44:
359:
218:
35:
603:
729:
883:
Hydroxyethylmethacrylate lends itself well to applications in 3D printing as it cures quickly at room temperature when exposed to UV light in the presence of photoinitiators. It may be used as a monomeric matrix in which 40nm silica particles are suspended for 3D glass printing. When combined with
1068:
Macret, M.; Hild, G. (1982). "Hydroxyalkyl methacrylates: Kinetic investigations of radical polymerizations of pure 2-hydroxyethyl methacrylate and 2, 3-dihydroxypropyl methacrylate and the radical copolymerization of their mixtures".
611:
583:
1198:
Kotz, Frederik; Arnold, Karl; Bauer, Werner; Schild, Dieter; Keller, Nico; Sachsenheimer, Kai; Nargang, Tobias M.; Richter, Christiane; Helmer, Dorothea; Rapp, Bastian E. (2017).
673:
70:
HEMA; hydroxyethylmethacrylate; glycol methacrylate; glycol monomethacrylate; hydroxyethyl methacrylate; ethylene glycol methacrylate; 2-(methacryloyloxy)ethanol
742:
1300:
875:
relative to the dry weight. Because of this property, it was one of the first materials to be used in the manufacture of soft contact lenses.
863:
and D. Lím described its use in synthesis of hydrophilic crosslinked networks, and these results had great importance for manufacture of soft
1099:
Rosenberg, M.; Bartl, P.; Lesko, J. (1960). "Water-soluble methacrylate as an embedding medium for the preparation of ultrathin sections".
408:
737:
17:
986:
Gerrits, P. O.; Horobin, R. W. (1996). "Glycol
Methacrylate Embedding for Light Microscopy: Basic Principles and Trouble-Shooting".
965:
1317:
1185:
373:
749:
116:
819:
564:
123:
1339:
868:
835:
647:
316:
213:
175:
337:
665:
602:
1018:"Glycol Methacrylate in Light Microscopy a Routine Method for Embedding and Sectioning Animal Tissues"
889:
685:
225:
661:
354:
1017:
792:
Hydroxyethylmethacrylate was first synthesized around 1925. Common methods of synthesis are:
625:
595:
531:
689:
1211:
1143:
776:. It is a colorless viscous liquid that readily polymerizes. Hydroxyethylmethacrylate is a
681:
325:
195:
56:
43:
8:
901:
92:
82:
1215:
1147:
358:
217:
155:
1280:
1159:
948:
846:
at 20°C and 0.005 Pa⋅s at 30°C. During polymerization, it shrinks by approximately 6%.
823:
135:
1112:
1344:
1313:
1284:
1272:
1237:
1229:
1181:
1116:
1082:
1045:
1037:
1305:
1264:
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1163:
1151:
1108:
1078:
1029:
995:
905:
797:
769:
520:
436:
1309:
1178:
The professional make-up artist : motion pictures, television, print, theatre
289:
811:
244:
912:
864:
860:
807:
801:
720:
653:
544:
1033:
999:
1333:
1233:
1041:
928:
916:
885:
843:
509:
499:
206:
1298:
Stoye, D.; Funke, W.; Hoppe, L.; et al. (2006). "Paints and
Coatings".
834:
Hydroxyethylmethacrylate is completely miscible with water and ethanol, but
34:
1276:
1268:
1241:
1120:
1049:
1255:
Wirth, D. (2020). "Highly
Expandable Foam for Lithographic 3D Printing".
708:
677:
1224:
1199:
669:
464:
226:
186:
1134:
Wichterle, O.; Lím, D. (1960). "Hydrophilic gels for biological use".
697:
1155:
839:
719:
Except where otherwise noted, data are given for materials in their
264:
701:
122:
115:
822:. During polymerization of hydroxyethylmethacrylate, it works as
781:
777:
657:
635:
485:
276:
915:, polyhydroxyethylmethacrylate makes a crosslinked polymer, an
166:
1200:"Three-dimensional printing of transparent fused silica glass"
872:
693:
300:
146:
105:
342:
871:
is hydrophilic: it is capable of absorbing from 10 to 600%
639:
255:
908:, hydroxyethylmethacrylate serves as an embedding medium.
1297:
966:"GPS Safety Summary 2-Hydroxyethyl methacrylate (HEMA)"
1197:
892:
it forms a foaming resin which expands when heated.
631:
1098:
382:
InChI=1S/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
392:InChI=1/C6H10O3/c1-5(2)6(8)9-4-3-7/h7H,1,3-4H2,2H3
838:is practically insoluble in common solvents. Its
1331:
1094:
1092:
288:
91:
1301:Ullmann's Encyclopedia of Industrial Chemistry
985:
981:
979:
977:
975:
1127:
1089:
1063:
1061:
1059:
919:, that is a useful component in some paints.
1133:
1016:Cole, Madison B.; Sykes, Stephen M. (1974).
818:Both these methods give also some amount of
355:DTXSID00891152 DTXSID7022128, DTXSID00891152
1011:
1009:
972:
810:of methacrylic acid with a large excess of
1067:
1056:
357:
216:
194:
1223:
1015:
324:
1006:
931:and can cause allergic skin reactions.
504:−99 °C (−146 °F; 174 K)
353:
14:
1332:
951:. ChemSrc: A Smart Chem-Search Engine.
941:
514:213 °C (415 °F; 486 K)
207:
1254:
960:
958:
878:
713:97 °C (207 °F; 370 K)
385:Key: WOBHKFSMXKNTIM-UHFFFAOYSA-N
174:
154:
1257:ACS Applied Materials and Interfaces
61:2-Hydroxyethyl 2-methylprop-2-enoate
927:Hydroxyethylmethacrylate is a mild
395:Key: WOBHKFSMXKNTIM-UHFFFAOYAH
279:
263:
24:
1101:Journal of Ultrastructure Research
955:
949:"2-hydroxyethyl methacrylate_msds"
25:
1356:
1176:Blasco, Joe; Kehoe, Vincent J-R;
854:
727:
601:
448:
42:
33:
1291:
1248:
849:
723:(at 25 °C , 100 kPa).
1191:
1170:
820:ethylene glycol dimethacrylate
565:Occupational safety and health
454:
442:
13:
1:
1310:10.1002/14356007.a18_359.pub2
1113:10.1016/s0022-5320(60)80024-x
934:
829:
780:that is used to make various
1083:10.1016/0032-3861(82)90020-9
869:Polyhydroxyethylmethacrylate
787:
7:
28:(Hydroxyethyl)methacrylate
10:
1361:
988:Journal of Histotechnology
922:
772:with the chemical formula
1034:10.3109/10520297409117016
1000:10.1179/his.1996.19.4.297
717:
582:
562:
557:
429:
404:
369:
75:
67:
55:
50:
41:
32:
18:Hydroxyethyl methacrylate
895:
762:Hydroxyethylmethacrylate
648:Precautionary statements
1304:. Weinheim: Wiley-VCH.
1269:10.1021/acsami.0c02683
1188:; LCC# PN2068.B53 2005
774:H2C\dC(CH3)CO2CH2CH2OH
57:Preferred IUPAC name
1340:Methacrylate esters
1263:(16): 19033–19043.
1225:10.1038/nature22061
1216:2017Natur.544..337K
1148:1960Natur.185..117W
902:electron microscopy
766:glycol methacrylate
521:Solubility in water
472: g·mol
136:Beilstein Reference
29:
911:When treated with
879:Use in 3D printing
824:crosslinking agent
750:Infobox references
480:Colourless liquid
27:
1210:(7650): 337–339.
1142:(4706): 117–118.
758:Chemical compound
756:
755:
626:Hazard statements
338:CompTox Dashboard
124:Interactive image
117:Interactive image
16:(Redirected from
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1156:10.1038/185117a0
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1125:
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1107:(3–4): 298–303.
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1087:
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1053:
1022:Stain Technology
1013:
1004:
1003:
983:
970:
969:
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953:
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906:light microscopy
798:methacrylic acid
775:
770:organic compound
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663:
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605:
552:
493:
471:
456:
450:
444:
437:Chemical formula
416:O=C(OCCO)\C(=C)C
362:
361:
346:
344:
328:
292:
281:
267:
245:Gmelin Reference
228:
220:
209:
198:
178:
158:
126:
119:
95:
46:
37:
30:
26:
21:
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1097:
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1057:
1014:
1007:
984:
973:
964:
963:
956:
947:
946:
942:
937:
925:
913:polyisocyanates
898:
881:
857:
852:
832:
812:ethylene glycol
790:
773:
764:(also known as
759:
752:
747:
746:
745: ?)
736:
732:
728:
724:
650:
628:
614:
598:
578:Eye irritation
575:
550:
523:
491:
469:
459:
453:
447:
439:
425:
422:
421:CC(=C)C(=O)OCCO
417:
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387:
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138:
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109:
98:
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71:
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23:
22:
15:
12:
11:
5:
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1318:
1290:
1247:
1190:
1169:
1126:
1088:
1055:
1028:(6): 387–400.
1005:
994:(4): 297–311.
971:
954:
939:
938:
936:
933:
924:
921:
897:
894:
880:
877:
865:contact lenses
856:
855:Contact lenses
853:
851:
848:
831:
828:
816:
815:
808:esterification
805:
802:ethylene oxide
789:
786:
757:
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753:
748:
726:
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721:standard state
718:
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674:P305+P351+P338
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545:Vapor pressure
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1319:3-527-30673-0
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1186:0-9771580-0-4
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950:
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932:
930:
929:skin irritant
920:
918:
917:acrylic resin
914:
909:
907:
903:
893:
891:
890:BOC anhydride
887:
886:blowing agent
876:
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510:Boiling point
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500:Melting point
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210:
208:ECHA InfoCard
205:
204:
197:
193:
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185:
184:
177:
176:ChEMBL1730239
173:
172:
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19:
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1100:
1077:(1): 81–90.
1074:
1070:
1025:
1021:
991:
987:
968:. July 2013.
943:
926:
910:
899:
882:
861:O. Wichterle
858:
850:Applications
833:
817:
796:reaction of
791:
765:
761:
760:
617:
584:
574:Main hazards
563:
533:
301:RTECS number
76:Identifiers
68:Other names
904:, later in
884:a suitable
836:its polymer
709:Flash point
612:Signal word
568:(OHS/OSH):
477:Appearance
430:Properties
214:100.011.621
156:CHEBI:34288
1334:Categories
935:References
842:is 0.0701
830:Properties
596:Pictograms
465:Molar mass
326:6E1I4IV47V
187:ChemSpider
104:3D model (
83:CAS Number
1285:215603770
1234:0028-0836
1042:0038-9153
859:In 1960,
840:viscosity
788:Synthesis
768:) is the
690:P337+P313
686:P333+P313
682:P332+P313
670:P302+P352
587:labelling
526:miscible
308:OZ4725000
235:212-782-2
227:EC Number
1345:Monomers
1277:32267677
1242:28425999
1121:13743397
888:such as
782:polymers
558:Hazards
141:1071583
93:868-77-9
1212:Bibcode
1164:4211987
1144:Bibcode
1071:Polymer
1050:4142140
923:Hazards
778:monomer
743:what is
741: (
618:Warning
486:Density
470:130.143
277:PubChem
250:936557
1316:
1283:
1275:
1240:
1232:
1204:Nature
1184:
1162:
1136:Nature
1119:
1048:
1040:
738:verify
735:
551:
492:
409:SMILES
265:C14530
167:ChEMBL
51:Names
1281:S2CID
1160:S2CID
896:Other
873:water
800:with
539:0.50
494:g/cm
374:InChI
290:13360
196:12791
147:ChEBI
106:JSmol
1314:ISBN
1273:PMID
1238:PMID
1230:ISSN
1182:ISBN
1117:PMID
1046:PMID
1038:ISSN
844:Pa⋅s
702:P501
698:P363
694:P362
678:P321
666:P280
662:P272
658:P264
654:P261
640:H319
636:H317
632:H315
553:hPa
549:0.08
532:log
490:1.07
317:UNII
256:KEGG
1306:doi
1265:doi
1220:doi
1208:544
1152:doi
1140:185
1109:doi
1079:doi
1030:doi
996:doi
900:In
585:GHS
343:EPA
280:CID
1336::
1312:.
1279:.
1271:.
1261:12
1259:.
1236:.
1228:.
1218:.
1206:.
1202:.
1180:;
1158:.
1150:.
1138:.
1115:.
1103:.
1091:^
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1008:^
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957:^
867:.
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1267::
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1222::
1214::
1166:.
1154::
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1111::
1105:4
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1081::
1052:.
1032::
1002:.
998::
814:.
804:;
733:Y
534:P
458:3
455:O
449:H
446:6
443:C
345:)
341:(
108:)
20:)
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