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US 2018/0237546 A1Published application
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.
Claims18
A modified diene polymer comprising:
- an in-chain substructure according to formula (X)
- and/or
- a terminal end-chain substructure according to formula (XI),
- —S—R1 (XI)
- where
- for formula (X), X is a halogen, and
- for formulae (X) and (XI), R1 is selected from a group consisting of
- an aromatic amide moiety of the formula (II)
- C6(R2)5—(C═O)—N(R3)—C5(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 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a dithiazyl disulphide moiety of the formula (III)
- where R4 are identical or different and are a hydrogen moiety, a halogen, nitro, hydroxy, a linear or branched alkyl moiety having 1 to 12 C atoms, a linear or branched alkoxy moiety having 1 to 12 C atoms, a phenyl moiety, a cycloalkyl moiety having 5 to 8 C atoms, or together form the cyclic moiety of the formula (IV);
- where R are identical or different and are a hydrogen moiety, hydroxy, a linear or branched alkyl moiety having 1 to 12 C atoms, a linear or branched alkoxy moiety having 1 to 12 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a bistrialkoxysilylalkyl polysulphide moiety of the formula (V)
- (R6O)3Si—(CH2)n—(Y)m— (V)
- where
- n is an integer 1 to 12;
- m is an integer 0 to 4;
- R6 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- Y is sulphur, a group of the formula (Via), (VIb), (Vic), (Vid), or (Vie)
- where
- x is an integer 1 to 8;
- p is an integer 1 to 12;
- R8 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, an alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a phenoxy moiety;
- thiuram moiety of the formula (VII)
- (R9)2N—(C═Z)— (VII)
- where
- Z is sulphur or oxygen,
- R9 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a dithioxanthogenate moiety according to the formula (VIII)
- R10—O—C(═S)— (VIII)
- where
- R10 are identical or different and are a hydrogen atom, linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a phosphonate moiety according to the formula (IX)
- (R11—O)(R11—O)P(Z)— (IX)
- where
- Z is a sulphur or oxygen atom, and
- R11 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms.
35 more elements
A process for producing a modified polymer, the process comprising reacting a diene polymer with at least one halogenated sulphidic organic compound, wherein the halogenated sulphidic organic compound is formed by reacting a halogen with a sulphidic compound with the general formula (I-a) and/or (I-b) and/or (I-c):
- R1—S—S—R1 (I-a),
- R1—S—(S)n—S—R1, where 1≤n≤8 (I-b),
- R1—SH (I-c),
- where R1 are identical or different and selected from a group consisting of:
- an aromatic amide moiety of the formula (II)
- C6(R2)5—(C═O)—N(R3)—C6(R3)4— (II)
- where R2 and R3 are identical or different and are a hydrogen moiety, a linear or branched alkyl moiety having 1 to 18 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a dithiazyl disulphide moiety of the formula (III)
- where R4 are identical or different and are a hydrogen moiety, a halogen, nitro, hydroxy, a linear or branched alkyl moiety having 1 to 12 C atoms, a linear or branched alkoxy moiety having 1 to 12 C atoms, a phenyl moiety, a cycloalkyl moiety having 5 to 8 C atoms, or together form the cyclic moiety of the formula (IV);
- where R5 are identical or different and are a hydrogen moiety, hydroxy, a linear or branched alkyl moiety having 1 to 12 C atoms, a linear or branched alkoxy moiety having 1 to 12 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a bistrialkoxysilylalkyl polysulphide moiety of the formula (V)
- (R6O)3Si—(CH2)n—(Y)m— (V)
- where
- n is an integer 1 to 12;
- m is an integer 0 to 4;
- R6 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, a cycloalkyl moiety having 5 to 8 C atoms;
- Y is sulphur, a group of the formula (Via), (VIb), (Vic), (Vid), or (Vie)
- where
- x is an integer 1 to 8;
- p is an integer 1 to 12;
- R8 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, an alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a phenoxy moiety;
- a thiuram moiety of the formula (VII)
- (R9)2N—(C═Z)— (VII)
- where
- Z is sulphur or oxygen,
- R9 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a dithioxanthogenate moiety according to the formula (VIII)
- R10—O—C(═S)— (VIII)
- where
- R10 are identical or different and are a hydrogen atom, linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms;
- a phosphonate moiety according to the formula (IX)
- (R11—O)(R11—O)P(Z)— (IX)
- where
- Z is a sulphur or oxygen atom, and
- R11 are identical or different and are a hydrogen atom, a linear or branched alkyl moiety having 1 to 16 C atoms, a phenyl moiety, or a cycloalkyl moiety having 5 to 8 C atoms.
32 more elements
Dependencies are inferred from the claim text.