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Publication numberUS3197366 A
Publication typeGrant
Publication dateJul 27, 1965
Filing dateSep 10, 1962
Priority dateSep 10, 1962
Publication numberUS 3197366 A, US 3197366A, US-A-3197366, US3197366 A, US3197366A
InventorsWilliam N Cannon, Edwin R Shepard
Original AssigneeLilly Co Eli
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Embalming fluids and processes
US 3197366 A
Abstract  available in
Images(5)
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Claims  available in
Description  (OCR text may contain errors)

arteries.

United States Patent 3,197,366 EMBALMING FLUID?) AND PROCESSES William N. Cannon, Greenwood, and Edwin 1R. Shepard, Indianapolis, Ind, assignors to Eli Lilly and Company, Indianapolis, Ind, a corporation of Indiana No Drawing. Filed Sept. It), 1962, Ser. No. 222,657 11 Claims. (Cl. 167-495) The present application is a continuation-in-part of our application Serial No. 123,448 filed July 12, 1961, now abandoned.

This invention relates to novel embalming fluids and to novel embalming processes utilizing these fluids.

Some of mans earliest records, such as the paintings found in caves in Southern France, testify to the belief of those primitive hunters-the first Homo sapiens-in the presence of an immortal part or soul in mans body. Later the Egyptians, the originators of the earliest civilization, believed that mans body even after death was a resting place for his soul and that destruction of the body was accompanied by destruction of the soul. Thus, in order to insure the souls immortality, the Egyptians sought methods of preserving mans body after death for an indefinite length of time. Consequently, the Egyptian process of cadaver preservation or mummification was developed. The precise nature of the preservatives used by the Egyptians in mummifying their dead is not known, but the excellent state of preservation of the mummies on view in many museums reflects the skill of the Egyptians in the art of embalming. Our modern culture does not demand such long-term preservation of the body. Instead, modern embalmers strive to preserve the body only until time for burial, but contrive to make the preserved body reseinble the appearance of the deceased during his lifetime as nearly as possible.

The exact constitution of the embalming fluids used by the Egyptians in preserving the bodies of the dead is not known, and there has been little attempt in modern times to duplicate these embalming fluids, since the mummified body generally bears little resemblance to the living person. Furthermore, since the Egyptians did not under stand the manner of the circulation of the blood, they did not use arterial injection of preservatives. Instead they attempted to preserve a cadaver by employing embalming materials either externally or in the larger body cavities. Modern embalming practice involves injection of embahning fluid into both the arteries and the body cavities. The most widely used modern embalming fluid is formaldehyde, which is customarily utilized as a 0.5- 1.5 percent aqueous solution when employed as an arterial fluid, and as a 20-30 percent aqueous solution when employed as a cavity fluid. Other additives are frequently present in both types of embalming fluids.

Despite the almost universal use of formaldehyde in embalming, its use entails inherent disadvantages as a result of its mode of action. Thus, for example, while a 1.5

percent solution of formaldehyde will kill many organisms which are present in the body and which cause decomposition of the body after death, it does not kill all of them, particularly the gas-producing anaerobes which tend to be present to a greater extent in tissues than in the Higher concentrations of formaldehyde, which would theoretically be more completely bacetericidal, are in actual practice less so, because formaldehyde reacts with the cell-wall material of the arteries, which are in a state of collapse, to set up a barrier to the further flow of formaldehyde. In other words, the higher the formaldehyde concentration in arterial fluids, the lower its actual preservative action on the body as a whole. Furthermore, formaldehyde, by reacting with the arterial wall material, sets up a similar barrier to the diffusion of 3,197,366 Patented July 27, 1965 formaldehyde through the cell walls into the tissues where most of the putrefactive bacteria are present. Besides the above-mentioned disadvantage accompanying the use of high concentrations of formaldehyde, there is another drawback in that the reaction between formaldehyde in high concentration and body tissues is so extensive that close resemblance between the living person and the embalmed body cannot be achieved.

In addition to these disadvantages of formaldehyde as an embalrning fluid, the embalmer faces still another problem which the use of formaldehyde alone cannot solve. This problem relates to the preservation of bodies which are found two or three days after death and in which considerable bacterial decomposition has already taken place. In general, the aforementioned shortcomings of formaldehyde as an embalming fluid in ordinary practice are magnified many times in these instances, since the putrefactive anaerobes already present in the body tissues are responsible for the bacterial decomposition which has ensued and, as previously stated, formaldehyde, by reaction with the tissues, forms a barrier to its further penetration, thus preventing the attainment of a bactericidal concentration of formaldehyde in those tissues.

Among the putrefactive anaerobes which cause much tissue destruction are gram-negative organisms of the family Enterobacteriaceae as well as certain anaerobic and aerobic spore formers belonging to the families Bacillus and Clostridium. The production of gases by these spore-forming organisms not only causes considerable disfigurement of the corpse, but is also an indication that the most destructive putrefactive bacteria are growing within the corpse and that there is danger that other far-reaching changes, such as skin slip, are imminent.

It is an object of this invention to provide a method of embalming which will satisfactorily preserve cadavers while minimizing undesirable cosmetic changes. It is a further object of this invention to prevent the growth of putrefactive organisms in cadavers. Other objects of this invention will become apparent from the description which follows.

This invention provides a novel method of embalming which comprises injecting into a corpse an embalming fluid comprising an aqueous solution of an aldehyde represented by the following formula:

R"CHO wherein R" is selected from the group consisting of hydrogen and (CH J CHO, and n is an integer from 0 to 6 plus an anionic salt of one of the following cations: dibenziodolium, 3,7-dichlorodibenziodolium, 2,4-dichlorodibenziodolium, 3,7-dinitrodibenziodolium, 3-nitrodibenziodolium, and 3,7-bis(trifluoromethyl)dibenziodolium. The dibenziodolium ring system is illustrated below in the form of a salt:

1 9 I I+ I 4 5 6 In the formula, X is an anion. The dibenziodolium salts employed in this invention have a water solubility greater than 0.1 mg./ml. at 20 C. Among the anions which furnish salts with the designated dibenziodolium cations having a greater solubility in water than 0.1 mg./ml. at

20 C. are the sulfate, bisulfate, phosphate, phenate, acetate, and the like, and particularly the anions derived from a-hydroxy organic acids, including lactic acid, citric acid, tartaric acid, etc.

The above dibenziodolium compounds are used in admixture with formaldehyde or a dialdehyde, or a combination thereof, to form embalming fluids, these embalming fluids being employed according to the novel processes of this invention. The embalming fluids can be arterial concentrates, diluted arterial concentrates or arterial fluids, and cavity fluids. The dibenziodolium compounds are generally admixed with formaldehyde or a dialdehyde, or a combination thereof, in'a ratio of from about 5 to about 20 parts of a soluble salt of the heterocyclic iodine compound for each 100 parts or" total aldehyde. Because of the adverse eifect of other formula components of proprietary embalming fluids upon the water solubility of dibenzioclolium salts, a nonionic surface active agent is customarily employed as a third constituent of the novel embalming fluids of this invention. A preferred surface active agent is an alkylphenoxypolyethanol, although many other nonionic surface active agents can be employed with equally favorable results. The surface active agent can be present in the embalming concentrates in a concentration of about 0.1 to 5 g. for about 3 g. of heterocyclic iodine salt. A preferred concentration of the surface active agent is about 0.5 to 3 g. for about 3 g. of the heterocyclic iodine salt. Optimally, about 0.5 to 1 g. of nonionic surface active agent is employed for each 3 g. of the dibenziodolium salt. The actual concentrations of the surface active agent will, of course, depend upon whether an arterial concentrate, cavity fluid, or arterial fluid is to be prepared. Various suitable nonionic surface active agents include lauroyl diethanolamide, nonylphenoxy polyethoxy ethanol, polyoxyalkylene alkyl laurate, ethoxylated cetyl and stearyl alcohols, glycerol monopalmitate, stearate, and oleate, polyoxyethylene sorbitan monoleate, polyoxyethylene sorbitan monolaurate, and the condensation product of ethylene oxide with polypropylene oxide.

Customarily, arterial concentrates having formaldehyde as the only aldehyde present contain from about 15 to about 37 percent of formaldehyde. Thus, an arterial concentrate which is to be diluted for use as an arterial fluid in the'novel processes of this invention can include from about 0.75 percent to about 7.5 percent of a dibenziodolium compound represented by the above formula. In an arterial fluid itself, the permissible concentrations of formaldehyde are far lower and are usually in the range of about 0.75 to about 1.5 percent formaldehyde, preferably from about 1.0 to about 1.25 percent. In these arterial fluids the dibenziodolium compounds can be present in concentrations of about 0.0375 percent to about 0.3 percent, depending upon the bacteriostatic activity of the compound and the desired level of "bacteriostasis. A third, even more dilute solution, known as a flushing solution, is also frequently used. This flushing solution can be prepared either by further dilution of an arterial fluid or by dilution of an arterial concentrate, and usually contains less than about 0.75 percent formaldehyde. The level of dibenziodolium preservative in these flushing solutions will, of course, be correspondingly lower. The cavity fluids are usually similar in composition to undiluted arterial concentrates and have the same content of heterocyclic iodine compound as previously set forth for the arterial concentrates, although it is customary to employ concentrations of formaldehyde greater than 20 percent in cavity fluids.

The surface active agent is present in these various embalrning fluids and embalming fluid concentrates in the same ratio as set forth above. For example, an arterial concentrate or cavity fluid containing from 15 to 37 percent formaldehyde and from 0.75 to 7.5 percent of a heterocyclic iodine disinfectant would contain in addition from 0.025 to 6.25 percent of a surface active agent. An especially preferred arterial concentrate contains about 20 percent by weight of formaldehyde, about 3 percent by weight of the dibenziodolium salt, and about 0.5 to 1 percent by weight of the nonionic surfactant. Likewise, the arterial fluids containing preferably from 0.75 to 1.5

percent of formaldehyde and from 0.0375 to 0.3 percent heterocyclic iodine disinfectant would contain from 0.0125 to 1.5 percent of the surface active agent.

When a dialdehyde is employed to replace all or part of the formaldehyde in one of the above embalming fluids, it is possible to use a lower total concentration of aldehyde. For example, the preferred range for a concentrate prepared from glyoxal plus formaldehyde is from 0.75 to 1 percent of aldehyde instead of the 1 to 1.25 percent range customary when formaldehyde alone is used. The presence of less aldehyde inherently gives a higher ratio of dibenziodolium antiseptic to aldehyde in the composition, since an antibacterial concentration of the antiseptic must be present at all times. For example, if an arterial concentrate is prepared using glyoxal as the predominant aldehyde, it will contain from 8 to 20 percent glyoxal and from 5 to 10 percent added formaldehyde, and the ratio of dibenziodolium compound to total aldehyde content will be somewhat higher than in a concentrate containing formaldehyde as the only aldehyde present.

PREPARATION OF ARTERIAL FLUID Five milliliters of a solution containing 63 mg. of dibenziodoliurn lactate per ml. was diluted first with 4.9 ml. of water and then with 0.1 ml. of octylphenoxypolyethoxyethanol. 0.50 ml. of this preparation was diluted with 15.1 ml. of one percent formaldehyde solution to give an arterial embalming fluid ready for use.

A 20 percent formaldehyde solution was diluted with 20 parts of water. 10 ml. of octylphenoxypolyethoxyethanol were added to 240 ml. of the diluted formaldehyde solution. 250 mg. of bis(dibenziodolium) sulfate were added to this solution. Stirring was continued until hhe solid had dissolved to prepare a suitable embalming uid.

Two different methods can be employed for preparing the embalming fluids of this invention. The first method involves the preparation of a concentrate containing formaldehyde, the dibenziodolium compound, and a nonionic surface active agent for dilution with cold water to give an arterial fluid. This concentrate can also be used undiluted as a cavity fluid. In the second method, the dibenziodolium compound and the nonionic surface active agent can be dissolved in water, and this solution can be used as the diluent for the usual 15 to 37 percent formaldehyde concentrate.

The novel embalming fluids comprising either an aldehyde and a dibenziodolium compound, or an aldehyde, a dibcnziodolium compound and a nonionic surfactant, are employed in embalming in the same way in which the formaldehyde solutions would be used in the absence of the surfactant and/or the dibenziodolium compound; that is to say, the dilute aldehyde solutions, containing from 0.5 to 1.5 percent total aldehyde, are used as arterial fluids and are injected directly into the main arteries of the cadavers. The cavity fluids, containing 15 to 37 percent formaldehyde, are injected into the peritoneal and chest cavities. The flushing fluids, containing 0.75 percent or less of aldehyde, are also injected into the arteries. Arterial concentrates are diluted to form arterial fluids, which are then later used as specified above.

The novel compositions of this invention have demonstrated their utility in several ways. For example, 2 ml. of a Staphylococcus aureus suspension having a titre of about 2x10 cells per ml. were injected into thirteen rabbits via a marginal ear vein. The rabbits were killed and their blood removed 20 minutes later. An embalming fluid containing one percent formaldehyde, 1,000 ppm. of bis(dibenziodolium) sulfate, and .4 percent octylphenoxypolyethoxyethanol was injected into the rabbit cadavers. Twenty-four hours later, the livers of these rabbits were removed and homogenized, diluted serially with distilled water, and the numbers of Staphylococcus aureus cells per milliliter were determined by bacterial iodide in 750 ml. of water. immediately. After the addition of the chilled diazonlum salt solution had been completed, the reaction mixture .Was then cooled. D formed in the reaction was extracted with 500 ml. of

cbunti Other rabbits similarly injected with Staphylococcus aureus cells were killed and embalmed with one percent formaldehyde alone. Four out of thirteen rabbits which were embalmed with a fluid containing formaldehyde plus a dibenziodolium salt showed no S. aureus, and the remaining'nine gave S. aureus cell counts ranging from between to 10 per milliliter. Only one out of ten rabbit-s embalmed with the one-percent formaldehyde solution alone showed no S. aureus in the liver, while the other-nine all had counts ranging from 10 to 10 cells per milliliter.

The same embalming fluid inhibited both intestinal and intraperitoneal gas formation in rabbit cadavers when injected'both arterially and intraperitoneally.

The dibenziodolium compounds represented by the aboveformula can be prepared by either of two methods. The first method utilizes the reaction of peracetic acid and an o-iodobiphenyl to give the corresponding iodoso acetate. Decomposition of this compound with a strong acid such as sulfuric acid yields the desired dibenziodolium compound as the sulfate or bisulfate. Alternatively, the suitably substituted o-iodobiphenyl compound can be converted to the iododichloride compound. Alkaline hydrolysis of this compound yield the o-iodosobiphenyl, which is converted to a heterocyclic iodine compound as specified above for the iodoso acetate. The preparation of some typical dibenziodolium salts is illustrated below. Preparative procedure for various other dibenziodolium salts which are within the scope of this invention'have been described in the literature.

Preparation 1 BIS (3,7-DICH-LORODIBENZIODOLIUM) SULFATE .The ,required intermediate, 2-iodo-4, 4'-dichlorobiphenyl, was prepared from 2-nitr0-4, 4-dichlorobiphenyl. Hydrogenation of a dioxane solution of the nitro compound was efiected using a Raney nickel catalyst. The catalyst was removed by filtration and the filtrate was evaporated to dryness inivacuo; Recrystallization of the residue from anhydrous ethanol afiorded 2amino-4,4- dichlorobiphenyl melting at about 8586 C.

Analysis.Cal.: C, 60.53; H, 3.81; N, 5.88. Found:

C, 60.61; H, 4.21; N, 6.04.

A slurry of 71.4 g. of 2-amino-4, 4'-dichlorobiphenyl in 500 ml. of water was prepared and 49 g. of 18 M minutes. The cold solution was filtered, and the filtrate was poured into a stirred solution of 75 g. of potassium Evolution of nitrogen began was warmed to about 100 C. for about 2 hours and The 2-iodo-4, 4'-dichlorobiphenyl ether. The ether extract was separated and was washed successively with water, 10 percent aqueous sodium thiosulfate, water, 10 percent aqueous sodium hydroxide, and

water. The ether layer was dried and the ether was removed by evaporation in vacuo. Distillation of the residue yielded 2-iodo-4, 4'-dichlorobiphenyl boiling in the range 135-136 C. at a pressure of about 0.1 mm. of

-mercury.-

. 0 C. until it became homogeneous, and was then warmed to room temperature. To 25 ml. of-a peracetic acid solution so prepared, there was added dropwise, with stirring,

a solution of 5 g. of 2-iodo-4,4'-dichlorobiphenyl in about 10 ml. of acetic anhydride. The reaction mixture was kept at ambient room temperature for about 12 hours, and was then chilled and stirred while 5 ml. of 18 M sulfuric acid were'added dropwise. After the addition of the sulfuric acid had been completed, the reaction mixture was allowed to warm to ambient room temperature. After standing at room temperature for four hours, the mixture was diluted with about ml. of cold water, stirred for about an hour, and filtered to separate the precipitated bis(3,7- dichlorodibenziodolium) sulfate. The crude product was slurried in benzene, filtered, reslurried in methanol, and again filtered to give purified bis(3,7-dichlorodibenziodolium) sulfate melting at about 274-275 C.

Preparation 2 DIBENZIODOIAIU'M BISULEATE A solution of 7.4 g. of 2-iodosobiphenyl, prepared from 2-iodobiphenyl dichloride by the procedure of Org. Syn. Col., III, 483, in 50 ml. of glacial acetic acid was chilled to about 15 C., and 5 ml. of 18 M sulfuric acid were added in dropwise fashion to the solution over a 15-minute period. The reaction mixture was kept at ambient room temperature for about 16 hours, cooled to about 10 C., and diluted with 250 ml. of an ice-water mixture. Dibenziodolium bisulfate precipitated and was separated by filtration. The filter cake was slurried in 100 m1. of benzene and the slurry was refiltered, thus yielding dibenziodolium bisulfate as a white crystalline solid melting at about 264-267 C. with decomposition.

Preparation 3 BIS 3,7 TRIFLUOROMETHYL) DIBENZIODOLIUM IODIDE Following the procedure of Searle and Adams, I. Am. Chem. Soc., 55, 1653 (1933), a slurry was prepared containing 14.7 g. of 2,2'-diamino-4,4'-bis(trifluorOmethyDbiphenyl in 50 ml. of 12 N hydrochloric acid and 50 ml. of water. The slurry was cooled to about 05 C. and was maintained at that temperature while a solution of 8 g. of sodium nitrite in 10 m1. of water was added in dropwise fashion. After the addition had been completed, the tetrazotization mixture was stirred for about 30 minutes, after which a solution of 26 g. of sodium iodide in 50 ml. of water was added, also in dropwise fashion. The reaction mixture was allowed to warm to ambient room temperature and was then heated at about 100 C. for about 2 minutes. The resulting mixture was cooled to precipi tate bis(3,7-trifluoromethyl)dibenziodolium iodide as a coal-black solid. The solid-precipitate was separated by filtration and was washed with copious quantities of cold water. The filter cake was slurried in about 100 ml. of

ethanol and the slurry was refiltered. This operation was repeated two more times to provide a lemon-yellow colored material melting at about 268270 C. with decomposition. Recrystallization of this material from a dimethylformamide-water solvent mixture yielded bis(3,7- trifluoromethyl)dibenziodolium iodide as a solvate with dimethylformamide. Melting point: 274-276 C.

-' Other salts can be prepared from the above salts by methods well known to the art, such as by metathesis, for example. 'Thus, an aqueous solution of bis(dibenzio- 'dolium) sulfate can be treated with an aqueous solution of "barium chloride or barium nitrate to form dibenziodolium nitrate or chloride and a readily separable insoluble precipitate of barium sulfate.- Alternatively, a solution of.

barium hydroxide can be-added to bis(dibenziodolium) sulfate to yieldan insoluble precipitate of barium sulfate plus a solution of diben ziodolium hydroxide. Neutralization'of the hydroxide with any suitable acid yields a dibenziodolium salt in which the anion of the acid becomes theanion of the dibenziodolium salt.

I I Preparation 4 31 s a t-morn.onopmuuzrononmn SULFATE A solution of 10 g. of 2-iodo-3,S-dichlorobiphenyl in 50 ml. of chloroform was cooled to about C. and maintained at 0-5 C. while chlorine gas was bubbled into the solution until it was saturated. The mixture was diluted with about 300 ml. of hexane and the introduction of chlorine gas was continued. Yellow crystals of 2-iodo- 3,5-dichlorobiphenyl dichloride precipitated and were removed by filtration. The compound melted at about An aqueous solution containing 10 g. of sodium hydroxide in 100 ml. of Water was added to a stirred mixture of 42 g. of 2-iodo3,S-dichlorobiphenyl dichloride, 100 g. of crushed ice, and 100 ml. of water. The addition required about 30 minutes. Stirring was continued for about four hours while the reaction mixture was allowed to come to room temperature. During this time, white crystals of 2-iodoso-3,S-dichlorobiphenyl separated and were removed by filtration. The product was partially dried on the filter, and was then dissolved in about 300 ml. of glacial acetic acid. After filtration to remove insoluble impurities, the solution was cooled to below 5 C. and maintained at that temperature for about 1.5 hours while 25 ml. of 18 M sulfuric acid were added dropwise. Bis(2,4-dichlorodibenziodolium) sulfate began to precipitate even before the addition was completed. The mix ture was stirred while warming to room temperature and for about 14 hours thereafter. The product was separated by filtration, washed with water, slurried with benzene, filtered and dried. The purified bis(2,4-dichlorodibenziodolium) sulfate melted at about 224225 C.

The preparation of various other salts from the corresponding sulfates, or bisulfates is illustrated by the following:

Preparation 5 DIBENZIOZDOLIUM IJACTATE A solution of 6.63 g. of barium hydroxide octahydrate in a minimum volume of water was added to a solution of 10.2 g. of bis(dibenziodolium) sulfate in 1,000 ml. of hot Water. A precipitate of barium sulfate was formed immediately. The reaction mixture was stirred and cooled to insure complete precipitation of barium sulfate, which was then separated by filtration. The pH of the solution was lowered from about 12 to about 3 by the slow addition of an 85 percent aqueous lactic acid solution. Evaporation of the solvent in vacuo yielded dibenziodolium lactate as a residue. Recrystallization of the residue from an ethanolether solvent mixture yielded dibenziodolium lactate melting at about 156-159 C.

Dibenziodolium glycolate was prepared from bis(dibenziodolium) sulfate and glycolic acid by the above procedure and melted with decomposition at about ISO-152 C.

Bis(dibenziodolium) sulfate was converted to dibenziodolium citrate by the above procedure using citric acid in place of lactic acid. The compound melted with decomposition at about 167l78 C.

Analysis.--Calc.: I, 26.99. Found: 1, 26.96.

Bis(dibenziodolium) sulfate was converted to dibenziodolium dihydrogen phosphate by the above procedure using phosphoric acid in place of lactic acid. The product melted at about 272-274 C.

Analysis.-Calc.: I, 35.75. Found: I, 35.55.

Dibenziodolium acetate was prepared from dibenziodolium bisulfate and acetic acid and melted with decomposition over a range of about 180190' C.

Analyris..-Calc.: I, 37.53. Found: I, 36.86.

Preparation 6 \DIBENZIODOIJIUM LACTATE A solution containing about 0.1 mole of barium lactate was prepared from lactic acid and barium hydroxide. About 9.9 g. of dibenziodolium bisulfate were added to the barium lactate solution with stirring. Stirring wascontinued overnight. The precipitated barium sulfate was separated by filtration and the filtrate, containing dibenziodolium lactate was evaporated to dryness, leaving the desired compound as a white crystalline residue. The compound was purified by recrystallization from an ethanol ether solvent mixture.

Dibenziodolium glycolate was prepared by the same procedure from glycolic acid. Melting point: 150-152 C. with decomposition.

3,7-dich1orodibenziodolium lactate is prepared by the above procedure using bis(3,7-dichlorodibenziodolium) sulfate in place of dibenziodolium bisulfate as the starting material.

Preparation 7 DIBENZIODOLIUM NITRATE A mixture of g. of dibenziodolium bisulfate and 2 liters of water was heated to reflux. A solution of 60 g. of sodium nitrate in 100 ml. of water was added rapidly to the refluxing solution. The reaction mixture was stirred while being cooled to ambient room temperature. Filtration of the cooled mixture yielded 73 g. of dibenziodolium nitrate melting at about 242 244 C.

Preparation 8 DIBENZIODOLIUM 2,4,5-TRICHLOROPHENATE A solution of 3.96 g. of 2,4,5-trichlorophenol in 30 ml. of 0.7 N sodium hydroxide solution was added rapidly to a solution of 6.54 g. of bis(dibenziodolium) sulfate in 500 ml. of hot water. An immediate yellow precipitate formed. The reaction mixture was cooled to about 0 C. was filtered to separate the precipitated dibenziodolium 2,4,5-trichlorophenate. The salt melted with decomposition at about 181--182 C. after recrystallization from a mixture of dimethylformaride and water.

Analysis.-Calc.: C, 45.59; H, 2.12. Found: C, 45.39; H, 2.38.

We claim:

1. A method for embalming which comprises injecting into the vascular system and the abdominal and chest cavities of a cadaver a solution containing an aldehyde represented by the formula:

R"CHO where R" is selected from the group consisting of hydrogen and (CH CHO, and n is a number from 0 to 6 plus an antiseptic anionic salt of a cation selected from the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodohum cation, the 3,7-dinitrodibenziodolium cation, the 3-nitrodibenziodolium cation, and the 3,7-bis(trifluoromethy1)dibenziodolium cation, said antiseptic salt having a water solubility greater than 0.1 mg./ml. at 20 C.

2. A method for embalming which comprises injecting into the vascular system and the abdominal and chest cavities of a cadaver a solution containing from about 5 to about 20 parts of an anionic salt of a member of the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodolium cation, the 3,7-dinitrodibenziodolium cation, the 3-nitrodibenziodolium cation, and the 3,7-bis(trifl-uoromethyl)dibenziodolium cation, said salt having a water solubility greater than 0.1 mg/ml. at 20 C., for each 100 parts of an aldehyde represented by the following formula:

R"CHO gen and (CH ),,CHO, and n is a number from 0 to 6.

3. The process of claim 2 wherein the antiseptic salt is his (dibenziodolium) sulfate.

4. The process of claim 2 wherein the antiseptic salt is bis(3,7-dichlor'odibenziodolium) lactate.

5. The process of claim 2 wherein the antiseptic salt is bis(3,7-bistrifluoromethyl)dibenziodolium sulfate.

6. A method for embalming which comprises injecting into the vascular system and the abdominal and chest cavities of a cadaver a solution containing from about 5 to about 20 parts of an antiseptic anionic salt of a member of the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodolium cation, the 3,7-dinitrodibenziodolium cation, the 3-nitrodibenziodolium cation, and the 3,7-bis (trifluoromethyl)dibenziodolium cation, said salt having a water solubility greater than 0.1 mg./ml. at 20 C., for each 100 parts of an aldehyde represented by the following formula:

R"CHO wherein R" is selected from the group consisting of hydrogen and (CH ),,CHO, and n is a number from to 6, and from about 0.1 to about 5 parts of a surface active agent for each 3 parts of antiseptic salt.

7. The process of claim 6 wherein the surface active agent is an alkyl phenoxypolyethoxyethanol.

8. An embalming concentrate containing from about 15 to about 37 percent of formaldehyde and from about 0.75 to about 7.5 percent of an anionic salt of a member of the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodolium cation, the 3,7-dinitrodibenziodolium cation, the 3-nitrodibenziodolium cation, and the 3,7-bis (-trifluoromethyl) dibenziodolium cation.

9. An embalming concentrate containing from about 15 to about 37 percent of formaldehyde, from about 0.75 to about 7.5 percent of an anionic salt of a member of the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodolium cation, the 3,7-dinitrodibenziodoliurn cation, the 3-nitrodibenziodolium cation, and the 3,7-bis(trifluoromethyl)dibenziodolium cation, and from about 0.025 to about 6.25 percent of a surface active agent.

10. An arterial fluid comprising from about 0.75 to about 1.5 percent formaldehyde and from about 0.0375 to about 0.3 percent of an anionic salt of a member of the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodolium cation, the 3,7-dinitrodibenziodolium cation, the 3-nitrodibenziodoliurn cation, and the 3,7-bis(trifluoromethyl)dibenziodolium cation.

11. An arterial fluid comprising from about 0.75 to 5 about 1.5 percent formaldehyde, from about 0.0375 to about 0.3 percent of an anionic salt of a member of the group consisting of the dibenziodolium cation, the 3,7-dichlorodibenziodolium cation, the 2,4-dichlorodibenziodolium cation, the 3,7-dinitrodibenziodolium cation, the

10 3-nitrodibenziodolium cation, and the 3,7-bis(trifluoromethyl) dibenziodolium cation, and from about 0.0125 to about 1.5 percent of a surface active agent.

References Cited by the Examiner UNITED STATES PATENTS 2,272,525 2/42 Jones 167-49.5 2,805,975 9/57 Hamilton 167-495 2,878,293 3/59 Kinger 260350 3,057,775 10/62 Rendon 167-49.5 OTHER REFERENCES Chem. Abst., vol. 39, p. 5938 (1945). Collette et a1., J.A.C.S., vol. 78, pp. 3819-20 (1956). Freelander et al., Chemical Abstracts, vol. 41, p. 2115 (1947 Irving et al.: Chemical Abstracts, vol. 54, 20443(b) (1960).

Masson et al.: J. Chem. Soc. (London), 1937, pp. 1,718-23. S'andin et al.: I.A.C.S., vol. 74, pp. 274-275, January Wasylewsky et al.: J.A.C.S., vol. 72, pp. 10381039.

JULIAN S. LEVITT, Primary Examiner.

5 LEWIS GO'ITS, Examiner.

Patent Citations
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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US5405606 *Dec 3, 1993Apr 11, 1995Efh, Inc.Mixture of glutaraldehyde, phenoxyethanol and alcohol
US5607668 *Sep 15, 1994Mar 4, 1997Efh, Inc.Glutaraldehyde, phenoxyethanol, alcohol, formaldehyde-free
US5622695 *Sep 15, 1994Apr 22, 1997Efh, Inc.Anatomical and biological preservative and method
US5827511 *Feb 27, 1997Oct 27, 1998Efh, Inc.Preservative and embalming fluid
Classifications
U.S. Classification424/75, 27/22.2, 514/695, 514/693, 514/574
International ClassificationC07D347/00
Cooperative ClassificationC07D347/00
European ClassificationC07D347/00