Antioxidants in Tires Improving Longevity and Performance
139 patents in this list
Updated:
Modern passenger vehicle tires undergo continuous oxidative stress, with surface temperatures regularly reaching 50-85°C during normal operation and exposure to ozone concentrations of 20-100 ppb in urban environments. Without proper stabilization, these conditions accelerate polymer chain degradation, reducing tire life by up to 60% and compromising critical performance properties like wet grip and rolling resistance.
The challenge lies in developing antioxidant systems that provide long-term protection against multiple degradation mechanisms while maintaining the delicate balance of mechanical properties that determine tire performance.
This page brings together solutions from recent research—including water-responsive dynamic modulus adjustments, novel phenylenediamine derivatives, phenolic antioxidant systems for ozone protection, and biodegradable elastomeric matrices. These and other approaches focus on extending tire longevity while preserving essential performance characteristics across varying environmental conditions.
1. Rubber Composition for Tires with Water-Responsive Dynamic Modulus Adjustment
Sumitomo Rubber Industries, Ltd., 2024
Rubber composition for tires with improved wet grip performance and dry grip performance. The composition has a dynamic modulus that reversibly changes with water. The dynamic modulus E* satisfies the relationship E* (wet) > E* (dry) when the rubber is wet versus dry. This prevents the road contact area from reducing when transitioning from dry to wet conditions, maintaining grip. The composition contains specific polymers, silane coupling agents, carbon black, oil, resin, wax, antioxidant, zinc oxide, and sulfur.
2. 7-((4-Methylpentan-2-yl)amino)-1,3,4,10-Tetrahydroacridin-9(2H)-one Compound and Synthesis Method
Continental Reifen Deutschland GmbH, 2024
A compound called 7-((4-methylpentan-2-yl)amino)-1,3,4,10-tetrahydroacridin-9(2H)-one (CAS 1436725-55-3) that can be used as an aging stabilizer in rubber compounds like vehicle tires. The compound has a formula of I: C12H22N2O. It provides improved aging resistance compared to traditional aging stabilizers like amines. The compound can be synthesized from starting materials like 1-bromo-4-methylpentane and 2-chloroacridinone. The compound can also be produced by reacting 2-chloroacridinone with a secondary amine like N,N-dimethylbutylamine.
3. Rubber Stabilizing Compound with Formula I and Reduced Blooming Characteristics
Continental Reifen Deutschland GmbH, 2024
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.
4. Tire Rubber Composition with Void-Introducing Agent and Amine-Based Antioxidant
BRIDGESTONE CORPORATION, 2024
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.
5. Tire Tread Compound Incorporating Propylene-Ethylene-Diene Terpolymers with Styrene-Butadiene and Polybutadiene Rubbers
ExxonMobil Engineering & Technology Company, 2024
Tire tread compound with propylene-ethylene-diene terpolymers to improve wet traction and rolling resistance balance. The composition contains a styrene-butadiene rubber (SBR), polybutadiene (BR), processing oil, filler, curative, antioxidant, and a specific amount of propylene-ethylene-diene terpolymer. The terpolymer balances wet traction and rolling resistance by selectively modifying the elastomer properties. It increases hysteresis in wet traction at 0°C and lowers hysteresis in rolling resistance at 60°C without changing overall compound glass transition temperature.
6. Antidegradant Composition with Specific Phenylenediamine Combinations for Rubber Compounds
Sennics Co., Ltd., 2024
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
7. N-Phenyl-N′-Dimethylphenyl-p-Phenylenediamine Antidegradant for Rubber
Sennics Co., Ltd., 2024
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.
8. Tyre Sidewall Composition with Phenolic Antioxidant-Based Ozone Protection System
PIRELLI TYRE S.p.A., 2024
Tyre sidewall with improved resistance to ozone cracking and color fading without using waxes or other polymeric static protective agents. The tyre sidewall composition contains a protective system against ozone that consists of a phenolic antioxidant in an amount of at least 3 phr. This provides static and dynamic ozone protection without the coloration issues caused by migrating antioxidants or blooming waxes. The high phenolic antioxidant level prevents ozone cracking and discoloration in the sidewall, even when decorated, without requiring waxes or other static protectants.
9. P-Phenylenediamine Compounds with Alkyl, Cycloalkyl, or Branched Alkyl Substituents Synthesized via Condensation and Reduction Reactions
Sennics Co.,Ltd., 2024
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.
10. Biodegradable Non-Pneumatic Tire with Elastomeric Matrix and Shape Memory Alloy Scaffold
Samuel H. Creelan, Duke E. Garschina, Nathan W. Khuu, 2024
Biodegradable tire with an elastomeric matrix and a shape memory alloy (SMA) scaffold that enables a non-pneumatic, airless tire design. The elastomeric matrix is made from biodegradable materials like flax seed, guayule rubber, metal oxide, carbon filler, antioxidant, and antizoonant. The SMA scaffold provides structure and shape memory. The biodegradable composition and non-pneumatic design aim for more sustainable and environmentally friendly tires.
11. Rubber Composition with Diamine Compound and Quinoline-Based Antioxidant for Ozone Resistance
Toyo Tire Corporation, 2024
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.
12. Rubber Composition with Hydroxylated Phenyl-p-Phenylenediamine and Quinoneimine Antiozonants
Compagnie Generale des Etablissements Michelin, 2024
Rubber composition that reduces or eliminates the quantity required of 6PPD to protect rubber products, including tires. The composition includes a highly unsaturated diene elastomer, a reinforcing filler, and an antiozonant of a hydroxylated form of substituted phenyl-p-phenylenediamine sPPD-OH or a quinoneimine form of the substituted p-(hydroxy)phenylamine sPAQI.
13. Rubber Composition with Diene Rubber, Silica, Phenylenediamine, Quinoline Antioxidant, and N-Cyclohexyl-2-Benzothiazolylsulfenamide
Toyo Tire Corporation, 2024
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.
14. Compounds with Multiple Organic Thiosulfate Groups Represented by S,S′,S″-((1,3,5-Triazinane-1,3,5-Triyl)tris(R1-1,1-Diyl)) Tris(Sulfurothioate)
Flexsys America L.P., 2024
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
15. Inner Liner Coating Method with Silyl-Terminated Polymer Composition for Enhanced Component Adhesion in Tires
Bridgestone Americas Tire Operations, LLC, 2023
A method to improve adhesion of components like noise barriers inside tires by coating the inner liner surface before installing components. The coating is applied to the lower, radially inward-facing surface of the cured inner liner. It is made from a composition containing a silyl-terminated polymer, tackifier, adhesion promoter, catalyst, antioxidant, etc. The coated inner liner surface provides a better adhesive interface for components compared to the original uncoated rubber.
16. Rubber Composition with Specific Additives for Enhanced Heat Aging Resistance
Toyo Tire Corporation, 2023
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.
17. Tire Sidewall Comprising Crosslinked Elastomeric Composition with High Phenolic Antioxidant Loading
PIRELLI TYRE S.p.A., 2022
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.
18. Rubber Compound with Formula (I) Structure Incorporating R, R1, R2 Substituents for Enhanced Anti-Aging and Discoloration Resistance
Sennics Co., Ltd., 2022
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.
19. Pneumatic Tire with Controlled Antioxidant Distribution in Bead Reinforcing Layer
Sumitomo Rubber Industries, Ltd., 2022
Pneumatic tire design to prevent migration of antioxidant from adjacent tire components into the bead reinforcing layer. This prevents performance degradation in the bead area caused by excessive antioxidant levels. The solution involves controlling the antioxidant content in the bead reinforcing layer and adjacent members relative to the rubber component. The antioxidant level in the bead layer should be 0.3-8 parts per 100 parts rubber, and the ratio of antioxidant levels between the bead layer and adjacent members should be 3-8. This suppresses migration of antioxidant from the adjacent members with high antioxidant content into the bead layer.
20. Rubber Antidegradant Composition with TMPPD, N3100-B, and N3100-C for Direct Use or Masterbatch Formulation
Sennics Co., Ltd., 2022
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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