224:
243:
291:
amorphous character of polymethyloxetanes. Oxetanes symmetrically bisubstituted on the same carbon, give crystalline polymers, such as 3,3-dimethyloxetane. Melting point of poly(3,3-dimethyloxetane) is 47 °C. Halogens increase melting point of oxetane polymers. The bigger halogen atom, the higher melting temperature is. Melting temperature of halogenated oxetanes vary from 135 to 290 °C. Amorphous low melting oxetanes are soluble in common organic solvents, on the other hand crystalline are not.
118:
19:
346:(Russia). Main use were sterilizable goods because of relatively high heat-distortion temperature and low water absorption. BCMO is self extinguishing (because of chlorine atoms present in polymer chain) and is highly chemically resistant. It stands up to most organic solvents and strong alkali. It dissolves in strong acids, such as concentrated HNO
290:
Polyoxetanes can be liquids or solids with high range of crystallinity and melting temperature. Final material characteristics depend on symmetry, bulkiness and polarity of the substituents. For example, melting temperature of POX is 35 °C. One methyl substituent in position 2 or 3 ensures
361:
Examples of parts that can be constructed from costly PBCMO are bearings, valves, parts for fitting cables and electrical parts, etc. It is a very good anti-corrosive coating with guarantee of corrosive stability with main use for chemical tanks. It's great material for desalination membranes.
329:
and polyamide elastomers. Particularly statistic copolymer of BCMO and THF is amorphous, tough rubber. Unhomopolymerizable derivatives of oxetane are able to copolymerize with homopolymerizable oxetanes. Most studied monomer in copolymerization problemstics have been BCMO. Also copolymers with
200:
Unsymmetrically substituted oxetanes polymerizes according to ability of attacking one or both alpha-carbons of the propagation centre. Unsubstituted and 3-substituted derivatives polymerize in symmetrical manner, but 2-substituted derivatives can form any of the basic types of polymer chain
253:
Mentioned side reactions compete in speed with propagation. The faster the propagation, the less side reactions take place. Speed of propagation depends on polymerized monomer, initiation system used and polymerization conditions set.
358:. A typical number-average molecular weight range between 250 000 nad 350 000 g/mol. It can be conventionally processed via injection moulding. Moulded goods exhibit low shrinkage and fantastic dimensional stability in general.
168:
F) are effective initiators of cationic polymerization of cyclic ethers, such as oxetane. For sufficient stability of propagation centre, a counterion X of low nucleophylity is required, such as SbCl
302:
has been used to break up polyoxetane to lower molecular weight POX glycols with hydroxyl (–OH) functional end groups. With the same result, degradation with ozone followed by reduction by LiAlH
1197:
338:
Polyoxetanes are engineering polymers. Only one oxetane polymer, derived from 3,3–bis(chloromethyl)oxetane (BCMO) had industrial application. It was available under trade mark
929:"Ring-opening polymerization, volumes 1 and 2 and indexes, K. J. Ivin and T. Saegusa, Eds., Elsevier Science, New York, 1984, Vol. 1, 521 pp.; Vol. 2,1131 pp. Price: $ 277.75"
235:. During polymerization of unsubstituted oxetane, mutual attack of two growing chains may occur, in very small number, to form acyclic oxonium ions. This process is so called
223:
192:
OH counterions. Propagation is very fast and thus preparation of lower molecular weight products (also with desired functional end groups) wasnlt performed until today.
1289:
417:–). Energetic polymers can be used as explosives and propellants or they are precursors for manufacturing of mentioned above. They burn with a great deal of smoke.
536:
E. J. Vandenberg and A. E. Robinson in E. J. Vandenberg, ed., Polyethers, ACS Symp, Ser. 6, American
Chemical Society, Washington, D.C., 1975, pp. 101–119
117:
389:
By replacing hydrogen(s) in position 3 by electron deficient groups, energetic polymers can be prepared. Desired functional groups are ethyl (CH3–CH
546:
Hirano, Tsuneo; Nakayama, Shinichi; Tsuruta, Teiji (June 1975). "A possibility of anionic polymerization of oxetane by a coordination mechanism".
242:
1160:"Book Reviews : ACOUSTIC DESIGN AND NOISE CONTROL VOLUME 1, ACOUSTIC DESIGN M. Rettinger Chemical Publishing Co., Inc., New York (1977)"
515:
282:
A series of substituted oxetanes have been synthesized and polymerized. The very first polymerized oxetane was 3,3-bis(chloromethyl)oxetane.
655:"Polymerization of 2-Methyltrimethylene Oxide with Organoaluminum Catalysts and a Microstructure Study of Its Polymer by C NMR Spectroscopy"
92:
Tens of oxetane derivatives have been synthesized and many of them are polymerizable. Reasons for inability to polymerize are different
1133:
1349:"Coughtrie, Thomas, (28 Oct. 1895–29 Oct. 1985), Chairman, Bruce Peebles Industries Ltd, and Bruce Peebles Ltd, Edinburgh, 1961–67"
1290:
https://www.ssi.shimadzu.com/sites/ssi.shimadzu.com/files/pim/pim_document_file/ssi/others/15911/SafetyDataSheet_220-94824-21.pdf
160:
tend to generate secondary oxonium ions, which are unreactive, thus they are not initiators of first choice. On the other hand
100:
and bulkiness of substituents also as their position. Major 3-substituted and 3,3-disubstituted monomers are summarized in the
1067:"p-Chlorophenyldiazonium hexafluorophosphate as a catalyst in the polymerization of tetrahydrofuran and other cyclic ethers"
84:
followed by other 3,3-disubstituted derivatives during the 1950s. Unsubstituted oxetane itself was polymerized in 1956.
81:
306:
can be used. Polyoxetane glycols can be used for manufacturing of polyurethane networks and preparation of copolymers.
266:
and petrol in -25 °C for 4 to 8 hours to obtain suspension of polymer. Catalytic system consists of 1-2 % BF
134:
979:"Characterization of block copolymers based on poly[3,3-bis(ethoxymethyl)oxetane] and other novel polyethers"
314:
Two main reasons to copolymerize oxetanes are adjustment of crystallinity and modification of material properties.
125:
Ring strain of unsubstituted oxetane is 107 kJ/mol. That is twenty times more, than non-polymerizable six-membered
274:
which acts as a cocatalyst. Final suspension is neutralised, stripped by water steam, filtered, washed and dried.
130:
213:. However, with right conditions and initiation system used, a stereospecific propagation can be achieved.
1191:
153:
145:
1302:
843:. J. Brandrup and E. H. Immergut, Eds. Interscience (Wiley), New York, 1966. 1276 pp., illus. $ 19.50"
149:
1078:
940:
893:
666:
619:
447:
1391:
378:
exhibit great friction-reducing properties and are potentially useful for gas separation membranes
1330:
1047:
819:
381:
Significant part of oxetanes are turned into polyoxetanes glycols and other polymeric materials.
495:
80:
was observed and developed through the 1930s and 1940s. The very first polymerized oxetane was
1386:
1322:
1272:
1233:
1179:
1129:
1094:
1039:
998:
956:
909:
862:
811:
756:
717:
682:
635:
588:
563:
511:
463:
1356:
1314:
1264:
1223:
1171:
1121:
1086:
1029:
990:
977:
Hardenstine, K. E.; Murphy, C. J.; Jones, R. B.; Sperling, L. H.; Manser, G. E. (May 1985).
948:
901:
854:
803:
748:
709:
674:
627:
555:
503:
455:
1360:
220:
propagation centre to either form cyclic oligomers (usually tetramers) or to depolymerize.
1348:
318:
271:
263:
126:
1253:"Novel ion-containing reverse osmosis membranes. I. Preparation and selected properties"
1113:
1082:
944:
897:
670:
623:
451:
1125:
1380:
1334:
1034:
1017:
838:
436:"Synthesis and properties of a new polyether: Poly-3,3-bis(chloromethyl)-1-oxabutene"
1051:
858:
322:
299:
1318:
1228:
1211:
608:"Structural Aspects of the Ring-Opening Polymerization of 2-Methyloxacyclobutane"
1303:"Perfluorinated polymers as materials of membranes for gas and vapor separation"
1252:
1251:
Bittencourt, E.; Stannett, V.; Williams, J. L.; Hopfenberg, H. B. (March 1981).
1159:
1066:
978:
928:
881:
559:
435:
217:
141:
1268:
1175:
1090:
994:
952:
905:
459:
507:
326:
1326:
1276:
1237:
1183:
1098:
1043:
1002:
960:
913:
866:
815:
760:
721:
686:
639:
592:
567:
467:
161:
77:
1216:
Proceedings of the
National Academy of Sciences of Belarus, Medical Series
701:
713:
654:
607:
97:
93:
1016:
Cabal, Luis A; Reed, John; Miller, Frank; Hodgman, Joan E (April 1981).
678:
631:
18:
823:
796:
Revue belge de
Musicologie / Belgisch Tijdschrift voor Muziekwetenschap
101:
61:
58:
38:
241:
222:
184:. First polymerizations were conducted with compounds consisting of BF
116:
791:
736:
582:
807:
752:
216:
Oxygen atoms of the main chain possess enough reactivity to attack
137:
mechanism. Special oxetanes are polymerizable by other mechanisms.
606:
Kops, Jørgen; Hvilsted, Søren; Spanggaard, Hans (September 1980).
502:, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. pst520,
65:
1018:"120 Elevated Blood Pressure in Infants of Pre-Eclamptic Mothers"
880:
Conjeevaram, S. V.; Benson, R. S.; Lyman, D. J. (February 1985).
157:
737:"The polymerization of oxetane with hexafluorophosphate salts"
882:"Block copolyurethanes based on polyoxytrimethylene glycols"
1301:
Yampolskii, Yu.; Belov, N.; Alentiev, A. (15 March 2020).
702:"111. Cationic polymerisation of oxacyclobutanes. Part I"
227:"Back-bitting" of polyoxetane leading to depolymerization
1114:"Cationic Ring-opening Polymerization: Copolymerization"
121:
Initiation and propagation of polyoxetane polymerization
792:"Dialogos. Lucien Goethals in gesprek met Philip Sioen"
1071:
Journal of
Polymer Science Part A-1: Polymer Chemistry
886:
Journal of
Polymer Science: Polymer Chemistry Edition
330:
thermoplastic elastomer behavior have been prepared.
231:
These reactions within one molecule are referred as
933:
Journal of
Polymer Science: Polymer Letters Edition
434:Farthing, Alan C.; Reynolds, R. J. William (1954).
37:, is synthetic organic heteroatomic thermoplastic
1196:: CS1 maint: DOI inactive as of September 2024 (
735:Black, P. E.; Worsfold, D. J. (1 November 1976).
1065:Dreyfuss, M. P.; Dreyfuss, P. (September 1966).
321:(THF) to produce precursors of soft segments of
1112:Dreyfuss, Patricia; Dreyfuss, M. Peter (1989),
500:Encyclopedia of Polymer Science and Technology
494:Dreyfuss, M. P.; Dreyfuss, P. (15 July 2011),
1118:Comprehensive Polymer Science and Supplements
972:
970:
777:Sv. 1. 2. vyd. Str. 268. Chimia, Moscov 1975.
653:Oguni, Nobuki; Hyoda, Junko (November 1980).
8:
1355:, Oxford University Press, 1 December 2007,
1212:"КЛИНИЧЕСКАЯ И ЭКСПЕРИМЕНТАЛЬНАЯ МЕДИЦИНА"
262:Polymerization is conducted in mixture of
1227:
1033:
773:Katajeva V.M., Popova V.A., Sažina B.I.:
706:Journal of the Chemical Society (Resumed)
790:Goethals, Lucien; Sioen, Philip (2000).
498:, in John Wiley & Sons, Inc. (ed.),
17:
426:
317:Oxetanes are copolymerized mainly with
1189:
1153:
1151:
785:
783:
140:The propagation centre is a tertiary
7:
1361:10.1093/ww/9780199540884.013.u163177
489:
487:
485:
483:
481:
479:
477:
96:and ring strain caused by different
1257:Journal of Applied Polymer Science
1126:10.1016/b978-0-08-096701-1.00115-4
983:Journal of Applied Polymer Science
837:Kline, G. M. (16 September 1966).
64:, which is a four-membered cyclic
14:
1158:Kleinschmidt, K. (1 March 1979).
397:–) or 2-oxa-4,4-dinitropentyl (CH
22:Chemical structure of polyoxetane
1035:10.1203/00006450-198104001-00129
258:Example of industrial production
859:10.1126/science.153.3742.1372-a
1164:The Shock and Vibration Digest
1120:, Elsevier, pp. 851–860,
1:
1178:(inactive 4 September 2024).
741:Canadian Journal of Chemistry
1319:10.1016/j.memsci.2019.117779
1229:10.29235/1814-6023-2020-17-3
362:Perfluorinated oxetanes (–CF
342:by Hercules, Inc. (USA) and
129:. Oxetane polymerizes via a
82:3,3-bis(chloromethyl)oxetane
41:with molecular formula (–OCH
1307:Journal of Membrane Science
927:Schmitt, G. C. (May 1985).
560:10.1002/macp.1975.021760628
1408:
1269:10.1002/app.1981.070260312
1176:10.1177/058310247901100307
1091:10.1002/pol.1966.150040913
995:10.1002/app.1985.070300522
953:10.1002/pol.1985.130230513
906:10.1002/pol.1985.170230217
839:"Chemical Reference Book:
775:Spravočnik po plastmassam.
548:Die Makromolekulare Chemie
460:10.1002/pol.1954.120120142
440:Journal of Polymer Science
295:Polymeranalogical reaction
508:10.1002/0471440264.pst520
57:. It is polymerized from
278:Substituted polyoxetanes
144:, mainly initialized by
587:. Gordon & Breach.
250:
228:
122:
23:
1222:(3). 29 August 2020.
584:Poly(tetrahydrofuran)
248:temporary termination
245:
237:temporary termination
226:
120:
21:
714:10.1039/jr9560000542
700:Rose, J. B. (1956).
581:Dreyfuss, P (1982).
1083:1966JPoSA...4.2179D
945:1985JPoSL..23..275S
898:1985JPoSA..23..429C
679:10.1021/ma60078a058
671:1980MaMol..13.1687O
632:10.1021/ma60077a007
624:1980MaMol..13.1058K
452:1954JPoSc..12..503F
270:and 0,1-0,4 %
156:and others. Strong
154:carbocationic salts
1022:Pediatric Research
496:"Oxetane Polymers"
385:Energetic polymers
264:methylene chloride
251:
229:
123:
24:
1218:(in Belarusian).
747:(21): 3325–3329.
517:978-0-471-44026-0
1399:
1371:
1370:
1369:
1367:
1345:
1339:
1338:
1298:
1292:
1287:
1281:
1280:
1248:
1242:
1241:
1231:
1208:
1202:
1201:
1195:
1187:
1155:
1146:
1145:
1144:
1142:
1109:
1103:
1102:
1077:(9): 2179–2200.
1062:
1056:
1055:
1037:
1013:
1007:
1006:
989:(5): 2051–2064.
974:
965:
964:
924:
918:
917:
877:
871:
870:
841:Polymer Handbook
834:
828:
827:
787:
778:
771:
765:
764:
732:
726:
725:
697:
691:
690:
665:(6): 1687–1690.
650:
644:
643:
618:(5): 1058–1062.
603:
597:
596:
578:
572:
571:
554:(6): 1897–1900.
543:
537:
534:
528:
527:
526:
524:
491:
472:
471:
431:
150:trialkyl oxonium
1407:
1406:
1402:
1401:
1400:
1398:
1397:
1396:
1377:
1376:
1375:
1374:
1365:
1363:
1347:
1346:
1342:
1300:
1299:
1295:
1288:
1284:
1250:
1249:
1245:
1210:
1209:
1205:
1188:
1157:
1156:
1149:
1140:
1138:
1136:
1111:
1110:
1106:
1064:
1063:
1059:
1015:
1014:
1010:
976:
975:
968:
926:
925:
921:
879:
878:
874:
836:
835:
831:
808:10.2307/3686877
789:
788:
781:
772:
768:
753:10.1139/v76-479
734:
733:
729:
699:
698:
694:
652:
651:
647:
605:
604:
600:
580:
579:
575:
545:
544:
540:
535:
531:
522:
520:
518:
493:
492:
475:
433:
432:
428:
423:
416:
412:
408:
404:
400:
396:
392:
387:
377:
373:
369:
365:
357:
353:
349:
336:
319:tetrahydrofuran
312:
305:
297:
288:
280:
269:
260:
198:
191:
187:
183:
179:
175:
171:
167:
127:tetrahydropyran
115:
110:
90:
74:
56:
52:
48:
44:
12:
11:
5:
1405:
1403:
1395:
1394:
1389:
1379:
1378:
1373:
1372:
1340:
1293:
1282:
1263:(3): 879–888.
1243:
1203:
1147:
1134:
1104:
1057:
1008:
966:
919:
892:(2): 429–444.
872:
853:(3742): 1372.
829:
779:
766:
727:
692:
659:Macromolecules
645:
612:Macromolecules
598:
573:
538:
529:
516:
473:
446:(1): 503–507.
425:
424:
422:
419:
414:
410:
406:
402:
398:
394:
390:
386:
383:
375:
371:
367:
363:
355:
351:
347:
335:
332:
311:
308:
303:
296:
293:
287:
284:
279:
276:
272:epichlorhydrin
267:
259:
256:
197:
196:Side reactions
194:
189:
185:
181:
177:
173:
169:
165:
114:
111:
109:
108:Polymerization
106:
89:
86:
73:
70:
54:
50:
46:
42:
13:
10:
9:
6:
4:
3:
2:
1404:
1393:
1390:
1388:
1385:
1384:
1382:
1362:
1358:
1354:
1350:
1344:
1341:
1336:
1332:
1328:
1324:
1320:
1316:
1312:
1308:
1304:
1297:
1294:
1291:
1286:
1283:
1278:
1274:
1270:
1266:
1262:
1258:
1254:
1247:
1244:
1239:
1235:
1230:
1225:
1221:
1217:
1213:
1207:
1204:
1199:
1193:
1185:
1181:
1177:
1173:
1169:
1165:
1161:
1154:
1152:
1148:
1137:
1135:9780080967011
1131:
1127:
1123:
1119:
1115:
1108:
1105:
1100:
1096:
1092:
1088:
1084:
1080:
1076:
1072:
1068:
1061:
1058:
1053:
1049:
1045:
1041:
1036:
1031:
1027:
1023:
1019:
1012:
1009:
1004:
1000:
996:
992:
988:
984:
980:
973:
971:
967:
962:
958:
954:
950:
946:
942:
938:
934:
930:
923:
920:
915:
911:
907:
903:
899:
895:
891:
887:
883:
876:
873:
868:
864:
860:
856:
852:
848:
844:
842:
833:
830:
825:
821:
817:
813:
809:
805:
801:
797:
793:
786:
784:
780:
776:
770:
767:
762:
758:
754:
750:
746:
742:
738:
731:
728:
723:
719:
715:
711:
707:
703:
696:
693:
688:
684:
680:
676:
672:
668:
664:
660:
656:
649:
646:
641:
637:
633:
629:
625:
621:
617:
613:
609:
602:
599:
594:
590:
586:
585:
577:
574:
569:
565:
561:
557:
553:
549:
542:
539:
533:
530:
519:
513:
509:
505:
501:
497:
490:
488:
486:
484:
482:
480:
478:
474:
469:
465:
461:
457:
453:
449:
445:
441:
437:
430:
427:
420:
418:
393:–), nitro (NO
384:
382:
379:
359:
345:
341:
333:
331:
328:
324:
323:polyurethanes
320:
315:
309:
307:
301:
294:
292:
285:
283:
277:
275:
273:
265:
257:
255:
249:
244:
240:
238:
234:
225:
221:
219:
214:
212:
211:tail-to-tail)
208:
204:
201:connections (
195:
193:
163:
159:
155:
151:
147:
143:
138:
136:
135:ring-openning
132:
128:
119:
112:
107:
105:
103:
99:
95:
87:
85:
83:
79:
71:
69:
67:
63:
60:
40:
36:
35:poly(oxetane)
32:
28:
20:
16:
1364:, retrieved
1352:
1343:
1310:
1306:
1296:
1285:
1260:
1256:
1246:
1219:
1215:
1206:
1192:cite journal
1170:(3): 27–28.
1167:
1163:
1139:, retrieved
1117:
1107:
1074:
1070:
1060:
1025:
1021:
1011:
986:
982:
936:
932:
922:
889:
885:
875:
850:
846:
840:
832:
799:
795:
774:
769:
744:
740:
730:
705:
695:
662:
658:
648:
615:
611:
601:
583:
576:
551:
547:
541:
532:
521:, retrieved
499:
443:
439:
429:
388:
380:
360:
343:
339:
337:
334:Applications
316:
313:
300:Butyllithium
298:
289:
281:
261:
252:
247:
246:Polyoxetane
236:
232:
230:
215:
210:
207:head-to-head
206:
203:head-to-tail
202:
199:
139:
124:
91:
75:
34:
30:
26:
25:
15:
1366:28 December
1353:Who Was Who
1141:28 December
233:backbitting
162:super acids
146:Lewis acids
142:oxonium ion
27:Polyoxetane
1392:Polyethers
1381:Categories
1313:: 117779.
939:(5): 275.
523:5 December
421:References
344:Pentaplast
327:polyethers
310:Copolymers
286:Properties
1335:214064049
1327:0376-7388
1277:0021-8995
1238:2524-2350
1184:0583-1024
1099:0449-296X
1044:0031-3998
1003:0021-8995
961:0360-6384
914:0360-6376
867:0036-8075
816:0771-6788
802:: 49–71.
761:0008-4042
722:0368-1769
687:0024-9297
640:0024-9297
593:636328269
568:0025-116X
468:0022-3832
113:Mechanism
104:article.
78:chemistry
1387:Polymers
1052:40895078
164:(eg. HSO
131:cationic
98:electron
94:basicity
88:Monomers
1079:Bibcode
1028:: 459.
941:Bibcode
894:Bibcode
847:Science
824:3686877
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667:Bibcode
620:Bibcode
448:Bibcode
325:(PUR),
218:oxonium
152:salts,
102:oxetane
76:Needed
72:History
62:monomer
59:oxetane
39:polymer
1333:
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180:or SbF
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1331:S2CID
1048:S2CID
820:JSTOR
413:–O–CH
401:–C(NO
188:or BF
176:, AsF
158:acids
66:ether
1368:2022
1323:ISSN
1273:ISSN
1234:ISSN
1198:link
1180:ISSN
1143:2022
1130:ISBN
1095:ISSN
1040:ISSN
999:ISSN
957:ISSN
910:ISSN
863:ISSN
812:ISSN
757:ISSN
718:ISSN
683:ISSN
636:ISSN
589:OCLC
564:ISSN
525:2022
512:ISBN
464:ISSN
350:or H
209:and
172:, PF
1357:doi
1315:doi
1311:598
1265:doi
1224:doi
1172:doi
1122:doi
1087:doi
1030:doi
991:doi
949:doi
902:doi
855:doi
851:153
804:doi
749:doi
710:doi
675:doi
628:doi
556:doi
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