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Glycidyl methacrylate

Manufactured by Merck Group
Sourced in United States, Germany, Italy, United Kingdom, Poland, Chile, France, Sao Tome and Principe

Glycidyl methacrylate is a chemical compound used in the production of various synthetic polymers. It is a bifunctional monomer, containing both an epoxide group and a methacrylate group, which allows it to participate in a range of polymerization reactions. The core function of glycidyl methacrylate is to serve as a building block in the synthesis of specialty polymers and copolymers, which find applications in diverse industries.

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136 protocols using glycidyl methacrylate

1

Epoxy Acrylic Resin Formulation via Bulk Photopolymerization

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The following components were used to prepare epoxy acrylic resins (EARs) via the bulk photopolymerization process:

base monomers: n-butyl acrylate (BA), glycidyl methacrylate (GMA), 2-hydroxyethyl acrylate (HEA) (Merck Group, Warsaw, Poland);

methacrylic monomers: methyl methacrylate (MMA), ethyl methacrylate (EMA), butyl methacrylate (BMA), lauryl methacrylate (LMA), (2-acetoacetoxy)ethyl methacrylate (AEM) (Merck Group, Warsaw, Poland)

vinyl monomers: N-vinylpyrrolidone (NVP) (BASF, Ludwigshafen, Germany) and styrene (STY) (Merck Group, Warsaw, Poland),

The chemical structures of the comonomers are shown in Table 1. As a radical photoinitiator, an acylphosphine oxide type photoinitiator was used, i.e., 2,4,6-trimethylbenzoyl-diphenyl phosphine oxide (Omnirad TPO, IGM Resins, Waalwijk, The Netherlands).
Epoxy-acrylate structural adhesive tapes (SATs) were compounded using EARs and the Bisphenol A-based liquid epoxy resin with an epoxy equivalent weight of 202 g/equiv. and viscosity of 25 Pa∙s (Epidian; Ciech Sarzyna, Nowa Sarzyna, Poland), radical photoinitiator Omnirad 127 (IGM Resin, The Netherlands), the multifunctional acrylic monomer (Laromer 9023; BASF, Ludwigshafen, Germany), the Lewis acid adduct (as a latent curing agent) (Nacure Super Catalyst A218; Worleé Chemie, Hamburg, Germany), and an adhesion promoter (Byk 4510 (Byk-Chemie, Wesel, Germany).
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2

Functionalized Cotton Waste Adsorbents

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The starting cotton waste material (CFT) was supplied by an Italian company (C.F.T. PIETRO MASSERINI S.R.L. Company, Gazzaniga, BG, Italy). Hydrogen peroxide (H2O2) solution 30% (w/w), glycidyl methacrylate (GMA), ferrous sulfate heptahydrate (FeSO4∙7H2O), 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO), sodium chloride (NaCl), potassium bromide (KBr), tetra-n-butylammonium fluoride (TBAF), allyl chloride, potassium dihydrogen phosphate (KH2PO4), phosphoric acid (H3PO4), sodium hydroxide (NaOH), sulfuric acid (H2SO4, 95.0–97.0% ACS grade), sodium hypochlorite solution (NaClO, 10%), chlorhexidine digluconate (20% in H2O), hydrochloric acid (HCl, 36.0–38.0% in water), dimethyl sulphoxide (DMSO), absolute ethanol (EtOH), methanol (MeOH), ciprofloxacin (≥98.0%), triethylamine (≥99%, TEA), n-hexane, water and acetonitrile (≥99.9%) for HPLC were purchased from Merck Life Science S.r.l. Milano Italy. Amoxicillin trihydrate and vancomycin Hikma were purchased from dott. Ambreck Pharmacy (Milano, Italy).
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3

Synthesis of MWCNT-Reinforced Epoxy Composites

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Monomers, glycidyl methacrylate (GMA), methyl methacrylate (MMA), allyl methacrylate (ALMA) from Merck Chemical Co., and butyl acrylate (BA) from Fluka were purchased and used as received. Emulsogen APS 100 from Clariant, ter-butyl perbenzoate (TBPB) from Merck Chemical Co., sodium formaldehyde sulfoxylate (SFS), ethylene diamine tertaacetic acid (EDTA), iron (II) sulfate heptahydrate (FeSO4. 7H2O), and ammonium persulphate (APS) from Aldrich, were used without any further purification. MWCNTs with the purity of > 95%, length of 5–15 µm, and outer diameter of 10–20 nm was purchased from Nutrino (Tehran, Iran). The epoxy resin was standard diglycidylether of bisphenol A (DGEBA) (Epon828 from HEXION) with an epoxy equivalent molecular weight between 185 g/eq and 192 g/eq. The curing agent was cycloaliphatic polyamine hardener (Epicure F205 from HEXION) with hydroxyl equivalent weight of 102–106 g/eq. Deionized water (DIW) was used in all recipes.
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4

Chondroitin Sulfate Hydrogel Synthesis

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All used reagents were of analytical grade. Type A gelatin (Gel) from porcine skin (~300 bloom), chondroitin sulfate A sodium salt, anhydrous dimethyl sulfoxide (DMSO), deuterated dimethyl sulfoxide (DMSO-d 6 ), deuterated water (D 2 O), methacrylic anhydride (MAA), nicotinamide (Nic), ammonium peroxydisulfate (APS), N,N,N ′ ,N ′ -tetramethylethylenediamine (TEMED), glycidyl methacrylate (GMA), 4-dimethyl aminopyridine (DMAP), tetrabutylammonium bromide (TBAB), sodium chloride, dialysis membranes (cut-off 12-14 kDa) and L-glutamine were purchased from Merck, (Milan, Italy). Spongostan TM Dental was purchased from Ethicon (Somerville, NJ, USA). Absolute ethanol (EtOH), 37% w/w hydrochloric acid (HCl), monobasic potassium phosphate (KH 2 PO 4 ) and sodium hydroxide in pellets (NaOH) were purchased from Carlo Erba (Milan, Italy). Vybrant ® CDFA SE cell tracer kit, alamarBlue™ cell viability reagent and Primocin TM were purchased from Invitrogen (ThermoFisher Scientific, Waltham, MA, USA) Fetal Bovine Serum (FBS) from Gibco (Buffalo, NY, USA), Dulbecco's Phosphate Buffered Saline (PBS, 1X) from Aurogene (Rome, Italy), DMEM, alpha MEM culture medium and penicillin-streptomycin solution (10,000 U/mL) from Euroclone (Milan, Italy).
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5

Synthesis of Magnetic Polymer Sorbents

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All chemicals used for magnetic sorbent synthesis were analytical grade products and were used as received. Glycidyl methacrylate (GMA), ethylene glycol dimethacrylate (EGDMA), diethylenetriamine (deta), 2,2′-Azobis(2-methylpropionitrile) (AIBN), cyclohexanol, and 1-tetradecanol were obtained from Merck (Darmstadt, Germany). Magnetite (nanopowder with particle size 50 nm, ≥98% trace metals basis) and APTMS were obtained from Sigma-Aldrich (Taufkirchen, Germany). Poly(N-vinyl pyrrolidone) (PVP, Kollidone 90) was purchased from BASF (Ludwigshafen, Germany). Toluene, methanol, and ethanol were obtained from Zorka Pharma (Šabac, Serbia). Potassium dichromate (K2Cr2O7, p.a. purity) was obtained from Merck (Darmstadt, Germany). Deionized water was used for the preparation of the solution.
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6

Photocurable Osteosarcoma Drug Delivery

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GC (≥60% calculated by titration, crystalline, MW ≈ 585,000 g/mol) and glycidyl methacrylate (GM) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Riboflavin 5′-monophosphate sodium salt (riboflavin; Santa Cruz Biotechnology, Inc., Santa Cruz, CA, USA) was used for photo-curing. Doxorubicin·hydrochloride (DOX·HCl; Tokyo Chemical Industry Co., Ltd., Tokyo, Japan) and cisplatin (CP; Sigma-Aldrich, St. Louis, MO, USA) were used for OSA therapy. (2-hydroxypropyl)-beta-cyclodextrin (HP-β-CD; St. Louis, MO, USA) was used to improve the water solubility of CP. Cellulose membrane (cut-off: 20 kDa) was purchased from Spectrum Laboratories Inc. (Rancho Dominguez, CA, USA). MG-63 and KHOS/NP human osteosarcoma cell lines were obtained from American Type Culture Collection (ATCC; Manassas, VA, USA). A cell counting kit-8 (CCK-8; Dojindo Molecular Technologies, Inc. Rockville, MD, USA) was used for in vitro cell viability assay. All chemicals were used as received.
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7

Glycol Chitosan-Based Biomaterial Synthesis

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Glycol chitosan (GC) and glycidyl methacrylate (GM) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Bone morphogenetic protein-2 (BMP-2) and transforming growth factor-beta1 (TGF-β1) were purchased from Thermo Fisher Scientific (Waltham, MA, USA). 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) was obtained from Wako Pure Chemical Industries (Osaka, Japan). Dialysis tubes (Spectrum Laboratories Inc., Rancho Dominguez, CA, USA) were used for purification. The MC3T3-E1 cell line was purchased from the American Type Culture Collection (ATCC; Manassas, VA, USA). α-Minimum Eagle’s medium, fetal bovine serum (FBS), and penicillin and streptomycin (PS) were supplied by Life Technologies (Grand Island, NY, USA). All chemicals were used as received.
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8

Synthesis and Characterization of Polymeric Biomaterials

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4,4-azobis(4-cyanopentanoic acid) (ABCPA), poly(ethylene glycol) methyl ether (Mw 5000 g/mol) (mPEG), N,N’-Dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP), and p-toluenesulfonic acid, L-lactide, N-(2-hydroxypropyl)methacrylamide (HPMAm), Tin(II) 2-ethylhexanoate (SnOct2), and 4-methoxyphenol were purchased from Sigma-Aldrich. All solvents: tetrahydrofuran (THF), dichloromethane (DCM), dimethylformamide (DMF), acetonitrile (ACN), and acetone were provided by Sigma-Aldrich or Fisher Chemical. Nuclear magnetic resonance (NMR) solvents: chloroform-d (CDCl3), deuterated dimethyl sulfoxide (DMSO-d6) and deuterium oxide (D2O) were purchased from Cambridge Isotope Laboratories, Inc. Gelatin from porcine skin (Gel strength 300, type A), methacrylic anhydride, hyaluronic acid sodium salt from Streptococcus equi, glycidyl methacrylate (GM), Eosin Y disodium salt, triethanolamine (TEA) and N-vinylcaprolactam (VC), Triton X-100 were all purchased from Sigma-Aldrich.
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9

Visible-Light-Cured Hydrogel for Cancer Therapy

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GC (≥60% calculated by titration, crystalline, MW ≈ 585,000 g/mol) and glycidyl methacrylate (GM) for visible-light-cured hydrogel preparation were purchased from Sigma-Aldrich (St. Louis, MO, USA). Riboflavin 5′-monophosphate sodium salt (riboflavin) used for photo curing was supplied by Santa Cruz Biotechnology, Inc. (Santa Cruz, CA, USA). Doxorubicin hydrochloride (DOX⋅HCl; Tokyo Chemical Industry Co., Ltd, Tokyo, Japan) and paclitaxel (PTX; Shin Poong Pharm, Co., Ltd.; Ansan, Kyunggi, Republic of Korea) were used for breast cancer therapy. β-CD (Sigma-Aldrich; St. Louis, MO, USA) was used to improve the water solubility of PTX. The cellulose membrane was purchased from Spectrum Laboratories Inc. (Rancho Dominguez, CA, USA) and theMCF-7 human breast cancer cell line was obtained from American Type Culture Collection (ATCC; Manassas, VA, USA). Cell counting kit-8 (CCK-8; Dojindo Molecular Technologies, Inc. Rockville, MD, USA) was used for the in vitro cell viability assay. All chemicals were used as received.
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10

Synthesis and Characterization of Functional Nanomaterials

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The following chemicals
were purchased from
Sigma-Aldrich: ammonia solution (NH4OH, 25%), ethyl ether
(≥99%), hexadecyl trimethylammonium bromide (CTAB, ≥98%),
tetraethylorthosilicate (TEOS, ≥99.99%), (3-aminopropyl)-triethoxysilane
(APTES, ≥98%), bromoacetyl bromide (≥98%), triethylamine
(≥99%), 2-bromoisobutyryl bromide (BIBB, 98%), N-isopropylacrylamide (NIPAm, ≥99%), glycidyl methacrylate
(GMA, ≥97%), tris(2-dimethylaminoethyl)amine (Me6TREN, 96%), copper(I) bromide (99.99%), copper(II) bromide (99%),
Alizarin Red S (ARS, grade certified by the Biological Stain Commission),
copper(II) sulfate (≥99%), sodium ascorbate, sodium azide (≥99.5%),
bovine serum albumin (BSA, ≥98%), ovalbumin from chicken egg
white (OVA, ≥98%), methanol (≥99.9%), tetrahydrofuran
(THF, ≥98%), isopropanol (99.5%), N,N-dimethylformamide (DMF, 99.8%), β-nicotinamide adenine
dinucleotide, reduced disodium salt hydrate (NADH, ≥97%), acetic
acid (≥99%), hydrochloric acid (37%), and lactate dehydrogenase
(LDH) from bovine heart (type III, crystalline suspended in ammonium
sulfate solution). Ethanol (99.5%) was purchased from Solveco. Prior
to use, CuBr was stirred in acetic acid for 24 h, collected by centrifugation,
washed with water and methanol, and dried in a vacuum desiccator.
3-(Prop-2-ynyloxycarbonylamino)phenylboronic acid (PCAPBA) was synthesized
by use of a literature method.22 (link)
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