertainty Gonzalez-Garay, Andres; Gonzalez-Miquel, Maria; Guillen-Gosalbez, Gonzalo ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 7 https://doi.org/10.1021/acssuschemeng.7b00286	journal	June 2017
What Is the True Cost of Producing Propylene from Methanol? The Role of Externalities Rodríguez-Vallejo, Daniel F.; Guillén-Gosálbez, Gonzalo; Chachuat, Benoît ACS Sustainable Chemistry & Engineering, Vol. 8, Issue 8 https://doi.org/10.1021/acssuschemeng.9b05516	journal	January 2020
Organocatalysis Paradigm Revisited: Are Metal-Free Catalysts Really Harmless? Nachtergael, Amandine; Coulembier, Olivier; Dubois, Philippe Biomacromolecules, Vol. 16, Issue 2 https://doi.org/10.1021/bm5015443	journal	January 2015
Preparation of sodium cobalt tetracarbonyl Edgell, Walter F.; Lyford, John Inorganic Chemistry, Vol. 9, Issue 8 https://doi.org/10.1021/ic50090a032	journal	August 1970
Synthesis of β-Lactones: A Highly Active and Selective Catalyst for Epoxide Carbonylation Getzler, Yutan D. Y. L.; Mahadevan, Viswanath; Lobkovsky, Emil B. Journal of the American Chemical Society, Vol. 124, Issue 7, p. 1174-1175 https://doi.org/10.1021/ja017434u	journal	February 2002
Installing Controlled Stereo-Defects Yields Semicrystalline and Biodegradable Poly(3-Hydroxybutyrate) with High Toughness and Optical Clarity Quinn, Ethan C.; Westlie, Andrea H.; Sangroniz, Ainara Journal of the American Chemical Society, Vol. 145, Issue 10 https://doi.org/10.1021/jacs.2c12897	journal	March 2023
Highly Isoselective Ring-Opening Polymerization of rac-β-Butyrolactone: Access to Synthetic Poly(3-hydroxybutyrate) with Polyolefin-like Material Properties Bruckmoser, Jonas; Pongratz, Stefanie; Stieglitz, Lucas Journal of the American Chemical Society, Vol. 145, Issue 21 https://doi.org/10.1021/jacs.3c02348	journal	May 2023
Weak Bonds in a Biomimetic Adhesive Enhance Toughness and Performance Mazzotta, Michael G.; Putnam, Amelia A.; North, Michael A. Journal of the American Chemical Society, Vol. 142, Issue 10 https://doi.org/10.1021/jacs.9b13356	journal	February 2020
Comparative Economic and Environmental Assessments of H₂O₂-based and Tertiary Butyl Hydroperoxide-based Propylene Oxide Technologies Ghanta, Madhav; Fahey, Darryl R.; Busch, Daryle H. ACS Sustainable Chemistry & Engineering, Vol. 1, Issue 2 https://doi.org/10.1021/sc300121j	journal	January 2013
Chemical synthesis of perfectly isotactic and high melting bacterial poly(3-hydroxybutyrate) from bio-sourced racemic cyclic diolide Tang, Xiaoyan; Chen, Eugene Y. -X. Nature Communications, Vol. 9, Issue 1 https://doi.org/10.1038/s41467-018-04734-3	journal	June 2018
Green synthesis of propylene oxide directly from propane Kube, Pierre; Dong, Jinhu; Bastardo, Nuria Sánchez Nature Communications, Vol. 13, Issue 1 https://doi.org/10.1038/s41467-022-34967-2	journal	December 2022
Chemical recycling to monomer for an ideal, circular polymer economy Coates, Geoffrey W.; Getzler, Yutan D. Y. L. Nature Reviews Materials, Vol. 5, Issue 7 https://doi.org/10.1038/s41578-020-0190-4	journal	April 2020
Sustainably sourced components to generate high-strength adhesives Westerman, Clayton R.; McGill, Bradley C.; Wilker, Jonathan J. Nature, Vol. 621, Issue 7978 https://doi.org/10.1038/s41586-023-06335-7	journal	September 2023
Bonding wood with uncondensed lignins as adhesives Yang, Guangxu; Gong, Zhenggang; Luo, Xiaolin Nature, Vol. 621, Issue 7979 https://doi.org/10.1038/s41586-023-06507-5	journal	August 2023
Designing a circular carbon and plastics economy for a sustainable future Vidal, Fernando; van der Marel, Eva R.; Kerr, Ryan W. F. Nature, Vol. 626, Issue 7997 https://doi.org/10.1038/s41586-023-06939-z	journal	January 2024
Chemical and biological catalysis for plastics recycling and upcycling Ellis, Lucas D.; Rorrer, Nicholas A.; Sullivan, Kevin P. Nature Catalysis, Vol. 4, Issue 7 https://doi.org/10.1038/s41929-021-00648-4	journal	July 2021
Early-stage evaluation of catalyst manufacturing cost and environmental impact using CatCost Van Allsburg, Kurt M.; Tan, Eric C. D.; Super, John D. Nature Catalysis, Vol. 5, Issue 4 https://doi.org/10.1038/s41929-022-00759-6	journal	March 2022
A new solution for removing metal-based catalyst residues from a biodegradable polymer Bahramian, B.; Ma, Y.; Rohanizadeh, R. Green Chemistry, Vol. 18, Issue 13 https://doi.org/10.1039/C5GC01687H	journal	January 2016
Chemically recyclable polymers: a circular economy approach to sustainability Hong, Miao; Chen, Eugene Y. -X. Green Chemistry, Vol. 19, Issue 16 https://doi.org/10.1039/C7GC01496A	journal	January 2017
Future opportunities for bio-based adhesives – advantages beyond renewability Heinrich, Lydia Alexandra Green Chemistry, Vol. 21, Issue 8 https://doi.org/10.1039/C8GC03746A	journal	January 2019
Alternating ring-opening copolymerization of phthalic anhydride with epoxides catalysed by salophen chromium(iii) complexes. An effect of substituents in salophen ligands Bester, K.; Bukowska, A.; Myśliwiec, B. Polymer Chemistry, Vol. 9, Issue 16 https://doi.org/10.1039/C8PY00048D	journal	January 2018
The economic outlook for converting CO ₂ and electrons to molecules Huang, Zhe; Grim, R. Gary; Schaidle, Joshua A. Energy & Environmental Science, Vol. 14, Issue 7 https://doi.org/10.1039/D0EE03525D	journal	January 2021
A microbial polyhydroxyalkanoates (PHA) based bio- and materials industry Chen, Guo-Qiang Chemical Society Reviews, Vol. 38, Issue 8 https://doi.org/10.1039/b812677c	journal	January 2009
Hazards associated with syngas storage Stolecka, Katarzyna; Rusin, Andrzej E3S Web of Conferences, Vol. 137 https://doi.org/10.1051/e3sconf/201913701022	journal	January 2019
Production, use, and fate of all plastics ever made Geyer, Roland; Jambeck, Jenna R.; Law, Kara Lavender Science Advances, Vol. 3, Issue 7 https://doi.org/10.1126/sciadv.1700782	journal	July 2017
Design of tough adhesive from commodity thermoplastics through dynamic crosslinking Rahman, Md Anisur; Bowland, Christopher; Ge, Sirui Science Advances, Vol. 7, Issue 42 https://doi.org/10.1126/sciadv.abk2451	journal	October 2021
Stereosequenced crystalline polyhydroxyalkanoates from diastereomeric monomer mixtures Tang, Xiaoyan; Westlie, Andrea H.; Watson, Eli M. Science, Vol. 366, Issue 6466 https://doi.org/10.1126/science.aax8466	journal	November 2019
Predicted growth in plastic waste exceeds efforts to mitigate plastic pollution Borrelle, Stephanie B.; Ringma, Jeremy; Law, Kara Lavender Science, Vol. 369, Issue 6510 https://doi.org/10.1126/science.aba3656	journal	September 2020
Recyclable surgical, consumer, and industrial adhesives of poly(α-lipoic acid) Pal, Subhajit; Shin, Jisoo; DeFrates, Kelsey Science, Vol. 385, Issue 6711 https://doi.org/10.1126/science.ado6292	journal	August 2024
The Critical Role of Process Analysis in Chemical Recycling and Upcycling of Waste Plastics Nicholson, Scott R.; Rorrer, Julie E.; Singh, Avantika Annual Review of Chemical and Biomolecular Engineering, Vol. 13, Issue 1 https://doi.org/10.1146/annurev-chembioeng-100521-085846	journal	March 2022
Biochemical Conversion of Lignocellulosic Biomass to Hydrocarbon Fuels and Products: 2022 State of Technology and Future Research Davis, Ryan; Bartling, Andrew https://doi.org/10.2172/1962809	report	March 2023
A Techno-Economic Comparison between Two Methanol-to-Propylene Processes Jasper, Sarah; El-Halwagi, Mahmoud Processes, Vol. 3, Issue 3 https://doi.org/10.3390/pr3030684	journal	September 2015

Similar Records

Synthetic biodegradable polyhydroxyalkanoates (PHAs): Recent advances and future challenges

Journal Article · 2022 · Progress in Polymer Science · OSTI ID:2424251

Westlie, Andrea H.; Quinn, Ethan C.; Parker, Celine R.; +1 more

Installing Controlled Stereo-Defects Yields Semicrystalline and Biodegradable Poly(3-Hydroxybutyrate) with High Toughness and Optical Clarity

Journal Article · 2023 · Journal of the American Chemical Society · OSTI ID:2007761

Quinn, Ethan C.; Westlie, Andrea H.; Sangroniz, Ainara; +6 more

Mono‐Materials Created by Engineering a Continuum of P3HB Stereomicrostructures in a One‐Step Catalytic Process

Journal Article · 2025 · Angewandte Chemie (International Edition) · OSTI ID:3017172

Quinn, Ethan C.; Parker, Celine R.; Gace, Maëlle T.; +8 more

Related Subjects

36 MATERIALS SCIENCE
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
P3HB stereomicrostructures
chemocatalytically tuning
non-biodegradable thermoplastic hot-melts
petroleum-based thermoset networks

Title: Stereomicrostructure-regulated biodegradable adhesives

Citation Formats

References (54)

Similar Records

Related Subjects