US2885305A - Polychloro-7, 8-disubstituted-2, 5-diimino glycoluril for use as an antivesicant - Google Patents
Polychloro-7, 8-disubstituted-2, 5-diimino glycoluril for use as an antivesicant Download PDFInfo
- Publication number
- US2885305A US2885305A US526309A US52630944A US2885305A US 2885305 A US2885305 A US 2885305A US 526309 A US526309 A US 526309A US 52630944 A US52630944 A US 52630944A US 2885305 A US2885305 A US 2885305A
- Authority
- US
- United States
- Prior art keywords
- diimino
- glycoluril
- disubstituted
- polychloro
- clothing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 title description 9
- 239000000126 substance Substances 0.000 claims description 8
- 230000001681 protective effect Effects 0.000 claims description 7
- 239000011148 porous material Substances 0.000 claims description 4
- VPVSTMAPERLKKM-XIXRPRMCSA-N cis-glycoluril Chemical compound N1C(=O)N[C@@H]2NC(=O)N[C@@H]21 VPVSTMAPERLKKM-XIXRPRMCSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
- 229910052801 chlorine Inorganic materials 0.000 description 10
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 238000010410 dusting Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical group ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- -1 ointments Chemical class 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 101000740162 Homo sapiens Sodium- and chloride-dependent transporter XTRP3 Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102100037189 Sodium- and chloride-dependent transporter XTRP3 Human genes 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- MOHQFYBUKQUPIQ-UHFFFAOYSA-N chloroarsane Chemical class [AsH2]Cl MOHQFYBUKQUPIQ-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001087 glyceryl triacetate Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S2/00—Apparel
- Y10S2/901—Antibacterial, antitoxin, or clean room
Definitions
- Substances'which are useful for decontamination of afiected areas must of course show instantaneous reactivity with. the vesicant vapors. If they are to be used for. impregnation of clothing they must additionally be harmless to the skin and stable to oxygen, water and sunlight. They must also cause little or no increase in flammability or deterioration of the cloth, they must withstand removal or decomposition by laundering and they must be thermally stable at all temperatures likely to be encountered in use.
- Other desirable properties include stability in solution or in the presence of a solvent so that appreciable decomposition does not occur during impregnation, easy preparation from readily available raw materials with simple apparatus, and high efliciency and protective time so. that great quantities of the substance and frequent replenishment are not required.
- This invention provides a new class of anti-vesicants which are characterized by their high efliciency and long protective times, and in this respect are similar to the above-mentioned chlorinated glycolurils to which they are chemically related. Unlike the chlorinated glycolurils, however, the new compounds are less irritating tofthe skin and do not adversely affect clothing to the same extent.
- the invention includes these new compounds per se and anti-vesicants containing them.
- protective materials containing the compounds particularly ointments, dusting powders and impregnated clothing.
- the anti-vesicants of this invention are of the class of chloroamides may be described as chlorinated 7,8-disubstituted-2,5-diimino glycolurils, having the following structural formula:
- R and R are aryl, or aralkyl radicals and X and X are hydrogen or chlorine.
- the preferred compounds are those in which X and X are hydrogen (i.e. the 1,3,4,6 tetrachloro-7,8-disubstituted-2,5-diimino gly colurils) and of these the 7,8-diphenyl compound'is particularly desirable.
- This compound has the structural formula EXAMPLE Condensation A solution of guanidine (1 mole, 59 grams) inl liter of 95% ethanol is prepared by heating one mole of sodium ethoxide (sodium hydroxide can be used) with the calculated amount of guanidine nitrate (1 mole), then cooling and filtering 01f the sodium nitrate formed..-
- the filtrate containing the guanidine is reacted with a solution of 0.5 mole of benzil in 3 liters of 95% ethanol by heating up to five hours or letting stand over night.
- a basic salt thereof such as guanidine carbonate, can be used directly in the condensation reaction.
- a buffer salt such as sodium bicarbonate or acetate
- a 1% solution of dioctyl sodium sulfosuccinate or similar wetting agent Chlorine gas is passed into the water with vigorous stirring until the calculated amount (about 80 grams), as determined by periodic weighing of the chlorine cylinder; has been absorbed. The material is filtered, washed with water and dried.
- Clothing may be impregnated with these compounds or mixtures thereof, with or without other materials, in any of the standard ways employed for other chloroarnide anti-vesicant compounds.
- talc is a suitable inert material with some substance added to keep the powder free flowing (e.g. various phosphate salts).
- the compounds may be incorporated in any standard inert ointment composition such as those using triacetin as a base.
- anti-vesicant refers to substances or compositions capable of rendering harmless or neutralizing vesicant materials, particularly mustard gas.
- R and R are selected from the group consisting of aryl and aralkyl radicals and X and X are selected from the group consisting of hydrogen and chlorine.
- An article of clothing protective against vesicants which comprises a porous material impregnated with a substance comprising essentially a 1,3,4,6-tetrachloro-7,8- diaryl-2,5-diimino glycoluril.
- An article of clothing protective against vesicants which comprises a porous material impregnated with a 1 substance comprising essentially a chemical compound having the structural formula 8.
- a dusting powder suitable for protection against vesicants which comprises an inert powder admixed with a 1,3,4,6-tetrachloro-7,8-diaryl-2,S-diimino glycoluril.
- a dusting powder suitable for protection against vesicants which comprises an inert powder admixed with a chemical compound having the structural formula 10.
- a vehicle with which is incorporated as an essential active ingredient a polychloro-7,8-disubstituted-2,5- diimino glycoluril of the general formula Cl R1 01 wherein R and R, are selected from the group consisting of aryl and aralkyl radicals and X and X are selected from the group consisting of hydrogen and chlorine.
Description
POLYCHLORO 7,8 DISUBUSTITUTED 2,5 DI- IMINO GLYCOLURIL FOR" use AS AN ANTI- VESICANT I John C. Speck, Jr., Bloomington, Ind.
No Drawing. Application March 13, 1944 Serial No. 526,309
Claims. (Cl. 117-121) (Granted under Title 35, US. Code (1952), sec. 266) such as mustard gas or organic chloroarsines, it is neces- I sary to neutralize the vesicant before the area can be safely entered. Also it is necessary to provide workers in contaminated areas with suitable protective clothing. Clothing which seals thebody'from contact with the air cannot be wom'ror long periods'in'hot weather, be- I cause the only way thebody temperature may be maintained is by evaporation of perspiration. Therefore, it is necessary to provide porous clothing which is impregnated with a substance which will neutralize substantially all vesicant vapor coming in contact with the clothing.)
the body In this way air is permitted to circulate around without harm.v Substances'which are useful for decontamination of afiected areas must of course show instantaneous reactivity with. the vesicant vapors. If they are to be used for. impregnation of clothing they must additionally be harmless to the skin and stable to oxygen, water and sunlight. They must also cause little or no increase in flammability or deterioration of the cloth, they must withstand removal or decomposition by laundering and they must be thermally stable at all temperatures likely to be encountered in use. Other desirable properties include stability in solution or in the presence of a solvent so that appreciable decomposition does not occur during impregnation, easy preparation from readily available raw materials with simple apparatus, and high efliciency and protective time so. that great quantities of the substance and frequent replenishment are not required.
It is well known that compounds containing reactive chlorine are useful neutralizers or anti-vesicants for mustard gas and other vesicant vapors, and organic com- .poundscontaining a chloroamide group are generally preferred, An eflicient class of compounds known heretofore are the tetrachloro disubstituted"glycolurils,such as 1,3,4,6-tetrachloro-7,S-dimethyl glycoluril which is used extensively. These chlorinated glycolurils, however, are more or less irritating-to the skin when in contact therewith -over prolonged periods of time, although they are less so than other generally known chloroamide compounds. Also, the chlorinated glycolurils are relatively hard on textile fibers, and clothing impregnated therewith will not Withstand for, long the rough treatinvent given army clothing under fighting conditions.
This invention provides a new class of anti-vesicants which are characterized by their high efliciency and long protective times, and in this respect are similar to the above-mentioned chlorinated glycolurils to which they are chemically related. Unlike the chlorinated glycolurils, however, the new compounds are less irritating tofthe skin and do not adversely affect clothing to the same extent. The invention includes these new compounds per se and anti-vesicants containing them. I Also included are protective materials containing the compounds, particularly ointments, dusting powders and impregnated clothing.
The anti-vesicants of this invention are of the class of chloroamides may be described as chlorinated 7,8-disubstituted-2,5-diimino glycolurils, having the following structural formula:
wherein R and R are aryl, or aralkyl radicals and X and X are hydrogen or chlorine. The preferred compounds are those in which X and X are hydrogen (i.e. the 1,3,4,6 tetrachloro-7,8-disubstituted-2,5-diimino gly colurils) and of these the 7,8-diphenyl compound'is particularly desirable. This compound has the structural formula EXAMPLE Condensation A solution of guanidine (1 mole, 59 grams) inl liter of 95% ethanol is prepared by heating one mole of sodium ethoxide (sodium hydroxide can be used) with the calculated amount of guanidine nitrate (1 mole), then cooling and filtering 01f the sodium nitrate formed..-
The filtrate containing the guanidine is reacted with a solution of 0.5 mole of benzil in 3 liters of 95% ethanol by heating up to five hours or letting stand over night. In place of the free guanidine solution, a basic salt thereof, such as guanidine carbonate, can be used directly in the condensation reaction.
Separation of base I-fguanidine carbonate is not used-, the alcoholic liquor is filtered and the filtrate saturated with carbon dioxide, with the formation of a copious precipitate. If guanidine carbonate is used, the liquor is filtered directly, as the base precipitates during reaction. The precipitate is purified by washing with cold ethanol and recrystallizing from a mixture of half alcohol and half water. -1-
Chlorination ass 5,305
about 1.25 moles of a buffer salt, such as sodium bicarbonate or acetate, and about 75 ml. of a 1% solution of dioctyl sodium sulfosuccinate or similar wetting agent. Chlorine gas is passed into the water with vigorous stirring until the calculated amount (about 80 grams), as determined by periodic weighing of the chlorine cylinder; has been absorbed. The material is filtered, washed with water and dried.
The above method of chlorination yielded essentially 1,3,4,6-tetrachloro-7,8-diphenyl-2,5-diimino glycoluril as only enough chlorine was added to give this compound. Where it is desirable to obtain the hexachloro derivative, the addition of chlorine is continued until the calculated mount for the addition of six chlorine atoms is absorbed. However, for use as an antivesicant the advantages of the higher active chlorine content of the hexachloro compound is offset to a large extent by the fact that the chlorine attached to the imino groups is less stable than the other chlorine and renders the compound somewhat more irritating to the skin and deleterious to fabrics.
Thermal stability tests and tests of hydrolytic stability and stability in chlorinated hydrocarbons have shown that the chlorinated diimino glycoluril derivatives of this invention are equally as stable as the corresponding chlorinated glycolurils and much more stable under many conditions. As already indicated, the diimino compounds are less irritating to the skin, less injurious to fabrics and provide equally effective protection against the action of vesicant vapors, particularly of the mustard type.
Clothing may be impregnated with these compounds or mixtures thereof, with or without other materials, in any of the standard ways employed for other chloroarnide anti-vesicant compounds.
The incorporation of the compounds of this invention in dusting powders is satisfactory because the powders do not plug the pores and provide good protection. For this purpose, talc is a suitable inert material with some substance added to keep the powder free flowing (e.g. various phosphate salts).
For use in ointments, the compounds may be incorporated in any standard inert ointment composition such as those using triacetin as a base.
The term anti-vesicant, as used herein, refers to substances or compositions capable of rendering harmless or neutralizing vesicant materials, particularly mustard gas.
The invention described herein may be manufactured and used by or for the Government of the United States of America for governmental purposes without the payment of any royalties thereon or therefor.
I claim:
1. A polychloro-7,8-disubstituted-2,5-diimino glycoluril of the general formula:
wherein R and R are selected from the group consisting of aryl and aralkyl radicals and X and X are selected from the group consisting of hydrogen and chlorine.
2. As a new compound, a 1,3,4,6-tetrachloro-7,8-diaryl-2,5-diimino glycoluril.
3. As a new compound, 1,3,4,6 tetrachloro 7,8 di phenyl-2,5-diimino glycoluril.
4. An article of clothing protective against vesicants which comprises a porous material impregnated with a substance comprising essentially a 1,3,4,6-tetrachloro-7,8- diaryl-2,5-diimino glycoluril.
5. An article of clothing protective against vesicants which comprises a porous material impregnated with a 1 substance comprising essentially a chemical compound having the structural formula 8. A dusting powder suitable for protection against vesicants which comprises an inert powder admixed with a 1,3,4,6-tetrachloro-7,8-diaryl-2,S-diimino glycoluril.
9. A dusting powder suitable for protection against vesicants which comprises an inert powder admixed with a chemical compound having the structural formula 10. A vehicle with which is incorporated as an essential active ingredient a polychloro-7,8-disubstituted-2,5- diimino glycoluril of the general formula Cl R1 01 wherein R and R, are selected from the group consisting of aryl and aralkyl radicals and X and X are selected from the group consisting of hydrogen and chlorine.
References Cited in the file of this patent UNITED STATES PATENTS 2,005,538 Engelmann June 18, 1938 2,155,914 Van der Lee Apr. 25, 1939 2,351,924 Carnaugh June 20, 1944
Claims (2)
1. A POLYCHLORO-7,8-DISUBSTITUTED-2,5-DIIMINO GLYCOLURIL OF THE GERERAL FORMULA:
4. AN ARTICLE OF CLOTHING PROTECTIVE AGAINST VESICANTS WHICH COMPRISES A POROUS MATERIAL IMPREGNATED WITH A SUBSTANCE COMPRISING ESSENTIALLY A 1,3,4,6-TETRACHLORO-7,8DIARYL-2,5-DIIMINO GLYCOLURIL.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US526309A US2885305A (en) | 1944-03-13 | 1944-03-13 | Polychloro-7, 8-disubstituted-2, 5-diimino glycoluril for use as an antivesicant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US526309A US2885305A (en) | 1944-03-13 | 1944-03-13 | Polychloro-7, 8-disubstituted-2, 5-diimino glycoluril for use as an antivesicant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2885305A true US2885305A (en) | 1959-05-05 |
Family
ID=24096816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US526309A Expired - Lifetime US2885305A (en) | 1944-03-13 | 1944-03-13 | Polychloro-7, 8-disubstituted-2, 5-diimino glycoluril for use as an antivesicant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2885305A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464847A (en) * | 1966-10-25 | 1969-09-02 | Us Army | Treatment of fabrics with anthranilic acid and silver nitrate solutions |
| US4594239A (en) * | 1984-03-14 | 1986-06-10 | Pluim Jr Arthur W | Method for neutralizing offensive chemicals |
| US4803047A (en) * | 1984-03-14 | 1989-02-07 | Pluim Jr Arthur W | Method for neutralizing offensive chemicals |
| US10072106B2 (en) | 2016-10-14 | 2018-09-11 | State of Israel, Prime Minister's Office, Israel Insitute For Biological Research | N-halamine melamine derivatives as novel decontamination and biocidal agents |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005538A (en) * | 1932-08-27 | 1935-06-18 | Du Pont | Alkoxy-phenyl-imidazoles |
| US2155914A (en) * | 1936-02-28 | 1939-04-25 | Ind Mij Nv Deventer | Process for the preparation of a bleaching and sterilizing agent |
| US2351924A (en) * | 1939-03-27 | 1944-06-20 | Carnauh Boruk | Disinfecting product and process for its manufacture and application |
-
1944
- 1944-03-13 US US526309A patent/US2885305A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2005538A (en) * | 1932-08-27 | 1935-06-18 | Du Pont | Alkoxy-phenyl-imidazoles |
| US2155914A (en) * | 1936-02-28 | 1939-04-25 | Ind Mij Nv Deventer | Process for the preparation of a bleaching and sterilizing agent |
| US2351924A (en) * | 1939-03-27 | 1944-06-20 | Carnauh Boruk | Disinfecting product and process for its manufacture and application |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3464847A (en) * | 1966-10-25 | 1969-09-02 | Us Army | Treatment of fabrics with anthranilic acid and silver nitrate solutions |
| US4594239A (en) * | 1984-03-14 | 1986-06-10 | Pluim Jr Arthur W | Method for neutralizing offensive chemicals |
| US4803047A (en) * | 1984-03-14 | 1989-02-07 | Pluim Jr Arthur W | Method for neutralizing offensive chemicals |
| US10072106B2 (en) | 2016-10-14 | 2018-09-11 | State of Israel, Prime Minister's Office, Israel Insitute For Biological Research | N-halamine melamine derivatives as novel decontamination and biocidal agents |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Fraenkel et al. | Decarboxylation of malonic acid in quinoline and related media | |
| US3922331A (en) | Preparation of microporous rare-earth oxyhalides | |
| US2885305A (en) | Polychloro-7, 8-disubstituted-2, 5-diimino glycoluril for use as an antivesicant | |
| US2649389A (en) | Antivesicant compounds and clothing impregnated therewith | |
| SE7609986L (en) | N-ALKYLDIPHENYLAMINE DERIVATIVES WITH RODENTICID EFFICIENCY, COMPOSITIONS CONTAINING THE SAME, AND THEIR USE FOR CONTROLING RATS AND MOSS | |
| Marcus et al. | The Reaction of Hydrazine with 3, 6-Diamino-s-tetrazine1 | |
| Beyer et al. | Boron-Nitrogen Compounds. VIII. 1, 2 2-Dimethylamino-1, 3, 2-benzodiazaboroline | |
| US2754177A (en) | Beta-aminoborazole compounds and their preparation | |
| US2649464A (en) | Phosphorus-containing organic compounds | |
| Abshire et al. | SYNTHESIS OF SOME ALKYLATED ADENINES AS POTENTIAL ANTIMETABOLITES | |
| US3175950A (en) | Sunscreening preparations | |
| DE3069173D1 (en) | Substituted phenylamino-2-imidazoline-2 derivatives, their acid addition salts, medicaments containing them and process for their preparation | |
| CA1183844A (en) | Preparation of isocyanuric esters | |
| US3681126A (en) | Flame retardant article containing tris-(3 - halo - 2-hydroxypropyl)-hydroxymethylphosphonium chloride | |
| US2678930A (en) | Nu-chloro-2-substituted imidazolines | |
| US2968675A (en) | Halogenated organic nitrogen compounds and method of preparation | |
| US3082254A (en) | Propynyl hydrazobenzenes | |
| US3899619A (en) | 1,3,5-Triaza-7-phosphaadamantane and derivatives as flame retardants for textiles | |
| Chambers et al. | Polyhalogenoheterocyclic compounds. Part XXVI. Nucleophilic substitution in trifluoropyrazines | |
| US3072673A (en) | Chlorinated 2-iminoisopyrroles | |
| US3464847A (en) | Treatment of fabrics with anthranilic acid and silver nitrate solutions | |
| JPS63316755A (en) | N-methyl-alpha-dialkylaminoacetohydroxamic acid derivative | |
| KR910002875A (en) | Dihydropyrimidothiazine Derivatives | |
| US3288840A (en) | 2-propynyl salicylate | |
| Anantakrishnan et al. | The kinetics of the olefine-bromine reaction: Part V. Influence of substituents on the applicability of the kinetic equation of the catalysed reaction |