IP Library Granted Patent US 10,442,872
Granted Patent B2
US 10,442,872 · App. 15/552,836 · Granted Oct 15, 2019

Biosourced polymer for manufacturing, via catalytic carbonation, a non-bituminous polyhydroxyurethane binder for roadway or civil engineering-related uses

Inventors: Vincent Besse (Chelles, FR); Sylvain Caillol (Montpellier, FR); Ghislain David (Montpellier, FR); Nicolas Illy (Courbevoie, FR)
Assignee: COLAS
C08B37/003C08G71/04C08L5/08C08L95/005C04B26/16C04B26/22
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Quick Facts
Patent No.
US 10,442,872
App. No.
15/552,836
Granted
Oct 15, 2019
Kind
B2
Abstract

Disclosed is a biosourced polymer obtained by dual chemical functionalization of chitosan, usable for catalytic carbonation of cyclic ethers by carbon dioxide, and a binder composition for creating layers and/or coatings for road construction and/or civil engineering, marking materials, or sealing or insulation materials. The composition contains a polyhydroxyurethane polymer binder resulting from the reaction of at least one polyamine with at least one polycyclocarbonate. The polycyclocarbonate was obtained by carbonating a (cyclic) poly(ether) with carbon dioxide catalyzed by the biosourced polymer.

Claims (23)

1. Biosourced polymer obtained by functionalization of chitosan in a manner such that it comprises monomer units of formulas A and B:

wherein M + is a cation, X − is an anion, L 1 and L 2 are, independently of one another, a divalent group, GA is an anionic group, and GC is a cationic group.

2. Biosourced polymer according to claim 1 , wherein GA is the carboxylate group.

3. Biosourced polymer according to claim 1 , wherein GC is a quaternary ammonium group.

4. Biosourced polymer according to claim 1 , further defined as being obtained by functionalization of chitosan so that it comprises monomer units of formulas A2 and B2:

wherein M + is a cation and X − is an anion.

5. Biosourced polymer according to claim 1 , wherein M + represents K + and X − represents I − .

6. Binder composition for making road construction and/or civil engineering layers and/or coatings, marking products, or sealants or insulating products, comprising a polymer binder of polyhydroxyurethane, derived from the reaction of at least one polyamine with at least one polycyclocarbonate, wherein the polycyclocarbonate was obtained by carbonation of a poly(cyclic ether) with carbon dioxide catalyzed by a biosourced polymer according to claim 1 .

7. Binder composition according to claim 6 , wherein the poly(cyclic ether) is a poly(epoxide).

8. Binder composition according to claim 7 , wherein the poly(cyclic ether) is a diepoxide.

9. Binder composition according to claim 6 , wherein the polyamine is a diamine and the polycyclocarbonate is a dicyclocarbonate.

10. Binder composition according to claim 6 , wherein the cyclocarbonate groups of the polycyclocarbonate are a 5 or 6-membered ring.

11. Binder composition according to claim 6 , wherein the polyhydroxyurethane was formed without using isocyanate reagents.

12. Method for carbonation with carbon dioxide, comprising the following steps:

providing a cyclic ether;

subjecting said cyclic ether to a carbonation reaction with carbon dioxide catalyzed by a biosourced polymer of claim 1 , and recovering a cyclocarbonate.

13. Method according to claim 12 , wherein the cyclic ether is a poly(cyclic ether) and the cyclocarbonate is a polycyclocarbonate.

14. Method according to claim 13 , further comprising the following step:

subjecting said polycyclocarbonate to a polycondensation reaction in the presence of at least one polyamine to obtain a polymer binder of polyhydroxyurethane, said binder comprising a polymer binder of polyhydroxyurethane, derived from the reaction of at least one polyamine with at least one polycyclocarbonate, wherein the polycyclocarbonate was obtained by carbonation of a poly(cyclic ether) with carbon dioxide catalyzed by a biosourced polymer obtained by functionalization of chitosan in a manner such that it comprises monomer units of formulas A and B:

wherein M + is a cation, X − is an anion, L 1 and L 2 are, independently of one another, a divalent group, GA is an anionic group, and GC is a cationic group.

15. Method according to claim 12 , wherein the carbonation reaction is carried out at a temperature of less than or equal to 100° C. under a carbon dioxide pressure of less than 10 bar for less than 4 hours.

16. Material for making road construction and/or civil engineering layers and/or coatings, comprising a binder composition according to claim 6 .

17. The material of claim 16 , further comprising an aggregate.

Assignments (2)
CHANGE OF ADDRESS Recorded Apr 5, 2019
From: COLAS
To: COLAS
Reel/Frame 048807/0931 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2017
From: BESSE, VINCENT; CAILLOL, SYLVAIN; DAVID, GHISLAIN; ILLY, NICOLAS
To: COLAS
Reel/Frame 043364/0850 →
Priority Claims (1)
FR 15 51536 · Feb 23, 2015 · national
Continuity (1)
Related Publication 20180037673A1 · Feb 8, 2018
Cited By (2)
US 50,456 US 12,304,377