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2 isocyanatoethyl methacrylate

Manufactured by Tokyo Chemical Industry
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Sourced in Japan

2-isocyanatoethyl methacrylate is a chemical compound used as a laboratory reagent. It is a clear, colorless liquid with a characteristic odor. The primary function of this product is to serve as a versatile building block in the synthesis of various polymeric materials and other chemical compounds.

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Lab products found in correlation

Dibutyltin dilaurate, by Merck Group (2 mentions) Dibutyltin dilaurate dbtdl, by Merck Group (1 mentions) Dimethyl sulfoxide (dmso), by Merck Group (1 mentions) Dimethylformamide, by Merck Group (1 mentions) Irgacure 2959, by Novartis (1 mentions) Choloroform, by Merck Group (1 mentions) Butylated hydroxytoluene, by Merck Group (1 mentions) Trimethylamine, by Merck Group (1 mentions) Dichloromethane, by Merck Group (1 mentions) 2 2 dimethoxy 2 phenylacetophenone, by Merck Group (1 mentions) Hexamethylene diisocyanate, by Merck Group (1 mentions) Triethylamine, by Tokyo Chemical Industry (1 mentions) Ethyl acrylate, by Tokyo Chemical Industry (1 mentions) Acrylic acid, by Tokyo Chemical Industry (1 mentions) Methyl ethyl ketone, by Samchun (1 mentions) Jsm 6380, by JEOL (1 mentions) Azobisisobutyronitrile, by Junsei (1 mentions) Butyl acrylate, by Tokyo Chemical Industry (1 mentions) 2 ethylhexyl acrylate, by Tokyo Chemical Industry (1 mentions) 2 hydroxyethyl acrylate, by Tokyo Chemical Industry (1 mentions)

6 protocols using 2 isocyanatoethyl methacrylate

1

Functionalization of Cellulose Nanocrystals

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Freeze-dried umCNCs were
provided by the
USDA Forest Products Laboratory and used as received. The CNCs were
freeze-dried from an aqueous CNC suspension prepared from a mixed
southern yellow pine dissolving pulp via a 64% sulfuric acid digestion,
as described in detail elsewhere.39 (link) The
umCNCs were determined to contain 0.96% sulfur as residual sulfate
esters. The counterion to the sulfate esters was Na+. The
bifunctional modifier molecule, 2-isocyanatoethyl methacrylate (IEM),
was purchased from TCI America, stabilized with butyl hydroxytoluene
at >98% purity. Dimethyl sulfoxide (DMSO, anhydrous, ≥99.9%),
dimethylformamide (DMF, anhydrous, 99.8%), benzoyl peroxide (BPO,
Luperox A98) and isocyanate catalyst, dibutyltin dilaurate (DBTDL),
were purchased from Sigma-Aldrich and used as received. Molecular
sieves (MS, type 3A, EMD Millipore MX 1583D-1) and toluene (ACS, 99.5%)
were purchased from Alfa Aesar and used as received.
Qu Z., Schueneman G.T., Shofner M.L, & Meredith J.C. (2020). Acrylic Functionalization of Cellulose Nanocrystals with 2-Isocyanatoethyl Methacrylate and Formation of Composites with Poly(methyl methacrylate). ACS Omega, 5(48), 31092-31099.
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2

Synthesis of Methacrylate-Based Hydrogels

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All monomers, reagents, and solvents were obtained from Sigma-Aldrich unless noted otherwise. Polyethylene glycol methacrylate (referred to here as ethoxylated hydroxyethyl methacrylate, EHEMA, to distinguish it as the monomethacrylate component) (Mn=526), urethane dimethacrylate (UDMA, Esstech), polyethylene glycol dimethacrylate (PEGDMA, Mn=550 or 750), tetraethylene glycol dimethacrylate (TTEGDMA), 2-mercaptoethanol (ME), dibutyltin dilaurate, hydroquinone, methyl ethyl ketone (MEK), methanol, hexane, 2-isocyanatoethyl methacrylate (IEM, TCI America) and Irgacure 2959 (Ciba) were used without further purification. Azobisisobutyronitrile (AIBN) was recrystallized from methanol.
Dailing E.A., Setterberg W.K., Shah P.K, & Stansbury J.W. (2015). Photopolymerizable Nanogels as Macromolecular Precursors to Covalently Crosslinked Water-Based Networks. Soft matter, 11(28), 5647-5655.
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3

Synthesis of Thiol-Acrylate Photopolymers

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Hexamethylene diisocyanate (HMDI), dibutyltin dilaurate (DBTDL), butylated hydroxytoluene (BHT), 2,2dimethoxy-2-phenylacetophenone (DMPA), trimethylamine (TEA), dichloromethane (DCM), ethyl ether, choloroform (≥99.5%) were obtained from Sigma-Aldrich. m-Xylene diisocyanate (XDI), 1,3-bis(isocyanatomethyl)cyclohexane (BIC), 2-isocyanatoethyl methacrylate (IEM), triethylene glycol dimethacrylate (TEGDMA) were purchased from TCI America. Polycaprolactone tetra(3mercaptopropionate) (PCL4MP, Mn = 1350), ethoxylated-trimethylolpropan tri(3-mercaptopropionate) (ETTMP, Mn= 700) were donated by Evans Chemetics. All materials were used as received.
Gao G., Shah P.K., Liu T, & Stansbury J.W. (2018). Step-growth Production of Nanogels for Use as Macromers with Dimethacrylate Monomers. Reactive & functional polymers, 134, 85-92.
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4

Graphite-Based Thermal Conductive Adhesive Synthesis

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Butyl acrylate (>99%), 2-ethylhexyl acrylate (>99%), ethyl acrylate (>99%), 2-hydroxyethyl acrylate (>95%), acrylic acid (>99%), abietic acid (>80%), triethylamine (>99%), and 2-isocyanatoethyl methacrylate (>98%) were purchased from Tokyo Chemical Industry. Tris(4-hydroxyphenyl)methane triglycidyl ether (>95%) and dibutyltin dilaurate (95%) were purchased from Sigma-Aldrich Korea Ltd. (Yongin, Korea). Toluene (99.5%), ethyl acetate (99.5%), and methyl ethyl ketone (99.5%) were purchased from Samchun Chemical (Pyeongtaek, Korea). Azobisisobutyronitrile (AIBN, 98%) was purchased from Junsei Chemical (Tokyo, Japan). All chemicals were used as received without further purification. The epoxy crosslinker was used after dilution to a solid content of 5 wt% with Toluene. A 17-μm-thick graphite sheet was purchased from Tanyuan technology (Changzhou, China). A silicone-coated polyethylene terephthalate (PET) film and a polyethylene terephthalate (PET) film were purchased from SKC (Seoul, Korea). A stainless steel (SS) plate was purchased from MMSTECH (Bucheon, Korea). The micro structure of the g-TC film was analyzed using a scanning electron microscope (SEM, JSM 6380, JEOL, Tokyo, Japan) and a digital microscope (MXB-5000REZ, HIROX, Tokyo, Japan).
Lee H.J., Lim G., Yang E., Kim Y.S., Kwak M.G, & Kim Y. (2021). Thermally Conductive Film Fabricated Using Perforated Graphite Sheet and UV-Curable Pressure-Sensitive Adhesive. Nanomaterials, 11(1), 93.
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5

Synthesis of Functional Polymer Materials

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Furfuryl alcohol (FA; 98%), poly(ethylene glycol) methyl ether methacrylate(PEGMMA; average Mn = 500, contains 100 ppm MEHQ and 200 ppm BHT as inhibitor), dibutyltin dilaurate (95%), 1,1′-(methylenedi-4,1-phenylene)bismaleimide (bM; 95%) and 2-hydroxyethyl methacrylate(HEMA; contains 250 ppm monomethyl ether hydroquinone as inhibitor, 97%) were purchased from Sigma-Aldrich and used as received. 2-Furoyl chloride (FC; 98%) and 2-isocyanato ethyl methacrylate (NCO-MA, stabilized with BHT; 98%) were purchased from Tokyo Chemical Industry and used as received. α,α′-Azobis(isobutyronitrile) (AIBN; 98%) was purchased from Tokyo Chemical Industry and recrystallized with ethanol before used. Methylene chloride (MC), N,N-dimethylformamide (DMF), tetrahydrofuran (THF), n-hexane, chloroform, diethyl ether and pyridine (99.5%) were purchased from Daejung Chemicals and used after dehydration with molecular sieves.
Byun K.S., Choi W.J., Lee H.Y., Sim M.J., Cha S.H, & Lee J.C. (2018). The effect of electron density in furan pendant group on thermal-reversible Diels–Alder reaction based self-healing properties of polymethacrylate derivatives. RSC Advances, 8(69), 39432-39443.
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6

Synthesis and Purification of MPC and BMA

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MPC was purchased from NOF Corp. (Tokyo, Japan), which was synthesized and purified at an industrial level and to medical grade specifications, according to a previously reported method. 30 BMA (Kanto Kagaku, Tokyo, Japan) was reagent grade and was purified by vacuum distillation. Fractions of BMA with a boiling point of 63 °C/ 24 mmHg were collected. Benzyl alcohol, n-butanol, and toluene were purchased from Kanto Kagaku and dried using 4A molecular sieves. Benzyl methacrylate (BZMA, FUJIFILM Wako Chemicals), 2,2 0bipyridyl (Bpy, FUJIFILM Wako Chemicals), copper (I) bromide (CuBr, Merck KGaA, Darmstadt, Germany), dibutyltin(IV) dilaurate (DBTL, FUJIFILM Wako Chemicals, Osaka, Japan), indomethacin (Tokyo Chemical Industry), 2-isocyanatoethyl methacrylate (IEMA, Tokyo Chemical Industry, Tokyo, Japan), PVP (Kollidon Ò K30, BASF, Ludwigshafen am Rhein, Germany), and all other reagents and solvents were commercially available extra-pure grade and used with no further purification.
Yoshie K., Yada S., Ando S, & Ishihara K. (2021). Chemical Structural Effects of Amphipathic and Water-soluble Phospholipid Polymers on Formulation of Solid Dispersions. Journal of pharmaceutical sciences, 110(8).
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