Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1995-12-13
1998-12-01
Truo, Duc
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
4242801, 4242831, 546269, 546270, C08G 1832
Patent
active
058440615
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel polyphenol derivative compositions and to their preparation.
The invention relates more particularly to compositions containing polyhydroxylated derivatives of flavan and especially of 3-flavanol.
It is recalled that the flavan ring system corresponds to the structure (x): ##STR2## the 3-flavanols possessing an --OH group in the 3-position.
Flavanols, polyhydroxylated on the benzene rings, may be obtained by extraction from various plant sources such as various species of pine, green tea or grape vine. The crude extracts isolated are formed of complex mixtures comprising monomers and polymers, more particularly oligomers ranging from diners and, most generally, up to decamers.
Industrial extraction processes are directed towards providing fractions consisting mainly of oligomers. These fractions will be referred to indiscriminately hereinbelow as flavanol oligomers or as procyanolide oligomers, abbreviated to OPC.
The phenol groups present on the flavanol moieties impart to these OPCs anti-radical and antioxidizing properties which offer a potential advantage for numerous applications.
Certain OPC extracts are used therapeutically as vascular protectors or in cosmetics.
The practical and wider use of these products is sometimes hampered by the problem of their instability, due to the presence of free phenolic groups.
In general, phenols are products which oxidize spontaneously on contact with atmospheric oxygen and/or in the presence of light, by involving a radical mechanism which may be represented by the following equation: ##STR3##
As the phenolate radical is stabilized by the resonance effect, radical derivatives of the following type are formed: ##STR4## which may then undergo ortho or para coupling to give condensation products of the following types: ##STR5##
The polyphenol derivatives which follow such a mechanism give radical condensation products. When rearomatization cannot take place, products of quinone type add to these derivatives. This set of compounds is responsible for the appearance of red-brown colors, which are incompatible with certain applications.
Furthermore, OPCs are water-soluble products, which poses a problem of compatibility with a good number of excipients used generally in the abovementioned applications, these excipients having, on the contrary, liposoluble properties.
The search for means which make it possible to impart satisfactory stability to the polyhydroxylated derivatives and in particular to OPCS, and at the same time to render them liposoluble, has led the inventors to develop a technique for the protection of the free --OH groups by esterification under specific conditions.
The aim of the invention is thus to provide highly stable polyphenol derivative compositions.
The invention is also directed towards providing a process for the esterification of the phenol functions of these compositions, which process is easy to carry out and may be exploited on the industrial scale.
The invention is also directed towards the exploitation of the anti-radical and anti-oxidizing properties of these compositions in various fields, in particular in therapy, in cosmetics and in dietetics.
The compositions of the invention are characterized in that they mainly contain oligomers or polymers whose monomer moieties correspond to the formula (I): ##STR6## in which A represents a group --OR, a hydrogen atom or a substituent R, R.sub.1 being a saturated or unsaturated, linear or branched alkyl radical of at least two carbon atoms, or an aryl, aralkyl or aralkylene radical, --COR.sub.1 being a hydrogen atom, an alkyl group, an acyl group --CO--C.sub.6 H.sub.2 --(OH).sub.3, a monosaccharide or a polysaccharide, and are numbers from 1 to 3, corresponding to the number of substitutions on a ring, and the diastereoisomers and the regioisomers of these moieties, the monomer moieties being connected by carbon--carbon bonds or by ether bridges between the rings which make up the flavan ring system.
The compositions thus esterified are of great stability. They may
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Bignon Jean
Bisson Jean-Louis
Vercauteren Joseph
Weber Jean-Frederic
Berkem
Truo Duc
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