Piers-Rubinsztajn reaction for BCB functionalized silphenylene/silbiphenylene siloxane oligomers to highly crosslinked low-k thermosets

Tian, Shichang; Li, Junyi; Cai, Zhe; Shi, Bingyao; Chen, Wenhao; Cheng, Yuanrong

doi:10.1016/j.eurpolymj.2018.09.015

Cited by 17 publications

(20 citation statements)

References 32 publications

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“…Nevertheless, this is a new idea for the preparation of a new bridge-link structure of polysiloxanes. Following our work, Tian et al [26] also prepared similar highly crosslinked polysiloxanes: linear polysiloxanes with benzocyclobutene groups were first synthesized by a PR reaction and then crosslinked by a cycloaddition reaction. However, our one-step PR reaction is more efficient and convenient.…”

Section: Morphology-controlled Synthesis Of Polysiloxanes Via the mentioning

confidence: 94%

“…The introduction of silphenylene units into the polysiloxane backbone can significantly improve their thermal stability, radiation resistance, and mechanical property [23,24,25]. By the PR reaction, a benzocyclobutene (BCB)-functionalized silphenylene-siloxane oligomer (PhBVSi) can be produced by polycondensation between 1,4-bis(dimethylsilyl)benzene and (1,2-dihydrobenzocyclobuten-4-yl)dimethoxy(vinyl)silane (DMVBS), and a BCB-functionalized silbiphenylene-siloxane oligomer (BPBVSi) can be produced by polycondensation between 4,4′-bis(dimethylsilyl)bibenzene and DMVBS, as shown in Figure 4 [26]. The molecular weights of these two polysiloxanes are not particularly large and their polydispersities are not broad (PhBVSi:Mw = 4829 g·mol −1 , Polydisperity (PDI) = 1.60; BPBVSi:Mw = 10,571 g·mol −1 , PDI = 1.57).…”

Section: Morphology-controlled Synthesis Of Polysiloxanes Via the mentioning

confidence: 99%

“…Synthesis of benzocyclobutene (BCB) oligomers by the PR reaction [26]. Reproduced with the copyright permission.…”

Section: Figurementioning

confidence: 99%

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Synthesis of Structurally Precise Polysiloxanes via the Piers–Rubinsztajn Reaction

Chen

et al. 2019

Materials

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Silicone materials are widely used, from daily life to the military industry. With the advancement of science and technology and the increasing demands of industry, the requirement for high-performance precise structural silicone materials has increased. Therefore, the most important aspect in this field is finding a breakthrough in the synthetic methods. In this review, the latest research developments in controllable morphological structure and composite structure optimized synthesis of silicone materials using the Piers–Rubinsztajn (PR) reaction are summarized. The advantages of the PR reaction compared with traditional synthetic routes to silicone materials are presented. The highly controllable spatial structure of silicone materials and the structural combination of biomass or inorganic materials with silicone materials results in an improvement in performance or function. The morphological control of more complex silicone materials and the synthesis of non-traditional silicone materials with composite structures through the PR reaction will be the main research directions for the development of silicone materials in the future.

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Section: Morphology-controlled Synthesis Of Polysiloxanes Via the mentioning

confidence: 94%

Section: Morphology-controlled Synthesis Of Polysiloxanes Via the mentioning

confidence: 99%

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Synthesis of Structurally Precise Polysiloxanes via the Piers–Rubinsztajn Reaction

Chen

et al. 2019

Materials

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“…The generation of Si-OH groups is also prevented in the P-R reaction; thus, the product formed has a low water absorption rate [ 6 ]. Recently, we have prepared a linear oligomer BCB functionalized polysiloxane by P-R reaction of BCB functionalized dimethoxysilane monomer (A2) with silphenylene/silbiphenylene hydrosilanes (B2) [ 26 ]. After cured, a linear oligomer showed low dielectric constants at 2.76 and 2.78 at 1 MHz.…”

Section: Introductionmentioning

confidence: 99%

Benzocyclobutene-functionalized hyperbranched polysiloxane for low-k materials with good thermostability

Shi

Cai

et al. 2021

Designed Monomers and Polymers

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Although hyperbranched polysiloxanes have been extensively studied, they have limited practical applications because of their low glass transition temperatures. In this study, we synthesized benzocyclobutene-functionalized hyperbranched polysiloxane (HB-BCB) via the Piers-Rubinsztajn reaction. The synthesized material was cured and crosslinking occurred at temperatures greater than 200 °C, forming a low-k thermoset resin with high thermostability. The structure of the resin was characterized using nuclear magnetic resonance (NMR) spectroscopy, viz. 1 H NMR and 13 C NMR spectroscopy. 29 Si NMR spectroscopy was used to calculate the degree of branching. Differential scanning calorimetry, dynamic mechanical analysis, and thermogravimetric analysis revealed that the cured resin possesses good high-temperature mechanical properties and exhibits a high thermal decomposition temperature (T d5 = 512 °C). In addition, the cured resin has a low dielectric constant (k = 2.70 at 1 MHz) and low dissipation factor (2.13 × 10 −3 at 1 MHz). Thus, the prepared resin can function as a low-k material with excellent high-temperature performance. These findings indicate that the performance of crosslinked siloxane is significantly attributed to the introduction of BCB groups and the formation of the highly crosslinked structure.

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“…Polysiloxanes, which are intrinsic and semi-inorganic polymers [18], are comprised of stable hydrophobic Si-O backbones [19], and they possess many outstanding attributes, including a low surface energy, high thermal stability, high gas permeability, low dielectric properties, good insulation properties, and an excellent biocompatibility [20]. As such, polysiloxane-based materials have been recognized as potential long-lasting and wide-ranging coating materials.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Silphenylene-Containing Siloxane Resins Exhibiting Strong Hydrophobicity and High Water Vapor Barriers

Chen

et al. 2019

Coatings

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The novel phenylenedisilane, 1,4-bis(dimethoxyphenylsilyl)benzene (BDMPD), was successfully synthesized via the reaction between trimethoxyphenylsilane (TMPS) and a Grignard reagent originating from 1,4-dibromobenzene. In comparison to common Grignard reactions, this process was a facile one-pot method. 1H NMR spectroscopy, FT-IR measurements, and elemental analysis confirmed the predicted structure of BDMPD. In addition, vinyl-terminated polysiloxanes containing silphenylene units (VPSSP), which were hydrolytically copolymerized from BDMPD, TMPS, and divinyltetramethyldisiloxane, exhibited excellent thermal stabilities (T10%: 502 °C, Rw%: 76.86 beyond 700 °C) and suitable refractive indices (1.542). Furthermore, water contact angle and water vapor permeability tests confirmed that the fully cured siloxane resins containing VPSSP-based silphenylene units exhibited strong hydrophobicity (water contact angle: 119°) and superior water vapor barrier properties, thereby indicating their potential to serve as strong waterproof coatings for moisture-proof applications or as adhesives for use in immersed equipment.

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Piers-Rubinsztajn reaction for BCB functionalized silphenylene/silbiphenylene siloxane oligomers to highly crosslinked low-k thermosets

Cited by 17 publications

References 32 publications

Synthesis of Structurally Precise Polysiloxanes via the Piers–Rubinsztajn Reaction

Synthesis of Structurally Precise Polysiloxanes via the Piers–Rubinsztajn Reaction

Benzocyclobutene-functionalized hyperbranched polysiloxane for low-k materials with good thermostability

Synthesis of Silphenylene-Containing Siloxane Resins Exhibiting Strong Hydrophobicity and High Water Vapor Barriers

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