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(12) Patent Application Publication (10) Pub. No.: US 2013/0261255 A1 Deyrail Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2013/0261255 A1 Deyrail Et Al US 2013026 1255A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0261255 A1 Deyrail et al. (43) Pub. Date: Oct. 3, 2013 (54) COMPOSITION INCLUDING A MIXTURE OF Publication Classification ATHERMOPLASTC CONDENSATION POLYMER AND A SUPRAMOLECULAR (51) Int. Cl. POLYMER, AND MANUFACTURING C08G 7L/02 (2006.01) METHOD (52) U.S. Cl. CPC ...................................... C08G 71/02 (2013.01) (75) Inventors: Yves Deyrail, Evreux (FR); Anthony USPC ........................................ 524/606; 525/420.5 Dufrenne, Theilleme (FR); Samuel Devisme, Rouen (FR); Nicolas Dufaure, (57) ABSTRACT Bernay (FR); Jean-Luc Couturier, Lyon (FR); Bruno Van Hemelryck, A subject matter of the present invention is a composition Chaponost (FR); Manuel Hidalgo, comprising: Brignais (FR) (i) from 0.1 to 49 parts by weight of at least one thermoplastic condensation polymer; and (73) Assignee: Arkema France, Colombes cedex (FR) (ii) from 51 to 99.9 parts by weight of at least one supramo (21) Appl. No.: 13/880,249 lecular polymer capable of being obtained by the reaction of at least one at least trifunctional compound (22) PCT Filed: Oct. 18, 2011 (A) carrying first and second functional groups with: at least one compound (B) carrying, on the one hand, at (86). PCT No.: PCT/FR2O11AOS2426 least one reactive group capable of reacting with the first S371 (c)(1), functional groups of (A) and, on the other hand, at least (2), (4) Date: Jun. 18, 2013 one associative group; and at least one at least bifunctional compound (C), the func (30) Foreign Application Priority Data tional groups of which are capable of reacting with the second functional groups of the compound (A) in order Oct. 21, 2010 (FR) ....................................... 1058,619 to form ester, thioester or amide bridges. US 2013/0261255 A1 Oct. 3, 2013 COMPOSITION INCLUDING AMIXTURE OF these materials is that these physical bonds are reversible, in ATHERMOPLASTC CONDENSATION particular under the influence of the temperature or by the POLYMER AND A SUPRAMOLECULAR action of a selective solvent. POLYMER, AND MANUFACTURING 0009. Some of them additionally have elastomeric prop METHOD erties. In contrast to conventional elastomers, these materials have the advantage of being able to fluidify above a certain CROSS REFERENCE TO RELATED temperature, which facilitates the processing thereof, in par APPLICATIONS ticular the satisfactory filling of the molds, and also the recy 0001. This application is the U.S. National Phase applica cling thereof. tion of PCT International Application No. PCT/FR2011/ 0010 Some of these supramolecular polymers are, fur 052426, filed Oct. 18, 2011, and claims priority to French thermore, composed of molecules bonded in networks exclu Patent Application No. 1058619, filed Oct. 21, 2010, the sively by reversible physical bonds. Despite the relatively disclosures of which are incorporated by reference in their modest physical bonding forces of the molecules of Such a entirety for all purposes. Supramolecular network, these materials are, like classic or conventional elastomers, capable of exhibiting a dimensional FIELD OF THE INVENTION stability over very long times and of recovering their initial form after large deformations. They can be used to manufac 0002 The present invention relates to compositions based ture, for example, leaktight seals, thermal or acoustic insula on thermoplastic polycondensation polymers and on tors, tires, cables, sheaths, footwear Soles, packagings, Supramolecular polymers, to their process of manufacture patches (cosmetic or dermopharmaceutical), dressings, elas and to their use in numerous industrial fields where recourse tic clamp collars, vacuum pipes, or pipes and flexible tubing is had to injection molding. for the transportation of fluids. 0011 Supramolecular materials have already been BACKGROUND OF THE INVENTION described by Arkema France. More particularly, Arkema France has already described supramolecular materials which 0003. Injection molding is a technique for the mass pro behave as elastomers. duction of parts on a large or very large scale. 0012. A self-healing elastomeric supramolecular material 0004 Injection-molded components are encountered in a is furthermore disclosed in the document WO 2006/087475. great many fields, such as the motor vehicle industry, the It comprises molecules including at least three associative electrical goods industry, computer hardware or furniture. In functional groups, such as imidazolidone groups, which are these industrial fields, the dimensions of the molds can vary capable of forming several physical bonds and which can be from a few millimeters to several meters, for motor vehicle obtained by reacting urea with the product of the reaction of bodywork components or garden tables, for example. a polyamine with triacids. The materials obtained according 0005 Molds, installed on a machine, are generally com to the teachings of the documents WO 03/059964 and WO posed of two shells which are pressed tightly against one 2006/087475 include triacids connected covalently, via another during the molding and then separated in order to amide functional groups, to intermediate junctions and/or to make possible the ejection of the molded part. In addition to endings, which are composed of the product of the reaction of these shells, the mold can comprise one or more cores the polyamine with urea and which thus comprise numerous intended to form the hollow portions of the part and punches associative groups, that is to say including N-H and C=O which make it possible to keep openings in its walls. It fre functional groups capable of combining with one another via quently happens that inserts are placed in the mold, which hydrogen bonds. Specifically, the publication by P. Cordier, inserts will subsequently be reencountered included in the L. Leibler, F. Tournilhac and C. Soulie-Ziakovic in Nature, part: they are generally threaded components which locally 451,977 (2008), mentions that a polymer synthesized accord compensate for the insufficient strength of the material mak ing to the procedure described in the document WO 2006/ ing up the body of the part. 087475 comprises amidoethyl-imidazolidone endings and 0006. In contrast to other processes where the mold is lost, di(amidoethyl)urea and diamidotetraethyl triurea junctions. injection molding makes it possible to reuse the molds, which It is understood that, due to the process of synthesis of these is highly advantageous. Injection molding also makes it pos materials, the chemical natures of the abovementioned junc sible to obtain very exact and well finished parts which very tions and endings are interdependent, in the sense that it is not often do not require any Subsequent machining. Injection possible to vary the nature of the amidoethyl-imidazolidone molding can thus be employed in particular for the manufac ending without affecting that of the two junctions. ture of parts constituting visible portions of household appli (0013 The document entitled “Versatile One-Pot Synthe ances, television sets and motor vehicle dashboards, for sis of Supramolecular Plastics, and Self-Healing Rubbers” by example. Damien Montarnal, François Tournilhac, Manuel Hidalgo, 0007. The materials employed in injection molding pro Jean-Luc Couturier and Ludwik Leibler, which appeared in cesses must exhibit a low degree of shrinkage. This property The Journal of the American Chemical Society, 131 (23), is particularly important when materials are injected into 7966; 17 Jun. 2009, describes an alternative process for the molds exhibiting cores. This is because the parts exhibiting a production of Supramolecular polymers, including those hav high shrinkage contract during the cooling and sometimes ing elastomeric properties of the type of those of the publica very tightly grip the cores around which they have been tion by P. Cordier et al. This method makes it possible, inter poured, which makes it difficult to extract the part. alia, to destroy the interdependence of the chemical natures 0008 “Supramolecular polymers are materials compris between the junctions and the endings of the Supramolecular ing compounds held together by noncovalent bonds, such as network. It thus becomes possible to control the chemical hydrogen, ionic and/or hydrophobic bonds. One advantage of nature of the endings independently of that of the junctions. US 2013/0261255 A1 Oct. 3, 2013 0014. These novel self-healing polymers have huge 0023 Thus, compositions in accordance with the inven advantages, such as those of being easy to process, of result tion exhibit both self-repair properties but also a significantly ing predominantly from renewable starting materials and of reduced degree of shrinkage in comparison with that of the being self repairable. Supramolecular polymers used alone. 0015. However, it is difficult to employ supramolecular 0024. The inventors have shown, in example 4, that these polymers in industrial processes involving injection. In par compositions exhibit a degree of shrinkage of 20% or less ticular, the Supramolecular polymers can be transported in while retaining the properties of the Supramolecular poly screws of injection molding machines and then poured into a mers, such as the self healing, whereas compositions not mold but, once removed from the mold, they exhibit a high comprising a thermoplastic condensation polymer having shrinkage, that is to say a decrease in the dimensions of the polyamide functional groups exhibit a shrinkage
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