Re-Mendable Polymers

Springer Series in Materials Science

Volumn 100, Issue , 2007, Pages 45-68

  Bergman, Sheba D ^a   Wudl, Fred ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Calcite Precipitation; Ethylene Adipate; Healing Agent; Maleamic Acid; Polymer Matrix Composite Material

Indexed keywords

EID: 61849094896     PISSN: 0933033X     EISSN: 21962812     Source Type: Book Series    
DOI: 10.1007/978-1-4020-6250-6_3     Document Type: Chapter

References (123)

1. Gandini A. (2005) The application of the Diels-Alder reaction to polymer syntheses based on furan/maleimide reversible couplings. Polímeros: Ciência e Tecnologia 15:95–101
2. Craven J.M. (1969) Cross-linked thermally reversible polymers produced from condensation polymers with pendant furan groups cross-linked with maleimides. US Patent 3,435,003
3. Stevens M., Jenkins A. (1979) Crosslinking of polystyrene via pendant maleimide groups. J Polym Sci 17:3675–3685
4. Chujo Y., Sada, K., Saegusa T. (1990) Reversible gelation of polyoxazoline by means of Diels-Alder reaction. Macromolecules 23:2636–2641
5. Imai Y., Itoh H., Naka K., Chujo Y. (2000) Thermally reversible IPN organic-inorganic polymer hybrids utilizing the Diels-Alder reaction. Macromolecules 33:4343–4346
6. Canary S.A., Stevens M.P. (1992) Thermally reversible crosslinking of polystyrene via the furan-maleimide Diels-Alder reaction. J Polym Sci: Polym Chem 30:1755–1760
7. Laita H., Boufi S., Gandini A. (1997) The application of the Diels-Alder reaction to polymers bearing furan moieties. 1. Reactions with maleimides. Eur Polym J 33:1203–1211
8. Goussé C., Gandini A., Hodge P. (1998) Application of the Diels-Alder reaction to polymers bearing furan moieties. 2. Diels-Alder and retro-Diels-Alder reactions involving furan rings in some styrene copolymers. Macromolecules 31:314–321
9. Gheneim R., Perez-Berumen C., Gandini A. (2002) Diels-Alder reactions with novel polymeric dienes and dienophiles: synthesis of reversibly cross-linked elastomers. Macromolecules 35:7246–7253
10. Goiti E., Huglin M.B., Rego J.M. (2001) Some observations on the copolymerization of styrene with furfuryl methacrylate. Polymer 42:10187–10193
11. Goiti E., Huglin M.B., Rego J.M. (2003) Thermal breakdown by the retro Diels-Alder reaction of crosslinking in poly[styrene-co-(furfuryl methacrylate)]. Macromol Rapid Commun 24:692–696
12. Goiti E., Huglin M.B., Rego J.M. (2004) Some properties of networks produced by the Diels-Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide. Eur Polym J 40:219–226
13. Goiti E., Huglin M.B., Rego J.M. (2004) Kinetic aspects of the Diels-Alder reaction between poly(styrene-co-furfuryl methacrylate) and bismaleimide. Eur Polym J 40:1451–1460
14. Gheneim R., Perez-Berumen C., Gandini A. (2002) Diels-Alder reactions with novel polymeric dienes and dienophiles: synthesis of reversibly cross-linked elastomers. Macromolecules 35:7246–7253
15. Kuramoto N., Hayashi K., Nagai K. (1994) Thermoreversible reaction of Diels-Alder polymer composed of difurfuryl adipate with bismaleimidodiphenylmethane. J Polym Sci: Polym Chem 32:2501–2504
16. Tesoro G.C., Sastri V.R. (1986) Synthesis of siloxane-containing bis(furans) and polymerization with bis(maleimides). Ind Eng Chem: Prod Res Dev 25:444–448
17. Diakoumakos C.D., Mikroyannidis J.A. (1992) Polyimides derived from Diels-Alder polymerization of furfuryl-substituted maleamic acids or from the reaction of bismaleamic with bisfurfurylpyromellitamic acids. J Polym Sci Polym Chem 30:2559–2567
18. Diakoumakos C.D., Mikroyannidis J.A. (1994) Heat-resistant resins derived from cyano-substituted Diels-Alder polymers. Eur Polym J 30:465–472
19. Goussé C., Gandini A. (1999) Diels-Alder polymerization of difurans with bismaleimides. Polym Intern 48:723–731
20. McElhanon J.R., Wheeler D.R. (2001) Thermally responsive dendrons and dendrimers based on reversible furan-maleimide Diels-Alder adducts. Org Lett 3:2681–2683
21. McElhanon J.R., Russick E.M., Wheeler D.R., Loy D.A., Aubert J.H. (2002) Removable foams based on an epoxy resin incorporating reversible Diels-Alder adducts. J Appl Polym Sci 85:1496–1502
22. Loy D.A., Wheeler D.R., McElhanon J.R., Durbin-Voss M.L. (2002) Method of making thermally removable Diels-Alder adduct-containing polyurethanes. US Patent 6403753
23. Loy D.A., Wheeler D.R., Russick E.M., McElhanon J.R., Sanders R.S. (2002) Method of making thermally removable epoxy resins. US Patent 6403753
24. Small J.H., Loy D.A., Wheeler D.R., McElhanon J.R., Saunders R.S. (2001) Method of making thermally removable polymeric encapsulants from maleimide resins. US Patent 6271335
25. Loy D.A., Wheeler D.R., Saunders R.S., McElhanon J.R., Small J.H. (2001) Method of making thermally removable polymeric encapsulants US Patent 6271335
26. Kamahori K., Tada S., Ito K., Itsuno S. (1999) Optically active polymer synthesis by Diels-Alder polymerization with chirally modified lewis acid catalyst. Macromolecules 32:541–547
27. Goussé C., Gandini A. (1998) Synthesis of 2-furfurylmaleimide and preliminary study of its Diels-Alder polycondensation. Polym Bull 40:389–394
28. Chen X., Dam M.A., Ono K., Mal A.K., Shen H., Nutt S.R., Sheran K., Wudl F. (2002) A thermally re-mendable cross-linked polymeric material. Science 295:1698–1702
29. Chen X., Wudl F., Mal A.K., Shen H., Nutt S.R. (2003) New thermally remendable highly cross-linked polymeric materials. Macromolecules 36:1802–1807
30. Wudl F., Chen X. (2004) Thermally re-mendable crosslinked polymers, monomers, their manufacture, and thermally mending. US Patent 2004014933
31. Liu Y.L., Hsieh C.Y. (2006) Crosslinked epoxy materials exhibiting thermal remendablility and removability from multifunctional maleimide and furan compounds. J Polym Sci: Polym Chem 44:905–913
32. Watanabe M., Yoshie N. (2006) Synthesis and properties of readily recyclable polymers from bisfuranic terminated poly(ethylene adipate) and multi-maleimide linkers. Polymer 47:4946–4952
33. Liu Y.L., Chen Y.W. (2007) Thermally reversible cross-linked polyamides with high toughness and self-repairing ability from maleimide-and furan-functionalized aromatic polyamides. Macromol Chem Phys 208:224–232
34. Gotsmann B., Duerig U., Frommer J., Hawker C.J. (2006) Exploiting chemical switching in a Diels-Alder polymer for nanoscale probe lithography and data storage. Adv Funct Mater 16:1499–1505
35. Stille J.K., Plummer L. (1961) Polymerization by the Diels-Alder reaction. J Org Chem 26: 4026–4029
36. Takeshita Y., Uoi M., Hirai Y., Uchiyama M. (1972) Polymers crosslinked through dicyclopentadiene rings. German Patent 2164022
37. Kennedy J.P., Castner K.F. (1979) Thermally reversible polymer systems by cyclopentadienylation. I. A model for termination by cyclopentadienylation of olefin polymerization. J Polym Sci: Polym Chem Ed 17:2039–2054
38. Kennedy J.P., Castner K.F. (1979) Thermally reversible polymer systems by cyclopentadienylation. II. The synthesis of cyclopentadiene-containing polymers. J Polym Sci: Polym Chem Ed 17:2055–2070
39. Miura M., Akutsu F., Usui T., Ikebukuro Y., Nagakubo K. (1985) Soluble cyclopentadieny-lated polymers. Makromol Chem 186:473–481
40. Salamone J.C., Chung Y., Clough S.B., Watterson A.C. (1988) Thermally reversible, covalently crosslinked polyphosphazenes. J Polym Sci: Polym Chem Ed 26:2923–2939
41. Chen X.N., Ruckenstein E.J. (1999) Thermally reversible linking of halide-containing polymers by potassium dicyclopentadienedicarboxylate. J Polym Sci: Polym Chem 37:4390–4401
42. Ruckenstein E.J., Chen X.N. (2000) Crosslinking of chlorine-containing polymers by dicyclopentadiene dicarboxylic salts. J Polym Sci: Polym Chem 38:818–825
43. Chen X.N., Ruckenstein E.J. (2000) Thermally reversible covalently bonded linear polymers prepared from a dihalide monomer and a salt of dicyclopentadiene dicarboxylic acid. J Polym Sci: Polym Chem 38:1662–1672
44. Murphy E., Bolanos E., Wudl F. (2007) Manuscript in preparation.
45. Stevens M.P. (1984) Diels-Alder polymer of N-(2-anthryl)maleimide. J Polym Sci: Polym Lett Ed 22:467–471
46. Grigoras M., Colotin G. (2001) Copolymerization of a bisanthracene compound with bismaleimides by Diels–Alder cycloaddition. Polym Int 50:1375–1378
47. Jones J.R., Liotta C.L., Collard D.M., Schiraldi D.A. (1999) Cross-linking and modification of poly(ethylene terephthalate-co-2,6-anthracenedicarboxylate) by Diels-Alder reactions with maleimides. Macromolecules 32:5786–5792
48. Brand T., Klapper M. (1999) Control of viscosity through reversible addition of telechelics via repetitive Diels-Alder reaction in bulk. Des Monomers Polym 2:287–309
49. Muehlebach A., Hafner A., Van Der Schaaf P.A. (1996) Crosslinkable polymers and process for crosslinking them. Int Patent 9623829
50. Chen Y., Geh J.L. (1996) Copolymers derived from 7-acryloyloxy-4-methylcoumarin and acrylates: 2. Reversible photocrosslinking and photocleavage. Polymer 37:4481–4486
51. Matsui J., Ochi Y., Tamaki K. (2006) Photodimerization of anthryl moieties in a poly(methacrylic acid) derivative as reversible cross-linking step in molecular imprinting. Chem Lett 35:80–81
52. Zheng Y., Micic M., Mello S.V., Mabrouki M., Andreopoulos F.M., Konka V., Pham S.M., Leblanc R.M. (2002) PEG-based hydrogel synthesis via the photodimerization of anthracene groups. Macromolecules 35:5228–5234
53. Torii T., Ushiki H., Horie K. (1993) Fluorescence study on dynamics and structure of polymer chain. II. Dependence of intramacromolecular photocrosslinking reaction of polymers with anthryl and eosinyl moieties on number of crosslinkable side chains. Polym J 25:173–183
54. Chujo Y., Sada K., Nomura R., Naka A., Saegusa T. (1993) Photogelation and redox properties of anthracene-disulfide-modified polyoxazolines. Macromolecules 26:5611–5614
55. Chang J.M., Aklonis J.J. (1983) A photothermal reversibly crosslinkable polymer system. J Polym Sci: Polym Lett Ed 21:999–1004
56. Chung C.M., Roh Y.S., Cho S.Y., Kim J.G. (2004) Crack healing in polymeric materials via photochemical [2+2] cycloaddition. Chem Mater 16:3982–3984
57. Serpe M.J., Craig S.L. (2007) Physical organic chemistry of supramolecular polymers. Langmuir 23:1626–1634
58. Harada A., Hashidzume A., Takashima Y. (2006) Cyclodextrin-based supramolecular polymers. Adv Polym Sci 201:1–43
59. Lehn J.M. (2005) Dynamers: dynamic molecular and supramolecular polymers. Prog Polym Sci 30:814–831
60. Ciferri A. (2005) Supramolecular polymers, 2nd edn. Taylor & Francis, Boca Raton, FL
61. Armstrong G., Buggy M. (2005) Hydrogen-bonded supramolecular polymers: a literature review. J Mater Sci 40:547–559
62. Brunsveld L., Folmer B.J.B., Meijer E.W., Sijbesma R.P. (2001) Supramolecular polymers. Chem Rev 101:4071–4097
63. Moore J.S. (1999) Supramolecular polymers. Curr Opin Coll Int Sci 4:108–116
64. Sijbesma R.P., Beijer F.H., Brunsveld L., Folmer B.J.B., Ky Hirschberg J.H.K., Lange R.F.M., Lowe J.K.L., Meijer E.W. (1997) Reversible polymers formed from self-complementary monomers using quadruple hydrogen bonding. Science 278:1601–1604
65. Beijer F.H., Sijbesma R.P., Kooijman H., Spek A.L., Meijer E.W. (1998) Strong dimerization of ureidopyrimidones via quadruple hydrogen bonding. J Am Chem Soc 120:6761–6769
66. Söntjens S.H.M., Sijbesma R.P., van Genderen M.H.P., Meijer E.W. (2000) Stability and lifetime of quadruply hydrogen bonded 2-ureido-4[1H]-pyrimidinone dimers. J Am Chem Soc 122: 7487–7493
67. Ky Hirschberg J.H.K., Beijer F.H., van Aert H.A., Magusin P.C.M.M., Sijbesma R.P., Meijer E.W. (1999) Supramolecular polymers from linear telechelic siloxanes with quadruple-hydrogen-bonded units. Macromolecules 32:2696–2705
68. Lange R.F.M., Van Gurp M., Meijer E.W. (1999) Hydrogen-bonded supramolecular polymer networks. J Polym Sci: Polym Chem 37:3657–3670
69. Folmer B.J.B., Sijbesma R.P., Versteegen R.M., van der Rijt J.A.J., Meijer E.W. (2000) Supramolecular polymer materials: chain extension of telechelic polymers using a reactive hydrogen-bonding synthon. Adv Mater 12:874–878
70. El-ghayoury A., Peeters E., Schenning A.P.H.J., Meijer E.W. (2000) Quadruple hydrogen bonded oligo(p-phenylene vinylene) dimers. Chem Commun 19:1969–1970
71. Ky Hirschberg J.H.K., Brunsveld L., Ramzi A., Vekemans J.A.J.M., Sijbesma R.P., Meijer E.W. (2000) Helical self-assembled polymers from cooperative stacking of hydrogen-bonded pairs. Nature 407:167–170
72. Schenning A.P.H.J., Jonkheijm P., Peeters E., Meijer E.W. (2001) Hierarchical order in supramolecular assemblies of hydrogen-bonded oligo(p-phenylene vinylene)s. J Am Chem Soc 123: 409–416
73. El-Ghayoury A., Schenning A.P.H.J., Van Hal P.A., Van Duren J.K.J., Janssen R.A.J., Meijer E.W. (2001) Supramolecular hydrogen-bonded oligo(p-phenylene vinylene) polymers. Angew Chem Int Ed 40:3660–3663
74. Keizer H.M., Sijbesma R.P., Jansen J.F.G.A., Pasternack G., Meijer E.W. (2003) Polymerization-induced phase separation using hydrogen-bonded supramolecular polymers. Macromolecules 36:5602–5606
75. Keizer H.M., van Kessel R., Sijbesma R.P., Meijer E.W. (2003) Scale-up of the synthesis of ureidopyrimidinone functionalized telechelic poly(ethylenebutylene). Polymer 44: 5505–5511
76. Bosman A.W., Brunsveld L., Folmer B.J.B., Sijbesma R.P., Meijer E.W. (2003) Supramolecular polymers: From scientific curiosity to technological reality. Macromol Symp 201:143–154
77. Bosman A.W., Sijbesma R.P., Meijer E.W. (2004) Supramolecular polymers at work. Mater Today 7:34–39
78. Ligthart G.B.W.L., Ohkawa H., Sijbesma R.P., Meijer E.W. (2005) Complementary quadruple hydrogen bonding in supramolecular copolymers. J Am Chem Soc 127:810–811
79. Scherman O.A., Ligthart G.B.W.L., Sijbesma R.P., Meijer E.W. (2006) A selectivity-driven supramolecular polymerization of an AB monomer. Angew Chem Int Ed 45:2072–2076
80. Kautz H., van Beek D.J.M., Sijbesma R.P., Meijer E.W. (2006) Cooperative end-to-end and lateral hydrogen-bonding motifs in supramolecular thermoplastic elastomers. Macromolecules 39:4265–4267
81. Ohkawa H., Ligthart G.B.W.L., Sijbesma R.P., Meijer E.W. (2007) Supramolecular graft copolymers based on 2,7-diamido-1,8-naphthyridines. Macromolecules 40:1453–1459
82. Bleay S.M., Loader C.B., Hawyes V.J., Humberstone L., Curtis P.T. (2001) A smart repair system for polymer matrix composites. Composites A 32:1767–1776
83. Zako M., Takano N. (1999) Intelligent material systems using epoxy particles to repair microcracks and delamination damage in GFRP. J Int Mater Sys Struct 10:836–841
84. Dry C. (1991) Alteration of matrix permeability, pore and crack structure by the time release of internal chemicals. Ceramic Trans: Adv Cem Mater 16:729–768
85. Dry C. (1994) Matrix cracking repair and filling using active and passive modes for smart timed release of chemicals from fibres into cement matrices. Smart Mater Struct 3:118–123
86. Dry C., McMillan W. (1996) Three-part methylmethacrylate adhesive system as an internal delivery system for smart responsive concrete. Smart Mater Struct 5:297–300
87. Dry C. (2001) Three designs for the internal release of sealants, adhesives and waterproofing chemical into concrete to release. Cement Concrete Res 30:1969–1977
88. Li V.C., Lim Y.M., Chan Y.W. (1998) Feasibility of a passive smart self-healing cementitious composite. Composites B 29B:819–827
89. Dry C., Corsaw M., Bayer E. (2003) A comparison of internal self-repair with resin injection in repair of concrete. J Adh Sci Tech 17:79–89
90. Dry C., Corsaw M. (2003) A comparison of bending strength between adhesive and steel reinforced concrete with steel only reinforced concrete. Cem Conc Res 33:1723–1727
91. Dry C. (2007) Multiple function, self-repairing laminated composites with special adhesives. Int Patent 2007005657
92. Dry C. (1996) Procedure developed for self-repair of polymer matrix composite materials. Comp Struct 35:263–269
93. Dry C., Sottos N. (1996) Passive smart self-repair in polymer matrix composite materials. Proc SPIE: Smart Mater Struct 1916:438–444
94. Dry C., McMillan W. (1997) A novel method to detect crack location and volume in opaque and semi-opaque brittle materials. Smart Mater Struct 6:35–39
95. Motuku M., Vaidya U.K., Janowski G.M. (1999) Parametric studies on self-repairing approaches for resin infused composites subjected to low velocity impact. Smart Mater Struct 8:623–638
96. White S.R., Sottos N.R., Geubelle P.H., Moore J.S., Kessler M.R., Sriram S.R., Brown E.N., Viswanathan S. (2001) Autonomic healing of polymer composites. Nature 409:794–797
97. Kessler M.R., White S.R. (2001) Self-activated healing of delamination damage in woven composites. Composites A 32:683–699
98. Kessler M.R., Sottos N.R., White S.R. (2003) Self-healing structural composite materials. Composites A 34:743–753
99. Brown E.N., Sottos N.R., White S.R. (2002) Fracture testing of a self-healing polymer composite. Exp Mech 42:372–379
100. Brown E.N., Kessler M.R., Sottos N.R., White S.R. (2003) In situ poly (ureaformaldehyde) microencapsulation of dicyclopentadiene. J Microencapsul 20:719–730
101. Brown E.N., White S.R., Sottos N.R. (2004) Microcapsule induced toughening in a self-healing polymer composite. J Mater Sci 39:1703–1710
102. Jones A.S., Rule J.D., Moore J.S., White S.R., Sottos N.R. (2006) Catalyst morphology and dissolution kinetics of self-healing polymers. Chem Mater 18:1312–1317
103. Liu X., Lee J.K., Yoon S.H., Kessler M.R. (2006) Characterization of diene monomers as healing agents for autonomic damage repair. J Appl Polym Sci 101:1266–1272
104. Maiti S., Shankar C., Geubelle P.H., Kieffer J. (2006) Continuum and molecular-level modeling of fatigue crack retardation in self-healing polymers. J Eng Mat Tech 128:595–602
105. Cho S.H., Andersson H.M., White S.R., Sottos N.R., Braun P.V. (2006) Polydimethylsiloxane-based self-healing materials. Adv Mater 18:997–1000
106. Pang J.W.C., Bond I.P. (2004) Bleeding composites – damage detection and self-repair using a biomimetic approach. Composites A 36:183–188
107. Pang J.W.C., Jody W.C., Bond I.P. (2005) A hollow fibre reinforced polymer composite encompassing self-healing and enhanced damage visibility. Comp Sci Tech 65:1791–1799
108. Gollapudi U.K., Knutson C.L., Bang S.S., Islam M.R. (1995) A new method for controlling leaching through permeable channels. Chemosphere 30:695–705
109. 3. Soil Bio Biochem 31:1563–1571
110. Bang S.S., Galinat J.K., Ramakrishnan V. (2001) Calcite precipitation induced by polyurethane-immobilized Bacillus pasteurii. Enz Microb Tech 28:404–409
111. Bachmeier K., Williams A.E., Warmington J., Bang S.S. (2002) Urease activity in microbiologically-induced calcite precipitation. J Biotech 93:171–181
112. http://ssbang.sdsmt.edu/PDF%20Files/MECR.pdf
113. Holliday L. (1975) Ionic polymers. Wiley, New York
114. http://www2.dupont.com/Surlyn/en US/and http://www2.dupont.com/Products/en RU/Nucrel en.html
115. Eisenberg A., Kim J.S. (1998) Introduction to ionomers. Wiley, New York
116. Tant M.R., Mauritz K.A., Wilkes G.L. (1997) Ionomers: Synthesis, structure, properties, and applications. Chapman & Hall, New York
117. Wilson A.D., Prosser H.J. (1983) Developments in ionic polymers. Applied Science, New York
118. Kalista S.J. (2003) Self-healing of thermoplastic poly(ethylene-co-methacrylic acid) copolymers following projectile puncture. M.Sc. Thesis, Virginia Tech http://scholar.lib.vt.edu/theses/available/etd-12162003–103411/
119. Kalista S.J., Ward T.C., Oyetunji Z. (2003) Self-healing behavior of ethylene-based ionomers. Proc Ann Meet Adhes Soc 26:176–178
120. Kalista S.J., Ward T.C. (2004) A quantitative comparison of puncture-healing in a series of ethylene based ionomers. Proc Ann Meet Adhes Soc 27:212–214
121. Fall R. (2001) Puncture reversal of ethylene ionomers-mechanistic studies. M.Sc. Thesis, Virginia Tech http://scholar.lib.vt.edu/theses/available/etd-08312001–084412/
122. Huber A., Hinkley J.A. (2005) Impression testing of self-healing polymers. NASA Tech Man 2005–213532
123. Kalista S.J., Ward T.C. (2006) Self-healing in carbon nanotube filled thermoplastic poly(ethylene-co-methacrylic acid) ionomer composites. Proc Ann Meet Adhes Soc 29: 244–246