Biorenewable Epoxy Resins Derived from Plant-Based Phenolic Acids

Yang, Guozhen; Rohde, Brian J.; Tesefay, Hiruy; Robertson, Megan L.

doi:10.1021/acssuschemeng.6b01343

Cited by 49 publications

(41 citation statements)

References 60 publications

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“…[181,182] Examples include the use of phenolic lipids (e.g., cardanol), phenolic acids (e.g., GA and hydroxybenzoic acid), and polyphenols (e.g., quercetin). [183][184][185][186][187] For polycarbonates, phenolic compounds such as ferulic acid, honokiol, and lignin can be used directly in the polymerization reactions. [151,161,188,189] The toolbox of natural phenolics has therefore allowed for a multitude of structural materials with different properties to act as replacements for conventionally used BPA.…”

Section: Reviewmentioning

confidence: 99%

Phenolic Building Blocks for the Assembly of Functional Materials

et al. 2018

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Phenolic materials have long been known for their use in inks, wood coatings, and leather tanning. However, recently there has been a renewed interest in engineering advanced materials from phenolic building blocks. The intrinsic properties of phenolic compounds, such as metal chelation, hydrogen bonding, pH responsiveness, redox potentials, radical scavenging, polymerization, and light absorbance, have made them a distinct class of structural motifs for the synthesis of functional materials. Materials prepared from phenolic compounds often retain many of these useful properties with synergistic effects in applications ranging from catalysis to biomedicine. The present review provides an overview of the diverse functional materials that can be prepared from phenolic building blocks, bridging the various fields currently studying and using phenolic compounds. Natural and synthetic phenolic compounds are first discussed, followed by the assembly of functional materials. The engineered phenolic materials are grouped under three broad categories: thin films (e.g., metal-phenolic networks and polydopamine); particles (e.g., metal-organic frameworks and superstructures); and bulk materials (e.g., gels). Applications of phenolic-based materials are then presented, focusing mainly on mechanical (e.g., adhesives), biological (e.g., drug delivery), and environmental and energy (e.g., separation and catalysis) applications. Several examples of their emerging applications are also included. Finally, potential routes for the continued integration of disparate fields using phenolic building blocks and fundamental questions still requiring investigation are highlighted, and an outlook of the field is provided.

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Section: Reviewmentioning

confidence: 99%

Phenolic Building Blocks for the Assembly of Functional Materials

et al. 2018

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“…Thus, our biobased epoxy resins, in particularly 1,6‐diamino hexane and IPDA‐cured resins 6 and 7 , displayed much higher T g values. Furthermore, glass transition temperatures of these hydrovanilloin epoxy resins are comparable to commercially available diglycidyl ether of bisphenol A (DGEBA)—polyamine epoxy resins—which are typically in the range of 120–150°C . The total heat absorbed in the glass transition (Δ H ) for 3‐7 are also listed in Table .…”

Section: Resultsmentioning

confidence: 94%

“…In a recent study on biobased epoxy resins, Robertson et al . prepared commercial polyamine‐cured epoxidized 4‐hydroxybenzoic and salicylic acid‐based epoxy resins and these resins showed T g values in the range of 81–112°C . Another vanillin‐based cured epoxy resins of 2,5‐bis(4‐hydroxy‐3‐methoxybenzylidene) cyclopenta‐none‐digycidyl ether showed T g values in 121–130°C range .…”

Section: Resultsmentioning

confidence: 99%

“…52 In addition, the commercial biosourced epoxy materials are known to have low T g values; for example: Epobiox Sandtech T g = 80 C and Greenpoxy Sicomin T g = 85 C. 53 Thus, our biobased epoxy resins, in particularly 1,6-diamino hexane and IPDA-cured resins 6 and 7, displayed much higher T g values. Furthermore, glass transition temperatures of these hydrovanilloin epoxy resins are comparable to commercially available diglycidyl ether of bisphenol A (DGEBA)-polyamine epoxy resins-which are typically in the range of 120-150 C. 51,53 The total heat absorbed in the glass transition (ΔH) for 3-7 are also listed in Table I. In amine-cured resins 4 and 5 cured with smaller amines showed higher ΔH values, whereas the high T g resins 6 and 7 cured with larger amines showed lower ΔH values.…”

Section: Thermal Properties Of Hydrovanilloin Epoxy Resinsmentioning

confidence: 92%

“…This difference in glass transition temperatures is probably due to optimal and close packing of polymer chains in polymers with longer diamine link between rigid aromatic units. In a recent study on biobased epoxy resins, Robertson et al prepared commercial polyamine-cured epoxidized 4-hydroxybenzoic and salicylic acid-based epoxy resins and these resins showed T g values in the range of 81-112 C. 51 Another vanillin-based cured epoxy resins of 2,5-bis(4-hydroxy-3-methoxybenzylidene) cyclopenta-none-digycidyl ether showed T g values in 121-130 C range. 52 In addition, the commercial biosourced epoxy materials are known to have low T g values; for example: Epobiox Sandtech T g = 80 C and Greenpoxy Sicomin T g = 85 C. 53 Thus, our biobased epoxy resins, in particularly 1,6-diamino hexane and IPDA-cured resins 6 and 7, displayed much higher T g values.…”

Section: Thermal Properties Of Hydrovanilloin Epoxy Resinsmentioning

confidence: 99%

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Vanillin‐based polymers: IV. Hydrovanilloin epoxy resins

Amarasekara

Garcia‐Obergon

Thompson

2018

J of Applied Polymer Sci

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In this study, hydrovanilloin synthesized by electrochemical dimerization of vanillin has been used as a renewable substitute for bisphenol A for the preparation of epoxy resins. The reaction of the disodium salt of hydrovanilloin:epichlorohydrin 1:2 mol ratio at 80°C for 30 min in water gave a hydrovanilloin – diglycidyl ether phenoxy resin. This hard thermoplastic resin showed Tg of 135°C and stable up to 255°C in air. On the other hand, the disodium salt of hydrovanilloin:epichlorohydrin 1:4 mol ratio at 80°C for 30 min in water gives a curable oligomer of hydrovanilloin – diglycidyl ether with 2.1 repeating units. This oligomer could be cured with aliphatic diamines: 1,2‐diaminoethane, 1,4‐diaminobutane, 1,6‐diaminohexane, and isophorone diamine to give hard epoxy resins with Tg values of 116, 118, 149 and 146°C, respectively. © 2018 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2019, 136, 47000.

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Phenolische Bausteine für die Assemblierung von Funktionsmaterialien

et al. 2018

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Phenolische Materialien sind seit langem für ihre Verwendung in Farbtinten, in Holzbeschichtungen und zur Ledergerbung bekannt. In letzter Zeit ist jedoch ein wachsendes Interesse an der Entwicklung moderner Werkstoffe aus phenolischen Bausteinen zu verzeichnen. Die intrinsischen Eigenschaften von phenolischen Verbindungen, wie Metallchelat‐Bildung, Wasserstoffbrücken, pH‐Ansprechverhalten, Redoxpotentiale, Radikalfänger, Polymerisation und Lichtabsorption, haben sie zu einer eigenständigen Klasse von Strukturelementen für die Synthese von funktionellen Materialien gemacht. Aus Phenolverbindungen hergestellte Materialien behalten viele ihrer nützlichen Eigenschaften, oft mit synergistischen Effekten bei Anwendungen, die von der Katalyse bis zur Biomedizin reichen. Dieser Aufsatz gibt einen Überblick über die verschiedenen funktionellen Materialien, die aus natürlichen und synthetischen phenolischen Bausteinen hergestellt werden können, und über ihre Anwendungen.

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Biorenewable Epoxy Resins Derived from Plant-Based Phenolic Acids

Cited by 49 publications

References 60 publications

Phenolic Building Blocks for the Assembly of Functional Materials

Phenolic Building Blocks for the Assembly of Functional Materials

Vanillin‐based polymers: IV. Hydrovanilloin epoxy resins

Phenolische Bausteine für die Assemblierung von Funktionsmaterialien

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