CYANOACRYLATE

ACRYLIC ESTERPOLYTffiRS - 2-CYANOACRYLIC ESTpRpOLYTffiRS] (Vol 1) -dyeing of pYES, APPLICATION AND EVALUATION] (Vol 8)... 

Table 2. Cured Bulk Properties of Common 2-Cyanoacrylic Esters...

Table 3. Adhesive Bond Properties of 2-Cyanoacrylic Esters with Metals and Various Polymeric Materials...

The 2-cyanoacryhc esters have sharp, pungent odors and are lacrimators, even at very low concentrations. These esters can be irritating to the nose and throat at concentrations as low as 3 ppm eye irritation is observed at levels of 5 ppm (13). The TLV for methyl 2-cyanoacrylate is 2 ppm and the short-term exposure limit is 4 ppm (14). Good ventilation when using the adhesives is essential. 

The diverse nature of the cyanoacrylate adhesives appHcations illustrates vividly that there is no truly typical appHcation. The number of appHcations ia which these adhesives are used is being expanded daily as technological improvements continue to broaden their capabiUties. 

Acrylic Ester Polymers, 2-Cyanoacrylic Ester Polymers" ia ECT 3rd ed., VoL 1, pp. 408—413, by H. W. Coover, Jr., andj. M. Mclatire, Tennessee Eastman Company. 

Acrylic Adhesives. Acryhc stmctural adhesives can be classified into three major types the surface-activated acryhcs (anaerobics), the surface-activated second-generation acryhcs, and the cyanoacrylates. 

Cyanoacrylate adhesives (Super-Glues) are materials which rapidly polymerize at room temperature. The standard monomer for a cyanoacrylate adhesive is ethyl 2-cyanoacrylate [7085-85-0], which readily undergoes anionic polymerization. Very rapid cure of these materials has made them widely used in the electronics industry for speaker magnet mounting, as weU as for wire tacking and other apphcations requiring rapid assembly. Anionic polymerization of a cyanoacrylate adhesive is normally initiated by water. Therefore, atmospheric humidity or the surface moisture content must be at a certain level for polymerization to take place. These adhesives are not cross-linked as are the surface-activated acryhcs. Rather, the cyanoacrylate material is a thermoplastic, and thus, the adhesives typically have poor temperature resistance. 

Acryhc stmctural adhesives have been modified by elastomers in order to obtain a phase-separated, toughened system. A significant contribution in this technology has been made in which acryhc adhesives were modified by the addition of chlorosulfonated polyethylene to obtain a phase-separated stmctural adhesive (11). Such adhesives also contain methyl methacrylate, glacial methacrylic acid, and cross-linkers such as ethylene glycol dimethacrylate [97-90-5]. The polymerization initiation system, which includes cumene hydroperoxide, N,1S7-dimethyl- -toluidine, and saccharin, can be apphed to the adherend surface as a primer, or it can be formulated as the second part of a two-part adhesive. Modification of cyanoacrylates using elastomers has also been attempted copolymers of acrylonitrile, butadiene, and styrene ethylene copolymers with methylacrylate or copolymers of methacrylates with butadiene and styrene have been used. However, because of the extreme reactivity of the monomer, modification of cyanoacrylate adhesives is very difficult and material purity is essential in order to be able to modify the cyanoacrylate without causing premature reaction. 

Tetraethylene glycol may be used direcdy as a plasticizer or modified by esterification with fatty acids to produce plasticizers (qv). Tetraethylene glycol is used directly to plasticize separation membranes, such as siHcone mbber, poly(vinyl acetate), and ceUulose triacetate. Ceramic materials utilize tetraethylene glycol as plasticizing agents in resistant refractory plastics and molded ceramics. It is also employed to improve the physical properties of cyanoacrylate and polyacrylonitrile adhesives, and is chemically modified to form polyisocyanate, polymethacrylate, and to contain siHcone compounds used for adhesives. 

Figure 4c illustrates interfacial polymerisation encapsulation processes in which the reactant(s) that polymerise to form the capsule shell is transported exclusively from the continuous phase of the system to the dispersed phase—continuous phase interface where polymerisation occurs and a capsule shell is produced. This type of encapsulation process has been carried out at Hquid—Hquid and soHd—Hquid interfaces. An example of the Hquid—Hquid case is the spontaneous polymerisation reaction of cyanoacrylate monomers at the water—solvent interface formed by dispersing water in a continuous solvent phase (14). The poly(alkyl cyanoacrylate) produced by this spontaneous reaction encapsulates the dispersed water droplets. An example of the soHd—Hquid process is where a core material is dispersed in aqueous media that contains a water-immiscible surfactant along with a controUed amount of surfactant. A water-immiscible monomer that polymerises by free-radical polymerisation is added to the system and free-radical polymerisation localised at the core material—aqueous phase interface is initiated thereby generating a capsule sheU (15). 

Only small amounts of nitromethane are used as solvent, but it is used in specialized appHcations such as the solublization of a-cyanoacrylate glue and acryhc polymers. Also, nitromethane is useflil as solvent for single-phase Friedel-Crafts reactions (115). 

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