METHOD FOR PRODUCING A COPOLYMER OF AT LEAST ONE CYCLIC MONOMER

• US 20100121024A1
• Filed: 02/15/2008
• Published: 05/13/2010
• Est. Priority Date: 02/16/2007
• Status: Abandoned Application

• Current Assignee: Arkema France (Arkema), Centre National De La Recherche Scientifique
• Original Assignee: Arkema France (Arkema), Centre National De La Recherche Scientifique
• Inventors: Magnet, Stèphanie, Gazeau-Bureau, Stèphanie, Bourissou, Didier, Martin-Vaca, Blanca, Navarro, Christophe
• Application Number:
  US12/527,105
• Publication Number:
  US 20100121024A1
• Time in Patent Office: Days
• US Class Current: 528/354
• CPC Class Codes: C08G 2261/126 block
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 63/823 for the preparation of polylactones or polylactides
• CPC Class Codes: C08G 69/04 Preparatory processes
• CPC Class Codes: C08G 69/16 Preparatory processes
• CPC Class Codes: C09K 3/16 Anti-static materials
• CPC Class Codes: D01F 6/78 from copolycondensation products
• CPC Class Codes: Y02P 70/50 Manufacturing or production processes characterised by the final manufactured product

Abstract

The present invention relates to a process for the preparation of a copolymer of at least one cyclic monomer chosen from a lactone, a lactam, a lactide and a glycolide, comprising the stage consisting in reacting said cyclic monomer with a polymeric initiator in the presence of a compound carrying a sulfonic acid functional group.

It also relates to the polymer composition obtained according to this process and to its uses, in particular as antistatic additive.

Claims

1. A process for the preparation of a copolymer of at least one cyclic monomer chosen from a lactone, a lactam, a lactide and a glycolide, comprising reacting said cyclic monomer with a polymeric initiator in the presence of a compound carrying a sulfonic acid functional group.

2. The process as claimed in claim 1, wherein the lactone is selected from the group consisting of ε

-caprolactone, δ

-valerolactone, β

-butyrolactone and γ

-butyrolactone.

3. The process as claimed in claim 2, wherein the lactone is ε

-caprolactone.

4. The process as claimed in claim 1, wherein the lactam is selected from the group consisting of caprolactam, enantholactam, laurinlactam, pyrrolidinone and piperidone.

5. The process as claimed in claim 1, wherein the cyclic monomer is chosen from lactide, and glycolide.

6. The process as claimed in claim 1, wherein the polymeric initiator is a polymer comprising at least one hydroxyl functional group.

7. The process as claimed in claim 6, wherein the polymeric initiator is a mono- or polyhydroxylated oligomer or polymer selected from the group consisting of (alkoxy)polyalkylene glycols;

poly(alkyl)alkylene adipate diols;

α

-hydroxylated or α

,ω

-dihydroxylated polydienes which are optionally hydrogenated;

mono- or polyhydroxylated polyalkylenes;

polylactides comprising end hydroxyl functional groups;

polyhydroxyalkanoates;

modified or unmodified polysaccharides; and

their blends.

8. The process as claimed in claim 7, wherein the polymer comprising at least one hydroxyl functional group is selected from the group consisting of (methoxy)polyethylene glycol, polypropylene glycol, polytetramethylene glycol, poly(2-methyl-1,3-propylene adipate) diol, poly(1,4-butylene adipate) diol, α

,ω

-dihydroxylated polybutadiene, α

,ω

-dihydroxylated polyisoprene, mono- or polyhydroxylated polyisobutylene, poly(3-hydroxybutyrate), poly(3-hydroxyvalerate), starch, chitin, chitosan, dextran, cellulose and their blends.

9. The process as claimed in claim 1, wherein the polymeric initiator is a polymer comprising at least one thiol functional group.

10. The process as claimed in claim 9, wherein the polymeric initiator is selected from the group consisting of α

-thiolated or α

,ω

-thiolated polystyrenes, α

-thiolated or α

,ω

-thiolated poly(meth)acrylates, α

-thiolated or α

,ω

-thiolated polybutadienes, and their blends.

11. The method as claimed in claim 1, wherein the polymeric initiator is a vinyl cooligomer or copolymer which results from copolymerization between acrylic, methacrylic, styrene or diene monomers and functional monomers exhibiting either a hydroxyl group or a thiol group.

12. The process as claimed in claim 1, wherein the compound carrying a sulfonic acid functional group is a compound of formula R—

SO₃H where R denotes;

a linear alkyl group including from 1 to 20 carbon atoms or a branched or cyclic alkyl group including from 3 to 20 carbon atoms, which said alkyl groups are optionally substituted by one or more substituents chosen independently from oxo and halo groups, or

an aryl group optionally substituted by at least;

one linear alkyl substituent including from 1 to 20 carbon atoms or one branched or cyclic alkyl group including from 3 to 20 carbon atoms, said alkyl substituent or group being itself optionally substituted by at least one halogen group chosen from fluorine, chlorine, bromine or iodine,, or by a nitro group, or

one halogen group chosen from fluorine, chlorine, bromine or iodine, or

one nitro group.

13. The process as claimed in claim 12, wherein the compound carrying a sulfonic acid functional group is (trifluoro)methanesulfonic acid or para-toluenesulfonic acid.

14. The process as claimed in claim 1, wherein the molar ratio of the cyclic monomer to the polymeric initiator ranges from 5 to 500.

15. The process as claimed in claim 1, wherein the process is carried out in a nonchlorinated solvent.

16. The process as claimed in claim 15, wherein the process is carried out in a nonchlorinated aromatic solvent.

17. The process as claimed in claim 1, wherein the process is carried out in an anhydrous medium.

18. The process as claimed in claim 1, wherein the molar ratio of the compound carrying a sulfonic acid functional group to each hydroxyl or thiol functional group of the polymeric initiator is 1.

19. The process as claimed in claim 1, wherein the process is carried out at a temperature ranging from 20°

C. to 105°

C.

20. A polymer composition capable of being obtained according to the process as claimed in claim 1.

21. The use of the composition as claimed in claim 20 as antistatic additive for polymeric resins.

22. The use of the composition as claimed in claim 20 in the manufacture of a membrane for the treatment of liquid or gaseous effluents or in electrochemical energy storage systems;

as a biocompatible material in the pharmaceutical or cosmetic field;

as an additive which improves the impact strength of resins or as plasticizer for PVC;

or in the manufacture of textile fibers