2-(Acetoacetoxy)ethyl methacrylate → 1-Methylcyclopentyl methacrylate

Participants

Reaction Steps

An exemplary AAEM-based photoresist polymer (Polymer 1) was prepared according to a procedure similar to the following procedure. A solution of 1-isopropyl-adamantanyl methacrylate (IPAMA) (20 mmol), 1-methylcyclopentyl methacrylate (MCPMA) (20 mmol), 2-oxo-tetrahydro-furan-3-yl methacrylate (α-GBLMA) (30 mmol), 3-oxo-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-yl methacrylate (ODOTMA) (20 mmol), and 2-(acetoacetyloxy)ethyl methacrylate (AAEM) (10 mmol) dissolved in 30 g of tetrahydrofuran (THF) is degassed by bubbling with nitrogen and charged to a 500 ml flask equipped with a condenser, nitrogen inlet and mechanical stirrer, along with an additional 10 g of degassed THF. The solution is brought to reflux, and 5 g of dimethyl-2,2-azodiisobutyrate is dissolved in 5 g of THF and charged in to the flask. The polymerization mixture is then stirred for about 4 hours at reflux, after which time the reaction is diluted with 5 g of THF and the polymerization mixture cooled to room temperature. The polymer is precipitated by addition to 1.0 L of isopropanol, collected by filtration, re-precipitated by dissolving in 50 g THF and addition to another 1.0 L isopropanol, and collected and dried under vacuum at 45° C. for 48 h. to yield the polymer poly(IAMA/_MCPMA/α-GBLMA/ODOTMA/AAEM) (20/20/30/20/10). Mw=10,400; Mw/Mn=1.53.

Provenance & Evidence