Triggered Decomposition of Polymeric Nanoparticles

Jhaveri, Sarav B.; Carter, Kenneth R.

doi:10.1021/ma071750x

Cited by 20 publications

(14 citation statements)

References 20 publications

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“…Photocurable resins are widely used as adhesives, coatings, etc., due to their toughness and wide availability. On the other hand, reworkable resins [1][2][3][4][5][6][7][8][9], which are thermosets thermally or chemically degradable under a given condition, have been extensively studied as environmentallyfriendly materials without damaging the underlying materials. Based on this information, we have developed a series of "reworkable" resins which are applicable to functional materials [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Rheological Studies of Reworkable Photocuring Resins

Okamura

Tachi

2018

J. Photopol. Sci. Technol.

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Rheological studies of reworkable photocuring resins were carried out using reworkable monomers. A dimethacrylate monomer containing tertiary ester units in a molecule and a methacrylate monomer, which has both an epoxy moiety and a thermally-cleavable tertiary ester moiety in a molecule, were employed as the reworkable monomers. When the cured reworkable monomers were irradiated and baked in the presence of a photoacid generator, the storage moduli of the cured resin decreased at elevated temperatures. The decreased storage moduli revealed by the rheological studies were due to the acid-catalyzed decomposition of the tertiary ester linkages in the cured reworkable monomers.

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Section: Introductionmentioning

confidence: 99%

Rheological Studies of Reworkable Photocuring Resins

Okamura

Tachi

2018

J. Photopol. Sci. Technol.

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“…Jhaveri and Carter exploited the well known acid-sensitivity of tertiary esters and prepared degradable PMMA microgels with 2,5-dimethyl-2,5-hexanediol dimethacrylate (DHDMA) as crosslinking agent. 172 These polymeric microgels were found to be degradable upon the addition of p-toluenesulfonic acid even in the absence of water, thereby representing an example for the specific degradability in dependency on one particular trigger (i.e. the presence of protons).…”

Section: Microgels Containing Hydrolytically Cleavable Crosslinkersmentioning

confidence: 99%

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Klinger

2013

Springer Theses

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This thesis focuses on the design, synthesis and characterization of novel photo-sensitive microgels and nanoparticles as potential materials for the loading and light-triggered release/accessibility of functional compounds. In order to realize this concept, different approaches to irradiation-dependent response mechanisms have been investigated.Novel light-cleavable divinyl functionalized monomeric crosslinkers based on o-nitrobenzyl derivatives were synthesized and used for the preparation of either PMMA or hydroxyl functionalized PHEMA microgels swellable and degradable in organic solvents. By the introduction of anionic MAA moieties into the PHEMA microgels, this concept was successfully transferred to double stimuli-responsive p(HEMA-co-MAA) hydrogel nanoparticles exhibiting a pH-dependent swelling and light-induced degradation behavior in aqueous media. This sensitivity to two orthogonal triggers is proposed to combine a pHinduced post-formation loading mechanism with a pH-and light-triggered release. In addition, a new class of enzyme-and light-sensitive PAAm microgels based on (meth-)acrylate functionalized dextrans as photo-and enzymatically degradable macromolecular crosslinkers was developed by introducing a photo-labile linker between the enzymatically degradable dextran chain and the polymerizable vinyl moieties. Here, the water solubility of the crosslinkers is assumed to enable an in situ loading approach of hydrophilic compounds.A different approach to the loading of microgels is based on photo-labile covalent microgel-drug conjugates. The first step to the realization of this concept was achieved by the development of a novel functional monomer consisting of a doxorubicin molecule covalently attached to a radically polymerizable methacrylate group via a photo-cleavable linker.Moreover, in order to enable the release of hydrophobic substances in aqueous media, hydrophobic nanoparticles consisting of a photo-resist polymer were designed to be degradable upon irradiation in water. Light-triggered conversion of the initial hydrophobic polymer into hydrophilic PMAA induced in situ particle dissolution and release of nile red.Since the introduction of a stimuli-responsive shell around a microgel is assumed to prevent leakage of embedded compounds, studies on non-stimuli-responsive shell formation around preformed microgel seed particles and the formation of microgel cores in polymeric shells were conducted to investigate potential synthetic pathways to this approach.In a last attempt, the surface of PHEMA and p(HEMA-co-MAA) microgels was functionalized with cinnamoyl groups in order to trigger the (reversible) particles interaction with each other by light-induced [2+2] cycloaddition reactions.

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“…To this aim, various materials with the ability to decompose via heat or light have been proposed. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Multi-functional (meth)acrylates with structures such as tertiary ester, 2-7,10-16 acetal, 8,9,[17][18][19] and carbonate, 20 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%

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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Triggered Decomposition of Polymeric Nanoparticles

Cited by 20 publications

References 20 publications

Rheological Studies of Reworkable Photocuring Resins

Rheological Studies of Reworkable Photocuring Resins

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

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

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