Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization

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1. Verfasser: Mayr, Norbert Thorsten 1978- (VerfasserIn)
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Veröffentlicht: 2013
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245 1 0 |a Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives  |b synthesis and characterization  |c Norbert Thorsten Mayr 
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_version_ 1819629813068988416
adam_text INTRODUCTION 1 TABLE OF CONTENTS PART I INTRODUCTION 15 1 INTRODUCTION 16 1.1 GENERAL 16 1.2 PYROTECHNICS 17 1.3 DEVELOPMENTS IN ENERGETIC MATERIALS RESEARCH 17 1.4 STABILITY AND PERFORMANCE 19 1.5 EXPLOSIVES AND ENVIRONMENT 19 2 OBJECTIVES OF THE RESEARCH IN THIS THESIS 20 3 PARTS AND CHAPTERS 21 4 INTRODUCTION OF USED METHODS 21 4. 1 THEORY OF EXPLOSION AND EXPLOSION PRODUCTS 22 4.1.1 PHYSICAL AND CHEMICAL EXPLOSION 22 4.1.2 BURNING, DEFLAGRATION AND DETONATION 22 4.1.3 DEFLAGRATION TO DETONATION TRANSITION 23 4.1.4 BRISANCE VS. EXPLOSIVENESS 23 4.2 CALCULATION OF ENERGETIC PROPERTIES USING EPXL05 CODE 1291 24 4.2.1 SHOCK WAVE PROPAGATION AND CHAPMAN-JOUGUET VELOCITY 24 4.2.2 BECKER-KISTIAKOVSKY-WILSON EQUATION OF STATE (BKW-EOS) 24 4.2.3 EXPLOSION PRODUCTS - KISTIAKOVSKY-WILSON AND SPRINGALL-ROBERTS RULES 12 * 24 4.2.4 INPUT PARAMETERS: OXYGEN BALANCE, HEAT OF FORMATION AND DENSITY 25 4.3 PRACTICAL METHODS 25 4.3.1 SENSITIVITY TESTING 25 4.3.2 DETERMINATION OF DENSITY 27 4.3.3 MEASURING THE HEAT OF FORMATION 28 5 REFERENCES 28 PART 11 EXPLOSIVE UREA DERIVATIVES 31 CHAPTER I A COMPREHENSIVE STUDY ON N,N -BIS{TRIS(NITRATOMETHYL)METHYL)OXAMIDE 33 1 INTRODUCTION 34 2 RESULTS AND DISCUSSION 35 2. 1 COMPARISON OF CRYSTAL STRUCTURES 35 2.2 VIBRATIONAL AND THERMODYNAMICAL DATA AND CALCULATIONS 39 2.2.1 THERMODYNAMICAL CALCULATION AND EXPERIMENTAL DATA 42 2.3 ELECTROSTATIC POTENTIAL (ESP) AND DECOMPOSITION 45 2.4 THERMOSTABILITY: DSC AND RADEX MEASUREMENTS 47 2.5 ENERGETIC PROPERTIES 48 2.5.1 COMPARISON OF ENERGETIC PROPERTIES OF BTNMMOXAMIDE TO COMMON EXPLOSIVES 48 2.5.2 KOENEN (STEEL SLEEVES) TEST 49 3 CONCLUSIONS 50 4 EXPERIMENTAL 51 4. 1 CRYSTAL STRUCTURES 51 4.2 PROPERTIES 51 4.3 SPECTROSCOPIC DATA AND ELEMENTAL ANALYSIS 51 4.4 PREPARATION 51 5 REFERENCES 52 CHAPTER II ENERGETIC CYANURIC ACID DERIVATIVES 55 1 INTRODUCTION 56 1.1.1 NITRO UREA COMPOUNDS 57 2 DISCUSSION 59 2.1 SYNTHESIS 59 HTTP://D-NB.INFO/1044668237 INTRODUCTION 2.2 VIBRATIONAL SPECTROSCOPY 59 2.2.1 N,N ,N -TRIS-(NITROXYMETHYL)-ISOCYANURIC ACID (3) 59 2.3 THERMOSTABILITY 61 2.3.1 N,N ,N -TRIS-(NITROXYMETHYL)-ISOCYANURIC ACID (3) 61 2.4 CRYSTAL STRUCTURE 62 2.4.1 N,N ,N -TRIS-(NITROXYMETHYL)-ISOCYANURIC ACID (3) 62 2.4.2 L,3,5-TRIS(HYDROXYETHYL)CYANURIC ACID(2) 65 2.4.3 L,3,5-TRIS(NITRATOETHYL)-CYANURIC ACID (4) 66 2.5 CALCULATION OF THERMODYNAMIC DATA AND SURFACE POTENTIAL 68 2.5.1 ELECTROSTATIC SURFACE POTENTIAL OF N,N ,N -TRIS-(NITROXYMETHYL)-ISOCYANURIC ACID(3) 68 2.5.2 ELECTROSTATIC SURFACE POTENTIAL OF N,N ,N -TRIS-(NITROXYETHYL)- ISOCYANURIC ACID (4) 69 2.5.3 CALCULATION OF THE ENTHALPY OF FORMATION 69 2.1 ENERGETIC PROPERTIES 71 2.1.1 DETONATION PARAMETERS 71 3 CONCLUSIONS 72 4 EXPERIMENTAL 73 4.1 CRYSTAL STRUCTURES 73 4.2 PROPERTIES 73 4.3 SPECTROSCOPIC DATA AND ELEMENTAL ANALYSIS 73 4.4 PREPARATION 73 5 REFERENCES 75 CHAPTER III N 2/ N 4 ,N 6 -TRIS(TRIS(NITRATOMETHYL)METHYL)-1,3,5-TRIAZINO-2,4,6-TRICARBOXAMIOE (NOX- 1) - BIG AND BANG 79 1 INTRODUCTION 80 2 DISCUSSION 81 2.1 STRUCTURE OF TRIAZINE DERIVATIVES 81 2.1.1 DESCRIPTION OF THE MOLECULE STRUCTURE AND THE MONOCLINIC CRYSTAL STRUCTURE IN COMPARISON TO THE REPORTED HEXAGONAL STRUCTURE 83 2.2 SYNTHESIS 88 2.3 THERMODYNAMICAL AND SPECTROSCOPIC CHARACTERIZATION 89 2.4 CRYSTAL STRUCTURE DATA 91 2.5 ENERGETIC DATA 93 3 CONCLUSIONS 93 4 EXPERIMENTAL PART 94 4.1 INSTRUMENTAL SETUPS T 94 PD-XRAY 94 IR SAMPLES 94 NMR-SAMPLES 94 RAMAN SAMPLES 94 DSC MEASUREMENTS 94 SC-XRAY DATA 94 NCS-ELEMENTAL ANALYSIS 94 MASS SPECTROMETRY 94 FRICTION AND IMPACT SENSITIVITY 94 4.2 PREPARTATION 94 4.2.1 [L,3,5]TRIAZINE-2,4,6-TRICARBOXYLIC ACID TRIETHYL ESTER (2) 94 4.2.2 N 2 ,N 4 ,N 6 -TRIS(TRIS(HYDROXYMETHYL)METHYL)-L,3,5-TRIAZINO-2,4,6-TRICARBOXAMIDE (TTHMM-TCA, 3) 95 4.2.3 N 2 ,N 4 ,N 6 -TRIS(TRIS(NITRATOMETHYL)METHYL)-L,3,5-TRIAZINO-2,4,6-TRICARBOXAMIDE (TTNMM-TCA, NOX, 4) 95 5 REFERENCES 96 PART 111 ENERGETIC MATERIALS BASED ON 1,2,4-OXADIAZOLE DERIVATIVES 99 INTRODUCTION CHAPTER IV 3,3 -BIS-{1,2,4-OXADIAZOL-5-ONE) AND DERIVATIVES - A COMPREHENSIVE STUDY^ 101 1 COMPARISON OF 3,3 -BIS-1,2,4-OXADIAZOL-5-ONE AND 5,5 -BIS-1H-TETRAZOLE 102 1.1 INTRODUCTION 102 1.2 DISCUSSION 102 1.3 SYNTHESIS 106 1.4 CONCLUSIONS 107 1.5 EXPERIMENTAL 107 1.5.1 CRYSTAL STRUCTURES 107 1.5.2 PROPERTIES 107 1.5.3 SPECTROSCOPIC DATA AND ELEMENTAL ANALYSIS 107 1.5.4 PREPARATION 107 1.6 REFERENCES 108 2 INSENSITIVE EXPLOSIVES AND PROPELLANTS BASED 1,2,4-OXADIAZOL DERIVATIVES 110 2.1 INTRODUCTION 110 2.2 SYNTHESES 111 2.3 CRYSTAL STRUCTURES 112 2.3.1 DIAMMONIUM BIS-(L,2,4-OXADIAZOL-5-ONATE ) 112 2.3.2 DIHYDRAZINIUM BIS-(L,2,4-OXADIAZOL-5-ONATE) 114 2.3.3 DIGUANIDINIUM BIS-(L,2,4-OXADIAZOL-5-ONATE) (G 2 OD, 6) 116 2.3.4 BIS-AMINOGUANIDINIUM 3,3 -BIS-(L,2,4-OXADIAZOL-5-ONATE) (AG 2 OD, 7) 119 2.3.5 DI-TRIAMINOGUANIDINIUM 3,3 -BIS-(L,2,4-OXADIAZOL-5-ONATE) (TA6 2 OD, 9) 121 2.4 ENERGETIC PROPERTIES 123 2.5 CONCLUSIONS 124 2.6 EXPERIMENTAL 125 2.6.1 CRYSTAL STRUCTURES 125 2.6.2 PROPERTIES 125 2.6.3 SPECTROSCOPIC DATA AND ELEMENTAL ANALYSIS 125 2.6.4 PREPARATION 125 2.7 REFERENCES 128 3 SMOKELESS PYROTECHNICAL COLORANTS BASED ON 3,3 -BIS-(1,2,4-OXADIAZOL-5-ONE SALTS 130 3.1 INTRODUCTION 130 3.2 DISCUSSION 131 3.2.1 SYNTHESES 131 3.2.2 CRYSTAL STRUCTURES 132 TETRAAQUA-3.3 -BIS( 1 ^^-OXADIAZOLO-ONVATO COPPER(II) 135 3.2.3 THERMOSTABILITY 142 3.3 CONCLUSION 144 3.4 EXPERIMENTAL 144 3.4.1 CRYSTAL STRUCTURES 144 3.4.2 PROPERTIES 144 3.4.3 SPECTROSCOPIC DATA AND ELEMENTAL ANALYSIS 144 3.4.4 PREPARATION 145 3.5 REFERENCES 146 CHAPTER V 3,5-DIAMINO-1,2,4-OXADIAZOLE - A SUBSTITUTE FOR GUANYLUREA IN ENERGETIC MATERIALS 149 1 INTRODUCTION 150 2 RESULTS AND DISCUSSION 151 2.1 SYNTHESIS AND CHARACTERIZATION OF 3,5-DIAMINO-L,2,4-OXADIAZOLE (DAOD, 1) 151 2.1.1 3,5-DIAMINO- 1,2,4-OXADIAZOLE (L, DAOD) 151 2.2 SYNTHESES OF3,5-DIAMINO-L,2,4(4H)-OXADIAZOLIUM SALTS 159 2.2.1 THE 3,5-DIAMINO-L,2,4(4H)-OXADIAZOLIUM CATION 159 2.2.2 3,5-DIAMINO-L,2,4-OXADIAZOLIUM NITRATE (2) 162 2.2.3 3,5-DIAMINO-L,2,4-OXADIAZOLIUM PERCHLORATE (3) 163 INTRODUCTION 2.2.4 3,5-DIAMINO-L,2,4-OXADIAZOLIUM PICRATE (4) 169 2.2.5 3,5-DIAMINO-L,2,4-OXADIAZOLIUM DINITRAMIDE (5) 172 2.2.6 2.3.6 3,5-DIAMINO-L,2,4-OXADIAZOLIUM-5-AMINOTETRAZOLATE (6) 174 2.2.7 3,5-DIAMINO-L,2,4-OXADIAZOLIUM-5-NITROTETRAZOLAT (IX) 175 2.2.8 3,5-DIAMINO-L,2,4-OXADIAZOLIUM-5,5 -AZOTETRAZOLATE (X) 176 2.2.9 3,5-DIAMINO-4-METHYL-L,2,4-OXADIAZOLIUM IODIDE (XI) 177 2.3 SYNTHESIS OF COMPLEX BOND 3,5-DIAMINO-L,2,4-OXADIAZOLE (7) 177 2.4 DIAZOTATION REACTION OF 1 BY SODIUM NITRITE (I) 178 2.5 OXIDATION AND NITRATION OF 3,5-DIAMINO-L,2,4-OXADIAZOLE (1) 179 2.5.1 OXIDATION OR NITRATION WITH HNOJ (100 %) 181 2.5.2 OXIDATION OR NITRATION WITH HN0 3 (100 %) AND H 2 S0 4 (CONC.) 181 2.5.3 OXIDATION OR NITRATION BY SODIUM NITRITE (II-IV) 181 2.5.4 OXIDATION WITH H 2 SO A (CONC.), H 2 0 2 (30 %) AND (NH 4 )JS 2 08 (V) 182 2.5.5 OXIDATION BY POTASSIUM PERMANGANATE (VI) 182 2.5.6 OXIDATION BY AMMONIUM DICHROMATE (VII) 183 2.5.7 OXIDATION BY BROMINE (VIII) 183 2.5.8 NITRATION WITH HN0 3 (100%) AND AC 2 0 184 2.6 ENERGETIC DATA 184 3 SUMMARY AND CONCLUSIONS 185 3.1 SUMMARY 185 3.1.1 ENERGETIC SALTS OF DAOD 186 3.1.2 OXIDATION, NITRATION AND DIAZOTATION OF DAOD. 186 3.2 CONCLUSION AND OUTLOOK 187 4 EXPERIMENTAL PART 187 4.1 COMMON 187 4.2 ANALYTICAL APPARATUS 187 4.3 CALCULATIONS 189 4.4 PREPARATION OF ENERGETIC DAOD (1) AND SALTS THEREOF 191 4.5 OXIDATION AND NITRATION PRODUCTS OF DAOD(L) 194 5 REFERENCES 197 CHAPTER VI 3-AMINO-1,2,4-OXADIAZOL-5-ONE - THE INSENSITIVE 5-AMINO-TETRAZOLE ? COMMONS AND DIFFERENCES 201 1 INTRODUCTION . 202 2 RESULTS AND DISCUSSION 204 2.1 SYNTHESIS OF AOD 204 2.1.1 OVERVIEW 205 2.1.2 SYNTHETIC ROUTE A 206 2.1.3 SYNTHESIS ROUTE B 209 2.1.4 ONE-POT-SYNTHESIS ACCORDING TO ROUTE B 219 2.1.5 SUMMARY .220 2.2 SOLUBILITY OFAOD 220 2.3 AZO-COUPLING OFAOD .221 2.4 SALTS OFAOD 222 2.4.1 COPPER AOD (9) 222 2.4.2 SILVER AOD (10) 223 2.4.3 STRONTIUM AOD (11) TRIHEMIHYDRATE 223 2.4.4 BARIUM AOD (12) 224 2.4.5 AMINOGUANIDINIUM AOD (13) 224 2.4.6 SODIUM AOD (14) MONOHYDRATE 225 2.4.7 SUMMARY 229 2.5 METHYLATION OF3-AMINO-L,2,4(4H)-OXADIAZOL-5-ONE 230 2.6 SYNTHESIS OF SALTS WITH AODH* AS CATION 231 2.6.1 SUMMARY 241 INTRODUCTION 2.7 ENERGETIC DATA 242 * 3 CONCLUSIONS,. 245 4 OUTLOOK 245 5 EXPERIMENTAL PART 246 5. 1 CHEMICALS AND METHODS 246 5.2 PREPARATION _ 246 5.2.1 DIPOTASSIUM CYANODITHIOIMIDOCARBONATE (4) 246 5.2.2 DIMETHYLCYANODITHIOIMIDOCARBONAT (5) 247 5.2.3 POTASSIUM S-METHYL-N-CYANOCARBAMATE (3) 247 5.2.4 3-AMINO-L,2,4(4H)-OXADIAZOL-5-ONE (A) {1) 248 5.2.5 (Z)-AMINO[{ETHOXYCARBONYL)AMINO]-N-HYDROXYMETHANIMINIUM CHLORIDE /N-(ETHOXYCARBONYL)- /V -HYDROXY-GUANIDINIUM CHLORIDE (8) 248 5.2.6 3-AMINO-L,2,4(4H)-OXADIAZOL-5-ONE (B) (X) 249 5.2.1 ONE-POT-SYNTHESIS OF AMINO-L,2,4(4H)-OXADIAZOL-5-ONE (B) (1) 250 5.2.1 COPPER AOD 2 H 2 0 (9) 251 5.2.2 SILVER AOD (10) __ 251 5.2.3 STRONTIUM AOD X 1.5 H 2 0 (11) _ 251 5.2.4 BARIUM AOD (12) 252 5.2.5 AMINOGUANIDINIUM AOD (13) 252 5.2.6 SODIUM AOD (14) 253 5.3 SOLUBILITY IN DIFFERENT SOLVENTS 253 5.4 FURTHER INVESTIGATED REACTIONS 253 5.4.1 (Z)-AMINO[(METHOXYCARBONYL)AMINO] A/-HYDROXYMETHANIMINIUM CHLORIDE (B I) 253 5.4.2 ALTERNATIVE RING CLOSURE REACTION FOR AOD (1) WITH DIPHOSGEN (B III, 6) 254 5.5 SYNTHESIS OF AOD SALTS WITH AODH + AS CATION: 254 5.5.1 SYNTHESIS OF AODH F NITRATE 254 5.5.2 SYNTHESIS OF AODH* PERCHLORATE 255 5.5.3 SYNTHESIS OF AODH* PICRATE 256 5.6 AZO-COUPLING OF AOD (15) 256 5. 7 METHYLATION OFAOD (16A, 16B) 257 6 REFERENCES 258 CHAPTER VII 3-DINITROMETHYLENYL-1,2,4(4H)-OXADIAZOL-5-ONE AND DERIVATIVES - HIGH EXPLOSIVE, STABLE, INSENSITIVE 261 1 INTRODUCTION 262 2 SYNTHESIS 263 2.1 BY-PRODUCT (6) 264 2.2 SALTS OF DNM-OD (7,9) 265 3 DISCUSSION 266 3.1 SPECTROSCOPIC PROPERTIES 266 3.2 CRYSTAL STRUCTURES 267 3.2.1 2- ETHYL-3-AMINO-3-(HYDROXYIMIN)-PROPANOATE (2) 267 3.2.1 ETHYL (3Z)-3-AMINO-{[(METHOXYCARBONYL)OXY]IMINO}-PROPANOAT (3A) 267 3.2.1 DINITRO-([L,2,4]OXADIAZOL-5-ON-3-YL)-ACETIC ACID ETHYL ESTER (5) 268 3.2.1 SODIUM (4-{2-[(ETHOXYCARBONYL)OXY]PROPAN-2-YL}-5-OXO-4,5-DIHYDRO-L,2,4-OXADIAZOL-3- YL)(DINITRO)METHANIDE MONOHYDRATE (REARRANGEMENT PRODUCT) (6) 269 3.2.2 DI-SODIUM DNM-OD DIHYDRATE (7B) 271 3.2.3 DI-AMMONIUM DNM-OD (9B) 272 3.2.4 BIS-GUANIDINIUM DNM-OD (9A) 274 3.3 CALCULATIONS - THERMODYNAMICAL PROPERTIES 275 3.4 STRUCTURE OPTIMIZATION OF DNM-OD AND DNM-OD 2 ~ 275 3.5 ENERGETIC PROPERTIES 276 3.5.1 PYROTECHNICAL COLORANTS 276 3.5.2 HIEH-NITROEEN CONTAINING CATIONS 276 INTRODUCTION 4 CONCLUSIONS 277 5 OUTLOOK 278 6 EXPERIMENTAL 278 6.1 COMMON 278 6.2 ANALYTICAL APPARATUS 278 6.3 PREPARATION 280 6.3.1 2-ETHYL-3-AMINO-3-(HYDROXYIMIN)-PROPANOATE (1) 280 6.3.1 ETHYL-2-(L,2,4-OXADIAZOL-5-ON-3-YL) ACETATE - TWO STEP REACTION (10) 280 6.3.2 ETHYL-(3Z)-3-AMINO-{[{METHOXYCARBONYL)OXY]IMINO}-PROPANOAT (9) 280 6.3.3 3-ETHYL (5-OXO-4,5-DIHYDRO-L,2,4-OXADIAZOL-3-YL)-ACETATE (2) 281 6.3.4 DINITRO-([L,2,4]OXADIAZOL-5-ON-3-YL)-ACETIC ACID ETHYL ESTER (3) 282 6.3.5 SODIUM (4-{2-[(ETHOXYCARBONYL)OXY]PROPAN-2-YL}-5-OXO-4,5-DIHYDRO-L,2,4-OXADIAZOL-3- YL)(DINITRO)METHANIDE MONOHYDRATE (REARRANGEMENT PRODUCT) (5) 282 6.4 ALKALINE AND ALKALINE EARTH METAL SALTS OF DNM-OD (7) 282 6.4.1 GENERAL PROCEDURE 282 6.4.2 LITHIUM DNM-OD 283 6.4.3 SODIUM DNM-OD X 2 H 2 0 283 6.4.4 POTASSIUM DNM-OD 283 6.4.5 BARIUM DNM-OD X 3.5 H 2 0 283 6.5 NITROGEN RICH SALTS OF DNM-OD 283 6.5.1 BIS-GUANIDINIUM DNM-OD X H 2 0 (9A) 284 6.5.1 DI-AMMONIUM DNM-OD X H 2 0 (9B) 284 7 REFERENCES 284 PART IV CONCLUSIONS AND OUTLOOK 287 1 PART II - UREA BASED DERIVATIVES 288 1.1 CONCLUSIONS 288 1.2 OUTLOOK 288 2 PART III -1,2,4- OXADIAZOLE AND 1,2,4-OXDIAZOL-5-ONE BASED COMPOUNDS 288 2.1 CONCLUSIONS 288 2.2 OUTLOOK 289 PARTV APPENDIX 291 CHAPTER VIII TABLES OF CRYSTAL STRUCTURES 293 1 COMPOUNDS- CHAPTER I 294 2 COMPOUNDS - CHAPTER II 295 3 COMPOUNDS - CHAPTER III 296 4 COMPOUNDS - CHAPTER IV 297 4.1 METAL SALTS 297 4.2 NITROGEN RICH SALTS 298 5 COMPOUNDS - CHAPTER V 299 6 COMPOUNDS - CHAPTER VI 300 7 COMPOUNDS-CHAPTER VII 301 CHAPTER IX INDEX OF ABBREVIATIONS 303 CHAPTER X ABSTRACT AND SUMMARY 307 CHAPTER XI CURRICULUM VITAE 309 PART VI INDEX 313 CHAPTER XII FIGURES 315 CHAPTER XIII TABLES 323
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author Mayr, Norbert Thorsten 1978-
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author_facet Mayr, Norbert Thorsten 1978-
author_role aut
author_sort Mayr, Norbert Thorsten 1978-
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dewey-hundreds 500 - Natural sciences and mathematics
dewey-ones 547 - Organic chemistry
dewey-raw 547.595
dewey-search 547.595
dewey-sort 3547.595
dewey-tens 540 - Chemistry and allied sciences
discipline Chemie / Pharmazie
format Thesis
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indexdate 2024-12-24T04:00:11Z
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physical XIV, 327 S. Ill., graph. Darst. 30 cm
psigel ebook
publishDate 2013
publishDateSearch 2013
publishDateSort 2013
record_format marc
spellingShingle Mayr, Norbert Thorsten 1978-
Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization
subject_GND (DE-588)4113937-9
title Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization
title_auth Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization
title_exact_search Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization
title_full Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization Norbert Thorsten Mayr
title_fullStr Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization Norbert Thorsten Mayr
title_full_unstemmed Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives synthesis and characterization Norbert Thorsten Mayr
title_short Energetic materials based on isocyanuric acid and 1,2,4-oxadiazole derivatives
title_sort energetic materials based on isocyanuric acid and 1 2 4 oxadiazole derivatives synthesis and characterization
title_sub synthesis and characterization
topic_facet Hochschulschrift
url http://edoc.ub.uni-muenchen.de/16237/
https://nbn-resolving.org/urn:nbn:de:bvb:19-162379
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