Reductants for polyperoxides to accelerate degradation at elevated temperatures

Sato, Eriko; Yuri, Michihiro; Matsumoto, Akikazu; Horibe, Hideo

doi:10.1016/j.polymdegradstab.2019.01.030

Cited by 8 publications

(9 citation statements)

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“…Not only the reductive decomposition of the polyperoxides but also the thermal decomposition of the polyperoxides occurred, and the relative M n in the presence of B(PhP,Ix) to that in the absence of additives was used to evaluate the solo effect of the reductive decomposition on the decrease in M n . 12 When the value of M n (red. )/M n (none) equals unity, a decrease in M n by the reductive decomposition is negligible, and the contribution of the reductive decomposition increases with the decreasing M n (red.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

“…We recently found that 1-phenyl-3-pyrazolidone (PhP), which has an active hydrogen, shows an interesting redox reaction behavior for the conjugated diene-based polyperoxides. 12 That is, the reducing ability of PhP toward the polyperoxides strongly depends on the regiospecificity of the diene monomers during the polymerization (Scheme 1(a) and (b)). The polyperoxides are degradable polymers having a peroxy bond as a repeating unit of the polymer main-chain, and undergo decomposition by heating, UV irradiation, and a redox reaction.…”

mentioning

confidence: 99%

“…20,21 In our recent report, it was found that the redox reaction of PhP with the sorbic ester-based polyperoxides proceeds even at room temperature and the molecular weight of the polyperoxide decreased (Scheme 1(a)). 12 In the case of the conjugated hydrocarbon diene-based polyperoxides, a decrease in the molecular weight by the redox reaction with PhP is negligible at 30 °C, but significantly occurs at 100 °C together with the thermal decomposition of the polyperoxides (Scheme 1(b)).…”

mentioning

confidence: 99%

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Thermal Latent Reductants for Controlled Degradation of Polyperoxides and Their Application to High Performance Dismantlable Adhesives

Sato

Omori

Yuri

et al. 2019

ACS Appl. Polym. Mater.

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1-Phenyl-3-pyrazolidone (PhP) having an active hydrogen was blocked by phenyl isocyanate derivatives to reduce its nucleophilicity, and the potential of the blocked PhP as a thermal latent reductant generating the organic reducing agent, PhP, was revealed for the first time. The degree of dissociation of the blocked PhP during heating in solution can be controlled by the steric hindrance of the isocyanate-blocking agents. The thermal latency of the blocked PhP for the sorbic ester-based polyperoxides, which undergo a serious reductive decomposition by PhP even at 30 °C, was investigated in order to accelerate the decomposition of the polyperoxides only at elevated temperatures. It was revealed that the stability of the polyperoxides was not significantly affected at 30 °C and marked reductive decomposition of the polyperoxides together with thermal decomposition took place at elevated temperatures. For the block PhPs, which are highly compatible with the polyperoxides, the decomposition promotion effect increased with increasing the steric hindrance of the blocking agents, and the controlled decomposition of the polyperoxides was successfully achieved. Moreover, the addition of the blocked PhP resulted in the complete solubilization of sorbic ester-based cross-linked polyperoxides by heating, which was not able to be achieved without the blocked PhP. The performance of the debondable adhesive using the sorbic ester-based cross-linked polyperoxides was improved by the addition of the blocked PhP, although hazardous isocyanate formation during the activation process may limit the practical application. Specifically, a faster decrease in the lap-shear adhesion strength by heating was accomplished. Furthermore, the same level of dismantlability was achieved in the wade range of heating temperatures and time, which is an 3 important requirement for polyperoxides undergoing significant exothermic decomposition bringing about undesired temperature rise.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Thermal Latent Reductants for Controlled Degradation of Polyperoxides and Their Application to High Performance Dismantlable Adhesives

Sato

Omori

Yuri

et al. 2019

ACS Appl. Polym. Mater.

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“…Polyperoxides degrade highly exothermically in contrast to common polymers which usually degrade endothermically . Even though polyperoxides are very much sensitive towards heat, enzyme, light, acid, and base, they find significant academic and industrial usefulness as thermal and photo initiators for radical copolymerization, auto‐combustible fuels, curators in coating and molding compositions, dismantlable adhesion, drug delivery, etc. Recently, Sato and coworkers explored the thermal latent properties of 1‐phenyl‐3‐pyrazolidones (PhPs) with an active hydrogen towards their addition effect for sorbic ester‐based polyperoxides.…”

Section: Introductionmentioning

confidence: 99%

Composition‐dependent crystallization behavior of copolyperoxides from methyl methacrylate and 4‐vinylbenzyl stearate

Mete

Goswami

2020

Journal of Polymer Science

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To study the composition‐dependent crystallization behavior of copolyperoxides, herein a series of copolymers were prepared by varying the ratios of methyl methacrylate (MMA) and 4‐vinylbenzyl stearate (VBS) under 100 psi oxygen pressure using AIBN as an initiator at 50°C in toluene. Both 13C NMR and electron impact mass spectroscopy (EI‐MS) approved an alternative placement of either of the monomer and peroxy (–O–O–) links throughout the polymer chain. Thermal stability of the resulting copolyperoxides was investigated by thermogravimetric analysis (TGA) and the degradation fragments have been recognized from EI‐MS study. In addition, differential scanning calorimetry (DSC) displayed an endothermic peak as well as an exotherm associated with the melting of the side chain crystalline domains and degradation of –O–O– links in the polymer main chain, respectively. Furthermore, DSC thermograms unveiled a systematic decrease of the crystalline melting temperature (Tm) with the enhancement of MMA content in the copolymers. Small angle X‐ray scattering (SAXS) revealed the existence of lamellar morphology (depends on VBS content in the copolyperoxide) in the synthesized polyperoxide materials, further supported by atomic force microscopy (AFM) analysis showing a layered fibrillar assembly with multiple heights of the lamella. The significant crystalline nature of the polyperoxides was further evidenced from the appearance of lattice fringes in the transmission electron microscope (TEM) micrographs. The crystalline morphology with birefringent texture was further evidenced from the polarized optical microscopy (POM) study. Thus, the present study reported the effective variation of crystalline behavior in copolyperoxide materials with the incorporation of MMA units in the copolyperoxide chains.

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Controlled deprotection of poly(2-(tert-butoxycarbonyloxy)ethyl methacrylate) using p-toluenesulfonic esters as thermally latent acid catalysts

Osada

Akahori²,

Suzuki

et al. 2022

Polymer Degradation and Stability

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Reductants for polyperoxides to accelerate degradation at elevated temperatures

Cited by 8 publications

References 46 publications

Thermal Latent Reductants for Controlled Degradation of Polyperoxides and Their Application to High Performance Dismantlable Adhesives

Thermal Latent Reductants for Controlled Degradation of Polyperoxides and Their Application to High Performance Dismantlable Adhesives

Composition‐dependent crystallization behavior of copolyperoxides from methyl methacrylate and 4‐vinylbenzyl stearate

Controlled deprotection of poly(2-(tert-butoxycarbonyloxy)ethyl methacrylate) using p-toluenesulfonic esters as thermally latent acid catalysts

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