2-Methacryloyloxy-2-methyladamantane

2-Methyl-2-adamantylmethacrylate (2-Methacryloyloxy-2-methyladamantane) is an aliphatic hydrocarbon with a trifluoromethyl group. It is a monomer that can be used to make polymers. 2-Methyl-2-adamantylmethacrylate has been shown to polymerize rapidly and form high molecular weight polymers. It reacts with hydroxyl groups to form ester linkages. This molecule also has the ability to self assemble, making it a supramolecular material. Impurities may affect the polymerization kinetics of this molecule and must be removed before use. As this compound is hydrophobic, it can only be patterned using a sublimable process.

Off-white powder.

2-Methyl-2-adamantylmethacrylate can be used to prepare Analog Semiconductors, Light-Emitting Diodes LED, Solar Photovoltaics PV.

2-Methacryloyloxy-2-methyladamantane as a guest molecule can be introduced onto the silicon substrate by interacting with β-cyclodextrin (β-CD) to construct supramolecular composite surfaces. After the assembly of hydrophilic guest molecules on the main surface, the wettability, water lubrication and resistance to algal cell adhesion of the supramolecular composite surface were improved. This host-guest interface supramolecule provides a new way to prepare water-based lubrication and antifouling materials^[2].

Three different methacrylic monomers (g-butyrolactone methacrylate (GBLMA), 3-hydroxyl-1-adamantyl methacrylate (HAMA), and 2-methyl-2- adamantyl methacrylate (MAMA)) are the most often terpolymerized for 193 nm photoresists. The lactone group of GBLMA plays a vital role in the etching rate, facilitating binding to the substrate. The hydroxyl group of HAMA aids in the solubility and stability of the polymer. MAMA is particularly sensitive to 193 nm light and improves the etching resolution (chemical amplification)[1].

The synthesis of 2-Methyl-2-adamantylmethacrylate is as follows:Add 3546ml of n-heptane in the 5L four-necked flask equipped with stirring paddle, condenser tube and thermometer, turn on stirring, add 126.3g of 2-methyladamantanol to the system, and slowly add 0.022g polymerization inhibitor tetrachlorobenzoquinone to the reaction, add 110.8g basic ion exchange resin, adjust pH=7-8, cool down to -13°C, slowly add 110.8g vinyl methacrylate dropwise to the reaction system, keep the reaction for 7h, monitor the reaction progress, and take samples for detection After the reaction was completed, 1000 ml of water was added to the reaction system, and the mixture was stirred and extracted for phase separation. The organic phase was dried, concentrated under reduced pressure and evaporated to dryness to obtain 167 g of 2-methyl-2-adamantyl methacrylate (2-Methacryloyloxy-2-methyladamantane) product with a yield of 93.78%.

[1] M. Maríc. “Nitroxide‐mediated polymerization of adamantyl‐functional methacrylates for 193 nm photoresists.” Canadian Journal of Chemical Engineering 95 1 (2017): 708–716.
[2] RONGNIAN XU. Promoting Lubricity and Antifouling Properties by Supramolecular-Recognition-Based Surface Grafting[J]. Langmuir, 2018. DOI:10.1021/acs.langmuir.8b02375.