Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions
Abstract
ABA triblock copolymers are used as thermoplastic elastomers (TPEs) for a wide variety of applications. In this paper, we describe incorporation of sugar-based glassy components to create sustainable triblock copolymers as alternatives for commodity TPEs. Poly(glucose-6-acrylate-1,2,3,4-tetraacetate) [PGATA] and poly(acetylated acrylic isosorbide) [PAAI] end blocks were chain-extended from a poly(n-butyl acrylate) [PnBA] midblock. PAAI–PnBA–PAAI exhibited excellent adhesion properties: peel = 8.74 N cm–1, loop tack = 2.96 N cm–2, no shear failure up to 100 h, and shear adhesion failure temperature (SAFT) = 60 °C. Although similar peel adhesion and higher loop tack were observed for PGATA–PnBA–PGATA, the shear strength and SAFT were moderate (18 h and 42 °C, respectively). PAAI–PnBA–PAAI are tough elastomers and demonstrated high stress and elongation at break (σ = 6.5 MPa and ε = 620%, respectively) while the GATA-based analogue exhibited weaker tensile properties (σ = 0.8 MPa and ε = 476%). To address this, the anomeric hydroxyl groups of GATA units were selectively deprotected to promote self-complementary hydrogen bonding in the glassy domains, resulting in 80% enhancement in the ultimate tensile stress at break (σ = 1.5 MPa). This study aims to demonstrate effects of noncovalent interactions, such as chain entanglements and self-complementary hydrogen bonding,more »
- Authors:
-
- Univ. of Minnesota, Minneapolis, MN (United States)
- Publication Date:
- Research Org.:
- Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)
- Sponsoring Org.:
- National Science Foundation (NSF); E.I. DuPont de Nemours & Co.; The Dow Chemical Company; Northwestern University; USDOE Office of Science (SC)
- OSTI Identifier:
- 1434739
- Grant/Contract Number:
- DMR-1420013; AC02-06CH11357
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Macromolecules
- Additional Journal Information:
- Journal Volume: 51; Journal Issue: 7; Journal ID: ISSN 0024-9297
- Publisher:
- American Chemical Society
- Country of Publication:
- United States
- Language:
- ENGLISH
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Organic compounds; Noncovalent interactions; Surface interactions; Polymers; Copolymers
Citation Formats
Nasiri, Mohammadreza, Saxon, Derek J., and Reineke, Theresa M. Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions. United States: N. p., 2018.
Web. doi:10.1021/acs.macromol.7b02248.
Nasiri, Mohammadreza, Saxon, Derek J., & Reineke, Theresa M. Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions. United States. https://doi.org/10.1021/acs.macromol.7b02248
Nasiri, Mohammadreza, Saxon, Derek J., and Reineke, Theresa M. Mon .
"Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions". United States. https://doi.org/10.1021/acs.macromol.7b02248. https://www.osti.gov/servlets/purl/1434739.
@article{osti_1434739,
title = {Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions},
author = {Nasiri, Mohammadreza and Saxon, Derek J. and Reineke, Theresa M.},
abstractNote = {ABA triblock copolymers are used as thermoplastic elastomers (TPEs) for a wide variety of applications. In this paper, we describe incorporation of sugar-based glassy components to create sustainable triblock copolymers as alternatives for commodity TPEs. Poly(glucose-6-acrylate-1,2,3,4-tetraacetate) [PGATA] and poly(acetylated acrylic isosorbide) [PAAI] end blocks were chain-extended from a poly(n-butyl acrylate) [PnBA] midblock. PAAI–PnBA–PAAI exhibited excellent adhesion properties: peel = 8.74 N cm–1, loop tack = 2.96 N cm–2, no shear failure up to 100 h, and shear adhesion failure temperature (SAFT) = 60 °C. Although similar peel adhesion and higher loop tack were observed for PGATA–PnBA–PGATA, the shear strength and SAFT were moderate (18 h and 42 °C, respectively). PAAI–PnBA–PAAI are tough elastomers and demonstrated high stress and elongation at break (σ = 6.5 MPa and ε = 620%, respectively) while the GATA-based analogue exhibited weaker tensile properties (σ = 0.8 MPa and ε = 476%). To address this, the anomeric hydroxyl groups of GATA units were selectively deprotected to promote self-complementary hydrogen bonding in the glassy domains, resulting in 80% enhancement in the ultimate tensile stress at break (σ = 1.5 MPa). This study aims to demonstrate effects of noncovalent interactions, such as chain entanglements and self-complementary hydrogen bonding, to enhance the adhesion and mechanical performance of sugar-derived TPEs.},
doi = {10.1021/acs.macromol.7b02248},
journal = {Macromolecules},
number = 7,
volume = 51,
place = {United States},
year = {Mon Mar 19 00:00:00 EDT 2018},
month = {Mon Mar 19 00:00:00 EDT 2018}
}
Web of Science
Works referenced in this record:
Rheology, composition, and peel-mechanism of block copolymer–tackifier-based pressure sensitive adhesives
journal, March 1992
- Nakajima, N.; Babrowicz, R.; Harrell, E. R.
- Journal of Applied Polymer Science, Vol. 44, Issue 8
Rheological properties of hot melt pressure-sensitive adhesives based on styrene--isoprene copolymers. Part 1: A rheological model for [sis-si] formulations
journal, August 2003
- Gibert, F. X.; Marin, G.; Derail, C.
- The Journal of Adhesion, Vol. 79, Issue 8-9
RHEOLOGICAL PROPERTIES OF HOT-MELT PRESSURE-SENSITIVE ADHESIVE (HMPSAs) BASED ON STYRENE–ISOPRENE COPOLYMERS. PART 2: INNOVATIVE MOLECULAR DESIGN FROM PREDICTIVE FORMUlATION
journal, December 2004
- Derail, C.; Cazenave, M. N.; Gibert, F. X.
- The Journal of Adhesion, Vol. 80, Issue 12
Experimental and Self-Consistent-Field Theoretical Study of Styrene Block Copolymer Self-Adhesive Materials
journal, June 2004
- Daoulas, Kostas Ch.; Theodorou, Doros N.; Roos, Alexandra
- Macromolecules, Vol. 37, Issue 13
New “All-Acrylate” Block Copolymers: Synthesis and Influence of the Architecture on the Morphology and the Mechanical Properties
journal, February 2007
- Jeusette, M.; Leclère, Ph.; Lazzaroni, R.
- Macromolecules, Vol. 40, Issue 4
Large-Strain Mechanical Behavior of Model Block Copolymer Adhesives
journal, October 2009
- Creton, Costantino; Hu, Guangjun; Deplace, Fanny
- Macromolecules, Vol. 42, Issue 20
Sustainable Block Copolymer-based Thermoplastic Elastomers [지속 가능한 블록 공중합체 기반 열가소성 탄성체]
journal, April 2014
- Shin, Jihoon; Kim, Young-Wun; Kim, Geon-Joong
- Applied Chemistry for Engineering, Vol. 25, Issue 2
Printable, Degradable, and Biocompatible Ion Gels from a Renewable ABA Triblock Polyester and a Low Toxicity Ionic Liquid
journal, September 2017
- Tang, Boxin; Schneiderman, Deborah K.; Zare Bidoky, Fazel
- ACS Macro Letters, Vol. 6, Issue 10
Strong, Resilient, and Sustainable Aliphatic Polyester Thermoplastic Elastomers
journal, May 2017
- Watts, Annabelle; Kurokawa, Naruki; Hillmyer, Marc A.
- Biomacromolecules, Vol. 18, Issue 6
Synthesis, characterization and degradation of ABA block copolymer of l-lactide and ε-caprolactone
journal, May 2000
- Qian, Haitao; Bei, Jianzhong; Wang, Shenguo
- Polymer Degradation and Stability, Vol. 68, Issue 3
Sustainable poly(ε-decalactone)−poly(l-lactide) multiarm star copolymer architectures for thermoplastic elastomers with fixed molar mass and block ratio
journal, March 2017
- Lee, Sangjun; Lee, Kyungchan; Jang, Jeongmin
- Polymer, Vol. 112
Preparation and Characterization of a Renewable Pressure-Sensitive Adhesive System Derived from ε-Decalactone, l -Lactide, Epoxidized Soybean Oil, and Rosin Ester
journal, August 2015
- Lee, Sangjun; Lee, Kyungchan; Kim, Young-Wun
- ACS Sustainable Chemistry & Engineering, Vol. 3, Issue 9
Poly(lactide)-block-poly(ε-caprolactone-co-ε-decalactone)-block-poly(lactide) copolymer elastomers
journal, January 2015
- Schneiderman, Deborah K.; Hill, Erin M.; Martello, Mark T.
- Polymer Chemistry, Vol. 6, Issue 19
Aliphatic Polyester Block Polymer Design
journal, March 2016
- Schneiderman, Deborah K.; Hillmyer, Marc A.
- Macromolecules, Vol. 49, Issue 7
Sustainable Polymers in the Organic Chemistry Laboratory: Synthesis and Characterization of a Renewable Polymer from δ-Decalactone and l -Lactide
journal, November 2013
- Schneiderman, Deborah K.; Gilmer, Chad; Wentzel, Michael T.
- Journal of Chemical Education, Vol. 91, Issue 1
Photo- and Biodegradable Thermoplastic Elastomers: Combining Ketone-Containing Polybutadiene with Polylactide Using Ring-Opening Polymerization and Ring-Opening Metathesis Polymerization
journal, May 2017
- Arrington, Kyle J.; Waugh, John B.; Radzinski, Scott C.
- Macromolecules, Vol. 50, Issue 11
Renewable-Resource Thermoplastic Elastomers Based on Polylactide and Polymenthide
journal, November 2007
- Wanamaker, Carolyn L.; O'Leary, Leslie E.; Lynd, Nathaniel A.
- Biomacromolecules, Vol. 8, Issue 11
Pressure-Sensitive Adhesives from Renewable Triblock Copolymers
journal, January 2011
- Shin, Jihoon; Martello, Mark T.; Shrestha, Mona
- Macromolecules, Vol. 44, Issue 1
Aliphatic Polyester Block Polymers: Renewable, Degradable, and Sustainable
journal, May 2014
- Hillmyer, Marc A.; Tolman, William B.
- Accounts of Chemical Research, Vol. 47, Issue 8
Biodegradable multiblock PEO/PLA thermoplastic elastomers: molecular design and properties
journal, March 2005
- Cohn, D.; Hotovely-Salomon, A.
- Polymer, Vol. 46, Issue 7
Multiblock Thermoplastic Elastomers Derived from Biodiesel, Poly(propylene glycol), and l -Lactide
journal, August 2017
- Lee, Sangjun; Yuk, Jeong Suk; Park, Hyejin
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 9
Characterization of Polylactide- b -polyisoprene- b -polylactide Thermoplastic Elastomers
journal, March 2003
- Frick, Esther M.; Zalusky, Andrew S.; Hillmyer, Marc A.
- Biomacromolecules, Vol. 4, Issue 2
Fully bio-based poly(l-lactide)-b-poly(ricinoleic acid)-b-poly(l-lactide) triblock copolyesters: investigation of solid-state morphology and thermo-mechanical properties
journal, January 2013
- Lebarbé, Thomas; Ibarboure, Emmanuel; Gadenne, Benoit
- Polymer Chemistry, Vol. 4, Issue 11
High Modulus, Strength, and Toughness Polyurethane Elastomer Based on Unmodified Lignin
journal, July 2017
- Li, Hui; Sun, Jiao-Tong; Wang, Cun
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 9
Sustainable Elastomers from Renewable Biomass
journal, June 2017
- Wang, Zhongkai; Yuan, Liang; Tang, Chuanbing
- Accounts of Chemical Research, Vol. 50, Issue 7
Sustainable polymers from renewable resources
journal, December 2016
- Zhu, Yunqing; Romain, Charles; Williams, Charlotte K.
- Nature, Vol. 540, Issue 7633
Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production
journal, November 2015
- Delidovich, Irina; Hausoul, Peter J. C.; Deng, Li
- Chemical Reviews, Vol. 116, Issue 3
Biobased Plastics and Elastomers from Renewable Rosin via “Living” Ring-Opening Metathesis Polymerization
journal, September 2016
- Ganewatta, Mitra S.; Ding, Wenyue; Rahman, Md Anisur
- Macromolecules, Vol. 49, Issue 19
Sustainable Thermoplastic Elastomers from Terpene-Derived Monomers
journal, July 2014
- Bolton, Justin M.; Hillmyer, Marc A.; Hoye, Thomas R.
- ACS Macro Letters, Vol. 3, Issue 8
Thermoplastic Elastomers Derived from Menthide and Tulipalin A
journal, September 2012
- Shin, Jihoon; Lee, Youngmin; Tolman, William B.
- Biomacromolecules, Vol. 13, Issue 11
High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers
journal, July 2015
- Ding, Keying; John, Alex; Shin, Jihoon
- Biomacromolecules, Vol. 16, Issue 8
Synthesis, morphology and mechanical properties of linear triblock copolymers based on poly(α-methylene-γ-butyrolactone)
journal, April 2009
- Mosnáček, Jaroslav; Yoon, Jeong Ae; Juhari, Azhar
- Polymer, Vol. 50, Issue 9
Progress in Renewable Polymers from Natural Terpenes, Terpenoids, and Rosin
journal, October 2012
- Wilbon, Perry A.; Chu, Fuxiang; Tang, Chuanbing
- Macromolecular Rapid Communications, Vol. 34, Issue 1
Physical Behavior of Triblock Copolymer Thermoplastic Elastomers Containing Sustainable Rosin-Derived Polymethacrylate End Blocks
journal, November 2017
- Ding, Wenyue; Wang, Shu; Yao, Kejian
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 12
Sustainable glucose-based block copolymers exhibit elastomeric and adhesive behavior
journal, January 2016
- Nasiri, Mohammadreza; Reineke, Theresa M.
- Polymer Chemistry, Vol. 7, Issue 33
Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives
journal, May 2016
- Gallagher, James J.; Hillmyer, Marc A.; Reineke, Theresa M.
- ACS Sustainable Chemistry & Engineering, Vol. 4, Issue 6
Single-Centered Hydrogen-Bonded Enhanced Acidity (SHEA) Acids: A New Class of Brønsted Acids
journal, November 2009
- Tian, Zhixin; Fattahi, Alireza; Lis, Lev
- Journal of the American Chemical Society, Vol. 131, Issue 46
Influence of the hydrogen bonding on the basicity of selected macrocyclic amines: INFLUENCE OF THE HYDROGEN BONDING ON THE BASICITY
journal, February 2012
- Nasiri, Mohammadreza; Shakourian-Fard, Mehdi; Fattahi, Alireza
- Journal of Physical Organic Chemistry, Vol. 25, Issue 9
Addition and Correction to Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates
journal, July 2017
- Parmar, Dixit; Sugiono, Erli; Raja, Sadiya
- Chemical Reviews, Vol. 117, Issue 15
Metal-free organocatalysis through explicit hydrogen bonding interactions
journal, January 2003
- Schreiner, Peter R.
- Chemical Society Reviews, Vol. 32, Issue 5
High-Throughput Excipient Discovery Enables Oral Delivery of Poorly Soluble Pharmaceuticals
journal, October 2016
- Ting, Jeffrey M.; Tale, Swapnil; Purchel, Anatolii A.
- ACS Central Science, Vol. 2, Issue 10
Diblock Terpolymers Are Tunable and pH Responsive Vehicles To Increase Hydrophobic Drug Solubility for Oral Administration
journal, September 2017
- Tale, Swapnil; Purchel, Anatolii A.; Dalsin, Molly C.
- Molecular Pharmaceutics, Vol. 14, Issue 11
Structure/property relationships in copolymers comprising renewable isosorbide, glucarodilactone, and 2,5-bis(hydroxymethyl)furan subunits
journal, January 2017
- Lillie, Leon M.; Tolman, William B.; Reineke, Theresa M.
- Polymer Chemistry, Vol. 8, Issue 24
Non-Isocyanate Polyurethane Thermoplastic Elastomer: Amide-Based Chain Extender Yields Enhanced Nanophase Separation and Properties in Polyhydroxyurethane
journal, May 2017
- Beniah, Goliath; Fortman, David J.; Heath, William H.
- Macromolecules, Vol. 50, Issue 11
Mechanical Property Enhancement of ABA Block Copolymer-Based Elastomers by Incorporating Transient Cross-Links into Soft Middle Block
journal, January 2015
- Hayashi, Mikihiro; Matsushima, Satoru; Noro, Atsushi
- Macromolecules, Vol. 48, Issue 2
Model Transient Networks from Strongly Hydrogen-Bonded Polymers
journal, November 2009
- Feldman, Kathleen E.; Kade, Matthew J.; Meijer, E. W.
- Macromolecules, Vol. 42, Issue 22
Highly Ordered Nanoporous Films from Supramolecular Diblock Copolymers with Hydrogen-Bonding Junctions
journal, July 2015
- Montarnal, Damien; Delbosc, Nicolas; Chamignon, Cécile
- Angewandte Chemie International Edition, Vol. 54, Issue 38
Dependence of the Ultimate Tensile Strength of Thermoplastic Elastomers of the Triblock Type on the Molecular Weight between Chain Entanglements of the Central Block
journal, March 2000
- Tong, Jiang-Dong; Jerôme, Robert
- Macromolecules, Vol. 33, Issue 5
Effect of chain length distribution on mechanical behavior of polymeric networks
journal, February 2017
- Tehrani, Mohammad; Sarvestani, Alireza
- European Polymer Journal, Vol. 87
Polymeric Nanocylinders by Combining Block Copolymer Self-Assembly and Nanoskiving
journal, September 2014
- Nasiri, Mohammadreza; Bertrand, Arthur; Reineke, Theresa M.
- ACS Applied Materials & Interfaces, Vol. 6, Issue 18
Theory and Analysis of Peel Adhesion: Adhesive Thickness Effects
journal, February 1992
- Kaelble, D. H.
- The Journal of Adhesion, Vol. 37, Issue 1-3
Micellization and Micellar Aggregation of Poly(ethylene- alt -propylene)- b -poly(ethylene oxide)- b -poly( N -isopropylacrylamide) Triblock Terpolymers in Water
journal, March 2011
- Zhou, Can; Hillmyer, Marc A.; Lodge, Timothy P.
- Macromolecules, Vol. 44, Issue 6
Synthesis of Harounoside, A Naturally Occurring Pentalongin Hydroquinone Bisglucoside
journal, September 2006
- Van, Tuyen; Claessens, Sven; Habonimana, Pascal
- Synlett, Vol. 2006, Issue 15
Works referencing / citing this record:
Cationic copolymerization of isosorbide towards value-added poly(vinyl ethers)
journal, January 2019
- Kieber, Robert J.; Ozkardes, Cuneyt; Sanchez, Natalie
- Polymer Chemistry, Vol. 10, Issue 25
Sustainable bio-based furan epoxy resin with flame retardancy
journal, January 2019
- Meng, Jingjing; Zeng, Yushun; Zhu, Guiqin
- Polymer Chemistry, Vol. 10, Issue 19
Loop-stabilized BAB triblock copolymer morphologies by PISA in water
journal, January 2018
- Biais, Pauline; Beaunier, Patricia; Stoffelbach, François
- Polymer Chemistry, Vol. 9, Issue 35
Novel functionalized polyamides prone to undergo thermal Claisen rearrangement in the solid state
journal, January 2018
- de la Viuda, Mónica R.; Tena, Alberto; Neumann, Silvio
- Polymer Chemistry, Vol. 9, Issue 29
Superior Electrochemical Performance of Thin-Film Thermoplastic Elastomer-Coated SnSb as an Anode for Li-ion Batteries
journal, March 2019
- Tesfaye, Alexander T.; Dumur, Frédéric; Gigmes, Didier
- Scientific Reports, Vol. 9, Issue 1
Interphase synergistic effects of dynamic bonds in multiphase thermoplastic elastomers
journal, January 2019
- Kawana, Saki; Nakagawa, Shintaro; Nakai, Shuya
- Journal of Materials Chemistry A, Vol. 7, Issue 37
Sub‐3 V ZnO Electrolyte‐Gated Transistors and Circuits with Screen‐Printed and Photo‐Crosslinked Ion Gel Gate Dielectrics: New Routes to Improved Performance
journal, May 2019
- Zare Bidoky, Fazel; Tang, Boxin; Ma, Rui
- Advanced Functional Materials, Vol. 30, Issue 20
Enhanced Heat Resistance and Adhesive Strength of Styrene–Acrylic Triblock Copolymer Elastomers by Incorporating Acrylic Acid
journal, February 2020
- Mogami, Hirokazu; Mori, Hideharu
- ACS Omega, Vol. 5, Issue 7