Five-membered cyclic biscarbonates bearing amide linkages, their preparation and their uses for the preparation of polymers

Patent metadata

Field	Value
Publication number	US-9926288-B2
Application number	US-201415104956-A
Country	US
Kind code	B2
Filing date	Dec 16, 2014
Priority date	Dec 16, 2013
Publication date	Mar 27, 2018
Grant date	Mar 27, 2018

Abstract

A compound is of formula (I):

in which A 1 and A 1 ′ are independently from each other a linear or branched alkylene radical including from 1 to 20 carbon atom(s); A 2 is in particular a linear or branched alkylene radical including from 1 to 200 carbon atom(s); A 3 is H or a linear or branched alkyl radical including from 1 to 15 carbon atom(s) and R 1 and R 1 ′ 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.

First claim

What is claimed is:

1. A compound of formula (I):

wherein:
A 1 and A 1 ′ are independently from each other a linear or branched alkylene radical comprising from 1 to 20 carbon atom(s);
A 2 is chosen from the group consisting of:
a linear or branched alkylene radical comprising from 1 to 200 carbon atom(s), one or more carbon atom(s) being optionally replaced by an oxygen atom;
an arylene radical comprising from 6 to 14 carbon atoms, optionally functionalized in ortho, meta or para, with a linear or branched alkyl radical comprising from 1 to 10 carbon atom(s), one or more carbon atom(s) being optionally replaced by an oxygen atom;
a radical of formula -B 1 -B 2 - wherein:
B 1 is a cycloalkylene comprising from 3 to 15 carbon atoms, in which one or more carbon atom(s) is optionally substituted by at least one linear or branched alkyl group comprising from 1 to 15 carbon atom(s), and
B 2 is a linear or branched alkylene radical comprising from 1 to 15 carbon atom(s);
A 3 is H or a linear or branched alkyl radical comprising from 1 to 15 carbon atom(s);

or wherein A 2 and A 3 , together with the two nitrogen atoms bearing them, may form a saturated heterocyclyl group comprising from 3 to 8 members; and
R 1 and R 1 ′ are independently from each other H or a linear or branched alkyl radical comprising from 1 to 20 carbon atom(s).

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

3. The compound of formula (I) according to claim 1 , wherein A 3 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 A 2 and A 3 , 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 R 1 and R 1 ′ 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):

wherein A 1 , A 1 ′, A 2 , A 3 , R 1 and R 1 ′ are as defined in claim 1 .

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′):

with a diamine having the following formula (V):

R 1 , R 1 ′, A 1 , A 1 ′, A 2 and A 3 being such as defined in claim 1 , R 2 representing a halogen atom or a radical OR 3 with R 3 being a linear or branched alkyl group comprising from 1 to 10 carbon atom(s).

10. 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.

11. The polymer according to claim 10 , wherein the polyamine is a diamine having the following formula (VI):

wherein B is chosen from the group consisting of:
a linear or branched alkylene comprising from 1 to 200 carbon atom(s), one or more carbon atom(s) being optionally replaced by an oxygen atom;
an arylene radical comprising from 6 to 14 carbon atoms, optionally functionalized in ortho, meta or para with a linear or branched alkylene comprising from 1 to 10 carbon atom(s), one or more carbon atom(s) being optionally replaced by an oxygen atom; and
a radical of formula —B 1 —B 2 - wherein:
B 1 is a cycloalkylene comprising from 3 to 15 carbon atoms, in which one or more carbon atom(s) is optionally substituted by at least one linear or branched alkyl group comprising from 1 to 15 carbon atom(s), and
B 2 is a linear or branched alkylene radical comprising from 1 to 15 carbon atom(s).

12. The polymer according to claim 11 , said polymer consisting of n repetitive units having the following formula (U)

13. 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.

14. An intermediate compound of formula (II):

wherein A 1 , A 1 ′, A 2 , A 3 , R 1 and R 1 ′ are as defined in claim 1 .

Assignees

• Univ Bordeaux
• Inst Polytechnique Bordeaux
• Centre Nat Rech Scient
• Institut Des Corps Gras Etudes Et Rech Techniques—Iterg
• Centre Nat Rech Scient

Inventors

• Cramail Henri
• Grau Etienne
• Alfos Carine
• Maisonneuve Lise

Classifications

• C08G71/04

  Polyurethanes · CPC title

• C07D317/38 Primary

  Ethylene carbonate · CPC title

• C07D303/46

  by amide or nitrile radicals · CPC title

• C08K5/20

  Carboxylic acid amides · CPC title