1266:
published between
January 1992 and February 2005 that investigated the association between personal hair dye use and cancer as identified through the PubMed search engine found "at least one well-designed study with detailed exposure assessment" that observed associations between personal hair dye use and non-Hodgkin's lymphoma, multiple myeloma, acute leukemia, and bladder cancer, but those associations were not consistently observed across studies. A formal meta-analysis was not possible due to the heterogeneity of the exposure assessment across the studies.
1097:
40:
49:
385:
246:
1148:
1087:
626:
631:
621:
806:
27:
1270:
811:
980:
1265:
of PPD is 0.028 mg/L. The U.S. Environmental
Protection Agency reported that in rats and mice chronically exposed to PPD in their diet, it simply depressed body weights, and no other clinical signs of toxicity were observed in several studies. One review of 31 English-language articles
809:
1660:
Zug, Kathryn A.; Warshaw, Erin M.; Fowler, Joseph F.; Maibach, Howard I.; Belsito, Donald L.; Pratt, Melanie D.; Sasseville, Denis; Storrs, Frances J.; Taylor, James S.; Mathias, C. G. Toby; Deleo, Vincent A.; Rietschel, Robert L.; Marks, James (2009).
1314:. Sensitization is a lifelong issue, which may lead to active sensitization to products, including but not limited to black clothing, various inks, hair dye, dyed fur, dyed leather, and certain photographic products. It was voted
639:
601:
1249:
to aid identification of lichens. PPD is used extensively as a cross-linking agent in the formation of COFs (covalent organic frameworks), which have a number of applications in dyes and aromatic compounds adsorption.
1483:
1609:
Rollison, DE; Helzlsouer, KJ; Pinney, SM (2006). "Personal hair dye use and cancer: a systematic literature review and evaluation of exposure assessment in studies published since 1992".
733:
1321:
Poisoning by PPD is rare in
Western countries. In contrast, poisoning by PPD has occurred in Eastern countries, such as Pakistan, where people have committed suicide by consuming it.
1817:
Omer Sultan, Muhammad; Inam Khan, Muhammad; Ali, Rahmat; Farooque, Umar; Hassan, Syed Adeel; Karimi, Sundas; Cheema, Omer; Pillai, Bharat; Asghar, Fahham; Javed, Rafay (2020-05-29).
810:
1469:
1413:
920:
993:
1092:
In the DuPont route, aniline is converted to diphenyltriazine, which is then converted by acid-catalysis to 4-aminoazobenzene. Hydrogenation of the latter affords PPD.
812:
1197:
434:
1298:. Exposure routes are through inhalation, skin absorption, ingestion, and skin and/or eye contact. Symptoms of exposure to PPD include throat irritation (
729:
1374:
1180:. Derivatives of diaminopyrazole give both red and violet colours. In these applications, the nearly colourless dye precursor oxidizes to the dye.
1200:). The substituents (naphthyl, isopropyl, etc.) affect the effectiveness of their antioxidant roles as well as their properties as skin irritants.
834:
1520:
1428:
1212:
color photographic film development process, reacting with the silver grains in the film and creating the colored dyes that form the image.
1442:
399:
1716:
1766:
Ashraf, W.; Dawling, S.; Farrow, L. J. (1994). "Systemic
Paraphenylenediamine (PPD) Poisoning: A Case Report and Review".
1741:
717:
721:
687:
332:
757:
630:
1291:
709:
363:
777:
1819:"Paraphenylenediamine (Kala Pathar) Poisoning at the National Poison Control Center in Karachi: A Prospective Study"
820:
625:
1000:
944:
931:
548:
253:
1046:
is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering
857:
39:
761:
741:
584:
241:
48:
1129:
1378:
183:
653:
620:
613:
1576:
1147:
1096:
765:
1775:
1618:
1315:
1071:
67:
679:
1742:"NIOSH Registry of Toxic Effects of Chemical Substances (RTECS) entry for p-Phenylenediamine (PPD)"
701:
380:
131:
97:
1128:
which allow the molecules to be strung together. This polymer arises from the reaction of PPD and
1799:
1698:
1642:
1259:
1246:
1220:
1173:
693:
143:
1086:
705:
1892:
1887:
1882:
1858:
1840:
1791:
1690:
1682:
1634:
1516:
1438:
203:
1208:
A substituted form of PPD sold under the name CD-4 is also used as a developing agent in the
1848:
1830:
1783:
1674:
1626:
1560:
1540:
1508:
1502:
1023:
527:
457:
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341:
749:
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737:
107:
1779:
1622:
769:
384:
245:
163:
1853:
1818:
1079:
971:
538:
1876:
1242:
1055:
516:
506:
234:
1803:
1702:
1646:
785:
1720:
1209:
1141:
697:
667:
1596:
1564:
1544:
26:
713:
305:
1745:
1357:
1189:
906:
884:
846:
1787:
1176:). Other popular derivatives include tetraaminopyrimidine and indoanilines and
1630:
1409:
1311:
1284:
1273:
1269:
1177:
1137:
485:
194:
1844:
1686:
1663:"Patch-test results of the North American Contact Dermatitis Group 2005-2006"
1512:
1461:
1124:. These applications exploit PPD's difunctionality, i.e. the presence of two
671:
1678:
1662:
1434:
1188:
PPD is easily oxidized, and for this reason, derivatives of PPD are used as
352:
1862:
1694:
1638:
1795:
663:
1295:
1280:
1227:
1165:
1133:
833:
826:
819:
792:
214:
1835:
223:
1611:
Journal of
Toxicology and Environmental Health Part B: Critical Reviews
1299:
1169:
1152:
1075:
1047:
1043:
292:
254:
1172:
analogues and derivatives such as 2,5-diamino(hydroxyethylbenzene and
1307:
1303:
1235:
1216:
1193:
1121:
1117:
1113:
1051:
174:
1555:
Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and
Additives" in
970:
Except where otherwise noted, data are given for materials in their
280:
1330:
1268:
1231:
1146:
1125:
1059:
659:
316:
154:
130:
120:
827:
773:
957:
781:
675:
271:
1466:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
753:
368:
47:
38:
511:
145 to 147 °C (293 to 297 °F; 418 to 420 K)
804:
1155:
subunit is bolded, dashed lines indicate hydrogen bonds.
988:
501:
White crystalline solid, darkens upon exposure to air
1470:
National
Institute for Occupational Safety and Health
1414:
National
Institute for Occupational Safety and Health
1318:
in 2006 by the
American Contact Dermatitis Society.
1215:
PPD is also used as a henna surrogate for temporary
1070:PPD is produced via three routes. Most commonly,
304:
1667:Dermatitis: Contact, Atopic, Occupational, Drug
808:
106:
1557:Ullmann's Encyclopedia of Industrial Chemistry
1537:Ullmann's Encyclopedia of Industrial Chemistry
1504:Ullmann's Encyclopedia of Industrial Chemistry
408:InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
1535:Thomas Clausen et al. "Hair Preparations" in
1058:and is occasionally used as a substitute for
418:InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
8:
1717:"The NIOSH Pocket Guide to Chemical Hazards"
1279:In 2005–06, it was the tenth-most-prevalent
564:2.97 (doubly protonated form; 20 °C, H
533:10% at 40°C, 87% at 107 C, 100% at 140 C
383:
244:
202:
15:
1852:
1834:
1497:
1495:
1493:
1375:"P-Phenylenediamine (1,4-Diaminobenzene)"
340:
1408:NIOSH Pocket Guide to Chemical Hazards.
1352:
1350:
1348:
1346:
1342:
1168:. Its use is being supplanted by other
439:
404:
379:
222:
1599:, U.S. Environmental Protection Agency
1456:
1454:
1403:
1401:
1399:
1397:
1395:
865:400 °C (752 °F; 673 K)
521:267 °C (513 °F; 540 K)
235:
1430:CRC Handbook of Chemistry and Physics
851:156 °C; 312 °F; 429 K
411:Key: CBCKQZAAMUWICA-UHFFFAOYSA-N
182:
162:
7:
1768:Human & Experimental Toxicology
1151:Molecular structure of Kevlar: the
571:6.31 (conjugate acid; 20 °C, H
421:Key: CBCKQZAAMUWICA-UHFFFAOYAD
295:
279:
14:
1507:(1 ed.). Wiley. 2003-03-11.
1427:Haynes, William M., ed. (2016).
1095:
1085:
978:
629:
624:
619:
475:
469:
25:
1219:. Its usage can lead to severe
974:(at 25 °C , 100 kPa).
1054:. It is also an ingredient in
463:
1:
1565:10.1002/14356007.a23_365.pub2
1559:, 2007, Wiley-VCH, Weinheim.
1545:10.1002/14356007.a12_571.pub2
1539:, 2007, Wiley-VCH, Weinheim.
1294:lists PPD as being a contact
925:(US health exposure limits):
895:145 mg/kg (guinea pig, oral)
1579:. The British Lichen Society
1132:. The reaction of PPD with
1116:plastics and fibers such as
1486:. Thermo Fisher Scientific.
873:or concentration (LD, LC):
34:
1909:
1788:10.1177/096032719401300305
1164:This compound is a common
1631:10.1080/10937400600681455
1484:"p-Phenylenediamine MSDS"
968:
919:
869:
600:
595:
450:
430:
395:
90:
78:
66:
61:
33:
24:
1513:10.1002/14356007.a19_405
913:250 mg/kg (rabbit, oral)
688:Precautionary statements
1679:10.2310/6620.2009.08097
585:Magnetic susceptibility
1276:
1226:PPD is also used as a
1156:
1130:terephthaloyl chloride
1112:PPD is a precursor to
1082:is then hydrogenated:
915:100 mg/kg (cat, oral)
815:
52:
43:
1462:"p-Phenylene diamine"
1272:
1192:in the production of
1150:
1108:Precursor to polymers
1042:. This derivative of
814:
51:
42:
1316:Allergen of the Year
1310:, and sensitization
1072:4-nitrochlorobenzene
1050:and composites like
893:98 mg/kg (rat, oral)
891:80 mg/kg (rat, oral)
797:(fire diamond)
85:1,4-Phenylenediamine
81:Paraphenylenediamine
68:Preferred IUPAC name
1836:10.7759/cureus.8352
1780:1994HETox..13..167A
1623:2006JTEHB...9..413R
528:Solubility in water
493: g·mol
144:Beilstein Reference
72:Benzene-1,4-diamine
21:
1597:p-Phenylenediamine
1277:
1228:histological stain
1221:contact dermatitis
1184:Rubber antioxidant
1174:2,5-diaminotoluene
1157:
1078:and the resulting
1026:with the formula C
1001:Infobox references
960:(Immediate danger)
816:
543:<1 mmHg (20°C)
83:1,4-Diaminobenzene
53:
44:
20:-Phenylenediamine
16:
1522:978-3-527-30385-4
1437:. pp. 5–89.
1433:(97th ed.).
1140:, a precursor to
1016:-Phenylenediamine
1009:Chemical compound
1007:
1006:
654:Hazard statements
591:-70.28·10 cm/mol
364:CompTox Dashboard
132:Interactive image
57:
56:
1900:
1867:
1866:
1856:
1838:
1814:
1808:
1807:
1763:
1757:
1756:
1754:
1753:
1744:. Archived from
1738:
1732:
1731:
1729:
1728:
1719:. Archived from
1713:
1707:
1706:
1657:
1651:
1650:
1606:
1600:
1594:
1588:
1587:
1585:
1584:
1577:"Chemical Tests"
1573:
1567:
1553:
1547:
1533:
1527:
1526:
1499:
1488:
1487:
1480:
1474:
1473:
1458:
1449:
1448:
1424:
1418:
1417:
1405:
1390:
1389:
1387:
1386:
1377:. Archived from
1371:
1365:
1361:, 11th Edition,
1354:
1196:products (e.g.,
1099:
1089:
1074:is treated with
1024:organic compound
991:
985:
982:
981:
907:lowest published
836:
829:
822:
807:
787:
783:
779:
775:
771:
767:
763:
759:
755:
751:
747:
743:
739:
735:
731:
727:
723:
719:
715:
711:
707:
703:
699:
695:
681:
677:
673:
669:
665:
661:
633:
628:
623:
492:
477:
471:
465:
458:Chemical formula
388:
387:
372:
370:
344:
308:
297:
283:
256:
248:
237:
226:
206:
186:
166:
134:
110:
35:
29:
22:
1908:
1907:
1903:
1902:
1901:
1899:
1898:
1897:
1873:
1872:
1871:
1870:
1816:
1815:
1811:
1765:
1764:
1760:
1751:
1749:
1740:
1739:
1735:
1726:
1724:
1715:
1714:
1710:
1659:
1658:
1654:
1608:
1607:
1603:
1595:
1591:
1582:
1580:
1575:
1574:
1570:
1554:
1550:
1534:
1530:
1523:
1501:
1500:
1491:
1482:
1481:
1477:
1460:
1459:
1452:
1445:
1426:
1425:
1421:
1407:
1406:
1393:
1384:
1382:
1373:
1372:
1368:
1355:
1344:
1339:
1327:
1263:
1256:
1241:PPD is used by
1206:
1186:
1162:
1110:
1105:
1068:
1041:
1037:
1033:
1029:
1010:
1003:
998:
997:
996: ?)
987:
983:
979:
975:
961:
948:
935:
914:
910:
904:
894:
892:
888:
882:
862:
859:
841:
840:
839:
838:
831:
824:
817:
813:
805:
690:
656:
642:
616:
588:
578:
574:
567:
557:
530:
490:
480:
474:
468:
460:
446:
443:
438:
437:
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419:
413:
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409:
403:
402:
391:
373:
366:
347:
327:
311:
298:
286:
266:
229:
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189:
169:
146:
137:
124:
113:
100:
86:
84:
82:
74:
73:
12:
11:
5:
1906:
1904:
1896:
1895:
1890:
1885:
1875:
1874:
1869:
1868:
1809:
1758:
1733:
1708:
1673:(3): 149–160.
1652:
1601:
1589:
1568:
1548:
1528:
1521:
1489:
1475:
1450:
1444:978-1498754286
1443:
1419:
1391:
1366:
1341:
1340:
1338:
1335:
1334:
1333:
1326:
1323:
1261:
1255:
1252:
1243:lichenologists
1205:
1202:
1185:
1182:
1161:
1158:
1109:
1106:
1104:
1101:
1080:4-nitroaniline
1067:
1064:
1039:
1035:
1031:
1027:
1008:
1005:
1004:
999:
977:
976:
972:standard state
969:
966:
965:
962:
956:
953:
952:
951:TWA 0.1 mg/m
949:
943:
940:
939:
938:TWA 0.1 mg/m
936:
930:
927:
926:
917:
916:
911:
902:
900:
897:
896:
889:
880:
878:
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867:
866:
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852:
849:
843:
842:
832:
825:
818:
803:
802:
801:
800:
798:
789:
788:
734:P305+P351+P338
691:
686:
683:
682:
657:
652:
649:
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583:
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579:
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569:
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541:
539:Vapor pressure
535:
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531:
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13:
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9:
6:
4:
3:
2:
1905:
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1855:
1850:
1846:
1842:
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1824:
1820:
1813:
1810:
1805:
1801:
1797:
1793:
1789:
1785:
1781:
1777:
1774:(3): 167–70.
1773:
1769:
1762:
1759:
1748:on 2010-03-31
1747:
1743:
1737:
1734:
1723:on 2017-10-24
1722:
1718:
1712:
1709:
1704:
1700:
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1668:
1664:
1656:
1653:
1648:
1644:
1640:
1636:
1632:
1628:
1624:
1620:
1617:(5): 413–39.
1616:
1612:
1605:
1602:
1598:
1593:
1590:
1578:
1572:
1569:
1566:
1562:
1558:
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1510:
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1505:
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1496:
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1471:
1467:
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1457:
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1432:
1431:
1423:
1420:
1415:
1411:
1404:
1402:
1400:
1398:
1396:
1392:
1381:on 2012-03-13
1380:
1376:
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1360:
1359:
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1347:
1343:
1336:
1332:
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1317:
1313:
1309:
1306:), bronchial
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1275:
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1233:
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1218:
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1211:
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1199:
1195:
1191:
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1179:
1175:
1171:
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1159:
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1123:
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1090:
1088:
1083:
1081:
1077:
1073:
1065:
1063:
1061:
1057:
1053:
1049:
1045:
1025:
1021:
1017:
1015:
1002:
995:
990:
973:
967:
963:
959:
955:
954:
950:
947:(Recommended)
946:
942:
941:
937:
934:(Permissible)
933:
929:
928:
924:
923:
918:
912:
908:
899:
898:
890:
886:
877:
876:
872:
868:
864:
861:
855:
854:
850:
848:
845:
844:
837:
830:
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442:Nc1ccc(N)cc1
317:RTECS number
184:ChEMBL403741
91:Identifiers
79:Other names
17:
1358:Merck Index
1285:patch tests
1178:indophenols
885:median dose
871:Lethal dose
860:temperature
847:Flash point
640:Signal word
498:Appearance
451:Properties
242:100.003.096
164:CHEBI:51403
1877:Categories
1752:2017-09-07
1727:2017-09-07
1583:2019-04-30
1385:2011-07-14
1337:References
1312:dermatitis
1274:Patch test
1204:Other uses
1144:polymers.
1138:isocyanate
1066:Production
614:Pictograms
486:Molar mass
342:U770QIT64J
195:ChemSpider
119:3D model (
98:CAS Number
1845:2168-8184
1687:2162-5220
1435:CRC Press
1056:hair dyes
778:P403+P233
762:P337+P313
758:P333+P313
730:P304+P340
726:P302+P352
722:P301+P310
605:labelling
353:UN number
324:SS8050000
263:203-404-7
255:EC Number
1893:Monomers
1888:Diamines
1883:Anilines
1863:32617225
1804:31229733
1703:24088485
1695:19470301
1647:23749135
1639:17492526
1472:(NIOSH).
1416:(NIOSH).
1325:See also
1296:allergen
1287:(5.0%).
1281:allergen
1234:such as
1166:hair dye
1142:urethane
1134:phosgene
1048:polymers
1022:) is an
964:25 mg/m
794:NFPA 704
596:Hazards
587:(χ)
215:DrugBank
204:13835179
108:106-50-3
1854:7325408
1796:7909678
1776:Bibcode
1619:Bibcode
1410:"#0495"
1300:pharynx
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1217:tattoos
1170:aniline
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435:SMILES
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