Multi-Functional Methacrylates Bearing Thermal Degradation Properties-Synthesis, Photo- and Thermal Curing, and Thermolysis-

Shirai, Masamitsu; Mitsukura, Kazuyuki; Okamura, Hitoshi; Miyasaka, Masahiro

doi:10.2494/photopolymer.18.199

Cited by 11 publications

(7 citation statements)

References 13 publications

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“…Methacrylate monomers (1)(2)(3) with acetal moieties were prepared from the reaction between the corresponding vinyl ethers and 2-hydroxyethly methacrylate. 16 The monomers were purified using column chromatography. The monomer synthesis yields were 62-79 %, depending on the monomer structure.…”

Section: Multifunctional Monomers With Degradable Properties Methacrymentioning

confidence: 99%

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Photocrosslinkable polymers with degradable properties

Shirai

2014

Polym J

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Photocrosslinkable polymers and ultraviolet (UV)-curable resins are significant applications such as coatings, adhesives, photoresists and printing plates. Crosslinked polymers are insoluble and infusible; therefore, it is very difficult to remove crosslinked materials from substrates. Recently, much attention has been paid to the recovery or recycling of crosslinked polymers due to environmental regulations. To this end, photocrosslinkable polymers with degradable properties have been studied. Photocrosslinkable polymers and UV-curable resins with degradable properties are also realized as highly functionalized photopolymers. This article reviews our recent research on photocrosslinkable polymers with degradable properties. Multifunctional methacrylates and epoxides with degradable properties were prepared, and their UV-curing and degradation profiles were studied. Furthermore, polymers with crosslinkable units and degradable side chains were prepared and characterized in a similar manner. Some potential applications of these monomers and polymers were also described.

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Section: Multifunctional Monomers With Degradable Properties Methacrymentioning

confidence: 99%

“…Multifunctional epoxides (12)(13)(14)(15)(16)(17)(18) bearing tertiary esters as degradable units were prepared. [24][25][26][27] Epoxide structures are shown in Figure 4.…”

Section: Epoxidesmentioning

confidence: 99%

Photocrosslinkable polymers with degradable properties

Shirai

2014

Polym J

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“…To this aim, various materials with the ability to decompose via heat or light have been proposed . Multi‐functional (meth)acrylates with structures such as tertiary ester, acetal, and carbonate, which experience bond cleavage in acid, have been reported. The research group of Osaka Prefecture University has developed a radically curable tri‐functional methacrylate resin with a decomposition function .…”

Section: Introductionmentioning

confidence: 99%

“…Multi‐functional (meth)acrylates with structures such as tertiary ester, acetal, and carbonate, which experience bond cleavage in acid, have been reported. The research group of Osaka Prefecture University has developed a radically curable tri‐functional methacrylate resin with a decomposition function . They succeeded in realizing both curing and decomposition using this resin with photosensitive compounds of different photosensitive wavelength.…”

Section: Introductionmentioning

confidence: 99%

Positive‐tone photoresist consisting of a multifunctional acrylate resin that can be patterned after photo‐crosslinking

Sugita

Miyashita

Suzuki

et al. 2017

J of Applied Polymer Sci

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A multifunctional acrylate resin having a tertiary ester structure is synthesized using a thiol‐acrylate Michael addition click reaction. By loading both a photo radical initiator and a photo acid generator into this resin, a positive‐tone photoresist, that can be patterned after photocrosslinking (PPaP), is formulated. After the thin film is irradiated with 365 nm light, radical crosslinking proceeds and a solvent resistant “frozen” film can be obtained. The frozen film works as a positive‐tone photoresist. When the frozen PPaP is irradiated with light containing a wavelength much shorter than 300 nm, the ester structure of the exposed region is decomposed by photo‐chemically generated acid and dissolved in an alkaline solution. Furthermore, a photochemical pattern transfer is achieved using the material. By performing the photo exposure on conventional photoresist patterns on the frozen PPaP underlayer, the photoresist patterns are successfully transferred to the underlayer. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45871.

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“…[8][9][10][11] In these systems, labile or degradable covalent bonds were incorporated into the crosslinked structures. We have reported the synthesis of several types of reworkable resins [12][13][14][15][16] and applied them to the UV-NIL process. 17,18 It was confirmed that the UV curable resin with reworkable properties was very attractive for UV-NIL because the cured resins remaining on the quartz mold were successfully de-crosslinked and dissolved away by washing with organic solvents.…”

Section: Introductionmentioning

confidence: 99%

Reworkable dimethacrylates with low shrinkage and their application to UV nanoimprint lithography

2011

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Four types of reworkable dimethacrylates bearing hemiacetal ester groups were synthesized and the UV curing and degradation were studied. UV nanoimprint lithography (UV-NIL) using these monomers was performed and fine line/space patterns were obtained. The shrinkage in height of the UV imprinted pattern was studied in relation to the monomer structure and UV imprint conditions such as light intensity and concentrations of photoradical initiator and chain transfer reagent. The effect of UV imprint conditions on the kinetic chain length of UV cured networks was investigated using size exclusion chromatography of the linear polymers obtained from the degradation of the UV imprinted patterns. A relationship between the kinetic chain length and shrinkage of the UV imprinted patterns was discussed.

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Multi-Functional Methacrylates Bearing Thermal Degradation Properties-Synthesis, Photo- and Thermal Curing, and Thermolysis-

Cited by 11 publications

References 13 publications

Photocrosslinkable polymers with degradable properties

Photocrosslinkable polymers with degradable properties

Positive‐tone photoresist consisting of a multifunctional acrylate resin that can be patterned after photo‐crosslinking

Reworkable dimethacrylates with low shrinkage and their application to UV nanoimprint lithography

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