Multilayer structure comprising a layer of supramolecular material and method for the production thereof

Patent metadata

Field	Value
Publication number	US-10093767-B2
Application number	US-201414786849-A
Country	US
Kind code	B2
Filing date	Apr 10, 2014
Priority date	Apr 26, 2013
Publication date	Oct 9, 2018
Grant date	Oct 9, 2018

Abstract

The invention relates to a multilayer structure comprising at least one layer of supramolecular material and one layer of rigid material, to a method for producing such a structure by casting a composition comprising a precursor of the supramolecular material, and to the uses of the structures produced, especially for applications where a dampening of impacts, vibrations and/or sound waves is desired, for example for producing locomotion vehicles such as automotive, rail, nautical, aeronautical or aerospace vehicles, or for the construction industry.

First claim

The invention claimed is:

1. A multilayer structure comprising at least two contiguous layers, referred to as first and second layers, the first layer comprising at least one rigid material and the second layer comprising at least one supramolecular material, said supramolecular material comprising arborescent molecules each comprising at least difunctional fragments and at least trifunctional fragments linked to one another by ester or thioester bridges, alone or in combination with amide or urea bridges, said bridges being formed from two functional groups carried by different fragments, said molecules additionally comprising, on the fragments located at the ends of the arborescences, end associative groups capable of associating with one another via hydrogen bonds and covalently connected to the functional groups not participating in said bridges, wherein the first layer is configured and arranged to exert sufficient stress on the second layer such that the second layer, once torn, self-heals.

2. The multilayer structure as claimed in claim 1 , wherein the second layer comprising the supramolecular material exhibits at least one portion, the thickness of which ranges from 5 μm to 20 mm.

3. The multilayer structure as claimed in claim 1 , wherein the second layer comprising the supramolecular material exhibits a shear modulus G′ ranging from 1 to 500 MPa.

4. The multilayer structure as claimed in claim 1 , wherein the second layer comprising the supramolecular material exhibits a tangent delta of greater than 0.5, over a broad temperature range of at least 30° C., as measured by dynamic mechanical thermoanalysis.

5. The multilayer structure as claimed in claim 1 , wherein the supramolecular material present in the second layer is such that said associative groups are selected from the group consisting of imidazolidonyl, triazolyl, triazinyl, bis-ureyl and ureido-pyrimidyl groups.

6. The multilayer structure as claimed in claim 1 , wherein the multilayer structure comprises at least one third layer contiguous with the second layer comprising the supramolecular material, so that the layer comprising the supramolecular material is sandwiched, at least partially, between said first and third layers.

7. A process for the manufacture of a multilayer structure according to claim 1 , comprising at least (i) a stage of pouring a composition comprising at least one supramolecular material precursor, in contact with the layer comprising at least one rigid material, in order to together form the two contiguous layers, and (ii) a curing stage carried out so as to convert said precursor into the supramolecular material comprising arborescent molecules each comprising at least difunctional fragments and at least trifunctional fragments linked to one another by ester or thioester bridges, alone or in combination with amide or urea bridges, said bridges being formed from two functional groups carried by different fragments, said molecules additionally comprising, on the fragments located at the ends of the arborescences, end associative groups capable of associating with one another via hydrogen bonds and covalently connected to the functional groups not participating in said bridges.

8. The process as claimed in claim 7 , wherein the supramolecular material precursor is obtained by at least the following successive stages:
(a) the reaction of at least one at least trifunctional compound (A) with at least one compound (B) carrying, on the one hand, at least one reactive group capable of reacting with the reactive functional groups of (A) and, on the other hand, at least one associative group,
(b) the mixing of the compound(s) obtained in stage (a) with at least one at least difunctional compound (C), the reactive functional groups of which are capable of reacting with the reactive functional groups of the compound (A) during the curing stage (ii), in order to form ester or thioester bridges, alone or in combination with amide or urea bridges.

9. The process as claimed in claim 8 , wherein the compound (A) carries at least three identical or different functional groups selected from the group consisting of acid, ester and acyl chloride functional groups.

10. The process as claimed in claim 8 , wherein the compound (B) carries at least one reactive group selected from the group consisting of alcohol and primary and secondary amine groups.

11. The process as claimed in claim 8 , wherein the compound (B) corresponds to any one of the formulae (B1) to (B3):

where:
R denotes a unit comprising at least one alcohol or primary or secondary amine group,
R′ denotes a hydrogen atom,
A denotes an oxygen or sulfur atom or an NH group.

12. The process as claimed in claim 8 , wherein the compound (B) is selected from the group consisting of 2-aminoethylimidazolidone (UTETA), 1-(2-[(2-aminoethyl)amino]ethyl)imidazolidone (UTETA), 1-(2-[2-{2-aminoethylamino}ethylamino]ethyl)imidazolidone (UTEPA), 3-amino-1,2,4-triazole and 4-amino-1,2,4-triazole.

13. The process as claimed in claim 8 , wherein the compound (C) carries at least two identical or different functional groups selected from the group consisting of epoxy, alcohol and amine functional groups.

14. The process as claimed in claim 7 , wherein the composition comprising the precursor is poured during stage (i) at a viscosity of less than 50 Pa·s, as measured by plate-plate rheometry at a shear rate of 50 s −1 .

15. The process as claimed in claim 7 , wherein the curing stage (ii) is carried out at a temperature ranging from 80° C. to 180° C.

16. An object comprising at least one multilayer structure defined according to claim 1 .

17. A method for damping at least one of impacts, vibrations or sound waves, comprising using a multilayer structure defined according to claim 1 .

18. A method for manufacturing a locomotion vehicle, comprising using a multilayer structure defined according to claim 1 .

19. The multilayer structure as claimed in claim 1 , wherein the supramolecular material present in the second layer is such that said associative groups are imidazolidonyl groups.

Assignees

• Arkema France

Inventors

• Disson Jean-Pierre
• Van Hemelryck Bruno

Classifications

• B29K2096/00

  Use of specified macromolecular materials not provided for in a single one of main groups B29K2001/00 - B29K2095/00, as moulding material · CPC title

• C09D201/005

  Dendritic macromolecules · CPC title

• B32B2307/56

  Damping, energy absorption · CPC title

• C09J201/005

  Dendritic macromolecules · CPC title

• B32B2553/02

  Shock absorbing · CPC title