Thiol–ene adhesives from clove oil derivatives

Donovan, Brian R.; Cobb, Jared S.; Hoff, Ethan F. T.; Patton, Derek L.

doi:10.1039/c4ra12020e

Cited by 26 publications

(19 citation statements)

References 38 publications

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“…Additionally, Raman spectroscopy of freshly emulsified nanoparticles prior to and after UV polymerization showed the disappearance of SH (2580 cm −1 ) and alkene stretches (1640–1680 cm −1 ) (Figure S2, Supporting Information). The ability to achieve high thiol‐ene monomer conversion in the presence of phenolic functional groups is in good agreement with our previous work . At near quantitative conversions, crosslink density (0.168 × 10 −3 mol cm –3 ) of the polythioether NPs was estimated from the rubbery plateau storage modulus (1.25 MPa, T g −12.1 °C, Figure S3, Supporting Information) of the base thiol‐ene resin (i.e., GDMP+PETMP+diallyl phthalate prepared at identical stoichiometric ratios used in the miniemulsions) at T g + 40 °C according to the theory of rubber elasticity .…”

Section: Resultssupporting

confidence: 88%

Destruction of Opportunistic Pathogens via Polymer Nanoparticle‐Mediated Release of Plant‐Based Antimicrobial Payloads

Amato

Mavrodi

et al. 2016

Adv Healthcare Materials

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The synthesis of antimicrobial thymol/carvacrol-loaded polythioether nanoparticles (NPs) via a one-pot, solvent-free miniemulsion thiol-ene photopolymerization process is reported. The active antimicrobial agents, thymol and carvacrol, are employed as “solvents” for the thiol-ene monomer phase in the miniemulsion to enable facile high capacity loading (≈50% w/w), excellent encapsulation efficiencies (>95%), and elimination of all postpolymerization purification processes. The NPs serve as high capacity reservoirs for slow-release and delivery of thymol/carvacrol-combination payloads that exhibit inhibitory and bactericidal activity (>99.9% kill efficiency at 24 h) against gram-positive and gram-negative bacteria, including both saprophytic (Bacillus subtilis ATCC 6633 and Escherichia coli ATCC 25922) and pathogenic species (E. coli ATCC 43895, Staphylococcus aureus RN6390, and Burkholderia cenocepacia K56-2). This report is among the first to demonstrate antimicrobial efficacy of essential oil-loaded nanoparticles against B. cenocepacia – an innately resistant opportunistic pathogen commonly associated with debilitating respiratory infections in cystic fibrosis. Although a model platform, these results point to promising pathways to particle-based delivery of plant-derived extracts for a range of antimicrobial applications, including active packaging materials, topical antiseptics, and innovative therapeutics.

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Section: Resultssupporting

confidence: 88%

Destruction of Opportunistic Pathogens via Polymer Nanoparticle‐Mediated Release of Plant‐Based Antimicrobial Payloads

Amato

Mavrodi

et al. 2016

Adv Healthcare Materials

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“…As the crosshatch adhesion test is described as a peel test, the higher flexibility of the PS‐2 films compared to the PS‐1 films allows greater energy absorption before any interactions at the film/substrate interface are ruptured, resulting in an improvement of adhesion. Additionally, the weight percentage of PETMP (known to be nonadhesive) within the film decreases as the molecular weight of the polysulfide increases. The PS‐1 films contain ∼20 wt % PETMP, compared to ∼7.5 wt % for the PS‐2 films, contributing to the low adhesion values measured for the PS‐1 films.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and thiol–ene photopolymerization of (meth)allyl‐terminated polysulfides

Brei

Donovan

Patton

et al. 2017

J of Applied Polymer Sci

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Thiol‐terminated polysulfides (PS) are cured by mixing with an oxidant, resulting in limited shelf‐ and/or pot‐life, depending on whether formulated as a one‐ or two‐component system. Mixtures of thiol‐ and alkene‐terminated polysulfides offer the potential for an on‐demand curing process through thiol–ene photopolymerization. Thiol end groups of commercial polysulfides, PS‐1 (1000 g/mol) and PS‐2 (3000 g/mol), were converted to alkene by reaction with (meth)allyl bromide. Photopolymerizations were performed by irradiating films of equimolar thiol:ene mixtures at 320–500 nm (30 mW/cm2) in the presence of 5 wt % 2,2‐dimethoxy‐2‐phenyl‐acetophenone (DMPA). Reaction kinetics were measured using real‐time FTIR by monitoring absorbances at 3075 cm−1 (alkene) or 2550 cm−1 (thiol). In the absence of any reactive diluent, mixtures of thiol and alkene polysulfides failed to gel notwithstanding high reaction conversion (>90%). Partial or total replacement of the thiol polysulfide component with pentaerythritol tetrakis(3‐mercaptopropionate) (PETMP) yielded solid elastomeric films and ultimate reaction conversions of 80–96% after 5 min irradiation. Crosshatch adhesion measured on glass, aluminum, and steel was very poor (0B) for (meth)allyl PS‐1/PETMP and poor (2B) for (meth)allyl PS‐2/PETMP without adhesion promoters. (3‐Mercaptopropyl)trimethoxysilane (1 wt %) significantly improved adhesion of (meth)allyl PS‐2/PETMP on all substrates (4B) but yielded no improvement for (meth)allyl‐terminated PS‐1/PETMP. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 45523.

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“…Apart from the applications mentioned above, Derek L. Patton reported eugenol-derived catechol-functionalized thiolene polymer networks as photocurable adhesives. 27 In addition, Deng et al developed a new-fashioned eugenol-based polymeric microsphere as oil-absorbent. 28 All the examples mentioned above indicate that eugenol as a renewable biomass has promising application prospect in the field of polymer materials.…”

Section: Introductionmentioning

confidence: 99%

Bio‐based aromatic copoly(ether ester)s with enhanced toughness and degradability: Influence of insertion of phenoxy‐ether linkage and eugenol‐derived composition on properties

Zhao

et al. 2016

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

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Thiol–ene adhesives from clove oil derivatives

Abstract: This paper reports the synthesis of catechol-functionalized thiol–ene networks as photocurable adhesives, where adhesive interactions are derived from 4-allylpyrocatechol – an alkene readily obtained from Syzygium aromaticum flower buds (clove oil).

Cited by 26 publications

References 38 publications

Destruction of Opportunistic Pathogens via Polymer Nanoparticle‐Mediated Release of Plant‐Based Antimicrobial Payloads

Destruction of Opportunistic Pathogens via Polymer Nanoparticle‐Mediated Release of Plant‐Based Antimicrobial Payloads

Synthesis and thiol–ene photopolymerization of (meth)allyl‐terminated polysulfides

Bio‐based aromatic copoly(ether ester)s with enhanced toughness and degradability: Influence of insertion of phenoxy‐ether linkage and eugenol‐derived composition on properties

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