All chemicals were purchased from Sigma-Aldrich unless otherwise stated. N-Isopropylacrylamide (NIPAAm, VWR) was recrystallized in hexane before use. 2-hydroxyethyl methacrylate (HEMA, Alfa Aesar) and acrylic acid (AAc) was passed through an inhibitor remover column to remove the inhibitors. Dimethyl-γ-butyrolactone acrylate (DBA) was synthesized by acylation of pantolactone [37 (link)]. 2,2′-Azobis(2-methyl-propionitrile), dioxane, hydrogen peroxide (30% aqueous solution), ascorbic acid (Asc), iron (III) chloride hexahydrate, cesium carbonate (Cs2CO3, BTC Beantown Chemical), potasium iodide (KI, BTC Beantown Chemical), nitrilotriacetic acid (NTA, Fisher Scientific), and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP, Oakwood Chemical) were used as received without further purification. TAM radical was synthesized following a previous report [38 (link)]. Bromoethyl methacrylate (BEMA) was synthesized using an established protocol [39 (link)].
2 hydroxyethyl methacrylate hema
Manufactured by Thermo Fisher Scientific
Sourced in United States
2-(Hydroxyethyl) methacrylate (HEMA) is a colorless, viscous liquid organic compound. It is a monomer commonly used in the production of various polymeric materials, including acrylic resins, adhesives, and coatings. HEMA plays a core function as a building block for the synthesis of these materials.
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Lab products found in correlation
Methyl methacrylate, by Thermo Fisher Scientific (2 mentions)
Ethyl 2 bromoisobutyrate, by Merck Group (2 mentions)
Tetrahydrofuran, by Merck Group (2 mentions)
Copper 1 bromide, by Merck Group (2 mentions)
Hydrogen peroxide, by Thermo Fisher Scientific (2 mentions)
2 hydroxy 2 methylbenzene acetone d 1173, by Merck Group (2 mentions)
Ethylene glycol dimethacrylate, by Thermo Fisher Scientific (2 mentions)
1 vinyl 2 pyrrolidinone, by Merck Group (2 mentions)
Anisole, by Thermo Fisher Scientific (1 mentions)
Acryloyl chloride, by Merck Group (1 mentions)
Triethylamine tea, by Avantor (1 mentions)
4 hydroxymethyl phenylboronic acid pinacol ester, by Merck Group (1 mentions)
Benzoyl peroxide bpo, by Thermo Fisher Scientific (1 mentions)
Hydrogen peroxide h2o2, by Merck Group (1 mentions)
Bovine liver catalase, by Thermo Fisher Scientific (1 mentions)
2 2 bipyridine bpy, by Thermo Fisher Scientific (1 mentions)
Ethyl 2 bromoisobutyrate ebib, by Merck Group (1 mentions)
N n dimethylformamide (dmf), by Duksan Pure Chemicals (1 mentions)
Triethylamine, by Avantor (1 mentions)
Copper 1 chloride, by Merck Group (1 mentions)
14 protocols using 2 hydroxyethyl methacrylate hema
1
Synthesis and Characterization of Functional Polymers
2
Synthesis of Cationic Polymers via ATRP
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Methyl methacrylate (MMA) and 2-(hydroxyethyl) methacrylate (HEMA) (both Alfa Aesar, Warsaw, Poland), were dried, whereas [2-(methacryloyloxy)ethyl]trimethylammonium chloride (TMAMA, 80% aq. solution, Sigma-Aldrich, Poznan, Poland) was concentrated to a constant weight by water evaporation. Anisole (99%, Alfa Aesar, Warsaw, Poland) was desiccated using 4Å molecular sieves (Chempure, Piekary Ślaskie, Poland). Copper(I) bromide and chloride (CuBr and CuCl; both Fluka, 98%, Steinheim, Germany) were purified by stirring in glacial acetic acid, followed by filtration and washing with ethanol and diethyl ether, then dried under vacuum; 2,2′-Bipyridine (bpy), 4,4′-dinonyl-2,2′-dipyridyl (dNbpy, 97%), tetrahydrofuran (THF), pyridine (99%), α-bromoisobutyrate bromide (BIBB, 98%), ethyl 2-bromoisobutyrate (EBiB), potassium clavunate (KCLV), and sodium p-aminosalicylate (NaPAS) were used as received (all Sigma Aldrich, Poznan, Poland).
3
Thermoresponsive Polymer Hydrogel Synthesis
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All chemicals were obtained from Sigma-Aldrich unless otherwise described. N-Isopropylacrylamide (NIPAAm, TCI) was recrystallized in hexane 3 times before use. 2-Hydroxyethyl methacrylate (HEMA, Alfa Aesar) was used after passing through a column filled with inhibitor removers. Benzoyl peroxide (BPO, Fisher Scientific) was freeze-dried before polymerization. Acryloyl chloride (Sigma), 4-(hydroxymethyl)-phenylboronic acid pinacol ester (Sigma-Aldrich, HPPE), triethylamine (TEA, VWR), and hydrogen peroxide (H2O2) (30%, Sigma-Aldrich) were used as received. rhMG53 protein was purified from E. coli fermentation as described previously [33 ].
4
Photocatalytic Polymer Synthesis
5
Synthesis and Characterization of Polyurethane-Based Materials
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5,5-dimethylhydantoin (DMH), 4-vinylbenzyl chloride, copper(I) bromide, [2-(Methacryloyloxy) ethyl] dimethyl-(3-sulfopropyl) ammonium hydroxide (SBMA), poly (ethyl glycol) methacrylate (PEGMA, Mn = 360 Da), and ethyl-2-bromoisobutyrate (EBIB) were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO, USA). 2-bromoisobutyryl bromide (BIBB), 2-(Dimethylamino) pyridine, 2-2’-bipyridine (bpy), and 2-hydroxyethyl methacrylate (HEMA) were purchased from Alfa Aesar (Lancashire, UK). Triethylamine and ethanol were purchased from J.T. Baker (Allentown, PA, USA). Methanol, dichloromethane, and toluene were from MACRON (Allentown, PA, USA). N,N-dimethylformamide (DMF) was acquired from Duksan (Ansan, Korea). All the above chemicals were purchased at the highest purity grade. The thermoplastic ester-based polyurethane pellet (TPU, Estane, S385A) was purchased from Lubrizol Advanced Materials, (Inc., Wickliffe, OH, USA).
6
Synthesis of Cationic Methacrylate Polymers
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Methyl methacrylate (MMA) and 2-(hydroxyethyl) methacrylate (HEMA) (both Alfa Aesar) were desiccated using 4 Å molecular sieves (Chempur). [2-(methacryloyloxy)ethyl]trimethylammonium chloride (ChMA/Cl, 80% aq. solution, Sigma-Aldrich) was concentrated to a constant weight by water evaporation. Copper(I) bromide, copper(I) chloride, 2,2′-bipyridine, sodium salicylate (NaSal), tetrahydrofuran (THF), N,N,N′,N″,N″-pentamethyldiethyltriamine (PMDETA) and ethyl 2-bromoisobutyrate (EBiB) were obtained from Sigma Aldrich. Methanol, acetone, DMF, were bought from Chempur.
7
Synthesis and Characterization of Charged Hydrogels
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3-Sulfopropylmethacrylate potassium (MASO3) (98%; Merck KGaA, Darmstadt, Germany), [2-(Methacryloyloxy)ethyl]trimethylammonium chloride (MATMA) (75 wt% in H2O; Merck KGaA, Darmstadt, Germany), [2-(Methacryloyloxy)ethyl]dimethyl-(3-sulfopropyl)ammo-niumhydroxide (MADMASO3) (95%; Merck KGaA, Darmstadt, Germany), (Vinylbenzyl)trimethylammonium chloride (VBTMA) (99%; ACROS Organics, Schwerte, Germany), 2-Acrylamido-2-methyl-1-propanesulfonic acid (AAMPSO3) (99%; Merck KGaA, Darmstadt, Germany), 2-Hydroxyethylmethacrylate (HEMA) (97%; Alfa Aesar, Landau, Germany), N,N’-Methylenebis(acrylamide) (MBAA) (99%; Merck KGaA, Darmstadt, Germany), N,N′-Bis-(acryloyl)-piperazin (BAP) (99%; Merck KGaA, Darmstadt, Germany), N,N, N’,N’-Tetramethylethylendiamine (TMEDA) (≥99.5%; Merck KGaA, Darmstadt, Germany) and Ammonium persulfate (APS) (98%; Roth, Karlsruhe, Germany) were used as received (Scheme 1 ). Additionally, ultrapure water was used throughout the study.
8
Synthesis and Characterization of Dentin Adhesives
9
PDMS-diol Hydrogel Preparation
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Poly(dimethylsiloxane) dialkanol (PDMS-diol, KF-6001) was purchased from Shin-Etsu Chemical Co. Ltd., Tokyo, Japan. 1-Vinyl-2-pyrrolidinone (NVP), tetraethyl orthosilicate (TEOS), and 2-hydroxy-2-methylbenzene acetone (D-1173) were purchased from Sigma-Aldrich (St. Louis, Mo USA). Further, 2-hydroxyethylmethacrylate (HEMA) and ethylene glycol dimethacrylate (EGDMA) were obtained from Acros Organics (NJ, USA). Phosphate buffered saline solution (PBS, 0.1 M, pH 7.4) was prepared in our laboratory.
10
Photosensitizer-based Oxidative Stress Assay
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Rose Bengal sodium salt (RB, MW: 1017.64 g/mol, ≥85%, Sigma, Madrid, Spain), tetrabutylammonium iodide (TBAI, MW: 369.37 g/mol, 98%, Aldrich Chemistry, Madrid, Spain), tetrabutylammonium chloride (TBACl, MW: 277.92 g/mol, ≥97%, Aldrich Chemistry, Madrid, Spain), Sodium iodide (NaI, Fisher Chemical, Madrid, Spain), 2-hydroxyethyl methacrylate (HEMA, MW: 130.14 g/mol, 97%, Acros Organics, Madrid, Spain), poly(ethylene glycol) dimethacrylate average Mn 550 (PEGDMA, Aldrich Chemistry, Madrid, Spain), 2,2′-azo-bis-isobutironitrile (AIBN, 98%, Merck, Madrid, Spain), 9,10-anthracenediyl-bis(methylene) dimalonic acid (ABDA, ≥90% (HPLC)), sodium phosphate monobasic dihydrate (≥99%, Sigma-Aldrich, Madrid, Spain), sodium phosphate dibasic anhydrous (≥99%, Fluka, Madrid, Spain), catalase from bovine liver (aqueous suspension, 10.000–40.000 units/mg protein, Sigma-Aldrich, Madrid, Spain), ammonium iron (II) sulfate hexahydrate (for analysis, Thermo Scientific, Madrid, Spain), xylenol orange sodium salt (Thermo Scientific, Madrid, Spain), sorbitol (≥97%, Fisher, Madrid, Spain), sulphuric acid (96%, Merck, Madrid, Spain) and hydrogen peroxide (for analysis, 35 wt.% solution in water, stabilized, Thermo Scientific, Madrid, Spain). All reagents were used as received.
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