Efficient synthesis and properties of soluble aliphatic oligo(spiroorthocarbonate)s from pentaerythritol derivatives

Mori, Yasuyuki; Sudo, Atsushi; Endō, Takeshi

doi:10.1002/pola.29327

Cited by 3 publications

(1 citation statement)

References 9 publications

(22 reference statements)

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“…The synthesis of oligo(spiroorthocarbonate)s by polycondensation of pentaerythritol derivatives and tetraethyl orthocarbonate was reported by Endo and coworkers ( Figure 15 A) [ 85 ]. Oligomers with a M n in the range of 1.1 to 1.3 kDa and dispersity indices in the range of Đ = 1.66 to 1.96 were obtained.…”

Section: Expanding Oxacyclesmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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Commonly, volumetric shrinkage occurs during polymerizations due to the shortening of the equilibrium Van der Waals distance of two molecules to the length of a (significantly shorter) covalent bond. This volumetric shrinkage can have severe influence on the materials’ properties. One strategy to overcome this volumetric shrinkage is the use of expanding monomers that show volumetric expansion during polymerization reactions. Such monomers exhibit cyclic or even oligocyclic structural motifs with a correspondingly dense atomic packing. During the ring-opening reaction of such monomers, linear structures with atomic packing of lower density are formed, which results in volumetric expansion or at least reduced volumetric shrinkage. This review provides a concise overview of expanding monomers with a focus on the elucidation of structure-property relationships. Preceded by a brief introduction of measuring techniques for the quantification of volumetric changes, the most prominent classes of expanding monomers will be presented and discussed, namely cycloalkanes and cycloalkenes, oxacycles, benzoxazines, as well as thiocyclic compounds. Spiroorthoesters, spiroorthocarbonates, cyclic carbonates, and benzoxazines are particularly highlighted.

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Section: Expanding Oxacyclesmentioning

confidence: 99%

Expanding Monomers as Anti-Shrinkage Additives

Marx

Wiesbrock

2021

Polymers

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Effect of oligo(spiroorthocarbonate)s on the volume shrinkage of epoxides during crosslinking by sulfonium salt‐initiated cationic polymerization of epoxides

Mori¹,

Sudo

Endo³

2019

J. Polym. Sci. Part A: Polym. Chem.

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Oligo(spiroorthocarbonate)s 1, which were synthesized by the polycondensation of pentaerythritol derivatives with tetraethylorthocarbonate, were employed as comonomers in the cationic polymerization of epoxide initiated by sulfonium salt. In the copolymerization, the spiroorthocarbonate moiety of 1 underwent double ring-opening reaction, leading to the efficient diminution of the volume shrinkage upon the copolymerization.Thermal properties of the resulting networked polymers were evaluated by TGA.

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Synthesis of oligo(spiroketal)s by polycondensation of silyl ethers derived from naturally occurring myo‐inositol with 1,4‐cyclohexanedione

Sudo

Yamasaki

Yamashita

et al. 2019

J. Polym. Sci. Part A: Polym. Chem.

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Oligo(spiroketal)s (OSKs) were synthesized from myo‐inositol, a naturally occurring cyclic compound bearing six hydroxyl groups. The successful synthesis of OSKs was achieved using silyl ethers 2 derived from 1,4‐di‐O‐alkylated myo‐inositol 1 as monomers, which underwent polycondensation with 1,4‐cyclohexanedione (CHD) at 0 °C in the presence of trimethylsilyl triflate as a catalyst. Because of the irreversible nature of the condensation reaction of silyl ethers with ketones, the resulting OSKs 7 had higher molecular weights than previously reported OSKs that were obtained by polycondensation of tetraols 1 with CHD, where backward hydrolysis of the ketal functions occurred. In addition, another series of OSKs, 8, were synthesized using silyl ethers 3 derived from 2,5‐di‐O‐alkylated myo‐inositol 6, which are more symmetric monomers than silyl ethers 2. Silyl ethers 3 underwent efficient polycondensation with CHD, whereas tetraol 6 did not, demonstrating that the derivation of such tetraols into the corresponding silyl ethers is a powerful strategy to access OSKs. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2407–2414

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Efficient synthesis and properties of soluble aliphatic oligo(spiroorthocarbonate)s from pentaerythritol derivatives

Cited by 3 publications

References 9 publications

Expanding Monomers as Anti-Shrinkage Additives

Expanding Monomers as Anti-Shrinkage Additives

Effect of oligo(spiroorthocarbonate)s on the volume shrinkage of epoxides during crosslinking by sulfonium salt‐initiated cationic polymerization of epoxides

Synthesis of oligo(spiroketal)s by polycondensation of silyl ethers derived from naturally occurring myo‐inositol with 1,4‐cyclohexanedione

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