FIVE-MEMBERED CYCLIC BISCARBONATES BEARING AMIDE LINKAGES, THEIR PREPARATION AND THEIR USES FOR THE PREPARATION OF POLYMERS

• US 20160326132A1
• Filed: 12/16/2014
• Published: 11/10/2016
• Est. Priority Date: 12/16/2013
• Status: Active Grant

• Current Assignee: Centre National De La Recherche Scientifique, Institut des Corps Gras Etudes et Recherches Techniques, Institut polytechnique de Bordeaux, Université de Bordeaux
• Original Assignee: Centre National De La Recherche Scientifique, Institut des Corps Gras Etudes et Recherches Techniques, Institut polytechnique de Bordeaux, Université de Bordeaux
• Inventors: Grau, Etienne, Cramail, Henri, Alfos, Carine, Maisonneuve, Lise
• Granted Patent: US 9,926,288 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: C07D 303/46 by amide or nitrile radicals
• CPC Class Codes: C07D 317/38 Ethylene carbonate
• CPC Class Codes: C08G 71/04 Polyurethanes
• CPC Class Codes: C08K 5/20 Carboxylic acid amides

Abstract

A compound is of formula (I):

in which A₁ and A₁′ are independently from each other a linear or branched alkylene radical including from 1 to 20 carbon atom(s); A₂ is in particular a linear or branched alkylene radical including from 1 to 200 carbon atom(s); A₃ is H or a linear or branched alkyl radical including from 1 to 15 carbon atom(s) and R₁ and R₁′ are independently from each other H or a linear or branched alkyl radical comprising from 1 to 20 carbon atom(s). The compounds of formula (I) can be used in particular for the preparation of poly(hydroxyurethane)s and epoxy resins.

Claims

1. A compound of formula (I):

2. The compound of formula (I) according to claim 1, wherein A₂ is a linear or branched alkylene comprising from 1 to 10 carbon atom(s).

3. The compound of formula (I) according to claim 1 or 2, wherein A₃ is H or an alkyl radical comprising from 1 to 10 carbon atom(s).

4. The compound of formula (I) according to claim 1, wherein A₂ and A₃, together with the two nitrogen atoms bearing them, form a saturated heterocyclyl group comprising from 5 to 8 members.

5. The compound of formula (I) according to claim 1, wherein R₁ and R₁′

are H.

6. The compound of formula (I) according to claim 1, having one of the following formulae:

7. A method for preparing a compound of formula (I) according to claim 1, comprising a carbonation step of a compound having formula (II):

8. The method for preparing the compound of formula (I) according to claim 7, wherein the compound of formula (II) is prepared by epoxidation of the compound having the following formula (III)

9. The method according to claim 7, wherein the compound of formula (III) is prepared by amidation of compounds having formulae (IV) and (IV′

);

11. A polymer susceptible to be obtained by the polymerisation of a compound of formula (I) according to claim 1 and of at least one polyamine.

12. The polymer according to claim 11, wherein the polyamine is a diamine having the following formula (VI):

13. The polymer according to claim 12, said polymer consisting of n repetitive units having the following formula (U)

14. A method for preparing a poly(hydroxyurethane), comprising a step of polymerisation of a compound of formula (I) according to claim 1, and of at least one polyamine, said step being carried out at a temperature comprised between 60°

C. and 150°

C., optionally in the presence of a catalyst such as a strong base and/or a nucleophile.

15. An intermediate compound of formula (II):

10. (canceled)