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. Tire Tread Compositions with Functionalized Polymer Additives for Enhanced Wet Traction and Rolling Resistance

EXXONMOBIL CHEMICAL PATENTS INC, 2025

Tire tread formulations with improved wet traction and rolling resistance. The tread compositions contain specific polymer additives based on butyl rubber, ethylene-propylene-diene terpolymer, poly(isobutylene-co-para-methylstyrene) polymer and poly(isobutylene-co-para-methylstyrene-co-isoprene) terpolymer. These functionalized polymers are added in small amounts to the tire rubber matrix to concentrate carbon black and antioxidant in their domains, improving abrasion resistance, cure state and UV stability. The immiscible functionalized polymers provide a robust interface between the polymer domain and the tread matrix to improve wet traction without changing the overall compound glass transition temperature.

2. 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.

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3. 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.

4. 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.

5. 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.

6. 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.

7. 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

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8. 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.

9. 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.

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10. 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.

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11. 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.

12. 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.

13. 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.

14. 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.

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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.

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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.

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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.

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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.

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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.

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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.

21. Tire Tread Structure with Diene-Based Rubber Cap and Antioxidant-Enhanced Jointless Band

SUMITOMO RUBBER INDUSTRIES, LTD., 2021

Tire that can improve wet grip performance while maintaining a good TGC resistance, even when the tire is stored as having a thin thickness of a subtread at a bottom of tread main grooves, and rim-assembled and mounted on a vehicle to be left to stand. The tire includes a tread part, a cap tread being formed of a rubber composition for a cap tread, a jointless band comprising fiber cords coated with a rubber composition for fiber cord toppings, the rubber composition for a cap tread comprises 3.0 parts by mass or more of antioxidant based on 100 parts by mass of a rubber component comprising a diene-based rubber, and wherein a subtread thickness at the bottom of tread main grooves is 0.1 to 3.0 mm.

22. p-Phenylenediamine Antidegradant with Alkyl Substituents for Low-Discoloration Rubber Compositions

Sennics Co, Ltd., 2021

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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23. Method for Producing Oxidation Resistant Natural Rubber via Antioxidant Binding During Latex Stage

Cooper Tire and Rubber Company, 2021

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.

24. Rubber Compound Incorporating Terpene-Functionalized Lignin as Antioxidant

BRIDGESTONE CORPORATION, 2021

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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25. N-Phenyl-N′-Disubstituted Phenyl-p-Phenylenediamine Compound for Rubber Antidegradation

Sennics Co., Ltd., 2020

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.

26. Rubber Composition Anti-Degradant with Novel Compound Structure for Enhanced Aging Resistance

Sennics Co., Ltd., 2020

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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27. Polymer with Styrene-Diene Repeating Units and Method of Synthesis Using Lewis Acid Catalyst

THE YOKOHAMA RUBBER CO., LTD., 2020

Polymer, method of producing it, and a rubber composition with improved resistance to oxidation degradation and toughness. The polymer contains a unique combination of repeating units: styrene units linked head-to-head or head-to-tail, and diene units with cis configuration. This structure provides oxidation resistance by eliminating certain linkages prone to oxidation. The polymer is made by reacting a diene polymer with an aromatic hydrocarbon in the presence of a Lewis acid catalyst. The resulting polymer has excellent oxidation resistance and is used in rubber compositions for tires and other applications.

28. Rubber Composition with Specific Wax Distribution for Enhanced Ozone and Discoloration Resistance

BRIDGESTONE CORPORATION, 2020

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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29. Bisimine-Derived Antidegradant and Antifatigue Compounds for Elastomers and Hydrocarbon Compositions

Eastman Chemical Company, 2020

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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30. Elastomer-Compatible Antioxidant Precursors with Reactive Functional Groups for Post-Cure Release

Firestone Industrial Products Company, LLC, 2020

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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31. Rubber Composition with Polyether, Carbon Black, and Antioxidant for Enhanced Tire Durability and Appearance

SUMITOMO RUBBER INDUSTRIES, LTD., 2020

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.

32. Tyre Sidewall with Crosslinked Elastomeric Composition Containing High Phenolic Antioxidant Concentration

Pirelli Tyre S.p.A., 2019

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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33. Composite Anti-Degradant Mixture for Rubber Compositions with Specified Compound Ratios

Sennics Co., Ltd., 2019

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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34. Rubber Compounds with Esterified Lignin-Terpene Antioxidant for Pneumatic Tires

BRIDGESTONE CORPORATION, 2019

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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35. Diamine Derivatives from Hydrogenated Bisimines for Vulcanized Rubber Antidegradation

Eastman Chemical Company, 2019

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.

36. Diamine Compound with N,N'-X-C6H4-1,4-N2 Structure for Enhanced Antidegradation and Antifatigue Properties

Eastman Chemical Company, 2019

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.

37. Composite Tire Sidewall Material with Hydrotalcite and Controlled Antioxidant Migration

Shandong Linglong Tire Co., Ltd., 2019

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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38. Rubber Compositions with Nonionic Surfactant, Silica, and Phenylenediamine Antioxidant for Discoloration Resistance

SUMITOMO RUBBER INDUSTRIES, LTD., 2019

Rubber compositions for tires that prevent discoloration and improve ozone resistance while maintaining good elongation at break. The compositions contain a specific nonionic surfactant, a silica, and a phenylenediamine antioxidant. The nonionic surfactant blooms to the tire surface with the antioxidant, flattening it to prevent white discoloration. The silica provides a surface-protecting layer that reduces brown discoloration. The compositions also contain carbon black, stearic acid, and a specific vulcanization accelerator.

39. Diamines with N,N'-(Alkane-1,2-diyl)bis(N-phenylbenzene-1,4-diamine) Structure for Vulcanized Rubber and Material Protection

Eastman Chemical Company, 2019

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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40. Rubber Composition with Modified Butadiene Polymerization Catalysts and Specific Sulfur-Silica Ratios

SUMITOMO RUBBER INDUSTRIES, LTD., 2019

Rubber composition for base treads of tires that improves steering stability, rolling resistance, and durability compared to conventional base tread compounds. The composition contains specific amounts of sulfur, silica filler, and a unique rubber component made by modifying butadiene polymerization catalysts. It also has other additives like oil, antioxidant, and mold release agent. The composition balances properties like elongation, tan delta, and extrusion processability to provide better steering stability, rolling resistance, and durability for base tread tires.

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41. Compounds with Butane-2,3-Diylideneazaneylylene Bis(N-Phenylaniline) Structure for Elastomer and Composition Durability

Eastman Chemical Company, 2019

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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42. Rubber Anti-Aging Agents with Hydroxyl or Alkyl-Substituted Phenyl Ring Structure

BRIDGESTONE CORPORATION, 2019

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.

43. Salts of Anti-Degradation Compounds via Polyoxyalkylene Acid Reaction in Elastomeric Compositions

Pirelli Tyre S.p.A., 2019

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.

44. Pneumatic Tire with Controlled Antioxidant Content in Bead Reinforcement and Adjacent Components

SUMITOMO RUBBER INDUSTRIES, LTD., 2019

Pneumatic tire design to prevent migration of antioxidant from adjacent tire components into the bead reinforcement layer. The migration of amine-based antioxidant from adjacent components like sidewalls into the bead reinforcement layer is suppressed by controlling the antioxidant content in the bead reinforcement and the adjacent components. The antioxidant content in the bead reinforcement is 0.3-8 parts per 100 parts rubber and the ratio of antioxidant content in the bead reinforcement to adjacent component is 3-8. This prevents performance deterioration in the tire bead due to antioxidant migration from adjacent components.

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45. Diimines Derived from p-Phenylenediamine and Dicarbonyl or Diol for Enhanced Oxidative Stability and Fatigue Resistance

Eastman Chemical Company, 2019

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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46. Diamine-Based Phenylene Bis(diamine) Compound for Rubber and Hydrocarbon Stability

Eastman Chemical Company, 2018

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.

47. Diamine Compounds Derived from p-Phenylenediamines and Alpha-Hydroxy Carbonyls

Eastman Chemical Company, 2018

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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48. Bisphenylene Diamine Compound with Specific Substitution Patterns for Elastomers, Lubricants, Fuels, and Coatings

Eastman Chemical Company, 2018

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.

49. Rubber Composition with Antioxidant and Methylene System Reinforcing Resin

Compagnie Generale des Etablissements Michelin, 2018

Rubber compositions with improved rigidity without compromising processability and cured cohesiveness. The compositions contain a combination of the antioxidant poly-2,2,4-trimethyl-1,2-dihydroquinoline (TMQ) and a methylene acceptor/donor system reinforcing resin. Adding both TMQ and the reinforcing resin to the rubber composition improves rigidity without significantly degrading green viscosity or cured cohesiveness.

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50. Tire Tread Compound with Anti-Aging Agents and High-Surface-Area Carbon Black for Radical Suppression

SUMITOMO RUBBER INDUSTRIES, LTD., 2018

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

51. Rubber Composition with Non-Oil or Oil Extended High Cis Polybutadiene, Nonionic Surfactant, Antioxidant, and Fillers

52. Pneumatic Tire Inner Liner with Styrene-Isobutylene-Styrene Triblock and Isobutylene-β-Pinene Copolymer Composition

53. Anti-Oxidative Rubber Stabilizing Agent for Polymer-Oxygen Reaction Inhibition

54. Rubber Composition with Styrene-Butadiene, Pluronic Surfactant, and Sulfur for Enhanced Discoloration Resistance

55. Bisimine Compounds Derived from p-Phenylenediamine and Dicarbonyls for Rubber Antidegradant and Antifatigue Properties

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