Thiol–enes: Chemistry of the past with promise for the future

Wiley - Tập 42 Số 21 - Trang 5301-5338 - 2004
Charles E. Hoyle1, Tai Yeon Lee1, Todd M. Roper1
1Department of Polymer Science, University of Southern Mississippi, Hattiesburg, Mississippi, 39406

Tóm tắt

Abstract

The photopolymerization of mixtures of multifunctional thiols and enes is an efficient method for the rapid production of films and thermoset plastics with unprecedented physical and mechanical properties. One of the major obstacles in traditional free‐radical photopolymerization is essentially eliminated in thiol–ene polymerizations because the polymerization occurs in air almost as rapidly as in an inert atmosphere. Virtually any type of ene will participate in a free‐radical polymerization process with a multifunctional thiol. Hence, it is possible to tailor materials with virtually any combination of properties required for a particular application. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 5301–5338, 2004

Từ khóa


Tài liệu tham khảo

10.1002/jctb.5000573206

Marvel C. S., 1948, J Am Chem Soc, 70, 933

10.1021/ja01147a062

Patai S., 1974, The Chemistry of the Thiol Group

Jacobine A. F., 1993, 219

Morgan C. R., 1980, J Radiat Cur, 7, 10

10.1002/pol.1977.170150311

Gush D. P., 1978, Mod Paint Coat, 58

Bush R. W., 1980, J Radiat Cur

10.1002/pol.1978.130160203

Morgan C. R.U.S. Patent 3 784 524 1974.

Ross J. S., 2000, RadTech NA Tech Conf Proc, 241

10.1002/apmc.1995.052240113

10.1080/00222339108054065

10.1002/actp.1991.010420106

10.1002/apmc.1991.051880117

10.1002/(SICI)1522-9505(19980201)254:1<11::AID-APMC11>3.0.CO;2-A

10.1002/apmc.1993.052070117

10.1002/apmc.1993.052120111

10.1002/apmc.1996.052420109

10.1002/macp.1990.021911018

Klemm E.;Bellstodt K.;Kuse A.;Martin R.;Riesenberg E.;Wolf H.German Patent DD 301155 1992.

10.1021/bk-1990-0417.ch013

Jacobine A. F.;Woods J. G.;Rakas M. A.U.S. Patent 5 516 455 1996.

Woods J. G.;Rakas M. A.;Alberino L. M.;Kropp P. L.;Sutkaitis D. M.;Nakos S. T.WO 95/00869 1995.

Jacobine A. F., 1991, 342

Woods J. G.;Rakas M. A.;Jacobine A. F.;Alberino L. M.;Kropp P.;Sutkaitis D. M.;Glaser D. M.;Nakos S. T.U.S. Patent 5 459 175 1995.

10.1002/app.1992.070450312

Glaser D. M.;Jacobine J. F.;Grabek P. J.U.S. Patent 5 399 624 1995.

10.1007/BF00318060

Woods J. G., 1992, RadTech NA Tech Conf Proc, 173

Glaser D. M.;Jacobine J. F.;Grabek P. J.U.S. Patent 5 459 173 1995.

Dowling J. P.;Richardson S. C.;Quigley K.U.S. Patent 5 358 976 1994.

10.1080/00218469208026529

Salamon P. A., 1992, RadTech NA Tech Conf Proc, 239

Diggins D. R.;Toh H. K.European Patent AU PL5865 1992.

Toh H. K.;Bateman I. R.;Diggins D. R.;Cielinski B. G.U.S. Patent 5 977 276 1999.

Toh H. K.;Fang C.WO 00/64956 2000.

Chen F.;Toh H. K.U.S. Patent 6 153 663 2000.

Toh H. K.;Chen F.;Kok C. M.U.S. Patent 6 172 140 2001.

Toh H. K.;Bateman I. R.;Diggins D. R.;Cieslinski B. G.U.S. Patent 6 313 251 2001.

Bateman I. R.;Toh H. K.;Diggins D. R.;Kloubek H.U.S. Patent 6 391 983 2002.

10.1002/pola.1314

Cramer N. B., 2003, Polym Prepr (Am Chem Soc Div Polym Chem), 44, 17

10.1021/ma034667s

10.1021/ma0200672

10.1021/ma034072x

10.1080/713935628

Cramer N. B., 2001, Polym Prepr (Am Chem Soc Div Polym Chem), 42, 699

Beckel E., 2002, Polym Prepr (Am Chem Soc Div Polym Chem), 43, 530

Reddy S. K., 2003, Polym Prepr (Am Chem Soc Div Polym Chem), 44, 543

10.1021/cm034291x

Cramer N. B., 2003, Polym Prepr (Am Chem Soc Div Polym Chem), 44, 23

Cramer N., 2003, Proc Int Waterborne High‐Solids Powder Coat Symp, 30, 311

10.1002/masy.200450228

10.1002/pola.20010

Hoyle C. E., 2001, Polym Prepr (Am Chem Soc Div Polym Chem), 42, 697

Lee T. Y., 2003, Polym Prepr (Am Chem Soc Div Polym Chem), 44, 21

Roper T. M., 2003, Polym Prepr (Am Chem Soc Div Polym Chem), 44, 111

10.1016/S0032-3861(98)00734-4

Hoyle C. E., 2002, RadTech NA Tech Conf Proc, 675

Cole M., 2002, RadTech NA Tech Conf Proc, 211

Hoyle C. E., 2002, RadTech NA Tech Conf Proc, 675

Nason C., 2002, RadTech NA Tech Conf Proc, 687

Roper T. M., 2002, RadTech NA Tech Conf Proc, 697

Lee T. Y., 2002, RadTech NA Tech Conf Proc, 705

Hoyle C. E., 2003, RadTech Eur Tech Conf Proc, 571

Hoyle C. E., 2003, RadTech Asia Tech Conf Proc, 267

10.1021/bk-2003-0847.ch005

10.1021/ma035751a

10.1016/j.polymer.2004.02.038

Roper T. M., 2004, RadTech NA Tech Conf Proc, 4, 3

10.1021/j150571a012

10.1002/macp.1966.020970125

Johansson M., 2003, Polym Prepr (Am Chem Soc Div Polym Chem), 44, 19

10.1016/S0257-8972(02)00784-3

10.1021/ja01514a032

10.1021/ja027428d

10.1021/ja038072o

Cole M. C.Dissertation University of Southern Mississippi 2001.

Rhenberg N.;Annby U.;Sjogreen C.‐A.;Davidson R. S.WO 01/14300 A1 2001.

Peterson P. M.;Harlan R. D.;Schoenberg J. E.U.S. Patent 6 201 099 2001.

10.1002/pola.10349

10.1081/MA-100101155

10.1081/MA-100101156

Johansson M., 1995, J Coat Technol, 67, 35

10.1002/masy.199509801104

Hoyle C. E.University of Southern Mississippi Hattiesburg MS. Unpublished results 2004.

10.1021/bk-2003-0847.ch039

10.1139/v73-211

10.1039/tf9383401238

Hoyle C. E.;Bowman C. N.University of Southern Mississippi Hattiesburg MS. Unpublished results 2004.

10.1021/ma960383e

10.1021/ma9708656

10.1021/bk-1997-0673.ch012

10.1021/ma010281a

Kloosterboer J. G., 1984, Polym Commun, 25, 354

10.1002/masy.19950930132

10.1021/cm021824d

10.1021/bk-2003-0847.ch006

Rehnberg N., 2001, Polym Prepr (Am Chem Soc Div Polym Chem), 42, 701

Scott G., 1981, Dev Polym Stab, 4, 1

Scott G., 1983, Dev Polym Stab, 6, 29

Shelton J. R., 1981, Dev Polym Stab, 4, 23

Sangermano M., 2002, Polym Prepr (Am Chem Soc Div Polym Chem), 43, 1013

10.1002/pola.10349

Davidson S., 2003, RadTech Eur Tech Conf Proc, 579

Rehnberg N.;Annby U.;Sjorgreen C. A.;Davidson R. S.PCT Pat. Appl. WO 2001044377 2001.

Christmas B. K., 2002, Proc RadTech NA Tech Conf Proc, 712

Christmas B. K., 2004, Proc Radtech NA Tech Conf Proc, 3, 2

Stahly E. E.U.S. Patent 3 619 393 1971.

Guthrie J. L.;Rendulic F. J.U.S. Patent 3 855 093 1974.

Kehr C. L.;Wszolek W. R.U.S. Patent 3 661 744 1992.

Kehr C. L., 1973, Proc Am Chem Soc Div Org Coat Plast Chem, 33, 295

10.1016/0144-2880(84)90014-9

Norland Optical Products Literature.http://www.norlandproducts.com accessed March2004.

10.1016/S0032-3861(00)00700-X

10.1016/S0032-3861(96)00758-6

Lee T. Y., 2002, RadTech NA Tech Conf Proc, 705

10.1021/ma035728p

10.1002/(SICI)1521-3935(19990801)200:8<1965::AID-MACP1965>3.0.CO;2-W

10.1002/1097-4628(20000829)77:9<1902::AID-APP6>3.0.CO;2-6

10.1016/S0032-3861(99)00649-7

10.1002/(SICI)1521-3935(19990201)200:2<358::AID-MACP358>3.0.CO;2-V

10.1080/00222338608063385

10.1002/(SICI)1099-0518(19970915)35:12<2333::AID-POLA2>3.0.CO;2-W

10.1002/pola.1993.080310111

10.1080/10601329608010869

Weissman P.U.S. Patent 6 310 161 2001.

Yagi T., 1989, Zairyo Gijyutsu, 7, 272

Yoshida H.;Takenoshita Y.Jpn. Kokai Tokkyo Koho 11 1988.

Kawaki T.;Kobayashi M.;Aoki O.;Yamazaki Y.;Iwai T.Jpn. Kokai Tokkyo Koho 4 1989.

10.1080/026782998207181

10.1002/jlac.199719971116

Lub J., 1999, Mol Cryst Liq Cryst Sci Tech Sect A: Mol Cryst Liq Cryst, 332, 2769

10.1021/ma020916l

10.1021/jp0215419

10.1080/0267829021000001746

10.1007/978-1-4899-0712-7_9

10.1080/00268949108029689

10.1021/ma981542s

10.1021/ma990707

10.1021/ma9907082

10.1021/ma021336r

10.1366/0003702963904764

10.1366/0003702971938902

Rafferty D. W., 2002, J Phys D: Appl Phys, 56, 284

10.1063/1.1290264

10.1080/02678290110078784

10.1021/ma9806460

10.1021/ma981556y

10.1021/ma9912296

10.1016/S0032-3861(00)00368-2

10.1021/cm00059a029

10.1088/0022-3727/27/10/023

10.1080/10587259708042014

10.1117/12.405323

Gill N. L., 1998, PMSE Book Abstr, 112

10.1088/0022-3727/35/9/310

10.1080/026782900750018564

10.1021/cm00046a027

10.1016/S0301-0104(99)00147-0

10.1080/02678299308027649

10.1080/10587259508033500

10.1021/cm950493k

Doane J. W.;Yang D. K.;Chien L. C.U.S. Patent 5 691 795 1991.

10.1103/PhysRevE.53.2412

10.1080/10587259408047172

10.1080/10587259408029743

10.1080/10587259408029746

10.1080/10587259308036224

10.1063/1.1516868

Kim J. H., 1997, Mol Cryst Liq Cryst, 302, 1067

Miller S. A.;Huffman W A.;Gilbert L. R.;Vesley G. F.U.S. Patent 5 876 238 1999.

Klosowicz S. J., 2002, Opt Appl, 32, 797

10.1063/1.124856

10.1080/10587250108025036

10.1063/1.116925

10.1063/1.1604943

10.1063/1.1519102

10.1080/026782900202507

10.1080/02678290110116204

Date M., 1998, J Soc Inf Display, 6, 37

10.1088/0022-3727/32/24/312

10.1088/0022-3727/31/18/004

10.1016/S0925-3467(02)00068-X

10.1021/cm021824d

10.1021/la980658e

10.1080/10587259808025103

10.1007/BF00326223

10.1063/1.1615315

10.1088/0268-1242/17/10/316

10.1002/1521-4095(20020404)14:7<514::AID-ADMA514>3.0.CO;2-4

10.1016/S0168-9002(01)00678-7

10.1002/(SICI)1099-0488(199710)35:14<2385::AID-POLB16>3.0.CO;2-8

10.1109/2944.979343

10.1021/la020169l

10.1063/1.371155

10.1080/10587259508033967

10.1063/1.1560870

10.1063/1.1480885

Hsu Y. Y.U.S. Patent 6 120 701 2000.

Hsu Y. Y.U.S. Patent 6 174 467 2001.

Hsu Y. Y.U.S. Patent 6 203 723 2001.

Lackritz H. S.;Kowalczyk T. C.;Lee Y. C.;Deacon D. A. G.U.S. Patent 6 236 774 2000.

Lackritz H. S.;Kowalczyk T. C.;Lee Y. C.;Deacon D. A. G.U.S. Patent 6 724 968 2004.

Debe M. K.U.S. Patent 5 336 558 1994.

Tanaka K.;Kato K.;Tsuru S.;Sakai S.U.S. Patent 5 751 452 1998.

10.1143/JJAP.40.6441

10.1063/1.1519102

10.1063/1.1604943

10.1021/ma035751a

Nason C., 2004, Polym Prepr (Am Chem Soc Div Polym Chem), 45