Structure-Property Relationships for Polycyanurate Networks Derived from Renewable Resources

Guenthner, Andrew J.; Harvey, Benjamin G.; Davis, Matthew C.; Ford, Michael; Meylemans, Heather A.; Wright, M.; Chafin, Andrew P.; Mabry, Joseph M.

doi:10.1021/bk-2015-1192.ch026

Cited by 3 publications

(3 citation statements)

References 17 publications

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“…This phenomenon could be explained from the chemical point of view. The hydroxyl group in 6FDABPA and Si–B has a positive effect on the prepolymerization of CY‐1 . Besides, the decrease of ‐OCN signal implied the copolymerization of CR‐1 and CR‐2 occurred at 180°C.…”

Section: Resultsmentioning

confidence: 96%

Thermal and water absorption properties of cyanate ester resins modified by fluoride‐containing and silicone‐containing components

Pei

Han

Guo

et al. 2020

Polymers for Advanced Techs

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resin matrix, hence reducing the water absorption of the materials. [22][23][24][25][26][27][28][29] More importantly, silicon-containing resins exhibited excellent heat resistance, weather resistance, and electrical insulation, 1,8,[30][31][32][33][34][35][36] while fluorine-containing resins also have advantages in heat resistance, dielectric properties, chemical stability, weather resistance, and nonflammability. These features were made silicon-containing and fluorine-containing resins suitable components for the modification of high temperature dielectric thermosets, and some successful examples were already realized in CE resins. Yang et al reported the preparation of epoxidized polysiloxane (E-Si), and the addition of E-Si into CE resin cannot only significantly decrease the curing temperature of the CE resin but also improve its water resistance and toughness. 22 Dai et al reported an epoxidized polysiloxane with amino silicone and used it as a modifier to effectively reduce the dielectric constant of CE resin. 28 Guenthner et al reported the preparation of a novel silyl cyanate monomer from bis (4-cyanophenyl) dimethylsilane (Simcy), and moisture absorption of the as-prepared CE resin was reduced by 50%, when compared with pure CE resin. 37 Gu's group synthesized high-quality and stable fluoride-containing compound 2-((3-(trifluoromethyl)phenoxy)methyl) oxirane (TFMPMO), and the results showed that TFMPMO was gifted with lower moisture absorption than cyanate ester resins. 25 Chao Yuan et al prepared a novel fluoropolymer, which could help reduce the moisture absorption of pure CE resin. 8 Guo et al 26 prepared a novel fluorinated allyl compound (6FDABPA) and used it to reduce water absorption of CE resins. As mentioned above, fluorine-and silicon-containing resins have demonstrated positive effect on the hygroscopicity of CE resins. However, comprehensive evaluation should be considered during the modification of CE resins, where the suppression of water absorption should not berealized at big costs of thermal and mechanical properties. 8,32,33 Herein in this paper, a series of novel silicone-containing and fluorine-containing components were prepared and introduced into CE resins, and the water absorption, thermal, mechanical, and dielectric properties were systematically characterized. The structure-property relationship was proposed and discussed.

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Section: Resultsmentioning

confidence: 96%

Thermal and water absorption properties of cyanate ester resins modified by fluoride‐containing and silicone‐containing components

Pei

Han

Guo

et al. 2020

Polymers for Advanced Techs

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“…For example, it was employed as the starting material by Pion et al (34) and Nguyen et al (54). A large number of polycyanurates from phenolic structures from renewable resources were studied in the chapter by Guenthner et al (56).…”

Section: Biobased Feedstockmentioning

confidence: 99%

Green Polymer Chemistry: Some Recent Developments and Examples

Cheng

Gross

Smith

2015

ACS Symposium Series

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“…For instance, epoxies, cyanate esters, and phthalonitriles can be synthesized via the reaction of phenolic compounds with epichlorohydrin, cyanogen halides, or 4-nitrophthalonitriles, respectively, under basic conditions. Considering there is an abundance of phenolic compounds with unique structures in nature, these synthetic approaches have been applied to obtain sustainable thermoset monomers with enhanced properties compared to those derived from petrochemicals. − …”

Section: Introductionmentioning

confidence: 99%

Heat-Resistant Polymer Networks Prepared from Processable Resveratrol-Based Propargyl Ether Monomers

Garrison

Lupton

Baca

et al. 2023

ACS Appl. Polym. Mater.

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Three propargyl ether thermosetting resins were prepared from biosynthetic trans-resveratrol (1), cis-resveratrol (2), and dihydroresveratrol (3). The cure chemistry of the monomers as well as the thermal stability and mechanical properties of cross-linked networks were then characterized by techniques including differential scanning calorimetry, thermal gravimetric analysis, and dynamic mechanical analysis. The monomers were highly processable, existing as low melting solids (1, T m = 81 °C; 3, supercooled liquid with an ultimate T m = 40 °C), or a permanent room-temperature liquid (2). All three resins exhibited broad processing windows and high degrees of cure ranging from 97–99%. The glass transition temperatures (T g) of 1 and 2 were 389 and 384 °C (loss modulus), respectively, while 3 did not exhibit a well-defined T g. All three of the networks exhibited outstanding thermal stability with char yields of 66, 64, and 54% at 1000 °C (under N2) for 1, 2, and 3, respectively. Heat release capacities of 1, 2, and 3 were 53, 41, and 114 J g–1K–1, respectively, consistent with self-extinguishing (3) or non-ignitable (1, 2) polymers. The networks also exhibited low water uptakes ranging from 3.64 to 1.59 wt %. The thermal stability, fire-resistance, and mechanical properties of the resveratrol-based resins represent significant improvements over monomers derived from conventional petroleum-based bisphenols (e.g., bisphenol A). This work demonstrates that the unique morphology afforded by bio-based monomers allows for the preparation of polymer networks with enhanced properties. The resveratrol networks have potential applications as components of high-temperature and fire-resistant composite materials for aerospace applications.

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Structure-Property Relationships for Polycyanurate Networks Derived from Renewable Resources

Cited by 3 publications

References 17 publications

Thermal and water absorption properties of cyanate ester resins modified by fluoride‐containing and silicone‐containing components

Thermal and water absorption properties of cyanate ester resins modified by fluoride‐containing and silicone‐containing components

Green Polymer Chemistry: Some Recent Developments and Examples

Heat-Resistant Polymer Networks Prepared from Processable Resveratrol-Based Propargyl Ether Monomers

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