The Effect of the Structure of <i>p</i>-Phenylenediamine Antiagers on the Physicomechanical and Hysteresis Properties of Filled Rubber Compounds

Poldushova, G.A.; Kandyrin, K. L.; Резниченко, С. В.

doi:10.1177/0307174x1604300205

Cited by 8 publications

(3 citation statements)

References 4 publications

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“…N , N ′-Substituted p -phenylenediamines (PPDs) are manufactured and widely used as antioxidants and antiozonants in the industry for production of tires, belts, hoses, and cables. − The chemicals provide superior capacity for protection of rubber and its products against heat degradation, breaking down, and ozone cracking. ,, However, the vast number of rubber products have resulted in an incredible release of PPDs and related degradation products into the environment. Various PPDs, as indicated in Table , such as N -(1,3-dimethylbutyl)- N ′-phenyl- p -phenylenediamine (6PPD), N , N ′-bis(1,4-dimethylpentyl)- p -phenylenediamine, N -phenyl- N ′-cyclohexyl- p -phenylenediamine (CPPD), N -isopropyl- N ′-phenyl-1,4-phenylenediamine (IPPD), N , N ′-di( o -tolyl)- p -phenylenediamine (DTPD), and N , N ′-diphenyl- p -phenylenediamine (DPPD), have been detected in different environmental matrices, including airborne particles, water, and sediments, − which has yielded grave concerns regarding their potential threats to the environment and human health.…”

Section: Introductionmentioning

confidence: 99%

New Evidence of Rubber-Derived Quinones in Water, Air, and Soil

Cao

Wang

Zhang

et al. 2022

Environ. Sci. Technol.

210

164

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p-Phenylenediamines (PPDs) have been extensively used in the rubber industry and found to be pervasive in various environmental compartments for decades, while their transformation products and associated ecological and human health risks remain largely unknown. Herein, we developed and implemented a mass spectrometrybased platform combined with self-synthesized standards for the investigation of rubber-derived quinones formed from PPD antioxidants. Our results demonstrated that five quinones are ubiquitously present in urban runoff, roadside soils, and air particles. All of the identified sources are closely related to mankind's activities. Among the identified quinones, N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine quinone has been recently found to be highly toxic, causing acute mortality of coho salmon in the Pacific Northwest. Ultrahigh-performance liquid chromatography coupled with triple quadrupole mass spectrometry was then applied for quantification of the five quinones and their corresponding PPD antioxidants. The results revealed interesting distinct distribution and concentration patterns of PPD-derived quinones in different environmental matrices. Daily intake rates of these quinones in a compact city of Hong Kong were estimated to be varied from 1.08 ng/(kg•day) for adults to 7.30 ng/(kg•day) for children, which were higher than the exposure levels of their parent compounds. Considering the prevalence of the use of rubber products, the outcome of this study strongly suggests for additional toxicological studies to investigate potential ecological and human health risks of the newly discovered quinones.

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Section: Introductionmentioning

confidence: 99%

New Evidence of Rubber-Derived Quinones in Water, Air, and Soil

Cao

Wang

Zhang

et al. 2022

Environ. Sci. Technol.

210

164

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“…p-Phenylenediamines derivatives (PPDs) have been widely added to many rubberrelated industrial and consumer products, such as rubber tires, gloves, cables, and belts [1][2][3]. These chemicals are effective in preventing the oxidative cracking, thermal degradation, and the aging of rubber-related products [4,5].…”

Section: Introductionmentioning

confidence: 99%

p-Phenylenediamine Derivatives in Tap Water: Implications for Human Exposure

Zhu,

Guo,

Ren

et al. 2024

Water

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Human exposure to p-phenylenediamine derivatives (PPDs) may induce hepatotoxicity and altered glycolipid metabolism. Recent studies have demonstrated the wide presence of PPDs in environmental matrixes. However, until now, the occurrence of PPDs in tap water has not been well known. This study analyzed nine PPDs in tap water collected from Hangzhou and Taizhou, China. The results showed that seven PPDs were detected in tap water samples from Hangzhou (n = 131), with the concentration of total detected PPDs ranging from 0.29 to 7.9 ng/L (mean: 1.6 ng/L). N-(1, 3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD; mean: 0.79 ng/L, <LOD−5.7 ng/L) was the predominant PPD in tap water from Hangzhou, followed by N, N′-di-2-butyl-p-phenylenediamine (44PD; 0.39 ng/L, <LOD−2.2 ng/L) and N-isopropyl-N′-phenyl-1, 4-phenylenediamine (IPPD; 0.31 ng/L, <LOD−1.4 ng/L). Five PPDs were detected in tap water collected from Taizhou (n = 30). N-phenyl-N′-cyclohexyl-p-phenylenediamine (CPPD; mean: 1.0 ng/L, <LOD−4.2 ng/L) was the predominant PPD in tap water from Taizhou, followed by 6PPD (0.93 ng/L, <LOD−2.6 ng/L) and 44PD (0.78 ng/L, <LOD−1.8 ng/L). The mean daily intake (DI) of PPDs for adults and children in Hangzhou was estimated to be 4.9–24 and 6.4–32 pg/kg bw/day, respectively. Meanwhile, the mean DI of PPDs for adults and children living in Taizhou was 11–31 and 14–40 pg/kg bw/day, respectively. To our knowledge, this study provides the first data on the occurrence of PPDs in tap water, which is vital for human exposure risk assessment.

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“…N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) is used ubiquitously as an antioxidant amendment for tires. − Recently, an ozonation byproduct of 6PPD, namely, 6PPD-quinone (6PPD-Q), was determined as the toxicant responsible for “urban stream syndrome,” i.e., the rapid mortality of adult coho salmon caused by urban stormwater. , Up to date, the lethal concentration (LC 50 ) of 6PPD-Q was determined for a range of species (coho salmon, zebrafish larvae, brook trout, rainbow trout, white sturgeon, water flea, scud, and Salvelinus leucomaenis pluvis), ranging from 0.095 μg/L (updated using HPC standard versus originally reported 0.95 μg/L) for coho salmon to up to 308.67 μg/L for zebrafish larvae. The acute toxicity and ubiquitous occurrence of 6PPD-Q have triggered a lot of concerns from the academic community and administrator entities regarding its impact on the ecosystem and human health. − …”

Section: Introductionmentioning

confidence: 99%

Investigation of 6PPD-Quinone in Rubberized Asphalt Concrete Mixtures

Lokesh,

Arunthavabalan,

Hajj

et al. 2023

ACS Environ. Au

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N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD)-quinone (6PPD-Q), a transformation byproduct of 6PPD used in tires as an antiozonant and antioxidant, was recently discovered as the chemical primarily responsible for the acute lethal toxicity of urban storm runoff to coho salmon. The asphalt concrete (AC) surface layer is the primary medium to contact 6PPD-Q immediately upon its release from tires, and the addition of recycled tire rubber (RTR) to the asphalt binder and mixture is a widely accepted practice in asphalt production. Therefore, it is urgent to understand the fate of 6PPD-Q at the asphalt concrete surface layer–water interface. This study analyzed the sorption and desorption of 6PPD-Q by compacted and crushed loose (loose particles, ∼5 mm) rubberized asphalt mixtures and their mobilization from compacted asphalt mixtures during simulated rainfall events. It should be noted that the crushed loose asphalt mixtures demonstrated the physicochemical properties of the asphalt materials, while the compacted asphalt mixtures represent in-service AC layers. Sorption of 6PPD-Q by crushed loose and compacted asphalt mixtures reached equilibrium within 12 days, with a sorption coefficient of 151.57–257.51 L/kg for compacted asphalt mixtures. Within 12 days, desorption of 6PPD-Q from crushed loose and compacted rubberized asphalt mixtures (20 g particles/L) to the double deionized (DDI) water and synthetic stormwater was 0.01–0.09 and 0.025–0.05 μg/L, respectively. Through the rainfall simulation experiments, 0.0015–0.0049 μg/L 6PPD-Q was detected in the runoff water, much lower than the lethal concentration (LC50) of 6PPD-Q of 0.095 μg/L and 308.67 μg/L for coho salmon and zebrafish larvae. Our results indicate that, while the release of 6PPD-Q from compacted rubberized asphalt mixtures is minor, the mixtures can serve as sorbents for tire-derived 6PPD-Q and retain this emerging contaminant.

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The Effect of the Structure of p-Phenylenediamine Antiagers on the Physicomechanical and Hysteresis Properties of Filled Rubber Compounds

Cited by 8 publications

References 4 publications

New Evidence of Rubber-Derived Quinones in Water, Air, and Soil

New Evidence of Rubber-Derived Quinones in Water, Air, and Soil

p-Phenylenediamine Derivatives in Tap Water: Implications for Human Exposure

Investigation of 6PPD-Quinone in Rubberized Asphalt Concrete Mixtures

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