RING-OPENING POLYMERIZATION in .NET

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RING-OPENING POLYMERIZATION
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The lactam anion reacts with monomer in the second step of the initiation process by a ring-opening transamidation to form the primary amine anion XXXV. Species XXXV, unlike
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O O O C H (CH2)5 N CO(CH2)5N M + XXXV
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7-60
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C C (CH2)5 N M + + HN (CH2)5
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the lactam anion, is not stabilized by conjugation with a carbonyl group. The primary amine anion is highly reactive and rapidly abstracts a proton from monomer to form the imide dimer XXXVI, N-(E-aminocaproyl)caprolactam, and regenerate the lactam anion.
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O O C C H (CH2)5 N CO(CH2)5N M + + (CH2)5 NH O O
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7-61
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C C (CH2)5 N CO(CH2)5NH2 + (CH2)5 N M + XXXVI
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The imide dimer has been isolated and is the actual initiating species necessary for the onset of polymerization [Hall, 1958; Rothe et al., 1962]. Lactam polymerization is characterized by an initial induction period of low reaction rate as the concentration of imide dimer builds up slowly. The imide dimer is necessary for polymerization because the amide linkage in the lactam is not suf ciently reactive (i.e., not suf ciently electron de cient) toward transamidation by lactam anion. The presence of the exo-carbonyl group attached to the nitrogen in the N-acyllactam increases the electron de ciency of the amide linkage. This increases the reactivity of the amide ring structure toward nucleophilic attack by the lactam anion. Propagation follows in the same manner as the reaction of a propagating N-acyllactam species (XXXVII) and the lactam anion (Eq. 7-62), followed by fast proton exchange with monomer to regenerate the lactam anion and the propagating N-acyllactam XXXVIII (Eq. 7-63).
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O C (CH2)5 N CO(CH2)5NH XXXVII O C M+ (CH2)5 N CO(CH2)5 N CO(CH2)5NH O C (CH2)5 N CO(CH2)5 O C (CH2)5 N CO(CH2)5NH XXXVIII M+ N CO(CH2)5NH O C + (CH2)5 N M +
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7-63 7-62
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O C + (CH2)5 N M +
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O C + (CH2)5 NH
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LACTAMS
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The anionic polymerization of lactams proceeds by a mechanism analogous to the activated monomer mechanism for anionic polymerization of acrylamide (Sec. 5-7b) and some cationic polymerizations of epoxides (Sec. 7-2b-3-b). The propagating center is the cyclic amide linkage of the N-acyllactam. Monomer does not add to the propagating chain; it is the monomer anion (lactam anion), often referred to as activated monomer, which adds to the propagating chain [Szwarc, 1965, 1966]. The propagation rate depends on the concentrations of lactam anion and N-acyllactam, both of which are determined by the concentrations of lactam and base.
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7-3c-2
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Addition of N-Acyllactam
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The use of a strong base alone for lactam polymerization is limiting. There are the induction periods previously noted and, more importantly, only the more reactive lactams, such as E-caprolactam and 7-heptanolactam (-enantholactam), readily undergo polymerization. The less reactive lactams, 2-pyrrolidinone and 2-piperidinone, are much more sluggish toward polymerization by strong base alone. Formation of the imide dimer is dif cult from these relatively unreactive lactams. Both limitations are overcome by forming an imide by reaction of lactam with an acylating agent such as acid chloride or anhydride, isocyanate, monocarbodiimide, and others [Luisier et al., 2002]. Thus, E-caprolactam can be readily converted to an N-acylcaprolactam XXXIX by reaction with an acid chloride. The N-acyllactam can be synthesized in situ or preformed and then added to the reaction system.
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O C (CH2)5 NH
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RCOCl
O C (CH2)5 N CO R XXXIX
7-64
Initiation consists of the reaction of the N-acyllactam with activated monomer followed by fast proton exchange with monomer
C C (CH2)5 N CO R + (CH2)5 N M + O C M+ (CH2)5 N CO(CH2)5 N CO R XL
monomer
7-65
7-66
C C (CH2)5 N CO(CH2)5 NH CO R + (CH2)5 N M + XLI
Species XL and XLI correspond to species XXXV and XXXVI for polymerization in the absence of an acylating agent. The acylating agent achieves facile polymerization of many
RING-OPENING POLYMERIZATION
lactams by substituting the fast initiation sequence in Eqs. 7-65 and 7-66 for the slower sequence in Eqs. 7-60 and 7-61. The use of an acylating agent is advantageous even for the more reactive lactams as induction periods are absent, polymerization rates are higher, and lower reaction temperatures can be used. Polymerizations in the absence and presence of an acylating agent are often referred to as nonassisted and assisted polymerizations, respectively. The terms nonactivated and activated polymerization are also used, but this is confusing since both reactions involve the lactam anion, which is usually referred to as activated monomer. The literature is also confusing with regard to terms used to describe the acylating agent. Activator, promoter, catalyst, and initiator are terms that have been used. Terminology for the strong base is also a problem since its role is not the same for activated and nonactivated polymerizations. The base is needed in both polymerizations for forming the lactam anion (activated monomer). For nonassisted polymerization, the lactam anion is not only the real monomer but is also the species required to form the initiating species (imide dimer). This text will avoid the use of any of these terms for the strong base and acylating agent. Propagation follows in the same manner as for propagation of species XXXVII except that the propagating chain has an acylated end group instead of the amine end group: