Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions

Nasiri, Mohammadreza; Saxon, Derek J.; Reineke, Theresa M.

doi:10.1021/acs.macromol.7b02248

Title: 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 »« less

Authors:

^[1];

^[1]

Univ. of Minnesota, Minneapolis, MN (United States)

Publication Date:: Mon Mar 19 00:00:00 EDT 2018

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.

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                    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

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                    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.

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@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}

}

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Title: Enhanced Mechanical and Adhesion Properties in Sustainable Triblock Copolymers via Non-covalent Interactions

Abstract

Citation Formats

Rheology, composition, and peel-mechanism of block copolymer–tackifier-based pressure sensitive adhesives journal, March 1992

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

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

Experimental and Self-Consistent-Field Theoretical Study of Styrene Block Copolymer Self-Adhesive Materials journal, June 2004

New “All-Acrylate” Block Copolymers: Synthesis and Influence of the Architecture on the Morphology and the Mechanical Properties journal, February 2007

Large-Strain Mechanical Behavior of Model Block Copolymer Adhesives journal, October 2009

Sustainable Block Copolymer-based Thermoplastic Elastomers [지속 가능한 블록 공중합체 기반 열가소성 탄성체] journal, April 2014

Printable, Degradable, and Biocompatible Ion Gels from a Renewable ABA Triblock Polyester and a Low Toxicity Ionic Liquid journal, September 2017

Strong, Resilient, and Sustainable Aliphatic Polyester Thermoplastic Elastomers journal, May 2017

Synthesis, characterization and degradation of ABA block copolymer of l-lactide and ε-caprolactone journal, May 2000

Sustainable poly(ε-decalactone)−poly(l-lactide) multiarm star copolymer architectures for thermoplastic elastomers with fixed molar mass and block ratio journal, March 2017

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

Poly(lactide)-block-poly(ε-caprolactone-co-ε-decalactone)-block-poly(lactide) copolymer elastomers journal, January 2015

Aliphatic Polyester Block Polymer Design journal, March 2016

Sustainable Polymers in the Organic Chemistry Laboratory: Synthesis and Characterization of a Renewable Polymer from δ-Decalactone and l -Lactide journal, November 2013

Photo- and Biodegradable Thermoplastic Elastomers: Combining Ketone-Containing Polybutadiene with Polylactide Using Ring-Opening Polymerization and Ring-Opening Metathesis Polymerization journal, May 2017

Renewable-Resource Thermoplastic Elastomers Based on Polylactide and Polymenthide journal, November 2007

Pressure-Sensitive Adhesives from Renewable Triblock Copolymers journal, January 2011

Aliphatic Polyester Block Polymers: Renewable, Degradable, and Sustainable journal, May 2014

Biodegradable multiblock PEO/PLA thermoplastic elastomers: molecular design and properties journal, March 2005

Multiblock Thermoplastic Elastomers Derived from Biodiesel, Poly(propylene glycol), and l -Lactide journal, August 2017

Characterization of Polylactide- b -polyisoprene- b -polylactide Thermoplastic Elastomers journal, March 2003

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

High Modulus, Strength, and Toughness Polyurethane Elastomer Based on Unmodified Lignin journal, July 2017

Sustainable Elastomers from Renewable Biomass journal, June 2017

Sustainable polymers from renewable resources journal, December 2016

Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production journal, November 2015

Biobased Plastics and Elastomers from Renewable Rosin via “Living” Ring-Opening Metathesis Polymerization journal, September 2016

Sustainable Thermoplastic Elastomers from Terpene-Derived Monomers journal, July 2014

Thermoplastic Elastomers Derived from Menthide and Tulipalin A journal, September 2012

High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers journal, July 2015

Synthesis, morphology and mechanical properties of linear triblock copolymers based on poly(α-methylene-γ-butyrolactone) journal, April 2009

Progress in Renewable Polymers from Natural Terpenes, Terpenoids, and Rosin journal, October 2012

Physical Behavior of Triblock Copolymer Thermoplastic Elastomers Containing Sustainable Rosin-Derived Polymethacrylate End Blocks journal, November 2017

Sustainable glucose-based block copolymers exhibit elastomeric and adhesive behavior journal, January 2016

Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives journal, May 2016

Single-Centered Hydrogen-Bonded Enhanced Acidity (SHEA) Acids: A New Class of Brønsted Acids journal, November 2009

Influence of the hydrogen bonding on the basicity of selected macrocyclic amines: INFLUENCE OF THE HYDROGEN BONDING ON THE BASICITY journal, February 2012

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

Metal-free organocatalysis through explicit hydrogen bonding interactions journal, January 2003

High-Throughput Excipient Discovery Enables Oral Delivery of Poorly Soluble Pharmaceuticals journal, October 2016

Diblock Terpolymers Are Tunable and pH Responsive Vehicles To Increase Hydrophobic Drug Solubility for Oral Administration journal, September 2017

Structure/property relationships in copolymers comprising renewable isosorbide, glucarodilactone, and 2,5-bis(hydroxymethyl)furan subunits journal, January 2017

Non-Isocyanate Polyurethane Thermoplastic Elastomer: Amide-Based Chain Extender Yields Enhanced Nanophase Separation and Properties in Polyhydroxyurethane journal, May 2017

Mechanical Property Enhancement of ABA Block Copolymer-Based Elastomers by Incorporating Transient Cross-Links into Soft Middle Block journal, January 2015

Model Transient Networks from Strongly Hydrogen-Bonded Polymers journal, November 2009

Highly Ordered Nanoporous Films from Supramolecular Diblock Copolymers with Hydrogen-Bonding Junctions journal, July 2015

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

Effect of chain length distribution on mechanical behavior of polymeric networks journal, February 2017

Polymeric Nanocylinders by Combining Block Copolymer Self-Assembly and Nanoskiving journal, September 2014

Physical Properties of Polymers Handbook book, January 2007

Theory and Analysis of Peel Adhesion: Adhesive Thickness Effects journal, February 1992

Micellization and Micellar Aggregation of Poly(ethylene- alt -propylene)- b -poly(ethylene oxide)- b -poly( N -isopropylacrylamide) Triblock Terpolymers in Water journal, March 2011

Synthesis of Harounoside, A Naturally Occurring Pentalongin Hydroquinone Bisglucoside journal, September 2006

Cationic copolymerization of isosorbide towards value-added poly(vinyl ethers) journal, January 2019

Sustainable bio-based furan epoxy resin with flame retardancy journal, January 2019

Loop-stabilized BAB triblock copolymer morphologies by PISA in water journal, January 2018

Novel functionalized polyamides prone to undergo thermal Claisen rearrangement in the solid state journal, January 2018

Superior Electrochemical Performance of Thin-Film Thermoplastic Elastomer-Coated SnSb as an Anode for Li-ion Batteries journal, March 2019

Interphase synergistic effects of dynamic bonds in multiphase thermoplastic elastomers journal, January 2019

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

Enhanced Heat Resistance and Adhesive Strength of Styrene–Acrylic Triblock Copolymer Elastomers by Incorporating Acrylic Acid journal, February 2020

Rheology, composition, and peel-mechanism of block copolymer–tackifier-based pressure sensitive adhesives
journal, March 1992

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

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

Experimental and Self-Consistent-Field Theoretical Study of Styrene Block Copolymer Self-Adhesive Materials
journal, June 2004

New “All-Acrylate” Block Copolymers: Synthesis and Influence of the Architecture on the Morphology and the Mechanical Properties
journal, February 2007

Large-Strain Mechanical Behavior of Model Block Copolymer Adhesives
journal, October 2009

Sustainable Block Copolymer-based Thermoplastic Elastomers [지속 가능한 블록 공중합체 기반 열가소성 탄성체]
journal, April 2014

Printable, Degradable, and Biocompatible Ion Gels from a Renewable ABA Triblock Polyester and a Low Toxicity Ionic Liquid
journal, September 2017

Strong, Resilient, and Sustainable Aliphatic Polyester Thermoplastic Elastomers
journal, May 2017

Synthesis, characterization and degradation of ABA block copolymer of l-lactide and ε-caprolactone
journal, May 2000

Sustainable poly(ε-decalactone)−poly(l-lactide) multiarm star copolymer architectures for thermoplastic elastomers with fixed molar mass and block ratio
journal, March 2017

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

Poly(lactide)-block-poly(ε-caprolactone-co-ε-decalactone)-block-poly(lactide) copolymer elastomers
journal, January 2015

Aliphatic Polyester Block Polymer Design
journal, March 2016

Sustainable Polymers in the Organic Chemistry Laboratory: Synthesis and Characterization of a Renewable Polymer from δ-Decalactone and l -Lactide
journal, November 2013

Photo- and Biodegradable Thermoplastic Elastomers: Combining Ketone-Containing Polybutadiene with Polylactide Using Ring-Opening Polymerization and Ring-Opening Metathesis Polymerization
journal, May 2017

Renewable-Resource Thermoplastic Elastomers Based on Polylactide and Polymenthide
journal, November 2007

Pressure-Sensitive Adhesives from Renewable Triblock Copolymers
journal, January 2011

Aliphatic Polyester Block Polymers: Renewable, Degradable, and Sustainable
journal, May 2014

Biodegradable multiblock PEO/PLA thermoplastic elastomers: molecular design and properties
journal, March 2005

Multiblock Thermoplastic Elastomers Derived from Biodiesel, Poly(propylene glycol), and l -Lactide
journal, August 2017

Characterization of Polylactide- b -polyisoprene- b -polylactide Thermoplastic Elastomers
journal, March 2003

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

High Modulus, Strength, and Toughness Polyurethane Elastomer Based on Unmodified Lignin
journal, July 2017

Sustainable Elastomers from Renewable Biomass
journal, June 2017

Sustainable polymers from renewable resources
journal, December 2016

Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production
journal, November 2015

Biobased Plastics and Elastomers from Renewable Rosin via “Living” Ring-Opening Metathesis Polymerization
journal, September 2016

Sustainable Thermoplastic Elastomers from Terpene-Derived Monomers
journal, July 2014

Thermoplastic Elastomers Derived from Menthide and Tulipalin A
journal, September 2012

High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers
journal, July 2015

Synthesis, morphology and mechanical properties of linear triblock copolymers based on poly(α-methylene-γ-butyrolactone)
journal, April 2009

Progress in Renewable Polymers from Natural Terpenes, Terpenoids, and Rosin
journal, October 2012

Physical Behavior of Triblock Copolymer Thermoplastic Elastomers Containing Sustainable Rosin-Derived Polymethacrylate End Blocks
journal, November 2017

Sustainable glucose-based block copolymers exhibit elastomeric and adhesive behavior
journal, January 2016

Acrylic Triblock Copolymers Incorporating Isosorbide for Pressure Sensitive Adhesives
journal, May 2016

Single-Centered Hydrogen-Bonded Enhanced Acidity (SHEA) Acids: A New Class of Brønsted Acids
journal, November 2009

Influence of the hydrogen bonding on the basicity of selected macrocyclic amines: INFLUENCE OF THE HYDROGEN BONDING ON THE BASICITY
journal, February 2012

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

Metal-free organocatalysis through explicit hydrogen bonding interactions
journal, January 2003

High-Throughput Excipient Discovery Enables Oral Delivery of Poorly Soluble Pharmaceuticals
journal, October 2016

Diblock Terpolymers Are Tunable and pH Responsive Vehicles To Increase Hydrophobic Drug Solubility for Oral Administration
journal, September 2017

Structure/property relationships in copolymers comprising renewable isosorbide, glucarodilactone, and 2,5-bis(hydroxymethyl)furan subunits
journal, January 2017

Non-Isocyanate Polyurethane Thermoplastic Elastomer: Amide-Based Chain Extender Yields Enhanced Nanophase Separation and Properties in Polyhydroxyurethane
journal, May 2017

Mechanical Property Enhancement of ABA Block Copolymer-Based Elastomers by Incorporating Transient Cross-Links into Soft Middle Block
journal, January 2015

Model Transient Networks from Strongly Hydrogen-Bonded Polymers
journal, November 2009

Highly Ordered Nanoporous Films from Supramolecular Diblock Copolymers with Hydrogen-Bonding Junctions
journal, July 2015

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

Effect of chain length distribution on mechanical behavior of polymeric networks
journal, February 2017

Polymeric Nanocylinders by Combining Block Copolymer Self-Assembly and Nanoskiving
journal, September 2014

Physical Properties of Polymers Handbook
book, January 2007

Theory and Analysis of Peel Adhesion: Adhesive Thickness Effects
journal, February 1992

Micellization and Micellar Aggregation of Poly(ethylene- alt -propylene)- b -poly(ethylene oxide)- b -poly( N -isopropylacrylamide) Triblock Terpolymers in Water
journal, March 2011

Synthesis of Harounoside, A Naturally Occurring Pentalongin Hydroquinone Bisglucoside
journal, September 2006

Cationic copolymerization of isosorbide towards value-added poly(vinyl ethers)
journal, January 2019

Sustainable bio-based furan epoxy resin with flame retardancy
journal, January 2019

Loop-stabilized BAB triblock copolymer morphologies by PISA in water
journal, January 2018

Novel functionalized polyamides prone to undergo thermal Claisen rearrangement in the solid state
journal, January 2018

Superior Electrochemical Performance of Thin-Film Thermoplastic Elastomer-Coated SnSb as an Anode for Li-ion Batteries
journal, March 2019

Interphase synergistic effects of dynamic bonds in multiphase thermoplastic elastomers
journal, January 2019

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

Enhanced Heat Resistance and Adhesive Strength of Styrene–Acrylic Triblock Copolymer Elastomers by Incorporating Acrylic Acid
journal, February 2020