ISSN:
0021-8995
Keywords:
Chemistry
;
Polymer and Materials Science
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Mechanical Engineering, Materials Science, Production Engineering, Mining and Metallurgy, Traffic Engineering, Precision Mechanics
,
Physics
Notes:
The extensive use of N-p-tolylglycine (NTG) and analogous compounds in adhesive bonding technologies requires a better understanding of their role in initiating free-radical polymerization. The fast oxidation and reduction reactions of NTG proceed via the formation of various free radicals and radical cation and anion intermediates. These intermediates were identified and their reactivity with oxygen, to produce the corresponding peroxyl radicals, was measured. Hydroxyl radicals (ȮH) were used to initiate oxidation reactions of NTG, while the reduction reactions were initiated with hydrated electrons (eaq-). OH radicals react with NTG predominately by addition to the aromatic ring followed by OHÞ elimination to produce NTG+· radical cations. In the presence of oxygen, the OH-NTG• adduct also reacts with oxygen to produce peroxyl radicals. The reaction of NTG with eaq- forms the radical anion, which subsequently protonates on the aromatic ring to produce cyclohexadienyl radicals, or undergoes an amine elimination to yield an acetic acid free radical and 4-methylaniline. Hydroperoxyl radicals (HO•2) abstract hydrogen from the α position of NTG to form the corresponding alkyl free radical. © 1994 John Wiley & Sons, Inc.This article is a US Government work and, as such, is in the public domain in the United States of America.
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/app.1994.070540807
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