6-aminoquinoline antidegradants
Patent Information
- Application Number
- BR112025020931
- Authority / Receiving Office
- BR · BR
- Patent Type
- Applications
- Publication Date
- 2026-08-25
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Description
1 / 76 “6-AMINOQUINOLINE ANTIDEGRADANTS” FIELD BACKGROUND
[001] This disclosure provides compounds with anti-degradant properties, for example, antiozonants, antioxidants and / or anti-fatigue agents, which are useful additives for vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels and other compositions that require such properties or in compositions that are themselves useful as compositions to impart such properties. BACKGROUND
[002] Many materials, such as plastics, elastomers, elastomeric products (tires, belts, hoses, bushings, supports, vibration isolators, etc.), lubricants, and petroleum-derived products (such as hydraulic fluids, oils, fuels, and oil / fuel additives for automotive and aviation applications) are prone to degradation after prolonged exposure to light, heat, oxygen, ozone, repetitive mechanical actions, and the like. Consequently, compounds and compositions that demonstrate anti-degradation efficacy are well known in the art. For example, US Patent No. 8,987,515 discloses an aromatic polyamine useful in inhibiting oxidative degradation, particularly in lubricating compositions. US Patent Application Publication No. 2014 / 0316163 discloses antioxidant macromolecules with purported improved solubility in many commercially available oils and lubricants.
[003] Antidegradants useful in the manufacture of articles made of elastomers, plastics and the like require a very specific combination of qualities that can be difficult to achieve. While antidegradants must obviously have commercially acceptable efficacy, they must also exhibit this efficacy over extended periods of time associated with the use of the article, particularly on exposed surfaces of the article where degradation primarily occurs due to environmental factors such as light, oxygen and ozone. Just as important as protecting exposed surface components is the effectiveness in protecting Petition 870250108891, dated 11 / 27 / 2025, page 6 / 99 2 / 76 The protection of incorporated components of composite materials against the effects of oxidative aging and repetitive mechanical action is extremely important. Antidegradants must achieve these results without negatively impacting the effectiveness of other additives or the desirable characteristics of the final article. Furthermore, antidegradants that provide or improve mechanical fatigue life after an article has been in service, oxidatively aged, or exposed to ozone are highly valued, as they will inherently improve the mechanical life of the article. Consequently, elastomeric articles that undergo repeated bending, extension, or mechanical compression during service would greatly benefit from such a discovery.
[004] Articles made of commonly used elastomers, such as natural rubber, particularly tires, are especially prone to degradation by oxygen and ozone. As discussed in U.S. Patent No. 2,905,654, the effect of oxygen degradation on rubber is different from the effect of ozone degradation; however, both effects can be detrimental to tire performance, appearance, and service life. Fatigue and crack propagation are also matters of particular concern, especially for areas of steel belt edges and tire sidewalls, which are subject to significant stresses and elongation forces while flexed, inflated, partially inflated, uninflated, and throughout the tire's service life. U.S. Patent No. 8,833,417 describes an antioxidant system that purportedly increases long-term resistance to fatigue and crack propagation relative to known antioxidants discussed immediately below.
[005] Materials with anti-degradation efficacy are well known in the art for use in tire applications and are commercially available. For example, disubstituted N,N'-paraphenylenediamines, such as those sold under the trademark Santoflex®, are generally preferred by many tire manufacturers for this purpose. Document EP 3147321 A1 discloses rubber compositions, tire compounds, amine compounds and anti-aging agents and, in particular, a rubber composition that is considered suitable for use in tire tread rubber. Petition 870250108891, dated 11 / 27 / 2025, page 7 / 99 3 / 76 tread or sidewall rubber of a tire. BRIEF SUMMARY
[006] This disclosure provides compounds that are useful as antidegradants, for example, antiozonants and / or antioxidants, and / or as additives in lubricants or flammable fuels, represented by any of the Formulas (I)-(III) below, collectively referred to herein as “Disclosure Compounds” or individually as a “Disclosure Compound”.
[007] This disclosure also provides compositions comprising:
[008] (i) a Disclosure Composite; and
[009] (ii) one or more elastomers; or
[010] (iii) one or more charges; or
[011] (iv) one or more rubber chemicals; or
[012] (v) one or more plasticizers; or
[013] (vi) one or more additional antidegradants; or
[014] (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers and / or one or more additional antidegradants, collectively referred to herein as “Disclosure Compositions” or individually as a “Disclosure Composition”.
[015] This disclosure also provides Disclosure Compositions comprising a Disclosure Compound and one or more elastomers.
[016] This disclosure also provides Disclosure Compositions comprising a Disclosure Compound and one or more payloads.
[017] This disclosure also provides Disclosure Compositions comprising a Disclosure Compound and one or more rubber chemicals.
[018] This disclosure also provides Disclosure Compositions comprising a Disclosure Compound and one or more plasticizers.
[019] This disclosure also provides Disclosure Compositions Petition 870250108891, dated 11 / 27 / 2025, p. 8 / 99 4 / 76 comprising a Disclosure Compound and one or more additional antidegradants.
[020] This disclosure also provides Disclosure Compositions comprising a Disclosure Compound and one or more carriers.
[021] This disclosure also provides processes for preparing a composition comprising a Disclosure Compound and one or more carriers, the process comprising mixing the compound and one or more carriers.
[022] The present disclosure also provides vulcanized elastomeric items comprising a Disclosure Compound.
[023] The present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein, for example, Disclosure Compositions or compositions comprising a Disclosure Compound and one or more carriers.
[024] This disclosure also provides a process for preparing the vulcanized elastomeric articles described herein, the process comprising:
[025] (a) to form a composition described here in a molded form; and
[026] (b) vulcanize the molded form;
[027] to provide a vulcanized elastomeric article.
[028] This disclosure also provides lubricating compositions comprising a lubricant and a Disclosure Compound.
[029] This disclosure also provides flammable fuel compositions comprising a flammable fuel and a Disclosure Compound.
[030] This disclosure also provides fuel additive compositions comprising a fuel additive and a Disclosure Compound.
[031] This disclosure also provides a process for retreading tires, the process comprising:
[032] (a) apply a composition described here to a tire;
[033] (b) to place a pre-vulcanized tread around the tire;
[034] (c) place a curing envelope around the tire; and Petition 870250108891, dated 11 / 27 / 2025, p. 9 / 99 5 / 76
[035] (d) vulcanize the tire.
[036] This disclosure also provides kits comprising a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition.
[037] This disclosure also provides kits comprising a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article.
[038] Other methods and advantages of disclosure will be presented, in part, in the following description and will flow from the description or can be learned through the practice of disclosure. The methods and advantages of disclosure will be realized and achieved through the elements and combinations particularly pointed out in the appended claims.
[039] It should be understood that both the preceding summary and the detailed description below are merely exemplary and explanatory and are not restrictive of the invention as claimed. BRIEF DESCRIPTION OF THE DRAWINGS
[040] Figure 1 is a line graph representing a 1H nuclear magnetic resonance (NMR) spectrum of the intermediate compound 1-I in d6-dimethyl sulfoxide (d6-DMSO).
[041] Figure 2 is a line graph depicting a 13C APT NMR spectrum of intermediate compound 1-I in d6-DMSO.
[042] Figure 3 is a liquid chromatography (LC) chromatogram of intermediate compound 1-I.
[043] Figure 4 is a line graph depicting a 13C APT NMR spectrum of Compound 1 in d-chloroform (CDCh).
[044] Figure 5 is an LC chromatogram of Compound 1.
[045] Figure 6 is a line graph depicting a 13C APT NMR spectrum of Compound 2 in d6-DMSO.
[046] Figure 7 is an LC chromatogram of Compound 2.
[047] Figure 8 is an LC chromatogram of intermediate compound 3-I. Petition 870250108891, dated 11 / 27 / 2025, page 10 / 99 6 / 76
[048] Figure 9 is a line graph depicting a 13C APT NMR spectrum of Compound 3 in d6-DMSO.
[049] Figure 10 is an LC chromatogram of Compound 3.
[050] Figure 11 is a line graph depicting a 13C APT NMR spectrum of the intermediate compound 4-I in d6-DMSO.
[051] Figure 12 is an LC chromatogram of intermediate compound 4-I.
[052] Figure 13 is a line graph depicting a 13C APT NMR spectrum of Compound 4 in α-DMSO.
[053] Figure 14 is an LC chromatogram of Compound 4.
[054] Figure 15 is a line graph depicting a 13C APT NMR spectrum of the intermediate compound 47-I in cfe-DMSO.
[055] Figure 16 is an LC chromatogram of the intermediate compound 47-I.
[056] Figure 17 is a line graph depicting a 13C APT NMR spectrum of Compound 47 in d6-DMSO.
[057] Figure 18 is an LC chromatogram of Compound 47. DETAILED DESCRIPTION
[058] In one embodiment, the Disclosure Compounds are compounds with Formula (I): R2b R3Í (I),
[059] or a salt, solvate or stereoisomer thereof, where:
[060] ----is a single or double link;
[061] R1a is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR1cR1d, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; Petition 870250108891, dated 11 / 27 / 2025, p. 11 / 99 7 / 76
[062] R1bé selected from the group consisting of hydrogen and C1-C9 alkyl;
[063] R1 is selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5 or 6 membered heteroaryl;
[064] R1dé selected from the group consisting of hydrogen and C1-C9 alkyl;
[065] R2a, R2b and R2c are selected independently from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -OH, -SH, -SC( =O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; or
[066] R2bé selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -OH, -SH, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; and
[067] R2ae R2c together with the two carbon atoms to which they are attached form a C5-C8 cycloalkyl, a 5- to 8-membered heterocyclyl or a C5-C6 aryl;
[068] R3a and R3b are selected independently from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl, provided that if = is a double bond, R3b is absent; or
[069] R3ae R3b together with the carbon atom to which they are attached form a C3-C12 cycloalkyl, with the condition that — is a single bond;
[070] R3c and R3d are selected independently from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl, provided that if — is a double bond, R3d is absent; or
[071] R3ce R3d together with the carbon atom to which they are attached Petition 870250108891, dated 11 / 27 / 2025, p. 12 / 99 8 / 76 form a C3-C12 cycloalkyl group, provided it is a single bond;
[072] R3ee R3fsão selected independently from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S) SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; or
[073] R3ee R3f taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl;
[074] R3g selected from the group consisting of hydrogen and C1-C9 alkyl; and
[075] R4e R5são, in each occurrence, selected independently from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl.
[076] In another embodiment, the Disclosure Compounds are compounds with Formula (I), provided that if R3ee / or R3f are hydrogen, R3ce R3d are selected independently from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl.
[077] In another form, the Disclosure Compounds are compounds with Formula (II):
[078] wherein R1a, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, and R3f are as defined in connection with Formula (I).
[079] In some forms, the Disclosure Compounds are composed Petition 870250108891, dated 11 / 27 / 2025, p. 13 / 99 9 / 76 of Formula (II), where:
[080] R3ce R3dsão selected independently from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl; or
[081] R3ce R3d together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.
[082] In some forms, the Disclosure Compounds are composed of Formula (II), where:
[083] R3ee R3fsão selected independently from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S) SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; or
[084] R3ee R3f when taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.
[085] In some embodiments, the Disclosure Compounds are compounds of Formula (I) or Formula (II), wherein R3bé hydrogen.
[086] In some forms, the Disclosure Compounds are compounds with Formula (III): R2br3í (III),
[087] wherein R1a, R2a, R2b, R2c, R3a, R3c, R3e, and R3f are as defined in connection with Formula (I).
[088] In some embodiments, the Disclosure Compounds are composed of any of Formulas (I)-(III), wherein R1a is optionally substituted phenyl. Petition 870250108891, dated 11 / 27 / 2025, p. 14 / 99 10 / 76
[089] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R1a is C1-C12 alkyl.
[090] In some embodiments, the Disclosure Compounds are composed of any of Formulas (I)-(III), wherein R1a is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl or nonyl.
[091] In some embodiments, the Disclosure Compounds are composed of any of Formulas (I)-(III), wherein R1a is isopropyl or sec-butyl.
[092] In some forms, the Disclosure Compounds are composed of any of the Formulas (I)-(III), where R1a is: or
[093] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R2a, R2b and R2c are selected independently from the group consisting of hydrogen and C1-C9 alkyl.
[094] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R2b and R2c are hydrogen.
[095] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R2a is selected from the group consisting of hydrogen and C1-C4 alkyl.
[096] In some embodiments, the Disclosure Compounds are compounds of any of the Formulas (I)-(III), wherein R3a is hydrogen.
[097] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3a is C1-C9 alkyl.
[098] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3a is C3-C6 cycloalkyl.
[099] In some embodiments, the Disclosure Compounds are composed of any of Formulas (I)-(III), wherein R3a is optionally substituted phenyl.
[0100] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3 is hydrogen. Petition 870250108891, dated 11 / 27 / 2025, p. 15 / 99 11 / 76
[0101] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3 is C1-C9 alkyl.
[0102] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3 is C3-C6 cycloalkyl.
[0103] In some embodiments, the Disclosure Compounds are composed of any of Formulas (I)-(III), wherein R3 is optionally substituted phenyl.
[0104] In some embodiments, the Disclosure Compounds are compounds of any of the Formulas (I)-(III), wherein R3e is hydrogen.
[0105] In some embodiments, the Disclosure Compounds are compounds of any of the Formulas (I)-(III), wherein R3e is C1-C8 alkoxy.
[0106] In some embodiments, the Disclosure Compounds are compounds of any of the Formulas (I)-(III), wherein R3e is -OH.
[0107] In some embodiments, the Disclosure Compounds are compounds of any of the Formulas (I)-(III), wherein R3eé -SH.
[0108] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3e is C1-C8 alkylthio.
[0109] In some embodiments, the Disclosure Compounds are compounds of any of the Formulas (I)-(III), wherein R3e is ariltio.
[0110] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3e is C1-C9 alkyl.
[0111] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3e is C3-C6 cycloalkyl.
[0112] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3e is optionally substituted phenyl.
[0113] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3f is hydrogen.
[0114] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3f is C1-C9 alkyl. Petition 870250108891, dated 11 / 27 / 2025, p. 16 / 99 12 / 76
[0115] In some embodiments, the Disclosure Compounds are compounds of any of Formulas (I)-(III), wherein R3f is C3-C6 cycloalkyl.
[0116] In some embodiments, the Disclosure Compounds are composed of any of Formulas (I)-(III), wherein R3fé is optionally substituted phenyl.
[0117] In some embodiments, the Disclosure Compounds are any one or more of the compounds in Table 1, or a salt or solvate thereof. Petition 870250108891, dated 11 / 27 / 2025, p. 17 / 99 13 / 76 4 Η 5 Η 1 1 ι ^y^NH 6 Η / xJx / x / 1 ΪΤ γ^'ΝΗ 7 Η \ / Ν\Μχ / 1 11 ^γ^ΝΗ οθ Petition 870250108891, dated 11 / 27 / 2025, p. 18 / 99 14 / 76 8 Η 9 Η Ti Ύ ^ ΝΗ 10 Η 11 Η 12 ύ\ Ύ Petition 870250108891, dated 11 / 27 / 2025, p. 19 / 99 15 / 76 13 Η r ΝΗ 14 Petition 870250108891, dated 11 / 27 / 2025, p. 20 / 99 16 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 21 / 99 17 / 76 23 Η (JIJ 24 H ( T 1 T γ^^ΝΗ 25 H (J IJ 26 H ^V^NH Petition 870250108891, dated 11 / 27 / 2025, p. 22 / 99 18 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 23 / 99 19 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 24 / 99 20 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 25 / 99 21 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 26 / 99 22 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 27 / 99 23 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 28 / 99 24 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 29 / 99 25 / 76 Petition 870250108891, dated 11 / 27 / 2025, p. 30 / 99 26 / 76
[0118] The compounds in the Disclosure may be useful as antidegradants, for example, antiozonants and / or antioxidants, as additives in lubricants and as additives in flammable fuels.
[0119] The compounds of the Disclosure can be prepared, for example, by a two-step process comprising i) reacting a 4-nitroaniline with an alkene and an aldehyde or ketone in acetonitrile or other suitable solvents and a catalyst, such as any suitable acid or I2, i.e., by means of a Povarov reaction, and ii) reacting the product of step i) with an aldehyde or ketone under reducing conditions, for example, pressurized H2 with a platinum catalyst, as shown in Scheme 1, wherein R1e is, for example, C1-C12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl or optionally substituted 5- or 6-membered heteroaryl, and R1fé is, for example, hydrogen or C1-C6 alkyl. SCHEME 1 Petition 870250108891, dated 11 / 27 / 2025, page 31 / 99 27 / 76 PUC H; Isopropanol Heat O
[0120] The Disclosure compounds can also be prepared by oxidizing the compound obtained in Scheme 1 by methods known in the art, as shown in Scheme 2. SCHEME 2 DEFINITIONS
[0121] The term “alkyl”, as used herein, alone or as part of another group, refers to a linear or branched chain aliphatic hydrocarbon containing from one to twelve carbon atoms, i.e., a C1-C12 alkyl or the number of carbon atoms designated, for example, C1-C3 alkyl, such as methyl, ethyl, propyl or isopropyl; a C1-C4 alkyl such as methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or t-butyl; and so forth. In one embodiment, the alkyl is a linear chain alkyl. In another embodiment, the alkyl is a branched chain alkyl. In one embodiment, the alkyl is a C1-C5 alkyl. In another embodiment, the alkyl is a C1-C6 alkyl. In another embodiment, the alkyl is a C1-C4 alkyl. In another embodiment, the alkyl group is a C1-C3 alkyl group. Exemplary non-limiting C1-C12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl. Petition 870250108891, dated 11 / 27 / 2025, p. 32 / 99 28 / 76
[0122] The term “optionally substituted alkyl”, as used herein alone or as part of another group, refers to an alkyl that is unsubstituted or substituted by one to three substituents, wherein the substituents are each independently nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, cycloalkyl or -C(=O)OR1i, where R1i is C1-C6 alkyl.
[0123] The term “aryl”, as used herein alone or as part of another group, refers to an aromatic ring system with six to fourteen carbon atoms, i.e., C6-C14 aryl. Non-limiting exemplary aryl groups include phenyl (abbreviated as “Ph”), naphthyl, phenantryl, anthracyl, indenyl, azulenyl, biphenyl, biphenylenyl, and fluorenyl groups. In one embodiment, the aryl group is phenyl or naphthyl. In another embodiment, the aryl group is phenyl.
[0124] The term “halo” or “halogen”, as used herein alone or as part of another group, refers to -Cl, -F, -Br or -I.
[0125] The term “nitro”, as used here alone or as part of another group, refers to -NO2.
[0126] The term “cyan”, as used here alone or as part of another group, refers to -CN.
[0127] The term “hydroxy”, as used here alone or as part of another group, refers to -OH.
[0128] The term “amino”, used alone or as part of another group, refers to a radical of the formula -NR1gR1h, wherein R1g and R1h are independently hydrogen or alkyl.
[0129] In one embodiment, amino is -NH2.
[0130] In another embodiment, the amino group is an “alkylamino”, that is, an amino group where R1 is C1-C6 alkyl and R1 is hydrogen. In one embodiment, R1 is C1-C4 alkyl. Exemplary non-limiting alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.
[0131] In another embodiment, the amino group is a “dialkylamino”, that is, an amino group in which R1 and R1h are each independently C1-C6 alkyl. In a Petition 870250108891, dated 11 / 27 / 2025, p. 33 / 99 29 / 76 embodiment, R1ge R1h are each independently C1-C4 alkyl. Exemplary non-limiting dialkylamino groups include -N(CH3)2 and -N(CH3)CH2CH(CH3)2.
[0132] The term “alkylcarbonyl”, as used herein alone or as part of another group, refers to a carbonyl group, i.e., -C(=O)-, substituted for an alkyl group. In one embodiment, the alkyl is a C1-C4 alkyl. An exemplary non-limiting alkylcarbonyl group is -COCH3.
[0133] The term “haloalkyl”, as used herein alone or as part of another group, refers to an alkyl substituted with one or more fluorine, chlorine, bromine and / or iodine atoms. In one embodiment, the alkyl is substituted with one, two or three fluorine and / or chlorine atoms. In another embodiment, the alkyl is substituted with one, two or three fluorine atoms. In another embodiment, the alkyl is a C1-C6 alkyl and the resulting haloalkyl is called a “C1-C6 haloalkyl”. In another embodiment, the alkyl is a C1-C4 alkyl and the resulting haloalkyl is called a “C1-C4 haloalkyl”. In another embodiment, the alkyl group is a C1 or C2 alkyl. Non-limiting exemplary haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.
[0134] The term “alkoxy”, as used herein alone or as part of another group, 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 called a “C1-C6 alkoxy”. In another embodiment, the alkyl group is a C1-C4 alkyl group, and therefore the resulting alkoxy group is called a “C1-C4 alkoxy”. Non-limiting specimen alkoxy groups include methoxy, ethoxy, and tert-butoxy.
[0135] The term “alkylthio”, as used herein alone or as part of another group, refers to an alkyl group attached to a terminal sulfur atom. In one embodiment, the alkyl is a C1-C6 alkyl, and the resulting alkylthio is termed “C1-C6 alkylthio”. In another embodiment, the alkyl group is a C1-C4 alkyl group and the resulting alkylthio is termed “C1-C4 alkylthio”. Exemplary non-limiting alkylthio groups include -SCH3 and -SCH2CH3.
[0136] The term “ariltio”, as used here alone or as part of Petition 870250108891, dated 11 / 27 / 2025, p. 34 / 99 30 / 76 another group, refers to an aryl group attached to a terminal sulfur atom. In some embodiments, the aryl group is phenyl or naphthyl.
[0137] The term “cycloalkyl”, as used herein, alone or as part of another group, refers to saturated and partially unsaturated aliphatic hydrocarbons, for example, containing one or two double bonds, monocyclic, bicyclic or tricyclic containing from three to twelve carbon atoms, i.e., a C3-C12 cycloalkyl, or the number of carbons designated, for example, a C3-C6 cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. In one embodiment, the cycloalkyl is bicyclic, i.e., it has two rings. In another embodiment, the cycloalkyl is monocyclic, i.e., it has one ring. In another embodiment, the cycloalkyl is a C3-C8 cycloalkyl. In another embodiment, the cycloalkyl is a C3-C6 cycloalkyl. In another embodiment, the cycloalkyl is a C5 cycloalkyl, i.e., cyclopentyl. In another embodiment, the cycloalkyl group is a C6 cycloalkyl group, that is, a cyclohexyl group.Non-limiting C3-C12 cycloalkyl exemplary groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbornyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.
[0138] The term “optionally substituted phenyl”, as used herein alone or as part of another group, refers to phenyl that is unsubstituted or substituted by one to five substituents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.
[0139] The term “heterocycle”, as used herein, alone or as part of another group, refers to saturated and partially unsaturated groups, for example, containing one or two double bonds, monocyclic, bicyclic or tricyclic containing from three to eighteen ring members, i.e., heterocycle of 3 to 18 members, comprising one, two, three or four heteroatoms. Each heteroatom is independently oxygen, sulfur or nitrogen. Each sulfur atom can be independently oxidized to give a sulfoxide, i.e., S(=O), or sulfone, i.e., S(=O)2. The term heterocycle includes groups in which one or more -CH2- groups are replaced by one or more -C(=O)- groups, including cyclic ureido groups, such as Petition 870250108891, dated 11 / 27 / 2025, page 35 / 99 31 / 76 imidazolidinyl-2-one, cyclic amide groups, such as pyrrolidin-2-one or piperidin-2-one, and cyclic carbamate groups, such as oxazolidinyl-2-one. The term heterocycle also includes groups having optionally substituted aryl or optionally substituted heteroaryl groups, such as indoline, indolin-2-one, 2,3-dihydro-1Hpyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-1H-benzo[d]azepine, or 1,3,4,5-tetrahydro2H-benzo[d]azepine-2-one. In some embodiments, the heterocycle is a 6-membered ring comprising a nitrogen atom. The heterocycle can be fused to the rest of the molecule to form a bicyclic group, for example, 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.
[0140] The term “optionally substituted heterocycle”, as used herein, alone or as part of another group, refers to a heterocycle group that is unsubstituted or substituted by one to four substituents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino (e.g., NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.
[0141] The term “heteroaryl”, as used herein, alone or as part of another group, refers to monocyclic aromatic ring systems with five to six ring members, i.e., a 5- to 6-membered heteroaryl comprising one, two, three, four, or five heteroatoms. Each heteroatom is independently oxygen, sulfur, or nitrogen. In one embodiment, the heteroaryl has three heteroatoms. In another embodiment, the heteroaryl has two heteroatoms. In another embodiment, the heteroaryl has one heteroatom. In another embodiment, the heteroaryl has 5 atoms in the ring, for example, furyl, a 5-membered heteroaryl with four carbon atoms and one oxygen atom. In another embodiment, the heteroaryl has 6 atoms in the ring, for example, pyridyl, a 6-membered heteroaryl with five carbon atoms and one nitrogen atom.Non-limiting heteroaryl specimen groups include tienyl, furyl, pyranyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl. In one embodiment, the heteroaryl is chosen from tienyl (e.g., tien-2-yl and tien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., ... Petition 870250108891, dated 11 / 27 / 2025, p. 36 / 99 32 / 76 example, 1H-pirrol-2-ila e 1H-pirrol-3-il), imidazolila (for example, 2H-imidazol-2-ila e 2H-imidazol-4-ila), pirazolila (for example, 1H-pirazol-3-ila, 1H-pirazol-4-ila e 1Hpirazol-5-il), piridila (for example, pyridin-2-ila, pyridin-3-ila e pyridin-4-ila), pyrimidinila (for example, pyrimidin-2-ila, pyrimidin-4-ila e pyrimidin-5-ila), tiazolil (for example, tiazol-2-ila, tiazol-4-il e tiazol-5-ila), isotiazolil (for example, isotiazol-3-ila, isotiazol-4ila and isotiazol-5-ila), oxazolila (for example, oxazol-2-ila, oxazol-4-ila and oxazol-5-ila) and isoxazolila (for example, isoxazol-3-ila, isoxazol-4-ila and isoxazol-5-ila). The term heteroaryl also includes N-oxides. An N-oxide example that is not limiting is the N-oxide of pyridila.
[0142] The term “optionally substituted heteroaryl”, as used herein alone or as part of another group, refers to a heteroaryl that is unsubstituted or substituted by one to four substituents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino (e.g., -NH2, alkylamino or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl or cycloalkyl.
[0143] As used herein, the term “stereoisomers” is a general term for all isomers of an individual molecule that differ only in the orientation of their atoms in space. It includes enantiomers and isomers of compounds with more than one chiral center that are not mirror images of each other (diastereoisomers).
[0144] The term “chiral center” or “asymmetric carbon atom” refers to a carbon atom to which four different groups are attached.
[0145] The terms “enantiomer” and “enantiomeric” refer to a molecule that cannot be superimposed on its mirror image and is therefore optically active, in which the enantiomer rotates the plane of polarized light in one direction and its mirror image compound rotates the plane of polarized light in the opposite direction.
[0146] The term “racemic” refers to a mixture of equal parts of enantiomers, and the mixture is optically inactive.
[0147] The term “absolute configuration” refers to the spatial arrangement of the atoms of a chiral molecular entity (or group) and its stereochemical description, for example, R or S. Petition 870250108891, dated 11 / 27 / 2025, p. 37 / 99 33 / 76
[0148] The stereochemical terms and conventions used in the specification shall be consistent with those described in Pure & Appl. Chem 68: 2193 (1996), unless otherwise indicated.
[0149] The term “enantiomeric 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 percent enantiomeric excess is defined as |R - S|*100, where R and S are the respective mole or weight fractions of the enantiomers in a mixture such that R + S = 1. With knowledge of the optical rotation of a chiral substance, the percent enantiomeric excess is defined as ([a]obs / [a]max)*100, where [a]obs is the optical rotation of the enantiomer mixture and [a]max is the optical rotation of the pure enantiomer. The determination of enantiomeric excess is possible using a variety of analytical techniques, including NMR spectroscopy, chiral column chromatography, or optical polarimetry.
[0150] In thin-layer chromatography (TLC), the term Rf stands for retention factor. Rf is defined as the distance traveled by an individual component divided by the total distance traveled by the eluent. Its value is always between zero and one.
[0151] Salts and solvates, for example, hydrates, of the Compounds of Disclosure may also be used in the methods disclosed herein.
[0152] This disclosure covers the preparation and use of salts of Disclosure Compounds. Salts of Disclosure Compounds may be prepared during the isolation and final purification of the compounds or separately by reacting the compound with an acid having a suitable cation. Salts of Disclosure Compounds may be acid addition salts formed with acceptable acids. Examples of acids that may be employed to form salts include inorganic acids such as nitric, boric, hydrochloric, hydrobromic, sulfuric, and phosphoric acids, and organic acids such as oxalic, maleic, succinic, and citric acids. Non-limiting examples of salts of disclosure compounds include, but are not limited to, hydrochloride, hydrobromide, iodide, sulfate, bisulfate, 2-hydroxyethanesulfonate, phosphate, hydrogen phosphate, acetate, adipate, alginate, aspartate, benzoate, bisulfate, butyrate, Petition 870250108891, dated 11 / 27 / 2025, page 38 / 99 34 / 76 camphorate, camphorsulfonate, digluconate, glycerol phosphate, hemisulfate, heptanoate, hexanoate, formate, succinate, fumarate, maleate, ascorbate, isethionate, salicylate, methanesulfonate, mesitylenesulfonate, naphthylenesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, pamoate, pectinate, persulfate, 3-phenylpropionate, picrate, pivalate, propionate, trichloroacetate, trifluoroacetate, phosphate, glutamate, bicarbonate, paratoluenesulfonate, undecanoate, lactate, citrate, tartrate, gluconate, methanesulfonate, ethanedisulfonate, benzenesulfonate and p-salts of toluenesulfonate. Furthermore, the available amino groups present in the disclosed compounds 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 and phenethyl bromides.In light of the foregoing, any reference to the Disclosure Compounds appearing herein must include the Disclosure Compounds as well as their salts, hydrates or solvates.
[0153] This disclosure covers the preparation and use of solvates of Compounds of the Disclosure. The term “solvate,” as used herein, is a combination, physical association, and / or solvation of a compound of the present disclosure with a solvent molecule, such as, for example, a dissolvate, monosolvate, or hemisolvate, where the ratio of solvent molecule to compound of the present 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 cases, the solvate may be isolated, such as when one or more solvent molecules are incorporated into the crystalline structure of a crystalline solid. Therefore, “solvate” encompasses both solution-phase solvates and isolable solvates.The Disclosure Compounds may be present as solvated forms with a solvent, such as water, methanol, and ethanol, and the Disclosure is intended to include both solvated and non-solvated forms of the Disclosure Compounds.
[0154] One type of solvate is the hydrate. A “hydrate” refers to a specific subgroup of solvates where the solvent molecule is water. The preparation of solvates is known in the art. See, for example, M. Caira et al., J. Pharmaceut. Sci., Petition 870250108891, dated 11 / 27 / 2025, p. 39 / 99 35 / 76 93(3):601-611 (2004), which describes the preparation of fluconazole solvates with ethyl acetate and with water. Similar preparations of solvates, hemisolvates, hydrates and the like are described by van Tonder et al., AAPS Pharm. Sci. Tech., 5(1):Article 12 (2004), and AL Bingham et al., Chem. Commun. 603-604 (2001). A typical and non-limiting process for preparing a solvate would involve dissolving a Disclosure Compound in a desired solvent (organic, water or a mixture thereof) at temperatures above 20 °C to about 25 °C, then cooling the solution at a rate sufficient to form crystals and isolating the crystals by known methods, e.g., filtration. Analytical techniques such as infrared spectroscopy can be used to confirm the presence of the solvent in a solvate crystal.
[0155] The use of the terms “a”, “an”, “the”, “the”, and similar referents in the context of the disclosure description (especially in the context of the claims) should be interpreted as encompassing both the singular and the plural, unless otherwise indicated. The citation of value ranges contained herein serves only as a shorthand method of individually referencing each separate value that falls within the range, unless otherwise indicated herein, and each separate value is incorporated into the specification as if it were individually cited herein. The use of any and all examples, or exemplary language (e.g., “such as”) provided herein, is intended to better illustrate the disclosure and is not a limitation on the scope of the disclosure, unless otherwise claimed. No language in the specification should be interpreted as indicating any unclaimed element as essential to the practice of disclosure.
[0156] Furthermore, “and / or”, when used herein, should be considered as specific disclosure of each of the two specified features or components, with or without the other. Thus, the term “and / or”, as used in a phrase such as “A and / or B” herein, is intended to include “A and B”, “A or B”, “A” (alone) and “B” (alone). Similarly, the term “and / or”, as used in a phrase such as “A, B and / or C”, is intended to encompass each of the following: A, B and C; A, B or C; A or C; A or B; B or C; A and C; A and B; B and C; A (alone); B (alone); and C (alone). Petition 870250108891, dated 11 / 27 / 2025, p. 40 / 99 36 / 76
[0157] It is understood that whenever aspects are described here using the language “including”, analogous aspects described in terms of “consisting of” and / or “consisting essentially of” will also be provided.
[0158] The term “% w / w” as used herein refers to the mass of a component in a composition or mixture, for example, a composition comprising a Disclosure Compound and one or more elastomers; or a Disclosure Composition and one or more fillers; or a mixture comprising two or more elastomers, etc., divided by the combined mass of all components in the composition or mixture, times 100. For example, the % w / w of a Disclosure Compound in a composition comprising 1 kg of the compound, 1 kg of natural rubber and 2 kg of synthetic rubber is 25% w / w (1 kg / 4 kg = 0.25 x 100 = 25%). The % w / w of a Disclosure Compound in a composition comprising 1 kg of the compound and 1 kg of carbon black is 50% w / w (1 kg / 2 kg = 0.50 x 100 = 50%). The percentage by weight (w / w) of a Disclosure Compound in a composition comprising 1 kg of the compound, 1 kg of natural rubber, 2 kg of synthetic rubber and 1 kg of carbon black is 20% by weight (1 kg / 5 kg = 0.20 x 100 = 20%).The percentage by weight (w / w) of natural rubber in a mixture of one or more elastomers comprising 20 kg of natural rubber and 30 kg of synthetic rubber is 40% by weight (20 kg / 50 kg = 0.40 x 100 = 40%).
[0159] As used herein, the term “masterbatch” refers to a composition comprising at least one elastomer and a Disclosure Compound. In some embodiments, the masterbatch comprises about 5% w / w about 95% w / w of at least one elastomer and about 5% w / w about 95% w / w of a Disclosure Compound. In some embodiments, the masterbatch comprises approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of a Compound of Petition 870250108891, dated 11 / 27 / 2025, p. 41 / 99 37 / 76 Disclosure. In some embodiments, the masterbatch comprises approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w, or approximately 95% w / w of at least one elastomer.
[0160] As used herein, the term “premix” refers to a composition comprising a Disclosure Compound and at least one additional component, for example, a filler, a rubber chemical, a plasticizer, an additional antidegradant, or a combination thereof. In some embodiments, the premix does not comprise an elastomer. In some embodiments, the premix comprises from about 5% w / w to about 95% w / w of a Disclosure Compound and from about 5% w / w to about 95% w / w of at least one additional component, for example, a filler, a rubber chemical, a plasticizer, an additional antidegradant, or a combination thereof.In some embodiments, the premix comprises about 5% w / w, about 10% w / w, about 15% w / w, about 20% w / w, about 25% w / w, about 30% w / w, about 35% w / w, about 40% w / w, about 45% w / w, about 50% w / w, about 55% w / w, about 60% w / w, about 65% w / w, about 70% w / w, about 75% w / w, about 80% w / w, about 85% w / w, about 90% w / w or about 95% w / w of a Disclosure Compound.In some embodiments, the premix comprises approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of at least one additional component, per For example, a filler, a rubber chemical, a plasticizer, an additional antidegradant, or a... Petition 870250108891, dated 11 / 27 / 2025, p. 42 / 99 38 / 76 combination of these.
[0161] The term “one or more”, as used herein, is intended to mean that at least one component in a relevant category of components, for example, one or more elastomers, or at least one component in a disclosed list, for example, one or more fluorine, chlorine, bromine and / or iodine atoms, is present and, in some embodiments, more than one component is present. In some embodiments, one or more means 1 to 50. In some embodiments, one or more means 1 to 40. In some embodiments, one or more means 1 to 30. In some embodiments, one or more means 1 to 20. In some embodiments, one or more means 1 to 10. In some embodiments, one or more means 1 to 5. In some embodiments, one or more means 1 to 3. In some embodiments, one or more means 1 or 2. In some embodiments, one or more means 1. COMPOSITIONS AND METHODS OF USE
[0162] In another modality, the disclosure provides compositions comprising:
[0163] (i) a Disclosure Composite; and
[0164] (ii) one or more elastomers; or
[0165] (iii) one or more charges; or
[0166] (iv) one or more rubber chemicals; or
[0167] (v) one or more plasticizers; or
[0168] (vi) one or more additional antidegradants; or
[0169] (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers and / or one or more additional antidegradants.
[0170] In some forms, the composition comprises approximately 0.1% p / p to approximately 10% p / p of the Disclosure Mix, for example, approximately 0.1% p / p to approximately 0.5% p / p, approximately 0.1% p / p to approximately 1% p / p, approximately 0.1% p / p to approximately 1.5% p / p, approximately 0.1% p / p to approximately 2% p / p, approximately 0.1% p / p to approximately 2.5% p / p, approximately 0.1% p / p to approximately 3% p / p, approximately 0.1% p / p to approximately 3.5% Petition 870250108891, dated 11 / 27 / 2025, p. 43 / 99 39 / 76 in w / w search 0.1% w / w search 4% w / w search 0.1% w / w search 4.5% w / w search 0.1% w / w search 5% w / w search 0.1% w / w search 6% w / w search 0.1% w / w search 7 % in w / p, search for 0.1% in w / p search for 8% in w / p, search for 0.1% in w / p search for 9% in w / p, search for 0.1% in w / p search for 10% in w / p, search for 0.5% in w / p search for 1% in p / p, search for 0.5% in w / p search for 1.5% in p / p, search of 0.5 % em w / w search 2% w / w w / w search 0.5% w / w w / w search 2.5% w / w w / w search 0.5% w / w w / w search 3% w / w w / w search 3.5% w / w w / w search 0.5% w / w w / w search 4% w / w w / w search 0.5% w / w search 4.5% em w / w, search 0.5% w / w search 5% w / w, search 0.5% w / w search 6% w / w, search 0.5% w / w search 7% w / w, search 0.5% w / w search 8% w / w, search 05% em w / w search 9% w / w search 0.5% w / w search 10% w / w search 1% w / w search 2% w / w search 1% w / w search 2.5% w / w search 1% w / w search 3% w / w search 1% w / w search 3.5% em w / w, search 1% w / w search 4% w / w search, 1% w / w search 4.5% w / w search, 1% w / w search 5% w / w search, 1% w / w search 6% w / w search, 1% w / w search 7% w / w search, 1% search em p / pa search of 8 % em p / p, search for 1% in p / p search for 9% in p / p, search for 1% in p / p search for 10% in p / p, search for 1.5% in p / p search for 2% in p / p, search for 1.5% in p / p search for 2.5% in p / p, search for 1.5% in p / p search for 3% in p / p, search for 1.5% em w / w search 3.5% w / w search 1.5% w / w search 4% w / w search 1.5% w / w search 4.5% w / w search 1.5% w / w search 5% w / w search 1.5% w / w about 6% w / w, about 1.5% w / w about 7% w / w, about 1.5% w / w about 8% w / w, about 1.5% w / w about 9% w / w, about 1.5% w / w about 10% w / w, about 2% w / w about 2.5% w / w, about 2% w / w about 3% w / w, about 2% w / w about 3.5% w / w, about 2% w / w about 4% w / w, about 2% w / w, Petition 870250108891, dated 11 / 27 / 2025, p. 44 / 99 40 / 76 search 4.5% em p / p, search 2% em p / pa search 5% em p / p, search 2% em p / pa search 6% em p / p, search 2% em p / pa search 7% em p / p, search 2% em p / pa search 8% em p / p, search 2% em p / pa search 9% em p / p, search 2% in p / pa search 10% in p / p, search 2.5% in p / pa search 3% in p / p, search 2.5% in p / pa search 3.5% in p / p, search 2.5% in p / pa search 4% in p / p, search 2.5% in p / pa search 4.5% in p / p, from search of 2.5 % em p / pa search of 5% em p / p, search 2.5% em p / pa search 6% em p / p, search 2.5% em p / pa search 7% em p / p, search 2.5% em p / pa search 8% em p / p, search 2.5% em p / pa search 9% em p / p, search 2.5% em p / pa search 10% em p / p, searching for 3% in p / pa searching for 4% in p / p, searching for 3% in p / pa searching for 4.5% in p / p, searching for 3% in p / pa searching for 5% in p / p, searching for 3% in p / pa searching for 6% in p / p,search 3% em p / pa search 7% em p / p search 3% em p / pa search 8% em p / p search 3% em p / pa search 9% em p / p search 3% em p / pa search 10% em p / p search 3.5% em p / pa search 4% em p / p search 3.5% em p / pa search 4.5% em p / p, search 3.5% em p / pa search 5% em p / p, search 3.5% em p / pa search 6% em p / p, search 3.5% em p / pa search 7% em p / p, search 3.5% em p / pa search 8% em p / p, search 3.5% em p / pa search 9% em p / p, search 3.5% em p / pa search 10% em p / p, search 4% em p / pa search 4.5% em p / p, search 4% em p / pa search 5% em p / p, search 4% em p / pa search 6% em p / p, search 4% em p / pa search 7% em p / p, search 4% em p / pa search 8% em p / p, search 4% em p / pa search 9% em p / p, search 4% em p / pa search 10% em p / p, search 4.5% em p / pa search 5% em p / p, search 4.5% em p / pa search 6% em p / p,from about 4.5% w / w to about 7% w / w, from about 4.5% w / w to about 8% w / w, from about 4.5% w / w to about 9% w / w, from about 4.5% w / w to about 10% w / w, from about 5% w / w to about 6% in w / w, from about 5% in w / w to about 7% in w / w, from about 5% in w / w to about 8% in w / w, from about 5% in w / w to about 9% in w / w, from about 5% in w / w to about 10% in w / w, from about 6% in w / w to about 7%, Petition 870250108891, dated 11 / 27 / 2025, p. 45 / 99 41 / 76 in p / p, of about 6% in p / pa about 8% in p / p, of about 6% in p / pa about 9% in p / p, of about 6% in p / pa about 10% in p / p, of about 7% in p / pa about 8% in p / p, of about 7% in p / pa about 9% in p / p, of about 8% in p / pa about 9% in p / p, of about 8% in p / pa about 10% in p / p, or of about 9% in p / pa about 10% in p / p of a Disclosure Composite.
[0171] In some forms, a Disclosure Composition comprises approximately 15% p / p to approximately 85% p / p of a Disclosure Composition. In some modalities, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 1% w / w, approximately 15% w / w, approximately 1% w / w, approximately 25% w / w, approximately 1% w / w, approximately 35% w / w, approximately 1% w / w, approximately 45% w / w, approximately 1% w / w, approximately 55% w / w, approximately 1% w / w, approximately 65% w / w, approximately 1% w / w, approximately 75% w / w, approximately 1% w / w, approximately 85% w / w, approximately 1% w / w, approximately 95% w / w, and approximately 5% w / w. w / w about 15% in w / w, about 5% in w / w about 25% in w / w, about 5% in w / w about 35% in w / w, about 5% in w / w about 45% in w / w about 65% w / w, from about 5% w / w about 75% w / w,from about 5% w / w to about 85% w / w, from about 5% w / w to about 95% w / w, from about 15% w / w to about 25% w / w, from about 15% w / w to about 35% w / w, from about 15% w / w to about 45% in w / w, from about 15% in w / w about 55% in w / w, from about 15% in w / w about 65% in w / w, from about 15% in w / w about 75% in w / w, from about 15% in w / w about 95% in w / w, from about 25% in w / w about 35 % w / w, around 25% in p / pa approximately 45% in p / p, approximately 25% in p / pa approximately 55% in p / p, approximately 25% in p / pa approximately 65% in p / p, approximately 25% in p / pa approximately 75% in p / p, approximately 25% in p / pa approximately 85% in p / p, approximately 25% in p / pa approximately 95% in p / p, approximately 35% in p / pa approximately 45% in p / p, approximately 35% in p / pa approximately 55% in p / p, approximately 35% in p / pa approximately 65% in, Petition 870250108891, dated 11 / 27 / 2025, p. 46 / 99 42 / 76 w / w, from about 35% in w / w to about 75% in w / w, from about 35% in w / w to about 85% in w / w, from about 35% in w / w about 95% in w / w approx. % in p / pa around 75% in p / p, of about 55% p / pa, about 85% p / p, of about 55% p / pa, about 95% p / p, of about 65% p / pa, about 75% p / p, of about 65% p / pa, about 85% p / p, of about 65% p / pa, about 95% p / p, of about 75% p / pa, about 85% p / p, of about 75% p / pa, about 95% p / p, or of about 85% p / pa, about 95% p / p of the Disclosure Composite.
[0172] In some forms, a Disclosure Composition comprises approximately 50% by weight (w / w) of a Disclosure Composite. In some forms, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w, or approximately 95% w / w of the Disclosure Mix.
[0173] In another embodiment, a Disclosure Composition comprises a Disclosure Compound and one or more elastomers.
[0174] The term “elastomer,” as used herein, is a polymer with viscoelasticity (i.e., having both viscosity and elasticity) that typically has low intermolecular forces, a low Young’s modulus, and high strain at failure. Elastomers can generally be crosslinked by heating in the presence of one or more crosslinking agents, a process called curing or vulcanization. Rubber is a type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and mixtures thereof. The term “natural rubber,” as used herein, refers to a natural elastomer that can be obtained from Petition 870250108891, dated 11 / 27 / 2025, page 47 / 99 43 / 76 Hevea rubber trees. Non-limiting types of synthetic rubbers include unsaturated rubbers, saturated rubbers, rubbers with fluoro and fluoroalkyl or fluoroalkoxy substituent groups in the polymer chain (FKM), silicone rubbers (Q), and mixtures thereof. Non-limiting examples of unsaturated rubbers include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene-butadiene rubber (SBR), nitrile-butadiene rubber (NBR), chloroprene rubber (CR), ethylene-propylene-diene rubber (EPDM), and mixtures thereof. These unsaturated rubbers undergo cyclization and crosslinking reactions that lead to hardening of the aged part. As oxidation occurs, these vulcanizates harden and eventually become brittle products. Partial oxidation of vulcanized materials leads to performance losses when used in applications such as vehicle tire sidewalls.Saturated rubbers are rubbers that do not contain C=C unsaturation and include, but are 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), rubbers with fluoro and fluoroalkyl or fluoroalkoxy substituent groups in the polymer chain (FKM), silicone rubber (Q), and mixtures thereof.
[0175] In some embodiments, natural rubber comprises rubber derived from an alternative rubber plant. The term “natural rubber comprises rubber derived from an alternative rubber plant”, as used herein, refers to a natural elastomer 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).
[0176] In some embodiments, one or more elastomers also comprise recycled rubber. The term “recycled rubber,” as used herein, refers to an elastomer that has been recovered from discarded materials, such as used tires.
[0177] In some modalities, a Disclosure Composition Petition 870250108891, dated 11 / 27 / 2025, page 48 / 99 44 / 76 comprises approximately 15% by weight (w / w) to approximately 85% by weight (w / w) of one or more elastomers. In some modalities, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 1% w / w, approximately 15% w / w, approximately 1% w / w, approximately 25% w / w, approximately 1% w / w, approximately 35% w / w, approximately 1% w / w, approximately 45% w / w, approximately 1% w / w, approximately 55% w / w, approximately 1% w / w, approximately 65% w / w, approximately 1% w / w, approximately 75% w / w, approximately 1% w / w, approximately 85% w / w, approximately 1% w / w, approximately 95% w / w, and approximately 5% w / w. w / w about 15% in w / w, about 5% in w / w about 25% in w / w, about 5% in w / w about 35% in w / w, about 5% in w / w about 45% in w / w about 65% w / w, about 5% w / w about 75% w / w, about 5% w / w about 85% w / w,search 5% in p / p search 95% in p / p search 15% in p / p search 25% in p / p search 15% in p / p search 35% in p / p search 15% in p / p search 45% in p / p search 15% in p / pa search 55% in p / p search 15% in p / pa search 65% in p / p, search 15% in p / pa search 75% in p / p, search 15% in p / pa search 95% in p / p, search 25% in p / pa search 35% in p / p, search 25% in p / pa search 45% in p / p, search 25% in p / pa search 55 % em p / p, search for 25% em p / pa search 65% em p / p, search 25% em p / pa search 75% em p / p, search 25% em p / pa search 85% em p / p, search 25% em p / pa search 95% em p / p, search 35% em p / pa search 45% em p / p, search 35% em p / pa search 55% in p / p, search 35% in p / pa search 65% in p / p, search 35% in p / p search 75% in p / p, search 35% in p / pa search 85% in p / p,from about 35% w / w to about 95% w / w, from about 45% w / w to about 55% w / w, from about 45% w / w to about 65% w / w, from about 45% w / w to about 75% w / w, from about 45% w / w to about 85% in w / w, from about 45% w / w to about 95% w / w, from about 55% w / w to about 65% w / w, from about 55% w / w to about 75% w / w, from about 55% w / w to about 85% w / w, to about 55% w / w, Petition 870250108891, dated 11 / 27 / 2025, p. 49 / 99 45 / 76 approximately 95% w / w, approximately 65% w / p approximately 75% w / w, approximately 65% w / p approximately 85% w / w, approximately 65% w / p approximately 95% w / w, approximately 75% w / p approximately 85% w / w, approximately 75% w / p approximately 95% w / w, or approximately 85% w / p approximately 95% w / p of one or more elastomers.
[0178] In some embodiments, a Disclosure Composition comprises about 50% by weight of one or more elastomers. In some embodiments, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of one or more elastomers.
[0179] The term “phr”, as used herein, refers to parts per hundred parts of rubber by weight. The parts by weight of the individual components are based on 100 parts by weight of the total mass of one or more elastomers present in the composition.
[0180] In some embodiments, a Disclosure Composition comprises from about 1 phr to about 5 phr of a Disclosure Compound.In some embodiments, the composition comprises from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 0.5 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 2 phr, from about 0.01 phr to about 3 phr, from about 0.01 phr to about 4 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.01 phr to about 20 phr, from about 0.1 phr to about 0.5 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 2 phr, from about 0.1 phr to about 3 phr, from about 0.1 phr to about 4 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 20 phr, from about 1 phr to about 2 phr, from about 1 phr to about 3 phr, from about 1 phr to about 4 phr, from about 1 phr to about 7.5 phr, from. Petition 870250108891, dated 11 / 27 / 2025, page 50 / 99 46 / 76 about 1 phr to about 10 phr, from about 1 phr to about 20 phr, from about 2 phr to about 3 phr, from about 2 phr to about 4 phr, from about 2 phr to about 5 phr, from about 2 phr to about 7.5 phr, from about 2 phr to about 10 phr, from about from 2 phr to about 20 phr, from about 3 phr to about 4 phr, from about 3 phr to about 5 phr, from about 3 phr to about 7.5 phr, from about 3 phr to about 10 phr, from about 3 phr to about 20 phr, from about 4 phr to about 5 phr, from about 4 phr to about 7.5 phr, from about 4 phr to about 10 phr, from about 4 phr to about 20 phr, from about 5 phr to about 7.5 phr, from about 5 phr to about 10 phr, from about 5 phr to about 20 phr, from about 7.5 phr to about 10 phr, from about 7.5 phr to about 20 phr, or from about 10 phr to about 20 phr of the Disclosure Compound.
[0181] In some embodiments, a Disclosure Composition comprises about 3 phr of a Disclosure Compound. 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 a Disclosure Compound.
[0182] In some forms, a Disclosure Composition comprises a Disclosure Compound and one or more payloads.
[0183] The term “filler,” as used herein, is a substance that reinforces an elastomeric composition or imparts to an elastomeric composition other properties, including, but not limited to, expanding the volume of the composition. Non-limiting examples of fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), high-carbon fibers (HCFs), graphite, graphene, aluminosilicates, starch and fibers, and combinations thereof.
[0184] In some embodiments, the filler is derived from natural sources. For example, silica can be derived from rice husks.
[0185] In some modalities, a Disclosure Composition comprises approximately 15% p / p or approximately 85% p / p of one or more loads. In some modalities, the composition comprises approximately 1% p / p or approximately Petition 870250108891, dated 11 / 27 / 2025, p. 51 / 99 47 / 76 of 5% in w / p, search of 1% in w / p search of 15% in w / p, search of 1% in w / p search of 25% in w / p, search of 1% in w / p search of 35% in w / p, search of 1% in p / p search of 45% in p / p, search of 1% in w / p search of 55% p / p, search 1% in p / pa search 65% in p / p, search 1% in p / pa search 75% in p / p, search 1% in p / pa search 85% in p / p, search 1% in p / pa search 95% in p / p, search 5% in p / pa search 15% in p / p, search 5% in p / pa search 25 % em p / p, search 5% in p / pa search 35% in p / p, search 5% in p / pa search 45% in p / p, search 5% in p / pa search 55% in p / p, search 5% in p / pa search 65% in p / p, search 5% in p / pa search 75% in p / p, search 5% in p / p search 85% in p / p, search 5% in p / p search 95% in p / p, search 15% in p / p search 25% in p / p, search 15% in p / pa search 35% in p / p,search 15% em p / pa search 45% em p / p search 15% em p / pa search 55% em p / p search 15% em p / pa search 65% em p / p search 15% em p / pa search 75% em p / p search 15% em p / pa search 95% em p / p search 25% em p / pa search 35% em p / p, search 25% em p / pa search 45% em p / p, search 25% em p / pa search 55% em p / p, search 25% em p / pa search 65% em p / p, search 25% em p / pa search 75% em p / p, search 25% em p / pa search 85% em p / p, looking for 25% em p / pa search 95% em p / p search 35% em p / pa search 45% em p / p search 35% em p / pa search 55% em p / p search 35% em p / pa search 65% em p / p search 35% em p / pa search 75% em p / p search 35% em p / p search 85% in p / p, search 35% in p / p search 95% in p / p, search 45% in p / p search 55% in p / p, search 45% in p / pa search 65% in p / p,from about 45% w / w to about 75% w / w, from about 45% w / w to about 85% w / w, from about 45% w / w to about 95% w / w, from about 55% w / w to about 65% w / w, from about 55% w / w to about 75% in w / w, from about 55% w / w about 85% w / w, from about 55% w / w about 95% w / w, from about 65% w / w about 75% w / w, from about 65% w / w about 85% w / w, from about 65% w / w about 95 % w / w, around 75 % in, Petition 870250108891, dated 11 / 27 / 2025, p. 52 / 99 48 / 76 p / pa approximately 85% p / p, approximately 75% p / pa approximately 95% p / p, or approximately 85% p / pa approximately 95% p / p of one or more loads.
[0186] In some forms, a Disclosure Composition comprises approximately 50% by weight of one or more charges. In some forms, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of one or more fillers.
[0187] In some forms, a Disclosure Composition comprises from about 30 phr to about 500 phr of one or more loads. In some embodiments, the composition comprises from about 30 phr to about 50 phr, from about 30 phr to about 100 phr, from about 30 phr to about 150 phr, from about 30 phr to about 200 phr, from about 30 phr to about 250 phr, from about 30 phr to about 300 phr, from about 30 phr to about 350 phr, from about 30 phr to about 400 phr, from about 30 phr to about 450 phr, from about 30 phr to about 500 phr, from about 50 phr to about 100 phr, from about 50 phr to about 150 phr, from about 50 phr to about 200 phr, from about 50 phr to about 250 phr, from about 50 phr to about 300 phr, from about 50 phr to about 350 phr, from about 50 phr to about 400 phr, from about 50 phr to about 450 phr, from about 50 phr to about 500 phr, from about 100 phr to about 150 phr, from about 100 phr to about 200 phr,from about 100 phr to about 250 phr, from about 100 phr to about 300 phr, from about 100 phr to about 350 phr, from about 100 phr to about 400 phr, from about 100 phr to about 450 phr, from about 100 phr to about 500 phr, from about 150 phr to about 200 phr, from about 150 phr to about 250 phr, from about 150 phr to about 300 phr, from about 150 phr to about 350 phr, from about 150 phr to about 400 phr, from about 150 phr to about 450 phr, from about 150 phr at about 500 phr, from about 200 phr to about 250 phr, from about 200 phr to about 300 phr, from about 200 phr to about 350 phr, from, Petition 870250108891, dated 11 / 27 / 2025, page 53 / 99 49 / 76 from about 200 phr to about 400 phr, from about 200 phr to about 450 phr, from about 200 phr to about 500 phr, from about 250 phr to about 300 phr, from about 250 phr to about 350 phr, from about 250 phr to about 400 phr, from about 250 phr to about 450 phr, from about 250 phr to about 500 phr, from about 300 phr to about 350 phr, from about 300 phr to about 400 phr, from about 300 phr to about 450 phr, from about 300 phr to about 500 phr, from about 350 phr to about 400 phr, from about 350 phr to about 450 phr, from about 350 phr to about 500 phr, from about 400 phr to about 450 phr, from about 400 phr to about 500 phr, or from about 450 phr to about 500 phr of one or more loads.
[0188] In some embodiments, a Disclosure Composition comprises approximately 300 phr of one or more payloads. In some embodiments, the composition comprises approximately 30 phr, approximately 50 phr, approximately 100 phr, approximately 150 phr, approximately 200 phr, approximately 250 phr, approximately 350 phr, approximately 400 phr, approximately 450 phr, or approximately 500 phr of one or more payloads.
[0189] In some embodiments, a Disclosure Composition comprises a Disclosure Compound and one or more rubber chemicals. The term “rubber chemicals,” as used herein, refers to a compound or substance used to facilitate the vulcanization of rubber. Rubber chemicals include, but are not limited to, vulcanizing agents, accelerators, activators, and pre-vulcanization inhibitors.
[0190] The term “vulcanization,” as used herein, refers to a process in which cross-links are formed between elastomers to effect changes in the material properties of the elastomers. In particular, vulcanization typically increases the stiffness and durability of elastomers. Vulcanization is carried out at room temperature or at elevated temperatures, depending on the nature of the elastomer(s), filler(s), and rubber chemical(s) used. The term “curing” is also used in the art to describe this process.
[0191] The term “vulcanizing agent”, as used herein, refers to any substance that allows crosslinking between elastomers. Vulcanizing agents may allow crosslinking between separate polymer chains of Petition 870250108891, dated 11 / 27 / 2025, page 54 / 99 50 / 76 an elastomer by several mechanisms, including, but not limited to, the formation of covalent bonds between the vulcanizing agent and two or more separate polymer chains or the generation of radical species in separate polymer chains that can combine to form covalent bonds between the two polymer chains. Non-limiting examples of vulcanizing agents include sulfur, peroxides, vulcanized vegetable oil, forceps, and resins. Non-limiting examples of sulfur include octasulfur (S8), cyclododecasulfur (S12), and polymeric sulfur. Non-limiting examples of peroxides include benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5-Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di-(tert-butylperoxy)valerate (VAL), and 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC). Non-limiting examples of resins include bonding resins.The term “bonding resin,” as used herein, refers to a chemical, such as resorcinol formaldehyde resins and phenolic resins, that reacts with methylene donors (such as hexamethylenetetramine (HMTA) or hexamethoxymethylmelamine (HMMM)) to promote adhesion.
[0192] The term “accelerator,” as used herein, refers to any substance that increases the kinetics of vulcanization. In some embodiments, accelerators allow vulcanization to be carried out at lower temperatures and / or allow the vulcanizing agent, for example, sulfur, to be used more efficiently. Non-limiting examples of accelerators include guanidines, thiazoles, sulfenamides, thiurams, dithiocarbamates, xanthates, and thiophosphates. Non-limiting examples of guanidines 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-benzothiazolesulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydiethylene benzothiazole sulfenamide (OBTS), N-oxydiethylenethiocarbamyl-N'-oxydiethylene sulfenamide (OTOS), and thiocarbamyl sulfenamide. Non-limiting examples of thiurams include dithioperoxyanhydride. Petition 870250108891, dated 11 / 27 / 2025, page 55 / 99 51 / 76 dimethylcarbamothioic acid (thiram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzyl thiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM). Non-limiting examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).
[0193] The term “activator,” as used herein, refers to any substance that activates a vulcanizing agent and enables it to cross-link elastomers as described above. Activators may act through various mechanisms, including, but not limited to, forming chemical complexes with accelerators or coordinating with sulfur (when sulfur is used as a vulcanizing agent). Non-limiting examples of activators include metal oxides, acids, and metal complexes. Non-limiting examples of metal oxides include zinc oxide, magnesium oxide, and lead oxide. Non-limiting examples of acids include stearic acid and lauric acid. Non-limiting examples of metal complexes include zinc ethylhexanoate.
[0194] The term “pre-vulcanization inhibitor”, as used herein, refers to compounds that retard the onset and / or rate of vulcanization. These compounds are also called “retarders”. Non-limiting examples of pre-vulcanization inhibitors include N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.
[0195] In some embodiments, a Disclosure Composition comprises from about 15% w / w to about 85% w / w of one or more rubber chemicals. In some embodiments, the composition comprises from about 1% w / w to about 5% w / w, from about 1% w / w to about 15% w / w, from about 1% w / w to about 25% w / w, from about 1% w / w to about 35% w / w, from about 1% w / w to about 45% w / w, from about 1% w / w to about 55% w / w, from about 1% w / w to about 65% w / w, Petition 870250108891, dated 11 / 27 / 2025, p. 56 / 99 52 / 76 search 1% em p / pa search 75% em p / p, search 1% em p / pa search 85% em p / p, search 1% em p / pa search 95% em p / p, search 5% em p / pa search 15% em p / p, search 5% em p / pa search 25% em p / p, search 5% em p / pa search 35% in p / p, search 5% in p / pa search 45% in p / p, search 5% in p / pa search 55% in p / p, search 5% in p / pa search 65% in p / p, search 5% in p / pa search 75% in p / p, search 5% in p / pa search 85% p / p, search of 5 % em p / pa search 95% in p / p, search 15% in p / pa search 25% in p / p, search 15% in p / pa search 35% in p / p, search 15% in p / pa search 45% in p / p, search 15% in p / pa search 55% in p / p, search 15% in p / pa search 65% em p / p, search 15% em p / p search 75% em p / p, search 15% em p / p search 95% em p / p, search 25% em p / p search 35% em p / p, search 25% em p / pa search 45% em p / p,search 25% in p / p search 55% in p / p search 25% in p / p search 65% in p / p search 25% in p / p search 75% in p / p search 25% in p / p search 85% in p / p search 25% in p / pa search 95% in p / p search 35% em p / pa search 45% em p / p, search 35% em p / pa search 55% em p / p, search 35% em p / pa search 65% em p / p, search 35% em p / pa search 75% em p / p, search 35% em p / pa search 85% em p / p, search 35% em p / pa search 95% em p / p, looking for 45% em p / pa search 55% em p / p search 45% em p / pa search 65% em p / p search 45% em p / pa search 75% em p / p search 45% em p / pa search 85% em p / p search 45% em p / pa search 95% em p / p search 55% em p / p search 65% in p / p, search 55% in p / p search 75% in p / p, search 55% in p / p search 85% in p / p, search 55% in p / pa search 95% in p / p,of about 65% w / w, about 75% w / w, about 65% w / w, about 85% w / w, about 65% w / w, about 95% w / w, about 75% w / w, about 85% w / w, about 75% w / w, about 95% w / w, or about 85% w / w, about 95% w / w of one or more rubber chemicals.
[0196] In some modalities, a Disclosure Composition Petition 870250108891, dated 11 / 27 / 2025, p. 57 / 99 53 / 76 comprises approximately 15% by weight of one or more rubber chemicals. In some embodiments, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 10% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of one or more rubber chemicals.
[0197] In some embodiments, a Disclosure Composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals. In some embodiments, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr,from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr, from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr phr, from about 20 phr to about from 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr to about 30 phr, from about 25 phr to about 35 phr, from about 25 phr to about 40 phr, from about 30 phr to about 35 phr, from about 30 phr at about 40 phr, or about 35, Petition 870250108891, dated 11 / 27 / 2025, pp. 58 / 99 54 / 76 phr to approximately 40 phr of one or more rubber chemicals.
[0198] In some embodiments, a Disclosure Composition comprises about 10 phr of one or more rubber chemicals. In some embodiments, the composition comprises about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr, or about 40 phr of one or more rubber chemicals.
[0199] The term “plasticizer,” as used herein, refers to a processing aid used to reduce viscosity, increase plasticity, and / or extend the volume of a composition. Plasticizers facilitate the mixing and forming process of a composition comprising an elastomer 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.
[0200] In some embodiments, a Disclosure Composition comprises approximately 15% by weight to approximately 85% by weight of one or more plasticizers. In some modalities, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 1% w / w, approximately 15% w / w, approximately 1% w / w, approximately 25% w / w, approximately 1% w / w, approximately 35% w / w, approximately 1% w / w, approximately 45% w / w, approximately 1% w / w, approximately 55% w / w, approximately 1% w / w, approximately 65% w / w, approximately 1% w / w, approximately 75% w / w, approximately 1% w / w, approximately 85% w / w, approximately 1% w / w, approximately 95% w / w, and approximately 5% w / w. w / w about 15% in w / w, about 5% in w / w about 25% in w / w, about 5% in w / w about 35% in w / w, about 5% in w / w about 45% in w / w about 65% w / w, from about 5% w / w about 75% w / w,from about 5% w / w to about 85% w / w, from about 5% w / w to about 95% w / w, from about 15% w / w to about 25% w / w, from about 15% w / w to about 35% w / w, from about 15% w / w to about 45% in p / w, of around 15% in p / pa, Petition 870250108891, dated 11 / 27 / 2025, p. 59 / 99 55 / 76 search 55% in p / p, search 15% in p / pa search 65% in p / p, search 15% in p / pa search 75% in p / p, search 15% in p / pa search 95% in p / pa, search 25% in p / pa search 35% in p / p, search 25% in p / pa search 45% em p / p, search 25% em p / pa search 55% em p / p, search 25% em p / pa search 65% em p / p, search 25% em p / pa search 75% em p / p, search 25% em p / pa search 85% em p / p, search 25% em p / pa search 95% em p / p, search of 35 % em p / pa search 45% in p / p, search 35% in p / pa search 55% in p / p, search 35% in p / pa search 65% in p / p, search 35% in p / pa search 75% in p / p, search 35% in p / pa search 85% in p / p, search 35% in p / pa search 95% em p / p search 45% em p / p search 55% em p / p search 45% em p / p search 65% em p / p search 45% em p / p search 75% em p / p search 45% em p / pa search 85% em p / p,from about 45% p / pa, from about 95% p / p, from about 55% p / pa, from about 65% p / p, from about 55% p / pa, from about 75% p / p, from about 55% p / pa, from about 85% p / p, from about 55% p / pa, from about 95% p / p, from about 65% p / pa, from about 75% p / p, from about 65% p / pa, from about 85% p / p, from about 65% p / pa, from about 95% p / p, from about 75% p / pa, from about 85% p / p, from about 75% p / pa, from about 95% p / p, or from about 85% by weight (w / w) approximately 95% by weight (w / w) of one or more plasticizers.
[0201] In some embodiments, a Disclosure Composition comprises approximately 15% by weight of one or more plasticizers. In some embodiments, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 10% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of one or more plasticizers.
[0202] In some embodiments, a Disclosure Composition comprises from about 1 phr to about 20 phr of one or more plasticizers. In Petition 870250108891, dated 11 / 27 / 2025, pp. 60 / 99 56 / 76 In some forms, the composition comprises from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 10 phr, from about 0.1 phr to about 15 phr, from about 0.1 phr to about 20 phr, from about 0.1 phr to about 25 phr, from about 0.1 phr to about 30 phr, from about 0.1 phr to about 35 phr, from about 0.1 phr to about 40 phr, from about 1 phr to about 5 phr, from about 1 phr to about 10 phr, from about 1 phr to about 15 phr, from about 1 phr to about 25 phr, from about 1 phr to about 30 phr, from about 1 phr to about 35 phr, from about 1 phr to about 40 phr, from about 5 phr to about 10 phr, from about 5 phr to about 15 phr, from about 5 phr to about 20 phr, from about 5 phr to about 25 phr, from about 5 phr to about 30 phr, from about 5 phr to about 35 phr, from about 5 phr to about 40 phr, from about 10 phr to about 15 phr, from about 10 phr to about 20 phr,from about 10 phr to about 25 phr, from about 10 phr to about 30 phr, from about 10 phr to about 35 phr, from about 10 phr to about 40 phr, from about 15 phr to about 20 phr, from about 15 phr to about 25 phr, from about 15 phr to about 30 phr, from about 15 phr to about 35 phr, from about 15 phr to about 40 phr, from about 20 phr to about 25 phr, from about 20 phr to about 30 phr, from about 20 phr to about 35 phr, from about 20 phr to about 40 phr, from about 25 phr to about 30 phr, from about 25 phr at about 35 phr, from about 25 phr to about 40 phr, from about 30 phr to about 35 phr, from about 30 phr to about 40 phr, or from about 35 phr to about 40 phr of one or more plasticizers.
[0203] In some embodiments, a Disclosure Composition comprises about 10 phr of one or more plasticizers. In some embodiments, the composition comprises about 0.1 phr, about 1 phr, about 5 phr, about 15 phr, about 20 phr, about 25 phr, about 30 phr, about 35 phr or about 40 phr of one or more plasticizers.
[0204] In some embodiments, a Disclosure Composition further comprises one or more additional antidegradants that are not a Disclosure Compound. In some embodiments, the one or more additional antidegradants are antioxidants. In some embodiments, the one or more antidegradants Petition 870250108891, dated 11 / 27 / 2025, p. 61 / 99 57 / 76 additional antiozonants. Non-limiting examples of antidegradants include paraphenylenediamines (PPDs), trimethyl-dihydroquinolines (TMQs), phenolics, alkylated diphenylamines (DPAs), diphenylamine ketone condensates, and natural antidegradants. Non-limiting examples of PPDs include N1-(4methylpentan-2-yl)-N4-phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N'-phenyl-pphenylenediamine (7PPD), N1-phenyl-N4-(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 NN-dioctyl-pphenylenediamine (88PD). Non-limiting examples of TMQs include 2,2,4-trimethyl-1,2dihydroquinoline and its oligomers or polymers.
[0205] In some embodiments, a Disclosure Composition comprises from about 15% by weight to about 85% by weight of one or more additional antidegradants. In some modalities, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 1% w / w, approximately 15% w / w, approximately 1% w / w, approximately 25% w / w, approximately 1% w / w, approximately 35% w / w, approximately 1% w / w, approximately 45% w / w, approximately 1% w / w, approximately 55% w / w, approximately 1% w / w, approximately 65% w / w, approximately 1% w / w, approximately 75% w / w, approximately 1% w / w, approximately 85% w / w, approximately 1% w / w, approximately 95% w / w, and approximately 5% w / w. w / w about 15% in w / w, about 5% in w / w about 25% in w / w, about 5% in w / w about 35% in w / w, about 5% in w / w about 45% in w / w about 65% w / w,from about 5% w / w to about 75% w / w, from about 5% w / w to about 85% w / w, from about 5% w / w to about 95% w / w, from about 15% w / w to about 25% w / w, from about 15% w / w to about 35% w / w, from about 15% w / w about 45% w / w, from about 15% w / w about 55% w / w, from about 15% w / w about 65% w / w, from about 15% w / w about 75% w / w, from about 15% w / w about 95% in w / w, of around 25% in w / w about 35% w / w, about 25% w / w about 45% w / w, about 25% w / w about 55% w / w, of, Petition 870250108891, dated 11 / 27 / 2025, p. 62 / 99 58 / 76 search 25% in p / p search 65% in p / p search 25% in p / p search 75% in p / p search 25% in p / p search 85% in p / p search 25% in p / p search 95% in p / p search 35% in p / p search 45% in p / p search from 35% em p / pa search 55% em p / p search 35% em p / pa search 65% em p / p search 35% em p / pa search 75% em p / p search 35% em p / pa search 85% em p / p search 35% em p / pa search 95% em p / p search 45% em p / pa search of 55 % em p / p, looking for 45% in p / pa looking for 65% in p / p, looking for 45% in p / pa looking for 75% in p / p, looking for 45% in p / pa looking for 85% in p / p, looking for 45% in p / pa looking for 95% in p / p, looking for 55% in p / pa looking for 65% in p / p, looking for 55% em p / pa search 75% em p / p, search 55% em p / pa search 85% em p / p, search 55% em p / pa search 95% em p / p, search 65% em p / pa search 75% em p / p,of about 65% w / w, about 85% w / w, about 65% w / w, about 95% w / w, about 75% w / w, about 85% w / w, about 75% w / w, about 95% w / w, or about 85% w / w, about 95% w / w of one or more additional antidegradants.
[0206] In some embodiments, a Disclosure Composition comprises approximately 15% by weight of one or more additional antidegradants. In some embodiments, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 10% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w of one or more additional antidegradants.
[0207] In some embodiments, a Disclosure Composition comprises from about 1 to about 5 phr of one or more additional antidegradants. In some embodiments, the composition comprises from about 0.001 phr to about 0.01 phr, from about 0.001 phr to about 0.1 phr, from about 0.001 phr to about 1 phr, from about 0.001 phr to about 5 phr, from about 0.001 phr to about 7.5 Petition 870250108891, dated 11 / 27 / 2025, p. 63 / 99 59 / 76 phr, from about 0.001 phr to about 10 phr, from about 0.01 phr to about 0.1 phr, from about 0.01 phr to about 1 phr, from about 0.01 phr to about 5 phr, from about 0.01 phr to about 7.5 phr, from about 0.01 phr to about 10 phr, from about 0.1 phr to about 1 phr, from about 0.1 phr to about 5 phr, from about 0.1 phr to about 7.5 phr, from about 0.1 phr to about 10 phr, from about 1 phr to about 7.5 phr, from about 1 phr to about 10 phr, from about 5 phr to about 7.5 phr, of about 5 phr to about 10 phr, or from about 7.5 phr to about 10 phr of some or more additional antidegradants.
[0208] In some embodiments, a Disclosure Composition comprises about 3 phr of one or more additional antidegradants. In some embodiments, the composition comprises 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 of one or more additional antidegradants.
[0209] In some embodiments, the disclosure provides a composition comprising a Disclosure Compound and one or more carriers. The term “carrier,” as used herein, refers to a solid that can adsorb 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 high surface area. In some embodiments, the carrier comprises particles with diameters smaller than 500 microns.
[0210] In some forms, the composition comprises approximately 15% by weight and approximately 85% by weight of one or more carriers. In some modalities, the composition comprises approximately 1% w / w, approximately 5% w / w, approximately 1% w / w, approximately 15% w / w, approximately 1% w / w, approximately 25% w / w, approximately 1% w / w, approximately 35% w / w, approximately 1% w / w, approximately 45% w / w, approximately 1% w / w, approximately 55% w / w, approximately 1% w / w, approximately 65% w / w, approximately 1% w / w, approximately 75% w / w, approximately 1% w / w, approximately 85% w / w, approximately 1% w / w, approximately 95% w / w, and approximately 5% w / w. p / pa approximately 15% in p / p, approximately 5% in p / pa approximately 25% in p / p, approximately 5% in p / pa approximately 35% in Petition 870250108891, dated 11 / 27 / 2025, p. 64 / 99 60 / 76 p / p, search 5% in p / p search 45% in p / p, search 5% in p / p search 55% in p / p, search 5% in p / p search 65% in p / p, search 5% in p / p search 75% in p / p, search 5% in p / pa search 85% in p / p, search from 5% em p / pa search 95% em p / p search 15% em p / pa search 25% em p / p search 15% em p / pa search 35% em p / p search 15% em p / pa search 45% em p / p search 15% em p / pa search 55% em p / p search 15% em p / pa search for 65 % em p / p, search for 15% in p / p search for 75% in p / p, search for 15% in p / p search for 95% in p / p, search for 25% in p / p search for 35% in p / p, search for 25% in p / p search for 45% in p / p, search for 25% in p / p search for 55% in p / p, search for 25% em p / pa search 65% em p / p, search 25% em p / pa search 75% em p / p, search 25% em p / pa search 85% em p / p, search 25% em p / pa search 95% em p / p,search 35% em p / pa search 45% em p / p search 35% em p / pa search 55% em p / p search 35% em p / pa search 65% em p / p search 35% em p / pa search 75% em p / p search 35% em p / pa search 85% em p / p search 35% em p / pa search 95% em p / p, search 45% em p / pa search 55% em p / p, search 45% em p / pa search 65% em p / p, search 45% em p / pa search 75% em p / p, search 45% em p / pa search 85% em p / p, search 45% em p / pa search 95% em p / p, looking for 55% em p / pa search 65% em p / p, search 55% em p / pa search 75% em p / p, search 55% em p / pa search 85% em p / p, search 55% em p / pa search 95% em p / p, search 65% em p / pa search 75% em p / p, search 65% em p / pa search 85% in p / p, search 65% in p / pa search 95% in p / p, search 75% in p / pa search 85% in p / p, search 75% in p / pa search 95% in p / p,or approximately 85% p / p, or approximately 95% p / p, from one or more carriers.
[0211] In some forms, the composition comprises approximately 15% by weight of one or more carriers. In some forms, the composition comprises approximately 1% by weight, approximately 5% by weight, approximately 10% by weight, approximately 20% by weight, approximately 25% by weight, approximately 30% by weight, approximately 35% by weight, approximately 40% by weight, approximately 45% by weight, approximately 50% by weight, approximately 55% by weight Petition 870250108891, dated 11 / 27 / 2025, p. 65 / 99 61 / 76 in p / p, approximately 60% in p / p, approximately 65% in p / p, approximately 70% in p / p, approximately 75% in p / p, approximately 80% in p / p, approximately 85% in p / p, approximately 90% in p / p or approximately 95% in p / p of one or more carriers.
[0212] This disclosure also provides processes for preparing a composition comprising a Disclosure Compound and one or more carriers, the process comprising mixing the compound and one or more carriers.
[0213] This disclosure also provides lubricating compositions comprising a Disclosure Compound and a lubricant. Non-limiting examples of lubricants include mineral oil, high molecular weight petroleum distillates such as aromatic, naphthenic and paraffinic distillates, synthetic oils such as polyalpha-olefin (PAO), synthetic esters, polyalkylene glycols (PAG), phosphate esters, perfluoropolyether (PFPE), alkylated naphthalenes (AN), silicate esters, ionic fluids and multiply alkylated cyclopentanes (MAC), solid lubricants such as polytetrafluoroethylene (PTFE), graphite, hexagonal boron nitride, molybdenum disulfide, tungsten disulfide, aqueous lubricants such as hydrated brush polymers, and biolubricants such as triglyceride esters, high oleic canola oil, castor oil, palm oil, sunflower seed oil and rapeseed oil.
[0214] This disclosure also provides flammable fuel compositions comprising a flammable fuel and a Disclosure Compound. Non-limiting examples of flammable fuel include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuel, and biodiesel.
[0215] This disclosure also provides fuel additive compositions comprising a fuel additive and a Disclosure Compound. Non-limiting examples of fuel additives include oxygenates such as alcohols and ethers, antioxidants, stabilizers, detergents, anti-knock agents, lead removers, fuel colorants, viscosity modifiers, and butyl rubber. In some embodiments, butyl rubber is in the form of polyisobutylene succinimide. In some embodiments, butyl rubber is added as a detergent to prevent fouling in diesel fuel injectors. Petition 870250108891, dated 11 / 27 / 2025, pp. 66 / 99 62 / 76
[0216] In some forms, the present disclosure provides a composition cited in Table 2. TABLE 2 Component 1 % w / w of Component 1 Type of Composition Component 2 % w / w of Component 2 Disclosure Compound 0.1-10 Tire or other rubber article (belt, hose, support, etc.) (vulcanized) Elastomer 5-95 Disclosure Compound 0.01-10 Tire component or constructed component or other end-use component (tread, polymer blends, etc.) (unvulcanized) Elastomer 5-95 Disclosure Compound 5-95 Masterbatch Elastomer 95-5 Disclosure Compound 5-95 Premix Filler 95-5 Disclosure Compound 5-95 Premix Rubber chemical 95-5 Disclosure Compound 5-95 Premix Plasticizer 95-5 Disclosure Compound 5-95 Premix Additional antidegradant(s) 95-5
[0217] In some embodiments, the composition of vulcanized tire or other rubber article of Table 2 comprises about 0.1% w / w, about 0.2% w / w, about 0.3% w / w, about 0.4% w / w, about 0.5% w / w, about Petition 870250108891, dated 11 / 27 / 2025, p. 67 / 99 63 / 76 of 0.6% p / p, approximately 0.7% p / p, approximately 0.8% p / p, approximately 0.9% p / p, approximately 1% p / p, approximately 2% p / p, approximately 3% p / p, approximately 4% p / p, approximately 5% p / p, approximately 6% p / p, approximately 7% p / p, approximately 8% p / p, approximately 9% p / p or approximately 10% p / p of a Disclosure Composite. In some embodiments, the vulcanized tire or other rubber article of Table 2 comprises approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w or approximately 95% w / w p / p of at least one elastomer.
[0218] In some embodiments, the unvulcanized tire component, the mounted component or other end-use component of Table 2 comprises approximately 0.01% w / w, approximately 0.02% w / w, approximately 0.03% w / w, approximately 0.04% w / w, approximately 0.05% w / w, approximately 0.06% w / w, approximately 0.07% w / w, approximately 0.08% w / w, approximately 0.09% w / w, approximately 0.1% w / w, approximately 0.2% w / w, approximately 0.3% w / w, approximately 0.4% w / w, approximately 0.5% w / w, approximately 0.6% w / w, approximately 0.7 % p / p, approximately 0.8% p / p, approximately 0.9% p / p, approximately 1% p / p, approximately 2% p / p, approximately 3% p / p, approximately 4% p / p, approximately 5% p / p, approximately 6% p / p, approximately 7% p / p, approximately 8% p / p, approximately 9% p / p or approximately 10% p / p of a Disclosure Composite.In some embodiments, the unvulcanized tire component, the mounted component, or other end-use component of Table 2 comprises approximately 5% w / w, approximately 10% w / w, approximately 15% w / w, approximately 20% w / w, approximately 25% w / w, approximately 30% w / w, approximately 35% w / w, approximately 40% w / w, approximately 45% w / w, approximately 50% w / w, approximately 55% w / w, approximately 60% w / w, approximately 65% w / w, approximately 70% w / w, approximately 75% w / w, approximately 80% w / w, approximately 85% w / w, approximately 90% w / w, or approximately 95% by weight / weight of at least one elastomer. Vulcanized elastomeric articles Petition 870250108891, dated 11 / 27 / 2025, pp. 68 / 99 64 / 76
[0219] This disclosure also provides vulcanized elastomeric articles comprising a Disclosure Compound. The term “vulcanized elastomeric article” refers to an article that is made by forming a composition comprising an elastomer in a specific shape and by vulcanizing the composition to provide the article.
[0220] This disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.
[0221] In some embodiments, the vulcanized elastomeric article is a tire. In some embodiments, the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, an earthmoving tire, an aircraft tire, or a racing tire.
[0222] In some embodiments, the vulcanized elastomeric article is a component of a tire. In some embodiments, the component is a bead, a belt, a carcass ply, an inner lining, a sidewall, a sub-tread or a tread.
[0223] In some embodiments, the vulcanized elastomeric article is a rubber spare, a sealing strip, an acoustic panel, an air spring, a bellows, a membrane, a tactile sensor, a protective pad, a hose, a conveyor belt or a floor. PROCESSES
[0224] This disclosure also provides processes for preparing a vulcanized elastomeric article, the process comprising:
[0225] (a) to form a composition described here in a molded form; and
[0226] (b) vulcanize the molded form,
[0227] to supply a vulcanized elastomeric article.
[0228] In some embodiments, vulcanization is carried out at an average temperature of about 140 °C to about 160 °C. In some embodiments, vulcanization is carried out at an average temperature of about 80 °C to about 100 °C, about 80 °C to about 120 °C, about 80 °C to about 140 °C, Petition 870250108891, dated 11 / 27 / 2025, pp. 69 / 99 65 / 76 from about 80°C to about 160°C, from about 80°C to about 180°C, from about 80°C to about 200°C, from about 100°C to about 120°C, from about 100°C to about 140°C, from about 100°C to about 160°C, from about 100°C to about 180°C, from about 100°C to about 200°C, from about 120°C to about 140°C, from about 120°C to about 160°C, from about 120°C to about 180°C, from about 120°C to about 200°C, from about 140°C at approx. 180°C, from about 140°C to about 200°C, from about 160°C to about 180°C, from about 160°C to about 200°C, or from about 180°C to about 200°C.
[0229] In some embodiments, vulcanization is carried out at an average temperature of about 150 °C. In other 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.
[0230] This disclosure also provides processes for tire retreading, the process comprising:
[0231] (a) apply a composition described here to a tire;
[0232] (b) to place a pre-vulcanized tread around the tire;
[0233] (c) place a curing envelope around the tire; and
[0234] (d) vulcanize the tire. KITS
[0235] This disclosure also provides kits comprising a composition described herein, packaged in a manner, for example, in a container, that facilitates the use of the composition to practice the processes and / or methods of this disclosure. In some embodiments, the kit comprises a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition. In some embodiments, the kit comprises a composition described herein and instructions for using the composition to prepare a vulcanizable elastomeric article. The composition may be packaged in any suitable container, such as a bottle or sealed container, with a label affixed to the container or included in the kit describing the composition and its proper use. EXAMPLES Petition 870250108891, dated 11 / 27 / 2025, pp. 70 / 99 66 / 76 EXAMPLE 1
[0236] Synthesis of N-isopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinolin-6amine (Compound 1) STAGE 1 Intermediate Compound 1-1
[0237] In a 1 L round-bottom flask equipped with a suspended stirrer, a thermometer, and a reflux condenser, 2-methyl-4-nitroaniline (30 g; 197 mmol) and acetonitrile (320 mL) were loaded. The mixture was stirred under N2 protection. To the resulting clear yellow solution, trifluoroacetic acid (16.0 mL; 209 mmol), 37% aqueous formaldehyde solution (26.0 mL; 349 mmol HCHO), and alpha-methylstyrene (46.0 mL; 354 mmol) were added in that order. The reaction mixture (paste formed after the addition of formaldehyde) was refluxed for 2 hours (internal temperature = 77-78 °C), after which a clear yellow solution formed. After cooling to room temperature, 1 mol / L aqueous sodium bicarbonate (300 mL) was added in portions. The resulting two-phase system was stirred until CO2 generation ceased and then transferred to a 2 L separatory funnel. Ethyl acetate (700 mL) was added. After stirring and decantation, the aqueous phase was discarded.The organic phase was washed with 1 mol / L aqueous sodium bisulfite (300 mL) and saturated aqueous sodium chloride (300 mL), dried over anhydrous magnesium sulfate, filtered, and de-volatiles were removed under reduced pressure (rotary evaporator; water bath = 50 °C). The dark oil obtained (69.5 g) was diluted with a mixture of isopropanol (100 mL) and hexanes (20 mL). The mixture was stirred until homogeneous and then kept at -20 °C overnight, at which point a yellow solid separated. The yellow solid was collected by vacuum filtration (20-micron disposable polyethylene frit) and washed with hexanes (50 mL) directly onto the frit. The wet material was... Petition 870250108891, dated 11 / 27 / 2025, pp. 71 / 99 67 / 76 was dried in a vacuum oven at 45-50 °C for a few hours and then at room temperature overnight to produce 24.1 g of 4,8-dimethyl-6-nitro-4-phenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 1-1) as a yellow powder. Intermediate compound 1-1 was characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopy, as shown in Figures 1 and 2, respectively. LC-UV analysis indicated 93.4% purity at 260 nm detection, as shown in Figure 3. STAGE 2 Intermediate Compound 1-1 Compound 1
[0238] In a 300 mL Parr autoclave, intermediate compound 1-1 (23.0 g; 81.5 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.4077 g wet), isopropanol (201 mL), and acetone (10.4 mL; 142 mmol) were loaded. The reaction mixture was stirred and heated to 120 °C under 250 PSI H2 for 1.5 hours. After cooling to room temperature, the post-reaction mixture was filtered through a 0.2 micron frit in-line. The clave was rinsed with fresh isopropanol (approximately 200 mL) and the resulting mixture was filtered through the 0.2 micron frit in-line. The combined filtrates were filtered through filter paper and their volatiles removed under reduced pressure (rotary evaporator; water bath = 50 °C). The crude material obtained (light brown oil) weighed 23.7 g. After remaining at room temperature for several weeks, the oil solidified as a dark solid mass. After cooling to -20 °C overnight, the solid mass was broken up with a spatula.A mixture of ethyl acetate and hexanes (10 mL and 51 mL respectively) was added to the dark powder obtained. The resulting paste was magnetically stirred at room temperature under N2 protection for 4 days. The solid was collected by vacuum filtration. Petition 870250108891, dated 11 / 27 / 2025, pp. 72 / 99 68 / 76 on 0.2 micron disposable polyethylene frit and rinsed quickly with several portions of hexanes (50 mL total). The wet powder (16.58 g) was dried under vacuum at 50-60 °C for a few hours and then at room temperature overnight to yield 14.48 g of N-isopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinolin-6-amine (Compound 1) (60% relative to intermediate compound 1-1) as a light brown powder. Compound 1 was characterized by 13C NMR spectroscopy, as shown in Figure 4. LC-UV analysis indicated 96.5% purity at 260 nm detection, as shown in Figure 5. Mass (m / z): 295.4 [M+1]+. EXAMPLE 2
[0239] Synthesis of 4,8-dimethyl-N-(pentan-3-yl)-4-phenyl-1,2,3,4-tetrahydroquinolin6-amine (Compound 2) Intermediate Compound 1-1 3% Pt / C sulfided HaPOi cat. aq. Hz pressurized heat Compound 2
[0240] In a 300 mL Parr autoclave, intermediate compound 1-1 (12.0 g; 42.5 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.42 g wet), 3-pentanone (180 mL; 1.70 mol), and 5% w / w aqueous phosphoric acid (1.8 g; 0.92 mmol H3PO4 solution) were loaded. The reaction mixture was stirred and heated to 150 °C under 250 PSI H2 for 2 hours. After cooling to room temperature, the post-reaction mixture was filtered through a 0.2 micron frit in-line. The clav was rinsed with isopropanol (approximately 150-200 mL) and the resulting mixture was filtered through the 0.2 micron frit in-line. The combined filtrates were stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The resulting residue was dissolved in hexane (14 mL), after which traces of insoluble material were separated. The mixture was vacuum filtered over Celite S and the cake was rinsed with hexane (100 mL). The combined filtrates were stripped... Petition 870250108891, dated 11 / 27 / 2025, pp. 73 / 99 69 / 76 of its volatiles were removed under reduced pressure (rotary evaporator; water bath = 50 °C). Drying under vacuum at 60 °C overnight yielded 12.5 g of a brown oil that darkened over time upon reaching room temperature to provide 4,8-dimethyl-N-(pentan-3-yl)-4-phenyl-1,2,3,4-tetrahydroquinolin-6-amine (Compound 2). Compound 2 was characterized by 13C NMR spectroscopy, as shown in Figure 6. LC-UV analysis indicated 91.0% purity at 260 nm detection, as shown in Figure 7. Mass (m / z): 323.4 [M+1]+. EXAMPLE 3
[0241] Synthesis of N-isopropyl-4,8-dimethyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 3) STAGE 1 Intermediate Compound 3-I
[0242] In a 1 L round-bottom flask equipped with a stirring bar, a thermometer, and a reflux condenser, 2-methyl-4-nitroaniline (9.96 g; 65.5 mmol) and acetonitrile (200 mL) were loaded. The mixture was stirred under N2 protection. To the resulting light yellow solution, trifluoroacetic acid (5.3 mL; 68.7 mmol), benzaldehyde (6.6 mL; 65.5 mmol), and alpha-methylstyrene (15.3 mL; 117.9 mmol) were added in that order. The reaction mixture was heated to 82 °C (oil bath temperature) for 4 hours. Upon cooling to room temperature, a yellow precipitate formed. A solution of sodium bicarbonate (10 g) in deionized water (200 mL) was added in portions. Ethyl acetate (200 mL) was added in portions to dissolve the precipitate. The resulting two-phase system was transferred to a separatory funnel. The aqueous phase was discarded. The organic phase was washed with a Petition 870250108891, dated 11 / 27 / 2025, p. 74 / 99 70 / 76 Sodium bisulfite solution (15.0 g) in deionized water (200 mL) and saturated aqueous sodium chloride (200 mL), dried over anhydrous magnesium sulfate, filtered, and removed of volatiles under reduced pressure (rotary evaporator; water bath = 45 °C). The residue was dried under vacuum at 20 mbar at 45 °C for 20 min. The resulting viscous orange oil was suspended in 1:1 v / v isopropanekhexane (100 mL) and heated to 55 °C for 15 minutes, after which the orange oil became a yellow solid. The mixture was allowed to cool to room temperature and then filtered to isolate the yellow solid. The solid was washed with hexanes (3 x 20 mL) and dried on a vacuum filter for approximately 20 minutes to yield 15.2 g of 4,8-dimethyl-6-nitro-2,4-diphenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 3-I) as a yellow powder. LC-UV analysis indicated 99.0% purity at 260 nm detection, as shown in Figure 8. STAGE 2
[0243] In a 300 mL Parr autoclave, the intermediate compound 3-I (10.6 g, 29.7 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.2467 g wet), isopropanol (200 mL), and acetone (5.6 mL, 75.5 mmol) were loaded. The reaction mixture was stirred and heated to 150 °C under 250 PSI H2 for 107 minutes. After cooling to room temperature, the mixture was filtered over a 0.2 micron frit in-line, the reactor was rinsed with 100 mL of isopropanol, and the combined filtrates were removed under reduced pressure (rotary evaporator; water bath = 50 °C) to yield a waxy beige solid (10.68 g). The solid was dried under vacuum for 16 hours at 55 °C to yield 9.27 g of N-isopropyl-4,8-dimethyl-2,4-diphenyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 3) as a waxy beige solid. Compound 3 was characterized by 13C NMR spectroscopy, as shown in Figure 9. LC-UV analysis Petition 870250108891, dated 11 / 27 / 2025, pp. 75 / 99 71 / 76 indicated 94.5% purity in the 260 nm detection, as shown in Figure 10. Mass (m / z): 371.4 [M+1]+. EXAMPLE 4
[0244] Synthesis of N,2-diisopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinolin6-amine (Compound 4) STAGE 1 Intermediate Compound 4-I
[0245] In a 250 mL flask equipped with a stirring bar and a reflux condenser, 2-methyl-4-nitroaniline (4.2 g; 27.6 mmol) and acetonitrile (50 mL) were loaded. The mixture was stirred under N2 protection (2-methyl-4-nitroaniline dissolved in a few minutes). To the resulting dark solution, trifluoroacetic acid (2.2 mL; 28.7 mmol), isobutyraldehyde (4.4 mL; 48 mmol), and alpha-methylstyrene (6.4 mL; 49.2 mmol) were sequentially added in that order. The reaction mixture was heated (oil bath set to 80 °C). Once the set temperature was reached, it was maintained for 5 hours. After cooling to room temperature (overnight), a solution of sodium bicarbonate (4.75 g; 56.5 mmol) in deionized water (60 mL) was added in portions. The resulting two-phase system was shaken until CO2 generation ceased, ethyl acetate (50 mL) was added, and the mixture was transferred to a separatory funnel. The flask was rinsed with ethyl acetate (2 x 20 mL).The organic solutions were transferred to a separatory funnel. After decantation, the aqueous layer was discarded. The organic layer was washed with aqueous saturated sodium bisulfite (30 mL), dried over MgSO4, filtered, and stripped of its volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). No attempt was made to remove excess alpha-methylstyrene (BP = 165-169). Petition 870250108891, dated 11 / 27 / 2025, pp. 76 / 99 (72 / 76 degrees C). To the impure orange oil obtained weighing approximately 9.9 g, a mixture of hexanes (20 mL) and isopropanol (10 mL) was added. After stirring for a few seconds, the resulting solution was kept at -20 °C for 1 hour, at which point a yellow crystalline solid and a dense dark mass separated. After heating to room temperature and vigorous stirring, the dark mass disappeared and additional quantities of yellow crystals formed. The solid was collected by vacuum filtration over a 0.2 micron disposable polyethylene frit and quickly rinsed with hexanes (10 mL). The wet solid (2.87 g) was dried under vacuum at 50-60 °C for a few hours and then at room temperature for a few hours, to give 2.78 g of 2-isopropyl-4,8-dimethyl-6-nitro-4-phenyl-1,2,3,4-tetrahydroquinoline (intermediate compound 4-I) as a yellow powder. The intermediate compound 4-I was characterized by 13C NMR spectroscopy, as shown in Figure 11.LC-UV analysis indicated 95.2% purity in the 260 nm detection, as shown in Figure 12. STAGE 2 Intermediate Compound 4-I Compound 4
[0246] In a 300 mL Parr autoclave, the intermediate compound 4-I (1.6 g; 4.93 mmol), 3% Pt / C sulfide (Johnson Matthey) (0.0366 g wet), isopropanol (130 mL), and acetone (0.99 mL; 13 mmol) were loaded. The reaction mixture was stirred and heated to 150 °C under 250 PSI H2 for 65–70 minutes. After cooling to room temperature, the post-reaction mixture was filtered through a 0.2 micron frit in-line. The clavate was rinsed with fresh isopropanol (150 mL), and the resulting mixture was filtered through the 0.2 micron frit in-line. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 55 °C). The residue was dissolved in 40% ethyl acetate in hexane (5 mL). The solution Petition 870250108891, dated 11 / 27 / 2025, pp. 77 / 99 The 73 / 76 fraction obtained was loaded onto a 41 mm internal diameter column previously prepared with silica gel (ultrapure; 60 Å; 60-200 pm) and 20% ethyl acetate in hexanes (silica height = 10-11 cm). The column was eluted with 20% ethyl acetate in hexanes. Each resulting fraction was analyzed by TLC on silica gel (20% ethyl acetate in hexanes). Fractions with Rf = 0.3 were collected, combined, and stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 55 °C). The light brown oil obtained was dried under vacuum (rotary evaporator; water bath = 55 °C; <2 mbars) for 1.5 hours and then in a vacuum oven at 75-80 °C overnight to yield 1.4 g of N,2-diisopropyl-4,8-dimethyl-4-phenyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 4) as a very viscous, light orange, transparent oil. Compound 4 was characterized by 13C NMR spectroscopy, as shown in Figure 13.LC-UV analysis indicated 97.2% purity in the 260 nm detection, as shown in Figure 14. Mass (m / z): 337.4 [M+1]+. EXAMPLE 5
[0247] Synthesis of N-isopropyl-3,3,8-trimethyl-1,2,3,4-tetrahydroquinolin-6-amine (Compound 47) STAGE 1
[0248] In a 100 mL flask equipped with a stirring bar and a reflux condenser, 2-methyl-4-nitroaniline (3.96 g; 26.0 mmol) and acetonitrile (42 mL) were loaded. The mixture was stirred under a N2 atmosphere. To the resulting dark solution, para-toluenesulfonic acid monohydrate (0.486 g; 2.56 mmol acid), 37% aqueous formaldehyde (2.4 mL; 32.2 mmol HCHO), and isobutyraldehyde (3.7 mL; 41 mmol) were sequentially added. A yellow solid separated after the addition of the formaldehyde solution. The reaction mixture was stirred without Petition 870250108891, dated 11 / 27 / 2025, pp. 78 / 99 74 / 76 Cooling or external heating for 2 days, after which a dark solution was obtained. Sodium bicarbonate (0.337 g; 4.01 mmol) was added and the mixture was stirred for 5-10 minutes. Anhydrous magnesium sulfate was added and the resulting paste was stirred for approximately 5 minutes. Insoluble materials were removed by gravimetric filtration through filter paper. The precipitate was rinsed with a little acetonitrile. The filtrate was stripped of its volatiles under reduced pressure (rotary evaporator; water bath = 50 °C). The crude material (6.35 g of moist yellow-orange solid) was triturated in isopropanol (20 mL) with a spatula until all the solid detached from the walls of the flask. The resulting paste was magnetically stirred for 10-15 minutes. Hexanes (20 mL) were added and the mixture was magnetically stirred for 30 minutes.The solid was collected by vacuum filtration over 0.2 micron disposable polyethylene frit and rinsed with several portions of hexane (total = 25 mL). The wet solid was dried under vacuum at approximately 50 °C for a few hours and then at room temperature overnight to yield 3.09 g of crude 3,3,8-trimethyl-6-nitro-1,2,3,4-tetrahydroquinolin-4-ol (intermediate compound 47-I) as a yellow powder. Crude intermediate compound 47-I was characterized by 13C APT NMR spectroscopy, as shown in Figure 15. LC-UV analysis indicated approximately 61% purity at 260 nm detection, as shown in Figure 16. The crude material was involved in the subsequent step without further purification. STAGE 2 Compound 47 Intermediate Compound 47-I
[0249] A 300 mL Parr autoclave was loaded with crude intermediate compound 47-I (2.8 g; <11.9 mmol), toluene (140 mL), acetone (1.7 mL; 23.2 mmol), and 3% Pt / C sulfide (Johnson Matthey) (150 mg wet). The reaction mixture Petition 870250108891, dated 11 / 27 / 2025, pp. 79 / 99 The 75 / 76 mixture was stirred and heated to 120 °C under 250 PSI H2 for 2 hours. After cooling to room temperature, the post-reaction mixture was filtered through a 0.2 micron in-line frit. The clave was rinsed with isopropanol (130 mL) and the resulting mixture was filtered through the 0.2 micron in-line frit. The combined filtrates were stripped of volatiles under reduced pressure (rotary evaporator; water bath = 60 °C). The residue was dissolved in hexanes (4 mL). The resulting solution was loaded onto a 41 mm internal diameter column previously prepared with silica gel (ultrapure; 60 Å; 60-200 μm) and 30% ethyl acetate in hexanes (silica height = 16-17 cm). The column was eluted with 30% ethyl acetate in hexanes. Each resulting fraction was analyzed by TLC on silica gel (30% ethyl acetate in hexanes). Fractions with Rf = 0.45 were collected, combined, and stripped of their volatiles under reduced pressure (rotary evaporator; water bath = 50 °C).The light brown oil obtained was dried under vacuum (rotary evaporator; water bath = 55 °C; <8 mbars) for 1.5 hours to yield 0.96 g of N-isopropyl-3,3,8-trimethyl-1,2,3,4-tetrahydroquinoline-6-amine (Compound 47) as a brown oil. Compound 47 was characterized by 13C APT NMR spectroscopy, as shown in Figure 17. LC-UV analysis indicated 94.6% purity at 260 nm detection, as shown in Figure 18. Mass (m / z): 233.3 [M+1]+. EXAMPLE 6 Oxidative Induction Time (OIT) Performance of Disclosure Compounds
[0250] The oxidative induction time (OIT) of selected compounds from the Disclosure was evaluated. The OIT is measured according to a procedure performed in a differential scanning calorimeter (DSC; TA Instruments, Q200). In this procedure, a sample is held in a cell and heated under a nitrogen atmosphere to a pre-selected temperature. Oxygen (O2) is then introduced into the cell and the time period before the onset of degradation, as observed by the start of an endothermic process in the DSC trace, is measured.
[0251] 0.5% by weight of a disclosure compound, N1-(4-methylpentan-2-yl)N4-phenylbenzene-1,4-diamine (6PPD), or no antidegradant (blank) was Petition 870250108891, dated 11 / 27 / 2025, pp. 80 / 99 76 / 76 mixed with polyisoprene and heated isothermally to 150 °C or 160 °C in O2. The OIT in minutes is shown in Table 3. As indicated by the data in Table 3, the compounds in the disclosure demonstrate antioxidant activity compared to the blank control.
[0252] The melting points of the disclosure compounds were also measured and are listed in Table 3. TABLE 3 Material Melting Point (°C) OIT at 150 °C (minutes) OIT at 160 °C (minutes) Blank N / A 2.0 1.85 6PPD 45-51 41.5 19.7 Compound 1 105 40.2 20.3 Compound 2 -5 40.3 17.4 Compound 3 127 75.9 43.8 Compound 4 10 41.5 19.6 Compound 47 < 20 8.6 3.2
[0253] Having now fully described the methods, compounds and compositions described herein, it will be understood by those skilled in the art that they can be carried out within a wide and equivalent range of conditions, formulations and other parameters without affecting the scope of the methods, compounds and compositions provided herein or any embodiment thereof. All patents, patent applications and publications cited herein are fully incorporated by reference herein in their entirety. Petition 870250108891, dated 11 / 27 / 2025, pp. 81 / 99
Claims
1 / 23 CLAIMS 1. Compound CHARACTERIZED in that it has Formula (I): or a salt, solvate or stereoisomer thereof, wherein: is a single or double bond; R1a is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR1cR1d, C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; R1b is selected from the group consisting of hydrogen and C1-C9 alkyl; R1c is selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl and optionally substituted 5- or 6-membered heteroaryl; R1d is selected from the group consisting of hydrogen and C1-C9 alkyl;R2a, R2b and R2c are selected independently from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -OH, -SH, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; or R2b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, C1-C8 alkoxy, C1-C8 alkylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -OH, -SH, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, phenyl optionally Petition 870250088230, dated 09 / 29 / 2025, pg 33 / 56 2 / 23 replaced and heteroaryl of 5 or 6 members optionally replaced;and R2a and R2c together with the two carbon atoms to which they are attached form a C5-C8 cycloalkyl, a 5- to 8-membered heterocyclyl or a C5-C6 aryl; R3a and R3b are selected independently from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl, provided that if it is a double bond, R3b is absent; or R3a and R3b together with the carbon atom to which they are attached form a C3-C12 cycloalkyl, provided that it is a single bond; R3c and R3d are selected independently from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl, provided that if it is a double bond, R3d is absent; or R3c and R3d together with the carbon atom to which they are attached form a C3-C12 cycloalkyl group, provided that it is a single bond;R3e and R3f are selected independently from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl, provided that If R3e and / or R3f are hydrogen, R3c and R3d are selected independently from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl; or R3e and R3f taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl; R3g is selected from the group consisting of hydrogen and C1-C9 alkyl;and Petition 870250088230, dated 09 / 29 / 2025, p. 34 / 56 3 / 23 R4 and R5 are, in each occurrence, selected independently from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl.; 2. Compound according to claim 1, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that it has Formula (II):
3. A compound according to claim 2, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that: R3c and R3d are independently selected from the group consisting of C1C9 alkyl, C3-C6 cycloalkyl and optionally substituted phenyl; or R3c and R3d together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.
4. Compound according to claim 2 or 3, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that: R3e and R3f are independently selected from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, C1-C8 alkoxy, C1-C8 alkylthio, arylthio, C(=O)OR4, -OC(=O)R4, -C(=O)NR4R5, -NR4C(=O)R5, -NHR4, -NR4R5, -SC(=O)R4, -SC(=O)SR4, -SC(=O)NHR4, -SC(=O)NR4R5, -NHC(=O)SR4, -NR4C(=O)SR5, -NHC(=S)SR4, -NR4C(=S)SR5, a 4- to 6-membered heterocyclyl, optionally substituted phenyl and optionally substituted 5- or 6-membered heteroaryl; or R3e and R3f taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.
5. Compound, according to any one of claims 1-4, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3b is hydrogen.
6. Compound according to claim 1, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that it has Formula (III):
7. A compound, according to any one of claims 1-6, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R1a is optionally phenyl substituted.
8. A compound according to any one of claims 1-6, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R1a is C11C12 alkyl.
9. Compound according to claim 8, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R1a is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl or nonyl.
10. Compound according to claim 9, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R1a is isopropyl or sec-butyl.
11. Compound according to claim 8, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R1a is: or 12. Compound, according to any of claims 1-11, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R2a, R2b and R2c are independently selected from the group consisting of hydrogen and C1-C9 alkyl.
13. Compound according to claim 12, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R2b and R2c are hydrogen.
14. Compound according to claim 13, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R2a is selected from the group consisting of hydrogen and C1-C4 alkyl.
15. A compound according to any one of claims 1-14, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3a is hydrogen.
16. A compound according to any one of claims 1-14, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3a is C1-C9 alkyl.
17. A compound according to any one of claims 1-14, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3a is C3-C6 cycloalkyl.
18. A compound according to any one of claims 1-14, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3a is optionally phenyl substituted.
19. A compound according to any one of claims 1-18, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3c is hydrogen.
20. A compound according to any one of claims 1-18, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3c is C1-C9 alkyl.
21. Compound, according to any of claims 1-18, or a Petition 870250088230, dated 09 / 29 / 2025, p. 37 / 56 6 / 23 salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3c is C3-C6 cycloalkyl.
22. A compound, according to any one of claims 1-18, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3c is optionally phenyl substituted.
23. A compound according to any one of claims 1-3 or 6, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3e is hydrogen.
24. A compound according to any one of claims 1-22, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3e is C1-C8 alkoxy.
25. Compound, according to any one of claims 1-22, CHARACTERIZED in that R3e is -OH.
26. Compound, according to any one of claims 1-22, CHARACTERIZED in that R3e is -SH.
27. Compound, according to any one of claims 1-22, CHARACTERIZED in that R3e is C1-C8 alkylthio.
28. Compound, according to any one of claims 1-22, CHARACTERIZED in that R3e is arylthio.
29. A compound according to any one of claims 1-22, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3e is C1-C9 alkyl.
30. A compound according to any one of claims 1-22, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3e is C3-C6 cycloalkyl.
31. Compound, according to any one of claims 1-22, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3e is optionally substituted phenyl.
32. Compound, according to any one of claims 1-31, CHARACTERIZED in that R3f is hydrogen.
33. A compound according to any one of claims 1-31, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3f is C1-C9 alkyl.
34. A compound according to any one of claims 1-31, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3f is C3-C6 cycloalkyl.
35. A compound, according to any one of claims 1-31, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that R3f is optionally phenyl substituted.
36. Compound, according to claim 1, or a salt, solvate or stereoisomer thereof, CHARACTERIZED in that it is selected from the group consisting of: Petition 870250088230, dated 09 / 29 / 2025, p. 39 / 56 8 / 23 Petition 870250088230, dated 09 / 29 / 2025, p. 40 / 56 9 / 23 Petition 870250088230, dated 09 / 29 / 2025, p. 41 / 56 10 / 23 Petition 870250088230, dated 09 / 29 / 2025, p. 42 / 56 11 / 23 37. Composition CHARACTERIZED in that it comprises: (i) the compound as defined in any one of claims 1-36; and (ii) one or more elastomers; or (iii) one or more fillers; or (iv) one or more rubber chemicals; or (v) one or more plasticizers; or (vi) one or more additional antidegradants; or (vii) a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers and / or one or more additional antidegradants.
38. Composition according to claim 37, CHARACTERIZED in that the composition comprises one or more elastomers.
39. Composition, according to claim 38, CHARACTERIZED in that the composition comprises about 15% by w / w and about 85% by w / w of the compound and about 15% by w / w and about 85% by w / w of one or more elastomers.
40. Composition, according to any one of claims 37-39, CHARACTERIZED in that one or more elastomers comprise natural rubber (NR).
41. Composition according to claim 40, CHARACTERIZED in that one or more elastomers comprise from about 5% by w / w to about 80% by w / w of natural rubber (NR).
42. Composition, according to claim 40 or 41, CHARACTERIZED in that the natural rubber comprises rubber derived from an alternative rubber plant.
43. Composition according to claim 42, CHARACTERIZED in that the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz (Russian dandelion).
44. Composition, according to any one of claims 38 to 43, CHARACTERIZED in that one or more elastomers comprise synthetic rubber.
45. Composition according to claim 44, CHARACTERIZED in that the synthetic rubber comprises an unsaturated rubber, a saturated rubber, a rubber with fluoro and fluoroalkyl or fluoroalkoxy substituent groups in the polymer chain (FKM), a silicone rubber (Q) or a mixture thereof.
46. Composition according to claim 45, CHARACTERIZED in that 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 mixture thereof.
47. Composition, according to claim 46, CHARACTERIZED by Petition 870250088230, dated 09 / 29 / 2025, page 44 / 56 13 / 23 fact that the unsaturated rubber comprises styrene-butadiene rubber (SBR).
48. Composition according to claim 47, CHARACTERIZED in that one or more elastomers comprise from about 5% by w / w to about 80% by w / w of styrene-butadiene rubber (SBR).
49. Composition, according to any one of claims 46-48, CHARACTERIZED in that the unsaturated rubber comprises polybutadiene rubber (BR).
50. Composition, according to claim 49, CHARACTERIZED in that one or more elastomers comprise from about 5% by w / w to about 80% by w / w of polybutadiene rubber (BR).
51. Composition, according to any one of claims 46-50, CHARACTERIZED in that the unsaturated rubber comprises butyl rubber (IIR).
52. Composition according to claim 51, CHARACTERIZED in that one or more elastomers comprise from about 1% by w / w to about 30% by w / w of butyl rubber (IIR).
53. Composition, according to any one of claims 45-52, CHARACTERIZED in that 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 mixture thereof.
54. Composition according to claims 37-53, CHARACTERIZED in that one or more elastomers further comprise recycled rubber.
55. Composition, according to any one of claims 37-54, CHARACTERIZED in that the composition comprises from about 0.1 phr to about 10 phr of the compound. Petition 870250088230, dated 09 / 29 / 2025, pp. 45 / 56 14 / 23 56. Composition according to claim 55, CHARACTERIZED in that the composition comprises from about 0.5 phr to about 5 phr of the compound.
57. Compound according to claim 56, CHARACTERIZED in that the composition comprises from about 1 phr to about 5 phr of the compound.
58. Composition, according to any one of claims 37-57, CHARACTERIZED in that the composition comprises one or more fillers.
59. Composition, according to claim 58, CHARACTERIZED in that the composition comprises about 15% by w / w and about 85% by w / w of the compound and about 15% by w / w and about 85% by w / w of one or more fillers.
60. Composition, according to claims 58 or 59, CHARACTERIZED in that the composition comprises from about 30 phr to about 500 phr of one or more charges.
61. Composition, according to any one of claims 58 to 60, CHARACTERIZED in that one or more fillers comprise carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNTs), carbon fibers (HCFs), graphite, graphene, aluminosilicates, starch, fibers or a combination thereof.
62. Composition according to claim 61, CHARACTERIZED in that one or more fillers comprise silica.
63. Composition according to claim 62, CHARACTERIZED in that the silica is derived from rice husks.
64. Composition, according to any one of claims 58-63, CHARACTERIZED in that one or more charges comprise carbon black. Petition 870250088230, dated 09 / 29 / 2025, pp. 46 / 56 15 / 23 65. Composition, according to any one of claims 37-64, CHARACTERIZED in that the composition comprises one or more rubber chemicals.
66. Composition, according to claim 65, CHARACTERIZED in that the composition comprises about 15% by w / w and about 85% by w / w of the compound and about 15% by w / w and about 85% by w / w of one or more rubber chemicals.
67. Composition, according to claims 65 or 66, CHARACTERIZED in that the composition comprises from about 0.1 phr to about 30 phr of one or more rubber chemicals.
68. Composition according to claim 67, CHARACTERIZED in that the composition comprises from about 1 phr to about 20 phr of one or more rubber chemicals.
69. Composition, according to any one of claims 64-68, CHARACTERIZED in that one or more rubber chemicals comprise one or more vulcanizing agents, one or more accelerators, one or more activators, one or more pre-vulcanization inhibitors or a combination thereof.
70. Composition according to claim 69, CHARACTERIZED in that one or more rubber chemicals comprise one or more vulcanizing agents.
71. Composition according to claim 70, CHARACTERIZED in that one or more vulcanizing agents comprise sulfur, peroxide, resin or a combination thereof.
72. Composition according to claim 71, CHARACTERIZED in that the sulfur is octasulfur (S8), cyclododecasulfur (S12), polymeric sulfur or a combination thereof. Petition 870250088230, dated 09 / 29 / 2025, pp. 47 / 56 16 / 23 73. Composition according to claim 71, CHARACTERIZED in that the peroxide is benzoyl peroxide, dicumyl peroxide (DC), 2,5-dimethyl-2,5-di-(tert-butylperoxy)-3-hexyne (2,5-Tri), 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane (DDPH), di-(2-tert-butylperoxyisopropyl)benzene (VC), butyl-4,4-di-(tert-butylperoxy)valerate (VAL), 1,1-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC) or a combination thereof.
74. Composition according to claim 71, CHARACTERIZED in that the resin is a bonding resin.
75. Composition according to claims 69-74, CHARACTERIZED in that one or more rubber chemicals comprise one or more accelerators.
76. Composition according to claim 75, CHARACTERIZED in that one or more accelerators comprise a guanidine, a thiazole, a sulfenamide, a thiuram, a dithiocarbamate, a xanthate, a thiophosphate or a combination thereof.
77. Composition according to claim 76, CHARACTERIZED in that the guanidine component is diphenylguanidine (DPG).
78. Composition according to claim 76, CHARACTERIZED in that the thiazole comprises 2-mercaptobenzothiazole (MBT), zinc 2-mercaptobenzothiazole (ZMBT), mercaptobenzothiazole disulfide (MBTS), N-tert-butyl-2-benzothiazole sulfenimide (TBSI) or a combination thereof.
79. Composition according to claim 76, CHARACTERIZED in that the sulfenamide comprises N-tert-butyl-2-benzothiazolesulfenamide (TBBS), N-cyclohexylbenzothiazole-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), N-oxydiethylene benzothiazole sulfenamide (OBTS), N-oxydiethylene thiocarbamyl-N'-oxydiethylene sulfenamide (OTOS), thiocarbamyl sulfenamide or a combination thereof. Petition 870250088230, dated 09 / 29 / 2025, pp. 48 / 56 17 / 23 80. Composition according to claim 76, CHARACTERIZED in that the thiuram is dithioperoxyanhydride dimethylcarbamothioic acid (tiram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzyl thiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), tetramethylthiuram monosulfide (TMTM) or a combination thereof.
81. Composition according to claim 76, CHARACTERIZED in that the dithiocarbamate comprises zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyldithiocarbamate (ZDBC), nickel dibutyldithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), zinc dibenzyldithiocarbamate (ZEBC) or a combination thereof.
82. Composition, according to any one of claims 69-81, CHARACTERIZED in that one or more rubber chemicals comprise one or more activators.
83. Composition according to claim 82, CHARACTERIZED in that one or more activators comprise a metal oxide, an acid, a metal complex or a combination thereof.
84. Composition according to claim 83, CHARACTERIZED in that the metal oxide comprises zinc oxide, magnesium oxide, lead oxide or a combination thereof.
85. Composition according to claim 83, CHARACTERIZED in that the acid comprises stearic acid, lauric acid or a combination thereof.
86. Composition according to claim 83, CHARACTERIZED in that the metal complex comprises zinc ethyl hexanoate.
87. Composition, according to any of claims 69-86, CHARACTERIZED in that one or more rubber chemicals Petition 870250088230, dated 09 / 29 / 2025, p. 49 / 56 18 / 23 comprise one or more pre-vulcanization inhibitors.
88. Composition according to claim 87, CHARACTERIZED in that one or more pre-vulcanization inhibitors comprise N-(cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, phthalic anhydride or a combination thereof.
89. Composition, according to any one of claims 37-88, CHARACTERIZED in that the composition comprises one or more plasticizers.
90. Composition, according to claim 89, CHARACTERIZED in that the composition comprises about 15% by w / w and about 85% by w / w of the compound and about 15% by w / w and about 85% by w / w of one or more plasticizers.
91. Composition, according to claims 89 or 90, CHARACTERIZED in that the composition comprises from about 0.1 phr to about 30 phr of one or more plasticizers.
92. Composition according to claim 91, CHARACTERIZED in that the composition comprises from about 1 phr to about 20 phr of one or more plasticizers.
93. Composition, according to any one of claims 89-92, CHARACTERIZED in that one or more plasticizers comprise a mineral oil, an organic ester, a resin, a wax, an ester plasticizer, a naturally derived oil or a combination thereof.
94. Composition according to claim 93, CHARACTERIZED in that the mineral oil is naphthenic oil, paraffinic oil or aromatic oil.
95. Composition, according to claim 93, CHARACTERIZED in that the naturally derived oil is soybean oil, vegetable oil or orange oil. Petition 870250088230, dated 09 / 29 / 2025, p. 50 / 56 19 / 23 96. Composition, according to any one of claims 37-95, CHARACTERIZED in that the composition further comprises one or more additional antidegradants.
97. Composition, according to claim 96, CHARACTERIZED in that the composition comprises about 15% by w / w and about 85% by w / w of the compound and about 15% by w / w and about 85% by w / w of one or more additional antidegradants.
98. Composition according to claim 96 or 97, CHARACTERIZED in that one or more additional antidegradants are present in an amount of about 0.001 phr to about 10 phr.
99. Composition according to claim 98, CHARACTERIZED in that one or more additional antidegradants are present in an amount of about 0.1 phr to about 5 phr.
100. Composition according to claim 99, CHARACTERIZED in that one or more additional antidegradants are present in an amount of about 0.5 phr to about 5 phr.
101. Composition according to claim 100, CHARACTERIZED in that one or more additional antidegradants are present in an amount of about 1 phr to about 5 phr.
102. Composition, according to any one of claims 96-101, CHARACTERIZED in that one or more additional antidegradants are an antioxidant.
103. Composition, according to any one of claims 96-101, CHARACTERIZED in that one or more additional antidegradants are an antiozonant.
104. Composition, according to any of claims 96-103, CHARACTERIZED in that one or more additional antidegradants are Petition 870250088230, dated 09 / 29 / 2025, page 51 / 56 20 / 23 a paraphenylenediamine (PPD), a trimethyldihydroquinoline (TMQ), a phenolic, an alkylated diphenylamine (DPA) or a diphenylamine ketone condensate.
105. Composition, according to claim 104, CHARACTERIZED by the fact that the PPD is N1-(4-methylpentan-2-yl)-N4-phenylbenzene-1,4-diamine (6PPD), N-(1,4-dimethylpentyl)-N-phenyl-p-phenylenediamine (7PPD), N1-phenyl-N4-(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 NN-dioctyl-p-phenylenediamine (88PD).
106. Composition according to claim 105, CHARACTERIZED in that the PPD is 6PPD.
107. Composition according to claim 104, CHARACTERIZED in that TMQ is 2,2,4-trimethyl-1,2-dihydroquinoline or an oligomer or polymer thereof.
108. Composition CHARACTERIZED in that it comprises the compound as defined in any one of claims 1-36 and one or more carriers.
109. Process for preparing the composition as defined in claim 108, the process CHARACTERIZED in that it comprises mixing the compound and one or more carriers.
110. Vulcanized elastomeric article CHARACTERIZED in that it comprises the compound as defined in any one of claims 1-36.
111. Vulcanized elastomeric article CHARACTERIZED in that it is prepared using the composition as defined in any one of claims 37-108.
112. Vulcanized elastomeric article, according to claims 110 or 111, CHARACTERIZED in that the vulcanized elastomeric article is a tire. Petition 870250088230, dated 09 / 29 / 2025, pp. 52 / 56 21 / 23 113. Vulcanized elastomeric article, according to claim 112, CHARACTERIZED in that the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, an excavator tire, an airplane tire or a racing tire.
114. Vulcanized elastomeric article, according to claims 110 or 111, CHARACTERIZED in that the vulcanized elastomeric article is a component of a tire.
115. Vulcanized elastomeric article, according to claim 114, CHARACTERIZED in that the component is a bead, a belt, a carcass ply, an inner lining, a sidewall, a sub-tread or a tread.
116. Vulcanized elastomeric article, according to claims 110 or 111, CHARACTERIZED in that the vulcanized elastomeric article is a rubber overlay, a sealing strip, an acoustic panel, an air spring, a bellows, a membrane, a tactile sensor, a protective pad, a hose, a conveyor belt or a floor.
117. Process for preparing a vulcanized elastomeric article, the process CHARACTERIZED in that it comprises: (a) forming the composition as defined in any one of claims 38-107 into a formed shape; and (b) vulcanizing the formed shape to provide a vulcanized elastomeric article.
118. Process according to claim 117, CHARACTERIZED in that the vulcanization is carried out at an average temperature of about 120 °C to about 180 °C.
119. Process, according to claim 118, CHARACTERIZED by Petition 870250088230, dated 09 / 29 / 2025, pp. 53 / 56 22 / 23 in that vulcanization is carried out at an average temperature of about 140 °C to about 160 °C.
120. Process, according to any one of claims 117-119, CHARACTERIZED in that the vulcanized elastomeric article is a tire.
121. Process according to claim 120, CHARACTERIZED in that the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agricultural tire, an excavator tire, an airplane tire or a racing tire.
122. Process, according to any one of claims 117-121, CHARACTERIZED in that the vulcanized elastomeric article is a component of a tire.
123. Process according to claim 122, CHARACTERIZED in that the component is a bead, a belt, a carcass ply, an inner lining, a sidewall, a sub-tread or a tread.
124. Process, according to any one of claims 117-119, CHARACTERIZED in that the vulcanized elastomeric article is a rubber overlay, a sealing strip, an acoustic panel, an air spring, a bellows, a membrane, a tactile sensor, a protective pad, a hose, a conveyor belt or a floor.
125. Lubricating composition CHARACTERIZED in that it comprises a lubricant and the compound as defined in any one of claims 1-36.
126. Fuel composition CHARACTERIZED in that it comprises a fuel and the compound as defined in any one of claims 1-36.
127. Fuel additive composition CHARACTERIZED by the fact that Petition 870250088230, dated 09 / 29 / 2025, pp. 54 / 56 23 / 23 comprises a fuel additive and the compound as defined in any of claims 1-36.
128. A process for retreading tires, the process CHARACTERIZED in that it comprises: (a) applying the composition as defined in any one of claims 37-108 to a tire; (b) placing a pre-vulcanized tread around the tire; (c) placing a curing envelope around the tire; and (d) vulcanizing the tire.
129. Kit CHARACTERIZED in that it comprises the composition as defined in any one of claims 37-108 and instructions for using the composition in a vulcanizable elastomeric composition.
130. Kit CHARACTERIZED in that it comprises the composition as defined in any one of claims 37-108 and instructions for using the composition to prepare a vulcanized elastomeric article.
131. Composition, according to any one of claims 37, 38, 40-58, 60-65, 67-89, 91-96 or 98-107, CHARACTERIZED in that the composition comprises about 0.1% by weight to about 10% by weight of the compound. Petition 870250088230, dated 09 / 29 / 2025, pp. 55 / 56