Protecting Tires with Anti-Degradants during Manufacturing
129 patents in this list
Updated:
Tire rubber compounds face continuous oxidative stress and ozone exposure during both manufacturing and service life. Without protection, these compounds experience chain scission and crosslinking reactions that lead to premature aging, with laboratory tests showing up to 40% loss in mechanical properties after accelerated aging at 70°C for 168 hours. Current manufacturing processes must balance protecting the rubber matrix while maintaining critical performance properties.
The fundamental challenge lies in incorporating anti-degradants that provide comprehensive protection against multiple degradation mechanisms while preventing unwanted side effects like blooming, discoloration, and environmental leaching.
This page brings together solutions from recent research—including new p-phenylenediamine derivatives with improved solubility, quinoline-based antioxidant systems, and specialized diamine compounds that resist migration. These and other approaches focus on achieving long-term protection while meeting increasingly strict requirements for environmental impact and tire appearance.
1. Process for Producing Vulcanizable Composite Materials Using Ethylene-Propylene-Diene or Butyl Rubbers with Specific Aging Stabilizers
Continental Reifen Deutschland GmbH, 2024
A process to produce vulcanizable composite materials for vehicle tires with improved aging resistance while maintaining optical transparency. The process involves using specific rubbers and aging stabilizers in the rubber mixture. The rubbers are ethylene-propylene-diene rubbers or butyl rubbers, and the aging stabilizers are p-phenylenediamines, dihydroquinolines, phenylnaphthylamines, substituted phenols, and substituted bisphenols. The composite material can be used to make tires with partially transparent rubber sections. The transparent rubberization has better aging resistance compared to conventional transparent rubber compounds.
2. Compound with Formula I for Rubber Aging Stabilization and Antiozonant Properties
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.
3. 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.
4. Rubber Composition with High Purity 6PPD and S-TMQ Quinoline Antidegradant Combination
Sennics Co., Ltd., 2024
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.
5. Rubber Compound Antidegradant Composition with TMPPD and Select Phenylenediamines
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
6. N-Phenyl-N′-Disubstituted Phenyl-p-Phenylenediamine Compound for Rubber with Methyl Substituents
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.
7. P-Phenylenediamine Compounds with Alkyl and Cycloalkyl Substituents Synthesized from Aniline and Nitrobenzene Derivatives
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.
8. p-Phenylenediamine Antidegradants with Branched Alkyl Substituents Synthesized via One-Pot Condensation and Reduction
Sennics Co., Ltd., 2024
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.
9. Rubber Composition with Specific Diamine and Quinoline Antioxidant for Ozone-Resistant, Non-Discoloring Tires
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.
10. Rubber Composition with Alternative Antiozonant Compounds sPPD-OH and sPAQI
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.
11. Rubber Composition with Diene Rubber, Silica Filler, and Specific Antioxidant and Vulcanization Additives
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.
12. Pneumatic Tire Sidewall Support with Elastomeric Eutectic Composition
Bridgestone Corporation, 2024
Preparing sidewall supports for pneumatic tires that demonstrate improved properties, including increased resistance to degradation while being operated at elevated temperatures for extended periods of time. The support includes an elastomer, a filler, a curative, and a eutectic composition.
13. 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
14. Phenothiazine Derivative with Branched Alkyl Amino Group for Aging Stabilization in Rubber Mixtures
Continental Reifen Deutschland GmbH, 2024
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.
15. Rubber Composition with Enhanced Heat Aging Resistance Containing Filler, Vulcanizing Agent, and Antiaging Additives
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.
16. Tire with Crosslinked Elastomeric Sidewalls Containing High-Loading Phenolic Antioxidant
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.
17. Rubber Compound with Formula (I) Structure Incorporating R, R1, and 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.
18. 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.
19. Sulfur-Crosslinked Rubber Mixture with Additives for Enhanced Aging and Cracking Resistance
Continental Reifen Deutschland GmbH, 2022
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.
20. Rubber Composition Incorporating Diene-Based Polymer, Alkylated Hydroquinone, and Amine Anti-Aging Agent
BRIDGESTONE CORPORATION, 2022
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.
Request the full report with complete details of these
+109 patents for offline reading.