Silane functional amine compositions and their use in rubber

Abstract

The present disclosures are directed to a composition comprising at least one silane functional amine; a method of preparing a silane functional amine; a rubber composition comprising at least one silane functional amine, at least one diene-based polymer, silica, at least one process aid, and a vulcanizing package comprising at least one vulcanizing agent comprising sulfur and at least one accelerator; and a process of preparing a rubber composition.

Description

[Technical Field]

[0001] This invention relates to a composition comprising at least one silane-functionalized amine and a method for preparing at least one silane-functionalized amine. Further, this invention relates to a rubber composition comprising a composition containing at least one silane-functionalized amine, at least one diene polymer, silica, at least one processing aid and a vulcanizing agent, and a method for preparing the rubber composition. [Previous Technology]

[0002] Historically, tire treads have been formulated using carbon black and natural rubber due to their excellent wear and tear properties. The disadvantage of using carbon black and natural rubber is that the resulting rubber tread compound exhibits high hysteresis (i.e., high rolling resistance), which negatively impacts fuel efficiency. Regulatory drivers, including Corporate Average Fuel Economy (CAFE) standards, greenhouse gas (GHG) regulations, Environmental Protection Agency (EPA) regulations, and European tire labeling regulations, all place great emphasis on energy conservation. Therefore, tire manufacturers are increasingly committed to producing tires with low rolling resistance while maintaining good wear and tear properties.

[0003] One method for improving rolling resistance (reducing hysteresis) is the use of sulfur-containing silanes and silica fillers, which are very effective for tires made of synthetic rubber. However, when standard sulfur-containing silanes are used in natural rubber silica blends, wear and tear properties are affected compared to carbon black natural rubber blends. The long-term goal of the tire industry is to produce tread compounds based on natural rubber that have similar good wear / tear properties to carbon black natural rubber blends and similar low rolling resistance to sulfur-containing silane natural rubber silica blends.

[0004] It is still necessary to manufacture natural rubber tread compounds with good abrasion / tear properties and low hysteresis properties. [Summary of the Invention]

[0005] The compositions disclosed herein comprise at least one silane-functionalized amine, wherein the at least one silane-functionalized amine is a compound of formula (I): (R1)aG-(NR2)b; and further wherein:

[0006] G represents a saturated or unsaturated cyclic portion;

[0007] Each R 1 is independently selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms;

[0008] Each R is independently selected from the group consisting of: hydrogen and -L-SiX1X2X3; subject to the condition that at least one R is hydrogen and at least one R is -L-SiX1X2X3;

[0009] Each L is independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0010] Each X1 is independently selected from the group consisting of: hydroxyl, -OR2 and -OC(=O)R2;

[0011] Each X2 and each X3 is independently selected from the group consisting of: hydroxyl, -OR2, -OC(=O)R2 and R2;

[0012] Each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms;

[0013] a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and

[0014] b is 1 or 2.

[0015] The present invention further relates to a method for preparing at least one silane-functionalized amine, the method comprising reacting a compound of formula (II): (R ​​1) aG-(NH 2) b with one or more compounds of formula (III): ML-SiX 1X 2X 3; and wherein the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 2b-1; and further wherein:

[0016] G is a saturated or unsaturated cyclic portion;

[0017] Each R 1 is independently selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms;

[0018] Each L is independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0019] Each X1 is independently selected from the group consisting of: hydroxyl, -OR2 and -OC(=O)R2;

[0020] Each X2 and each X3 is independently selected from the group consisting of: hydroxyl, -OR2, -OC(=O)R2 and R2;

[0021] Each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms;

[0022] Each M is independently a halogen;

[0023] a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and

[0024] b is 1 or 2.

[0025] The present invention further relates to a rubber composition comprising: a. a composition comprising at least one silane-functionalized amine; b. at least one diene polymer; c. silicon dioxide; d. at least one processing aid; and e. a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator.

[0026] The present invention further provides a rubber composition comprising: (i) about 100 parts of rubber, wherein the weight of the rubber is the sum of the weight of each diene polymer containing at least one functional group used in the formulation and the weight of each diene polymer without functional group used in the formulation; (ii) about 1 to about 20 parts by weight of a composition containing at least one silane functional amine per 100 parts of rubber (i); (iii) about 5 to about 140 parts by weight of silicon dioxide per 100 parts of rubber (i); (iv) about 0.1 to about 10 parts by weight of at least one processing aid per 100 parts of rubber (i); and (v) about 0.1 to about 20 parts by weight of a vulcanizing package containing at least one sulfur-containing vulcanizing agent and at least one accelerator per 100 parts of rubber (i).

[0027] The present invention also provides a method for preparing a rubber composition, comprising adding a composition containing at least one silane functional amine and silicon dioxide to at least one diene polymer.

[0028] The method provided by the present invention further includes adding at least one processing aid while containing a vulcanizing package containing at least one sulfur-containing vulcanizing agent and at least one accelerator.

[0029] The present invention provides a rubber composition comprising: a. about 0.05% to about 12% by weight of a composition comprising at least one silane-functionalized amine; b. about 5% to about 70% by weight of at least one diene polymer; c. about 10% to about 40% by weight of silica; d. about 0.05% to about 5% by weight of at least one processing aid; and e. about 0.05% to about 5% by weight of a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator.

[0030] The present invention further provides a rubber composition prepared by the method.

[0031] The present invention also provides an article comprising the rubber composition.

Implementation Method

[0034] As used above and throughout the specification, unless otherwise specified, the following terms shall be understood to have the following meanings.

[0035] Unless otherwise stated, the terms "a," "an," and "the," and similar references used in the context of describing a particular aspect of this application (particularly in the context of the claims), are to be interpreted as encompassing both the singular and the plural. The description of the range of values ​​herein is intended only as a way of individually referring to each individual value belonging to that range. Unless otherwise indicated herein, each individual value is incorporated into this specification as if it were individually described herein.

[0036] Furthermore, when used herein, "and / or" should be considered to specifically reveal the presence or absence of one of the two specified features or components. Thus, the term "and / or" as used in phrases such as "A and / or B" herein is intended to include "A and B", "A or B", "A" (alone) and "B" (alone). Similarly, the term "and / or" as used in phrases such as "A, B and / or C" is intended to cover each of the following states: A, B and C; A, B or C; A or C; A or B; B or C; A and C; A and B; B and C; A (alone); B (alone); and C (alone).

[0037] It should be understood that whenever a state is described in this document using the language “comprising”, similar states described using the terms “composed of” and / or “substantially composed of” are also provided.

[0038] The term "polymer" means a substance, compound, or mixture of compounds having a molecular structure consisting mainly or entirely of a large number of similar units (e.g., monomer units) bonded together.

[0039] The terms “functionalized diene polymer” and “diene polymer containing at least one functional group (i)(a)” are synonymous and therefore interchangeable.

[0040] The terms “nonfunctionalized diene polymer” and “diene polymer without functional groups (i)(b)” are synonymous and therefore interchangeable.

[0041] The term "about" covers the range of experimental error that occurs in any measurement. The term "about" includes ±10% of the stated number. Therefore, "about 10" means 9 to 11.

[0042] The terms "elastomer" and "rubber" are synonymous and therefore interchangeable.

[0043] The terms “vulcanization” and “curing” are synonymous and therefore interchangeable.

[0044] The term "coupling agent" means an agent capable of establishing effective chemical and / or physical bonds between a diene polymer and a filler, or an agent capable of establishing effective chemical or physical bonds between two diene polymers. An effective coupling agent has functional groups capable of physical and / or chemical bonding with a filler or a second diene polymer, for example, between a silanol group of the coupling agent and a hydroxyl (OH) surface group of the filler (e.g., surface silanol in the case of silicon dioxide), or for example, between a silanol group of one diene polymer connected to a silanol group of another polymer and a sulfur atom that can physically and / or chemically bond with the diene polymer due to vulcanization (curing).

[0045] The term "filler" refers to a substance added to a diene polymer (rubber) to stretch the rubber or reinforce the elastomer network. A reinforcing filler is a material whose modulus is higher than that of the diene polymer in the elastomer composition and which can absorb stress from the diene polymer when the elastomer is strained. Fillers include fibrous, needle-like, nanotube, particulate, and sheet-like structures and may be composed of inorganic minerals, silicates, silica, clay, ceramics, carbon, organic polymers, and diatomaceous earth.

[0046] As used herein, "hydrocarbon" refers to any chemical structure containing hydrogen and carbon atoms.

[0047] The term "alkyl" means any monovalent saturated straight-chain or branched hydrocarbon group; the term "alkenyl" means any monovalent straight-chain or branched hydrocarbon group containing one or more carbon-carbon double bonds, wherein the connection point of the group may be at a carbon-carbon double bond or elsewhere; and the term "alkynyl" means any monovalent straight-chain or branched hydrocarbon group containing one or more carbon-carbon reference bonds and, as appropriate, one or more carbon-carbon double bonds, wherein the connection point of the group may be at a carbon-carbon reference bond, a carbon-carbon double bond or elsewhere.

[0048] Representative examples of alkyl groups include methyl, ethyl, propyl, and isobutyl. Examples of alkenyl groups include vinyl, propenyl, allyl, methylallyl, vinylidene norbornene, ethylidene norbornenealkyl, vinylidene norbornene, and ethylidene norborneneyl. Examples of alkynyl groups include ethynyl, propynyl, and methylethynyl.

[0049] The term "cycloalkyl" means any monovalent cyclic aliphatic hydrocarbon group; the term "cycloalkenyl" means any monovalent cyclic aliphatic hydrocarbon group containing one or more carbon-carbon double bonds, wherein the connection point of the group may be at a carbon-carbon double bond or elsewhere; and the term "cycloalkynyl" means any monovalent cyclic aliphatic hydrocarbon group containing one or more carbon-carbon reference bonds and, as appropriate, one or more carbon-carbon double bonds, wherein the connection point of the group may be at a carbon-carbon reference bond, a carbon-carbon double bond or elsewhere.

[0050] Representative examples of cycloalkyl groups include cyclopentyl, cyclobutyl, cycloheptyl, and cyclooctyl. Examples of cycloalkenyl groups include cyclopentenyl, cycloheptenyl, and cyclooctenyl. An example of cycloynyl group is cycloheptynyl.

[0051] The terms "cycloalkyl", "cycloalkenyl" and "cycloalkynyl" include bicyclic, tricyclic and higher cyclic structures, as well as the aforementioned cyclic structures further substituted with alkyl, alkenyl and / or alkynyl groups. Representative examples include norbornelalkyl, norbornelalyl, ethylnorbornelalkyl, ethylnorbornelalyl, cyclohexyl, ethylcyclohexyl, ethylcyclohexenyl, cyclohexylcyclohexyl and cyclododecanetrienyl.

[0052] The term "aryl" includes any aromatic hydrocarbon in which one hydrogen atom has been removed; "aralkyl" includes any of the aforementioned alkyl groups in which one or more hydrogen atoms have been replaced by the same number of the same and / or different aryl (as defined herein) substituents; and "arenyl" includes any of the aforementioned aryl groups in which one or more hydrogen atoms have been replaced by the same number of the same and / or different alkyl (as defined herein) substituents. Specific non-limiting examples of aryl include phenyl and naphthyl. Specific non-limiting examples of aralkyl include benzyl and phenethyl. Specific non-limiting examples of arenyl include tolyl and xylyl.

[0053] The term "alkyl group" is a divalent saturated aliphatic group derived from an alkane by removing two hydrogen atoms.

[0054] The term "heteroatom" means any of the elements in Groups 13 to 17 except carbon, and includes, for example, oxygen, nitrogen, silicon, sulfur, phosphorus, fluorine, chlorine, bromine and iodine.

[0055] The term "halogen" or "halogen" as used alone or as part of another group refers to -CI, -F, -Br or -I.

[0056] The term "hydroxyl" as used alone or as part of another group refers to -OH.

[0057] The term "alkoxy" as used alone or as part of another group refers to an alkyl group, a cycloalkyl group, an alkenyl group, or an alkynyl group, which is optionally substituted and attached to a terminal oxygen atom. Alkoxy groups are selected from C1-20 alkyl groups, such as methoxy, ethoxy, and tert-butoxy.

[0058] Except as indicated in the working example or otherwise, all figures representing the amount of material, reaction conditions, duration, quantitative properties of material, etc., stated in the specification and claims shall be understood to be modified by the term “about” in all cases.

[0059] It should be understood that any numerical range described herein includes all subranges accompanying the range and any combination of the different endpoints of such ranges or subranges.

[0060] It should be further understood that any compound, material or substance that is expressly or implicitly disclosed in this specification and / or described in the claims as belonging to a group of compounds, materials or substances that are structurally, compositionally and / or functionally related includes individual representatives of that group and all combinations thereof.

[0061] The compositions disclosed herein comprise at least one silane-functionalized amine, wherein the at least one silane-functionalized amine is a compound of formula (I): (R1)aG-(NR2)b; and further wherein:

[0062] G is a saturated or unsaturated cyclic portion;

[0063] Each R1 is independently selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms;

[0064] Each R is independently selected from the group consisting of: hydrogen and -L-SiX1X2X3; subject to the condition that at least one R is hydrogen and at least one R is -L-SiX1X2X3;

[0065] Each L is independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0066] Each X1 is independently selected from the group consisting of: hydroxyl, -OR2 and -OC(=O)R2;

[0067] Each X2 and each X3 are independently selected from the group consisting of: hydroxyl, -OR2, -OC(=O)R2 and R2;

[0068] Each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms;

[0069] a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11; and

[0070] b is 1 or 2.

[0071] In some states, b is 1, a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, and at least one R1 group located in the ortho position of the amino group has at least one α hydrogen atom.

[0072] In some states, b is 1, a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, and at least one R1 group located at the para position of the amino group has at least one α hydrogen atom.

[0073] In some states, b is 1, a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, and at least one R1 group is located at the meta position of an amino group.

[0074] In some states, G is a saturated or unsaturated cyclic moiety selected from the group of the following components: benzene ring, naphthalene ring, anthracene ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, decahydronaphthalene ring, dialkyl ring, pyridine ring, pyrimidine ring, piperan ring, isoquinoline ring, quinoline ring, and α-cyclopentane ring.

[0075] In some states, G is selected from the group consisting of: benzene ring, cyclohexane ring and pyridine ring.

[0076] In some states, G is a benzene ring, b is 1 or 2, and a is 0, 1, 2, 3, 4 or 5; the restriction condition is that the sum of a and b is equal to or less than 6.

[0077] In some states, G is a benzene ring, b is 1, and a is 1, 2, 3, 4 or 5.

[0078] In some states, G is a benzene ring, b is 2, and a is 0, 1, 2, 3 or 4.

[0079] In some samples, G is a cyclohexane ring, b is 1 or 2, and a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the restriction condition is that the sum of a and b is equal to or less than 12.

[0080] In some samples, G is a cyclohexane ring, b is 1, and a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0081] In some samples, G is a cyclohexane ring, b is 2, and a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0082] In some states, G is a pyridine ring, b is 1 or 2, and a is 0, 1, 2, 3 or 4; the restriction condition is that the sum of a and b is equal to or less than 5.

[0083] In some states, G is a pyridine ring, b is 1, and a is 1, 2, 3 or 4.

[0084] In some states, G is a pyridine ring, b is 2, and a is 0, 1, 2 or 3.

[0085] In one state sample, G is a benzene ring, b is 1, a is 1, 2, 3, 4 or 5, one R is -L-SiX 1X 2X 3, and the other R is hydrogen.

[0086] In some samples, G is a benzene ring, b is 1, a is 1, one R is -L-SiX 1X 2X 3, and the other R is hydrogen.

[0087] In some states, G is a benzene ring, b is 1, a is 1, one R is -L-SiX 1X 2X 3, and the other R is hydrogen; wherein the R 1 group is located in the ortho position of the amino group, and the R 1 group has at least one α hydrogen atom.

[0088] In some states, G is a benzene ring, b is 1, a is 1, one R is -L-SiX 1X 2X 3, and the other R is hydrogen; and wherein the R 1 group is located at the para position of the amino group, and the R 1 group has at least one α hydrogen atom.

[0089] In some states, G is a benzene ring, b is 1, a is 1, one R is -L-SiX 1X 2X 3, and the other R is hydrogen; and the R 1 group is located at the meta position of the amino group.

[0090] In some states, the compound of formula (I) is: and the R1 group has at least one α hydrogen atom.

[0091] In some states, R1 is selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms.

[0092] In some states, R1 is an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms.

[0093] In some states, R1 is an alkyl group having 1 to 20 carbon atoms.

[0094] In some states, R1 is -CH2CH3.

[0095] In some states, L is selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0096] In some states, L is an alkyl group having 1 to 20 carbon atoms and at least one heteroatom as appropriate, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0097] In some states, L is an alkyl group having 1 to 20 carbon atoms and, as appropriate, at least one heteroatom.

[0098] In some states, L is an alkyl group having 1 to 20 carbon atoms.

[0099] In some states, L is -CH 2CH 2CH 2-.

[0100] In some states, X1 is a hydroxyl group, -OR2 or -OC(=O)R2.

[0101] In some states, X2 is a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0102] In some states, X3 is a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0103] In some states, each X1, X2 and X3 is independently -OR 2.

[0104] In some states, each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms.

[0105] In some states, each R2 is independently an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0106] In some states, each R2 is independently an alkyl group having 1 to 20 carbon atoms.

[0107] In some states, each R2 is independently -CH2CH3.

[0108] In some states, the compound of formula (I) is.

[0109] In another state, G is a benzene ring, b is 2, a is 0, 1, 2, 3 or 4, at least one R is hydrogen, and at least one R is -L-SiX 1X 2X 3.

[0110] In some states, G is a benzene ring, b is 2, a is 0, at least one R is hydrogen, and at least one R is -L-SiX 1X 2X 3.

[0111] In some states, one amino group is located adjacent to another amino group.

[0112] In some states, one amino group is located at the para position of another amino group.

[0113] In some states, one amino group is located between another amino group.

[0114] In some states, the compounds of formula (I) are selected from the group of the following compositions: and combinations thereof.

[0115] In some states, the compound of formula (I) is.

[0116] In some states, the compound of formula (I) is.

[0117] In some states, the compound of formula (I) is.

[0118] In some states, the compound of formula (I) is.

[0119] In some states, each L is independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0120] In some states, each L is independently an alkyl group having 1 to 20 carbon atoms and, as appropriate, at least one heteroatom, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0121] In some states, each L is independently an alkyl group having 1 to 20 carbon atoms and, as appropriate, at least one heteroatom.

[0122] In some states, each L is independently an alkyl group having 1 to 20 carbon atoms.

[0123] In some states, each L is independently -CH 2CH 2CH 2-.

[0124] In some states, each X1 is independently a hydroxyl group, -OR2 or -OC(=O)R2.

[0125] In some states, each X2 is independently a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0126] In some states, each X3 is independently a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0127] In some states, each X1, X2 and X3 is independently -OR 2.

[0128] In some states, each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms.

[0129] In some states, each R2 is independently an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0130] In some states, each R2 is independently an alkyl group having 1 to 20 carbon atoms.

[0131] In some states, each R2 is independently -CH2CH3.

[0132] In some states, the compounds of formula (I) are selected from the group of the following compositions: and combinations thereof.

[0133] In some states, the compound of formula (I) is.

[0134] In some states, the compound of formula (I) is.

[0135] In some states, the compound of formula (I) is.

[0136] In some states, the compound of formula (I) is.

[0137] The present invention further relates to a method for preparing at least one silane-functionalized amine, the method comprising reacting a compound of formula (II): (R ​​1) aG-(NH 2) b with one or more compounds of formula (III): ML-SiX 1X 2X 3; and wherein the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 2b-1; and further wherein:

[0138] G is a saturated or unsaturated cyclic portion;

[0139] Each R 1 is independently selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms;

[0140] Each L is independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0141] Each X1 is independently selected from the group consisting of: hydroxyl, -OR2 and -OC(=O)R2;

[0142] Each X2 and each X3 is independently selected from the group consisting of: hydroxyl, -OR2, -OC(=O)R2 and R2;

[0143] Each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms;

[0144] Each M is an independent halogen;

[0145] a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and

[0146] b is 1 or 2.

[0147] In some states, b is 1, a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, and at least one R1 group located in the ortho position of the amino group has at least one α hydrogen atom.

[0148] In some states, b is 1, a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, and at least one R1 group located at the para position of the amino group has at least one α hydrogen atom.

[0149] In some states, b is 1, a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11, and at least one R1 group is located at the meta position of an amino group.

[0150] In some samples, the molar ratio of the total compound of formula (III) to the compound of formula (II) is about 3.0 to about 0.1, about 2.9 to about 0.1, about 2.8 to about 0.1, about 2.7 to about 0.2, about 2.6 to about 0.2, about 2.5 to about 0.2, about 2.4 to about 0.3, about 2.3 to about 0.3, about 2.2 to about 0.4, about 2.1 to about 0.4, about 2.0 to about 0.5, about 1.9 to about 0.5, about 1.8 to about 0.6, about 1.7 to about 0.6, about 1.6 to about 0.7, about 1.5 to about 0.7, about 1.4 to about 0.8, about 1.3 to about 0.8, about 1.2 to about 0.9, or about 1.1 to about 0.9. In some samples, the molar ratio of the total compound of formula (III) to the compound of formula (II) is about 1.

[0151] In some states, G is a saturated or unsaturated cyclic moiety selected from the group of the following components: benzene ring, naphthalene ring, anthracene ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, cyclooctane ring, decahydronaphthalene ring, dialkyl ring, pyridine ring, pyrimidine ring, piperan ring, isoquinoline ring, quinoline ring, and α-cyclopentane ring.

[0152] In some states, G is selected from the group consisting of: benzene ring, cyclohexane ring and pyridine ring.

[0153] In some states, G is a benzene ring, b is 1 or 2, and a is 0, 1, 2, 3, 4 or 5; the restriction condition is that the sum of a and b is equal to or less than 6.

[0154] In some states, G is a benzene ring, b is 1, and a is 1, 2, 3, 4 or 5.

[0155] In some states, G is a benzene ring, b is 2, and a is 0, 1, 2, 3 or 4.

[0156] In some samples, G is a cyclohexane ring, b is 1 or 2, and a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; the constraint is that the sum of a and b is equal to or less than 12.

[0157] In some states, G is a cyclohexane ring, b is 1, and a is 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11.

[0158] In some states, G is a cyclohexane ring, b is 2, and a is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0159] In some states, G is a pyridine ring, b is 1 or 2, and a is 0, 1, 2, 3 or 4; the constraint is that the sum of a and b is equal to or less than 5.

[0160] In some states, G is a pyridine ring, b is 1, and a is 1, 2, 3 or 4.

[0161] In some states, G is a pyridine ring, b is 2, and a is 0, 1, 2 or 3.

[0162] In one state sample, G is a benzene ring, b is 1, and a is 1, 2, 3, 4 or 5; and the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1.5.

[0163] In one state sample, G is a benzene ring, b is 1, and a is 1, 2, 3, 4 or 5; and the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1.

[0164] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of compound (III) to compound (II) is equal to or less than 1.5.

[0165] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of compound (III) to compound (II) is equal to or less than 1.

[0166] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1.5; the R1 group is located in the ortho position of the amino group; and the R1 group has at least one α hydrogen atom.

[0167] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1; the R1 group is located in the ortho position of the amino group; and the R1 group has at least one α hydrogen atom.

[0168] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1.5; the R1 group is located at the para position of the amino group; and the R1 group has at least one α hydrogen atom.

[0169] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1; the R1 group is located at the para position of the amino group; and the R1 group has at least one α hydrogen atom.

[0170] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of compound (III) to compound (II) is equal to or less than 1.5; and the R1 group is located at the meta position of the amino group.

[0171] In some states, G is a benzene ring, b is 1, and a is 1; and the molar ratio of compound (III) to compound (II) is equal to or less than 1; and the R1 group is located at the meta position of the amino group.

[0172] In some states, the compound of formula (II) is: and the R1 group has at least one α hydrogen atom.

[0173] In some states, R1 is selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms.

[0174] In some states, R1 is an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an alkenyl group having 2 to 20 carbon atoms.

[0175] In some states, R1 is an alkyl group having 1 to 20 carbon atoms.

[0176] In some samples, R1 is -CH2CH3.

[0177] In some states, the compound of formula (II) is.

[0178] In some states, at least one silane functional amine is prepared by reacting a compound of formula (II) with a compound of formula (III) in the form of ML-SiX 1X 2X 3; wherein the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1.5.

[0179] In some states, at least one silane functional amine is prepared by reacting a compound of formula (II) with a compound of formula (III) in the form of ML-SiX 1X 2X 3; wherein the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 1.

[0180] In some states, L is selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0181] In some states, L is an alkyl group having 1 to 20 carbon atoms and at least one heteroatom as appropriate, an alkenyl group having 2 to 20 carbon atoms, or an aryl group having 6 to 12 carbon atoms.

[0182] In some states, L is an alkyl group having 1 to 20 carbon atoms and, as appropriate, at least one heteroatom.

[0183] In some states, L is -CH 2CH 2CH 2-.

[0184] In some states, X1 is a hydroxyl group, -OR2 or -OC(=O)R2.

[0185] In some states, X2 is a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0186] In some states, X3 is a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0187] In some states, each X1, X2 and X3 is independently -OR 2.

[0188] In some states, each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms.

[0189] In some states, each R2 is independently an alkyl group having 1 to 20 carbon atoms.

[0190] In some states, each R2 is independently -CH2CH3.

[0191] In some states, M is a halogen.

[0192] In some samples, M is chlorine, bromine or iodine.

[0193] In some samples, M is chlorine.

[0194] In some states, the compound of formula (III) is.

[0195] In some samples, the molar ratio of compound (III) to compound (II) is equal to or less than 1.5.

[0196] In some samples, the molar ratio of compound (III) to compound (II) is about 1.0 to about 0.1, about 0.8 to about 0.2, about 0.7 to about 0.3, or about 0.6 to about 0.4. In some samples, the molar ratio of compound (III) to compound (II) is about 0.5.

[0197] In another state, G is a benzene ring, b is 2, and a is 0, 1, 2, 3 or 4; and the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 3.

[0198] In some states, G is a benzene ring, b is 2, and a is 0; and the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 3.

[0199] In some states, one amino group is located adjacent to another amino group.

[0200] In some states, one amino group is located at the para position of another amino group.

[0201] In some states, one amino group is located between another amino group.

[0202] In some states, the compound of formula (II) is.

[0203] In some states, at least one silane functional amine is prepared by reacting a compound of formula (II) with one or more compounds of formula (III): ML-SiX 1X 2X 3; and wherein the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 3.

[0204] In some states, at least one silane functional amine is prepared by reacting a compound of formula (II) with three compounds of formula (III): ML-SiX 1X 2X 3; and wherein the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 3.

[0205] In some states, at least one silane functional amine is prepared by reacting a compound of formula (II) with two compounds of formula (III): ML-SiX 1X 2X 3; and wherein the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 3.

[0206] In some states, at least one silane functional amine is prepared by reacting a compound of formula (II) with a compound of formula (III) ML-SiX 1X 2X 3; wherein the molar ratio of the compound of formula (III) to the compound of formula (II) is equal to or less than 3.

[0207] In some states, L is selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms.

[0208] In some states, L is an alkyl group having 1 to 20 carbon atoms and, as appropriate, at least one heteroatom.

[0209] In some states, L is -CH 2CH 2CH 2-.

[0210] In some states, X1 is a hydroxyl group, -OR2 or -OC(=O)R2.

[0211] In some states, X2 is a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0212] In some states, X3 is a hydroxyl group, -OR2, -OC(=O)R2 or R2.

[0213] In some states, each X1, X2 and X3 is independently -OR 2.

[0214] In some states, each R2 is independently selected from the group consisting of: alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms and aralkyl having 7 to 14 carbon atoms.

[0215] In some states, each R2 is independently an alkyl group having 1 to 20 carbon atoms.

[0216] In some states, each R2 is independently -CH2CH3.

[0217] In some samples, M is a halogen.

[0218] In some samples, M is chlorine, bromine or iodine.

[0219] In some samples, M is chlorine.

[0220] In some states, the compound of formula (III) is.

[0221] In some samples, the reaction system is carried out in the presence of a base.

[0222] In some samples, the base is an alkali metal alkoxide.

[0223] In some samples, the base is sodium ethoxide.

[0224] In some states, the molar ratio of compound (III) to compound (II) is about 3.0 to about 0.1, about 2.9 to about 0.1, about 2.8 to about 0.1, about 2.7 to about 0.2, about 2.6 to about 0.2, about 2.5 to about 0.2, about 2.4 to about 0.3, about 2.3 to about 0.3, about 2.2 to about 0.4, about 2.1 to about 0.4, about 2.0 to about 0.5, about 1.9 to about 0.5, about 1.8 to about 0.6, about 1.7 to about 0.6, about 1.6 to about 0.7, about 1.5 to about 0.7, about 1.4 to about 0.8, about 1.3 to about 0.8, about 1.2 to about 0.9, or about 1.1 to about 0.9.

[0225] In some samples, the molar ratio of compound (III) to compound (II) is equal to or less than 1.5.

[0226] In some samples, the molar ratio of compound (III) to compound (II) is about 1.

[0227] In some states, at least one silane-functionalized amine is a compound of the above formula (I): (R ​​1) aG-(NR 2) b.

[0228] The present invention further relates to a rubber composition comprising: a. a composition comprising at least one silane functionalized amine of formula (I) above: (R1)aG-(NR2)b; b. at least one diene polymer; c. silicon dioxide; d. at least one processing aid; and e. a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator. In some embodiments, the diene polymer is a diene polymer containing at least one functional group, a diene polymer without a functional group, or a combination thereof.

[0229] In some states, the diene polymer is a diene polymer containing at least one functional group.

[0230] In some states, the diene polymer is a diene polymer without functional groups.

[0231] In some samples, the diene polymer is natural rubber, cis-1,4-polyisoprene, cis-1,4-polybutadiene, or a combination thereof.

[0232] In some samples, the diene polymer is natural rubber.

[0233] In some samples, the diene polymer is cis-1,4-polyisoprene.

[0234] In some samples, the diene polymer is cis-1,4-polybutadiene.

[0235] In some samples, the diene polymer is natural rubber, polyisoprene, polybutadiene, styrene-butadiene copolymer (SBR) or a combination thereof.

[0236] In some samples, the processing aid is 2,2,4-trimethyl-1,2-dihydroquinoline, octyltriethoxysilane, triethoxysilane or a combination thereof.

[0237] In some samples, the processing aid is 2,2,4-trimethyl-1,2-dihydroquinoline.

[0238] In some samples, the processing aid is octyltriethoxysilane.

[0239] In some samples, the processing aid is triethoxysilane.

[0240] In some samples, the sulfur system in the vulcanizing agent is selected from the group consisting of elemental sulfur, sulfur-donating compounds and their combinations.

[0241] In some samples, the sulfur in the vulcanizing agent is elemental sulfur.

[0242] In some samples, the sulfur in the vulcanizing agent is a sulfur-donating compound.

[0243] In some samples, the accelerator is selected from the group consisting of benzothiazole, guanidine derivatives, thiocarbamates and combinations thereof.

[0244] In some samples, the accelerator is benzothiazole.

[0245] In some samples, the accelerator is a guanidine derivative.

[0246] In some samples, the accelerator is a thiocarbamate.

[0247] In some samples, the accelerator is selected from the group consisting of: mercaptobenzothiazole, benzothiazole disulfide, diphenylguanidine, zinc dithiocarbamate, alkylphenol disulfide, zinc butyl xanthate, N-dicyclohexyl-2-benzothiazole sulfinamide, N-cyclohexyl-2-benzothiazole sulfinamide, N-oxodiethylbenzothiazole-2-sulfinamide, N,N-diphenylthiourea, dithioaminomethyl sulfinamide, N,N-diisopropylbenzothiazole-2-sulfinamide, zinc-2-mercaptotolide, dithiobis(N-methylpiperazine), dithiobis(N-β-hydroxyethylpiperazine), dithiobis(diphenylmethylamine), and combinations thereof.

[0248] In some samples, the accelerator is N-cyclohexyl-2-benzothiazolylsulfinamide.

[0249] In some samples, the accelerator is diphenylguanidine.

[0250] In some samples, the rubber composition further comprises at least one filler.

[0251] In some samples, the filler is selected from the group consisting of: titanium dioxide, alumina, aluminosilicate, silicate material, carbon black, acetylene black, calcium carbonate, barium sulfate, and combinations thereof.

[0252] In some samples, the filler is carbon black.

[0253] In some samples, the rubber composition further comprises at least one processing oil.

[0254] In some samples, the processed oil is a treated distillate aromatic extract (TDAE) oil.

[0255] In some samples, the rubber composition further comprises at least one activator.

[0256] In some samples, the activator is zinc oxide.

[0257] In some samples, the activator is stearic acid.

[0258] In some samples, the rubber composition further comprises at least one anti-breakage agent.

[0259] In some samples, the anti-disintegration agent is N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine.

[0260] In some samples, the anti-disintegration agent is a 2,2,4-trimethyl-1,2-dihydroquinoline polymer.

[0261] In some samples, the anti-collapse agent is microcrystalline wax.

[0262] In some states, at least one silane-functionalized amine can react with at least one dienyl polymer.

[0263] In some states, at least one silane-functionalized amine can react with silicon dioxide.

[0264] In some samples, the composition is curable.

[0265] In some samples, the Mooney viscosity of the composition, as measured using ASTM D-1646, is approximately 75 MU to approximately 160 MU, approximately 80 MU to approximately 160 MU, approximately 85 MU to approximately 160 MU, approximately 90 MU to approximately 160 MU, approximately 95 MU to approximately 160 MU, approximately 100 MU to approximately 155 MU, approximately 105 MU to approximately 155 MU, approximately 110 MU to approximately 155 MU, approximately 115 MU to approximately 155 MU, approximately 120 MU to approximately 155 MU, approximately 125 MU to approximately 150 MU, approximately 130 MU to approximately 150 MU, approximately 135 MU to approximately 150 MU, approximately 140 MU to approximately 148 MU, approximately 141 MU to approximately 147 MU, approximately 142 MU to approximately 146 MU, or approximately 143 MU. From MU to approximately 145 MU. In some samples, the composition has a Menner viscosity of approximately 144 MU.

[0266] In some samples, the Mooney scorch (3 pt rise) of the composition, as measured using ASTM D-1646, was about 1 minute to about 20 minutes, about 1 minute to about 19 minutes, about 1 minute to about 18 minutes, about 2 minutes to about 17 minutes, about 2 minutes to about 16 minutes, about 2 minutes to about 15 minutes, about 3 minutes to about 14 minutes, about 3 minutes to about 13 minutes, about 3 minutes to about 12 minutes, about 4 minutes to about 11 minutes, about 5 minutes to about 10 minutes, about 6 minutes to about 10 minutes, or about 7 minutes to about 9 minutes. In some samples, the composition had a Mooney scorch (3 pt rise) of about 8 minutes.

[0267] In some samples, the tensile strength of the composition, as measured using ASTM D-412, is about 5 MPa to about 30 MPa, about 6 MPa to about 30 MPa, about 7 MPa to about 29 MPa, about 8 MPa to about 29 MPa, about 9 MPa to about 28 MPa, about 10 MPa to about 28 MPa, about 11 MPa to about 27 MPa, about 12 MPa to about 26 MPa, about 13 MPa to about 25 MPa, about 14 MPa to about 24 MPa, about 15 MPa to about 23 MPa, about 16 MPa to about 22 MPa, about 17 MPa to about 21 MPa, or about 18 MPa to about 20 MPa. In some samples, the composition has a tensile strength of about 19 MPa.

[0268] In some samples, the DIN wear loss of the composition, as measured using ASTM D-5963, is approximately 80 mm³ to approximately 120 mm³, approximately 80 mm³ to approximately 118 mm³, approximately 81 mm³ to approximately 116 mm³, approximately 81 mm³ to approximately 114 mm³, approximately 82 mm³ to approximately 112 mm³, approximately 82 mm³ to approximately 110 mm³, approximately 83 mm³ to approximately 108 mm³, approximately 83 mm³ to approximately 106 mm³, approximately 84 mm³ to approximately 104 mm³, approximately 85 mm³ to approximately 102 mm³, approximately 86 mm³ to approximately 100 mm³, approximately 87 mm³ to approximately 99 mm³, approximately 88 mm³ to approximately 98 mm³, approximately 89 mm³ to approximately 97 mm³, approximately 90 mm³ to approximately 96 mm³, and approximately 91 mm³ to approximately 95 mm³. mm 3 or about 92 mm 3 to about 94 mm 3. In some samples, the composition has a DIN wear loss of about 93 mm 3.

[0269] In some samples, the composition exhibits a rebound of about 40% to about 80% at 70°C, as measured using ASTM D-7121-05. In some samples, the rebound of the composition at 70°C is about 41% to about 79%, about 42% to about 78%, about 43% to about 77%, about 44% to about 76%, about 45% to about 75%, about 46% to about 74%, about 47% to about 73%, about 48% to about 72%, about 49% to about 71%, about 50% to about 70%, about 51% to about 69%, about 52% to about 68%, about 53% to about 67%, about 54% to about 66%, about 55% to about 66%, about 56% to about 65%, about 57% to about 65%, about 58% to about 64%, about 59% to about 63%, or about 60% to about 62%. In some samples, the composition exhibits a rebound of about 61% at 70°C.

[0270] The present invention further provides a rubber composition comprising: (i) about 100 parts of rubber, wherein the weight of the rubber is the sum of the weight of each diene polymer containing at least one functional group used in the formulation and the weight of each diene polymer without functional group used in the formulation; (ii) about 1 to about 20 parts by weight of a composition comprising at least one silane functionalized amine of formula (I) above: (R1)aG-(NR2)b per 100 parts of rubber (i); (iii) about 5 to about 140 parts by weight of silicon dioxide per 100 parts of rubber (i); (iv) about 0.1 to about 10 parts by weight of at least one processing aid per 100 parts of rubber (i); and (v) about 0.1 to about 20 parts by weight of a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator per 100 parts of rubber (i).

[0271] In some formulations, the composition comprising at least one silane-functionalized amine is in the form of about 1 to 20 parts by weight, about 1 to 18 parts, about 1 to 16 parts, about 2 to 14 parts, about 2 to 12 parts, about 2 to 10 parts, about 3 to 8 parts, about 3 to 6 parts, or about 3 to 5 parts per 100 parts of rubber. In some formulations, the composition comprising at least one silane-functionalized amine is in the form of about 4 parts by weight per 100 parts of rubber.

[0272] In some samples, silicon dioxide is present in quantities of about 5 to about 140 parts by weight, about 10 to about 130 parts, about 15 to about 120 parts, about 20 to about 110 parts, about 25 to about 100 parts, about 30 to about 90 parts, about 35 to about 80 parts, about 40 to about 70 parts, about 40 to about 60 parts, or about 45 to about 55 parts per 100 parts of rubber. In some samples, silicon dioxide is present in quantities of about 50 parts by weight per 100 parts of rubber.

[0273] In some samples, at least one processing aid is present in amounts of about 0.1 to about 10 parts by weight, about 0.1 to about 8 parts by weight, about 0.1 to about 6 parts by weight, about 0.1 to about 4 parts by weight, about 0.1 to about 2 parts by weight, about 0.1 to about 1 part by weight, about 0.1 to about 0.9 parts by weight, about 0.2 to about 0.8 parts by weight, about 0.3 to about 0.7 parts by weight, or about 0.4 to about 0.6 parts by weight per 100 parts of rubber. In some samples, at least one processing aid is present in amounts of about 0.5 parts by weight per 100 parts of rubber.

[0274] In some samples, the vulcanizing package containing at least one sulfur-containing vulcanizing agent and at least one accelerator is approximately 0.1 to 20 parts by weight, approximately 0.5 to 15 parts by weight, approximately 1.0 to 10 parts by weight, approximately 1.5 to 8 parts by weight, approximately 2 to 6 parts by weight, or approximately 3 to 5 parts by weight per 100 parts of rubber. In some samples, the vulcanizing package containing at least one sulfur-containing vulcanizing agent and at least one accelerator is approximately 4 parts by weight per 100 parts of rubber.

[0275] The present invention also provides a method for preparing a rubber composition, the method comprising adding a composition comprising at least one silane functional amine of formula (I) above: (R1)aG-(NR2)b and silicon dioxide to at least one diene polymer.

[0276] The method provided by the present invention further includes adding at least one processing aid while containing a vulcanizing package containing at least one sulfur-containing vulcanizing agent and at least one accelerator.

[0277] In some forms, at least one silane functional amine is prepared by a method comprising reacting a compound of formula (II): (R ​​1) aG-(NH 2) b with one or more of the above-mentioned compounds of formula (III): ML-SiX 1X 2X 3.

[0278] In some states, at least one silane-functionalized amine can react with at least one dienyl polymer.

[0279] In some states, at least one silane-functionalized amine can react with silicon dioxide.

[0280] In some embodiments, the rubber composition comprises: a. about 0.05% to about 12% by weight of a composition comprising at least one of the above-mentioned silane-functionalized amines; b. about 5% to about 70% by weight of at least one diene polymer; c. about 10% to about 40% by weight of silicon dioxide; d. about 0.05% to about 5% by weight of at least one processing aid; and e. about 0.05% to about 5% by weight of a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator.

[0281] In some formulations, the rubber composition comprises about 0.05% to about 12% by weight of a composition comprising at least one silane-functionalized amine, about 0.1% to about 11% by weight, about 0.2% to about 10% by weight, about 0.3% to about 9% by weight, about 0.4% to about 8% by weight, about 0.5% to about 7% by weight, about 0.6% to about 6%, about 0.7% to about 5.5%, about 0.8% to about 5%, about 0.9% to about 4.5%, about 1.0% to about 4%, about 1.25% to about 3.5%, about 1.5% to about 3.0%, about 1.75% to about 2.75%, or about 2.0% to about 2.5%. In some formulations, the rubber composition comprises about 2.25% by weight of a composition comprising at least one silane-functionalized amine.

[0282] In some embodiments, the rubber composition comprises about 5% to about 70% by weight of at least one diene polymer, about 15% to about 68% by weight, about 25% to about 66% by weight, about 35% to about 64% by weight, about 45% to about 62% by weight, about 50% to about 60% by weight, about 52% to about 59% by weight, about 54% to about 58% by weight, or about 55% to about 57% by weight. In some embodiments, the rubber composition comprises about 56% by weight of at least one diene polymer.

[0283] In some embodiments, the rubber composition comprises about 10% to about 40% by weight of silicon dioxide, about 15% to about 38% by weight, about 20% to about 36% by weight, about 22% to about 34% by weight, about 24% to about 32% by weight, about 26% to about 30% by weight, or about 27% to about 29% by weight. In some embodiments, the rubber composition comprises about 28% by weight of silicon dioxide.

[0284] In some embodiments, the rubber composition comprises at least one processing aid in the form of about 0.05% to about 5% by weight, about 0.10% to about 4%, about 0.15% to about 3%, about 0.18% to about 2%, about 0.20% to about 1%, about 0.21% to about 0.8%, about 0.22% to about 0.7%, about 0.23% to about 0.6%, about 0.24% to about 0.5%, about 0.25% to about 0.4%, about 0.26% to about 0.3%, or about 0.27% to about 0.29%. In some embodiments, the rubber composition comprises at least one processing aid in the form of about 0.28% by weight.

[0285] In some formulations, the rubber composition comprises about 0.05% to about 5% by weight of a vulcanizing package, the vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator, in amounts of about 0.10% to about 4.5%, about 0.50% to about 4%, about 1% to about 3.5%, about 1.5% to about 3%, about 1.75% to about 2.75%, or about 2% to about 2.5%. In some formulations, the rubber composition comprises about 2.25% by weight of a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator.

[0286] The present invention further provides a rubber composition prepared by the above method.

[0287] The present invention also provides an article comprising the above-described rubber composition. In some embodiments, the article includes, but is not limited to, tires, conveyor belts, engine frames, and shoe soles. In some embodiments, the article is a tire or an engine frame. Examples

[0288] The components used to prepare the rubber composition are:

[0289] The natural rubber is cis-1,4-polyisoprene rubber, which is available from HB Chemical under the trade name Standard Indonesian Rubber SIR-20.

[0290] High cis-1,4-polybutadiene rubber is available from Chi Mei Corporation under the trade name Kibipol® HBR PR-040G.

[0291] The precipitated synthetic amorphous silica is a highly dispersed silica (HDS) microsphere with a BET surface area of ​​165 m² / g, which is available from Solvay Group (formerly known as Rhodia) under the trade name ZEOSIL 1165 MP.

[0292] Carbon black is available from Cabot Corporation under the trade name Vulcan® 9.

[0293] The processed oil is a treated distillate aromatic extract (TDAE) oil, which is available from H&R Group under the trade name Vivatec 500.

[0294] TESPT silane is bis[3-(triethoxysilyl)propyl]tetrasulfide, available from Struktol Company of America under the trade name SCA 98.

[0295] Composition A is a mixture of silane-functionalized amines synthesized by Momentive Performance Materials.

[0296] Activator 1 is zinc oxide, which is available from Harwick Standard under the trade name Zinc Oxide CR-40.

[0297] Activator 2 is stearic acid, which is available from Harwick Standard under the trade name Stearic Acid F-2000.

[0298] Anti-disintegration agent 1 is N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, which is available from Harwick Standard under the trade name Stangard® 6PPD.

[0299] Anti-disintegration agent 2 is a 2,2,4-trimethyl-1,2-dihydroquinoline polymer, available from Harwick Standard under the trade name Stangard®TMQ.

[0300] Anti-collapse agent 3 is a microcrystalline-paraffin wax mixture, available from Akrochem under the trade name AKROWAX® 5084.

[0301] The curing agent is sulfur, which is available from Georgia Gulf Sulfur Corp under the trade name Rubber Makers Sulfur.

[0302] Accelerator 1 is N-cyclohexyl-2-benzothiazole sulfinamide, which is available from Harwick Standard under the trade name KEMAI CBS GR.

[0303] Accelerator 2 is diphenylguanidine, which is available from Harwick Standard under the trade name Ekaland DPG C.

[0304] Table 1 lists the test procedures for evaluating vulcanized (cured) rubber compositions. Table 1 Performance indicators Measurement equipment method Processing indicators Menner viscosity, ML(1+4) 100℃ Monsanto MV2000 ASTM D-1646 Processing indicators Menna coking, 3 points rise Monsanto MV2000 ASTM D-1646 Rolling resistance index RPA strain scan G' at 60℃ TA INSTRUMENTS RPA MPM Internal Testing Methodology Rolling resistance index At 60℃, the maximum RPA tanδ is... TA INSTRUMENTS RPA MPM Internal Testing Methodology Rolling resistance index RPA Payne Effect TA INSTRUMENTS RPA MPM Internal Testing Methodology Wear indicators DIN wear (mass loss) DIN Rotary Abrasion Tester ASTM D-5963 Processing indicators Shore A hardness Zwick Shore Hardness Tester ASTM D-2240 Grip strength index Rebound at 70℃ and 100℃ Zwick 5109 Resilience Tester ASTM D-7121 Wear indicators Enhancement Index Zwick Ring Tester ASTM D-412 Durability High-Speed ​​Tearing Energy (HSTE) Zwick HIT50P ASTM D-624 Machinability viscosity Monsanto mobile model rheometer, model MDR 2000 ASTM F-5289-12 Wear indicators Tensile strength Zwick Ring Tester ASTM D-412 Processing indicators Modulus Zwick Ring Tester ASTM D-412 Wear indicators Elongation % Zwick Ring Tester ASTM D-412

[0305] Rubber Processing Analyzer is abbreviated as RPA. Example 1: Preparation of Composition A

[0306] Chloropropyltriethoxysilane (133.6 g, 0.56 moles), o-phenylenediamine (60.0 g, 0.56 moles), and xylene (100.0 g) were charged into a 1-L round-bottom flask equipped with a mechanical stirrer, a feeding funnel, a 6-inch Vigreux column, a short-path distillation head, a heating mantle, and a temperature controller. Sodium ethoxide (21% by weight in ethanol, 170.8 g, 0.53 moles) was charged into the feeding funnel. The reaction mixture in the flask was stirred and heated to 160°C and maintained for 2 hours. Sodium ethoxide was then added via the feeding funnel. Sodium ethoxide was added slowly over a period of 7-8 hours while maintaining the reaction temperature at 160°C. After the addition of sodium ethoxide was complete, the temperature was slowly lowered.

[0307] The solid was removed from the reaction mixture by centrifugation. The organic matter was washed three times with a 30% ethylenediamine / ethylenediamine hydrochloride solution to remove unreacted o-phenylenediamine. After washing, the organic matter was stripped under vacuum to remove the solvent and low-boiling-point washing reagent, and 122 grams of composition A were recovered. Example 2 Preparation of Composition A

[0308] A mixture of o-phenylenediamine (220.4 g, 2.04 moles) and xylene isomers (406.4 g) was charged into a reactor. The reactor was a 5-liter round-bottom flask supported by a heating mantle powered by a temperature controller. The flask was equipped with a mechanical stirrer, a feeding funnel, and a 15-cm Viglous column with a distillation head having controlled distillation. Subsequently, a mixture of chloropropyltriethoxysilane (492.7 g, 2.05 moles) and hexadecane (42.3 g) was added to the flask. The reaction mixture was maintained under a dry nitrogen atmosphere with stirring. The reaction mixture was heated to 160°C and held for 67 minutes, after which sodium ethoxide was added via the feeding funnel. Sodium ethoxide (21% by weight in ethanol, 616.0 g, 1.90 moles) was then added via the feeding funnel at a constant rate over 6 hours.

[0309] The reaction mixture was then cooled to room temperature and the liquid layer was decanted from the solid. The solid was then washed with toluene. The organic layers were combined and stripped under vacuum at 0.1 Torr, producing a deep purple liquid, which was placed in a freezer at -20°C for approximately 2 days. An additional solid was formed and the organic layer was again decanted from this solid. The organic layer was further stripped under vacuum at 0.1 Torr at high temperature, leaving a clear deep purple liquid composition A. Example 3 Preparation of Composition B

[0310] Chloropropyltriethoxysilane (0.25 moles), chlorobutyldimethylethoxysilane (0.28 moles), o-phenylenediamine (0.50 moles), and xylene (100.0 g) were charged into a 1-L round-bottom flask equipped with a mechanical stirrer, a feeding funnel, a 6-inch Vigglüf column, a short-path distillation head, a heating mantle, and a temperature controller. Sodium ethoxide (170.8 g, 21% in ethanol, 0.53 moles) was charged into the feeding funnel. The reaction mixture in the flask was stirred and heated to 160°C and maintained for 2 hours, after which sodium ethoxide was added. Sodium ethoxide was slowly added over a period of 7-8 hours while maintaining the reaction temperature at 160°C. Subsequently, the reaction mixture was slowly cooled.

[0311] The solid was removed from the reaction mixture by centrifugation. The organic matter was washed three times with a 30% ethylenediamine / ethylenediamine hydrochloride solution to remove unreacted o-phenylenediamine. After washing, the organic matter was stripped under vacuum to remove the solvent and low-boiling-point washing reagent, and composition B was recovered. Example 4 Preparation of Composition B

[0312] Chloropropyltriethoxysilane (0.25 moles), o-phenylenediamine (0.50 moles), and xylene (100.0 g) were placed in a 1-L round-bottom flask equipped with a mechanical stirrer, a feeding funnel, a 6-inch Viggl column, a short-path distillation head, a heating mantle, and a temperature controller. The reaction mixture in the flask was stirred and heated to 160°C and maintained for 2 hours. Subsequently, chlorobutyldimethylethoxysilane (0.28 moles) was added to the flask. The reaction mixture in the flask continued to react for 2 hours. Then, sodium ethoxide (170.8 g, 21% in ethanol, 0.53 moles) was slowly added over a period of 7-8 hours, while maintaining the reaction temperature at 160°C. The reaction mixture was then slowly cooled.

[0313] The solid was removed from the reaction mixture by centrifugation. The organic matter was washed three times with a 30% ethylenediamine / ethylenediamine hydrochloride solution to remove unreacted o-phenylenediamine. After washing, the organic matter was stripped under vacuum to remove the solvent and low-boiling-point washing reagent, and composition B was recovered. Comparative Example: Preparation and Evaluation of Rubber Compositions

[0314] Table 2 lists the components used to prepare a rubber composition using an 80 / 20 blend of natural rubber / cis-1,4-polybutadiene and containing Vulcan® 9 carbon black (control) and silica-coupled silane (in the case of using TESPT), as well as composition A. Composition A is the silane of this invention. Table 2 Rubber containing carbon black (PHR (parts per 100 parts of rubber)) Rubber containing TESPT silane (PHR (parts per hundred parts of rubber)) Rubber containing composition A (PHR (parts per hundred parts of rubber)) Element First unproductive (NP1) natural rubber 80.0 80.0 80.0 cis-1,4-polybutadiene 20.0 20.0 20.0 Silicon dioxide 0.0 50.0 50.0 carbon black 25.0 5.0 5.0 TDAE processing oil 1.0 1.0 1.0 TESPT silane 0.0 4.0 0.0 Composition A 0.0 0.0 4.0 Zinc oxide 1.5 1.5 1.5 stearic acid 1.0 1.0 1.0 NP1 total 128.5 162.5 162.5 Second unproductive (NP2) carbon black 25.0 5.0 5.0 N-(1,3-Dimethylbutyl)-N'-Phenylacetyl-p-phenylenediamine (6-PPD) 2.0 2.0 2.0 2,2,4-Trimethyl-1,2-dihydroquinoline polymer (TMQ) 0.5 0.5 0.5 Microcrystalline wax 1.3 1.3 1.3 Zinc oxide 1.5 1.5 1.5 stearic acid 1.0 1.0 1.0 NP2 total 159.8 173.8 173.8 Productivity sulfur 1.600 1.600 1.600 N-Cyclohexyl-2-benzothiazole sulfinamide (CBS) 1.100 2.000 2.000 Diphenylguanidine (DPG) 0.4 0.4 0.4 Final production mixture total 162.9 177.8 177.8

[0315] Because silica tends to absorb this accelerator to its surface, silica-containing formulations require slightly more N-cyclohexyl-2-benzothiazole sulfinamide (CBS). The three formulations are mixed in a rubber mixer using a mixing process comprising two consecutive non-productive mixing steps followed by a final productive mixing. During the two non-productive processes, the silica formulation containing TESPT is heat-treated at 145°C for 150 seconds (to drive the desired silanization reaction). During the two non-productive processes, the silica formulation containing composition A is heat-treated at 155°C for 90 seconds.

[0316] Mix all three formulations and the curing agent in the final production mixture at 105°C for 180 seconds. Cure the rubber composition at 160°C for 15 minutes.

[0317] Table 3 lists the physical and dynamic properties of the three rubber compositions. Table 3 sample carbon black TESPT silane Composition A Menna Plasticity ML1+4 (MU) at 100℃ 75.4 70.2 144.2 Coking Ts3 (minutes) 8.3 12.6 7.6 Rheometer, 160℃ Maximum torque, dNm 21.26 22.80 19.35 Minimum torque, dNm 3.13 2.78 3.57 Δtorque, dNm 18.1 20.0 15.8 Stress-Strain Tensile strength, MPa 22.7 21.7 19.2 Elongation at break, % 504 498 454 100% Modulus, MPa 2.3 2.4 1.8 300% modulus, MPa 12.4 12.5 11.3 Enhancement Index 5.5 5.2 6.4 Shore A hardness At 25℃, Shore A 62.0 63.3 58.7 Durability High-Speed ​​Tear Energy (HSTE), MJ / m 3 6.7 6.9 6.7 DIN wear loss, mm 3 95.8 99.7 92.8 Dynamic characteristics Strain scan of RPA during curing (G'), at 10% strain, 60℃, MPa 2.2 2.4 1.8 Curing RPA Tan δ at 10% strain and 60°C 0.164 0.140 0.100 Curing RPA Payne effect, MPa 6.58 5.23 2.74 Rebound at 70℃ 55.1 58.7 60.9 Rebound at 100℃ 59.0 62.4 63.9

[0318] The Shore A hardness of the rubber composition containing composition A is less than that of both carbon black and TESPT rubber compositions.

[0319] The higher Menner viscosity observed in the rubber composition containing composition A may be due to the crosslinking of silane with the polymer via the Diels Alder mechanism or direct crosslinking of the polymer with free radicals during the mixing process.

[0320] The charring safety and curing behavior of the rubber composition containing composition A are comparable to those of the TESPT rubber composition. The higher minimum torque observed in the rubber composition containing composition A is due to the much higher viscosity of the biocompound. Δtorque is generally related to the degree of sulfur crosslinking; therefore, the rubber composition containing composition A may have a lower degree of crosslinking compared to carbon black and TESPT rubber compositions. This is also possible through the potential pre-crosslinking of the polymer via silane during the mixing process.

[0321] The rubber composition containing composition A has a higher hardness (strength index) than both carbon black and TESPT rubber compositions. The increased strength is a positive indicator of improved wear resistance and abrasion resistance.

[0322] The slightly lower tensile strength and elongation of the rubber composition containing composition A can be attributed to the presence of shorter, slightly stronger CN bonds in the matrix. All three batches exhibited considerable high-speed tear energy, an indicator of cut and shatter resistance in natural rubber tire formulations.

[0323] The rubber composition containing composition A provides excellent abrasion resistance in silica compounds, as measured using a DIN abrasion tester.

[0324] The Payne effect, a measure of the degree of filler-filler interaction, is significantly lower for rubber compositions containing composition A. This may also be due to the pre-crosslinking between silane and polymer during the mixing process, which minimizes the possibility of re-flocculation of filler aggregates. Tire rolling resistance is related to tire deformation at frequencies of 10-100 Hz and temperatures of 50-70°C, and is proportional to tan δ, which is the ratio of the viscous modulus to the elastic modulus under cyclic deformation. Table 3 shows that rubber compositions containing composition A have much lower tan δ values ​​than carbon black and TESPT rubber compositions. Therefore, rubber compositions containing composition A appear to minimize the trade-off between abrasion resistance and rolling resistance in natural rubber tire formulations. [Simplified Explanation of the Diagram]

[0032] The accompanying drawings, which are incorporated herein by reference and form part of this specification, illustrate embodiments of the invention. These drawings, together with this specification, further serve to explain the principles of embodiments of the invention and enable those skilled in the art to make and use embodiments of the invention. These drawings are intended to be illustrative and not restrictive.

[0033] Figure 1 is a line graph showing the rheological curing behavior (including coking safety) of a rubber composition containing composition A compared to a rubber composition containing carbon black or TESPT.

Claims

1. A composition comprising at least one silane-functionalized amine, wherein the at least one silane-functionalized amine is a compound of formula (I): (R1)aG-(NR2)b; and further wherein: G is a saturated or unsaturated cyclic moiety; each R 1 is independently selected from the group consisting of: alkoxy groups having 1 to 20 carbon atoms, alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms, and aralkyl groups having 7 to 14 carbon atoms; each R is independently selected from the group consisting of: hydrogen and -L-SiX 1X 2X 3; The limiting conditions are that at least one R is hydrogen and at least one R is -L-SiX1X2X3; each L is independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms and, where appropriate, at least one heteroatom; alkenyl groups having 2 to 20 carbon atoms; cycloalkyl groups having 3 to 10 carbon atoms; aryl groups having 6 to 12 carbon atoms; and arylalkyl groups having 7 to 14 carbon atoms; each X1 is independently selected from the group consisting of: hydroxyl, -OR2, and -OC(=O)R2; each X2 and each X3 is independently selected from the group consisting of: hydroxyl, -OR2, -OC(=O)R2, and R2; each R 2. Independently selected from the group consisting of: alkyl groups having 1 to 20 carbon atoms, alkenyl groups having 2 to 20 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 12 carbon atoms and aralkyl groups having 7 to 14 carbon atoms; a being 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or 11; and b being 1 or 2.

2. The composition of claim 1, wherein G is selected from the group consisting of a benzene ring, a cyclohexane ring, and a pyridine ring.

3. The composition of claim 1 or 2, wherein the compound of formula (I) is selected from the group consisting of: and combinations thereof.

4. The composition of any one of claims 1 to 3, wherein the compound of formula (I) is selected from the group consisting of: and combinations thereof.

5. A method for preparing at least one silane-functionalized amine as claimed in any one of claims 1 to 4, the method comprising reacting a compound of formula (II): (R ​​1) aG-(NH 2) b with one or more compounds of formula (III): ML-SiX 1X 2X 3; each M being independently a halogen; and wherein the molar ratio of the total compound of formula (III) to the compound of formula (II) is equal to or less than 2b-1.

6. The method of claim 5, wherein the molar ratio of compound (III) to compound (II) is equal to or less than 1.

5.

7. The method as requested in item 5 or 6, wherein M is chlorine, bromine or iodine.

8. The method of any one of claims 5 to 7, wherein the reaction is carried out in the presence of a base.

9. The method of claim 8, wherein the base is an alkali metal alkoxide.

10. A rubber composition comprising: a. a composition comprising at least one silane-functionalized amine as claimed in any one of claims 1 to 4; b. at least one diene polymer; c. silicon dioxide; d. at least one processing aid; and e. a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator.

11. The rubber composition of claim 10, wherein the at least one diene polymer is a diene polymer containing at least one functional group, a diene polymer without a functional group, or a combination thereof.

12. The rubber composition of claim 11, wherein the at least one diene polymer is natural rubber, polyisoprene, polybutadiene, styrene-butadiene copolymer (SBR), or a combination thereof.

13. The rubber composition of claim 12, wherein the at least one diene polymer is natural rubber, cis-1,4-polyisoprene, cis-1,4-polybutadiene, or a combination thereof.

14. A rubber composition comprising: (i) about 100 parts of rubber, wherein the weight of the rubber is the sum of the weight of each diene polymer containing at least one functional group used in the formulation and the weight of each diene polymer without functional group used in the formulation; (ii) about 1 to about 20 parts by weight of a composition comprising at least one silane functionalized amine as claimed in any one of claims 1 to 4 per 100 parts of rubber (i); (iii) about 5 to about 140 parts by weight of silicon dioxide per 100 parts of rubber (i); (iv) about 0.1 to about 10 parts by weight of at least one processing aid per 100 parts of rubber (i); and (v) about 0.1 to about 20 parts by weight of a vulcanizing package comprising at least one sulfur-containing vulcanizing agent and at least one accelerator per 100 parts of rubber (i).

15. A method for preparing a rubber composition comprising adding a composition comprising at least one silane-functionalized amine as claimed in any one of claims 1 to 4 and silica to at least one diene polymer.

16. An article comprising the rubber composition of claim 14, wherein the article is a tire or an engine frame.

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