Heteroatom containing modified diene polymers
AssigneeArlanxeo Deutschland GmbH
InventorsHeike Kloppenburg, Thomas Ruenzi
Life of this patent
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Abstract
Modified diene polymers containing heteroatoms are disclosed, as is their production, rubber mixtures comprising these modified diene rubbers, and to their use for the production of rubber vulcanizates, which serve, in particular, for the production of rubber moldings and the production of tires.
Claims19
A modified diene polymer comprising:
- an in-chain substructure according to formula (X):
- where
- X is a halogen, and
- R1 is selected from a group consisting of
- an aromatic amide moiety of formula (II):
- C6(R2)5—(C═O)—N(R3)—C6(R2)4— (II)
- where R2 and R3 are identical or different and are a hydrogen moiety, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a dithiazyl disulphide moiety of formula (III):
- where R4a and R4b are identical or different and are a hydrogen moiety, a halogen, a nitro, a hydroxy, a linear or branched alkyl moiety having 1 to 12 carbon atoms, a linear or branched alkoxy moiety having 1 to 12 carbon atoms, a phenyl moiety, a cycloalkyl moiety having 5 to 8 carbon atoms, or together form the cyclic moiety of formula (IV):
- where R5a, R5b, R5c, and R5d are identical or different and are a hydrogen moiety, a hydroxy, a linear or branched alkyl moiety having 1 to 12 carbon atoms, a linear or branched alkoxy moiety having 1 to 12 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a thiuram moiety of formula (VII):
- where
- Z is sulphur or oxygen,
- R9a and R9b are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a dithioxanthogenate moiety according to formula (VIII):
- R10—O—C(═S)— (VIII)
- where R10 is a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- and
- a phosphonate moiety according to formula (IX):
- (R11a—O)(R11b—O)P(Z)— (IX)
- where
- Z is a sulphur or oxygen atom, and
- R11a and R11b are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms.
A rubber mixture comprising the modified diene polymer according to claim 1 and 10 to 500 parts by weight of filler, based on 100 parts by weight of the modified diene polymer.
A process for producing a modified diene polymer, the process comprising reacting a diene polymer with at least one halogenated sulphidic organic compound, wherein the at least one halogenated sulphidic organic compound is formed by reacting a halogen with at least one sulphidic compound having at least one of formula (I-a), (I-b), and (I-c):
- R1a—S—S—R1b (I-a),
- R1a—S—(S)n—S—R1b, where 1≤n≤8 (I-b),
- R1a—SH (I-c),
- where R1a and R1b are identical or different and selected from a group consisting of:
- an aromatic amide moiety of formula (II):
- C6(R2)5—(C═O)—N(R3)—C6(R2)4— (II)
- where R2 and R3 are identical or different and are a hydrogen moiety, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a dithiazyl disulphide moiety of formula (III):
- where R4a and R4b are identical or different and are a hydrogen moiety, a halogen, a nitro, a hydroxy, a linear or branched alkyl moiety having 1 to 12 carbon atoms, a linear or branched alkoxy moiety having 1 to 12 carbon atoms, a phenyl moiety, a cycloalkyl moiety having 5 to 8 carbon atoms, or together form the cyclic moiety of formula (IV):
- where R5a, R5b, R5c, and R5d are identical or different and are a hydrogen moiety, a hydroxy, a linear or branched alkyl moiety having 1 to 12 carbon atoms, a linear or branched alkoxy moiety having 1 to 12 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a thiuram moiety of formula (VII):
- where
- Z is sulphur or oxygen,
- R9a and R9b are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a dithioxanthogenate moiety according to formula (VIII):
- R10—O—C(═S)— (VIII)
- where R10 is a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms;
- a phosphonate moiety according to formula (IX):
- (R11a—O)(R11b—O)P(Z)— (IX)
- where
- Z is a sulphur or oxygen atom, and
- R11a and R11b are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 carbon atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 carbon atoms.
Dependencies are inferred from the claim text.