AQUEOUS COMPOSITION BASED ON POLYOXYMETHYLENE DIALKYL ETHERS (POM) AND THEIR USE FOR THE PRESERVATION AND/OR EMBALMING OF THE HUMAN OR ANIMAL BODY

Abstract

The invention relates to a composition comprising: a) a mixture of polyoxymethylene dialkyl ethers (POM) having a restricted specific molecular distribution b) at least one biocidal agent c) at least one pro-penetrating agent d) at least one dye e) optionally, another additive and water as diluent.

It also relates to a non-therapeutic method of preserving and/or embalming a dead human or animal body using the composition, such as the use of this composition for anatomopathological purposes.

Claims

1. Aqueous composition wherein it comprises the following components: a) a mixture of polyoxymethylene dialkyl ethers (POM) selected from a mixture of compounds of the general formula R(OCH.sub.2).sub.nOR, with R,R being identical or different and chosen from methyl and/or ethyl for at least 90%, preferably at least 95 mol %, of the total R+R and the rest of R,R being identical or different alkyls chosen from among those having 3 to 8 carbons and representing less than 10%, preferably less than 5 mol % of the total R+R, and provided that: a1) when RR=methyl, the mixture comprises the 3 compounds with n=3 to 5 or both compounds with n=3 to 4, and the weight of the compounds (with n=3 to 5 or n=3 to 4) represents at least 95%, preferably at least 99% of the total weight of the mixture and a2) when RR=ethyl, the mixture comprises the 3 compounds with n=2 to 4 or both compounds with n=2 to 3 and the weight of the compounds (with n=2 to 4 or n=2 to 3) is at least 95%, preferably at least 99% of the total weight of the mixture a3) when R=methyl and R=ethyl, the mixture comprises the 4 compounds with n=2 to 5 or the 3 compounds with n=2 to 4 and the weight of the compounds (with n=2 to 5 or n=2 to 4) represents at least 95%, preferably at least 99% of the total weight of the mixture, b) at least one biocidal agent (c) at least one pro-penetrating agent d) at least one dye, e) optionally, at least one other additive and water as diluent.

2. Composition according to claim 1, wherein the proportion by weight of components a)+b)+c)+d)+e) represents from 0.5 to 30%, preferably from 1 to 25% and more. preferably from 1 to 20%, of the total weight of the aqueous composition.

3. Composition according to claim 1, wherein the component a) represents from 20 to 50%, preferably from 30 to 40% by weight with respect to a)+b)+c)+d)+e), and from 0.5 to 15%, preferably from 0.8 to 8%, of the total weight of the aqueous composition.

4. Composition according to claim 1, wherein the component a) is a mixture according to a1) with RR=methyl with n=3 to 5 or n=3 to 4.

5. Composition according to claim 1, wherein the component a) is the mixture according to a2) with RR=ethyl and with n=2 to 4 or with n=2 to 3.

6. Composition according to claim 1, wherein the mixture is according to a3), with R=methyl and R=ethyl and with n=2 to 5 or n=2 to 4.

7. Composition according to claim 1, wherein the biocidal component b) is selected from: iodine, polyvinylpyrrolidone iodine (polyvinylpyrrolidone-iodine complex), bronopol or 2-bromo-2-nitro-1,3 propylene glycol, alkyl chloride (C12-C18) dimethylbenzylammonium (ADBAC C12-18), alkyl chloride (C12-C16) dimethylbenzylammonium (ADBAC/BKC C12-16), alkyl chloride (C12-C14) dimethylbenzylammonium (ADBAC C12-14); alkyl chloride (C12-C14) dimethyl ethyl benzyl ammonium (ADEBAC C12-14), glutaraldehyde; ethanol, peracetic acid, methyl ethyl ketone peroxide, butanedial, diethylacetal, glyoxal, diethylene glycol, organic acids such as ascorbic acid or citric acid, phenolics such as vanilic aldehyde, guaiacol, eugenol, phenol, methylparaben, propylparaben 1-hexadecylpyridinium chloride, a compound of the formula (C.sub.3H.sub.4O)n.(C.sub.3H.sub.4O.sub.2)m where n>m.

8. Composition according to claim 1, wherein the biocidal component b) is chosen from: iodine, polyvinylpyrrolidone iodine (polyvinylpyrrolidone-iodine complex), bronopol, alkyl chloride (C12-C18) dimethylbenzylammonium (ADBAC C12-18), alkyl chloride (C12-C16) dimethyl benzyl ammonium (ADBAC/BKC C12-16), alkyl chloride (C12-C14) dimethyl benzyl ammonium chloride (ADBAC C12-14), alkyl chloride (C12-C14) dimethyl ethyl benzyl ammonium (ADEBAC C12-14), glutaraldehyde, a compound of formula (C.sub.3H.sub.4O)n.(CH.sub.4O.sub.2)m where n>m.

9. Composition according to claim 1, wherein the pro-penetrating component c) is chosen from: propylene glycol, monoethylene glycol, glycerol, propanol-2, dimethyl sulfoxide, polyethylene glycol, 2-ethoxyethanol, 2 phenoxyethanol, tetrahydrofurfuryl alcohol, linear or branched C.sub.2-C.sub.6 monoalcohol; a glycol such as 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 2,3-butanediol, hexylene glycol; a C.sub.8-C.sub.22 fatty acid; a cyclodextrin; a surfactant; C.sub.1-C.sub.4 alkyl acetate; a mono- or polyester of fatty acid and glycerol or propylene glycol; a fatty alcohol ester of lactic acid or glycolic acid; an ester of fatty acid and isopropyl; a C.sub.8-C1.sub.8 fatty alcohol; an azone; an alkyl N,N-dialkylaminoalkanoate; an amide, urea; a urea derivative; a terpene; a terpenoid; methyl or benzyl nicotinate; a sulfoxide; isosorbide.

10. Composition according to claim 1, wherein the pro-penetrating component c) is selected from propylene glycol, monoethylene glycol, glycerol, propanol-2, dimethylsulfoxide.

11. Composition according to claim 1, wherein it comprises: 0.5 to 10%, preferably 0.8 to 8% by weight of component a) relative to the total weight of the aqueous composition, from 0.1 to 3%, preferably from 0.15 to 2% by weight of component b) relative to the total weight of the aqueous composition from 0.5 to 10%, preferably from 0.8 to 8% by weight of component c) relative to the total weight of the aqueous composition from 0.1 to 8%, preferably from 0.2 to 5% by weight of component d) relative to the total weight of the aqueous composition.

12. Composition according to claim 1, wherein it comprises in addition to at least one other additive selected from: perfume as flower extracts such as rose (rose oil), lilac, or perfumes synthetic (aromatic esters with rather fresh notes like eucalyptus), borax, potassium nitrate, boric acid, sodium citrate, sodium hexametaphosphate, sodium acetate, hydrochloric acid, bis(tributyltin) oxide, sodium phosphate dibasic, sodium phosphate monobasic, ethylenediamine tetracetic acid (EDTA), sodium alkylsulfonate, potassium carbonate, trichloroacetaldehyde.

13. Non-therapeutic method for preserving a human or animal body and/or embalming a dead body, the method comprising administering to the body a composition according to any claim 1.

14. Method according to claim 13, wherein the composition is injected intra-arterially into the body.

15. Method according to claim 13, wherein the composition is infused into the body.

16. Method according to claim 13, wherein the composition is applied topically on the body.

17. A method of preservation of organs, tissues or cells of a living or dead, human or animal organism/body, comprising the step of immersion of said organs, tissues or cells in the composition of claim 1.

18. The method of claim 17, wherein said preservation is for anatomopathology purposes.

Description

EXAMPLES

1) Raw Materials Used

[0056] All raw materials used in synthesis and application are presented in the summary table 1 below. [0057] Raw materials used in synthesis and application formulation

TABLE-US-00001 TABLE 1 Technical func- tion according Raw material Name or chemical nature to the invention Synthesis Methylal CH.sub.3OCH.sub.2OCH.sub.3 Raw material Ethylal CH.sub.3CH.sub.2OCH.sub.2OCH.sub.2CH.sub.3 Raw material Paraformaldehyde (CH.sub.2O).sub.n Raw material Trioxane (CH.sub.2O).sub.3 Raw material Amberlyst.sup.R resin A15 (from Dow/Rhm & Catalyst Haas) Application formulation POMs R(OCH.sub.2).sub.nOR Component a) see synthesis examples (ADBAC/BKC (C12-16) Alkyl chloride (C12-16) Biocide b) CAS# 68424-85-1 dimethyl benzyl Ammonium (ADBAC (C12-14)) Alkyl chloride (C12-14) Biocide b) CAS#85409-22-9 dimethyl benzyl ammonium (ADBAC (C12-18)) Alkyl chloride (C12-18) Biocide b) CAS# 68391-01-5 dimethyl benzyl ammonium (ADEBAC (C12-14)) Alkyl chloride (C12-14) Biocide b) CAS# 85409-23-0 dimethyl ethyl benzyl ammonium Propylene glycol CH.sub.2(OH)CH(OH)CH.sub.3 Propenetrating agent c) Borax Additive e) Glycerin CH.sub.2(OH)CH(OH)CH.sub.2(OH) Propenetrating agent c) Potassium nitrate KNO.sub.3 Additive e) Dye Eosin Dye d) Perfume Rose essence Additive e)

Preparation of POMM (RR: Methyl) and POME (RR=Ethyl

Synthesis Example 1

Preparation of POMM.SUB.2-8 .(R(CH.SUB.2.O).SUB.n.OR with n=2 to 8 and RR=Methyl)

[0058] 100 g of methylalalso called dimethoxymethane(1.32 mol) and 30 g of trioxane (1 mol) are loaded into a 500 ml double-jacketed Schott reactor equipped with mechanical stirring, a condenser, and a temperature probe. 5 g of Amberlyst.sup.R A15 resin, previously washed with methanol and dried under vacuum, are added. The mixture is heated to 50 C. and allowed to react for 1 hour. The reaction mixture is filtered and then washed with 10 g of 15% aqueous sodium hydroxide solution. The methylal is removed by evaporation under reduced pressure (90 C., 650 mbar (65,000 Pa absolute) measured at the evaporator) on a rotary evaporator. 55 g are obtained from a cut POMM.sub.2-8 (CH.sub.3(CH.sub.2O).sub.nOCH.sub.3 where n is 2 to 8.

[0059] The mass distribution of the product obtained is determined by GC analysis as shown in Table 2. The analysis is performed on an Agilent 5890 chromatograph equipped with an Agilent sample changer, a split injector and an FID detector. An OV1701 column (14% cyanopropylmethylmethylpolysiloxane), 30 m in length, 0.25 mm in diameter, with a film thickness of 0.25 m is used. The split is 46 mL/min, 1 L is injected, the column pressure is 5 psi (34474 Pa relative), the oven temperature is programmed to 50 C. for 5 minutes, then a ramp of 10 C./min up to 250 C., then maintained for 15 minutes. The temperature of the injector is 200C, that of the detector 270 C. A satisfactory separation of the products is thus obtained.

Synthesis Example 2

Preparation of POMM.SUB.3-8 .with n=3 to 8 and RR=Methyl

[0060] 100 g of methylal (also called dimethoxymethane CH.sub.3OCH.sub.2OCH.sub.3) (1.32 mol) and 30 g of trioxane (1 mol) were loaded into a 500 ml jacketed Schott reactor equipped with mechanical stirring, a condenser, and a temperature probe). 5 g of Amberlyst.sup.R A15 resin, previously washed with methanol and dried under vacuum, are added. The mixture is heated to 50 C. and allowed to react for 1 hour. The reaction mixture is filtered and then washed with 10 g of 15% aqueous sodium hydroxide solution. The methylal is removed by evaporation under reduced pressure (90 C., 600 mBar (60,000 Pa) measured at the evaporator) on a rotary evaporator, then the POMM2 and the residual water are then removed by vacuum distillation. (Oldershaw type column with 10 trays) operating at a pressure of 200 mBar (20,000 Pa) at 90 C. 32 g of a cut POMM.sub.3-8 (CH.sub.3(CH.sub.2O).sub.nOCH.sub.3 where n is 3 to 8) are obtained.

[0061] The mass distribution of the product obtained is determined by GPC analysis as shown in Table 2.

Synthesis Example 3

Preparation of POMM.SUB.3-4 .with n=3 to 4 and RR=Methyl

[0062] On the product of Synthesis Example 2, the distillation cut is collected between 60 C. under 65 mbar (6500 Pa) and 90 C. under 10 mbar (1000 Pa) corresponding to POMM.sub.3-4 where n is 3-4.

Synthesis Example 4

Preparation of POMM.SUB.3-5 .with n=3 to 5 and RR=Methyl

[0063] On the product of Synthesis Example 2, the distillation cut is collected between 60 C. under 65 mbar (6500 Pa) (measured at the column) and 86 C. under 1 mbar (100 Pa) corresponding to POMM.sub.3-5.

Synthesis Example 5

Preparation of POME.SUB.2-8 .with n=2 to 8 and RR=Ethyl

[0064] The procedure is identical to that of Synthesis Example 2 using 137 g of ethylal-diethoxymethane (CH.sub.3CH.sub.2OCH.sub.2OCH.sub.2CH.sub.3)-(1.32 mol), 30 g of trioxane (1 mol), and 7 g of Amberlyst.sup.R resin A15. After reaction, the catalyst is filtered, the product is neutralized with sodium hydroxide to remove all traces of acid, then the light fractions are evaporated under a partial vacuum of 65 mbar (6500 Pa) at 60 C.

[0065] A C.sub.2H.sub.5(CH.sub.2O).sub.nC.sub.2H.sub.5 mixture is obtained with n from 2 to 8 (RR=ethyl). The mass distribution of the product obtained is determined by GPC analysis as shown in Table 2.

Synthesis Example 6

Preparation of POME.SUB.2-4., with n=2 to 4 and RR=Ethyl

[0066] On the product of Synthesis Example 5, the distillation cut is collected up to 79 C. under 1 mbar (100 Pa) corresponding to POME.sub.3-4.

Synthesis Example 7

Preparation of POME.SUB.2-3., with n=2 to 3 and RR=Ethyl

[0067] On the product of Synthesis Example 5, the distillation cut is collected at 79 C. under 13 mbar (1300 Pa) corresponding to POME.sub.2-3.

Synthesis Example 8

Preparation of a Mixture of Compounds POMM.SUB.3-5 .(n=3 to 5 and RR=Methyl)+POMM/E.SUB.2-4 .(n=2 to 4 and RR=Ethyl)+POMM/E.SUB.2-5 .(n=2 to 5 and R=Methyl and R=Ethyl) from a Methylal/Ethylal Reaction Mixture=75/25 in Moles

[0068] In a 1 L double-jacketed Schott reactor equipped with a mechanical stirrer, a condenser and a temperature probe, 271 g of methylal (3.57 mol), 122 g of ethylal (1.17 mol) and 107 g of trioxane (3.57 mol CH.sub.2O). 25 g of Amberlyst.sup.R A15 resin, previously washed with methanol and dried under vacuum, are added. The mixture is heated to 50 C. and allowed to react for 1 hour. The reaction mixture is filtered and then washed with 100 g of an aqueous solution of sodium hydroxide at 15% by weight. The product is rectified by evaporation under reduced pressure on a rotary evaporator at 60 C. under 100 mbar (10,000 Pa).

[0069] 180 g of a mixture of compounds of formula: CH.sub.3(CH.sub.2O).sub.nOCH.sub.3 (n=3 to 8 or POMM.sub.3-8 (n=3 to 8 and RR=methyl) of formula C.sub.2H.sub.5(CH.sub.2O).sub.nC.sub.2H.sub.5 or POME.sub.2-8 (n=2 to 8 and RR=ethyl) and of formula CH.sub.3(CH.sub.2O).sub.nOC.sub.2H.sub.5 POMM/E.sub.2-8 (n=2 to 8 and R=methyl and R=ethyl), are obtained.

[0070] The product is then vacuum distilled using a scraped film evaporator under a vacuum of 1 mbar (100 Pa) at 90 C. 167 g of a mixture consisting essentially of compounds of formula: CH.sub.3(CH.sub.2O).sub.nOCH.sub.3 (n=3 to 5 or POMM.sub.3-5 (n=3 to 5 and RR=methyl), of formula C.sub.2H.sub.5(CH.sub.2O).sub.nC.sub.2H.sub.5 or POME.sub.2-8 (n=2 to 4 and RR=ethyl) and of formula CH(CH.sub.2O).sub.nOC.sub.2H.sub.5 POMM/E.sub.2-5 (n=2 to 5 and R=methyl and R=ethyl).

[0071] The statistical distribution of the masses of the mixture obtained is determined by GC analysis as shown in Table 4. Table 4 groups the compositions and molecular distributions as a function of n (determined by GPC) for all the POM products prepared in the synthesis examples 1 to 7 described above.

Synthesis Example 9

Preparation of POMM.SUB.3-4 .with n=3 to 4 and RR=Methyl, by Recycling Distillation Heads and Feet of Synthesis Examples 2 and 3

[0072] In a 1 L double-jacketed Schott reactor equipped with a mechanical stirrer, a condenser and a temperature probe, 100 g of methylal (also called dimethoxymethaneCH.sub.3OCH.sub.2OCH.sub.3) (1.32 mol) and 30 g of trioxane (1 mol CH.sub.2O). The heads of the evaporation of Example 2, i.e. methylal and POMM2, are added after removing the water contained therein by drying over magnesium sulphate. The foot of the distillation of Example 3 is also added.

[0073] 10 g of Amberlyst A15 resin, previously washed with methanol and dried under vacuum, are added. The mixture is heated to 50 C. and allowed to react for 1 hour. The reaction mixture is filtered and then washed with 10 g of 15% aqueous sodium hydroxide solution. The methylal is removed by evaporation under reduced pressure (90 C., 650 mBar (65,000 Pa) measured at the evaporator) on a rotary evaporator, then the POMM.sub.2 and the residual water are then removed by vacuum distillation. (Oldershaw type column with 10 trays) operating at a pressure of 200 mBar (20,000 Pa) at 90 C. 60 g of a cut POMM.sub.3-8 (CH.sub.3OCH.sub.2OCH.sub.3), where n is 3 to 8, are obtained.

[0074] On the product obtained, the distillation cut is collected between 60 C. under 65 mbar (6500 Pa) and 90 C. under 10 mbar (1000 Pa) corresponding to POMM.sub.3-4, where n is 3-4.

POMM Characteristics of Synthesis Examples 1 to 4 and 9

[0075]

TABLE-US-00002 TABLE 2 Synthesis POMM n = 3-5 examples composition n = 2% n = 3% n = 4% n = 5% (n = 3-4) % n < 3% n > 5% Synthesis POMM.sub.2-8 48% 33% 12% 4% 49 (45) 48 3% example 1 Synthesis POMM.sub.3-8 47% 29% 14% 90 (76) 0 10% example 2 Synthesis POMM.sub.3-4 62% 37% 1% 100 (99) 0 0 example 3 Synthesis POMM.sub.3-5 55% 32% 13% 100 0 0 example 4 Synthesis POMM.sub.3-4 60% 38% 2% 100 (98) 0 0 example 9 The % s reported are percent areas of the chromatography peaks comparable to % by weight.

POME Characteristics of Synthesis Examples 5 to 7

[0076]

TABLE-US-00003 TABLE 3 POMM Synthesis composition n = 2-4 examples POME n = 2% n = 3% n = 4% n = 5% (n = 2-3) n < 2% n > 5% Synthesis POME.sub.2-8 48 30 13 6 91 (78) 0 3 example 5 Synthesis POME.sub.2-4 56 30 13 1 100 (86) 0 0 example 6 Synthesis POME.sub.2-3 61 38 1 100 (99) 0 0 example 7 The % s reported are percent areas of the chromatography peaks comparable to % by weight.

POMM/POME and POMM/E Blend Characteristics of Synthesis Example 8

[0077]

TABLE-US-00004 TABLE 4 Relative distribution POMM, POME in the respective Synthesis and POMM/E POMM, POME and examples composition n = 2% n = 3% n = 4% n = 5% POMM/E families Synthesis POMM.sub.3-5 0 22 11 5 n = 3 5: 100% rel example 8 n = 3 4: 86.8% rel POME.sub.2-4 4 2 1 0.3 n = 2 4: 95.9% rel, n > 4: 4.1% n = 2 3: 82.2% rel POMM/E.sub.2-5 27 15 7 2.5 n = 2 5: 100% rel n = 2 4: 95.2% rel The % s reported are percent areas of the chromatography peaks comparable to % by weight.

Application Examples of Embalming/Preservation Compositions

[0078] The application examples were made following the application guide Transitional Guidance on the Biocidal Products Regulation. Transitional Guidance on Efficacy Assessment for Product; Type 22 Embalming Products, of August 2014, Published by ECHA.

Application Example 1 (Comparative Outside the Invention)

[0079] 900 g of POMM.sub.2-8 of Synthesis Example 1 and 100 g of 1,2-propanediol (propylene glycol) are mixed.

[0080] 200 ml of the mixture diluted in 4.3 liters of water are injected with an electric pump, into the femoral artery of the mortal remains of a woman of 50 kg, then 500 ml of the mixture is injected into a cavity. The total volume drained during arterial injection is 3 liters. The diffusion of the product in the organism is excellent. During the operation, a slight solvent odor is noted by the operators. The skin appears hydrated and supple. After 4 days at room temperature, body preservation is good, and the suppleness and hydration of the skin are maintained.

[0081] After 10 days at room temperature, the preservation of the body is good, but it is observed that the skin is dry and rigid, especially in the nose. The product does not meet expectations.

Application Example 2 (Comparative Outside the Invention)

[0082] 300 ml of POMM-.sub.2-8 as produced according to the Synthesis Example 1 diluted in 7.2 liters of water are injected with an electric pump into the femoral artery of the mortal remains of a man of 80 kg, then 500 ml of POMM-.sub.2-8 are injected into a cavity. The total volume drained during arterial injection is 6 liters.

[0083] After 5 days at room temperature, body preservation is good. After 15 days at room temperature, there is a strong degradation of the body accompanied by unpleasant odors. The product does not meet expectations.

Application Example 3 (According to the Invention)

[0084] A mixture of a formulation containing POMM.sub.3-5 (4.8% by weight) of Synthesis Example 4, propane-1,2-diol (1.2% by weight), biocide, alkyl chloride (C12-16) dimethyl benzyl ammonium (ADBAC/BKC (C12-16)-CAS #68424-85-1 (1.5% wt) glycerin (3.7% by weight), a red-resin dye (2% by weight) and water to complete, are prepared.

[0085] A first solution of 1.5 liters of the formulation is prepared in 6 liters of water.

[0086] 5 liters of the aqueous solution are injected with an electric pump into the femoral artery of a mortal remains of a man of 83 kg, then again 2.5 liters of the solution. Then 500 ml of the formulation (containing the 4.8% by weight POMM) is injected into a cavity. The total volume drained during arterial injection is 6 liters.

[0087] After 4 days at room temperature, body preservation is good; no swelling is observed. After 10 days at room temperature, body preservation is good, no odor is detected. After 15 days at room temperature, a dissection is performed by the doctors, the muscles were well colored, no odor. The doctor did not notice any difference with a dead body just deceased. Sampling by doctors of the liver, which was found to be of good quality. The other organs were well preserved. The suppleness of the body gives the appearance of a body not embalmed and recent, appreciated for the practical work of surgery.

Conditions of Application Examples 1 to 3

[0088]

TABLE-US-00005 TABLE 5a Injection/ Refrig- C = Carotid: Application Sex/Age Estimated Adiposity erated Whole F = Femoral: Arterial Cavity example (years) weight (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 1 F 50 nr nr nr nr F/electrical 4.4% by 0.5 L 3 L HI weight POMM in 4.3 L 2 H 80 Average Average Yes yes nr 4% by 0.5 L 6 L HI weight POMM2-8 in 7.2 L 3 H 83 Average Average 24 hr yes C-D + F-D/ 7.5 L @ 0.5 L 6 L electrical 20% Vol nr = not reported; HI = outside invention; H: Man; F: Woman; F-D: right femoral; F-G: left femoral; C-D: right carotid, C-G: left carotid;/electric: electric pump./manual: manual pump

Results of Application Examples 1 to 3

[0089]

TABLE-US-00006 TABLE 5b Application Observation at treatment Observation Observation Observation example Before After at 2 days at 5 days at 15 days 1 - outside Odor Good Odor of Good Good Bad invention solvent Coloring Good Good Good Good Bad Skin Good Good Good Good Acceptable suppleness 2 - outside Odor Acceptable Good - Odor of Good Good Bad invention solvent Coloring Acceptable Good Acceptable Acceptable Bad Skin Good Good Good Good Acceptable suppleness 3 Odor Good Good Good Good Good Coloring Good Good Good Good Good Skin Good Good Good Good Good suppleness

Application Example 4 (Comparative, Outside the Invention)

[0090] Preparation of a mixture of a formulation containing POMM.sub.3-8 (9.0% by weight) of Synthesis Example 2, propane-diol-1.2 (1.2% by weight), biocide alkyl chloride (C12-14) dimethyl benzyl ammonium CAS #85409-22-9 (1.5% by weight), borax Na.sub.2B.sub.4O.sub.7 (0.4% wt), red dye (2% by weight) and water to complete. It is found that the product of the water-POMM.sub.3-8 mixture is not clear. When the final mixture is exposed to cold (+1 C.) flakes form which settle in the bottom of the flask. The product is therefore not stable and therefore not in line with expectations.

[0091] A first solution of 1.8 liters of the formulation is prepared in 7.2 liters of water.

[0092] 9 kg of the aqueous solution is injected with a manual pump into the right and left carotid of the mortal remains of a man weighing 60 kg. 500 ml of the pure formulation are then injected in a cavity. The total volume drained during arterial injection is 5 liters.

Conditions of the Application Example 4

[0093]

TABLE-US-00007 TABLE 6a Estimated Injection/C = Carotid; Application Sex/Age weight Adiposity Refrigerated Whole F = Femoral; Arterial Cavity example (years) (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 4 H/40 60 Average Low 24 hr yes C D + 9 L (at 0.5 L 5 L G/manual 20% vol) pure.

[0094] Preservation after 15 days is not good. There are significant odors (see Table 6b).

Results of Application Example 4

[0095]

TABLE-US-00008 TABLE 6b Observation at treatment Observation Observation Observation before after at 2 days at 5 days at 15 days 4 Odor Good Good Good Good Bad Coloring Good Good Good Good Acceptable Skin Good Good Good Good Good suppleness

Application Example 5 (According to the Invention)

[0096] Preparation of a mixture of a formulation containing POMM.sub.3-4 (4.8% by weight) of Synthesis Example 3, propanediol-1.2 (1.2% by weight), alkyl chloride (C12-18) dimethyl benzyl ammonium (ADBAC (C12-18)) CAS #68391-01-5 (1.5% by weight), potassium nitrate (0.3% by weight) red dye (2% by weight) and water to complete.

[0097] A first solution of 1.5 liters of the formulation is prepared in 7.5 liters of water.

[0098] 6 liters of the aqueous solution are injected with a manual pump into the right carotide of the mortal remains of a woman of 75 kg, then again 3 liters of the solution. 500 ml of the pure formulation are then injected in a cavity. The total volume drained during arterial injection was not reported.

Conditions of Application Example 5

[0099]

TABLE-US-00009 TABLE 7a Application Estimated Injection/C = Carotid; example Sex/Age weight Adiposity Refrigerated Whole F = Femoral; Arterial Cavity appli (years) (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 5 F/90 75 Average Average 24 hr yes C D/manual 9 L (at 0.5 L nr 17% vol)

[0100] Preservation after 15 days is excellent (see Table 7b).

Results of Application Example 5

[0101]

TABLE-US-00010 TABLE 7b Application Observation at treatment Observation Observation Observation Example Before After at 2 days at 5 days at 15 days 5 Odor Acceptable Good Good Good Good Coloring Acceptable Good Acceptable Acceptable Acceptable Skin suppleness Good Good Good Good Good

Application Example 6 (Comparative Outside the Invention)

[0102] Preparation of a mixture of a formulation containing POME.sub.2-8 (6% by weight) of Synthesis Example 5, propanediol-1.2 (1.2% by weight), alkyl chloride (C12-14) dimethyl ethyl benzyl ammonium (ADEBAC (C12-14)) CAS #85409-23-0 (1.5% by weight), perfume (0.1% by weight), glycerin (3% by weight), a red dye (2% by weight) and water to complete. When the product is exposed to cold (+1 C.), a haze is formed, and a material in suspension settles towards the bottom of the flask. The product is therefore not stable and is not in line with expectations.

[0103] A first solution of 1.6 liters of the formulation is prepared in 6.4 liters of water.

[0104] 6 liters of the aqueous solution are injected with an electric pump into the right and left carotid of the mortal remains of a man of 120 kg, then again 2 liters of the solution. Then 1000 ml of the pure formulation is injected in a cavity. The total volume drained during arterial injection is 6 liters.

Conditions of Application Example 6

[0105]

TABLE-US-00011 TABLE 8a Estimated Injection/C = Carotid; Application Sex/Age weight Adiposity Refrigerated Whole F = Femoral; Arterial Cavity example (years) (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 6 H 120 strong average yes yes C D + 8 L (@ 1 L 6 L G/electric 20% vol)

[0106] Preservation after 15 days is not acceptable. Color and body flexibility are severely degraded (see Table 8b).

Results of Application Example 6

[0107]

TABLE-US-00012 TABLE 8b Application Observation at treatment Observation Observation Observation example before after at 2 days at 5 days at 15 days 6 Odor Good Good Good Good Acceptable Coloring Acceptable Good Good Acceptable Bad Skin Good Good Good Acceptable Bad suppleness

Application Example 7 (According to the Invention)

[0108] Preparation of a mixture of a formulation containing POME.sub.2-4 (4.8% by weight) of Synthesis Example 6, propanediol-1.2 (1.2% by weight), alkyl chloride (C12-C16) dimethyl benzyl ammonium (ADBAC/BKC (C12-16)) CAS #68424-85-1 (1.5% by weight), borax (0.5% by weight), red dye (2% by weight) and water to complete.

[0109] A first solution of 1.5 liters of the formulation is prepared in 4.5 liters of water.

[0110] 4 liters of the aqueous solution are injected with a manual pump into the right carotid artery and into the right femoral artery of the mortal remains of a 95 kg woman, then again 2 liters of the solution. 500 ml of the pure formulation are then injected in a cavity. The total volume drained during arterial injection is not reported.

Conditions of the Application Example 7

[0111]

TABLE-US-00013 TABLE 9a Estimated Injection/C = Carotid; Sex/Age weight Adiposity Refrigerated Whole F = Femoral; Arterial Cavity (years) (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 7 F/90 95 Strong Significant 48 hr yes C D + 6 L (@ 0.5 L nr F D/manual 17% vol)

[0112] Preservation after 15 days is good (see Table 9b).

Results of Application Example 7

[0113]

TABLE-US-00014 TABLE 9b Application Observation at treatment Observation Observation Observation example Characteristic before after at 2 days at 5 days at 15 days 7 Odor Good Good Good Good Good Coloring Acceptable Acceptable Acceptable Acceptable Acceptable Skin suppleness Good Good Good Acceptable Acceptable

Application Example 8 (According to the Invention)

[0114] A mixture of a formulation containing POME2-3 (4.8% by weight) of Synthesis Example 7, propane-1,2-diol (1.2% by weight), alkyl chloride (C.sub.12-C.sub.16) dimethyl benzyl ammonium (ADBAC/BKC (C12-16)) CAS #68424-85-1 (1.5% by weight), borax (0.5% by weight), red dye (2% by weight) and water to complete.

[0115] A first solution of 1.5 liters of the formulation is prepared in 7.5 liters of water.

[0116] 6 liters of the aqueous solution are injected with a manual pump to the right carotid artery and into the right femoral artery of the mortal remains of a man of 95 kg, then again 3 liters of the solution. Then, 500 ml of the pure formulation are injected in a cavity. The total volume drained during arterial injection has not been reported.

Conditions of Application Example 8

[0117]

TABLE-US-00015 TABLE 10a Application Estimated Injection/C = Carotid; example Sex/Age weight Adiposity Refrigerated Whole F = Femoral; Arterial Cavity appli (years) (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 8 H 95 Strong Average yes yes C D + F D/manual 9 L (@ 0.5 L nr 17% vol)

[0118] Preservation of the body after 15 days is good (see table 10b).

Results of Application Example 8

[0119]

TABLE-US-00016 TABLE 10b Application Observation at treatment Observation Observation Observation Example Characteristic before after at 2 days at 5 days at 15 days 8 Odor Good Good Good Good Good Coloring Acceptable Acceptable Acceptable Acceptable Acceptable Skin Good Acceptable Acceptable Acceptable Acceptable suppleness

Application Example 9 (According to the Invention)

[0120] Preparation of a mixture of a formulation containing a mixture of POMM.sub.3-5, POME.sub.2-4 and POMM/E.sub.2-5 (4.8% by weight) of Synthesis Example 8, propane-1,2-diol (1.2% by weight), alkyl chloride (C12-C16) dimethyl benzyl ammonium (ADBAC/BKC (C.sub.12-16)) CAS #68424-85-1 (1.5% by weight), borax (0.5% by weight), a red dye (2% by weight) and water to complete.

[0121] A first solution of 1.5 liters of the formulation is prepared in 7.5 liters of water.

[0122] 6 liters of the aqueous solution are injected into the right and left carotid artery of the mortal remains of a man, then again 3 liters of the solution. 500 ml of the pure formulation are then injected in a cavity. The total volume drained during arterial injection is 7 liters.

Conditions of Application Example 9

[0123]

TABLE-US-00017 TABLE 11a Application Estimated example Sex/Age weight Adiposity Refrigerated Whole Injection/C = Carotid; Arterial Cavity appli (years) (Kg) Corpulence level body body F = Femoral; fluid treatment Drainage 9 H 90 Average Average yes yes C D + 9 L 0.5 L 7 L G/nd (@17% vol)

[0124] After 15 days, body preservation is good (see Table 11 b).

Results of Application Example 9

[0125]

TABLE-US-00018 TABLE 11b Application Observation at treatment Observation Observation Observation Example Characteristic Before after at 2 days at 5 days at 15 days 9 Odor Acceptable Acceptable Acceptable Acceptable Acceptable Coloring Bad Good Good Acceptable Acceptable Skin suppleness Acceptable Good Good Good Good

Application Example 10 (According to the Invention)

[0126] Preparation of mixture of a formulation containing POMM3-4 (4.8% by weight) of Synthesis Example 9, propanediol-1.2 (1.2% by weight) of the alkyl chloride (C.sub.12-C.sub.16) dimethyl benzyl ammonium (ADBAC/BKC (C.sub.12-C.sub.16)) CAS #68424-85-1 (1.5% by weight), borax (0.5% by weight), red dye (2% by weight) and water to complete.

[0127] A first solution of 1.5 liters of the formulation is prepared in 7.5 liters of water.

[0128] 6 liters of the aqueous solution are injected with a manual pump into the right and left carotid artery of the mortal remains of a man of 80 kg, then again 3 liters of the solution. 500 ml of the pure formulation are then injected in a cavity. The total volume drained during arterial injection is 6 liters.

Conditions of the Application Example 10

[0129]

TABLE-US-00019 TABLE 12a Application Estimated Injection/C = Carotid; example Sex/Age weight Adiposity Refrigerated Whole F = Femoral; Arterial Cavity appli (years) (Kg) Corpulence level body body A = Axillary fluid treatment Drainage 10 H/90 80 Average Average 24 hr yes C D + 9L (@ 0.5 L 6 L G/manual 17% vol)

[0130] After 15 days, the body preservation is good (see Table 12b).

Results of Application Example 10

[0131]

TABLE-US-00020 TABLE 12b Application Observation at treatment Observation Observation Observation example Characteristic before after at 2 days at 5 days at 15 days 10 Odor Acceptable Good Good Good Good Coloring Acceptable Good Acceptable Acceptable Acceptable Skin suppleness Good Good Good Acceptable Acceptable