Stock material or miscellaneous articles – Coated or structually defined flake – particle – cell – strand,... – Particulate matter
Patent
2000-03-21
2000-12-05
Acquah, Samuel A.
Stock material or miscellaneous articles
Coated or structually defined flake, particle, cell, strand,...
Particulate matter
560179, 560205, 568303, 568376, 528220, 528271, 528354, 528361, 528370, 528403, 528481, 525450, 525471, 428357, B32B 1502, C08G 1000
Patent
active
06156429&
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel monomers with a dilactone ring and to the corresponding polymers, their preparation and the materials in which they are present.
It is known that, in the medical and surgical field, biocompatible and bioabsorbable polymers are currently being used, and also researched, for producing e.g. parts for osteosynthesis, implants capable of gradual drug release, suture threads, etc.
Biocompatible and/or biodegradable polymers are also of great value in the production of packaging products for products manufactured in industry, including the agri-foodstuffs industry, because of the ever-increasing constraints associated with environmental protection.
It is therefore important to be able to have a range of polymers which are degradable to non-toxic products and which have varied properties (especially mechanical, thermomechanical, physicochemical properties, etc.).
Novel monomers have now been discovered which afford polymers of great value in the fields which have just been mentioned.
To produce biodegradable polymers based on non-toxic products, it is desirable to use vegetable or animal raw materials of agricultural origin, which have the advantage in particular of avoiding complex chemical syntheses, when it is desired to obtain products degradable to non-toxic compounds and particularly to natural products.
Among the products of agricultural origin, oses and derivatives thereof represent an abundant and relatively inexpensive raw material. However, their use presents several problems, particularly the presence of numerous hydroxyl groups which are all capable of reacting and which therefore make it difficult to obtain definite products.
These problems can sometimes be solved by selectively protecting some of the hydroxyls in known manner, temporarily or definitively, with appropriate protecting groups. Nevertheless, the use of protecting groups is not sufficient to solve all the problems encountered. Thus, in the course of their researches, the authors of the present invention found that although .delta.-lactones are well known to be polymerizable, .delta.-gluconolactone, in which the hydroxyl groups not involved in the formation of the lactone ring are protected, only forms low molecular oligomers at best.
A novel type of monomer has now been discovered which has a dilactone ring and which, in particular, affords polymers with degrees of polymerization which, if desired, can be sufficiently high. It is thus possible to have e.g. a whole range of copolymers whose properties can easily be adjusted, especially by varying the respective proportions of the comonomers. The compound with a dilactone ring which constitutes the monomer of the invention has formula IIIa: ##STR2## in which: R is the radical of an acid R--CHOH--CO.sub.2 H derived from an ose, the functional groups present in R optionally being substituted, and --C(R.sub.1)(R.sub.2)--C(R.sub.3)(R.sub.4)--, in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 independently are --H or an alkyl, allyl, aryl or aralkyl group.
The invention further relates to polymers (homopolymers and copolymers) obtained from a monomer of formula III and optionally other comonomers. These polymers contain units of formula I:
In the present patent application, the aryl groups, including those present in the aralkyl groups, are in particular optionally substituted phenyl groups, and the alkyl groups have in particular from 1 to 4 carbon atoms.
The polymers of the invention are especially linear polymers with average molecular weights which can range e.g. from 1000 to about 3 million.
The acids derived from an ose can be selected for example from those derived from an ose having from 3 to 7 carbon atoms, particularly from 4 to 6 carbon atoms, including glyceraldehyde, erythrose, threose, lyxose, xylose, arabinose, ribose, glucose, galactose and mannose, in the form of their various isomers, particularly those of the D series. The acids derived from oses are especially aldonic, uronic and aldaric acids.
Gluconic, mannonic, galactonic, ribonic, arabinonic,
Boustta Mahfoud
Coudane Jean
Marcincinova Katarina
Vert Michel
Acquah Samuel A.
Centre National de la Recherche Scientifique "CNRS"
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