Abstract
AbstractProton magnetic resonance spectra were obtained for a number of representative phenol–formaldehyde dimers and trimers of known structure and for related compounds having methyl or chloro substituents on the aromatic ring. The data thus obtained, particularly for the methylene protons, were used in the interpretation of the structure of well characterized, linear phenol–formaldehyde polymers and the corresponding halogenated polymers prepared by the condensation of o‐ and p‐chlorophenol with formaldehyde. In all cases there was a shift to lower field as the methylene linkage was varied from para‐para to ortho‐para to ortho‐ortho, although in certain instances the ortho‐para and ortho‐ortho peaks moved very close together. The spectra obtained indicated that the condensation of o‐chlorophenol with formaldehyde proceeds in an essentially random manner, since the ratio of ortho‐ortho to ortho‐para to para‐para methylene linkages was found to be 1:2:1, within the limits of experimental error. The preliminary results obtained in this work clearly demonstrate the potential utility of PMR as a valuable tool in the characterization of the highly complex products obtained from phenol–formaldehyde systems.
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