Preparation and Characterization of a Renewable Pressure-Sensitive Adhesive System Derived from ε-Decalactone, <scp>l</scp>-Lactide, Epoxidized Soybean Oil, and Rosin Ester

Lee, Sang-Jun; Lee, Kyungchan; Kim, Young‐Wun; Shin, Jihoon

doi:10.1021/acssuschemeng.5b00580

Cited by 93 publications

(130 citation statements)

References 58 publications

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“…The thermal degradation of MBM also was characterized in air flow, and the thermal stability was much lower, with a 5% degradation temperature of 285 °C ( Figure S7 ). Furthermore, when comparing SaBSa to other model bioinspired PSAs reported in the literature, the lignin-derived materials herein have thermal degradation temperatures in air that are at least 30 °C higher than acrylate-functionalized glucose, acrylate-functionalized isosorbide, and polyester-based systems, 38 , 39 , 42 providing a much larger temperature window for processing.…”

Section: Resultsmentioning

confidence: 99%

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: 99%

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

et al. 2018

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“…Recently, the performance of TPEs have been significantly improved by inducting self‐healable properties, stimuli‐responsive properties and tunable morphology . In addition, environment‐friendly TPEs have also been successfully developed using sustainable and renewable resources . These strategies to develop new types of linear TPEs are also expected to advance the design and synthesis of multigraft TPEs.…”

Section: Resultsmentioning

confidence: 99%

Design and Synthesis of Multigraft Copolymer Thermoplastic Elastomers: Superelastomers

Wang

et al. 2017

Macro Chemistry & Physics

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worldwide elastomer market, as sealants, coatings, adhesives, sporting good components, automotive parts, footwear, and as biomedical materials. [1] Prepared by living anionic polymerization, styrenic thermoplastic elastomers (S-TPEs), including polystyrene-blockpolyisoprene-block-polystyrene (SIS) and polystyrene-block-polybutadiene-blockpolystyrene (SBS), were first developed by Holden and Millkvich in the early 1960s and have since then become widely used in our daily life. [2,3] The exceptional mechanical properties of S-TPEs are attributed to the microphase separation between the two chemically incompati ble domains where hard polystyrene (PS) domains serve as physical cross-links for the soft polybutadiene (PB) or polyisoprene (PI) matrix. Mechani cal properties, such as tensile strength, Young's modulus, and elasticity, are tunable based on volume fractions of hard and soft domains. One limitation of S-TPEs is the restricted upper service temperature (UST), which is limited by the glass transition temperature (T g ) of polystyrene (T g ≈ 100 °C). When the service temperature is approaching 100 °C, softening of PS domains disrupts the physical cross-links, leading to a sharp drop of storage modulus. Numerous studies have been carried to increase the UST of S-TPEs by either replacing polystyrene with another higher T g polymer [4][5][6][7][8] or using catalytic hydrogenation to fully saturate PS into polyvinylcyclohexane (T g ≈ 150 °C). [9] With recent advances in living/controlled polymerization, various nonlinear architectures, including star, [10][11][12][13][14] graft, and cyclic [15,16] architectures, or their combinations, [17][18][19][20] have been synthesized during the past three decades. These nonlinear macromolecular architectures deliver additional parameters for chemists to use in tuning mechanical properties, as well as incorporating additional functionality to TPEs [21] (Figure 1).In this short review, we focus on the progress in design and synthesis of well-defined multigraft copolymers and their application as thermoplastic elastomers. Progress in precise synthesis of graft copolymers and mechanical properties of multigraft copolymers is first summarized. Recent work on all-acrylic graft copolymer TPEs and a low-cost emulsion polymerization approach to prepare multigraft copolymers are introduced subsequently. Finally, we finish the review with conclusions and some future prospectives. Living Anionic PolymerizationsThermoplastic elastomers (TPEs) have been widely studied because of their recyclability, good processibility, low production cost, and unique performance. The building of graft-type architectures can greatly improve mechanical properties of TPEs. This review focuses on the advances in different approaches to synthesize multigraft copolymer TPEs. Anionic polymerization techniques allow for the synthesis of well-defined macromolecular structures and compositions, with great control over the molecular weight, polydispersity, branch spacing, number of branch points, and branch point ...

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“…According to Miao et al , the biocompatibility of polyurethane using a lactic acid initiator was tested in mice, and cell proliferation was confirmed on polyurethane. Polyurethane made from plant oil based 10‐Undecenoic acid is also known to be biocompatible . Gonzalez‐Paz et al reported that the polyurethane made by polymerizing the diol prepared by linking a hydroxyl group to a double bond and the carboxyl group of 10‐undecenoic acid and the 4,4’‐ethylenebis(phenylisocyanate) was found not to be biotoxic.…”

Section: C3–c30 Oil Derivativesmentioning

confidence: 99%

Feasibility of unsaturated fatty acid feedstocks as green alternatives in bio‐oil refinery

Jeon

Han

Kim

et al. 2019

Biofuels Bioprod Bioref

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Bio‐oil contains plant, animal, fish, and micro‐algae oil, and more than 200 million tons are produced annually. However, many edible and non‐edible bio‐oils are still under development, and their value and feasibility have yet to be determined. The vast majority of bio‐oils produced in the world have a very high unsaturated fatty acid content (70–98%), which could be used as a renewable, eco‐friendly alternative to petroleum. Hydrolysis (or transesterification) with ethylene metathesis technology converts unsaturated fatty acids to C4–C30 oil fragments. These oil fragments are a sustainable chemical technology used in chemical industry platform technology and carbon dioxide abatement green chemical technology, and as a petrochemical substitute. These platform chemicals also have their own market but are used as raw materials for other products (polymers, surfactants, synthetic lubricants, plasticizers, other specialty chemicals, general purpose chemicals, biofuels, etc.). The biodegradability and biocompatibility of the polymeric materials made from the oil mean that it is also possible to develop diverse functional products with high added value such as toothpaste, dandruff treatment shampoo, and melanin pigment removal cosmetics, medical and shape memory polymer materials. According to the cradle‐to‐gate analysis for environmental impact and economics, the total carbon dioxide emission reduction per ton of soybean oil was estimated to be 1.5 kg kg−1 products. Moreover, the metathesis of soybean oil ($680/ton) with additional raw materials ($237.4) will generate a value that is 7.5 times higher at $6857. Due to the biodegradability and biocompatibility of the products made from bio‐oils, it is expected that various functional products with high added value will be developed and that industrial applicability will be greatly expanded in the near future. In addition, for the development of various derivatives, fusion and cooperative research in chemical fields such as catalytic engineering, organic chemistry, polymer chemistry, maintenance chemistry, and reaction engineering are essential. © 2019 Society of Chemical Industry and John Wiley & Sons, Ltd

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Preparation and Characterization of a Renewable Pressure-Sensitive Adhesive System Derived from ε-Decalactone, l-Lactide, Epoxidized Soybean Oil, and Rosin Ester

Cited by 93 publications

References 58 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

Design and Synthesis of Multigraft Copolymer Thermoplastic Elastomers: Superelastomers

Feasibility of unsaturated fatty acid feedstocks as green alternatives in bio‐oil refinery

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