31:
316:
197:
477:
472:
482:
704:, where it migrates to the surface of the rubber. 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, however this also increases the
490:
452:
584:
960:
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".
849:
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".
355:
795:
Cataldo, Franco (January 2018). "Early stages of p-phenylenediamine antiozonants reaction with ozone: Radical cation and nitroxyl radical formation".
737:
728:. It is the compound responsible for coining the term "Volkswagen Dermatitis". There is some preliminary evidence for it being harmful to fish.
835:
134:
1100:
330:
995:
Jordan, William P. Jr. (1971-01-01). "Contact
Dermatitis From N-Isopropyl-N-Phenylparaphenylenediamine: "Volkswagen Dermatitis"".
693:
N–O•), with the ozone being converted to a hydroperoxyl radical (HOO•), these species can then be scavenged by other antioxidant
576:
588:
572:
639:
542:
263:
604:
481:
476:
1095:
564:
294:
933:
Lammintausta, K; Kalimo, K (1985). "Sensitivity to Rubber. Study with Rubber Mixes and
Individual Rubber Chemicals".
471:
876:
Cao, Guodong; Wang, Wei; Zhang, Jing; Wu, Pengfei; Zhao, Xingchen; Yang, Zhu; Hu, Di; Cai, Zongwei (5 April 2022).
30:
530:
204:
608:
526:
712:
instead, as this migrates more slowly. Oxidation of IPPD converts the central phenylenediamine ring into a
192:
154:
1085:
822:
Choi, Sung-Seen (5 July 1997). "Migration of
Antidegradants to the Surface in NR and SBR Vulcanizates".
504:
464:
889:
705:
43:
534:
694:
560:
311:
100:
1061:
765:
Lewis, P.M. (January 1986). "Effect of ozone on rubbers: Countermeasures and unsolved problems".
674:
552:
1030:
Zhong, Liqiao; Peng, Weijuan; Liu, Chunsheng; Gao, Lei; Chen, Daqing; Duan, Xinbin (July 2022).
592:
548:
1090:
1053:
1012:
977:
942:
915:
678:
1043:
1004:
969:
905:
897:
858:
831:
804:
774:
666:
378:
596:
272:
808:
580:
315:
196:
174:
1008:
685:
faster than ozone will react with rubber. This reaction converts it to the corresponding
110:
893:
612:
910:
877:
633:
1079:
1065:
973:
778:
701:
437:
339:
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
185:
624:
556:
514:
1048:
1031:
568:
236:
670:
406:
165:
1016:
901:
283:
1057:
919:
836:
10.1002/(SICI)1097-4628(19970705)65:1<117::AID-APP15>3.0.CO;2-0
981:
946:
522:
725:
686:
713:
427:
223:
205:
862:
708:
of IPPD into the environment. Many tire producers have moved to using
518:
145:
632:
Except where otherwise noted, data are given for materials in their
510:
682:
247:
133:
123:
878:"New Evidence of Rubber-Derived Quinones in Water, Air, and Soil"
616:
709:
620:
1032:"IPPD-induced growth inhibition and its mechanism in zebrafish"
747:- a phenylenediamine based antioxidant used as a fuel additive
600:
299:
935:
Dermatosen in Beruf und Umwelt. Occupation and
Environment
677:-based antiozonants it works by virtue of its low
235:
109:
962:Journal of the American Academy of Dermatology
8:
790:
788:
314:
195:
173:
15:
1047:
909:
271:
757:
360:
335:
310:
1036:Ecotoxicology and Environmental Safety
882:Environmental Science & Technology
186:
809:10.1016/j.polymdegradstab.2017.11.020
442:75 °C (167 °F; 348 K)
342:Key: OUBMGJOQLXMSNT-UHFFFAOYSA-N
153:
7:
1009:10.1001/archderm.1971.04000130087014
226:
824:Journal of Applied Polymer Science
14:
797:Polymer Degradation and Stability
767:Polymer Degradation and Stability
745:′-Di-2-butyl-1,4-phenylenediamine
55:-(propan-2-yl)benzene-1,4-diamine
700:IPPD is prone to process called
681:, which allows it to react with
480:
475:
470:
396:
390:
29:
851:Rubber Chemistry and Technology
636:(at 25 °C , 100 kPa).
363:CC(C)NC1=CC=C(C=C1)NC2=CC=CC=C2
384:
24:′-phenyl-1,4-phenylenediamine
1:
659:′-phenyl-1,4-phenylenediamine
67:4-Isopropylaminodiphenylamine
1049:10.1016/j.ecoenv.2022.113614
974:10.1016/0190-9622(93)70163-N
779:10.1016/0141-3910(86)90004-2
1117:
630:
451:
446:
371:
351:
326:
93:
61:
42:
37:
28:
1101:Isopropylamino compounds
543:Precautionary statements
997:Archives of Dermatology
902:10.1021/acs.est.1c07376
673:in rubbers. Like other
669:commonly used as an
661:(often abbreviated
44:Preferred IUPAC name
894:2022EnST...56.4142C
695:polymer stabilizers
414: g·mol
25:
1096:Plastics additives
675:p-phenylenediamine
640:Infobox references
16:
863:10.5254/1.3547765
679:ionization energy
648:Chemical compound
646:
645:
505:Hazard statements
422:dark grey flakes
295:CompTox Dashboard
135:Interactive image
76:Rhenogran IPPD-80
1108:
1070:
1069:
1051:
1027:
1021:
1020:
992:
986:
985:
957:
951:
950:
930:
924:
923:
913:
888:(7): 4142–4150.
873:
867:
866:
846:
840:
839:
819:
813:
812:
792:
783:
782:
762:
724:IPPD is a human
667:organic compound
626:
622:
618:
614:
610:
606:
602:
598:
594:
590:
586:
582:
578:
574:
570:
566:
562:
558:
554:
550:
536:
532:
528:
524:
520:
516:
512:
484:
479:
474:
413:
398:
392:
386:
379:Chemical formula
319:
318:
303:
301:
275:
239:
228:
207:
199:
188:
177:
157:
137:
113:
33:
26:
1116:
1115:
1111:
1110:
1109:
1107:
1106:
1105:
1076:
1075:
1074:
1073:
1029:
1028:
1024:
994:
993:
989:
959:
958:
954:
932:
931:
927:
875:
874:
870:
848:
847:
843:
821:
820:
816:
794:
793:
786:
764:
763:
759:
754:
734:
722:
692:
649:
642:
637:
545:
507:
493:
467:
411:
401:
395:
389:
381:
367:
364:
359:
358:
347:
344:
343:
340:
334:
333:
322:
304:
297:
278:
258:
242:
229:
217:
180:
160:
140:
127:
116:
103:
89:
88:
57:
56:
12:
11:
5:
1114:
1112:
1104:
1103:
1098:
1093:
1088:
1078:
1077:
1072:
1071:
1022:
987:
968:(2): 176–180.
952:
925:
868:
857:(3): 747–768.
841:
830:(1): 117–125.
814:
784:
756:
755:
753:
750:
749:
748:
733:
730:
721:
718:
690:
647:
644:
643:
638:
634:standard state
631:
628:
627:
585:P305+P351+P338
546:
541:
538:
537:
508:
503:
500:
499:
494:
489:
486:
485:
468:
463:
460:
459:
449:
448:
444:
443:
440:
434:
433:
430:
424:
423:
420:
416:
415:
409:
403:
402:
399:
393:
387:
382:
377:
374:
373:
369:
368:
366:
365:
362:
354:
353:
352:
349:
348:
346:
345:
341:
338:
337:
329:
328:
327:
324:
323:
321:
320:
307:
305:
293:
290:
289:
286:
280:
279:
277:
276:
268:
266:
260:
259:
257:
256:
252:
250:
244:
243:
241:
240:
232:
230:
222:
219:
218:
216:
215:
211:
209:
201:
200:
190:
182:
181:
179:
178:
170:
168:
162:
161:
159:
158:
150:
148:
142:
141:
139:
138:
130:
128:
121:
118:
117:
115:
114:
106:
104:
99:
96:
95:
91:
90:
87:
86:
83:
80:
79:Santoflex IPPD
77:
74:
71:
68:
64:
63:
59:
58:
47:
46:
40:
39:
35:
34:
13:
10:
9:
6:
4:
3:
2:
1113:
1102:
1099:
1097:
1094:
1092:
1089:
1087:
1084:
1083:
1081:
1067:
1063:
1059:
1055:
1050:
1045:
1041:
1037:
1033:
1026:
1023:
1018:
1014:
1010:
1006:
1002:
998:
991:
988:
983:
979:
975:
971:
967:
963:
956:
953:
948:
944:
940:
936:
929:
926:
921:
917:
912:
907:
903:
899:
895:
891:
887:
883:
879:
872:
869:
864:
860:
856:
852:
845:
842:
837:
833:
829:
825:
818:
815:
810:
806:
802:
798:
791:
789:
785:
780:
776:
772:
768:
761:
758:
751:
746:
744:
740:
736:
735:
731:
729:
727:
719:
717:
715:
711:
707:
703:
698:
696:
688:
684:
680:
676:
672:
668:
664:
660:
658:
654:
641:
635:
629:
547:
544:
540:
539:
509:
506:
502:
501:
498:
495:
492:
488:
487:
483:
478:
473:
469:
466:
462:
461:
457:
455:
450:
445:
441:
439:
438:Melting point
436:
435:
431:
429:
426:
425:
421:
418:
417:
410:
408:
405:
404:
383:
380:
376:
375:
370:
361:
357:
350:
336:
332:
325:
317:
313:
312:DTXSID1025485
309:
308:
306:
296:
292:
291:
287:
285:
282:
281:
274:
270:
269:
267:
265:
262:
261:
254:
253:
251:
249:
246:
245:
238:
234:
233:
231:
225:
221:
220:
213:
212:
210:
208:
203:
202:
198:
194:
191:
189:
187:ECHA InfoCard
184:
183:
176:
172:
171:
169:
167:
164:
163:
156:
155:ChEMBL1449018
152:
151:
149:
147:
144:
143:
136:
132:
131:
129:
125:
120:
119:
112:
108:
107:
105:
102:
98:
97:
92:
85:Vulkanox 4010
84:
81:
78:
75:
72:
69:
66:
65:
60:
54:
50:
45:
41:
36:
32:
27:
23:
19:
1086:Antioxidants
1039:
1035:
1025:
1003:(1): 85–87.
1000:
996:
990:
965:
961:
955:
941:(6): 204–8.
938:
934:
928:
885:
881:
871:
854:
850:
844:
827:
823:
817:
800:
796:
773:(1): 33–66.
770:
766:
760:
742:
738:
723:
699:
662:
656:
652:
651:
650:
496:
453:
248:RTECS number
94:Identifiers
62:Other names
52:
48:
21:
17:
803:: 132–141.
671:antiozonant
655:-Isopropyl-
491:Signal word
419:Appearance
372:Properties
193:100.002.700
70:Flexzone 3C
20:-Isopropyl-
1080:Categories
1042:: 113614.
752:References
689:radical (R
465:Pictograms
407:Molar mass
273:0M7PSL4100
166:ChemSpider
122:3D model (
101:CAS Number
1066:248728812
1017:0003-987X
609:P337+P313
605:P333+P313
589:P309+P311
581:P302+P352
577:P301+P312
456:labelling
284:UN number
255:ST2650000
214:202-969-7
206:EC Number
1091:Diamines
1058:35567929
920:35316033
732:See also
726:allergen
706:leaching
702:blooming
687:aminoxyl
665:) is an
447:Hazards
111:101-72-4
82:Vanox 3C
73:Nonox 3C
51:-Phenyl-
982:8335734
947:2936592
911:8988306
890:Bibcode
714:quinone
428:Density
412:226.323
224:PubChem
1064:
1056:
1015:
980:
945:
918:
908:
720:Safety
497:Danger
356:SMILES
146:ChEMBL
38:Names
1062:S2CID
683:ozone
432:1.04
331:InChI
288:1673
124:JSmol
1054:PMID
1013:ISSN
978:PMID
943:PMID
916:PMID
710:6PPD
663:IPPD
625:P501
621:P405
617:P391
613:P363
601:P330
597:P321
593:P314
573:P280
569:P273
565:P272
561:P270
557:P264
553:P261
549:P260
535:H410
531:H373
527:H372
523:H371
519:H320
515:H317
511:H302
264:UNII
237:7573
175:7292
1044:doi
1040:239
1005:doi
1001:103
970:doi
906:PMC
898:doi
859:doi
832:doi
805:doi
801:147
775:doi
697:.
454:GHS
300:EPA
227:CID
1082::
1060:.
1052:.
1038:.
1034:.
1011:.
999:.
976:.
966:29
964:.
939:33
937:.
914:.
904:.
896:.
886:56
884:.
880:.
855:76
853:.
828:65
826:.
799:.
787:^
771:15
769:.
716:.
623:,
619:,
615:,
611:,
607:,
603:,
599:,
595:,
591:,
587:,
583:,
579:,
575:,
571:,
567:,
563:,
559:,
555:,
551:,
533:,
529:,
525:,
521:,
517:,
513:,
458::
394:18
388:15
1068:.
1046::
1019:.
1007::
984:.
972::
949:.
922:.
900::
892::
865:.
861::
838:.
834::
811:.
807::
781:.
777::
743:N
741:,
739:N
691:2
657:N
653:N
400:2
397:N
391:H
385:C
302:)
298:(
126:)
53:N
49:N
22:N
18:N
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
