Anti-Degradants for Tire Protection

A compound for use as an aging stabilizer, antiozonant, and dye in rubber products like tires. The compound has the formula I: [1] The compound improves rubber durability by reducing aging and preventing blooming compared to traditional aromatic amine aging stabilizers. It provides sufficient solubility in rubber matrices like natural and synthetic rubbers. The compound has lower hazard potential compared to aromatic amine stabilizers which are suspected carcinogens. The compound can be produced by a process involving steps a) and b) starting from compound A.

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Tire rubber composition, tire rubber member, and tire that have improved on-ice performance and breaking resistance despite having voids in the rubber. The composition contains a rubber component, a void-introducing agent, and an amine-based antioxidant. The antioxidant improves aging resistance and prevents rubber property losses after high temperature exposure. This balances the void-introduction benefits for on-ice traction with better overall breaking strength.

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Rubber composition with reduced odor and improved aging resistance for tires and other rubber articles. The composition contains a diene elastomer, reinforcing filler, antidegradant, and crosslinker. The antidegradant is a combination of a high purity 6PPD and an S-TMQ quinoline antidegradant. This combination significantly reduces tire odor compared to lower purity 6PPD and regular TMQ. It also improves thermal aging resistance and tension fatigue of the rubber composition with less antidegradant.

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Antidegradant composition for rubber compounds that improves discoloration and fatigue resistance of tires without using excessive amounts of antidegradants or saturated rubbers. The composition contains a specific combination of antidegradants, namely 2,4,6-tri-(N-1,4-dimethylpentyl-p-phenylenediamine) (TMPPD) and either N-phenyl-N′-(2-methylphenyl)p-phenylenediamine (N3100-B) or N-phenyl-N′-(2,6-dimethylphenyl) p-phenylenediamine (N3100-C). The composition can be used as a masterbatch in rubber compounds or directly added to unvulcanized rubber. This allows reducing the overall amount of

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Low-pollution antidegradant compound for rubber that improves resistance to discoloration of rubber articles while maintaining mechanical and aging properties. The compound has structure N-phenyl-N′-disubstituted phenyl-p-phenylenediamine, where R1 and R2 are methyl. It reduces discoloration compared to pollution-type antidegradants like 6PPD. The low-pollution compound can be used alone or in combination with pollution-type antidegradants in rubber compositions.

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P-phenylenediamine antidegradant compounds for rubber applications with improved aging resistance. The compounds have novel structures with alkyl, cycloalkyl, or branched alkyl substituents on the phenylenediamine rings. They are synthesized via condensation and reduction reactions starting from aniline and nitrobenzene derivatives. The compounds can be used in rubber compositions to improve thermal oxidative aging and UV aging resistance of rubber products like tires.

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A new class of p-phenylenediamine antidegradants for rubber compounds, like tires, with improved ozone and aging resistance compared to traditional p-phenylenediamine antidegradants. The new antidegradants have novel structures with branched alkyl groups on the phenyl rings. They are synthesized using a one-pot condensation and reduction reaction of aniline and nitrobenzene derivatives. The condensation uses a base catalyst and the reduction uses a metal catalyst like Raney nickel. The new antidegradants can be used in rubber compositions to improve thermal oxidative aging and UV resistance of rubber products like tires.

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Rubber composition for tires that provides ozone resistance without discoloration of the tire surface. The composition contains a diene-based rubber, a filler, a specific diamine compound, and a quinoline-based antioxidant. It omits the commonly used diamine antioxidants IPPD and 6PPD that can transfer to the tire surface and cause discoloration. The replacement diamine compound improves ozone resistance without mobility issues.

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Rubber composition for tires that provides excellent low heat generation, aging resistance, and ozone resistance, without using common antioxidants like IPPD and 6PPD. The composition contains a diene rubber, filler (silica), phenylenediamine, quinoline-based antioxidant, and N-cyclohexyl-2-benzothiazolylsulfenamide vulcanization accelerator. The silica content is limited to 70% or less based on total filler. This allows sufficient antioxidant effectiveness without adsorbing to the silica.

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Compounds with multiple organic thiosulfate groups for improving aging, adhesion, and vulcanization properties in rubber compositions. The compounds are represented by formula I: S,S′,S″-((1,3,5-triazinane-1,3,5-triyl)tris(R1-1,1-diyl)) tris(sulfurothioate), where R1 is a methyl, ethyl, or propyl group. These compounds can be made by reacting a haloalkylamine hydrohalide with a metal thiosulfate to form a Bunte salt, followed by deprotonation and reaction with an aldehyde. They can be used in vulcanizable elastomeric formulations at 0.1-5 parts per 100 parts elastomer to improve aging, adhesion, and

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Compound, rubber mixture, tire, and process for aging stabilization of rubber articles like tires. The compound is a phenothiazine derivative with a branched alkyl amino group. It is an alternative to aromatic amine aging stabilizers like 6PPD. The compound improves aging stability and reduces blooming compared to aromatic amines. It can be used in rubber compounds at 0.1-60 phr. The rubber mixture contains the compound instead of or along with other aging stabilizers. The tire can have the compound-containing rubber in components like the tread. The compound can be made by reacting 3-aminophenothiazine with a branched alkyl amine.

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Rubber composition that improves the heat aging resistance of a resultant vulcanized rubber. The composition includes a vulcanized rubber of the rubber composition, a filler, a vulcanizing agent, a vulcanization accelerator, an antiaging agent, a softener such as wax or oil, a processing aid, and a rubber component.

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Tire with improved resistance to ozone cracking on the sidewalls. The tire has a crosslinked elastomeric composition containing a high loading of phenolic antioxidant (3 phr or more) to protect against ozone without using waxes or other static protective agents. This prevents staining and coloration issues on the sidewalls. The phenolic antioxidant offers sufficient ozone protection without the blooming and migration issues of waxes.

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Compound with improved anti-aging and discoloration resistance for rubber applications like tires. The compound has a specific structure represented by formula (I) with R, R1, and R2 substituents. It provides longer-lasting anti-aging protection compared to existing agents and reduces discoloration compared to conventional anti-aging compounds. The compound can be used as an anti-aging agent in rubber products like tires to prevent aging and deterioration from factors like light, heat, oxygen, and fatigue during use.

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Sulfur-crosslinked rubber mixture for vehicle tires that improves aging and cracking resistance. The mixture contains specific additives like para-phenylenediamine, dihydroquinoline, and anti-reversion agents. The mixture can have network node spacing via defined numbers of sulfur atoms or efficient vulcanization systems. The additive amounts and ratios provide improved reversion stability and cracking properties after aging. The mixture can be used in tire components like the flange profile to optimize durability.

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Rubber composition for tires and other rubber products that provides both high mechanical strength and excellent ozone crack resistance. The composition contains a diene-based rubber, a hydroquinone compound with a 4-6 carbon alkyl group, and an amine-based anti-aging agent. The hydroquinone compound improves ozone crack resistance while maintaining vulcanization properties. The amine-based anti-aging agent prevents deterioration. The composition allows making tires with both high strength and ozone resistance.

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Antidegradant composition for rubber compounds that improves discoloration, fatigue resistance, and aging performance of rubber articles like tires. The composition contains a specific combination of antidegradants: TMPPD, N3100-B, and N3100-C. The composition can be used directly in rubber compounds or as a masterbatch with a diene elastomer. The masterbatch formulation has the antidegradant composition plus optional additives like forming agent and bonding agent. The antidegradant composition and masterbatch promote rubber properties like fatigue resistance, discoloration resistance, and ozone resistance. The masterbatch further improves fatigue resistance compared to directly adding the antidegradant composition.

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Pneumatic tire with improved heat aging resistance and crack growth resistance of the belt pad while reducing the use of raw materials that can have environmental impacts. The tire uses a rubber composition for the belt pad that contains a specific vulcanization accelerator (N,N-dibenzylbenzothiazole-2-sulfenamide) and additional compounds (1,6-bis(N,N-dibenzylthiocarbamoyldithio)hexane and hexamethylene bis-thiosulfate disodium salt dihydrate) to significantly improve heat aging and crack growth resistance compared to traditional compositions. This allows the belt pad to maintain rigidity and prevent failure even after aging and repetitive loading, without needing cobalt compounds that have environmental concerns.

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Low-pollution antidegradant compound for rubber compositions that reduces discoloration of rubber articles without sacrificing aging properties. The compound is a p-phenylenediamine antidegradant with the structure N-[R1-C6-R2]-N'-C6H5, where R1 and R2 are alkyl groups. The compound improves resistance to discoloration of rubber articles compared to conventional pollution-type antidegradants like 6PPD. It can be used alone or with additional antidegradants in rubber compositions for tires, belts, etc. to reduce discoloration while maintaining aging properties.

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A method to produce oxidation resistant natural rubber from sources like guayule that involves chemically binding antioxidants to the rubber in the latex stage before extracting resins. This prevents the antioxidants from being removed during resin extraction. The antioxidant, like MADA, reacts with the rubber in the latex via a free radical addition reaction where the sulfur group becomes bound to the rubber backbone. This bound antioxidant resists extraction during resin removal steps. This allows producing oxidation resistant rubber with lower residual proteins and resins compared to traditional extraction methods.

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Using functionalized lignin as an antioxidant in rubber compounds for pneumatic tires. The lignin is chemically modified by esterifying or etherifying some of its phenolic hydroxyl groups with terpene groups. This functionalization improves the antioxidant properties of the lignin compared to non-functionalized lignin. The functionalized lignin replaces conventional petroleum-based antioxidants in rubber compounds for tires, providing a more sustainable and renewable alternative.

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Antidegradant composition that improves the resistance to appearance discoloration while maintaining the excellent resistance to aging and mechanical property in the rubber articles. The composition includes methyl, ethyl, isobutyl, and cyclohexyl, each being independently selected from C1-C12 alkyl and C3-C8 cycloalkyl.

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A low-pollution type antidegradant compound for rubber that improves resistance to discoloration in the appearance of rubber articles while maintaining mechanical and anti-aging properties. The compound has a structure of N-phenyl-N′-disubstituted phenyl-p-phenylenediamine. It can replace polluting antidegradants like 6PPD in rubber compositions to reduce discoloration without compromising performance. The compound promotes resistance of rubber articles to appearance discoloration.

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A long-lasting anti-degradant for rubber compositions, like tires, that provides improved resistance to thermo-oxidative aging and ozone aging compared to conventional antidegradants. The anti-degradant is a combination of two or more compounds, selected from specific formulas. These compounds have different structures compared to traditional antidegradants like p-phenylenediamines. The anti-degradant composition can replace or supplement conventional antidegradants in rubber compounds, like tire rubber, to provide enhanced long-term durability.

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Salts of anti-degradation compounds like 6PPD for tire elastomers that improve processability, reduce volatility, and enhance surface appearance compared to the free base compounds. The salts are formed by reacting the anti-degradation compound with a weak acid like stearic acid. The salts have better surface uniformity and reduced migration compared to the free compounds. They also have lower volatility during processing. The salts are used in tire elastomer compositions to provide improved anti-degradation protection against ozone and oxygen without the same issues of excessive volatility, migration, and discoloration of the free compounds.

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Rubber composition and tire for balancing ozone resistance, dynamic ozone resistance, and discoloration resistance. The composition contains a rubber, petroleum wax, and antidegradant. The wax has a specific composition range: 15-30% C20-C34 wax and 70-85% C35+ wax. This balance provides optimal static ozone resistance, dynamic ozone resistance, and color stability compared to conventional compositions.

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Antidegradant and antifatigue additives for rubber, lubricants, fuels, and other compositions that provide improved resistance to environmental degradation and mechanical fatigue. The additives are compounds derived from bisimines formed by reacting a p-phenylenediamine with a dicarbonyl. The bisimines are then reduced to the target antidegradant compounds. Examples include N1,N1′-(ethane-1,2-diyl)bis(N4-phenylbenzene-1,4-diamine) and N1,N1′-(1,4-phenylenebis(ethane-1,1-diyl))bis(N4-phenylbenzene-1,4-diamine). These compounds can be used as antidegradants in elastom

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Antioxidant precursors for elastomers that release antioxidants after cure. The precursors have functional groups that can react with elastomer double bonds during vulcanization. After curing, the functional groups can be hydrolyzed to release antioxidants that migrate through the elastomer to protect against oxygen and ozone degradation. This provides better antioxidant effectiveness compared to directly adding antioxidants to the elastomer. The precursors have formulas like dihydroxy-2,4-di-tert-butylphenoxy-[3-mercaptopropyl]silane.

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Rubber composition for tires that improves crack resistance, ozone resistance, discoloration resistance, and tire appearance while maintaining a good balance between them. The composition contains specific amounts of polyether, carbon black, and antioxidant relative to the rubber component. The polyether has a high glycol ether content and HLB range, the carbon black amount is moderate, and the antioxidant amount is limited.

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Tyre with improved resistance to ozone cracking on the sidewalls. The tyre has a crosslinked elastomeric composition in the sidewalls that contains a high amount (3 phr or more) of phenolic antioxidant without wax or other static protective agents. This provides ozone protection without staining or discoloration compared to using waxes or other static agents. The high phenolic antioxidant content prevents ozone damage to the sidewall elastomer.

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A composite anti-degradant for rubber compositions used in tire applications like sidewalls and belts. The anti-degradant is a mixture of two or more compounds selected from formulas I, II, III-a, and III-b. The compounds have different formulas and are used in specific mass ratios. The anti-degradant provides superior long-term resistance to thermo-oxidative aging and ozone aging compared to traditional p-phenylenediamine anti-degradants. The composite anti-degradant can be used in rubber compositions for tires at 0.1-5 parts per 100 parts rubber.

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Rubber compounds for pneumatic tires containing functionalized lignin as an antioxidant instead of traditional petroleum-based antioxidants. The functionalized lignin has phenolic hydroxyl groups esterified with terpene groups. The terpene groups prevent excessive hydroxyl group loss when the lignin oxidizes, preserving antioxidant activity. The lignin is derived from paper industry waste and provides sustainability benefits compared to petroleum antioxidants.

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Rubber compositions with improved tear resistance for tires and related methods to prepare them. The compositions contain hemp oil, which is added in an amount of 5 to 50 parts per hundred parts (phr) of rubber. The hemp oil improves tear strength of the rubber, making it more resistant to chipping and chunking in tires. The compositions can include other components like carbon black, silica, reinforcing fillers, vulcanizing agents, and antidegradants.

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Antidegradant compounds for vulcanized rubber articles and other compositions that provide improved resistance to environmental degradation and fatigue. The compounds are diamine derivatives formed by hydrogenating bisimines made from a p-phenylenediamine and a dicarbonyl compound. They can be used as antidegradant additives in vulcanizable elastomeric formulations, lubricants, fuels, and other compositions. The compounds provide long-lasting antidegradant efficacy and antifatigue properties after aging and oxidative exposure.

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Compound with antidegradant and antifatigue efficacy that improves the performance of vulcanized rubber articles, lubricants, fuels, and other compositions by preventing degradation and fatigue failure. The compound is a diamine with a specific structure represented by the formula N,N'-X-C6H4-1,4-N2. It provides multiple benefits like increased antidegradant efficacy, longer efficacy periods, and improved fatigue resistance compared to conventional antidegradants. The compound can be added to elastomeric formulations, lubricants, fuels, etc. to enhance their durability and service life.

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Rubber composition and tire with balanced ozone resistance and discoloration resistance. The composition contains a rubber component, petroleum wax, and antidegradant. The wax is a mixture of C20-C34 and C35+ hydrocarbons with specific proportions. The C20-C34 component is 15-30% and the C35+ component is 70-85% of the total wax mass. This balancing of the wax components provides rubber compositions and tires with improved static ozone resistance, dynamic ozone resistance, and discoloration resistance compared to traditional compositions.

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A process for producing tires that improves rubber properties and prevents deterioration during storage. The process involves mixing a filler, dispersant, and rubber latex to create a slurry. The slurry is then solidified and dehydrated, with a compound added during dehydration. The compound, represented by formula (I), is dispersed into the dehydrating slurry as it dries. This step prevents rubber property loss during long-term storage. The compound adds during dehydration to counteract any rubber deterioration caused by water removal. The final step is completing the tire curing.

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A method for producing tires that provides tires with improved antiaging and abrasion resistance compared to conventional tires. The method involves using a unique process to disperse an antiaging compound in the tire rubber. The process involves mixing carbon black, a dispersing solvent, and rubber latex to form a latex solution containing carbon black. The latex is solidified, then the antiaging compound is added and dispersed while dehydrating the rubber. This step yields a wet rubber masterbatch with the compound dispersed in the rubber. The compound is further added and dried with the masterbatch. This two-step dispersion process allows better dispersion of the antiaging compound in the tire rubber compared to direct addition.

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Composite materials for tire sidewall rubber that provide good aging resistance without coloring the sidewall surface. The composition includes rubber, hydrotalcite, carbon black, treated distillate aromatic extract, antioxidants, wax, tackifying resin, zinc oxide, stearic acid, sulfur, and accelerator. The antioxidants are used in a specific range to prevent sidewall cracking without excessive migration to the surface. The hydrotalcite improves aging resistance. The composition is prepared by mixing the components in stages and milling to obtain the final tire sidewall rubber.

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Compounds with antidegradant and antifatigue efficacy for vulcanized rubber articles, lubricants, fuels, fuel additives, and coatings. The compounds are diamines with a specific structure that provide multiple benefits like inhibiting degradation, improving fatigue resistance, and preventing crack propagation. The diamines have the formula N,N'-(alkane-1,2-diyl)bis(N-phenylbenzene-1,4-diamine) where the alkane group is ethane, butane, octane, or phenylene. The compounds are used in low concentrations (0.1-5 pph) to protect rubber, plastics, lubricants, fuels, and coatings against degradation and fatigue.

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Compounds and compositions with antidegradant and antifatigue properties for improving the durability of elastomers, lubricants, fuels, and other compositions. The compounds, represented by formula I, contain a butane-2,3-diylideneazaneylylene bis(N-phenylaniline) structure. They can be used as antidegradant and antifatigue additives to prevent degradation and improve fatigue resistance in vulcanized rubber, lubricants, fuels, and other compositions after aging and service. The compounds inhibit degradation from heat, light, oxidation, ozone, and mechanical forces. They can be added in amounts of 0.1-20 parts per 100 parts of elastomer or functional ingredient.

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Anti-aging agents for rubber compounds like tire rubber that prevent deterioration due to oxidation and ozone. The new anti-aging agents have a specific chemical structure with substituents that are either hydroxyl (-OH) or a chain of 2-4 carbon atoms (-(CH2)n-) connected to a phenyl ring (-C6H5). These compounds are used in rubber mixtures to protect the polymer from oxidative degradation during aging. The unique structure allows them to be mixed with the rubber base prior to adding other ingredients and vulcanization system. This avoids degradation during compounding and provides better protection against oxidation.

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Salts of anti-degradation compounds, elastomeric compositions, tyre components, and tyres with improved performance and reduced volatility compared to traditional anti-degradation agents like 6PPD. The salts are formed by reacting the anti-degradation compound with a polyoxyalkylene acid like Akypo RLM 45CA. These salts have reduced volatility during processing and better surface appearance compared to the free anti-degradation compound. The salts are used in elastomeric compositions for tyres, especially sidewall compounds, to provide improved anti-degradation properties against oxygen and ozone. The salts can be formed by reacting the anti-degradation compound with the acid in a modified Williamson ether synthesis.

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Antidegradant and antifatigue compounds for improving the oxidative stability and fatigue resistance of vulcanized rubber articles, lubricants, fuels, and other compositions. The compounds are diimines derived from reacting a p-phenylenediamine with a dicarbonyl or diol. They can be prepared by catalyzed reduction of the diimines. The compounds have antidegradant efficacy over prolonged periods of time, especially at exposed surfaces of the composition, and improve fatigue resistance after aging and oxidation. They can be used as additives in elastomers, lubricants, fuels, etc., to prevent degradation and fatigue failure.

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Antidegradant and antifatigue compound for rubber articles, lubricants, fuels, and fuel additives that improves resistance to aging, oxidation, ozone, and mechanical fatigue. The compound is a diamine with a phenylene bis(diamine) structure. It can be added to elastomers, lubricants, fuels, and fuel additives to protect against degradation and extend useful life.

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Antidegradant compounds for elastomers, lubricants, fuels, and other compositions that provide improved antidegradant and antifatigue properties. The compounds are diamines derived from p-phenylenediamines and alpha-hydroxy carbonyls. They have structures represented by formula I. These compounds can be synthesized by reducing the enediamine intermediates obtained from reacting p-phenylenediamines with alpha-hydroxy carbonyls. The compounds can be used as additives in vulcanized rubber, lubricants, fuels, and other compositions to improve resistance to degradation and fatigue.

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Antidegradant and antifatigue compound for elastomers, lubricants, fuels, and coatings that provides improved resistance to aging, oxidation, ozone, and fatigue compared to conventional antidegradants. The compound is a bisphenylene diamine structure with specific substitution patterns. It can be used at lower concentrations than conventional antidegradants to achieve similar or better efficacy. The compound provides multiple benefits like antioxidant, antiozonant, and antifatigue properties. It can be added to elastomer compositions, lubricants, fuels, and coatings to improve durability and service life.

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Stabilizing brominated elastomers prepared by regenerative bromination to prevent excessive increase in viscosity over time. The stabilization involves adding a specific combination of hindered amine stabilizers (HAS) and acid scavengers to the bromination process. The HAS has a nitrogen with lower pKa than the acid scavenger's protonatable atom. This synergistic additive package prevents oxidative degradation and crosslinking that causes viscosity growth. It allows using regenerative bromination without excessive viscosity increase. The stabilized brominated elastomers have lower delta Mooney viscosity compared to unstabilized ones.

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Tire tread compound that reduces aging and improves performance by suppressing radical chain reactions during kneading. The compound contains specific anti-aging agents and carbon black levels to prevent radical propagation during mixing. The anti-aging agents are represented by formulas (1) or (2): - Formula (1): N-phenyl-N’-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD) derivative with a dihydroquinoline ring: - Formula (2): Thiomethylated o-cresol derivatives: The compound also has 3 parts or more of a high-surface-area carbon black (80 m2/g or more). This combination prevents radical chain reactions during kneading, reducing consumption of the anti-aging agents and preserving their lifespan. It also improves tread performance by suppressing radical

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Rubber composition for tires that provides improved ozone resistance and reduces discoloration compared to conventional tire rubber compounds. The composition contains specific rubber components, antioxidant, surfactant, and fillers. The rubber components are non-oil extended polybutadiene or oil extended polybutadiene with high cis content and viscosity. The surfactant is a nonionic compound. These along with the antioxidant and fillers allow preventing discoloration and ozone degradation without compromising elongation and fuel economy.

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