N-Isopropyl-N'-phenyl-1,4-phenylenediamine

Source: Wikipedia, the free encyclopedia.
N-Isopropyl-N′-phenyl-1,4-phenylenediamine
Names
Preferred IUPAC name
N1-Phenyl-N4-(propan-2-yl)benzene-1,4-diamine
Other names
  • 4-Isopropylaminodiphenylamine
  • Flexzone 3C
  • Nonox 3C
  • Rhenogran IPPD-80
  • Santoflex IPPD
  • Vanox 3C
  • Vulkanox 4010
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.002.700 Edit this at Wikidata
EC Number
  • 202-969-7
RTECS number
  • ST2650000
UNII
UN number 1673
  • 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,1-2H3
    Key: OUBMGJOQLXMSNT-UHFFFAOYSA-N
  • CC(C)NC1=CC=C(C=C1)NC2=CC=CC=C2
Properties
C15H18N2
Molar mass 226.323 g·mol−1
Appearance dark grey flakes
Density 1.04
Melting point 75 °C (167 °F; 348 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H302, H317, H320, H371, H372, H373, H410
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, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Isopropyl-N′-phenyl-1,4-phenylenediamine (often abbreviated IPPD) is an

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]

See also

References

  1. doi:10.1016/0141-3910(86)90004-2
    .
  2. ^
    doi:10.1016/j.polymdegradstab.2017.11.020
    .
  3. doi:10.1002/(SICI)1097-4628(19970705)65:1<117::AID-APP15>3.0.CO;2-0
    .
  4. doi:10.5254/1.3547765
    .
  5. PMID 35316033
    .
  6. PMID 2936592
    .
  7. PMID 8335734
    .
  8. ISSN 0003-987X
    .
  9. S2CID 248728812
    .
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