Anti-degradation agent bis (dihydro and tetrahydroquinoline) compounds and uses thereof

Abstract

The present disclosure provides a compound represented by formula (I), or a salt or solvate thereof, wherein X, R1a, R1b, R1c, R1d, R2a, R2b, R2c, R2d, R4, R5, R6, R7, R8, and R9 are as defined in the specification. 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 methods of retreading a tire using the compositions described herein. The present disclosure also provides kits comprising the compositions described herein.

Description

TECHNICAL FIELD

[0001] The present disclosure provides compounds having anti-degradation (e.g., anti- ozone, antioxidant, and / or anti-fatigue) properties that are useful additives for vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels, and other compositions where such properties are desired or are themselves useful as compositions to impart such properties in compositions. BACKGROUND

[0002] Many materials such as plastics, elastomers, elastomer products (tires, belts, hoses, bushings, mounts, isolators, etc.), lubricants, and petroleum products (such as hydraulic fluids, oils, fuels, and oil / fuel additives for automotive and aerospace applications) are susceptible to degradation upon prolonged exposure to light, heat, oxygen, ozone, repeated mechanical action, and the like. Accordingly, compounds and compositions that exhibit anti-degradation efficacy are well known in the art. For example, U.S. Patent No. 8,987,515 discloses an aromatic polyamine that is useful, inter alia, in lubricant compositions to inhibit oxidative degradation. U.S. Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules that are said to have improved solubility in many commercially available oils and lubricants.

[0003] Anti-degradation agents useful in the manufacture of articles formed from elastomers, plastics, and the like require a very specific combination of qualities that can be difficult to achieve. While anti-degradation agents must obviously have commercially acceptable efficacy, they must also exhibit that efficacy over the long period of time associated with the use of the article, particularly on the exposed surfaces of the article, as degradation caused by environmental factors such as light, oxygen, and ozone primarily occurs on those surfaces. Equally important as protecting the surface-exposed components, efficacy in protecting the embedded components of a composite from oxidative aging and repeated mechanical action is critical. Anti-degradation agents must achieve these results while not negatively impacting the efficacy of other additives or the desirable properties of the final article. Furthermore, anti-degradation agents that provide or improve mechanical fatigue life after use, oxidative aging, or exposure to ozone are highly valued as these will inherently improve the useful mechanical service life of the article. Thus, elastomer articles that are subjected to repeated mechanical flexing, stretching, or compression during use would greatly benefit from this discovery.

[0004] Articles, particularly tires, formed from general elastomers such as natural rubber are especially susceptible to degradation by oxygen and ozone. As described in U.S. Patent No. 2,905,654, the effects of oxygen degradation on rubber are different from the effects of ozone degradation on rubber; however, both effects are detrimental to the performance, appearance, and life of a tire. Fatigue and crack propagation are also issues of particular concern, especially in the steel belt edge region and the tire sidewall, which are subjected to great stress and tensile forces when the tire is flexed during inflation, partial inflation, and throughout its useful life. U.S. Patent No. 8,833,417 describes an antioxidant system that is said to improve long-term fatigue and crack propagation resistance better than the known antioxidants discussed immediately below.

[0005] Materials having antidegradant efficacy for tire applications are well known in the art and are commercially available. For example, N , N' Di-substituted-p-phenylenediamines such as those sold under the trademark Santoflex® are generally favored for this purpose by many tire manufacturers. EP 3147321 Al discloses rubber compositions, tires, amine compounds, and anti-aging agents, in particular rubber compositions said to be suitable for use in a tread rubber or sidewall rubber of a tire. SUMMARY

[0006] The present disclosure provides compounds useful as antidegradants (e.g., antiozonants and / or antioxidants) and / or as additives in lubricants or combustible fuels, which are represented by any one of the following Formulas (I)-(III), collectively referred to herein as “the compounds of the present disclosure” or individually as “the compounds of the present disclosure.”

[0007] The present disclosure also provides compositions comprising: (i) the compounds of the present disclosure; 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 additional antidegradants; or (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and / or one or more additional antidegradants, collectively referred to herein as “the compositions of the present disclosure” or individually as “the compositions of the present disclosure.”

[0008] The present disclosure also provides the compositions of the present disclosure comprising the compounds of the present disclosure and one or more elastomers.

[0009] This disclosure also provides compositions comprising the compounds of this disclosure and one or more fillers.

[0010] This disclosure also provides compositions comprising the compounds of this disclosure and one or more rubber chemicals.

[0011] This disclosure also provides compositions comprising the compounds of this disclosure and one or more plasticizers.

[0012] This disclosure also provides compositions comprising the compounds of this disclosure and one or more additional anti-degradation agents.

[0013] This disclosure also provides compositions comprising the compounds of this disclosure and one or more carriers.

[0014] This disclosure also provides a method for preparing a composition comprising the compound of this disclosure and one or more carriers, the method comprising mixing the compound and one or more carriers.

[0015] This disclosure also provides vulcanized elastomer articles comprising compounds of this disclosure.

[0016] 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).

[0017] This disclosure also provides a method for preparing the vulcanized elastomer article described herein, the method comprising: (a) Forming the composition described herein into a shaped form; and (b) Vulcanization of the formed shape To provide vulcanized elastomer products.

[0018] This disclosure also provides lubricant compositions comprising a lubricant and compounds of this disclosure.

[0019] This disclosure also provides combustible fuel compositions comprising combustible fuel and compounds of this disclosure.

[0020] This disclosure also provides fuel additive compositions comprising fuel additives and compounds of this disclosure.

[0021] This disclosure also provides a method for retreading tires, the method comprising: (a) Applying the composition described herein to a tire; (b) A pre-cured tread is provided around the tire; (c) Providing a cured encapsulation around the tire; and (d) Vulcanizing the tire.

[0022] This disclosure also provides a kit comprising the composition described herein and instructions for using the composition in a vulcanizable elastomer composition.

[0023] This disclosure also provides a kit comprising the compositions described herein and instructions for preparing vulcanized elastomer articles using the compositions.

[0024] Further embodiments and advantages of this disclosure will be set forth in part in the description which follows, and will be apparent from the description, or may be learned by practice of this disclosure. The embodiments and advantages of this disclosure will be realized and achieved by means of the elements and combinations particularly pointed out in the appended claims.

[0025] It should be understood that the above overview and the following detailed description are merely exemplary and illustrative, and do not limit the claimed invention. Detailed Implementation

[0026] In one embodiment, the compound disclosed herein is a compound having formula (I): (I), Or its salts or solvates, wherein: Each It can be a single bond or a double bond; R 1a and R 2a Each member independently chooses from the following groups: C1-C 12 Alkyl groups, -C(=O)OR', -C(=O)NR'R'', -C(=O)SR', -CH2OR', -CH2OC(=O)R' and ; R 1b and R 2b Each is independently selected from hydrogen and C1-C 12 The group consisting of alkyl groups; R 1c and R 2c Each member independently chooses from the following groups: C1-C 12 Alkyl groups, -C(=O)OR', -C(=O)NR'R'', -C(=O)SR', -CH2OR', -CH2OC(=O)R' and , The condition is R 1a R 1c R 2a and R 2cAt least one of them is selected from the following groups: -C(=O)OR', -C(=O)NR'R'', -C(=O)SR', -CH2OR', -CH2OC(=O)R' and ; R 1d and R 2d Each is independently selected from hydrogen and C1-C 12 The group consisting of alkyl groups; R' and R'' are independently selected from hydrogen, C1-C each time they appear. 12 The group consisting of alkyl groups, C3-C6 cycloalkyl groups, and optionally substituted phenyl groups; X Choose Freedom - CHR 3a -、-NR 3b The group consisting of -, -O- and -S-; Z is independently chosen from -O-, -S-, and -NR each time it appears. 11 -A group; R 10a R 10b R 10c and R 10d Each is independently selected from hydrogen, C1-C 12 The group consisting of alkyl groups and optionally substituted phenyl groups; R 11 Each time it appears, select the group consisting of free hydrogen and C1-C6 alkyl groups; R 3a Choose free hydrogen, C1-C 12 The group consisting of alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycles and optionally substituted 5- or 6-membered heteroaryl groups; R 3b Choose free hydrogen, C1-C 12 The group consisting of alkyl groups, C3-C6 cycloalkyl groups, optionally substituted phenyl groups, optionally substituted 5- or 6-membered heterocycles, and optionally substituted 5- or 6-membered heteroaryl groups; and R 4 R 5 R 6 R 7 R 8 and R 9 It is independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio groups.

[0027] In some embodiments, the compounds disclosed herein are compounds having formula (II): (II), Or its salts or solvates, wherein X, R1a R 1b R 1c R 1d R 2a R 2b R 2c R 2d R 4 R 5 R 6 R 7 R 8 and R 9 As defined by associative formula (I).

[0028] In some embodiments, the compounds disclosed herein are compounds having formula (III): (III), Or its salts or solvates, wherein X, R 1a R 1b R 1c R 1d R 2a R 2b R 2c R 2d R 4 R 5 R 6 R 7 R 8 and R 9 As defined by associative formula (I).

[0029] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is -C(=O)OR'.

[0030] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is -C(=O)NR'R''.

[0031] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is -C(=O)NR'R''.

[0032] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is -C(=O)SR'.

[0033] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is -CH2OR'.

[0034] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is -CH2OC(=O)R'.

[0035] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a for: .

[0036] In some implementations, Z is -O-. In some implementations, Z is -S-. In some implementations, Z is -NH-. In some implementations, R 10a R 10b R 10c and R 10d It is hydrogen.

[0037] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a and R 2a It is a C1-C6 alkyl group.

[0038] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is -C(=O)OR'.

[0039] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is -C(=O)NR'R''.

[0040] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is -C(=O)NR'R''.

[0041] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is -C(=O)SR'.

[0042] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is -CH2OR'.

[0043] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is -CH2OC(=O)R'.

[0044] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c for: .

[0045] In some embodiments, Z is -O-. In some embodiments, Z is -S-. In some embodiments, Z is -NH-. In some embodiments, Z is -NH-. In some embodiments, R 10a R 10b R 10c and R 10d It is hydrogen.

[0046] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1c and R 2c It is a C1-C6 alkyl group.

[0047] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a R 1c R 2a and R 2c It is -C(=O)OR'.

[0048] In some embodiments, the compounds disclosed herein are compounds of any of formulas (I)-(III), wherein each R' is independently hydrogen or C1-C6 alkyl.

[0049] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein each R' is independently methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, or sec-butyl.

[0050] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein each R' is an ethyl group.

[0051] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein each R' is hydrogen.

[0052] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1b and R 2b Each is independently a C1-C6 alkyl group.

[0053] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1b and R 2b It is a methyl group.

[0054] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1d and R 2d It is hydrogen.

[0055] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein X is -CHR. 3a -

[0056] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is hydrogen.

[0057] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a For C1-C 12 alkyl.

[0058] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It can be methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, or sec-butyl.

[0059] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is isopropyl.

[0060] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a The phenyl group is optionally substituted.

[0061] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a It is a 5- or 6-membered heteroaryl group that can be substituted.

[0062] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3a for: .

[0063] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein X is -NR. 3b -

[0064] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 3b It is hydrogen.

[0065] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein X is -O-.

[0066] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein X is -S-.

[0067] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 4 R 5 R 6 R 7 R 8 and R 9 Each is independently hydrogen or C1-C6 alkyl.

[0068] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 4 R 5 R 6 R 7 R 8 and R 9 Each can be either hydrogen or methyl.

[0069] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 4 R 5 R 6 R 7 R 8 and R 9 It is hydrogen.

[0070] In some embodiments, the compounds disclosed herein are compounds of any one of formulas (I)-(III), wherein R 1a R 1c R 2aand R 2c R is -C(=O)OR'; R' is selected from the group consisting of hydrogen and ethyl groups; R 1b and R 2b Methyl; R 1d and R 2d It is hydrogen; and X is free-CHR. 3a -、-NR 3b The group consists of -, -O-, and -S-. In some implementations, X is CHR. 3a - In some implementations, X is -NR 3b - In some implementations, X is -O-. In some implementations, X is -S-.

[0071] In some embodiments, the compounds disclosed herein are any one or more of the compounds in Table 1, or their salts or solvates.

[0072] Table 1 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.

[0073] The compounds disclosed herein can be prepared by reacting methylene, amino, ether or thiobisphenylamine with methyl ketone (e.g. ethyl pyruvate) in the presence of an acid, as shown in Scheme 1.

[0074] Option 1 The compounds disclosed herein can also be prepared by reducing the compound obtained in the reaction described in Scheme 1, as shown in Scheme 2. The reduction can be carried out using any method known in the art, such as exposure to hydrogen on a carbon-supported palladium (Pd / C) catalyst.

[0075] Option 2 definition As used in this article, the term "alkyl" alone or as part of another group refers to a straight-chain or branched aliphatic hydrocarbon containing one to twelve carbon atoms, i.e., C1-C2. 12 Alkyl group, or a specified number of carbon atoms, for example ，C1-C3 alkyl groups, such as methyl, ethyl, propyl, or isopropyl; C1-C4 alkyl groups, such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl. In one embodiment, the alkyl group is a straight-chain alkyl group. In another embodiment, the alkyl group is a branched-chain 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 12 Alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, secondary Butyl, tertiary Butyl, iso Butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0076] The term “halogen” or “halogen” as used in this article, whether alone or as part of another group, refers to -Cl, -F, -Br, or -I.

[0077] As used in this article, the term "nitro" alone or as part of another group refers to -NO2.

[0078] As used in this article, the term "cyano" alone or as part of another group refers to -CN.

[0079] As used in this article, the term "hydroxyl group" alone or as part of another group refers to -OH.

[0080] The term "amino" as used alone or as part of another group refers to the formula -NR 12 R 13 The group, wherein R 12 and R 13 It can be hydrogen, alkyl, or aryl independently.

[0081] In one embodiment, the amino group is -NH2.

[0082] In another embodiment, the amino group is an "alkylamino group", i.e., wherein R 12 C 1-6 Alkyl and R 13 The amino group is hydrogen. In one embodiment, R 12 It is a C1-C4 alkyl group. Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0083] In another embodiment, the amino group is a "dialkylamino", i.e., wherein R 12 and R 13 Each independently is C 1-6An alkyl amino group. In one embodiment, R 12 and R 13 Each is independently a C1-C4 alkyl group. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0084] In another embodiment, the amino group is an "arylamino group", i.e., wherein R 12 It is aryl and R 13 The amino group is hydrogen. In one embodiment, R 12 It is an optionally substituted phenyl group. In another embodiment, R 12 It can be phenyl, 2-methylphenyl, 3-methylphenyl or 4-methylphenyl.

[0085] In another embodiment, the amino group is a "diarylamino", i.e., wherein R 12 and R 13 Each is an aryl amino group. In one embodiment, R 12 and R 13 It is a phenyl group.

[0086] As used in this article, the term "aryl" alone 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, naphthyl, phenanthryl, anthraceneyl, indene, azulel, biphenyl, biphenylene, and fluorene groups. In one embodiment, the aryl group is phenyl.

[0087] As used herein, the term "alkyl carbonyl" alone 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.

[0088] As used herein, the term "haloalkyl" alone 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 groups.

[0089] As used herein, either alone or as part of another group, the term "alkoxy" 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 therefore the resulting alkoxy group is referred to as "C1-C4 alkoxy". Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and... tertiary Butoxyl group.

[0090] As used herein, the term "alkathio" alone 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 alkathio group is referred to as "C1-C6 alkathio". In one embodiment, the alkyl group is a C1-C4 alkyl group, and the resulting alkathio group is referred to as "C1-C4 alkathio". Non-limiting exemplary alkathio groups include -SCH3 and -SCH2CH3.

[0091] As used herein, the term "cycloalkyl" alone or as part of another group refers to saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic, or tricyclic aliphatic hydrocarbons containing three to twelve carbon atoms, i.e., C3-C4. 12 Cycloalkyl, or a specified number of carbon atoms, such as C3-C6 cycloalkyl, including cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, the cycloalkyl is bicyclic, i.e., it has two rings. In another embodiment, the cycloalkyl is monocyclic, i.e., it has one ring. In another embodiment, the cycloalkyl is C3-C8 cycloalkyl. In yet another embodiment, the cycloalkyl is C6-C6 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].

[0092] The term “optionally substituted phenyl” as used hereof, alone or as part of another group, refers to an unsubstituted or substituted phenyl group, wherein each substituent is independently a halogen, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, dialkylamino, arylamino, or diarylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0093] As used herein, the term "heterocycle" alone or as part of another group refers to a saturated and partially unsaturated (e.g., containing one or two double bonds) monocyclic, bicyclic, or tricyclic group containing one, two, three, or four heteroatoms, comprising three to eighteen ring members, i.e., 3-membered to 18-membered heterocycles. 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]azapyridine, or 1,3,4,5-tetrahydro-2H-benzo[d]azapyridine-2-one. In some embodiments, the heterocycle is a 6-membered ring containing one nitrogen atom. The heterocycle may fused with the remainder of the molecule to form a bicyclic group, such as 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0094] The term “optionally substituted heterocycle” as used herein, either alone or as part of another group, refers to an unsubstituted heterocyclic group or a heterocyclic group substituted with one to four substituents, which are independently halogenated, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0095] As used herein, either alone or as part of another group, the term "heteroaryl" refers to a monocyclic aromatic ring system having five to six ring members, i.e., a 5- to 6-membered heteroaryl, comprising 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, for example, furanyl, i.e., a 5-membered heteroaryl having four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl has six ring atoms, for example, pyridyl, i.e., a 6-membered heteroaryl having five carbon atoms and one nitrogen atom. Non-limiting exemplary heteroaryl groups include thiophene, furanyl, pyranyl, 2 H -Pyrroloyl, pyrroloyl, imidazoyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazoyl, 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 pyridinyl (e.g., pyridin-2-yl, pyridinyl...). The terms "-3-yl and pyridin-4-yl" include pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin-4-yl, and pyrimidin-5-yl), thiazolyl (e.g., thiazolyl-2-yl, thiazolyl-4-yl, and thiazolyl-5-yl), isothiazolyl (e.g., isothiazol-3-yl, isothiazol-4-yl, and isothiazol-5-yl), oxazolyl (e.g., oxazol-2-yl, oxazol-4-yl, and oxazol-5-yl), and isoxazolyl (e.g., isoxazol-3-yl, isoxazol-4-yl, and isoxazol-5-yl). The term "heteroaryl" also includes N-oxides. A non-limiting exemplary N-oxide is a pyridinyl N-oxide.

[0096] The term “optionally substituted heteroaryl” as used hereof, alone or as part of another group, refers to an unsubstituted heteroaryl group or a heteroaryl group substituted with one to four substituents, wherein the substituents are independently halogenated, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.

[0097] As used herein, the term "stereoisomer" is a general term for all isomers of a single molecule that differ only in the spatial orientation of its atoms. It includes enantiomers and isomers of compounds that have more than one chiral center and are not mirror images of each other (diastereomers).

[0098] The term "chiral center" or "asymmetric carbon atom" refers to a carbon atom that is attached to four different groups.

[0099] The terms “enantiomer” and “enantiomer” refer to molecules that cannot be superimposed on their mirror images and are therefore optically active, where an enantiomer rotates the plane of polarization in one direction, while its mirror compound rotates the plane of polarization in the opposite direction.

[0100] The term "racemic" refers to a mixture of equal parts of enantiomers that is optically inactive.

[0101] 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.

[0102] Unless otherwise stated, the stereochemical terms and conventions used in this specification are intended to be consistent with... Pure&Appl. Chem 68 It is consistent with those described in :2193 (1996).

[0103] The term "enantiomer excess" or "ee" refers to a measure of how much one enantiomer exists compared to another. For R and S A mixture of enantiomers, the percentage of enantiomer excess is defined as │ R - S │*100, where R and S It is the corresponding molar or weight fraction of enantiomers in the mixture, such that R + S = 1. Based on the knowledge of the optical rotation of chiral substances, the enantiomeric excess percentage is defined as ([α]). obs / [α] max )*100, where [α] obs [α] is the optical rotation of an enantiomer mixture. max It is the optical rotation of the pure enantiomer. The enantiomer excess can be determined using a variety of analytical techniques (including NMR spectroscopy, chiral column chromatography, or optical rotation).

[0104] In thin-layer chromatography (TLC), the term R... f R represents the retention factor. f 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.

[0105] Salts and solvates (e.g., hydrates) of the compounds disclosed herein can also be used in the methods disclosed herein.

[0106] 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 solely 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, 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, digluconate, glyceryl phosphates, hemisulfates, heptanates, hexanoates, formates, succinates, fumarates, maleates, ascorbic acid salts, hydroxyethyl sulfonates, salicylates, methanesulfonates, trimethylbenzenesulfonates, naphthalenesulfonates, nicotinates, 2-naphthalenesulfonates, oxalates, dihydroxynaphthaleneates, pectates, persulfates, 3-phenylpropionates, picrates, neopentanoates, propionates, trichloroacetates, trifluoroacetates, phosphates, glutamates, bicarbonates, undecanoates, lactates, citrates, tartrates, gluconates, methanesulfonates, ethanesulfonates, benzenesulfonates, and p-toluenesulfonates. Furthermore, the available amino groups present in the compounds of this disclosure can be quaternized with the following substances: methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dimethyl, diethyl, dibutyl, and dipentyl sulfates; decyl, lauryl, myristyl, and stearyl chlorides, bromides, and iodides; and benzyl and phenethyl bromides. In view of the foregoing, any references to the compounds of this disclosure herein are intended to include the compounds of this disclosure and their salts, hydrates, or solvates.

[0107] 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, a monosolvate, or a 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" includes both a solution phase and a separable solvate. The compounds of this disclosure may exist in a solvated form with solvents such as water, methanol, and ethanol, and this disclosure is intended to include both solvated and unsolvated forms of the compounds of this disclosure.

[0108] One type of solvate is a hydrate. The term "hydrate" refers to a specific subgroup 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) References 601-611 (2004) describe the preparation of solvates of fluconazole with ethyl acetate and water. Similar preparations of solvates, semi-solvates, hydrates, etc., were described by van Tonder et al. AAPS Pharm. Sci. Tech., 5(1) Article 12 (2004) and AL Bingham et al., Chem. Commun. Descriptions in 603-604 (2001) describe a typical, non-limiting process for preparing the solvate, which involves 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). The presence of the solvent in the solvate crystals can be confirmed using analytical techniques such as infrared spectroscopy.

[0109] Unless otherwise stated, in the context of describing this disclosure (especially in the context of the claims), the use of the terms “a,” “an,” “the,” and similar references should be interpreted as covering both the singular and plural. Unless otherwise stated herein, references to ranges of values ​​herein are intended only to serve as a shorthand method for individually referring to each individual value within that range, and each individual value is incorporated into the specification as if it were individually referenced herein. Unless otherwise stated, the use of any and all instances or exemplary language (e.g., “such as”) provided herein is intended to better illustrate this disclosure and not to limit the scope of this disclosure. The language in this specification should not be construed as indicating that any unclaimed element is necessary for practicing this disclosure.

[0110] Furthermore, the term “and / or” as used herein should be considered as a specific disclosure of each of the two specified features or components having or not having the other. Thus, the term “and / or” as used in phrases such as “A and / or B” herein is intended to include “A and B”, “A or B”, “A” (alone), and “B” (alone). Similarly, the term “and / or” as used in phrases such as “A, B, and / or C” is intended to include 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).

[0111] It should be understood that whenever the language “contains” is used in this document to describe an aspect, other similar aspects described by “consisting of” and / or “substantially consisting of” are also provided.

[0112] As used herein, the term "weight / weight%" refers to the mass of one 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 total mass of all components in the composition or blend multiplied by 100. For example, in a composition comprising 1 kg of a compound of the present disclosure, 1 kg of natural rubber, and 2 kg of synthetic rubber, the weight / weight% of the compound is 25 weight / weight% (1 kg / 4 kg = 0.25 x 100 = 25 weight / weight%). In a composition comprising 1 kg of a compound of the present disclosure and 1 kg of carbon black, the weight / weight% of the compound is 50 weight / weight% (1 kg / 2 kg = 0.50 x 100 = 50 weight / weight%). In a composition comprising 1 kg of the disclosed compound, 1 kg of natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black, the compound has a weight / weight percentage of 20 wt% (1 kg / 5 kg = 0.20 x 100 = 20 wt%). In a blend comprising 20 kg of natural rubber and 30 kg of synthetic rubber, one or more elastomers, the natural rubber has a weight / weight percentage of 40 wt% (20 kg / 50 kg = 0.40 x 100 = 40 wt%).

[0113] 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 of 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%.

[0114] 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 a 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, such as a filler, rubber chemical, plasticizer, additional anti-degradation agent, or a combination thereof. In some embodiments, the premix 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 the compounds disclosed herein. In some embodiments, the premix comprises at least one additional component, such as filler, rubber chemicals, plasticizer, additional anti-degradation agent, or combinations thereof, of 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%.

[0115] As used herein, the term "one or more" is intended to indicate the presence of at least one component from a relevant category of components, such as one or more elastomers, or at least one component from a disclosed list, such as 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.

[0116] Composition and method of use In another embodiment, this disclosure provides a composition comprising: (i) the compounds disclosed herein; 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 additional anti-degradation agents; or (vii) A combination of 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.

[0117] 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%, about 0.1 wt% to about 6 wt%, about 0.1 wt% to about 7 wt%, about 0.1 wt% to about 8 wt%, about 0.1 wt% to about 9 wt%, about 0.1 wt% to about 10 wt%, about 0.5 wt% to about 1 wt%, about 0.5 wt% to about 1.5 wt%, about 0.5 wt% to about 2 wt%, about 0.5 wt% to about 2.5 wt%, about 0.5 wt% to about 3 wt%, about 0.5 wt% to about 3.5 wt%, about 0.5 wt% to about 4 wt% / weight%, about 0.5 weight / weight% to about 4.5 weight / weight%, about 0.5 weight / weight% to about 5 weight / weight%, about 0.5 weight / weight% to about 6 weight / weight%, about 0.5 weight / weight% to about 7 weight / weight%, about 0.5 weight / weight% to about 8 weight / weight%, about 0.5 weight / weight% to about 9 weight / weight%, about 0.5 weight / weight% to about 10 weight / weight%, about 1 weight / weight% to about 2 weight / weight%, about 1 weight / weight% to about 2.5 weight / weight%, about 1 weight / weight% to about 3 weight / weight%, about 1 weight / weight% to about 3.5 weight / weight%, about 1 weight / weight% to about 4 weight / weight%, about 1 weight / weight% From to about 4.5 wt%, about 1 wt% to about 5 wt%, about 1 wt% to about 6 wt%, about 1 wt% to about 7 wt%, about 1 wt% to about 8 wt%, about 1 wt% to about 9 wt%, about 1 wt% to about 10 wt%, about 1.5 wt% to about 2 wt%, about 1.5 wt% to about 2.5 wt%, about 1.5 wt% to about 3 wt%, about 1.5 wt% to about 3.5 wt%, about 1.5 wt% to about 4 wt%, about 1.5 wt% to about 4.5 wt%, about 1.5 wt% to about 5 wt%, about 1.5 wt% to about 6 wt%, about 1.5 wt% to about 7 wt%, about 1.5 wt% to about 8 wt%, about 1.5 wt% to about 9 wt%, about 1.5 wt% to about 10 wt%, about 2 wt% to about 2.5 wt%, about 2 wt% to about 3 wt%, about 2 wt% to about 3.5 wt%, about 2 wt% to about 4 wt%, about 2 wt% to about 4.5 wt%, about 2 wt% to about 5 wt%, about 2 wt% to about 6 wt%. Weight%, about 2% to about 7% to about 8% to about 9% to about 10% to about 2.5% to about 3% to about 3.5% to about 4% to about 4.5% to about 5% to about 6% to about 7% to about 8% to about 8% to about 2.5% to about 8%. From approximately 9% by weight to 9% by weight, approximately 2.5% by weight to 10% by weight, approximately 3% by weight to 4% by weight, approximately 3% by weight to 4.5% by weight, approximately 3% by weight to 5% by weight, approximately 3% by weight to 6% by weight, approximately 3% by weight to 7% by weight, approximately 3% by weight to 8% by weight, approximately 3% by weight to 9% by weight, approximately 3% by weight to 10% by weight, approximately 3.5% by weight to 4% by weight, approximately 3.5% by weight to 4.5% by weight, approximately 3.5% by weight to 5% by weight, approximately 3.5% by weight Amount / weight % to about 6 weight / weight%, about 3.5 weight / weight% to about 7 weight / weight%, about 3.5 weight / weight% to about 8 weight / weight%, about 3.5 weight / weight% to about 9 weight / weight%, about 3.5 weight / weight% to about 10 weight / weight%, about 4 weight / weight% to about 4.5 weight / weight%, about 4 weight / weight% to about 5 weight / weight%, about 4 weight / weight% to about 6 weight / weight%, about 4 weight / weight% to about 7 weight / weight%, about 4 weight / weight% to about 8 weight / weight%, about 4 weight / weight% to about 9 weight / weight%, about 4 weight / weight% to about 10 weight / weight%, about 4.5 weight / weight% to about 5 weight / weight%, about 4.5% by weight to about 6% by weight, about 4.5% by weight to about 7% by weight, about 4.5% by weight to about 8% by weight, about 4.5% by weight to about 9% by weight, about 4.5% by weight to about 10% by weight, about 5% by weight to about 6% by weight, about 5% by weight to about 7% by weight, about 5% by weight to about 8% by weight, about 5% by weight to about 9% by weight, about 5% by weight to about 10% by weight, about 6% by weight From about 7 wt% to about 8 wt% to about 9 wt% to about 10 wt% to about 7 wt% to about 8 wt% to about 9 wt% to about 10 wt% to about 10 wt% to about 8 wt% to about 9 wt% to about 10 wt% to about 10 wt% to about 8 wt% to about 10 wt% to about 10 wt% to about 10 wt% to about 8 wt% to about 9 wt% to about 10 ...

[0118] 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 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%. % by weight, about 5% by weight to about 35% by weight, about 5% by weight to about 45% by weight, about 5% by weight to about 55% by weight, about 5% by weight to about 65% by weight, about 5% by weight to about 75% by weight, about 5% by weight to about 85% by weight, about 5% by weight to about 95% by weight, about 15% by weight to about 25% by weight, about 15% by weight to about 35% by weight, about 15% by weight to about 45% by weight, about 15% by weight to about 55% by weight, about 15% by weight to about 65% by weight, about 1 5% by weight to about 75% by weight, about 15% by weight to about 95% by weight, about 25% by weight to about 35% by weight, about 25% by weight to about 45% by weight, about 25% by weight to about 55% by weight, about 25% by weight to about 65% by weight, about 25% by weight to about 75% by weight, about 25% by weight to about 85% by weight, about 25% by weight to about 95% by weight, about 35% by weight to about 45% by weight, about 35% by weight to about 55% by weight, about 35% by weight to about 65% by weight, about 35% by weight to about 75% by weight, about 35% by weight to about 85% by weight, about 35% by weight to about 95% by weight, about 45% by weight to about 55% by weight, about 45% by weight to about 65% by weight, about 45% by weight to about 75% by weight, about 45% by weight to about 85% by weight, about 45% by weight to about 95% by weight, about 55% by weight to about 65% by weight, about 55% by weight to about 75% by weight, about 55% by weight to about 85% by weight, about 55% by weight to about 95% by weightThe composition comprises 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%. In some embodiments, the composition comprises 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 95 wt%. % to about 5 wt%, about 0.1 wt% to about 6 wt%, about 0.1 wt% to about 7 wt%, about 0.1 wt% to about 8 wt%, about 0.1 wt% to about 9 wt%, about 0.1 wt% to about 10 wt%, about 0.5 wt% to about 1 wt%, about 0.5 wt% to about 1.5 wt%, about 0.5 wt% to about 2 wt%, about 0.5 wt% to about 2.5 wt%, about 0.5 wt% to about 3 wt%. From about 0.5 wt% to about 3.5 wt%, from about 0.5 wt% to about 4 wt%, from about 0.5 wt% to about 4.5 wt%, from about 0.5 wt% to about 5 wt%, from about 0.5 wt% to about 6 wt%, from about 0.5 wt% to about 7 wt%, from about 0.5 wt% to about 8 wt%, from about 0.5 wt% to about 9 wt%, from about 0.5 wt% to about 10 wt%, from about 1 wt% to about 2 wt%, from about 1 wt% to about 2.5 wt%, about 1 wt% to about 3 wt%, about 1 wt% to about 3.5 wt%, about 1 wt% to about 4 wt%, about 1 wt% to about 4.5 wt%, about 1 wt% to about 5 wt%, about 1 wt% to about 6 wt%, about 1 wt% to about 7 wt%, about 1 wt% to about 8 wt%, about 1 wt% to about 9 wt%, about 1 wt% to about 10 wt%, about 1.5 wt% to about 2 wt%.From about 1.5 wt% to about 2.5 wt%, from about 1.5 wt% to about 3 wt%, from about 1.5 wt% to about 3.5 wt%, from about 1.5 wt% to about 4 wt%, from about 1.5 wt% to about 4.5 wt%, from about 1.5 wt% to about 5 wt%, from about 1.5 wt% to about 6 wt%, from about 1.5 wt% to about 7 wt%, from about 1.5 wt% to about 8 wt%, from about 1.5 wt% to about 9 wt%, from about 1.5 wt% to about 10 wt%, from about 2 wt% to about 2.5 wt%. From about 2% to about 3% to about 3.5% to about 4% to about 4.5% to about 5% to about 6% to about 7% to about 8% to about 9% to about 10 ... %, about 2.5 wt% to about 4.5 wt%, about 2.5 wt% to about 5 wt%, about 2.5 wt% to about 6 wt%, about 2.5 wt% to about 7 wt%, about 2.5 wt% to about 8 wt%, about 2.5 wt% to about 9 wt%, about 2.5 wt% to about 10 wt%, about 3 wt% to about 4 wt%, about 3 wt% to about 4.5 wt%, about 3 wt% to about 5 wt%, about 3 wt% to about 6 wt%, about 3 wt% to about 7 wt%, about 3 wt% to About 8 wt%, about 3 wt% to about 9 wt%, about 3 wt% to about 10 wt%, about 3.5 wt% to about 4 wt%, about 3.5 wt% to about 4.5 wt%, about 3.5 wt% to about 5 wt%, about 3.5 wt% to about 6 wt%, about 3.5 wt% to about 7 wt%, about 3.5 wt% to about 8 wt%, about 3.5 wt% to about 9 wt%, about 3.5 wt% to about 10 wt%, about 4 wt% to about 4.5 wt%, about 4 wt% to about 5 wt%.From about 4 wt% to about 6 wt%, from about 4 wt% to about 7 wt%, from about 4 wt% to about 8 wt%, from about 4 wt% to about 9 wt%, from about 4 wt% to about 10 wt%, from about 4.5 wt% to about 5 wt%, from about 4.5 wt% to about 6 wt%, from about 4.5 wt% to about 7 wt%, from about 4.5 wt% to about 8 wt%, from about 4.5 wt% to about 9 wt%, from about 4.5 wt% to about 10 wt%, from about 5 wt% to about 6 wt%, from about 5 wt% to about 7 wt%. About 5 wt% to about 8 wt%, about 5 wt% to about 9 wt%, about 5 wt% to about 10 wt%, about 6 wt% to about 7 wt%, about 6 wt% to about 8 wt%, about 6 wt% to about 9 wt%, about 6 wt% to about 10 wt%, about 7 wt% to about 8 wt%, about 7 wt% to about 9 wt%, about 8 wt% to about 10 wt%, about 8 wt% to about 9 wt%, about 8 wt% to about 10 wt%, or about 9 wt% to about 10 wt% of the compounds disclosed herein.

[0119] In some embodiments, the compositions of this disclosure comprise about 50 wt% of the compounds of this disclosure. In some embodiments, the compositions comprise about 1 wt%, 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 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 the compounds of this disclosure. In some embodiments, the composition comprises about 0.1 wt%, about 0.5 wt%, about 1 wt%, about 1.5 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt%, about 5 wt%, about 5.5 wt%, about 6 wt%, about 6.5 wt%, about 7 wt%, about 7.5 wt%, about 8 wt%, about 8.5 wt%, about 9 wt%, or about 10 wt% of the compounds disclosed herein.

[0120] In another embodiment, the composition of this disclosure comprises the compound of this disclosure and one or more elastomers.

[0121] As used herein, the term "elastomer" is a polymer that is viscoelastic (i.e., possesses 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 called 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 rubber trees. Non-limiting types of synthetic rubber include unsaturated rubber, saturated rubber, rubber (FKM) with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain, silicone rubber (Q), and blends thereof. Non-limiting examples of unsaturated rubber include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), nitrile rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and cross-linking reactions, leading to hardening of aged components. With oxidation, these vulcanized rubbers harden and eventually become brittle products. In applications such as vehicle tire sidewalls, partial oxidation of vulcanized rubber can result in performance loss. Saturated rubbers are rubbers without C=C unsaturation and include, but are not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), chlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubbers with fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), and their blends.

[0122] In some embodiments, natural rubber includes rubber derived from alternative rubber plants. As used herein, the term "natural rubber includes rubber derived from alternative rubber plants" refers to a naturally occurring elastomer available from "non-rubber tree" sources. In some embodiments, the alternative rubber plant is *Gynostemma pentaphyllum*. (Parthenium argentatum) (Guayule) or rubber grass (Taraxacum kok-saghyz) (Russian dandelion)

[0123] 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.

[0124] In some embodiments, the compositions disclosed herein comprise one or more elastomers from about 15 wt% to about 85 wt%. 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%, about 5 wt% to about 35 wt%, about 5 wt% to about 45 wt%, about 5 wt% to about 55 wt%, about 5 wt% to about 65 wt%, about 5 wt% to about 75 wt%, about 5 wt% to about 85 wt%, about 5 wt% to about 95 wt%, about 15 wt% to about 25 wt%, about 15 wt% to about 35 wt%, about 15 wt% to about 45 wt%, about 15 wt% to about 55 wt%, about 15 wt% to about 6 5 wt%, about 15 wt% to about 75 wt%, about 15 wt% to about 95 wt%, about 25 wt% to about 35 wt%, about 25 wt% to about 45 wt%, about 25 wt% to about 55 wt%, about 25 wt% to about 65 wt%, about 25 wt% to about 75 wt%, about 25 wt% to about 85 wt%, about 25 wt% to about 95 wt%, about 35 wt% to about 45 wt%, about 35 wt% to about 55 wt%, about 35 wt% weight% to about 65 weight / weight%, about 35 weight / weight% to about 75 weight / weight%, about 35 weight / weight% to about 85 weight / weight%, about 35 weight / weight% to about 95 weight / weight%, about 45 weight / weight% to about 55 weight / weight%, about 45 weight / weight% to about 65 weight / weight%, about 45 weight / weight% to about 75 weight / weight%, about 45 weight / weight% to about 85 weight / weight%, about 45 weight / weight% to about 95 weight / weight%, about 55 weight / weight% to about 65 weight / weight%, about 55 weight / weight% to about 75 weight / weight%, about 55 weight / weight% to about 85 weight / weight%.One or more elastomers comprising about 55% by weight to about 95% by weight, about 65% by weight to about 75% by weight, about 65% by weight to about 85% by weight, about 65% by weight to about 95% by weight, about 75% by weight to about 85% by weight, about 75% by weight to about 95% by weight, or about 85% by weight to about 95% by weight.

[0125] In some embodiments, the compositions disclosed herein comprise about 50 wt% of one or more elastomers. In some embodiments, the composition comprises about 1 wt%, 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 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 one or more elastomers.

[0126] As used herein, the term "phr" refers to the number of parts per hundred parts by weight of rubber. The parts by weight of each component are based on 100 parts by weight of the total mass of one or more elastomers present in the composition.

[0127] In some embodiments, the compositions of this disclosure comprise about 1 phr to about 5 phr of the compounds of this disclosure. In some embodiments, the composition comprises 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, about 0.01 phr to about 20 phr, about 0.1 phr to about 0.5 phr, about 0.1 phr to about 1 phr, about 0.1 phr to about 2 phr, about 0.1 phr to about 3 phr, about 0.1 phr to about 4 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 0.1 phr to about 20 phr, about 1 phr to about 2 phr. phr, approximately 1 phr to approximately 3 phr, approximately 1 phr to approximately 4 phr, approximately 1 phr to approximately 7.5 phr, approximately 1 phr to approximately 10 phr, approximately 1 phr to approximately 20 phr, approximately 2 phr to approximately 3 phr, approximately 2 phr to approximately 4 phr, approximately 2 phr to approximately 5 phr, approximately 2 phr to approximately 7.5 phr, approximately 2 phr to approximately 10 phr, approximately 2 phr to approximately 20 phr, approximately 3 phr to approximately 4 phr, approximately 3 phr to approximately 5 phr, approximately 3 phr to approximately 7.5 phr, approximately 3 phr to approximately 10 phr, approximately 3 phr to approximately 20 phr, approximately 4 phr to approximately 5 phr, approximately 4 phr to approximately 7.5 phr, approximately 4 phr to approximately 10 phr, approximately 4 phr to approximately 20 phr, approximately 7.5 phr to approximately 1 ... The compounds of this disclosure, in phr to about 20 phr, or in phr to about 10 phr to about 20 phr.

[0128] In some embodiments, the composition of this disclosure comprises about 3 phr of the compound of this disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, 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 compound of this disclosure.

[0129] In some embodiments, the compositions of this disclosure comprise the compounds of this disclosure and one or more fillers.

[0130] As used herein, the term "filler" is a substance that enhances 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.

[0131] In some implementations, the filler is derived from a natural source. For example, silica may be derived from rice husks.

[0132] In some embodiments, the compositions disclosed herein comprise one or more fillers from about 15 wt% to about 85 wt%. 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%. % by weight, about 5% by weight to about 35% by weight, about 5% by weight to about 45% by weight, about 5% by weight to about 55% by weight, about 5% by weight to about 65% by weight, about 5% by weight to about 75% by weight, about 5% by weight to about 85% by weight, about 5% by weight to about 95% by weight, about 15% by weight to about 25% by weight, about 15% by weight to about 35% by weight, about 15% by weight to about 45% by weight, about 15% by weight to about 55% by weight, about 15% by weight to about 65% by weight, about 1 5% by weight to about 75% by weight, about 15% by weight to about 95% by weight, about 25% by weight to about 35% by weight, about 25% by weight to about 45% by weight, about 25% by weight to about 55% by weight, about 25% by weight to about 65% by weight, about 25% by weight to about 75% by weight, about 25% by weight to about 85% by weight, about 25% by weight to about 95% by weight, about 35% by weight to about 45% by weight, about 35% by weight to about 55% by weight, about 35% by weight to about 65% by weight, about 35% by weight to about 75% by weight, about 35% by weight to about 85% by weight, about 35% by weight to about 95% by weight, about 45% by weight to about 55% by weight, about 45% by weight to about 65% by weight, about 45% by weight to about 75% by weight, about 45% by weight to about 85% by weight, about 45% by weight to about 95% by weight, about 55% by weight to about 65% by weight, about 55% by weight to about 75% by weight, about 55% by weight to about 85% by weight, about 55% by weight to about 95% by weightOne or more fillers, approximately 65 wt% to approximately 75 wt%, approximately 65 wt% to approximately 85 wt%, approximately 65 wt% to approximately 95 wt%, approximately 75 wt% to approximately 85 wt%, approximately 75 wt% to approximately 95 wt%, or approximately 85 wt% to approximately 95 wt%.

[0133] In some embodiments, the compositions disclosed herein comprise about 50 wt% of one or more fillers. In some embodiments, the compositions comprise about 1 wt%, 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 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 one or more fillers.

[0134] In some embodiments, the compositions disclosed herein comprise one or more fillers of about 30 phr to about 500 phr.In some embodiments, the composition comprises 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, about 50 phr to about 300 phr, about 50 phr to about 350 phr, about 50 phr to about 400 phr, about 50 phr to about 450 phr, about 50 phr to about 500 phr, about 100 phr to about 150 phr. 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, 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 One or more packing materials, approximately 200 phr to approximately 500 phr, approximately 250 phr to approximately 300 phr, approximately 250 phr to approximately 350 phr, approximately 250 phr to approximately 400 phr, approximately 250 phr to approximately 450 phr, approximately 250 phr to approximately 500 phr, approximately 300 phr to approximately 350 phr, approximately 300 phr to approximately 400 phr, approximately 300 phr to approximately 450 phr, approximately 300 phr to approximately 500 phr, approximately 350 phr to approximately 400 phr, approximately 350 phr to approximately 450 phr, approximately 350 phr to approximately 500 phr, approximately 400 phr to approximately 450 phr, approximately 400 phr to approximately 500 phr, or approximately 450 phr to approximately 500 phr.

[0135] 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.

[0136] 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.

[0137] As used herein, the term "vulcanization" refers to the process in which crosslinks are formed between elastomers to influence changes in the material properties of the elastomers. Specifically, vulcanization typically increases the stiffness and durability of elastomers. Vulcanization is carried out at room temperature or high temperatures, depending on the nature of one or more elastomers, one or more fillers, and one or more rubber chemicals used. The term "curing" is also used in the art to describe this process.

[0138] 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 those by forming covalent bonds between the vulcanizing agent and two or more individual polymer chains, or by generating free radicals on individual polymer chains that can be combined to form covalent bonds between two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, vulcanized 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 hexamethoxymethylmelamine (HMMM), to promote adhesion, such as resorcinol-formaldehyde resins and phenolic resins.

[0139] As used herein, the term "accelerator" refers to any substance that increases vulcanization kinetics. In some embodiments, accelerators enable vulcanization to proceed at lower temperatures and / or utilize the vulcanizing agent (e.g., sulfur) more efficiently. Non-limiting examples of accelerators include guanidine, thiazoles, sulfinamides, thiurams, 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 sulfinylimide (TBSI). Non-limiting examples of sulfinamides include... N - tertiary Butyl-2-benzothiazolylsulfinamide (TBBS) N -Cyclohexylbenzothiazole-2-sulfinamide (CBS), dicyclohexyl-2-benzothiazole-sulfinamide (DCBS) N 2-O-diethylbenzothiazole sulfinamide (OBTS) N -O-diethylidene thiocarbamoyl- N' β-O-diethylethylene sulfinamide (OTOS) and thiocarbamoyl sulfinamide. Non-limiting examples of thiuram include dimethylthiocarbamate dithioperoxyanhydride (thiram), dipentamethylenethiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyldithiurame (ZDMC), zinc diethyldithiurame (ZDEC), zinc dibutyldithiurame (ZDBC), nickel dibutyldithiurame (NDBC), sodium dibenzyldithiurame (SBEC), sodium diethyldithiurame (SDEC), tellurium diethyldithiurame (TDEC), and zinc dibenzyldithiurame (ZEBC).

[0140] As used herein, the term "activator" refers to any substance that activates a vulcanizing agent and enables it to crosslink the elastomer as described above. Activators can function through various mechanisms, including but not limited to, by forming a chemical complex with a promoter or by 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.

[0141] 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 known as "retarders." Non-limiting examples of pre-vulcanization inhibitors include... N -(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride and phthalic anhydride.

[0142] 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 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%, about 5 wt% to about 35 wt%, about 5 wt% to about 45 wt%, about 5 wt% to about 55 wt%, about 5 wt% to about 65 wt%, about 5 wt% to about 75 wt%, about 5 wt% to about 85 wt%, about 5 wt% to about 95 wt%, about 15 wt% to about 25 wt%, about 15 wt% to about 35 wt%, about 15 wt% to about 45 wt%, about 15 wt% to about 55 wt%, about 15 wt% to about 6 5 wt%, about 15 wt% to about 75 wt%, about 15 wt% to about 95 wt%, about 25 wt% to about 35 wt%, about 25 wt% to about 45 wt%, about 25 wt% to about 55 wt%, about 25 wt% to about 65 wt%, about 25 wt% to about 75 wt%, about 25 wt% to about 85 wt%, about 25 wt% to about 95 wt%, about 35 wt% to about 45 wt%, about 35 wt% to about 55 wt%, about 35 wt% weight% to about 65 weight / weight%, about 35 weight / weight% to about 75 weight / weight%, about 35 weight / weight% to about 85 weight / weight%, about 35 weight / weight% to about 95 weight / weight%, about 45 weight / weight% to about 55 weight / weight%, about 45 weight / weight% to about 65 weight / weight%, about 45 weight / weight% to about 75 weight / weight%, about 45 weight / weight% to about 85 weight / weight%, about 45 weight / weight% to about 95 weight / weight%, about 55 weight / weight% to about 65 weight / weight%, about 55 weight / weight% to about 75 weight / weight%, about 55 weight / weight% to about 85 weight / weight%.One or more rubber chemicals, approximately 55 wt% to approximately 95 wt%, approximately 65 wt% to approximately 75 wt%, approximately 65 wt% to approximately 85 wt%, approximately 65 wt% to approximately 95 wt%, approximately 75 wt% to approximately 85 wt%, approximately 75 wt% to approximately 95 wt%, or approximately 85 wt% to approximately 95 wt%.

[0143] In some embodiments, the compositions disclosed herein comprise about 15 wt% of one or more rubber chemicals. In some embodiments, the composition comprises about 1 wt%, about 5 wt%, about 10 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 one or more rubber chemicals.

[0144] 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, about 5 One or more rubber chemicals, ranging from about 10 phr to about 40 phr, about 10 phr to about 15 phr, about 10 phr to about 20 phr, about 10 phr to about 25 phr, about 10 phr to about 30 phr, about 10 phr to about 35 phr, about 10 phr to about 40 phr, about 15 phr to about 20 phr, about 15 phr to about 25 phr, about 15 phr to about 30 phr, about 15 phr to about 35 phr, about 15 phr 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, or about 35 phr to about 40 phr.

[0145] In some embodiments, the compositions disclosed herein comprise one or more rubber chemicals at about 10 phr. In some embodiments, the compositions comprise one or more rubber chemicals 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.

[0146] As used herein, the term "plasticizer" refers to a processing aid used to reduce the viscosity of a composition, increase its plasticity, and / or increase its volume. Plasticizers facilitate the process of mixing and forming a composition containing an elastomer prior to vulcanization. Non-limiting examples of plasticizers include mineral oils (paraffin oils, aromatic oils, or naphthenic oils), organic esters, resins, waxes, ester plasticizers, and naturally derived oils such as soybean oil, vegetable oil, or orange oil.

[0147] In some embodiments, the compositions disclosed herein comprise one or more plasticizers from about 15 wt% to about 85 wt%. 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%, about 5 wt% to about 35 wt%, about 5 wt% to about 45 wt%, about 5 wt% to about 55 wt%, about 5 wt% to about 65 wt%, about 5 wt% to about 75 wt%, about 5 wt% to about 85 wt%, about 5 wt% to about 95 wt%, about 15 wt% to about 25 wt%, about 15 wt% to about 35 wt%, about 15 wt% to about 45 wt%, about 15 wt% to about 55 wt%, about 15 wt% to about 6 5 wt%, about 15 wt% to about 75 wt%, about 15 wt% to about 95 wt%, about 25 wt% to about 35 wt%, about 25 wt% to about 45 wt%, about 25 wt% to about 55 wt%, about 25 wt% to about 65 wt%, about 25 wt% to about 75 wt%, about 25 wt% to about 85 wt%, about 25 wt% to about 95 wt%, about 35 wt% to about 45 wt%, about 35 wt% to about 55 wt%, about 35 wt% weight% to about 65 weight / weight%, about 35 weight / weight% to about 75 weight / weight%, about 35 weight / weight% to about 85 weight / weight%, about 35 weight / weight% to about 95 weight / weight%, about 45 weight / weight% to about 55 weight / weight%, about 45 weight / weight% to about 65 weight / weight%, about 45 weight / weight% to about 75 weight / weight%, about 45 weight / weight% to about 85 weight / weight%, about 45 weight / weight% to about 95 weight / weight%, about 55 weight / weight% to about 65 weight / weight%, about 55 weight / weight% to about 75 weight / weight%, about 55 weight / weight% to about 85 weight / weight%.One or more plasticizers, from about 55 wt% to about 95 wt%, from about 65 wt% to about 75 wt%, from about 65 wt% to about 85 wt%, from about 65 wt% to about 95 wt%, from about 75 wt% to about 85 wt%, from about 75 wt% to about 95 wt%, or from about 85 wt% to about 95 wt%.

[0148] In some embodiments, the compositions disclosed herein comprise about 15 wt% of one or more plasticizers. In some embodiments, the composition comprises about 1 wt%, about 5 wt%, about 10 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 one or more plasticizers.

[0149] 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, about 5 phr to about 35 phr, about 5 One or more plasticizers of phr to about 40 phr, about 10 phr to about 15 phr, about 10 phr to about 20 phr, about 10 phr to about 25 phr, about 10 phr to about 30 phr, about 10 phr to about 35 phr, about 10 phr to about 40 phr, about 15 phr to about 20 phr, about 15 phr to about 25 phr, about 15 phr to about 30 phr, about 15 phr to about 35 phr, about 15 phr 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.

[0150] In some embodiments, the compositions disclosed herein comprise one or more plasticizers of about 10 phr. In some embodiments, the compositions comprise one or more plasticizers of 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.

[0151] In some embodiments, the compositions of this disclosure further comprise one or more additional anti-degradation agents that are not compounds disclosed herein. In some embodiments, one or more additional anti-degradation agents are antioxidants. In some embodiments, 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 -Phenylen-1,4-Diamine (6PPD) N -(1,4-Dimethylpentyl)- N' 7-Phenyl-p-phenylenediamine (7PPD) N 1 -phenyl- N 4 1,4-(propyl-2-yl)phenyl-1,4-diamine (IPPD) N , N' -two- secondary Butyl- para phenylenediamine (44PD), N,N'- Bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N , N' -bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD) and N - N' -Disinki- para Phenylenediamine (88PD). Non-limiting examples of TMQ include 2,2,4-trimethyl-1,2-dihydroquinoline and its oligomers or polymers.

[0152] In some embodiments, the compositions disclosed herein comprise one or more additional anti-degradation agents from about 15 wt% to about 85 wt%. 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%, about 5 wt% to about 35 wt%, about 5 wt% to about 45 wt%, about 5 wt% to about 55 wt%, about 5 wt% to about 65 wt%, about 5 wt% to about 75 wt%, about 5 wt% to about 85 wt%, about 5 wt% to about 95 wt%, about 15 wt% to about 25 wt%, about 15 wt% to about 35 wt%, about 15 wt% to about 45 wt%, about 15 wt% to about 55 wt%, about 15 wt% to about 6 5 wt%, about 15 wt% to about 75 wt%, about 15 wt% to about 95 wt%, about 25 wt% to about 35 wt%, about 25 wt% to about 45 wt%, about 25 wt% to about 55 wt%, about 25 wt% to about 65 wt%, about 25 wt% to about 75 wt%, about 25 wt% to about 85 wt%, about 25 wt% to about 95 wt%, about 35 wt% to about 45 wt%, about 35 wt% to about 55 wt%, about 35 wt% weight% to about 65 weight / weight%, about 35 weight / weight% to about 75 weight / weight%, about 35 weight / weight% to about 85 weight / weight%, about 35 weight / weight% to about 95 weight / weight%, about 45 weight / weight% to about 55 weight / weight%, about 45 weight / weight% to about 65 weight / weight%, about 45 weight / weight% to about 75 weight / weight%, about 45 weight / weight% to about 85 weight / weight%, about 45 weight / weight% to about 95 weight / weight%, about 55 weight / weight% to about 65 weight / weight%, about 55 weight / weight% to about 75 weight / weight%, about 55 weight / weight% to about 85 weight / weight%.One or more additional anti-degradation agents, approximately 55% by weight to approximately 95% by weight, approximately 65% ​​by weight to approximately 75% by weight, approximately 65% ​​by weight to approximately 85% by weight, approximately 65% ​​by weight to approximately 95% by weight, approximately 75% by weight to approximately 85% by weight, approximately 75% by weight to approximately 95% by weight, or approximately 85% by weight to approximately 95% by weight.

[0153] In some embodiments, the compositions disclosed herein comprise about 15 wt% of one or more additional anti-degradation agents. In some embodiments, the composition comprises about 1 wt%, about 5 wt%, about 10 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 one or more additional anti-degradation agents.

[0154] In some embodiments, the compositions disclosed herein contain one or more additional anti-degradation agents of about 1 to about 5 phr. In some embodiments, the composition comprises 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 0.01 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. One or more additional anti-degradation agents, or about 7.5 phr to about 10 phr.

[0155] 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.

[0156] In some embodiments, this disclosure provides compositions comprising the compounds of this disclosure and one or more carriers. As used herein, the term "carrier" refers to a solid capable of adsorbing liquids while retaining the general properties of a solid at room temperature. In some embodiments, the carrier is an inert material. In some embodiments, the carrier has a high surface area. In some embodiments, the carrier comprises particles with a diameter of less than 500 micrometers.

[0157] In some embodiments, the composition comprises one or more carriers from about 15 wt% to about 85 wt%. 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%. % by weight, about 5% by weight to about 35% by weight, about 5% by weight to about 45% by weight, about 5% by weight to about 55% by weight, about 5% by weight to about 65% by weight, about 5% by weight to about 75% by weight, about 5% by weight to about 85% by weight, about 5% by weight to about 95% by weight, about 15% by weight to about 25% by weight, about 15% by weight to about 35% by weight, about 15% by weight to about 45% by weight, about 15% by weight to about 55% by weight, about 15% by weight to about 65% by weight, about 1 5% by weight to about 75% by weight, about 15% by weight to about 95% by weight, about 25% by weight to about 35% by weight, about 25% by weight to about 45% by weight, about 25% by weight to about 55% by weight, about 25% by weight to about 65% by weight, about 25% by weight to about 75% by weight, about 25% by weight to about 85% by weight, about 25% by weight to about 95% by weight, about 35% by weight to about 45% by weight, about 35% by weight to about 55% by weight, about 35% by weight to about 65% by weight, about 35% by weight to about 75% by weight, about 35% by weight to about 85% by weight, about 35% by weight to about 95% by weight, about 45% by weight to about 55% by weight, about 45% by weight to about 65% by weight, about 45% by weight to about 75% by weight, about 45% by weight to about 85% by weight, about 45% by weight to about 95% by weight, about 55% by weight to about 65% by weight, about 55% by weight to about 75% by weight, about 55% by weight to about 85% by weight, about 55% by weight to about 95% by weightOne or more carriers, approximately 65 wt% to approximately 75 wt%, approximately 65 wt% to approximately 85 wt%, approximately 65 wt% to approximately 95 wt%, approximately 75 wt% to approximately 85 wt%, approximately 75 wt% to approximately 95 wt%, or approximately 85 wt% to approximately 95 wt%.

[0158] In some embodiments, the composition comprises about 15 wt% of one or more carriers. In some embodiments, the composition comprises about 1 wt%, about 5 wt%, about 10 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 one or more carriers.

[0159] This disclosure also provides a method for preparing a composition comprising the compound of this disclosure and one or more carriers, the method comprising mixing the compound and one or more carriers.

[0160] This disclosure also provides lubricant compositions comprising the compounds and lubricants of this disclosure. Non-limiting examples of lubricants include mineral oils, higher 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).

[0161] This disclosure also provides combustible fuel compositions comprising a combustible fuel and the compounds of this disclosure. Non-limiting examples of combustible fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0162] This disclosure also provides fuel additive compositions comprising fuel additives and compounds of this disclosure. Non-limiting examples of fuel additives include oxygen-containing substances (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 injectors.

[0163] In some embodiments, this disclosure provides the compositions listed in Table 2.

[0164] Table 2

[0165] In some embodiments, the vulcanized tire or other rubber article compositions of Table 2 comprise about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the compounds of this disclosure. In some embodiments, the vulcanized tires or other rubber articles in Table 2 contain at least one elastomer of 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%.

[0166] In some embodiments, the uncured tire inner component or assembly component or other end-use component compositions of Table 2 comprise about 0.01 wt%, about 0.02 wt%, about 0.03 wt%, about 0.04 wt%, about 0.05 wt%, about 0.06 wt%, about 0.07 wt%, about 0.08 wt%, about 0.09 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the compounds of this disclosure. In some embodiments, the uncured tire inner component or assembly component or other end-use component compositions in Table 2 comprise at least one elastomer of 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%.

[0167] Vulcanized elastomer products 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.

[0168] This disclosure also provides vulcanized elastomer articles prepared using the compositions described herein.

[0169] 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.

[0170] In some embodiments, the vulcanized elastomer article is a component of the tire. In some embodiments, the component is a bead, belt ply, carcass ply, inner liner, sidewall, bottom tread, or tread layer.

[0171] In some implementations, vulcanized elastomer products are rubber overshoes, sealing strips, sound-absorbing panels, air springs, bellows, membranes, tactile sensors, anti-collision pads, hoses, conveyor belts, or flooring.

[0172] method This disclosure also provides a method for preparing vulcanized elastomer articles, the method comprising: (a) Forming the composition described herein into a shaped form; and (b) Vulcanizing the formed shape, To provide vulcanized elastomer products.

[0173] In some implementations, 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.

[0174] 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.

[0175] This disclosure also provides a method for retreading tires, the method comprising: (a) Applying the composition described herein to a tire; (b) A pre-cured tread is provided around the tire; (c) Providing a cured encapsulation around the tire; and (d) Vulcanizing the tire.

[0176] Reagent test kit This disclosure also provides kits comprising the compositions described herein, packaged in, for example, containers in a manner that facilitates the use of the compositions in carrying out 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 preparing vulcanizable elastomer articles using the compositions. The compositions may be packaged in any suitable container, such as a sealed bottle or vessel, wherein a label is affixed to the container or included in a kit describing the compositions and their proper use.

[0177] Example 1 Synthesis of Compound 1 Add 4,4'-methylenediphenylamine (3.6 g; 18.2 mmol) and acetonitrile (53 mL) to a 250-mL round-bottom flask equipped with a stir bar. Stir the mixture under N2 protection. Add ethyl pyruvate (8.5 mL; 76.1 mmol) and iodine (0.285 g; 1.12 mmol) sequentially to the flask. Heat the reaction mixture (oil bath set to 60°C). Maintain the temperature for 3 hours. After cooling to room temperature (cold tap water bath), add sodium sulfite (approximately 1.19 g) and stir the mixture vigorously at room temperature for 30 minutes. Strip the volatiles under reduced pressure (rotary evaporator; water bath = 50°C). Dilute the resulting oil-containing salt with AcOEt (50 mL) and deionized water (30 mL). Stir the two-phase system and then transfer it to a separatory funnel. Discard the aqueous layer. The organic layer was washed with deionized water (30 mL), dried over anhydrous magnesium sulfate, filtered, and the volatiles were stripped under reduced pressure (rotary evaporator; water bath = 50–55 °C). The crude product (light brown oil; 10.9 g) was dissolved in DCM (6.2 mL). The resulting solution was loaded into a 41 mm inner diameter column prepared with silica gel 60 and DCM. The height of the silica gel in the column was 20–21 cm. The column was eluted with DCM. The fractions (30 mL) were analyzed by silica gel TLC (30% AcOEt in hexane solution). The fractions containing the title product (Rf = 0.3) were combined, and the volatiles were stripped under reduced pressure (rotary evaporator; water bath = 45 °C). The product was dried on a rotary evaporator (50 °C; <10 mbar; 2.25 h) to give an oil containing a large amount of DCM. The sample was further dried in a vacuum oven at 60 °C for several hours, then left overnight at room temperature to obtain a translucent, semi-solid yellow substance weighing 2.15 g (20% relative to 4,4'-methylenediphenylamine). The structure was identified by proton and carbon-13 APT NMR spectroscopy. The purity was 97.7% by area, as measured by HPLC-UV detection at 260 nm. MS (APCI+): m / z: [M+1] 591 amu. 13C APT NMR (DMSO-d6): δ 173.50 (do, 2C=O); 165.41 (do, 2C=O), 142.06 (do, 2C); 132.11 (up, 2CH); 129.87 (do, 2C); 129.68 (up, 2CH); 128.23 (do, 2C); 125.66 (up, 2CH); 115.21 (do, 2C); 113.78 (up,2CH); 60.95 (do, 2CH2O); 60.64 (do, 2CH2O); 58.02 (do, 2C); 40.13 (do, CH2);39.52 (DMSO); 26.44 (up, 2CH3); 13.95 (up, 4CH3).

[0178] Example 2 Oxidation-inducing time (OIT) performance of the compounds disclosed herein To demonstrate the antioxidant efficacy of the compounds of this disclosure, the oxidation-inducing time (OIT) of selected embodiments was evaluated. OIT was measured according to a procedure performed on a differential scanning calorimeter (TA Instruments, Q200) (also known as DSC) and used to predict the thermal oxidation properties of the substances. In this procedure, each sample was held in a sample cell and heated to a preselected temperature under a nitrogen atmosphere. Oxygen was then introduced into the sample cell, and the length of time before degradation began (as observed by the initial increase in heat flux) was measured.

[0179] 0.5% by weight of the compound disclosed herein, N 1 -(4-Methylpent-2-yl)-N 4 1,4-phenylbenzene-1,4-diamine (6PPD) or without an antioxidant (blank) was mixed with polyisoprene and isothermally heated in O2 at 150°C and / or 160°C. The peak time (in minutes) of the OIT test was measured and is shown in Table 3. Compared with the blank control, compound 1 exhibited antioxidant properties, indicating its utility in rubber and other applications that could benefit from active antioxidants.

[0180] Table 3

[0181] The methods, compounds, and compositions described herein have now been fully described, and those skilled in the art will understand that the same operations can be performed under broad and equivalent 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 in their entirety through reference.

Claims

1. A compound having formula (I): (I)， Or its salts or solvates, wherein: Each It can be a single bond or a double bond; R 1a and R 2a Each member independently chooses from the following groups: C1-C 12 Alkyl groups, -C(=O)OR', -C(=O)NR'R'', -C(=O)SR', -CH2OR', -CH2OC(=O)R' and ； R 1b and R 2b Each is independently selected from hydrogen and C1-C 12 The group consisting of alkyl groups; R 1c and R 2c Each member independently chooses from the following groups: C1-C 12 Alkyl groups, -C(=O)OR', -C(=O)NR'R'', -C(=O)SR', -CH2OR', -CH2OC(=O)R' and ， The condition is R 1a R 1c R 2a and R 2c At least one of them is selected from the following groups: -C(=O)OR', -C(=O)NR'R'', -C(=O)SR', -CH2OR', -CH2OC(=O)R' and ； R 1d and R 2d Each is independently selected from hydrogen and C1-C 12 The group consisting of alkyl groups; R' and R'' are independently selected from hydrogen, C1-C each time they appear. 12 The group consisting of alkyl groups, C3-C6 cycloalkyl groups, and optionally substituted phenyl groups; X Choose Freedom - CHR 3a -、-NR 3b The group consisting of -, -O- and -S-; Z is independently chosen from -O-, -S-, and -NR each time it appears. 11 -A group; R 10a R 10b R 10c and R 10d Each is independently selected from hydrogen, C1-C 12 The group consisting of alkyl groups and optionally substituted phenyl groups; R 11 Each time it appears, select the group consisting of free hydrogen and C1-C6 alkyl groups; R 3a Choose free hydrogen, C1-C 12 The group consisting of alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heterocycles and optionally substituted 5- or 6-membered heteroaryl groups; R 3b Choose free hydrogen, C1-C 12 The group consisting of alkyl groups, C3-C6 cycloalkyl groups, optionally substituted phenyl groups, optionally substituted 5- or 6-membered heterocycles, and optionally substituted 5- or 6-membered heteroaryl groups; and R 4 R 5 R 6 R 7 R 8 and R 9 It is independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, C1-C6 alkoxy and C1-C6 alkylthio groups.

2. The compound of claim 1 or a salt or solvate thereof, having formula (II): (II)。 3. The compound of claim 1 or its salt or solvate, having formula (III): (III)。 4. The compound according to any one of claims 1 to 3, wherein R 1a and R 2a It is -C(=O)OR'.

5. The compound according to any one of claims 1 to 4, wherein R 1c and R 2c It is -C(=O)OR'.

6. The compound according to any one of claims 1 to 5, wherein R 1a R 1c R 2a and R 2c R' is -C(=O)OR', and R' is C1-C 12 alkyl.

7. The compound according to any one of claims 1 to 6, wherein each R' is independently hydrogen or a C1-C6 alkyl group.

8. The compound of claim 7, wherein each R' is independently methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, or sec-butyl.

9. The compound of claim 8, wherein each R' is an ethyl group.

10. The compound of claim 7, wherein each R' is hydrogen.

11. The compound according to any one of claims 1 to 10, wherein R 1b and R 2b Each is independently a C1-C6 alkyl group.

12. The compound of claim 11, wherein R 1b and R 2b It is a methyl group.

13. The compound according to any one of claims 1 to 12, wherein R 1d and R 2d It is hydrogen.

14. The compound according to any one of claims 1 to 13, wherein X is -CHR 3a - 15. The compound of claim 14, wherein R 3a It is hydrogen.

16. The compound of claim 14, wherein R 3a For C1-C 12 alkyl.

17. The compound of claim 14, wherein R 3a It can be methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, or sec-butyl.

18. The compound of claim 17, wherein R 3a It is isopropyl.

19. The compound of claim 14, wherein R 3a The phenyl group is optionally substituted.

20. The compound of claim 14, wherein R 3a It is a 5- or 6-membered heteroaryl group that can be substituted.

21. The compound of claim 20, wherein R 3a for: 。 22. The compound according to any one of claims 1 to 13, wherein X is -NR 3b - 23. The compound of claim 22, wherein R 3b It is hydrogen.

24. The compound according to any one of claims 1 to 13, wherein X is -O-.

25. The compound according to any one of claims 1 to 13, wherein X is -S-.

26. The compound according to any one of claims 1 to 25, wherein R 4 R 5 R 6 R 7 R 8 and R 9 Each is independently hydrogen or C1-C6 alkyl.

27. The compound of claim 26, wherein R 4 R 5 R 6 R 7 R 8 and R 9 Each can be either hydrogen or methyl.

28. The compound of claim 27, wherein R 4 R 5 R 6 R 7 R 8 and R 9 It is hydrogen.

29. The compound of claim 1 or its salt or solvate, wherein the compound is selected from any one or more compounds in Table 1.

30. A composition comprising: (i) the compound as claimed in any one of claims 1 to 29; 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 additional anti-degradation agents; or (vii) A combination of 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.

31. The composition of claim 30, wherein the composition comprises one or more elastomers.

32. The composition of claim 31, 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.

33. The composition of any one of claims 30 to 32, wherein the one or more elastomers comprise natural rubber (NR).

34. The composition of claim 33, wherein the one or more elastomers comprise about 5 wt% to about 80 wt% of natural rubber (NR).

35. The composition of claim 33 or 34, wherein the natural rubber comprises rubber derived from alternative rubber plants.

36. The composition of claim 35, wherein the alternative rubber plant is Grey-white silver chrysanthemum (Silver Glutinous Chrysanthemum) or oak Rubber grass (Russian dandelion) 37. The composition of any one of claims 31 to 36, wherein the one or more elastomers comprise synthetic rubber.

38. The composition of claim 37, wherein the synthetic rubber comprises unsaturated rubber, saturated rubber, rubber having fluorine and fluoroalkyl or fluoroalkoxy substituent groups on the polymer chain (FKM), silicone rubber (Q), or blends thereof.

39. The composition of claim 38, wherein the unsaturated rubber comprises polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-butadiene rubber (SBR), nitrile rubber (NBR), chloroprene rubber (CR), ethylene propylene diene monomer (EPDM) rubber, or blends thereof.

40. The composition of claim 39, wherein the unsaturated rubber comprises styrene-butadiene rubber (SBR).

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

42. The composition of any one of claims 39 to 41, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

43. The composition of claim 42, wherein the one or more elastomers comprise about 5 wt% to about 80 wt% of polybutadiene rubber (BR).

44. The composition of any one of claims 39 to 43, wherein the unsaturated rubber comprises butyl rubber (IIR).

45. The composition of claim 44, wherein the one or more elastomers comprise about 1 wt% to about 30 wt% butyl rubber (IIR).

46. ​​The composition of any one of claims 38 to 45, wherein the saturated rubber comprises acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyl ethylene oxide (CO), ethylene-ethyl acrylate copolymer (EAM), chlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), or blends thereof.

47. The composition of any one of claims 30 to 46, wherein the one or more elastomers further comprises recycled rubber.

48. The composition of any one of claims 30 to 47, wherein the composition comprises about 0.1 phr to about 10 phr of the compound.

49. The composition of claim 48, wherein the composition comprises about 0.5 phr to about 5 phr of the compound.

50. The compound of claim 49, wherein the composition comprises about 1 phr to about 5 phr of the compound.

51. The composition of any one of claims 30 to 50, wherein the composition comprises one or more fillers.

52. The composition of claim 51, 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.

53. The composition of claim 51 or 52, wherein the composition comprises one or more fillers of about 30 phr to about 500 phr.

54. The composition of any one of claims 51 to 53, wherein the one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fibers (HCF), graphite, graphene, aluminosilicates, starch, fibers, or combinations thereof.

55. The composition of claim 54, wherein one or more fillers comprise silicon dioxide.

56. The composition of claim 55, wherein the silica is derived from rice husks.

57. The composition of any one of claims 51 to 56, wherein the one or more fillers comprise carbon black.

58. The composition of any one of claims 30 to 57, wherein the composition comprises one or more rubber chemicals.

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 one or more rubber chemicals.

60. The composition of claim 58 or 59, wherein the composition comprises one or more rubber chemicals in an amount of about 0.1 phr to about 30 phr.

61. The composition of claim 60, wherein the composition comprises one or more rubber chemicals of about 1 phr to about 20 phr.

62. The composition of any one of claims 58 to 61, 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.

63. The composition of claim 62, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

64. The composition of claim 63, wherein one or more vulcanizing agents comprise sulfur, peroxides, resins, or combinations thereof.

65. The composition of claim 64, wherein the sulfur is octasulfur (S8) or cyclododecylsulfur (S2). 12 ), polymeric sulfur, or combinations thereof.

66. The composition of claim 64, 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.

67. The composition of claim 64, wherein the resin is an adhesive resin.

68. The composition of claims 62 to 67, wherein the one or more rubber chemicals comprise one or more accelerators.

69. The composition of claim 68, wherein one or more promoters comprise guanidine, thiazole, sulfinamide, thiuram, dithiocarbamate, xanthate, thiophosphate, or combinations thereof.

70. The composition of claim 69, wherein the guanidine is diphenylguanidine (DPG).

71. The composition of claim 69, wherein the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), or mercaptobenzothiazole disulfide (MBTS). N- tert-butyl-2-benzothiazole sulfinimide (TBSI) or combinations thereof.

72. The composition of claim 69, wherein the sulfinamide comprises N - Uncle Butyl-2-benzothiazolylsulfinamide (TBBS) N -Cyclohexylbenzothiazole-2-sulfinamide (CBS), dicyclohexyl-2-benzothiazole-sulfinamide (DCBS) N 2-O-diethylbenzothiazole sulfinamide (OBTS) N -O-diethylidene thiocarbamoyl- N' 2-O-diethylethylene sulfinamide (OTOS), thiocarbamoyl sulfinamide, or combinations thereof.

73. The composition of claim 69, wherein the thiram is dimethylthiocarbamate dithioperoxyanhydride (thiram), dipentamethylenethiram tetrasulfide (DPIT), tetrabenzylthiram disulfide (TBzTD), tetraethylthiram disulfide (TETD), tetramethylthiram disulfide (TMTD), tetramethylthiram monosulfide (TMTM), or a combination thereof.

74. The composition of claim 69, 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.

75. The composition of any one of claims 62 to 74, wherein the one or more rubber chemicals comprise one or more activators.

76. The composition of claim 75, wherein the one or more activators comprise metal oxides, acids, metal complexes, or combinations thereof.

77. The composition of claim 76, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

78. The composition of claim 76, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

79. The composition of claim 76, wherein the metal complex comprises zinc ethylhexanoate.

80. The composition of any one of claims 62 to 79, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

81. The composition of claim 80, wherein one or more pre-vulcanization inhibitors comprise N -(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride or combinations thereof.

82. The composition of any one of claims 30 to 81, wherein the composition comprises one or more plasticizers.

83. The composition of claim 82, 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.

84. The composition of claim 82 or 83, wherein the composition comprises one or more plasticizers of about 0.1 phr to about 30 phr.

85. The composition of claim 84, wherein the composition comprises one or more plasticizers of about 1 phr to about 20 phr.

86. The composition of any one of claims 81 to 85, wherein the one or more plasticizers comprise mineral oils, organic esters, resins, waxes, ester plasticizers, naturally derived oils, or combinations thereof.

87. The composition of claim 86, wherein the mineral oil is a naphthenic oil, paraffin oil, or aromatic oil.

88. The composition of claim 86, wherein the naturally sourced oil is soybean oil, vegetable oil, or orange oil.

89. The composition of any one of claims 30 to 88, wherein the composition further comprises one or more additional anti-degradation agents.

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 the one or more additional anti-degradation agents.

91. The composition of claim 89 or 90, wherein the one or more additional anti-degradation agents are present in an amount of about 0.001 phr to about 10 phr.

92. The composition of claim 91, wherein the one or more additional anti-degradation agents are present in an amount of about 0.1 phr to about 5 phr.

93. The composition of claim 92, wherein the one or more additional anti-degradation agents are present in an amount of about 0.5 phr to about 5 phr.

94. The composition of claim 93, wherein the one or more additional anti-degradation agents are present in an amount of about 1 phr to about 5 phr.

95. The composition of any one of claims 89 to 94, wherein the one or more additional anti-degradation agents are antioxidants.

96. The composition of any one of claims 89 to 94, wherein the one or more additional anti-degradation agents are anti-ozone agents.

97. The composition of any one of claims 89 to 96, wherein the one or more additional anti-degradation agents are p-phenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), or diphenylamine-ketone condensates.

98. The composition of claim 97, wherein the PPD is N 1 -(4-Methylpent-2-yl)- N 4 -Phenylen-1,4-Diamine (6PPD) N -(1,4-Dimethylpentyl)- N' 7-Phenyl-p-phenylenediamine (7PPD) N 1 -phenyl- N 4 1,4-(propyl-2-yl)phenyl-1,4-diamine (IPPD) N , N' -two- Zhong Butyl- right phenylenediamine (44PD), N,N'- Bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N , N' -bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD) and N - N' -Disinki- right phenylenediamine (88PD).

99. The composition of claim 98, wherein the PPD is 6 PPD.

100. The composition of claim 97, wherein the TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline or an oligomer or polymer thereof.

101. A composition comprising the compound as described in any one of claims 1 to 29 and one or more carriers.

102. A method for preparing the composition of claim 101, the method comprising mixing the compound with one or more carriers.

103. A vulcanized elastomer article comprising the compound as described in any one of claims 1 to 29.

104. A vulcanized elastomer article prepared using the composition as described in any one of claims 30 to 101.

105. The vulcanized elastomer article as claimed in claim 103 or 104, wherein the vulcanized elastomer article is a tire.

106. The vulcanized elastomer article of claim 105, 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.

107. The vulcanized elastomer article as claimed in claim 103 or 104, wherein the vulcanized elastomer article is a component of a tire.

108. The vulcanized elastomer article of claim 105, wherein the component is a bead, belt layer, carcass ply, liner, sidewall, bottom tread, or tread.

109. The vulcanized elastomer article as claimed in claim 103 or 104, wherein the vulcanized elastomer article is a rubber overshoe, sealing strip, sound-absorbing plate, air spring, bellows, membrane, tactile sensor, shock-absorbing pad, hose, conveyor belt, or flooring material.

110. A method for preparing vulcanized elastomer articles, the method comprising: (a) Forming the composition as described in any one of claims 30 to 101 into a shaped form; as well as (b) Vulcanization of the formed shape To provide vulcanized elastomer products.

111. The method of claim 110, wherein the vulcanization is carried out at an average temperature of about 120°C to about 180°C.

112. The method of claim 111, wherein the vulcanization is carried out at an average temperature of about 140°C to about 160°C.

113. The method of any one of claims 110 to 112, wherein the vulcanized elastomer article is a tire.

114. The method of claim 113, 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.

115. The method of any one of claims 110 to 112, wherein the vulcanized elastomer article is a component of a tire.

116. The method of claim 115, wherein the component is a bead, belt layer, carcass ply, liner, sidewall, bottom tread, or tread.

117. The method of any one of claims 110 to 112, wherein the vulcanized elastomer article is a rubber overshoe, sealing strip, sound-absorbing plate, air spring, bellows, membrane, tactile sensor, shock-absorbing pad, hose, conveyor belt, or flooring material.

118. A lubricant composition comprising a lubricant and a compound as claimed in any one of claims 1 to 29.

119. A combustible fuel composition comprising a combustible fuel and a compound as claimed in any one of claims 1 to 29.

120. A fuel additive composition comprising a fuel additive and a compound as claimed in any one of claims 1 to 29.

121. A method for retreading tires, the method comprising: (a) Applying the composition as described in any one of claims 30 to 101 to a tire; (b) A pre-cured tread is provided around the tire; (c) Providing a cured encapsulation around the tire; and (d) Vulcanizing the tire.

122. A kit comprising the composition as described in any one of claims 30 to 101 and instructions for using the composition in a vulcanizable elastomer composition.

123. A kit comprising the composition as described in any one of claims 30 to 101 and instructions for using said composition to prepare vulcanized elastomer articles.

124. The composition of claim 30, wherein the composition comprises about 0.1 wt% to about 10 wt% of the compound.

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