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WO2024206789A2 - Agents antidégradants à base de 6-aminoquinoline - Google Patents

Agents antidégradants à base de 6-aminoquinoline Download PDF

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Publication number
WO2024206789A2
WO2024206789A2 PCT/US2024/022189 US2024022189W WO2024206789A2 WO 2024206789 A2 WO2024206789 A2 WO 2024206789A2 US 2024022189 W US2024022189 W US 2024022189W WO 2024206789 A2 WO2024206789 A2 WO 2024206789A2
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Prior art keywords
composition
phr
compound
rubber
solvate
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WO2024206789A3 (fr
Inventor
Judicael Jacques Chapelet
Malik Hani AL-AFYOUNI
Frederick Ignatz-Hoover
Jonathan Michael Penney
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Flexsys America LP
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Flexsys America LP
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Priority to CN202480027285.XA priority Critical patent/CN121001718A/zh
Publication of WO2024206789A2 publication Critical patent/WO2024206789A2/fr
Publication of WO2024206789A3 publication Critical patent/WO2024206789A3/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present disclosure provides compounds with antidegradant, e.g., antiozonant, antioxidant and/or antifatigue, properties that are useful additives for vulcanized rubber articles, compositions comprising elastomers, lubricants, fuels, and other compositions which require such properties or in compositions which are themselves useful as compositions to impart such properties.
  • antidegradant e.g., antiozonant, antioxidant and/or antifatigue
  • Anti degradants useful in the manufacture of articles formed from elastomers, plastics and the like require a very specific combination of qualities that can be difficult to achieve. While the anti degradants must obviously have commercially acceptable efficacy, they must also exhibit that efficacy over prolonged periods of time associated with use of the article, particularly at exposed surfaces of the article where degradation from environmental factors such as light, oxygen and ozone primarily occurs. Just as important to the protection of surface exposed components, efficacy in protecting imbedded components of composite materials from the effects of oxidative aging and repetitive mechanical action are critically important. The anti degradants must achieve these results while not negatively impacting other additives' efficacy or desirable characteristics in the final article.
  • anti degradants which provide or improve the mechanical fatigue life after an article has been in service, aged oxidatively or by exposure to ozone are highly valued since these will inherently improve the useful mechanical service life of article. Consequently, elastomeric articles which undergo repeated mechanical flexure, extension, or compression during service would greatly benefit from such a discovery.
  • the present disclosure provides compounds that are useful as anti degradants, e.g., antiozonants, and/or antioxidants, and/or as additives in lubricants or combustible fuels, represented by any one of Formulae (I)-(III), below, collectively referred to herein as "Compounds of the Disclosure” or individually as a “Compound of the Disclosure.”
  • compositions comprising:
  • compositions of the Disclosure a combination of one or more elastomers, one or more fillers, one or more rubber chemicals, one or more plasticizers, and/or one or more additional anti degradants, collectively referred to herein as "Compositions of the Disclosure” or individually as a “Composition of the Disclosure.”
  • compositions of the Disclosure comprising a Compound of the Disclosure and one or more elastomers.
  • compositions of the Disclosure comprising a Compound of the Disclosure and one or more fillers.
  • compositions of the Disclosure comprising a Compound of the Disclosure and one or more rubber chemicals.
  • compositions of the Disclosure comprising a Compound of the Disclosure and one or more plasticizers.
  • compositions of the Disclosure comprising a Compound of the Disclosure and one or more additional anti degradants.
  • compositions of the Disclosure comprising a Compound of the Disclosure and one or more carriers.
  • the present disclosure also provides processes for preparing a composition comprising a Compound of the Disclosure and one or more carriers, the process comprising admixing the compound and the one or more carriers.
  • the present disclosure also provides vulcanized elastomeric articles comprising a Compound of the Disclosure.
  • the present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein, e.g., Compositions of the Disclosure or compositions comprising a Compound of the Disclosure and one or more carriers.
  • the present disclosure also provides a process for preparing the vulcanized elastomeric articles described herein, the process comprising:
  • the present disclosure also provides lubricant compositions comprising a lubricant and a Compound of the Disclosure. [0019] The present disclosure also provides combustible fuel compositions comprising a combustible fuel and a Compound of the Disclosure.
  • the present disclosure also provides fuel additive compositions comprising a fuel additive and a Compound of the Disclosure.
  • the present disclosure also provides a process for retreading tires, the process comprising:
  • kits comprising a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition.
  • kits comprising a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article.
  • Fig. l is a line graph depicting a J H nuclear magnetic resonance (NMR) spectrum of intermediate compound 1-1 in tAdimethyl sulfoxide (t/e-DMSO).
  • Fig. 2 is a line graph depicting a 13 C APT NMR spectrum of intermediate compound 1-1 in t/e-DMSO.
  • Fig. 3 is a liquid chromatography (LC) chromatogram of intermediate compound
  • Fig. 4 is a line graph depicting a 13 C APT NMR spectrum of Compound 1 in ⁇ /-chloroform (CDCh).
  • Fig. 5 is an LC chromatogram of Compound 1.
  • Fig. 6 is a line graph depicting a 13 C APT NMR spectrum of Compound 2 in MSO.
  • Fig. 7 is an LC chromatogram of Compound 2.
  • Fig. 8 is an LC chromatogram of intermediate compound 3-1.
  • Fig. 9 is a line graph depicting a 13 C APT NMR spectrum of Compound 3 in MSO.
  • Fig. 10 is an LC chromatogram of Compound 3.
  • Fig. 11 is a line graph depicting a 13 C APT NMR spectrum of intermediate compound 4-1 in tL-DMSO.
  • Fig. 12 is an LC chromatogram of intermediate compound 4-1.
  • Fig. 13 is a line graph depicting a 13 C APT NMR spectrum of Compound 4 in MSO.
  • Fig. 14 is an LC chromatogram of Compound 4.
  • Fig. 15 is a line graph depicting a 13 C APT NMR spectrum of intermediate compound 47-1 in tL-DMSO.
  • Fig. 16 is an LC chromatogram of intermediate compound 47-1.
  • Fig. 17 is a line graph depicting a 13 C APT NMR spectrum of Compound 47 in MSO.
  • Fig. 18 is an LC chromatogram of Compound 47.
  • R la is selected from the group consisting of optionally substituted C1-C12 alkyl, -CHR lc R ld , C3-C6 cycloalkyl, 4- to 6-membered heterocyclyl, optionally substituted phenyl, and optionally substituted 5- or 6-membered heteroaryl;
  • R lb is selected from the group consisting of hydrogen and C1-C9 alkyl
  • R lc is selected from the group consisting of optionally substituted phenyl, C3-C6 cycloalkyl, and optionally substituted 5- or 6-membered heteroaryl;
  • R ld is selected from the group consisting of hydrogen and C1-C9 alkyl
  • R 2a , R 2b , and R 2c are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, Ci-Cs alkoxy, Ci-Cs alkylthio,
  • R 2b is selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, Ci-Cs alkoxy, Ci-Cs alkylthio,
  • R 2a and R 2c together with the two carbon atoms to which they are attached form a C5-C8 cycloalkyl, a 5- to 8-membered heterocyclyl, or a Cs-Ce aryl;
  • R 3C and R 3d together with the carbon atom to which they are attached form a C3-C12 cycloalkyl, with the proviso that is a single bond;
  • R 3e and R 3f are independently selected from the group consisting of hydrogen, halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, Ci-Cs alkoxy, Ci-Cs alkylthio, arylthio,
  • R 3e and R 3f taken together with the carbon atom to which they are attached form a C3-C12 cycloalkyl
  • R 3g is selected from the group consisting of hydrogen and C1-C9 alkyl
  • R 4 and R 5 are at each occurrence independently selected from the group consisting of hydrogen, C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.
  • Compounds of the Disclosure are compounds having
  • R 3e and/or R 3f are hydrogen
  • R 3c and R 3d are independently selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl.
  • Compounds of the Disclosure are compounds having
  • Compounds of the Disclosure are compounds of Formula (II), wherein:
  • R 3C and R 3d are independently selected from the group consisting of C1-C9 alkyl, C3-C6 cycloalkyl, and optionally substituted phenyl; or
  • R 3C and R 3d together with the carbon atom to which they are attached form a C3-C12 cycloalkyl.
  • Compounds of the Disclosure are compounds of Formula (II), wherein:
  • R 3e and R 3f are independently selected from the group consisting of halogen, C1-C9 alkyl, C1-C9 haloalkyl, C3-C8 cycloalkyl, -OH, -SH, Ci-Cs alkoxy, Ci-Cs alkylthio, arylthio,
  • Compounds of the Disclosure are compounds of Formula (I) or Formula (II), wherein R 3b is hydrogen.
  • Compounds of the Disclosure are compounds having Formula (III): wherein R la , R 2a , R 2b , R 2c , R 3a , R 3c , R 3e , and R 3f are as defined in connection with Formula (I).
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R la is optionally substituted phenyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R la is C1-C12 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R la is methyl, ethyl, propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, or nonyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein wherein R la is iso-propyl or sec-butyl. [0075] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein wherein R la is:
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 2a , R 2b , and R 2c are independently selected from the group consisting of hydrogen and C1-C9 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 2b and R 2c are hydrogen.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 2a is selected from the group consisting of hydrogen and C1-C4 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3a is hydrogen.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3a is C1-C9 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3a is C3-C6 cycloalkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3a is optionally substituted phenyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3c is hydrogen.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3c is C1-C9 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3c is C3-C6 cycloalkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3c is optionally substituted phenyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is hydrogen.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is Ci-Cs alkoxy. [0089] In some embodiments, Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is -OH.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is -SH.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is Ci-Cs alkylthio.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is arylthio.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is C1-C9 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is C3-C6 cycloalkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3e is optionally substituted phenyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3f is hydrogen.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3f is C1-C9 alkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3f is C3-C6 cycloalkyl.
  • Compounds of the Disclosure are compounds of any one of Formulae (I)-(III), wherein R 3f is optionally substituted phenyl.
  • Compounds of the Disclosure are any one or more of the compounds of Table 1, or a salt or solvate thereof.
  • Compounds of the Disclosure can be useful as anti degradants, e.g., antiozonants and/or antioxidants, as additives in lubricants, and as additives in combustible fuels.
  • 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., via a Povarov reaction, and ii) reacting the product of step i) with an aldehyde or ketone under reductive conditions, e.g., pressurized H2 with a platinum catalyst, as shown in Scheme 1, wherein R le is, for example, C1-C12 alkyl, C3-C6 cycloalkyl, optionally substituted phenyl, or optionally substituted 5- or 6-membered heteroaryl, and R lf is, for example, hydrogen or Ci-Ce alkyl.
  • alkyl refers to a straight- or branched-chain aliphatic hydrocarbon containing one to twelve carbon atoms, i.e., a C1-C12 alkyl, or the number of carbon atoms designated, e.g., 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 on.
  • the alkyl is a straight-chain alkyl. In another embodiment, the alkyl is a branched-chain alkyl. In one embodiment, the alkyl is a Ci-Cs alkyl. In another embodiment, the alkyl is a Ci-Ce alkyl. In another embodiment, the alkyl is a C1-C4 alkyl. In another embodiment, the alkyl is a C1-C3 alkyl.
  • Non-limiting exemplary C1-C12 alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, ec-butyl, /e/7-butyl, zso-butyl, 3-pentyl, hexyl, heptyl, octyl, nonyl, and decyl.
  • aryl refers to an aromatic ring system having six to fourteen carbon atoms, i.e., C6-C14 aryl.
  • Non-limiting exemplary aryl groups include phenyl (abbreviated as "Ph"), naphthyl, phenanthryl, anthracyl, indenyl, azulenyl, biphenyl, biphenylenyl, and fluorenyl groups.
  • the aryl group is phenyl or naphthyl.
  • the aryl group is phenyl.
  • halo or halogen as used herein by itself or as part of another group refers to -Cl, -F, -Br, or -I.
  • nitro as used herein by itself or as part of another group refers to -NO2.
  • cyano as used herein by itself or as part of another group refers to -CN.
  • amino as used by itself or as part of another group refers to a radical of the formula -NR lg R lh , wherein R lg and R lh are independently hydrogen or alkyl.
  • the amino is -NH2.
  • the amino is an "alkylamino," i.e., an amino group wherein R lg is Ci-Ce alkyl and R lh is hydrogen.
  • R lg is C1-C4 alkyl.
  • Non-limiting exemplary alkylamino groups include -N(H)CH3 and -N(H)CH2CH3.
  • the amino is a "dialkylamino," i.e., an amino group wherein R lg and R lh are each independently Ci-Ce alkyl. In one embodiment, R lg and R lh are each independently C1-C4 alkyl.
  • Non-limiting exemplary dialkylamino groups include -N(CH 3 ) 2 and -N(CH 3 )CH 2 CH(CH3)2.
  • the alkyl is a C1-C4 alkyl.
  • a non-limiting exemplary alkylcarbonyl group is -COCH3.
  • haloalkyl refers to an alkyl substituted by one or more fluorine, chlorine, bromine, and/or iodine atoms. In one embodiment, the alkyl is substituted by one, two, or three fluorine and/or chlorine atoms. In another embodiment, the alkyl is substituted by one, two, or three fluorine atoms.
  • the alkyl is a Ci-Ce alkyl and the resulting haloalkyl is referred to as a "Ci-Ce haloalkyl.”
  • the alkyl is a C1-C4 alkyl and the resulting haloalkyl is referred to as a "C1-C4 haloalkyl.”
  • the alkyl group is a Ci or C2 alkyl.
  • Non-limiting exemplary haloalkyl groups include fluorom ethyl, difluorom ethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and trichloromethyl groups.
  • alkoxy refers to an alkyl attached to a terminal oxygen atom.
  • the alkyl is a Ci-Ce alkyl, and the resulting alkoxy is referred to as a "Ci-Ce alkoxy.”
  • the alkyl is a C1-C4 alkyl group and thus the resulting alkoxy is referred to as a "C1-C4 alkoxy.”
  • Non-limiting exemplary alkoxy groups include methoxy, ethoxy, and tertbutoxy.
  • alkylthio refers to an alkyl group attached to a terminal sulfur atom.
  • the alkyl is a Ci-Ce alkyl, and the resulting alkylthio is referred to as a "Ci-Ce alkylthio.”
  • the alkyl group is a C1-C4 alkyl group and the resulting alkylthio is referred to as a "C1-C4 alkylthio.”
  • Non-limiting exemplary alkylthio groups include -SCH3, and -SCH2CH3.
  • arylthio as used herein by itself or as part of another group refers to an aryl group attached to a terminal sulfur atom.
  • the aryl is group is phenyl or naphthyl.
  • cycloalkyl refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic aliphatic hydrocarbons containing three to twelve carbon atoms, i.e., a C3-C12 cycloalkyl, or the number of carbons designated, e.g., a C3-C6 cycloalkyl such a cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • the cycloalkyl is bicyclic, i.e., it has two rings.
  • the cycloalkyl is monocyclic, i.e., it has one ring.
  • the cycloalkyl is a C3-C8 cycloalkyl.
  • the cycloalkyl is a C3-C6 cycloalkyl.
  • the cycloalkyl is a Cs cycloalkyl, i.e., cyclopentyl.
  • the cycloalkyl is a Ce cycloalkyl, i.e., cyclohexyl.
  • Non-limiting exemplary C3-C12 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, norbomyl, decalin, adamantyl, cyclohexenyl, and spiro[3.3]heptane.
  • phenyl that is either unsubstituted or substituted with one to five substitutents, wherein the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.
  • heterocyclo refers to saturated and partially unsaturated, e.g., containing one or two double bonds, monocyclic, bicyclic, or tricyclic groups containing three to eighteen ring members, i.e., a 3- to 18-membered heterocyclo, comprising one, two, three, or four heteroatoms.
  • Each heteroatom is independently oxygen, sulfur, or nitrogen.
  • heterocyclo also includes groups having fused optionally substituted aryl or optionally substituted heteroaryl groups such as indoline, indolin-2-one, 2,3-dihydro-lH-pyrrolo[2,3-c]pyridine, 2,3,4,5-tetrahydro-lH- benzo[d]azepine, or l,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one.
  • heterocyclo is a 6-membered ring comprising one nitrogen atom.
  • the heterocyclo may be fused to the rest of the molecule to form a bicyclic group, e.g., 1,2-dihydroquinoline or 1,2,3,4-tetrahydroquinoline.
  • optionally substituted heterocyclo refers to a heterocyclo group that is either unsubstituted or substituted with one to four substituents, wheren the substituents are each independently halo, nitro, cyano, hydroxyl, amino, (e.g., -NH2, alkylamino, or dialkylamino), alkoxy, alkylthio, alkylcarbonyl, alkyl, or cycloalkyl.
  • heteroaryl refers to monocyclic aromatic ring systems having five to six ring members, i.e., a 5- to 6-membered heteroaryl, comprising one, two, three, four, or five heteroatoms.
  • Each heteroatom is independently oxygen, sulfur, or nitrogen.
  • the heteroaryl has three heteroatoms.
  • the heteroaryl has two heteroatoms.
  • the heteroaryl has one heteroatom.
  • the heteroaryl has 5 ring atoms, e.g., furyl, a 5-membered heteroaryl having four carbon atoms and one oxygen atom.
  • the heteroaryl has 6 ring atoms, e.g., pyridyl, a 6-membered heteroaryl having five carbon atoms and one nitrogen atom.
  • Non-limiting exemplary heteroaryl groups include thienyl, furyl, pyranyl, 2/7-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, thiazolyl, isothiazolyl, and isoxazolyl.
  • the heteroaryl is chosen from thienyl (e.g., thien-2-yl and thien-3-yl), furyl (e.g., 2-furyl and 3-furyl), pyrrolyl (e.g., 1H- pyrrol-2-yl and lH-pyrrol-3-yl), imidazolyl (e.g., 2H-imidazol-2-yl and 2H-imidazol-4- yl), pyrazolyl (e.g., lH-pyrazol-3-yl, lH-pyrazol-4-yl, and lH-pyrazol-5-yl), pyridyl (e.g., pyridin-2-yl, pyridin-3-yl, and pyridin-4-yl), pyrimidinyl (e.g., pyrimidin-2-yl, pyrimidin- 4-yl, and pyrimidin-5-yl), thienyl
  • optionally substituted heteroaryl refers to a heteroaryl that is either unsubstituted or substituted with 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.
  • 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 one another (diastereomers).
  • chiral center or "asymmetric carbon atom” refers to a carbon atom to which four different groups are attached.
  • enantiomer and “enantiomeric” refer to a molecule that cannot be superimposed on its mirror image and hence is optically active wherein 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.
  • racemic refers to a mixture of equal parts of enantiomers and which mixture is optically inactive.
  • absolute configuration refers to the spatial arrangement of the atoms of a chiral molecular entity (or group) and its stereochemical description, e.g., R or S.
  • enantiomeric excess refers to a measure for how much of one enantiomer is present compared to the other.
  • percent enantiomeric excess is defined as
  • * 100, where R and S are the respective mole or weight fractions of enantiomers in a mixture such that R + S 1.
  • the percent enantiomeric excess is defined as ([a]obs/[a]max)*100, where [a]obs is the optical rotation of the mixture of enantiomers and [a]max is the optical rotation of the pure enantiomer. Determination of enantiomeric excess is possible using a variety of analytical techniques, including NMR spectroscopy, chiral column chromatography, or optical polarimetry.
  • Rf retention factor
  • Rf is defined as the distance travelled by an individual component divided by the total distance travelled by the eluent. Its value is always between zero and one.
  • Salts and solvates, e.g., hydrates, of the Compounds of the Disclosure can also be used in the methods disclosed herein.
  • the present disclosure encompasses the preparation and use of salts of Compounds of the Disclosure.
  • Salts of Compounds of the Disclosure can be prepared during the final isolation and purification of the compounds or separately by reacting the compound with an acid having a suitable cation.
  • Salts of Compounds of the Disclosure can be acid addition salts formed with acceptable acids. Examples of acids which can be employed to form salts include inorganic acids such as nitric, boric, hydrochloric, hydrobromic, sulfuric, and phosphoric, and organic acids such as oxalic, maleic, succinic, and citric.
  • Non-limiting examples of salts of compounds of the disclosure include, but are not limited to, the hydrochloride, hydrobromide, hydroiodide, sulfate, bisulfate, 2- hydroxyethansulfonate, phosphate, hydrogen phosphate, acetate, adipate, alginate, aspartate, benzoate, bisulfate, butyrate, camphorate, camphorsulfonate, digluconate, glycerolphosphate, hemi sulfate, heptanoate, hexanoate, formate, succinate, fumarate, maleate, ascorbate, isethionate, salicylate, methanesulfonate, mesitylenesulfonate, naphthylenesulfonate, nicotinate, 2-naphthalenesulfonate, oxalate, pamoate, pectinate, persulfate, 3-phenylproprionate, picrate
  • available amino groups present in the compounds of the disclosure can be quaternized with methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides; dimethyl, diethyl, dibutyl, and diamyl sulfates; decyl, lauryl, myristyl, and steryl chlorides, bromides, and iodides; and benzyl and phenethyl bromides.
  • any reference to Compounds of the Disclosure appearing herein is intended to include Compounds of the Disclosure as well as salts, hydrates, or solvates thereof.
  • 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, e.g., a disolvate, 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.
  • solvent molecule such as, e.g., a disolvate, monosolvate or hemisolvate
  • This physical association involves varying degrees of ionic and covalent bonding, including hydrogen bonding.
  • the solvate can be isolated, such as when one or more solvent molecules are incorporated into the crystal lattice of a crystalline solid.
  • solvate encompasses both solution-phase and isolatable solvates.
  • Compounds of the Disclosure can be present as solvated forms with a solvent, such as water, methanol, and ethanol, and it is intended that the disclosure includes both solvated and unsolvated forms of Compounds of the Disclosure.
  • solvate is a hydrate.
  • a "hydrate” relates to a particular subgroup of solvates where the solvent molecule is water.
  • Preparation of solvates is known in the art. See, for example, M. Caira et al, J. Pharmaceut. Sci., 93(3):601-611 (2004), which describes the preparation of solvates of fluconazole with ethyl acetate and with water. Similar preparation of solvates, hemisolvates, hydrates, and the like are described by van Tender et al., AAPS Pharm. Sci. Tech., 5(7):Article 12 (2004), and A.L. Bingham et al., Chem. Commun. 603-604 (2001).
  • a typical, non-limiting, process of preparing a solvate would involve dissolving a Compound of the Disclosure 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 crystal of the solvate.
  • wt/wt % refers to the mass of one component in a composition or blend, e.g., a composition comprising a Compound of the Disclosure and one or more elastomers; or a Composition of the Disclosure and one or more fillers; or a blend comprising two or more elastomers, etc., divided by the combined mass of all components in the composition or blend, times 100.
  • the term "masterbatch” refers to a composition comprising at least one elastomer and a Compound of the Disclosure.
  • the masterbatch comprises from about 5 wt/wt % to about 95 wt/wt % of at least one elastomer and from about 5 wt/wt % to about 95 wt/wt % of a Compound of the Disclosure.
  • the masterbatch comprises about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of a Compound of the Disclosure.
  • the masterbatch comprises about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of at least one elastomer.
  • the term "premix” refers to a composition comprising a Compound of the Disclosure and at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof.
  • the premix does not comprise an elastomer.
  • the premix comprises from about 5 wt/wt % to about 95 wt/wt % of a Compound of the Disclosure and from about 5 wt/wt % to about 95 wt/wt % of the least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or a combination thereof.
  • the premix comprises about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of at least one additional component, e.g., a filler, a rubber chemical, a plasticizer, an additional anti degradant, or about 95 wt
  • one or more as used herein is intended to mean that at least one component in a relevant category of components, e.g. one or more elastomers, or at least one component in a disclosed list, e.g., one or more fluorine, chlorine, bromine, and/or iodine atoms, is present and, in some embodiments, more than one component is present.
  • one or more means 1 to 50.
  • one or more means 1 to 40.
  • one or more means 1 to 5.
  • compositions comprising:
  • the composition comprises from about 0.1 wt/wt% to about 10 wt/wt% of the Compound of the Disclosure, e.g., from about 0.1 wt/wt% to about 0.5 wt/wt%, from about 0.1 wt/wt% to about 1 wt/wt%, from about 0.1 wt/wt% to about 1.5 wt/wt%, from about 0.1 wt/wt% to about 2 wt/wt%, from about 0.1 wt/wt% to about 2.5 wt/wt%, from about 0.1 wt/wt% to about 3 wt/wt%, from about 0.1 wt/wt% to about 3.5 wt/wt%, from about 0.1 wt/wt% to about 4 wt/wt%, from about 0.1 wt/wt% to about 4.5 wt/wt%, from about 0.1 wt/wt%,
  • a Composition of the Disclosure comprises from about
  • the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85 wt/wt %, from about 1 wt/wt %
  • a Composition of the Disclosure comprises about 50 wt/wt % of a Compound of the Disclosure.
  • the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of
  • a Composition of the Disclosure comprises a Compound of the Disclosure and one or more elastomers.
  • elastomer as used herein is a polymer with viscoelasticity (i.e., having both viscosity and elasticity) that typically has low intermolecular forces, low Young's modulus, and high failure strain. Elastomers can typically be cross-linked by heating in the presence of one or more cross-linking agents, a process called curing or vulcanization. Rubber is one type of elastomer. Non-limiting types of rubber include natural rubber (NR), synthetic rubber, and blends thereof.
  • natural rubber as used herein refers to a naturally occurring elastomer that can be obtained from Hevea rubber trees.
  • Non-limiting types of synthetic rubbers include unsaturated rubbers, saturated rubbers, rubbers with fluoro and fluoralkyl or fluoralkoxy substituent groups on the polymer chain (FKM), silicone rubbers (Q), and blends thereof.
  • unsaturated rubbers include polyisoprene rubber (IR), butyl rubber (IIR), polybutadiene rubber (BR), styrene-isoprene-butadiene rubber (SIBR), styrene butadiene rubber (SBR), nitrile butadiene rubber (NBR), chloroprene rubber (CR), ethylene propylene diene rubber (EPDM), and blends thereof.
  • ACM acrylic rubber
  • CM chlorinated polyethylene
  • CSM chlorosulfonated polyethylene
  • CO poly chloromethyloxiran
  • EAM ethylene-ethyl acrylate copolymer
  • ECO epichlorohydrin rubber
  • EPM ethylene propylene rubber
  • EVM ethylenevinylacetate copolymer
  • the 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 naturally occurring elastomer that can be obtained from “non-Hevea” sources.
  • the alternative rubber plant is Parthenium argentatum (guayule) or Taraxacum kok-saghyz ( Russian dandelion).
  • the one or more elastomers further comprises recycled rubber.
  • recycled rubber refers to an elastomer that has been reclaimed from scrap materials such as used tires.
  • a Composition of the Disclosure comprises from about 15 wt/wt % to about 85 wt/wt % of one or more elastomers. In some embodiments, the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85
  • a Composition of the Disclosure comprises about 50 wt/wt % of one or more elastomers.
  • the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of
  • the term "phr” as used herein refers to parts per hundred parts of rubber by weight. The parts by weight of individual components are based on 100 parts by weight of the total mass of the one or more elastomers present in the composition.
  • a Composition of the Disclosure comprises from about 1 phr to about 5 phr of a Compound of the Disclosure.
  • 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
  • a Composition of the Disclosure comprises about 3 phr of a Compound of the Disclosure. In some embodiments, the composition comprises about 0.01 phr, about 0.1 phr, about 0.5 phr, about 1 phr, about 2 phr, about 3 phr, about 4 phr, about 5 phr, about 7.5 phr, about 10 phr, or about 20 phr of a Compound of the Disclosure.
  • a Composition of the Disclosure comprises a Compound of the Disclosure and one or more fillers.
  • filler is a substance that reinforces an elastomeric composition or gives an elastomeric composition other properties, including but not limited to expanding the volume of the composition.
  • fillers include carbon black, silica, kaolin, calcium silicate, talc, carbon nanotubes (CNT), carbon fibers (HCF), graphite, graphenes, aluminosilicates, starch, and fibers, and combinations thereof.
  • the filler is derived from natural sources.
  • silica may be derived from rice husks.
  • a Composition of the Disclosure comprises from about
  • the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85 wt/wt %, from about 1 wt/wt % to about
  • a Composition of the Disclosure comprises about 50 wt/wt % of one or more fillers.
  • the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of one or more fillers.
  • the composition comprises about 1
  • a Composition of the Disclosure comprises from about 30 phr to about 500 phr of one or more fillers.
  • 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 ph
  • a Composition of the Disclosure comprises about 300 phr of one or more fillers. In some embodiments, the composition comprises about 30 phr, about 50 phr, about 100 phr, about 150 phr, about 200 phr, about 250 phr, about 350 phr, about 400 phr, about 450 phr, or about 500 phr of one or more fillers.
  • a Composition of the Disclosure comprises a Compound of the Disclosure and one or more rubber chemicals.
  • rubber chemicals 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.
  • vulcanization refers to a process wherein cross-links are formed between elastomers to effect changes in the material properties of elastomers.
  • vulcanization typically increases the rigidity 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) being used.
  • curing is also used in the art to describe this process.
  • vulcanizing agent refers to any substance that enables cross-linking between elastomers. Vulcanizing agents can enable cross-linking between separate polymer chains of an elastomer by various mechanisms, including, but not limited to, by formation of covalent bonds between the vulcanizing agent and two or more separate polymer chains or by generating radical species on 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, factices and resins.
  • sulfur include octasulfur (Ss), 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 l,l-di(tert-butylperoxy)-3,3,5-trimethylcyclohexane (TMC).
  • Nonlimiting examples of resins include bonding resins.
  • bonding resin refers to a chemical such as resorcinol formaldehyde resins and phenolic resins that reacts with methylene donors (such as hexamethylenetetramine (HMTA) or hexamethoxymethyl melamine (HMMM)) to promote adhesion.
  • methylene donors such as hexamethylenetetramine (HMTA) or hexamethoxymethyl melamine (HMMM)
  • accelerators refers to any substance that increases the kinetics of vulcanization.
  • accelerators enable vulcanization to be performed at lower temperatures and/or to use the vulcanization agent, e.g., sulfur, 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 V-/ert-butyl-2-benzothi azole sulfenimide (TBSI).
  • MBT 2-mercaptobenzothiazole
  • ZMBT zinc 2-mercaptobenzothiazole
  • MBTS mercaptobenzothiazole disulfide
  • TBSI V-/ert-butyl-2-benzothi azole sulfenimide
  • Non-limiting examples of sulfenamides include N-/c/7-butyl-2- benzothiazylsulfenamide (TBBS), 7V-cyclohexylbenzothiazol-2-sulfenamide (CBS), dicyclohexyl-2-benzothiazolesulfenamide (DCBS), V-oxy di ethylene benzothiazole sulfenamide (OBTS), V-oxy di ethylenethiocarbamyl-V'-oxy di ethylene sulfenamide (OTOS), and thiocarbamyl sulfenamide.
  • TBBS N-/c/7-butyl-2- benzothiazylsulfenamide
  • CBS 7V-cyclohexylbenzothiazol-2-sulfenamide
  • DCBS dicyclohexyl-2-benzothiazolesulfenamide
  • OBTS V-oxy di ethylene benzothiazole sulfenamide
  • OTOS V
  • Non-limiting examples of thiurams include dimethylcarbamothioic dithioperoxyanhydride (thiram), dipentamethylene thiuram tetrasulfide (DPIT), tetrabenzyl thiuram disulfide (TBzTD), tetraethylthiuram disulfide (TETD), tetramethylthiuram disulfide (TMTD), and tetramethylthiuram monosulfide (TMTM).
  • thiram dimethylcarbamothioic dithioperoxyanhydride
  • DPIT dipentamethylene thiuram tetrasulfide
  • TzTD tetrabenzyl thiuram disulfide
  • TETD tetraethylthiuram disulfide
  • TMTD tetramethylthiuram disulfide
  • TMTM tetramethylthiuram monosulfide
  • Non-limiting examples of dithiocarbamates include zinc dimethyldithiocarbamate (ZDMC), zinc diethyldithiocarbamate (ZDEC), zinc dibutyl di thiocarbamate (ZDBC), nickel dibutyl dithiocarbamate (NDBC), sodium dibenzyldithiocarbamate (SBEC), sodium diethyldithiocarbamate (SDEC), tellurium diethyldithiocarbamate (TDEC), and zinc dibenzyldithiocarbamate (ZEBC).
  • ZDMC zinc dimethyldithiocarbamate
  • ZDEC zinc diethyldithiocarbamate
  • ZDBC zinc dibutyl di thiocarbamate
  • NDBC nickel dibutyl dithiocarbamate
  • SBEC sodium dibenzyldithiocarbamate
  • SDEC sodium diethyldithiocarbamate
  • TDEC tellurium diethyld
  • activator refers to any substance that activates a vulcanizing agent and enables it to cross-link elastomers as described above. Activators may act via various mechanisms, including, but not limited to, by forming chemical complexes with accelerators or by coordinating to sulfur (when sulfur is used as a vulcanizing agent).
  • Non-limiting examples of activators include metal oxides, acids, and metal complexex.
  • 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.
  • metal complexes include zinc ethylhexanoate.
  • pre-vulcanization inhibitor refers to compounds that delay the onset and/or the rate of vulcanization. These compounds are also referred to as "retarders.”
  • pre-vulcanization inhibitors include A- (cyclohexylthio)phthalimide (CTP), benzoic anhydride, salicylic anhydride, and phthalic anhydride.
  • a Composition of the Disclosure comprises from about
  • the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85 wt/wt %, from about 1 wt/wt % to about
  • a Composition of the Disclosure comprises about 15 wt/wt % of one or more rubber chemicals.
  • the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of one or more
  • a Composition of the Disclosure comprises from about 1 phr to about 20 phr of one or more rubber chemicals.
  • 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
  • a Composition of the Disclosure 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.
  • plasticizer refers to a processing aid used to reduce the viscosity, increase the plasticity, and/or extend the volume of a composition. Plasticizers facilitate the process of mixing and forming a composition comprising an elastomer before the composition is vulcanized.
  • 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.
  • a Composition of the Disclosure comprises from about
  • the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85 wt/wt %, from about 1 wt/wt % to about 85 wt/wt %, from about 1 wt/wt % to about 5 wt/wt
  • a Composition of the Disclosure comprises about 15 wt/wt % of one or more plasticizers.
  • the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of one or
  • a Composition of the Disclosure comprises from about 1 phr to about 20 phr of one or more plasticizers.
  • 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, from about 1 phr
  • a Composition of the Disclosure 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.
  • a Composition of the Disclosure further comprises one or more additional anti degradants that is not a Compound of the Disclosure.
  • the one or more additional anti degradants is an antioxidant.
  • the one or more additional anti degradants is an antiozonant.
  • anti degradants include paraphenylenediamines (PPDs), trimethyldihydroquinolines (TMQs), phenolics, alkylated diphenylamines (DP As), diphenylamineketone condensates, and natural anti degradants.
  • Non-limiting examples of PPDs include 7V 1 -(4-methylpentan-2-yl)-A 4 -phenylbenzene- 1 ,4-diamine (6PPD), N-( 1 ,4- dimethylpentyl)- '-phenyl-p-phenylenediamine (7PPD), 7V 1 -phenyl-A 4 -(propan-2- yl)benzene-l,4-diamine (IPPD), A( '-di -scc-butyl - -phenylenedi amine (44PD), N,N' ⁇ bis(l,3-dimethylbutyl)-p-phenylenediamine (66PD), 7V,A-bis(l,4-dimethylpentyl)-p- phenylenediamine (77PD), and N-N'-dioctyl- -phenylenediamine (88PD).
  • TMQs include 2,2,
  • a Composition of the Disclosure comprises from about 15 wt/wt % to about 85 wt/wt % of one or more additional anti degradants.
  • the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85
  • a Composition of the Disclosure comprises about 15 wt/wt % of one or more additional anti degradants.
  • the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of
  • a Composition of the Disclosure comprises from about 1 to about 5 phr of one or more additional anti degradants.
  • 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 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 0.01 phr to about 5 phr, from about
  • a Composition of the Disclosure comprises about 3 phr of one or more additional anti degradants. 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 anti degradants.
  • the disclosure provides a composition comprising a Compound of the Disclosure and one or more carriers.
  • carrier refers to a solid that can adsorb a liquid while retaining the general properties of a solid at room temperature.
  • the carrier is an inert material.
  • the carrier has a high surface area.
  • the carrier comprises particles with diameters of less than 500 microns.
  • the composition comprises from about 15 wt/wt % to about 85 wt/wt % of one or more carriers. In some embodiments, the composition comprises from about 1 wt/wt % to about 5 wt/wt %, from about 1 wt/wt % to about 15 wt/wt %, from about 1 wt/wt % to about 25 wt/wt %, from about 1 wt/wt % to about 35 wt/wt %, from about 1 wt/wt % to about 45 wt/wt %, from about 1 wt/wt % to about 55 wt/wt %, from about 1 wt/wt % to about 65 wt/wt %, from about 1 wt/wt % to about 75 wt/wt %, from about 1 wt/wt % to about 85 wt/wt %,
  • the composition comprises about 15 wt/wt % of one or more carriers. In some embodiments, the composition comprises about 1 wt/wt %, about 5 wt/wt %, about 10 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of one or more carriers.
  • the present disclosure also provides processes for preparing a composition comprising a Compound of the Disclosure and one or more carriers, the process comprising admixing the compound and the one or more carriers.
  • lubricant compositions comprising a Compound of the Disclosure and a lubricant.
  • lubricants include mineral oil, higher 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 naphthlalenes (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
  • the present disclosure also provides combustible fuel compositions comprising a combustible fuel and a Compound of the Disclosure.
  • combustible fuel include gasoline, diesel, kerosene, liquefied petroleum gas, synthetic fuel, and biodisesel.
  • the present disclosure also provides fuel additive compositions comprising a fuel additive and a Compound of the Disclosure.
  • fuel additives include oxygenates such as alcohols and ethers, antioxidants, stabilizers, detergents, antiknock agents, lead scavengers, fuel dyes, viscosity modifiers, and butyl rubber.
  • the butyl rubber is in the form of polyisobutylene succinimide.
  • the butyl rubber is added as a detergent to prevent fouling of diesel fuel injectors.
  • the present disclosure provides a composition recited in Table 2.
  • the vulcanized tire or other rubber article composition of Table 2 comprises about 0.1 wt/wt %, about 0.2 wt/wt %, about 0.3 wt/wt %, about 0.4 wt/wt %, about 0.5 wt/wt %, about 0.6 wt/wt %, about 0.7 wt/wt %, about 0.8 wt/wt %, about 0.9 wt/wt %, about 1 wt/wt %, about 2 wt/wt %, about 3 wt/wt %, about 4 wt/wt %, about 5 wt/wt %, about 6 wt/wt %, about 7 wt/wt %, about 8 wt/wt %, about 9 wt/wt %, or about 10 wt/wt % of a Compound of the Disclosure.
  • the vulcanized tire or other rubber article of Table 2 comprises comprises about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of at least one elastomer.
  • the unvulcanized in-tire component or built up component or other end use component composition of Table 2 comprises about 0.01 wt/wt %, about 0.02 wt/wt %, about 0.03 wt/wt %, about 0.04 wt/wt %, about 0.05 wt/wt %, about 0.06 wt/wt %, about 0.07 wt/wt %, about 0.08 wt/wt %, about 0.09 wt/wt %, about 0.1 wt/wt %, about 0.2 wt/wt %, about 0.3 wt/wt %, about 0.4 wt/wt %, about 0.5 wt/wt %, about 0.6 wt/wt %, about 0.7 wt/wt %, about 0.8 wt/wt %, about 0.9 wt/wt %, about 1 wt/w
  • the unvulcanized in-tire component or built up component or other end use component composition of Table 2 comprises comprises about 5 wt/wt %, about 10 wt/wt %, about 15 wt/wt %, about 20 wt/wt %, about 25 wt/wt %, about 30 wt/wt %, about 35 wt/wt %, about 40 wt/wt %, about 45 wt/wt %, about 50 wt/wt %, about 55 wt/wt %, about 60 wt/wt %, about 65 wt/wt %, about 70 wt/wt %, about 75 wt/wt %, about 80 wt/wt %, about 85 wt/wt %, about 90 wt/wt %, or about 95 wt/wt % of at least one elastomer.
  • the present disclosure also provides vulcanized elastomeric articles comprising a Compound of the Disclosure.
  • vulcanized elastomeric article refers to an article that is made by forming a composition comprising an elastomer into a specific shape and vulcanizing the composition to provide the article.
  • the present disclosure also provides vulcanized elastomeric articles prepared using a composition described herein.
  • the vulcanized elastomeric article is a tire.
  • the tire is a passenger vehicle tire, a light truck tire, a heavy truck or bus tire, a motorcycle tire, an agriculture tire, an earthmover tire, an airplane tire, or a racing tire.
  • the vulcanized elastomeric article is a component of a tire.
  • the component is a bead, a belt, a body ply, an inner liner, a sidewall, an undertread, or a tread.
  • the vulcanized elastomeric article is a rubber overshoe, a sealing strip, an acoustic panel, an air spring, a bellow, a membrane, a tactile sensor, a crash pad, a hose, a conveyor belt, or a flooring.
  • the present disclosure also provides processes for preparing a vulcanized elastomeric article, the process comprising:
  • the vulcanizing is performed at an average temperature of from about 140 °C to about 160 °C. In some embodiments, the vulcanizing is performed at an average temperature of from about 80 °C to about 100 °C, from about 80 °C to about 120 °C, from about 80 °C to about 140 °C, 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, from about 120 °C to about 160
  • the vulcanizing is performed at an average temperature of about 150 °C. In some embodiments, the vulcanizing is performed 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.
  • the present disclosure alsp provides processes for retreading tires, the process comprising:
  • kits comprising a composition described herein, packaged in a manner, e.g., in a container, that facilitates use of the composition to practice the processes and/or methods of the present disclosure.
  • the kit comprises a composition described herein and instructions for using the composition in a vulcanizable elastomeric composition.
  • the kit comprises a composition described herein and instructions for using the composition to prepare a vulcanized elastomeric article.
  • the composition may be packaged in any suitable container, such as a sealed bottle or vessel, with a label affixed to the ceontainer or included in the kit that describes the composition and proper use thereof.
  • aqueous 1 mol/L sodium bicarbonate 300 mL was added by portions.
  • the obtained 2-phase system was stirred until CO2 generation ceased, then transferred to a 2-L separatory funnel.
  • Ethyl acetate 700 mL was added. After shaking and decanting, the aqueous phase was discarded.
  • the obtained dark oil (69.5 g) was diluted with a mixture of isopropanol (100 mL) and hexanes (20 mL). The mixture was swirled until homogenous then kept at -20 °C overnight whereupon a yellow solid separated.
  • the obtained crude material (light-brown oil) weighed 23.7 g.
  • the oil solidified as a dark solid mass.
  • the solid mass was broken apart with a spatula.
  • To the obtained dark powder was added a mixture of ethyl acetate and hexanes (10 mL and 51 mL respectively).
  • the obtained slurry was magnetically stirred at room temperature under N2 protection for 4 days.
  • the reaction mixture was stirred without external cooling or heating for 2 days whereupon 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 obtained slurry was stirred for approx. 5 minutes.
  • the insoluble materials were removed by gravimetric filtration over filter paper. The cake was rinsed with some acetonitrile.
  • the crude material (6.35 g of damp yellow-orange solid) was triturated in isopropanol (20 mL) with a spatula until all the solid had detached from the flask walls.
  • Oxidative Induction Time (OIT) Performance of Compounds of the Disclosure [0214] The oxidative induction time (OIT) of selected Compounds of the Disclosure was evaluated. OIT is measured according to a procedure carried out 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 preselected temperature. Oxygen (O2) is then introduced to the cell and the length of time before the onset of degradation, as observed by the initiation of an endothermic process in the DSC trace, is measured.
  • DSC differential scanning calorimeter

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Tires In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente divulgation propose des composés représentés par la formule (I), ou des sels, des solvates ou des stéréoisomères de ceux-ci, R1a, R1b, R2a, R2b, R2c, R3a, R3b, R3c, R3d, R3e, R3f et R3g étant tels que définis dans la description. La présente divulgation propose également des compositions, des articles élastomères vulcanisés, des compositions lubrifiantes, des compositions de carburant combustible et des compositions d'additifs pour carburant comprenant un composé divulgué. La présente divulgation propose également des processus de préparation des compositions et des articles élastomères vulcanisés décrits. La présente divulgation propose également un processus de rechapage de pneus à l'aide d'une composition décrite. La présente divulgation propose également des kits comprenant une composition décrite.
PCT/US2024/022189 2023-03-31 2024-03-29 Agents antidégradants à base de 6-aminoquinoline Pending WO2024206789A2 (fr)

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