Phenyl bis 2 4 6 trimethylbenzoyl phosphine oxide bapo

Manufactured by Merck Group

Sourced in United States, Italy, Germany

Phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO) is a photoinitiator compound used in various applications. It is a white to pale yellow crystalline solid. BAPO absorbs light in the visible and near-UV spectrum, which makes it suitable for use in photopolymerization processes.

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Lab products found in correlation

Methacrylic anhydride, by Merck Group (4 mentions) Acetone, by Avantor (2 mentions) Dichloromethane dcm, by Thermo Fisher Scientific (2 mentions) Vanillin, by Merck Group (2 mentions) Sodium bicarbonate, by Merck Group (2 mentions) Magnesium sulfate mgso4, by Thermo Fisher Scientific (1 mentions) Dichloromethane dcm, by Scharlab (1 mentions) Tert butyl peroxide, by Merck Group (1 mentions) Luperox di, by Merck Group (1 mentions) Sodium hydroxide (naoh), by Avantor (1 mentions) Magnesium sulfate mgso4, by Avantor (1 mentions) Isosorbide, by Merck Group (1 mentions) Zinc acetate zn oac 2, by Merck Group (1 mentions) Deuterated chloroform cdcl3, by Avantor (1 mentions) Ethanol etoh, by Avantor (1 mentions) Hydrochloric acid (hcl), by Merck Group (1 mentions) 4 dimethylaminopyridine dmap, by Merck Group (1 mentions) Ethylene carbonate, by Merck Group (1 mentions) Magnesium sulfate, by Avantor (1 mentions) Hydrochloric acid (hcl), by Avantor (1 mentions)

8 protocols using phenyl bis 2 4 6 trimethylbenzoyl phosphine oxide bapo

Polymer Synthesis via Photochemical Crosslinking

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4-(Dimethylamino) pyridine
(DMAP), hexamethylenediamine (HMDA), methacrylic anhydride (MAA),
ethylene glycol phenyl ether methacrylate (EGPMA), benzophenone (BP),
2,2-dimethoxy-2-phenylacetophenone (DMPA) and phenyl bis(2,4,6-trimethylbenzoyl)
phosphine oxide (BAPO) were purchased from Sigma-Aldrich. Vanillin
(Van) and sodium bicarbonate (NaHCO₃) were provided from
ACROS Organics. Diphenyl (2,4,6-trimethylbenzoyl) phosphine oxide
(TPO) was supplied by Ciba Specialty Chemicals Inc. 1,1-Di(t-amyl peroxy) cyclohexane (LUPEROX 531 M60) was kindly
supplied by ARKEMA. Magnesium sulfate (MgSO₄) was obtained
from ThermoFisher Scientific, and sodium hydroxide (granulated, NaOH)
and dichloromethane (DCM) were obtained from Scharlau.

Vilanova-Pérez A., De la Flor S., Fernández-Francos X., Serra À, & Roig A. (2024). Biobased Imine Vitrimers Obtained by Photo and Thermal Curing Procedures—Promising Materials for 3D Printing. ACS Applied Polymer Materials, 6(6), 3364-3372.

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Isosorbide Dimethacrylate Synthesis

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Sorbitol (D-glucitol, 98%) used for the synthesis of isosorbide was purchased from Fichema s.r.o. (Brno, Czech Republic). The catalyst for the dehydration (para-toluenesulfonic acid (p-TSA), monohydrate, 98%, for synthesis) was acquired from Sigma-Aldrich (St. Louis, MO, USA). Methacrylic anhydride (94%, for synthesis) used for the modification of isosorbide to isosorbide dimethacrylate was obtained from Sigma-Aldrich (St. Louis, MO, USA). Other chemicals used in the described syntheses, namely potassium acetate (p.a.) as catalyst and sodium hydroxide (p.a.) as neutralizing agent, were obtained from PENTA s.r.o. (Prague, Czech Republic). Initiators for the curing experiments such as Luperox^® DI, tert-Butyl peroxide (for synthesis), or phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO, 97%) were purchased from Sigma-Aldrich (St. Louis, MO, USA).

Jašek V., Fučík J., Krhut J., Mravcova L., Figalla S, & Přikryl R. (2023). A Study of Isosorbide Synthesis from Sorbitol for Material Applications Using Isosorbide Dimethacrylate for Enhancement of Bio-Based Resins. Polymers, 15(17), 3640.

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Isosorbide-Based Photopolymerizable Hydrogel

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Isosorbide(I) (98%), vanillin(V) (99%), methacrylic
anhydride (MAA) (≥94%), 4-(dimethylamino)pyridine (DMAP) (≥99%),
phenylbis(2,4,6-trimethylbenzoyl)-phosphine oxide (BAPO) (97%), hydrochloric
acid (HCl) (37%), and zinc acetate (Zn(OAc)₂) (99.99%)
were purchased from Sigma-Aldrich. 2,2′-(Ethylenedioxy)bis(ethylamine)
(Dom) (≥97%) and dichloromethane (DCM) (≥99%) were obtained
from Fisher Scientific and sodium bicarbonate (≥99.7%) from
Merck. Sodium hydroxide (NaOH) (99%), magnesium sulfate (MgSO₄) (≥99%), acetone (≥99%), ethanol (EtOH) (100%),
and deuterated chloroform (CDCl₃) (99.8 atom % D) were
received from VWR. All chemicals and solvents were used without any
additional purification.

Liguori A., Oliva E., Sangermano M, & Hakkarainen M. (2023). Digital Light Processing 3D Printing of Isosorbide- and Vanillin-Based Ester and Ester–Imine Thermosets: Structure–Property Recyclability Relationships. ACS Sustainable Chemistry & Engineering, 11(39), 14601-14613.

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Photocurable Polymer Nanocomposite Synthesis

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2-Hydroxy-2-phenoxypropyl acrylate (HPPA), glycerol 1,3-diglycerolate diacrylate (GDGDA), trimethylolpropane tri(3-mercaptopropionate) (TMPMP), Fe(ii,iii) oxide nanoparticles (d₅₀ = 50 nm), and phenylbis(2,4,6-trimethylbenzoyl) phosphine oxide (BAPO) were purchased from Sigma-Aldrich. Miramer A99 was used as stabilizer and transesterification catalyst, and was received from Miwon Speciality Chemical (Korea). All chemicals were used without further purification.

Cazin I., Rossegger E., Roppolo I., Sangermano M., Granitzer P., Rumpf K, & Schlögl S. (2023). Digital light processing 3D printing of dynamic magneto-responsive thiol-acrylate composites. RSC Advances, 13(26), 17536-17544.

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Thermoset Polymer Synthesis and Characterization

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Vanillin
(V) (99%), ethylene carbonate (EC)
(98%), potassium carbonate (K₂CO₃) (≥99%), N,N-dimethylformamide (DMF) (≥99%),
methacrylic anhydride (MAA) (94%), ethylenediamine (ED) (≥99%),
2,2′-(ethylenedioxy)bis(ethylamine) (Dom) (>97%), phenylbis(2,4,6-trimethylbenzoyl)phosphine
oxide (BAPO) (97%), and deuterium dimethyl sulfoxide (DMSO-d₆) (99.9% atom % D) were purchased from Sigma-Aldrich
and used without any additional purification. 4-(Dimethylamino)pyridine
(DMAP) (≥99.0%, Fluka), magnesium sulfate (99%, VWR), sodium
bicarbonate (≥99%, Merck), sodium hydroxide (NaOH) (≥99%,
Fisher Scientific), ethyl acetate (EtOAc) (≥99%, VWR), dichloromethane
(DCM) (≥99%, Fisher Scientific), hydrochloric acid (HCl) (37%),
and acetone (≥99.5%, VWR) were all used as received. Sodium
lignosulfonate for the coating of the thermosets and 2,2-diphenyl-1-picrylhydrazyl
(DPPH°) for the antioxidant assay were acquired from Tokyo Chemical
Industry Co., Ltd.

Liguori A., Xu H., Hazarika D, & Hakkarainen M. (2023). Simple Non-Equilibrium Atmospheric Plasma Post-Treatment Strategy for Surface Coating of Digital Light Processed 3D-Printed Vanillin-Based Schiff-Base Thermosets. ACS Applied Polymer Materials, 5(10), 8506-8517.

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Photocurable Protein Conjugate Synthesis

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Materials: Trimethylolpropane tris(3mercaptopropionate) (TMPMP) as multi-functional thiol and phenylbis (2,4,6-trimethylbenzoyl)phosphine oxide (BAPO) as photoinitiator were provided from Sigma-Aldrich (Milan, Italy) and were used without further purification. (2-nitro-1,4 phenylene) bis(methylene) acetate (vinyl-NBE) was synthesized as reported in previous work. [21] For the post functionalization step, 2-(N-morpholino)ethanesulfonic acid (MES, 99.5%), sodium chloride (99.5%), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC, 99%), Nhydroxysulfosuccinimide sodium salt (sulfo-NHS, 98%), Dulbecco's phosphate-buffered saline (PBS) and poly(oxyethylene) glycol sorbitan monolaurate (Tween™ 20) were purchased from Sigma-Aldrich (Milan, Italy) and used without further purification. Protein A, Alexa Fluor™ 546 conjugated was purchased from Thermo Fischer Scientific (Monza, Italy) and used according to the manufacturer's instructions.

Romano A., Angelini A., Rossegger E., Palmara G., Castellino M., Frascella F., Chiappone A., Chiadò A., Sangermano M., Schlögl S, & Roppolo I. (2020). Laser-Triggered Writing and Biofunctionalization of Thiol-Ene Networks. Macromolecular rapid communications, 41(10).

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Synthesis of Poly(2-hydroxyethyl acrylate)

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The poly(ethylene glycol) methyl ether acrylate (PEGMEA480, MW 480), poly(ethylene glycol) dimethacrylate (PEGDMA550, Mw 550), sodium hydroxide (NaOH), 3-(acryloyloxy)-2-hydroxypropyl methacrylate, acetic acid, Sudan I, phenylbis(2,4,6-trimethyl benzoyl) phosphine oxide (BAPO), and phosphate-buffered saline (PBS, pH 7,4) were supplied by Merck and used as received without further purification.
The Jeffamine ED-600 (supplied by Huntsman) and glycerol monomethacrylate (GMM, supplied by Polysciences) were used as received.
2-hydroxy ethyl acrylate (HEA, supplied by TCI), azo-bis-isobutirenitrile (AIBN, supplied by Glentham) and dioxane (supplied by Panreac) were used as received.
The HCL was prepared as described previously from 3-(acryloyloxy)-2-hydroxypropyl methacrylate and Jeffamine using a catalytic quantity of acetic acid [20 ].
The synthesis of poly-HEA (pHEA) was carried out by thermal polymerization in solution. 665 mg of HEA were introduced into a vial, with a stirrer inside, and dissolved in 10 mL of dioxane. Next, 25 mg of AIBN were added. After that, the solution was left stirring for about 5–10 min for its complete homogenization and then nitrogen was bubbled for 5 min. Finally, the polymerization was allowed to proceed overnight in an oven at 60 °C. The next day, upon cooling to 5 °C separation into two phases was observed, which allows the dioxane to be easily removed.

Liz-Basteiro P., Reviriego F., Martínez-Campos E., Reinecke H., Elvira C., Rodríguez-Hernández J, & Gallardo A. (2023). Vat Photopolymerization 3D Printing of Hydrogels with Re-Adjustable Swelling. Gels, 9(8), 600.

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Formulation and 3D Printing of PEG-Based Resins

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Three resin compositions were used. The commercial resin PlasCLEAR (Litholabs/Asiga, Heidelberg, Germany) was directly printed. The resins PEG-1 and PEG-2 were first formulated and then printed. As PEG-1 we refer to poly(ethylene glycol) diacrylate (PEG-DA) M w 200 (Merck KGaA, Darmstadt, Germany) mixed with 0.4 wt/vol% phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO) (Merck KGaA, Darmstadt, Germany) as photo initiator. PEG-2 is a mixture of PEG-DA with 0.4 wt/vol% BAPO as photo initiator and 0.1 wt/vol% 2-isopropylthioxanthone (ITX) (abcr GmbH, Karlsruhe, Germany) as photo sensitizer. The PEG-DA based resins were prepared by adding the powder photo initiator and sensitizer to the liquid PEG-DA, followed by stirring with a magnetic stir bar on a heating plate at 40 °C for one hour.

Fritschen A., Bell A.K., Königstein I., Stühn L., Stark R.W, & Blaeser A. (2022). Investigation and comparison of resin materials in transparent DLP-printing for application in cell culture and organs-on-a-chip. Biomaterials science, 10(8).

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