6-aminoquinoline anti-degradation agent

Abstract

The present disclosure provides a compound represented by formula (I): wherein R1a, R1b, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, R3f, and R3g are as defined in the specification, or a salt, solvate, or stereoisomer thereof. The present disclosure also provides compositions, vulcanized elastomer articles, lubricant compositions, combustible fuel compositions, and fuel additive compositions comprising the compounds disclosed herein. The present disclosure also provides methods for making the compositions and vulcanized elastomeric articles described herein. The present disclosure also provides a method for retreading a tire using the composition described herein. The present disclosure also provides kits comprising the compositions described herein. (I)

Description

Technical Field

[0001] This disclosure provides compounds having anti-degradation agent (e.g., anti-ozone agent, antioxidant, and / or anti-fatigue agent) properties, said compounds being useful additives among: vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels, and other compositions requiring such properties, or compositions that can themselves be used as compositions imparting such properties. Background Technology

[0002] Many materials, such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, brackets, vibration isolators, etc.), lubricants, and petroleum products (such as hydraulic fluids, oils, fuels, and oil / fuel additives for automotive and aerospace applications), are prone to degradation upon prolonged exposure to light, heat, oxygen, ozone, repetitive mechanical action, etc. Therefore, compounds and compositions exhibiting anti-degradation effects are well known in the art. For example, U.S. Patent No. 8,987,515 discloses an aromatic polyamine that can be used to inhibit oxidative degradation, particularly in lubricant compositions. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules, which are claimed to have improved solubility in many commercially available oils and lubricants.

[0003] Anti-degradation agents used in the manufacture of articles formed from elastomers, plastics, etc., require a very specific combination of qualities, which can be difficult to achieve. While anti-degradation agents must demonstrate commercially acceptable efficacy, they must also exhibit that efficacy over a long period associated with the use of the article, particularly at exposed surfaces (where degradation from environmental factors such as light, oxygen, and ozone primarily occurs). As protecting surface-exposed components is important, the efficacy of protecting embedded components of composite materials from oxidative aging and repeated mechanical action is crucial. Anti-degradation agents must achieve these results without negatively impacting the efficacy or desired properties of other additives in the final article. Furthermore, anti-degradation agents that provide or enhance mechanical fatigue life after the article has been put into use, oxidatively aged, or exposed to ozone are highly valuable because they fundamentally improve the useful mechanical life of the article. Therefore, elastomer articles undergoing repeated mechanical bending, stretching, or compression during use will greatly benefit from this finding.

[0004] Articles made from general-purpose elastomers such as natural rubber (particularly tires) are particularly susceptible to degradation by both oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effects of oxygen degradation on rubber differ from those of ozone degradation; however, both effects can be detrimental to tire performance, appearance, and expected life. Fatigue and crack propagation are also of particular concern, especially for the steel belt edge areas and tire sidewalls (whether inflated, partially inflated, or uninflated), which are subjected to significant stress and tensile forces during bending, and this continues throughout the tire's lifespan. U.S. Patent No. 8,833,417 describes an antioxidant system that is claimed to provide greater long-term resistance to fatigue and crack propagation than known antioxidants discussed below.

[0005] Materials with anti-degradation properties are well known in the art for tire applications and are commercially available. For example, N,N'-disubstituted p-phenylenediamines (such as those marketed under the Santoflex® brand) are generally favored by many tire manufacturers. EP 3147321 A1 discloses rubber compositions, tires, amine compounds, and anti-aging agents, and particularly rubber compositions allegedly suitable for tread or sidewall rubbers of tires. Summary of the Invention

[0006] This disclosure provides compounds that can be used as anti-degradation agents (e.g., anti-ozone agents and / or antioxidants) and / or as additives in lubricants or combustible fuels, said compounds being represented by any of the following formulas (I)-(III), collectively referred to herein as "Compounds of the Disclosure" or individually as "Compound of the Disclosure".

[0007] This disclosure also provides compositions comprising:

[0008] (i) the compounds disclosed herein; and

[0009] (ii) One or more elastomers; or

[0010] (iii) One or more fillers; or

[0011] (iv) One or more rubber chemicals; or

[0012] (v) One or more plasticizers; or

[0013] (vi) One or more other anti-degradation agents; or

[0014] (vii) Combinations of the following: one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers and / or one or more additional anti-degradation agents, collectively referred to herein as "Compositions of the Disclosure" or individually as "Composition of the Disclosure".

[0015] This disclosure also provides compositions comprising the compounds of this disclosure and one or more elastomers.

[0016] This disclosure also provides compositions comprising the compounds of this disclosure and one or more fillers.

[0017] This disclosure also provides compositions comprising the compounds of this disclosure and one or more rubber chemicals.

[0018] This disclosure also provides compositions comprising the compounds of this disclosure and one or more plasticizers.

[0019] This disclosure also provides compositions comprising the compounds of this disclosure and one or more additional anti-degradation agents.

[0020] This disclosure also provides compositions comprising the compounds of this disclosure and one or more carriers.

[0021] This disclosure also provides a method for preparing a composition comprising the compound of this disclosure and one or more supports, the method comprising mixing the compound with one or more supports.

[0022] This disclosure also provides vulcanized elastomer articles comprising compounds of this disclosure.

[0023] This disclosure also provides vulcanized elastomer articles prepared using the compositions described herein (e.g., compositions of this disclosure or compositions comprising compounds of this disclosure and one or more carriers).

[0024] This disclosure also provides a method for preparing the vulcanized elastomer article described herein, the method comprising:

[0025] (a) Forming the composition described herein into a shaped form; and

[0026] (b) Vulcanize the shaped material.

[0027] To provide vulcanized elastomer products.

[0028] This disclosure also provides lubricant compositions comprising a lubricant and compounds of this disclosure.

[0029] This disclosure also provides combustible fuel compositions comprising combustible fuel and compounds of this disclosure.

[0030] This disclosure also provides fuel additive compositions comprising fuel additives and compounds of this disclosure.

[0031] This disclosure also provides a method for retreading tires, the method comprising:

[0032] (a) Applying the composition described herein to a tire;

[0033] (b) A pre-cured tread is placed around the tire;

[0034] (c) Applying a cured coating around the tire; and

[0035] (d) Vulcanize the tire.

[0036] This disclosure also provides a kit comprising the composition described herein and instructions for using the composition in a vulcanizable elastomer composition.

[0037] This disclosure also provides a kit comprising the composition described herein and instructions for preparing vulcanized elastomer articles using the composition.

[0038] Further embodiments and advantages of this disclosure will be set forth in part in the description which follows, and will be learned from the description or by practice of the disclosure. The embodiments and advantages of this disclosure will be realized and obtained by means of the elements and combinations particularly pointed out in the appended claims.

[0039] It should be understood that the foregoing description of the invention and the following detailed description are merely exemplary and illustrative, and do not limit the scope of the claimed invention. Attached Figure Description

[0040] Figure 1 This describes the intermediate compound 1-I in d6-dimethyl sulfoxide (d6-DMSO). 1 Line plot of H nuclear magnetic resonance (NMR) spectrum.

[0041] Figure 2 This describes the intermediate compound 1-I in d6-DMSO. 13 Line plot of C APT NMR spectrum.

[0042] Figure 3This is a liquid chromatography (LC) chromatogram of intermediate compound 1-I.

[0043] Figure 4 This describes compound 1 in d-chloroform (CDCl3). 13 Line plot of C APT NMR spectrum.

[0044] Figure 5 This is the LC chromatogram of compound 1.

[0045] Figure 6 This describes compound 2 in d6-DMSO. 13 Line plot of C APT NMR spectrum.

[0046] Figure 7 This is the LC chromatogram of compound 2.

[0047] Figure 8 This is the LC chromatogram of the intermediate compound 3-I.

[0048] Figure 9 This describes compound 3 in d6-DMSO 13 Line plot of C APT NMR spectrum.

[0049] Figure 10 This is the LC chromatogram of compound 3.

[0050] Figure 11 This describes the intermediate compound 4-I in d6-DMSO. 13 Line plot of C APT NMR spectrum.

[0051] Figure 12 This is the LC chromatogram of the intermediate compound 4-I.

[0052] Figure 13 This describes compound 4 in d6-DMSO. 13 Line plot of C APT NMR spectrum.

[0053] Figure 14 This is the LC chromatogram of compound 4.

[0054] Figure 15 This describes the intermediate compound 47-I in d6-DMSO. 13 Line plot of C APT NMR spectrum.

[0055] Figure 16 This is the LC chromatogram of intermediate compound 47-I.

[0056] Figure 17 This describes compound 47 in d6-DMSO. 13 Line plot of C APT NMR spectrum.

[0057] Figure 18 This is the LC chromatogram of compound 47. Detailed Implementation

[0058] In one embodiment, the compound disclosed herein is a compound having formula (I):

[0059] (I),

[0060] Or its salts, solvates or stereoisomers, wherein:

[0061] Is it a single bond or a double bond?

[0062] R 1a Choose from the following groups: C1-C arbitrarily substituted 12 Alkyl, -CHR 1c R 1d C3-C6 cycloalkyl, 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups;

[0063] R 1b Select from the group consisting of hydrogen and C1-C9 alkyl groups;

[0064] R 1c Choose from the group consisting of: optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5- or 6-membered heteroaryl;

[0065] R 1d Select from the group consisting of hydrogen and C1-C9 alkyl groups;

[0066] R 2a R 2b and R 2c Independently selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; or

[0067] R 2b Choose from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; and

[0068] R 2a and R 2c Together with the two carbon atoms they are attached to, they form C5-C8 cycloalkyl, 5- to 8-membered heterocyclic groups, or C5-C6 aryl groups;

[0069] R 3a and R 3b Independently selected from the group consisting of: hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that if If it is a double bond, then R 3b Does not exist; or

[0070] R 3a and R 3bTogether with the carbon atoms they are attached to, they form C3-C. 12 cycloalkyl, under the condition that It is a single key;

[0071] R 3c and R 3d Independently selected from the group consisting of: hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that if If it is a double bond, then R 3d Does not exist; or

[0072] R 3c and R 3d Together with the carbon atoms they are attached to, they form C3-C. 12 cycloalkyl, under the condition that It is a single key;

[0073] R 3e and R 3f Independently selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; or

[0074] R 3e and R 3f Together with the carbon atoms they are attached to, they form C3-C. 12 cycloalkyl;

[0075] R 3gSelected from the group consisting of hydrogen and C1-C9 alkyl groups; and

[0076] R 4 and R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

[0077] In another embodiment, the compound disclosed herein is a compound having formula (I), provided that R 3e and / or R 3f If it is hydrogen, then R 3c and R 3d Independently selected from the group consisting of: C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

[0078] In another embodiment, the compound disclosed herein is a compound having formula (II):

[0079] (II)

[0080] Where R 1a R 2a R 2b R 2c R 3a R 3b R 3c R 3d R 3e and R 3f As defined by associative formula (I).

[0081] In some embodiments, the compounds disclosed herein are compounds of formula (II), wherein:

[0082] R 3c and R 3d Independently selected from the group consisting of: C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; or

[0083] R 3c and R 3d Together with the carbon atoms they are attached to, they form C3-C. 12 Cycloalkyl.

[0084] In some embodiments, the compounds disclosed herein are compounds of formula (II), wherein:

[0085] R 3e and R 3fIndependently selected from the group consisting of: halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; or

[0086] R 3e and R 3f Together with the carbon atoms they are attached to, they form C3-C. 12 Cycloalkyl.

[0087] In some embodiments, the compounds disclosed herein are compounds of formula (I) or formula (II), wherein R 3b It is hydrogen.

[0088] In some embodiments, the compounds disclosed herein are compounds having formula (III):

[0089] (III)

[0090] Where R 1a R 2a R 2b R 2c R 3a R 3c R 3e and R 3f As defined by associative formula (I).

[0091] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R1a It is an optional substituted phenyl group.

[0092] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a It is C1-C 12 alkyl.

[0093] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a It is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0094] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a It is isopropyl or sec-butyl.

[0095] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a yes:

[0096] or .

[0097] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 2a R 2b and R 2c The group consisting of hydrogen and C1-C9 alkyl groups is selected independently.

[0098] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 2b and R 2c It is hydrogen.

[0099] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 2a Choose from the group consisting of hydrogen and C1-C4 alkyl groups.

[0100] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is hydrogen.

[0101] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is a C1-C9 alkyl group.

[0102] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is a C3-C6 cycloalkyl group.

[0103] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is an optional substituted phenyl group.

[0104] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3c It is hydrogen.

[0105] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3c It is a C1-C9 alkyl group.

[0106] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3c It is a C3-C6 cycloalkyl group.

[0107] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3c It is an optional substituted phenyl group.

[0108] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is hydrogen.

[0109] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is a C1-C8 alkoxy group.

[0110] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is -OH.

[0111] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e Yes -SH.

[0112] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is a C1-C8 alkylthio group.

[0113] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R3e It is an arylthio group.

[0114] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is a C1-C9 alkyl group.

[0115] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is a C3-C6 cycloalkyl group.

[0116] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3e It is an optional substituted phenyl group.

[0117] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3f It is hydrogen.

[0118] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3f It is a C1-C9 alkyl group.

[0119] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3f It is a C3-C6 cycloalkyl group.

[0120] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3f It is an optional substituted phenyl group.

[0121] In some embodiments, the compounds disclosed herein are any one or more compounds listed in Table 1, or their salts or solvates.

[0122] Table 1

[0123]

[0124] The compounds disclosed herein can be used as anti-degradation agents (e.g., anti-ozone agents and / or antioxidants), as additives in lubricants, and as additives in combustible fuels.

[0125] The compounds disclosed herein can be prepared, for example, by a two-step method comprising i) reacting 4-nitroaniline with an alkene and an aldehyde or ketone in acetonitrile or other suitable solvent and catalyst (such as any suitable acid or I2), i.e., by a Povarov reaction, and ii) reacting the product of step i) with an aldehyde or ketone under reducing conditions (e.g., pressurized H2 using a platinum catalyst), as shown in Scheme 1, wherein R 1e For example, C1-C 12 Alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, or optionally substituted 5- or 6-membered heteroaryl, and R 1f It is, for example, hydrogen or C1-C6 alkyl.

[0126] Option 1

[0127]

[0128] The compounds disclosed herein can also be prepared by methods known in the art, by oxidizing the compounds obtained in Scheme 1, as shown in Scheme 2.

[0129] Option 2

[0130]

[0131] definition

[0132] As used herein, the term "alkyl" itself, or as part of another group, refers to a group containing one to twelve carbon atoms (i.e., C1-C2). 12 An alkyl group is a straight-chain or branched aliphatic hydrocarbon with a specified number of carbon atoms (e.g., C1-C3 alkyl (such as methyl, ethyl, propyl, or isopropyl); C1-C4 alkyl (such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl) etc.). In one embodiment, the alkyl group is a straight-chain alkyl group. In another embodiment, the alkyl group is a branched alkyl group. In one embodiment, the alkyl group is a C1-C8 alkyl group. In another embodiment, the alkyl group is a C1-C6 alkyl group. In another embodiment, the alkyl group is a C1-C4 alkyl group. In another embodiment, the alkyl group is a C1-C3 alkyl group. Non-limiting exemplary C1-C 12Alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0133] As used herein, the term "optionally substituted alkyl" itself, or as part of another group, refers to an unsubstituted alkyl group or an alkyl group substituted with one to three substituents, wherein each substituent is independently a nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, cycloalkyl, or -C(=O)OR 1i , where R 1i It is a C1-C6 alkyl group.

[0134] As used herein, the term "aryl" itself, or as part of another group, refers to an aromatic ring system having six to fourteen carbon atoms, i.e., C6-C. 14 Aryl. Non-limiting exemplary aryl groups include phenyl (abbreviated as "Ph"), naphthyl, phenanthryl, anthraceneyl, indene, azulel, biphenyl, biphenylenyl, and fluorenyl. In one embodiment, the aryl group is phenyl or naphthyl. In another embodiment, the aryl group is phenyl.

[0135] As used herein, the term “halogenated” or “halogen” itself or as part of another group refers to -Cl, -F, -Br, or -I.

[0136] As used herein, the term "nitro" itself, or as part of another group, refers to -NO2.

[0137] As used herein, the term "cyano" itself, or as part of another group, refers to -CN.

[0138] As used herein, the term "hydroxyl group" itself, or as part of another group, refers to -OH.

[0139] As used herein, the term "amino" itself, or as part of another group, refers to the formula -NR. 1g R 1h The group, wherein R 1g and R 1h It is either hydrogen or alkyl.

[0140] In one embodiment, the amino group is -NH2.

[0141] In another embodiment, the amino group is an "alkylamino group", i.e., wherein R 1g It is a C1-C6 alkyl group and R 1h It is an amino group of hydrogen. In one embodiment, R 1gIt is a C1-C4 alkyl group. Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0142] In another embodiment, the amino group is a "dialkylamino", i.e., wherein R 1g and R 1h Each is independently a C1-C6 alkyl amino group. In one embodiment, R 1g and R 1h Each is independently a C1-C4 alkyl group. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0143] As used herein, the term "alkyl carbonyl" itself, or as part of another group, refers to a carbonyl group substituted with an alkyl group, i.e., -C(=O)-. In one embodiment, the alkyl group is a C1-C4 alkyl group. A non-limiting exemplary alkyl carbonyl group is -COCH3.

[0144] As used herein, the term "haloalkyl" itself, or as part of another group, refers to an alkyl group substituted with one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl group is substituted with one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl group is substituted with one, two, or three fluorine atoms. In another embodiment, the alkyl group is C1-C6 alkyl, and the resulting haloalkyl group is referred to as "C1-C6 haloalkyl". In another embodiment, the alkyl group is C1-C4 alkyl, and the resulting haloalkyl group is referred to as "C1-C4 haloalkyl". In another embodiment, the alkyl group is C1 or C2 alkyl. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl.

[0145] As used herein, the term "alkoxy" itself, or as part of another group, refers to an alkyl group attached to a terminal oxygen atom. In one embodiment, the alkyl group is a C1-C6 alkyl group, and the resulting alkoxy group is referred to as "C1-C6 alkoxy". In another embodiment, the alkyl group is a C1-C4 alkyl group, and the resulting alkoxy group is referred to as "C1-C4 alkoxy". Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and tert-butoxy groups.

[0146] As used herein, the term "alkathioyl" itself, or as part of another group, refers to an alkyl group attached to a terminal sulfur atom. In one embodiment, the alkyl group is a C1-C6 alkyl group, and the resulting alkathioyl group is referred to as "C1-C6 alkathioyl". In one embodiment, the alkyl group is a C1-C4 alkyl group, and the resulting alkathioyl group is referred to as "C1-C4 alkathioyl". Non-limiting exemplary alkathioyl groups include -SCH3 and -SCH2CH3.

[0147] As used herein, the term "arylthio" on its own or as part of another group refers to an aryl group attached to a terminal sulfur atom. In some embodiments, the aryl group is phenyl or naphthyl.

[0148] As used herein, the term "cycloalkyl" itself, or as part of another group, refers to saturated and partially unsaturated (e.g., containing one or two double bonds) containing three to twelve carbon atoms (i.e., C3-C2). 12 A cycloalkyl group is a monocyclic, bicyclic, or tricyclic aliphatic hydrocarbon with a specified number of carbon atoms (e.g., C3-C6 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl). In one embodiment, the cycloalkyl group is bicyclic, meaning it has two rings. In another embodiment, the cycloalkyl group is monocyclic, meaning it has one ring. In another embodiment, the cycloalkyl group is C3-C8 cycloalkyl. In yet another embodiment, the cycloalkyl group is C6-C8 cycloalkyl. 3- C6 cycloalkyl. In another embodiment, the cycloalkyl group is a C5 cycloalkyl group, namely cyclopentyl. In another embodiment, the cycloalkyl group is a C6 cycloalkyl group, namely cyclohexyl. Non-limiting exemplary C3-C 12 Cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decahydronaphthalene, adamantyl, cyclohexenyl and spiroheptane[3.3].

[0149] As used herein, the term “optionally substituted phenyl” itself or as part of another group refers to an unsubstituted or substituted alkyl group, wherein each of the substituents is independently a halogen, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.

[0150] As used herein, the term "heterocycle," either on its own or as part of another group, refers to a monocyclic, bicyclic, or tricyclic group containing three to eighteen ring members, either saturated or partially unsaturated (e.g., containing one or two double bonds), i.e., a 3- to 18-membered heterocycle containing one, two, three, or four heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom can be independently oxidized to yield sulfoxide (i.e., S(=O)) or sulfone (i.e., S(=O)2). The term heterocycle includes groups in which one or more -CH2- groups are replaced by one or more -C(=O)- groups, including cyclic urea groups (such as imidazolidinyl-2-one), cyclic amide groups (such as pyrrolidine-2-one or piperidin-2-one), and cyclic carbamate groups (such as oxazolidinyl-2-one). The term heterocycle also includes groups having fused optional substituted aryl or optional substituted heteroaryl groups, such as indoline, indoline-2-one, 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]azaheptanyl or 1,3,4,5-tetrahydro-2H-benzo[d]azaheptanyl-2-one. In some embodiments, the heterocycle is a 6-membered ring containing one nitrogen atom. The heterocycle may be fused with the remainder of the molecule to form a bicyclic group, such as 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0151] As used herein, the term “optionally substituted heterocycle” refers, either on its own or as part of another group, to an unsubstituted or substituted heterocyclic group, wherein each of the substituents is independently a halogen, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.

[0152] As used herein, the term "heteroaryl" itself, or as part of another group, refers to a monocyclic aromatic ring system having five to six ring members, i.e., a 5- to 6-membered heteroaryl containing one, two, three, four, or five heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl has three heteroatoms. In another embodiment, the heteroaryl has two heteroatoms. In another embodiment, the heteroaryl has one heteroatom. In another embodiment, the heteroaryl has five ring atoms (e.g., furanyl, a 5-membered heteroaryl having four carbon atoms and one oxygen atom). In another embodiment, the heteroaryl has six ring atoms (e.g., pyridyl, a 6-membered heteroaryl having five carbon atoms and one nitrogen atom). Non-limiting exemplary heteroaryls include thiophene, furanyl, pyranyl, 2H-pyrroleyl, pyrroleyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, the heteroaryl group is selected from thienyl (e.g., thien-2-yl and thien-3-yl), furanyl (e.g., 2-furanyl and 3-furanyl), pyrroloyl (e.g., 1H-pyrrolo-2-yl and 1H-pyrrolo-3-yl), imidazoyl (e.g., 2H-imidazo-2-yl and 2H-imidazo-4-yl), pyrazolyl (e.g., 1H-pyrazol-3-yl, 1H-pyrazol-4-yl and 1H-pyrazol-5-yl), and pyridyl (e.g., pyridin-2-yl, ...). The terms pyridinyl-3-yl and pyridinyl-4-yl, pyrimidinyl (e.g., pyrimidinyl-2-yl, pyrimidinyl-4-yl, and pyrimidinyl-5-yl), thiazolyl (e.g., thiazolyl-2-yl, thiazolyl-4-yl, and thiazolyl-5-yl), isothiazolyl (e.g., isothiazolyl-3-yl, isothiazolyl-4-yl, and isothiazolyl-5-yl), oxazolyl (e.g., oxazolyl-2-yl, oxazolyl-4-yl, and oxazolyl-5-yl), and isoxazolyl (e.g., isoxazolyl-3-yl, isoxazolyl-4-yl, and isoxazolyl-5-yl). The term heteroaryl also includes N-oxides. A non-limiting exemplary N-oxide is a pyridinyl N-oxide.

[0153] As used herein, the term “optionally substituted heteroaryl” refers, either on its own or as part of another group, to an unsubstituted heteroaryl group or substituted with one to four substituents, wherein each substituent is independently a halogen, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.

[0154] As used herein, the term "stereoisomer" refers to the collective term for all isomers of a single molecule that differ only in the spatial orientation of their atoms. It includes enantiomers and isomers of compounds that are not mirror images of each other (diastereomers).

[0155] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom that is attached to four different groups.

[0156] The terms “enantiomer” and “enantiomer” refer to molecules that cannot be superimposed on their mirror images and are therefore optically active, wherein an enantiomer rotates the plane of polarized light in one direction and its mirror compound rotates the plane of polarized light in the opposite direction.

[0157] The term "racemic" refers to a mixture of equal parts of enantiomers, and the mixture is optically inert.

[0158] The term "absolute configuration" refers to the spatial arrangement of atoms in a chiral molecular entity (or group) and its stereochemical description, such as R or S.

[0159] Unless otherwise stated, the stereochemical terminology and conventions used in this specification are intended to be consistent with those described in Pure & Appl. Chem 68:2193 (1996).

[0160] The term "enantiomer excess" or "ee" refers to a measure of the amount of one enantiomer present relative to another. For a mixture of R and S enantiomers, the enantiomer excess percentage is defined as |R - S| * 100, where R and S are the corresponding molar or weight fractions of the enantiomers in the mixture such that R + S = 1. Knowing the optical rotation of the chiral substance, the enantiomer excess percentage is defined as ([α]). obs / [α] max ) * 100, where [α] obs It is the optical rotation of a mixture of enantiomers, and [α] max It is the optical rotation of the pure enantiomer. Various analytical techniques (including NMR spectroscopy, chiral column chromatography, or optical polarization determination) can be used to determine the excess of the enantiomer.

[0161] In thin-layer chromatography (TLC), the term R... f R represents the retention factor. f It is defined as the distance traveled by a single component divided by the total distance traveled by the eluent. Its value always lies between zero and one.

[0162] Salts and solvates (e.g., hydrates) of the compounds disclosed herein can also be used in the methods disclosed herein.

[0163] This disclosure covers the preparation and use of salts of the compounds of this disclosure. Salts of the compounds of this disclosure may be prepared during the final separation and purification of the compounds, or may be prepared separately by reacting the compounds with an acid having a suitable cation. Salts of the compounds of this disclosure may be acid addition salts formed with an acceptable acid. Examples of acids that can be used to form salts include inorganic acids (such as nitric acid, boric acid, hydrochloric acid, hydrobromic acid, sulfuric acid, and phosphoric acid) and organic acids (such as oxalic acid, maleic acid, succinic acid, tartaric acid, and citric acid). Non-limiting examples of salts of the compounds disclosed herein include, but are not limited to, hydrochlorides, hydrobroms, hydroiodates, sulfates, hydrogen sulfates, 2-hydroxyethanesulfonates, phosphates, hydrogen phosphates, acetates, adipates, alginates, aspartates, benzoates, hydrogen sulfates, butates, camphorates, camphor sulfonates, diglucose, glyceryl phosphates, hemisulfates, heptanates, hexanoates, formates, succinates, fumarates, maleates, ascorbic acid salts, hydroxyethyl sulfonates, salicylates, methanesulfonates, trimethylbenzenesulfonates, naphthalenesulfonates, nicotinates, 2-naphthalenesulfonates, oxalates, dihydroxynaphthaleneates, pectinates, persulfates, 3-phenylpropionates, picrates, neopentanoates, propionates, trichloroacetates, trifluoroacetates, phosphates, glutamates, bicarbonates, p-toluenesulfonates, undecanoates, lactates, citrates, tartrates, glucose, methanesulfonates, ethanesulfonates, benzenesulfonates, and p-toluenesulfonates. Furthermore, the amino groups in the compounds of this disclosure may be quaternized using the following: chlorides, bromides, and iodides of methyl, ethyl, propyl, and butyl groups; dimethyl sulfate, diethyl sulfate, dibutyl sulfate, and dipentyl sulfate; chlorides, bromides, and iodides of decyl, lauryl, myristyl, and stearoyl groups; and benzyl bromide and phenethyl bromide. In view of the foregoing, any reference to the compounds of this disclosure herein is intended to include the compounds of this disclosure as well as their salts, hydrates, or solvates.

[0164] This disclosure covers the preparation and use of solvates of the compounds of this disclosure. As used herein, the term "solvate" is a combination, physical association, and / or solvation of the compounds of this disclosure with solvent molecules, such as a disolvate, monosolvate, or hemisolvate, wherein the ratio of solvent molecules to the compounds of this disclosure is about 2:1, about 1:1, or about 1:2, respectively. Such physical association involves varying degrees of ionic and covalent bonding, including hydrogen bonding. In some cases, solvates can be separated, such as when one or more solvent molecules are incorporated into the lattice of a crystalline solid. Therefore, "solvate" encompasses both the solution phase and the separable solvate. The compounds of this disclosure can exist in a solvated form with solvents such as water, methanol, and ethanol, and this disclosure is intended to include both the solvated and unsolvated forms of the compounds of this disclosure.

[0165] One type of solvate is a hydrate. "Hydrate" is associated with a specific subset of solvates in which the solvent molecule is water. The preparation of solvates is known in the art. See, for example, M. Caira et al., J. Pharmaceut. Sci., 93(3):601-611 (2004), which describes the preparation of solvates of fluconazole with ethyl acetate and with water. Van Tonder et al., AAPS Pharm. Sci. Tech., 5(1): 12 (2004) and AL Bingham et al., Chem. Commun. 603-604 (2001) describe similar preparations of solvates, hemisolvates, hydrates, etc. Typical non-limiting methods for preparing solvates involve dissolving the compound of this disclosure in a desired solvent (organic solvent, water, or a mixture thereof) at a temperature above 20°C to about 25°C, then cooling the solution at a rate sufficient to form crystals, and separating the crystals by known methods (e.g., filtration). Analytical techniques such as infrared spectroscopy can be used to confirm the presence of solvent in solvate crystals.

[0166] Unless otherwise indicated, the terms “a,” “an,” and “the,” and similar pronouns used in the context of describing this disclosure (especially in the context of the claims) should be interpreted as encompassing both the singular and plural. Unless otherwise specified herein, descriptions of value ranges herein are intended only to serve as a shorthand for individually referring to each individual value falling within the range, and each individual value is incorporated into this specification as if individually described herein. Unless otherwise stated, the use of any and all example or exemplary language (e.g., “such”) provided herein is intended to better elucidate this disclosure and is not intended to limit the scope of this disclosure. No language in this specification should be construed as indicating any unclaimed element as necessary for practicing this disclosure.

[0167] Furthermore, the use of “and / or” herein should be understood as explicitly disclosing each of the two specified features or components with or without the other. Therefore, the term “and / or” as used in phrases such as “A and / or B” 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: 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).

[0168] It should be understood that when the term “contains” is used to describe an aspect wherever it is used in this document, other similar aspects described as “consisting of” and / or “substantially consisting of” are also provided.

[0169] As used herein, the term "wt / wt%" refers to the mass of a component in a composition or blend (e.g., a composition comprising a compound of the present disclosure and one or more elastomers); or a composition of the present disclosure and one or more fillers; or a blend comprising two or more elastomers, etc., divided by the combined mass of all components in the composition or blend multiplied by 100. For example, in a composition comprising 1 kg of the compound, 1 kg of natural rubber, and 2 kg of synthetic rubber, the wt / wt% of the compound of the present disclosure is 25 wt / wt% (1 kg / 4 kg = 0.25 × 100 = 25 wt / wt%). In a composition comprising 1 kg of the compound and 1 kg of carbon black, the wt / wt% of the compound of the present disclosure is 50 wt / wt% (1 kg / 2 kg = 0.50 × 100 = 50 wt / wt%). In a composition comprising 1 kg of the compound, 1 kg of natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black, the wt / wt% of the compound disclosed herein is 20 wt / wt% (1 kg / 5 kg = 0.20 × 100 = 20 wt / wt%). In a blend comprising 20 kg of natural rubber and 30 kg of synthetic rubber, the wt / wt% of the natural rubber is 40 wt / wt% (20 kg / 50 kg = 0.40 × 100 = 40 wt / wt%).

[0170] As used herein, the term "masterbatch" refers to a composition comprising at least one elastomer and a compound of the present disclosure. In some embodiments, the masterbatch comprises about 5 wt% to about 95 wt% of at least one elastomer and about 5 wt% to about 95 wt% of a compound of the present disclosure. In some embodiments, the masterbatch comprises about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt% of a compound of the present disclosure. In some embodiments, the masterbatch comprises at least one elastomer at about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0171] As used herein, the term "premix" refers to a composition comprising the compounds of this disclosure and at least one additional component (e.g., filler, rubber chemical, plasticizer, additional anti-degradation agent, or combination thereof). In some embodiments, the premix does not contain an elastomer. In some embodiments, the premix comprises about 5 wt% to about 95 wt% of the compounds of this disclosure and about 5 wt% to about 95 wt% of at least one additional component (e.g., filler, rubber chemical, plasticizer, additional anti-degradation agent, or combination thereof). In some embodiments, the premix comprises about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the compounds of this disclosure. In some embodiments, the premix comprises at least one additional component (e.g., filler, rubber chemicals, plasticizer, additional anti-degradation agent, or combination thereof) of about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0172] As used herein, the term "one or more" is intended to mean the presence of at least one component of the relevant category of components, such as one or more elastomers or at least one component from the disclosed list (e.g., one or more fluorine, chlorine, bromine, and / or iodine atoms), and in some embodiments, more than one component is present. In some embodiments, "one or more" means 1 to 50. In some embodiments, "one or more" means 1 to 40. In some embodiments, "one or more" means 1 to 30. In some embodiments, "one or more" means 1 to 20. In some embodiments, "one or more" means 1 to 10. In some embodiments, "one or more" means 1 to 5. In some embodiments, "one or more" means 1 to 3. In some embodiments, "one or more" means 1 or 2. In some embodiments, "one or more" means 1.

[0173] Composition and method of use

[0174] In another embodiment, this disclosure provides a composition comprising:

[0175] (i) the compounds disclosed herein; and

[0176] (ii) One or more elastomers; or

[0177] (iii) One or more fillers; or

[0178] (iv) One or more rubber chemicals; or

[0179] (v) One or more plasticizers; or

[0180] (vi) One or more other anti-degradation agents; or

[0181] (vii) A combination of the following: one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers and / or one or more additional anti-degradation agents.

[0182] In some embodiments, the composition comprises about 0.1 wt% to about 10 wt% of the compounds disclosed herein, for example, about 0.1 wt% to about 0.5 wt%, about 0.1 wt% to about 1 wt%, about 0.1 wt% to about 1.5 wt%, about 0.1 wt% to about 2 wt%, about 0.1 wt% to about 2.5 wt%, about 0.1 wt% to about 3 wt%, about 0.1 wt% to about 3.5 wt%, about 0.1 wt% to about 4 wt%, about 0.1 wt% to about 4.5 wt%, about 0.1 wt% to about 5 wt / wt%, about 0.1 wt / wt% to about 6 wt / wt%, about 0.1 wt / wt% to about 7 wt / wt%, about 0.1 wt / wt% to about 8 wt / wt%, about 0.1 wt / wt% to about 9 wt / wt%, about 0.1 wt / wt% to about 10 wt / wt%, about 0.5 wt / wt% to about 1 wt / wt%, about 0.5 wt / wt% to about 1.5 wt / wt%, about 0.5 wt / wt% to about 2 wt / wt%, about 0.5 wt / wt% to about 2.5 wt / wt%, about 0.5 wt / wt% to about 3 wt / wt%, about 0.5 wt / wt% to about 3.5 wt / wt%, about 0.5 wt / wt% to about 4 wt / wt% / wt%, about 0.5wt / wt% to about 4.5wt / wt%, about 0.5wt / wt% to about 5wt / wt%, about 0.5wt / wt% to about 6wt / wt%, about 0.5wt / wt% to about 7wt / wt%, about 0.5wt / wt% to about 8wt / wt%, about 0.5wt / wt% to about 9wt / wt%, about 0.5wt / wt% to about 10wt / wt%, about 1wt / wt% to about 2wt / wt%, about 1wt / wt% to about 2.5wt / wt%, about 1wt / wt% to about 3wt / wt%, about 1wt / wt% to about 3.5wt / wt%, about 1wt / wt% to about 4wt / wt%, about 1wt / wt% From about 4.5 wt / wt%, about 1 wt / wt% to about 5 wt / wt%, about 1 wt / wt% to about 6 wt / wt%, about 1 wt / wt% to about 7 wt / wt%, about 1 wt / wt% to about 8 wt / wt%, about 1 wt / wt% to about 9 wt / wt%, about 1 wt / wt% to about 10 wt / wt%, about 1.5 wt / wt% to about 2 wt / wt%, about 1.5 wt / wt% to about 2.5 wt / wt%, about 1.5 wt / wt% to about 3 wt / wt%, about 1.5 wt / wt% to about 3.5 wt / wt%, about 1.5 wt / wt% to about 4 wt / wt%, about 1.5 wt / wt% to about 4.5 wt / wt%, about 1.5 wt / wt% to about 5 wt / wt%, about 1.5 wt / wt% to about 6 wt / wt%, about 1.5 wt / wt% to about 7 wt / wt%, about 1.5 wt / wt% to about 8 wt / wt%, about 1.5 wt / wt% to about 9 wt / wt%, about 1.5 wt / wt% to about 10 wt / wt%, about 2 wt / wt% to about 2.5 wt / wt%, about 2 wt / wt% to about 3 wt / wt%, about 2 wt / wt% to about 3.5 wt / wt%, about 2 wt / wt% to about 4 wt / wt%, about 2 wt / wt% to about 4.5 wt / wt%, about 2 wt / wt% to about 5 wt / wt%, about 2 wt / wt% to about 6 wt / wt% t%, about 2wt / wt% to about 7wt / wt%, about 2wt / wt% to about 8wt / wt%, about 2wt / wt% to about 9wt / wt%, about 2wt / wt% to about 10wt / wt%, about 2.5wt / wt% to about 3wt / wt%, about 2.5wt / wt% to about 3.5wt / wt%, about 2.5wt / wt% to about 4wt / wt%, about 2.5wt / wt% to about 4.5wt / wt%, about 2.5wt / wt% to about 5wt / wt%, about 2.5wt / wt% to about 6wt / wt%, about 2.5wt / wt% to about 7wt / wt%, about 2.5wt / wt% to about 8wt / wt%, about 2.5wt / w t% to about 9 wt / wt%, about 2.5 wt / wt% to about 10 wt / wt%, about 3 wt / wt% to about 4 wt / wt%, about 3 wt / wt% to about 4.5 wt / wt%, about 3 wt / wt% to about 5 wt / wt%, about 3 wt / wt% to about 6 wt / wt%, about 3 wt / wt% to about 7 wt / wt%, about 3 wt / wt% to about 8 wt / wt%, about 3 wt / wt% to about 9 wt / wt%, about 3 wt / wt% to about 10 wt / wt%, about 3.5 wt / wt% to about 4 wt / wt%, about 3.5 wt / wt% to about 4.5 wt / wt%, about 3.5 wt / wt% to about 5 wt / wt%, about 3.5 w t / wt% to about 6wt / wt%, about 3.5wt / wt% to about 7wt / wt%, about 3.5wt / wt% to about 8wt / wt%, about 3.5wt / wt% to about 9wt / wt%, about 3.5wt / wt% to about 10wt / wt%, about 4wt / wt% to about 4.5wt / wt%, about 4wt / wt% to about 5wt / wt%, about 4wt / wt% to about 6wt / wt%, about 4wt / wt% to about 7wt / wt%, about 4wt / wt% to about 8wt / wt%, about 4wt / wt% to about 9wt / wt%, about 4wt / wt% to about 10wt / wt%, about 4.5wt / wt% to about 5wt / wt%, about 4.5 wt / wt% to about 6 wt / wt%, about 4.5 wt / wt% to about 7 wt / wt%, about 4.5 wt / wt% to about 8 wt / wt%, about 4.5 wt / wt% to about 9 wt / wt%, about 4.5 wt / wt% to about 10 wt / wt%, about 5 wt / wt% to about 6 wt / wt%, about 5 wt / wt% to about 7 wt / wt%, about 5 wt / wt% to about 8 wt / wt%, about 5 wt / wt% to about 9 wt / wt%, about 5 wt / wt% to about 10 wt / wt%, about The compounds of this disclosure in amounts of 6 wt / wt% to about 7 wt / wt%, about 6 wt / wt% to about 8 wt / wt%, about 6 wt / wt% to about 9 wt / wt%, about 6 wt / wt% to about 10 wt / wt%, about 7 wt / wt% to about 8 wt / wt%, about 7 wt / wt% to about 9 wt / wt%, about 8 wt / wt% to about 10 wt / wt%, about 8 wt / wt% to about 9 wt / wt%, about 8 wt / wt% to about 10 wt / wt%, or about 9 wt / wt% to about 10 wt / wt%.

[0183] In some embodiments, the compositions of this disclosure comprise about 15 wt% to about 85 wt% of the compounds of this disclosure. In some embodiments, the compositions comprise about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 25wt / wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 6 5wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% wt% to about 65wt / wt%, about 35wt / wt% to about 75wt / wt%, about 35wt / wt% to about 85wt / wt%, about 35wt / wt% to about 95wt / wt%, about 45wt / wt% to about 55wt / wt%, about 45wt / wt% to about 65wt / wt%, about 45wt / wt% to about 75wt / wt%, about 45wt / wt% to about 85wt / wt%, about 45wt / wt% to about 95wt / wt%, about 55wt / wt% to about 65wt / wt%, about 55wt / wt% to about 75wt / wt%, about 55wt / wt% to about 85wt / wt%.The compounds of this disclosure in approximately 55 wt / wt% to approximately 95 wt / wt%, approximately 65 wt / wt% to approximately 75 wt / wt%, approximately 65 wt / wt% to approximately 85 wt / wt%, approximately 65 wt / wt% to approximately 95 wt / wt%, approximately 75 wt / wt% to approximately 85 wt / wt%, approximately 75 wt / wt% to approximately 95 wt / wt%, or approximately 85 wt / wt% to approximately 95 wt / wt%.

[0184] In some embodiments, the compositions of this disclosure comprise about 50 wt / wt% of the compounds of this disclosure. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the compounds of this disclosure.

[0185] In another embodiment, the composition of this disclosure comprises the compound of this disclosure and one or more elastomers.

[0186] As used herein, the term "elastomer" is a polymer that is viscoelastic (i.e., possessing both viscosity and elasticity), typically exhibiting low intermolecular forces, low Young's modulus, and high breaking strain. Elastomers can generally be crosslinked by heating in the presence of one or more crosslinking agents; this process is known as curing or vulcanization. Rubber is a type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and blends thereof. As used herein, the term "natural rubber" refers to naturally occurring elastomers obtainable from the rubber tree (Hevea brasiliensis). Non-limiting types of synthetic rubber include unsaturated rubber, saturated rubber, rubber (FKM) having fluorine and fluoroalkyl or fluoroalkoxy substituents on the polymer chain, silicone rubber (Q), and blends thereof. Non-limiting examples of unsaturated rubbers include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions, which lead to hardening of aged components. With oxidation, these vulcanized rubbers harden and eventually become brittle products. Partial oxidation of vulcanized rubber results in performance loss in applications such as vehicle tire sidewalls. Saturated rubber is rubber that does not contain C=C unsaturation, and includes, but is not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxetine (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber with fluorine and fluoroalkyl or fluoroalkoxy substituents on the polymer chain (FKM), silicone rubber (Q), and blends thereof.

[0187] In some embodiments, the natural rubber comprises rubber derived from alternative rubber plants. As used herein, the term "natural rubber comprises rubber derived from alternative rubber plants" refers to a natural elastomer that can be obtained from a "non-Hevea brasiliensis" source. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0188] In some embodiments, one or more elastomers further comprise recycled rubber. As used herein, the term "recycled rubber" refers to an elastomer recovered from waste materials such as waste tires.

[0189] In some embodiments, the compositions disclosed herein comprise about 15 wt% to about 85 wt% of one or more elastomers. In some embodiments, the compositions comprise about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about [missing information - likely a percentage]. 25wt / wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 6 5wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% wt% to about 65wt / wt%, about 35wt / wt% to about 75wt / wt%, about 35wt / wt% to about 85wt / wt%, about 35wt / wt% to about 95wt / wt%, about 45wt / wt% to about 55wt / wt%, about 45wt / wt% to about 65wt / wt%, about 45wt / wt% to about 75wt / wt%, about 45wt / wt% to about 85wt / wt%, about 45wt / wt% to about 95wt / wt%, about 55wt / wt% to about 65wt / wt%, about 55wt / wt% to about 75wt / wt%, about 55wt / wt% to about 85wt / wt%.One or more elastomers comprising about 55 wt% to about 95 wt% , about 65 wt% to about 75 wt% , about 65 wt% to about 85 wt% , about 65 wt% to about 95 wt% , about 75 wt% to about 85 wt% , about 75 wt% to about 95 wt% , or about 85 wt% to about 95 wt% .

[0190] In some embodiments, the compositions of this disclosure comprise about 50 wt / wt% of one or more elastomers. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more elastomers.

[0191] As used herein, the term "phr" refers to the number of parts per 100 parts by weight of rubber. Parts by weight of a single component are based on 100 parts by weight of the total mass of one or more elastomers present in the composition.

[0192] In some embodiments, the compositions of this disclosure comprise about 1 phr to about 5 phr of the compound of this disclosure. In some embodiments, the compositions comprise about 0.01 phr to about 0.1 phr, about 0.01 phr to about 0.5 phr, about 0.01 phr to about 1 phr, about 0.01 phr to about 2 phr, about 0.01 phr to about 3 phr, about 0.01 phr to about 4 phr, about 0.01 phr to about 5 phr, about 0.01 phr to about 7.5 phr, about 0.01 phr to about 10 phr, or about 0.01 phr. From approximately 20 phr, from approximately 0.1 phr to approximately 0.5 phr, from approximately 0.1 phr to approximately 1 phr, from approximately 0.1 phr to approximately 2 phr, from approximately 0.1 phr to approximately 3 phr, from approximately 0.1 phr to approximately 4 phr, from approximately 0.1 phr to approximately 5 phr, from approximately 0.1 phr to approximately 7.5 phr, from approximately 0.1 phr to approximately 10 phr, from approximately 0.1 phr to approximately 20 phr, from approximately 1 phr to approximately 2 phr, from approximately 1 phr to approximately 3 phr, from approximately 1 phr hr to about 4 phr, about 1 phr to about 7.5 phr, about 1 phr to about 10 phr, about 1 phr to about 20 phr, about 2 phr to about 3 phr, about 2 phr to about 4 phr, about 2 phr to about 5 phr, about 2 phr to about 7.5 phr, about 2 phr to about 10 phr, about 2 phr to about 20 phr, about 3 phr to about 4 phr, about 3 phr to about 5 phr, about 3 phr to about 7.5 phr, about 3 phr The compounds of this disclosure in the form of hr to about 10 phr, about 3 phr to about 20 phr, about 4 phr to about 5 phr, about 4 phr to about 7.5 phr, about 4 phr to about 10 phr, about 4 phr to about 20 phr, about 5 phr to about 7.5 phr, about 5 phr to about 10 phr, about 5 phr to about 20 phr, about 7.5 phr to about 10 phr, about 7.5 phr to about 20 phr, or about 10 phr to about 20 phr.

[0193] In some embodiments, the compositions of this disclosure comprise about 3 phr of the compounds of this disclosure. In some embodiments, the compositions comprise about 0.01 phr, about 0.1 phr, and about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of the compounds of this disclosure.

[0194] In some embodiments, the compositions of this disclosure comprise the compounds of this disclosure and one or more fillers.

[0195] As used herein, the term "filler" is a substance that reinforces an elastomer composition or imparts other properties to an elastomer composition, including but not limited to increasing the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fibers (HCF), graphite, graphene, aluminosilicates, starch, and fibers, as well as combinations thereof.

[0196] In some implementations, the filler is derived from a natural source. For example, silica can be derived from rice husks.

[0197] In some embodiments, the compositions disclosed herein comprise about 15 wt% to about 85 wt% of one or more fillers. In some embodiments, the compositions comprise about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 25wt / wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 6 5wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% wt% to about 65wt / wt%, about 35wt / wt% to about 75wt / wt%, about 35wt / wt% to about 85wt / wt%, about 35wt / wt% to about 95wt / wt%, about 45wt / wt% to about 55wt / wt%, about 45wt / wt% to about 65wt / wt%, about 45wt / wt% to about 75wt / wt%, about 45wt / wt% to about 85wt / wt%, about 45wt / wt% to about 95wt / wt%, about 55wt / wt% to about 65wt / wt%, about 55wt / wt% to about 75wt / wt%, about 55wt / wt% to about 85wt / wt%.One or more fillers comprising about 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt%.

[0198] In some embodiments, the compositions of this disclosure comprise about 50 wt / wt% of one or more fillers. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more fillers.

[0199] In some embodiments, the compositions of this disclosure comprise one or more fillers of about 30 phr to about 500 phr. In some embodiments, the compositions comprise about 30 phr to about 50 phr, about 30 phr to about 100 phr, about 30 phr to about 150 phr, about 30 phr to about 200 phr, about 30 phr to about 250 phr, about 30 phr to about 300 phr, about 30 phr to about 350 phr, about 30 phr to about 400 phr, about 30 phr to about 450 phr, about 30 phr to about 500 phr, about 50 phr to about 100 phr, about 50 phr to about 150 phr, about 50 phr to about 200 phr, about 50 phr to about 250 phr. phr, approximately 50 phr to approximately 300 phr, approximately 50 phr to approximately 350 phr, approximately 50 phr to approximately 400 phr, approximately 50 phr to approximately 450 phr, approximately 50 phr to approximately 500 phr, approximately 100 phr to approximately 150 phr, approximately 100 phr to approximately 200 phr, approximately 100 phr to approximately 250 phr, approximately 100 phr to approximately 300 phr, approximately 100 phr to approximately 350 phr, approximately 100 phr to approximately 400 phr, approximately 100 phr to approximately 450 phr, approximately 100 phr to approximately 500 phr, approximately 150 phr to approximately 200 phr r, approximately 150 phr to approximately 250 phr, approximately 150 phr to approximately 300 phr, approximately 150 phr to approximately 350 phr, approximately 150 phr to approximately 400 phr, approximately 150 phr to approximately 450 phr, approximately 150 phr to approximately 500 phr, approximately 200 phr to approximately 250 phr, approximately 200 phr to approximately 300 phr, approximately 200 phr to approximately 350 phr, approximately 200 phr to approximately 400 phr, approximately 200 phr to approximately 450 phr, approximately 200 phr to approximately 500 phr, approximately 250 phr to approximately 300 phr, approximately 250 phr to approximately 350 phr One or more fillers of 0 phr, about 250 phr to about 400 phr, about 250 phr to about 450 phr, about 250 phr to about 500 phr, about 300 phr to about 350 phr, about 300 phr to about 400 phr, about 300 phr to about 450 phr, about 300 phr to about 500 phr, about 350 phr to about 400 phr, about 350 phr to about 450 phr, about 350 phr to about 500 phr, about 400 phr to about 450 phr, about 400 phr to about 500 phr, or about 450 phr to about 500 phr.

[0200] In some embodiments, the compositions disclosed herein comprise one or more fillers of about 300 phr. In some embodiments, the compositions comprise one or more fillers of about 30 phr, about 50 phr, about 100 phr, about 150 phr, about 200 phr, about 250 phr, about 350 phr, about 400 phr, about 450 phr, or about 500 phr.

[0201] In some embodiments, the compositions of this disclosure comprise the compounds of this disclosure and one or more rubber chemicals. As used herein, the term "rubber chemical" refers to a compound or substance used to promote the vulcanization of rubber. Rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and pre-vulcanization inhibitors.

[0202] As used herein, the term "vulcanization" refers to the process by which cross-links are formed between elastomers, influencing changes in the material properties of the elastomers. Specifically, vulcanization typically improves the stiffness and durability of elastomers. Vulcanization is carried out at room temperature or high temperatures, depending on the nature of the elastomers, fillers, and rubber chemicals used. The term "curing" is also used in the art to describe this process.

[0203] As used herein, the term "vulcanizing agent" refers to any substance that enables crosslinking between elastomers. Vulcanizing agents can enable crosslinking between individual polymer chains of an elastomer through various mechanisms, including but not limited to forming covalent bonds between the vulcanizing agent and two or more individual polymer chains, or generating free radical species on individual polymer chains that can combine to form covalent bonds between two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, sulfurized vegetable oils, ointments, and resins. Non-limiting examples of sulfur include octasulfur (S8) and cyclododecyl sulfate (S2). 12 ), and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne (2,5-Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di(tert-butylperoxy) valerate (VAL), and 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC). Non-limiting examples of resins include adhesive resins. As used herein, the term "adhesive resin" refers to chemicals that react with methylene donors, such as hexamethylenetetramine (HMTA) or hexamethoxymethyl melamine (HMMM), to promote adhesion, such as resorcinol-formaldehyde resins and phenolic resins.

[0204] As used herein, the term "accelerator" refers to any substance that increases the kinetics of vulcanization. In some embodiments, accelerators enable vulcanization to be carried out at lower temperatures and / or more efficiently utilize the vulcanizing agent (e.g., sulfur). Non-limiting examples of accelerators include guanidine, thiazoles, sulfinamides, thiuram, dithiocarbamates, xanthates, and thiophosphates. Non-limiting examples of guanidine include diphenylguanidine (DPG). Non-limiting examples of thiazoles include 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), and N-tert-butyl-2-benzothiazole sulfinamide (TBSI). Non-limiting examples of sulfinamides include N-tert-butyl-2-benzothiazole sulfinamide (TBBS), N-cyclohexylbenzothiazole-2-sulfinamide (CBS), dicyclohexyl-2-benzothiazole sulfinamide (DCBS), N-oxydiethylbenzothiazole sulfinamide (OBTS), N-oxydiethylthiocarbamoyl-N'-oxydiethylbenzothiazole sulfinamide (OTOS), and thiocarbamoyl sulfinamide. Non-limiting examples of thiuram include dimethylthiocarbamate dithioperoxyanhydride (thiram), bispentamethylene thiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyl dithiocarbamate (ZDMC), zinc diethyl dithiocarbamate (ZDEC), zinc dibutyl dithiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyl dithiocarbamate (SDEC), tellurium diethyl dithiocarbamate (TDEC), and zinc dibenzyl dithiocarbamate (ZEBC).

[0205] As used herein, the term "activator" refers to any substance that activates a vulcanizing agent and enables it to crosslink an elastomer as described above. Activators can function through a variety of mechanisms, including but not limited to forming chemical complexes with a promoter or coordinating with sulfur (when sulfur is used as a vulcanizing agent). Non-limiting examples of activators include metal oxides, acids, and metal complexes. Non-limiting examples of metal oxides include zinc oxide, magnesium oxide, and lead oxide. Non-limiting examples of acids include stearic acid and lauric acid. Non-limiting examples of metal complexes include zinc ethylhexanoate.

[0206] As used herein, the term "pre-vulcanization inhibitor" refers to a compound that delays the onset and / or rate of vulcanization. These compounds are also referred to as "restrictors". Non-limiting examples of pre-vulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0207] In some embodiments, the compositions disclosed herein comprise about 15 wt% to about 85 wt% of one or more rubber chemicals. In some embodiments, the compositions comprise about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about [missing information - likely a percentage] 25wt / wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 6 5wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% wt% to about 65wt / wt%, about 35wt / wt% to about 75wt / wt%, about 35wt / wt% to about 85wt / wt%, about 35wt / wt% to about 95wt / wt%, about 45wt / wt% to about 55wt / wt%, about 45wt / wt% to about 65wt / wt%, about 45wt / wt% to about 75wt / wt%, about 45wt / wt% to about 85wt / wt%, about 45wt / wt% to about 95wt / wt%, about 55wt / wt% to about 65wt / wt%, about 55wt / wt% to about 75wt / wt%, about 55wt / wt% to about 85wt / wt%.One or more rubber chemicals, expressed in quantities of about 55 wt% to about 95 wt%; about 65 wt% to about 75 wt%; about 65 wt% to about 85 wt%; about 65 wt% to about 95 wt%; about 75 wt% to about 85 wt%; about 75 wt% to about 95 wt%; or about 85 wt% to about 95 wt%.

[0208] In some embodiments, the compositions disclosed herein comprise about 15 wt / wt% of one or more rubber chemicals. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more rubber chemicals.

[0209] In some embodiments, the compositions disclosed herein comprise one or more rubber chemicals of about 1 phr to about 20 phr. In some embodiments, the composition comprises about 0.1 phr to about 1 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 10 phr, about 0.1 phr to about 15 phr, about 0.1 phr to about 20 phr, about 0.1 phr to about 25 phr, about 0.1 phr to about 30 phr, about 0.1 phr to about 35 phr, about 0.1 phr to about 40 phr, about 1 phr to about 5 phr, about 1 phr to about 10 phr, about 1 phr to about 15 phr, about 1 phr to about 25 phr, about 1 phr to about 30 phr, about 1 phr to about 35 phr, about 1 phr to about 40 phr, about 5 phr to about 10 phr, about 5 phr to about 15 phr, about 5 phr to about 20 phr, about 5 phr to about 25 phr, about 5 phr to about 30 phr, about 5 phr to about 35 phr. Approximately 5 phr to approximately 40 phr, approximately 10 phr to approximately 15 phr, approximately 10 phr to approximately 20 phr, approximately 10 phr to approximately 25 phr, approximately 10 phr to approximately 30 phr, approximately 10 phr to approximately 35 phr, approximately 10 phr to approximately 40 phr, approximately 15 phr to approximately 20 phr, approximately 15 phr to approximately 25 phr, approximately 15 phr to approximately 30 phr, approximately 15 phr to approximately 35 phr, approximately 15 phr One or more rubber chemicals of about 40 phr, about 20 phr to about 25 phr, about 20 phr to about 30 phr, about 20 phr to about 35 phr, about 20 phr to about 40 phr, about 25 phr to about 30 phr, about 25 phr to about 35 phr, about 25 phr to about 40 phr, about 30 phr to about 35 phr, about 30 phr to about 40 phr, or about 35 phr to about 40 phr.

[0210] In some embodiments, the compositions disclosed herein comprise about 10 phr of one or more rubber chemicals. In some embodiments, the compositions comprise about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr of one or more rubber chemicals.

[0211] As used herein, the term "plasticizer" refers to a processing aid used to reduce viscosity, improve plasticity, and / or increase the volume of a composition. Plasticizers facilitate mixing and the formation of a composition containing an elastomer before the composition is vulcanized. Non-limiting examples of plasticizers include mineral oils (paraffin, aromatic, or naphthenic), organic esters, resins, waxes, ester plasticizers, and naturally derived oils such as soybean oil, vegetable oil, or orange oil.

[0212] In some embodiments, the compositions disclosed herein comprise about 15 wt% to about 85 wt% of one or more plasticizers. In some embodiments, the compositions comprise about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 25wt / wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 6 5wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% wt% to about 65wt / wt%, about 35wt / wt% to about 75wt / wt%, about 35wt / wt% to about 85wt / wt%, about 35wt / wt% to about 95wt / wt%, about 45wt / wt% to about 55wt / wt%, about 45wt / wt% to about 65wt / wt%, about 45wt / wt% to about 75wt / wt%, about 45wt / wt% to about 85wt / wt%, about 45wt / wt% to about 95wt / wt%, about 55wt / wt% to about 65wt / wt%, about 55wt / wt% to about 75wt / wt%, about 55wt / wt% to about 85wt / wt%.One or more plasticizers comprising about 55 wt% to about 95 wt% , about 65 wt% to about 75 wt% , about 65 wt% to about 85 wt% , about 65 wt% to about 95 wt% , about 75 wt% to about 85 wt% , about 75 wt% to about 95 wt% , or about 85 wt% to about 95 wt% .

[0213] In some embodiments, the compositions of this disclosure comprise about 15 wt / wt% of one or more plasticizers. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more plasticizers.

[0214] In some embodiments, the compositions disclosed herein comprise one or more plasticizers of about 1 phr to about 20 phr. In some embodiments, the composition comprises about 0.1 phr to about 1 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 10 phr, about 0.1 phr to about 15 phr, about 0.1 phr to about 20 phr, about 0.1 phr to about 25 phr, about 0.1 phr to about 30 phr, about 0.1 phr to about 35 phr, about 0.1 phr to about 40 phr, about 1 phr to about 5 phr, about 1 phr to about 10 phr, about 1 phr to about 15 phr, about 1 phr to about 25 phr, about 1 phr to about 30 phr, about 1 phr to about 35 phr, about 1 phr to about 40 phr, about 5 phr to about 10 phr, about 5 phr to about 15 phr, about 5 phr to about 20 phr, about 5 phr to about 25 phr, about 5 phr to about 30 phr, and about 5 phr to about 35 phr. Approximately 5 phr to approximately 40 phr, approximately 10 phr to approximately 15 phr, approximately 10 phr to approximately 20 phr, approximately 10 phr to approximately 25 phr, approximately 10 phr to approximately 30 phr, approximately 10 phr to approximately 35 phr, approximately 10 phr to approximately 40 phr, approximately 15 phr to approximately 20 phr, approximately 15 phr to approximately 25 phr, approximately 15 phr to approximately 30 phr, approximately 15 phr to approximately 35 phr, approximately 15 phr One or more plasticizers of about hr to about 40 phr, about 20 phr to about 25 phr, about 20 phr to about 30 phr, about 20 phr to about 35 phr, about 20 phr to about 40 phr, about 25 phr to about 30 phr, about 25 phr to about 35 phr, about 25 phr to about 40 phr, about 30 phr to about 35 phr, about 30 phr to about 40 phr, or about 35 phr to about 40 phr.

[0215] In some embodiments, the compositions disclosed herein comprise one or more plasticizers at about 10 phr. In some embodiments, the compositions comprise one or more plasticizers at about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr.

[0216] In some embodiments, the compositions of this disclosure further comprise one or more additional anti-degradation agents that are not compounds of this disclosure. In some embodiments, the one or more additional anti-degradation agents are antioxidants. In some embodiments, the one or more additional anti-degradation agents are anti-ozone agents. Non-limiting examples of anti-degradation agents include p-phenylenediamine (PPD), trimethyl-dihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), diphenylamine-ketone condensates, and natural anti-degradation agents. Non-limiting examples of PPD include N... 1 -(4-Methylpent-2-yl)-N 4 -Phenylenyl-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N 1 -Phenyl-N 4 -(propyl-2-yl)phenyl-1,4-diamine (IPPD), N,N'-disec-butyl-p-phenylenediamine (44PD), N,N'-bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD) and N,N'-dioctyl-p-phenylenediamine (88PD). Non-limiting examples of TMQ include 2,2,4-trimethyl-1,2-dihydroquinoline and its oligomers or polymers.

[0217] In some embodiments, the compositions of this disclosure comprise about 15 wt% to about 85 wt% of one or more additional anti-degradation agents. In some embodiments, the compositions comprise about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 25wt / wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 6 5wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% wt% to about 65wt / wt%, about 35wt / wt% to about 75wt / wt%, about 35wt / wt% to about 85wt / wt%, about 35wt / wt% to about 95wt / wt%, about 45wt / wt% to about 55wt / wt%, about 45wt / wt% to about 65wt / wt%, about 45wt / wt% to about 75wt / wt%, about 45wt / wt% to about 85wt / wt%, about 45wt / wt% to about 95wt / wt%, about 55wt / wt% to about 65wt / wt%, about 55wt / wt% to about 75wt / wt%, about 55wt / wt% to about 85wt / wt%.One or more additional anti-degradation agents, comprising about 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt%.

[0218] In some embodiments, the compositions of this disclosure comprise about 15 wt / wt% of one or more additional anti-degradation agents. In some embodiments, the compositions comprise about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more additional anti-degradation agents.

[0219] In some embodiments, the compositions of this disclosure comprise one or more additional anti-degradation agents in amounts of about 1 phr to about 5 phr. In some embodiments, the compositions comprise amounts of about 0.001 phr to about 0.01 phr, about 0.001 phr to about 0.1 phr, about 0.001 phr to about 1 phr, about 0.001 phr to about 5 phr, about 0.001 phr to about 7.5 phr, about 0.001 phr to about 10 phr, about 0.01 phr to about 0.1 phr, about 0.01 phr to about 1 phr, about 0.01 phr to about 5 phr, about 0. One or more other anti-degradation agents of about 0.1 phr to about 7.5 phr, about 0.01 phr to about 10 phr, about 0.1 phr to about 1 phr, about 0.1 phr to about 5 phr, about 0.1 phr to about 7.5 phr, about 0.1 phr to about 10 phr, about 1 phr to about 7.5 phr, about 1 phr to about 10 phr, about 5 phr to about 7.5 phr, about 5 phr to about 10 phr, or about 7.5 phr to about 10 phr.

[0220] In some embodiments, the compositions disclosed herein comprise one or more additional anti-degradation agents at about 3 phr. In some embodiments, the compositions comprise one or more additional anti-degradation agents at about 0.001 phr, about 0.01 phr, about 0.1 phr, about 1 phr, about 2 phr, about 4 phr, about 5 phr, about 7.5 phr, or about 10 phr.

[0221] In some embodiments, this disclosure provides a composition comprising a compound of this disclosure and one or more supports. As used herein, the term "support" refers to a solid capable of adsorbing liquids while retaining the general properties of a solid at room temperature. In some embodiments, the support is an inert material. In some embodiments, the support has a high surface area. In some embodiments, the support comprises particles having a diameter of less than 500 micrometers.

[0222] In some embodiments, the composition comprises about 15 wt% to about 85 wt% of one or more carriers. In some embodiments, the composition comprises about 1 wt% to about 5 wt%, about 1 wt% to about 15 wt%, about 1 wt% to about 25 wt%, about 1 wt% to about 35 wt%, about 1 wt% to about 45 wt%, about 1 wt% to about 55 wt%, about 1 wt% to about 65 wt%, about 1 wt% to about 75 wt%, about 1 wt% to about 85 wt%, about 1 wt% to about 95 wt%, about 5 wt% to about 15 wt%, about 5 wt% to about 25 wt%. wt%, about 5wt / wt% to about 35wt / wt%, about 5wt / wt% to about 45wt / wt%, about 5wt / wt% to about 55wt / wt%, about 5wt / wt% to about 65wt / wt%, about 5wt / wt% to about 75wt / wt%, about 5wt / wt% to about 85wt / wt%, about 5wt / wt% to about 95wt / wt%, about 15wt / wt% to about 25wt / wt%, about 15wt / wt% to about 35wt / wt%, about 15wt / wt% to about 45wt / wt%, about 15wt / wt% to about 55wt / wt%, about 15wt / wt% to about 65wt / wt%, about 1 5 wt / wt% to about 75 wt / wt%, about 15 wt / wt% to about 95 wt / wt%, about 25 wt / wt% to about 35 wt / wt%, about 25 wt / wt% to about 45 wt / wt%, about 25 wt / wt% to about 55 wt / wt%, about 25 wt / wt% to about 65 wt / wt%, about 25 wt / wt% to about 75 wt / wt%, about 25 wt / wt% to about 85 wt / wt%, about 25 wt / wt% to about 95 wt / wt%, about 35 wt / wt% to about 45 wt / wt%, about 35 wt / wt% to about 55 wt / wt%, about 35 wt / wt% to about 65 wt / wt%, about 35 wt / wt% to about 75 wt / wt%, about 35 wt / wt% to about 85 wt / wt%, about 35 wt / wt% to about 95 wt / wt%, about 45 wt / wt% to about 55 wt / wt%, about 45 wt / wt% to about 65 wt / wt%, about 45 wt / wt% to about 75 wt / wt%, about 45 wt / wt% to about 85 wt / wt%, about 45 wt / wt% to about 95 wt / wt%, about 55 wt / wt% to about 65 wt / wt%, about 55 wt / wt% to about 75 wt / wt%, about 55 wt / wt% to about 85 wt / wt%, about 55 wt / wt% to about 95 wt / wt%.One or more carriers, comprising approximately 65 wt / wt% to approximately 75 wt / wt%, approximately 65 wt / wt% to approximately 85 wt / wt%, approximately 65 wt / wt% to approximately 95 wt / wt%, approximately 75 wt / wt% to approximately 85 wt / wt%, approximately 75 wt / wt% to approximately 95 wt / wt%, or approximately 85 wt / wt% to approximately 95 wt / wt%.

[0223] In some embodiments, the composition comprises about 15 wt / wt% of one or more carriers. In some embodiments, the composition comprises about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of one or more carriers.

[0224] This disclosure also provides a method for preparing a composition comprising the compound of this disclosure and one or more supports, the method comprising mixing the compound with one or more supports.

[0225] This disclosure also provides lubricant compositions comprising the compounds of this disclosure and lubricants. Non-limiting examples of lubricants include mineral oils, high molecular weight petroleum fractions (such as aromatic, naphthenic, and paraffinic fractions), synthetic oils (such as polyalphaolefins (PAO)), synthetic esters, polyalkylene glycols (PAG), phosphate esters, perfluoropolyethers (PFPE), alkylated naphthalenes (AN), silicates, ion fluids and polyalkylated cyclopentanes (MAC), solid lubricants (such as polytetrafluoroethylene (PTFE), graphite, hexagonal boron nitride, molybdenum disulfide, and tungsten disulfide), waterborne lubricants (such as hydrated brush polymers), and bio-lubricants (such as triglycerides, high-oleic rapeseed oil, castor oil, palm oil, sunflower oil, and rapeseed oil).

[0226] This disclosure also provides combustible fuel compositions comprising a combustible fuel and compounds of this disclosure. Non-limiting examples of combustible fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0227] This disclosure also provides fuel additive compositions comprising fuel additives and compounds of this disclosure. Non-limiting examples of fuel additives include oxygenators (such as alcohols and ethers), antioxidants, stabilizers, detergents, antiknock agents, lead removers, fuel dyes, viscosity modifiers, and butyl rubber. In some embodiments, the butyl rubber is in the form of polyisobutylene succinimide. In some embodiments, butyl rubber is added as a detergent to prevent scale buildup on diesel fuel injectors.

[0228] In some embodiments, this disclosure provides the compositions described in Table 2.

[0229] Table 2

[0230]

[0231] In some embodiments, the vulcanized tire or other rubber article compositions of Table 2 comprise about 0.1 wt / wt%, about 0.2 wt / wt%, about 0.3 wt / wt%, about 0.4 wt / wt%, about 0.5 wt / wt%, about 0.6 wt / wt%, about 0.7 wt / wt%, about 0.8 wt / wt%, about 0.9 wt / wt%, about 1 wt / wt%, about 2 wt / wt%, about 3 wt / wt%, about 4 wt / wt%, about 5 wt / wt%, about 6 wt / wt%, about 7 wt / wt%, about 8 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of the compounds of this disclosure. In some embodiments, the vulcanized tire or other rubber article compositions of Table 2 comprise at least one elastomer comprising about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0232] In some embodiments, the uncured tire internal components or other end-use component compositions of Table 2 comprise about 0.01 wt / wt%, about 0.02 wt / wt%, about 0.03 wt / wt%, about 0.04 wt / wt%, about 0.05 wt / wt%, about 0.06 wt / wt%, about 0.07 wt / wt%, about 0.08 wt / wt%, about 0.09 wt / wt%, about 0.1 wt / wt%, about 0.2 wt / wt%, about 0.3 wt / wt%, about 0.4 wt / wt%, about 0.5 wt / wt%, about 0.6 wt / wt%, about 0.7 wt / wt%, about 0.8 wt / wt%, about 0.9 wt / wt%, about 1 wt / wt%, about 2 wt / wt%, about 3 wt / wt%, about 4 wt / wt%, about 5 wt / wt%, about 6 wt / wt%, about 7 wt / wt%, about 8 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of the compounds of this disclosure. In some embodiments, the uncured tire internal components or other end-use component compositions in Table 2 comprise at least one elastomer comprising about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt%.

[0233] Vulcanized elastomer products

[0234] This disclosure also provides vulcanized elastomer articles comprising compounds of this disclosure. The term "vulcanized elastomer article" refers to an article made by forming a composition comprising an elastomer into a particular shape and vulcanizing the composition to provide an article.

[0235] This disclosure also provides vulcanized elastomer articles prepared using the compositions described herein.

[0236] In some embodiments, the vulcanized elastomer product is a tire. In some embodiments, the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

[0237] In some embodiments, the vulcanized elastomer article is a component of the tire. In some embodiments, the component is a bead, belt, body ply, liner, sidewall, bottom tread, or tread layer.

[0238] In some implementations, vulcanized elastomer products are rubber overshoes, sealing strips, sound insulation panels, air springs, bellows, membranes, tactile sensors, anti-collision pads, hoses, conveyor belts, or flooring.

[0239] method

[0240] This disclosure also provides a method for preparing vulcanized elastomer articles, the method comprising:

[0241] (a) Forming the composition described herein into a shaped form; and

[0242] (b) Vulcanize the formed shape.

[0243] To provide vulcanized elastomer products.

[0244] In some embodiments, vulcanization is carried out at an average temperature of about 140°C to about 160°C. In some embodiments, vulcanization is carried out at an average temperature of about 80°C to about 100°C, about 80°C to about 120°C, about 80°C to about 140°C, about 80°C to about 160°C, about 80°C to about 180°C, about 80°C to about 200°C, about 100°C to about 120°C, about 100°C to about 140°C, about 100°C to about 160°C, about 100°C to about 180°C, about 100°C to about 200°C, about 120°C to about 140°C, about 120°C to about 160°C, about 120°C to about 200°C, about 140°C to about 180°C, about 140°C to about 200°C, about 160°C to about 180°C, about 160°C to about 200°C, or about 180°C to about 200°C.

[0245] In some embodiments, vulcanization is carried out at an average temperature of about 150°C. In some embodiments, vulcanization is carried out at an average temperature of about 80°C, about 100°C, about 120°C, about 140°C, about 160°C, about 180°C, or about 200°C.

[0246] This disclosure also provides a method for retreading tires, the method comprising:

[0247] (a) Applying the composition described herein to a tire;

[0248] (b) A pre-cured tread is placed around the tire;

[0249] (c) Applying a cured coating around the tire; and

[0250] (d) Vulcanize the tire.

[0251] Reagent test kit

[0252] This disclosure also provides kits comprising the compositions described herein, packaged, for example, in containers, which facilitate the use of the compositions to practice the processes and / or methods of this disclosure. In some embodiments, the kit comprises the compositions described herein and instructions for using the compositions in vulcanizable elastomer compositions. In some embodiments, the kit comprises the compositions described herein and instructions for using the compositions to prepare vulcanizable elastomer articles. The compositions may be packaged in any suitable container (such as a sealed bottle or vessel labeled) or included in a kit describing the compositions and their proper use.

[0253] Example

[0254] Example 1

[0255] Synthesis of N-isopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 1)

[0256] Step 1

[0257]

[0258] 2-Methyl-4-nitroaniline (30 g; 197 mmol) and acetonitrile (320 mL) were charged into a 1-L round-bottom flask equipped with a top stirrer, thermometer, and reflux condenser. The mixture was stirred under N2 protection. Trifluoroacetic acid (16.0 mL; 209 mmol), 37% formaldehyde aqueous solution (26.0 mL; 349 mmol HCHO), and α-methylstyrene (46.0 mL; 354 ​​mmol) were added sequentially to the resulting clear yellow solution. The reaction mixture (the slurry formed after the addition of formaldehyde) was refluxed for 2 hours (internal temperature = 77-78 °C), thus forming a clear yellow solution. Upon cooling to room temperature, 1 mol / L sodium bicarbonate aqueous solution (300 mL) was added in portions. The resulting two-phase system was stirred until CO2 production ceased, and then transferred to a 2-L separatory funnel. Ethyl acetate (700 mL) was added. After shaking and decanting, the aqueous phase was discarded. The organic phase was washed with 1 mol / L sodium bisulfite aqueous solution (300 mL) and saturated sodium chloride aqueous solution (300 mL), dried over anhydrous magnesium sulfate, filtered, and the volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting dark oily substance (69.5 g) was diluted with a mixture of isopropanol (100 mL) and hexane (20 mL). The mixture was rotated until homogeneous and then kept overnight at -20 °C, thus separating the yellow solid. The yellow solid was collected by vacuum filtration (disposable 20 μm polyethylene melt) and washed directly on the melt with hexane (50 mL). The wet material was dried in a vacuum oven at 45–50 °C for several hours and then overnight at room temperature to give 24.1 g of 4,8-dimethyl-6-nitro-4-phenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 1-I) as a yellow powder. Intermediate compound 1-I was obtained by... 1 H and 13 Characterized by C nuclear magnetic resonance (NMR) spectra, as follows: Figure 1 and 2 As shown. LC-UV analysis indicates a purity of 93.4% detected at 260 nm, as... Figure 3 As shown.

[0259] Step 2

[0260]

[0261] Intermediate compound 1-I (23.0 g; 81.5 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.4077 g wet), isopropanol (201 mL), and acetone (10.4 mL; 142 mmol) were charged into a 300 mL Parr autoclave. The reaction mixture was stirred and heated to 120 °C at 250 PSI H₂ for 1.5 hours. After cooling to room temperature, the resulting mixture was filtered through an inline 0.2 μm melt filter. The autoclave was rinsed with fresh isopropanol (approximately 200 mL), and the resulting mixture was filtered through an inline 0.2 μm melt filter. The combined filtrates were filtered through filter paper, and their volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting crude material (light brown oil) weighed 23.7 g. After standing at room temperature for several weeks, the oil solidified into a dark solid. After cooling to -20°C overnight, the solids were broken down with a spatula. A mixture of ethyl acetate and hexane (10 mL and 51 mL, respectively) was added to the resulting dark powder. The resulting slurry was magnetically stirred at room temperature for 4 days under N2 protection. The solids were collected by vacuum filtration onto a 0.2 μm melt of disposable polyethylene and quickly washed with several portions of hexane (50 mL in total). The wet powder (16.58 g) was dried under vacuum at 50–60°C for several hours, then overnight at room temperature to give 14.48 g of N-isopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 1) as a light brown powder (60% relative to intermediate compound 1-I). Compound 1 was obtained by... 13 Characterized by C NMR spectra, such as Figure 4 As shown. LC-UV analysis indicates a purity of 96.5% detected at 260 nm, as... Figure 5 As shown. Mass (m / z): 295.4 [M+1] + .

[0262] Example 2

[0263] Synthesis of 4,8-dimethyl-N-(pent-3-yl)-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 2)

[0264]

[0265] An intermediate compound 1-I (12.0 g; 42.5 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.42 g wet), 3-pentanone (180 mL; 1.70 mol), and 5 wt% aqueous phosphoric acid solution (1.8 g solution; 0.92 mmol H3PO4) were charged into a 300-mL Palermo-Pak autoclave. The reaction mixture was stirred and heated to 150 °C at 250 PSI H2 for 2 hours. After cooling to room temperature, the resulting mixture was filtered through an inline 0.2 μm melt filter. The autoclave was rinsed with isopropanol (approximately 150-200 mL), and the resulting mixture was filtered through an inline 0.2 μm melt filter. The volatiles in the combined filtrate were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting residue was dissolved in hexane (14 mL), thus separating trace amounts of insoluble material. The mixture was vacuum filtered through diatomaceous earth S and the filter cake was washed with hexane (100 mL). The volatiles in the combined filtrates were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The mixture was dried overnight under vacuum at 60 °C to give 12.5 g of a brown oil that darkened over time upon standing at room temperature, thus yielding 4,8-dimethyl-N-(pent-3-yl)-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 2). Compound 2 was obtained by... 13 CNMR spectra were used for characterization, such as Figure 6 As shown. LC-UV analysis indicates a purity of 91.0% detected at 260 nm, as... Figure 7 As shown. Mass (m / z): 323.4 [M+1] + .

[0266] Example 3

[0267] Synthesis of N-isopropyl-4,8-dimethyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 3)

[0268] Step 1

[0269]

[0270] 2-Methyl-4-nitroaniline (9.96 g; 65.5 mmol) and acetonitrile (200 mL) were charged into a 1-L round-bottom flask equipped with a stir bar, thermometer, and reflux condenser. The mixture was stirred under nitrogen protection. Trifluoroacetic acid (5.3 mL; 68.7 mmol), benzaldehyde (6.6 mL; 65.5 mmol), and α-methylstyrene (15.3 mL; 117.9 mmol) were added sequentially to the resulting clear yellow solution. The reaction mixture was heated to 82 °C (oil bath temperature) for 4 hours. Upon cooling to room temperature, a yellow precipitate formed. A solution of sodium bicarbonate (10 g) in deionized water (200 mL) was added in portions. Ethyl acetate (200 mL) was added in portions to dissolve the precipitate. The resulting two-phase system was transferred to a separatory funnel. The aqueous phase was discarded. The organic phase was washed with a solution of sodium bisulfite (15.0 g) in deionized water (200 mL) and a saturated sodium chloride aqueous solution (200 mL), dried over anhydrous magnesium sulfate, filtered, and the volatiles were stripped under reduced pressure (rotary evaporator; water bath = 45 °C). The residue was dried under vacuum at 45 °C to 20 mbar for 20 minutes. The resulting viscous orange oil was suspended in a 1:1 v / v isopropanol:hexane (100 mL) and heated to 55 °C for 15 minutes, at which point the orange oil turned into a yellow solid. The mixture was cooled to room temperature and then filtered to separate the yellow solid. The solid was washed with hexane (3 × 20 mL) and dried over a vacuum filter for approximately 20 minutes to give 15.2 g of 4,8-dimethyl-6-nitro-2,4-diphenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 3-I) as a yellow powder. LC-UV analysis indicated a purity of 99.0% at 260 nm. Figure 8 As shown.

[0271] Step 2

[0272]

[0273] Intermediate compound 3-I (10.6 g, 29.7 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.2467 g wet), isopropanol (200 mL), and acetone (5.6 mL, 75.5 mmol) were charged into a 300 mL Pal autoclave. The reaction mixture was stirred and heated to 150 °C at 250 PSI H₂ for 107 min. Upon cooling to room temperature, the mixture was filtered through an inline 0.2 μm melt filter, the reactor was washed with 100 mL of isopropanol, and the combined filtrates were removed under reduced pressure (rotary evaporator; water bath = 50 °C) to give a waxy beige solid (10.68 g). The solid was dried under vacuum at 55 °C for 16 h to give 9.27 g of N-isopropyl-4,8-dimethyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 3) as a waxy beige solid. Compound 3 via 13 Characterized by C NMR spectra, such as Figure 9 As shown. LC-UV analysis indicates a purity of 94.5% detected at 260 nm, as... Figure 10 As shown. Mass (m / z): 371.4 [M+1] + .

[0274] Example 4

[0275] Synthesis of N,2-diisopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 4)

[0276] Step 1

[0277]

[0278] 2-Methyl-4-nitroaniline (4.2 g; 27.6 mmol) and acetonitrile (50 mL) were added to a 250 mL flask equipped with a stir bar and a reflux condenser. The mixture was stirred under N2 protection (2-methyl-4-nitroaniline dissolved within minutes). Trifluoroacetic acid (2.2 mL; 28.7 mmol), isobutyraldehyde (4.4 mL; 48 mmol), and α-methylstyrene (6.4 mL; 49.2 mmol) were added sequentially to the resulting dark solution. The reaction mixture was heated (oil bath set to 80 °C). Once the set temperature was reached, it was maintained for 5 hours. After cooling to room temperature (overnight), sodium bicarbonate (4.75 g; 56.5 mmol) in a solution of deionized water (60 mL) was added in portions. The resulting two-phase system was stirred until CO2 production ceased, ethyl acetate (50 mL) was added, and the mixture was transferred to a separatory funnel. The flask was rinsed with ethyl acetate (2 × 20 mL). The organic solution was transferred to a separatory funnel. After decanting, the aqueous layer was discarded. The organic layer was washed with a saturated sodium bisulfite aqueous solution (30 mL), dried over MgSO4, filtered, and its volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). Excess α-methylstyrene was not stripped (BP = 165–169 °C). A mixture of hexane (20 mL) and isopropanol (10 mL) was added to the obtained impure orange oily substance weighing approximately 9.9 g. After rotating for a few seconds, the resulting solution was kept at -20 °C for 1 hour, thus separating a yellow crystalline solid and a dark, dense substance. When warmed to room temperature and vigorously rotated, the dark substance disappeared, and a further amount of yellow crystals formed. The solid was collected by vacuum filtration onto a 0.2 μm melt of disposable polyethylene and quickly washed with hexane (10 mL). The moist solid (2.87 g) was dried under vacuum at 50-60 °C for several hours, then at room temperature for several hours to give 2.78 g of 2-isopropyl-4,8-dimethyl-6-nitro-4-phenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 4-I) as a yellow powder. Intermediate compound 4-I was obtained by... 13 Characterized by C NMR spectra, such as Figure 11 As shown. LC-UV analysis indicates a purity of 95.2% detected at 260 nm, as... Figure 12 As shown.

[0279] Step 2

[0280]

[0281] An intermediate compound 4-I (1.6 g; 4.93 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.0366 g wet), isopropanol (130 mL), and acetone (0.99 mL; 13 mmol) were charged into a 300 mL Pal autoclave. The reaction mixture was stirred and heated to 150 °C at 250 PSI H₂ for 65–70 min. After cooling to room temperature, the resulting mixture was filtered through an inline 0.2 μm melt filter. The autoclave was rinsed with fresh isopropanol (150 mL), and the resulting mixture was filtered through an inline 0.2 μm melt filter. The volatiles in the combined filtrate were stripped under reduced pressure (rotary evaporator; water bath = 55 °C). The residue was dissolved in 40% ethyl acetate in hexane (5 mL). The obtained solution was packed into a 41 mm inner diameter column previously prepared with silica gel (ultrapure; 60 Å; 60–200 μm) and ethyl acetate in 20% hexane (silica gel height = 10–11 cm). An elution column of ethyl acetate in 20% hexane was used. Each fraction was analyzed by silica gel TLC (ethyl acetate in 20% hexane). R was collected. f Fractions of 0.3 were combined and their volatiles were stripped under reduced pressure (rotary evaporator; water bath = 55°C). The resulting light brown oil was dried under vacuum (rotary evaporator; water bath = 55°C; < 2 mbar) for 1.5 hours, then in a vacuum oven at 75–80°C overnight to give 1.4 g of a very viscous, transparent light orange oil, N,2-diisopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 4). Compound 4 was obtained by... 13 Characterized by C NMR spectra, such as Figure 13 As shown. LC-UV analysis indicates a purity of 97.2% detected at 260 nm, as... Figure 14 As shown. Mass (m / z): 337.4 [M+1] + .

[0282] Example 5

[0283] Synthesis of N-isopropyl-3,3,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 47)

[0284] Step 1

[0285]

[0286] 2-Methyl-4-nitroaniline (3.96 g; 26.0 mmol) and acetonitrile (42 mL) were charged into a 100 mL flask equipped with a stir bar and a reflux condenser. The mixture was stirred under N2 cover. To the resulting dark solution, p-toluenesulfonic acid monohydrate (0.486 g; 2.56 mmol acid), 37% formaldehyde aqueous solution (2.4 mL; 32.2 mmol HCHO), and isobutyraldehyde (3.7 mL; 41 mmol) were added sequentially. A yellow solid separated after the addition of the formaldehyde solution. The reaction mixture was stirred for 2 days without external cooling or heating to obtain a dark solution. Sodium bicarbonate (0.337 g; 4.01 mmol) was added, and the mixture was stirred for 5–10 minutes. Anhydrous magnesium sulfate was added, and the resulting slurry was stirred for about 5 minutes. Insoluble material was removed by gravimetric filtration through filter paper. The filter cake was washed with some acetonitrile. The volatiles in the filtrate were stripped under reduced pressure (rotary evaporator; water bath = 50°C). The crude material (6.35 g of moist yellow-orange solid) was ground in isopropanol (20 mL) with a scraper until all solids detached from the flask wall. The resulting slurry was magnetically stirred for 10–15 minutes. Hexane (20 mL) was added and the mixture was magnetically stirred for 30 minutes. The solids were collected by vacuum filtration onto a disposable 0.2 μm polyethylene melt and washed with several portions of hexane (total = 25 mL). The moist solids were dried under vacuum at approximately 50°C for several hours, then overnight at room temperature to give 3.09 g of crude 3,3,8-trimethyl-6-nitro-1,2,3,4-tetrahydroquinoline-4-ol (intermediate compound 47-I) as a yellow powder. Crude intermediate compound 47-I was obtained by… 13 Characterized by C APT NMR spectra, such as Figure 15 As shown. LC-UV analysis indicates a purity of approximately 61% detected at 260 nm, as... Figure 16 As shown. The crude material is used in subsequent steps without further purification.

[0287] Step 2

[0288]

[0289] Crude intermediate compound 47-I (2.8 g; < 11.9 mmol), toluene (140 mL), acetone (1.7 mL; 23.2 mmol), and 3% Pt / C sulfide (Johnson Matthey) (150 mg wet) were charged into a 300 mL Pal autoclave. The reaction mixture was stirred and heated to 120 °C at 250 PSI H₂ for 2 hours. After cooling to room temperature, the resulting mixture was filtered through an inline 0.2 μm melt filter. The autoclave was rinsed with isopropanol (130 mL), and the resulting mixture was filtered through an inline 0.2 μm melt filter. The volatiles in the combined filtrate were stripped under reduced pressure (rotary evaporator; water bath = 60 °C). The residue was dissolved in hexane (4 mL). The obtained solution was packed into a 41 mm inner diameter column previously prepared with silica gel (ultrapure; 60 Å; 60–200 μm) and ethyl acetate in 30% hexane (silica gel height = 16–17 cm). An elution column of ethyl acetate in 30% hexane was used. Each fraction was analyzed by silica gel TLC (ethyl acetate in 30% hexane). Fractions with Rf = 0.45 were collected, combined, and their volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting light brown oil was dried under vacuum (rotary evaporator; water bath = 55 °C; < 8 mbar) for 1.5 h to give 0.96 g of N-isopropyl-3,3,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 47) as a brown oil. Compound 47 was analyzed by… 13 Characterized by CAPT NMR spectra, such as Figure 17 As shown. LC-UV analysis indicates a purity of 94.6% detected at 260 nm, as... Figure 18 As shown. Mass (m / z): 233.3 [M+1] + .

[0290] Example 6

[0291] Oxidation-inducing time (OIT) performance of the compounds disclosed herein

[0292] The oxidation-induction time (OIT) of the selected compounds of this disclosure was evaluated. OIT was measured according to a procedure performed in a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, the sample was held in the cell and heated to a pre-selected temperature under a nitrogen atmosphere. Oxygen (O2) was then introduced into the cell and the length of time prior to the onset of degradation, as observed at the start of the endothermic process in the DSC trace, was measured.

[0293] 0.5 wt% of the compound N disclosed herein 1 -(4-Methylpent-2-yl)-N 41,4-phenylphenyl-1,4-diamine (6PPD) or without an anti-degradation agent (blank) was mixed with polyisoprene and isothermally heated in O2 at 150°C and / or 160°C. OIT (in minutes) is shown in Table 3. As indicated by the data in Table 3, the compounds of this disclosure exhibit antioxidant activity compared to the blank control.

[0294] The melting points of the compounds disclosed herein were also measured and are listed in Table 3.

[0295] Table 3

[0296]

[0297] The methods, compounds, and compositions described herein have now been fully described, and those skilled in the art will understand that they can be carried out within a wide and equivalent range of conditions, formulations, and other parameters without affecting the scope of the methods, compounds, and compositions provided herein or any embodiments thereof. All patents, patent applications, and publications cited herein are incorporated herein by reference in their entirety.

Claims

1. A compound having formula (I): （I）， Or its salts, solvates or stereoisomers, wherein: Is it a single bond or a double bond? R 1a Choose from the following groups: C1-C arbitrarily substituted 12 Alkyl, -CHR 1c R 1d C3-C6 cycloalkyl, 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; R 1b Select from the group consisting of hydrogen and C1-C9 alkyl groups; R 1c Choose from the group consisting of: optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5- or 6-membered heteroaryl; R 1d Select from the group consisting of hydrogen and C1-C9 alkyl groups; R 2a R 2b and R 2c Independently selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; or R 2b Choose from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; and R 2a and R 2c Together with the two carbon atoms they are attached to, they form C5-C8 cycloalkyl, 5- to 8-membered heterocyclic groups, or C5-C6 aryl groups; R 3a and R 3b Independently selected from the group consisting of: hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that if If it is a double bond, then R 3b Does not exist; or R 3a and R 3b Together with the carbon atoms they are attached to, they form C3-C. 12 cycloalkyl, under the condition that It is a single key; R 3c and R 3d Independently selected from the group consisting of: hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that if If it is a double bond, then R 3d Does not exist; or R 3c and R 3d Together with the carbon atoms they are attached to, they form C3-C. 12 cycloalkyl, under the condition that It is a single key; R 3e and R 3f Independently selected from the group consisting of: hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups, provided that R 3e and / or R 3f If it is hydrogen, then R 3c and R 3d Independently selected from the group consisting of: C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; or R 3e and R 3f Together with the carbon atoms they are attached to, they form C3-C. 12 cycloalkyl; R 3g Selected from the group consisting of hydrogen and C1-C9 alkyl groups; and R 4 and R 5 Each time it appears, it is independently selected from the group consisting of: hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

2. The compound according to claim 1, or a salt, solvate, or stereoisomer thereof, wherein the compound has formula (II): (II)。 3. The compound or its salt, solvate or stereoisomer according to claim 2, wherein: R 3c and R 3d Independently selected from the group consisting of: C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; or R 3c and R 3d Together with the carbon atoms they are attached to, they form C3-C. 12 Cycloalkyl.

4. The compound or its salt, solvate or stereoisomer according to claim 2 or 3, wherein: R 3e and R 3f Independently selected from the group consisting of: halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 -NR 4 C(=O)R 5 -NHR 4 -NR 4 R 5 -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 -NHC(=O)SR 4 -NR 4 C(=O)SR 5 -NHC(=S)SR 4 -NR 4 C(=S)SR 5 4- to 6-membered heterocyclic groups, optionally substituted phenyl groups, and optionally substituted 5- or 6-membered heteroaryl groups; or R 3e and R 3f Together with the carbon atoms they are attached to, they form C3-C. 12 Cycloalkyl.

5. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 4, wherein R 3b It is hydrogen.

6. The compound according to claim 1, or a salt, solvate, or stereoisomer thereof, wherein the compound has formula (III): (III)。 7. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 6, wherein R 1a It is an optional substituted phenyl group.

8. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 6, wherein R 1a It is C1-C 12 alkyl.

9. The compound of claim 8 or its salt, solvate or stereoisomer, wherein R 1a It is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

10. The compound of claim 9 or its salt, solvate or stereoisomer, wherein R 1a It is isopropyl or sec-butyl.

11. The compound of claim 8 or a salt, solvate or stereoisomer thereof, wherein R 1a yes: or .

12. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 11, wherein R 2a R 2b and R 2c The group consisting of hydrogen and C1-C9 alkyl groups is selected independently.

13. The compound of claim 12 or a salt, solvate or stereoisomer thereof, wherein R 2b and R 2c It is hydrogen.

14. The compound of claim 13 or its salt, solvate or stereoisomer, wherein R 2a Choose from the group consisting of hydrogen and C1-C4 alkyl groups.

15. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 14, wherein R 3a It is hydrogen.

16. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 14, wherein R 3a It is a C1-C9 alkyl group.

17. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 14, wherein R 3a It is a C3-C6 cycloalkyl group.

18. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 14, wherein R 3a It is an optional substituted phenyl group.

19. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 18, wherein R 3c It is hydrogen.

20. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 18, wherein R 3c It is a C1-C9 alkyl group.

21. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 18, wherein R 3c It is a C3-C6 cycloalkyl group.

22. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 18, wherein R 3c It is an optional substituted phenyl group.

23. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 3 or 6, wherein R 3e It is hydrogen.

24. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 22, wherein R 3e It is a C1-C8 alkoxy group.

25. The compound according to any one of claims 1 to 22, wherein R 3e It is -OH.

26. The compound according to any one of claims 1 to 22, wherein R 3e Yes -SH.

27. The compound according to any one of claims 1 to 22, wherein R 3e It is a C1-C8 alkylthio group.

28. The compound according to any one of claims 1 to 22, wherein R 3e It is an arylthio group.

29. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 22, wherein R 3e It is a C1-C9 alkyl group.

30. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 22, wherein R 3e It is a C3-C6 cycloalkyl group.

31. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 22, wherein R 3e It is an optional substituted phenyl group.

32. The compound according to any one of claims 1 to 31, wherein R 3f It is hydrogen.

33. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 31, wherein R 3f It is a C1-C9 alkyl group.

34. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 31, wherein R 3f It is a C3-C6 cycloalkyl group.

35. The compound or its salt, solvate or stereoisomer according to any one of claims 1 to 31, wherein R 3f It is an optional substituted phenyl group.

36. The compound or its salt, solvate or stereoisomer according to claim 1, wherein the compound or its salt, solvate or stereoisomer is selected from the group consisting of: , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , as well as .

37. A composition comprising: (i) the compound according to any one of claims 1 to 36; and (ii) One or more elastomers; or (iii) One or more fillers; or (iv) One or more rubber chemicals; or (v) One or more plasticizers; or (vi) One or more other anti-degradation agents; or (vii) A combination of the following: one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers and / or one or more additional anti-degradation agents.

38. The composition of claim 37, wherein the composition comprises one or more elastomers.

39. The composition of claim 38, wherein the composition comprises about 15 wt% to about 85 wt% of the compound and about 15 wt% to about 85 wt% of the one or more elastomers.

40. The composition according to any one of claims 37 to 39, wherein the one or more elastomers comprise natural rubber (NR).

41. The composition of claim 40, wherein the one or more elastomers comprise about 5 wt% to about 80 wt% of natural rubber (NR).

42. The composition according to claim 40 or 41, wherein the natural rubber comprises rubber derived from alternative rubber plants.

43. The composition according to claim 42, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

44. The composition according to any one of claims 38 to 43, wherein the one or more elastomers comprise synthetic rubber.

45. The composition of claim 44, wherein the synthetic rubber comprises unsaturated rubber, saturated rubber, rubber having fluorine and fluoroalkyl or fluoroalkoxy substituents on the polymer chain (FKM), silicone rubber (Q), or blends thereof.

46. ​​The composition of claim 45, wherein the unsaturated rubber comprises polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), or blends thereof.

47. The composition of claim 46, wherein the unsaturated rubber comprises styrene-butadiene rubber (SBR).

48. The composition of claim 47, wherein the one or more elastomers comprise about 5 wt% to about 80 wt% styrene-butadiene rubber (SBR).

49. The composition according to any one of claims 46 to 48, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

50. The composition of claim 49, wherein the one or more elastomers comprise about 5 wt% to about 80 wt% of polybutadiene rubber (BR).

51. The composition according to any one of claims 46 to 50, wherein the unsaturated rubber comprises butyl rubber (IIR).

52. The composition of claim 51, wherein the one or more elastomers comprises about 1 wt% to about 30 wt% butyl rubber (IIR).

53. The composition according to any one of claims 45 to 52, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxetine (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), or blends thereof.

54. The composition according to any one of claims 37 to 53, wherein the one or more elastomers further comprise recycled rubber.

55. The composition according to any one of claims 37 to 54, wherein the composition comprises about 0.1 phr to about 10 phr of the compound.

56. The composition of claim 55, wherein the composition comprises about 0.5 phr to about 5 phr of the compound.

57. The compound of claim 56, wherein the composition comprises about 1 phr to about 5 phr of the compound.

58. The composition according to any one of claims 37 to 57, wherein the composition comprises one or more fillers.

59. The composition of claim 58, wherein the composition comprises about 15 wt% to about 85 wt% of the compound and about 15 wt% to about 85 wt% of the one or more fillers.

60. The composition according to claim 58 or 59, wherein the composition comprises one or more fillers of about 30 phr to about 500 phr.

61. The composition according to any one of claims 58 to 60, wherein the one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fibers (HCF), graphite, graphene, aluminosilicate, starch, fiber, or combinations thereof.

62. The composition of claim 61, wherein the one or more fillers comprise silicon dioxide.

63. The composition according to claim 62, wherein the silica is derived from rice husks.

64. The composition according to any one of claims 58 to 63, wherein the one or more fillers comprise carbon black.

65. The composition according to any one of claims 37 to 64, wherein the composition comprises one or more rubber chemicals.

66. The composition of claim 65, wherein the composition comprises about 15 wt% to about 85 wt% of the compound and about 15 wt% to about 85 wt% of one or more rubber chemicals.

67. The composition according to claim 65 or 66, wherein the composition comprises one or more rubber chemicals at about 0.1 phr to about 30 phr.

68. The composition of claim 67, wherein the composition comprises one or more rubber chemicals of about 1 phr to about 20 phr.

69. The composition according to any one of claims 64 to 68, wherein the one or more rubber chemicals comprise one or more vulcanizing agents, one or more accelerators, one or more activators, one or more pre-vulcanization inhibitors, or combinations thereof.

70. The composition of claim 69, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

71. The composition of claim 70, wherein the one or more vulcanizing agents comprise sulfur, peroxide, resin, or a combination thereof.

72. The composition according to claim 71, wherein the sulfur is octasulfur (S8) or cyclododecylsulfur (S2). 12 ), polysulfide, or combinations thereof.

73. The composition according to claim 71, wherein the peroxide is benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di(tert-butylperoxy)-3-hexyne (2,5 Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di(tert-butylperoxy) valerate (VAL), 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC), or combinations thereof.

74. The composition according to claim 71, wherein the resin is an adhesive resin.

75. The composition according to claims 69 to 74, wherein the one or more rubber chemicals comprise one or more accelerators.

76. The composition of claim 75, wherein the one or more promoters comprises guanidine, thiazole, sulfinamide, thiuram, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

77. The composition of claim 76, wherein the guanidine is diphenylguanidine (DPG).

78. The composition of claim 76, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), N-tert-butyl-2-benzothiazole sulfinamide (TBSI), or a combination thereof.

79. The composition of claim 76, wherein the sulfinamide comprises N-tert-butyl-2-benzothiazole sulfinamide (TBBS), N-cyclohexylbenzothiazole-2-sulfinamide (CBS), dicyclohexyl-2-benzothiazole sulfinamide (DCBS), N-oxydiethylbenzothiazole sulfinamide (OBTS), N-oxydiethylthiocarbamoyl-N'-oxydiethylbenzothiazole sulfinamide (OTOS), thiocarbamoyl sulfinamide, or combinations thereof.

80. The composition according to claim 76, wherein the thiuram is dimethylthiocarbamate dithioperoxyanhydride (thiram), bispentamethylene thiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), tetramethylthiuram monosulfide (TMTM), or a combination thereof.

81. The composition of claim 76, wherein the dithiocarbamate comprises zinc dimethyl dithiocarbamate (ZDMC), zinc diethyl dithiocarbamate (ZDEC), zinc dibutyl dithiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyl dithiocarbamate (SDEC), tellurium diethyl dithiocarbamate (TDEC), zinc dibenzyl dithiocarbamate (ZEBC), or combinations thereof.

82. The composition according to any one of claims 69 to 81, wherein the one or more rubber chemicals comprise one or more activators.

83. The composition of claim 82, wherein the one or more activators comprise metal oxides, acids, metal complexes, or combinations thereof.

84. The composition of claim 83, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

85. The composition of claim 83, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

86. The composition of claim 83, wherein the metal complex comprises zinc ethylhexanoate.

87. The composition according to any one of claims 69 to 86, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

88. The composition of claim 87, wherein the one or more pre-vulcanization inhibitors comprise N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or combinations thereof.

89. The composition according to any one of claims 37 to 88, wherein the composition comprises one or more plasticizers.

90. The composition of claim 89, wherein the composition comprises about 15 wt% to about 85 wt% of the compound and about 15 wt% to about 85 wt% of one or more plasticizers.

91. The composition according to claim 89 or 90, wherein the composition comprises one or more plasticizers of about 0.1 phr to about 30 phr.

92. The composition of claim 91, wherein the composition comprises one or more plasticizers of about 1 phr to about 20 phr.

93. The composition according to any one of claims 89 to 92, wherein the one or more plasticizers comprise mineral oil, organic ester, resin, wax, ester plasticizer, natural source oil, or a combination thereof.

94. The composition according to claim 93, wherein the mineral oil is a naphthenic oil, paraffin oil, or aromatic oil.

95. The composition according to claim 93, wherein the natural source oil is soybean oil, vegetable oil, or orange oil.

96. The composition according to any one of claims 37 to 95, wherein the composition further comprises one or more additional anti-degradation agents.

97. The composition of claim 96, wherein the composition comprises about 15 wt% to about 85 wt% of the compound and about 15 wt% to about 85 wt% of one or more other anti-degradation agents.

98. The composition according to claim 96 or 97, wherein the one or more additional anti-degradation agents are present in an amount of about 0.001 phr to about 10 phr.

99. The composition of claim 98, wherein the one or more additional anti-degradation agents are present in an amount of about 0.1 phr to about 5 phr.

100. The composition of claim 99, wherein the one or more additional anti-degradation agents are present in an amount of about 0.5 phr to about 5 phr.

101. The composition of claim 100, wherein the one or more additional anti-degradation agents are present in an amount of about 1 phr to about 5 phr.

102. The composition according to any one of claims 96 to 101, wherein one or more additional anti-degradation agents are antioxidants.

103. The composition according to any one of claims 96 to 101, wherein one or more additional anti-degradation agents are anti-ozone agents.

104. The composition according to any one of claims 96 to 103, wherein one or more additional anti-degradation agents are p-phenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), or diphenylamine-ketone condensates.

105. The composition according to claim 104, wherein the PPD is N 1 -(4-Methylpent-2-yl)-N 4 -Phenylenyl-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N 1 -Phenyl-N 4 -(propyl-2-yl)phenyl-1,4-diamine (IPPD), N,N'-disec-butyl-p-phenylenediamine (44PD), N,N'-bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD) or N-N'-dioctyl-p-phenylenediamine (88PD).

106. The composition of claim 105, wherein the PPD is 6 PPD.

107. The composition of claim 104, wherein the TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline or an oligomer or polymer thereof.

108. A composition comprising a compound according to any one of claims 1 to 36 and one or more carriers.

109. A method for preparing the composition according to claim 108, the method comprising mixing the compound with one or more carriers.

110. A vulcanized elastomer article comprising the compound according to any one of claims 1 to 36.

111. A vulcanized elastomer article, said vulcanized elastomer article being prepared using the composition according to any one of claims 37 to 108.

112. The vulcanized elastomer article according to claim 110 or 111, wherein the vulcanized elastomer article is a tire.

113. The vulcanized elastomer article according to claim 112, wherein the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

114. The vulcanized elastomer article according to claim 110 or 111, wherein the vulcanized elastomer article is a tire component.

115. The vulcanized elastomer article of claim 114, wherein the component is a bead, belt, body layer, liner, sidewall, bottom tread, or tread.

116. The vulcanized elastomer article according to claim 110 or 111, wherein the vulcanized elastomer article is a rubber overshoe, sealing strip, sound insulation board, air spring, bellows, membrane, tactile sensor, anti-collision pad, hose, conveyor belt or floor.

117. A method for preparing vulcanized elastomer articles, the method comprising: (a) Forming the composition according to any one of claims 38 to 107 into a shaped form; and (b) Vulcanize the shaped material. To provide vulcanized elastomer products.

118. The method of claim 117, wherein the vulcanization is carried out at an average temperature of about 120°C to about 180°C.

119. The method of claim 118, wherein the vulcanization is carried out at an average temperature of about 140°C to about 160°C.

120. The method according to any one of claims 117 to 119, wherein the vulcanized elastomer article is a tire.

121. The method of claim 120, wherein the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a bulldozer tire, an aircraft tire, or a racing tire.

122. The method according to any one of claims 117 to 121, wherein the vulcanized elastomer article is a component of a tire.

123. The method of claim 122, wherein the component is a bead, belt, body layer, liner, sidewall, bottom tread, or tread.

124. The method according to any one of claims 117 to 119, wherein the vulcanized elastomer article is a rubber overshoe, sealing strip, sound insulation board, air spring, bellows, membrane, tactile sensor, anti-collision pad, hose, conveyor belt or floor.

125. A lubricant composition comprising a lubricant and a compound according to any one of claims 1 to 36.

126. A combustible fuel composition comprising a combustible fuel and a compound according to any one of claims 1 to 36.

127. A fuel additive composition comprising a fuel additive and a compound according to any one of claims 1 to 36.

128. A method for retreading tires, the method comprising: (a) Applying the composition according to any one of claims 37 to 108 to a tire; (b) A pre-cured tread is placed around the tire; (c) Applying a cured coating around the tire; and (d) Vulcanize the tire.

129. A kit comprising the composition according to any one of claims 37 to 108 and instructions for using the composition in a vulcanizable elastomer composition.

130. A kit comprising the composition according to any one of claims 37 to 108 and instructions for preparing vulcanized elastomer articles using the composition.

131. The composition according to any one of claims 37, 38, 40 to 58, 60 to 65, 67 to 89, 91 to 96 or 98 to 107, wherein the composition comprises about 0.1 wt / wt% to about 10 wt / wt% of the compound.

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