Dismantlable Thermosetting Adhesives Composed of a Cross-Linkable Poly(olefin sulfone) with a Photobase Generator

Sasaki, Takeo; Hashimoto, Shouta; Nogami, Nana; Sugiyama, Yuichi; Mori, Mitsuo; Naka, Yumiko; Le, Khoa V.

doi:10.1021/acsami.5b10110

Cited by 35 publications

(30 citation statements)

References 17 publications

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“…The results showed that depolymerizable polymers can act as detachable adhesives. The adhesive strength of a poly(olefin sulfone) composed of a volatile olefin monomer and a second olefin monomer possessing a crosslinkable moiety has been evaluated [28]. This polymer was expected to act as a detachable adhesive, as illustrated in Figure 20.…”

Section: Application Of Photo-depolymerizable Poly (Olefin Sulfone)s mentioning

confidence: 99%

Poly(olefin sulfone)s

Sasaki¹,

Le²,

Naka³

2018

Alkenes

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In this chapter, we introduce poly(olefin sulfone)s and review the recent progress on the photoinduced depolymerization of poly(olefin sulfone)s as well as their applications. Poly(olefin sulfone)s combined with photobase generators (PBGs) are depolymerized upon irradiation with light. A poly(olefin sulfone) is a 1:1 alternating copolymer of olefin monomer and sulfur dioxide in which the protons on the carbons adjacent to the sulfonyl groups can be readily abstracted by a base. This removal leads to a depolymerization chain reaction, resulting in incorporation of a photobase generating chromophore that can undergo a photoinduced unzipping reaction. During this reaction, the original olefin monomer and sulfur dioxide are regenerated from the primary chain of the poly(olefin sulfone). The photoinduced depolymerization of poly(olefin sulfone)s has been investigated for a wide variety of applications, including stereolithography, printable microcircuit fabrication, and removable adhesives.

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Section: Application Of Photo-depolymerizable Poly (Olefin Sulfone)s mentioning

confidence: 99%

Poly(olefin sulfone)s

Sasaki¹,

Le²,

Naka³

2018

Alkenes

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“…(10–12) Examples for these types of self-immolating polymers include low-ceiling temperature polyaldehydes, polyglyoxylates, metallo-supramolecular polymers, and poly(olefin sulfone)s (POSs). (13–17) POSs exhibit low ceiling temperatures and have been shown to undergo triggered depolymerization when exposed to heat,(18) base,(19,20) or ionizing radiation. (21,22) POSs possess main chain sulfonyl (SO 2 ) groups and can be easily synthesized by low temperature free radical polymerization of olefin monomers in liquefied sulfur dioxide.…”

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“…As a result of their characteristics, POSs have been targeted for the development of photoresists and other degradable materials. (19) The generation of radicals, abstraction of acidic protons, or the removal of an electron from the polymer backbone can lead to polymer chain scission, and therefore one triggering event can cause the whole polymer to decompose.…”

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Resistive and Capacitive γ-Ray Dosimeters Based On Triggered Depolymerization in Carbon Nanotube Composites

Zeininger

Hobson

et al. 2018

ACS Sens.

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We report γ-ray dosimeters using carbon nanotubes wrapped with metastable poly(olefin sulfone)s (POSs) that readily depolymerize when exposed to ionizing radiation. New POSs, designed for wrapping single-walled carbon nanotubes (SWCNTs), are synthesized and characterized. The resulting POS-SWCNT composites serve as the active transducer in a novel class of γ-ray dosimeters. In our devices, polymer degradation results in immediate changes in the electronic potential of the POS-SWCNT active layers by decreasing the electron tunneling barriers between individualized tubes and by creating enhanced cofacial π-π electron contacts. By incorporating the SWCNT-POS composites into small resistive device platforms, we establish a rare example of real-time detection and dosimetry of radioactive ionizing radiation using organic-based materials. We show that the sensitivity of our platform closely depends on the intrinsic stability of the polymer matrix, the opacity toward γ-rays, and the dispersion efficiency (i.e., the individualization and isolation of the individual SWCNT charge carriers). Resistance decreases up to 65% after irradiation with a 40 krad dose demonstrates the high sensitivity of this novel class of γ-ray sensors. In addition, the detection mechanism was evaluated using a commercial capacitive device platform. The ease of fabrication and low power consumption of these small and inexpensive sensor platforms combined with appealing sensitivity parameters establishes the potential of the poly(olefin sulfone)-SWCNT composites to serve as a new transduction material in γ-ray sensor applications.

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“…Sasaki et al utilized a photodepolymerizable cross‐linked polyolefin sulfone as photodetachable adhesive . A poly(olefin sulfone) copolymer carrying pendant carboxylic acid groups was mixed with a polycarbodiimide cross‐linker and 4,4′‐[bis[[methyl(2‐nitrobenzyl)oxy]carbonyl]‐trimethylene]di‐piperidine] as a photobase generator, which was included to induce photodepolymerization.…”

Section: Irreversible Switching Of the Adhesive Propertiesmentioning

confidence: 99%

(De)bonding on Demand with Optically Switchable Adhesives

Hohl

Weder

2019

Advanced Optical Materials

100

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nature of polymer-based adhesives prevent their easy removal and stifle or complicate debonding, rebonding, (end-of-life) recycling, and repair. In this context, the development of debonding-on-demand (DoD) adhesive technologies is attracting rapidly growing interest. Indeed, DoD techniques have already entered commercial exploitation in applications such as easily removable wound dressings, [2,3] temporal fixation in semiconductor manufacturing, [4][5][6] and the repair, replacement, or recycling of components. [7][8][9] While many debonding technologies employ heat to reduce the adhesive strength by imparting physical property changes of the adhesive, [10][11][12][13][14] light-induced debonding technologies represent an emerging field and have been much less explored. Photoirradiation is an attractive alternative to thermal debonding as it allows an efficient, contactless, remote stimulation that can be temporally and spatially controlled. [15][16][17][18] Moreover, factors such as the irradiation wavelength, intensity, and time can easily be tuned and it is often possible to focus the energy entry to the adhesive and minimize or avoid exposure of (sensitive) substrates. Of course, the approach requires that at least one of the substrates to be bonded is sufficiently transparent.The design of a light-debondable adhesive system is strongly related to the adhesive type and the requirements imparted by the application(s) for which the adhesive is designed. For instance, pressure-sensitive adhesives (PSAs), such as used in adhesive tapes, need to efficiently adhere under ambient conditions with only a brief application of pressure, they should withstand the (comparably small) loads experienced while bonded, and they must also be easily removable, ideally without leaving any residues on the substrate. [19,20] PSAs are therefore normally based on lightly physically or chemically cross-linked rubbery polymers such as natural rubber, styrene butadiene block copolymers, and acrylics. These materials provide a balance between adhesive and cohesive performance, i.e., adequate stiffness and strength to resist deformation and cohesive failure, and appropriate elasticity in order to establish adequate contact with the substrate. [1] On the other hand, structural adhesives must be able to effectively transmit large loads across the bonded joint and the high strength and high rigidity required for this function are usually achieved by the formation of glassy networks. Examples of such materials include cross-linked epoxy resins, which may possess shear strengths of >35 MPa, cyanoacrylates (superglues), acrylics, and polyurethanes. [19] Adhesives that enable bonding and especially debonding on demand (DoD) have attracted rapidly growing interest in the last decade, as these capabilities greatly improve the functionality of adhesives, particularly in connection with temporal fixation, repair, and recycling. Indeed, DoD techniques have already entered commercial exploitation in applications such as easily removable wound dressin...

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Dismantlable Thermosetting Adhesives Composed of a Cross-Linkable Poly(olefin sulfone) with a Photobase Generator

Cited by 35 publications

References 17 publications

Poly(olefin sulfone)s

Poly(olefin sulfone)s

Resistive and Capacitive γ-Ray Dosimeters Based On Triggered Depolymerization in Carbon Nanotube Composites

(De)bonding on Demand with Optically Switchable Adhesives

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