Acrylonitrile methacrylonitrile

Copolymerization of butadiene with another monomer such as acrylonitrile, methacrylonitrile, styrene, or methyl vinyl ketone increases perceptibly the proportion of 1,4 units at the expense of 1,2. The ratio of cis to trans is not materially altered, however. One is obliged to conclude that the co-monomer shows a greater preference for addition to the terminal carbon (i.e., to carbon 4) of the resonating chain radical than does the butadiene Foster and... 

Hashimoto S, Bandow H, Akimoto H, et al. 1984. Products and mechanism for the OH radical initiated oxidation of acrylonitrile, methacrylonitrile and allylcyanide in the presence of NO. International Journal of Chemical Kinetics 16 1385-1399. 

Dimethylstyrene a-Methylstyrene o-Chlorostyrene Acrylonitrile Methacrylonitrile Acrylic acid... 

The fact that allyltributyltin and styrene which are electroneutral were successfully added to PCTFE led us to the question "Can electron-rich or electron-poor trapping agents be used ". The electron-rich agents that we examined were ethyl ethynyl ether and ethyl vinyl ether. On the side of the electron-poor alkenes, eight were investigated ethyl acrylate, methyl methacrylate, methyl vinyl ketone, acrylonitrile, methacrylonitrile, vinyl bromide, chloromethyl styrene, and 4-vinylpyridine. The details of each reaction are summarized. 

In the case of the electron poor alkenes, results were more varied. Under all conditions examined, reactions with methyl vinyl ketone, acrylonitrile, methacrylonitrile and 4-vinyl pyridine afforded products with IR spectra equivalent to those obtained without the addition of the alkene (side reaction). In the cases of vinyl bromide and chloromethyl styrene, unreacted PCTFE was recovered unchanged. It is speculated that electron transfer to the alkene proceeded in each case. While the product of vinyl bromide reduction was not observed, perhaps because of volatility, one could isolate poly(chloromethylstyrene) in the latter case. 

Ohashi et al. [136,139] have proposed a scheme describing the formation of ortho adducts and substitution products from anisole and the three dimethoxyben-zenes with acrylonitrile, methacrylonitrile, and crotonitrile (Scheme 39). Here, the ortho cycloadduct is supposed to be formed directly from an encounter complex or exciplex, whereas the substitution product arises via formation of an ion pair from the complex, followed by protonation of the radical anion and radical... 

Similar results were obtained [139] with the three dimethoxybenzenes and acrylonitrile, methacrylonitrile, and crotonitrile. The amounts of substitution products decrease in the order acrylonitrile (49%) > methacrylonitrile (45%) > crotonitrile (6%), which agrees with the electron affinities of these compounds. Simultaneously, the amount of addition product increases acrylonitrile, 0% methacrylonitrile, 38% crotonitrile, 67%. In the series of anisole and the dimethoxybenzenes with crotonitrile, the amount of substitution products decrease in the order ortho- and para-dim ethoxy benzene > meta-dimethoxyben-zene > anisole, which is just the reverse of the order of their oxidation potentials. Ohashi et al. [139] have attempted to relate the photochemical behavior of these systems to the free enthalpy of electron transfer in the excited state as calculated with the Rehm-Weller equation, AG = E(D/D+) - E(A /A) - el/eR - AE00. 

Nitriles are cyanogenic substances — substances that produce cyanide when metabolized. It is likely that nitriles are teratogens because of maternal production of cyanide in pregnant females. A study of the teratogenic effects on rats of saturated nitriles, including acetonitrile, propionitrile, and n-butyronitrile, and of unsaturated nitriles, including acrylonitrile, methacrylonitrile, allylnitrile, m-2-pcntenenitrile, and 2-chloroacrylonitrile, has shown a pattern of abnormal embryos similar to those observed from administration of inorganic cyanide.6... 

The polar monomers cited include acrylic acid, acrylic esters, meth-acrylic acid, methacrylic esters, acrylonitrile, methacrylonitrile, acrolein, and vinyl acetate. While this list is reasonable, it also includes vinyl halides and vinylidene halides, although no examples with the latter are given. In view of the fact that the vinyl and vinylidene halides do not form complexes with Friedel-Crafts catalysts, these monomers would not be expected to be operable, as demonstrated by the results of Imoto (30). 

Other vinyl monomers, such as acrylonitrile, methacrylonitrile, tert.-butyl vinyl ketone and methyl isopropenyl ketone, polymerize at 203 K, i. e. most probably by non-radical mechanisms. Even here, conversion of monomer to polymer is not complete, and utilization of the initiator is low. Only the polymerization of acrylate momomers proceeds to full monomer consumption at low temperatures. Additional monomer, even when introduced after some delay, is also polymerized. This indicates that a part of the active centres remains living for some time. However, the number of high-molecular-weight chains is lower than the number of added initiator molecules. At the same time, initiation is very rapid [163]. 

The chain tacticity of PMMA synthesized by GTP catalyzed by nucleophiles at different temperatures was analyzed by Webster and coworkers The syndiotactic content increases from 50% at 60 °C up to 80% at —90°C in THF, using tris(dimethylamino)sulfonium bifluoride [(Me2N)3S+ HF2 ] as catalyst . In contrast to the anionic polymerization of MMA, the stereoselectivity of GTP is less sensitive to solvent. It must be noted that PMMA is less syndiotactic when the GTP is catalyzed by nucleophiles rather than by Lewis acids . GTP was extended to the living polymerization of many acrylates and methacrylates, such as nBuMA, glycidyl-MA, 2-ethylhexyl-MA, Me3SiOCH2CH2-MA, sorbyl-MA, allyl-MA, lauryl-MA), acrylates (EA, BuA), acrylonitrile, methacrylonitrile and Al,A-dimethylacrylamide . 

In formations of ternary complexes, the acceptor vinyl compound must have a double bond conjugated to a cyano or to a carbonyl group. Such acceptors are acrylonitrile, methacrylonitrile, acrylic and methacrylic esters and acids, methyl vinyl ketone, acrylamide, etc. Donor monomers are styrene, a-methyl styrene, butadiene, 2-3-dimethyl butadiene, isoprene, chloroprene, etc. 

Acrylonitrile/methacrylonitrile copolymer Synonyms Poly (acrylonitrile-co-methacrylonitrile)... 

Poly (acrylonitrile-butadiene-styrene) Poly (acrylonitrile-co-butadiene-co-styrene). See Acrylonitrile/butadiene/styrene copolymer Poly (acrylonitrile-co-methacrylonitrile). See Acrylonitrile/methacrylonitrile copolymer Poly (acrylonitrile), fibers. See Polyacrylonitrile Polyaldo 2010 KFG. See Polyglyceryl-10 dioleate... 

Acrylonitrile/methacrylonitrile copolymer dental alloys Aluminum Gold Silver dental amalgam Zinc... 

Just like acrylonitrile, methacrylonitrile does not polymerize thermally but polymerizes readily in the presence of free-radical initiators. Unlike polyacrylonitrile, polymethacrylonitrile is soluble in some ketone solvents. Bulk polymerizations of methacrylonitrile have the disadvantage of long reaction time. The rate, however, accelerates with temperature. The polymer is soluble in the monomer at ambient conditions [262]. 

MA)-methyl methacrylate, (p-dioxene-MA)-2-chloroethyl acrylate, (l,3-cyclooctadiene-MA)-acrylonitrile, and (anethole-MA) with acrylonitrile, methacrylonitrile, or 2-chloroethyl acrylate, the event can possibly be explained by assuming that each free-radical has acceptor properties. Raetzsch et discuss this concept. 

Typical examples of monomers, which can polymerize in anionic way are 2-nitropropene, acrylonitrile, methacrylonitrile, esters of acrylic and methacrylic acid, butadiene, styrene and izopropene. 

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