Process for the preparation of polylactones and polylactams
The present invention relates to a process for the preparation of a lactone or lactam homopolymer, comprising the stage consisting in reacting a lactone or lactam with a nonpolymeric initiator comprising at least one hydroxyl or thiol functional group in a nonchlorinated solvent in the presence of a sulfonic acid of formula R—SO 3 H. It also relates to the polymer composition thus obtained and to its uses, in particular as antistatic additive.
1. A process for the preparation of a polylactone or polylactam, comprising reacting a lactone or lactam with a nonpolymeric initiator in a nonchlorinated aromatic solvent in the presence of a sulfonic acid of formula R—SO 3 H, 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, 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 2 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, or
one CR 1 R 2 R 3 group, where R 1 denotes a halogen atom and R 2 and R 3 independently denote a hydrogen atom or a halogen atom.
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 initiator is a compound of formula CH(Ra)(Rb)(XH) where X denotes O or S and Ra and Rb independently denote a hydrogen atom, a linear or branched C 1 -C 22 , alkyl group, an aryl group, or an arylalkyl group, the arylalkyl group including an alkyl chain of from 1 to 22 carbon atoms.
6. The process as claimed in claim 5 , wherein X═O.
7. The process as claimed in claim 6 , wherein the initiator is selected from the group consisting of methanol, ethanol, n-propanol, n-butanol, n-pentanol, n-hexanol, neopentyl alcohol and benzyl alcohol.
8. The process as claimed in claim 1 wherein the initiator is selected from the group consisting of bioethanol, starch, chitin, chitosan, dextran, cellulose, propanediol, glycerol, propylene glycol, isosorbide, xylitol, mannitol, maltitol, erythritol, fructose, ribose and glucose.
9. The process as claimed in claim 1 , wherein the initiator is selected from the group consisting of methanethiol, n-propyl mercaptan, isopropyl mercaptan, butyl mercaptan, pentyl mercaptan, n-octyl mercaptan, t-nonyl mercaptan, n-dodecyl mercaptan, t-dodecyl mercaptan, 2-mercaptoethanol, 2-(4-methylcyclohex-3-enyl)propane-2-thiol and their mixtures.
10. The process as claimed in claim 1 , wherein the process is carried out in an anhydrous medium.
11. The process as claimed in claim 1 , wherein the sulfonic acid is (trifluoro)methanesulfonic acid.
12. The process as claimed in claim 1 , wherein the molar ratio of the lactone or lactam to the initiator ranges from 5 to 500.
13. The process as claimed in claim 1 , wherein the nonchlorinated solvent is an aromatic solvent.
14. The process as claimed in claim 1 , wherein the molar ratio of the sulfonic acid of formula R—SO 3 H to each hydroxyl or thiol functional group of the initiator is 1.
15. The process as claimed in claim 1 , wherein the process is carried out at a temperature ranging from 20° C. to 105° C.
16. The process as claimed in claim 1 , wherein the process does not employ a metal entity.
17. A polymer composition, characterized in that it is capable of being obtained according to the process as claimed in claim 1 .
18. The use of the composition as claimed in claim 17 as an antistatic additive for polymeric resins.
19. The use of the composition as claimed in claim 17 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.