Abstract
The pyrrolidimium structure resulting from the cyclopolymerization of the water soluble monomer diallyldimethylammonium chloride is present in a variety of advanced polymeric materials. These materials range from water soluble polyelectrolytes to highly ordered solids. Applied research on diallyldimethylammonium chloride has been performed in order to optimize the monomer and polymer syntheses, characterize the polymers produced, improve the material properties as well as the applied technologies, and to develop new products. In addition, fundamental research has included the study of polyelectrolyte behavior of diallyldimethylammonium chloride polymers in solution. This article comprehensively reviews the work on diallyldimethylammonium chloride summarizing the current knowledge and recent progress in the field of kinetics and mechanism of homo- and copolymer syntheses, chemical structures, polyelectrolyte behavior in solution, molecular characterization, and interactions in solution and at interfaces. In particular, peculiarities of the syntheses and characterization resulting from polyelectrolyte influences are discussed in detail. A variety of current and emerging applications are presented.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Butler GB (1992) Cyclopolymerization and cyclocopolymerization, Marcel Dekker, New York
Butler GB, Zhang NZ (1991) In: Water soluble polymers, ACS Symposium Series 467, Washington DC, 25
Butler GB, Angelo RJ (1957) J Am Chem Soc 79:3128
Butler GB (1966) U.S. Pat 3,288,770
Butler GB, Ingley FL (1951) J Am Chem Soc 72:894
Wandrey C, Jaeger W, Reinisch G (1981) Acta Polym 32:197
Wandrey C, Jaeger W, Reinisch G (1981) Acta Polym 32:257
Topchiev DA, Nashmetdinova GT (1983) Vysokomol Soed A25:636
Topchiev DA, Nashmetdinova GT, Kartashewskij AI, Netshaeva AV, Kabanov VA, (1983) Isv Akad Nauk SSR, Ser Khim: 2232
Hahn M, Jaeger W, Wandrey C, Reinisch G (1984) Acta Polym 35:350
Jaeger W, Hahn M, Wandrey C, Seehaus F, Reinisch G (1984) J Macromol Sci Chem A21:593
Kabanov VA, Topciev DA (1988) Vysokomol Soed A30:675
Huang PC, Reichert KH (1988) Angew Makromol Chem 162:19
Huang PC, Reichert KH (1989) Angew Makromol Chem 165:1
Jaeger W, Gohlke U, Hahn M, Wandrey C, Dietrich K (1989) Acta Polym 40:161
Jaeger W, Hahn M, Wandrey C (1989) In: Polymer reaction engineering. Reichert KH, Geiseler W (eds) VCH Weinheim:239
Lancaster JE, Bacchei L, Panzer HP (1976) J Polym Sci, Polym Lett 14:549
Ottenbrite RM, Shillady DD (1980) In: Polymeric amines and ammonium salts. Goethals E (ed) Pergamon Press, Oxford:143
Wandrey C, Jarger W, Reinisch G, Hahn M, Engelhard G, Jancke H, Ballschuh D (1981) Acta Polym 32:179
Hoover MF (1970) J Macromol Sci-Chem A4:1327
Ottenbrite RM, Ryan WS (1980), Ind Eng Chem Prod Res Dev 19:529
Butler GB (1980) In: Polymeric amines and ammonium salts. Goethals E (ed) Pergamon Press, Oxford: 125
Hoover FM, Carr HE (1968) Tappi 51:552
Nicke R (1982) Zellstoff Papier 31:19
Jaeger W, Hong LT, Philipp B, Reinisch G, Wandrey C (1979) Zellstoff Papier 28:268
Wandrey C, Jaeger W, Starke W, Wotzka J (1984) Wasserwirtschaft Wassertechnik 34:18
Dautzenberg H, Jaeger W, Kötz J, Philipp B, Seidel C, Stscherbina D (1994) Polyelectrolytes. Formation, characterization, application. Carl Hanser Verlag, München
Mandel M (1988) In: Encycl Polym Sci Eng vol 11: Wiley & Sons, New York: 739
Anonymous (1968) Chem Eng News: 46
Negi Y, Harada S, Hishizuka O (1967) J Polym Sci A1, 5:1951
Harada S, Arai K (1967) Makromol Chem 107:64
Wandrey C (1980) Dissertation, FB Chemie AdW, Berlin
Ballschuh D, Jaeger W, Hahn M, Reinisch G, Ohme R (1977) DD-PS 128 392
Hunter WE, Sieder TP (1979) U.S. Pat 4,151,202
Wandrey C, Görnitz E (1992) Acta Polym 43:320
Ohme R, Ballschuh D, Seibt H (1991) Tenside Surf. Det. 28:180
Martin V, Ringsdorf H, Thunig D (1977) In: Polymerization of organized systems. Midland Macromolecular Monographs, Gardon & Breack Sci Publ 3:175
Wandrey C (1997) Polyelektrolyte-Makromolekulare Parameter und Elektrolytverhalten. Cuvillier Verlag, Göttingen
Wedler G (1987) Lehrbuch der Physikalischen Chemie. VCH, Weinheim
Butler GB (1960) J Polym Sci 48:279
Masterman TC, Dando NR, Weaver DG, Seyferth D (1994) J Polym Sci, Part B: Polym Physics 32:2263
Wehrman C (1974) Diploma Thesis, TU Dresden
Birnstein D (1975) Diploma Thesis, TU Dresden
Jaeger W, Wandrey C, Hahn M, Ballschuh D, Ohme R, Staeck R, Biering H (1987) EP 0,264,710
Ruppelt D, Kötz J, Jaeger W, Friberg SE, Mackay RA (1997) Langmuir 13:3316
Brand F (1995) Thesis, TU Berlin
Brand F, Dautzenberg H, Jaeger W, Hahn M (1997) Angew Makromol Chem 248:41
Truong ND, Galin JC, Francois J (1986) Polymer 27:459
Vu C, Cabestany J (1991) J Appl Polym Sci 42:2857
Murphy PD, Pietro RAD, Lund CJ Weber WD (1994) Macromolecules 24:279
Hahn M, Jaeger W (1992) Angew Makromol Chem 198:165
Jaeger W, Hahn M, Lieske A, Zimmermann A (1996) Macromol Symp 111:95
Hahn M (1983) Dissertation, FB Chemie AdW, Berlin
Martynenko AI, Wandrey C, Jaeger W, Hahn M, Topchiev DA, Reinisch G, Kabanov VA (1985) Acta Polym 36:516
Hunkeler D (1991) Macromolecules 24:2160
Jaeger W, Hong LT, Philipp B, Reinisch G, Wandrey C (1980) In: Polymeric amines and ammonium salts. Goethals E (ed) Pergamon Press, Oxford: 155
Kabanov VA, Topchiev DA, Nazhmetdinova GT (1983) Izv Akad Nauk SSSR Ser Khim 9:2146
Babaev HA, Martynenko AI, Topchiev DA, Kabanov VA, Wandrey C, Hahn M, Jaeger W, Reinisch G (1985) Acta Polym 36:396
Wyroba A (1981) Polymeri 26:139
Hahn M, Jaeger W, Reinisch G (1983) Acta Polymer 34:322
Schuller WHJ, Price JA, Moore ST Thomas WM (1959) J Chem Eng Data 4:273
Mayo FR, Lewis FM (1944) J Am Chem Soc 66:1595
Riggs JP, Podriguez FJ (1967) J Polym Sci A1 5:3151
Wandrey C, Jaeger W (1985) Acta Polym 36:100
Tanaka H (1986) J Polym Sci Polym Chem Ed 24:29
Matsumoto A, Wakabayashi S, Oiwa M, Butler GB (1989) J Macromol Sci Chem A26:1475
Brand F, Dautzenberg H, Jaeger W, Hahn M (1997) Angew Makromol Chem 248:41
Huang PC, Singh P, Reichert KH (1986) In: Polymer Reaction Engineering. Reichert KH, Geiseler W (eds) VCH Weinheim:125
Singh P (1986) DFG Report 223/13-1. Inst Techn Chem TU Berlin
Hunkeler D, Hamielec AE (1991) Polymer 32:2626
Kelen T, Tüdös F (1975) J Macromol Sci Chem A9:1
Reilly PM, Blau GE (1974) Can J Chem Eng 52:289
Baade W, Hunkeler D, Hamielec AE (1988) J Appl Polym Sci 38:185
Wandrey C, Görnitz E (1995) Polym News 22:377
Janietz S, Hahn M, Jaeger W (1992) Acta Polym 43:230
Schuller WH, Thomas WM, Moore ST House RA (1959) U.S. Pat 2,884,054
Nixon AC, Berrigan PJ, Williams PH (1966) US Pat: 3,278,474
Deng YL, Pelton R (1995) Macromolecules 28:4617
Moench D, Hartmann H, Buechner KH (1990) OS DE 3,909,005
Jen Y (1960) U.S. Pat 2,958,673
Harada S, Katayama (1968) U.S. Pat 3,375,233
Bhattacharyya BR, Dalsin PD (1987) U.S, Pat 4,713,431
Amjad Z, Masler, WF (1989) U.S. Pat 4,889,637
Chung DK, Ramesh M (1997) U.S. Pat 5,597,490
Tibbits D, (1996) U.S. Pat 5,529,696
Shetty, CS, Ramesh M (1996) U.S. Pat 5,527,431
John St MR, Alexander RL (1990) U.S. Pat 5,013,456
Amjad Z, Masler WF (1989) U.S. Pat 4,885,097
Bhattacharyya BR, Srivatsa SR, Dwyer ML (1987) U.S. Pat 4,715,962
Gopoakrishnan S, Butler BG, Hogen-Esch TE, Zhang NZ (1991) ACS Symp Ser 467:175
Butler GB, Do CH (1991) ACS Symp Ser 467:151
Kevelam J, Engberts BFN (1995) Langmuir 11:793
Topchiev DA, Sivov NA, Goethals EJ (1994) Russ Chem Bull 43:1864
Becker LW, Larson EH (1986) U.S. Pat 4,617,362
Polyelectrolytes: Science and technology. Harada M ed (1993) Marcel Decker, New York
Schmitz KS (1993) Macroions in solution and colloidal suspension, VCH, New York
Förster S, Schmidt M (1995) Adv Polym Sci 120:51
Fuoss RM, Katchalsky A, Lifson S (1951) Proc Acad Sci 37:579
Alexandrowicz Z, Katchalsky A (1963) J Polym Sci A1:3231
Oosawa F (1971) Polyelectrolytes, Marcel Dekker, New York
Manning GS, Zimm BH (1965) J Chem Phys 43:4250
Manning GS (1965) J Chem Phys 43:4260
Manning GS (1969) J Chem Phys 51:924
Manning GS (1969) J Chem Phys 51:934
Manning GS (1977) Biophys Chem 7:95
Manning GS (1978) Biophys Chem 9:65
Manning GS (1978) Quart Rev Biophys 11:179
Manning GS (1979) Acc Chem Res 12:443
Gennes de PG (1979) Scaling conceps in polymer physics, Cornell Univ Press, Ithaca, New York
Odijk T (1977) J Polym Sci Polym Phys Ed 15:477
Odijk T (1979) Macromolecules 12:688
Odijk T, Houwaart AC (1978) J Polym Sci, Polym Phys Ed 16:627
Skolnik J, Fixman M (1977) Macromolecules 10:944
Iwasa K, Quarrie Mc DA, Kwak JCT (1978) J Phys Chem 82:1979
Gueron M, Weisbuch G (1979) J Phys Chem 83:1991
Yoshida N (1978) J Chem Phys 69:4867
Yoshida N (1982) Chem Phys Lett 90:207
Leeuven v HP, Cleven FRM, Valenta P (1991) Pure Appl Chem 63:1251
Manning GS (1970) Biopolymers 9:1543
Huzienga JR, Grieger PF, Wall FT (1950) J Am Chem Soc 72:2636
Eisenberg H (1958) J Polym Sci 30:47
Kuruczev T, Steel BJ, (1967) Rev Pure Appl Chem 17:149
Manning GS (1975) 79:262
Schmitz KS ed (1994) Macro-ion characterization. ACS Symp Ser 548, Washington
Oehme F (1986) Ionenselektive Elektroden. Hüthig, Heidelberg
Rios HE, Gamboa C, Ternero G (1991) J Polym Sci, Part B: Polym Phys 29:805
Kwak JCT (1973) J Polym Sci Chem 77:2790
Vink H (1982) Makromol Chem 183:2273
Wandrey C, Zarras P, Vogl O (1995) Acta Polym 46:247
Wandrey C (1996) Ber Bunsenges Phys Chem 100:869
Görnitz E, Hahn M, Jaeger W, Dautzenberg H (1997) Progr Colloid Polym Sci 107:127
Burkhardt CW, McCarthy KJ, Parazak DP (1987) J Polym Sci, Polym Lett Ed 25:209
Wandrey C, Jaeger W, Reinisch G (1982) Acta Polym 33:156
Timofejeva GI, Pavlova SA, Wandrey C, Jaeger W, Linow KJ, Görnitz E (1990) Acta Polym 41:479
Dubin PL, The SS, Gan LM, Chew CH (1990) Macromolecules 23:2500
Xia J, Dubin PL, Edwards S, Havel H (1995) J Polym Sci, Part B: Polym Phys 33:1117
Dautzenberg H, Görnitz E, Jaeger W (1998) Macromol Chem Phys 199:1561
Dautzenberg H, Rother G (1991) J Appl Polym Sci, Appl Polym Symp 48:351
Bekturov EA, Kudaibergenov SE, Ushanov VZ, Saltybaeva SS (1985) Makromol Chem 186:71
Okay O, Schindlbauer H (1984) Angew Makromol Chem 122:21
Janado M (1988) In: Aqueous size exclusion chromatography. Dubin PL (ed), Elsevier, Amsterdam
Strege HA, Dubin PL (1989) J Chromatogr 463:165
Bruessau RJ (1992) Makromol Chem Makromol Symp 61:199
Wandrey C, Jaeger W, Reinisch G (1982) Acta Polym 33:442
Thielking H, Adolphi U, Kulicke WM (1996) Nachr Chem Tech Lab 44:370
Butler GB, Wu C (1976), U.S. Pat 3,962,206
Dubin PL, Levy IJ (1982) J Chromatogr 235:377
Levy IJ, Dubin PL (1982) Ind Eng Chem Prod Res Dev 21:59
Kokufuta E, Takahashi K (1986) Macromolecules 19:351
Philipp B, Dautzenberg H, Linow KJ, Kötz J, Dawydoff W (1989) Progr Polym Sci 14:91
Philipp B, Kötz J, Linow KJ, Dautzenberg H (1991) Polym News 16:106
Bowman WA, Rubinstein M, Tan JS (1997) Macromolecules 30:3262
Tabellenbuch Chemie (1968) Dt Verlag Grundstoffind, 288
Bekturov EA, Kudaibergenov SE, Ushanov VZ, Saltybaeva SS (1985) Makromol Chem 186:71
Wei YC, Hudson SM (1995) J Macromol Sci, Rev Macromol Chem Phys C35:15
Quigg Mc DW, Kaplan JI, Dubin PL (1992) J Phys Chem 96:1973
Xia J, Zhang H, Rigsbee DR, Dubin PL, Shaikh T (1993) Macromolecules 26:2759
Swanson-Vethamuthu M, Dubin PL, Almgren M, Li, Y (1997) J Colloid Interface Sci 186:414
Ober CK, Wegner G (1997) Adv Mater 9:17
Antonietti M, Kaul A, Thünemann A (1995) Langmuir 11:2633
Antonietti M, Wenzel A, Thünemann A (1996) Langmuir 12:2111
Antonietti M, Henke S, Thünemann A (1996) Adv. Mater 8:41
Mikulik J, Vinklarek Z, Vondruska M (1993) Collect Czech Chem Commun 58:713
Dautzenberg H, Koetz J, Linow KJ, Philipp B, Rother G (1994) In: Macromolecular complexes in chemistry and biology. Dubin PL (ed) Springer, Berlin, New York
Kabanov VA (1994) In: Macromolecular complexes in chemistry and biology. Dubin PL (ed) Springer, Berlin, New York
Dautzenberg H, Loth F, Fechner K, Mehlis B, Pommerenning K (1985) Macromol Chem Suppl 9:203
Dautzenberg H, Lukanoff B, Eckert U, Tiersch B, Schuldt U (1996) Ber Bunsenges Phys Chem 100:1045
Schwarz HH, Richau K, Paul D (1992) Polym Bull 25:95
Dautzenberg H, Hartmann, Grunewald S, Brand F (1996) Ber Bunsenges Phys Chem 100:1024
Decher G, Schmitt J (1992) Progr Colloid Polym Sci 89: 160
Lvov Y, Ariga K, Ichinise I, Kunitake T (1996) Thin Solid Films 284/285:797
Wang Y, Gao, JY, Dubin PL (1996) Biotechnol Prog 12:356
Fleer GJ, Cohen Stuart MA, Scheutchens JMHM, Cosgrove T, Vincent B (1993) Polymers at Interfaces, Capman & Hall, London
Horn D, Linhart F (1991) In: Paper chemistry. Roberts CJ (ed) Blackie, Glasgow
Wandrey C (1998) Polym News 23:123
Biermann CJ (1996) Handbook of pulping and papermaking, Academic Press, San Diego
Coscia AT, Williams LL (1971) U.S. Pat 3,556,932
Williams LL, Coscia AT (1971) U.S. Pat 3,556,933
Ballweber EG, Jansma RH, Phillips KG (1980) U.S. Pat 4,217,425
Bjorkquist DW, Schmidt WW (1986) U.S. Pat 4,603,176
Furman, Jr. GS (1993) U.S. Pat 5,187,219
Noda, I (1993) U.S. Pat 5,200,036
Dauplaise DL, Kozakiewicz JJ, Schmitt JM (1994) U.S. Pat 5,320,711
Darlington WB, Lanier WG (1995) U.S. Pat 5,427,652
Darlington WB, Lanier WG (1995) U.S. Pat 5,466,337
Jansma RH, Begala AJ, Furman GS (1996) U.S. Pat 5,490,904
Unbehend JE, Britt KW (1981) In: Pulp and paper. Chemistry and chemical technology, vol. 3. James P. Casey (ed), John Wiley&Sons, New York
Lim SK, Bloomquist AE, Shaper RJ (1978) U.S. Pat 4,077,930
Hund R, Philibert E (1995) U.S. Pat 5,393,381
St. John MR (1992) U.S. Pat 5,131,882
Shetty CS, Ramesh M (1996) U.S. Pat 5,510,439
Finck MR, Greer CS, Ramesh, M (1993) U.S. Pat 5,246,547
Greer CS, James NP (1993) U.S. Pat 5,230,774
Hurlock JR, Ballweber EG, Connelly LJ (1975) U.S. Pat 3,920,599
Antonetti JM, Snow GF (1979) U.S. Pat 4,141,691
Sykes RC, Connelly LJ, Roe WJ (1985) U.S. Pat 4,555,329
Kerr EM, Ramesh M (1997) U.S. Pat 5,622,647
Kerr EM (1995) U.S. Pat 5,603,841
Kerr EM, Ramesh M (1995) U.S. Pat 5,476,522
Kerr EM, Ramesh M (1997) U.S. Pat 5,597,475
Pillai KJ, Kerr EM (1996) U.S. Pat 5,518,634
Tippett JM, Groesz M (1993) U.S. Pat 5,215,784
Richardson PF, Bhattacharyya, BR (1987) U.S. Pat 4,673,511
Marble RA, Braden ML (1992) U.S. Pat 5,128,046
Meyer EM, Wood, MR (1993) U.S. Pat 5,256,304
Waldmann JJ (1994) U.S. Pat 5,294,352
Chung DK, Ramesh M (1997) U.S. Pat 5,624,569
Chung DK, Shetty CS, Ramesh M (1997) U.S. Pat 5,601,725
Ramesh M, Sivakumar A (1997) U.S. Pat 5,635,112
Sivakumar A, Ramesh M (1996) U.S. Pat 5,560,832
Demorest DM, Werner WE, Wiktorowics JE, (1993) U.S. Pat 5,264,101
Bernas SM, Oades JM, Churchman GJ (1995) Australian J Soil Research 33:805
Bernas SM, Oades JM, Churchman GJ, Grant CD (1995) Australian J Soil Research 33:369
Krokhin OV, Hoshino H, Shpigun OA, Yotsuyanagi T (1997) J Chromatogr 776:329
Deng YL, Xiao HN, Pelton R (1996) J Colloid Interface Sci 179:188
Masadome T, Imato T (1995) Fresenius J Analyt Chem 352:596
Philipp B, Jaeger W, Gohlke U, Wandrey C, Hahn M, Dietrich K, Reinisch, G, Linow, KJ, Dautzenberg H, Kötz J (1986) Paperi ja Puu 5:419
Philipp B, Gohlke U, Jaeger, H, Kötz J (1989) Wiss Fortschritt 39:137
Mortimer DA (1991), Polym Internat 25:29
Itaya T, Kawabata Y, Ochiai H, Ueda K, Imamura A (1994) Bull Chem Soc Jpn 67:2047
Author information
Authors and Affiliations
Editor information
Rights and permissions
Copyright information
© 1999 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Wandrey, C., Hernández-Barajas, J., Hunkeler, D. (1999). Diallyldimethylammonium Chloride and its Polymers. In: Capek, I., Hernfández-Barajas, J., Hunkeler, D., Reddinger, J.L., Reynolds, J.R., Wandrey, C. (eds) Radical Polymerisation Polyelectrolytes. Advances in Polymer Science, vol 145. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-70733-6_3
Download citation
DOI: https://doi.org/10.1007/3-540-70733-6_3
Received:
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-65210-6
Online ISBN: 978-3-540-70733-2
eBook Packages: Springer Book Archive