Photopolymerization of 1‐adamantyl acrylate pohotoinitiated by free radical photoinitiators

Wang, Kemin; Cui, Rong; Gu, Junfeng; Yu, Qiang; Ma, Guiping; Nie, Jun

doi:10.1002/app.34496

Cited by 10 publications

(4 citation statements)

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“…34,35 Such complexes have shown distinct self-healing behavior. 36,37 Even though AdA has been previously polymerized through radical polymerization, 38,39 and anionic polymerizations of styrene 40 and methacrylate 31 bearing 1-adamantyl pendent groups were also studied, the anionic synthesis of PAdA and its block copolymers has not been reported, mainly because of the inherent difficulty in the anionic polymerization of acrylates as discussed above. We expected that the bulky size of adamantane and its tertiary carbon connected with the ester group might make the anionic polymerization less problematic than that of PtBA.…”

Section: ■ Introductionmentioning

confidence: 99%

Poly(1-adamantyl acrylate): Living Anionic Polymerization, Block Copolymerization, and Thermal Properties

Huang

Hong

et al. 2016

Macromolecules

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Living anionic polymerization of acrylates is challenging due to intrinsic side reactions including backbiting reactions of propagating enolate anions and aggregation of active chain ends. In this study, the controlled synthesis of poly(1-adamatyl acrylate) (PAdA) was performed successfully for the first time via living anionic polymerization through investigation of the initiation systems of sec-butyllithium/diphenylethylene/lithium chloride (sec-BuLi/DPE/LiCl), diphenylmethylpotassium/diethylzinc (DPMK/Et2Zn), and sodium naphthalenide/dipenylethylene/diethylzinc (Na-Naph/DPE/Et2Zn) in tetrahydrofuran at −78 °C using custom glass-blowing and high-vacuum techniques. PAdA synthesized via anionic polymerization using DPMK with a large excess (more than 40-fold to DPMK) of Et2Zn as the ligand exhibited predicted molecular weights from 4.3 to 71.8 kg/mol and polydispersity indices of around 1.10. In addition, the produced PAdAs exhibit a low level of isotactic content (mm triads of 2.1%). The block copolymers of AdA and methyl methacrylate (MMA) were obtained by sequential anionic polymerization, and the distinct living property of PAdA over other acrylates was demonstrated based on the observation that the resulting PAdA-b-PMMA block copolymers were formed with no residual PAdA homopolymer. The PAdA homopolymers exhibit a very high glass transition temperature (133 °C) and outstanding thermal stability (T d: 376 °C) as compared to other acrylic polymers such as poly(tert-butyl acrylate) and poly(methyl acrylate). These merits make PAdA a promising candidate for acrylic-based thermoplastic elastomers with high upper service temperature and enhanced mechanical strength.

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Section: ■ Introductionmentioning

confidence: 99%

Poly(1-adamantyl acrylate): Living Anionic Polymerization, Block Copolymerization, and Thermal Properties

Huang

Hong

et al. 2016

Macromolecules

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“…2) They are entirely composed of a carbon "cage" framework that can be superimposed on a diamond lattice, with the number of cages called the order of the diamondoid, n. The hydrogen terminations of diamondoids can be substituted by other groups, and derivatives of adamantane (n ¼ 1, C 10 H 16 ) have been used as pharmaceutical drugs for treating Parkinson's and Alzheimer's diseases, 3,4) and as additives in photoresists 5) to reduce shrinking and increase thermal stability. 6) Moreover, higher diamondoids (n > 3) are expected to be useful for optoelectronic devices 7,8) and as molecular building blocks. 9) Diamondoids with up to 11 cages have been isolated from crude oil; 10,11) however, higher diamondoids (n > 4) were only present in trace amounts.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and investigation of reaction mechanisms of diamondoids produced using plasmas generated inside microcapillaries in supercritical xenon

Oshima

Stauss

Inose

et al. 2013

Jpn. J. Appl. Phys.

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We have synthesized diamondoids using dielectric barrier discharge microplasmas generated inside a microcapillary reactor in supercritical xenon. The plasmas were generated near the critical temperature ( ) and pressure ( ) of xenon in the ranges of and under both batch-type and continuous flow conditions with gas flow rates of 0.01–0.5 mL min−1. Micro-Raman spectra of the synthesized particles showed features characteristic of diamondoids, while gas chromatography–mass spectrometry measurements revealed that diamondoids up to undecamantane were possibly synthesized. Further, the amount of obtained diamantane was greater than those obtained using previously reported diamondoid synthesis processes that involve plasmas in supercritical fluids. This increase is attributed to the higher solubility of the supercritical medium, i.e., xenon, and the higher efficiency of the microreactor. A detailed gas chromatography–mass spectrometry analysis showed that higher diamondoids grow in a stepwise manner via the alternate removal of hydrogen atoms and the addition of methyl groups.

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“…These properties make the polymers valuable as optical plastics for lenses, viewfinders, data storage media, light-diffusing elements, etc. [1] It was found that the introduction of adamantyl moieties in poly(1-adamantyl acrylate) increase thermal stability of the polymer in comparison with poly (methyl methacrylate) (PMMA) [2]. A similar result was obtained for 1,3-bis(4-phenyl)adamantane based polysiloxane P1 [3] that has thermal stability (T d5 ) higher than 520 • C in N 2 .…”

Section: Introductionmentioning

confidence: 59%

2-(Bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-adamantan-2-ol

Levchenko

Chudov

Demin³

et al. 2020

Molbank

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Photopolymerization of 1‐adamantyl acrylate pohotoinitiated by free radical photoinitiators

Cited by 10 publications

References 50 publications

Poly(1-adamantyl acrylate): Living Anionic Polymerization, Block Copolymerization, and Thermal Properties

Poly(1-adamantyl acrylate): Living Anionic Polymerization, Block Copolymerization, and Thermal Properties

Synthesis and investigation of reaction mechanisms of diamondoids produced using plasmas generated inside microcapillaries in supercritical xenon

2-(Bicyclo[4.2.0]octa-1,3,5-trien-3-yl)-adamantan-2-ol

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