Synthesis of silane compounds

Abstract

The present disclosure is directed to a silane coupling agent, two silane-functional polymers, a method for making the silane coupling agent, use of the silane coupling agent to make a silane-functional polymer, a method for making a silane-functional polymer by removing a protecting group, and compositions comprising one or more silane-functional polymers.

Description

[Technical field]

[0001] The present disclosure relates to silane coupling agents, silane-functional polymers, methods for producing silane coupling agents, and the use of silane coupling agents to produce silane-functional polymers. The present disclosure further relates to compositions comprising one or more silane-functional polymers, as well as compositions for a number of applications. [Background technology]

[0002] Adding silane functionality to solution polymerized styrene butadiene rubber (SSBR) polymers is desirable to polymer manufacturers and tire compounders as it produces rubber compounds with improved properties (wear, rolling resistance, handling, etc.) Traditionally, adding aminosilanes / thiosilanes / oxysilanes to SSBR polymers has been problematic as the NH / SH / OH functionality poisons the living polymer resulting in the silane functionality not being added to the SSBR polymer.

[0003] To overcome this technical difficulty of standard silane compounds, it is known to use tertiary aminosilanes without NH functionality (US2021 / 0130591A1) or to use protected aminosilanes (JP11349632). Due to the lack of NH / SH / OH functionality, tertiary silane compounds are not preferred. The presence of NH / SH / OH functionality allows hydrogen bonding to silica in rubber compounds, which improves the polymer / silica interaction and leads to improved rubber properties.

[0004] In addition, the use of protecting groups in silane compounds has led to technical challenges with respect to the stability of the protecting groups (US10457697B2).Therefore, there is a need for improved methods for preparing silane compounds. Summary of the Invention

[0005] The silane compounds disclosed herein are represented by formula (I) [ka] wherein:

[0006] M is selected from the group consisting of nitrogen, sulfur, and oxygen;

[0007] Y is a protecting group;

[0008] Q 1 -L-Si-(X 1 ) d (X 2 ) 3-d or R 1 ;

[0009] each L is independently selected from absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom;

[0010] X 1 Each of the following is independent:-OR 1 or -OC(=O)R 1 ;

[0011] X 2 Each of R 1 ;

[0012] R 1each of R is independently selected from the group consisting of an optionally substituted alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or two R 1 A divalent group formed by bonding two R 1 When the groups are linked together b is 2 or 3;

[0013] a is 0 or 1; except that when M is nitrogen, a is 1; when M is sulfur or oxygen, a is 0;

[0014] b is 1, 2, or 3; and

[0015] d is 0, 1, 2, or 3.

[0016] The present disclosure further provides a compound represented by formula (II) [ka] For a polymer having the formula:

[0017] M, Y, L, X 1 Each of X 2 Each of R 1 Each of a, b, and d is as described in formula (I).

[0018] Q 2 Ha-L-Si-(G)e (X 1 ) d-e (X 2 ) 3-d or R 1 and;

[0019] G is a polymer fragment having main chain carbon atoms covalently bonded to each other by C-C single bonds, C-C double bonds, or a combination of C-C single bonds and C-C double bonds;

[0020] c is 1, 2, or 3, where c is less than or equal to b; and

[0021] e is 0, 1, 2, or 3, where e is less than or equal to d.

[0022] The present disclosure also provides a compound of formula (III): [ka] For a polymer having the formula:

[0023] M, L, X 1 Each of X 2 Each of R 1 Each of Q 2 , G, a, b, c, d and e are as described in formula (II).

[0024] The present disclosure further provides a compound represented by formula (IV) [ka] providing a polymer fragment G having the formula:

[0025] R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R14 , R 15 , R 16 , R 17 and R 18 each independently is an alkyl group having 1 to 20 carbon atoms, or hydrogen;

[0026] R 6 each is independently selected from the group consisting of hydrogen, an alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkenyl group having 4 to 14 carbon atoms, an aryl group having 6 to 16 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms; and

[0027] f, g and h are integers, where f is greater than or equal to 0, g is greater than or equal to 0, and h is greater than or equal to 0, with the proviso that the sum of f, g and h is greater than or equal to 1.

[0028] The present disclosure also provides a silane compound of formula (I) [ka] The present invention provides a method for preparing a compound of formula (V): [ka] with a protecting agent; 1 , L, X 1 Each of X 2 Each of R 1 Each of a, b, and d is as described in formula (I).

[0029] The present disclosure also provides a polymer of formula (II) [ka] The present invention provides a method for preparing a polymer fragment G comprising reacting a chain of C—C unsaturated carbon atom monomers with an anionic initiator to form a polymer fragment G; and reacting the polymer fragment G with a silane compound of formula (I), where Q 1 -L-Si-(X 1 ) d (X 2 ) 3-d , Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d ; and Q 1 R 1 Then Q 2 is R 1 It is.

[0030] The present disclosure further provides a polymer of formula (III) [ka] The present invention provides a method for producing a polymer of formula (II) [ka] under suitable conditions, wherein:

[0031] M, Y, L, X 1 Each of X 2 Each of R 1 Each of Q 2 , G, a, b, c, d and e are as described in formula (II). DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0032] As used above, and throughout the detailed description, the following terms, unless otherwise stated, shall be understood to have the following meanings:

[0033] The terms "a," "an," and "the," and similar expressions used in the context of describing particular embodiments of this application (particularly in the context of the claims), can be construed to include both the singular and the plural, unless otherwise indicated. Reference to ranges of values ​​in this application is intended to serve as a shorthand way of referring to each individual value within the range individually. Unless otherwise indicated in this application, each individual value is incorporated into the specification as if it were separately recited in this application.

[0034] Furthermore, "and / or" as used herein should be understood as a specific disclosure of each of the two specified features or components with or without the other. Thus, the term "and / or" when used herein in phrases such as "A and / or B" is intended to include "A and B," "A or," "A" (single), and "B" (single). Similarly, the term "and / or" when used herein in phrases such as "A, B, and / or C" is intended to include each of the following embodiments: 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 (single); B (single); and C (single).

[0035] Where embodiments are described herein using the term "comprising," it will be understood that otherwise similar embodiments described using the terms "consisting of" and / or "consisting essentially of" are also presented.

[0036] The term "polymer" refers to a substance, chemical compound, or mixture of compounds having a molecular structure that consists primarily or entirely of many smaller units (eg, monomeric units) bonded together.

[0037] The term "about" encompasses the range of experimental error that occurs in all measurements.

[0038] The expression "coupling agent" means an agent capable of establishing an effective chemical and / or physical bond between a diene-based polymer and a filler, or an agent capable of establishing an effective chemical and / or physical bond between two diene-based polymers. An effective coupling agent has functional groups capable of chemically and / or physically bonding with a filler or a second diene-based polymer, for example between silanol groups of the coupling agent and hydroxyl (OH) groups on the surface of the filler (for example surface silanols in the case of silica), or between silanol groups bonded to one diene-based polymer and silanol groups of another polymer, and also has sulfur atoms capable of chemically and / or physically bonding with the diene-based polymer, for example as a result of vulcanization (curing).

[0039] The term "hydrocarbon" as used herein refers to any chemical structure containing hydrogen and carbon atoms.

[0040] The term "alkyl" means any monovalent, saturated, straight or branched chain hydrocarbon group; the term "alkenyl" means any monovalent, straight or branched chain hydrocarbon containing one or more carbon-carbon double bonds, where the point of attachment of the group can be the carbon-carbon double bond or elsewhere; and the term "alkynyl" means any monovalent, straight or branched chain hydrocarbon containing one or more carbon-carbon triple bonds, and optionally one or more carbon-carbon double bonds, where the point of attachment of the group can be the carbon-carbon triple bond, carbon-carbon double bond or elsewhere.

[0041] Representative examples of alkyl include methyl, ethyl, propyl, and isobutyl. Examples of alkenyl include vinyl, propenyl, allyl, methallyl, ethylidenylnorbornane, ethylidenenorbornyl, ethylidenylnorbornene, and ethylidenenorbornenyl. Examples of alkynyl include acetylenyl, propargyl, and methylacetylenyl.

[0042] 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, where the points of attachment of the group can be carbon-carbon double bonds or elsewhere; and the term "cycloalkynyl" means any monovalent cyclic aliphatic hydrocarbon group containing one or more carbon-carbon triple bonds, and optionally one or more carbon-carbon double bonds, where the points of attachment of the group can be carbon-carbon triple bonds, carbon-carbon double bonds or elsewhere.

[0043] Representative examples of cycloalkyl include cyclopentyl, cyclobutyl, cyclopentyl, cycloheptyl, and cyclooctyl. Examples of cycloalkenyl include cyclopentenyl, cycloheptenyl, and cyclooctatrienyl. An example of cycloalkynyl is cycloheptynyl.

[0044] The terms "cycloalkyl", "cycloalkenyl", and "cycloalkynyl" include bicyclic, tricyclic, and higher cyclic structures, as well as those cyclic structures further substituted with alkyl, alkenyl, and / or alkynyl groups. Representative examples include norbornyl, norbornenyl, ethylnorbornyl, ethylnorbornenyl, cyclohexyl, ethylcyclohexyl, ethylcyclohexenyl, cyclohexylcyclohexyl, and cyclododecatrienyl.

[0045] The term "aryl" includes any aromatic hydrocarbon having one hydrogen atom removed; "aralkyl" includes any of the alkyl groups listed above where one or more hydrogen atoms are replaced with the same number of similar and / or different aryl (as defined herein) substituents; and "arenyl" includes any of the aryl groups listed above where one or more hydrogen atoms are replaced with the same number of similar and / or different alkyl (as defined herein) substituents. Specific non-limiting examples of aryl groups include phenyl and naphthyl. Specific non-limiting examples of aralkyl groups include benzyl and phenethyl. Specific non-limiting examples of arenyl groups include tolyl and xylyl.

[0046] The term "alkylene" refers to a divalent saturated aliphatic radical derived by removing two hydrogen atoms from an alkane.

[0047] The term "heteroatom" means any of the elements in Groups 13-17, excluding carbon, and includes, for example, oxygen, nitrogen, silicon, sulfur, phosphorus, fluorine, chlorine, bromine, and iodine.

[0048] The terms "halo" or "halogen," by themselves or as part of another group, refer to -Cl, -F, -Br, or -I.

[0049] Other than in the examples, or unless otherwise noted, all numbers expressing quantities of ingredients, reaction conditions, lengths of time, quantified properties of materials, and the like described in the specification and claims are understood to be modified in all instances by the term "about."

[0050] Any numerical ranges recited herein are understood to include all subranges within that range, and any combination of the various endpoints of such ranges or subranges.

[0051] Furthermore, all compounds, materials or substances explicitly or implicitly disclosed and / or claimed herein as belonging to a group of structurally, compositionally and / or functionally related compounds, materials or substances are understood to include the individual members of that group and all combinations thereof.

[0052] The silane compound disclosed herein has the formula (I): [ka] wherein:

[0053] M is selected from the group consisting of nitrogen, sulfur, and oxygen;

[0054] Y is a protecting group;

[0055] Q 1 -L-Si-(X 1 ) d (X 2 ) 3-d or R 1 ;

[0056] each L is independently selected from absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom;

[0057] X 1 Each of the following is independent:-OR 1 or -OC(=O)R 1 ;

[0058] X 2 Each of R 1 ;

[0059] R 1 each of R is independently selected from the group consisting of an optionally substituted alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or two R 1 A divalent group formed by bonding two R 1 When the groups are linked together b is 2 or 3;

[0060] a is 0 or 1; except that when M is nitrogen, a is 1; when M is sulfur or oxygen, a is 0;

[0061] b is 1, 2, or 3; and

[0062] d is 0, 1, 2, or 3.

[0063] In some embodiments, Y is [ka] and further comprising the formula:

[0064] R 2each is independently selected from the group consisting of optionally substituted alkyl groups having 1 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkenyl groups having 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted cycloalkyl groups having 3 to 14 carbon atoms and optionally at least one heteroatom, optionally substituted aryl groups having 6 to 16 carbon atoms and optionally at least one heteroatom, and optionally substituted aralkyl groups having 7 to 20 carbon atoms and optionally at least one heteroatom.

[0065] In some embodiments, Y is [ka] [ka] [ka] is selected from the group consisting of:

[0066] In some embodiments, Y is [ka] It is.

[0067] In some embodiments, M is nitrogen, a is 1, and the silane compound of formula (I) is [ka] It is.

[0068] In some embodiments, Q 1 -L-Si-(X 1 ) d (X 2 ) 3-dand the silane compound of formula (I) [ka] It is.

[0069] In some embodiments, each L is an optionally substituted alkylene group having 1 to 20 carbon atoms.

[0070] In some embodiments, each L is -CH2CH2CH2-.

[0071] In some embodiments, X 1 Each of -OR 1 It is.

[0072] In some embodiments, R 1 Each of is an optionally substituted alkyl group having 1 to 20 carbon atoms.

[0073] In some embodiments, R 1 Each of is an ethyl group.

[0074] In some embodiments, b is 3.

[0075] In some embodiments, d is 3.

[0076] In some embodiments, the silane compound of formula (I) [ka] It is.

[0077] In some embodiments, Q 1 is R 1 and the silane compound of formula (I) [ka] It is.

[0078] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0079] In some embodiments, X 1 Each of -OR 1 It is.

[0080] In some embodiments, R 1 Each of R is independently an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 12 carbon atoms. 1 is an ethyl group. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is a phenyl group.

[0081] In some embodiments, b is 3.

[0082] In some embodiments, the silane compound of formula (I) [ka] It is.

[0083] In some embodiments, the silane compound of formula (I) [ka] It is.

[0084] In some embodiments, M is sulfur, a is 0, and the silane compound of formula (I) is [ka] It is.

[0085] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0086] In some embodiments, X 1 Each of -OR 1 It is.

[0087] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0088] In some embodiments, b is 3.

[0089] In some embodiments, the silane compound of formula (I) [ka] It is.

[0090] In some embodiments, Y is [ka] It is.

[0091] In some embodiments, M is oxygen, a is 0, and the silane compound of formula (I) is [ka] It is.

[0092] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0093] In some embodiments, X 1 Each of -OR1 It is.

[0094] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0095] In some embodiments, b is 3.

[0096] In some embodiments, the silane compound of formula (I) [ka] It is.

[0097] The present disclosure further provides a compound of formula (II): [ka] For a polymer having the formula:

[0098] M, Y, L, X 1 Each of X 2 Each of R 1 Each of a, b, and d is as described in formula (I).

[0099] Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 and;

[0100] G is a polymer fragment having main chain carbon atoms covalently bonded to each other by C-C single bonds, C-C double bonds, or a combination of C-C single bonds and C-C double bonds;

[0101] c is 1, 2, or 3, where c is less than or equal to b; and

[0102] e is 0, 1, 2, or 3, where e is less than or equal to d.

[0103] In some embodiments, Y is [ka] and further wherein R 2 Each of these is as described above.

[0104] In some embodiments, Y is [ka] [ka] [ka] is selected from the group consisting of:

[0105] In some embodiments, Y is [ka] It is.

[0106] In some embodiments, M is nitrogen, a is 1, and the polymer of formula (II) is [ka] It is.

[0107] In some embodiments, Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d and the polymer of formula (II) [ka] It is.

[0108] In some embodiments, each L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, each L is -CH2CH2CH2-.

[0109] In some embodiments, X 1 Each of -OR 1 It is.

[0110] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0111] In some embodiments, c is 1.

[0112] In some embodiments, b is 3.

[0113] In some embodiments, e is 1.

[0114] In some embodiments, d is 3.

[0115] In some embodiments, the polymer of formula (II) is [ka] It is.

[0116] In some embodiments, Q 2 is R 1 and the polymer of formula (II) [ka] It is.

[0117] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0118] In some embodiments, X 1 Each of -OR 1 It is.

[0119] In some embodiments, R 1 Each of R is independently an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 12 carbon atoms. 1 is an ethyl group. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is a phenyl group.

[0120] In some embodiments, c is 1.

[0121] In some embodiments, b is 3.

[0122] In some embodiments, the polymer of formula (II) is [ka] It is.

[0123] In some embodiments, the polymer of formula (II) is [ka] It is.

[0124] In some embodiments, M is sulfur, a is 0, and the polymer of formula (II) is [ka] It is.

[0125] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0126] In some embodiments, X 1 Each of -OR 1 It is.

[0127] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0128] In some embodiments, c is 1.

[0129] In some embodiments, b is 3.

[0130] In some embodiments, the polymer of formula (II) is [ka] It is.

[0131] In some embodiments, Y is [ka] It is.

[0132] In some embodiments, M is oxygen, a is 0, and the polymer of formula (II) is [ka] It is.

[0133] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0134] In some embodiments, X 1 Each of -OR 1 It is.

[0135] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0136] In some embodiments, c is 1.

[0137] In some embodiments, b is 3.

[0138] In some embodiments, the polymer of formula (II) is [ka] It is.

[0139] The present disclosure also provides a compound of formula (III): [ka] For a polymer having the formula:

[0140] M, L, X 1 Each of X 2 Each of R 1 Each of a, b, and d is as described in formula (I).

[0141] Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R1 and;

[0142] G is a polymer fragment having main chain carbon atoms covalently bonded to each other by C-C single bonds, C-C double bonds, or a combination of C-C single bonds and C-C double bonds;

[0143] c is 1, 2, or 3, where c is less than or equal to b; and

[0144] e is 0, 1, 2, or 3, where e is less than or equal to d.

[0145] In some embodiments, M is nitrogen, a is 1, and the polymer of formula (III) is [ka] It is.

[0146] In some embodiments, Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d and the polymer of formula (III) [ka] It is.

[0147] In some embodiments, each L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, each L is -CH2CH2CH2-.

[0148] In some embodiments, X 1 Each of -OR 1 It is.

[0149] In some embodiments, R 1Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0150] In some embodiments, c is 1.

[0151] In some embodiments, b is 3.

[0152] In some embodiments, e is 1.

[0153] In some embodiments, d is 3.

[0154] In some embodiments, the polymer of formula (III) is [ka] It is.

[0155] In some embodiments, Q 2 is R 1 and the polymer of formula (III) [ka] It is.

[0156] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0157] In some embodiments, X 1 Each of -OR 1 It is.

[0158] In some embodiments, R 1 Each of R is independently an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 12 carbon atoms.1 is an ethyl group. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is a phenyl group.

[0159] In some embodiments, c is 1.

[0160] In some embodiments, b is 3.

[0161] In some embodiments, the polymer of formula (III) is [ka]

[0162] [ka] It is.

[0163] In some embodiments, M is sulfur, a is 0, and the polymer of formula (III) is [ka] It is.

[0164] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0165] In some embodiments, X 1 Each of -OR 1 It is.

[0166] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0167] In some embodiments, c is 1.

[0168] In some embodiments, b is 3.

[0169] In some embodiments, the polymer of formula (III) is [ka] It is.

[0170] In some embodiments, M is oxygen, a is 0, and the polymer of formula (III) is [ka] It is.

[0171] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0172] In some embodiments, X 1 Each of -OR 1 It is.

[0173] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0174] In some embodiments, c is 1.

[0175] In some embodiments, b is 3.

[0176] In some embodiments, the polymer of formula (III) is [ka] It is.

[0177] In some embodiments, G is a group represented by formula (IV): [ka] is a polymer fragment of the formula:

[0178] R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 each independently is an alkyl group having 1 to 20 carbon atoms, or hydrogen;

[0179] R 6 each is independently selected from the group consisting of hydrogen, an alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkenyl group having 4 to 14 carbon atoms, an aryl group having 6 to 16 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms; and

[0180] f, g and h are integers, where f is greater than or equal to 0, g is greater than or equal to 0, and h is greater than or equal to 0, with the proviso that the sum of f, g and h is greater than or equal to 1.

[0181] In some embodiments, f is between 0 and 10,000. In some embodiments, f is between 1 and 5,000. In some embodiments, f is between 100 and 2,500.

[0182] In some embodiments, g is between 0 and 10,000. In some embodiments, g is between 0 and 5,000. In some embodiments, g is between 100 and 2,500.

[0183] In some embodiments, h is between 0 and 10,000. In some embodiments, h is between 0 and 5,000. In some embodiments, h is between 100 and 2,500.

[0184] In some embodiments, the sum of f, g and h is from 100 to 5,000.

[0185] In some embodiments, R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 Each of is hydrogen.

[0186] In some embodiments, R 6 Each of R is an aryl group having 6 to 16 carbon atoms. 6 Each of is a phenyl group.

[0187] In some embodiments, the polymer fragment G is a styrene butadiene polymer.

[0188] The present disclosure relates to a silane compound of formula (I) [ka] The present invention provides a method for producing a compound of formula (V) [ka] with a protecting agent; 1 , L, X 1 Each of X 2 Each of R 1 Each of a, b, and d is as described in formula (I).

[0189] In some embodiments, the protective agent is [ka] and further wherein X is a halogen or OR 2 ; and R 2 Each of these is as described above.

[0190] In some embodiments, the protective agent is [ka] [ka] [ka] is selected from the group consisting of:

[0191] In some embodiments, the protective agent is [ka]

[0192] In some embodiments, Y is [ka] and further wherein R 2 Each of these is as described above.

[0193] In some embodiments, Y is [ka] [ka] [ka] is selected from the group consisting of:

[0194] In some embodiments, Y is [ka] It is.

[0195] In some embodiments, M is nitrogen, a is 1, and the silane compound has formula (I): [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0196] In some embodiments, Q 1 -L-Si-(X 1 ) d (X 2 ) 3-d and a silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0197] In some embodiments, each L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, each L is -CH2CH2CH2-.

[0198] In some embodiments, X 1 Each of -OR 1 It is.

[0199] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0200] In some embodiments, b is 3.

[0201] In some embodiments, d is 3.

[0202] In some embodiments, the silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0203] In some embodiments, Q1 is R 1 and a silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0204] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0205] In some embodiments, X 1 Each of -OR 1 It is.

[0206] In some embodiments, R 1 Each of R is independently an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 12 carbon atoms. 1 is an ethyl group. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is a phenyl group.

[0207] In some embodiments, b is 3.

[0208] In some embodiments, the silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0209] In some embodiments, the silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0210] In some embodiments, M is sulfur, a is 0, and the silane compound has formula (I): [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0211] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0212] In some embodiments, X 1 Each of -OR 1 It is.

[0213] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0214] In some embodiments, b is 3.

[0215] In some embodiments, the silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0216] In some embodiments, the protective agent is [ka] It is.

[0217] In some embodiments, Y is [ka] It is.

[0218] In some embodiments, M is oxygen, a is 0, and the silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0219] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0220] In some embodiments, X 1 Each of -OR 1 It is.

[0221] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0222] In some embodiments, b is 3.

[0223] In some embodiments, the silane compound of formula (I) [ka] is a compound of formula (V) [ka] Protective agent [ka] It is prepared by reacting with

[0224] In some embodiments, the reaction is carried out in the presence of a base, heat, or under exothermic conditions.

[0225] In some embodiments, the base is selected from the group consisting of 4-dimethylaminopyridine, pyridine, sodium carbonate, sodium bicarbonate, N,N-diisopropylethylamine, and magnesium oxide. In some embodiments, the base is 4-dimethylaminopyridine. In some embodiments, the base is sodium carbonate. In some embodiments, the base is N,N-diisopropylethylamine.

[0226] In some embodiments, the reaction occurs in the presence of heat.

[0227] In some embodiments, the reaction occurs under exothermic conditions.

[0228] In some embodiments, the molar ratio of the compound of Formula (V) to the protecting agent is about 1:1 to about 1:1.5. In some embodiments, the molar ratio of the compound of Formula (V) to the protecting agent is about 1:1 to about 1:1.3. In some embodiments, the molar ratio of the compound of Formula (V) to the protecting agent is about 1:1.

[0229] The present disclosure also relates to a polymer of formula (II) [ka] The present invention also provides a method for preparing a polymer fragment G by reacting a chain of C—C unsaturated carbon atom monomers with an anionic initiator to form a polymer fragment G; and reacting the polymer fragment G with a silane compound of formula (I) [ka] with the formula:

[0230] M, Y, Q 1 , L, X 1 Each of X 2 Each of R 1Each of a, b, and d is as described in formula (I).

[0231] Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 where Q 1 -L-Si-(X 1 ) d (X 2 ) 3-d When Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d ; and Q 1 R 1 When Q 2 is R 1 and;

[0232] c is 1, 2, or 3, where c is less than or equal to b; and

[0233] e is 0, 1, 2, or 3, where e is less than or equal to d.

[0234] In some embodiments, Y is [ka] and further wherein R 2 Each of these is as described above.

[0235] In some embodiments, Y is [ka] [ka] [ka] is selected from the group consisting of:

[0236] In some embodiments, Y is [ka] It is.

[0237] In some embodiments, the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0238] In some embodiments, Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d , Q 1 -L-Si-(X 1 ) d (X 2 ) 3-d and a polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0239] In some embodiments, each L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, each L is -CH2CH2CH2-.

[0240] In some embodiments, X 1 Each of -OR 1 It is.

[0241] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0242] In some embodiments, c is 1.

[0243] In some embodiments, b is 3.

[0244] In some embodiments, e is 1.

[0245] In some embodiments, d is 3.

[0246] In some embodiments, the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0247] In some embodiments, Q 2 is R 1 , Q 1 is R 1 and a polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0248] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0249] In some embodiments, X 1 Each of -OR 1 It is.

[0250] In some embodiments, R 1 Each of R is independently an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 12 carbon atoms. 1 is an ethyl group. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is a phenyl group.

[0251] In some embodiments, c is 1.

[0252] In some embodiments, b is 3.

[0253] In some embodiments, the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0254] In some embodiments, the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0255] In some embodiments, M is sulfur, a is 0, and the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0256] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0257] In some embodiments, X 1 Each of -OR 1 It is.

[0258] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0259] In some embodiments, c is 1.

[0260] In some embodiments, b is 3.

[0261] In some embodiments, the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0262] In some embodiments, Y is [ka] It is.

[0263] In some embodiments, M is oxygen, a is 0, and the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0264] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0265] In some embodiments, X 1 Each of -OR 1 It is.

[0266] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0267] In some embodiments, c is 1.

[0268] In some embodiments, b is 3.

[0269] In some embodiments, the polymer of formula (II) [ka] The polymer fragment G is reacted with a silane compound of formula (I) [ka] It is prepared by reacting with

[0270] In some embodiments, the anionic initiator is n-butyllithium.

[0271] In some embodiments, the ratio between the anionic initiator and the monomer is from about 1:1 to about 1:10,000, from about 1:10 to about 1:9,000, from about 1:50 to about 1:8,000, from about 1:100 to about 1:7,000, from about 1:200 to about 1:6,000, from about 1:300 to about 1:5,000, from about 1:400 to about 1:4,000, from about 1:500 to about 1:3,000, from about 1:600 ​​to about 1:2,000, from about 1:700 to about 1:1,000, and from about 1:800 to about 1:900.

[0272] In some embodiments, the ratio between the anionic initiator and the silane compound of formula (I) is about 10:1 to about 1:1, about 9:1 to about 1:1, about 8:1 to about 1:1, about 6:1 to about 1:1, about 5:1 to about 1:1, about 4:1 to about 1:1, and about 3:1 to about 1:1. In some embodiments, the ratio between the anionic initiator and the silane compound of formula (I) is about 2:1. In some embodiments, the ratio between the anionic initiator and the silane compound of formula (I) is about 1:1.

[0273] The present disclosure further provides a polymer of formula (III) [ka] The present invention provides a method for producing a polymer of formula (II) [ka] under suitable conditions, wherein:

[0274] M, Y, L, X 1 Each of X 2 Each of R 1 Each of a, b, and d is as described in formula (I).

[0275] Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d or R 1 and;

[0276] G is a polymer fragment having main chain carbon atoms covalently bonded to each other by C-C single bonds, C-C double bonds, or a combination of C-C single bonds and C-C double bonds;

[0277] c is 1, 2, or 3, where c is less than or equal to b; and

[0278] e is 0, 1, 2, or 3, where e is less than or equal to d.

[0279] In some embodiments, Y is [ka] and further wherein R 2 Each of these is as described above.

[0280] In some embodiments, Y is [ka] [ka] [ka] is selected from the group consisting of:

[0281] In some embodiments, Y is [ka] It is.

[0282] In some embodiments, M is nitrogen, a is 1, and the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0283] In some embodiments, Q 2 Ha-L-Si-(G) e (X 1 ) d-e (X 2 ) 3-d and a polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0284] In some embodiments, each L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, each L is -CH2CH2CH2-.

[0285] In some embodiments, X 1 Each of -OR 1 It is.

[0286] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0287] In some embodiments, c is 1.

[0288] In some embodiments, b is 3.

[0289] In some embodiments, e is 1.

[0290] In some embodiments, d is 3.

[0291] In some embodiments, the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0292] In some embodiments, Q 2 is R 1 and a polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0293] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0294] In some embodiments, X 1 Each of -OR 1 It is.

[0295] In some embodiments, R 1 Each of R is independently an optionally substituted alkyl group having 1 to 20 carbon atoms, or an optionally substituted aryl group having 6 to 12 carbon atoms. 1 is an ethyl group. In some embodiments, R 1 is a methyl group. In some embodiments, R 1 is a phenyl group.

[0296] In some embodiments, c is 1.

[0297] In some embodiments, b is 3.

[0298] In some embodiments, the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0299] In some embodiments, the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0300] In some embodiments, M is sulfur, a is 0, and the polymer has formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0301] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0302] In some embodiments, X 1 Each of -OR 1 It is.

[0303] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0304] In some embodiments, c is 1.

[0305] In some embodiments, b is 3.

[0306] In some embodiments, the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0307] In some embodiments, Y is [ka] It is.

[0308] In some embodiments, M is oxygen, a is 0, and the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0309] In some embodiments, L is an optionally substituted alkylene group having 1 to 20 carbon atoms. In some embodiments, L is -CH2CH2CH2-.

[0310] In some embodiments, X 1 Each of -OR 1 It is.

[0311] In some embodiments, R 1 Each of R is an optionally substituted alkyl group having 1 to 20 carbon atoms. 1 Each of is an ethyl group.

[0312] In some embodiments, c is 1.

[0313] In some embodiments, b is 3.

[0314] In some embodiments, the polymer of formula (III) [ka] is a polymer of formula (II) [ka] under appropriate conditions.

[0315] In some embodiments, the reaction occurs in the presence of a base, an acid, heat, or free radicals. In some embodiments, the reaction occurs in the presence of a base. In some embodiments, the base is selected from the group consisting of sodium hydroxide, sodium methoxide, sodium ethoxide, potassium carbonate, potassium tert-butoxide, aluminum oxide, diisobutylaluminum hydride, methyllithium, lithium hydroxide, lithium methoxide, lithium ethoxide, tetrabutylammonium hydroxide, methylamine, and ethylmagnesium bromide. In some embodiments, the reaction occurs in the presence of an acid. In some embodiments, the acid is selected from the group consisting of stearic acid, hydrochloric acid, hydrobromic acid, and trifluoroacetic acid. In some embodiments, the acid is hydrochloric acid. In some embodiments, the acid is trifluoroacetic acid. In some embodiments, the acid is stearic acid. In some embodiments, the reaction occurs in the presence of heat. In some embodiments, the reaction occurs in the presence of free radicals. In some embodiments, the free radicals are organic or inorganic radical species.

[0316] In some embodiments, the polymer fragment G is as described above.

[0317] The present disclosure relates to compositions comprising one or more of the polymers described above.

[0318] The present disclosure further relates to compositions comprising one or more polymers prepared by the methods described above.

[0319] The present disclosure provides a rubber composition comprising the above-described composition.

[0320] The present disclosure further provides a rubber composition comprising: (i) about 100 parts rubber, where the weight of the rubber is the sum of the weights of each of (a) the diene-based polymer containing at least one functional group, (b) the diene-based polymer not containing a functional group, and (c) the diene-based polymer containing at least one functional group that is Formula II and / or Formula III; (iii) from about 5 to about 140 parts by weight of silica per 100 parts of rubber (i); (iv) from about 0.1 to about 10 parts by weight per 100 parts of rubber (i) of at least one processing aid; and (v) from about 0.1 to about 20 parts by weight per 100 parts of rubber (i) of a vulcanization package comprising at least one vulcanizing agent comprising sulfur and at least one accelerator.

[0321] In some embodiments, the diene-based polymer is a diene-based polymer that contains at least one functional group, a diene-based polymer that does not contain a functional group, or a combination thereof.

[0322] In some embodiments, the diene-based polymer is natural rubber, styrene butadiene rubber, cis 1,4-polyisoprene, cis 1,4-polybutadiene, trans 1,4-polybutadiene, 1,2-polybutadiene, or combinations thereof.

[0323] In some embodiments, the processing aid is 2,2,4-trimethyl-1,2-dihydroquinoline, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, octyltriethoxysilane, triethoxysilylated hydrocarbons, zinc stearate, stearic acid, fatty acid zinc soaps, paraffin wax, microcrystalline wax, paraffinic processing oil, naphthenic processing oil, aromatic processing oil, or combinations thereof.

[0324] In some embodiments, the sulfur in the vulcanizing agent is selected from the group consisting of elemental sulfur, sulfur donor compounds, and combinations thereof.

[0325] In some embodiments, the accelerator is selected from the group consisting of benzothiazoles, guanidine derivatives, thiocarbamates, and combinations thereof.

[0326] In some embodiments, the accelerator is selected from the group consisting of mercaptobenzothiazole, benzothiazole disulfide, diphenyl guanidine, zinc dithiocarbamate, alkylphenol disulfide, zinc butylxanthate, N-dicyclohexyl-2-benzothiazole sulfenamide, N-cyclohexyl-2-benzothiazole sulfenamide, N-oxydiethylenebenzothiazole-2-sulfenamide, N,N-diphenylthiourea, dithiocarbamylsulfenamide, N,N-diisopropylbenzothiozole-2-sulfenamide, zinc-2-mercaptotoluimidazole, dithiobis(N-methylpiperazine), dithiobis(N-β-hydroxyethylpiperazine), dithiobis(dibenzylamine), and combinations thereof.

[0327] In some embodiments, the rubber composition further comprises at least one filler, hi some embodiments, the filler is selected from the group consisting of titanium dioxide, alumina, aluminosilicates, siliceous materials, carbon black, acetylene black, calcium carbonate, barium sulfate, and combinations thereof.

[0328] In some embodiments, the rubber composition further comprises at least one processing oil. In some embodiments, the processing oil is a treated distillate aromatic extract (TDAE) oil.

[0329] In some embodiments, the rubber composition further comprises at least one activator, hi some embodiments, the activator is zinc oxide or stearic acid.

[0330] In some embodiments, the rubber composition further comprises at least one antidegradant. In some embodiments, the antidegradant is N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine. In some embodiments, the antidegradant is 2,2,4-trimethyl-1,2-dihydroquinoline polymer or microcrystalline wax.

[0331] The present disclosure further provides articles of manufacture comprising the rubber compositions described above, in some embodiments, including, but not limited to, tires, conveyor belts, engine mounts, shoe soles, tubes, gloves, windshield wipers, brake pads, erasers, rubber bands, grips, print rollers, flame retardants, and scouring pads. Working Example

[0332] Having now generally described the invention, the same will be understood by reference to the following examples, which are provided herein for illustrative purposes only and are not intended to be limiting unless expressly stated. Example 1 Preparation of aminosilane 1

[0333] A three-neck round bottom flask was fitted with a magnetic stirrer, temperature probe, addition funnel, and nitrogen inlet. Di-tertiary butyl dicarbonate (75.05 g, 0.34 mol) was added to the three-neck round bottom flask. Bis-(3-triethoxysilylpropyl)amine (121.8 g, 0.29 mol) was then added to the flask through the addition funnel over a period of 30 minutes starting at ambient temperature under nitrogen protection. The product of this reaction was stripped and then distilled in a Kugelrohr apparatus at 0.02 mm Hg and a temperature of 140-158°C. 102.44 grams of aminosilane 1 was recovered with a purity of 97.36% by GC. 1 Characterized by 1 H NMR. 1 H NMR (CDCl3, 600MHz): δH 3.83-3.77(12H), 3.23-3.11(4H), 1.79-1.66(4H), 1.44(9H), 1.30-1.17(18H), 0.65-055(4H). Example 2 Preparation of aminosilane 2

[0334] A three-neck round bottom flask was fitted with a magnetic stirrer, temperature probe, addition funnel, and nitrogen inlet. Di-tert-butyl dicarbonate (135.2 g, 0.62 moles) and acetonitrile (111.8 g) were added to the flask. N-phenyl-3-aminopropyltrimethoxysilane (123.4 g, 0.48 moles) was then added to the flask. 4-Dimethylaminopyridine (0.1 g) was then added to the mixture at ambient temperature. The reaction product was stripped and then distilled at 0.02 mm Hg and a temperature of 117.8° C. by Kugelrohr apparatus. 131.07 grams of aminosilane 2 was recovered with a purity of 95.6% by GC. 1 Characterized by 1 H NMR. 1 H NMR (CDCl3, 600MHz): δH 7.38-7.30(2H), 7.22-7.16(3H), 3.62-3.59(2H), 3.60-3.57(9H), 1.77-1.64(2H), 1.43(9H), 0.61-.059(2H). Example 3 Preparation of aminosilane 3

[0335] A three-neck round bottom flask was equipped with a magnetic stirrer, temperature probe, addition funnel, and nitrogen inlet. Di-tert-butyl dicarbonate (50.7 g, 0.23 moles) and acetonitrile (49.4 g) were added to the flask. N-phenyl-3-aminopropyltriethoxysilane (60.2 g, 0.20 moles) was then added to the flask. 4-Dimethylaminopyridine (0.1 g) was then added to the mixture at ambient temperature. The reaction product was stripped and then distilled at 0.02 mm Hg and a temperature of 115-125°C by Kugelrohr apparatus. 66.82 grams of aminosilane 3 was recovered with a purity of 91.5% by GC. 1 Characterized by 1 H NMR. 1 H NMR (CDCl3, 600MHz):δH 7.38-7.30(2H), 7.22-7.16(3H), 3.83-3.77(6H), 3.62-3.59(2H), 1.77-1.66(2H), 1.43(9H), 1.30-1.18(9H), 0.61-0.57(2H). Example 4 Preparation of thiosilane 1

[0336] A three-neck round bottom flask was fitted with a magnetic stirrer, temperature probe, addition funnel and nitrogen inlet. Di-tert-butyl dicarbonate (0.23 mol) and acetonitrile (50.0 g) were added to the flask. (3-mercaptopropyl)triethoxysilane (0.20 mol) was then added to the flask. Sodium carbonate (0.1 g) was then added to the mixture at ambient temperature. The reaction product was heated at 28°C for 1 hour. The reaction product was purified by distilling off the excess di-tert-butyl dicarbonate at 50-55°C at 0.5 mmHg and thiosilane 1 at 90°C at 0.5 mmHg. Thiosilane 1 was recovered and 1 H NMR, 29 Characterized by Si NMR.

[0337] 1H NMR (CDCl3, 400MHz): δH 3.76-3.69(6H,q), 3.57-3.55(2H,t), 1.70-1.65(2H,q), 1.50(9H,s), 1.10-1.05(9H,t)0.702-0.65(2H,t).

[0338] 29 Si NMR (CDCl3, 79MHz): δ-45.14. Example 5 Preparation of non-functionalized SSBR

[0339] Since anionic polymerizations initiated by n-butyllithium are very sensitive to moisture, the following precautions were taken to ensure that polymerizations would occur without quenching the initiator. First, styrene and 1,3-butadiene monomers were stirred separately in basic alumina (to remove inhibitors) and 3A molecular sieves (to trap moisture) for 2 hours. All glassware was dried in an oven at 150°C and assembled hot with all open ports covered. A 4-neck round bottom flask was set up with a condenser, addition funnel, pocket thermometer, and a silicone septum port for adding initiator via syringe. This flask was used with a heating mantle and stirrer. The flask was dried. The flask was then purged with nitrogen and vacuum pulled for 10 minutes each time, three times.

[0340] The flask was charged with toluene (218 mL), 1,3-butadiene (15 wt % in hexane) (140.22 g, 2.59 mol), styrene (30 g, 0.288 mol), and tetrahydrofuran (23.9 ml) via an addition funnel filled with molecular sieves. n-Butyllithium (2 M solution in cyclohexane) (0.92 g, 0.014 mol) was then added via syringe under nitrogen and injected all at once into the reaction mixture. The reaction mixture was heated from room temperature to 50° C. in 5 minutes. The reaction was carried out at 50° C. for 4 hours. No precipitation was observed during the polymerization. The reaction was homogeneous and clear from the start of the polymerization to completion.

[0341] After polymerization was complete, the reaction mixture was quenched with methanol. Heating was then stopped and the reaction mixture was allowed to cool to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55°C to give the non-functionalized SBR. The volatiles were further stripped under high vacuum at 70°C for approximately 5 hours to give a rubbery polymer. 1 It was characterized by HNMR and GPC.

[0342] 1 H NMR (CDCl3, 400MHz): δH 7.36-6.95(9H,m), 5.73-5.13(18H,m), 5.12-4.63(18H,m), 2.73-0.745(53H,m).

[0343] GPC: Mn = 27440 g / mol. Example 6 Preparation of SSBR functionalized with aminosilane 1

[0344] The flask was charged with toluene (218 mL), 1,3-butadiene (15 wt % in hexane) (140.22 g, 2.59 mol), styrene (30 g, 0.288 mol), and tetrahydrofuran (23.9 ml) via an addition funnel filled with molecular sieves. n-Butyllithium (2 M solution in cyclohexane) (0.92 g, 0.014 mol) was then added via syringe under nitrogen and injected all at once into the reaction mixture. The reaction mixture was heated from room temperature to 50° C. in 5 minutes. The reaction was carried out at 50° C. for 4 hours. No precipitation was observed during the polymerization. The reaction was homogeneous and clear from the start of the polymerization to completion. After the polymerization was completed, carbamic acid, N,N-bis[3-(triethoxysilyl)propyl]-1,1-dimethylethyl ester (aminosilane 1) (3.8 g, 0.007 mol) was further added to the flask as a coupling agent. The reaction took place overnight for end-capping to be complete. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55°C to give the aminosilane 1 functionalized SBR. The volatiles were further stripped under high vacuum at 70°C for about 5 hours to give a rubbery polymer. The sample was 1 HNMR, 29 It was characterized by Si NMR and GPC. 1 H NMR (CDCl3, 400MHz): δH 7.32 6.98(18H,m), 5.89-5.11(29H,m), 5.09-4.64(28H,m), 3.90-3.56(12H,m), 3.24-3.02(4H,m), 2.73-2.48(3H,m)2.32-0.363(170H,m). 29 Si NMR (CDCl3, 79MHz): δ10.01, -10.980. GPC: Mn = 26040 g / mol. Example 7 Preparation of SSBR functionalized with aminosilane 2

[0345] The flask was charged with toluene (32 mL), 1,3-butadiene (15 wt % in hexane) (10.28 g, 0.19 mol), styrene (2.20 g, 0.021 mol), and tetrahydrofuran (3.5 ml) via an addition funnel filled with molecular sieves. n-Butyllithium (2 M solution in cyclohexane) (0.135 g, 0.0021 mol) was then added via syringe under nitrogen and injected all at once into the reaction mixture. The reaction mixture was heated from room temperature to 50° C. in 5 minutes. The reaction was carried out at 50° C. for 4 hours. No precipitation was observed during the polymerization. The reaction was homogeneous and clear from the start of the polymerization to completion. After the polymerization was completed, carbamic acid, N-phenyl-N-[3-(trimethoxysilyl)propyl]-1,1-dimethylethyl ester (aminosilane 2) (0.7 g, 0.002 mol) was further added to the flask as a coupling agent. The reaction took place overnight for end-capping to be complete. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55°C to give the aminosilane 2 functionalized SBR. The volatiles were further stripped under high vacuum at 70°C for about 5 hours to give a rubbery polymer. The sample was 1 HNMR and 29 It was characterized by Si NMR. 1 H NMR (CDCl3, 400MHz): δH 7.54-6.98(177H,m), 5.84-5.26(146H,m), 5.21-4.72(183H,m), 3.92-3.51(9H,m), 2.61-0.963(520H,m). 29 Si NMR (CDCl3, 79MHz): δ 9.84, -21.82. Example 8 Preparation of SSBR functionalized with aminosilane 3

[0346] The flask was charged with toluene (32 mL), 1,3-butadiene (15 wt % in hexane) (10.28 g, 0.19 mol), styrene (2.20 g, 0.021 mol), and tetrahydrofuran (3.5 ml) via an addition funnel filled with molecular sieves. n-Butyllithium (2 M solution in cyclohexane) (0.135 g, 0.0021 mol) was then added via syringe under nitrogen and injected all at once into the reaction mixture. The reaction mixture was heated from room temperature to 50° C. in 5 minutes. The reaction was carried out at 50° C. for 4 hours. No precipitation was observed during the polymerization. The reaction was homogeneous and clear from the start of the polymerization to completion.

[0347] After the polymerization was completed, carbamic acid, N-phenyl-N-[3-(triethoxysilyl)propyl]-1,1-dimethylethyl ester (aminosilane 3) (0.8 g, 0.002 mol) was further added to the flask as a coupling agent. The reaction took place overnight for end-capping to be complete. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55°C to give the aminosilane 3 functionalized SBR. The volatiles were further stripped under high vacuum at 70°C for about 5 hours to give a rubbery polymer. The sample was 1 HNMR and 29 It was characterized by Si NMR.

[0348] 1 H NMR (CDCl3, 400MHz): δH 7.43-6.809(168H,m), 5.74-5.12(79H,m), 5.093-4.607(93H,m), 3.893-3.60(6H,m), 2.758-0.814(359H,m).

[0349] 29 Si NMR (CDCl3, 79MHz): δ -21.82, -45.30. Example 9 Preparation of SSBR functionalized with thiosilane 1

[0350] The flask was charged with toluene (32 mL), 1,3-butadiene (15 wt % in hexane) (10.28 g, 0.19 mol), styrene (2.20 g, 0.021 mol), and tetrahydrofuran (3.5 ml) via an addition funnel filled with molecular sieves. n-Butyllithium (2 M solution in cyclohexane) (0.135 g, 0.0021 mol) was then added via syringe under nitrogen and injected all at once into the reaction mixture. The reaction mixture was heated from room temperature to 50° C. in 5 minutes. The reaction was carried out at 50° C. for 4 hours. No precipitation was observed during the polymerization. The reaction was homogeneous and clear from the start of the polymerization to completion.

[0351] After the polymerization was completed, O-(tertiary butyl)S-(3-(triethoxysilyl)propyl)carbonothioate (thiosilane 1) (0.68 g, 0.002 mol) was further added to the flask as a coupling agent. The reaction took place overnight for end-capping to be complete. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55°C to give the thiosilane 1 functionalized SBR. The volatiles were further stripped under high vacuum at 70°C for approximately 5 hours to give a rubbery polymer. The sample was 1 HNMR and 29 It was characterized by Si NMR.

[0352] 1 H NMR (CDCl3, 400MHz): δH 7.20-6.809(30H,m), 5.89-5.04(45H,m), 4.93-4.207(42H,m), 3.93-3.60(6H,m), 2.758-0.814(180H,m).

[0353] 29 Si NMR (CDCl3, 79MHZ): δ -21.90, -46.00, -51.17. Example 10 Preparation of SSBR functionalized with deprotected aminosilane 1

[0354] A flask was charged with toluene (200 mL), tetrahydrofuran (25 ml), SBR functionalized with aminosilane 1 (180 g), and hydrochloric acid (2 M aqueous solution) (0.007 mol, 3.5 mL). The reaction was carried out at 65 °C for 2 h. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55 °C to give the deprotected SBR functionalized with aminosilane 1. The volatiles were further stripped under high vacuum at 70 °C for approximately 5 h to give a rubbery polymer. This sample was 1 HNMR, 13 CNMR, 29 It was characterized by Si NMR, FTIR, TGA and GPC. Example 11 Preparation of SSBR functionalized with deprotected aminosilane 2

[0355] A flask was charged with toluene (35 mL), tetrahydrofuran (5 ml), aminosilane 2-functionalized SBR (14 g), and hydrochloric acid (2 M aqueous solution) (0.002 mol, 1 mL). The reaction was carried out at 65° C. for 2 h. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was rotary evaporated under vacuum at ∼55° C. to give the deprotected aminosilane 2-functionalized SBR. Volatiles were further stripped under high vacuum at 70° C. for approximately 5 h to give a rubbery polymer. This sample was 1 HNMR, 13 CNMR, 29 It was characterized by Si NMR, FTIR, TGA and GPC. Example 12 Preparation of SSBR functionalized with deprotected aminosilane 3

[0356] A flask was charged with toluene (35 mL), tetrahydrofuran (5 ml), SBR functionalized with aminosilane 3 (14 g), and hydrochloric acid (2 M aqueous solution) (0.002 mol, 1 mL). The reaction was carried out at 65° C. for 2 h. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ∼55° C. to give the deprotected SBR functionalized with aminosilane 3. The volatiles were then stripped under high vacuum at 70° C. for approximately 5 h to give a rubbery polymer. This sample was 1 HNMR, 13 CNMR, 29 It was characterized by Si NMR, FTIR, TGA and GPC. Example 13 Preparation of SSBR functionalized with deprotected thiosilane 1

[0357] A flask was charged with toluene (35 mL), tetrahydrofuran (5 ml), SBR functionalized with thiosilane 1 (14 g), and hydrochloric acid (2 M aqueous solution) (0.002 mol, 1 mL). The reaction was carried out at 65 °C for 2 h. Heating was then stopped and the reaction mixture was cooled to room temperature. The solvent was evaporated under vacuum on a rotary evaporator at ~55 °C to give the deprotected SBR functionalized with thiosilane 1. The volatiles were then stripped at 70 °C under high vacuum for approximately 5 h to give a rubbery polymer. This sample was 1 HNMR, 13 CNMR, 29 It was characterized by Si NMR, FTIR, TGA and GPC. Example 14 Preparation of SSBR functionalized with deprotected aminosilane 3

[0358] A flask was charged with dichloromethane (5 mL), aminosilane 3-functionalized SBR (0.25 g), and trifluoroacetic acid (0.002 mol, 1 mL). The reaction was allowed to proceed at room temperature for 1 h. The solvent was rotary evaporated under vacuum at 55 °C to give the deprotected aminosilane 3-functionalized SBR. The sample was then stripped under high vacuum at 60 °C for approximately 4 h to give a rubbery polymer. 1 Characterization was performed by HNMR and FTIR. FTIR at 1699 cm -1 It is clear that the carbonyl peak at 100° C. has disappeared, indicating the deprotection of the tert-butoxycarbonyl protecting group. Example 15 Preparation of aminosilane 4

[0359] 250.17 g of bis(trimethoxysilylpropyl)amine (available as Silquest A-1170 from Momentive Performance Materials, Inc., 0.73 moles), 72.08 g of dimethyl carbonate (0.80 moles), and 6.5 g of sodium methoxide solution (25% in methanol) were charged to a 500 mL round bottom flask equipped with a magnetic stir bar, heating mantle, temperature probe, and short path distillation head. The mixture was heated to 80-90 °C for a total of 54 hours. The resulting product mixture was neutralized with 2.42 g of glacial acetic acid, filtered, stripped, and distilled. Aminosilane 4 was collected as the fraction distilling between 141-143 °C at 0.1-0.2 mm Hg. Aminosilane 4 was characterized by GC / MS. Example 16 Rubber compounding process

[0360] Table 1 lists the ingredients used to prepare rubber compositions using a 75 / 25 blend of non-functionalized solution-polymerized polystyrene butadiene rubber (SSBR) / cis 1,4-polybutadiene and containing 15 parts of non-functionalized SBR oligomer (Comparative Example 5 (Comparative EX5)) or functionalized SBR oligomer (Example 6 (EX6)). The two compounds were mixed in an internal rubber mixer using a mixing procedure that included two non-productive mix steps NP1 and NP2, followed by a final productive mix step FM. Between the two non-productive steps, the silica compound is heat treated at 150°C for about 110 seconds (to promote the necessary silanization reaction). The two compounds are mixed with the curative in the final productive mix at 105°C for about 180 seconds. The rubber compositions shown in Table 1 were cured at 160°C for 20 minutes. [Table 1]

[0361] The physical and dynamic properties obtained are shown in Table 2. Modulus and tensile / elongation were measured according to ASTM D412 using a ZwickRoell ring tester; rebound was measured according to ASTM D7121-05 using a ZwickRoell 5109 rebound machine; Shore A was measured according to ASTM D-2240-15 using a ZwickRoell durometer; RPA modulus was measured at 60°C, 10 Hz, and 10% deformation using an RPA2000 instrument. Hysteresis was measured using a Metravib model 1000+ DMA and values ​​were taken at 10 Hz during a temperature sweep from 0°C to 60°C. [Table 2]

Claims

1. A silane compound having the formula (I): 【Chemistry 156】 wherein: M is selected from the group consisting of nitrogen, sulfur, and oxygen; Y is a protecting group; Q １ is -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ or R １ ; each L is independently absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom; X １ Each of the groups independently represents -OR １ or -OC(=O)R １ ; X ２ Each of these is R １ ; R １ are each independently selected from the group consisting of an optionally substituted alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or two R １ groups are bonded to each other via a covalent bond, provided that two R １ When the groups are linked together, b is 2 or 3; a is 0 or 1, provided that when M is nitrogen, a is 1, or when M is sulfur or oxygen, a is 0; b is 1, 2, or 3; and A silane compound wherein d is 0, 1, 2, or 3.

2. Y is 【Chemistry 157】 The silane compound of claim 1, wherein

3. X １ Each of these is -OR １ The silane compound of claim 1, wherein

4. R １ 2. The silane compound of claim 1, wherein each of is an optionally substituted alkyl group having 1 to 20 carbon atoms.

5. (a) When M is nitrogen, a is 1 and Y is 【Chemistry 158】 and the silane compound of formula (I) is 【Chemistry 159】 and or (b) Q １ is -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ , and Y is [Chemical 160] and the silane compound of formula (I) is 【Chemistry 161】 and or (c) When M is sulfur, a is 0 and Y is 【Chemistry 162】 and the silane compound of formula (I) is 【Chemistry 163】 The silane compound of claim 1, wherein

6. The silane compound of formula (I) 【Chemistry 164】 【Chemistry 165】 The silane compound of claim 1, wherein

7. (a) Formula (II) 【Chemistry 166】 wherein: M is selected from the group consisting of nitrogen, sulfur, and oxygen; Y is a protecting group; Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ or R １ and each L is independently absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom; X １ Each of the groups independently represents -OR １ or -OC(=O)R １ ; X ２ Each of these is R １ ; R １ are each independently selected from the group consisting of an optionally substituted alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or two R １ groups are bonded to each other via a covalent bond, provided that two R １ When the groups are linked together, b is 2 or 3; G is a polymer fragment having main chain carbon atoms covalently bonded to each other by a C-C single bond, a C-C double bond, or a combination of C-C single and C-C double bonds; a is 0 or 1, provided that when M is nitrogen, a is 1, or when M is sulfur or oxygen, a is 0; b is 1, 2, or 3; c is 1, 2, or 3, provided that c is less than or equal to b; d is 0, 1, 2, or 3; and e is 0, 1, 2, or 3, where e is equal to or less than d; or (b) Formula (III) 【Chemistry 167】 wherein: M is selected from the group consisting of nitrogen, sulfur, and oxygen; Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ or R １ and each L is independently absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom; X １ Each of the groups independently represents -OR １ or -OC(=O)R １ ; X ２ Each of these is R １ ; R １ are each independently selected from the group consisting of an optionally substituted alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or two R １ groups are bonded to each other via a covalent bond, provided that two R １ When the groups are linked together, b is 2 or 3; G is a polymer fragment having main chain carbon atoms covalently bonded to each other by a C-C single bond, a C-C double bond, or a combination of C-C single and C-C double bonds; a is 0 or 1, provided that when M is nitrogen, a is 1, or when M is sulfur or oxygen, a is 0; b is 1, 2, or 3; c is 1, 2, or 3, provided that c is less than or equal to b; d is 0, 1, 2, or 3; and e is 0, 1, 2, or 3, provided that e is equal to or less than d;

8. Y in formula (II) is 【Chemical 168】 selected from the group consisting of: and further wherein: R ２ are independently selected from the group consisting of optionally substituted alkyl groups having from 1 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkenyl groups having from 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted cycloalkyl groups having from 3 to 14 carbon atoms and optionally at least one heteroatom, optionally substituted aryl groups having from 6 to 16 carbon atoms and optionally at least one heteroatom, and optionally substituted aralkyl groups having from 7 to 20 carbon atoms and optionally at least one heteroatom.

9. 8. The polymer of claim 7, wherein each L is an optionally substituted alkylene group having 1 to 20 carbon atoms.

10. X １ Each of these is -OR １ 8. The polymer of claim 7, wherein:

11. R １ 8. The polymer of claim 7, wherein each of is an optionally substituted alkyl group having 1 to 20 carbon atoms.

12. (a) When M is nitrogen, a is 1 and Y is 【Chemistry 169】 and the polymer of formula (II) is 【Chemistry 170】 and or (b) When M is nitrogen, a is 1, Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ , and Y is 【Chemistry 171】 and the polymer of formula (II) is 【Chemistry 172】 and or (c) When M is nitrogen, a is 1, Q ２ is R １ , and Y is 【Chemistry 173】 and the polymer of formula (II) is 【Chemistry 174】 and or (d) When M is nitrogen and a is 1, the polymer of formula (III) is 【Chemistry 175】 and or (e) When M is nitrogen, a is 1 and Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ and the polymer of formula (III) is 【Chemistry 176】 8. The polymer of claim 7, wherein:

13. (a) The polymer of formula (II) 【Chemistry 177】 or (b) A polymer of formula (III) 【Chemistry 178】 8. The polymer of claim 7, wherein:

14. G is a polymer fragment of formula (IV) 【Chemistry 179】 wherein: R ３ , R ４ , R ５ , R ７ , R ８ , R ９ , R １０ , R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ and R １８ each independently an alkyl group having 1 to 20 carbon atoms, or hydrogen; R ６ are each independently selected from the group consisting of hydrogen, an alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 14 carbon atoms, a cycloalkenyl group having 4 to 14 carbon atoms, an aryl group having 6 to 16 carbon atoms, and an aralkyl group having 7 to 20 carbon atoms; and 8. The polymer of claim 7, wherein f, g, and h are integers, where f is greater than or equal to 0, g is greater than or equal to 0, and h is greater than or equal to 0, with the proviso that the sum of f, g, and h is greater than or equal to 1.

15. 8. The polymer of claim 7, wherein polymer fragment G is a styrene butadiene polymer.

16. A silane compound of formula (I) according to any one of claims 1 to 6. 【Transformation 180】 1. A method for producing a compound comprising: Compound of formula (V) 【Chemistry 181】 with a protecting agent; M is selected from the group consisting of nitrogen, sulfur, and oxygen; Y is a protecting group; Q １ is -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ or R １ ; each L is independently absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom; X １ Each of the groups independently represents -OR １ or -OC(=O)R １ ; X ２ Each of these is R １ ; R １ are each independently selected from the group consisting of an optionally substituted alkyl group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkynyl group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted aryl group having 6 to 12 carbon atoms and optionally at least one heteroatom, an optionally substituted aralkyl group having 7 to 16 carbon atoms and optionally at least one heteroatom, and an optionally substituted cyclic silane; or two R １ groups are bonded to each other via a covalent bond, provided that two R １ When the groups are linked together, b is 2 or 3; a is 0 or 1, provided that when M is nitrogen, a is 1, or when M is sulfur or oxygen, a is 0; b is 1, 2, or 3; and The method wherein d is 0, 1, 2, or 3.

17. The protective agent 【Chemistry 182】 and further wherein: X is a halogen or OR ２ ;and R ２ are independently selected from the group consisting of optionally substituted alkyl groups having from 1 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkenyl groups having from 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted cycloalkyl groups having from 3 to 14 carbon atoms and optionally at least one heteroatom, optionally substituted aryl groups having from 6 to 16 carbon atoms and optionally at least one heteroatom, and optionally substituted aralkyl groups having from 7 to 20 carbon atoms and optionally at least one heteroatom.

18. (a) When M is nitrogen, a is 1 and Y is 【Chemistry 183】 and the silane compound of formula (I) is 【Chemistry 184】 and a compound of formula (V) 【Chemistry 185】 Protective agent 【Chemistry 186】 or prepared by reacting (b) When M is nitrogen, a is 1 and Y is 【Chemistry 187】 And Q １ is -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ The silane compound of formula (I) 【Chemical 188】 and a compound of formula (V) 【Chemical 189】 Protective agent 【Chemistry 190】 or prepared by reacting (c) When M is nitrogen, a is 1, d is 3, and Y is 【Chemistry 191】 And Q １ is -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ , L is -CH ２ CH ２ CH ２ -, X １ Ha-OR １ , and R １ Ha-CH ２ CH ３ and the silane compound of formula (I) is 【Chemistry 192】 and a compound of formula (V) 【Chemistry 193】 Protective agent 【Chemistry 194】 or prepared by reacting (d) When M is nitrogen, a is 1 and Y is 【Chemistry 195】 And Q １ is R １ The silane compound of formula (I) 【Chemistry 196】 and a compound of formula (V) 【Chemistry 197】 Protective agent 【Chemistry 198】 or prepared by reacting (e) When M is sulfur, a is 0 and Y is 【Chemistry 199】 and the silane compound of formula (I) is 【Chemistry 200】 and a compound of formula (V) 【Chemical Engineering 201】 Protective agent 【Chemical Engineering 202】 17. The method of claim 16, wherein the compound is prepared by reacting

19. 16. A method for producing the polymer of any one of claims 7 to 15, wherein the polymer is of formula (II) 【Chemical 203】 is represented by (i) reacting a chain of C-C unsaturated carbon atom monomers with an anionic initiator to form a polymer fragment G; and (ii) reacting the polymer fragment G with a silane compound of formula (I) 【Chemical 204】 prepared by reacting In the formula: M is selected from the group consisting of nitrogen, sulfur, and oxygen; Y is a protecting group; Q １ is -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ or R １ ; Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ or R １ where Q １ -L-Si-(X １ ) ｄ (X ２ ) ３－ｄ When Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ and Q １ is R １ When Q ２ is R １ and each L is independently absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom; X １ Each of the groups independently represents -OR １ or -OC(=O)R １ ; X ２ Each of these is R １ ; R １ each is independently selected from the group consisting of optionally substituted alkyl groups having 1 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkenyl groups having 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkynyl groups having 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted cycloalkyl groups having 3 to 10 carbon atoms and optionally at least one heteroatom, optionally substituted aryl groups having 6 to 12 carbon atoms and optionally at least one heteroatom, and optionally substituted aralkyl groups having 7 to 16 carbon atoms and optionally at least one heteroatom; a is 0 or 1; provided that when M is nitrogen, a is 1, or when M is sulfur or oxygen, a is 0; b is 1, 2, or 3; c is 1, 2, or 3, provided that c is less than or equal to b; d is 0, 1, 2, or 3; and The method wherein e is 0, 1, 2, or 3, where e is less than or equal to d.

20. (a) When M is nitrogen, a is 1 and Y is 【Chemical 205】 and the polymer of formula (II) is 【Chemical 206】 and the polymer fragment G is converted into a silane compound of formula (I) 【Chemical 207】 or prepared by reacting (b) When M is nitrogen, a is 1 and Y is 【Chemical 208】 and Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ , the polymer of formula (II) 【Chemical Engineering 209】 and the polymer fragment G is converted into a silane compound of formula (I) 【Chemical 210】 or prepared by reacting (c) When M is nitrogen, a is 1 and Y is 【Chemistry 211】 and Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ , d is 3, L is -CH ２ CH ２ CH ２ -, e is 1, X １ Ha-OR １ , and R １ Ha-CH ２ CH ３ and the polymer of formula (II) is 【Chemical Engineering 212】 and the polymer fragment G is converted into a silane compound of formula (I) 【Chemistry 213】 prepared by reacting (d) When M is nitrogen, a is 1 and Y is 【Chemical 214】 And Q ２ is R １ , the polymer of formula (II) 【Chemical 215】 and the polymer fragment G is converted into a silane compound of formula (I) 【Chemical 216】 or prepared by reacting (e) When M is sulfur, Y is 【Chemical 217】 where a is 0 and the polymer of formula (II) is 【Chemistry 218】 and the polymer fragment G is converted into a silane compound of formula (I) 【Chemical 219】 20. The method of claim 19, wherein the compound is prepared by reacting

21. 20. The method of claim 19, wherein the anionic initiator is n-butyllithium.

22. 16. A method for producing the polymer of any one of claims 7 to 15, wherein the polymer has formula (III): 【Chemical 220】 and the method is represented by the formula (II) 【Chemistry 221】 with an acid, a base, or heat, wherein: M is selected from the group consisting of nitrogen, sulfur, and oxygen; Y is a protecting group; Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ or R １ and each L is independently absent, an optionally substituted alkylene group having 1 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted alkenylene group having 2 to 20 carbon atoms and optionally at least one heteroatom, an optionally substituted cycloalkylene group having 3 to 10 carbon atoms and optionally at least one heteroatom, an optionally substituted arylene group having 6 to 12 carbon atoms and optionally at least one heteroatom, or an optionally substituted aralkylene group having 7 to 16 carbon atoms and optionally at least one heteroatom; X １ Each of the groups independently represents -OR １ or -OC(=O)R １ ; X ２ Each of these is R １ ; R １ each is independently selected from the group consisting of optionally substituted alkyl groups having 1 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkenyl groups having 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted alkynyl groups having 2 to 20 carbon atoms and optionally at least one heteroatom, optionally substituted cycloalkyl groups having 3 to 10 carbon atoms and optionally at least one heteroatom, optionally substituted aryl groups having 6 to 12 carbon atoms and optionally at least one heteroatom, and optionally substituted aralkyl groups having 7 to 16 carbon atoms and optionally at least one heteroatom; G is a polymer fragment having main chain carbon atoms covalently bonded to each other by a C-C single bond, a C-C double bond, or a combination of C-C single and C-C double bonds; a is 0 or 1, provided that when M is nitrogen, a is 1, or when M is sulfur or oxygen, a is 0; b is 1, 2, or 3; c is 1, 2, or 3, provided that c is less than or equal to b; d is 0, 1, 2, or 3; and The method wherein e is 0, 1, 2, or 3, where e is less than or equal to d.

23. (a) When M is nitrogen, a is 1, and the polymer of formula (III) is 【Chemistry 222】 and a polymer of formula (II) 【Chemistry 223】 in the presence of an acid, a base, or heat; or (b) When M is nitrogen, a is 1 and Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ and the polymer of formula (III) is 【Chemistry 224】 and a polymer of formula (II) 【Chemical 225】 in the presence of an acid, a base, or heat; or (c) When M is nitrogen, a is 1 and Y is 【Chemistry 226】 and Q ２ -L-Si-(G) ｅ (X １ ) ｄ－ｅ (X ２ ) ３－ｄ , d is 3, L is -CH ２ CH ２ CH ２ -, e is 1, b is 3, X １ Ha-OR １ , and R １ Ha-CH ２ CH ３ and the polymer of formula (III) is 【Chemistry 227】 and a polymer of formula (II) 【Chemistry 228】 in the presence of an acid, a base, or heat; or (d) When M is nitrogen, a is 1 and Q ２ is R １ and the polymer of formula (III) is 【Chemistry 229】 and the polymer (II) 【Chemistry 230】 in the presence of an acid, a base, or heat.

24. A rubber composition comprising one or more polymers according to any one of claims 7 to 15.

25. Use of a polymer according to any one of claims 7 to 15 in a rubber composition.

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