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Methyl cyanoacrylate (MCA; also sometimes referred to as α-cyanoacrylate or alpha-cyanoacrylate) [3] is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues.
Specific cyanoacrylates include methyl 2-cyanoacrylate (MCA), ethyl 2-cyanoacrylate (ECA, commonly sold under trade names such as "Super Glue" and "Krazy Glue"), n-butyl cyanoacrylate (n-BCA), octyl cyanoacrylate, and 2-octyl cyanoacrylate (used in medical, veterinary and first aid applications
Ethyl cyanoacrylate (ECA), a cyanoacrylate ester, is an ethyl ester of 2-cyano-acrylic acid. It is a colorless liquid with low viscosity and a faint sweet smell in pure form. It is the main component of cyanoacrylate glues and can be encountered under many trade names . [ 2 ]
Structure of the backbone of a cyanoacrylate polymer. In the same way that several variants of acrylic esters are known, so too are the corresponding polymers. Their properties strongly depends on the substituent. A large family of acrylate-like polymers are derived from methyl methacrylate and many related esters, especially polymethyl ...
"Super glue" is a formulation of cyanoacrylate. Polymethyl methacrylate is the clear break-resistant sheeting sold as acrylic glass (or simply acrylic sheet) or under the trade name Plexiglas, Perspex, etc. Polyacrylates are used in cosmetic products as rheology modifiers and film formers, and these are typically polymers of acrylic acid fluids.
Methyl acrylate can be prepared by debromination of methyl 2,3-dibromopropanoate with zinc. [10] Methyl acrylate is formed in good yield on pyrolysis of methyl lactate in the presence of ethenone (ketene). [11] Methyl lactate is a renewable "green chemical". Another patent [12] describes the dehydration of methyl lactate over zeolites.
Ethyl acrylate reacts with amines catalyzed by Lewis acids in a Michael addition to β-alanine derivatives in high yields: [13]. The nucleophilic addition at ethyl acrylate as an α,β-unsaturated carbonyl compound is a frequent strategy in the synthesis of pharmaceutical intermediates.
NBCA in monomer form is soluble in acetone, methyl ethyl ketone, nitromethane, and methylene chloride. [4] It polymerizes rapidly in presence of ionic substances such as moisture, blood, or tissue fluids. NBCA has unique properties compared to other cyanoacrylates such as octyl cyanoacrylate or isoamyl cyanoacrylate.