Soluble and processable thermoplastic hybrid polyimides containing POSS in main chains

Kamitani, Tasuku; Imoto, Hiroaki; Naka, Kensuke

doi:10.1039/d2py00980c

Cited by 16 publications

(12 citation statements)

References 43 publications

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“…The DSC analysis of 3 exhibited T g ranging from 102 to 170 °C (Table and Figure S11). The flexible aminopropyl substituents on the DDSQ monomer may have contributed to the low T g values of 3 , similar to the polyimides from 1 . The lowest T g among the polymers was 102 °C observed in 3f , possibly due to the increase of the flexible aliphatic linkages.…”

Section: Resultsmentioning

confidence: 86%

“…The polymerization of 1 with several tetracarboxylic dianhydrides resulted in soluble thermoplastic polyimides with low glass-transition temperatures ( T g s) of approx. 135 °C, which were lower than those of the previously reported thermoplastic polyimides . Although freestanding films of the DDSQ containing polyimides were obtained, these films were too brittle to be suitable for practical applications.…”

Section: Introductionmentioning

confidence: 66%

“…The flexible aminopropyl substituents on the DDSQ monomer may have contributed to the low T g values of 3, similar to the polyimides from 1. 35 The lowest T g among the polymers was 102 °C observed in 3f, possibly due to the increase of the flexible aliphatic linkages. The highest T g of 170 °C was observed in 3e.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

“…135 °C, which were lower than those of the previously reported thermoplastic polyimides. 35 Although freestanding films of the DDSQ containing polyimides were obtained, these films were too brittle to be suitable for practical applications. A short linker length may inhibit the entanglement of the polymer chains, resulting in brittle films.…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis of Low-Dielectric Polyureas by Incorporating Phenyl-Substituted Cage Silsesquioxanes in the Main Chain

Kamitani

Nakamura

Watase

et al. 2023

ACS Appl. Polym. Mater.

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Establishing a design concept for low-dielectric constant (ε r ) and low dissipation factor (tan δ) polymeric materials is vital to improve signal transmission rates. Polyurea-based polymers with strong dipole moments have been reported to achieve higher ε r (above 5.0) than most of the traditional polymer dielectrics. However, polyurea-based polymers with low ε r and tan δ values have not been reported yet. In this study, bis(3-aminopropyl)-doubledecker-shaped phenyl-substituted silsesquioxane (DDSQ) (1) was polymerized with various diisocyanates, i.e., methylenediphenyl 4,4′-diisocyanate (2a), 4,4′diisocyanato-3,3′-dimethylbiphenyl diisocyanate (2b), m-xylene diisocyanate (2c), 1,3-bis(isocyanatomethyl)cyclohexane (2d), 4,4′-methylenebis-(cyclohexyl isocyanate) (2e), and hexamethylene diisocyanate (2f), to obtain the corresponding polyureas (3a−f). Optically transparent, colorless, and flexible freestanding films were obtained by casting the polyurea solutions in tetrahydrofuran. Among the tested polymers, polyureas from 2a and 2e exhibited ε r less than 3.0. Incorporation of the DDSQ units produced free volume, resulting in low ε r . Polyureas from 2e and 2f exhibited the lowest tan δ of approx. 7 × 10 −3 . The polyurea from 2e had the lowest urea content and thus had the lowest density and lowest ε r . Additionally, strong hydrogen bonding in the polyurea from 2e inhibited local motion, resulting in a low tan δ even though the urea content was low. Water vapor permeability measurements revealed greater free volume content introduced by the co-oligomerization of polyhedral oligomeric silsesquioxanes (POSS), especially in the polyurea from 2e. Among the reported combinations, the combination of DDSQ and urea groups provides unique low ε r and low tan δ polymeric materials.

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Section: Resultsmentioning

confidence: 86%

Section: Introductionmentioning

confidence: 66%

Section: ■ Results and Discussionmentioning

confidence: 93%

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of Low-Dielectric Polyureas by Incorporating Phenyl-Substituted Cage Silsesquioxanes in the Main Chain

Kamitani

Nakamura

Watase

et al. 2023

ACS Appl. Polym. Mater.

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“…18 Similar to T 8 SQs, DDSQ and its derivatives have good temperature resistance, extreme mechanical properties, excellent dielectric properties and certain flexibility, providing more opportunities for the development of new silsesquioxane-based materials, which attracted an extensive attention. [19][20][21] For example, it is easy to modify the polymer backbone through chemical reaction, 22,23 Kuo et al synthesized two different types of organic-inorganic hybrid porous polymers based on bromine functionalized double-decker SQ, which display good properties for high-performance energy storage. 24 However, there are still some intricate problems in the above-mentioned method, such as complex synthesis steps, expensive catalysts and broken cages.…”

Section: Introductionmentioning

confidence: 99%

Hybrid porous polymers based on double‐decker and cage‐ype silsesquioxanes for the high‐efficiency removal of neonicotinoid insecticides and dyes

Zhao

Liu

2023

Journal of Polymer Science

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Different ratios of octavinylsilsesquioxane (OVS) reacted with phenyl‐substituted double‐decker silsesquioxane (Ph‐DDSQ) via the simple Friedel‐Crafts reaction provides several innovative silsesquioxane‐based porous polymers (PCS‐ODs). The hybrid polymers show adjustable porosity (specific surface areas of 1235 m2 g−1 and large pore volumes >1.07 cm3 g−1). FTIR, SEM, BET, TGA, solid‐state 13C and 29Si MAS NMR spectra were employed to fully characterize these hybrid materials. They display good adsorption capacities for neonicotinoid insecticides (imidacloprid [IMI], acetamidine [ACE] and thiamethoxam [THI]), with capacities up to 117 ± 2, 70 ± 1 and 61 ± 4 mg g−1, respectively. Dyes (Congo red [CR] and rhodamine B [RB]) can also be sufficiently removed, the adsorption capacities are 1822 ± 4 and 912 ± 3 mg g−1. In addition, PCS‐ODs can be cycled at least five times.

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Thermoplastic polyimide with low dielectric properties enabled by the 2,2′‐spirobifluorene group

Jian,

Lu,

Zhang

et al. 2024

J of Applied Polymer Sci

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Thermoplastic polyimides (TPIs) have melt‐processability and adhesive ability, besides the intrinsic advantages of polyimides. To meet the requirements of applications in high‐frequency communication, TPIs with low dielectric constant (Dk)/dielectric loss factor (Df) at high frequency are also desirable. Enhancing the rigidity of polymer chains and simultaneously intermolecular interaction are effective ways to ensure low Dk/Df, which also benefit to heat resistance. However, it is not conducive to thermoplasticity, due to limited movement of polymer chains. To balance the trade‐off between them, we introduce noncoplanar 2,2′‐spirobifluorene groups to modify the rigidity of polymer chains and regulate the twist between electron‐donor moieties (diamine units) and electron‐acceptor moieties (dianhydride units). It leads to rigid polymer chains, which benefits to good heat resistance and dielectric properties. Meanwhile, the resultant irregular chain structure is difficult to crystallize, which results in thermoplasticity.

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Soluble and processable thermoplastic hybrid polyimides containing POSS in main chains

Cited by 16 publications

References 43 publications

Synthesis of Low-Dielectric Polyureas by Incorporating Phenyl-Substituted Cage Silsesquioxanes in the Main Chain

Synthesis of Low-Dielectric Polyureas by Incorporating Phenyl-Substituted Cage Silsesquioxanes in the Main Chain

Hybrid porous polymers based on double‐decker and cage‐ype silsesquioxanes for the high‐efficiency removal of neonicotinoid insecticides and dyes

Thermoplastic polyimide with low dielectric properties enabled by the 2,2′‐spirobifluorene group

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