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The weakness of the allylic C bond arises from the high resonance stability of the allylic H radical (XXXIV) that is formed Degradative chain transfer competes exceptionally well with normal propagation, and the polymer chains are terminated by transfer after the addition of only a very few monomer units That the allylic C bond is the one broken in the transfer H reaction has been shown [Bartlett and Tate, 1953] by experiments with CH2 CH 2 CD OCOCH3 The deuterated allyl acetate polymerizes 19 29 times as fast as normal allyl acetate and has a degree of polymerization 24 times as large under the same conditions This is what would be expected since the C bond is stronger than the C bond because of its D H lower zero-point energy and degradative chain transfer would therefore be decreased in the deuterated monomer.

The allylic radicals that are formed are too stable to initiate polymerization, and the kinetic chain also terminates when the transfer occurs The allylic radicals undergo termination by reaction with each other or, more likely, with propagating radicals [Litt and Eirich, 1960] Reaction 3-155 is equivalent to termination by an inhibitor, which is the monomer itself in this case In this polymerization the propagation and termination reactions will have the same general kinetic expression with rst-order dependencies on initiator and monomer concentrations, since the same reactants and stoichiometry are involved The degree of polymerization is simply the ratio of the rate constants for propagation and termination and is independent of the initiator concentration The low reactivity of a-ole ns such as propylene or of 1,1-dialkyl ole ns such as isobutylene toward radical polymerization is probably a consequence of degradative chain transfer with the allylic hydrogens.

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Deferred 6s of 1790, paying 6% after 1800, same redemption terms. 3s of 1790, redeemable at the pleasure of the government at 100.

It should be pointed out, however, that other monomers such as methyl methacrylate and methacrylonitrile, which also contain allylic C bonds, do not H undergo extensive degradative chain transfer This is due to the lowered reactivity of the propagating radicals in these monomers The ester and nitrile substituents stabilize the radicals and decrease their reactivity toward transfer Simultaneously the reactivity of the monomer toward propagation is enhanced These monomers, unlike the a-ole ns and 1,1-dialkyl ole ns, yield high polymers in radical polymerizations..

fact, considered as one molecule. The nongel portion of the polymer remains soluble in solvents and is referred to as sol. As the polymerization and gelation proceed beyond the gel point, the amount of gel increases at the expense of the sol as more and more polymer chains in the sol are crosslinked to the gel. There is a dramatic physical change that occurs during the process of gelation. The reaction mixture is transformed into a polymer of in nite viscosity. The crosslinking reaction is an extremely important one from the commercial standpoint. Crosslinked plastics are increasingly used as engineering materials because of their excellent stability toward elevated temperatures and physical stress. They are dimensionally stable under a wide variety of conditions due to their rigid network structure. Such polymers will not ow when heated and are termed thermosetting polymers or simply thermosets. More than 10 billion pounds of thermosets are produced annually in the United States. Plastics that soften and ow when heated, that is, uncrosslinked plastics, are called thermoplastics. Most of the polymers produced by chain polymerization are thermoplastics. Elastomers are a category of polymers produced by chain polymerization that are crosslinked (Sec. 1-3), but the crosslinking reactions are different from those described here (Sec. 9-2). In order to control the crosslinking reaction so that it can be used properly, it is important to understand the relationship between gelation and the extent of reaction. Two general approaches have been used to relate the extent of reaction at the gel point to the composition of the polymerization system based on calculating when X n and X w , respectively, reach the limit of in nite size. 2-10a 2-10a-1 Carothers Equation: X n ! 1 Stoichiometric Amounts of Reactants

GROUND (Connected to negative side of power)

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