US3759806A - Preparation of perfumes and similar products - Google Patents

Preparation of perfumes and similar products Download PDF

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Publication number
US3759806A
US3759806A US00070933A US3759806DA US3759806A US 3759806 A US3759806 A US 3759806A US 00070933 A US00070933 A US 00070933A US 3759806D A US3759806D A US 3759806DA US 3759806 A US3759806 A US 3759806A
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perfume
present
perfumes
alcohol
actinic radiation
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H Doctor
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R D T INTERNATIONAL INC US
RDT INT Inc
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RDT INT Inc
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/022—Refining

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  • FIG. 1 PREPARATION OF PERFUMES AND SIMILAR PRODUCTS Filed Sept. 9, 1970 4 Sheets-Sheet 1 FIG. 1
  • FIG. 5 PREPARATION OF PERFUMES AND SIMILAR PRODUCTS Filed Sept. 9, 1970 4 Sheets-Sheet 3 FIG. 5
  • This application is directedto a method of improving the properties of perfumes and other toilet or cosmetic preparations; more particularly, the present invention is directedto a method of improving the characteristics of perfumes, including the staying power, by treating the perfume or its component parts with actinic radiation.
  • a perfume may be said to consist of three parts: the odoriferous or fragrance-imparting part, the fixative part and the diluent.
  • the odoriferous component serves to impart the odor or fragrance to the perfume.
  • consideration must be given to the intensity of its odor, and sufficient odoriferous constituents are employed to impart the desired fragrance to the final blend.
  • the percentage composition of a perfume may indicate a component to be present in rather minor quantity, its contribution to the fragrance of the finished product may be quite dominant.
  • the fixative serves primarily to control the degree of volatilization of the different, more or less volatile components of the perfume. In some instances these materials may possess their own distinctive odors and contribute as well to the emergent odor. Because of this, a given perfume type :may require a particular fixative which may not be suitable for a perfume of another type.
  • the function of the perfume diluent or solvent is primarily that of reduction and masking of odor of the blend and in a smaller measure to contribute to the odor of the final product. While various perfume diluents and solvents can be employed, a particularly useful diluent is an aliphatic alcohol, particularly ethyl alcohol. Accordingly, it has been with respect to such perfumes employing such alcoholic bases that considerable research has been conducted in the manner by which such perfumes can be improved so as to increase the lasting or staying properties of the perfume while creating suflicient body in the toilet preparation.
  • the perfume or similar cosmetic or toilet preparation can be improved with respect to its body, staying power and masking of odor by contacting the perfume or its component parts, i.e., solvent or diluent, or solvent or diluent combined with the odiferous or fragrant imparting essences, with actinic radiation for a period of time sufficient to alter the characteristics of the perfume.
  • a substantial improvement in the characteristics of the perfume or similar cosmetic or toilet article can be produced by subjecting the perfume or its component parts to the action of actinic light within the wave length range of from about 3900 to 4800 A.
  • a still further object of the present invention relates to a process for, improving the properties of perfumes and similar toilet and cosmetic articles having an alcoholic base wherein such improvement is associated with contacting such products or component parts thereof with actinic radiation within the wave length region of 3900 to 4800 A.
  • the aforementioned objects and advantages of the of the novel process of the present invention are achieved by contacting the perfume or similar toilet or cosmetic preparation or its component parts with actinic radiation within the wavelength range of 3900 to 4800 A. It is within this wave length range that the treatment of the perfume or its component parts, principally the alcoholic diluent or solvent, provides for an alteration in the character of the preparation so as to allow for enhanced body, greater lasting power, decreased solvent flash-back and a general accelerated maturing or aging of the product. In this later regard, it is pointed out that the best perfumes are generally allowed to age or mature by standing and storage for a limited period of time so as to create a well rounded and full bodied character. The treatment in accordance with the present invention has been found to provide an acceleration of such natural maturing or aging without any prolonged storage or standing period through the action of actinic radiation.
  • the process of the present invention can be carried out by contacting the perfume or its constituents with actinic radiation within the wave length region as set forth above.
  • either the final perfume consisting of the essences and solvent or diluents may be subjected to the reaction of the light or something less than the final perfume can be subjected to such radiation.
  • the solvent or diluent alone i.e., ethyl alcohol or similar material to the action of actinic radiation or a combination of such solvent and diluent with one or more essences making up a portion of the final perfume.
  • the process of the present invention is conducted with respect to the solvent or diluent alone, the solvent or diluent in admixture with one or more essences making up a small portion of the whole, or with respect to the entire final perfume or similar cosmetic or toilet product, the effect is the same, that is, the treatment in accordance with the present invention provides for a product having a more rounded body, greater lasting power, and other characteristics associated with the finest matured and aged products.
  • a good perfume should have an agreeable top note, that is, a scent fraction that in a profusive way properly penetrates the surrounding environment largely for the purpose of calling attention to'its pres once, or, more precisely, the presence of its wearer.
  • body that is, possess a quality of substance rather than being weak and insipid. It should diffuse in an even note, that is, the scent characteristics should not change significantly as the perfume is diluted by the atmosphere.
  • both the middle note and end note should be pleasant, that is, the less volatile fractions which appear after the perfume has been exposed to the atmosphere for a time should be perfumes of quality in themselves, although it is not necessary, or even desirable, that these later notes have the exact characteristics of the top note.”
  • a good perfume must have an extended lasting power so that its fragrance does not quickly disappear.
  • the treatment in accordance with the process as described above is not substantially dependent upon the type or nature of the essence employed in the production of the perfume.
  • the essence if of a natural or synthetic character the same does not appear to be in any way deteriorated or reduced in quality to the process of the present invention and, in fact, it is hypothesized that many of the essences conventionally employed in the production of perfumes have their odors improved through the treatment to which the perfume or substituent is subjected.
  • the perfume upon which the process of the present invention is conducted may contain any suitable conventionally employed essence of a natural or synthetic character either raw or extracted and with or without the medium by which such essences are extracted.
  • specific representative essences which are conventionally employed in the production of perfumes include such as: the flower oils, such as rose and jasmin; the essential oils, such as oil of geranium and oil of bergamot; the citrus oils; ambergris; aleo resins extracted from beaver pods and civet as well as the various derivatives and products of refinement, such as rhodinol' from geranium bourbon, geraniol from the citronellas, linalool from bois de rose Cayenne, and many others.
  • a suitable jasminefragrance may comprise the following components: I JASMINE FRAGRANCE Benzyl acetate Benzyl alcohol Linalool Linalyl acetate Terpineol Amyl cinnamic aldehyde Cyclamen aldehyde Ylang ylang oil Benzyl salicyclate 2-nonynal dimethyl acetal 'Phenyl ethyl alcohol Decyl aldehyde Ehenyl acetaldehyde I Methyl ionone ,Iso-cyclo icitral V 2 nonynal dimethyl acetal Citronellol ,R Geraniol Phenyl ethyl alcohol 7 Nerol j 'Methylionone Phenylacetic acid (10% strength) Phenylacetaldehyde 10% strength) Diisopropylpyrocatechol ketal Nonyl aldehyde (10% strength) In a. likemanner, a suitable
  • the time of subjecting the perfume or its component parts to the actinic radiation is from a period of from about 2 seconds to about 30 seconds.
  • the time period and within the wave length region set forth above it has been found possible to improve the characteristics of the perfume in a manner in which it was heretofore impossible with previous processes.
  • the intensity of the light incident upon the perfume or its component parts may to some extent effect the characteristics of the final product and the extent to which the same are effected by the treatment of the present invention.
  • the light incident upon the perfume or its component parts should be within the range of 2 10 to 5 X10 quanta/secJcmF. It is within this intensity and the above noted wave length region that it has been found possible to irradiate the perfume or its component parts in order to provide a product having greater body, less alcohol flash-back, a longer staying power and an artifically matured or aged character.
  • the time or period of irradiation is inversely proportional to the intensity of the actinic light incident upon the perfumed! its component parts.
  • the intensity of light can be at or near the minimum level described aboveQit'being inversely true that if a short or minimum period of irradiation is employed, the intensity of the light incident upon the perfume or its component parts can be or should be at the maximum level.
  • the temperature of the perfume or its component part does not, to any extent, effect the treatment to which the perfume is subjected. Accordingly, when passing the perfume or its component parts in contact with the actinic radiation, the perfume can be at room or elevated temperatures or slightly chilled depending upon the various conditions employed in production. In this regard, temperature is found to be a noncritical characteristic of the process of the present invention which need not be controlled to any great extent.
  • the process of the present invention is conducted by passing the perfume or its component parts through an apparatus adapted to subject the perfume to the action of actinic light for a time period and an intensity as described above.
  • an apparatus for irradition through which a liquid can be passed and forced to follow a tortuous path so that the liquid is irradiated as a thin film of, for example, 2-50 mm. in thickness.
  • Such an apparatus can be advantageously employed in accordance with the process of the present invention by which the perfume or its components are irradiated with actlnic light by one or more passes of the same before the light source. It is, of course, obvious that other equivalent apparatus capable of subjecting the perfume or its component parts to the action of actinic light as afore described can be advantageously employed in accordance with the instant process.
  • the effects of the process of the present invention are most pronounced when the solvent employed in the production of the perfume is an alcohol, primarily ethyl alcohol. It should be pointed out, however, that where other diluents or solvents are employed in addition to ethyl alcohol or in lieu of ethyl alcohol, the same type of improvement is seen to exist. This is apparently due to the fact that the irradiation of the perfume or its component parts acts to accentuate the relationship between the essences and the solvents or diluents, such that a final product is produced having a fuller body and a longer staying power.
  • the process of the present invention is applicable to colognes, toilet waters, after shave lotions, bath oils, deodorants, hair and scalp preparations and other fragrances employed for cosmetic or toilet purposes.
  • the expression perfume is meant to embrace any and all such preparations which, owing to the presence of a diluent and solvent and essence, can be effectively treated in accordance with the instant process.
  • the process of the present invention can be conducted with regard to the diluent portion, the essences, or the final perfume it ispreferred in accordance with the present invention to treat the diluent or solvent fraction e.g., ethyl alcohol prior to combining the same with the essences or oils in the production of the final perfume product.
  • the solvent or diluent portion prior to compounding it is possibleto further accentuate the improvement in the longer staying power, elimination of the flash back and alcohol odor and other general characteristics of the perfume product. Accordingly, such treatment of the diluent or solvent fraction in accordance with the present invention constitutes a preferred embodiment of the instant process.
  • the principal component of the diluent or solvent portion of a perfume, toilet water, cologne, deodorant or similar cosmetic or toilet preparation constitutes ethyl alcohol.
  • the ethyl alcohol that is generally utilized in the solvent or diluent portion of the perfume, etc. generally comprises one of many denatured ethyl alcohols which have been specifically formulated for per fumes and other similar products;
  • suitable denatured alcohols which have been specifically designated for use in perfumes and similar products include such materials as SDA 38-B, SDA 39, SDA 39-B, SDA 39-C, SDA 40 and SDA 40-A.
  • denatured alcohols are prepared by adding to the ethyl alcohol a specifically defined amount of a denaturantso that the ethyl alcohol is no longer fit for internal consumption.
  • denatured alcohol is prepared by adding to every gallons of ethyl alcohol 10 pounds of a specifically defined oil.
  • SDA 39 is prepared by adding to every 100 gallons of ethyl alcohol 9 pounds of sodium salicylate or salicylic acid, 1.25 gallons fluid extract of quassia and gallon of tert-butyl alcohol.
  • SDA 39-B is prepared by denaturing every 100 gallons of ethyl alcohol with two and one-half gallons of diethyl phthalate and gallon of tert-butyl alcohol.
  • SDA 39-C is prepared by denaturing every 100 gallons of ethyl alcohol with one gallon of diethyl phthalate while SDA 40 is prepared by adding to every 100 gallons of ethyl alcohol one and one-half ounces of brucine or brucine sulfate or quassin or one and one-half ounces of the foregoing and /8 gallon of tert-butyl alcohol.
  • SDA 40-A is prepared by denaturing every 100 gallons of ethyl alcohol with one pound of sucrose octaacetate and A; gallon of tert-butyl alcohol.
  • denatured alcohol preparations are specifically suitable for use in perfumes
  • other toilet preparations can be provided by the use of other conventional denatured alcohols.
  • deodorants can be prepared utilizing SDA 23-A
  • hair and scalp preparations can be produced utilizing an alcohol system such as SDA 3-B, SDA 23-F, SDA 23-H, SDA 37, SDA 39-D etc.
  • shampoos and similar preparations can be produced from denatured alcohol systems such as SDA 3-A, SDA 3-B, SDA 23-A, SDA 27-B, SDA 31- A, SDA 36 etc.
  • the present invention is applicable to other synthetic alcohols as Well as fermentation alcohols utilized in the production of perfumes and similar cosmetic and toilet preparations. Accordingly the treatment of alcohols, specifically ethyl alcohol through radiation with actinic light in the wave region of 3900 to 4800 A. constitutes a specific preferred embodiment of the present invention, when such alcohols are later utilized as the solvent or diluent portion of a perfume, toilet water, cologne, deodorant, bath oil or similar cosmetic and toilet preparation.
  • any of the aforementioned denatured alcohols or ethyl alcohol derived from sugar, corn etc. i.e., naturally fermented alcohol or a synthetic alcohol made from petro chemicals can be advantageously utilized. It is often preferred to employ fermentation alcohols in such products as colognes and toilet waters since the odor of the synthetic alcohols is not considered equal to the fermentation ethyl alcohol.
  • the use of the treatment with actinic light within the wave length region of 3900 to 4800 A. allows for the production of synthetic alcohols which have less flash back and alcohol odor. Accordingly through the process of the present invention any of the conventional alcohol materials can be advantageously utilized in the production of a superior perfume or similar toilet preparation.
  • perfume extracts does not usually present much difficulty and, in fact, various methods have been developed to obtain clear products having acceptable olfactory characteristics. In preparing such products, it is the general practice to follow a few well recognized steps. In this regard, for the preparation of perfume extracts, it is customary to employ a 95% alcohol solvent and an 80% to 95% solvent for toilet waters etc. In such alcohol, perfume oils are usually soluble in all proportions. In this regard it has been found that the quality of the alcohol plays an important role in the characteristics of the perfume, it generally being necessary to choose an alcohol entirely devoid from any foreign odor and denatured with an odorless substance.
  • the amount of perfume oils employed in the perfume extracts varies between 150 to 200 grams per liter of solution and from 30 to 50 grams per liter of solution in toilet waters. It is, of course, obvious that slightly greater or lesser amounts of the perfume oils can be employed depending upon the strength of the essence and desired product etc.
  • a suitable perfume extract may-be prepared by the addition of about 18% perfume oil and an alcohol of 95%.
  • perfume oil may be added to an 80% alcohol while for the production of a masculine toilet water, 3% of the perfume may be added to the alcohol.
  • Such amounts are only exemplary and do not form a portion of the present invention which, as indicated previously is concerned with the treatment of any and all perfumes and similar products and component parts thereof with actinic radiation under the conditions described above.
  • the mix ture of perfume oils is generally first prepared and allowed to stand for a period of 48 hours or longer. Such perfume oils are poured into the alcohol solvent or diluent and stirred.
  • the solution of perfume oils in alochol is kept for at least 3 months in a hermetically closed vessel so that the alcohol does not evaporate, with shaking from time to time. During this period of standing, the product will mature and the waxes or resins which are only slightly soluble in the alcohol will be deposited. It is this standing for at least 3 months effecting a maturation of the perfume or similar product which can be reduced somewhat in accordance with the present invention in that an artificial maturing or aging of the product is produced through the treatment with actinic radiation.
  • a filtering aid can be used to assist in the removal of the waxes and resins. It is noted, however, that certain filtering aids tend to absorb certain constituents of the perfume oils and thus, under some conditions, may alter the olfactory characteristics of the extract. After filtering the solution of perfume oils, it is again brought to normal room temperature and poured into suitable containers for sale.
  • the process of the present invention can be carried out on the alcohol alone, on the perfume oils alone, on a mixture of one or more perfume oils or extracts with the solvent or diluent, or on the total perfume prepared after addition of all perfume oils and essences to the solvent.
  • the treatment of the perfume or its component parts with actinic radiation under the conditions described above effects the advantages set forth previously with respect to the production of a product having a fuller body with less solvent flash-back etc.
  • EXAMPLE 1 In order to determine the effectiveness of the process of the present invention in altering and ameliorating the olfactory characteristics of perfumes and similar products various commercial perfumes were subjected to irradiation in accordance with the present invention.
  • the perfumes were passed through apparatus such as described in the US. Pat. 3,037,116 for periods of time ranging from 30 seconds to 30 minutes. After subjecting the perfumes to the treatment with actinic radiation within the wavelength region of 3900 to 4800 A; the perfumes were analysed by a gas chromatogram and physically observed by those skilled in noting differences in perfumes and other fragrances.
  • the gas chromatographic analysis of the samples, both treated and untreated, were made so as to obtain an indication of the chemical change effected through the treatment of the perfume in accordance with the present invention.
  • the analyses were made by passing the treated and untreated perfumes through a column 6 feet long and having an inside diameter of Mt mm. A helium carrier gas was employed and the temperature of the column was maintained at 150 to 200 C. with a detector maintained at a temperature of 275 C.
  • Such apparatus was a conventional gas chromatogram.
  • the perfumes subjected to the process of the present invention were:
  • FIGS. 1 through 8 The gas chromatograms resulting from the analyses of the untreated and treated perfumes are shown in FIGS. 1 through 8.
  • FIG. 1 is the gas chromatogram of a natural Dunhill perfume not subjected to the process of the present invention
  • FIG. 2 is a gas chromatogram of the same Dunhill perfume after being subjected to the action of actinic radiation for a period of 30 seconds;
  • FIG. 3 is a gas chromatogram of a natural Arpege perfume not subjected to the process of the present invention
  • FIG. 4 is a gas chromatogram of the same perfume after having been subjected to the action of actinic radiation for a period of 10 minutes;
  • FIG. 5 is a gas chromatogram of natural My Sin perfume not subjected to the process of the present invention.
  • FIG. 6 is a gas chromatogram of the same perfume after having been subjected to the action of actinic radiation for a period of 30 seconds;
  • FIG. 7 is a gas chromatogram of the same My Sin perfume after having been. subjected to the action of actinic radiation for a period of minutes;
  • FIG. 8 is a gas chromatogram of the same My Sin perfume after having been subjected to the action of actinic radiation for a period of 30 minutes.
  • FIGS. 3 and 4 indicate that the relative intensities of peaks A and B have changed and that the relative intensities of peaks E and F have been reversed.
  • peaks C and D are seen to be With respect to FIGS. 7 and 8, similar changes can be noticed.
  • FIGS. 7 and .8 with FIG. 5, the gas chromatogram for the My Sin perfume not treated in accordance with the present invention.
  • the gas chromatograms merely fortify the observances of the samplers by showing that there are some definite chemical changes when the perfumes are treated with actinic radiation in accordance with the process of the present invention.
  • Example 2 The essences of Example 2 were employed to prepare perfumes, feminine toilet waters and masculine toilet waters utilizing the isopropyl alcohol subjected to treatment in accordance with the process of the present invention.
  • the extracts were employed in an amount of 18% in a 95% alcohol; or toilet waters, the essences were employed in an amount of in an 80% alcohol; and for masculine toilet waters, the essences were employed in an amount of 3% in an 80% alcohol.
  • EXAMPLE 4 Various commercial grade synthetic denatured alcohols were treated in accordance with the present invention by subjecting the same to actinic light within the wave length region of 3900 to 4800 A.
  • the alcohols that were utilized were those which contain 95% alcohol (5% water) and 100% alcohol.
  • the former group are designated as regular alcohols and the latter as anhydrous alcohols. All the untreated alcohol was stored in glass bottles and kept at room tempertaure and 5 different samples were treated by exposure to actinic light within the Wave length region of 3900 to 4800 A. for different time intervals.
  • Samples were run on SDA 40 alcohols and SDA 39-C alcohols, utilizing both the regular and anhydrous alcohols. Time exposures to the light was varied from 3 seconds to 30 seconds. Exposures were run at 3 seconds, 5 seconds, seconds, seconds, seconds, seconds and seconds. After being exposed to the actinic light an odor evaluation was conducted by direct application of the alcohol to a perfume blotter and by diluting the alcohol with distilled water in a ratio of 2:1 and evaluation in snifters.
  • a process for the treatment of a perfume comprising an essence portion and a denatured ethanol, so as to improve its olfactory characteristics, which process comprises subjecting said perfume, or a component part thereof, selected from the denatured ethanol alone or a mixture of the denatured ethanol and less than the total essence portion to actinic radiation from a lamp source, said radiation being within the wave length region of 3,900 to 4,800 A.
  • the final perfume is prepared by adding non-irradiated essence to the irradiated component.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
US00070933A 1970-09-09 1970-09-09 Preparation of perfumes and similar products Expired - Lifetime US3759806A (en)

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US (1) US3759806A (fr)
AU (1) AU2872171A (fr)
BE (1) BE772223A (fr)
DE (1) DE2144841A1 (fr)
ES (1) ES390072A1 (fr)
FR (1) FR2131204A5 (fr)
NL (1) NL7105166A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5342829A (en) * 1993-03-16 1994-08-30 Alan Kesten Diisopropyl adipate as a solvent for fragrance extracts
US20070125805A1 (en) * 2005-10-11 2007-06-07 Meadwestvaco Corporation Fragrance product, dispenser, and dispenser assembly
WO2017087258A1 (fr) * 2015-11-17 2017-05-26 The Procter & Gamble Company Procédé de fabrication de compositions de parfum
WO2021156213A1 (fr) 2020-02-04 2021-08-12 Clariant International Ltd Nanoparticules lipidiques permettant l'administration retardée d'un parfum ayant une solubilité améliorée dans l'eau, leur préparation et utilisation

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8802848A (nl) * 1988-11-18 1990-06-18 Naarden International Nv Werkwijze voor het bereiden van aroma- en reukstoffen.

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5342829A (en) * 1993-03-16 1994-08-30 Alan Kesten Diisopropyl adipate as a solvent for fragrance extracts
US20070125805A1 (en) * 2005-10-11 2007-06-07 Meadwestvaco Corporation Fragrance product, dispenser, and dispenser assembly
US20070125804A1 (en) * 2005-10-11 2007-06-07 James Thomson Fragrance product, dispenser, and dispenser assembly
US7718132B2 (en) 2005-10-11 2010-05-18 Meadwestvaco Calmar, Inc. Fragrance product, dispenser, and dispenser assembly
US7722819B2 (en) * 2005-10-11 2010-05-25 Meadwestvaco Calmar, Inc. Fragrance product, dispenser, and dispenser assembly
US20100219262A1 (en) * 2005-10-11 2010-09-02 Meadwestvaco Corp. Fragrance product, dispenser, and dispenser assembly
US8852528B2 (en) 2005-10-11 2014-10-07 Meadwestvaco Corporation Fragrance product, dispenser, and dispenser assembly
WO2017087258A1 (fr) * 2015-11-17 2017-05-26 The Procter & Gamble Company Procédé de fabrication de compositions de parfum
WO2021156213A1 (fr) 2020-02-04 2021-08-12 Clariant International Ltd Nanoparticules lipidiques permettant l'administration retardée d'un parfum ayant une solubilité améliorée dans l'eau, leur préparation et utilisation

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DE2144841A1 (de) 1972-03-16
FR2131204A5 (fr) 1972-11-10
ES390072A1 (es) 1973-06-01
NL7105166A (fr) 1972-03-13
BE772223A (fr) 1972-01-17
AU2872171A (en) 1972-11-16

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