6-aminoquinoline-based degradation inhibitor

Abstract

This disclosure provides compounds represented by formula (I), or salts, solvates, or stereoisomers thereof, wherein R1a, R1b, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, R3f, and R3g as defined herein. This disclosure also provides compositions, vulcanized elastomer articles, lubricant compositions, flammable fuel compositions, and fuel additive compositions comprising the compounds disclosed herein. This disclosure also provides processes for preparing the compositions and vulcanized elastomer articles described herein. This disclosure also provides processes for retreading tires using the compositions described herein. This disclosure also provides kits comprising the compositions described herein. TIFF2026519908000052.tif3755

Description

[Technical Field]

[0001] This disclosure provides compounds having properties as degradation inhibitors, such as anti-ozone agents, antioxidants, and / or anti-fatigue agents, which are useful additives to compositions including vulcanized rubber articles, elastomers, lubricants, and fuels, and other compositions that require such properties, or compositions that themselves impart such properties. [Background technology]

[0002] Many materials, such as plastics, elastomers, elastomer products (tires, belts, hoses, bushings, mounts, vibration dampers, etc.), lubricants, and petroleum products (e.g., working fluids, oils, fuels, and oil / fuel additives for automotive and aerospace applications), tend to degrade when exposed to light, heat, oxygen, ozone, and repetitive mechanical action for extended periods. Therefore, compounds and compositions demonstrating the effectiveness of degradation inhibitors are well known in the art. For example, U.S. Patent No. 8,987,515 discloses aromatic polyamines useful for inhibiting oxidative degradation, particularly in lubricant compositions. U.S. Patent Application Publication 2014 / 0316163 discloses antioxidant macromolecules with improved solubility in many commercially available oils and lubricants.

[0003] Anti-degradation agents useful in the manufacture of articles formed from elastomers, plastics, etc., require a very specific combination of qualities that may be difficult to achieve. While anti-degradation agents must obviously possess commercially acceptable efficacy, they must also demonstrate their effectiveness over the long term associated with the use of the article, particularly on the exposed surfaces of the article where decomposition primarily occurs due to environmental factors such as light, oxygen, and ozone. Effectiveness in protecting embedded components of composite materials from the effects of oxidative aging and repetitive mechanical action is crucial, as is the protection of surface-exposed components. Anti-degradation agents must achieve these results without adversely affecting the effectiveness or desirable properties of other additives in the final article. Furthermore, anti-degradation agents that provide or improve mechanical fatigue life due to oxidative aging or ozone exposure after the article has been used are highly valued because they essentially improve the useful mechanical service life of the article. As a result, elastomer articles that undergo repeated mechanical bending, stretching, or compression during use will greatly benefit from such findings.

[0004] Articles formed from natural rubber, particularly general-purpose elastomers such as tires, are susceptible to degradation from both oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effects of oxygen decomposition on rubber differ from those of ozone decomposition, but both effects can adversely impact tire performance, appearance, and lifespan. Fatigue and crack propagation are also issues of particular concern, especially in the edge regions of steel belts and tire sidewalls, which are subjected to significant stress and tensile forces during flexing throughout the tire's service life, whether inflated, partially inflated, or deflated. U.S. Patent No. 8,833,417 describes an antioxidant system that is said to increase long-term resistance to fatigue and crack propagation compared to known antioxidants discussed below. Materials having degradation-preventive properties are well known and commercially available in the art for use in tire applications. For example, N,N'-disubstituted paraphenylenediamine, such as those sold under the trademark Santoflex®, is commonly preferred by many tire manufacturers for this purpose. EP3147321A1 discloses rubber compositions, tires, amine compounds, and antioxidants, particularly rubber compositions said to be suitable for use in tire tread rubber or sidewall rubber. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] U.S. Patent No. 8,987,515 [Patent Document 2] U.S. Patent Application Publication No. 2014 / 0316163 [Patent Document 3] U.S. Patent No. 2,905,654 [Patent Document 4] U.S. Patent No. 8,833,417 [Patent Document 5] European Patent Application Publication No. 3147321A1 [Overview of the project]

[0006] This disclosure provides compounds, represented by any one of the following formulas (I) to (III), collectively referred to herein as “the Disclosed Compounds” or individually referred to as “the Disclosed Compounds,” that are useful as degradation inhibitors, for example, anti-ozone agents and / or antioxidants, and / or as additives in lubricants or flammable fuels.

[0007] This disclosure also states, (i) Compounds of the present disclosure, and (ii) One or more elastomers, or (iii) One or more fillers, (iv) One or more rubber chemicals, (v) One or more plasticizers, (vi) One or more additional anti-deterioration agents, (vii) A composition comprising 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 degradation inhibitors, which is collectively referred to herein as the “Disclosed Compositions” or individually as the “Disclosed Compositions”.

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

[0009] The Disclosure also provides compositions of the Disclosure, comprising the compounds of the Disclosure and one or more fillers.

[0010] The Disclosure also provides compositions of the Disclosure, comprising the compounds of the Disclosure and one or more rubber chemicals.

[0011] The Disclosure also provides compositions comprising the compounds of the Disclosure and one or more plasticizers.

[0012] The Disclosure also provides compositions comprising the compounds of the Disclosure and one or more additional degradation inhibitors.

[0013] The Disclosure also provides compositions comprising the compounds of the Disclosure and one or more carriers.

[0014] The Disclosure also provides a process for preparing a composition comprising the compound of the Disclosure and one or more carriers, the process comprising mixing the compound and one or more carriers.

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

[0016] This disclosure also provides vulcanized elastomer articles prepared using the compositions described herein, for example, the compositions of this disclosure, or compositions comprising the compounds of this disclosure and one or more carriers.

[0017] This disclosure also provides a process for preparing the vulcanized elastomer articles described herein, the process is (a) Forming the compositions described herein into a molded shape, (b) including vulcanizing the formed shape, We provide vulcanized elastomer articles.

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

[0019] This disclosure also provides flammable fuels and flammable fuel compositions comprising the compounds of this disclosure.

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

[0021] This disclosure also provides a process for refurbishing tires, and this process is (a) Applying the composition described herein to a tire, (b) Placing a pre-vulcanized tread around the tire, (c) Placing a hardening envelope around the tire, (d) including vulcanizing the tires.

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

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

[0024] Additional embodiments and advantages of the Disclosure are partially described below, derived from the Description, or can be learned through practice of the Disclosure. These embodiments and advantages will be realized and achieved by the elements and combinations specifically indicated in the appended claims.

[0025] Please understand that both the above summary and the following embodiments for carrying out the invention are merely illustrative and explanatory, and do not limit the invention as described in the claims. [Brief explanation of the drawing]

[0026] [Figure 1] This is a broken line graph showing the 1H nuclear magnetic resonance (NMR) spectrum of intermediate compound 1-I in d6-dimethyl sulfoxide (d6-DMSO).

[0027] [Figure 2] This is a broken line graph showing the 13C APT NMR spectrum of intermediate compound 1-I in d6-DMSO.

[0028] [Figure 3] This is a liquid chromatography (LC) chromatogram of intermediate compound 1-I.

[0029] [Figure 4] This is a broken line graph showing the 13C APT NMR spectrum of compound 1 in d-chloroform (CDCl3).

[0030] [Figure 5] This is the LC chromatogram of compound 1.

[0031] [Figure 6] This is a broken line graph showing the 13C APT NMR spectrum of compound 2 in d6-DMSO.

[0032] [Figure 7] This is the LC chromatogram of compound 2.

[0033] [Figure 8] This is the LC chromatogram of intermediate compound 3-I.

[0034] [Figure 9] This is a broken line graph showing the 13C APT NMR spectrum of compound 3 in d6-DMSO.

[0035] [Figure 10] This is the LC chromatogram of compound 3.

[0036] [Figure 11] This is a broken line graph showing the 13C APT NMR spectrum of intermediate compound 4-I in d6-DMSO.

[0037] [Figure 12] This is the LC chromatogram of intermediate compound 4-I.

[0038] [Figure 13] This is a broken line graph showing the 13C APT NMR spectrum of compound 4 in d6-DMSO.

[0039] [Figure 14] This is the LC chromatogram of compound 4.

[0040] [Figure 15] This is a broken line graph showing the 13C APT NMR spectrum of intermediate compound 47-I in d6-DMSO.

[0041] [Figure 16] This is the LC chromatogram of intermediate compound 47-I.

[0042] [Figure 17] This is a broken line graph showing the 13C APT NMR spectrum of compound 47 in d6-DMSO.

[0043] [Figure 18] It is the LC chromatogram of Compound 47.

Mode for Carrying Out the Invention

[0044] In one embodiment, the compound of the present disclosure has the formula (I):

Chemical formula

[0045]

Chemical formula

[0046] [[ID=:31]] R 1a is selected from the group consisting of optionally substituted C1-C 12 alkyl, -CHR 1c R 1d C3-C6 cycloalkyl, 4-6 member heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-member heteroaryl;

[0047] R 1b is selected from the group consisting of hydrogen and C1-C9 alkyl;

[0048] R 1c is selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-member heteroaryl;

[0049] R 1d is selected from the group consisting of hydrogen and C1-C9 alkyl;

[0050] R 2a R 2b and R 2cHowever, independently, hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 Selected from the group consisting of 4-6 membered heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 membered heteroaryls, or

[0051] R 2b However, hydrogen, halogens, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR 4 -OC(=O)R 4 -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5, -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 Selected from the group consisting of 4-6 membered heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 membered heteroaryls,

[0052] R 2a and R 2c However, together with the two carbon atoms to which they are bonded, they form a C5-C8 cycloalkyl, a 5-8 membered heterocyclyl, or a C5-C6 aryl.

[0053] R 3a and R 3b However, independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that, [ka] If R is a double bond, 3b Either it does not exist, or

[0054] R 3a and R 3b However, along with the carbon atoms to which they are bonded, C3~C 12 It forms a cycloalkyl group, however, [ka] It is a single bond,

[0055] R 3c and R 3d However, independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, provided that, [ka] If R is a double bond, 3d Either it does not exist, or

[0056] R 3c and R3d together with the carbon atom to which they are attached, form a C3-C 12 cycloalkyl, provided that

Chemical formula

[0057] R 3e and R 3f are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR 4 , -OC(=O)R 4 , -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 , -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NHR 4 , -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 , a 4- to 6-membered heterocyclyl, an optionally substituted phenyl, and an optionally substituted 5- or 6-membered heteroaryl, or

[0058] R 3e and R 3f together with the carbon atom to which they are attached, form a C3-C 12 cycloalkyl,

[0059] R 3g is selected from the group consisting of hydrogen and C1-C9 alkyl,

[0060] R4 and R 5 is, in each occurrence, independently, a compound selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl, or a salt, solvate, or stereoisomer thereof.

[0061] In another embodiment, the compound of the present disclosure is a compound having formula (I), provided that R 3e and / or R 3f is hydrogen, R 3c and R 3d is, independently, a compound selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.

[0062] In another embodiment, the compound of the present disclosure is of formula (II): [Chemical formula] a compound having, wherein R 1a , R 2a , R 2b , R 2c , R 3a , R 3b , R 3c , R 3d , R 3e , and R 3f is as defined in relation to formula (I).

[0063] In some embodiments, the compound of the present disclosure is a compound of formula (II), wherein

[0064] ​​​​​​​​​​​​​​​​

[0066] In some embodiments, the compounds disclosed herein are compounds of formula (II), wherein,

[0067] R 3e and R 3f However, independently, halogens, C1-C9 alkyls, C1-C9 haloalkyls, C3-C8 cycloalkyls, -OH, -SH, C1-C8 alkoxys, C1-C8 alkylthios, arylthios, and C(=O)ORs exist. 4 -OC(=O)R 4 -C(=O)NR 4 R 5 , -NR 4 C(=O)R 5 , -NHR 4 , -NR 4 R 5 -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NHR 4 -SC(=O)NR 4 R 5 , -NHC(=O)SR 4 , -NR 4 C(=O)SR 5 , -NHC(=S)SR 4 , -NR 4 C(=S)SR 5 Selected from the group consisting of 4-6 membered heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 membered heteroaryls, or

[0068] R 3e and R 3f However, along with the carbon atoms to which they are bonded, C3~C 12 It is a compound that forms a cycloalkyl group.

[0069] In some embodiments, the compounds of the present disclosure are compounds of formula (I) or formula (II), where R 3b However, it is hydrogen, a compound.

[0070] In some embodiments, the compounds of the present disclosure are of formula (III): [ka] A compound having, in the formula, R 1a , R 2a , R 2b , R 2c , R 3a , R 3c , R 3e , and R 3f However, it is a compound as defined in relation to formula (I).

[0071] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 1a However, it is a compound in which phenyl is optionally substituted.

[0072] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 1a However, C1~C 12 It is an alkyl compound.

[0073] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 1a The compound is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0074] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 1a However, it is a compound that is isopropyl or sec-butyl.

[0075] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 1a but, [ka] It is a compound.

[0076] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 2a , R 2b , and R 2c However, it is a compound independently selected from the group consisting of hydrogen and C1-C9 alkyl groups.

[0077] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 2b and R 2c However, it is hydrogen, a compound.

[0078] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 2a However, it is a compound selected from the group consisting of hydrogen and C1-C4 alkyl groups.

[0079] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3a However, it is hydrogen, a compound.

[0080] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3a However, it is a compound that is C1-C9 alkyl.

[0081] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3a However, it is a compound that is a C3-C6 cycloalkyl group.

[0082] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3a However, it is a compound in which phenyl is optionally substituted.

[0083] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3c However, it is hydrogen, a compound.

[0084] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3c However, it is a compound that is C1-C9 alkyl.

[0085] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3c However, it is a compound that is a C3-C6 cycloalkyl group.

[0086] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3c However, it is a compound in which phenyl is optionally substituted.

[0087] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is hydrogen, a compound.

[0088] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is a compound that is a C1-C8 alkoxy.

[0089] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is a compound with an -OH group.

[0090] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3eHowever, it is a compound that is -SH.

[0091] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is a compound that is C1-C8 alkylthio.

[0092] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is an arylthio compound.

[0093] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is a compound that is C1-C9 alkyl.

[0094] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is a compound that is a C3-C6 cycloalkyl group.

[0095] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3e However, it is a compound in which phenyl is optionally substituted.

[0096] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3f However, it is hydrogen, a compound.

[0097] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3f However, it is a compound that is C1-C9 alkyl.

[0098] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3f However, it is a compound that is a C3-C6 cycloalkyl group.

[0099] In some embodiments, the compounds of the present disclosure are any one of the compounds of formulas (I) to (III), where R 3f However, it is a compound in which phenyl is optionally substituted.

[0100] In some embodiments, the compounds of the present disclosure are one or more of the compounds in Table 1, or salts or solvates thereof. [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9] [Table 1-10] [Table 1-11] [Table 1-12] [Table 1-13] [Table 1-14]

[0101] The compounds of this disclosure can be useful as degradation inhibitors, for example, as anti-ozone agents and / or antioxidants, as additives in lubricants and as additives in flammable fuels.

[0102] The compounds of this disclosure can be prepared, for example, by a two-step process, which comprises: i) reacting 4-nitroaniline with an alkene and an aldehyde or ketone in acetonitrile or another suitable solvent and any suitable acid or catalyst such as I2, i.e., via a Povarov reaction; and ii) reacting the product of step i) with an aldehyde or ketone under reducing conditions (e.g., pressurized H2 with a platinum catalyst) as shown in Scheme 1, where R 1e For example, C1~C 12 Alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, or optionally substituted 5 or 6-membered heteroaryl, R 1f These are, for example, hydrogen or C1-C6 alkyl groups. Scheme 1 [ka]

[0103] The compounds of this disclosure can also be prepared by oxidizing the compounds obtained in Scheme 1 by methods known in the art, as shown in Scheme 2. Scheme 2 [ka]

[0104] definition When used herein, either alone or as part of another group, the term "alkyl" means a linear or branched aliphatic hydrocarbon containing 1 to 12 carbon atoms, i.e., C1 to C2. 12 Alkyl refers to a specified number of carbon atoms, such as C1-C3 alkyls like methyl, ethyl, propyl, or isopropyl, or C1-C4 alkyls like methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In one embodiment, alkyl is a linear alkyl. In another embodiment, alkyl is a branched alkyl. In one embodiment, alkyl is a C1-C8 alkyl. In another embodiment, alkyl is a C1-C6 alkyl. In another embodiment, alkyl is a C1-C4 alkyl. In another embodiment, alkyl is a C1-C3 alkyl. Non-limiting and exemplary C1-C 12 Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0105] When used herein, either alone or as part of another group, the term “optionally substituted alkyl” means an unsubstituted alkyl or one to three substituents, each independently of a nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, cycloalkyl, or -C(=O)OR 1i And in the formula, R 1i However, this refers to alkyl groups that are C1-C6 alkyl and substituted with 1-3 substituents.

[0106] When used herein, either alone or as part of another group, the term "aryl" refers to an aromatic ring system having 6 to 14 carbon atoms, i.e., C6-C 14This refers to aryl groups. Non-limiting and exemplary aryl groups include phenyl (abbreviated as "Ph"), naphthyl, phenanthryl, anthrasyl, indenyl, azlenyl, biphenyl, biphenylenyl, and fluorenyl groups. In one embodiment, the aryl group is phenyl or naphthyl. In another embodiment, the aryl group is phenyl.

[0107] Where used herein, either alone or as part of another group, the term "halo" or "halogen" refers to -Cl, -F, -Br, or -I.

[0108] Where used herein, either alone or as part of another group, the term "nitro" refers to -NO2.

[0109] Where used herein, either alone or as part of another group, the term "cyano" refers to -CN.

[0110] Where used herein, either alone or as part of another group, the term "hydroxy" refers to the -OH group.

[0111] Where used herein, either alone or as part of another group, the term "amino" is defined as formula -NR 1g R 1h A radical of which, in the formula, R 1g and R 1h However, it refers to a radical that is independently hydrogen or alkyl.

[0112] In one embodiment, the amino acid is -NH2.

[0113] In another embodiment, amino is "alkylamino," i.e., R 1g The C1-C6 alkyl group is R 1h It is an amino group which is hydrogen. In one embodiment, R 1g These are C1-C4 alkyl groups. Non-restrictive and exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0114] In another embodiment, amino is a "dialkylamino," i.e., R 1g and R 1h However, each is independently an amino group that is C1-C6 alkyl. In one embodiment, R 1g and R 1h Each of these is independently a C1-C4 alkyl group. Non-restrictive and exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0115] Where used herein, either alone or as part of another group, the term "alkylcarbonyl" refers to a carbonyl group, i.e., a -C(=O)- substituted with an alkyl group. In one embodiment, the alkyl is a C1-C4 alkyl group. A non-limiting and exemplary alkylcarbonyl group is -COCH3.

[0116] Where used herein, either alone or as part of another group, the term “haloalkyl” refers to an alkyl group substituted with one or more fluorine, chlorine, bromine, and / or iodine atoms. In one embodiment, the alkyl is substituted with one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl is substituted with one, two, or three fluorine atoms. In another embodiment, the alkyl is a C1-C6 alkyl group, and the resulting haloalkyl group is referred to as a “C1-C6 haloalkyl group”. In another embodiment, the alkyl is a C1-C4 alkyl group, and the resulting haloalkyl group is referred to as a “C1-C4 haloalkyl group”. In another embodiment, the alkyl group is a C1 or C2 alkyl group. Non-limiting and 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.

[0117] Where used herein, either alone or as part of another group, the term "alkoxy" refers to an alkyl group bonded 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 a "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 a "C1-C4 alkoxy." Non-limiting and exemplary alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0118] Where used herein, either alone or as part of another group, the term "alkylthio" refers to an alkyl group bonded to a terminal sulfur atom. In one embodiment, the alkyl is a C1-C6 alkyl group, and the resulting alkylthio is referred to as "C1-C6 alkylthio". In one embodiment, the alkyl is a C1-C4 alkyl group, and the resulting alkylthio is referred to as "C1-C4 alkylthio". Non-limiting and exemplary alkylthio groups include -SCH3 and -SCH2CH3.

[0119] Where used herein, either alone or as part of another group, the term "arylthio" refers to an aryl group bonded to a terminal sulfur atom. In some embodiments, the aryl is phenyl or naphthyl.

[0120] Where used herein, either alone or as part of another group, the term "cycloalkyl" means a monocyclic, bicyclic, or tricyclic aliphatic hydrocarbon containing 3 to 12 carbon atoms, i.e., C3-C3 12This refers to cycloalkyls, or aliphatic hydrocarbons containing a specified number of carbon atoms, such as C3-C6 cycloalkyls including cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, the cycloalkyl is bicyclic, i.e., has two rings. In another embodiment, the cycloalkyl is monocyclic, i.e., has one ring. In yet another embodiment, the cycloalkyl is C3-C8 cycloalkyl. In yet another embodiment, the cycloalkyl is C 3~ It is a C6 cycloalkyl. In another embodiment, the cycloalkyl is a C5 cycloalkyl, i.e., cyclopentyl. In another embodiment, the cycloalkyl is a C6 cycloalkyl, i.e., cyclohexyl. Non-limiting and exemplary C3-C 12 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0121] Where used herein, either alone or as part of another group, the term “optionally substituted phenyl” means an unsubstituted phenyl or a phenyl substituted with 1 to 5 substituents, each independently being a halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl group.

[0122] Where used herein, either alone or as part of another group, the term “heterocyclic” refers to monocyclic, bicyclic, or tricyclic groups, saturated and partially unsaturated (e.g., containing one or two double bonds), that contain a 3- to 18-membered heterocyclic ring, i.e., containing one, two, three, or four heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom may be independently oxidized to obtain a sulfoxide, i.e., S(=O), or a sulfone, i.e., S(=O)2. The term heterocyclic includes groups in which one or more -CH2- groups are substituted with one or more -C(=O)- groups, including cyclic ureido groups such as imidazolidinyl-2-one, cyclic amide groups such as pyrrolidine-2-one or piperidine-2-one, and cyclic carbamate groups such as oxazolidinyl-2-one. The term heterocycle also includes groups formed by the condensation of an optionally substituted aryl group or an optionally substituted heteroaryl group, such as indoline, indoline-2-one, 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]azepine, or 1,3,4,5-tetrahydro-2H-benzo[d]azepine-2-one. In some embodiments, the heterocycle is a six-membered ring containing one nitrogen atom. The heterocycle may be condensed with the rest of the molecule to form a bicyclic group, such as 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0123] Where used herein, either alone or as part of another group, the term “optionally substituted heterocycle” means an unsubstituted heterocycle group or a heterocycle group substituted with 1 to 4 substituents, each independently being halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0124] When used herein, either alone or as part of another group, the term “heteroaryl” refers to a monocyclic aromatic ring system having a 5-6 member heteroaryl, i.e., a 5-6 member heteroaryl containing 5-6 ring members, i.e., 1, 2, 3, 4, or 5 heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl has 3 heteroatoms. In another embodiment, the heteroaryl has 2 heteroatoms. In another embodiment, the heteroaryl has 1 heteroatom. In another embodiment, the heteroaryl has 5 ring atoms, e.g., furyl, a 5-membered heteroaryl having 4 carbon atoms and 1 oxygen atom. In another embodiment, the heteroaryl has 6 ring atoms, e.g., pyridyl, a 6-membered heteroaryl having 5 carbon atoms and 1 nitrogen atom. Examples of non-restrictive and exemplary heteroaryl groups include thienyl, furyl, pyranyl, 2H-pyrrolyl, pyrrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridadinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, the heteroaryl is thienyl (e.g., thien-2-yl and thien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., 1H-pyrrole-2-yl and 1H-pyrrole-3-yl), imidazolyl (e.g., 2H-imidazole-2-yl and 2H-imidazole-4-yl), pyrazolyl (e.g., 1H-pyrazole-3-yl, 1H-pyrazole-4-yl, and 1H-pyrazole-5-yl), pyridyl (e.g., pyridine-2-yl, pyridine-3-yl, and pyridine-4-yl), pyrimidinyl (e.g., Selected from pyrimidine-2-yl, pyrimidine-4-yl, and pyrimidine-5-yl), thiazolyl (e.g., thiazole-2-yl, thiazole-4-yl, and thiazole-5-yl), isothiazolyl (e.g., isothiazole-3-yl, isothiazole-4-yl, and isothiazole-5-yl), oxazolyl (e.g., oxazole-2-yl, oxazole-4-yl, and oxazole-5-yl), and isoxazolyl (e.g., isoxazole-3-yl, isoxazole-4-yl, and isoxazole-5-yl).The term heteroaryl also includes N-oxides. A non-limiting and exemplary N-oxide is pyridyl N-oxide.

[0125] Where used herein, either alone or as part of another group, the term “optionally substituted heteroaryl” means an unsubstituted heteroaryl, or a heteroaryl having 1 to 4 substituents, each independently being a halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0126] As used herein, the term “stereoisomer” is a general term for all isomers of individual molecules that differ only in the orientation of their atoms in space. Stereoiomers include enantiomers and diastereomers (isomers of compounds having two or more chiral centers that are not mirror images of each other).

[0127] The term "chiral center" or "chiral carbon atom" refers to a carbon atom to which four different groups are bonded.

[0128] The terms "enantiomer" and "of an enantiomer" refer to molecules that cannot be superimposed on their mirror image and are therefore optically active, where the enantiomer rotates the plane of polarization in one direction, and the enantiomer rotates the plane of polarization in the opposite direction.

[0129] The term "racemic" refers to a mixture of equal amounts of enantiomers, which is optically inert.

[0130] The term "absolute configuration" refers to the spatial arrangement of atoms in a chiral molecule (or group), and its stereochemical description, such as R or S.

[0131] Unless otherwise indicated, the stereochemical terms and notation used herein are consistent with those found in Pure & Appl. Chem 68:2193 (1996).

[0132] The term "enantiomer excess" or "ee" refers to a measure of how much of one enantiomer is present compared to the other. For a mixture of R and S enantiomers, the enantiomer excess percentage is defined as |RS|*100, where R and S are the respective mole or weight fractions of the enantiomers in the mixture such that R+S=1. In knowledge of the optical rotation of chiral substances, the enantiomer excess percentage is ([α] obs / [α] max )*100 is defined as, in the formula, [α] obs This is the optical rotation of a mixture of enantiomers, [α] max This represents the optical rotation of pure enantiomers. Determining enantiomer excess can be done using various analytical techniques, including NMR spectroscopy, chiral column chromatography, or optical polarization measurements.

[0133] In thin-layer chromatography (TLC), R f The term R represents the retention coefficient. f This value is defined as the distance traveled by each individual component divided by the total distance traveled by the eluent. This value is always between 0 and 1.

[0134] Salts and solvates of the compounds disclosed herein, such as hydrates, can also be used in the manner disclosed herein.

[0135] This disclosure encompasses the preparation and use of salts of the compounds of this disclosure. Salts of the compounds of this disclosure can be prepared during the final isolation and purification of the compounds, or separately by reacting the compounds with an acid having a suitable cation. Salts of the compounds of this disclosure may be acid-added 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, as well as organic acids such as oxalic acid, maleic acid, succinic acid, and citric acid. Non-limiting examples of salts of the compounds disclosed herein include hydrochloride, hydrobromide, hydroiodide, sulfate, hydrogen sulfate, 2-hydroxyethanesulfonate, phosphate, hydrogen phosphate, acetate, adipine, alginate, aspartate, benzoate, hydrogen sulfate, butyrate, camphorate, camphorsulfonate, digluconate, glycerol phosphate, hemisulfonate, heptaneate, hexanoate, formate, succinate, fumarate, maleate, ascorbate, isethionate, salicylate, methanesulfonate, and mesitylene. Examples of available amino groups present in the compounds of this disclosure include, but are not limited to, sulfonates, naphthylene sulfonates, nicotinates, 2-naphthalene sulfonates, oxalates, pamoates, pectinates, persulfates, 3-phenylpropionates, picrinates, pivaphosphates, propions, trichloroacetates, trifluoroacetates, phosphates, glutamates, bicarbonates, p-toluenesulfonates, undecanoates, lactates, citrates, tartrates, glucons, methanesulfonates, ethanedisulfonates, benzenesulfonates, and p-toluenesulfonates. In addition, available amino groups present in the compounds of this disclosure can be quaternized with methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dimethyl, diethyl, dibutyl, and diamyl sulfates, decyl, lauryl, myristyl, and steryl chlorides, bromides, and iodides; and benzyl bromide and phenethyl bromide. In consideration of the foregoing, any reference to the compounds of the Disclosure appearing herein is intended to include the compounds of the Disclosure, as well as their salts, hydrates, or solvates.

[0136] This disclosure encompasses the preparation and use of solvates of the compounds of this disclosure. As used herein, the term “solvate” refers to a combination, physical association, and / or solvation of a compound of this disclosure with a solvent molecule, such as a disolvate, monosolvate, or hemisolvate, where the ratio of the solvent molecule to the compound of this disclosure is about 2:1, about 1:1, or about 1:2, respectively. This physical association involves varying degrees of ionic and covalent bonding, including hydrogen bonding. In certain examples, solvates can be isolated, such as when one or more solvent molecules are incorporated into the crystal lattice of a crystalline solid. Thus, “solvate” encompasses both the solution phase and the isolateable solvate. The compounds of this disclosure can exist in solvated form with solvents such as water, methanol, and ethanol, and this disclosure is intended to encompass both solvated and unsolvated forms of the compounds of this disclosure.

[0137] 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 well known in the art. For example, see M. Caira et al, J. Pharmaceut. Sci., 93(3):601-611 (2004), which describes the preparation of a solvate of fluconazole using ethyl acetate and water. Similar preparations of solvates, semi-solvates, hydrates, etc., are described in van Tonder et al., AAPS Pharm. Sci. Tech., 5(1): Article 12 (2004), and ALBingham et al., Chem. Commun. 603-604 (2001). A typical and non-limiting process for preparing a solvate involves dissolving the compound of the disclosure in a desired solvent (organic matter, water, or a mixture thereof) at a temperature greater than 20°C to about 25°C, then cooling the solution at a rate sufficient to form crystals, and isolating the crystals by known methods, such as filtration. The presence of the solvent in the solvate crystals can be confirmed using analytical techniques such as infrared spectroscopy.

[0138] Unless otherwise indicated, in the context describing this disclosure (particularly in the context of the claims), the use of “a,” “an,” “the,” and similar referring terms should be interpreted to encompass both singular and plural forms. Unless otherwise indicated herein, the enumeration of value ranges is intended to function merely as a simplified way of referring individually to each individual value within that range, and each individual value is incorporated herein as if it were individually enumerated herein. Any and all examples or illustrative language provided herein (e.g., “etc.”) is intended to better illustrate this disclosure and, unless otherwise asserted, does not limit the scope of this disclosure. No language herein should be interpreted to indicate that any unclaimed element is essential to the practice of this disclosure.

[0139] Furthermore, when used herein, “and / or” is construed to mean that each of the two specified features or components is specifically disclosed, whether in combination with the other or not. Thus, when used in phrases such as “A and / or B” herein, the term “and / or” is intended to include “A and B,” “A or B,” “A” (alone), and “B” (alone). Similarly, when used in phrases such as “A, B, and / or C,” the term “and / or” is intended to include each of the following embodiments: A, B, and C; A, B, or C; A or C; A or B; B or C; A and C; A and B; B and C; A (alone); B (alone); and C (alone).

[0140] Where an aspect is described in this specification using the language “comprising,” similar aspects described using other expressions such as “consisting of” and / or “consisting essentially of” are also provided.

[0141] As used herein, the term "wt / wt%" refers to the mass of one component in a composition or blend, for example, a composition containing the compound of the disclosure and one or more elastomers, or a blend containing the composition of the disclosure and one or more fillers, or two or more elastomers, etc., divided by the total mass of all components in the composition or blend, multiplied by 100. For example, the wt / wt% of the compound of the disclosure in a composition containing 1 kg of the compound, 1 kg of natural rubber, and 2 kg of synthetic rubber is 25 wt / wt% (1 kg / 4 kg = 0.25 × 100 = 25 wt / wt%). The wt / wt% of the compound of the disclosure in a composition containing 1 kg of the compound and 1 kg of carbon black is 50 wt / wt% (1 kg / 2 kg = 0.50 × 100 = 50 wt / wt%). In a composition containing 1 kg of the compound, 1 kg of natural rubber, 2 kg of synthetic rubber, and 1 kg of carbon black, the wt / wt% of the compound of this disclosure is 20 wt / wt% (1 kg / 5 kg = 0.20 × 100 = 20 wt / wt%). In a blend of one or more elastomers containing 20 kg of natural rubber and 30 kg of synthetic rubber, the wt / wt% of natural rubber is 40 wt / wt% (20 kg / 50 kg = 0.40 × 100 = 40 wt / wt%).

[0142] As used herein, the term “masterbatch” refers to a composition comprising at least one elastomer and a compound of the Disclosure. In some embodiments, the masterbatch comprises at least one elastomer in an amount of about 5 wt / wt% to about 95 wt / wt% and a compound of the Disclosure in an amount of about 5 wt / wt% to about 95 wt / wt%. In some embodiments, the masterbatch contains about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the Compounds of the Disclosure. In some embodiments, the masterbatch contains at least one elastomer in an amount of approximately 5 wt / wt%, approximately 10 wt / wt%, approximately 15 wt / wt%, approximately 20 wt / wt%, approximately 25 wt / wt%, approximately 30 wt / wt%, approximately 35 wt / wt%, approximately 40 wt / wt%, approximately 45 wt / wt%, approximately 50 wt / wt%, approximately 55 wt / wt%, approximately 60 wt / wt%, approximately 65 wt / wt%, approximately 70 wt / wt%, approximately 75 wt / wt%, approximately 80 wt / wt%, approximately 85 wt / wt%, approximately 90 wt / wt%, or approximately 95 wt / wt%.

[0143] As used herein, the term “premix” refers to a composition comprising the compounds of the Disclosure and at least one additional component, for example, a filler, a rubber chemical, a plasticizer, an additional degradation inhibitor, or a combination thereof. In some embodiments, the premix does not contain an elastomer. In some embodiments, the premix comprises about 5 wt / wt% to about 95 wt / wt% of the compounds of the Disclosure and about 5 wt / wt% to about 95 wt / wt% of at least one additional component, for example, a filler, a rubber chemical, a plasticizer, an additional degradation inhibitor, or a combination thereof. In some embodiments, the premix contains about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the compounds of the Disclosure. In some embodiments, the premix includes at least one additional component in about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%, such as fillers, rubber chemicals, plasticizers, additional degradation inhibitors, or a combination thereof.

[0144] As used herein, the term “one or more” means that there is at least one component in the category of components in question (e.g., one or more elastomers) or at least one component in the disclosed list (e.g., one or more fluorine, chlorine, bromine, and / or iodine atoms), and in some embodiments, it is intended to mean that there is two or more components. 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.

[0145] Composition and method of use In another embodiment, the present disclosure is a composition, (i) Compounds of the present disclosure, and (ii) One or more elastomers, or (iii) One or more fillers, (iv) One or more rubber chemicals, (v) One or more plasticizers, (vi) One or more additional anti-deterioration agents, (vii) A composition comprising 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 degradation inhibitors.

[0146] The actual form of this composition is approximately 0.1 wt / wt% to approximately 10 wt / wt% of the compound disclosed herein. For example, approximately 0.1 wt / wt% to approximately 0.5 wt / wt%, approximately 0.1 wt / wt% to approximately 1 wt / wt%, approximately 0.1 wt / wt% to approximately 1.5 wt / wt%, approximately 0.1 wt / wt% to approximately 2 wt / wt%, approximately 0.1 wt / wt% to approximately 2.5 wt / wt%, approximately 0.1 wt / wt% to approximately 3 wt / wt%, approximately 0.1 wt / wt% to approximately 3.5 wt / wt%, approximately 0.1 wt / wt% to approximately 4 wt / wt%, approximately 0.1 wt / wt% to approximately 4.5 wt / wt%, approximately 0.1 wt / wt%~approx. 5wt / wt%, approx. 0.1wt / wt%~approx. 6wt / wt%, approx. 0.1wt / wt%~approx. 7wt / wt%, approx. 0.1wt / wt%~approx. 8wt / wt%, approx. 0.1wt / wt%~approx. 9wt / wt%, approx. 0.1wt / wt%~approx. 10wt / wt%, approx. 0.5wt / wt%~approx. 1wt / wt%, approx. 0.5wt / wt%~approx. 1.5wt / wt%, approx. 0.5wt / wt%~approx. 2wt / wt%, approx. 0.5wt / wt%~approx. 2.5wt / wt%, approx. 0.5wt / wt%~approx. 3wt / wt%, approx. 0.5wt / wt%~approx. 3.5wt / wt%, approx. 0.5wt / wt% t%~approx. 4wt / wt%, approx. 0.5wt / wt%~approx. 4.5wt / wt%, approx. 0.5wt / wt%~approx. 5wt / wt%, approx. 0.5wt / wt%~approx. 6wt / wt%, approx. 0.5wt / wt%~approx. 7wt / wt%, approx. 0.5wt / wt%~approx. 8wt / wt%, approx. 0.5wt / wt%~approx. 9wt / wt%, approx. 0.5wt / wt%~approx. 10wt / wt%, approx. 1wt / wt%~approx. 2wt / wt%, approx. 1wt / wt%~approx. 2.5wt / wt%, approx. 1wt / wt%~approx. 3wt / wt%, approx. 1wt / wt%~approx. 3.5wt / wt%, approx. 1wt / wt%~approx. 4wt / wt% Approximately 1 wt% to approximately 4.5 wt%; approximately 1 wt% to approximately 5 wt%; approximately 1 wt% to approximately 6 wt%; approximately 1 wt% to approximately 7 wt%; approximately 1 wt% to approximately 8 wt%; approximately 1 wt% to approximately 9 wt%; approximately 1 wt% to approximately 10 wt%; approximately 1.5 wt% to approximately 2 wt%; approximately 1.5 wt% to approximately 2.5 wt%; approximately 1.5 wt% to approximately 3 wt%; approximately 1.5 wt% to approximately 3.5 wt%; approximately 1.5 wt% to approximately 4 wt%; approximately 1.5 wt% to approximately 4 wt%.5wt / wt%, about 1.5wt / wt% to about 5wt / wt%, about 1.5wt / wt% to about 6wt / wt%, about 1.5wt / wt% to about 7wt / wt%, about 1.5wt / wt% to about 8wt / wt%, about 1.5wt / wt% to about 9wt / wt%, about 1.5wt / wt% to about 10wt / wt%, about 2wt / wt% to about 2.5wt / wt%, about 2wt / wt% to about 3wt / wt%, about 2wt / wt% to about 3.5wt / wt%, about 2wt / wt% to about 4wt / wt%, about 2wt / wt% to about 4.5wt / wt%, about 2wt / wt% to about 5wt / wt%, about 2wt / wt% %~approx. 6wt / wt%, approx. 2wt / wt%~approx. 7wt / wt%, approx. 2wt / wt%~approx. 8wt / wt%, approx. 2wt / wt%~approx. 9wt / wt%, approx. 2wt / wt%~approx. 10wt / wt%, approx. 2.5wt / wt%~approx. 3wt / wt%, approx. 2.5wt / wt%~approx. 3.5wt / wt%, approx. 2.5wt / wt%~approx. 4wt / wt%, approx. 2.5wt / wt%~approx. 4.5wt / wt%, approx. 2.5wt / wt%~approx. 5wt / wt%, approx. 2.5wt / wt%~approx. 6wt / wt%, approx. 2.5wt / wt%~approx. 7wt / wt%, approx. 2.5wt / wt%~approx. 8wt / wt%, approx. 2 0.5wt / wt%~approx. 9wt / wt%, approx. 2.5wt / wt%~approx. 10wt / wt%, approx. 3wt / wt%~approx. 4wt / wt%, approx. 3wt / wt%~approx. 4.5wt / wt%, approx. 3wt / wt%~approx. 5wt / wt%, approx. 3wt / wt%~approx. 6wt / wt%, approx. 3wt / wt%~approx. 7wt / wt%, approx. 3wt / wt%~approx. 8wt / wt%, approx. 3wt / wt%~approx. 9wt / wt%, approx. 3wt / wt%~approx. 10wt / wt%, approx. 3.5wt / wt%~approx. 4wt / wt%, approx. 3.5wt / wt%~approx. 4.5wt / wt%, approx. 3.5wt / wt%~approx. 5wt / wt%, approx. 3 0.5wt / wt%~approx. 6wt / wt%, approx. 3.5wt / wt%~approx. 7wt / wt%, approx. 3.5wt / wt%~approx. 8wt / wt%, approx. 3.5wt / wt%~approx. 9wt / wt%, approx. 3.5wt / wt%~approx. 10wt / wt%, approx. 4wt / wt%~approx. 4.5wt / wt%, approx. 4wt / wt%~approx. 5wt / wt%, approx. 4wt / wt%~approx. 5wt / wt%, approx. 4wt / wt%~approx. 6wt / wt%, approx. 4wt / wt%~approx. 7wt / wt%, approx. 4wt / wt%~approx. 8wt / wt%, approx. 4wt / wt%~approx. 9wt / wt%, approx. 4wt / wt%~approx. 10wt / wt%, approx. 4.5wt / wt%~approx. 5wt / wt%, approx. 4wt / wt%.5wt / wt%~approx. 6wt / wt%, approx. 4.5wt / wt%~approx. 7wt / wt%, approx. 4.5wt / wt%~approx. 8wt / wt%, approx. 4.5wt / wt%~approx. 9wt / wt%, approx. 4.5wt / wt%~approx. 10wt / wt%, approx. 5wt / wt%~approx. 6wt / wt%, approx. 5wt / wt%~approx. 7wt / wt%, approx. 5wt / wt%~approx. 8wt / wt%, approx. 5wt / wt%~approx. 9wt / wt%, approx. 5wt / wt%~approx. 10wt / wt%, approx. 6wt / wt% / wt%~approx. 7wt / wt%, approx. 6wt / wt%~approx. 8wt / wt%, approx. 6wt / wt%~approx. 9wt / wt%, approx. 6wt / wt%~approx. 10wt / wt%, approx. 7wt / wt%~approx. 8wt / wt%~approx. 9wt / wt%~approx. 10wt / wt%, approx. 8wt / wt%~approx. 9wt / wt%~approx. 10wt / wt%, and also contains approximately 9wt / wt%~approx. 10wt / wt% of the compounds disclosed in this publication.

[0147] The composition of the invention is in the form of the present disclosure, and the compound of the disclosure is about 15wt / wt% to about 85wt / wt%. The actual form of this composition is approximately 1 wt / wt% to 5 wt / wt%, approximately 1 wt / wt% to 15 wt / wt%, approximately 1 wt / wt% to 25 wt / wt%, approximately 1 wt / wt% to 35 wt / wt%, approximately 1 wt / wt% to 45 wt / wt%, approximately 1 wt / wt% to 55 wt / wt%, approximately 1 wt / wt% to 65 wt / wt%, approximately 1 wt / wt% to 75 wt / wt%, approximately 1 wt / wt% to 85 wt / wt%, approximately 1 wt / wt% to 95 wt / wt%, approximately 5 wt / wt% to 15 wt / wt%, approximately 5 wt / wt%. ~approx. 25 wt / wt%, approx. 5 wt / wt% to approx. 35 wt / wt%, approx. 5 wt / wt% to approx. 45 wt / wt%, approx. 5 wt / wt% to approx. 55 wt / wt%, approx. 5 wt / wt% to approx. 65 wt / wt%, approx. 5 wt / wt% to approx. 75 wt / wt%, approx. 5 wt / wt% to approx. 85 wt / wt%, approx. 5 wt / wt% to approx. 95 wt / wt%, approx. 15 wt / wt% to approx. 25 wt / wt%, approx. 15 wt / wt% to approx. 35 wt / wt%, approx. 15 wt / wt% to approx. 45 wt / wt%, approx. 15 wt / wt% to approx. 55 wt / wt%, approx. 15 wt / wt% to approx. 65wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%, approx. 45wt / wt%~approx. 85wt / wt%, approx. 45wt / wt%~approx. 95wt / wt%, approx. 55wt / wt%~approx. 65wt / wt%, approx. 55wt / wt%~approx. 75wt / wt%, approx. 55wt / wt%~approx. 85wt / wt%.Approximately 55wt / wt% to approximately 95wt / wt%, approximately 65wt / wt% to approximately 75wt / wt%, approximately 65wt / wt% to approximately 85wt / wt%, approximately 65wt / wt% to approximately 95wt / %, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt% of a compound of the present disclosure. ,

[0148] In some embodiments, the compositions of the Disclosure contain about 50 wt / wt% of the Compounds of the Disclosure. In some embodiments, the compositions contain about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt% of the Compounds of the Disclosure.

[0149] In another embodiment, the composition of the Disclosure comprises the compound of the Disclosure and one or more elastomers.

[0150] As used herein, the term “elastomer” refers to a viscoelastic (i.e., having both viscosity and elasticity) polymer that typically has low intermolecular forces, a low Young's modulus, and a high fracture strain. Elastomers can typically be crosslinked by heating in the presence of one or more crosslinking agents, a process called curing or vulcanization. Rubber is one 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 a naturally occurring elastomer that can be obtained from the Hevea rubber tree. Non-limiting types of synthetic rubber include unsaturated rubber, saturated rubber, rubber having fluoro and fluoroalkyl or fluoroalkoxy substituents on the polymer chain (FKM), silicone rubber (Q), or blends thereof. Non-exclusive examples of unsaturated rubbers include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), and blends thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions, which lead to hardening of aged portions. When oxidation occurs, these vulcanized products harden and eventually become brittle. Partial oxidation of vulcanized products results in reduced performance when used in applications such as vehicle tire sidewalls. Saturated rubber is a type of rubber that does not contain C=C unsaturated rubber and includes, but is not limited to, acrylic rubber (ACM), chlorinated polyethylene (CM), chlorosulfonated polyethylene (CSM), polychloromethyloxirane (CO), ethylene-ethyl acrylate copolymer (EAM), epichlorohydrin rubber (ECO), ethylene propylene rubber (EPM), ethylene vinyl acetate copolymer (EVM), rubber having fluoro and fluoroalkyl or fluoroalkoxy substituents on the polymer chain (FKM), silicone rubber (Q), or blends thereof.

[0151] 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 naturally occurring elastomers that can be obtained from “non-hevea” sources. In some embodiments, the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

[0152] In some embodiments, one or more elastomers further comprise recycled rubber. As used herein, the term “recycled rubber” refers to elastomers recycled from scrap materials such as used tires.

[0153] The composition of the invention is in the form of the present invention, and the composition is about 15wt / wt%~about 85wt / wt% or more. The actual form of this composition is approximately 1 wt / wt% to 5 wt / wt%, approximately 1 wt / wt% to 15 wt / wt%, approximately 1 wt / wt% to 25 wt / wt%, approximately 1 wt / wt% to 35 wt / wt%, approximately 1 wt / wt% to 45 wt / wt%, approximately 1 wt / wt% to 55 wt / wt%, approximately 1 wt / wt% to 65 wt / wt%, approximately 1 wt / wt% to 75 wt / wt%, approximately 1 wt / wt% to 85 wt / wt%, approximately 1 wt / wt% to 95 wt / wt%, approximately 5 wt / wt% to 15 wt / wt%, approximately 5 wt / wt%. ~approx. 25 wt / wt%, approx. 5 wt / wt% to approx. 35 wt / wt%, approx. 5 wt / wt% to approx. 45 wt / wt%, approx. 5 wt / wt% to approx. 55 wt / wt%, approx. 5 wt / wt% to approx. 65 wt / wt%, approx. 5 wt / wt% to approx. 75 wt / wt%, approx. 5 wt / wt% to approx. 85 wt / wt%, approx. 5 wt / wt% to approx. 95 wt / wt%, approx. 15 wt / wt% to approx. 25 wt / wt%, approx. 15 wt / wt% to approx. 35 wt / wt%, approx. 15 wt / wt% to approx. 45 wt / wt%, approx. 15 wt / wt% to approx. 55 wt / wt%, approx. 15 wt / wt% to approx. 65wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%, approx. 45wt / wt%~approx. 85wt / wt%, approx. 45wt / wt%~approx. 95wt / wt%, approx. 55wt / wt%~approx. 65wt / wt%, approx. 55wt / wt%~approx. 75wt / wt%, approx. 55wt / wt%~approx. 85wt / wt%.It contains one or more elastomers in the following concentrations: approximately 55 wt / wt% to approximately 95 wt / wt%, approximately 65 wt / wt% to approximately 75 wt / wt%, approximately 65 wt / wt% to approximately 85 wt / wt%, approximately 65 wt / wt% to approximately 95 wt / wt%, approximately 75 wt / wt% to approximately 85 wt / wt%, approximately 75 wt / wt% to approximately 95 wt / wt%, or approximately 85 wt / wt% to approximately 95 wt / wt%.

[0154] In some embodiments, the compositions of the present disclosure include one or more elastomers in an amount of about 50 wt / wt%. In some embodiments, the compositions include one or more elastomers in an amount of about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0155] As used herein, the term "phr" refers to parts per 100 parts by weight of rubber. The parts by weight of individual components is based on 100 parts by weight of the total mass of one or more elastomers present in the composition.

[0156] In some embodiments, the compositions of the present disclosure comprise from about 1 phr to about 5 phr of the compounds of the present disclosure. In some embodiments, the composition comprises from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 0.5 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 2 phr, from about 0.01 phr to about 3 phr, from about 0.01 phr to about 4 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.01 phr to about 20 phr, from about 0.1 phr to about 0.5 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 2 phr, from about 0.1 phr to about 3 phr, from about 0.1 phr to about 4 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 20 phr, from about 1 phr to about 2 phr, from about 1 phr to about 3 phr, from about 1 phr to about 4 phr, from about 1 phr to about 7.5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 20 phr, from about 2 phr to about 3 phr, from about 2 phr to about 4 phr, from about 2 phr to about 5 phr, from about 2 phr to about 7.5 phr, from about 2 phr to about 10 phr, from about 2 phr to about 20 phr, from about 3 phr to about 4 phr, from about 3 phr to about 5 phr, from about 3 phr to about 7.5 phr, from about 3 phr to about 10 phr, from about 3 phr to about 20 phr, from about 4 phr to about 5 phr, from about 4 phr to about 7.5 phr, from about 4 phr to about 10 phr, from about 4 phr to about 20 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, from about 5 phr to about 20 phr, from about 7.5 phr to about 10 phr, from about 7.5 phr to about 20 phr, or from about 10 phr to about 20 phr of the compounds of the present disclosure.

[0157] In some embodiments, the compositions of the present disclosure comprise about 3 phr of the compounds of the present 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 compounds of the present disclosure.

[0158] In some embodiments, the compositions of the present disclosure comprise the compounds of the present disclosure and one or more fillers.

[0159] As used herein, the term "filler" refers to a substance that strengthens an elastomeric composition or imparts other properties, 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 (CNT), carbon fibers (HCF), graphite, graphene, aluminosilicates, starch, and fibers, as well as combinations thereof.

[0160] In some embodiments, the filler is derived from a natural source. For example, silica can be derived from rice husks.

[0161] The shape of the product, the composition of this disclosure, and the filling content of about 15wt / wt% to about 85wt / wt% or more. The actual form of this composition is approximately 1 wt / wt% to 5 wt / wt%, approximately 1 wt / wt% to 15 wt / wt%, approximately 1 wt / wt% to 25 wt / wt%, approximately 1 wt / wt% to 35 wt / wt%, approximately 1 wt / wt% to 45 wt / wt%, approximately 1 wt / wt% to 55 wt / wt%, approximately 1 wt / wt% to 65 wt / wt%, approximately 1 wt / wt% to 75 wt / wt%, approximately 1 wt / wt% to 85 wt / wt%, approximately 1 wt / wt% to 95 wt / wt%, approximately 5 wt / wt% to 15 wt / wt%, approximately 5 wt / wt%. ~approx. 25 wt / wt%, approx. 5 wt / wt% to approx. 35 wt / wt%, approx. 5 wt / wt% to approx. 45 wt / wt%, approx. 5 wt / wt% to approx. 55 wt / wt%, approx. 5 wt / wt% to approx. 65 wt / wt%, approx. 5 wt / wt% to approx. 75 wt / wt%, approx. 5 wt / wt% to approx. 85 wt / wt%, approx. 5 wt / wt% to approx. 95 wt / wt%, approx. 15 wt / wt% to approx. 25 wt / wt%, approx. 15 wt / wt% to approx. 35 wt / wt%, approx. 15 wt / wt% to approx. 45 wt / wt%, approx. 15 wt / wt% to approx. 55 wt / wt%, approx. 15 wt / wt% to approx. 65wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%, approx. 45wt / wt%~approx. 85wt / wt%, approx. 45wt / wt%~approx. 95wt / wt%, approx. 55wt / wt%~approx. 65wt / wt%, approx. 55wt / wt%~approx. 75wt / wt%, approx. 55wt / wt%~approx. 85wt / wt%.It contains one or more fillers in the following proportions: approximately 55 wt / wt% to approximately 95 wt / wt%, approximately 65 wt / wt% to approximately 75 wt / wt%, approximately 65 wt / wt% to approximately 85 wt / wt%, approximately 65 wt / wt% to approximately 95 wt / wt%, approximately 75 wt / wt% to approximately 85 wt / wt%, approximately 75 wt / wt% to approximately 95 wt / wt%, or approximately 85 wt / wt% to approximately 95 wt / wt%.

[0162] In some embodiments, the compositions of the present disclosure include one or more fillers in an amount of about 50 wt / wt%. In some embodiments, the compositions include one or more fillers in an amount of about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0163] In some embodiments, the composition of the present disclosure comprises one or more fillers ranging from 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, and 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, about 100 phr to about 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, Approx. 150phr~Approx. 250phr, Approx. 150phr~Approx. 300phr, Approx. 150phr~Approx. 350phr, Approx. 150phr~Approx. 400phr, Approx. 150phr~Approx. 450phr, Approx. , about 200 phr to about 300 phr, about 200 phr to about 350 phr, about 200 phr to about 400 phr, about 200 phr to about 450 phr, about 200 phr to about 500 phr, about 250 phr to about 300 phr, about 250 phr to about 350 phr It contains one or more fillers of approximately 250 phr to 400 phr, approximately 250 phr to 450 phr, approximately 250 phr to 500 phr, approximately 300 phr to 350 phr, approximately 300 phr to 400 phr, approximately 300 phr to 450 phr, approximately 300 phr to 500 phr, approximately 350 phr to 400 phr, approximately 350 phr to 450 phr, approximately 350 phr to 500 phr, approximately 400 phr to 450 phr, approximately 400 phr to 500 phr, or approximately 450 phr to 500 phr.

[0164] In some embodiments, the compositions of the present disclosure include one or more fillers in an amount of about 300 phr. In some embodiments, the compositions include one or more fillers in an amount 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.

[0165] In some embodiments, the compositions of the Disclosure comprise the compounds of the Disclosure and one or more rubber chemicals. As used herein, the term “rubber chemical” refers to a compound or substance used to accelerate the vulcanization of rubber. Examples of rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and pre-vulcanization inhibitors.

[0166] As used herein, the term "vulcanization" refers to the process of forming crosslinks between elastomers to alter the material properties of the elastomer. In particular, vulcanization typically increases the stiffness and durability of the elastomer. Vulcanization is carried out at room temperature or high temperature, depending on the properties of the elastomer, filler, and rubber chemicals used. The term "curing" is also used in the art to describe this process.

[0167] As used herein, the term “vulcanizing agent” refers to any substance that enables crosslinking between elastomers. Vulcanizing agents can enable crosslinking between separate polymer chains of elastomers by various mechanisms, including, but not limited to, forming covalent bonds between the vulcanizing agent and two or more separate polymer chains, or generating radical species on separate polymer chains that can be combined to form covalent bonds between two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, vulcanizing vegetable oils, fungi, and resins. Non-limiting examples of sulfur include octa-sulfur (S8), cyclododeculfur (S8), and cyclododeculfur (S8). 12Examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexine (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). Examples of resins include binding resins. As used herein, the term “binding resin” refers to chemical substances such as resorcinol formaldehyde resins and phenolic resins that react with a methylene donor (e.g., hexamethylenetetramine (HMTA) or hexamethoxymethylmelamine (HMMM)) to promote adhesion.

[0168] As used herein, the term “accelerator” refers to any substance that increases the rate of vulcanization. In some embodiments, accelerators enable vulcanization to be carried out at a lower temperature and / or enable the more efficient use of vulcanizing agents, such as sulfur. Non-limiting examples of accelerators include guanidine, thiazole, sulfenamide, thiuram, dithiocarbamate, xanthate, and thiophosphate. 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 sulfenimide (TBSI). Non-limiting examples of sulfenamides include N-tert-butyl-2-benzothiadylsulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydiethylenebenzothiazolesulfenamide (OBTS), N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide (OTOS), and thiocarbamylsulfenamides. Non-limiting examples of thiuram include dimethylcarbamothioic acid dithioperoxyanhydride (thiuram), dipentamethylenethiuram tetrasulfide (DPIT), tetrabenzylthiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-exclusive examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), telluride diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).

[0169] As used herein, the term “activator” refers to any substance that activates a vulcanizing agent, enabling the crosslinking of the elastomer as described above. Activators may act through a variety of mechanisms, including, but not limited to, forming a chemical complex with an accelerator, or (when sulfur is used as a vulcanizing agent) coordinating with sulfur. 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.

[0170] As used herein, the term “pre-vulcanization inhibitor” refers to a compound that delays the initiation and / or rate of vulcanization. These compounds are also referred to as “delays.” Non-exclusive examples of pre-vulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.

[0171] The composition of the invention is in the form of the present disclosure, and the product contains about 15wt / wt% to about 85wt / wt% or more. The actual form of this composition is approximately 1 wt / wt% to 5 wt / wt%, approximately 1 wt / wt% to 15 wt / wt%, approximately 1 wt / wt% to 25 wt / wt%, approximately 1 wt / wt% to 35 wt / wt%, approximately 1 wt / wt% to 45 wt / wt%, approximately 1 wt / wt% to 55 wt / wt%, approximately 1 wt / wt% to 65 wt / wt%, approximately 1 wt / wt% to 75 wt / wt%, approximately 1 wt / wt% to 85 wt / wt%, approximately 1 wt / wt% to 95 wt / wt%, approximately 5 wt / wt% to 15 wt / wt%, approximately 5 wt / wt%. ~approx. 25 wt / wt%, approx. 5 wt / wt% to approx. 35 wt / wt%, approx. 5 wt / wt% to approx. 45 wt / wt%, approx. 5 wt / wt% to approx. 55 wt / wt%, approx. 5 wt / wt% to approx. 65 wt / wt%, approx. 5 wt / wt% to approx. 75 wt / wt%, approx. 5 wt / wt% to approx. 85 wt / wt%, approx. 5 wt / wt% to approx. 95 wt / wt%, approx. 15 wt / wt% to approx. 25 wt / wt%, approx. 15 wt / wt% to approx. 35 wt / wt%, approx. 15 wt / wt% to approx. 45 wt / wt%, approx. 15 wt / wt% to approx. 55 wt / wt%, approx. 15 wt / wt% to approx. 65wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%, approx. 45wt / wt%~approx. 85wt / wt%, approx. 45wt / wt%~approx. 95wt / wt%, approx. 55wt / wt%~approx. 65wt / wt%, approx. 55wt / wt%~approx. 75wt / wt%, approx. 55wt / wt%~approx. 85wt / wt%.Contains one or more rubber chemicals in the following concentrations: approximately 55 wt / wt% to approximately 95 wt / wt%, approximately 65 wt / wt% to approximately 75 wt / wt%, approximately 65 wt / wt% to approximately 85 wt / wt%, approximately 65 wt / wt% to approximately 95 wt / wt%, approximately 75 wt / wt% to approximately 85 wt / wt%, approximately 75 wt / wt% to approximately 95 wt / wt%, or approximately 85 wt / wt% to approximately 95 wt / wt%.

[0172] In some embodiments, the compositions of the present disclosure contain one or more rubber chemicals in about 15 wt / wt%. In some embodiments, the compositions contain one or more rubber chemicals in about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0173] In some embodiments, the compositions of the present disclosure contain one or more rubber chemicals ranging from about 1 phr to about 20 phr. In some embodiments, the compositions contain 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, and about 1 phr to about 5 phr. hr, 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 phr to approximately 40 phr, approximately 10 phr to approximately 15 phr, approximately 10 phr to approximately 20 phr, approximately 10 phr to approximately 25 phr, approximately 10 phr to approximately 30 phr, approximately 10 phr to approximately 35 phr, approximately 10 phr to approximately 40 phr, approximately 15 phr to approximately 20 phr, approximately 15 phr to approximately 25 phr, approximately 15 phr to approximately 30 phr, approximately 15 phr to approximately 35 phr, approximately 15 phr to approximately Contains one or more rubber chemicals in the following concentrations: 40 phr, approximately 20 phr to 25 phr, approximately 20 phr to 30 phr, approximately 20 phr to 35 phr, approximately 20 phr to 40 phr, approximately 25 phr to 30 phr, approximately 25 phr to 35 phr, approximately 25 phr to 40 phr, approximately 30 phr to 35 phr, approximately 30 phr to 40 phr, or approximately 35 phr to 40 phr.

[0174] In some embodiments, the compositions of the present disclosure include one or more rubber chemicals in about 10 phr. In some embodiments, the compositions include one or more rubber chemicals in 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.

[0175] As used herein, the term “plasticizer” refers to processing aids used to reduce the viscosity, increase the plasticity, and / or increase the volume of a composition. Plasticizers facilitate the process of mixing and forming compositions containing elastomers before the composition is vulcanized. Non-limiting examples of plasticizers include mineral oils (paraffinic, aromatic, or naphthenic), organic esters, resins, waxes, ester plasticizers, and naturally derived oils, such as soybean oil, vegetable oil, or orange oil.

[0176] The shape of the product is the same, the composition of this disclosure is about 15wt / wt% to about 85wt / wt%, and the plasticity content is more than 15wt / wt%. The actual form of this composition is approximately 1 wt / wt% to 5 wt / wt%, approximately 1 wt / wt% to 15 wt / wt%, approximately 1 wt / wt% to 25 wt / wt%, approximately 1 wt / wt% to 35 wt / wt%, approximately 1 wt / wt% to 45 wt / wt%, approximately 1 wt / wt% to 55 wt / wt%, approximately 1 wt / wt% to 65 wt / wt%, approximately 1 wt / wt% to 75 wt / wt%, approximately 1 wt / wt% to 85 wt / wt%, approximately 1 wt / wt% to 95 wt / wt%, approximately 5 wt / wt% to 15 wt / wt%, approximately 5 wt / wt%. ~approx. 25 wt / wt%, approx. 5 wt / wt% to approx. 35 wt / wt%, approx. 5 wt / wt% to approx. 45 wt / wt%, approx. 5 wt / wt% to approx. 55 wt / wt%, approx. 5 wt / wt% to approx. 65 wt / wt%, approx. 5 wt / wt% to approx. 75 wt / wt%, approx. 5 wt / wt% to approx. 85 wt / wt%, approx. 5 wt / wt% to approx. 95 wt / wt%, approx. 15 wt / wt% to approx. 25 wt / wt%, approx. 15 wt / wt% to approx. 35 wt / wt%, approx. 15 wt / wt% to approx. 45 wt / wt%, approx. 15 wt / wt% to approx. 55 wt / wt%, approx. 15 wt / wt% to approx. 65wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%, approx. 45wt / wt%~approx. 85wt / wt%, approx. 45wt / wt%~approx. 95wt / wt%, approx. 55wt / wt%~approx. 65wt / wt%, approx. 55wt / wt%~approx. 75wt / wt%, approx. 55wt / wt%~approx. 85wt / wt%.It contains one or more plasticizers in the following proportions: approximately 55 wt / wt% to approximately 95 wt / wt%, approximately 65 wt / wt% to approximately 75 wt / wt%, approximately 65 wt / wt% to approximately 85 wt / wt%, approximately 65 wt / wt% to approximately 95 wt / wt%, approximately 75 wt / wt% to approximately 85 wt / wt%, approximately 75 wt / wt% to approximately 95 wt / wt%, or approximately 85 wt / wt% to approximately 95 wt / wt%.

[0177] In some embodiments, the compositions of the present disclosure contain one or more plasticizers in about 15 wt / wt%. In some embodiments, the compositions contain one or more plasticizers in about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0178] In some embodiments, the compositions of the present disclosure contain one or more plasticizers in amounts of about 1 phr to about 20 phr. In some embodiments, the compositions contain 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, and about 1 phr to about 5 phr. hr, 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 phr to approximately 40 phr, approximately 10 phr to approximately 15 phr, approximately 10 phr to approximately 20 phr, approximately 10 phr to approximately 25 phr, approximately 10 phr to approximately 30 phr, approximately 10 phr to approximately 35 phr, approximately 10 phr to approximately 40 phr, approximately 15 phr to approximately 20 phr, approximately 15 phr to approximately 25 phr, approximately 15 phr to approximately 30 phr, approximately 15 phr to approximately 35 phr, approximately 15 phr to approximately It contains one or more plasticizers in the following amounts: 40 phr, approximately 20 phr to approximately 25 phr, approximately 20 phr to approximately 30 phr, approximately 20 phr to approximately 35 phr, approximately 20 phr to approximately 40 phr, approximately 25 phr to approximately 30 phr, approximately 25 phr to approximately 35 phr, approximately 25 phr to approximately 40 phr, approximately 30 phr to approximately 35 phr, approximately 30 phr to approximately 40 phr, or approximately 35 phr to approximately 40 phr.

[0179] In some embodiments, the compositions of the present disclosure contain one or more plasticizers in about 10 phr. In some embodiments, the compositions contain one or more plasticizers in 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.

[0180] In some embodiments, the compositions of the Disclosure further comprise one or more additional degradation inhibitors that are not compounds of the Disclosure. In some embodiments, the one or more additional degradation inhibitors are antioxidants. In some embodiments, the one or more additional degradation inhibitors are anti-ozone agents. Non-limiting examples of degradation inhibitors include paraphenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), diphenylamine-ketone condensates, and natural degradation inhibitors. Non-limiting examples of PPD include N 1 -(4-methylpentan-2-yl)-N 4 -Phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N 1 -phenyl-N 4 Examples include -(propan-2-yl)benzene-1,4-diamine (IPPD), N,N'-di-sec-butyl-p-phenylenediamine (44PD), N,N'-bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD), and N-N'-dioctyl-p-phenylenediamine (88PD). Non-limiting examples of TMQ include 2,2,4-trimethyl-1,2-dihydroquinoline and its oligomers or polymers.

[0181] The application form and composition of this disclosure include about 15wt / wt% to about 85wt / wt% and above, and additional deterioration prevention means. The actual form of this composition is approximately 1 wt / wt% to 5 wt / wt%, approximately 1 wt / wt% to 15 wt / wt%, approximately 1 wt / wt% to 25 wt / wt%, approximately 1 wt / wt% to 35 wt / wt%, approximately 1 wt / wt% to 45 wt / wt%, approximately 1 wt / wt% to 55 wt / wt%, approximately 1 wt / wt% to 65 wt / wt%, approximately 1 wt / wt% to 75 wt / wt%, approximately 1 wt / wt% to 85 wt / wt%, approximately 1 wt / wt% to 95 wt / wt%, approximately 5 wt / wt% to 15 wt / wt%, approximately 5 wt / wt%. ~approx. 25 wt / wt%, approx. 5 wt / wt% to approx. 35 wt / wt%, approx. 5 wt / wt% to approx. 45 wt / wt%, approx. 5 wt / wt% to approx. 55 wt / wt%, approx. 5 wt / wt% to approx. 65 wt / wt%, approx. 5 wt / wt% to approx. 75 wt / wt%, approx. 5 wt / wt% to approx. 85 wt / wt%, approx. 5 wt / wt% to approx. 95 wt / wt%, approx. 15 wt / wt% to approx. 25 wt / wt%, approx. 15 wt / wt% to approx. 35 wt / wt%, approx. 15 wt / wt% to approx. 45 wt / wt%, approx. 15 wt / wt% to approx. 55 wt / wt%, approx. 15 wt / wt% to approx. 65wt / wt%, about 15wt / wt% to about 75wt / wt%, about 15wt / wt% to about 95wt / wt%, about 25wt / wt% to about 35wt / wt%, about 25wt / wt% to about 45wt / wt%, about 25wt / wt% to about 55wt / wt%, about 25wt / wt% to about 65wt / wt%, about 25wt / wt% to about 75wt / wt%, about 25wt / wt% to about 85wt / wt%, about 25wt / wt% to about 95wt / wt%, about 35wt / wt% to about 45wt / wt%, about 35wt / wt% to about 55wt / wt%, about 35wt / wt% / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%, approx. 45wt / wt%~approx. 85wt / wt%, approx. 45wt / wt%~approx. 95wt / wt%, approx. 55wt / wt%~approx. 65wt / wt%, approx. 55wt / wt%~approx. 75wt / wt%, approx. 55wt / wt%~approx. 85wt / wt%.It includes one or more additional anti-degradants of about 55 wt / wt% to about 95 wt / wt%, about 65 wt / wt% to about 75 wt / wt%, about 65 wt / wt% to about 85 wt / wt%, about 65 wt / wt% to about 95 wt / wt%, about 75 wt / wt% to about 85 wt / wt%, about 75 wt / wt% to about 95 wt / wt%, or about 85 wt / wt% to about 95 wt / wt%.

[0182] In some embodiments, the composition of the present disclosure includes one or more additional anti-degradants of about 15 wt / wt%. In some embodiments, the composition includes one or more additional anti-degradants of about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0183] In some embodiments, the composition of the present disclosure includes one or more additional anti-degradants of about 1 to about 5 phr. In some embodiments, the composition includes one or more additional anti-degradants of about 0.001 phr to about 0.01 phr, about 0.001 phr to about 0.1 phr, about 0.001 phr to about 1 phr, about 0.001 phr to about 5 phr, about 0.001 phr to about 7.5 phr, about 0.001 phr to about 10 phr, about 0.01 phr to about 0.1 phr, about 0.01 phr to about 1 phr, about 0.01 phr to about 5 phr, about 0.01 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, or about 7.5 phr to about 10 phr.

[0184] In some embodiments, the compositions of the present disclosure include one or more additional degradation inhibitors in an amount of about 3 phr. In some embodiments, the compositions include one or more additional degradation inhibitors in an amount of 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.

[0185] In some embodiments, the Disclosure provides compositions comprising the compounds of the Disclosure and one or more carriers. As used herein, the term "carrier" refers to a solid capable of adsorbing a liquid 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 large surface area. In some embodiments, the carrier comprises particles having a diameter of less than 500 microns.

[0186] In some embodiments, the composition comprises one or more carriers in an amount of from about 15 wt / wt% to about 85 wt / wt%. In some embodiments, the composition is from about 1 wt / wt% to about 5 wt / wt%, from about 1 wt / wt% to about 15 wt / wt%, from about 1 wt / wt% to about 25 wt / wt%, from about 1 wt / wt% to about 35 wt / wt%, from about 1 wt / wt% to about 45 wt / wt%, from about 1 wt / wt% to about 55 wt / wt%, from about 1 wt / wt% to about 65 wt / wt%, from about 1 wt / wt% to about 75 wt / wt%, from about 1 wt / wt% to about 85 wt / wt%, from about 1 wt / wt% to about 95 wt / wt%, from about 5 wt / wt% to about 15 wt / wt%, from about 5 wt / wt% to about 25 wt / wt%, from about 5 wt / wt% to about 35 wt / wt%, from about 5 wt / wt% to about 45 wt / wt%, from about 5 wt / wt% to about 55 wt / wt%, from about 5 wt / wt% to about 65 wt / wt%, from about 5 wt / wt% to about 75 wt / wt%, from about 5 wt / wt% to about 85 wt / wt%, from about 5 wt / wt% to about 95 wt / wt%, from about 15 wt / wt% to about 25 wt / wt%, from about 15 wt / wt% to about 35 wt / wt%, from about 15 wt / wt% to about 45 wt / wt%, from about 15 wt / wt% to about 55 wt / wt%, from about 15 wt / wt% to about 65 wt / wt%, from about 15 wt / wt% to about 75 wt / wt%, from about 15 wt / wt% to about 95 wt / wt%, from about 25 wt / wt% to about 35 wt / wt%, from about 25 wt / wt% to about 45 wt / wt%, from about 25 wt / wt% to about 55 wt / wt%, from about 25 wt / wt% to about 65 wt / wt%, from about 25 wt / wt% to about 75 wt / wt%, from about 25 wt / wt% to about 85 wt / wt%, from about 25 wt / wt% to about 95 wt / wt%, from about 35 wt / wt% to about 45 wt / wt%, from about 35 wt / wt% to about 55 wt / wt%, from about 35 wt / wt% to about 65 wt / wt%, from about 35 wt / wt% to about 75 wt / wt%, from about 35 wt / wt% to about 85 wt / wt%, from about 35 wt / wt% to about 95 wt / wt%, from about 45 wt / wt% to about 55 wt / wt%, from about 45 wt / wt% to about 65 wt / wt%, from about 45 wt / wt% to about 75 wt / wt%, from about 45 wt / wt% to about 85 wt / wt%, from about 45 wt / wt% to about 95 wt / wt%, from about 55 wt / wt% to about 65 wt / wt%, from about 55 wt / wt% to about 75 wt / wt%, from about 55 wt / wt% to about 85 wt / wt%,Contains one or more carriers of approximately 55 wt / wt% to 95 wt / wt%, approximately 65 wt / wt% to 75 wt / wt%, approximately 65 wt / wt% to 85 wt / wt%, approximately 65 wt / wt% to 95 wt / wt%, approximately 75 wt / wt% to 85 wt / wt%, approximately 75 wt / wt% to 95 wt / wt%, or approximately 85 wt / wt% to 95 wt / wt%.

[0187] In some embodiments, the composition comprises one or more carriers in an amount of about 15 wt / wt%. In some embodiments, the composition comprises one or more carriers in an amount of about 1 wt / wt%, about 5 wt / wt%, about 10 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0188] The Disclosure also provides a process for preparing a composition comprising the compound of the Disclosure and one or more carriers, the process comprising mixing the compound and one or more carriers.

[0189] This disclosure also provides lubricant compositions comprising the compounds and lubricants of this disclosure. Non-limiting examples of lubricants include mineral oils, high molecular weight petroleum distillates, e.g., aromatic, naphthenic, and paraffinic distillates; synthetic oils, e.g., polyalphaolefins (PAO), synthetic esters, polyalkylene glycols (PAG), phosphate esters, perfluoropolyethers (PFPE), alkylated naphthalenes (AN), silicate esters, ionic fluids, and multiple alkylated cyclopentanes (MAC); solid lubricants, e.g., polytetrafluoroethylene (PTFE), graphite, hexagonal boron nitride, molybdenum disulfide, tungsten disulfide; aqueous lubricants, e.g., hydrated brush polymers; and biolubricants, e.g., triglyceride esters, high oleic canola oil, castor oil, palm oil, sunflower seed oil, and rapeseed oil.

[0190] This disclosure also provides flammable fuels and flammable fuel compositions comprising compounds of this disclosure. Non-limiting examples of flammable fuels include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuels, and biodiesel.

[0191] This disclosure also provides fuel additives and fuel additive compositions comprising compounds of this disclosure. Non-limiting examples of fuel additives include oxygenated substances such as alcohols and ethers, antioxidants, stabilizers, detergents, knock inhibitors, lead scavengers, fuel dyes, viscosity modifiers, and butyl rubber. In some embodiments, the butyl rubber is in the form of polyisobutylene succinimide. In some embodiments, the butyl rubber is added as a detergent to prevent fouling of diesel fuel injectors.

[0192] In some embodiments, the present disclosure provides compositions listed in Table 2. [Table 2]

[0193] In some embodiments, the vulcanized tire or other rubber article compositions of Table 2 contain about 0.1 wt / wt%, about 0.2 wt / wt%, about 0.3 wt / wt%, about 0.4 wt / wt%, about 0.5 wt / wt%, about 0.6 wt / wt%, about 0.7 wt / wt%, about 0.8 wt / wt%, about 0.9 wt / wt%, about 1 wt / wt%, about 2 wt / wt%, about 3 wt / wt%, about 4 wt / wt%, about 5 wt / wt%, about 6 wt / wt%, about 7 wt / wt%, about 8 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of the compounds of the Disclosure. In some embodiments, the vulcanized tires or other rubber articles of Table 2 include at least one elastomer in an amount of about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0194] In some embodiments, the unvulcanized tire internal components, or assembled components, or other end-use component compositions in Table 2 are approximately 0.01 wt / wt%, approximately 0.02 wt / wt%, approximately 0.03 wt / wt%, approximately 0.04 wt / wt%, approximately 0.05 wt / wt%, approximately 0.06 wt / wt%, approximately 0.07 wt / wt%, approximately 0.08 wt / wt%, approximately 0.09 wt / wt%, approximately 0.1 wt / wt%, and approximately 0.2 wt / wt%. The compounds disclosed herein are present in amounts of t%, approximately 0.3 wt / wt%, approximately 0.4 wt / wt%, approximately 0.5 wt / wt%, approximately 0.6 wt / wt%, approximately 0.7 wt / wt%, approximately 0.8 wt / wt%, approximately 0.9 wt / wt%, approximately 1 wt / wt%, approximately 2 wt / wt%, approximately 3 wt / wt%, approximately 4 wt / wt%, approximately 5 wt / wt%, approximately 6 wt / wt%, approximately 7 wt / wt%, approximately 8 wt / wt%, approximately 9 wt / wt%, or approximately 10 wt / wt%. In some embodiments, the unvulcanized tire internal components, or assembled components, or other end-use component compositions of Table 2 include, and contain, at least one elastomer in an amount of about 5 wt / wt%, about 10 wt / wt%, about 15 wt / wt%, about 20 wt / wt%, about 25 wt / wt%, about 30 wt / wt%, about 35 wt / wt%, about 40 wt / wt%, about 45 wt / wt%, about 50 wt / wt%, about 55 wt / wt%, about 60 wt / wt%, about 65 wt / wt%, about 70 wt / wt%, about 75 wt / wt%, about 80 wt / wt%, about 85 wt / wt%, about 90 wt / wt%, or about 95 wt / wt%.

[0195] Vulcanized elastomer articles This disclosure also provides vulcanized elastomer articles comprising the compounds of this disclosure. The term “vulcanized elastomer article” refers to an article produced by forming an elastomer-containing composition into a specific shape and vulcanizing the composition to obtain an article.

[0196] This disclosure also provides vulcanized elastomer articles prepared using the compositions described herein.

[0197] In some embodiments, the vulcanized elastomer article 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 construction machine tire, an airplane tire, or a racing tire.

[0198] In some embodiments, the vulcanized elastomer article is a component of the tire. In some embodiments, the component is a bead, belt, body ply, inner liner, sidewall, undertread, or tread.

[0199] In some embodiments, the vulcanized elastomer article is a rubber overshoe, sealing strip, acoustic panel, air spring, bellows, membrane, tactile sensor, crash pad, hose, conveyor belt, or flooring material.

[0200] process This disclosure also provides a process for preparing vulcanized elastomer articles, the process being (a) Forming the compositions described herein into a molded shape, (b) including vulcanizing the formed shape, We provide vulcanized elastomer articles.

[0201] In some embodiments, vulcanization is carried out at an average temperature of about 140°C to about 160°C. In some embodiments, vulcanization is carried out at 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 The process is carried out at an average temperature of 100°C to approximately 200°C, approximately 120°C to approximately 140°C, approximately 120°C to approximately 160°C, approximately 120°C to approximately 180°C, approximately 120°C to approximately 200°C, approximately 140°C to approximately 180°C, approximately 140°C to approximately 200°C, approximately 160°C to approximately 180°C, approximately 160°C to approximately 200°C, or approximately 180°C to approximately 200°C.

[0202] 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.

[0203] This disclosure also provides a process for refurbishing tires, and this process is (a) Applying the composition described herein to a tire, (b) Placing a pre-vulcanized tread around the tire, (c) Placing a hardening envelope around the tire, (d) including vulcanizing the tires.

[0204] kit The Disclosure also provides kits containing the compositions described herein, for example, in a form packaged in a container, which facilitate the use of the compounds for practicing the processes and / or methods of the Disclosure. In some embodiments, the kit includes the compositions described herein and instructions for using the compositions in vulcanizable elastomer compositions. In some embodiments, the kit includes the compositions described herein and instructions for using the compositions to prepare vulcanizable elastomer articles. The compositions may be packaged in any suitable container, such as a sealed bottle or container, and a label may be attached to the container or included in a kit describing the compositions and their proper use. [Examples]

[0205] Example 1 Synthesis of N-isopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 1) Step 1 [ka] A 1 L round-bottom flask equipped with an overhead stirrer, thermometer, and reflux condenser was filled with 2-methyl-4-nitroaniline (30 g, 197 mmol) and acetonitrile (320 mL). The mixture was stirred under N2 protection. To the resulting clear yellow solution, trifluoroacetic acid (16.0 mL, 209 mmol), 37% formaldehyde aqueous solution (26.0 mL, 349 mmol HCHO), and α-methylstyrene (46.0 mL, 354 mmol) were added in that order. The reaction mixture (slurry formed after the addition of formaldehyde) was refluxed for 2 hours (internal temperature = 77-78°C), where a clear yellow solution was formed. After cooling to room temperature, 1 mol / L sodium bicarbonate aqueous solution (300 mL) was added in several portions. The resulting two-phase system was stirred until CO2 evolution stopped, and then transferred to a 2 L separatory funnel. Ethyl acetate (700 mL) was added. After shaking and decantation, the aqueous phase was discarded. The organic phase was washed with 1 mol / L sodium bisulfite aqueous solution (300 mL) and saturated sodium chloride aqueous solution (300 mL), dried over anhydrous magnesium sulfate, filtered, and volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). The resulting dark oil (69.5 g) was diluted with a mixture of isopropanol (100 mL) and hexane (20 mL). The mixture was swirled until homogenized, then held overnight at -20°C, where a yellow solid separated. The yellow solid was collected by vacuum filtration (disposable 20 micron polyethylene frit) and washed directly on the frit with hexane (50 mL). The moist material was dried in a vacuum oven at 45-50°C for several hours, then at room temperature overnight, to obtain 24.1 g of 4,8-dimethyl-6-nitro-4-phenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 1-I) as a yellow powder. Intermediate compound 1-I was then processed as shown in Figures 1 and 2, respectively. 1 H and 13 The 13C sample was characterized by nuclear magnetic resonance (NMR) spectroscopy. LC-UV analysis showed a purity of 93.4% at 260 nm detection, as shown in Figure 3.

[0206] Step 2 [ka] A 300 mL Parr autoclave was packed with intermediate compound 1-I (23.0 g, 81.5 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.4077 g wet), isopropanol (201 mL), and acetone (10.4 mL, 142 mmol). The reaction mixture was stirred and heated to 120 °C under 250 PSI of H2, and held for 1.5 hours. After cooling to room temperature, the reaction mixture was filtered through an in-line 0.2 micron frit. The autoclave was rinsed with fresh isopropanol (approximately 200 mL), and the resulting mixture was filtered through an in-line 0.2 micron frit. The combined filtrate was filtered through filter paper, and its volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50 °C). The resulting crude material (light brown oil) weighed 23.7 g. After being left at room temperature for several weeks, the oil solidified as a dark solid mass. After cooling to -20°C overnight, the solid mass was broken up with a spatula. To the resulting dark powder, a mixture of ethyl acetate and hexane (10 mL and 51 mL, respectively) was added. The resulting slurry was magnetically stirred at room temperature for 4 days under N2 protection. The solid was collected by vacuum filtration using disposable 0.2 micron polyethylene frit and rapidly rinsed in several portions with hexane (50 mL total). The wet powder (16.58 g) was dried under vacuum at 50-60°C for several hours, then at room temperature overnight, to obtain 14.48 g of N-isopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 1) (60% relative to intermediate compound 1-I) as a light brown powder. Compound 1 was prepared as shown in Figure 4. 13 Characterized by 13C NMR spectroscopy. LC-UV analysis showed a purity of 96.5% at 260 nm detection, as shown in Figure 5. Mass (m / z): 295.4 [M+1] + .

[0207] Example 2 Synthesis of 4,8-dimethyl-N-(pentan-3-yl)-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 2) [ka] A 300 mL Parr autoclave was packed with intermediate compound 1-I (12.0 g, 42.5 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.42 g wet), 3-pentanone (180 mL, 1.70 mol), and 5 wt% aqueous phosphoric acid solution (1.8 g solution, 0.92 mmol H3PO4). The reaction mixture was stirred and heated to 150 °C under 250 PSI of H2, and held for 2 hours. After cooling to room temperature, the reaction mixture was filtered through an in-line 0.2 micron frit. The autoclave was rinsed with isopropanol (approximately 150-200 mL), and the resulting mixture was filtered through an in-line 0.2 micron frit. The combined filtrate was removed under reduced pressure to remove volatile substances (rotary evaporator, water bath = 50 °C). The resulting residue was dissolved in hexane (14 mL), where trace amounts of insoluble material were separated. The mixture was vacuum filtered through Celite S, and the cake was rinsed with hexane (100 mL). The combined filtrate was removed under reduced pressure to remove volatile substances (rotary evaporator, water bath = 50°C). Drying overnight under vacuum at 60°C yielded 12.5 g of brown oil, which darkened over time after being left at room temperature, yielding 4,8-dimethyl-N-(pentan-3-yl)-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 2). Compound 2 was converted as shown in Figure 6. 13 Characterized by 13C NMR spectroscopy. LC-UV analysis showed a purity of 91.0% at detection at 260 nm, as shown in Figure 7. Mass (m / z), 323.4 [M+1] + .

[0208] Example 3 Synthesis of N-isopropyl-4,8-dimethyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 3) Step 1 [ka] A 1 L round-bottom flask equipped with a stirring rod, thermometer, and reflux condenser was filled with 2-methyl-4-nitroaniline (9.96 g, 65.5 mmol) and acetonitrile (200 mL). The mixture was stirred under an N2 blanket. To the resulting clear yellow solution, trifluoroacetic acid (5.3 mL, 68.7 mmol), benzaldehyde (6.6 mL, 65.5 mmol), and α-methylstyrene (15.3 mL, 117.9 mmol) were added in that order. The reaction mixture was heated to 82 °C (oil bath temperature) and held for 4 hours. After cooling to room temperature, a yellow precipitate formed. A solution of sodium bicarbonate (10 g) in deionized water (200 mL) was added in several portions. Ethyl acetate (200 mL) was added in several portions to dissolve the precipitate. The resulting two-phase system was transferred to a separatory funnel. The aqueous phase was discarded. The organic phase was washed with a solution of sodium bisulfite (15.0 g) in deionized water (200 mL) and a saturated sodium chloride aqueous solution (200 mL), dried over anhydrous magnesium sulfate, filtered, and volatile substances were removed under reduced pressure (rotary evaporator, water bath = 45°C). The residue was dried under vacuum at 20 mbar and 45°C for 20 minutes. The resulting viscous orange oil was suspended in 1:1 v / v isopropanol:hexane (100 mL) and heated at 55°C for 15 minutes, thereby converting the orange oil into a yellow solid. The mixture was cooled to room temperature and then filtered to isolate the yellow solid. The solid was washed with hexane (3 × 20 mL) and dried on a vacuum filter for approximately 20 minutes to obtain 15.2 g of 4,8-dimethyl-6-nitro-2,4-diphenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 3-I) as a yellow powder. LC-UV analysis showed a purity of 99.0% at 260 nm detection, as shown in Figure 8.

[0209] Step 2 [ka] A 300 mL Parr autoclave was packed with intermediate compound 3-I (10.6 g, 29.7 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.2467 g wet), isopropanol (200 mL), and acetone (5.6 mL, 75.5 mmol). The reaction mixture was stirred and heated to 150 °C under 250 PSI of H2, and held for 107 minutes. After cooling to room temperature, the mixture was filtered through an in-line 0.2 micron frit, the reactor was rinsed with 100 mL of isopropanol, and the combined filtrate was removed under reduced pressure (rotary evaporator, water bath = 50 °C) to obtain a waxy beige solid (10.68 g). The solid was dried under vacuum at 55°C for 16 hours to obtain 9.27 g of N-isopropyl-4,8-dimethyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 3) as a waxy, beige solid. Compound 3 was prepared as shown in Figure 9. 13 Characterized by 13C NMR spectroscopy. LC-UV analysis showed a purity of 94.5% at detection at 260 nm, as shown in Figure 10. Mass (m / z): 371.4 [M+1] + .

[0210] Example 4 Synthesis of N,2-diisopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 4) Step 1 [ka] A 250 mL flask equipped with a stirring rod and reflux condenser was filled with 2-methyl-4-nitroaniline (4.2 g, 27.6 mmol) and acetonitrile (50 mL). The mixture was stirred under N2 protection (dissolving the 2-methyl-4-nitroaniline within a few minutes). Trifluoroacetic acid (2.2 mL, 28.7 mmol), isobutyraldehyde (4.4 mL, 48 mmol), and α-methylstyrene (6.4 mL, 49.2 mmol) were added sequentially to the resulting dark solution. The reaction mixture was heated (oil bath set to 80°C). After reaching the set temperature, it was maintained for 5 hours. After cooling to room temperature (overnight), a solution of sodium bicarbonate (4.75 g, 56.5 mmol) in deionized water (60 mL) was added in small amounts. The resulting two-phase system was stirred until CO2 evolution stopped, ethyl acetate (50 mL) was added, and then the mixture was transferred to a separatory funnel. The flask was rinsed with ethyl acetate (2 × 20 mL). The organic solution was transferred to a separatory funnel. After decantation, the aqueous layer was discarded. The organic layer was washed with saturated sodium bisulfite aqueous solution (30 mL), dried over MgSO4, filtered, and volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). No attempt was made to remove excess α-methylstyrene (BP = 165~169°C). To the obtained low-purity orange oil, weighing approximately 9.9 g, a mixture of hexane (20 mL) and isopropanol (10 mL) was added. After swirling for several seconds, the resulting solution was held at -20°C for 1 hour, where a yellow crystalline solid and a dark, dense mass separated. After warming to room temperature and vigorously swirling, the dark mass disappeared and an additional amount of yellow crystals formed. The solid was collected by vacuum filtration using disposable 0.2 micron polyethylene frit and rapidly rinsed with hexane (10 mL). A moist solid (2.87 g) was dried under vacuum at 50-60°C for several hours, then at room temperature for several hours to obtain 2.78 g of 2-isopropyl-4,8-dimethyl-6-nitro-4-phenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 4-I) as a yellow powder. Intermediate compound 4-I was processed as shown in Figure 11. 13 The sample was characterized by 13C NMR spectroscopy. LC-UV analysis showed a purity of 95.2% at 260 nm detection, as shown in Figure 12.

[0211] Step 2 [ka] A 300 mL Parr autoclave was packed with intermediate compound 4-I (1.6 g, 4.93 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.0366 g wet), isopropanol (130 mL), and acetone (0.99 mL, 13 mmol). The reaction mixture was stirred and heated to 150 °C under 250 PSI of H2, and held for 65–70 minutes. After cooling to room temperature, the reaction mixture was filtered through an in-line 0.2 micron frit. The autoclave was rinsed with fresh isopropanol (150 mL), and the resulting mixture was filtered through an in-line 0.2 micron frit. The combined filtrate was removed under reduced pressure to remove volatile substances (rotary evaporator, water bath = 55 °C). The residue was dissolved in 40% ethyl acetate (5 mL) in hexane. The obtained solution was packed into a 41 mm inner diameter column (silica height = 10-11 cm) pre-prepared with silica gel (ultra-high purity, 60 Å, 60-200 μm) and 20% ethyl acetate in hexane. The column was eluted with 20% ethyl acetate in hexane. Each resulting fraction was analyzed by silica gel TLC (20% ethyl acetate in hexane). f Fractions containing =0.3 were collected, combined, and their volatile substances were removed under reduced pressure (rotary evaporator, water bath = 55°C). The resulting light brown oil was dried under vacuum (rotary evaporator, water bath = 55°C, less than 2 mbars) for 1.5 hours, and then overnight in a vacuum oven at 75-80°C to obtain 1.4 g of N,2-diisopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 4) as a clear, pale orange, very viscous oil. Compound 4 was converted as shown in Figure 13. 13 Characterized by 13C NMR spectroscopy. LC-UV analysis showed a purity of 97.2% at detection at 260 nm, as shown in Figure 14. Mass (m / z), 337.4 [M+1] + .

[0212] Example 5 Synthesis of N-isopropyl-3,3,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 47) Step 1 [ka] A 100 mL flask equipped with a stirring bar and reflux condenser was filled with 2-methyl-4-nitroaniline (3.96 g, 26.0 mmol) and acetonitrile (42 mL). The mixture was stirred under an N2 blanket. To the resulting dark-colored solution, p-toluenesulfonic acid monohydrate (0.486 g, 2.56 mmol of acid), 37% aqueous formaldehyde solution (2.4 mL, 32.2 mmol of HCHO), and isobutyraldehyde (3.7 mL, 41 mmol) were added sequentially. A yellow solid separated after the addition of the formaldehyde solution was obtained. The reaction mixture was stirred for 2 days without external cooling or heating, and a dark-colored solution was obtained. Sodium bicarbonate (0.337 g, 4.01 mmol) was added, and the mixture was stirred for 5-10 minutes. Anhydrous magnesium sulfate was added, and the resulting slurry was stirred for approximately 5 minutes. Insoluble materials were removed by gravimetric filtration using filter paper. The cake was rinsed with acetonitrile. The filtrate was de-volatile under reduced pressure (rotary evaporator, water bath = 50°C). The crude material (6.35 g of moist yellow-orange solid) was pulverized in isopropanol (20 mL) using a spatula until all solid was removed from the flask walls. The resulting slurry was magnetically stirred for 10-15 minutes. Hexane (20 mL) was added, and the mixture was magnetically stirred for 30 minutes. The solid was collected by vacuum filtration using disposable 0.2 micron polyethylene frit and rinsed in several portions with hexane (25 mL total). The moist solid was dried under vacuum at approximately 50°C for several hours, then at room temperature overnight, to obtain 3.09 g of crude 3,3,8-trimethyl-6-nitro-1,2,3,4-tetrahydroquinoline-4-ol (intermediate compound 47-I) as a yellow powder. Crude intermediate compound 47-I is prepared as shown in Figure 15. 13The material was characterized by C APT NMR spectroscopy. LC-UV analysis showed a purity of approximately 61% at detection at 260 nm, as shown in Figure 16. The crude material proceeded to subsequent steps without further purification.

[0213] Step 2 [ka] A 300 mL Parr autoclave was packed with crude intermediate compound 47-I (2.8 g, <11.9 mmol), toluene (140 mL), acetone (1.7 mL, 23.2 mmol), and 3% Pt / C sulfide (Johnson Matthey) (150 mg wet). The reaction mixture was stirred and heated to 120 °C under 250 PSI of H2, and held for 2 hours. After cooling to room temperature, the reaction mixture was filtered through an in-line 0.2 micron frit. The autoclave was rinsed with isopropanol (130 mL), and the resulting mixture was filtered through an in-line 0.2 micron frit. The combined filtrate was removed under reduced pressure to remove volatile substances (rotary evaporator, water bath = 60 °C). The residue was dissolved in hexane (4 mL). The obtained solution was packed into a 41 mm inner diameter column (silica height = 16-17 cm) pre-prepared with silica gel (ultra-high purity, 60 Å, 60-200 μm) and 30% ethyl acetate in hexane. The column was eluted with 30% ethyl acetate in hexane. Each resulting fraction was analyzed by silica gel TLC (30% ethyl acetate in hexane). Fractions with Rf = 0.45 were collected, combined, and their volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). The resulting light brown oil was dried under vacuum (rotary evaporator, water bath = 55°C, less than 8 mbars) for 1.5 hours to obtain 0.96 g of N-isopropyl-3,3,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-amine (compound 47) as a brown oil. Compound 47 was analyzed as shown in Figure 17. 13 Characterized by C APT NMR spectroscopy. LC-UV analysis showed a purity of 94.6% at detection at 260 nm, as shown in Figure 18. Mass (m / z), 233.3 [M+1] + .

[0214] Example 6 Oxidative Induction Time (OIT) performance of the compounds disclosed herein The oxidation induction time (OIT) of selected compounds in this disclosure was evaluated. The OIT was measured according to a procedure performed using a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, the sample is held in a cell and heated to a pre-selected temperature under a nitrogen atmosphere. Oxygen (O2) is then introduced into the cell, and the length of time before the onset of decomposition is measured, as observed by the initiation of an endothermic process in the DSC trace.

[0215] N, which is 0.5 wt% of the compound disclosed herein. 1 -(4-methylpentan-2-yl)-N 4 -Phenylbenzene-1,4-diamine (6PPD), or no antioxidant (blank), was mixed with polyisoprene and heated isothermally in O2 at 150°C or 160°C. OIT in minutes is shown in Table 3. As shown by the data in Table 3, the compounds of this disclosure demonstrate antioxidant activity compared to the blank control.

[0216] The melting points of the compounds disclosed herein were also measured and are listed in Table 3. [Table 3]

[0217] While the methods, compounds, and compositions described herein have been fully explained, it will be understood by those skilled in the art that the same can be carried out within a broad and equivalent range of conditions, formulations, and other parameters without affecting the scope of the methods, compounds, and compositions provided herein or any embodiment thereof. All patents, patent applications, and publications cited herein are incorporated herein in their entirety by reference.

Claims

1. Equation (I): 【Chemistry 21】 A compound having, or a salt, solvate, or stereoisomer thereof, 【Chemistry 22】 However, it is either a single bond or a double bond. R １ａ However, C is replaced by an optional choice. １ ~C １２ Alkyl, -CHR １ｃ R １ｄ , C ３ ~C ６ Selected from the group consisting of cycloalkyls, 4- to 6-membered heterocyclines, optionally substituted phenyls, and optionally substituted 5 or 6-membered heteroaryls, R １ｂ is selected from the group consisting of hydrogen and C １ -C ９ to C alkyl, R １ｃ However, phenyl and C are optionally substituted. ３ ~C ６ Selected from the group consisting of cycloalkyls and optionally substituted 5- or 6-membered heteroaryls, R １ｄ However, hydrogen and C １ ~C ９ Selected from the group consisting of alkyl groups, R ２ａ , R ２ｂ , and R ２ｃ However, independently, hydrogen, halogen, C １ ~C ９ Alkyl, C １ ~C ９ Haloalkyl, C ３ ~C ８ Cycloalkyl, C １ ~C ８ Alkoxy, C １ ~C ８ Alkylthio, C(=O)OR ４ -OC(=O)R ４ , -C(=O)NR ４ R ５ , -NR ４ C(=O)R ５ , - NHR ４ , -NR ４ R ５ , -OH, -SH, -SC(=O)R ４ , -SC(=O)SR ４ , -SC(=O)NHR ４ , -SC(=O)NR ４ R ５ , -NHC(=O)SR ４ , -NR ４ C(=O)SR ５ , -NHC(=S)SR ４ , -NR ４ C(=S)SR ５ Selected from the group consisting of 4-6 membered heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 membered heteroaryls, or R ２ｂ However, hydrogen, halogen, C １ ~C ９ Alkyl, C １ ~C ９ Haloalkyl, C ３ ~C ８ Cycloalkyl, C １ ~C ８ Alkoxy, C １ ~C ８ Alkylthio, C(=O)OR ４ -OC(=O)R ４ , -C(=O)NR ４ R ５ , -NR ４ C(=O)R ５ , - NHR ４ , -NR ４ R ５ , -OH, -SH, -SC(=O)R ４ , -SC(=O)SR ４ , -SC(=O)NHR ４ , -SC(=O)NR ４ R ５ , -NHC(=O)SR ４ , -NR ４ C(=O)SR ５ , -NHC(=S)SR ４ , -NR ４ C(=S)SR ５ Selected from the group consisting of 4-6 membered heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 membered heteroaryls, R ２ａ and R ２ｃ However, along with the two carbon atoms to which they are bonded, C ５ ~C ８ Cycloalkyl, 5-8 membered heterocyclyl, or C ５ ~C ６ Forming an aryl group, R ３ａ and R ３ｂ are each, independently, hydrogen, C １ -C ９ alkyl, C ３ -C ６ cycloalkyl, and optionally substituted phenyl, provided that 【Chemistry 23】 If R is a double bond, ３ｂ Either it does not exist, or R ３ａ and R ３ｂ together with the carbon atoms to which they are attached form a C ３ -C １２ -cycloalkyl, provided that 【Chemistry 24】 It is a single bond, R ３ｃ and R ３ｄ However, independently, hydrogen, C １ ~C ９ Alkyl, C ３ ~C ６ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, however, 【Chemistry 25】 If R is a double bond, ３ｄ Either it does not exist, or R ３ｃ and R ３ｄ However, along with the carbon atoms to which they are bonded, C ３ ~C １２ It forms a cycloalkyl group, however, 【Chemistry 26】 It is a single bond, R ３ｅ and R ３ｆ However, independently, hydrogen, halogen, C １ ~C ９ Alkyl, C １ ~C ９ Haloalkyl, C ３ ~C ８ Cycloalkyl, -OH, -SH, C １ ~C ８ Alkoxy, C １ ~C ８ Alkylthio, arylthio, C(=O)OR ４ -OC(=O)R ４ , -C(=O)NR ４ R ５ , -NR ４ C(=O)R ５ , - NHR ４ , -NR ４ R ５ , -SC(=O)R ４ , -SC(=O)SR ４ , -SC(=O)NHR ４ , -SC(=O)NR ４ R ５ , -NHC(=O)SR ４ , -NR ４ C(=O)SR ５ , -NHC(=S)SR ４ , -NR ４ C(=S)SR ５ Selected from the group consisting of 4-6 member heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 member heteroaryls, provided that R ３ｅ and / or R ３ｆ If R is hydrogen, ３ｃ and R ３ｄ However, independently, C １ ~C ９ Alkyl, C ３ ~C ６ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, or R ３ｅ and R ３ｆ However, along with the carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R ３ｇ However, hydrogen and C １ ~C ９ Selected from the group consisting of alkyl groups, R ４ and R ５ However, in each appearance, hydrogen and C appear independently. １ ~C ９ Alkyl, C ３ ~C ６ A compound, or a salt, solvate, or stereoisomer thereof, selected from the group consisting of cycloalkyl and optionally substituted phenyl.

2. Formula (II): 【Chemistry 27】 A compound according to claim 1, having (II), or a salt, solvate, or stereoisomer thereof.

3. R ３ｃ and R ３ｄ However, independently, C １ ~C ９ Alkyl, C ３ ~C ６ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, or R ３ｃ and R ３ｄ However, along with the carbon atoms to which they are bonded, C ３ ~C １２ The compound according to claim 2, or a salt, solvate, or stereoisomer thereof, which forms a cycloalkyl group.

4. R ３ｅ and R ３ｆ However, independently, halogen, C １ ~C ９ Alkyl, C １ ~C ９ Haloalkyl, C ３ ~C ８ Cycloalkyl, -OH, -SH, C １ ~C ８ Alkoxy, C １ ~C ８ Alkylthio, arylthio, C(=O)OR ４ -OC(=O)R ４ , -C(=O)NR ４ R ５ , -NR ４ C(=O)R ５ , - NHR ４ , -NR ４ R ５ , -SC(=O)R ４ , -SC(=O)SR ４ , -SC(=O)NHR ４ , -SC(=O)NR ４ R ５ , -NHC(=O)SR ４ , -NR ４ C(=O)SR ５ , -NHC(=S)SR ４ , -NR ４ C(=S)SR ５ Selected from the group consisting of 4-6 membered heterocyclyls, optionally substituted phenyls, and optionally substituted 5 or 6 membered heteroaryls, or R ３ｅ and R ３ｆ However, along with the carbon atoms to which they are bonded, C ３ ~C １２ A compound according to claim 2 or 3 that forms a cycloalkyl group, or a salt, solvate, or stereoisomer thereof.

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

6. Formula (III): 【Chemistry 28】 A compound according to claim 1, having (III), or a salt, solvate, or stereoisomer thereof.

7. R １ａ The compound according to any one of claims 1 to 6, or a salt, solvate, or stereoisomer thereof, wherein the phenyl is optionally substituted.

8. R １ａ However, C １ ~C １２ A compound according to any one of claims 1 to 6, which is alkyl, or a salt, solvate, or stereoisomer thereof.

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

10. R １ａ The compound according to claim 9, or a salt, solvate, or stereoisomer thereof, wherein the compound is isopropyl or sec-butyl.

11. R １ａ but, 【Chemistry 29】 The compound according to claim 8, or a salt, solvate, or stereoisomer thereof.

12. R ２ａ , R ２ｂ , and R ２ｃ However, independently, hydrogen and C １ ~C ９ A compound according to any one of claims 1 to 11, selected from the group consisting of alkyl groups, or a salt, solvate, or stereoisomer thereof.

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

14. R ２ａ However, hydrogen and C １ ~C ４ A compound according to claim 13, selected from the group consisting of alkyl groups, or a salt, solvate, or stereoisomer thereof.

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

16. R ３ａ However, C １ ~C ９ A compound according to any one of claims 1 to 14, which is alkyl, or a salt, solvate, or stereoisomer thereof.

17. R ３ａ However, C ３ ~C ６ A compound according to any one of claims 1 to 14, which is a cycloalkyl compound, or a salt, solvate, or stereoisomer thereof.

18. R ３ａ The compound according to any one of claims 1 to 14, or a salt, solvate, or stereoisomer thereof, wherein the phenyl is optionally substituted.

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

20. R ３ｃ However, C １ ~C ９ A compound according to any one of claims 1 to 18, which is alkyl, or a salt, solvate, or stereoisomer thereof.

21. R ３ｃ However, C ３ ~C ６ A compound according to any one of claims 1 to 18, which is a cycloalkyl compound, or a salt, solvate, or stereoisomer thereof.

22. R ３ｃ The compound according to any one of claims 1 to 18, or a salt, solvate, or stereoisomer thereof, wherein the phenyl is optionally substituted.

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

24. R ３ｅ However, C １ ~C ８ A compound according to any one of claims 1 to 22, which is an alkoxy, or a salt, solvate, or stereoisomer thereof.

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

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

27. R ３ｅ However, C １ ~C ８ A compound according to any one of claims 1 to 22, wherein it is an alkylthio compound.

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

29. R ３ｅ However, C １ ~C ９ A compound according to any one of claims 1 to 22, which is alkyl, or a salt, solvate, or stereoisomer thereof.

30. R ３ｅ However, C ３ ~C ６ A compound according to any one of claims 1 to 22, which is a cycloalkyl compound, or a salt, solvate, or stereoisomer thereof.

31. R ３ｅ The compound according to any one of claims 1 to 22, or a salt, solvate, or stereoisomer thereof, wherein the phenyl is optionally substituted.

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

33. R ３ｆ However, C １ ~C ９ A compound according to any one of claims 1 to 31, which is alkyl, or a salt, solvate, or stereoisomer thereof.

34. R ３ｆ However, C ３ ~C ６ A compound according to any one of claims 1 to 31, which is a cycloalkyl compound, or a salt, solvate, or stereoisomer thereof.

35. R ３ｆ The compound according to any one of claims 1 to 31, or a salt, solvate, or stereoisomer thereof, wherein the phenyl is optionally substituted. 【Request Item 36】 【Chemistry 30-1】 【Chemistry 30-2】 【Transformation 30-3】 【Chemistry 30-4】 【Transformation 30-5】 A compound according to claim 1, or a salt, solvate, or stereoisomer thereof, selected from the group consisting of the above.

37. A composition, (i) The compound according to any one of claims 1 to 36, and (ii) One or more elastomers, (iii) One or more fillers, (iv) One or more rubber chemicals, (v) One or more plasticizers, (vi) One or more additional anti-deterioration agents, (vii) A composition comprising 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 degradation inhibitors.

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

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

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

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

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

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

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

45. The composition according to claim 44, wherein the synthetic rubber comprises an unsaturated rubber, a saturated rubber, a rubber having fluoro and fluoroalkyl or fluoroalkoxy substituents on the polymer chain (FKM), a silicone rubber (Q), or a blend thereof.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

62. The composition according to claim 61, wherein one or more fillers include silica.

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

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

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

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

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

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

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

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

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

72. The aforementioned sulfur is octa-sulfur (S ８ ), cyclododeculfur (S １２ The composition according to claim 71, which is polymeric sulfur, or a combination thereof.

73. The composition according to claim 71, wherein the peroxide is benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexine (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 a combination thereof.

74. The composition according to claim 71, wherein the resin is a binding resin.

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

76. The composition according to claim 75, wherein the one or more accelerators include guanidine, thiazole, sulfenamide, thiram, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

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

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

79. The composition according to claim 76, wherein the sulfenamide comprises N-tert-butyl-2-benzothiadylsulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydiethylenebenzothiazolesulfenamide (OBTS), N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide (OTOS), thiocarbamylsulfenamide, or a combination thereof.

80. The composition according to claim 76, wherein the thiram is dimethylcarbamothioate dithioperoxy anhydride (thiram), dipentamethylenethiram tetrasulfide (DPIT), tetrabenzylthiram disulfide (TBzTD), tetraethylthiram disulfide (TETD), tetramethylthiram disulfide (TMTD), tetramethylthiram monosulfide (TMTM), or a combination thereof.

81. The composition according to claim 76, wherein the dithiocarbamate comprises zinc dimethyl dithiocarbamate (ZDMC), zinc diethyl dithiocarbamate (ZDEC), zinc dibutyl dithiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyl dithiocarbamate (SBEC), sodium diethyl dithiocarbamate (SDEC), telluride diethyl dithiocarbamate (TDEC), zinc dibenzyl dithiocarbamate (ZEBC), or a combination thereof.

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

83. The composition according to claim 82, wherein the one or more activators include a metal oxide, an acid, a metal complex, or a combination thereof.

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

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

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

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

88. The composition according to claim 87, wherein the one or more pre-vulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

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

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

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

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

93. The composition according to any one of claims 89 to 92, wherein the one or more plasticizers include mineral oil, organic esters, resins, waxes, ester plasticizers, naturally derived oils, or a combination thereof.

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

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

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

97. The composition according to claim 96, wherein the composition comprises about 15 wt / wt% to about 85 wt / wt% of the compound and one or more additional degradation inhibitors in about 15 wt / wt% to about 85 wt / wt%.

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

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

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

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

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

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

104. The composition according to any one of claims 96 to 103, wherein the one or more additional degradation inhibitors are paraphenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenolic compounds, alkylated diphenylamine (DPA), or diphenylamine-ketone condensates.

105. The aforementioned PPD is N １ -(4-methylpentan-2-yl)-N ４ -Phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-p-phenylenediamine (7PPD), N １ -phenyl-N ４ The composition according to claim 104, wherein the composition is -(propan-2-yl)benzene-1,4-diamine (IPPD), N,N'-di-sec-butyl-p-phenylenediamine (44PD), N,N'-bis(1,3-dimethylbutyl)-p-phenylenediamine (66PD), N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine (77PD), or N-N'-dioctyl-p-phenylenediamine (88PD).

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

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

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

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

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

111. A vulcanized elastomer article prepared using the composition described in any one of claims 37 to 108.

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

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

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

115. The vulcanized elastomer article according to claim 114, wherein the constituent elements are beads, belts, body plies, inner liners, sidewalls, undertreads, or treads.

116. The vulcanized elastomer article according to claim 110 or 111, wherein the vulcanized elastomer article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or flooring material.

117. A process for preparing a vulcanized elastomer article, wherein the process comprises: (a) Forming the composition according to any one of claims 38 to 107 into a molded shape, (b) vulcanizing the formed shape, A process for providing vulcanized elastomer articles.

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

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

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

121. The process according to claim 120, wherein the tire is a passenger car tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, a construction machine tire, an airplane tire, or a racing tire.

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

123. The process according to claim 122, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

124. The process according to any one of claims 117 to 119, wherein the vulcanized elastomer article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or flooring.

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

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

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

128. A process for regrowing a tire, wherein the process is (a) Applying the composition according to any one of claims 37 to 108 to a tire, (b) Placing a pre-vulcanized tread around the tire, (c) Placing a hardening envelope around the tire, (d) A process comprising vulcanizing the tire.

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

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

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

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