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Title: Diels–Alder Reversible Thermoset 3D Printing: Isotropic Thermoset Polymers via Fused Filament Fabrication

Journal Article · · Advanced Functional Materials
ORCiD logo [1];  [2];  [3];  [4];  [5];  [3];  [6]
  1. Department of Chemistry and Biochemistry The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA, Center for Engineering Innovation The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA
  2. Department of Bioengineering The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA
  3. Department of Chemistry and Biochemistry The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA
  4. Center for Engineering Innovation The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA
  5. Adaptive 3D Technologies 17217 Waterview Pkwy Dallas TX 75252 USA
  6. Department of Chemistry and Biochemistry The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA, Center for Engineering Innovation The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA, Department of Bioengineering The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA, Adaptive 3D Technologies 17217 Waterview Pkwy Dallas TX 75252 USA, Department of Materials Science and Engineering The University of Texas at Dallas 800 W. Campbell Rd Richardson TX 75080 USA

This study presents a new 3D printing process, the Diels–Alder reversible thermoset (DART) process, and a first generation of printable DART resins, which exhibit thermoset properties at use temperatures, ultralow melt viscosity at print temperatures, smooth part surface finish, and as‐printed isotropic mechanical properties. This study utilizes dynamic covalent chemistry based on reversible furan‐maleimide Diels–Alder linkages in the polymers, which can be decrosslinked and melt‐processed during printing between 90 and 150 °C, and recrosslinked at lower temperatures to their entropically favored state. This study compares the first generation of DART materials to commonly 3D printed high‐toughness thermoplastics. Parts printed from typical fused filament fabrication compatible materials exhibit anisotropy of more than 50% and sometimes upward of 98% in toughness when deformed along the build direction, while the first generation of DART materials exhibit less than 4% toughness reduction when deformed along the build direction. At room temperature, the toughest DART materials exhibit baseline toughness of 18.59 ± 0.91 and 18.36 ± 0.57 MJ m −3 perpendicular and parallel to the build direction, respectively. DART printing will enable chemists, polymer engineers, materials scientists, and industrial designers to translate new robust materials possessing targeted thermomechanical properties, multiaxial toughness, smooth surface finish, and low anisotropy.

Sponsoring Organization:
USDOE
OSTI ID:
1401785
Journal Information:
Advanced Functional Materials, Journal Name: Advanced Functional Materials Vol. 27 Journal Issue: 24; ISSN 1616-301X
Publisher:
Wiley Blackwell (John Wiley & Sons)Copyright Statement
Country of Publication:
Germany
Language:
English
Citation Metrics:
Cited by: 106 works
Citation information provided by
Web of Science

References (40)

Anisotropic material properties of fused deposition modeling ABS journal October 2002
Enhancement of Mechanical and Self-Healing Performance in Multiwall Carbon Nanotube/Rubber Composites via Diels-Alder Bonding journal February 2016
The future of dental devices is digital journal January 2012
Exploiting Chemical Switching in a Diels–Alder Polymer for Nanoscale Probe Lithography and Data Storage journal July 2006
Synthesis of siloxane-containing bis(furans) and polymerization with bis(maleimides) journal September 1986
New Thermally Remendable Highly Cross-Linked Polymeric Materials journal March 2003
Multi-Maleimides Bearing Electron-Donating Chromophores:  Reversible Fluorescence and Aggregation Behavior journal October 2004
Deformation of an amorphous polymer during the fused-filament-fabrication method for additive manufacturing journal March 2017
Synthesis and characterization of linear self-healing polyurethane based on thermally reversible Diels–Alder reaction journal January 2013
Use of Diels–Alder Chemistry for Thermoreversible Cross-Linking of Rubbers: The Next Step toward Recycling of Rubber Products? journal September 2015
Additively manufactured medical products – the FDA perspective journal December 2016
Influence of processing and orientation print effects on the mechanical and thermal behavior of 3D-Printed ULTEM® 9085 Material journal January 2017
Cross-Linking and Modification of Poly(ethylene terephthalate- co -2,6-anthracenedicarboxylate) by Diels−Alder Reactions with Maleimides journal September 1999
A Dual-Cure, Solid-State Photoresist Combining a Thermoreversible Diels–Alder Network and a Chain Growth Acrylate Network journal May 2014
Additive manufacturing of carbon fiber-reinforced plastic composites using fused deposition modeling: Effects of process parameters on tensile properties journal July 2016
A self-healing, re-moldable and biocompatible crosslinked polysiloxane elastomer journal January 2016
3D Printing of Ultratough Polyion Complex Hydrogels journal November 2016
A benchmark study on rapid prototyping processes and machines: Quantitative comparisons of mechanical properties, accuracy, roughness, speed, and material cost journal February 2008
Preparation, solubility and thermal behaviour of new bismaleimides containing silicone linkages journal March 1999
3-D printing of multifunctional carbon nanotube yarn reinforced components journal October 2016
Self-healing bio-based furan polymers cross-linked with various bis-maleimides journal September 2013
An experimental demonstration of effective Curved Layer Fused Filament Fabrication utilising a parallel deposition robot journal October 2015
Highly Efficient and Thermally Stable Electro-optic Polymer from a Smartly Controlled Crosslinking Process journal October 2003
3D printing with polymers: Challenges among expanding options and opportunities journal January 2016
Thermally reversible cross-linked polyamides and thermo-responsive gels by means of Diels–Alder reaction journal April 2006
On reducing anisotropy in 3D printed polymers via ionizing radiation journal November 2014
Healable Capacitive Touch Screen Sensors Based on Transparent Composite Electrodes Comprising Silver Nanowires and a Furan/Maleimide Diels–Alder Cycloaddition Polymer journal November 2014
Design Paradigm Utilizing Reversible Diels–Alder Reactions to Enhance the Mechanical Properties of 3D Printed Materials journal June 2016
Hot-melt extruded filaments based on pharmaceutical grade polymers for 3D printing by fused deposition modeling journal July 2016
Scaffolded Thermally Remendable Hybrid Polymer Networks journal January 2016
Recycling Tires? Reversible Crosslinking of Poly(butadiene) journal February 2015
Rheological and Chemical Analysis of Reverse Gelation in a Covalently Cross-Linked Diels−Alder Polymer Network journal December 2008
Furans in polymer chemistry journal January 1997
Fused filament 3D printing of ionic polymer-metal composites (IPMCs) journal November 2015
A Thermally Re-mendable Cross-Linked Polymeric Material journal March 2002
Slightly crosslinked polyurethane with Diels-Alder adducts from trimethylolpropane journal June 2016
Ultrasound healable shape memory dynamic polymers journal January 2014
Thermally reversible and self‐healing novolac epoxy resins based on DielsAlder chemistry journal March 2015
A novel approach to improve mechanical properties of parts fabricated by fused deposition modeling journal September 2016
Simple and Versatile 3D Printed Microfluidics Using Fused Filament Fabrication journal April 2016

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