Anionic polymerization initiator, use thereof for synthesizing a diene elastomer having an alkyne function at the chain end, and functionalized diene elastomer
AssigneesCompagnie Generale Des Etablissements Michelin, Michelin Recherche et Technique S.A.
InventorsRachid Matmour, Nicolas Seeboth
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Abstract
An anionic polymerization initiator of formula: in which: Met, which can be borne by the ortho, meta or para position, denotes an alkali metal, R1 and R2, and also R3 and R4, which can be borne by the ortho, meta or para position, denote a hydrogen atom or an alkyl, cycloalkyl, aryl or arylalkyl group, and R5 denotes an alkyl, cycloalkyl, aryl or arylalkyl group or a protective group for the alkyne functional group. The use of such a polymerization initiator makes possible the synthesis of a diene elastomer bearing, at one or each of its chain ends, a group comprising an alkyne functional group with a high degree of functionalization.
Claims4
A process for the synthesis of a diene elastomer bearing, at one or each of its chain ends, a group comprising an alkyne functional group, comprising the anionic polymerization of at least one conjugated diene monomer initiated by an organometallic compound comprising an alkyne bond of formula 1:
- wherein
- Met, which can be borne by the ortho, meta or para position with respect to the group comprising the carbon-carbon triple bond, denotes an alkali metal, and
- R1 and R2, and also R3 and R4, which can be borne by the ortho, meta or para position, denote, independently of one another, a hydrogen atom, a C1-C15 alkyl group, a C5-C15 cycloalkyl group, a C6-C15 aryl group or a C7-C15 arylalkyl group which can be separated from the aromatic nucleus by a heteroatom, and
- R5 denotes a C1-C5 alkyl group, a C5-C15 cycloalkyl group, a C6-C15 aryl group, a C7-C15 arylalkyl group or a protective group for the alkyne functional group.
A diene elastomer bearing, at one or each of its chain ends, a group comprising an alkyne functional group, corresponding to the following formula 3:
- (A-E)n-X Formula 3
- wherein:
- X denotes a hydrocarbon group of valency n or a group resulting from a functionalization, coupling or star-branching agent comprising at least one atom chosen from O, N, Si or Sn;
- A is a monovalent radical corresponding to the following formula 2:
- wherein:
- R1 and R2, and also R3 and R4, which can be borne by the ortho, meta or para position, denote, independently of one another, a hydrogen atom, a C1-C15 alkyl group, a C5-C15 cycloalkyl group, a C6-C15 aryl group or a C7-C15 arylalkyl group which can be separated from the aromatic nucleus by a heteroatom,
- R5 denotes a hydrogen atom, a C1-C5 alkyl group, a cycloalkyl group, a C6-C15 aryl group, a C7-C15 arylalkyl group or a protective group for the alkyne functional group, and
- * indicates a point of bonding with the elastomer E,
- E, which can be borne by the ortho, meta or para position of A with respect to the group comprising the carbon-carbon triple bond, denotes the diene elastomer, and
- n is an integer ranging from 1 to 12.
Dependencies are inferred from the claim text.