Use of latent metathesis polymerization systems for additive manufacturing

Appelhans, Leah; Leguizamon, Samuel; Jones, Brad Howard; Cook, Adam Wade

Use of latent metathesis polymerization systems for additive manufacturing

Patent · Mon Dec 11 23:00:00 EST 2023

OSTI ID:2293974

Appelhans, Leah; Leguizamon, Samuel; Jones, Brad Howard; Cook, Adam Wade

The invention is directed to latent metathesis-active resin compositions and additive manufacturing approaches. The latent metathesis-active compositions comprise at least one latent metathesis catalyst, at least one curable metathesis-active monomer, and optional fillers, photosensitizers, and/or a secondary monomer resin system for dual-cure. A method comprises extruding a latent metathesis-active resin from a dispensing apparatus and spatially triggering a ring-opening metathesis polymerization by directed irradiation with light or directed application of a thermal stimuli for direct-ink write printing of objects. Another method uses a latent metathesis-active resin for vat photopolymerization and stereolithographic printing of objects.

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Research Organization:: Sandia National Laboratories (SNL-NM), Albuquerque, NM (United States)

Sponsoring Organization:: USDOE National Nuclear Security Administration (NNSA)

DOE Contract Number:: NA0003525

Assignee:: National Technology & Engineering Solutions of Sandia, LLC (Albuquerque, NM)

Patent Number(s):: 11,840,586

Application Number:: 17/677,558

OSTI ID:: 2293974

Country of Publication:: United States

Language:: English

References (19)

Alkyl Phosphite Inhibitors for Frontal Ring-Opening Metathesis Polymerization Greatly Increase Pot Life Robertson, Ian D.; Dean, Leon M.; Rudebusch, Gabriel E. ACS Macro Letters, Vol. 6, Issue 6 https://doi.org/10.1021/acsmacrolett.7b00270	journal	May 2017
Synthesis and Characterization of New Ruthenium-Based Olefin Metathesis Catalysts Coordinated with Bidentate Schiff-Base Ligands Chang, Sukbok; Jones, LeRoy; Wang, Chunming Organometallics, Vol. 17, Issue 16 https://doi.org/10.1021/om970910y	journal	July 1998
Turning the Light On: Recent Developments in Photoinduced Olefin Metathesis Eivgi, Or; Lemcoff, N. Synthesis, Vol. 50, Issue 01 https://doi.org/10.1055/s-0036-1589113	journal	September 2017
Thermally Stable, Latent Olefin Metathesis Catalysts Thomas, Renee M.; Fedorov, Alexey; Keitz, Benjamin K. Organometallics, Vol. 30, Issue 24 https://doi.org/10.1021/om200911e	journal	November 2011
Rapid energy-efficient manufacturing of polymers and composites via frontal polymerization Robertson, Ian D.; Yourdkhani, Mostafa; Centellas, Polette J. Nature, Vol. 557, Issue 7704 https://doi.org/10.1038/s41586-018-0054-x	journal	May 2018
Ruthenium indenylidene “1^st generation” olefin metathesis catalysts containing triisopropyl phosphite Guidone, Stefano; Nahra, Fady; Slawin, Alexandra M. Z. Beilstein Journal of Organic Chemistry, Vol. 11 https://doi.org/10.3762/bjoc.11.166	journal	September 2015
Employing Photosensitizers for Rapid Olefin Metathesis Additive Manufacturing of Poly(dicyclopentadiene) Leguizamon, Samuel C.; Cook, Adam W.; Appelhans, Leah N. Chemistry of Materials, Vol. 33, Issue 24 https://doi.org/10.1021/acs.chemmater.1c03298	journal	December 2021
A Tandem Approach to Photoactivated Olefin Metathesis: Combining a Photoacid Generator with an Acid Activated Catalyst Keitz, Benjamin K.; Grubbs, Robert H. Journal of the American Chemical Society, Vol. 131, Issue 6 https://doi.org/10.1021/ja807187u	journal	January 2009
Light-Activated Olefin Metathesis: Catalyst Development, Synthesis, and Applications Eivgi, Or; Phatake, Ravindra S.; Nechmad, Noy B. Accounts of Chemical Research, Vol. 53, Issue 10 https://doi.org/10.1021/acs.accounts.0c00495	journal	September 2020
Light-induced olefin metathesis Vidavsky, Yuval; Lemcoff, N. Gabriel Beilstein Journal of Organic Chemistry, Vol. 6 https://doi.org/10.3762/bjoc.6.127	journal	January 2010
Photoinitiated ring‐opening metathesis polymerization Joo, Wontae; Chen, Christopher H.; Moerdyk, Jonathan P. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 57, Issue 17 https://doi.org/10.1002/pola.29449	journal	August 2019
Photothermal Initiation of Frontal Polymerization Using Carbon Nanoparticles Dean, Leon M.; Ravindra, Amogha; Guo, Allen X. ACS Applied Polymer Materials, Vol. 2, Issue 11 https://doi.org/10.1021/acsapm.0c00726	journal	August 2020
Photoactivation of Ruthenium Phosphite Complexes for Olefin Metathesis Eivgi, Or; Guidone, Stefano; Frenklah, Alexander ACS Catalysis, Vol. 8, Issue 7 https://doi.org/10.1021/acscatal.8b01637	journal	May 2018
In Situ Generated Ruthenium–Arene Catalyst for Photoactivated Ring‐Opening Metathesis Polymerization through Photolatent N‐Heterocyclic Carbene Ligand Pinaud, Julien; Trinh, Thi Kim Hoang; Sauvanier, David Chemistry – A European Journal, Vol. 24, Issue 2 https://doi.org/10.1002/chem.201705145	journal	December 2017
Survey of Catalysts for Frontal Ring-Opening Metathesis Polymerization Suslick, Benjamin A.; Stawiasz, Katherine J.; Paul, Justine E. Macromolecules, Vol. 54, Issue 11 https://doi.org/10.1021/acs.macromol.1c00566	journal	May 2021
Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis Eivgi, Or; Vaisman, Anna; Nechmad, Noy B. ACS Catalysis, Vol. 10, Issue 3 https://doi.org/10.1021/acscatal.9b05079	journal	December 2019
Latent, Yet Highly Active Photoswitchable Olefin Metathesis Precatalysts Bearing Cyclic Alkyl Amino Carbene (CAAC)/Phosphite Ligands Eivgi, Or; Vaisman, Anna; Lemcoff, N. Gabriel ACS Catalysis, Vol. 11, Issue 2 https://doi.org/10.1021/acscatal.0c04909	journal	December 2020
Visible-Light-Controlled Ruthenium-Catalyzed Olefin Metathesis Theunissen, Cédric; Ashley, Melissa A.; Rovis, Tomislav Journal of the American Chemical Society, Vol. 141, Issue 17 https://doi.org/10.1021/jacs.8b13663	journal	April 2019
Photoexcitation of Grubbs’ Second-Generation Catalyst Initiates Frontal Ring-Opening Metathesis Polymerization Stawiasz, Katherine J.; Paul, Justine E.; Schwarz, Kevin J. ACS Macro Letters, Vol. 9, Issue 11 https://doi.org/10.1021/acsmacrolett.0c00486	journal	October 2020

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