Quinolineamine and pyridoquinoline degradation inhibitor compounds and their use

Abstract

The present disclosure relates to a compound represented by formula (I): (I), or a salt or solvate thereof, wherein R 1 ,, R 1c ,, R 2a ,, R 2b ,, R 2c ,, R 3a ,, R 3b ,, R 3c ,, R 3d ,, R 3e , and JPEG2026521397000088.jpg1011 are as defined herein, and provides a compound, or a salt or solvate thereof. The present disclosure relates to a compound represented by formula (IV): (IV), or a salt or solvate thereof, wherein R 8a ,, R 8b ,, R 9a ,, R 9b ,, R[[ID=3l]] 9c ,, R 9d ,, R 9e ,, R 10a ,, R 10b ,, R 10c ,, R 10d ,, R 10e , and JPEG2026521397000089.jpg1010 are as defined herein, and provides a compound, or a salt or solvate thereof. The present disclosure also provides a composition, a vulcanized elastomer article, a lubricant composition, a combustible fuel composition, and a fuel additive composition comprising a compound disclosed herein. The present disclosure also provides a process for preparing the compositions and vulcanized elastomer articles described herein. JPEG2026521397000090.jpg52135

Description

[Technical Field]

[0001] This disclosure provides compounds having the properties of degradation inhibitors, such as ozone degradation inhibitors, antioxidants, and / or anti-fatigue agents, which are useful additives in compositions that are useful for vulcanized rubber articles, elastomers, lubricants, fuels, and other compositions that require such properties, or as compositions that impart such properties themselves. [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 repeated 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 decomposition by 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 with anti-degradation 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 anti-aging agents, 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] U.S. Patent Application Publication No. 3147321A1 [Overview of the project]

[0006] This disclosure provides compounds represented by any one of the following formulas (I), (II), (IIa), (III), (IIIa), (IV), (V), and (VI) that are useful as degradation inhibitors, such as ozone degradation inhibitors and / or antioxidants, and / or as additives in lubricants or flammable fuels, and which are collectively referred to herein as “Compounds of the Disclosure” or individually as “Compounds of the Disclosure”.

[0007] This disclosure also provides compositions comprising the following: (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 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 are collectively referred to as “Compositions of the Disclosure” or individually as “Compositions of the Disclosure” in this Specification.

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

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

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

[0011] The Disclosure also provides the Compounds of the Disclosure and the Compositions of the Disclosure comprising 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 the compounds of the Disclosure and compositions of the Disclosure comprising 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 compositions described herein, for example, compositions or compounds of the disclosure, and compositions comprising 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 compositions described herein to tires, (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 a kit including the compositions described herein and instructions for using the compositions in a vulcanizable elastomer composition.

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

[0024] 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 13C nuclear magnetic resonance (NMR) spectrum of intermediate compound 1-I in d6-dimethyl sulfoxide (d6-DMSO). [Figure 2] This is a broken line graph showing the 1H NMR spectrum of compound 1 in d6-DMSO. [Figure 3] This is a broken line graph showing the 13C NMR spectrum of compound 1 in d6-DMSO. [Figure 4] This is a broken line graph showing the 1H NMR spectrum of compound 3 in d6-DMSO. [Figure 5] This is a broken line graph showing the 13C NMR spectrum of compound 3 in d6-DMSO. [Figure 6] This is a broken line graph showing the 13C NMR spectrum of compound 6 in d8-THF. [Figure 7] This is a broken line graph showing the 1H NMR spectrum of compound B1 in d-trifluoroacetic acid (d-TFA). [Figure 8] This is a broken line graph showing the 13C NMR spectrum of compound B1 in d-TFA. [Figure 9] This is a broken line graph showing the 1H NMR spectrum of compound B2 in d-trifluoroacetic acid (d-TFA). [Figure 10]This is a broken line graph showing the 13C NMR spectrum of compound B2 in d-TFA. [Figure 11] This is a broken line graph showing the 13C NMR spectrum of compound 33. [Figure 12] This is a broken line graph showing the 13C NMR spectrum of compound 32. [Figure 13] This is a piecewise line graph showing the force retention as a function of time for sidewall compounds containing compound 1 or not containing a degradation inhibitor, under dynamic conditions. [Figure 14] This is a piecewise line graph showing the force retention as a function of time for sidewall compounds containing compound B1 or not containing a degradation inhibitor, under dynamic conditions. [Figure 15] This is a piecewise line graph showing the force retention as a function of time for tread compounds containing compound 1 or those without degradation inhibitors, under dynamic conditions. [Figure 16] This is a piecewise line graph showing the force retention as a function of time for sidewall compounds containing compound 6 or not containing a degradation inhibitor, under dynamic conditions. [Figure 17] This is a piecewise line graph showing the force retention as a function of time for tread compounds containing compound 6 or those not containing degradation inhibitors, under dynamic conditions. [Modes for carrying out the invention]

[0027] In one embodiment, the compound of the present disclosure is of formula (I): [ka] Compounds having, or its salt, solvate, or stereoisomer, in the formula, [ka] However, it is either a single bond or a double bond. R 1 However, C1~C were replaced by arbitrary selection. 12Alkyl, optionally substituted C2-C6 alkenyl, -CHR 1a R 1b , C3-C7 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, -C(=O)R 4 , -C(=O)OR 4 , and -SO2R 4 selected from the group consisting of, R 1a is selected from the group consisting of optionally substituted phenyl, 4- to 6-membered heterocyclyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl, R 1b is selected from the group consisting of hydrogen and C1-C9 alkyl, R 1c is selected from the group consisting of hydrogen and C1-C6 alkyl, R 2a , R 2b , and R 2c are 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 , -NR 4 R 5 , -OH, -SH, -SC(=O)R 4 , -SC(=O)SR 4 , -SC(=O)NR 4 R 5 , -NR 4 C(=O)SR 5 , -NR 4 C(=S)SR​​​​​​4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , and [ka] Selected from the group consisting of, R 3b However, it is selected from the group consisting of hydrogen, halogens, C1-C9 alkyls, and optionally substituted phenyls, or R 3a and R 3b However, together with the carbon atoms to which they are bonded, C3~C 12 Forming a cycloalkyl group, R 3c However, hydrogen, halogens, C1-C9 alkyl groups, optionally substituted phenyl, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , and [ka] Selected from the group consisting of, R 3d However, it is selected from the group consisting of hydrogen, halogens, C1-C9 alkyls, and optionally substituted phenyls, or R 3c and R 3d However, together with the two carbon atoms to which they are bonded, C3~C 12 Forming a cycloalkyl group, R 3e However, hydrogen, C1-C6 alkyl, optionally substituted C2-C6 alkenyl, C3-C7 cycloalkyl, -C(=O)R 4 , -C(=O)OR 4 , and -SO2R 4 Selected from the group consisting of, In each occurrence, Z independently represents -O-, -S-, and -NR. 7 - Selected from the group consisting of, R 4 However, in each occurrence, independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C7 cycloalkyl, and optionally substituted phenyl, R 5 However, in each occurrence, an independent selection is made from the group consisting of hydrogen, C1-C9 alkyl, C3-C7 cycloalkyl, and optionally substituted phenyl. R 6a , R 6b , R 6c , and R 6d However, in each appearance, hydrogen, C1~C 12 Selected from the group consisting of alkyl groups and optionally substituted phenyl groups, R 7 However, in each appearance, a compound is independently selected from the group consisting of hydrogen and C1-C6 alkyl, provided that the compound of formula (I) is 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine, 2,2,4-trimethyl-N-phenyl-1,2,3,4-tetrahydroquinoline-6-amine, or 2,2,4-trimethyl-N-(p-tolyl)-1,2-dihydroquinoline-6-amine. [ka] It is a compound, or a salt, solvate, or stereoisomer thereof, provided that it is not a compound.

[0028] In some embodiments, the compounds disclosed herein are compounds having formula (I), wherein R 2a , R 2b , and R 2c However, it is hydrogen, a compound.

[0029] In some embodiments, the compounds disclosed herein are compounds having formula (I), and R 2a , R 2b , and R 2c However, it is hydrogen, and R 3a, R 3b , and R 3c is methyl and R 3d is hydrogen, R 1 is optionally substituted C1 - C 12 alkyl, -CHR 1a R 1b is a compound selected from the group consisting of C3 - C7 cycloalkyl, 4 - to 6 - membered heterocyclyl, and optionally substituted 5 - or 6 - membered heteroaryl.

[0030] In some embodiments, the compound of the present disclosure is a compound having the formula (I), wherein R 1 is phenyl, R 2a , R 2b , and R 2c are hydrogen, R 3b is methyl, R 3d is hydrogen, R 3a is hydrogen, halogen, C2 - C9 alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , CH2OC(=O)R 4 , and

Chemical formula

[0031] R 3c is hydrogen, halogen, C2 - C9 alkyl, optionally substituted phenyl, -C(=O)OR 4 , -C(=O)NR 4 R 5 , -C(=O)SR 4 , -CH2OR 4 , -CH2OC(=O)R 4 , and

Chemical formula

[0032] In another embodiment, the compound of the present disclosure is of formula (II): [ka] Compounds having, or its salt, solvate, or stereoisomer, in which R 1 , R 1c , R 2a , R 2b , R 2c , R 3a , R 3b , R 3c , R 3d , and R 3e However, it is a compound, or a salt, solvate, or stereoisomer thereof, as defined in relation to formula (I).

[0033] In another embodiment, the compound of the present disclosure is of formula (IIa): [ka] Compounds having, or its salt, solvate, or stereoisomer, in which R 1 , R 1c , R 3a , R 3b , R 3c , R 3d , and R 3e However, it is a compound, or a salt, solvate, or stereoisomer thereof, as defined in relation to formula (I).

[0034] In another embodiment, the compound of the present disclosure is of formula (III): [ka] Compounds having, or its salt, solvate, or stereoisomer, in which R 1 , R 1c , R 2a , R 2b , R 2c , R 3a , R 3b , R 3c , R3d , and R 3e However, it is a compound, or a salt, solvate, or stereoisomer thereof, as defined in relation to formula (I).

[0035] In another embodiment, the compound of the present disclosure is of formula (IIIa): [ka] Compounds having,

[0036] or its salt, solvate, or stereoisomer, in which R 1 , R 1c , R 3a , R 3b , R 3c , R 3d , and R 3e However, it is a compound, or a salt, solvate, or stereoisomer thereof, as defined in relation to formula (I).

[0037] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (II), (IIa), (III), or (IIIa), provided that the compound of formula (II), (IIa), (III), or (IIIa) is not 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine or 2,2,4-trimethyl-N-phenyl-1,2,3,4-tetrahydroquinoline-6-amine.

[0038] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a , R 3b , and R 3c However, these are compounds independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0039] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a , R 3b , and R 3c However, it is a compound that is methyl, ethyl, or isobutyl.

[0040] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a and R 3c However, it is a methyl compound.

[0041] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a and R 3c However, it is ethyl, a compound.

[0042] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a and R 3c However, it is an isobutyl compound.

[0043] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3b However, it is a methyl compound.

[0044] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a and R 3b However, it is methyl, and R 3c and R 3d However, it is hydrogen, a compound.

[0045] In some embodiments, the compound of the present disclosure is a compound having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3a and R 3b are ethyl, and R 3c and R 3d are hydrogen.

[0046] In some embodiments, the compound of the present disclosure is a compound having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3a is ethyl, R 3b is methyl, and R 3c and R 3d are hydrogen.

[0047] In some embodiments, the compound of the present disclosure is a compound having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3a is -C(=O)OR 4 、-C(=O)NR 4 R 5 、-C(=O)SR 4 、-CH2OR 4 、-CH2OC(=O)R 4 、or

Chemical formula

[0048] In some embodiments, the compound of the present disclosure is a compound having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3a is -C(=O)OR 4 . In some embodiments, R 3a is -C(=O)OEt.

[0049] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a However, -C(=O)NR 4 R 5 It is a compound.

[0050] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a However, -C(=O)SR 4 It is a compound.

[0051] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a However, -CH2OR 4 It is a compound.

[0052] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a However, -CH2OC(=O)R 4 It is a compound.

[0053] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3a but, [ka] It is a compound.

[0054] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c However, -C(=O)OR 4It is a compound. In some embodiments, R 3c This is -C(=O)OEt.

[0055] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c However, -C(=O)NR 4 R 5 It is a compound.

[0056] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c However, -C(=O)SR 4 It is a compound.

[0057] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c However, -CH2OR 4 It is a compound.

[0058] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c However, -CH2OC(=O)R 4 It is a compound.

[0059] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c but, [ka] It is a compound.

[0060] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein Z is -O-. In some embodiments, Z is -S-. In some embodiments, Z is -NR 7 -. In some embodiments, R 7 is hydrogen. In some embodiments, R 6a , R 6b , R 6c , and R 6d are hydrogen.

[0061] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3a and R 3b together with the carbon atom to which they are attached form a C3-C 12 cycloalkyl.

[0062] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3a and R 3b together with the carbon atom to which they are attached form cyclobutyl, cyclopentyl, or cyclohexyl.

[0063] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), wherein R 3c and R 3d together with the two carbon atoms to which they are attached form a C3-C 12 cycloalkyl.

[0064] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3c and R 3d However, these compounds, together with the two carbon atoms to which they are bonded, form cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl.

[0065] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where each R 4 However, it is a compound that is either hydrogen or a C1-C9 alkyl group.

[0066] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where each R 4 However, it is ethyl, a compound.

[0067] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where each R 4 However, it is hydrogen, a compound.

[0068] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1 However, it is a compound in which phenyl is optionally substituted.

[0069] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1 However, C1~C 12 It is an alkyl compound.

[0070] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1 The compound is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

[0071] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1 but, [ka] It is a compound.

[0072] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1 However, -CHR 1a R 1b It is a compound.

[0073] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1a However, it is a compound in which phenyl is optionally substituted.

[0074] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1a However, it is a compound that is a C3-C6 cycloalkyl group.

[0075] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1aHowever, it is a compound in which a five-membered or six-membered heteroaryl is optionally substituted.

[0076] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1a However, it is a compound that is phenyl, 2-furyl, or 2-tetrahydrofuryl.

[0077] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1a However, it is a compound, which is phenyl.

[0078] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1a However, it is a compound that is 2-furyl.

[0079] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1a However, it is a compound called 2-tetrahydrofuryl.

[0080] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1b However, it is a compound that is either hydrogen or methyl.

[0081] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1b However, it is hydrogen, a compound.

[0082] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1b However, it is a methyl compound.

[0083] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1c However, it is a compound that is C1-C6 alkyl.

[0084] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1c However, it is a methyl compound.

[0085] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 1c However, it is hydrogen, a compound.

[0086] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound that is C1-C6 alkyl.

[0087] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a methyl compound.

[0088] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is ethyl, a compound.

[0089] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is hydrogen, a compound.

[0090] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound that is a C3-C7 cycloalkyl group.

[0091] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound that is cyclohexen-1-yl.

[0092] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, -C(=O)R 4 It is a compound.

[0093] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound with the structure -C(=O)CH3.

[0094] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, -C(=O)OR 4 It is a compound.

[0095] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound with the structure -C(=O)OC(CH3)3.

[0096] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, -SO2R 4 It is a compound.

[0097] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound with the structure -SO2CH3.

[0098] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound with the formula -SO2(C6H5CH3).

[0099] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e However, it is a compound in which C2-C6 alkenyls are optionally substituted.

[0100] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (I), (II), (IIa), (III), or (IIIa), where R 3e but, [ka] It is a compound.

[0101] In some embodiments, the compounds of the present disclosure are one or more of the compounds in Table 1, or their salts or solvates. [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8]

[0102] In another embodiment, the compound of the present disclosure is of formula (IV): [ka] Compounds having, or its salt, solvate, or stereoisomer, in the formula, each [ka] However, independently, they are single bonds or double bonds. R 8a and R 8b However, 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 R5 , -NR 4 C(=O)R 5 , -NR 4 R 5 -OH, -SH, -SC(=O)R 4 -SC(=O)SR 4 -SC(=O)NR 4 R 5 , -NR 4 C(=O)SR 5 , -NR 4 C(=S)SR 5 Selected from the group consisting of 4- to 6-membered heterocyclyls, optionally substituted phenyls, optionally substituted 5- or 6-membered heteroaryls, aryloxys, arylthios, and arylaminos, R 9a However, hydrogen, halogens, C1-C9 alkyl groups, optionally substituted phenyl, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , and [ka] Selected from the group consisting of, R 9b However, it is selected from the group consisting of hydrogen, halogens, C1-C9 alkyls, and optionally substituted phenyls, or R 9a and R 9b However, together with the carbon atoms to which they are bonded, C3~C 12 Forming a cycloalkyl group, R 9c However, hydrogen, halogens, C1-C9 alkyl groups, optionally substituted phenyl, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , and [ka] Selected from the group consisting of, R 9d However, it is selected from the group consisting of hydrogen, halogens, C1-C9 alkyls, and optionally substituted phenyls, or R 9c and R 9d However, together with the two carbon atoms to which they are bonded, C3~C 12 Forming a cycloalkyl group, R 9e However, hydrogen, C1-C6 alkyl, optionally substituted C2-C6 alkenyl, -C(=O)R 4 , -C(=O)OR 4 , and -SO2R 4 Selected from the group consisting of, R 10a However, hydrogen, halogens, C1-C9 alkyl groups, optionally substituted phenyl, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , and [ka] Selected from the group consisting of, R 10b However, it is selected from the group consisting of hydrogen, halogens, C1-C9 alkyls, and optionally substituted phenyls, or R 10a and R 10b However, together with the carbon atoms to which they are bonded, C3~C 12 Forming a cycloalkyl group, R 10c However, hydrogen, halogens, C1-C9 alkyl groups, optionally substituted phenyl, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , and [ka] Selected from the group consisting of, R 10d However, it is selected from the group consisting of hydrogen, halogens, C1-C9 alkyls, and optionally substituted phenyls, or R 10c and R 10d However, together with the two carbon atoms to which they are bonded, C3~C 12 Forming a cycloalkyl group, R 10e However, hydrogen, C1-C6 alkyl, optionally substituted C2-C6 alkenyl, -C(=O)R 4 , -C(=O)OR 4 , and -SO2R 4 Selected from the group consisting of, In each occurrence, Z independently represents -O-, -S-, and -NR. 7 - Selected from the group consisting of, R 4 However, in each occurrence, independently selected from the group consisting of hydrogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C7 cycloalkyl, and optionally substituted phenyl, R 5 However, in each occurrence, an independent selection is made from the group consisting of hydrogen, C1-C9 alkyl, C3-C7 cycloalkyl, and optionally substituted phenyl. R 6a , R 6b , R 6c , and R 6d However, in each appearance, hydrogen, C1~C 12 Selected from the group consisting of alkyl groups and optionally substituted phenyl groups, R 7 However, in each instance, the compound, or its salt, solvate, or stereoisomer, is independently selected from the group consisting of hydrogen and C1-C6 alkyl groups.

[0103] In another embodiment, the compound of the present disclosure is of formula (V): [ka] Compounds having,

[0104] or its salt, solvate, or stereoisomer, in which R 8a , R 8b , R 9a , R 9b , R 9c , R 9d , R 9e , R 10a , R 10b , R 10c , R 10d , and R 10e However, it is a compound, or a salt, solvate, or stereoisomer thereof, as defined in relation to formula (IV).

[0105] In another embodiment, the compound of the present disclosure is of formula (VI): [ka] Compounds having,

[0106] or its salt, solvate, or stereoisomer, in which R 8a , R 8b , R 9a , R 9b , R 9c , R 9d , R 9e , R 10a , R 10b , R 10c , R 10d , and R 10e However, it is a compound, or a salt, solvate, or stereoisomer thereof, as defined in relation to formula (IV).

[0107] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 8a and R 8b However, it is hydrogen, a compound.

[0108] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 8a and R 8b However, it is a methyl compound.

[0109] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a , R 9b , and R 9c However, these are compounds independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0110] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a , R 9b , and R 9c However, it is a compound that is methyl, ethyl, or isobutyl.

[0111] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9c However, it is a methyl compound.

[0112] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9c However, it is ethyl, a compound.

[0113] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9c However, it is an isobutyl compound.

[0114] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9b However, it is a methyl compound.

[0115] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9b However, it is methyl, and R 9c and R 9d However, it is hydrogen, a compound.

[0116] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9b However, it is ethyl, and R 9c and R 9d However, it is hydrogen, a compound.

[0117] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, it is ethyl, and R 9b However, it is methyl, and R 9c and R 9d However, it is hydrogen, a compound.

[0118] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , or [ka] It is a compound.

[0119] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, -C(=O)OR 4 It is a compound. In some embodiments, R 9a This is -C(=O)OEt.

[0120] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, -C(=O)NR 4 R 5 It is a compound.

[0121] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, -C(=O)SR 4 It is a compound.

[0122] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, -CH2OR 4 It is a compound.

[0123] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a However, -CH2OC(=O)R 4 It is a compound.

[0124] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a but, [ka] It is a compound.

[0125] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c However, -C(=O)OR 4 It is a compound. In some embodiments, R 9c This is -C(=O)OEt.

[0126] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c However, -C(=O)NR 4 R 5 It is a compound.

[0127] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c However, -C(=O)SR 4 It is a compound.

[0128] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c However, -CH2OR 4 It is a compound.

[0129] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c However, -CH2OC(=O)R 4 It is a compound.

[0130] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c but, [ka] It is a compound.

[0131] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a , R 10b , and R 10c However, these are compounds independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

[0132] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a , R 10b , and R 10c However, it is a compound that is methyl, ethyl, or isobutyl.

[0133] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a and R 10c However, it is a methyl compound.

[0134] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a and R 10c However, it is ethyl, a compound.

[0135] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a and R 10c However, it is an isobutyl compound.

[0136] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10b However, it is a methyl compound.

[0137] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a and R 10b However, it is methyl, and R 10c and R 10d However, it is hydrogen, a compound.

[0138] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a and R 10b However, it is ethyl, and R 10c and R 10d However, it is hydrogen, a compound.

[0139] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, it is ethyl, and R 10b However, it is methyl, and R 10c and R 10d However, it is hydrogen, a compound.

[0140] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, -C(=O)OR 4 -C(=O)NR 4 R 5 -C(=O)SR 4 -CH2OR 4 -CH2OC(=O)R 4 , or [ka] It is a compound.

[0141] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, -C(=O)OR 4 It is a compound. In some embodiments, R 10aThis is -C(=O)OEt.

[0142] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, -C(=O)NR 4 R 5 It is a compound.

[0143] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, -C(=O)SR 4 It is a compound.

[0144] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, -CH2OR 4 It is a compound.

[0145] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a However, -CH2OC(=O)R 4 It is a compound.

[0146] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a but, [ka] It is a compound.

[0147] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c However, -C(=O)OR 4 It is a compound. In some embodiments, R 10c This is -C(=O)OEt.

[0148] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c However, -C(=O)NR 4 R 5 It is a compound.

[0149] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c However, -C(=O)SR 4 It is a compound.

[0150] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c However, -CH2OR 4 It is a compound.

[0151] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c However, -CH2OC(=O)R 4 It is a compound.

[0152] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c but, [ka] It is a compound.

[0153] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where Z is -O-. In some embodiments, Z is -S-. In some embodiments, Z is -NR 7 - In some embodiments, R 7 is hydrogen. In some embodiments, R 6a , R 6b , R6c , and R 6d It is hydrogen.

[0154] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9b However, together with the carbon atoms to which they are bonded, C3~C 12 It is a compound that forms a cycloalkyl group.

[0155] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 9b However, these compounds combine with the carbon atoms to which they are bonded to form cyclobutyl, cyclopentyl, or cyclohexyl compounds.

[0156] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10a and R 10b However, together with the carbon atoms to which they are bonded, C3~C 12 It is a compound that forms a cycloalkyl group.

[0157] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), and R 10a and R 10b However, these compounds, when combined with the carbon atoms to which they are bonded, form cyclobutyl, cyclopentyl, or cyclohexyl compounds.

[0158] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), and R 9c and R 9d However, together with the two carbon atoms to which they are bonded, C3~C 12 It is a compound that forms a cycloalkyl group.

[0159] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), and R 9c and R 9d However, these compounds, together with the two carbon atoms to which they are bonded, form cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl.

[0160] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10c and R 10d However, together with the two carbon atoms to which they are bonded, C3~C 12 It is a compound that forms a cycloalkyl group.

[0161] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), and R 10c and R 10d However, these compounds, together with the two carbon atoms to which they are bonded, form cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl.

[0162] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where each R 4 However, it is a compound that is either hydrogen or a C1-C9 alkyl group.

[0163] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 4 However, it is ethyl, a compound.

[0164] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 4 However, it is hydrogen, a compound.

[0165] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9a and R 10a However, they are the same, for example, R 9a and R 10a However, both are methyl, both are ethyl, or both are isobutyl compounds.

[0166] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9b and R 10b However, they are the same, for example, R 9a and R 10a However, both are methyl, both are ethyl, or both are isobutyl compounds.

[0167] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9c and R 10c However, they are the same, for example, R 9a and R 10a However, both are methyl, both are ethyl, or both are isobutyl compounds.

[0168] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9d and R 10d However, they are the same, for example, R 9a and R 10a However, both are hydrogen compounds.

[0169] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound that is C1-C6 alkyl.

[0170] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R9e However, it is a methyl compound.

[0171] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is ethyl, a compound.

[0172] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is hydrogen, a compound.

[0173] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound that is a C3-C7 cycloalkyl group.

[0174] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound that is cyclohexen-1-yl.

[0175] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, -C(=O)R 4 It is a compound.

[0176] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound with the structure -C(=O)CH3.

[0177] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, -C(=O)OR 4 It is a compound.

[0178] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound with the structure -C(=O)OC(CH3)3.

[0179] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, -SO2R 4 It is a compound.

[0180] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound with the structure -SO2CH3.

[0181] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 9e However, it is a compound with the formula -SO2(C6H5CH3).

[0182] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound that is C1-C6 alkyl.

[0183] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a methyl compound.

[0184] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is ethyl, a compound.

[0185] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10eHowever, it is hydrogen, a compound.

[0186] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound that is a C3-C7 cycloalkyl group.

[0187] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound that is cyclohexen-1-yl.

[0188] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, -C(=O)R 4 It is a compound.

[0189] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound with the structure -C(=O)CH3.

[0190] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, -C(=O)OR 4 It is a compound.

[0191] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound with the structure -C(=O)OC(CH3)3.

[0192] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, SO2R 4 It is a compound.

[0193] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound with the structure -SO2CH3.

[0194] In some embodiments, the compounds of the present disclosure are compounds having any one of formulas (IV) to (VI), where R 10e However, it is a compound with the formula -SO2(C6H5CH3).

[0195] In some embodiments, the compounds of the present disclosure are one or more of the compounds listed in Table 2, or their salts or solvates. [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5]

[0196] The compounds of this disclosure can be useful as degradation inhibitors, for example, as ozone degradation inhibitors and / or antioxidants, as additives in lubricants and as additives in flammable fuels.

[0197] The compounds of this disclosure can be prepared by a three-step process, as shown in Scheme 1, comprising: i) reacting a secondary arylamine with sodium nitrite in an acid; ii) reducing the resulting nitroso intermediate to an amine; and iii) reacting the resulting amine with a ketone, such as acetone, or an aldehyde. The reduction of the nitroso intermediate to an amine can be carried out using any method known in the art, such as treatment with sodium borohydride (NaBH4) in ethanol. Scheme 1 [ka]

[0198] The compounds of this disclosure can also be prepared by reacting 1,4-diaminobenzene with a ketone, such as acetone or an aldehyde, as shown in Scheme 2. Scheme 2 [ka]

[0199] The compounds of this disclosure can also be prepared by further reduction of compounds synthesized using Scheme 1 or 2, as shown in Scheme 3 and 4, respectively. The reduction may be carried out using any method known in the art, such as exposure to hydrogen on a carbon-palladium (Pd / C) catalyst. Scheme 3 [ka] Scheme 4 [ka]

[0200] definition When used herein, either alone or as part of another group, the term "alkyl" means 1 to 12 carbon atoms, i.e., C1 to C2 12Alkyl refers to a linear or branched aliphatic hydrocarbon containing an alkyl group, or a specified number of carbon atoms, such as C1-C3 alkyl groups including methyl, ethyl, propyl, or isopropyl, or C1-C4 alkyl groups including methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In one embodiment, alkyl is a linear alkyl group. In another embodiment, alkyl is a branched alkyl group. In one embodiment, alkyl is a C1-C8 alkyl group. In another embodiment, alkyl is a C1-C6 alkyl group. In another embodiment, alkyl is a C1-C4 alkyl group. In another embodiment, alkyl is a C1-C3 alkyl group. Non-limiting exemplary C1-C 12 Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, iso-butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.

[0201] Where used herein, either alone or as part of another group, the term “optionally substituted alkyl” means an alkyl that is either unsubstituted or substituted with one to three substituents, each substituent independently of being nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, cycloalkyl, or -C(=O)OR 1h And in the formula, R 1h These are C1-C6 alkyl groups.

[0202] Where used herein, either alone or as part of another group, the term "alkenyl" refers to an alkyl group containing one, two, or three carbon-carbon double bonds. In one embodiment, the alkenyl group is a C2-C6 alkenyl group. In another embodiment, the alkenyl group is a C2-C4 alkenyl group. In yet another embodiment, the alkenyl group has one carbon-carbon double bond. Non-limiting exemplary alkenyl groups include ethenyl, propenyl, isopropenyl, butenyl, sec-butenyl, pentenyl, and hexenyl.

[0203] Where used herein, either alone or as part of another substituent, the term “optionally substituted alkenyl” means an alkenyl group that is either unsubstituted or substituted with one, two, or three substituents, each substituent independently being halo, nitro, cyano, hydroxy, amino (e.g., alkylamino, dialkylamino), haloalkyl, hydroxyalkyl, alkoxy, haloalkoxy, aryloxy, aralkyloxy, alkylthio, carboxamide, sulfonamide, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, ureido, guanidino, carboxy, carboxyalkyl, optionally substituted cycloalkyl, alkenyl, alkynyl, optionally substituted aryl, optionally substituted heteroaryl, or optionally substituted heterocyclo. In some embodiments, the alkenyl is substituted with a carboxyalkyl group, e.g., -C(=O)OCH2CH3. In some embodiments, the alkenyl is substituted with an optionally substituted phenyl group, e.g., 4-(trifluoromethyl)phenyl.

[0204] Where used herein, either alone or as part of another group, the term "halo" or "halogen" refers to -Cl, -F, -Br, or -I.

[0205] Where used herein, either alone or as part of another group, the term "nitro" refers to -NO2.

[0206] Where used herein, either alone or as part of another group, the term "cyano" refers to -CN.

[0207] Where used herein, either alone or as part of another group, the term "hydroxy" refers to the -OH group.

[0208] Where used herein, either alone or as part of another group, the term "amino" is defined as formula -NR 1f R 1g It refers to the radical of, in the formula, R 1fand R 1g These are independently hydrogen or alkyl.

[0209] In one embodiment, the amino acid is -NH2.

[0210] In another embodiment, amino is "alkylamino," i.e., R 1f C 1~6 It is alkyl, R 1g It is an amino group which is hydrogen. In one embodiment, R 1f These are C1-C4 alkyl groups. Non-exclusive exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.

[0211] In another embodiment, amino is a "dialkylamino," i.e., R 1f and R 1g Each of them is independent of C 1~6 It is an alkyl amino group. In one embodiment, R 1f and R 1g Each of these is independently a C1-C4 alkyl group. Non-limiting exemplary dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.

[0212] Where used herein, either alone or as part of another group, the term "alkylcarbonyl" refers to a carbonyl group substituted with an alkyl group, i.e., -C(=O)-. In one embodiment, the alkyl is a C1-C4 alkyl group. A non-limiting exemplary alkylcarbonyl group is -COCH3.

[0213] 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 group is substituted with one, two, or three fluorine and / or chlorine atoms. In another embodiment, the alkyl group is substituted with one, two, or three fluorine atoms. In another embodiment, the alkyl group is a C1-C6 alkyl group, and the resulting haloalkyl group is referred to as a “C1-C6 haloalkyl group”. In another embodiment, the alkyl group 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. Examples of non-exclusive 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.

[0214] 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 exemplary alkoxy groups include methoxy, ethoxy, and tert-butoxy.

[0215] 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-exclusive exemplary alkylthio groups include -SCH3 and -SCH2CH3.

[0216] When used herein, either alone or as part of another group, the term "cycloalkyl" refers to saturated and partially unsaturated groups, for example, those with 3 to 12 carbon atoms, i.e., C3-C3 12 This refers to a cycloalkyl group containing one or two double bonds, a monocyclic, bicyclic, or tricyclic aliphatic hydrocarbon, or a specified number of carbon atoms, such as C3-C6 cycloalkyls, including cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. In one embodiment, the cycloalkyl group is bicyclic, i.e., has two rings. In another embodiment, the cycloalkyl group is monocyclic, i.e., has one ring. In another embodiment, the cycloalkyl group is C3-C8 cycloalkyl. In another embodiment, the cycloalkyl group is C3-C6 cycloalkyl. In another embodiment, the cycloalkyl group is C5 cycloalkyl, i.e., cyclopentyl. In another embodiment, the cycloalkyl group is C6 cycloalkyl, i.e., cyclohexyl. Non-limiting exemplary C3-C 12 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.

[0217] Where used herein, either alone or as part of another group, the term “optionally substituted phenyl” means phenyl that is either unsubstituted or substituted with 1 to 5 substituents, each substituent independently being halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0218] Where used herein, either alone or as part of another group, the terms “heterocyclo” or “heterocyclyl” refer to a group containing one or two double bonds, monocyclic, bicyclic, or tricyclic groups containing a 3- to 18-membered heterocyclo, i.e., a saturated or partially unsaturated heterocyclo, i.e., containing 3 to 18 ring members, i.e., 1, 2, 3, or 4 heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. Each sulfur atom can be independently oxidized to obtain a sulfoxide, i.e., S(=O), or a sulfone, i.e., S(=O)2. The term heterocyclo includes groups in which one or more -CH2- groups are replaced by 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 heterocyclo also includes groups having optionally substituted aryl or optionally substituted heteroaryl groups, such as indoline, indoline-2-one, 2,3-dihydro-1H-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]azepine, or 1,3,4,5-tetrahydro-2H-benzo[d]azepine-2-one. In some embodiments, the heterocyclo is a six-membered ring containing one nitrogen atom. The heterocyclo may be fused to the rest of the molecule to form a bicyclic group, such as 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.

[0219] Where used herein, either alone or as part of another group, the terms "optionally substituted heterocyclo" or "optionally substituted heterocyclyl" refer to a heterocyclo group that is either unsubstituted or substituted with 1 to 4 substituents, each substituent independently being halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0220] Where used herein, either alone or as part of another group, the term “heteroaryl” refers to a monocyclic aromatic ring system having a 5-6 membered heteroaryl comprising 5-6 ring members, i.e., one, two, three, four, or five heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl has three heteroatoms. In another embodiment, the heteroaryl has two heteroatoms. In another embodiment, the heteroaryl has one heteroatom. In another embodiment, the heteroaryl has a 5-membered heteroaryl having five ring atoms, e.g., furyl, with four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl has a 6-membered heteroaryl having six ring atoms, e.g., pyridyl, with five carbon atoms and one nitrogen atom. Examples of non-exclusive 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., For example, the following are selected: 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-exclusive example of an N-oxide is pyridyl N-oxide.

[0221] Where used herein, either alone or as part of another group, the term “optionally substituted heteroaryl” means a heteroaryl that is either unsubstituted or substituted with one to four substituents, each substituent independently being halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.

[0222] As used herein, the term “stereoisomer” is a general term referring to all isomers of individual molecules that differ only in the orientation of their atoms in space. It includes enantiomers and diastereomers of compounds that have two or more chiral centers that are not mirror images of each other.

[0223] The terms "chiral center" or "asymmetric carbon atom" refer to a carbon atom to which four different groups are bonded.

[0224] The terms "enantiomer" and "enantiomeric" refer to molecules that cannot be superimposed on their mirror image, and therefore are optically active such that the enantiomer rotates the plane of polarization in one direction, while its mirror image compound rotates the plane of polarization in the opposite direction.

[0225] The term "racemic" refers to a mixture of equal amounts of enantiomers, which is optically inert.

[0226] The term "absolute configuration" refers to the spatial arrangement of atoms in a chiral molecular entity (or group) and its stereochemical description, such as R or S.

[0227] The stereochemical terms and rules used herein, unless otherwise indicated, are to be consistent with those set forth in Pure & Appl. Chem 68:2193 (1996).

[0228] 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 is defined as |RS|*100, where R and S are the respective mole or weight fractions of enantiomers in the mixture such that R+S=1. In knowledge of the optical rotation of chiral substances, the percentage enantiomer excess is ([α] obs / [α] max )*100 is defined as [α] obs This is the optical rotation of a mixture of enantiomers, [α] max This is the optical rotation of pure enantiomers. Determination of the enantiomer excess is possible using various analytical techniques, including NMR spectroscopy, chiral column chromatography, or optical polarization spectroscopy.

[0229] In thin-layer chromatography (TLC), the term R f This represents the retaining factor. 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.

[0230] Salts and solvates of the compounds disclosed herein, such as hydrates, can also be used in the manner disclosed herein.

[0231] 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, pivalates, 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.

[0232] 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 include both solvated and unsolvated forms of the compounds of this disclosure.

[0233] 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.

[0234] 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 individually referring 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.

[0235] Furthermore, as used herein, “and / or” is construed to specifically disclose each of the two specified features or components, whether in combination with the other or not. Thus, as used herein in phrases such as “A and / or B,” the term “and / or” is intended to include “A and B,” “A or B,” “A” (alone), and “B” (alone). Similarly, as 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).

[0236] Where an aspect is described herein in the language “comprising,” it is understood that similar aspects described in other terms such as “consisting of” and / or “consisting essentially of” are also provided.

[0237] 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%).

[0238] 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 about 5 wt% to about 95 wt% of at least one elastomer and about 5 wt% to about 95 wt% of a compound of the Disclosure. In some embodiments, the masterbatch comprises about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt% of a compound of the Disclosure. In some embodiments, the masterbatch comprises at least one elastomer in an amount of about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt%.

[0239] 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% to about 95 wt% of the compounds of the Disclosure and about 5 wt% to about 95 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%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt% of the compounds of the Disclosure. In some embodiments, the premix includes at least one additional component in about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt%, such as fillers, rubber chemicals, plasticizers, additional degradation inhibitors, or a combination thereof.

[0240] As used herein, the term “one or more” is intended to mean 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 list of disclosures, e.g., one or more fluorine, chlorine, bromine, and / or iodine atoms, and in some embodiments, there are 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.

[0241] Composition and method of use In another embodiment, the present disclosure provides a composition comprising: (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 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.

[0242] 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%~approximately 95wt / wt%, approximately 65wt / wt%~approximately 75wt / wt%, approximately 65wt / wt%~approximately 85wt / wt%, approximately 65wt / wt%~approximately 95wt / wt%, approximately 75wt / wt%~approximately 85wt / wt%, approximately 75wt / wt%~approximately 95wt / wt%, and approximately 85wt / wt%~approximately 95wt / wt%. Also, approximately 85wt / wt%~approximately 95wt / wt% of the compound contained in this book. The composition of this product is 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% to about 5 wt / wt%, about 0.1 wt / wt% to about 6 wt / wt%, about 0.1 wt / wt% to about 7 wt / wt%, about 0.1 wt / wt% to about 8 wt / wt%, about 0.1 wt / wt% to about 9 wt / wt%, about 0.1 wt / wt% to about 10 wt / wt%, about 0.5 wt / wt% to about 1 wt / wt%, about 0.5 wt / wt% to about 1.5 wt / wt%, about 0.5 wt / wt% to about 2 wt / wt%, about 0.5 wt / wt% to about 2.5 wt / wt%, about 0.5 wt / wt% t%~approx. 3wt / wt%, approx. 0.5wt / wt%~approx. 3.5wt / wt%, approx. 0.5wt / wt%~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%, about 1wt / wt% to about 2.5wt / wt%, about 1wt / wt% to about 3wt / wt%, about 1wt / wt% to about 3.5wt / wt%, about 1wt / wt% to about 4wt / wt%, about 1wt / wt% to about 4.5wt / wt%, about 1wt / wt% to about 5wt / wt%, about 1wt / wt% to about 6wt / wt%, about 1wt / wt% to about 7wt / wt%, about 1wt / wt% to about 8wt / wt%, about 1wt / wt% to about 9wt / wt%, about 1wt / wt% to about 10wt / 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 4.5 wt%; approximately 1.5 wt% to approximately 5 wt%; approximately 1.5 wt% to approximately 6 wt%; approximately 1.5 wt% to approximately 7 wt%; approximately 1.5 wt% to approximately 8 wt%; approximately 1.5 wt% to approximately 9 wt%; approximately 1.5 wt% to approximately 10 wt% Approximately 2 wt% to approximately 2.5 wt%, approximately 2 wt% to approximately 3 wt%, approximately 2 wt% to approximately 3.5 wt%, approximately 2 wt% to approximately 4 wt%, approximately 2 wt% to approximately 4.5 wt%, approximately 2 wt% to approximately 5 wt%, approximately 2 wt% to approximately 6 wt%, approximately 2 wt% to approximately 7 wt%, approximately 2 wt% to approximately 8 wt%, approximately 2 wt% to approximately 9 wt%, approximately 2 wt% to approximately 10 wt%, approximately 2.5 wt% to approximately 3 wt%, approximately 2.5 wt% to approximately 3.5 wt%. Approximately 2.5 wt / wt% to approximately 4 wt / wt%, approximately 2.5 wt / wt% to approximately 4.5 wt / wt%, approximately 2.5 wt / wt% to approximately 5 wt / wt%, approximately 2.5 wt / wt% to approximately 6 wt / wt%, approximately 2.5 wt / wt% to approximately 7 wt / wt%, approximately 2.5 wt / wt% to approximately 8 wt / wt%, approximately 2.5 wt / wt% to approximately 9 wt / wt%, approximately 2.5 wt / wt% to approximately 10 wt / wt%, approximately 3 wt / wt% to approximately 4 wt / wt%, approximately 3 wt / wt% to approximately 4.5 wt / wt%, approximately 3 wt / wt% to approximately 5 wt / wt%, approximately 3 wt / wt% to approximately 6 wt / wt%, approximately 3 wt / wt% to approximately 6 wt / wt%. Approximately 7 wt / wt%, approximately 3 wt / wt% to approximately 8 wt / wt%, approximately 3 wt / wt% to approximately 9 wt / wt%, approximately 3 wt / wt% to approximately 10 wt / wt%, approximately 3.5 wt / wt% to approximately 4 wt / wt%, approximately 3.5 wt / wt% to approximately 4.5 wt / wt%, approximately 3.5 wt / wt% to approximately 5 wt / wt%, approximately 3.5 wt / wt% to approximately 6 wt / wt%, approximately 3.5 wt / wt% to approximately 7 wt / wt%, approximately 3.5 wt / wt% to approximately 8 wt / wt%, approximately 3.5 wt / wt% to approximately 9 wt / wt%, approximately 3.5 wt / wt% to approximately 10 wt / wt%, approximately 4 wt / wt% to approximately 4.5 wt / wt%.Approximately 4 wt / wt% to approximately 5 wt / wt%, approximately 4 wt / wt% to approximately 6 wt / wt%, approximately 4 wt / wt% to approximately 7 wt / wt%, approximately 4 wt / wt% to approximately 8 wt / wt%, approximately 4 wt / wt% to approximately 9 wt / wt%, approximately 4 wt / wt% to approximately 10 wt / wt%, approximately 4.5 wt / wt% to approximately 5 wt / wt%, approximately 4.5 wt / wt% to approximately 6 wt / wt%, approximately 4.5 wt / wt% to approximately 7 wt / wt%, approximately 4.5 wt / wt% to approximately 8 wt / wt%, approximately 4.5 wt / wt% to approximately 9 wt / wt%, approximately 4.5 wt / wt% to approximately 10 wt / wt%, approximately 5 wt / wt% to approximately 6 wt / wt%, approximately 5 wt / wt% to approximately 7 wt / wt%. wt / wt%, approximately 5wt / wt% to approximately 8wt / wt%, approximately 5wt / wt% to approximately 9wt / wt%, approximately 5wt / wt% to approximately 10wt / wt%, approximately 6wt / wt% to approximately 7wt / wt%, approximately 6wt / wt% to approximately 8wt / wt%, approximately 6wt / wt% to approximately 9wt / wt%, approximately 6wt / wt% to approximately 10wt / wt%, approximately 7wt / wt% to approximately 8wt / wt%, approximately 7wt / wt% to approximately 9wt / wt%, approximately 8wt / wt% to approximately 10wt / wt%, approximately 8wt / wt% to approximately 9wt / wt%, approximately 8wt / wt% to approximately 10wt / wt%, and approximately 9wt / wt% to approximately 10wt / wt%. Also, approximately 9wt / wt% to approximately 10wt / wt% of the compounds disclosed herein contain this content.

[0243] 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. In some embodiments, the composition contains about 0.1 wt / wt%, about 0.5 wt / wt%, about 1 wt / wt%, about 1.5 wt / wt%, about 2 wt / wt%, about 2.5 wt / wt%, about 3 wt / wt%, about 3.5 wt / wt%, about 4 wt / wt%, about 4.5 wt / wt%, about 5 wt / wt%, about 5.5 wt / wt%, about 6 wt / wt%, about 6.5 wt / wt%, about 7 wt / wt%, about 7.5 wt / wt%, about 8 wt / wt%, about 8.5 wt / wt%, about 9 wt / wt%, or about 10 wt / wt% of the compounds of the Disclosure.

[0244] In another embodiment, the composition of the Disclosure comprises the compound of the Disclosure and one or more elastomers.

[0245] 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.

[0246] 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).

[0247] 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.

[0248] The composition of the invention is in the form of the present invention, and the composition is about 15wt / wt% ~ about 100wt / 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 1 wt / wt% to 100 wt / wt%, and approximately 5 wt / wt%. ~approx. 15wt / wt%, approx. 5wt / wt%~approx. 25wt / wt%, approx. 5wt / wt%~approx. 35wt / wt%, approx. 5wt / wt%~approx. 45wt / wt%, approx. 5wt / wt%~approx. 55wt / wt%, approx. 5wt / wt%~approx. 65wt / wt%, approx. 5wt / wt%~approx. 75wt / wt%, approx. 5wt / wt%~approx. 85wt / wt%, approx. 5wt / wt%~approx. 95wt / wt%, approx. 5wt / wt%~approx. 100wt / wt%, approx. 15wt / wt%~approx. 25wt / wt%, approx. 15wt / wt%~approx. 35wt / wt%, approx. 15wt / wt%~approx. 4 5wt / wt%, about 15wt / wt%~about 55wt / wt%, about 15wt / wt%~about 65wt / wt%, about 15wt / wt%~about 75wt / wt%, about 15wt / wt%~about 95wt / wt%, about 15wt / wt%~about 100wt / wt%, about 25wt / wt%~about 35wt / wt%, about 25wt / wt%~about 45wt / wt%, about 25wt / wt%~about 55wt / wt%, about 25wt / wt%~about 65wt / wt%, about 25wt / wt%~about 75wt / wt%, about 25wt / wt%~about 85wt / wt%, about 25wt / wt%~approx. 95wt / wt%, approx. 25wt / wt%~approx. 100wt / wt%, approx. 35wt / wt%~45wt / wt%, approx. 35wt / wt%~approx. 55wt / wt%, approx. 35wt / wt%~approx. 65wt / wt%, approx. 35wt / wt%~approx. 75wt / wt%, approx. 35wt / wt%~approx. 85wt / wt%, approx. 35wt / wt%~approx. 95wt / wt%, approx. 35wt / wt%~approx. 100wt / wt%, approx. 45wt / wt%~approx. 55wt / wt%, approx. 45wt / wt%~approx. 65wt / wt%, approx. 45wt / wt%~approx. 75wt / wt%.Approximately 45wt / wt% to approximately 85wt / wt%, approximately 45wt / wt% to approximately 95wt / wt%, approximately 45wt / wt% to approximately 100wt / wt%, approximately 55wt / wt% to approximately 65wt / wt%, approximately 55wt / wt% ~Approx. 75wt / wt%, approx. 55wt / wt% ~ approx. 85wt / wt%, approx. 55wt / wt% ~ approx. 95wt / wt%, approx. 55wt / wt% ~ approx. 100wt / wt%, approx. 65wt / wt% ~ approx. 75wt / wt Contains one or more elastomers in the following proportions: approximately 65 wt / wt% to 85 wt / wt%, approximately 65 wt / wt% to 95 wt / wt%, approximately 65 wt / wt% to 100 wt / wt%, approximately 75 wt / wt% to 85 wt / wt%, approximately 75 wt / wt% to 95 wt / wt%, approximately 75 wt / wt% to 100 wt / wt%, approximately 85 wt / wt% to 95 wt / wt%, or 95 wt / wt% to 100 wt / wt%.

[0249] 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%, about 95 wt / wt%, or about 100 wt / wt%.

[0250] 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.

[0251] In some embodiments, the composition of the Disclosure comprises about 1 phr to about 5 phr of the compound of the Disclosure. In some embodiments, the composition comprises about 0.01 phr to about 0.1 phr, about 0.01 phr to about 0.5 phr, about 0.01 phr to about 1 phr, about 0.01 phr to about 2 phr, about 0.01 phr to about 3 phr, about 0.01 phr to about 4 phr, about 0.01 phr to about 5 phr, about 0.01 phr to about 7.5 phr, about 0.01 phr to about 10 phr, and about 0.01 phr. ~20phr, 0.1phr~0.5phr, 0.1phr~1phr, 0.1phr~2phr, 0.1phr~3phr, 0.1phr~4phr, 0.1 phr~about 5phr, about 0.1phr~about 7.5phr, about 0.1phr~about 10phr, about 0.1phr~about 20phr, about 1phr~about 2phr, about 1phr~about 3phr, about 1phr r ~ about 4phr, about 1phr - about 7.5phr, about 1phr - about 10phr, about 1phr - about 20phr, about 2phr - about 3phr, about 2phr - about 4phr, about 2phr - about 5phr, Approximately 2 phr to approximately 7.5 phr, approximately 2 phr to approximately 10 phr, approximately 2 phr to approximately 20 phr, approximately 3 phr to approximately 4 phr, approximately 3 phr to approximately 5 phr, approximately 3 phr to approximately 7.5 phr, approximately 3 phr ~ This includes compounds of the present disclosure in amounts of approximately 10 phr, approximately 3 phr to approximately 20 phr, approximately 4 phr to approximately 5 phr, approximately 4 phr to approximately 7.5 phr, approximately 4 phr to approximately 10 phr, approximately 4 phr to approximately 20 phr, approximately 5 phr to approximately 7.5 phr, approximately 5 phr to approximately 10 phr, approximately 5 phr to approximately 20 phr, approximately 7.5 phr to approximately 10 phr, approximately 7.5 phr to approximately 20 phr, or approximately 10 phr to approximately 20 phr.

[0252] In some embodiments, the composition of the Disclosure comprises about 3 phr of the compound of the Disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of the compound of the Disclosure.

[0253] In some embodiments, the compositions of the Disclosure comprise the compounds of the Disclosure and one or more fillers.

[0254] As used herein, the term “filler” refers to a substance that strengthens an elastomer composition or imparts to an elastomer composition 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 (CNTs), carbon fibers (HCF), graphite, graphene, aluminosilicate, starch, and fibers, as well as combinations thereof.

[0255] In some embodiments, the filler is derived from a natural source. For example, silica may be derived from rice husks.

[0256] 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%.

[0257] 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%.

[0258] 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.

[0259] 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.

[0260] 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.

[0261] 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.

[0262] 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.

[0263] 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).

[0264] 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.

[0265] 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.

[0266] 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%.

[0267] 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%.

[0268] 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.

[0269] 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.

[0270] As used herein, the term “plasticizer” refers to processing aids used to reduce the viscosity of a composition, increase its plasticity, and / or increase its volume. 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.

[0271] 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%.

[0272] 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%.

[0273] 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.

[0274] 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.

[0275] 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 ozone degradation inhibitors. Non-limiting examples of degradation inhibitors include paraphenylenediamine (PPD), trimethyl-dihydroquinoline (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.

[0276] 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%.Contains one or more additional degradation inhibitors 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%.

[0277] In some embodiments, the compositions of the present disclosure include one or more additional degradation inhibitors in an amount of about 15 wt / wt%. In some embodiments, the compositions include one or more degradation inhibitors 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%.

[0278] In some embodiments, the compositions of the disclosed herein include one or more additional degradation inhibitors in amounts of about 1 phr to about 5 phr. In some embodiments, the compositions include 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, and about 0.01 Contains one or more additional degradation inhibitors in the following ranges: phr to approximately 7.5 phr, approximately 0.01 phr to approximately 10 phr, approximately 0.1 phr to approximately 1 phr, approximately 0.1 phr to approximately 5 phr, approximately 0.1 phr to approximately 7.5 phr, approximately 0.1 phr to approximately 10 phr, approximately 1 phr to approximately 7.5 phr, approximately 1 phr to approximately 10 phr, approximately 5 phr to approximately 7.5 phr, approximately 5 phr to approximately 10 phr, or approximately 7.5 phr to approximately 10 phr.

[0279] 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.

[0280] 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.

[0281] 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 in an amount of 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 aboutContains 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%.

[0282] 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%.

[0283] The Disclosure also provides a process for preparing a composition comprising the compound or composition of the Disclosure and one or more carriers, the process comprising mixing the compound and one or more carriers.

[0284] 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.

[0285] 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.

[0286] 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.

[0287] In some embodiments, the present disclosure provides compositions listed in Table 3. [Table 3-1] [Table 3-2]

[0288] In some embodiments, the vulcanized tire or other rubber article compositions of Table 3 contain about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the compounds of the Disclosure. In some embodiments, the vulcanized tires or other rubber articles of Table 3 include at least one elastomer in an amount of about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt%.

[0289] In some embodiments, the unvulcanized tire internal components, or assembled components, or other end-use component compositions of Table 3 contain about 0.01 wt%, about 0.02 wt%, about 0.03 wt%, about 0.04 wt%, about 0.05 wt%, about 0.06 wt%, about 0.07 wt%, about 0.08 wt%, about 0.09 wt%, about 0.1 wt%, about 0.2 wt%, about 0.3 wt%, about 0.4 wt%, about 0.5 wt%, about 0.6 wt%, about 0.7 wt%, about 0.8 wt%, about 0.9 wt%, about 1 wt%, about 2 wt%, about 3 wt%, about 4 wt%, about 5 wt%, about 6 wt%, about 7 wt%, about 8 wt%, about 9 wt%, or about 10 wt% of the compounds of the Disclosure. In some embodiments, the unvulcanized tire internal components, or assembled components, or other end-use component compositions of Table 3 include at least one elastomer in an amount of about 5 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt%, about 30 wt%, about 35 wt%, about 40 wt%, about 45 wt%, about 50 wt%, about 55 wt%, about 60 wt%, about 65 wt%, about 70 wt%, about 75 wt%, about 80 wt%, about 85 wt%, about 90 wt%, or about 95 wt%.

[0290] 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.

[0291] This disclosure also provides vulcanized elastomer articles prepared using the compositions described herein.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] 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.

[0298] This disclosure also provides a process for refurbishing tires, and this process is (a) Applying the compositions described herein to tires, (b) Placing a pre-vulcanized tread around the tire, (c) Placing a hardening envelope around the tire, (d) including vulcanizing the tires.

[0299] 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 compositions to practice 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 they may be included in a kit describing the compositions and their proper use. [Examples]

[0300] Example 1 Synthesis of N-(furan-2-ylmethyl)-2,2,4-trimethyl-1,2-dihydroquinoline-6-amine (compound 1) Step 1 [ka] A 500 mL flask equipped with an overhead mechanical stirrer, a 50 mL pressure equalization funnel, and a thermometer was filled with 1,4-phenylenediamine (20.9 g, 180 mmol) and methanol (150 mL). The mixture was stirred under N2 protection. A solution of furfural (15.0 g, 12.9 mL, 155.7 mmol) in methanol (19 mL) was filled into the addition funnel. After completely dissolving the 1,4-phenylenediamine, the furfural solution was slowly added to the flask over 8-10 minutes. After the addition was complete, the reaction mixture was stirred at room temperature for 30 minutes (formation of an imine intermediate). The flask was cooled in an ice bath. Sodium borohydride (7.4 g, 195 mmol) was added in small amounts to maintain the temperature below 35°C. After about 30 minutes, the ice bath was removed. The reaction mixture was stirred for 90 minutes without external cooling or heating (reducing the imine to the desired amine product). The reaction was quenched by slowly adding DI water (150 mL) to the flask. After the exothermic reaction subsided, the mixture was transferred to a 1 L beaker equipped with a stirring bar. Ethyl acetate (400 mL) was added. The two-phase system was vigorously stirred and then transferred to a 1 L separatory funnel. The aqueous layer was discarded. The organic layer was washed with water (100 mL) and saturated NaCl aqueous solution (50 mL), and then volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). The crude product was diluted with toluene (10 mL). The resulting solution was packed into a column (73 mm inner diameter) prepared with silica gel 60 (height 20 cm) and 50% ethyl acetate in hexane. The column was eluted with 50% ethyl acetate in hexane. Each resulting fraction was analyzed by silica gel TLC (50% ethyl acetate in hexane). f The fraction containing a dot of =0.8 was discarded (excess alkylation byproduct N 1 ,N 4 -Bis(furan-2-ylmethyl)benzene-1,4-diamine). R f Fractions containing dots of =0.4 were collected, combined, and volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). Further drying was performed in a rotary evaporator (50°C, <3 mbar) for 30 minutes, followed by N2. 1-(furan-2-ylmethyl)benzene-1,4-diamine (intermediate compound 1-I) was obtained as a deep red liquid (18.3 g, 83% yield relative to furfural). The desired structure was obtained as shown in Figure 1. 13 Authentication was performed by 13C NMR spectroscopy.

[0301] Step 2 [ka] In a 250 mL flask equipped with a stirring rod and reflux condenser, N 1 -(furan-2-ylmethyl)benzene-1,4-diamine (intermediate compound 1-I, 15.367 g, 81.64 mmol) was packed into the container, and acetone dried on a molecular sieve (25.0 mL, 338 mmol) was added. The mixture was stirred under N2 protection and immersed in an oil bath at room temperature. Zinc(II) triflate (3.0139 g, 8.29 mmol) was added in a single load. The reaction mixture was heated for 6.5 hours (oil bath temperature = 61°C) and then cooled to room temperature overnight. The reaction mixture was again heated for 6.5 hours (oil bath temperature = 61°C) and then cooled to room temperature. Additional acetone dried on a molecular sieve (10 mL, 135.5 mmol) was added. The reaction mixture was stirred overnight at room temperature and then heated for 6.5 hours (oil bath temperature = 61°C). The total reflux time was 19.5 hours. As the mixture cooled to room temperature (2 days), the crude material was packed into a 73 mm inner diameter column prepared with silica gel 60 (70-230 mesh, 29 cm height) and 20% ethyl acetate in hexane. The flask was rinsed with a small amount of acetone, and the washing solution was packed into the column. The column was eluted with 20% ethyl acetate in hexane. Each resulting fraction was analyzed by silica gel TLC (20% ethyl acetate in hexane). After the desired product began to appear (R f (=0.5), the column was eluted with 50% ethyl acetate in hexane. fAll fractions containing a dot of =0.5 (20% ethyl acetate in hexane) were combined, and volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). The resulting yellow oil was dried in a rotary evaporator (50°C, <10 mbar) for 1.5 hours to obtain N-(furan-2-ylmethyl)-2,2,4-trimethyl-1,2-dihydroquinoline-6-amine (compound 1) = 13.7 g (62.5% relative to N1-(furan-2-ylmethyl)benzene-1,4-diamine) as yellow oil. Compound 1 was prepared as shown in Figures 2 and 3, respectively. 1 H and 13 The sample was characterized by 13C NMR spectroscopy. LC-UV analysis showed a purity of 94.1% at detection at 260 nm.

[0302] Example 2 Synthesis of 2-methyl-6-(phenylamino)-1,2-dihydroquinoline-2,4-dicarboxylate (compound 3) [ka] In a 250 mL round-bottom flask equipped with a stirring rod and reflux condenser, N 1 -Phenylbenzene-1,4-diamine (4-ADPA, 14.6 g, 79.2 mmol) and acetone (85 mL) were packed into the flask. The mixture was stirred under N2 protection. After the 4-ADPA was completely dissolved, ethyl pyruvate (18.5 mL, 166 mmol) and iodine (0.623 g, 2.45 mmol) were sequentially added to the flask. After the addition of iodine, the solution darkened. The mixture was heated (oil bath temperature set to 60°C). The temperature was maintained for about 2 hours. After cooling to room temperature, sodium sulfite (2.4 g, 19.0 mmol) was added, and the mixture was stirred for about 2 hours. Volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). The crude material was diluted with toluene (16 mL). The obtained solution was packed into a column (73 mm inner diameter) that had been pre-prepared with silica gel 60 and ethyl acetate in hexane. The height of the silica gel in the column was approximately 24 cm. The column was eluted with 30% ethyl acetate in hexane. Each fraction was analyzed by silica gel TLC (30% ethyl acetate in hexane). fFractions containing dots of =0.5 were collected, combined, and their volatile substances were removed under reduced pressure (rotary evaporator, water bath = 50°C). Drying was performed in a rotary evaporator (55°C, <8 mbar) for approximately 1 hour to obtain 20.0 g of dimethyl 2-methyl-6-(phenylamino)-1,2-dihydroquinoline-2,4-dicarboxylate (compound 3) as a dark red viscous oil (66% yield relative to 4-ADPA). Compound 3 was then processed as shown in Figures 4 and 5, respectively. 1 H and 13 The sample was characterized by C APT NMR spectroscopy. LC-UV analysis showed a purity of 98.4% at 260 nm detection.

[0303] Example 3 Synthesis of 2,4-diethyl-2-methyl-N-phenyl-1,2-dihydroquinoline-6-amine (compound 6) [ka] A 250 mL round-bottom flask equipped with a stirring bar and reflux condenser was packed with 4-ADPA (5.08 g, 27.6 mmol) and methyl ethyl ketone (40 mL, 447 mmol). The mixture was stirred under N2 protection. Zinc(II) triflate (1.005 g, 2.77 mmol) was added, and the reaction mixture was refluxed for 14 hours (oil bath set to 80°C). The majority of impurities were removed by first purification by column chromatography (silica gel 60, ethyl acetate in hexane at 20%). Subsequently, a second column chromatography (silica gel 60, gradient from ethyl acetate in hexane at 10% to ethyl acetate in hexane at 20%) was performed to obtain a product of acceptable purity. LC-UV analysis showed a purity of 95.0% at detection at 260 nm.

[0304] Alternative procedure A mixture of 4-ADPA (30 g, 163 mmol), methyl ethyl ketone (75 mL, 838 mmol), and zinc(II) triflate (6.0 g, 16.5 mmol) was refluxed overnight under an N2 blanket. After cooling, the reaction mixture was purified by column chromatography on silica gel using 10-20% AcOEt in hexane as the eluent. After removing volatile substances under reduced pressure, purified compound 6 was obtained. The structure is shown in Figure 6. 13 Authentication was performed using C APT NMR spectroscopy (THF-d8).

[0305] Example 4 Synthesis of 2,2,4,7,7,9-hexamethyl-1,2,6,7-tetrahydropyrido[2,3-g]quinoline (compound B1) [ka] In a 250 mL flask equipped with a stirring rod and reflux condenser, 1,4-phenylenediamine (12.6 g, 117 mmol) and acetone, dried using a molecular sieve (57 mL, 771 mmol), were added. The mixture was stirred under N2 protection. Most of the 1,4-phenylenediamine remained insoluble. The flask was immersed in an oil bath at room temperature. Zinc(II) triflate (4.5039 g, 12.4 mmol) was added in a single load. Most of the solid dissolved readily. The reaction mixture was refluxed for 26 hours (oil bath temperature = 63 °C) (some insoluble yellow substances were separated). After cooling to room temperature, the mixture was partitioned in a separatory funnel between dichloromethane (250 mL) and DI water (100 mL). After shaking and decantation, the aqueous phase was discarded. The organic phase was washed with DI water (2 × 100 mL) and saturated NaCl aqueous solution (100 mL), and then volatile substances were removed under reduced pressure (rotary evaporator, water bath = 45°C). The crude material was dissolved in dichloromethane (100 mL). The resulting solution (with some insoluble material remaining) was carefully packed into a sintered filter (inner diameter 7.2 cm) prepared in advance with silica gel (high purity, 60 Å, 230-400 mesh, 40-63 μm, approximately 7.0 cm high, dry) and eluent (70% dichloromethane-25% hexane-5% ethyl acetate). The filter was eluted by gravimetric method with additional eluent. The colored filtrate was collected (approximately 700 mL), and volatile substances were removed under reduced pressure (rotary evaporator, water bath = 45°C). The obtained solid was dried in a rotary evaporator (water bath = 45°C, <5 mbar) for 15 minutes to obtain 10.3 g of 2,2,4,7,7,9-hexamethyl-1,2,6,7-tetrahydropyrido[2,3-g]quinoline (compound B1) (33% relative to 1,4-phenylenediamine) as a yellow solid. Compound B1 was prepared as shown in Figures 7 and 8, respectively. 1 H and 13 The sample was characterized by C APT NMR spectroscopy. LC-UV analysis showed a purity of 91.9% at detection at 260 nm.

[0306] Example 5 Synthesis of 2,2,4,7,7,9-hexamethyl-1,2,3,4,6,7,8,9-octahydropyrido[2,3-g]quinoline (compound B2) [ka] A 300 mL Parr autoclave was packed with compound B1 (3.0 g, 11.2 mmol), ethyl acetate (100 mL), and 10% C-superphosphate (Sigma, 0.61 g). The reaction mixture was stirred under pressure H2 (50 PSIG) at room temperature for 35 minutes. The reaction mixture was filtered through Celite S under suction, and the cake was rinsed with a large amount of ethyl acetate. The combined filtrate was removed under reduced pressure to remove volatile substances (rotary evaporator, water bath = 50°C) to obtain 2,2,4,7,7,9-hexamethyl-1,2,3,4,6,7,8,9-octahydropyrido[2,3-g]quinoline (compound B2) as a light brown solid weighing 2.1 g. Compound B2 was prepared as shown in Figures 9 and 10, respectively. 1 H and 13 The mixture was characterized by C APT NMR spectroscopy. LC-UV analysis showed a purity of 93.1% as a mixture of diastereomers at 260 nm detection.

[0307] Example 6 Synthesis of compound (32) and compound (33) [ka] A 250 mL round-bottom flask fitted with a stirring bar was filled with 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine (5.0 g, 18.9 mmol). The flask was placed under N2 protection and dry DMF (27 mL) was added. Stirring was started. After the 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine was completely dissolved, anhydrous potassium carbonate (3.317 g, 24.0 mmol) was added. The flask was cooled in a cold tap water bath. Iodomethane (1.5 mL, 24.0 mmol) was added over 1-2 minutes. No significant heat was generated. The cooling bath was removed. The reaction mixture was stirred for 21.5 hours without external cooling or heating. Deionized water (27 mL) was added and the mixture was stirred for 30 minutes. AcOEt (100 mL) and deionized water (20 mL) were added, and the mixture was stirred until the gummy material was dissolved. The resulting two-phase system was transferred to a separatory funnel, and the organic layer was collected. The aqueous layer was extracted with AcOEt (70 mL). The combined organic layers were washed with 1 mol / L NaOH aqueous solution (3 × 50 mL) and NaCl aqueous solution, dried over MgSO4, filtered, and then volatile substances were removed under reduced pressure (rotary evaporator; water bath = 50°C). The mixture was further dried in a rotary evaporator (60°C, <10 mbar, 1 hour) to obtain the crude material (brown oil, 4.1 g). The crude material was dissolved in 5% AcOEt in hexane (7 mL). The obtained solution was packed into a 41 mm inner diameter column prepared with silica gel 60 and 5% AcOEt in hexane. The height of the silica gel in the column was 25-26 cm. The column was eluted with 5% AcOEt in hexane. Each resulting portion was analyzed by silica gel TLC. Fraction 1 containing material with an Rf of 0.4 (5% AcOEt in hexane) was collected. The column was eluted with 20% AcOEt in hexane. Fraction 2 containing material with an Rf of 0.15 (5% AcOEt in hexane) was collected. Volatile substances were removed from each fraction independently under reduced pressure (rotary evaporator, water bath = 50°C). The final product was obtained by further drying in a rotary evaporator (60°C, 9-10 mbar) until a certain weight was reached.

[0308] Compound (33) (Fraction 1, chemical name: N,1,2,2,4-pentamethyl-N-phenyl-1,2-dihydroquinoline-6-amine, isolation yield = 0.8 g, pale yellow oil, LC-UV purity = 99.0 area % detected at 260 nm. The structure was verified by LC-MS (M+1 = 293.2) and carbon-13 APT NMR spectroscopy (Figure 11).

[0309] Compound (32) (Fraction 2, chemical name: 1,2,2,4-tetramethyl-N-phenyl-1,2-dihydroquinoline-6-amine, isolation yield = 3.2 g, pale yellow oil, LC-UV purity = 95.5 area% detected at 260 nm. The structure was verified by LC-MS (M+1 = 279.2) and carbon-13 APT NMR spectroscopy (Figure 12).

[0310] Example 7 Synthesis of compound (26) [ka] 2-methylbuta-3-yn-2-ol (73.1 g, 0.869 mol) was added at room temperature to a stirred solution of 4-aminodiphenylamine (100.0 g, 0.543 mol) in toluene (600 mL). The reaction mixture was purged with nitrogen for 10-15 minutes, followed by the addition of CuCl2 (7.3 g, 0.054 mol) and CuCl (5.3 g, 0.065 mol). The resulting reaction mixture was heated to 110-115°C and stirred for 6 hours. After the reaction was complete (monitored by TLC), the mixture was cooled to room temperature, filtered through Celite, the bed was washed with toluene (300 mL), and the collected filtrate was evaporated under vacuum to obtain 128 g of residue. This residue was dissolved in the minimum amount of toluene, packed onto silica gel (100-220 mesh), and eluted with 7-10% ethyl acetate in hexane to obtain 32 g of the crude compound as a dark brown solid. The solid was suspended in 5% IPA in hexane (100 mL), stirred for 16 hours, filtered, and dried under vacuum to obtain a pale yellow solid (purity >95% by HPLC at 260 nm, mass (m / z): 251.14 [M+H]). + 21.1 g of compound (26) was obtained as follows.

[0311] 1 H NMR (400MHz, DMSO-d6): δ7.41(s,1H),7.08(dd,J=8.0,3.2Hz,1H),6.75(d,J=8.0Hz,2H),6.68(dd,J=8.0,2.4Hz,1H),6.64(d,J=2. 4Hz,1H),6.59(t,J=7.2Hz,1H),6.40(d,J=8.0Hz,1H),6.17(d,J=9.6Hz,1H),5.58(s,1H),5.44(dd,J=9.6,1.6Hz,1H),1.21(s,6H)

[0312] 13 C NMR (100MHz, DMSO-d6): δ147.20,140.15,131.94,131.74,129.42,123.76,122.81,120.30,120.06,117.41,114.13,113.30,51.88,31.01

[0313] Example 8 Synthesis of compound (34)

change

[0314] 1 H NMR(400MHz,DMSO-d6):δ7.11(t,J=2.4Hz,2H),6.75-6.71(m,2H),6.62-6.59(m,3H),6 .47(d,J=8.4Hz,1H),5.85(s,1H),5.29(s,1H),3.12(s,3H),1.83(s,3H),1.21(s,6H).

[0315] 13 C NMR(100MHz,DMSO-d6):δ150.46,142.36,137.17,129.12,127.73,127.14,122.01,121.48,116.88,113.85,113.53,51.70,31.41,18.68

[0316] Example 9 Synthesis of compound (35) [ka] 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine (40.0 g, 1 equivalent, 151 mmol) and acetic anhydride (17.0 g, 15.7 mL, 1.1 equivalents, 166 mmol) were added to a 250 mL round-bottom flask equipped with a stirring bar. The reaction mixture was sealed with a septum and stirred at 90°C for 5 hours. After this time, the reaction mixture was diluted with 200 mL of ethyl acetate and transferred to a separatory funnel. The organic layer was washed with saturated aqueous solution. After washing with NaHCO3 (3 × 100 mL), water (2 × 100 mL), and brine (50 mL), it was dried over Na2SO4. The organic layer was concentrated by rotary evaporation and subsequently recrystallized in methanol. The obtained solid was isolated by vacuum filtration, washed with cold methanol, and dried under high vacuum to obtain the desired compound (35) as a white powder (41.086 g, 134.09 mmol, 88.6%). The product was 97.2% at HPLC 260 nm. NMR obtained with DMSO-d6.

[0317] 1 H NMR (81MHz): δ7.56-7.19(m,5H),6.88(d,J=6.7Hz,2H),6.44(d,J=8.8Hz,1 H),6.04(s,1H),5.30(s,1H),1.92(s,3H),1.88-1.75(m,3H),1.20(s,6H).

[0318] 13 C NMR(20MHz):δ169.73,143.73,143.22,131.15,128.78,128.04,126.93,12 6.65,126.64,125.85,122.94,120.30,112.37,51.27,31.13,23.27,18.13.

[0319] Example 10 Synthesis of compound (36) [ka] 2,2,4-trimethyl-N-phenyl-1,2-dihydroquinoline-6-amine (50.00 g, 1 equivalent, 189.1 mmol) and pyridine (100.0 mL) were added to a 500 mL round-bottom flask equipped with a stirring bar. The reaction mixture was stirred at 0°C for 20 minutes, after which 4-methylbenzenesulfonyl chloride (37.14 g, 1.03 equivalents, 194.8 mmol) was slowly added over 20 minutes. The reaction mixture was warmed to room temperature and stirred for 4 hours. After this time, the reaction mixture was diluted with 200 mL of siRNA and poured into a separatory funnel. The organic layer was washed with water (2 × 100 mL), saturated NaHCO3 aqueous solution (2 × 100 mL), water (1 × 100 mL), and brine (1 × 50 mL). The organic layer was dried over Na2SO4 and then concentrated by rotary evaporation. The obtained dark brown oil was pulverized with boiling methanol, the collected powder was released by vacuum filtration, and washed with ice-cold methanol. The solid was dried under high vacuum to obtain compound (36) as white (49.24 g, 118 mmol, 62.2%). The product was 98.9% pure by HPLC at 260 nm. NMR obtained with DMSO-d6.

[0320] 1 H NMR (81MHz): δ7.76-7.16(m,9H),6.93-6.64(m,1H),6.40(d,J=8.3Hz,1H),6.14(s,1H),5.30(s,1H),2.40(s,3H),2.02-1.71(s,3H),1.21(s,6H)

[0321] 13 C NMR(20MHz):δ144.17,143.73,142.51,137.59,129.94,129.79,129.43,129.05,128.4 3,127.79,127.42,126.99,126.89,124.42,120.25,112.53,51.76,31.50,21.26,18.16

[0322] Example 11 Synthesis of compound (42) [ka] A solution of 4-aminodiphenylamine (100.0 g, 0.543 mol) in acetone (500 mL) was purged with nitrogen for 30 minutes, followed by the addition of zinc triflate (39.4 g, 0.108 mol) under a nitrogen atmosphere at room temperature. The resulting reaction mixture was heated at 75-80°C and stirred for 16 hours. After the reaction was complete (monitored by TLC), the system was cooled to room temperature and partitioned between ethyl acetate (500 mL) and water (250 mL). The organic layer was separated, washed with saturated sodium bicarbonate solution (250 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure to obtain 156.0 g of crude product. The crude product was purified by column chromatography using silica gel (100-200 mesh) and eluted with 4-7% siRNA in hexane, yielding a light brown solid (>96% pure by HPLC at 260 nm, mass (m / z): 345.20 [M+H]). + Compound (42) was obtained as a result.

[0323] 1 H NMR (400MHz, DMSO-d6): δ7.47(s,1H),7.10-7.06(m,2H),6.79-6.75(m,4H),6.70(dd,J=8.4,2.4Hz,1H),6.61-6.57 (m,1H),5.44(s,1H),2.26-2.21(m,2H),2.09-2.04(m,2H),1.68-1.55(m,8H),1.47-1.41(m,4H),1.15-1.09(m,1H)

[0324] 13 C NMR(100MHz,DMSO-d6):δ147.19,138.92,136.36,132.40,129.39,124.50,124.19,122.57,12 0.34,117.35,115.79,114.35,114.09,54.80,32.76,25.56,25.38,25.00,23.19,22.59,20.58

[0325] Example 12 Synthesis of compound (43) [ka] A solution of 4-aminodiphenylamine (100.0 g, 0.543 mol) in DMF (1.0 L) was mixed with cyclopentanone (240.6 mL, 5.0 equivalents), followed by p-TSA monohydrate (20.6 g, 0.108 mol), at room temperature under a nitrogen atmosphere. The resulting reaction mixture was heated to 115-120°C and stirred for 16 hours. After the reaction was complete (monitored by TLC), it was cooled to room temperature, quenched with ice-cold water (500 mL), and extracted with ethyl acetate (1.0 L). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated under reduced pressure to obtain 138.0 g of crude product. The obtained crude product was purified by column chromatography using silica gel (100-200 mesh) and eluted with 4-7% SiO2 in hexane, resulting in a pale yellow solid (>96% pure by HPLC at 260 nm, mass (m / z): 317.6 [M+H]). + 38 g of compound (43) was obtained as follows.

[0326] 1 H NMR (400MHz, DMSO-d6): δ7.43(s,1H),7.07(d,J=7.6Hz,2H),6.75(d,J=8.0Hz,2H),6.66(dd,J=8.4,2.0Hz,1H),6.56(t,J=7.6Hz,1H) ),5.54(d,J=2.4Hz,1H),6.48(d,J=8.4,1H),5.64(s,1H),2.47-2.44(m,4H),1.95-1.88(m,2H),1.82-1.73(m,4H),1.63-1.54(m,4H)

[0327] 13 CNMR (100MHz, DMSO-d6): δ147.34,139.66,139.52,131.44,131.29,129.40, 121.74,120.12,117.25,113.96,112.63,64.61,32.21,31.07,24.21,22.26

[0328] Example 13 Oxidation 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 by 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.

[0329] 0.5 wt% of the compound disclosed herein, N 1 -(4-methylpentan-2-yl)-N 4 -Phenylbenzene-1,4-diamine (6PPD), or no antioxidant (blank), was mixed with polyisoprene and heated isothermally at 150°C or 160°C in O2. OIT in minutes is shown in Table 4. As shown by the data in Table 4, the compounds of this disclosure demonstrate antioxidant activity compared to the blank control. [Table 4]

[0330] Example 14 Use of the Compounds of this Disclosure in Sidewall Formulations Rubber sidewall compounds were prepared using the compounds of this disclosure as degradation inhibitors in sidewall formulations. As shown in Table 5, the rubber sidewall compounds were 50 / 50 blends of natural rubber and butadiene rubber with N500 series carbon black. Example 1 is a sidewall compound containing compound 1, Example B1 is a sidewall compound containing compound B1, and Example 6 is a sidewall compound containing compound 6. Control sidewall compounds without degradation inhibitors were also prepared. According to the American Society for Testing and Materials (ASTM) test method D5289, the vulcanization properties of all compounds were characterized by a movable direometer (Alpha Technologies MDR2000), also known as an MDR, at a temperature of 160°C for 60 minutes. The oscillation strain and frequency were set to 0.5°C and 1.667 Hz, respectively. The MDR test results are summarized in Table 6. [Table 5] [Table 6]

[0331] Example 15 Ozone degradation inhibitor performance of the compounds disclosed herein in sidewall compounds The rubber sidewall compound prepared in Example 14 was cured at 160°C for a period equivalent to T90+2 minutes. Ozone test specimens were punched from vulcanized tensile sheets using a die conforming to the American Society for Testing and Materials (ASTM) D1329 standard. The ozone test specimens were stored in the ambient environment for more than 24 hours prior to ozone degradation inhibitor performance testing in an ozone chamber maintained at an ozone concentration of 10±2 parts per hundred million (pphm) and 40±2°C. The ozone test specimens were simultaneously stretched and contracted within the ozone chamber under dynamic conditions. The ozone test specimens were alternately relaxed and stretched to a 25% strain at a rate of 90 cycles per minute during dynamic exposure. Exposure consisted of 16 or 24-hour increments, followed by at least 1 hour of relaxation, after removal from the ozone chamber and before measurement of force at 100% strain.

[0332] The ozone degradation inhibitor performance of the degradation inhibitor formulation compound was evaluated by the percentage of force retention. The percentage of force retention is defined by Equation 1. Equation 1: Force retention ratio = F / F0 * 100% In the formula, F0 is the force at 100% strain before the ozone test, and F is the force at 100% strain after the sample has been aged in the ozone chamber for 16-hour cycles under dynamic exposure. A higher force retention rate is an indicator of better ozone degradation inhibitor performance of the degradation inhibitor compound incorporated into the vulcanized rubber compound.

[0333] The forces of aged and unaged ozone specimens were measured at 100% strain using a tensometer (Alpha Technologies, 2000). The force retention rate of the sidewall compound was calculated and plotted as a function of ozone aging time in Figures 13 (Example 1), 14 (Example B1), and 16 (Example 6).

[0334] Example 16 Use of the Compounds Disclosed in Tread Formulations Rubber tread compounds were prepared using the compounds of this disclosure as degradation inhibitors in tread formulations. As shown in Table 7, these rubber tread compounds are styrene-butadiene rubber and a 70 / 30 blend of butadiene rubber with silica and carbon black. Example 1a is a tread compound containing compound 1, and Example 6a is a tread compound containing compound 6. Control tread compounds without degradation inhibitors were also prepared. According to the American Society for Testing and Materials (ASTM) test method D5289, the vulcanization properties of all compounds were characterized by a movable direometer (Alpha Technologies MDR2000), also known as an MDR, at a temperature of 160°C for 60 minutes. The oscillation strain and frequency were set to 0.5°C and 1.667 Hz, respectively. The MDR test results are summarized in Table 8. [Table 7] [Table 8]

[0335] Example 17 Ozone degradation inhibitor performance of the compounds disclosed in tread compounds Each of the rubber tread compounds prepared in Example 16 was cured at 160°C for a period equivalent to T90+2 minutes. Ozone test specimens were punched from vulcanized tensile sheets using dies compliant with the American Society for Testing and Materials (ASTM) D1329 standard. The ozone test specimens were stored in the ambient environment for more than 24 hours prior to ozone degradation inhibitor performance testing in an ozone chamber maintained at an ozone concentration of 10 ± 2 parts per 100 million (pphm) and 40 ± 2°C. The ozone test specimens were simultaneously stretched and contracted within the ozone chamber under dynamic conditions. During dynamic exposure, the ozone test specimens were stretched to a 25% strain at a rate of 90 cycles per minute. Exposure consisted of 16-hour increments followed by at least 1 hour of relaxation after removal from the ozone chamber and before measurement of force at 100% strain.

[0336] The ozone degradation inhibitor performance of the degradation inhibitor formulation compound was evaluated by the force retention rate defined in Example 15 and Figure 17.

[0337] The force retention rate of the tread compound was calculated and plotted as a function of ozone aging time in Figure 15.

[0338] 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 48】 Compounds having, or its salt, solvate, or stereoisomer, in the formula, 【Chemistry 49】 However, it is either a single bond or a double bond. R １ is optionally substituted C １ to C １２ alkyl, optionally substituted C ２ to C ６ alkenyl, -CHR １ａ R １ｂ 、C ３ to C ７ cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, optionally substituted 5- or 6-membered heteroaryl, -C(=O)R ４ 、-C(=O)OR ４ 、and -SO ２ R ４ is selected from the group consisting of, R １ａ However, optionally substituted phenyl, 4- to 6-membered heterocyclyl, C ３ ~C ６ Selected from the group consisting of cycloalkyls and optionally substituted five-membered or six-membered heteroaryls, R １ｂ However, hydrogen and C １ ~C ９ Selected from the group consisting of alkyl groups, R １ｃ However, hydrogen and C １ ~C ６ Selected from the group consisting of alkyl groups, R ２ａ , R ２ｂ , and R ２ｃ However, it is hydrogen, R ３ａ However, hydrogen, halogen, C １ ~C ９ Alkyl, optionally substituted phenyl, -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , and [Transformation 50] Selected from the group consisting of, R ３ｂ However, hydrogen, halogen, C １ ~C ９ Selected from the group consisting of alkyl and optionally substituted phenyl, or R ３ａ and R ３ｂ However, together with the carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R ３ｃ However, hydrogen, halogen, C １ ~C ９ Alkyl, optionally substituted phenyl, -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , and 【Chemistry 51】 Selected from the group consisting of, R ３ｄ However, hydrogen, halogen, C １ ~C ９ Selected from the group consisting of alkyl and optionally substituted phenyl, or R ３ｃ and R ３ｄ However, together with the two carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R ３ｅ However, hydrogen, C １ ~C ６ Alkyl, optionally substituted C ２ ~C ６ Alkenyl, -C(=O)R ４ , -C (=O) OR ４ , and -SO ２ R ４ Selected from the group consisting of, In each occurrence, Z independently represents -O-, -S-, and -NR ７ - Selected from the group consisting of, R ４ However, in each appearance, hydrogen and C appear independently. １ ~C ９ Alkyl, C １ ~C ９ Haloalkyl, C ３ ~C ７ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, R ５ However, in each appearance, hydrogen and C appear independently. １ ~C ９ Alkyl, C ３ ~C ７ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, R ６ａ , R ６ｂ , R ６ｃ , and R ６ｄ However, in each appearance, hydrogen and C appear independently. １ ~C １２ Selected from the group consisting of alkyl groups and optionally substituted phenyl groups, R ７ is, in each occurrence, independently selected from the group consisting of hydrogen and C １ -C ６ alkyl, but However, the compound of formula (I) is 【Chemistry 52】 A compound, or a salt, solvate, or stereoisomer thereof, provided that it is not a compound.

2. Formula (IIa): 【Chemistry 53】 A compound according to claim 1, or a salt, solvate, or stereoisomer thereof, having the above characteristics.

3. Formula (IIIa): 【Chemistry 54】 A compound according to claim 1, or a salt, solvate, or stereoisomer thereof, having the above characteristics.

4. R ３ａ , R ３ｂ , and R ３ｃ However, the compound according to any one of claims 1 to 3, or a salt, solvate, or stereoisomer thereof, is independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

5. R ３ａ , R ３ｂ , and R ３ｃ is methyl, ethyl, or iso-butyl, the compound according to claim 4, or a salt, solvate, or stereoisomer thereof.

6. R ３ａ and R ３ｃ The compound according to claim 5, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

7. R ３ａ and R ３ｃ The compound according to claim 5, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

8. R ３ａ and R ３ｃ The compound according to claim 5, or a salt, solvate, or stereoisomer thereof, wherein the compound is isobutyl.

9. R ３ｂ The compound according to any one of claims 5 to 8, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

10. R ３ａ and R ３ｂ The compound according to claim 4, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

11. R ３ａ and R ３ｂ The compound according to claim 4, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

12. R ３ａ However, it is ethyl, and R ３ｂ The compound according to claim 4, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

13. R ３ｃ The compound according to any one of claims 10 to 12, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

14. R ３ａ and R ３ｃ is -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , or 【Transformation 55】 The compound according to any one of claims 1 to 3, or a salt, solvate, or stereoisomer thereof.

15. R ３ａ and R ３ｃ is -C(=O)OR ４ The compound according to claim 14, or a salt, solvate, or stereoisomer thereof.

16. Each R ４ The compound according to claim 15, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen, methyl, or ethyl.

17. Each R ４ The compound according to claim 16, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

18. R ３ｂ The compound according to any one of claims 14 to 17, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

19. R ３ｄ 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 １ The compound according to any one of claims 1 to 19, or a salt, solvate, or stereoisomer thereof, wherein the phenyl is optionally substituted.

21. R １ However, C １ ~C １２ A compound according to any one of claims 1 to 19, which is alkyl, or a salt, solvate, or stereoisomer thereof.

22. R １ The compound according to claim 21, 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.

23. R １ but, 【Transformation 56】 The compound according to claim 22, or a salt, solvate, or stereoisomer thereof.

24. R １ However, -CHR １ａ R １ｂ The compound according to any one of claims 1 to 19, or a salt, solvate, or stereoisomer thereof.

25. R １ａ The compound according to claim 24, or a salt, solvate, or stereoisomer thereof, wherein the compound is phenyl, 2-furyl, or 2-tetrahydrofuryl.

26. R １ｂ The compound according to claim 24 or 25, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen or methyl.

27. R １ｃ However, C １ ~C ６ A compound according to any one of claims 1 to 26, which is alkyl, or a salt, solvate, or stereoisomer thereof.

28. R １ｃ The compound according to claim 27, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

29. R １ｃ The compound according to any one of claims 1 to 26, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

30. R ３ｅ However, C １ ~C ６ A compound according to any one of claims 1 to 29, which is alkyl, or a salt, solvate, or stereoisomer thereof.

31. R ３ｅ The compound according to claim 30, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

32. R ３ｅ The compound according to any one of claims 1 to 29, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

33. R ３ｅ However, -C(=O)R ４ The compound according to any one of claims 1 to 29, or a salt, solvate, or stereoisomer thereof.

34. R ４ The compound according to claim 33, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

35. R ３ｅ However, -SO ２ R ４ The compound according to any one of claims 1 to 29, or a salt, solvate, or stereoisomer thereof.

36. R ４ However, C ６ H ５ CH ３ The compound according to claim 35, or a salt, solvate, or stereoisomer thereof.

37. R ３ａ and R ３ｂ However, together with the carbon atoms to which they are bonded, C ３ ~C １２ A compound according to any one of claims 1 to 3, or a salt, solvate, or stereoisomer thereof, which forms a cycloalkyl group.

38. R ３ａ and R ３ｂ The compound according to claim 37, or a salt, solvate, or stereoisomer thereof, wherein these atoms, together with the carbon atoms to which they are bonded, form cyclobutyl, cyclopentyl, or cyclohexyl.

39. R ３ｃ and R ３ｄ However, together with the two carbon atoms to which they are bonded, C ３ ~C １２ A compound according to any one of claims 1 to 3 or 36 to 38, or a salt, solvate, or stereoisomer thereof, which forms a cycloalkyl group.

40. R ３ｃ and R ３ｄ The compound according to claim 39, or a salt, solvate, or stereoisomer thereof, wherein they combine with the two carbon atoms to which they are bonded to form cyclopentyl, cyclopentenyl, cyclohexyl, or cyclohexenyl.

41. A compound according to claim 1, or a salt, solvate, or stereoisomer thereof, selected from one or more of the compounds in Table 1.

42. Formula (IV): 【Chemistry 57】 Compounds having, or its salt, solvate, or stereoisomer, in the formula, each 【Transformation 58】 However, independently, they are single bonds or double bonds. R ８ａ and R ８ｂ 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 , -NR ４ R ５ , -OH, -SH, -SC(=O)R ４ , -SC(=O)SR ４ , -SC(=O)NR ４ R ５ , -NR ４ C(=O)SR ５ , -NR ４ C(=S)SR ５ Selected from the group consisting of 4- to 6-membered heterocyclyls, optionally substituted phenyls, optionally substituted 5- or 6-membered heteroaryls, aryloxys, arylthios, and arylaminos. R ９ａ However, hydrogen, halogen, C １ ~C ９ Alkyl, optionally substituted phenyl, -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , and 【Chemistry 59】 Selected from the group consisting of, R ９ｂ However, hydrogen, halogen, C １ ~C ９ Selected from the group consisting of alkyl groups and optionally substituted phenyl groups, R ９ａ and R ９ｂ However, together with the carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R ９ｃ However, hydrogen, halogen, C １ ~C ９ Alkyl, optionally substituted phenyl, -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , and 【Transformation 60】 Selected from the group consisting of, R ９ｄ However, hydrogen, halogen, C １ ~C ９ Selected from the group consisting of alkyl and optionally substituted phenyl, or R ９ｃ and R ９ｄ However, together with the two carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R ９ｅ However, hydrogen, C １ ~C ６ Alkyl, optionally substituted C ２ ~C ６ Alkenyl, -C(=O)R ４ , -C (=O) OR ４ , and -SO ２ R ４ Selected from the group consisting of, R １０ａ However, hydrogen, halogen, C １ ~C ９ Alkyl, optionally substituted phenyl, -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , and 【Chemistry 61】 Selected from the group consisting of, R １０ｂ However, hydrogen, halogen, C １ ~C ９ Selected from the group consisting of alkyl and optionally substituted phenyl, or R １０ａ and R １０ｂ However, together with the carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R １０ｃ However, hydrogen, halogen, C １ ~C ９ Alkyl, optionally substituted phenyl, -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , and 【Transformation 62】 Selected from the group consisting of, R １０ｄ However, hydrogen, halogen, C １ ~C ９ Selected from the group consisting of alkyl and optionally substituted phenyl, or R １０ｃ and R １０ｄ However, together with the two carbon atoms to which they are bonded, C ３ ~C １２ Forming a cycloalkyl group, R １０ｅ However, hydrogen, C １ ~C ６ Alkyl, optionally substituted C ２ ~C ６ Alkenyl, -C(=O)R ４ , -C (=O) OR ４ , and -SO ２ R ４ Selected from the group consisting of, In each occurrence, Z independently represents -O-, -S-, and -NR ７ - Selected from the group consisting of, R ４ However, in each appearance, hydrogen and C appear independently. １ ~C ９ Alkyl, C １ ~C ９ Haloalkyl, C ３ ~C ７ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, R ５ However, in each appearance, hydrogen and C appear independently. １ ~C ９ Alkyl, C ３ ~C ７ Selected from the group consisting of cycloalkyls and optionally substituted phenyls, R ６ａ , R ６ｂ , R ６ｃ , and R ６ｄ However, in each appearance, hydrogen and C appear independently. １ ~C １２ Selected from the group consisting of alkyl groups and optionally substituted phenyl groups, R ７ However, in each appearance, hydrogen and C appear independently. １～ C ６ A compound selected from the group consisting of alkyl groups, or a salt, solvate, or stereoisomer thereof.

43. Formula (V): 【Transformation 63】 The compound according to claim 42, or a salt, solvate, or stereoisomer thereof, having the above characteristics.

44. Equation (VI): 【Chemistry 64】 The compound according to claim 42, or a salt, solvate, or stereoisomer thereof, having the above characteristics.

45. R ８ａ and R ８ｂ The compound according to any one of claims 42 to 44, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen or methyl.

46. R ９ａ , R ９ｂ , and R ９ｃ The compound according to any one of claims 42 to 45, or a salt, solvate, or stereoisomer thereof, independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.

47. R ９ａ , R ９ｂ , and R ９ｃ The compound according to claim 46, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl, ethyl, or isobutyl.

48. R ９ａ and R ９ｃ The compound according to claim 47, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

49. R ９ａ and R ９ｃ The compound according to claim 47, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

50. R ９ａ and R ９ｃ The compound according to claim 47, or a salt, solvate, or stereoisomer thereof, which is isobutyl.

51. R ９ａ and R ９ｂ The compound according to claim 46, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

52. R ９ａ and R ９ｂ The compound according to claim 46, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

53. R ９ａ However, it is ethyl, and R ９ｂ The compound according to claim 46, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

54. R ９ｃ The compound according to any one of claims 51 to 53, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

55. R ９ａ and R ９ｃ is -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , or 【Transformation 65】 The compound according to any one of claims 42 to 45, or a salt, solvate, or stereoisomer thereof.

56. R ９ａ and R ９ｃ is -C(=O)OR ４ The compound according to claim 55, or a salt, solvate, or stereoisomer thereof.

57. Each R ４ The compound according to claim 56, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen, methyl, or ethyl.

58. Each R ４ The compound according to claim 57, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

59. R ９ｂ The compound according to any one of claims 55 to 58, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

60. R ９ｄ The compound according to any one of claims 42 to 59, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

61. R １０ａ , R １０ｂ , and R １０ｃ The compound according to any one of claims 42 to 60, or a salt, solvate, or stereoisomer thereof, independently selected from the group consisting of hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, and nonyl.

62. R １０ａ , R １０ｂ , and R １０ｃ The compound according to claim 61, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl, ethyl, or isobutyl.

63. R １０ａ and R １０ｃ The compound according to claim 62, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

64. R １０ａ and R １０ｃ The compound according to claim 63, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

65. R １０ａ and R １０ｃ The compound according to claim 63, or a salt, solvate, or stereoisomer thereof, wherein the compound is isobutyl.

66. R １０ａ and R １０ｂ The compound according to claim 61, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

67. R １０ａ and R １０ｂ The compound according to claim 61, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

68. R １０ａ However, it is ethyl, and R １０ｂ The compound according to claim 61, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

69. R １０ｃ The compound according to any one of claims 66 to 68, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

70. R １０ａ and R １０ｃ is -C(=O)OR ４ , -C(=O)NR ４ R ５ , -C(=O)SR ４ ien-CH ２ OR ４ ien-CH ２ OC(=O)R ４ , or 【Chemical Formula 66】 The compound according to any one of claims 42 to 60, or a salt, solvate, or stereoisomer thereof.

71. R １０ａ and R １０ｃ is -C(=O)OR ４ The compound according to claim 70, or a salt, solvate, or stereoisomer thereof.

72. Each R ４ The compound according to claim 71, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen, methyl, or ethyl.

73. Each R ４ The compound according to claim 72, or a salt, solvate, or stereoisomer thereof, wherein the compound is ethyl.

74. R １０ｂ The compound according to any one of claims 58 to 73, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

75. R １０ｄ The compound according to any one of claims 42 to 74, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

76. R ９ａ and R １０ａ However, the compound described in any one of claims 42 to 75, or a salt, solvate, or stereoisomer thereof, is the same.

77. R ９ｂ and R １０ｂ However, the compound described in any one of claims 42 to 76, or a salt, solvate, or stereoisomer thereof, is the same.

78. R ９ｃ and R １０ｃ However, the compound described in any one of claims 42 to 77, or a salt, solvate, or stereoisomer thereof, is the same.

79. R ９ｄ and R １０ｄ However, the compound described in any one of claims 42 to 78, or a salt, solvate, or stereoisomer thereof, is the same.

80. R ９ｅ However, C １ ~C ６ A compound according to any one of claims 42 to 79, which is alkyl, or a salt, solvate, or stereoisomer thereof.

81. R ９ｅ The compound according to claim 80, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

82. R ９ｅ The compound according to any one of claims 42 to 79, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

83. R １０ｅ However, C １ ~C ６ A compound according to any one of claims 42 to 82, which is alkyl, or a salt, solvate, or stereoisomer thereof.

84. R １０ｅ The compound according to claim 83, or a salt, solvate, or stereoisomer thereof, wherein the compound is methyl.

85. R １０ｅ The compound according to any one of claims 42 to 82, or a salt, solvate, or stereoisomer thereof, wherein the compound is hydrogen.

86. A compound according to claim 42, selected from one or more of the compounds in Table 2, or a salt, solvate, or stereoisomer thereof.

87. A composition, (i) The compound according to any one of claims 1 to 86, 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.

88. The composition according to claim 87, wherein the composition comprises one or more elastomers.

89. The composition according to claim 88, wherein the composition comprises about 0.1 wt / wt% to about 10 wt / wt% of the compound and about 5 wt / wt% to about 95 wt / wt% of one or more elastomers.

90. The composition according to any one of claims 87 to 89, wherein the one or more elastomers comprises natural rubber (NR).

91. The composition according to claim 90, wherein the one or more elastomers comprises about 5 wt / wt% to about 100 wt / wt% of natural rubber (NR).

92. The composition according to claim 90 or 91, wherein the natural rubber includes rubber derived from alternative rubber plants.

93. The composition according to claim 92, wherein the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).

94. The composition according to any one of claims 88 to 93, wherein the one or more elastomers include synthetic rubber.

95. The composition according to claim 94, 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.

96. The composition according to claim 95, 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.

97. The composition according to claim 96, wherein the unsaturated rubber comprises styrene-butadiene rubber (SBR).

98. The composition according to claim 97, wherein the one or more elastomers comprises about 5 wt / wt% to about 100 wt / wt% of styrene-butadiene rubber (SBR).

99. The composition according to any one of claims 96 to 98, wherein the unsaturated rubber comprises polybutadiene rubber (BR).

100. The composition according to claim 99, wherein the one or more elastomers comprises about 5 wt / wt% to about 80 wt / wt% of polybutadiene rubber (BR).

101. The composition according to any one of claims 96 to 100, wherein the unsaturated rubber comprises butyl rubber (IIR).

102. The composition according to claim 101, wherein the one or more elastomers comprises about 1 wt / wt% to about 30 wt / wt% of butyl rubber (IIR).

103. The composition according to any one of claims 95 to 102, 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.

104. The composition according to any one of claims 87 to 103, wherein the one or more elastomers further comprises recycled rubber.

105. The composition according to any one of claims 87 to 104, wherein the composition comprises about 0.1 phr to about 10 phr of the compound.

106. The composition according to claim 105, wherein the composition comprises about 0.5 phr to about 5 phr of the compound.

107. The composition according to claim 106, wherein the composition comprises about 1 phr to about 5 phr of the compound.

108. The composition according to any one of claims 87 to 107, wherein the composition comprises one or more fillers.

109. The composition according to claim 108, 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.

110. The composition according to claim 108 or 109, wherein the composition comprises one or more fillers in an amount of about 30 phr to about 500 phr.

111. The composition according to any one of claims 108 to 110, 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.

112. The composition according to claim 111, wherein one or more fillers include silica.

113. The composition according to claim 112, wherein the silica is derived from rice husks.

114. The composition according to any one of claims 108 to 113, wherein the one or more fillers include carbon black.

115. The composition according to any one of claims 87 to 114, wherein the composition comprises one or more rubber chemicals.

116. The composition according to claim 115, 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%.

117. The composition according to claim 115 or 116, wherein the composition comprises one or more rubber chemicals in an amount of about 0.1 phr to about 30 phr.

118. The composition according to claim 117, wherein the composition comprises one or more rubber chemicals in an amount of about 1 phr to about 20 phr.

119. The composition according to any one of claims 115 to 118, 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.

120. The composition according to claim 119, wherein the one or more rubber chemicals comprise one or more vulcanizing agents.

121. The composition according to claim 120, wherein the one or more vulcanizing agents include sulfur, peroxide, resin, or a combination thereof.

122. The aforementioned sulfur is octa-sulfur (S ８ ), cyclododeculfur (S １２ The composition according to claim 121, which is polymerized sulfur, or a combination thereof.

123. The composition according to claim 121, 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.

124. The composition according to claim 121, wherein the resin is a binding resin.

125. The composition according to claims 119 to 124, wherein the one or more rubber chemicals comprise one or more accelerators.

126. The composition according to claim 125, wherein the one or more accelerators include guanidine, thiazole, sulfenamide, thiram, dithiocarbamate, xanthate, thiophosphate, or a combination thereof.

127. The composition according to claim 126, wherein the guanidine is diphenylguanidine (DPG).

128. The composition according to claim 126, 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.

129. The composition according to claim 126, wherein the sulfenamide includes 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.

130. The composition according to claim 126, 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.

131. The composition according to claim 126, 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.

132. The composition according to any one of claims 119 to 131, wherein the one or more rubber chemicals comprises one or more activators.

133. The composition according to claim 132, wherein the one or more activators include a metal oxide, an acid, a metal complex, or a combination thereof.

134. The composition according to claim 133, wherein the metal oxide comprises zinc oxide, magnesium oxide, lead oxide, or a combination thereof.

135. The composition according to claim 133, wherein the acid comprises stearic acid, lauric acid, or a combination thereof.

136. The composition according to claim 133, wherein the metal complex comprises zinc ethylhexanoate.

137. The composition according to any one of claims 119 to 136, wherein the one or more rubber chemicals comprise one or more pre-vulcanization inhibitors.

138. The composition according to claim 137, wherein the one or more pre-vulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride, or a combination thereof.

139. The composition according to any one of claims 87 to 138, wherein the composition comprises one or more plasticizers.

140. The composition according to claim 139, 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.

141. The composition according to claim 139 or 140, wherein the composition comprises one or more plasticizers in an amount of about 0.1 phr to about 30 phr.

142. The composition according to claim 141, wherein the composition comprises one or more plasticizers in an amount of about 1 phr to about 20 phr.

143. The composition according to any one of claims 139 to 142, wherein the one or more plasticizers include mineral oil, organic esters, resins, waxes, ester plasticizers, naturally derived oils, or a combination thereof.

144. The composition according to claim 143, wherein the mineral oil is naphthenic oil, paraffinic oil, or aromatic oil.

145. The composition according to claim 143, wherein the naturally derived oil is soybean oil, vegetable oil, or orange oil.

146. The composition according to any one of claims 87 to 145, wherein the composition further comprises one or more additional degradation inhibitors.

147. The composition according to claim 146, 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%.

148. The composition according to claim 146 or 147, wherein one or more additional degradation inhibitors are present in an amount of about 0.001 phr to about 10 phr.

149. The composition according to claim 148, wherein one or more additional degradation inhibitors are present in an amount of about 0.1 phr to about 5 phr.

150. The composition according to claim 149, wherein one or more additional degradation inhibitors are present in an amount of about 0.5 phr to about 5 phr.

151. The composition according to claim 149, wherein one or more additional degradation inhibitors are present in an amount of about 1 phr to about 5 phr.

152. The composition according to any one of claims 146 to 151, wherein one or more additional degradation inhibitors are antioxidants.

153. The composition according to any one of claims 146 to 151, wherein one or more additional degradation inhibitors are ozone degradation inhibitors.

154. The composition according to any one of claims 146 to 153, wherein one or more additional degradation inhibitors are paraphenylenediamine (PPD), trimethyldihydroquinoline (TMQ), phenols, alkylated diphenylamine (DPA), or diphenylamine-ketone condensates.

155. 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 154, 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).

156. The composition according to claim 155, wherein the PPD is 6PPD.

157. The composition according to claim 154, wherein TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline, or an oligomer or polymer thereof.

158. A composition comprising a compound according to any one of claims 1 to 86, and one or more carriers.

159. A process for preparing the composition according to claim 158, wherein the process comprises mixing the compound and one or more carriers.

160. A vulcanized elastomer article comprising a compound according to any one of claims 1 to 86.

161. A vulcanized elastomer article prepared using the composition described in any one of claims 87 to 158.

162. The vulcanized elastomer article according to claim 160 or 161, wherein the vulcanized elastomer article is a tire.

163. The vulcanized elastomer article according to claim 162, 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.

164. The vulcanized elastomer article according to claim 160 or 161, wherein the vulcanized elastomer article is a component of a tire.

165. The vulcanized elastomer article according to claim 164, wherein the constituent elements are beads, belts, body plies, inner liners, sidewalls, undertreads, or treads.

166. The vulcanized elastomer article according to claim 160 or 161, 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.

167. A process for preparing a vulcanized elastomer article, wherein the process comprises: (a) Forming the composition according to any one of claims 88 to 157 into a molded shape, (b) vulcanizing the formed shape, A process for providing vulcanized elastomer articles.

168. The process according to claim 167, wherein the vulcanization is carried out at an average temperature of about 120°C to about 180°C.

169. The process according to claim 168, wherein the vulcanization is carried out at an average temperature of about 140°C to about 160°C.

170. The process according to any one of claims 167 to 169, wherein the vulcanized elastomer article is a tire.

171. The process according to claim 170, 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.

172. The process according to any one of claims 167 to 171, wherein the vulcanized elastomer article is a component of a tire.

173. The process according to claim 172, wherein the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.

174. The process according to any one of claims 167 to 169, 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.

175. A lubricant composition comprising a lubricant and a compound according to any one of claims 1 to 86.

176. A combustible fuel composition comprising a combustible fuel and a compound according to any one of claims 1 to 86.

177. A fuel additive composition comprising a fuel additive and a compound according to any one of claims 1 to 86.

178. A process for regrowing a tire, wherein the process is (a) Applying the composition according to any one of claims 87 to 168 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.

179. A kit comprising a composition according to any one of claims 87 to 168, and instructions for using the composition in a vulcanizable elastomer composition.

180. A kit comprising a composition according to any one of claims 87 to 168, and instructions for preparing a vulcanized elastomer article using the composition.

181. The composition according to claim 87, wherein the composition comprises about 0.1 wt / wt% to about 10 wt / wt% of the compound.

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