Premium
A study of the oxidative degradation of phenol‐formaldehyde polycondensates using infrared spectroscopy
Author(s) -
Conley Robert T.,
Bieron Joseph F.
Publication year - 1963
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.1963.070070110
Subject(s) - phenol , methylene bridge , chemistry , quinone , degradation (telecommunications) , formaldehyde , infrared spectroscopy , methylene , organic chemistry , polymer chemistry , photochemistry , oxygen , reaction mechanism , phenol formaldehyde resin , catalysis , telecommunications , computer science
An infrared spectrophotometric examination of the oxidative degradation of acid‐ and base‐catalyzed phenol‐formaldehyde polycondensates, novolaks and resoles, respectively, has been carried out in the temperature range form 100–200°C. The existence of structural moieties such as quinone methides and dibenzyl ethers in the cured phenolic resins systems could not be substantiated. The oxidation of phenolic resins was shown to be a stepwise degradation. Attack of oxygen, a surface reaction, was shown to be at the doubly activated methylene bridge linkage to form a substituted dihydroxybenzophenone system. This species was substantiated by the synthesis of polymers containing the ketonic linkage and their spectral identity to the degrading resin. The initial oxidation was shown to continue through the formation of quinone structures and secondary oxidation was shown to continue through the formation of quinone structures and secondary oxidation at these functional linkages to produce carboxylic acids as one of the fragments during chain scission. This degradation mechanism is in good agreement with other supporting experimental data concerning phenolic resin degradation.