High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers

Ding, Keying; John, Alex; Shin, Jihoon; Lee, Young-Min; Quinn, Thomas; Tolman, William B.

doi:10.1021/acs.biomac.5b00754

Cited by 47 publications

(62 citation statements)

References 20 publications

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“… 43 The peel and loop tack forces of biomass-derived SaBSa also were as good as or better than those reported in potentially biobased polyesters-based PSAs (with the addition of tackifier) and acrylic PSAs with glucose or isosorbide components (no addition of tackifier). 38 , 39 , 42 − 44 These comparisons reveal that biomass-derived SaBSa polymers are extremely promising for PSA applications, without the addition of tackifiers or any other additives.…”

Section: Resultsmentioning

confidence: 93%

From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass

et al. 2018

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We report a new and robust strategy toward the development of high-performance pressure sensitive adhesives (PSAs) from chemicals directly obtained from raw biomass deconstruction. A particularly unique and translatable aspect of this work was the use of a monomer obtained from real biomass, as opposed to a model compound or lignin-mimic, to generate well-defined and nanostructure-forming polymers. Herein, poplar wood depolymerization followed by minimal purification steps (filtration and extraction) produced two aromatic compounds, 4-propylsyringol and 4-propylguaiacol, with high purity and yield. Efficient functionalization of those aromatic compounds with either acrylate or methacrylate groups generated monomers that could be easily polymerized by a scalable reversible addition–fragmentation chain-transfer (RAFT) process to yield polymeric materials with high glass transition temperatures and robust thermal stabilities, especially relative to other potentially biobased alternatives. These lignin-derived compounds were used as a major component in low-dispersity triblock polymers composed of 4-propylsyringyl acrylate and n-butyl acrylate (also can be biobased). The resulting PSAs exhibited excellent adhesion to stainless steel without the addition of any tackifier or plasticizer. The 180° peel forces were up to 4 N cm–1, and tack forces were up to 2.5 N cm–1, competitive with commercial Fisherbrand labeling tape and Scotch Magic tape, demonstrating the practical significance of our biomass-derived materials.

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Section: Resultsmentioning

confidence: 93%

From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass

et al. 2018

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“…Researchers have found ways to sustainably source a variety of thermoplastics including polyhydroxyalkanoate, polylactic acid, poly(butylene succinate), poly(trimethylene terephthalate), polyethylene, polypropylene, polyethylene terephthalate, and others . There has even been a significant amount of work in the area of thermoplastic elastomers including triblock copolymers consisting of bio‐derived poly(lactide) sourced from corn and sugar beets reacted with a variety of end groups including poly(menthide) synthesized from (−)‐menthol found in mint leaves, as well as bio‐sourced poly(ethylene glycol), poly(isoprene), and poly(ricinoleic acid) …”

Section: Introductionmentioning

confidence: 99%

“…leaves, as well as bio-sourced poly(ethylene glycol), poly(isoprene), and poly(ricinoleic acid). [24][25][26][27][28][29] There is also a significant amount of research on the development of sustainable thermoset polymers; in particular, with regard to the adhesives and coatings industries. Previous researchers have developed sustainably-sourced acrylics using acrylic acid and methacrylic acid soured from biomass.…”

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confidence: 99%

Tannic acid: A sustainable crosslinking agent for high glass transition epoxy materials

Korey

Mendis

Youngblood

et al. 2018

J. Polym. Sci. Part A: Polym. Chem.

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Epoxy thermosets have revolutionized the coating, adhesive, and composite industries but the chemicals from which they are synthesized have significant effects on the environment and human health not only precure but also after crosslinking has occurred. In this study, we propose tannic acid (TA) as an alternative epoxy hardening agent for commercially available epoxy resin, the diglycidyl ether of bisphenol A (DGEBA). The resulting thermosets were characterized by Fourier transform infrared spectroscopy, optical microscopy, dynamic mechanical analysis, differential scanning calorimetry, compression testing, and thermogravimetric analysis. The results from this study showed that at temperatures above 100 °C, the compatibility of TA in DGEBA was significantly increased for loading levels up to 37% weight of TA in DGEBA, something that has not been seen before in literature. It was also discovered that at high loading levels, the resulting materials had glass transition temperatures at and above 200 °C. The resulting material was proposed as a more sustainable alternative to amine or acid hardened epoxy thermosets and was particularly useful in high‐temperature applications. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1468–1480

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“…). MBL has been shown to be compatible with a wide variety of controlled polymerization strategies such as atom‐transfer radical‐polymerization . Additionally, poly(MBL) (PMBL) has been established as a suitable surrogate for petroleum‐derived poly(methyl methacrylate) (PMMA), due to its similar structure and optical properties .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methylene butyrolactone polymers from itaconic acid

Trotta

Jin

Stawiasz

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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Herein, we report the transformation of bmonomethyl itaconate, an inexpensive and biorenewable alternative to petroleum feedstocks, to the high-value monomer amethylene-c,c-dimethyl-c-butyrolactone (Me 2 MBL) through a selective addition strategy. This strategy is also applied to the synthesis of a-methylene-c-butyrolactone (MBL, tulipalin A), a monomer that can be polymerized to give materials with desirable properties (high decomposition temperature, glass transition temperature, and refractive index). Subsequent polymerization of both Me 2 MBL and MBL through reversible addition-fragmentation chain-transfer polymerization generates well-defined poly(Me 2 MBL) and poly(MBL) (PMBL). Physical characterization of poly(Me 2 MBL) shows good physical properties comparable with known PMBL materials.

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High-Performance Pressure-Sensitive Adhesives from Renewable Triblock Copolymers

Cited by 47 publications

References 20 publications

From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass

From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass

Tannic acid: A sustainable crosslinking agent for high glass transition epoxy materials

Synthesis of methylene butyrolactone polymers from itaconic acid

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