IP Library Granted Patent US 8,389,668
Granted Patent B2
US 8,389,668 · App. 10/599,020 · Granted Mar 5, 2013

Use of a catalytic system for lactide and glycolide (co) oligomerization

Inventors: Frédéric Ben (Toulouse, FR); Didier Bourissou (Plaisance du Touch, FR); Roland Cherif-Cheikh (Castelldefels, ES); Anne De Sousa Delgado (Moilins de Rei, ES); Magalie Graullier (Toulouse, FR); Blanca Martin-Vaca (Toulouse, FR)
Assignee: Ipsen Pharma S.A.S.
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Quick Facts
Patent No.
US 8,389,668
App. No.
10/599,020
Granted
Mar 5, 2013
Kind
B2
Abstract

The use of a catalytic ring-opening lactide and glycolide (co)oligomerization system consisting of a strongly acidic ion-exchange resin-type polymeric catalyst and a (co)oligomerization additive, and a lactide and glycolide (co)oligomerization method using said catalytic system, are disclosed.

Claims (44)

1. A catalytic system comprising:

(a) a styrene and divinylbenzene-based macroreticular resin with sulphonic acid that functions as a strongly acidic ion-exchange resin polymeric catalyst;

(b) a (co)oligomerization additive of general formula (2)

H—O—R 2   (2)

R 2 represents a hydrogen atom or a group of formula -E 14 (R 14 )(R′ 14 )(R″ 14 );

wherein E 14 is a carbon atom; R 14 , R′ 14 and R″ 14 represent, independently, a hydrogen atom, or a substituted or non-substituted alkyl radical;

wherein said substituent or substituents comprise alkyls, carboxys, and alkoxycarbonyls, or mixtures thereof; and

(c) lactide and/or glycolide monomers;

wherein the quantity of monomer relative to the quantity of (co)oligomerization additive ranges from 4 to 10 molar equivalents and the conversion of monomer is greater than 95%.

2. The catalytic system of claim 1 , wherein the polymeric catalyst comprises a macroreticular Amberlyst® or Dowex® resin.

3. The catalytic system of claim 2 , wherein the polymeric catalyst comprises an Amberlyst® resin.

4. The catalytic system of claim 1 , wherein the compound of general formula (2) is such that

E represents an oxygen atom;

R 1 represents a hydrogen atom;

R 2 represents a hydrogen atom or a group of formula -E 14 (R 14 )(R′ 14 )(R″ 14 )

wherein E 14 represents a carbon atom and

R 14 , R′ 14 , and R″ 14 represent, independently, a hydrogen atom or an alkyl radical.

5. The catalytic system of claim 1 , wherein the compound of general formula (2) comprises water or an alcohol.

6. The catalytic system of claim 5 , wherein the compound of general formula (2) comprises an aliphatic alcohol.

7. The catalytic system of claim 6 , wherein the compound of general formula (2) comprises isopropanol, pentan-1-ol, dodecan-1-ol, or mixtures thereof.

8. The catalytic system of claim 1 , wherein the (co)oligomerization results in a degree of polymerization is less than 30.

9. A catalytic system comprising:

(a) a styrene and divinylbenzene-based macroreticular resin with sulphonic acid that functions as a strongly acidic ion-exchange resin polymeric catalyst;

(b) a (co)oligomerization additive of general formula (2)

R 1 -E-R 2 (2)  (2)

wherein:

E represents an element of group 16;

R 1 represents a hydrogen or deuterium atom;

R 2 represents a hydrogen or deuterium atom, or a group of formula -E 14 (R 14 )(R′ 14 )(R″ 14 );

wherein:

E 14 is an element of group 14;

R 14 , R′ 14 and R″ 14 represent, independently, a hydrogen atom; a deuterium atom;

or a substituted or non-substituted alkyl, cycloalkyl or aryl,

wherein said substituent or substituents comprise: halos, hydroxys, alkyls, alkoxys, cycloalkyls, cycloalkoxys, aryls, aryloxys, carboxys, alkoxycarbonyls, cycloalkoxycarbonyls and aryloxycarbonyls or mixtures thereof;

and

(c) lactide and/or glycolide monomers;

wherein the quantity of monomer relative to the quantity of (co)oligomerization additive ranges from 4 to 10 molar equivalents and the conversion of monomer is greater than 95%; and

wherein the catalytic system is capable of producing a (co)polymer where the (co)polymer comprises R2-alcohol ends; and/or the polydispersity indexes of the (co)polymer are between 1.0 and 1.4.

10. The catalytic system of claim 1 , wherein said catalytic system produces (co)polymers with a mass between 300 and 5,000 Daltons.

11. The catalytic system of claim 10 , wherein said catalytic system produces (co)polymers with a mass between 500 and 3,000 Daltons.

12. The catalytic system of claim 1 , wherein said catalytic system produces (co)polymers with a mass less than 5,000 Daltons.

13. The catalytic system of claim 9 , wherein said catalytic system produces (co)polymers with a mass between 300 and 5,000 Daltons.

14. The catalytic system of claim 13 , wherein said catalytic system produces (co)polymers with a mass between 500 and 3,000 Daltons.

15. The catalytic system of claim 9 , wherein said catalytic system produces (co)polymers with a mass less than 5,000 Daltons.

Assignments (1)
CHANGE OF NAME Recorded May 31, 2011
From: SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)
To: IPSEN PHARMA S.A.S.
Reel/Frame 026359/0316 →
Priority Claims (1)
FR 04 02671 · Mar 16, 2004 · national
Continuity (1)
Related Publication 20070185304A1 · Aug 9, 2007