Lactide polymerisation

Patent metadata

Field	Value
Publication number	US-10035878-B2
Application number	US-201515302581-A
Country	US
Kind code	B2
Filing date	Apr 8, 2015
Priority date	Apr 9, 2014
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

The present invention relates to a compound having the formula L a M(OR 1 ) b R 2 c X d wherein M is a metal selected from Ti, Zr and Hf; L is a ligand selected from permethylpentalene, (hydro)permethyl-pentalene, (hydro)pentalene, cyclopentadiene, indene and ethylene- or silane-bridged indene, preferably (bis)indene; R 1 is a 1-6C alkyl, substituted or unsubstituted phenyl, or a substituted or unsubstituted phenylalkylene group; R 2 is Me or Et; X is halogen; a=1 to 3, b=1 to 3, c=0 or 1 and d=0, 1, 2 or 3; and dimers thereof, the use of the compound as an initiator in the polymerization of lactide monomer and a process for producing a polylactide performed by contacting a lactide monomer with the compound.

First claim

The invention claimed is:

1. A compound having the formula
L a M(OR 1 ) b R 2 c X d
wherein
M is a metal selected from Ti, Zr and Hf;
L is a ligand selected from permethylpentalene, (hydro)permethyl-pentalene, and (hydro)pentalene;
R 1 is a 1-6C alkyl, substituted or unsubstituted phenyl, or a substituted or unsubstituted phenylalkylene group;
R 2 is Me or Et;
X is halogen;
a=1 to 3, b=1 to 3, c=0 or 1 and d=0, 1, 2 or 3;
or a dimer thereof.

2. The compound according to claim 1 , wherein L is permethylpentalene and X is Cl.

3. The compound according to claim 1 , wherein R 1 is a group selected from — t Bu, —C 6 H 3 (R 3 ) 2 , where R 3 is 1-4C alkyl, and —CH(R 4 )Ph, where R 4 is H or 1-4C alkyl.

4. The compound according to claim 3 , wherein R 1 is selected from 2,6-dimethylphenyl, 2,6-diisopropylphenyl and 2,6-di t butylphenyl.

5. The compound according to claim 3 , wherein R 4 is Me.

6. The compound according to claim 1 , wherein M is Ti.

7. The compound according to claim 1 , wherein M is Zr.

8. The compound according to claim 1 , wherein M is Hf.

9. A method for polymerizing a lactide monomer, wherein an initiator in the polymerisation of a lactide monomer is a compound having the formula
L a M(OR 1 ) b R 2 c X d
wherein
M is a metal selected from Ti, Zr and Hf;
L is a ligand selected from permethylpentalene, (hydro)permethyl-pentalene, and (hydro)pentalene;
R 1 is a 1-6C alkyl, substituted or unsubstituted phenyl, or a substituted or unsubstituted phenylalkylene group;
R 2 is Me or Et;
X is halogen;
a=1 to 3, b=1 to 3, c=0 or 1 and d=0, 1, 2 or 3;
or a dimer thereof.

10. The method according to claim 9 , wherein the lactide monomer is L-lactide.

11. The method according to claim 9 , wherein the lactide monomer is rac-lactide.

12. A process for producing a polylactide which comprises contacting a lactide monomer with a compound having the formula
L a M(OR 1 ) b R 2 c X d
wherein
M is a metal selected from Ti, Zr and Hf;
L is a ligand selected from permethylpentalene, (hydro)permethyl-pentalene, and (hydro)pentalene;
R 1 is a 1-6C alkyl, substituted or unsubstituted phenyl, or a substituted or unsubstituted phenylalkylene group;
R 2 is Me or Et;
X is halogen;
a=1 to 3, b=1 to 3, c=0 or 1 and d=0, 1, 2 or 3;
or a dimer thereof.

13. The process according to claim 12 , wherein the lactide monomer is L-lactide and the polylactide is isotactic polylactide.

14. The process according to claim 12 , wherein the lactide monomer is rac-lactide and the polylactide is atactic polylactide.

Assignees

• Scg Chemicals Co Ltd

Inventors

• O'Hare Dermot
• Buffet Jean-Charles
• Turner Zoe

Classifications

• C08G77/70

  Siloxanes defined by use of the MDTQ nomenclature · CPC title

• C08G65/336

  containing silicon · CPC title

• C08G63/823 Primary

  for the preparation of polylactones or polylactides · CPC title

• C08G63/08

  Lactones or lactides · CPC title

• C07F17/00 Primary

  Metallocenes · CPC title