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24 protocols using glycidol

1

Synthesis of Functionalized Polyether Macromonomers

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All glassware used for the polymerisations was dried overnight at 120 °C prior to use. Potassium tert butoxide (KOtBu, ≥98%), 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6, ≥99%), 1,2-butylene oxide (BO, 99%), ethyl vinyl ether (EVE, ≥98%), glycidol (96%), calcium hydride (CaH2, 95%), potassium (K, chunks in mineral oil, 98%) and naphthalene (Naph, 99%) were purchased from Sigma-Aldrich (Switzerland) and used as received. Dry THF was obtained from an inert solvent purification system PureSolv MD 5 (Inert Technology, USA), dry 1,4-dioxane was purchased from Acros Organics (Belgium). The chemicals were stored under argon in a glovebox (MBraun Labstar, Germany). All other solvents used were in HPLC grade and purchased from JT Baker (USA), VWR (Switzerland) or Scharlau (Germany). Deionised water was obtained from a Milli-Q Q-POD device (Merck, Germany). Dulbecco's PBS buffer was purchased from Bioconcept Ltd (Switzerland).
Potassium naphthalenide (KNaph) was prepared by adding potassium (1.19 g, 30.5 mmol, 1 eq.) to a stirred solution of naphthalene (4.11 g, 32.0 mmol, 1.05 eq.) in dry THF (61 mL, 0.5 mol L−1) under argon. EEGE was synthesised following the standard protocol49 (link) from glycidol and EVE and dried over CaH2. The synthesis protocol and the 1H-NMR spectrum (Fig. S1) can be found in the ESI.
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2

Fluorescence Labeling of Hemoglobin

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Glycidol (purity 96.0%), fluorescein‐5‐isothiocyanate (FITC purity ≥90.0%), human hemoglobin lyophilized powder, and 1,2‐propanediol (purity 99.5%) were purchased from Sigma‐Aldrich. Acetonitrile and glyceraldehyde (purity 98.0%) were obtained from Tokyo Chemical Industry Co., Ltd., Kanto Chemical Industry Co., Ltd., and Nacalai Tesque, Inc., respectively. Other chemicals (L‐valine, L‐d8‐valine, sodium chloride, potassium bicarbonate, hydrochloric acid, ethyl acetate, sodium sulfate, toluene, ethyl acetate, ethanol, methanol, ammonium hydroxide, 3‐MCPD (purity 98.0%), epichlorohydrin (purity 99.0%), and acrylic acid (purity 98.0%) were purchased from Wako Pure Chemical Ind., Ltd.
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3

RNA Purification and Characterization

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Sodium methoxide, methanol and acetone were purchased from Merck. β-cyclodextrin, glycidol and Baker’syeast RNA from Sigma Chemical (St. Louis, MO) were employed without further purification. The absorbance band at 280 nm was utilized to check the protein content of RNA solutions. The A260/A280 ratio for RNA was 2.10, indicating that the RNA samples were nearly free from protein 30 (link). Other chemicals were of reagent grade and used without further purification.
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4

Glycidyl Ether Monomer Synthesis

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Glycidol, triethylamine (NEt3), tetrabutylammonium hydrogensulfate (TBAHSO4), phosphazene base t-BuP4 solution (0.8 M in hexane), anhydrous toluene, and anhydrous benzyl alcohol were purchased from Sigma-Aldrich. Epichlorohydrin (ECH), 3,5-dimethoxyphenol trityl chloride, 4-phenyl phenol, (s)-trityl glycidyl ether ((s)-TGE), and 4-methoxyphenyl glycidyl ether (MPG) were obtained from Tokyo Chemical Industry. Moreover, 4-dimethylaminopyridine (DMAP) was purchased from Alfa Aesar. Potassium hydroxide (KOH) flakes and ethyl acetate (EtOAc) were obtained from Daejung. Anhydrous magnesium sulfate (MgSO4) was purchased from Duksan. Furthermore, (s)-TGE and MPG were purified via azeotropic distillation using toluene cosolvent to remove moisture prior to polymerization. All other reagents were used as received without further purification. The deuterated NMR solvents CDCl3 and CD2Cl2 were purchased from Cambridge Isotope Laboratory.
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5

Synthesis of Eco-Polyols and Rigid Polyurethane Foams

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A 40% solution of water glass (sodium silicate, Dragon, Skawina, Poland) and a 35% solution of hydrochloric acid (POCh, Gliwice, Poland) were used to obtain MSA. In a further step, it was used for the reaction with glycidol (GL, Sigma-Aldrich, Saint Louis, MO, USA) and ethylene carbonate (EC, Sigma-Aldrich, Saint Louis, MO, USA) in the presence of potassium carbonate (POCh, Gliwice, Poland) as a catalyst. Eco-polyol was obtained as a result of the glycolysis reaction of PLA waste from various sources with ethylene glycol (MEG, Chempur, Piekary Śląskie, Poland) in the presence of a catalyst—zinc stearate (ZC, Chempur, Piekary Śląskie, Poland). A mixture of two newly synthesized polyols was used for the synthesis of rigid polyurethane foams. Besides new polyol raw materials, polymeric diphenylmethane diisocyanate (pMDI, Merck, Darmstadt, Germany) was used as a isocyanate raw material for synthesis of RPUFs. The other additives for the preparation of RPUFs were triethylamine (TEA, Sigma-Aldrich, Saint Louis, MO, USA) as a catalyst, Silicon L-6900 (Momentive, Strongsville, OH, USA) as a surfactant, and distilled water to form a blowing agent.
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6

Multifunctional Dendrimer-Based Nanoparticles

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G4 and G5 PAMAM dendrimers, rhodamine B isothiocyanate (RITC), folic acid (FA), glycidol, tin(II)2-ethylhexanoate, poly(ethylene glycol) monomethyl ether (mPEG) (MW 5,000 Da), poly(vinyl alcohol) (PVA, 87–89% hydrolyzed, MW 13,000–23,000 Da), dimethyl sulfoxide (DMSO), dimethylformamide (DMF), and dichloromethane (DCM) were all obtained from Sigma-Aldrich (St. Louis, MO). D,L-lactide and Boc-NH-PEG5K-OH were purchased from Polysciences Inc. (Warrington, PA) and Jenkem Technology (Beijing, China), respectively. All other chemicals used in this study were purchased from Sigma-Aldrich unless specified otherwise.
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7

Synthesis of Novel Tris(hydroxymethyl)propane Derivatives

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1,1,1-Tris(hydroxymethyl)propane
was purchased from Sigma-Aldrich. It was dissolved under reflux in
acetone, precipitated with ethyl ether, and then dried prior to use.
NaH (60 wt %) in mineral oil was purchased from Merck. The oil was
removed by washing with dry 1,4-dioxane and then drying under reduced
pressure. Glycidol (Sigma-Aldrich) was dried over CaH2 and
distilled before use. Tetrahydrofuran (THF) was purchased from Sigma-Aldrich
and dried over Na/K alloy. 2,2-Dimethoxypropane (TCI), benzoyl chloride,
phenyl isocyanate (Alfa Aesar), and 4-biphenylyl isocyanate (Sigma-Aldrich)
were used as received. p-Toluenesulfonic acid (PTSA)
was purchased from Sigma-Aldrich and dried with benzene before use.
CLT (Sigma-Aldrich) was used as received. Clodital MAX 500 mg, USP
Health, a CLT-loaded commercially available tablet, was used as a
reference.
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8

Synthesis and Evaluation of Paclitaxel Conjugates

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Ethyl vinyl ether (99%), glycidol (96%), p-toluene sulfonic acid monohydrate (TsOH, 98%), oxalic acid (98%), potassium tert-butoxide (>98%), ɛ-caprolactone (97%), tin(II) 2-ethylhexanoate (92.5–100%), 3-aminophenylboronic acid hydrochloride (3-APBA, 98%), folic acid (97%), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimidehydrochloride (EDC, 98%), N-hydroxysuccinimide (NHS), and 4′,6-diamidino-2-phenylindole (DAPI), were purchased from Sigma-Aldrich (St. Louis, Mo, USA). Lipiodol was purchased from Guerbet (Aulnay-sous-Bois, France), and paclitaxel (>97%) from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Human cervical epithelial carcinoma (HeLa) cells were purchased from the Korean Cell Line Bank (Seoul, Republic of Korea). A Cell-Counting Kit-8 (CCK-8) was obtained from Dojindo Laboratories (Kumamoto, Japan). Dulbecco’s modified Eagle’s medium (DMEM), phosphate buffered saline (PBS), and fetal bovine serum (FBS) were purchased from Invitrogen (Carlsbad, CA, USA).
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9

Antimicrobial Polyvinyl Butyral Polymer

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Polyvinyl butyral (Mw = 60,000 g mol−1; Mowital B 60T, kindly provided by Kuraray Specialities Europe, Troisdorf, Germany) was dissolved in ethanol (at the quality of p.a., Penta, Czech Republic). The structure of the Mowital B 60T comprised vinyl butyral, vinyl alcohol and vinyl acetate, at 75–81%, 24–27% and 1–4%, respectively. Decanoic acid, glycidol and chromium acetate hydroxide were supplied by Sigma-Aldrich (St. Louis, MO, USA). All the chemicals were applied as received without further purification. Both of the bacterial strains were obtained from the Czech Collection of Microorganism (CCM, Brno, Czech Republic), i.e., Gram-negative rods of Escherichia coli ATCC 25922 (CCM 3954), and Gram-positive cocci of Staphylococcus aureus ATCC 25923 (CCM 3953).
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10

Glyoxyl Agarose Bead Preparation

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Glyoxyl cross-linked 4% agarose beads was from was Agarose Bead Technologies (Torrejón de Ardoz, Spain) and prepared as previously described [64 (link)]. Boc-Ala-ONp (NPA) was from Bachem AG (Budendorf, Switzerland). Sodium periodate, glycidol, sodium borohydride, glutaraldehyde (25% (v/v)), ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC), ethylenediamine (EDA), were purchased from Sigma Chemical Co. (St. Louis, MO, USA). Alcalase 2.4 L type FG (liquid form) was a gift from Novo Nordisk A/S (Bagsvaerd, Denmark). All other reagents were of analytical grade.
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