Process of preparation of polyols and polyamines, and products as obtained

Patent metadata

Field	Value
Publication number	US-9605145-B2
Application number	US-201214358078-A
Country	US
Kind code	B2
Filing date	Nov 15, 2012
Priority date	Nov 15, 2011
Publication date	Mar 28, 2017
Grant date	Mar 28, 2017

Abstract

The present invention relates to the use of a compound of formula (I): wherein: —R represents —OH or —NH 2 ; —A 1 represents a divalent alkylene radical, straight or branched, having from 2 to 20 carbon atoms; —A 2 represents a divalent alkylene radical, straight or branched, having from 1 to 20 carbon atoms; —X 1 and X 2 represent, independently of each other, —NH— or —O—; —A 3 represents a divalent alkylene radical, straight or branched, having from 1 to 10 carbon atoms; —Z represents a hydrogen or a group of formula (A′): wherein A 1 , A 3 and R are as defined above in formula (I), for the preparation of a polymer chosen among polyurethane, polyester and polyamide.

First claim

The invention claimed is:

1. A method of preparing a polyurethane, polyester or polyamide polymer comprising polymerizing a compound of formula (I):

wherein:
R represents —OH or —NH 2 ;
A 1 represents a divalent alkylene radical, straight or branched, having from 2 to 20, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
A 2 represents a divalent alkylene radical, straight or branched, having from 1 to 20, and optionally comprising at least one double bond and/or optionally substituted by at least one hydroxyl or amine group;
X 1 and X 2 represent, independently of each other, —NH— or —O—;
A 3 represents a divalent alkylene radical, straight or branched, having from 1 to 10, and optionally comprising at least one double bond and/or optionally substituted by at least one hydroxyl or amine group; and
Z represents a hydrogen or a group of formula (A′):

 and wherein A 1 , A 3 and R are as defined above in formula (I);
wherein said compound has the following formula (I-1):

and wherein the compound is selected from the group consisting of:

2. Compound having the following formula (I):

wherein:
R represents —OH or —NH 2 ;
A 1 represents a straight divalent alkylene radical, having from 3 to 20 carbon atoms, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
A 2 represents a divalent alkylene radical, straight or branched, having from 3 to 20 carbon atoms, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
X 1 and X 2 represent, independently of each other, —NH— or —O—;
A 3 represents a divalent alkylene radical, straight or branched, having from 1 to 10 carbon atoms, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
Z represents a hydrogen or a group of formula (A′):

 wherein A 1 , A 3 and R are as defined above in formula (I);
 and wherein when X 1 and X 2 represent —O—, then R represents —NH 2 ;
wherein said compound has the following formula (I-1):

and wherein the compound is selected from the group consisting of:

3. Compound having the following formula (I):

wherein:
R represents —OH or —NH 2 ;
A 1 represents a straight divalent alkylene radical, having from 3 to 20 carbon atoms, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
A 2 represents a divalent alkylene radical, straight or branched, having from 3 to 20 carbon atoms, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
X 1 and X 2 represent, independently of each other, —NH— or —O—;
A 3 represents a divalent alkylene radical, straight or branched, having from 1 to 10 carbon atoms, and optionally comprising at least one double bond, and/or optionally substituted by at least one hydroxyl or amine group;
Z represents a hydrogen or a group of formula (A′):

 wherein A 1 , A 3 and R are as defined above in formula (I);
and wherein when X 1 and X 2 represent —O—, then R represents —NH 2 ;
wherein the compound has the following formula (I-2):

4. Compound according to claim 3 , wherein the compound is selected from the group consisting of:

5. Polymer obtainable by polymerization of the compound of claim 2 , and of a polyisocyanate.

6. Polymer according to claim 5 , wherein the polyisocyanate is a diisocyanate of formula (O)CN-A 4 -NC(O), wherein A 4 represents:
an alkylene radical, straight or branched, having from 2 to 20 carbon atoms; or
a cycloalkylene-alkylene-cycloalkylene radical, having from 6 to 30 carbon atoms; or
a arylene-alkylene-arylene radical, having from 6 to 30 carbon atoms; or
a cycloalkylene radical, having from 3 to 10 carbon atoms; or
a alkylene-cycloalkylene, having from 3 to 15 carbon atoms; or
an arylene radical, having from 6 to 10 carbon atoms,

and wherein the alkylene, cycloalkylene and arylene radicals are optionally substituted by at least one substituent selected from the group consisting of alkyl, aryl and cycloalkyl.

7. Polymer according to claim 6 , said polymer having the following formula (VII):

wherein:
n is comprised from 1 to 10;
m is comprised from 2 to 20;
p is comprised from 1 to 20;
X 1 and X 2 represent, independently of each other, —NH— or —O—;
A 4 is as defined in claim 6 ;
X 4 represents —NH— or —O—; and
t represents a integer comprised from 1 to 50000.

8. Polymer obtainable by polymerization of the compound of claim 2 , and of a polyester.

9. Polymer according to claim 8 , wherein the polyester is a diester of formula (VI):

wherein:
R′ represents H, an alkyl group having from 1 to 10 carbon atoms, or a —C(O)R 3 , R 3 being an alkyl group straight or branched, and having from 1 to 20 carbon atoms, and optionally comprising at least one double bond and/or optionally substituted by at least one hydroxyl or amine group;
X 5 represents —CH 2 — or —CH 2 S—;

A 5 represents an alkylene radical, straight or branched, having from 1 to 12 carbon atoms, said alkylene radical being eventually substituted by an alkyl group having from 1 to 10 carbon atoms, and said alkylene radical eventually comprising a double bond.

10. Polymer according to claim 8 , said polymer having the following formula (VIII):

wherein:
n is comprised from 1 to 10;
m is comprised from 2 to 20;
p is comprised from 1 to 20;
X 1 and X 2 represent, independently of each other, —NH— or —O—;
X 5 represents —CH 2 — or —CH 2 S—;
A 5 represents represents an alkylene radical, straight or branched, having from 1 to 12 carbon atoms, said alkylene radical being eventually substituted by an alkyl group having from 1 to 10 carbon atoms, and said alkylene radical eventually comprising a double bond; X 4 represents —NH— or —O—; and
u represents a integer comprised from 1 to 50000.

Assignees

• Centre Nat De La Rech Scient (C N R S)
• Inst Des Corps Gras Etudes Et Rech Techniques—Iterg
• Centre Nat Rech Scient
• Inst Des Corps Gras Etudes Et Rech Techniques-Iterg

Inventors

• Maisonneuve Lise
• Lebarbe Thomas
• Cramail Henri
• Alfos Carine
• Gadenne Benoît
• Cloutet Eric

Classifications

• C07C323/52 Primary

  the carbon skeleton being acyclic and saturated · CPC title

• C08G69/44

  Polyester-amides · CPC title

• C08G63/688

  containing sulfur · CPC title

• C08L67/04 Primary

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence) · CPC title

• C07C323/60

  with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms · CPC title