轮胎橡胶老化过程中微橡胶及<italic style="font-style: italic">N</italic>-‍(1,‍3-二甲基丁基)-<italic style="font-style: italic">N</italic>'-苯基对苯二胺转化产物分析

王建凤; 张裕祥; 王佳敏; 丁兆阳; 勾新磊; 钱冲; 高原; 刘艳; 高峡

doi:10.11777/j.issn1000-3304.2024.24180;

您当前的位置：

首页 >

文章列表页 >

轮胎橡胶老化过程中微橡胶及N-‍(1,‍3-二甲基丁基)-N'-苯基对苯二胺转化产物分析

研究论文 | 更新时间：2025-01-10

- 轮胎橡胶老化过程中微橡胶及N-‍(1,‍3-二甲基丁基)-N'-苯基对苯二胺转化产物分析
  增强出版
- Determination of Microrubber and N-(1,3-dimethylbutyl)-N'-phenyl-1,4-phenylenediamin Associated Transformation Products in Rubber Aging Process
- 高分子学报 2024年55卷第12期页码：1763-1772
- 作者机构：
  
  1.北京市科学技术研究院分析测试研究所(北京市理化分析测试中心) 有机材料检测技术与质量评价北京市重点实验室北京 100094
  2.首都师范大学化学系北京100048
- 作者简介：
  
  E-mail: liuyan@bcpca.ac.cn
  gaoxia@bcpca.ac.cn
- 基金信息：
  
  国家重点研发计划(2022YFF0606702);北京市改革与发展项目(24CB003-10)
- DOI：10.11777/j.issn1000-3304.2024.24180;
  中图分类号：
- CSTR：32057.14.GFZXB.2024.7285
- 纸质出版日期：2024-12-20，
  
  网络出版日期：2024-10-29，
  
  收稿日期：2024-07-26，
  
  录用日期：2024-08-28
- 稿件说明：
移动端阅览
王建凤, 张裕祥, 王佳敏, 丁兆阳, 勾新磊, 钱冲, 高原, 刘艳, 高峡. 轮胎橡胶老化过程中微橡胶及N-(1,3-二甲基丁基)-N'-苯基对苯二胺转化产物分析. 高分子学报, 2024, 55(12), 1763-1772

Wang, J. F.; Zhang, Y. X.; Wang, J. M.; Ding, Z. Y.; Gou, X. L.; Qian, C.; Gao, Y.; Liu, Y.; Gao, X. Determination of microrubber and N-‍(1,‍3-dimethylbutyl)‍-N'-phenyl-1,‍4-phenylenediamin associated transformation products in rubber aging process. Acta Polymerica Sinica, 2024, 55(12), 1763-1772
王建凤, 张裕祥, 王佳敏, 丁兆阳, 勾新磊, 钱冲, 高原, 刘艳, 高峡. 轮胎橡胶老化过程中微橡胶及N-(1,3-二甲基丁基)-N'-苯基对苯二胺转化产物分析. 高分子学报, 2024, 55(12), 1763-1772 DOI： 10.11777/j.issn1000-3304.2024.24180;. CSTR： 32057.14.GFZXB.2024.7285.

Wang, J. F.; Zhang, Y. X.; Wang, J. M.; Ding, Z. Y.; Gou, X. L.; Qian, C.; Gao, Y.; Liu, Y.; Gao, X. Determination of microrubber and N-‍(1,‍3-dimethylbutyl)‍-N'-phenyl-1,‍4-phenylenediamin associated transformation products in rubber aging process. Acta Polymerica Sinica, 2024, 55(12), 1763-1772 DOI： 10.11777/j.issn1000-3304.2024.24180;. CSTR： 32057.14.GFZXB.2024.7285.

摘要

-(1

3-二甲基丁基)-

'-苯基对苯二胺(6-PPD)是一种广泛应用于轮胎橡胶中的抗氧化剂，可在臭氧存在时氧化成6-PPD醌(6-PPDQ)，6-PPDQ对某些鱼类(如银鲑鱼)能产生急性致死毒性. 为了探究6-PPD是否能在自然光条件下产生6-PPDQ，本研究首先利用自制高分子材料力学加速老化装置对橡胶进行力学老化，对其产生的微橡胶进行了分析. 并通过模拟自然光的人工加速氙灯老化试验，考察微橡胶在老化后6-PPD的转化产物，同时利用6-PPD标准品老化实验对其转化产物进行验证. 结果表明，车辆在理想路面和较轻的负荷下就能够产生较小的微橡胶，且呈正态分布，平均粒径为4.12 μm；6-PPD在老化后消失，经验证后，发现6-PPD转化成6种转化产物，包括4-甲基-2-戊酮(MIBK)、

-苯甲酰-对苯二胺(PFPDA)、对氨基二苯胺(4-ADPA)、6-PPDQ、4-异丙氨基二苯胺(IPPD)和

'-二苯基对苯二胺(DPPD). 采用毒性评估软件(T.E.S.T)对6种转化产物进行毒性预测，除DPPD和MIBK外，其他产物的大鼠半数致死率都高于6-PPD本身. 本研究表明车辆行驶时会产生大量的微橡胶颗粒，对于微橡胶环境生态毒理学评价和6-PPD使用安全及其风险评估有着重要的意义.

Abstract

-‍(1

‍3-Dimethylbutyl)‍-

'-phenyl-1

4-phenylenediamin

(6-PPD) is a widely used antioxidant in tire rubber

which can be oxidized into a highly toxic compound 6-PPD quinone (6-PPDQ) by ozone

resulting in extreme acute toxicity in some fish species (

e.g

coho salmon). To explore whether 6-PPD can produce 6-PPDQ under natural light conditions

the experiment of the artificial accelerated xenon lamp aging test was designed. A self-made mechanical accelerated aging device of polymer materials was used to simulate aging tire rubber samples. Microrubber particles was determined. Then the associated transformation products of 6-PPD were analyzed and verified by chromatography-mass spectrometry after further xenon lamp aging test. The results showed that vehicles can produce smaller amounts of micro rubber on ideal road surfaces under lighter loads. The recovered tire rubber samples were changed into microrubbers. The size of microrubbers showed normally distributed with the average particle size of 4.12 μm. The antioxidant 6-PPD disappears after aging. After verification

it is found that 6-PPD can be changed into six transformation products under xenon lamp. They are 4-methyl-2-pentanone

-phenylformyl-p-phenyldiamine (PFPDA)

4-Aminodiphenylamine

(4-ADPA)

6-PPD-quinone

4-isopropylamino-diphenylamine (IPPD)

and

‍

'-diphenyl-p-phenylenediamine (DPPD)

whose toxicities were predicted using T.E.S. T software. Except for DPPD a

nd 4-methyl-2-pentanone

the median lethal dose of other products was higher than that of 6-PPD itself. This study shows that a large number of micronrubber particles are produced during vehicle driving

which has great significance for ecotoxicological evaluation of microrubber environment and safety and risk assessment of 6-PPD.

关键词

N-(13-二甲基丁基)-N'-苯基对苯二胺老化高分辨质谱微橡胶

Keywords

N-‍(1‍3-Dimethylbutyl)-N'-phenyl-1‍4-phenylenediaminAgingHigh resolution mass spectrometryMicrorubber

references

Liu Q. F.; Li L.; Zhang X. M.; Saini A.; Li W. L.; Hung H.; Hao C. Y.; Li K.; Lee P.; Wentzell J. J. B.; Huo C. Y.; Li S. M.; Harner T.; Liggio J.Uncovering global-scale risks from commercial chemicals in air. Nature, 2021, 600(7889), 456-461. doi:10.1038/s41586-021-04134-6http://dx.doi.org/10.1038/s41586-021-04134-6

Tian Z. Y.; Zhao H. Q.; Peter K. T.; Gonzalez M.; Wetzel J.A ubiquitous tire rubberderived chemical induces acute mortality in coho salmon. Sci., 2022, 376(6592), 470-470.

Hu X. M.; Zhao H. N.; Tian Z. Y.; Peter K. T.; Dodd M. C.; Kolodziej E. P.Transformation product formation upon heterogeneous ozonation of the tire rubber antioxidant 6PPD (N-‍(1,‍3-dimethylbutyl)‍-N'-phenyl-p-phenylenediamine). Environ. Sci. Technol. Lett., 2022, 9(5), 413-419. doi:10.1021/acs.estlett.2c00187http://dx.doi.org/10.1021/acs.estlett.2c00187

Tian Z. Y.; Gonzalez M.; Rideout C. A.; Zhao H. N.; Hu X. M.; Wetzel J.; Mudrock E.; James C. A.; McIntyre J. K.; Kolodziej E. P.6PPD-quinone: revised toxicity assessment and quantification with a commercial standard. Environ. Sci. Technol. Lett., 2022, 9(2), 140-146. doi:10.1021/acs.estlett.1c00910http://dx.doi.org/10.1021/acs.estlett.1c00910

Hiki K.; Asahina K.; Kato K.; Yamagishi T.; Omagari R.; Iwasaki Y.; Watanabe H.; Yamamoto H.Acute toxicity of a tire rubber-derived chemical, 6PPD quinone, to freshwater fish and crustacean species. Environ. Sci. Technol. Lett., 2021, 8(9), 779-784. doi:10.1021/acs.estlett.1c00453http://dx.doi.org/10.1021/acs.estlett.1c00453

McIntyre J. K.; Prat J.; Cameron J.; Wetzel J.; Mudrock E.; Peter K. T.; Tian Z. Y.; MacKenzie C.; Lundin J.; Stark J. D.; King K.; Davis J. W.; Kolodziej E. P.; Scholz N. L.Treading water: tire wear particle leachate recreates an urban runoff mortality syndrome in coho but not chum salmon. Environ. Sci. Technol., 2021, 55(17), 11767-11774. doi:10.1021/acs.est.1c03569http://dx.doi.org/10.1021/acs.est.1c03569

Brinkmann M.; Montgomery D.; Selinger S.; Miller J. G. P.; Stock E.; Alcaraz A. J.; Challis J. K.; Weber L.; Janz D.; Hecker M.; Wiseman S.Acute toxicity of the tire rubber-derived chemical 6PPD-quinone to four fishes of commercial, cultural, and ecological importance. Environ. Sci. Technol. Lett., 2022, 9(4), 333-338. doi:10.1021/acs.estlett.2c00050http://dx.doi.org/10.1021/acs.estlett.2c00050

Mahoney H.; da Silva Junior F. C.; Roberts C.; Schultz M.; Ji X. W.; Alcaraz A. J.; Montgomery D.; Selinger S.; Challis J. K.; Giesy J. P.; Weber L.; Janz D.; Wiseman S.; Hecker M.; Brinkmann M.Exposure to the tire rubber-derived contaminant 6PPD-quinone causes mitochondrial dysfunction in vitro. Environ. Sci. Technol. Lett., 2022, 9(9), 765-771. doi:10.1021/acs.estlett.2c00431http://dx.doi.org/10.1021/acs.estlett.2c00431

Du B. B.; Liang B. W.; Li Y.; Shen M. J.; Liu L. Y.; Zeng L. X.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. Environ. Sci. Technol. Lett., 2022, 9(12), 1056-1062. doi:10.1021/acs.estlett.2c00821http://dx.doi.org/10.1021/acs.estlett.2c00821

Chen L.; Hu J. R.; Borthwick A. G. L.; Sun W. L.; Zhang H. X.; Jia D. T.; Liu W.Solar-light-activated periodate for degradation and detoxification of highly toxic 6PPD-quinone at environmental levels. Nat. Water, 2024, 2, 453-463. doi:10.1038/s44221-024-00236-3http://dx.doi.org/10.1038/s44221-024-00236-3

Jin R. H.; Wu Y.; He Q.; Sun P.; Chen Q. Q.; Xia C. J.; Huang Y.; Yang J.; Liu M.Ubiquity of amino accelerators and antioxidants in road dust from multiple land types: targeted and nontargeted analysis. Environ. Sci. Technol., 2023, 57(28), 10361-10372. doi:10.1021/acs.est.3c01448http://dx.doi.org/10.1021/acs.est.3c01448

Cao G. D.; Wang W.; Zhang J.; Wu P. F.; Zhao X. C.; Yang Z.; Hu D.; Cai Z. W.New evidence of rubber-derived quinones in water, air, and soil. Environ. Sci. Technol., 2022, 56(7), 4142-4150. doi:10.1021/acs.est.1c07376http://dx.doi.org/10.1021/acs.est.1c07376

邹文奇, 王佳敏, 王建凤, 张裕祥, 魏晓晓, 汤庆峰, 钟怀宁, 刘艳, 高峡. 高分子材料全生命周期环境影响评估及关键表征技术. 高分子通报, 2024, 37(8), 1011-1023.

Worek J.; Badura X.; Białas A.; Chwiej J.; Kawoń K.; Styszko K.Pollution from transport: detection of tyre particles in environmental samples. Energies, 2022, 15(8), 2816. doi:10.3390/en15082816http://dx.doi.org/10.3390/en15082816

Goßmann I.; Halbach M.; Scholz-Böttcher B. M.Car and truck tire wear particles in complex environmental samples—a quantitative comparison with "traditional" microplastic polymer mass loads. Sci. Total Environ., 2021, 773, 145667. doi:10.1016/j.scitotenv.2021.145667http://dx.doi.org/10.1016/j.scitotenv.2021.145667

Wilkinson T.; Järlskog I.; de Lima J. A.; Gustafsson M.; Mattsson K.; Andersson Sköld Y.; Hassellöv M.Shades of grey—tire characteristics and road surface influence tire and road wear particle (TRWP) abundance and physicochemical properties. Front. Environ. Sci., 2023, 11, 1258922. doi:10.3389/fenvs.2023.1258922http://dx.doi.org/10.3389/fenvs.2023.1258922

Federico L.; Masseroni A.; Rizzi C.; Villa S.Silent contamination: the state of the art, knowledge gaps, and a preliminary risk assessment of tire particles in urban parks. Toxics, 2023, 11(5), 445. doi:10.3390/toxics11050445http://dx.doi.org/10.3390/toxics11050445

Ushmarin N. F.; Kavun S. M.New antiozonants for rubber compounds based on oxyalkylated derivatives of 4-aminodiphenylamine. Int. Polym. Sci. Technol., 2017, 44(11), 29-36. doi:10.1177/0307174x1704401107http://dx.doi.org/10.1177/0307174x1704401107

李威, 徐艺, 王大鹏, 王苗苗, 邓彩霞. 防老剂6PPD对胎侧胶变色的影响研究. 轮胎工业, 2020, 40(8), 507-510.

Li C. G.; Zhang Y. L.; Yin S. Q.; Wang Q.; Li Y. Y.; Liu Q.; Liu L.; Luo X. X.; Chen L. Y.; Zheng H.; Li F. M.First insights into 6PPD-quinone formation from 6PPD photodegradation in water environment. J. Hazard. Mater., 2023, 459, 132127. doi:10.1016/j.jhazmat.2023.132127http://dx.doi.org/10.1016/j.jhazmat.2023.132127

Johannessen C.; Helm P.; Lashuk B.; Yargeau V.; Metcalfe C. D.The tire wear compounds 6PPD-quinone and 1,3-diphenylguanidine in an urban watershed. Arch. Environ. Contam. Toxicol., 2022, 82(2), 171-179. doi:10.1007/s00244-021-00878-4http://dx.doi.org/10.1007/s00244-021-00878-4

Grasse N.; Seiwert B.; Massei R.; Scholz S.; Fu Q. G.; Reemtsma T.Uptake and biotransformation of the tire rubber-derived contaminants 6-PPD and 6-PPD quinone in the zebrafish embryo (danio rerio). Environ. Sci. Technol., 2023, 57(41), 15598-15607. doi:10.1021/acs.est.3c02819http://dx.doi.org/10.1021/acs.est.3c02819

Wang W.; Cao G. D.; Zhang J.; Qiao H.; Li H. K.; Yang B. W.; Chen Y. Y.; Zhu L.; Sang Y. C.; Du L.; Cai Z. W.UV-induced photodegradation of emerging para-phenylenediamine quinones in aqueous environment: kinetics, products identification and toxicity assessments. J. Hazard. Mater., 2024, 465, 133427. doi:10.1016/j.jhazmat.2024.133427http://dx.doi.org/10.1016/j.jhazmat.2024.133427

Gamboa-Becerra R.; Desgarennes D.; Molina-Torres J.; Ramírez-Chávez E.; Kiel-Martínez A. L.; Carrión G.; Ortiz-Castro R.Plant growth-promoting and non-promoting rhizobacteria from avocado trees differentially emit volatiles that influence growth of Arabidopsis thaliana. Protoplasma, 2022, 259(4), 835-854. doi:10.1007/s00709-021-01705-2http://dx.doi.org/10.1007/s00709-021-01705-2

Zhong L. Q.; Peng W. J.; Liu C. S.; Gao L.; Chen D. Q.; Duan X. B.IPPD-induced growth inhibition and its mechanism in zebrafish. Ecotoxicol. Environ. Saf., 2022, 239, 113614. doi:10.1016/j.ecoenv.2022.113614http://dx.doi.org/10.1016/j.ecoenv.2022.113614

Draper H. H.; Goodyear S.; Barbee K. D.; Johnson B. C.Tolerance of the rat for N,N'-diphenyl-P-phenylenediamine. Exp. Biol. Med., 1956, 93(2), 186-189. doi:10.3181/00379727-93-22702http://dx.doi.org/10.3181/00379727-93-22702

浏览量

下载量

CSCD

文章被引用时，请邮件提醒。

提交

工具集

关联资源

暂无数据

轮胎橡胶老化过程中微橡胶及N-‍(1,‍3-二甲基丁基)-N'-苯基对苯二胺转化产物分析

Determination of Microrubber and N-(1,3-dimethylbutyl)-N'-phenyl-1,4-phenylenediamin Associated Transformation Products in Rubber Aging Process

DOI：10.11777/j.issn1000-3304.2024.24180;

摘要

Abstract

关键词

Keywords

references