Synthetic Tannins, Their Synthesis, Industrial Production and ApplicationGrasser, Georg
Science
Synthetic Tannins, Their Synthesis, Industrial Production and Application
Grasser, Georg
Tannins
The phenolsulphonic acids are strong, rather stable acids; their
alcoholic hydroxyl-hydrogen atom may, similarly to that of the phenols,
be substituted by a metal or an alkyl radical.
From [Greek: a]- and [Greek: b]-naphthol a number of sulphonic acids may
easily be prepared; viz., mono-, di-, and trisulphonic acids. Nearly
all these acids are important as basic materials in the dyestuff
industry, especially 2,6-[Greek: b]-naphtholmonosulphonic acid (S-acid),
2,3,6-[Greek: b]-naphtholdisulphonic acid (R-acid) and 2,6,8-[Greek:
b]-naphtholdisulphonic acid (G-acid).
2. Condensation of Phenols
Phenolsulphonic acids exhibit pronounced tendencies to condensation, for
which purpose A. v. Baeyer (1872) employed aldehydes. The reaction is
rather violent, and yields, in addition to well-defined crystalline
substances, amorphous bodies resembling rosins. In addition to
formaldehyde, paraformaldehyde, trioxymethylene, methylal,
hexamethylene-tetramine, and other substances containing a reactive
methylene group, as well as acetaldehyde, benzaldehyde and other
aldehydes may be employed to induce reaction.
A number of these condensation products are derivatives of diphenylamine
or hydroxybenzyl alcohols. When the latter are heated, either by
themselves or in presence of acids, anhydrides and polymerisation
products are formed producing hard, brittle, fusible substances,
insoluble in water but fairly soluble in organic solvents. The same
substances are formed when phenols are condensed with formaldehyde,
especially in the presence of acid contact substances and excess of
phenol by sufficiently long heating at certain temperatures. The
substances referred to are termed "Novolak": similar to these are the
so-called "Resols," insoluble and non-fusible substances, very resistant
to chemical and physical action. Another member of the series is the
so-called "Bakelite" or "Resitol," which does not fuse but softens when
heated and swells in organic solvents. The ultimate product of this
class of substances is "Resit" which is obtained when concentrated
hydrochloric acid is allowed to act upon a mixture of phenol and
formaldehyde; the temperature rises spontaneously, and a hard, porous,
insoluble mass of great resistance is obtained. By heating resols,
resitols are formed which, on further heating, are finally converted
into resits. [Footnote: _Ber.,_ 1892, 25, 3213.]
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