Reinforcement of bio‐based network polymer with wine pomace

Morinaga, Hisatoyo; Haibara, Shunsuke; Ashizawa, S.

doi:10.1002/pc.26030

Cited by 10 publications

(9 citation statements)

References 29 publications

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“…Limonene is a low-cost and readily available terpene with a variety of applications in different areas such as food and beverages [ 19 , 20 ], pharmaceutical [ 21 ], bio-solvent [ 22 ], cosmetics and personal care [ 23 , 24 ]. Limonene has also been used as a building block to prepare various types of biobased polymers [ 25 , 26 , 27 , 28 ]. This terpene is obtained from distillation or by solvent extraction from the peels of citrus fruits.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

et al. 2022

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This study describes the synthesis of a curing agent derived from limonene as well as its application to prepare biobased thermoset polymers via the epoxy/thiol-ene photopolymerization (ETE) method. A biobased commercial epoxy resin was used to synthesize a crosslinked polymeric matrix of polyether-polythioether type. The preparation of the curing agent required two steps. First, a diamine intermediate was prepared by means of a thiol-ene coupling reaction between limonene and cysteamine hydrochloride. Second, the primary amino groups of the intermediate compound were alkylated using allyl bromide. The obtained ditertiary amine-functionalized limonene compound was purified and characterized by FTIR and NMR spectroscopies along with GC-MS. The curing agent was formulated with a tetrafunctional thiol in stoichiometric ratio, and a photoinitiator at 1 mol % concentration, as the components of a thiol-ene system (TES). Two formulations were prepared in which molar concentrations of 30 and 40 mol % of the TES were added to the epoxy resin. The kinetics of the ETE photopolymerizations were determined by means of Real-Time FTIR spectroscopy, which demonstrated high reactivity by observing photopolymerization rates in the range of 1.50–2.25 s−1 for the epoxy, double bonds and thiol groups. The obtained polymers were analyzed by thermal and thermo-mechanical techniques finding glass transition temperatures (Tg) of 60 °C and 52 °C for the polymers derived from the formulations with 30 mol % and 40 mol % of TES, respectively. Potential applications for these materials can be foreseen in the area of coatings.

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Section: Introductionmentioning

confidence: 99%

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

et al. 2022

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“…18 Limonene oxide (LO), one of the limonene derivatives, is a promising candidate for the development of a wide variety of polymers such as thermoplastic 6,7,[18][19][20] and thermoset polymers. [8][9][10][11]21 In our study, we found that bis-functional epoxide derived from trans-LO (bis-trans-LO) shows excellent reactivity in the cross-linking reactions of epoxides with amines, resulting in high polymer yield, thermal resistance, and mechanical strength. 10 Another important cross-linking system for epoxy resins is based on an epoxy/carboxylic acid reaction.…”

Section: Introductionmentioning

confidence: 85%

“…The production of limonene ranges approximately between 50 × 10 3 and 75 × 10 3 tons per year 18 . Limonene oxide (LO), one of the limonene derivatives, is a promising candidate for the development of a wide variety of polymers such as thermoplastic 6,7,18–20 and thermoset polymers 8–11,21 . In our study, we found that bis‐functional epoxide derived from trans ‐LO (bis‐ trans ‐LO) shows excellent reactivity in the cross‐linking reactions of epoxides with amines, resulting in high polymer yield, thermal resistance, and mechanical strength 10 .…”

Section: Introductionmentioning

confidence: 93%

“…1,2 For example, chitosan is obtained by the deacetylation of chitin derived from crustacean shells, which is applicable to membranes and fibers. [3][4][5] The second is the polymerization of natural compounds with low-molecular weights, such as vegetable oil [6][7][8][9][10][11][12] and amino acids. 13,14 The third is the biosynthesis of polymers such as polyhydroxybutyrate (PHB) from naturally occurring carbon sources by specific bacteria.…”

Section: Introductionmentioning

confidence: 99%

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Cross‐linking reaction of diastereomeric bis‐limonene oxide with polyhydric carboxylic acid

Morinaga

Koike

2022

J of Applied Polymer Sci

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In this study, the epoxy‐carboxylic acid reaction was examined using two diastereomers of biobased bis‐functional epoxides (bis‐trans‐LO and bis‐cis‐LO derived from trans‐ and cis‐limonene oxide, respectively) and polyhydric carboxylic acid. The network polymers derived from bis‐trans‐LO had a higher polymer yield as well as superior thermal properties and mechanical strength than those derived from bis‐cis‐LO, since bis‐trans‐LO was cross‐linked effectively owing to the direct nucleophilic attack on the methine carbon of the epoxy ring by carboxy groups. The reprocessability of the network polymer in the presence of Zn(acac)2 was confirmed in both cases, whereas the tensile strength decreased after the 2nd cycle.

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“…In order to reduce dependence on fossil fuels and alleviate environmental problem, researchers are beginning to develop bio-based polymers and innovative process technology. 2 Poly (lactic acid) (PLA) is safe and non-toxic. PLA can be hydrolyzed by acids or enzymes to lactic acid, which is a normal cellular metabolite and can be further metabolized to water and carbon dioxide.…”

Section: Introductionmentioning

confidence: 99%

Study on the property of mesoporous silica nanoparticles loaded with nisin for poly (lactic acid)‐based packaging film

Jiang

Zhu

et al. 2023

Polymer Composites

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Nisin was loaded in mesoporous silica nanoparticles (MSN) (0, 1, 2 and 3 wt%) and incorporated into poly (lactic acid) (PLA) matrix by casting method. The mechanical property, water vapor permeability, thermal property, and antimicrobial property of PLA nanocomposite films were measured. And the internal structure of the composite film was observed through the Scanning electron microscope. Meanwhile, the kinetic of nisin releasing from food simulated solution was investigated and the migration model was established. The result showed that mesoporous silica had an effect on the mechanical and thermal property of the composite films. Both water vapor transmission rate (WVP) and oxygen permeation rate (OTR) decreased, especially for 3MSN/NI/PLA, where WVP decreased by about 9.64% and OTR decreased by 35.19%, which was beneficial to improve the preservation effect. With the addition of MSN, the amount of loaded nisin increased, and at 3MSN/NI, the nisin loading reached 88.75%, and the mesoporous silica could effectively control the release of nisin, thus prolonging the preservation effect. The release kinetic of nisin was described by Fick's law and Weibull's model. In short, the PLA nanocomposite film has the potential to be used as an antimicrobial active film by adding nisin as an antimicrobial agent.Highlights A biodegradable antimicrobial food grade film was prepared. Nisin was added to the films as an antimicrobial agent. The ordered mesoporous structure of MSN was used as a carrier of antimicrobial agent. The film effectively inhibits E. coli and S. aureus by controlling the release of nisin. Fick's law and Weibull's model were used to describe the release kinetics of Nisin.

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Reinforcement of bio‐based network polymer with wine pomace

Cited by 10 publications

References 29 publications

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

Synthesis of a Curing Agent Derived from Limonene and the Study of Its Performance to Polymerize a Biobased Epoxy Resin Using the Epoxy/Thiol-Ene Photopolymerization Technique

Cross‐linking reaction of diastereomeric bis‐limonene oxide with polyhydric carboxylic acid

Study on the property of mesoporous silica nanoparticles loaded with nisin for poly (lactic acid)‐based packaging film

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