Nucleophilic Polymers and Gels in Hydrolytic Degradation of Chemical Warfare Agents

ACS Applied Materials and Interfaces

Volumn 7, Issue 39, 2015, Pages 22001-22011

  Bromberg, Lev ^a   Creasy, William R ^b   McGarvey, David J ^c   Wilusz, Eugene ^d   Hatton, T Alan ^a  

^a Massachusetts Institute of Technology   (United States)

^b FREDERICK NATIONAL LABORATORY FOR CANCER RESEARCH   (United States)

^c EDGEWOOD CHEMICAL BIOLOGICAL CENTER   (United States)

^d DEVELOPMENT AND ENGINEERING CENTER   (United States)

Author keywords

chemical warfare agents; HD; hydrogels; nucleophilic polymers; polyallylamine; polyvinylamine; self decontaminating fabrics; VX

Indexed keywords

CHEMICAL COMPOUNDS; CHEMICAL WARFARE; CROSSLINKING; DEGRADATION; GELS; HYDROGELS; HYDROLYSIS; PH; RATE CONSTANTS; SOLUBILITY; SUSPENSIONS (FLUIDS); SWELLING;

CHEMICAL WARFARE AGENTS; HD; POLYALLYLAMINE; POLYVINYLAMINES; SELF-DECONTAMINATING; VX;

POLYMERS;

EID: 84943645492     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/acsami.5b06905     Document Type: Article

References (68)

1. Gibson, P. W.; Schreuder-Gibson, H. L. Influence of Hydration State on Permeation Testing and Vapor Transport Properties of Protective Clothing Layers J. Engineered Fibers and Fabrics 2009, 4, 11-20
2. Chen, L.; Bromberg, L.; Hatton, T. A.; Rutledge, G. C. Catalytic Hydrolysis of p-Nitrophenyl Acetate by Electrospun Polyacrylamidoxime Nanofibers Polymer 2007, 48, 4675-4682 10.1016/j.polymer.2007.05.084
3. Chen, L.; Bromberg, L.; Schreuder-Gibson, H.; Walker, J.; Hatton, T. A.; Rutledge, G. C. Chemical Protection Fabrics via Surface Oximation of Electrospun Polyacrylonitrile Fiber Mats J. Mater. Chem. 2009, 19, 2432-2438 10.1039/b818639a
4. Chen, L.; Bromberg, L.; Lee, J. A.; Zhang, H.; Schreuder-Gibson, H.; Gibson, P.; Walker, J.; Hammond, P. T.; Hatton, T. A.; Rutledge, G. C. Multifunctional Electrospun Fabrics via Layer-by-layer Electrostatic Assembly for Chemical and Biological Protection Chem. Mater. 2010, 22, 1429-1436 10.1021/cm902834a
5. Turaga, U.; Kendall, R. J.; Singhg, V.; Lalagiri, M.; Ramkumar, S. S. Advances in Materials for Chemical, Biological, Radiological and Nuclear (CBRN) Protective Clothing, Advances in Military Textiles and Personal Equipment; Sparks, E., Ed.; Woodhead: Oxford, U.K., 2012; pp 26-287
6. Narang, S. C.; Ventura, S.; Ramharack, R. Polymeric Dialkylaminopyridines as Supernucleophilic Catalysts, Chemical Reactions on Polymers ACS Symp. Ser. 1988, 364, 72-80 10.1021/bk-1988-0364.ch006
7. Yang, Y. C.; Baker, J. A.; Ward, J. R. Decontamination of Chemical Warfare Agents Chem. Rev. 1992, 92, 1729-1743 10.1021/cr00016a003
8. Bromberg, L.; Hatton, T. A. Nerve Agent Destruction by Recyclable Catalytic Magnetic Nanoparticles Ind. Eng. Chem. Res. 2005, 44, 7991-7998 10.1021/ie0506926
9. Bromberg, L.; Hatton, T. A. Decomposition of Toxic Environmental Contaminants by Recyclable Catalytic, Superparamagnetic Nanoparticles Ind. Eng. Chem. Res. 2007, 46, 3296-3303 10.1021/ie061351a
10. Bromberg, L.; Zhang, H.; Hatton, T. A. Functional Organic-Inorganic Colloids Modified by Iodoxybenzoic Acid Chem. Mater. 2008, 20, 2001-2008 10.1021/cm702883c
11. Bromberg, L.; Hatton, T. A. Poly(N-vinylguanidine): Characterization, and Catalytic and Bactericidal Properties Polymer 2007, 48, 7490-7498 10.1016/j.polymer.2007.10.040
12. Bromberg, L.; Schreuder-Gibson, H.; Creasy, W. R.; McGarvey, D. J.; Fry, R. A.; Hatton, T. A. Degradation of Chemical Warfare Agents by Reactive Polymers Ind. Eng. Chem. Res. 2009, 48, 1650-1659 10.1021/ie801150y
13. Kim, K.; Tsay, O. G.; Atwood, D. A.; Churchill, D. G. Destruction and Detection of Chemical Warfare Agents Chem. Rev. 2011, 111, 5345-5403 10.1021/cr100193y
14. Wagner, G. W.; Chen, Q.; Wu, Y. Reactions of VX, GD, and HD with Nanotubular Titania J. Phys. Chem. C 2008, 112, 11901-11906 10.1021/jp803003k
15. Wagner, G. W.; Peterson, G. W.; Mahle, J. J. Effect of Adsorbed Water and Surface Hydroxyls on the Hydrolysis of VX, GD, and HD on Titania Materials: The Development of Self-Decontaminating Paints Ind. Eng. Chem. Res. 2012, 51, 3598-3603 10.1021/ie202063p
16. Jocic, D.; Tourrette, A.; Glampedaki, P.; Warmoeskerken, M. M. C. G. Application of Temperature and pH Responsive Microhydrogels for Functional Finishing of Cotton Fabric Mater. Technol. 2009, 24, 14-23 10.1179/175355509X417963
17. Glampedaki, P.; Jocic, D.; Warmoeskerken, M. M.C.G. Moisture Absorption Capacity of Polyamide 6,6 Fabrics Surface Functionalised by Chitosan-Based Hydrogel Finishes Prog. Org. Coat. 2011, 72, 562-571 10.1016/j.porgcoat.2011.06.019
18. Glampedaki, P.; Dutschk, V. Superabsorbent Finishes for Textiles, Functional Finishes for Textiles: Improving Comfort, Performance and Protection. Roshan, P., Ed.; Woodhead Publishing Series in Textiles; Elsevier: Cambridge, UK, 2014, 283-298
19. Bashari, A.; Hemmati Nejad, N.; Pourjavadi, A. Applications of Stimuli Responsive Hydrogels: a Textile Engineering Approach J. Text. Inst. 2013, 104, 1145-1155 10.1080/00405000.2013.780787
20. Gopalkrishna, K. M.; Thakaji, K. S.; Babu, B. S. Process for the Preparation of Crosslinked Polyallylamine Polymer, U.S. Patent 7,388,056, June 17, 2008
21. Shek, E.; Higuchi, T.; Bodor, N. Improved Delivery Through Biological Membranes. 2. Distribution, Excretion and Metabolism of N- Methyl-1, 6-dihydropyridine- 2- Carbaldoxime Hydrochloride, a Pro-drug of N- Methylpyridinium-2 carbaldoxime chloride J. Med. Chem. 1976, 19, 108-112 10.1021/jm00223a018
22. Chennamaneni, S. R.; Vobalaboina, V.; Garlapati, A. Quaternary Salts of 4,30 and 4,40 bis-Pyridinium Monooximes: Synthesis and Biological Activity Bioorg. Med. Chem. Lett. 2005, 15, 3076-3080 10.1016/j.bmcl.2005.04.026
23. Bailey, M. M.; Heddleston, J. M.; Davis, J.; Staymates, J. L.; Hight Walker, A. R. Functionalized, Carbon Nanotube Material for the Catalytic Degradation of Organophosphate Nerve Agents Nano Res. 2014, 7, 390-398 10.1007/s12274-014-0405-3
24. Blacker, N. C.; Findlay, P. H.; Sherrington, D. C. Synthesis of Cu-II-Complexed Polymers and Use as Catalysts in the Hydrolytic Decontamination of Sarin Nerve Agent Polym. Adv. Technol. 2001, 12, 183-196 10.1002/pat.133
25. Narang, S.; Ventura, S. Immobilized 4-Dialkylaminopyridines: Supernucleophilic Chemical Decontaminating Agents, US Army Research Office Technical Report 23208.1-CH, 1987; http://handle.dtic.mil/100.2/ADA190999
26. Narang, S. C.; Ramharack, R. Poly(4-N-pyrrolidinopyridine) Copolymers as Supernucleophilic Reagents J. Polym. Sci., Polym. Lett. Ed. 1985, 23, 147-150 10.1002/pol.1985.130230305
27. Castro, E. A.; Echevarria, G. R.; Opazo, A.; Robert, P. S.; Santos, J. G. Kinetics and Mechanism of the Reactions of Polyallylamine with Aryl Acetates and Aryl Methyl Carbonates J. Phys. Org. Chem. 2006, 19, 129-135 10.1002/poc.1007
28. Bromberg, L.; Temchenko, M.; Hatton, T. A. Smart Microgel Studies. Polyelectrolyte and Drug-Absorbing Properties of Microgels from Polyether-Modified Poly(acrylic acid) Langmuir 2003, 19, 8675-8684 10.1021/la030187i
29. Harris, J. C. Rate of Hydrolysis In Handbook of Chemical Property Estimation Methods. Environmental Behavior of Organic Compounds; Lyman, W. J.; Reehl, W. F.; Rosenblatt, D. H., Eds. McGraw-Hill, New York, 1981; 7-48
30. Khan, S. A.; Kirby, A. J. The reactivity of Phosphate Esters. Multiple Structure-Reactivity Correlations for the Reactions of Triesters with Nucleophiles J. Chem. Soc. B 1970, 1172-1182 10.1039/j29700001172
31. Wolfe, N. L. Organophosphate and Organophosphorothionate Esters: Application of Linear Free Energy Relationships to Estimate Hydrolysis Rate Constants for Use in Environmental Fate Assessment Chemosphere 1980, 9, 571-579 10.1016/0045-6535(80)90075-2
32. Pregel, M. J.; Dunn, E. J.; Nagelkerke, R.; Thatcher, G. R. J.; Buncel, E. Alkali-Metal Ion Catalysis and Inhibition in Nucleophilic Displacement Reaction of Phosphorus-Sulfur-and Carbon-Based Esters Chem. Soc. Rev. 1995, 24, 449-455 10.1039/cs9952400449
33. Jencks, W. P. A Primer for the Bema Hapothle. An Empirical Approach to the Characterization of Changing Transition-State Structures Chem. Rev. 1985, 85, 511-527 10.1021/cr00070a001
34. Herschlag, D.; Jencks, W. P. Nucleophiles of High Reactivity in Phosphoryl Transfer Reactions: α-Effect Compounds and Fluoride Ion J. Am. Chem. Soc. 1990, 112, 1951-1956 10.1021/ja00161a047
35. Bunnett, J. F. Nucleophilic Reactivity Annu. Rev. Phys. Chem. 1963, 14, 271-290 10.1146/annurev.pc.14.100163.001415
36. Edwards, J. O.; Pearson, R. G. The Factors Determining Nucleophilic Reactivities J. Am. Chem. Soc. 1962, 84, 16-24 10.1021/ja00860a005
37. Larson, R. A.; Weber, E. J. Reaction Mechanisms in Environmental Organic Chemistry; CRC Press: Boca Raton, FL, 1994, 448
38. Höfle, G.; Steglich, W.; Vorbrüggen, H. Dialkylaminopyridines as Highly Active Acylation Catalysts Angew. Chem., Int. Ed. Engl. 1978, 17, 569-583 10.1002/anie.197805691
39. Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I. A. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales J. Org. Chem. 2005, 70, 1019-1028 10.1021/jo048252w
40. Öʇretir, C.; Öztürk, ̄. ̄.; Tay, N. F. Quantum Chemical Studies on Acidity-Basicity Behaviors of Some Bipyridine Derivatives ARKIVOC 2009, xiv) 235-254
41. Smith, D. T.; Shi, R.; Borgens, R. B.; McBride, J. M.; Jackson, K.; Byrn, S. R. Development of Novel 4-Aminopyridine Derivatives as Potential Treatments for Neurological Injury and Disease Eur. J. Med. Chem. 2005, 40, 908-917 10.1016/j.ejmech.2005.04.017
42. Turarova, I.; Halamelc, K.; Koblina, Z. Study on Reactivation of Enzyme-Inhibitor Complexes by Oximes Using Acetylcholine Esterase Inhibited by Organophosphate Chemical Warfare Agents Enzyme Microb. Technol. 1999, 25 (3-5) 400-403 10.1016/S0141-0229(99)00063-0
43. Rageh, N. M. Acidity Constants of Some Hydroxy Azo Pyrazolopyrimidines in Mixed Aqueous-Organic Solvents J. Chem. Eng. Data 1998, 43, 373-377 10.1021/je970167g
44. Tiwari, S.; Ghosh, K. K. et al. Spectrophotometric Determination of the Acidity Constants of Some Oxime-Based r-Nucleophiles J. Chem. Eng. Data 2010, 55, 1153-1157 10.1021/je9005773
45. Sumaru, K.; Matsuoka, H.; Yamaoka, H. Exact Evaluation of Characteristic Protonation of Poly(vinylamine) in Aqueous Solution J. Phys. Chem. 1996, 100, 9000-9005 10.1021/jp953385u
46. Katchalsky, A.; Mazur, J.; Spitnik, P. General Behavior of Biocolloids and Polyelectrolytes in Solution. Polybase Properties of Polyvinylamine J. Polym. Sci. 1957, 23, 513-532 10.1002/pol.1957.1202310401
47. Petrov, A. I.; Antipov, A. A.; Sukhorukov, G. B. Base-Acid Equilibria in Polyelectrolyte Systems: From Weak Polyelectrolytes to Interpolyelectrolyte Complexes and Multilayered Polyelectrolyte Shells Macromolecules 2003, 36, 10079-10086 10.1021/ma034516p
48. Shi, L.; Berkland, C. Acid-Labile Polyvinylamine Micro- and Nanogel Capsules Macromolecules 2007, 40, 4635-4643 10.1021/ma070443o
49. Kirby, A. J.; Jencks, W. P. The Reactivity of Nucleophilic Reagents toward the p-Nitrophenyl Phosphate Dianion J. Am. Chem. Soc. 1965, 87, 3209-3216 10.1021/ja01092a036
50. Gresser, M. J.; Jencks, W. P. Ester Aminolysis. Structure-Reactivity Relationships and the Rate-Determining Step in the Aminolysis of Substituted Diphenyl Carbonates J. Am. Chem. Soc. 1977, 99, 6963-6970 10.1021/ja00463a032
51. Ward, R. J.; Yang, Y.; Wilson, R. B.; Burrows, W. D.; Ackerman, L. L. Base-Catalyzed Hydrolysis of 1,2,2-Trimethylpropyl Methylphosphonofluoridate-An Examination of the Saturation Effect Bioorg. Chem. 1988, 16, 12-16 10.1016/0045-2068(88)90033-8
52. Yang, Y.-C.; Baker, J. A.; Ward, J. R. Decontamination of Chemical Warfare Agents Chem. Rev. 1992, 92, 1729-1743 10.1021/cr00016a003
53. Yli-Kauhaluoma, J.; Humppi, T.; Yliniemelä, A. et al. Hydrolysis of Organophosphorus Nerve Agent Soman by the Monoclonal Antibodies Elicited against an Oxyphosphorane Hapten Acta Chem. Scand. 1999, 53, 473-479 10.3891/acta.chem.scand.53-0473
54. Hiscock, J. R.; Sambrook, M. R.; Cranwell, P. B.; Watts, P.; Vincent, J. C.; Xuereb, D. J.; Wells, N. J.; Raja, R.; Gale, P. A. Tripodal Molecules for the Promotion of Phosphoester Hydrolysis Chem. Commun. 2014, 50, 6217-6220 10.1039/c4cc00333k
55. Barba-Bon, A.; Costero, A. M.; Parra, M.; Gil, S.; Martnez-Manez, R.; Sancenon, F.; Gale, P. A.; Hiscock, J. R. Neutral 1,3-Diindolylureas for Nerve Agent Remediation Chem.-Eur. J. 2013, 19, 1586-1590 10.1002/chem.201202028
56. Yang, Y.-C.; Szafraniec, L. L.; Beaudry, W. T.; Rohrbaugh, D. K.; Procell, L. R.; Samuel, J. B. Autocatalytic Hydrolysis of V-Type Nerve Agents J. Org. Chem. 1996, 61, 8407-8413 10.1021/jo9614506
57. Yang, Y.-C. Chemical Detoxification of Nerve Agent VX Acc. Chem. Res. 1999, 32, 109-115 10.1021/ar970154s
58. Wang, Q.-Q.; Begum, R. A.; Day, V. W.; Bowman-James, K. Sulfur, Oxygen, and Nitrogen Mustards: Stability and Reactivity Org. Biomol. Chem. 2012, 10, 8786-8793 10.1039/c2ob26482j
59. Yang, Y. C.; Szafraniec, L. L.; Beaudry, W. T.; Ward, J. R. Kinetics and Mechanism of the Hydrolysis of 2-Chloroethyl Sulfides J. Org. Chem. 1988, 53, 3293-3297 10.1021/jo00249a029
60. Yang, Y. C.; Szafraniec, L. L.; Beaudry, W. T.; Ward, J. R. Direct NMR Measurements of Sulfonium Chlorides Produced from the Hydrolyses of 2-Chloroethyl Sulfides J. Org. Chem. 1987, 52, 1637-16338 10.1021/jo00384a058
61. Connors, T. A. Mechanism of Action of 2-Chloroethylamine Derivatives, Sulfur Mustards, Epoxides, and Aziridines, Antineoplastic and Immunosuppressive Agents Handbook of Experimental Pharmacology 1975, 38, 18-34 10.1007/978-3-642-65806-8-3
62. Hsu, F. L.; Szafraniec, L. L.; Beaudry, W. T.; Yang, Y. C. Oxidation of 2-Chloroethyl Sulfides to Sulfoxides by Dimethyl sulfoxide J. Org. Chem. 1990, 55, 4153-4155 10.1021/jo00300a036
63. 13C{1H} NMR Spectral Parameters of Sulfur Mustards, Nitrogen Mustards, and Lewisites: Computing and Predicting of Reference Spectra for Chemical Identification Magn. Reson. Chem. 2012, 50, 196-207 10.1002/mrc.2867
64. Logan, T. P.; Sartori, D. A. Nuclear Magnetic Resonance Analysis of the Solution and Solvolysis of Sulfur Mustard in Deuterium Oxide Toxicol. Mech. Methods 2003, 13, 235-240 10.1080/15376510309831
65. Brevett, C. A. S.; Sumpter, K. B.; Wagner, G. W.; Rice, J. S. Degradation of the Blister Agent Sulfur Mustard, Bis(2-chloroethyl) Sulfide on Concrete J. Hazard. Mater. 2007, 140, 353-360 10.1016/j.jhazmat.2006.09.067
66. Brevett, C. A. S.; Sumpter, K. B.; Nickol, R. G. Kinetics of the Degradation of Sulfur Mustard on Ambient and Moist Concrete J. Hazard. Mater. 2009, 162, 281-291 10.1016/j.jhazmat.2008.05.033
67. Love, A. H.; Bailey, C. G.; Hanna, M. L.; Hok, S.; Vu, A. K.; Reutter, D. J.; Raber, E. Efficacy of Liquid and Foam Decontamination Technologies for Chemical Warfare Agents on Indoor Surfaces J. Hazard. Mater. 2011, 196, 115-122 10.1016/j.jhazmat.2011.09.005
68. Wagner, G. W.; Procell, L. R.; Sorrick, D. C.; Lawson, G. E.; Wells, C. M.; Reynolds, C. M.; Ringelberg, D. B.; Foley, K. L.; Lumetta, G. J.; Blanchard, D. L. All-Weather Hydrogen Peroxide-Based Decontamination of CBRN Contaminants Ind. Eng. Chem. Res. 2010, 49, 3099-3105 10.1021/ie9019177