N-Isopropyl-N′-phenyl-1,4-phenylenediamine (often abbreviated IPPD) is an organic compound commonly used as an antiozonant in rubbers,[1] particularly those used for tires. Like other p-phenylenediamine-based antiozonants it works by virtue of its low ionization energy, which allows it to react with ozone faster than ozone will react with rubber.[2] This reaction converts it to the corresponding aminoxyl radical (R2N–O•), with the ozone being converted to a hydroperoxyl radical (HOO•),[2] these species can then be scavenged by other antioxidant polymer stabilizers.
IPPD is prone to process called blooming, where it migrates to the surface of the rubber.[3] This can be beneficial to the tire, as ozone attacks the tire surface and blooming therefore moves the antiozonant to where it is most needed,[4] however this also increases the leaching of IPPD into the environment. Many tire producers have moved to using 6PPD instead, as this migrates more slowly. Oxidation of IPPD converts the central phenylenediamine ring into a quinone.[5]
Safety
IPPD is a human allergen.[6][7] It is the compound responsible for coining the term "Volkswagen Dermatitis".[8] There is some preliminary evidence for it being harmful to fish.[9]
^Lewis, P.M. (January 1986). "Effect of ozone on rubbers: Countermeasures and unsolved problems". Polymer Degradation and Stability. 15 (1): 33–66. doi:10.1016/0141-3910(86)90004-2.
^ abCataldo, Franco (January 2018). "Early stages of p-phenylenediamine antiozonants reaction with ozone: Radical cation and nitroxyl radical formation". Polymer Degradation and Stability. 147: 132–141. doi:10.1016/j.polymdegradstab.2017.11.020.
^Choi, Sung-Seen (5 July 1997). "Migration of Antidegradants to the Surface in NR and SBR Vulcanizates". Journal of Applied Polymer Science. 65 (1): 117–125. doi:10.1002/(SICI)1097-4628(19970705)65:1<117::AID-APP15>3.0.CO;2-0.
^Ignatz-Hoover, Frederick; To, Byron H.; Datta, R. N.; De Hoog, Arie J.; Huntink, N. M.; Talma, A. G. (1 July 2003). "Chemical Additives Migration in Rubber". Rubber Chemistry and Technology. 76 (3): 747–768. doi:10.5254/1.3547765.
^Cao, Guodong; Wang, Wei; Zhang, Jing; Wu, Pengfei; Zhao, Xingchen; Yang, Zhu; Hu, Di; Cai, Zongwei (5 April 2022). "New Evidence of Rubber-Derived Quinones in Water, Air, and Soil". Environmental Science & Technology. 56 (7): 4142–4150. doi:10.1021/acs.est.1c07376.
^Lammintausta, K; Kalimo, K (1985). "Sensitivity to Rubber. Study with Rubber Mixes and Individual Rubber Chemicals". Dermatosen in Beruf und Umwelt. Occupation and Environment. 33 (6): 204–8. PMID 2936592.
^Conde-Salazar, Luis; del-Río, Emilio; Guimaraens, Dolores; Domingo, Antonia González (August 1993). "Type IV Allergy to Rubber Additives: A 10-Year Study of 686 Cases". Journal of the American Academy of Dermatology. 29 (2): 176–180. doi:10.1016/0190-9622(93)70163-N.
^Jordan, William P., Jr. (1971-01-01). "Contact Dermatitis From N-Isopropyl-N-Phenylparaphenylenediamine: "Volkswagen Dermatitis"". Archives of Dermatology. 103 (1): 85–87. doi:10.1001/archderm.1971.04000130087014. ISSN 0003-987X.
^Zhong, Liqiao; Peng, Weijuan; Liu, Chunsheng; Gao, Lei; Chen, Daqing; Duan, Xinbin (July 2022). "IPPD-induced growth inhibition and its mechanism in zebrafish". Ecotoxicology and Environmental Safety. 239: 113614. doi:10.1016/j.ecoenv.2022.113614.
January 13, 2023
isopropyl, phenyl, phenylenediamine, isopropyl, phenyl, phenylenediamine, often, abbreviated, ippd, organic, compound, commonly, used, antiozonant, rubbers, particularly, those, used, tires, like, other, phenylenediamine, based, antiozonants, works, virtue, io. N Isopropyl N phenyl 1 4 phenylenediamine often abbreviated IPPD is an organic compound commonly used as an antiozonant in rubbers 1 particularly those used for tires Like other p phenylenediamine based antiozonants it works by virtue of its low ionization energy which allows it to react with ozone faster than ozone will react with rubber 2 This reaction converts it to the corresponding aminoxyl radical R2N O with the ozone being converted to a hydroperoxyl radical HOO 2 these species can then be scavenged by other antioxidant polymer stabilizers N Isopropyl N phenyl 1 4 phenylenediamine NamesPreferred IUPAC name N1 Phenyl N4 propan 2 yl benzene 1 4 diamineOther names 4 IsopropylaminodiphenylamineFlexzone 3CNonox 3CRhenogran IPPD 80Santoflex IPPDVanox 3CVulkanox 4010IdentifiersCAS Number 101 72 43D model JSmol Interactive imageChEMBL ChEMBL1449018ChemSpider 7292ECHA InfoCard 100 002 700EC Number 202 969 7PubChem CID 7573RTECS number ST2650000UNII 0M7PSL4100UN number 1673CompTox Dashboard EPA DTXSID1025485InChI InChI 1S C15H18N2 c1 12 2 16 14 8 10 15 11 9 14 17 13 6 4 3 5 7 13 h3 12 16 17H 1 2H3Key OUBMGJOQLXMSNT UHFFFAOYSA NSMILES CC C NC1 CC C C C1 NC2 CC CC C2PropertiesChemical formula C 15H 18N 2Molar mass 226 323 g mol 1Appearance dark grey flakesDensity 1 04Melting point 75 C 167 F 348 K HazardsGHS labelling PictogramsSignal word DangerHazard statements H302 H317 H320 H371 H372 H373 H410Precautionary statements P260 P261 P264 P270 P272 P273 P280 P301 P312 P302 P352 P305 P351 P338 P309 P311 P314 P321 P330 P333 P313 P337 P313 P363 P391 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references IPPD is prone to process called blooming where it migrates to the surface of the rubber 3 This can be beneficial to the tire as ozone attacks the tire surface and blooming therefore moves the antiozonant to where it is most needed 4 however this also increases the leaching of IPPD into the environment Many tire producers have moved to using 6PPD instead as this migrates more slowly Oxidation of IPPD converts the central phenylenediamine ring into a quinone 5 Safety EditIPPD is a human allergen 6 7 It is the compound responsible for coining the term Volkswagen Dermatitis 8 There is some preliminary evidence for it being harmful to fish 9 See also EditN N Di 2 butyl 1 4 phenylenediamine a phenylenediamine based antioxidant used as a fuel additiveReferences Edit Lewis P M January 1986 Effect of ozone on rubbers Countermeasures and unsolved problems Polymer Degradation and Stability 15 1 33 66 doi 10 1016 0141 3910 86 90004 2 a b Cataldo Franco January 2018 Early stages of p phenylenediamine antiozonants reaction with ozone Radical cation and nitroxyl radical formation Polymer Degradation and Stability 147 132 141 doi 10 1016 j polymdegradstab 2017 11 020 Choi Sung Seen 5 July 1997 Migration of Antidegradants to the Surface in NR and SBR Vulcanizates Journal of Applied Polymer Science 65 1 117 125 doi 10 1002 SICI 1097 4628 19970705 65 1 lt 117 AID APP15 gt 3 0 CO 2 0 Ignatz Hoover Frederick To Byron H Datta R N De Hoog Arie J Huntink N M Talma A G 1 July 2003 Chemical Additives Migration in Rubber Rubber Chemistry and Technology 76 3 747 768 doi 10 5254 1 3547765 Cao Guodong Wang Wei Zhang Jing Wu Pengfei Zhao Xingchen Yang Zhu Hu Di Cai Zongwei 5 April 2022 New Evidence of Rubber Derived Quinones in Water Air and Soil Environmental Science amp Technology 56 7 4142 4150 doi 10 1021 acs est 1c07376 Lammintausta K Kalimo K 1985 Sensitivity to Rubber Study with Rubber Mixes and Individual Rubber Chemicals Dermatosen in Beruf und Umwelt Occupation and Environment 33 6 204 8 PMID 2936592 Conde Salazar Luis del Rio Emilio Guimaraens Dolores Domingo Antonia Gonzalez August 1993 Type IV Allergy to Rubber Additives A 10 Year Study of 686 Cases Journal of the American Academy of Dermatology 29 2 176 180 doi 10 1016 0190 9622 93 70163 N Jordan William P Jr 1971 01 01 Contact Dermatitis From N Isopropyl N Phenylparaphenylenediamine Volkswagen Dermatitis Archives of Dermatology 103 1 85 87 doi 10 1001 archderm 1971 04000130087014 ISSN 0003 987X Zhong Liqiao Peng Weijuan Liu Chunsheng Gao Lei Chen Daqing Duan Xinbin July 2022 IPPD induced growth inhibition and its mechanism in zebrafish Ecotoxicology and Environmental Safety 239 113614 doi 10 1016 j ecoenv 2022 113614 Retrieved from https en wikipedia org w index php title N Isopropyl N 27 phenyl 1 4 phenylenediamine amp oldid 1111875808, wikipedia, wiki, book, books, library,
