IP Library Granted Patent US 9,487,629
Granted Patent B2
US 9,487,629 · App. 14/433,112 · Granted Nov 8, 2016

Method for preparing a statistical copolymer based on diene monomers and cyclic carbosilane monomers

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Quick Facts
Patent No.
US 9,487,629
App. No.
14/433,112
Granted
Nov 8, 2016
Kind
B2
Abstract

The present invention relates to a process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers. This process is characterized in that it comprises a stage of copolymerization, in the presence of an anionic initiator in a reaction medium comprising a polar solvent, of at least one diene monomer and of a cyclic carbosilane monomer corresponding to the Formula I: in which: R 1 and R 2 , which are identical or different, are each a C 1 -C 5 alkyl, C 6 -C 14 aryl or C 7 -C 11 alkylaromatic group; R 3 and R 4 , which are identical or different, are each a hydrogen atom or a C 1 -C 5 alkyl, C 6 -C 14 aryl or C 7 -C 11 alkylaromatic group; and x is an integer with a value ranging from 2 to 5 and is preferably 3.

Claims (25)

1. A process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers, comprising a stage of copolymerization, in the presence of an anionic initiator in a polymerization solvent comprising an inert polar solvent, of at least one diene monomer and of at least one cyclic carbosilane monomer corresponding to the Formula I:

with:

R1 and R2, which are identical or different, each being a C1-C5 alkyl, C6-C14 aryl or C7-C11 alkylaromatic group;

R3 and R4, which are identical or different, each being a hydrogen atom or a C1-C5 alkyl, C6-C14 aryl or C7-C11 alkylaromatic group; and

x being an integer with a value ranging from 2 to 5.

2. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 1 , wherein a fraction by volume of inert polar solvent with respect to a total volume of solvent is at least 10%.

3. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 1 , wherein the polymerization solvent also comprises an inert nonpolar solvent.

4. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 1 , wherein the anionic initiator comprises an alkali metal.

5. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 1 , wherein the diene monomer is 1,3-butadiene.

6. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 1 , wherein at least one other monomer copolymerizes during the copolymerization stage.

7. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 6 , wherein the other monomer is a vinylaromatic compound.

8. A random copolymer comprising, distributed randomly within a main linear chain of the copolymer, unsaturated units resulting from at least one diene monomer and dialkylcarbosilane units resulting from at least one cyclic carbosilane monomer of Formula I:

with:

R1 and R2, which are identical or different, each being a C1-C5 alkyl, C6-C14 aryl or C7-C11 alkylaromatic group;

R3 and R4, which are identical or different, each being a hydrogen atom or a C1-C5 alkyl, C6-C14 aryl or C7-C11 alkylaromatic group; and

x being an integer with a value ranging from 2 to 5,

the diene monomer being inserted predominantly according to an enchainment of 1,4-type.

9. The random diene copolymer according to claim 8 , wherein the diene monomer is 1,3-butadiene.

10. The random diene copolymer according to claim 8 , further comprising, in addition to these unsaturated units and these dialkylcarbosilane units, units resulting from at least one other monomer.

11. The random diene copolymer according to claim 10 , wherein this other monomer is styrene.

12. A random diene copolymer, prepared according to the process defined in claim 1 .

13. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 4 , wherein the anionic initiator comprises an aliphatic organolithium compound.

14. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 7 , wherein the vinylaromatic compound is styrene.

15. The process for the preparation of a random copolymer based on diene monomers and on cyclic carbosilane monomers according to claim 1 , wherein x has a value of 3.

16. The random diene copolymer according to claim 8 , wherein x has a value of 3.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2020
From: MICHELIN RECHERCHE ET TECHNIQUE S.A.
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN
Reel/Frame 052863/0624 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 24, 2015
From: MATMOUR, RACHID; SEEBOTH, NICOLAS; CHATARD, JULIEN
To: COMPAGNIE GENERALE DES ETABLISSEMENTS MICHELIN; MICHELIN RECHERCHE ET TECHNIQUE, S.A.
Reel/Frame 035892/0405 →