Reference

Process of preparing substituted acrylates

Process of preparing substituted acrylates. Ponticello, Ignazio S.; McIntire, John M. (Engl.). 6203-08-3 and 12597-69-2 are also occured in this study. Res. Discl., 151, 31-2 (English) 1976. CODEN: RSDSBB. DOCUMENT TYPE: Journal CA Section: 36 (Plastics Manufacture and Processing) Methylenemalonates are prepd. by treating a substituted norbornene with an electrophilic material in the presence of a Li-amide complex, and pyrolyzing the product; they are useful as fast-setting adhesives. Thus, 1 mol BuLi in hexane was added to a soln. of 1 mol N-isopropylcyclohexylamine in 1 L THF at 0.degree., and the soln. was treated drop-wise with 1 mol 5-carbomethoxy-2-norbornene [6203-08-3] at -78.degree.. The soln. was stirred 15 min at -78.degree., and treated drop-wise with 1 mol allyl chloroformate [2937-50-0] at -78.degree., and stirred 30 min. The resulting norbornene [61518-70-5] (100 g) was pyrolized during 2 h at 650.degree. to yield Me allyl methylenemalonate [61503-51-3], which was spread onto steel plates and polymd. in a few s. The bond exhibited av. lap shear strength 800 psi, which increased to to 2018 psi after 1600 h accelerated weathering. .

Monomers with allylic and methacrylic or acrylic functions

Monomers with allylic and methacrylic or acrylic functions. (Societe Nationale des Poudres et Explosifs, Fr.). Neth. Appl. NL 7709579 9 Mar 1978, 11 pp. (Dutch). (Netherlands). CODEN: NAXXAN. CLASS: IC: C07C125-06. PRIORITY: FR 76-26913 7 Sep 1976. DOCUMENT TYPE: Patent CA Section: 36 (Plastics Manufacture and Processing) Monomers of structure CH2:CHCH2O2CNHZO2CO(CH2)2O2CCR:CH2 (I, Z = C1-4 alkylene, R = H, Me) are prepd. and polymd. to hard, transparent products. Thus, allyl chloroformate [2937-50-0] was condensed with monoethanolamine [141-43-5] to give allyl N-(2-hydroxyethyl)carbamate [66471-00-9], which was phosgenated to allyl N-[2-(chlorocarbonyloxy)ethyl]carbamate (II) [66471-01-0]. Treating II with 2-hydroxyethyl methacrylate [868-77-9] gave the desired compd. I (R = Me, Z = CH2CH2) (III) [66470-38-0]. A soln. of 135 g III in 765 g CHCl3 was heated to 50°, mixed with 0.1844 g Bz2O2, and polymd. 10 h, giving a transparent polymer [66470-39-1] with mol. wt. 150,000, polydispersity 3, and glass temp. -23°. Mixing the polymer with 2% 1,3-bis(tert-butylperoxyisopropyl)benzene, and compression molding 5 min at 170°, and curing 2 h at 110° gave a transparent sheet with Barcol hardness 44 and d. 1.354.