All solvents (dimethylformamide (DMF), ethyl aceteate (AcOEt), hexane, heptane, toluene, methanol (MeOH), ethanol (EtOH), isopropyl alcohol (IPA)) were purchased from POCH (Gliwice, Poland) and distilled prior to use. DMF was dried by vacuum distillation over P2O5 under the N2 atmosphere. Heptane and toluene were distilled in the same way but under normal pressure. The remaining reagents were purchased from SigmaAldrich (Poznań, Poland) (glycidyl methacrylate (GMA, ≥97% GC), ethyl methacrylate (EMA, ≥99% GC), ethanolamine (ETA, ≥99%), l -ornithine hydrochloride (Orn), xylitol (Xyl), azobisisobutyronitrile (AIBN, ≥95%), 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), sodium hydroxide (NaOH), hydrochloric acid (HCl), agarose, phosphate-buffered saline (PBS, pH = 7.4), methylene blue (MB) and were of analytical grade, and used without prior purification. Before using methacrylic esters for polymerization, these monomers were filtered through a short layer of dry silica gel (40–60 mm) to remove polymerization inhibitors.
Ethyl methacrylate
Manufactured by Merck Group
Sourced in United Kingdom
Ethyl methacrylate is a colorless liquid chemical compound. It is used as a monomer in the production of polymethyl methacrylate (PMMA), a type of plastic commonly known as acrylic. Ethyl methacrylate is a key ingredient in the manufacturing of various laboratory equipment and supplies.
Automatically generated - may contain errors
Lab products found in correlation
Methyl methacrylate, by Merck Group (3 mentions)
2 2 azobisisobutyronitrile, by Merck Group (2 mentions)
Methanol, by Merck Group (2 mentions)
L ornithine hydrochloride, by Merck Group (1 mentions)
Ethanolamine, by Merck Group (1 mentions)
Xylitol, by Merck Group (1 mentions)
Azobisisobutyronitrile, by Merck Group (1 mentions)
Glycidyl methacrylate, by Merck Group (1 mentions)
Benzoyl peroxide, by Merck Group (1 mentions)
Milli q water purification system, by Merck Group (1 mentions)
Ethanol, by Merck Group (1 mentions)
Toluene, by Merck Group (1 mentions)
Acetonitrile, by Merck Group (1 mentions)
N n dimethylformamide (dmf), by Thermo Fisher Scientific (1 mentions)
4 cyano 4 phenylcarbonothioylthio pentanoic acid cpa db, by Merck Group (1 mentions)
2 hydroxyethyl methacrylate hema, by Merck Group (1 mentions)
Chloroform, by Avantor (1 mentions)
Trimethylsilyldiazomethane solution, by Merck Group (1 mentions)
Benzyl bromide, by Merck Group (1 mentions)
Deuterated acetone, by Merck Group (1 mentions)
10 protocols using ethyl methacrylate
1
Synthesis of Functionalized Polymers
2
Curcuminoid Extraction and Characterization
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All chemicals used were of analytical reagent grade. Deionized distilled water was used throughout the experiment (Milli-Q water purification system, Millipore Co., USA). A curcuminoid standard sample (purity: 99%) was purchased from Wako Pure Chemical, Osaka, Japan. Ethyl methacrylate (EMA), styrene, methacrylic acid (MAA), ethylene glycol dimethacrylate (EGDMA), and benzoyl peroxide (BPO) were purchased from Sigma–Aldrich (United Kingdom). Tetrahydrofuran (THF), trichloroacetic acid (TCA), sulfuric acid, ethanol, and toluene were purchased from Aldrich (Poole, Dorset, United Kingdom). Methanol and acetonitrile (HPLC grade) were purchased from E. Merck (Darmstadt, Germany).
3
Synthesis and Purification of Polymeric Monomers
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4-Cyano-4-(phenylcarbonothioylthio)pentanoic
acid (CPADB) >97% was obtained from Sigma-Aldrich. N,N-Dimethylformamide (DMF) 99+% extra pure was purchased
from Acros Organics. Ethanol (EtOH), pentane, chloroform (CHCl3), and diethyl ether were acquired from Avantor. All chemicals
were used as received. α,α′-Azoisobutyronitrile
(AIBN) >98% was obtained from Sigma-Aldrich and recrystallized
twice
from methanol prior to use. 2-Hydroxyethyl methacrylate (HEMA) 98%
and ethyl methacrylate (EMA) 99% were purchased from Sigma-Aldrich,
and purification was done by passing them through the basic Al2O3 column. 2-(β-glucosyloxy)ethyl methacrylate
(GEMA) monomer was synthesized according to literature.29 (link)
acid (CPADB) >97% was obtained from Sigma-Aldrich. N,N-Dimethylformamide (DMF) 99+% extra pure was purchased
from Acros Organics. Ethanol (EtOH), pentane, chloroform (CHCl3), and diethyl ether were acquired from Avantor. All chemicals
were used as received. α,α′-Azoisobutyronitrile
(AIBN) >98% was obtained from Sigma-Aldrich and recrystallized
twice
from methanol prior to use. 2-Hydroxyethyl methacrylate (HEMA) 98%
and ethyl methacrylate (EMA) 99% were purchased from Sigma-Aldrich,
and purification was done by passing them through the basic Al2O3 column. 2-(β-glucosyloxy)ethyl methacrylate
(GEMA) monomer was synthesized according to literature.29 (link)
4
Synthesis of Methacrylate Polymer Precursors
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Methyl
methacrylate (MMA, 99%), ethyl methacrylate
(EMA, 99%), n-butyl methacrylate (BMA, 99%), n-hexyl methacrylate (HMA, 99%), DMAEMA (99%), and MAA (99.5%)
were purchased from Sigma-Aldrich (Gillingham, U.K.) and were passed
through a basic alumina column to remove inhibitor prior to polymerization.
2-Ethylhexyl methacrylate (EHMA, 98%) was purchased from Alfa Aesar
(Heysham, U.K.), and its inhibitor was removed using an alumina column.
Isopropanol (IPA, 99.9%), triethanolamine (TEA, 99%), 4,4′-azobis(4-cyanovaleric
acid) (ACVA), 1,4-dioxane (99.5%), trimethylsilyldiazomethane solution
(2.0 M in diethyl ether), benzyl bromide (BzBr, 98%), and deuterated
acetone were purchased from Sigma-Aldrich. Deuterated chloroform (CDCl3) and deuterated dimethyl sulfoxide (DMSO-d6) for NMR spectroscopy measurements were purchased from
VWR (Lutterworth, U.K.). Deionized water was obtained using an Elgastat
Option 3A water purifier (Elga, High Wycombe, U.K.). 4-Cyano-4-(2-phenylethanesulfanylthiocarbonyl)sulfanylpentanoic
acid (PETTC) used for RAFT polymerization was prepared and purified
in-house, as reported previously.35 (link) Unless
stated otherwise, all materials were used as received.
methacrylate (MMA, 99%), ethyl methacrylate
(EMA, 99%), n-butyl methacrylate (BMA, 99%), n-hexyl methacrylate (HMA, 99%), DMAEMA (99%), and MAA (99.5%)
were purchased from Sigma-Aldrich (Gillingham, U.K.) and were passed
through a basic alumina column to remove inhibitor prior to polymerization.
2-Ethylhexyl methacrylate (EHMA, 98%) was purchased from Alfa Aesar
(Heysham, U.K.), and its inhibitor was removed using an alumina column.
Isopropanol (IPA, 99.9%), triethanolamine (TEA, 99%), 4,4′-azobis(4-cyanovaleric
acid) (ACVA), 1,4-dioxane (99.5%), trimethylsilyldiazomethane solution
(2.0 M in diethyl ether), benzyl bromide (BzBr, 98%), and deuterated
acetone were purchased from Sigma-Aldrich. Deuterated chloroform (CDCl3) and deuterated dimethyl sulfoxide (DMSO-d6) for NMR spectroscopy measurements were purchased from
VWR (Lutterworth, U.K.). Deionized water was obtained using an Elgastat
Option 3A water purifier (Elga, High Wycombe, U.K.). 4-Cyano-4-(2-phenylethanesulfanylthiocarbonyl)sulfanylpentanoic
acid (PETTC) used for RAFT polymerization was prepared and purified
in-house, as reported previously.35 (link) Unless
stated otherwise, all materials were used as received.
5
Synthesis and Characterization of Functionalized Monomers
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tert-Butyl-3-hydroxypropanoate, methyl 3-mercaptopropionate, and ethyl methacrylate were purchased from Acros Organics. 2,2′-Azobis-(isobutyronitrile) (AIBN) and ethyl methacrylate were purchased from Sigma-Aldrich Co. Trifluoroacetic acid (TFA) and solvents were purchased from Thermo Fisher Scientific, Inc. The chemicals were used without further purification, with the exception of methacryloyl chloride which was distilled before use and AIBN which was recrystallized from hot methanol. Boc-amino ethyl methacrylate was synthesized according to the previous reported procedure.61 (link)1H NMR was performed using a Varian MR400 (400 MHz), 13C NMR was performed using a Bruker NEO600 (600 MHz) and the data was analyzed using VNMRJ 3.2 and MestReNova. Gel permeation chromatography (GPC) analysis was performed using a Waters 1515 HPLC instrument equipped with Waters Styragel (7.8 × 300 mm) HR 0.5, HR 1, and HR 4 columns in sequence and detected by a differential refractometer (RI). Mueller Hinton broth (MHB, BD and Company) and phosphate buffered saline (PBS, pH = 7.4, Gibco) were prepared according to manufacturer instructions and sterilized prior to use. Human red blood cells (RBCs) (leukocytes reduced adenine saline added) were obtained from the American Red Cross Blood Services Southeastern Michigan Region and used prior to the out date indicated on each unit.
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tert-Butyl-3-hydroxypropanoate, methyl 3-mercaptopropionate, and ethyl methacrylate were purchased from Acros Organics. 2,2′-Azobis-(isobutyronitrile) (AIBN) and ethyl methacrylate were purchased from Sigma-Aldrich Co. Trifluoroacetic acid (TFA) and solvents were purchased from Thermo Fisher Scientific, Inc. The chemicals were used without further purification, with the exception of methacryloyl chloride which was distilled before use and AIBN which was recrystallized from hot methanol. Boc-amino ethyl methacrylate was synthesized according to the previous reported procedure.61 (link)1H NMR was performed using a Varian MR400 (400 MHz), 13C NMR was performed using a Bruker NEO600 (600 MHz) and the data was analyzed using VNMRJ 3.2 and MestReNova. Gel permeation chromatography (GPC) analysis was performed using a Waters 1515 HPLC instrument equipped with Waters Styragel (7.8 × 300 mm) HR 0.5, HR 1, and HR 4 columns in sequence and detected by a differential refractometer (RI). Mueller Hinton broth (MHB, BD and Company) and phosphate buffered saline (PBS, pH = 7.4, Gibco) were prepared according to manufacturer instructions and sterilized prior to use. Human red blood cells (RBCs) (leukocytes reduced adenine saline added) were obtained from the American Red Cross Blood Services Southeastern Michigan Region and used prior to the out date indicated on each unit.
6
Synthetic Nanostructured Materials Fabrication
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Tetraethylorthosilicate (TEOS) 99% and benzoin methyl ether (BME) 97% were purchased from ABCR; GmbH, 3-(trimethoxysilyl) propylamine 98% (APTES), 3, (3-glycidoxypropyl)trimethoxysilane (GLYMO), divinylbenzene (DVB) technical grade 80%, benzyl metacrylate (BM) 96% containing monomethyl ether hydroquinone as inhibitor, tert-butyl acrylate (tBA) 98% containing 10–20 ppm monomethyl ether hydroquinone as inhibitor, methyl methacrylate (MM) 99% stabilized for synthesis with monomethyl ether hydroquinone as inhibitor, 2-(Dimethylamino)ethyl methacrylate (DAEMA) containing 700–1000 ppm monomethyl ether hydroquinone as inhibitor 98%, ethyl methacrylate (EM) 98% stabilized with 200 ppm hydroquinone, 2,4-dyhydroxy benzaldehyde, ammonium chloride, sodium azide, aluminum oxide (active basic) Brockmann I and N,N-Dimethylformamide anhydrous 99.8% were purchased from Sigma-Aldrich; absolute ethanol (EtOH, 99.3%), hydrochloric acid (HCl), Cu(CH3COO)2·H2O and Co(CH3COO)2·4H2O were purchased from Chemical Company; ammonium hydroxide solution (28–30%) for analysis was purchased from EMSURE ACS. Reag. Ph Eur. Supelco.
7
Enzymatic Biosensor Development Protocol
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Laccase (E.C. 1.10.3.2) (0.5 µg, Sigma Aldrich, St. Louis, MO, USA), Sunset Yellow (98%, Sigma Aldrich), acrylamide (98%, Sigma Aldrich), ethyl methacrylate (97%, Sigma Aldrich), 2,2-dimethoxy-2-phenylacetophenone (99%, Sigma Aldrich), potassium dihydrogen phosphate (99%, Systerm, Shah Alam, Malaysia), alumina (Autolab, Ultrecht, The Netherlands), and dipotassium hydrogen phosphate (99%, Systerm) were used as received without further purification. The biosensor response was measured using a potentiostat (DropSens, Asturias, Spain) and GCE (Autolab).
8
Synthesis and Characterization of Methacrylate Polymers
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Methyl methacrylate (MMA, 99%), ethyl methacrylate (EMA, 99%), butyl methacrylate (BMA, 99%), lauryl methacrylate (LMA, 96%), stearyl methacrylate (SMA, 89.5%), methyl acrylate (MA, 99%), iron(II) bromide (FeBr2, 98%), 2,2-azobis(isobutyronitrile) (AIBN, 98%), glyoxal solution (40 wt% in H2O), 2,6-diisopropylaniline (97%), 2,4,6-trimethylaniline (98%), and shark squalene were purchased from Sigma-Aldrich (Gillingham, UK). Cobalt(II) bromide (CoBr2, 98%) and dimethyl glyoxime (DMG, 99%) were purchased from Acros Organics (Verona, Italy). Diphenyl glyoxime (DPG, 99%) was purchased from Alfa Aesar (Heysham, UK). Bis[(difluoroboryl) diphenylglyoximato]cobalt(II) (PhCoBF) was supplied by DuPont (Wilmington, DE, USA). Technical-grade toluene, propan-2-ol, and diethyl ether were obtained from campus departmental stores. Amaranth squalene was purchased from Wilshire Technologies (Princeton, NJ, USA). Napa Valley Naturals (Stonewall Kitchen, York, ME, USA) grapeseed oil was purchased from a local grocery store. 1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) was obtained from Lipoid (Ludwigshafen, Germany). Poloxamer 188 and glycerol were obtained from Spectrum Chemical (New Brunswick, NJ, USA). Buffer components were obtained from J.T.Baker (Phillipsburg, NJ, USA) or Fluka (Charlotte, NC, USA). All materials were used as supplied without further purification.
9
Antifungal Nail Lacquer Formulation
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Amorolfine HCl was purchased from Ranbaxy Research Laboratories (Haryana, India) and terbinafine HCl from AK Scientific (CA, USA). Diurethane dimethacrylate, ethyl methacrylate, isobornyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxy-2-methylpropiophenone, absolute ethanol, methanol, propan-2-ol, sodium chloride, triethylamine, phosphoric acid 85% wt solution in water and trifluoroacetic acid and a dialysis tubing cellulose membrane (MW 10281) were purchased from Sigma-Aldrich (Dorset, UK). Acetonitrile HPLC gradient grade was purchased from Fisher Scientific (Hertfordshire, UK). A 36 Watt Cuccio Professional UVA nail lamp was purchased from Amazon UK. Nail & Beauty Emporium lintfree wipes (4 ply) were purchased from Just Beauty UK, an online retailer specialising in professional beauty, hair and skin products. Sabouraud dextrose agar was purchased from Oxoid Ltd (Basingstoke, UK). One dermatophyte strain, Trichophyton rubrum (CBS 118892), was used. Curanail® nail lacquer was used as a control in some experiments and was purchased from pharmacies in the UK. Human nail clippings (fingernails) were obtained from healthy volunteers aged between 18 and 65 years (following ethics approval).
10
Monomer Solubility in Aqueous Solutions
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Methyl methacrylate (MMA) (Lot No. EPE1650, Wako Pure Chemical Industries, Osaka, Japan), ethyl methacrylate (EMA) (Lot No. 69796APV, Sigma-Aldrich, St. Louis, Mo, USA), propyl methacrylate (PMA) (Lot No. MKBH9041V, Sigma-Aldrich), butyl methacrylate (BMA) (Lot No. 404N2347, Kanto Chemical, Tokyo, Japan), hydroxyethyl methacrylate (HEMA) (Lot No. 207N2155, Kanto Chemical), and hydroxypropyl methacrylate (HPMA) (Lot No. MKBL8856V, Sigma-Aldrich), were used without further purification. The chemical structures of these compounds are shown in Fig. 2. The solubility of the hydrophobic derivatives MMA, EMA, PMA, and BMA in distilled water at 37°C was determined with HPLC analyses. Aqueous solubility of each monomer is shown in Fig. 3.
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