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Rubber anti-aging agent 6PPD and its ozonation product 6-PPDQ: Environmental distribution and biological toxicity |
LI Jia-yao, SHEN Hui-min, XU Ting-ting, GUO Ying |
Guangdong Key Laboratory of Environmental Pollution and Health, School of Environment, Jinan University, Guangzhou 510632, China |
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Abstract In the present review, we discussed the environmental distribution of 6PPD-quinone (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine quinone) and its precursor 6PPD (N-(1,3-Dimethyl-butyl)-N'-phenyl-p-phenylenediamine) in the air, aquatic environment, and soil, and summarized their cytotoxicity and biota toxicity, as well as potential effect on human health. The present knowledge indicated that 6PPD and 6PPD-Q are mainly from the rubber tire wear particles. They are transported with particles in air, water and soil. 6PPD and 6PPD-Q may inhibit cell proliferation, cause acute death of several fish species, and induce developmental toxicity, and may induce allergic dermatitis for humans. The future researches should pay more attention on the joint toxicity of 6PPD and 6PPD-Q with other rubber tire additives, and the related ecological risk assessment.
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Received: 24 June 2022
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[1] |
简颖涛,邹利林,张洲.我国橡胶行业挥发性有机物排放情况[C]//中国环境科学学会2021年科学技术年会——环境工程技术创新与应用分会场论文集(三), 2021:340-345. Jian Y T, Zhou L L, Zhang Z. Emisson of volatile organic compounds from rubber industry in China[C]//Science and Technology Annual Conference of China Environmental Science-Society of Environmental Sciences-Proceedings of Environmental Engineering Technology Innovation and Application, 2021:340-345.
|
[2] |
范丽雄.橡胶的老化现象及其老化机理[J]. 化工设计通讯, 2018, 44(8):54-66. Fan L X. Study on rubber aging and its mechanism[J]. Chemical Engineering Design Communications, 2018,44(8):54-66.
|
[3] |
季振青,郭睿,王永昌,等.橡胶用抗氧剂及抗臭氧剂的发展趋势[J]. 合成橡胶工业, 2010,33(1):77-80. Ji Z Q, Guo R, Wang Y C, et al. Developing trends of antioxidant and antiozonant used in rubber[J]. China Synthetic Rubber Industry, 2010,33(1):77-80.
|
[4] |
Ahmed F S, Shafy M, Abd El-Megeed A A, et al. The effect of γ-irradiation on acrylonitrile-butadiene rubber NBR seal materials with different antioxidants[J]. Materials & Design (1980-2015), 2012,36:823-828.
|
[5] |
Olejnik A, Smejda-Krzewicka A, Strzelec K. Effect of antioxidants on aging of the chloroprene rubber/butadiene rubber (CR/BR) blends[J]. International Journal of Polymer Analysis and Characterization, 2019,24(6):475-486.
|
[6] |
何伟.对苯二胺类防老剂前景广阔[J]. 中国石油和化工, 2006,(3):40-42. He W. Promising future for p-phenylenediamine based antioxidants[J]. China Petroleum and Chemical Industry, 2006,(3):40-42.
|
[7] |
防老剂4020[J]. 老化通讯, 1975,(1):49. Antioxidants 4020[J]. Synthetic Materials Aging and Application, 1975,(1):49.
|
[8] |
Tian Z, Zhao H, Peter K T, et al. A ubiquitous tire rubber-derived chemical induces acute mortality in coho salmon[J]. Science, 2021,371(6525):185-189.
|
[9] |
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.
|
[10] |
Zhang Y, Xu C, Zhang W, et al. p-Phenylenediamine antioxidants in PM2.5:The underestimated urban air pollutants[J]. Environmental Science & Technology, 2022,56(11):6914-6921.
|
[11] |
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.
|
[12] |
Johannessen C, Helm P, Lashuk B, et al. The tire wear compounds 6PPD-Quinone and 1,3-Diphenylguanidine in an urban watershed[J]. Archives of Environmental Contamination and Toxicology, 2022, 82(2):171-179.
|
[13] |
Cao G, 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.
|
[14] |
刘丽园.两种胺类防老剂对天然橡胶热氧老化防护机理的实验及分子模拟研究[D]. 北京:北京化工大学, 2018. Liu L Y. Study on the anti-oxidative mechanisms of two amine antioxidants in natural rubber by experiments and molecular simulations[D]. Beijing:Beijing University of Chemical Technology, 2018.
|
[15] |
王思静,熊金平,左禹.橡胶老化特征及防护技术研究进展[J]. 合成材料老化与应用, 2009,38(3):41-46. Wang S J, Xiong J P, Zuo Y. Study on protection technology for rubbers[J]. Synthetic Materials Aging and Application, 2009,38(3):41-46.
|
[16] |
于文龙.橡胶防老剂4020合成工艺的研究[D]. 青岛:青岛科技大学, 2013. Yu W L. Study on preparation of antioxidant 4020 by catalytic hydrogenation[D]. Qingdao:Qingdao University of Science and Technology, 2013.
|
[17] |
王芳,孙诚,徐林.缩合,加氢两步合成防老剂4020的研究[J]. 上海化工, 2017,10:17-20. Wang F, Sun C, Xu L. Two-step synthesis of antioxidant 4020 via condensation and hydrogenation[J]. Shanghai Chemical Industry, 2017,10:17-20.
|
[18] |
张帆.橡胶防老剂6PPD合成工艺优化研究[J]. 能源化工, 2019,40(3):12-15. Zhang F. Study on optimization of synthesis process of rubber antioxidant 6PPD[J]. Energy Chemical Industry, 2019,40(3):12-15.
|
[19] |
Xu W, Ni J, Zhang Q F, et al. Tailoring supported palladium sulfide catalysts through H-2-assisted sulfidation with H2S[J]. Journal of Materials Chemistry A, 2013,1(41):12811-12817.
|
[20] |
Yu W, Yu S, Ding J, et al. Effects of pore structure of MgO-templated mesoporous carbon on its supported Pt catalysts for reductive alkylation of p-aminodiphenylamine with methyl isobutyl ketone[J]. New Journal of Chemistry, 2019,43(13):5109-5115.
|
[21] |
Narathichat M, Sahakaro K, Nakason C. Assessment degradation of natural rubber by moving die processability test and FTIR spectroscopy[J]. Journal of Applied Polymer Science, 2010,115(3):1702-1709.
|
[22] |
姚水良.复合防老剂概况[J]. 合成材料老化与应用, 1990,(3):23-27. Yao S L. Overview of compound antioxidants[J]. Synthetic Materials Aging and Application, 1990,(3):23-27.
|
[23] |
Cibulkova Z, Simon P, Lehocky P, et al. Antioxidant activity of p-phenylenediamines studied by DSC[J]. Polymer Degradation and Stability, 2005,87(3):479-486.
|
[24] |
Cerna A, Cibulkova Z, Simon P, et al. DSC study of selected antioxidants and their binary mixtures in styrene-butadiene rubber[J]. Polymer Degradation and Stability, 2012,97(9):1724-1729.
|
[25] |
Carpenedo G, Demori R, Carli L, et al. Evaluation of stabilizing additives content in the mechanical properties of elastomeric compositions subject to environmental and accelerated aging[J]. Materials Research, 2020,23(5):20201039.
|
[26] |
Huntink N M, Datta R N. A novel slow release antidegradant for the rubber industry[J]. Kautschuk und Gummi, Kunststoffe, 2003,56(6):310-315.
|
[27] |
国钦瑞,邵华锋.橡胶的老化机理及老化行为的研究进展[J]. 高分子通报, 2022,(2):17-24. Guo Q R, Shao H F. Progress in aging mechanism and behavior of rubbers[J]. Polymer Bulletin, 2022,(2):17-24.
|
[28] |
李瑞端,潘宵,王金利,等.不同种类抗氧剂的应用与发展[J]. 化学工程与装备, 2020,12:251-252. Li R R, Fan X, Wang J L, et al. Application and development of different types of antioxidants[J]. Chemical Engineering & Equipment, 2020,12:251-252.
|
[29] |
王建鑫.对苯二胺衍生物结构因素和其抗降解活性的相关性[J]. 橡胶译丛, 1993,(5):1-6. Wang J X. Correlation between structural factors of p-phenylenediamine derivatives and their antidegrading activity[J]. World Rubber Industry, 1993,(5):1-6.
|
[30] |
谭向东.聚合物抗降解剂的功能与抗降解机理[J]. 橡胶工业, 1996,10:622-632. Tan X D. Function and anti-degradation mechanism of polymer anti-degrading agent[J]. China Rubber Industry, 1996,10:622-632.
|
[31] |
刘春芳.对苯二胺类防老剂在橡胶热氧老化过程中的消耗及反应机理[J]. 世界橡胶工业, 2014,41(4):39-44. Liu C F. Consumption and reaction mechanism of p-phenylenediamine antioxidants in the thermal-oxidative ageing process of rubber[J]. World Rubber Industry, 2014,41(4):39-44.
|
[32] |
辜晓乐.对苯二胺类防老剂的分子结构与有效性的关系[J]. 橡胶参考资料, 1994,24(10):31-35. Gu X L. Molecular structure of p-phenylenediamine antioxidants in relation to their effectiveness[J]. Rubber references, 1994,24(10):31-35.
|
[33] |
Cataldo F. A study on the reaction between N-substituted p-phenylenediamines and ozone:Experimental results and theoretical aspects in relation to their antiozonant activity[J]. European Polymer Journal, 2002,38(5):885-893.
|
[34] |
Cataldo F, Faucette B, Huang S, et al. On the early reaction stages of ozone with N,N¢-substituted p-phenylenediamines (6PPD, 77PD) and N,N¢,N²-substituted-1,3,5-triazine "Durazone®":An electron spin resonance (ESR) and electronic absorption spectroscopy study[J]. Polymer Degradation and Stability, 2015,111:223-231.
|
[35] |
Lattimer R, Hooser E, Layer R, et al. Mechanisms of ozonation of N-(1, 3-dimethylbutyl)-N¢-phenyl-p-phenylenediamine[J]. Rubber Chemistry and Technology, 1983,56(2):431-439.
|
[36] |
赵秋月,李荔,李慧鹏.国内外近地面臭氧污染研究进展[J]. 环境科技, 2018,31(5):72-76. Zhao Q Y, Li L, Li H P. Research progress on surface ozone pollution in domestic and overseas[J]. Environmental Science and Technology, 2018,31(5):72-76.
|
[37] |
Prosser R S, Parrott J L, Galicia M, et al. Toxicity of sediment-associated substituted phenylamine antioxidants on the early life stages of pimephales promelas and a characterization of effects on freshwater organisms[J]. Environmental Toxicology and Chemistry, 2017,36(10):2730-2738.
|
[38] |
Meyer A, Fischer K. Oxidative transformation processes and products of para-phenylenediamine (PPD) and para-toluenediamine (PTD)-a review[J]. Environmental Sciences Europe, 2015,27(1):11.
|
[39] |
Hartwig A, MAK Commission. N-(1, 3-Dimethylbutyl)-N¢-phenyl-p-phenylenediamine (6-PPD)[MAK Value Documentation, 2013] [J]. The MAK-Collection for Occupational Health and Safety:Annual Thresholds and Classifications for the Workplace, 2002,1(2):746-770.
|
[40] |
Datta R N, Huntink N M, Datta S, et al. Rubber vulcanizates degradation and stabilization[J]. Rubber Chemistry and Technology, 2007,80(3):436-480.
|
[41] |
杨宏辉.市场向好,轮胎产量累计同比首现正增长[J]. 中国橡胶, 2021,37(2):6-7. Yang H H. The market is good, and the cumulative tire production is growing for the first time year-on-year[J]. China Rubber, 2021,37(2):6-7.
|
[42] |
Dall'osto M, Beddows D C S, Gietl J K, et al. Characteristics of tyre dust in polluted air:Studies by single particle mass spectrometry (ATOFMS)[J]. Atmospheric Environment, 2014,94:224-230.
|
[43] |
焦萌,曹秉帝,张涛.环境中的轮胎磨损颗粒:从路面到海洋[J]. 环境科学学报, 2020,40(12):4263-4278. Jiao M, Cao B D, Zhang T. Tire wear particles in the environment:From road to ocean[J]. Acta Scientiae Circumstantiae, 2020,40(12):4263-4278.
|
[44] |
Hu X, Zhao H N, Tian Z, et al. Transformation Product Formation upon Heterogeneous Ozonation of the Tire Rubber Antioxidant 6PPD (N-(1,3-dimethylbutyl)-N¢-phenyl-p-phenylenediamine)[J]. Environmental Science & Technology Letters, 2022,9(5):413-419.
|
[45] |
Müller K, Hübner D, Huppertsberg S, et al. Probing the chemical complexity of tires:Identification of potential tire-borne water contaminants with high-resolution mass spectrometry[J]. Science of The Total Environment, 2022,802:149799.
|
[46] |
Mcintyre J K, Prat J, Cameron J, et al. Treading Water:Tire Wear Particle Leachate Recreates an Urban Runoff Mortality Syndrome in Coho but Not Chum Salmon[J]. Environmental Science & Technology, 2021,55(17):11767-11774.
|
[47] |
陈瑶,刘金,张颖昕,等.环境中的黑色微塑料——轮胎磨损颗粒的来源、迁移扩散及环境风险[J]. 应用生态学报, 2022,33(8):2260-2270. Chen Y, Liu J, Zhang Y X, et al. Black microplastics in the environmen:Origin, transport and risk of tire wear particles[J]. Chinese Journal of Applied Ecology, 2022,33(8):2260-2270.
|
[48] |
Unice K M, Bare J L, Kreider M L, et al. Experimental methodology for assessing the environmental fate of organic chemicals in polymer matrices using column leaching studies and OECD 308water/sediment systems:Application to tire and road wear particles[J]. Science of The Total Environment, 2015,533:476-487.
|
[49] |
Kruger R H, Boissiere C, Klein-Hartwig K, et al. New phenylenediamine antiozonants for commodities based on natural and synthetic rubber[J]. Food Additives and Contaminants, 2005,22(10):968-974.
|
[50] |
Huang W, Shi Y, Huang J, et al. Occurrence of Substituted p-Phenylenediamine Antioxidants in Dusts[J]. Environmental Science & Technology Letters, 2021,8(5):381-385.
|
[51] |
Wolfgang G H, Jolly R A, Donarski W J, et al. Inhibition of diquat-induced lipid peroxidation and toxicity in precision-cut rat liver slices by novel antioxidants[J]. Toxicology and Applied Pharmacology, 1991,108(2):321-329.
|
[52] |
Yanagitai M, Kitagawa T, Okawa K, et al. Phenylenediamine derivatives induce GDF-15/MIC-1and inhibit adipocyte differentiation of mouse 3T3-L1cells[J]. Biochemical and Biophysical Research Communications, 2012,417(1):294-298.
|
[53] |
Masset T B, Ferrari B J D, William D, et al., Bio accessibility of tire-associated organic chemicals in fish gut (Oncorhynchus mykiss):insights from an in vitro digestion model[C]//Micropol & Ecohazard 2022, Satiago de Compostela, Spain, 2022.
|
[54] |
Sakemi K, Usami M, Kurebayashi H, et al.[Teratogenicity study of N-methylphenyl-N'-methylphenyl-p-phenylenediamine (MMPD) in rats by oral administration] [J]. Bulletin of National Institute of Health Sciences, 2001,119:47-51.
|
[55] |
Grigoratos T, Gustafsson M, Eriksson O, et al. Experimental investigation of tread wear and particle emission from tyres with different treadwear marking[J]. Atmospheric Environment, 2018, 182:200-212.
|
[56] |
Panko J M, Chu J, Kreider M L, et al. Measurement of airborne concentrations of tire and road wear particles in urban and rural areas of France, Japan, and the United States[J]. Atmospheric Environment, 2013,72:192-199.
|
[57] |
赵兴敏,杨扬,郭欣欣,等.长春市典型高架公路大气环境颗粒物中重金属污染特征[J]. 环境科学学报, 2017,37(9):3280-3288. Zhao X M, Yang Y, Guo X X, et al. Pollution characteristics of heavy metals in atmospheric particulates from typical elevated highway in Changchun City[J]. Acta Scientiae Circumstantiae, 2017,37(9):3280-3288.
|
[58] |
张静,王婷,门正宇,等.颗粒物中苯并噻唑及其衍生物的污染特征及暴露评价[J]. 中国环境科学, 2020,40(2):851-856. Zhang J, Wang T, Men Z Y, et al. Pollution characteristics and exposure assessment of benzothiazole and its derivatives in ambient air particulates[J]. China Environmental Science, 2020,40(2):851-856.
|
[59] |
陈乾刚,樊儒,封旭升,等.宝鸡冬季PM2.5中多环芳烃的来源解析及健康风险评估[J]. 环境保护前沿, 2021,11:926. Chen Q G, Fan R, Feng X S, et al. Assessment of PM2.5-Bound polycyclic aromatic hydrocarbons in winter of Baoji. Advances in Environmental Protection, 2021,11:926.
|
[60] |
Zhang Y, Xu C, Zhang W, et al. p-Phenylenediamine antioxidants in PM2.5:The underestimated urban air pollutants[J]. Environmental Science & Technology, 2022,56(11):6914-6921.
|
[61] |
Kole P J, Löhr A J, Van Belleghem F G A J, et al. Wear and tear of tyres:A stealthy source of microplastics in the environment[J]. International Journal of Environmental Research and Public Health, 2017,14(10):1265.
|
[62] |
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
|
[63] |
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.
|
[64] |
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, 2022,302:119082.
|
[65] |
Liu R, Li Y, Lin Y, et al. Emerging aromatic secondary amine contaminants and related derivatives in various dust matrices in China[J]. Ecotoxicology and Environmental Safety, 2019,170:657-663.
|
[66] |
Jiao M, Cao B, Zhang T. Tire wear particles in the environment:From road to ocean[J]. Acta Scientiae Circumstantiae, 2020,40(12):4263-4278.
|
[67] |
Johannessen C, Helm P, Lashuk B, et al. The tire wear compounds 6PPD-Quinone and 1,3-Diphenylguanidine in an urban watershed[J]. Archives of environmental contamination and toxicology, 2022,82(2):171-179.
|
[68] |
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, 2022,212:118122-118122.
|
[69] |
Johannessen C, Helm P, Metcalfe C D. Detection of selected tire wear compounds in urban receiving waters*[J]. Environmental Pollution, 2021,287:117659.
|
[70] |
Monaghan J, Jaeger A, Agua A R, et al. A direct mass spectrometry method for the rapid analysis of ubiquitous tire-derived toxin N-(1,3-Dimethylbutyl)-N '-phenyl-p-phenylenediamine Quinone (6-PPDQ)[J]. Environmental Science & Technology Letters, 2021, 8(12):1051-1056.
|
[71] |
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.
|
[72] |
Ding J, Lv M, Zhu D, et al. Tire wear particles:An emerging threat to soil health[J]. Critical Reviews in Environmental Science and Technology, 2022:1-19.
|
[73] |
Wagner S, Hueffer T, Kloeckner P, et al. Tire wear particles in the aquatic environment-A review on generation, analysis, occurrence, fate and effects[J]. Water Research, 2018,139:83-100.
|
[74] |
Thomas J, Moosavian S K, Cutright T, et al. Investigation of abiotic degradation of tire cryogrinds[J]. Polymer Degradation and Stability, 2022,195:109814.
|
[75] |
丁秀臣,陈蕾,于俊荣,等.聚对苯二甲酰对苯二胺降解性研究[J]. 合成纤维, 2008,37(8):15-17. Ding X C, Chen L, Yu J R, et al. Preparation of poly(ethylene terephthalate) nanofibers by Gas-Jet/Electrospinning[J]. Synthetic Fiber in China, 2008,37(8):15-17.
|
[76] |
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.
|
[77] |
Ali Shah A, Hasan F, Shah Z, et al. Biodegradation of natural and synthetic rubbers:A review[J]. International Biodeterioration & Biodegradation, 2013,83:145-157.
|
[78] |
Banks D, Soliman M R. Protective effects of antioxidants against benomyl-induced lipid peroxidation and glutathione depletion in rats[J]. Toxicology, 1997,116(1-3):177-181.
|
[79] |
Ahmed E A, Omar H M, Abd Elghaffar S K, et al. The antioxidant activity of Vitamin C, DPPD and L-cysteine against Cisplatin-induced testicular oxidative damage in rats[J]. Food and Chemical Toxicology, 2011,49(5):1115-1121.
|
[80] |
Qunnguan J, Moldéus P. Effect of the antioxidant N,N1=Diphenyl=p phenylenediamine (DPPD) on bromobenzene metabolism and toxicity in isolated hepatocytes[J]. Pharmacology & toxicology, 1988,62(2):104-106.
|
[81] |
Satoh T, Izumi M. Neuroprotective effects of phenylenediarnine derivatives independent of an antioxidant pathway in neuronal HT22cells[J]. Neuroscience Letters, 2007,418(1):102-105.
|
[82] |
Zanoni T B, Hudari F, Munnia A, et al. The oxidation of p-phenylenediamine, an ingredient used for permanent hair dyeing purposes, leads to the formation of hydroxyl radicals:Oxidative stress and DNA damage in human immortalized keratinocytes[J]. Toxicology Letters, 2015,239(3):194-204.
|
[83] |
Cha H J, Lee O K, Kim S Y, et al. MicroRNA expression profiling of p-phenylenediamine treatment in human keratinocyte cell line[J]. Molecular & Cellular Toxicology, 2015,11(1):19-28.
|
[84] |
Hyunju W, Hayeon K, Seoungwoo S, et al. Rhus semialata M. extract ameliorate para-phenylenediamine-induced toxicity in keratinocytes[J]. Toxicology Reports, 2021,8:96-105.
|
[85] |
Huang Y C, Hung W C, Kang W Y, et al. p-Phenylenediamine induced DNA damage in SV-40immortalized human uroepithelial cells and expression of mutant p53 and COX-2proteins[J]. Toxicology Letters, 2007,170(2):116-123.
|
[86] |
Huang Y C, Hung W C, Chye S M, et al. para-Phenylenediamine-induced autophagy in human uroepithelial cell line mediated mutant p53 and activation of ERK signaling pathway[J]. Toxicology In Vitro, 2011,25(8):1630-1637.
|
[87] |
朱勇,丁璐,徐艳琼.橡胶防老剂4020, 4010NA对人胚肺成纤维细胞的毒性对比[J]. 职业与健康, 2016,14:1991-1992. Zhu Y, Ding L, Xu Y Q. A comparative study of toxicity of rubber antioxidant 4020 and 4010 NA on human embryonic lung fibroblast cells[J]. Occupation and Health, 2016,14:1991-1992.
|
[88] |
徐艳琼,龚伟,王建锋,等.橡胶防老剂对作业人员健康的影响及可能机制[J]. 职业与健康, 2015,16:2180-2183. Xu Y Q, Gong W, Wang J F, et al. Effect of antioxidant on the health of workers and its possible molecular mechanism[J]. Occupation and Health, 2015,16:2180-2183.
|
[89] |
Chen S C, Chen C H, Tioh Y L, et al. Para-phenylenediamine induced DNA damage and apoptosis through oxidative stress and enhanced caspase-8and-9activities in Mardin-Darby canine kidney cells[J]. Toxicology In Vitro, 2010,24(4):1197-1202.
|
[90] |
Elyoussoufi Z, Mounaji K, Cadi R, et al. Induction of oxidative stress and apoptosis in human neutrophils by p-phenylenediamine[J]. Journal of Toxicology and Environmental Health Sciences, 2013, 5(8):142-149.
|
[91] |
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.
|
[92] |
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.
|
[93] |
Blair S I, Barlow C H, Mcintyre J K. Acute cerebrovascular effects in juvenile coho salmon exposed to roadway runoff[J]. Canadian Journal of Fisheries and Aquatic Sciences, 2021,78(2):103-109.
|
[94] |
Varshney S, Gora A H, Siriyappagouder P, et al. Toxicological effects of 6PPD and 6PPD quinone in zebrafish larvae[J]. Journal of Hazardous Materials, 2022,424:127623.
|
[95] |
Peng W, Liu C, Chen D, et al. Exposure to N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine (6PPD) affects the growth and development of zebrafish embryos/larvae[J]. Ecotoxicology and Environmental Safety, 2022,232:113221.
|
[96] |
Ji J, Huang J, Cao N, et al. Multiview behavior and neurotransmitter analysis of zebrafish dyskinesia induced by 6PPD and its metabolites[J]. Science of The Total Environment, 2022,838:156013.
|
[97] |
Klauschies T, Isanta-Navarro J. The joint effects of salt and 6PPD contamination on a freshwater herbivore[J]. Science of The Total Environment, 2022,829:154675.
|
[98] |
Sandré F, Huynh N, Gromaire M-C, et al. Road runoff characterization:Ecotoxicological assessment combined with (non-) target screenings of micropollutants for the identification of relevant toxicants in the dissolved phase[J]. Water, 2022,14(4):511.
|
[99] |
Laplaca S B, Van den hurk P. Toxicological effects of micronized tire crumb rubber on mummichog (Fundulus heteroclitus) and fathead minnow (Pimephales promelas)[J]. Ecotoxicology, 2020,29(5):524-534.
|
[100] |
Wik A, Dave G. Acute toxicity of leachates of tire wear material to Daphnia magna-Variability and toxic components[J]. Chemosphere, 2006,64(10):1777-1784.
|
[101] |
Masset T B, Breider F, William D, et al. Effects of tire particles on the reproduction of earthworms Eisenia fetida) and bioaccumulation potential of tire related chemicals[R]. Denmark:SETAC Europe 2022,2022.
|
[102] |
Gilbert M D, Elfving D C, Lisk D J. Protection of plants against ozone injury using the antiozonant N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine[J]. Bulletin of Environmental Contamination and Toxicology, 1977,18(6):783-786.
|
[103] |
Matsumoto M, Yamaguchi M, Yoshida Y, et al. An antioxidant, N,N¢-diphenyl-p-phenylenediamine (DPPD), affects labor and delivery in rats:A 28-day repeated dose test and reproduction/developmental toxicity test[J]. Food and Chemical Toxicology, 2013,56:290-296.
|
[104] |
Chung K-T, Murdock C A, Stevens S E, et al. Mutagenicity and toxicity studies of p-phenylenediamine and its derivatives[J]. Toxicology Letters, 1995,81(1):23-32.
|
[105] |
Erin W M, Jenna R L, Joel D G, et al. Contact dermatitis associated with hair care products:A retrospective analysis of the North American contact dermatitis group data, 2001~2016[J]. Dermatitis, 2022,33(1):91-102.
|
[106] |
Warshaw E M, Kullberg S A, Atwater A R, et al. Currently relevant p-phenylenediamine patch test reactions associated with hair dye and nonscalp anatomic areas:Retrospective cross-sectional analysis of North American Contact Dermatitis Group data, 2001 to 2016[J]. Journal of the American Academy of Dermatology, 2021,84(3):e175-e177.
|
[107] |
DePaul S, DelBuono N, Khalid M M. Contact dermatitis from p-Phenylenediamine in beard dye[J]. Visual Journal of Emergency Medicine, 2021,22:100939.
|
[108] |
Bacharewicz-Szczerbicka J, Reduta T, Pawlos A, et al. Paraphenylenediamine and related chemicals as allergens responsible for allergic contact dermatitis[J]. Archives of Medical Science, 2021, 17(3):714-723.
|
[109] |
Hansson C. Allergic contact dermatitis from N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine and from compounds in polymerized 2,2,4-trimethyl-1,2-dihydroquinoline[J]. Contact Dermatitis, 1994, 30(2):114-115.
|
[110] |
Herve-bazin B, Gradiski D, Duprat P, et al. Occupational eczema from N-isopropyl-N'-phenylparaphenylenediamine (IPPD) and N-dimethy-1, 3butyl-N'-phenylparaphenylenediamine (DMPPD) in tyres[J]. Contact Dermatitis, 1977,3(1):1-15.
|
[111] |
Schneider K, De Hoogd M, Madsen M P, et al. ERASSTRI-European risk assessment study on synthetic turf rubber infill-Part 1:Analysis of infill samples[J]. Science of The Total Environment, 2020,718:137174.
|
[112] |
Kretzschmar H J, Kelm J, Tobisch K, et al. Migration of primary aromatic amines from rubber based commodity articles into food[J]. Deutsche Lebensmittel-Rundschau, 1999,95(6):223-230.
|
[113] |
Kretzschmar H J. Toxic amines and isothiocyanates formed during accelerated vulcanisation[C]//Proceedings of symposium on hazards in the European rubber industry organized by Rapra Technology LTD in Manchester, UK. Paper. 1999,6.
|
[114] |
Nhi B D, Thao M T, Ngo V D, et al. Synthesis of antioxidant for natural rubber using new heterogeneous catalytic system[J]. Chemical Papers, 2019,73(12):3115-3121.
|
[115] |
Халдеева А Р, Давыдова М Л, Соколова М Д, et al. Influence of hindered phenolic stabilizers on the climatic stability of rubbers based on epichlorohydrin caoutchouc[J]. Нефтегазовое дело, 2021,19(2):78-90.
|
[116] |
El-Wakil A E A A, El-Mogy S, Halim S F, et al. Enhancement of aging resistance of EPDM rubber by natural rubber-g-N (4-phenylenediamine) maleim -ide as a grafted antioxidant[J]. Journal of Vinyl & Additive Technology, 2022,28(2):367-378.
|
[117] |
Sahakaro K, Naskar N, Datta R N, et al. Reactive blending, reinforcement and curing of NR/BR/EPDM compounds for tire sidewall applications[J]. Rubber Chemistry and Technology, 2007, 80(1):115-138.
|
[118] |
Sahakaro K, Datta R N, Baaij J, et al. Blending of NR/BR/EPDM by reactive processing for tire sidewall applications. III. Assessment of the blend ozone-and fatigue-resistance in comparison with a conventional NR/BR compound[J]. Journal of Applied Polymer Science, 2007,103(4):2555-2563.
|
[119] |
Kataoka T, Zetterlund P B, Yamada B. Prevention of rubber degradation by use of microencapsulated antioxidants[J]. Rubber Chemistry and Technology, 2003,76(4):948-956.
|
[120] |
Huntink N M, Datta R N, Talma A, et al. Ozonolysis of model olefins-Efficiency of antiozonants[J]. Journal of Applied Polymer Science, 2006,100(2):853-866.
|
[121] |
Venkatesan G, Dancik Y, Sinha A, et al. Development of novel alternative hair dyes to hazardous para-phenylenediamine[J]. Journal of Hazardous Materials, 2021,402:123712.
|
|
|
|