Methyl isobutyl ketone

Materials were obtained from commercial suppliers and used without further purification. OCA was generously donated by Ethicon, Inc., Raleigh, NC. Methyl ethyl ketone (MEK), methyl isobutyl ketone (MIBK), and cyclohexanone (Sigma Aldrich) were used as solvents and 2,4-toluene diisocyanate (TDI) and 1,4-butanediol (1,4-BD) (Sigma Aldrich) were used to synthesize the polyurethane prepolymer (pPUR) following the protocol outlined by Yang et al. and reported by the authors previously [10 , 18 ]. Pluronic F-68 (Sigma Aldrich) was used as a surfactant. Para-Toluenesulfonic acid (Sigma Aldrich, PTSA) was added to the organic phase as a stabilizer for the OCA monomer. Commercially available Palacos R PMMA bone cement (Zimmer) was used for all experiments reported herein.

All reagents and solvents, including deuterated acetone (acetone-d₆), acetone, methyl isobutyl ketone, 2-heptanone, propanal, acrolein, crotonaldehyde and methanol, were purchased from Sigma-Aldrich. ATM (1, Scheme 1),^{[18 (link)]} and AMAH (2)^{[19 ]} were prepared according to literature procedures. ADMH was synthesized in three steps as follows (Scheme 2): (1) reaction of ethanolamine with N-hydroxyphthalimide (NHP) under standard conditions^{[20 ]} to obtain phthaloyloxy amine 6; (2) hydrazinolyis by treatment of 6 with methylhydrazine at 0 °C in dry dichloromethane followed by Kugelrohr distillation of the deprotected aminooxy product; and (3) acidification using aqueous hydrochloric acid. Recrystallization of the crude salt from isopropyl alcohol afforded ADMH as a white solid.