[1] CAO G D, WANG W, ZHANG J, et al. New evidence of rubber-derived quinones in water, air, and soil[J]. Environmental Science & Technology, 2022, 56(7): 4142-4150.
[2] SIEBER R, KAWECKI D, NOWACK B. Dynamic probabilistic material flow analysis of rubber release from tires into the environment[J]. Environmental Pollution, 2020, 258: 113573. doi: 10.1016/j.envpol.2019.113573
[3] 戴情园, 谭弘李, 张婧, 等. 我国对苯二胺类抗氧化剂及其衍生醌类化合物污染现状及健康风险研究进展[J]. 环境化学, 2024, 43(10): 3207-3223. doi: 10.7524/j.issn.0254-6108.2024062201 DAI Q Y, TAN H L, ZHANG J, et al. A review of contaminations and health risks of p-phenylenediamine antioxidants and their derived novel quinones[J]. Environmental Chemistry, 2024, 43(10): 3207-3223 (in Chinese). doi: 10.7524/j.issn.0254-6108.2024062201
[4] 姜锦林, 吴慧毅, 王蕾, 等. 土壤中典型橡胶防老剂及其衍生物的环境行为及陆生生态风险综述[J]. 土壤学报, 2025, 62(1): 29-39 JIANG J L, WU H Y, WANG L, et al. Environmental behavior and terrestrial ecological risks of typical rubber antioxidants and their derivatives[J]. Acta Pedologica Sinica, 2025, 62(1): 29-39 (in Chinese).
[5] TIAN Z Y, ZHAO H Q, PETER K T, et al. A ubiquitous tire rubber-derived chemical induces acute mortality in coho salmon[J]. Science, 2021, 371(6525): 185-189. doi: 10.1126/science.abd6951
[6] ZHANG H Y, HUANG Z, LIU Y H, et al. Occurrence and risks of 23 tire additives and their transformation products in an urban water system[J]. Environment International, 2023, 171: 107715. doi: 10.1016/j.envint.2022.107715
[7] CHALLIS J K, POPICK H, PRAJAPATI S, et al. Occurrences of tire rubber-derived contaminants in cold-climate urban runoff[J]. Environmental Science & Technology Letters, 2021, 8(11): 961-967.
[8] RAUERT C, CHARLTON N, OKOFFO E D, et al. Concentrations of tire additive chemicals and tire road wear particles in an Australian urban tributary[J]. Environmental Science & Technology, 2022, 56(4): 2421-2431.
[9] SEIWERT B, NIHEMAITI M, TROUSSIER M, et al. Abiotic oxidative transformation of 6-PPD and 6-PPD quinone from tires and occurrence of their products in snow from urban roads and in municipal wastewater[J]. Water Research, 2022, 212: 118122. doi: 10.1016/j.watres.2022.118122
[10] ZHANG X, PENG Z F, HOU S J, et al. Ubiquitous occurrence of p-Phenylenediamine (PPD) antioxidants and PPD-quinones in fresh atmospheric snow and their amplification effects on associated aqueous contamination[J]. Journal of Hazardous Materials, 2024, 465: 133409. doi: 10.1016/j.jhazmat.2023.133409
[11] ZHANG Y H, XU C H, ZHANG W F, et al. p-phenylenediamine antioxidants in PM2.5: The underestimated urban air pollutants[J]. Environmental Science & Technology, 2022, 56(11): 6914-6921.
[12] JOHANNESSEN C, METCALFE C D. The occurrence of tire wear compounds and their transformation products in municipal wastewater and drinking water treatment plants[J]. Environmental Monitoring and Assessment, 2022, 194(10): 731. doi: 10.1007/s10661-022-10450-9
[13] CAO G D, WANG W, ZHANG J, et al. Occurrence and fate of substituted p-phenylenediamine-derived quinones in Hong Kong wastewater treatment plants[J]. Environmental Science & Technology, 2023, 57(41): 15635-15643.
[14] LI Z M, KANNAN K. Mass loading, removal, and emission of 1, 3-diphenylguanidine, benzotriazole, benzothiazole, N-(1, 3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine, and their derivatives in a wastewater treatment plant in New York State, USA[J]. Environmental Science & Technology Water, 2024, 4(6): 2721-2730.
[15] JOHANNESSEN C, SAINI A, ZHANG X M, et al. Air monitoring of tire-derived chemicals in global megacities using passive samplers[J]. Environmental Pollution, 2022, 314: 120206. doi: 10.1016/j.envpol.2022.120206
[16] OLUBUSOYE B S, CIZDZIEL J V, BEE M, et al. Toxic tire wear compounds (6PPD-Q and 4-ADPA) detected in airborne particulate matter along a highway in Mississippi, USA[J]. Bulletin of Environmental Contamination and Toxicology, 2023, 111(6): 68. doi: 10.1007/s00128-023-03820-7
[17] ZHANG Y Y, YAN L, WANG L X, et al. A nation-wide study for the occurrence of PPD antioxidants and 6PPD-quinone in road dusts of China[J]. Science of the Total Environment, 2024, 922: 171393. doi: 10.1016/j.scitotenv.2024.171393
[18] HUANG W, SHI Y M, HUANG J L, et al. Occurrence of substituted p-phenylenediamine antioxidants in dusts[J]. Environmental Science & Technology Letters, 2021, 8(5): 381-385.
[19] ZHANG Y J, XU T T, YE D M, et al. Widespread N-(1, 3-dimethylbutyl)-N’-phenyl-p-phenylenediamine quinone in size-fractioned atmospheric particles and dust of different indoor environments[J]. Environmental Science & Technology Letters, 2022, 9(5): 420-425.
[20] KLÖCKNER P, SEIWERT B, WEYRAUCH S, et al. Comprehensive characterization of tire and road wear particles in highway tunnel road dust by use of size and density fractionation[J]. Chemosphere, 2021, 279: 130530. doi: 10.1016/j.chemosphere.2021.130530
[21] ZHANG Z X, DAI C X, CHEN S Y, et al. Spatiotemporal variation of 6PPD and 6PPDQ in dust and soil from e-waste recycling areas[J]. Science of the Total Environment, 2024, 923: 171495. doi: 10.1016/j.scitotenv.2024.171495
[22] XU Q, LI G, FANG L, et al. Enhanced formation of 6PPD-Q during the aging of tire wear particles in anaerobic flooded soils: The role of iron reduction and environmentally persistent free radicals[J]. Environmental Science & Technology, 2023, 57(14): 5978-5987.
[23] PAROLINI M, BINELLI A, MATOZZO V, et al. Persistent organic pollutants in sediments from the lagoon of Venice—a possible hazard for sediment-dwelling organisms[J]. Journal of Soils and Sediments, 2010, 10(7): 1362-1379. doi: 10.1007/s11368-010-0277-4
[24] ZENG L X, LI Y, SUN Y X, et al. Widespread occurrence and transport of p-phenylenediamines and their quinones in sediments across urban rivers, estuaries, coasts, and deep-sea regions[J]. Environmental Science & Technology, 2023, 57(6): 2393-2403.
[25] ZHU J Q, GUO R Y, REN F F, et al. Occurrence and partitioning of p-phenylenediamine antioxidants and their quinone derivatives in water and sediment[J]. Science of the Total Environment, 2024, 914: 170046. doi: 10.1016/j.scitotenv.2024.170046
[26] TIAN Z Y, GONZALEZ M, RIDEOUT C A, et al. 6PPD-quinone: Revised toxicity assessment and quantification with a commercial standard[J]. Environmental Science & Technology Letters, 2022, 9(2): 140-146.
[27] LO B P, MARLATT V L, LIAO X J, et al. Acute toxicity of 6PPD-Quinone to early life stage juvenile Chinook (Oncorhynchus tshawytscha) and coho (Oncorhynchus kisutch) salmon[J]. Environmental Toxicology and Chemistry, 2023, 42(4): 815-822. doi: 10.1002/etc.5568
[28] BRINKMANN M, MONTGOMERY D, SELINGER S, et al. Acute toxicity of the tire rubber-derived chemical 6PPD-quinone to four fishes of commercial, cultural, and ecological importance[J]. Environmental Science & Technology Letters, 2022, 9(4): 333-338.
[29] FRENCH B F, BALDWIN D H, CAMERON J, et al. Urban roadway runoff is lethal to juvenile coho, steelhead, and Chinook salmonids, but not congeneric sockeye[J]. Environmental Science & Technology Letters, 2022, 9(9): 733-738.
[30] HIKI K, YAMAMOTO H. The tire-derived chemical 6PPD-quinone is lethally toxic to the white-spotted char salvelinus leucomaenis pluvius but not to two other salmonid species[J]. Environmental Science & Technology Letters, 2022, 9: 1050-1055.
[31] FOLDVIK A, KRYUCHKOV F, SANDODDEN R, et al. Acute toxicity testing of the tire rubber-derived chemical 6PPD-quinone on Atlantic salmon (Salmo salar) and brown trout (Salmo trutta)[J]. Environmental Toxicology and Chemistry, 2022, 41(12): 3041-3045. doi: 10.1002/etc.5487
[32] HIKI K, ASAHINA K, KATO K, et al. Acute toxicity of a tire rubber-derived chemical, 6PPD quinone, to freshwater fish and crustacean species[J]. Environmental Science & Technology Letters, 2021, 8(9): 779-784.
[33] McINTYRE J K, SPROMBERG J, CAMERON J, et al. Bioretention filtration prevents acute mortality and reduces chronic toxicity for early life stage coho salmon (Oncorhynchus kisutch) episodically exposed to urban stormwater runoff[J]. Science of the Total Environment, 2023, 902: 165759. doi: 10.1016/j.scitotenv.2023.165759
[34] HIKI K, YAMAMOTO H. Concentration and leachability of N-(1, 3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) and its quinone transformation product (6PPD-Q) in road dust collected in Tokyo, Japan[J]. Environmental Pollution (Barking, Essex, 2022, 302: 119082. doi: 10.1016/j.envpol.2022.119082
[35] MAHONEY H, Da SILVA JUNIOR F C, ROBERTS C, et al. Exposure to the tire rubber-derived contaminant 6PPD-quinone causes mitochondrial dysfunction in vitro[J]. Environmental Science & Technology Letters, 2022, 9(9): 765-771.
[36] MONTGOMERY D, JI X W, CANTIN J, et al. Interspecies differences in 6PPD-quinone toxicity across seven fish species: Metabolite identification and semiquantification[J]. Environmental Science & Technology, 2023, 57(50): 21071-21079.
[37] HUA X, FENG X, LIANG G Y, et al. Long-term exposure to tire-derived 6-PPD quinone causes intestinal toxicity by affecting functional state of intestinal barrier in Caenorhabditis elegans[J]. Science of the Total Environment, 2023, 861: 160591. doi: 10.1016/j.scitotenv.2022.160591
[38] HUA X, FENG X, LIANG G Y, et al. Long-term exposure to 6-PPD quinone reduces reproductive capacity by enhancing germline apoptosis associated with activation of both DNA damage and cell corpse engulfment in Caenorhabditis elegans[J]. Journal of Hazardous Materials, 2023, 454: 131495. doi: 10.1016/j.jhazmat.2023.131495
[39] HUA X, FENG X, LIANG G Y, et al. Exposure to 6-PPD quinone at environmentally relevant concentrations causes abnormal locomotion behaviors and neurodegeneration in Caenorhabditis elegans[J]. Environmental Science & Technology, 2023, 57(12): 4940-4950.
[40] WANG Y X, HUA X, WANG D Y. Exposure to 6-PPD quinone enhances lipid accumulation through activating metabolic sensors of SBP-1 and MDT-15 in Caenorhabditis elegans[J]. Environmental Pollution, 2023, 333: 121937. doi: 10.1016/j.envpol.2023.121937
[41] FANG L Y, FANG C L, DI S S, et al. Oral exposure to tire rubber-derived contaminant 6PPD and 6PPD-quinone induce hepatotoxicity in mice[J]. Science of the Total Environment, 2023, 869: 161836. doi: 10.1016/j.scitotenv.2023.161836
[42] ZHAO H N, THOMAS S P, ZYLKA M J, et al. Urine excretion, organ distribution, and placental transfer of 6PPD and 6PPD-quinone in mice and potential developmental toxicity through nuclear receptor pathways[J]. Environmental Science & Technology, 2023, 57(36): 13429-13438.
[43] ZHANG J, CAO G D, WANG W, et al. Stable isotope-assisted mass spectrometry reveals in vivo distribution, metabolism, and excretion of tire rubber-derived 6PPD-quinone in mice[J]. Science of the Total Environment, 2024, 912: 169291. doi: 10.1016/j.scitotenv.2023.169291
[44] YANG Y, SUN N, LV J, et al. Environmentally realistic dose of tire-derived metabolite 6PPD-Q exposure causes intestinal jejunum and ileum damage in mice via cannabinoid receptor-activated inflammation[J]. Science of the Total Environment, 2024, 918: 170679. doi: 10.1016/j.scitotenv.2024.170679
[45] YAO K Z, KANG Q M, LIU W B, et al. Chronic exposure to tire rubber-derived contaminant 6PPD-quinone impairs sperm quality and induces the damage of reproductive capacity in male mice[J]. Journal of Hazardous Materials, 2024, 470: 134165. doi: 10.1016/j.jhazmat.2024.134165
[46] DU B B, LIANG B W, LI Y, et al. First report on the occurrence of N-(1, 3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and 6PPD-quinone as pervasive pollutants in human urine from South China[J]. Environmental Science & Technology Letters, 2022, 9(12): 1056-1062.
[47] SONG S M, GAO Y X, FENG S, et al. Widespread occurrence of two typical N, N’-substituted p-phenylenediamines and their quinones in humans: Association with oxidative stress and liver damage[J]. Journal of Hazardous Materials, 2024, 468: 133835. doi: 10.1016/j.jhazmat.2024.133835
[48] LIU C Y, ZHAO X C, GUO L Q, et al. Emerging N-(1, 3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) and 6PPD quinone in paired human plasma and urine from Tianjin, China: Preliminary assessment with demographic factors[J]. Journal of Hazardous Materials, 2024, 476: 134818. doi: 10.1016/j.jhazmat.2024.134818
[49] FANG J C, WANG X X, CAO G D, et al. 6PPD-quinone exposure induces neuronal mitochondrial dysfunction to exacerbate Lewy neurites formation induced by α-synuclein preformed fibrils seeding[J]. Journal of Hazardous Materials, 2024, 465: 133312. doi: 10.1016/j.jhazmat.2023.133312
[50] LIANG B W, GE J L, DENG Q, et al. Occurrence of multiple classes of emerging synthetic antioxidants, including p-phenylenediamines, diphenylamines, naphthylamines, macromolecular hindered phenols, and organophosphites, in human milk: Implications for infant exposure[J]. Environmental Science & Technology Letters, 2024, 11(3): 259-265.
[51] WANG W, CAO G D, ZHANG J, et al. Beyond substituted p-phenylenediamine antioxidants: Prevalence of their quinone derivatives in PM2.5[J]. Environmental Science & Technology, 2022, 56(15): 10629-10637.
[52] ZHANG R L, ZHAO S Z, LIU X, et al. Aquatic environmental fates and risks of benzotriazoles, benzothiazoles, and p-phenylenediamines in a catchment providing water to a megacity of China[J]. Environmental Research, 2023, 216: 114721. doi: 10.1016/j.envres.2022.114721
[53] WEI L N, WU N N, XU R, et al. First evidence of the bioaccumulation and trophic transfer of tire additives and their transformation products in an estuarine food web[J]. Environmental Science & Technology, 2024, 58(14): 6370-6380.
[54] U. S. Tire manufactures. Largest global tire industry consortium releases preliminary 6ppd alternatives analysis report. March 29, 2024.
[55] ZEYNALOV E, W AGNER M, FRIEDRICH J, et al. Antioxidant traits of some nanocarbon moieties integrated in polymer materials (a review)[J]. Chemistry & Chemical Technology, 2016, 10(4s): 581-586.
[56] 娄昀璟, 李雪花, 陈景文. 氧分子在碳纳米颗粒表面吸附的密度泛函理论研究[J]. 环境化学, 2015, 34(9): 1587-1593. doi: 10.7524/j.issn.0254-6108.2015.09.2015042201 LOU Y J, LI X H, CHEN J W. Oxygen adsorption on carbon nanoparticles: A density functional theory study[J]. Environmental Chemistry, 2015, 34(9): 1587-1593 (in Chinese). doi: 10.7524/j.issn.0254-6108.2015.09.2015042201
[57] ZHAO L L, ZHANG M, MUJUMDAR A S, et al. Application of carbon dots in food preservation: A critical review for packaging enhancers and food preservatives[J]. Critical Reviews in Food Science and Nutrition, 2023, 63(24): 6738-6756. doi: 10.1080/10408398.2022.2039896
[58] WU S W, WENG P J, TANG Z H, et al. Sustainable carbon nanodots with tunable radical scavenging activity for elastomers[J]. ACS Sustainable Chemistry & Engineering, 2016, 4(1): 247-254.