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SYNTANS
Syntans: abbreviation for synthetic tannins.
It covers substances which are manufactured to
replace partially or completely, the natural vegetable extracts, to accelerate
production and to make it cheaper.
Introduction of new functional groups which do
not occur in vegetable tannins such as sulfonic groups opened new prospects
for tanning. Syntans are frequently used in retanning chrome leather.
There are replacement syntans and auxiliary (assisting
to the tanning process) syntans.
Sizes of 800 or less, which correspond to 2-4
aromatic rings are of practical importance. Molecules of greater sizes
do not tan or tan only superficially.
Bonds between aromatic rings in syntans are essential
for their properties. For example extension of a molecule by a CH2
member weakens tanning ability of syntan. Replacement of such a bridge
by a sulfonyl group one increases tanning and improves resistance to light.
Resistance to light is also improved by a -SO2-NH- sulfonamide
sequence. Bonding groups can be put in the following order of increasing
light resistance:
-CH2-<-CHR-<-CH2NH-CO-NHCH2-<-CR2-<-CO2-<-SO2-NH-
Apart from the bridges connecting Ar rings, the
amount, kind and position of functional groups built into these rings are
significant. Only hydroxyls, sulfo groups and amino groups have been applied.
Thus factors characterizing a syntan are:
1) number and kind of rings in the molecule
2) number and kind of functional groups
3) molecular weight
Syntans may contain chromium components as well.
Syntans produced in industry generally are not chemical individua, chemical
species, generally one speaks of an average of the properties mentioned.
Hydroxyls: attached
to aromatic rings,have phenolic character; it is desirable to introduce
them into the molecule in greatest possible amount. Regular distribution
of hydroxyls is adventageous since maximum possible conjugated bonds can
be formed.
It is known that derivatives of a-napthol
are better tanning agents than those of b-napthol.
Presence of other substituents in the ring influences
reactivity. R substituents decrease tanning ability of syntans; sulfo and
carboxylic groups in orto and para position improve the tanning ability,
whereas they decrease this ability in meta position. As rule hydroxylic
groups do not occur in syntan side chains.
Sulfonic group: as
a substituent on the aromatic ring, it is strongly dissociated, and gives
acidic character to the compound.It affects the tanning ability negatively
but increases its water solubility. As a rule compound which have one sulfonic
group per 3 to 4 rings are applied.
Amino groups: occur
sometimes in syntans, may act as hydrophiles, however their action is limited
to acidic medium only. If the amino groups are the only functional groups
they participate in the binding of collagen. They probably form H-bonds
with oxygen from the peptide group. The solubility of syntans containing
only amino groups decreases with the acidity of the solution, whereas under
the same conditions its ability to bind to hide increases.
Among synthetic tannins of special importance
are chromium salts, complexed with condensation products of benzene and
napthalene derivatives.For example, Rotanin CR is a product of this kind
containing 12-13% of Cr2O3 and derivatives of napthalenesulphonic,
hydroxybenzenesulfonic and o-pthalic acids.It is a tanning agent that may
be applied alone; it gives very bright leather of Ts about 100 C, of properties
similar to those of chromium leather.
Auxiliary syntans may be dispersing agents,bleaching
agents,resin tannins etc. This group leads us to macromolecular products
produced in industry of many classes(novolacs, diene and acrylic resins
etc.).
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