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Diphenyliodonium hexafluorophosphate

Manufactured by Merck Group
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Diphenyliodonium hexafluorophosphate is a laboratory reagent used as a photoinitiator in photochemical reactions. It is a solid, crystalline compound that generates free radicals upon exposure to light, which can then initiate polymerization or other photochemical processes.

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11 protocols using diphenyliodonium hexafluorophosphate

1

Resin-Based Pit and Fissure Sealants with Metallic Monomers

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Self-adhesive resin-based pit and fissure sealant were formulated using a resin matrix containing triethylene glycol dimethacrylate, bisphenol A glycidyl methacrylate, glycerol dimethacrylate phosphate and water (Esstech, Essington, PA). Then, phenylbis (2,4,6-trimethylbenzoyl)-phosphine oxide and diphenyliodonium hexafluorophosphate were added as a photoinitiator and catalyst, respectively (Sigma-Aldrich, Saint Luis, MO). Finally, nanometric silica Aerosil® OX80 (Evonik, Essen, Germany) was added to the resin matrix. Zinc methacrylate or di-n-butyl-dimethacrylate-tin (Gute Chemie, Karlsruhe, Germany) (Figure 1) were added to form four experimental groups: ZnM 2.5 %; ZnM 5 %; SnM 2.5 %; SnM 5 %. A sealant without the incorporation of metallic monomers was used as a control.
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2

Antimicrobial Biomaterial Synthesis

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Chlorhexidine digluconate (CHX) was from Sigma-Aldrich. BD™ Bacto™ brain heart infusion, BD BBL dehydrated brain heart infusion agar, and Corning™ Clear polystyrene 96-well microplates, Corning™ 3370 were obtained from Fisher. AlamarBlue assay kit was obtained from Fisher.
Triethylene glycol dimethacrylate (TEGDMA), 2-hydroxyethylmethacrylate (HEMA) and 2-methacryloyloxyethyl phosphorylcholine (MPC) were used as received (Sigma-Aldrich) without further purification. Camphorquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB) and diphenyliodonium hexafluorophosphate (DPIHP) were obtained from Sigma-Aldrich (St. Louis, MO, USA) and used as a three-component-photoinitiator system without further purification. ε-pL hydrochloride was purchased from Bonding Chemical (Katy, TX, USA). To obtain ε-pL), 10 g ε-pL hydrochloride was dissolved in 60 mL sodium bicarbonate buffer (NaHCO3, 1.5M) and dialyzed with membrane (Spectra/Por®7 Dialysis Tubing, MWCO 1kD) in deionized water for 4 days. Then the solution was dried at 37 °C and ε-pL was obtained.
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3

Synthesis and Characterization of Dental Monomers

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BisGMA (Polysciences, Warrington, PA) and HEMA (Acros Organics, NJ) were used as received without further purification as monomers in dentin adhesives. BMPB was synthesized as reported previously in our laboratory.30 (link) 4-((1,3-Bis(methacryloyloxy)propan-2-yl)oxy)– 2-methylene-4-oxo-butanoic acid (BMPMOB) was synthesized in our laboratory and used as a comonomer (Figure 1). Itaconic anhydride (IAA) and glycerol dimethacrylate (GDMA) were obtained from Sigma-Aldrich (St. Louis, MO). Camphoroquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB), and diphenyliodonium hexafluorophosphate (DPIHP) were obtained from Sigma-Aldrich. All other chemicals were reagent grade and used without further purification.
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4

Synthesis and Characterization of Photocurable Dental Composites

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The following monomers and photoinitiators were purchased from Sigma-Aldrich (St. Louis, MO, USA): 2-hydroxyethyl methacrylate (HEMA), bisphenol A glycerolate dimethacrylate (BisGMA), diphenyliodonium hexafluorophosphate (DPIHP), camphoroquinone (CQ), and ethyl-4-(dimethylamino) benzoate (EDMAB). The organosilanes, methacryloxyethoxytrimethylsilane (MES), and γ-methacryloxypropyl trimethoxysilane (MPS) were purchased from Gelest Inc. (Morrisville, PA, USA) and MP Biomedicals (Solon, OH, USA), respectively. All materials were utilized as received without performing further purification. Scheme 2 lists the chemical structures of the monomers and photoinitiators.
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5

Antibacterial Resin Composite Synthesis

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Triethylene glycol dimethacrylate (TEGDMA), 2-hydroxyethyl methacrylate (HEMA), 2-methacryloyloxyethyl-phosphorylcholine (MPC), methacrylic acid (MA), camphoroquinone (CQ), ethyl 4-(dimethylamino)benzoate (EDMAB), diphenyliodonium hexafluorophosphate (DPIHP), dodecyltrichlorosilane, chlorhexidine digluconate (CHX), N,N-dimethylformamide (DMF), dichloromethane (DCM), and N-methylmorpholine (NMM) were obtained from Sigma-Aldrich (St. Louis, MO) and were used as received without further purification. Piperidine and alamarBlue Reagent were obtained from Fisher. Rink amide resin, Fmoc-amino acid building blocks, and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluranium hexafluorophosphate (HBTU) were purchased from AAPPTec LLC. BD Bacto brain heart infusion, BD BBL dehydrated brain heart infusion agar, and Corning Clear polystyrene 96-well microplates (Corning 3370) were obtained from Fisher. S. mutans UA159 bacterial strain was from American Type Culture Collection (ATCC 700610). Methacrylated AMP monomers (MA-AMP) were synthesized within our laboratory.
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6

Antimicrobial Peptide Synthesis and Evaluation

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Triethyleneglycol dimethacrylate (TEGDMA), 2-hydroxyethyl methacrylate (HEMA), 2-methacryloyloxyethyl phosphorylcholine (MPC), methacrylic acid (MA), camphoroquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB), diphenyliodonium hexafluorophosphate (DPIHP), dodecyltrichlorosilane, chlorhexidine digluconate (CHX), N, N-Dimethylformamide (DMF), dichloromethane (DCM) and N-methyl morpholine (NMM) were obtained from Sigma-Aldrich (St. Louis, MO, USA) and were used as received without further purification. γ‒methacryloxypropyl trimethoxysilane (MPS) was used as received from MP Biomedicals (Solon, OH, USA). Piperidine and AlamarBlue Reagent were obtained from Fisher (Thermo Fisher Scientific, Waltham, MA, USA). Rink amide resin, Fmoc-resin, Fmoc-amino acid building blocks, and 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluranium hexafluorophosphate (HBTU) were purchased from AAPPTec LLC (Louisville, KY, USA). BD™ (Becton, Dickinson, and Company; Franklin Lakes, NJ, USA) Bacto™ brain heart infusion, BD BBL dehydrated brain heart infusion agar, and Corning™ (Corning, NY, USA) Clear polystyrene 96-well microplates, Corning™ 3370 were obtained from Fisher. S. mutans UA159 bacterial strain was from American Type Culture Collection (ATCC 700610; Manassas, VA, USA).
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7

Antimicrobial Biomaterial Synthesis

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Chlorhexidine digluconate (CHX) was from Sigma-Aldrich. BD™ Bacto™ brain heart infusion, BD BBL dehydrated brain heart infusion agar, and Corning™ Clear polystyrene 96-well microplates, Corning™ 3370 were obtained from Fisher. AlamarBlue assay kit was obtained from Fisher.
Triethylene glycol dimethacrylate (TEGDMA), 2-hydroxyethylmethacrylate (HEMA) and 2-methacryloyloxyethyl phosphorylcholine (MPC) were used as received (Sigma-Aldrich) without further purification. Camphorquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB) and diphenyliodonium hexafluorophosphate (DPIHP) were obtained from Sigma-Aldrich (St. Louis, MO, USA) and used as a three-component-photoinitiator system without further purification. ε-pL hydrochloride was purchased from Bonding Chemical (Katy, TX, USA). To obtain ε-pL), 10 g ε-pL hydrochloride was dissolved in 60 mL sodium bicarbonate buffer (NaHCO3, 1.5M) and dialyzed with membrane (Spectra/Por®7 Dialysis Tubing, MWCO 1kD) in deionized water for 4 days. Then the solution was dried at 37 °C and ε-pL was obtained.
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8

Synthesis and Characterization of BP Derivatives

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The chemical structures
of BP derivatives are presented in Scheme 1. The synthesis and characterization of BP1
were published in the previous study,51 (link) while the second molecule BP2 is presented in the Supporting Information. The study by Asadi et al. was taken
as a reference in the synthesis of BP2.52 (link) Triethylamine (TEA), silver nitrate (AgNO3, 99.99%),
gold (III) chloride hydrate (HAuCl4 99.99%), methanol,
and diphenyl iodonium hexafluorophosphate (Ph2 I+) were obtained from Sigma-Aldrich. The structures of some compounds
used in this study are given in Scheme 2.
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9

Dual Photopolymerization for 3D Printing

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Example 1

In this example, 500 grams of photopolymer formulation were prepared by mixing trimethylol propane triacrylate (TMPTA, Miramer M300, Miwon) 35% wt, 1,6-haxanediol diacrylate (HDDA, Miramer M200, Miwon) 25% wt and 3,3-dimethyloxetane (Sigma-Aldrich) 30% wt in a black flask. This mixture was stirred form 10 minutes to obtain a homogenous solution, then, 2-methyl-4′-(methylthio)-2-morpholinopropiophenone (Sigma Aldrich) 2% wt, zinc tetraphenyl porphyrin (Sigma Aldrich) 3% wt and diphenyl iodonium hexafluorophosphate (Sigma Aldrich), 5% wt were added slowly and the reaction mixture was sonicated at 50° C. until all solids dissolved.

The 3D object was created using the setup described above and shown in FIG. 6, allowing for the selective use of UV light and visible light below 460 nm. These wavelengths were used in order to selectively induce the radical photopolymerisation. The bottom part of the 3D object was built using radical photopolymerisation. After completion of the bottom part of the 3D object, the red subpixels were used in order to selectively induce the cationic photopolymerisation. The top part of the 3D object was built using a cationic photopolymerisation process. After completion of the 3D printing process, the finished object was removed from the platform and post exposed under UV light and red light for 60 minutes, respectively.

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10

Silane-Functionalized Dental Monomers Synthesis

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2,2-Bis[4-(2-hydroxy-3-methacryloxypropoxy) phenyl]propane (BisGMA), 2-hydroxyethyl methacrylate (HEMA), camphoroquinone (CQ), ethyl-4-(dimethylamino) benzoate (EDMAB), diphenyliodonium hexafluorophosphate (DPIHP), L(+)-lactic acid (LA), dibutyltin dilaurate (DBTL), 3-morpholino-1,2-propanediolb (MPD), and (3-isocyanatopropyl) triethoxysilane (IPTES), were obtained from Sigma-Aldrich (St. Louis, MO) and used as received without further purification. (3-isocyanatopropyl) trimethoxysilane (IPTMS, 95%) was purchased from Gelest Inc., (Morrisville, PA). 2-hydroxy-3-morpholinopropyl (3-(triethoxysilyl)propyl) carbamate (SNE), 2-hydroxy-3-morpholinopropyl (3- (trimethoxysilyl)propyl) carbamate (SNM) were synthesized in our laboratory and used as co-monomers (see SI Scheme 1). All other chemicals were used as received without further purification.
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