Methacrylic acid

Manufactured by Thermo Fisher Scientific

Sourced in United Kingdom, United States

Methacrylic acid is a colorless, flammable liquid organic compound with the chemical formula CH₃C(CH₃)COOH. It is a weakly acidic carboxylic acid that is used as a monomer in the production of various types of polymers and copolymers.

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Poly(methacrylic acid (2 citations) Methacrylic acid (MAAc) (2 citations) Methacrylic acid (MAA), (2 citations)

18 protocols using methacrylic acid

Synthesis and Characterization of Fluorescent Polymer Nanoparticles

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N-(3-Aminopropyl) methacrylamide hydrochloride (APMA) and N-(2-hydroxypropyl) methacrylamide (HPMA) were purchased from Polysciences, Inc. (Warrington, PA). Methacrylic acid (MAA) was obtained from Acros Organics (Belgium, NJ). 4, 4’-Azobis(4-cyanovaleric acid) (ACVA), 4-cyano-4-(phenyl carbonothioylthio) pentanoic acid (CPAD) and fluorescein O-methacrylate (FMA) were from Sigma-Aldrich (St. Louis, MO). RPMI-1640 medium and Phosphate Buffered Saline (PBS) were from Hyclone (Logan, UT). Fetal bovine serum (FBS) was from Atlanta Biologicals (Flowery Branch, GA). Mouse renal tubular epithelial cells (MCT) were a kind gift from Dr. Rick Schnellmann to Dr. Padanilam and cultured in RPMI supplemented with 10% FBS.

Chen Y., Tang W., Yu F., Xie Y., Jaramillo L., Jang H.S., Li J., Padanilam B.J, & Oupický D. (2019). Determinants of preferential renal accumulation of synthetic polymers in acute kidney injury. International journal of pharmaceutics, 568, 118555.

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Synthesis of Functional Polymeric Materials

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BIS (Fluka, 99.0%), methacrylic acid (MAA; Acros Organics, 99.5%), potassium persulfate (KPS; Sigma-Aldrich, 99.0%), isopropanol (Fisher Chemical, 99.97%), toluene (Fluka Analytical, 99.7%), n-hexane (Sigma-Aldrich; high-performance liquid chromatography–grade, 95%), n-hexadecane (Acros Organics, 99.0%), and 1-decanol (Sigma-Aldrich, ≥98%) were used without further purification. NIPAM (TCI, 98.0%) was purified by recrystallization in 40/60 (v/v) toluene/hexane.

Vialetto J., Ramakrishna S.N, & Isa L. (2022). In situ imaging of the three-dimensional shape of soft responsive particles at fluid interfaces by atomic force microscopy. Science Advances, 8(45), eabq2019.

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Synthesis of Stimuli-Responsive Polymeric Nanocarriers

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Methacrylic acid (MAA, 99%), 2,2′-Azobisisobutyronitrile (AIBN, 98%) and N,N′-methylenebisacrylamide (MBA, 96%) were purchased from Acros. N,N-dimetilaminoethylethacrylate (DMAEMA), Poly(ethyleneglycol)methylethermethacrylate (PEGMA; Mn = 475) and acetonitrile (ACN) were obtained from Sigma-Aldrich., N′-bis(acryloyl)cystamine (BAC, 98%) was purchased from Alfa Aesar. Daunorubicin HCl (DNR) was provided by Pharmacia & Upjohn.

Toniolo G., Efthimiadou E.K., Kordas G, & Chatgilialoglu C. (2018). Development of multi-layered and multi-sensitive polymeric nanocontainers for cancer therapy: in vitro evaluation. Scientific Reports, 8, 14704.

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Synthesis and Characterization of Polymeric Materials

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Methacrylic acid (MAA,
99.5%), IA (99%), and ethylene glycol dimethylacrylate (EGDMA, 98%)
were purchased from Acros Organics. Methyl methacrylate (MMA, 99%),
styrene (St, 99%), N-isopropylacrylamide (NIPAM,
97%), and CDCl₃ (99.8%) used to record ¹H NMR
spectra were purchased from Sigma-Aldrich. Azobisisobutyronitrile
(AIBN, 98%) was purchased from Fluka. Absolute ethanol (EtOH, 99.8%),
hydrochloric acid (HCl) 37% aqueous solution, EtOAc (99.8%), dichloromethane
(DCM, 99.8%), methanol (MeOH, 99.8%), and acetonitrile (MeCN, 99.9%)
of HPLC grade were purchased from Fisher Scientific. Methyl tert-butyl ether (MTBE, 99.9%) was purchased from Lab Scan.
Potassium hydroxide (KOH, 85.8%) pellets and sodium hydrogenphosphate
(Na₂HPO₄, 99%) were purchased from Panreac.
1,3,5-Trimethoxybenzene 99% was purchased from Alfa Aesar. Soxhlet
thimbles were purchased from Merck. Lupanine, with 82% purity, determined
by ¹H NMR, was obtained following a published procedure.^{31 (link)}

Esteves T., Ferreira F.A., Mota A.T., Sánchez-González Á., Gil A., Andrade K.H., Afonso C.A, & Ferreira F.C. (2022). Greener Strategy for Lupanine Purification from Lupin Bean Wastewaters Using a Molecularly Imprinted Polymer. ACS Applied Materials & Interfaces, 14(16), 18910-18921.

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Synthesis and Characterization of Advanced Materials

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The following chemicals were used as received: sodium hydroxide (1 M), sulfuric acid (0.5 M), hexanes (> 99%), anhydrous sodium sulfate and ferrous sulfate were obtained from Fisher Scientific. Sodium borohydride (99.99%), sodium carboxymethyl cellulose (M_w~90k), potassium tetrachloropalladate (II) (98%), biphenyl_d₁₀ (99 atom % D), trichloroethylene (99.5%) and tetrachloroethylene (> 99%) were purchased from Sigma-Aldrich. PVDF powder was purchased from Polysciences, Inc. Potassium persulfate (98%), N,N′-methylenebisacrylamide (NNMA, 99%) and methacrylic acid (99.5%, stabilized) were received from Acros Organics. Nitric Acid (AR select ACS) was ordered from Macron Fine Chemicals. 2-chlorobiphenyl (> 97%) and its analytical solution (100 ppm in hexane) as well as the analytical standards of chloroform (100 ppm in methanol), carbon tetrachloride (100 ppm in methanol) and hexachlorobutadiene (100 ppm in methanol) were obtained from Ultra Scientific. Ethanol (200 proof) was bought from EMD Millipore Corporation. Full scale PVDF 700 microfiltration membranes were obtained from Solecta, Inc. DVPP04700 membranes were purchased from Millipore. Deoxygenated water was obtained by purging N₂ into deionized ultra-filtered (DIUF) water for 30 min.

Wan H., Islam M.S., Briot N.J., Schnobrich M., Pacholik L., Ormsbee L, & Bhattacharyya D. (2019). Pd/Fe nanoparticle integrated PMAA-PVDF membranes for chloro-organic remediation from synthetic and site groundwater. Journal of membrane science, 594, 117454.

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Vitamin K-based Polymer Thin Films

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Methacrylic Acid (MAA), chloroform, and aluminum oxide were purchased from Acros Organics. Methanol absolute, acetic acid, and toluene were bought from Biosolve Chimie SARL (Valkenswaar, The Netherlands). Phylloquinone (vitamin K₁), PolyVinylChloride (PVC), and Menadione (vitamin K₃) were supplied by Sigma-Aldrich (Zwijndrecht, The Netherlands). Acetone pure and Phosphate-Buffered Saline (PBS) tablets were purchased from VWR chemicals (Amsterdam, The Netherlands). Ethylene Glycol DiMethAcrylate (EGDMA) was procured from Merck Schuchardt OHG (Hohenbrunn, Germany). dl-α-Tocopherol, 97+% (Vitamin E) was supplied by Alfa Aesar (Karlsruhe, Germany). PolyDiMethySiloxane (PDMS) stamps were made with the Sylgard 184 elastomer kit from Mavom NV (Kontich, Belgium). Aluminum chips were purchased at Brico NV (Korbeek-Lo, Belgium) and cut to the desired dimensions.

Eersels K., Diliën H., Lowdon J.W., Steen Redeker E., Rogosic R., Heidt B., Peeters M., Cornelis P., Lux P., Reutelingsperger C.P., Schurgers L.J., Cleij T.J, & van Grinsven B. (2018). A Novel Biomimetic Tool for Assessing Vitamin K Status Based on Molecularly Imprinted Polymers. Nutrients, 10(6), 751.

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Polymer Synthesis and Characterization

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Ethylene glycol dimethacrylate (EGDMA), methacrylic acid (MAA), dopamine hydrochloride salt (99%), and methanol were purchased from Acros (Loughborough, Leicestershire, UK). Prior to polymerization, the stabilizers in the MAA and EGDMA were removed by passing the solutions over a column packed with alumina. 4,4’-Azobis(4-cyanovaleric acid) and serotonin creatinine sulfate monohydrate (98%) were purchased from Sigma Aldrich (Gillingham, UK). For the heat-transfer measurements, a 1× phosphate buffered saline (PBS) solution was prepared with Dulbecco tablets obtained from Oxoid Limited (Basingstoke, UK).

Peeters M.M., van Grinsven B., Foster C.W., Cleij T.J, & Banks C.E. (2016). Introducing Thermal Wave Transport Analysis (TWTA): A Thermal Technique for Dopamine Detection by Screen-Printed Electrodes Functionalized with Molecularly Imprinted Polymer (MIP) Particles. Molecules, 21(5), 552.

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Fabrication and Characterization of pMA Bioimprint

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pMA polymer was prepared from a 6:3:1 mixture of ethylene glycol dimethacrylate (EGDMA) (Sigma Aldrich, St Louis, MO, USA): methacrylic acid (Acros Organics, Thermo Fisher Scientific): Irgacure^® 2022 (Ciba Specialty Chemicals, Basel, Switzerland). Next, the EGDMA mixture was cured rapidly (240 seconds) under 40% ultraviolet (UV) light (Omnicure S2000; EXFO, Toronto, ON Canada). Next, the EGDMA mixture was pipetted over the fixed cells, which formed an imprinted disk; the surface of the pMA disk captured the impression of the cells. On the other hand, flat pMA was made by curing the same mixture on cell-free glass slides.
Disks of pMA Bioimprint and flat disks were cleaned by sonication in 10% sodium dodecyl sulfate (SDS), followed by shaking with trypsin (0.05%) for at least 40 minutes. The disks were then soaked in double-distilled water overnight, followed by sterilization in absolute ethanol and washing with DMEM-F12 without FBS. Prior to cell seeding, disks were fitted into 24-well plates and cells were grown on their surfaces.

Tan L.H., Sykes P.H., Alkaisi M.M, & Evans J.J. (2015). The characteristics of Ishikawa endometrial cancer cells are modified by substrate topography with cell-like features and the polymer surface. International Journal of Nanomedicine, 10, 4883-4895.

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Molecularly Imprinted Polymer Synthesis

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The chemicals for the MIP synthesis, ethylene
glycol dimethacrylate (EGDMA), methacrylic acid (MAA), dopamine hydrochloride
salt (purity 99%), and the initiator 4,4′-azobis(4-cyanovaleric
acid), were purchased from Acros (Loughborough, United Kingdom). Hydrocortisone
(purity 98%) and azobis(isobutyronitrile) were purchased from Acros
(The Netherlands). Stabilizers in the monomers MAA and EGDMA were
removed by running the solutions over an alumina packed column. PLLA
1010, used as the adhesive layer, was ordered from Corbion Purac (Amsterdam,
The Netherlands). Thermocouples type K (0.5 mm × 30 mm) were
obtained from TC Direct (Maarssen, The Netherlands).

Diliën H., Peeters M., Royakkers J., Harings J., Cornelis P., Wagner P., Steen Redeker E., Banks C.E., Eersels K., van Grinsven B, & Cleij T.J. (2017). Label-Free Detection of Small Organic Molecules by Molecularly Imprinted Polymer Functionalized Thermocouples: Toward In Vivo Applications. ACS Sensors, 2(4), 583-589.

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Synthesis and Characterization of Novel Psychoactive Substances

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Ethylene glycol dimethacrylate (EGDMA), divinylbenzene (DVB), trimethylolpropane trimethacrylate (TRIM) and methacrylic acid (MAA) were purchased from Acros (Loughborough, UK). Prior to polymerization, the stabilizers in the monomers and crosslinker monomers were removed by passing the solutions over a column packed with alumina. Initiator 4,4′-azobis(4-cyanovaleric acid), ketamine hydrochloride, 3,4-methylenedioxymethamphetamine hydrochloride (MDMA), caffeine and solvents were obtained from Sigma Aldrich (Gillingham, UK). Diphenidine and the positional isomers of methoxphenidine (Scheme 1) were prepared, under UK Home Office license, as their corresponding hydrochloride salts using the procedure reported by Geyer et al. 5 The street sample was obtained from BRC Fine Chemicals (http://www.brc-finechemicals.com) prior to the legislative change. The Psychoactive Substances Act (2016), which came in effect on the 26 th May 2016, makes it an offence to manufacture, supply, possess and import and export psychoactive substances named in this Act, which includes MXP derivatives and their isomers. Structure and purity (>99%) of the target compounds was determined by NMR analysis and GCMS respectively. 5 All solutions were prepared with deionized water of a resistivity of 18.2 Ω cm or with home-made phosphate buffered saline (1× PBS) solutions.

Lowdon J.W., Alkirkit S.M.O., Mewis R.E., Fulton D., Banks C.E., Sutcliffe O.B, & Peeters M. (2018). Engineering molecularly imprinted polymers (MIPs) for the selective extraction and quantification of the novel psychoactive substance (NPS) methoxphenidine and its regioisomers. The Analyst, 143(9).

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