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

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

Names
IUPAC name 1-N-phenyl-4-N-propan-2-ylbenzene-1,4-diamine
Other names 4-Isopropylaminodiphenylamine Flexzone 3C Nonox 3C Rhenogran IPPD-80 Santoflex IPPD Vanox 3C Vulkanox 4010
Identifiers
CAS Number	101-72-4
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1449018
ChemSpider	7292
ECHA InfoCard	100.002.700
EC Number	202-969-7
PubChem CID	7573
RTECS number	ST2650000
UNII	0M7PSL4100
UN number	1673
CompTox Dashboard (EPA)	DTXSID1025485
InChI 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
SMILES CC(C)NC1=CC=C(C=C1)NC2=CC=CC=C2
Properties
Chemical formula	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H302, H317, H320, H371, H372, H373, H400, H410
GHS precautionary statements	P260, P261, P264, P270, P272, P273, P280, P301+312, P302+352, P305+351+338, P309+311, P314, P321, P330, P333+313, P337+313, P363, P391, P405, P501
Except 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]

Safety

IPPD is a human allergen.[4][5]

See also

• N,N'-Di-2-butyl-1,4-phenylenediamine - a phenylenediamine based antioxidant used as a fuel additive
• 6PPD another phenylenediamine antiozonant

References

1. 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.
2. 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.
3. 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.
4. 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.
5. 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.