UV-thermal dual cured anti-bacterial thiol-ene networks with superior performance from renewable resources

Dai, Jinyue; Ma, Songqi; Zhu, Lixia; Wang, Sheng; Yang, Lijing; Song, Zhenlun; Liu, Xiaoqing; Zhu, Jin

doi:10.1016/j.polymer.2016.11.068

Cited by 53 publications

(35 citation statements)

References 46 publications

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“…Additional considerations for these materials are extensive, as their 3D printing opens up avenues into 3D printable antimicrobial agents, recyclable printing resins, optically transparent printed parts, and even biomaterials with tunable thermomechanical and surface properties. [41][42][43]…”

Section: D Printingmentioning

confidence: 99%

Terpene- and terpenoid-based polymeric resins for stereolithography 3D printing

et al. 2019

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Section: D Printingmentioning

confidence: 99%

Terpene- and terpenoid-based polymeric resins for stereolithography 3D printing

et al. 2019

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“…Moreover, eugenol exhibits several pharmacological properties, such as antibacterial and antioxidant properties, because of the presence of phenol groups, leading to its utilization in perfume, cosmetic and flavoring applications . So far numerous studies have used eugenol as a building block for the synthesis of bio‐based polymers, such as benzoxazine resins, allyl‐etherified eugenol, polyester resins, cyanate ester resins, bismaleimide, epoxy resins, methacrylated eugenol (ME), etc . Among them, ME, prepared by incorporation of a polymerizable methacrylate group to eugenol, shows promising potential for use as a co‐monomer replacement for styrene in VE resins because both methacrylate groups and allyl groups can participate in free radical polymerization.…”

Section: Introductionmentioning

confidence: 99%

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

Zhang

Thakur

et al. 2018

Polymer International

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A renewable chemical, eugenol, is methacrylated to produce methacrylated eugenol (ME) employing the Steglich esterification reaction without any solvent. The resulting ME is used as a low‐viscosity co‐monomer to replace styrene in a commercial epoxy‐based vinyl ester resin (VE). The volatility and viscosity of ME and styrene are compared. The effect of ME loading and temperature on the viscosity of the VE–ME resin is investigated. Moreover, the thermomechanical properties, curing extent and thermal stability of the fully cured VE–ME thermosets are systematically examined. The results indicate that ME is a monomer with low volatility and low viscosity, and therefore the incorporation of ME monomer in VE resins allows significant reduction of viscosity. Moreover, the viscosity of the VE–ME resin can be tailored by adjusting the ME loadings and processing temperature to meet commercial liquid molding technology requirements. The glass transition temperatures of VE–ME thermosets range from 139 to 199 °C. In addition, more than 95% of the monomer is incorporated and fixed in the crosslinked network structure of VE–ME thermosets. Overall, the developed ME monomer exhibits promising potential for replacing styrene as an effective low‐viscosity co‐monomer. The VE–ME resins show great advantages for use in polymer matrices for high‐performance fiber‐reinforced composites. This work is of great significance to the vinyl ester industry by providing detailed experimental support. © 2018 Society of Chemical Industry

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“…In the 1 H‐NMR spectra of DAI, the characteristic peaks of protons 1, 2, 3, 12, 13, and 14 on the double bonds CH 2 ═CH─CH 2 ─ backbone are observed at 5.10 to 5.24 and 5.75 to 5.84 ppm; the peaks of other protons 8 and 9 on the double bond CH 2 ═C─ at 5.64 to 6.25 ppm; other peak of protons 4, 5, 10, and 11 on the C‐atom next to the terminal double bond CH 2 ═CH─ at 4.45 to 4.55 ppm; and the peaks of protons 6 and 7 on the C‐atom between the pendant CH 2 ═C─ and CH 2 ─COO─ at 3.27 ppm …”

Section: Resultsmentioning

confidence: 99%

“…Cross proposed a model capable to predict smoother and longer transition behavior from 0 shear rate to the power law. Cross proposed a model that is represented Equation

\frac{η - η_{\infty}}{η_{0} - η_{\infty}} = \frac{1}{[1 + {((), λγ)}^{normalm}]}

…”

Section: Resultsmentioning

confidence: 99%

“…Fourier transform infrared (FT-IR) spectra of A, itaconic acid (IA), B, diallyl itaconate (DAI), and C, trifunctional epoxy resin (TEIA) [Colour figure can be viewed at wileyonlinelibrary.com]In the 1 H-NMR spectra of DAI, the characteristic peaks of protons 1, 2, 3, 12, 13, and 14 on the double bonds CH 2 CH─CH 2 ─ backbone are observed at 5.10 to 5.24 and 5.75 to 5.84 ppm; the peaks of other protons 8 and 9 on the double bond CH 2 C─ at 5.64 to 6.25 ppm; other peak of protons 4, 5, 10, and 11 on the C-atom next to the terminal double bond CH 2 CH─ at 4.45 to 4.55 ppm; and the peaks of protons 6 and 7 on the C-atom between the pendant CH 2 C─ and CH 2 ─COO─ at 3.27 ppm 44,45. After epoxidation of DAI, all proton peaks of TEIA spectra disappeared except the characteristic peak of protons 1 to 3, 8, 9, and 12 to 14 on the glycidyl epoxides CH 2 ─(O)─CH and pendant epoxide (CH 2 (O)─C─); protons 6 and 7 on the C-atom between the pendent epoxide and ester bond (CH 2 ─(O)─C─CH 2 ─COO─) at 2.64 to 3.25 ppm; and peak of the protons 4, 5, 10, and 11 observed at 3.92 to 4.04 and 4.42 to 4.52 ppm, which confirmed the chemical structure of TEIA 35,37.…”

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Synthesis and characterization of itaconic‐based epoxy resins

Kumar

Samal

Mohanty

et al. 2017

Polymers for Advanced Techs

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A trifunctional epoxy resin from itaconic acid (TEIA) was synthesized from a renewable resource-based itaconic acid by allylation of itaconic acid to form diallyl itaconate by using m-chloroperoxybenzoic acid as oxidizing agents followed by epoxidation of allylic C═C bond of diallyl itaconate methylhexahydropthalic anhydride as curing agent in the presence of 2-methyl imidazole as a catalyst. The chemical structure of the synthesized resins was confirmed by Fourier transform infrared and nuclear magnetic resonance ( 1 H-NMR and Pan et al [26] synthesized a highly functional bio-based epoxy resin from sucrose fatty acids. The higher epoxy value means that the highest number of epoxy rings, the more cross-linking occurs.Therefore, the result shows that higher mechanical properties and glass transition temperature contrast to commercialized bio-based epoxidized soybean oil (ESO). The overall properties of ESO were not similar to the conventional DGEBA, while they both are cured with methylhexahydrophthalic anhydride (MHHPA) curing agent because of the presence of long triglyceride aliphatic chain structure.Xin et al 27 synthesized cinnamic acid (Cin-epoxy)-based liquid epoxy resin with lower viscosity (0.67 Pa s) at room temperature than epoxy resin (DER 332; 3.31 Pa s), which indicates that Cin-epoxy systems have better processability and similar (T g 85°C) value of the biobased dimethylpropionic acid cured Cin-epoxy/dimethylpropionic acid networks and petroleum-based Cin-epoxy/HHPA network (T g 90°C).Samantha et al studied that the bio-based quercetin epoxy monomer that displayed comparable T g and thermal and mechanical properties than DGEBA was cured with nadic methyl anhydride curing agent.Wan et al 28 described that a eugenol-based epoxy resin (DEU-EP) with higher bio-based content of 70.2 wt% showed a higher storage,

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UV-thermal dual cured anti-bacterial thiol-ene networks with superior performance from renewable resources

Cited by 53 publications

References 46 publications

Terpene- and terpenoid-based polymeric resins for stereolithography 3D printing

Terpene- and terpenoid-based polymeric resins for stereolithography 3D printing

High‐performance thermosets with tailored properties derived from methacrylated eugenol and epoxy‐based vinyl ester

Synthesis and characterization of itaconic‐based epoxy resins

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