1277:
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.
1108:
51:
60:
396:
257:
1159:
1098:
637:
642:
632:
817:
38:
1281:
822:
991:
1276:
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
820:
1671:
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).
1325:. 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
650:
612:
1260:
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.
1494:
1620:
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".
744:
1332:
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.
1828:
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).
821:
1480:
1424:
931:
1004:
1103:
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.
823:
1208:
445:
1309:. Exposure routes are through inhalation, skin absorption, ingestion, and skin and/or eye contact. Symptoms of exposure to PPD include throat irritation (
740:
1385:
1191:. Derivatives of diaminopyrazole give both red and violet colours. In these applications, the nearly colourless dye precursor oxidizes to the dye.
1211:). The substituents (naphthyl, isopropyl, etc.) affect the effectiveness of their antioxidant roles as well as their properties as skin irritants.
845:
1531:
1439:
1223:
color photographic film development process, reacting with the silver grains in the film and creating the colored dyes that form the image.
1453:
410:
1727:
1777:
Ashraf, W.; Dawling, S.; Farrow, L. J. (1994). "Systemic
Paraphenylenediamine (PPD) Poisoning: A Case Report and Review".
1752:
728:
732:
698:
343:
768:
641:
1302:
720:
374:
788:
1830:"Paraphenylenediamine (Kala Pathar) Poisoning at the National Poison Control Center in Karachi: A Prospective Study"
831:
636:
1011:
955:
942:
559:
264:
1057:
is a white solid, but samples can darken due to air oxidation. It is mainly used as a component of engineering
868:
50:
772:
752:
595:
252:
59:
1140:
1389:
194:
664:
631:
624:
1587:
1158:
1107:
776:
1786:
1629:
1326:
1082:
78:
690:
1753:"NIOSH Registry of Toxic Effects of Chemical Substances (RTECS) entry for p-Phenylenediamine (PPD)"
712:
391:
142:
108:
1139:
which allow the molecules to be strung together. This polymer arises from the reaction of PPD and
1810:
1709:
1653:
1270:
1257:
1231:
1184:
704:
154:
1097:
716:
1903:
1898:
1893:
1869:
1851:
1802:
1701:
1693:
1645:
1527:
1449:
214:
1219:
A substituted form of PPD sold under the name CD-4 is also used as a developing agent in the
1859:
1841:
1794:
1685:
1637:
1571:
1551:
1519:
1513:
1034:
538:
468:
756:
352:
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736:
748:
118:
1790:
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780:
395:
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174:
1864:
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982:
549:
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1253:
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527:
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245:
1814:
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17:
1731:
1220:
1152:
708:
678:
1607:
1575:
1555:
37:
724:
316:
1756:
1368:
1200:
917:
895:
857:
1798:
1187:). Other popular derivatives include tetraaminopyrimidine and indoanilines and
1641:
1420:
1322:
1295:
1284:
1280:
1188:
1148:
496:
205:
1855:
1697:
1674:"Patch-test results of the North American Contact Dermatitis Group 2005-2006"
1523:
1472:
1135:. These applications exploit PPD's difunctionality, i.e. the presence of two
682:
1689:
1673:
1445:
1199:
PPD is easily oxidized, and for this reason, derivatives of PPD are used as
363:
1873:
1705:
1649:
1806:
674:
1306:
1291:
1238:
1176:
1144:
844:
837:
830:
803:
225:
1846:
234:
1622:
Journal of
Toxicology and Environmental Health Part B: Critical Reviews
1310:
1180:
1163:
1086:
1058:
1054:
303:
265:
1183:
analogues and derivatives such as 2,5-diamino(hydroxyethylbenzene and
1318:
1314:
1246:
1227:
1204:
1132:
1128:
1124:
1062:
185:
1566:
Hans-Wilhelm Engels et al., "Rubber, 4. Chemicals and
Additives" in
981:
Except where otherwise noted, data are given for materials in their
291:
1341:
1279:
1242:
1157:
1136:
1070:
670:
327:
165:
141:
131:
838:
784:
968:
792:
686:
282:
1477:
Immediately
Dangerous to Life or Health Concentrations (IDLH)
764:
379:
58:
49:
522:
145 to 147 °C (293 to 297 °F; 418 to 420 K)
815:
1166:
subunit is bolded, dashed lines indicate hydrogen bonds.
999:
512:
White crystalline solid, darkens upon exposure to air
1481:
National
Institute for Occupational Safety and Health
1425:
National
Institute for Occupational Safety and Health
1329:
in 2006 by the
American Contact Dermatitis Society.
1226:
PPD is also used as a henna surrogate for temporary
1081:PPD is produced via three routes. Most commonly,
315:
1678:Dermatitis: Contact, Atopic, Occupational, Drug
819:
117:
1568:Ullmann's Encyclopedia of Industrial Chemistry
1548:Ullmann's Encyclopedia of Industrial Chemistry
1515:Ullmann's Encyclopedia of Industrial Chemistry
419:InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
1546:Thomas Clausen et al. "Hair Preparations" in
1069:and is occasionally used as a substitute for
429:InChI=1/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
8:
1728:"The NIOSH Pocket Guide to Chemical Hazards"
1290:In 2005–06, it was the tenth-most-prevalent
575:2.97 (doubly protonated form; 20 °C, H
544:10% at 40°C, 87% at 107 C, 100% at 140 C
394:
255:
213:
26:
1863:
1845:
1508:
1506:
1504:
1386:"P-Phenylenediamine (1,4-Diaminobenzene)"
351:
1419:NIOSH Pocket Guide to Chemical Hazards.
1363:
1361:
1359:
1357:
1353:
1179:. Its use is being supplanted by other
450:
415:
390:
233:
1610:, U.S. Environmental Protection Agency
1467:
1465:
1414:
1412:
1410:
1408:
1406:
876:400 °C (752 °F; 673 K)
532:267 °C (513 °F; 540 K)
246:
1441:CRC Handbook of Chemistry and Physics
862:156 °C; 312 °F; 429 K
422:Key: CBCKQZAAMUWICA-UHFFFAOYSA-N
193:
173:
7:
1779:Human & Experimental Toxicology
1162:Molecular structure of Kevlar: the
582:6.31 (conjugate acid; 20 °C, H
432:Key: CBCKQZAAMUWICA-UHFFFAOYAD
306:
290:
25:
1518:(1 ed.). Wiley. 2003-03-11.
1438:Haynes, William M., ed. (2016).
1106:
1096:
989:
640:
635:
630:
486:
480:
36:
1230:. Its usage can lead to severe
985:(at 25 °C , 100 kPa).
1065:. It is also an ingredient in
474:
1:
1576:10.1002/14356007.a23_365.pub2
1570:, 2007, Wiley-VCH, Weinheim.
1556:10.1002/14356007.a12_571.pub2
1550:, 2007, Wiley-VCH, Weinheim.
1305:lists PPD as being a contact
936:(US health exposure limits):
906:145 mg/kg (guinea pig, oral)
1590:. The British Lichen Society
1143:. The reaction of PPD with
1127:plastics and fibers such as
1497:. Thermo Fisher Scientific.
884:or concentration (LD, LC):
45:
1920:
1799:10.1177/096032719401300305
1175:This compound is a common
1642:10.1080/10937400600681455
1495:"p-Phenylenediamine MSDS"
979:
930:
880:
611:
606:
461:
441:
406:
101:
89:
77:
72:
44:
35:
1524:10.1002/14356007.a19_405
924:250 mg/kg (rabbit, oral)
699:Precautionary statements
1690:10.2310/6620.2009.08097
596:Magnetic susceptibility
1287:
1237:PPD is also used as a
1167:
1141:terephthaloyl chloride
1123:PPD is a precursor to
1093:is then hydrogenated:
926:100 mg/kg (cat, oral)
826:
63:
54:
1473:"p-Phenylene diamine"
1283:
1203:in the production of
1161:
1119:Precursor to polymers
1053:. This derivative of
825:
62:
53:
1327:Allergen of the Year
1321:, and sensitization
1083:4-nitrochlorobenzene
1061:and composites like
904:98 mg/kg (rat, oral)
902:80 mg/kg (rat, oral)
808:(fire diamond)
96:1,4-Phenylenediamine
92:Paraphenylenediamine
79:Preferred IUPAC name
18:Paraphenylenediamine
1847:10.7759/cureus.8352
1791:1994HETox..13..167A
1634:2006JTEHB...9..413R
539:Solubility in water
504: g·mol
155:Beilstein Reference
83:Benzene-1,4-diamine
32:
1608:p-Phenylenediamine
1288:
1239:histological stain
1232:contact dermatitis
1195:Rubber antioxidant
1185:2,5-diaminotoluene
1168:
1089:and the resulting
1037:with the formula C
1012:Infobox references
971:(Immediate danger)
827:
554:<1 mmHg (20°C)
94:1,4-Diaminobenzene
64:
55:
31:-Phenylenediamine
27:
1533:978-3-527-30385-4
1448:. pp. 5–89.
1444:(97th ed.).
1151:, a precursor to
1027:-Phenylenediamine
1020:Chemical compound
1018:
1017:
665:Hazard statements
602:-70.28·10 cm/mol
375:CompTox Dashboard
143:Interactive image
68:
67:
16:(Redirected from
1911:
1878:
1877:
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1849:
1825:
1819:
1818:
1774:
1768:
1767:
1765:
1764:
1755:. Archived from
1749:
1743:
1742:
1740:
1739:
1730:. Archived from
1724:
1718:
1717:
1668:
1662:
1661:
1617:
1611:
1605:
1599:
1598:
1596:
1595:
1588:"Chemical Tests"
1584:
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1416:
1401:
1400:
1398:
1397:
1388:. Archived from
1382:
1376:
1372:, 11th Edition,
1365:
1207:products (e.g.,
1110:
1100:
1085:is treated with
1035:organic compound
1002:
996:
993:
992:
918:lowest published
847:
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833:
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469:Chemical formula
399:
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217:
197:
177:
145:
121:
46:
40:
33:
21:
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1884:
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1822:
1776:
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1771:
1762:
1760:
1751:
1750:
1746:
1737:
1735:
1726:
1725:
1721:
1670:
1669:
1665:
1619:
1618:
1614:
1606:
1602:
1593:
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1565:
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1534:
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1511:
1502:
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1471:
1470:
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1456:
1437:
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1432:
1418:
1417:
1404:
1395:
1393:
1384:
1383:
1379:
1366:
1355:
1350:
1338:
1274:
1267:
1252:PPD is used by
1217:
1197:
1173:
1121:
1116:
1079:
1052:
1048:
1044:
1040:
1021:
1014:
1009:
1008:
1007: ?)
998:
994:
990:
986:
972:
959:
946:
925:
921:
915:
905:
903:
899:
893:
873:
870:
852:
851:
850:
849:
842:
835:
828:
824:
816:
701:
667:
653:
627:
599:
589:
585:
578:
568:
541:
501:
491:
485:
479:
471:
457:
454:
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448:
437:
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384:
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338:
322:
309:
297:
277:
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220:
200:
180:
157:
148:
135:
124:
111:
97:
95:
93:
85:
84:
23:
22:
15:
12:
11:
5:
1917:
1915:
1907:
1906:
1901:
1896:
1886:
1885:
1880:
1879:
1820:
1769:
1744:
1719:
1684:(3): 149–160.
1663:
1612:
1600:
1579:
1559:
1539:
1532:
1500:
1486:
1461:
1455:978-1498754286
1454:
1430:
1402:
1377:
1352:
1351:
1349:
1346:
1345:
1344:
1337:
1334:
1272:
1266:
1263:
1254:lichenologists
1216:
1213:
1196:
1193:
1172:
1169:
1120:
1117:
1115:
1112:
1091:4-nitroaniline
1078:
1075:
1050:
1046:
1042:
1038:
1019:
1016:
1015:
1010:
988:
987:
983:standard state
980:
977:
976:
973:
967:
964:
963:
962:TWA 0.1 mg/m
960:
954:
951:
950:
949:TWA 0.1 mg/m
947:
941:
938:
937:
928:
927:
922:
913:
911:
908:
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900:
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864:
863:
860:
854:
853:
843:
836:
829:
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813:
812:
811:
809:
800:
799:
745:P305+P351+P338
702:
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550:Vapor pressure
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42:
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24:
14:
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10:
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2:
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1835:
1831:
1824:
1821:
1816:
1812:
1808:
1804:
1800:
1796:
1792:
1788:
1785:(3): 167–70.
1784:
1780:
1773:
1770:
1759:on 2010-03-31
1758:
1754:
1748:
1745:
1734:on 2017-10-24
1733:
1729:
1723:
1720:
1715:
1711:
1707:
1703:
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1679:
1675:
1667:
1664:
1659:
1655:
1651:
1647:
1643:
1639:
1635:
1631:
1628:(5): 413–39.
1627:
1623:
1616:
1613:
1609:
1604:
1601:
1589:
1583:
1580:
1577:
1573:
1569:
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1560:
1557:
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1509:
1507:
1505:
1501:
1496:
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1468:
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1462:
1457:
1451:
1447:
1443:
1442:
1434:
1431:
1426:
1422:
1415:
1413:
1411:
1409:
1407:
1403:
1392:on 2012-03-13
1391:
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1354:
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1328:
1324:
1320:
1317:), bronchial
1316:
1312:
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1299:
1297:
1293:
1286:
1282:
1278:
1275:
1264:
1262:
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1235:
1233:
1229:
1224:
1222:
1214:
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1194:
1192:
1190:
1186:
1182:
1178:
1170:
1165:
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1156:
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1150:
1146:
1142:
1138:
1134:
1130:
1126:
1118:
1113:
1111:
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1099:
1094:
1092:
1088:
1084:
1076:
1074:
1072:
1068:
1064:
1060:
1056:
1036:
1032:
1028:
1026:
1013:
1006:
1001:
984:
978:
974:
970:
966:
965:
961:
958:(Recommended)
957:
953:
952:
948:
945:(Permissible)
944:
940:
939:
935:
934:
929:
923:
919:
910:
909:
901:
897:
888:
887:
883:
879:
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328:RTECS number
195:ChEMBL403741
102:Identifiers
90:Other names
28:
1369:Merck Index
1296:patch tests
1189:indophenols
896:median dose
882:Lethal dose
871:temperature
858:Flash point
651:Signal word
509:Appearance
462:Properties
253:100.003.096
175:CHEBI:51403
1888:Categories
1763:2017-09-07
1738:2017-09-07
1594:2019-04-30
1396:2011-07-14
1348:References
1323:dermatitis
1285:Patch test
1215:Other uses
1155:polymers.
1149:isocyanate
1077:Production
625:Pictograms
497:Molar mass
353:U770QIT64J
206:ChemSpider
130:3D model (
109:CAS Number
1856:2168-8184
1698:2162-5220
1446:CRC Press
1067:hair dyes
789:P403+P233
773:P337+P313
769:P333+P313
741:P304+P340
737:P302+P352
733:P301+P310
616:labelling
364:UN number
335:SS8050000
274:203-404-7
266:EC Number
1904:Monomers
1899:Diamines
1894:Anilines
1874:32617225
1815:31229733
1714:24088485
1706:19470301
1658:23749135
1650:17492526
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1427:(NIOSH).
1336:See also
1307:allergen
1298:(5.0%).
1292:allergen
1245:such as
1177:hair dye
1153:urethane
1145:phosgene
1059:polymers
1033:) is an
975:25 mg/m
805:NFPA 704
607:Hazards
598:(χ)
226:DrugBank
215:13835179
119:106-50-3
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1807:7909678
1787:Bibcode
1630:Bibcode
1421:"#0495"
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1181:aniline
1164:monomer
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