journal article·2019-06

Covalent cross-linking of polymers at room temperature

Silke Lorke, Uwe Müller, Robert Meissl, Oliver Brüggemann

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Abstract

Abstract Thermoplastic materials used in coatings, paints and adhesives as well as structural applications for sensitive substrates, such as wood, paper or polymers, often lack the required chemical and environmental resistance for many applications, which can be overcome by covalent cross-linking. Covalent cross-linking improves chemical and mechanical properties of the material and has been used for many different materials and applications. Room temperature cross-linking can be initiated by different mechanisms and eliminates energy intensive heating as well as conditions potentially harmful for the substrate. The present article focuses on cross-linking strategies applied for different materials, such as thermoplastics and thermosets. It is organized by material class, followed by an overview about triggering mechanisms for cross-linking reactions at room temperature. The authors hope to provide helpful insights about the methods for covalent cross-linking already published.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Polymer composites and self-healing · Synthetic Organic Chemistry Methods · Advanced Polymer Synthesis and Characterization

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (100+)

Show source-provided references
1. Low temperature curing epoxies for structural repair10.1016/0079-6700(94)90002-7 ↗
2. Evolution of the automotive body coating process - a review10.3390/coatings6020024 ↗
3. Development of low temperature curing, 120textdegreeC, durable, corrosion protection powder coatings for temperature sensitive substrates10.1007/BF02774595 ↗
4. Photochemical treatment of powder coatings and VOC-free coatings with NIR lasers exhibiting line-shaped focus: physical and chemical solidification
5. Christensen · 1997
6. Self-healing of densely crosslinked thermoset polymers - a critical review
7. Allonas · 2012
8. Makuuchi · 2011
9. 17 - crosslinked thermoplastics
10. Peroxide crosslinking of isotactic and syndiotactic polypropylene10.1016/S0032-3861(98)00519-9 ↗
11. 34 - the plastic piping industry in North America
12. Polyethylene cross-linking by two-step silane method: a review
13. Taege F, Hoffmann D, Häusler K-G, Timpe H-J, Müller U, Gladigau G. Photochemisches Vefahren zur Herstellung von Zahnprothesen mit druckäquilibrierenden Eigenschaften. DD 295 978 A5, 1991.
14. Baur · 2013
15. Koltzenburg · 2014
16. Whiteley · 2000
17. Kaiser · 2007
18. Domininghaus · 2012
19. The theory of permanent set at elevated temperatures in natural and synthetic rubber vulcanizates10.1063/1.1707724 ↗
20. Nitrogen-centered free radicals. IX. The ease of formation of thionitroxide radicals10.1021/ja00418a031 ↗
21. Kinetic applications of electron paramagnetic resonance spectroscopy. XXII. Dialkylaminothiyl radicals10.1021/ja00418a032 ↗
22. Dynamic hydrogels with an environmental adaptive self-healing ability and dual responsive sol–gel transitions10.1021/mz200195n ↗
23. Self-healing systems based on disulfide-thiol exchange reactions10.1039/c3py00087g ↗
24. Swelling kinetics of disulfide cross-linked microgels10.1021/ma025874f ↗
25. Using the dynamic bond to access macroscopically responsive structurally dynamic polymers10.1038/nmat2891 ↗
26. Synthesis and application of unprotected cyclic peptides as building blocks for peptide dendrimers10.1021/ja9621105 ↗
27. Making insoluble polymer networks malleable via olefin metathesis10.1021/ja303356z ↗
28. Crosslinkable poly(vinyl acetate)/clay nanocomposite films cast from soap-free emulsion-polymerized latices10.1002/app.28066 ↗
29. Corrosion behavior of three nanoclay dispersion MMethod of epoxy/organoclay nanocomposites
30. Aranguiz · 2004
31. Hardt · 2007
32. Hardtmann · 2003
33. Lehman · 2008
34. Tomasino · 1992
35. Arkles · 1992
36. Silane curing agents in waterwater coatings
37. Schilling · 1989
38. Crosslinked poly(vinyl alcohol) membranes10.1016/j.progpolymsci.2009.05.003 ↗
39. Amide-blocked aldehyde-functional monomers synthesis and chemistry
40. Degradable cross-linkers and strippable imaging materials for step-and-flash imprint lithography10.1021/ma702291k ↗
41. Materials for step and flash imprint lithography (S-FIL(R))10.1039/b705388f ↗
42. Jakob · 2002
43. Pervaporation separation of water-acetic acid mixtures through poly(vinyl alcohol) membranes crosslinked with glutaraldehyde
44. Ein neuer Weg bei der Naßfestausrüstung in der Papiermasse
45. Pinschmidt · 1988 · 467
46. 2015
47. Chemical reactions of polymer crosslinking and post-crosslinking at room and medium temperature10.1016/j.progpolymsci.2010.08.003 ↗
48. Nanocapsules for self-healing materials10.1016/j.compscitech.2007.07.021 ↗
49. Microcapsules filled with reactive solution for self-healing materials10.1016/j.polymer.2008.12.040 ↗
50. Fracture testing of a self-healing polymer composite10.1007/BF02412141 ↗
51. Microcapsule induced toughening in a self-healing polymer composite10.1023/B:JMSC.0000016173.73733.dc ↗
52. Polydimethylsiloxane-based self-healing materials
53. Self-healing polymer coatings
54. Properties of poly(urea-formaldehyde) microcapsules containing an epoxy resin10.1002/app.26263 ↗
55. Programmable microcapsules from self-immolative polymers10.1021/ja104812p ↗
56. Mechanical properties of melamine formaldehyde microcapsules for self-healing materials10.1016/j.matchemphys.2009.07.004 ↗
57. Self-healing thermoset using encapsulated epoxy-amine healing chemistry10.1016/j.polymer.2011.12.005 ↗
58. Mechanical properties of microcapsules used in a self-healing polymer10.1007/s11340-006-9659-3 ↗
59. Synthesis and characterization of melamine-urea-formaldehyde microcapsules containing ENB-based self-healing agents10.1002/mame.200900015 ↗
60. Nesterova · 2012
61. Microencapsulation of self-healing agents containing a fluorescent dye10.3144/expresspolymlett.2013.8 ↗
62. Self-repairing coatings containing active nanoreservoirs10.1002/smll.200700064 ↗
63. Self-healing epoxy composites - preparation and effect of the healant consisting of microencapsulated epoxy and latent curing agent10.1016/j.compscitech.2006.07.028 ↗
64. Formation of liquid core-polymer shell microcapsules10.1039/B606965G ↗
65. Preparation and characterization of poly(urea-formaldehyde) microcapsules filled with epoxy resins10.1016/j.polymer.2006.05.051 ↗
66. Synthesis and characterization of microencapsulated dicyclopentadiene with melamine–formaldehyde resins10.1007/s00396-006-1621-5 ↗
67. Self-healing polymeric materials using epoxy/mercaptan as the healant10.1021/ma800028d ↗
68. Self-healing polymeric materials based on microencapsulated healing agents: from design to preparation10.1016/j.progpolymsci.2015.07.002 ↗
69. Self-healing materials with microvascular networks10.1038/nmat1934 ↗
70. Self-healable polymer networks based on the crosslinking of epoxidised soybean oil by an aqueous citric acid solution10.1039/c3gc41384e ↗
71. Reorganizable chemical polymer gels based on dynamic covalent exchange and controlled monomer insertion10.1021/ma901746n ↗
72. Repeatable photoinduced self-healing of covalently cross-linked polymers through reshuffling of trithiocarbonate units10.1002/anie.201003888 ↗
73. Self‐healing of covalently cross‐linked polymers by reshuffling thiuram disulfide moieties in air under visible light
74. Kovalente adaptive netzwerke: reversible bindungen in polymernetzwerken10.1002/ange.201200708 ↗
75. Polylactide vitrimers10.1021/mz500269w ↗
76. Metal-catalyzed transesterification for healing and assembling of thermosets10.1021/ja302894k ↗
77. Catalytic control of the vitrimer glass transition10.1021/mz300239f ↗
78. Multiple welding of long fiber epoxy vitrimer10.1039/C6SM00257A ↗
79. Reconfigurable surface patterns on covalent adaptive network polymers using nanoimprint lithography10.1016/j.polymer.2014.09.024 ↗
80. Vinylogous urethane vitrimers
81. Vitrimers: permanent organic networks with glass-like fluidity10.1039/C5SC02223A ↗
82. Controllable reversible addition-fragmentation termination monomers for advances in photochemically controlled covalent adaptable networks10.1021/ma402548e ↗
83. Allene chemistry. IV. Unsymmetrical terminal thiol—allene diadducts. The effect of allylic Reversal 110.1021/jo01022a054 ↗
84. Role of allylic reversal in free-radical thiol additions to allylic halides10.1021/jo01282a007 ↗
85. A thermodynamic polymer cross-linking system based on radically exchangeable covalent bonds10.1021/ma052093g ↗
86. Stress relaxation and self-adhesion of rubbers with exchangeable links10.1021/acs.macromol.5b02751 ↗
87. Stress relaxation via Addition−Fragmentation chain transfer in a thiol-ene photopolymerization10.1021/ma802771b ↗
88. Covalent adaptable networks (CANs): a unique paradigm in cross-linked polymers10.1021/ma902596s ↗
89. Mechanophotopatterning on a photoresponsive elastomer
90. Covalent adaptable networks: smart, reconfigurable and responsive network systems10.1039/C3CS60046G ↗
91. Modeling the mechanics of covalently adaptable polymer networks with temperature-dependent bond exchange reactions10.1039/c3sm27945f ↗
92. Transient mechanochromism in epoxy vitrimer composites containint aromatic disulfide crosslinks
93. A photoviscoplastic model for photoactivated covalent adaptive networks10.1016/j.jmps.2014.05.008 ↗
94. Silica-like malleable materials from permanent organic networks10.1126/science.1212648 ↗
95. Synthesis of acyclic, symmetrical 3,3′-allyl dithioethers, from the alkylation of 3-Mercapto-2-mercaptomethylprop-1-ene in the presence of sodium hydride10.1071/CH11117 ↗
96. Responsive gels based on a dynamic covalent trithiocarbonate cross-linker10.1021/ma100378r ↗
97. Otera · Transesterification. ChemRev · 1993 · 93 · 1449
98. Covalent adaptable networks as dental restorative resins: stress relaxation by addition–fragmentation chain transfer in allyl sulfide-containing resins10.1016/j.dental.2010.06.007 ↗
99. Stress relaxation via addition–fragmentation chain transfer in high tg, high conversion methacrylate-based systems10.1021/ma300228z ↗
100. Mouldable liquid-crystalline elastomer actuators with exchangeable covalent bonds10.1038/nmat3812 ↗