US3060096A - Cosmetic preparation and process for manufacture thereof - Google Patents

Cosmetic preparation and process for manufacture thereof Download PDF

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Publication number
US3060096A
US3060096A US826923A US82692359A US3060096A US 3060096 A US3060096 A US 3060096A US 826923 A US826923 A US 826923A US 82692359 A US82692359 A US 82692359A US 3060096 A US3060096 A US 3060096A
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United States
Prior art keywords
lotion
gluconic acid
emulsion
lactone
skin
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Expired - Lifetime
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US826923A
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English (en)
Inventor
Wei Ling
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Colgate Palmolive Co
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Colgate Palmolive Co
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Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co
Priority to US826923A priority Critical patent/US3060096A/en
Priority to DEC21890A priority patent/DE1201951B/de
Priority to GB24221/60A priority patent/GB915816A/en
Priority to BE592913A priority patent/BE592913A/fr
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Publication of US3060096A publication Critical patent/US3060096A/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • This invention relates to a cosmetic for application to the human skin. More particularly the invention is a stable cosmetic emulsion of a degree of controlled acidity approximating that of normal human skin and possessed of substantial neutralizing power sufiicient to' return to its normal, acid condition skin that has become abnormally alkaline or acidic.
  • the controlled acidity of the emulsion and its desirable neutralizing power are attributable to a special buffering system comprising a water soluble ionizable inorganic gluconate salt and gluconic acid.
  • a process of making such a stable cosmetic emulsion is also included within the invention.
  • hand lotions are cosmetic products in which it is especially desirable to maintain an acidic pH.
  • the ordinary fatty acid soaps which are among the most frequently employed emulsifiers in the cosmetic art, are alkaline in solution and are considered unsuitable for use in acidic emulsions because they lose emulsifying power and break down to form water-insoluble fatty acids or acid soaps.
  • a stable acidic cosmetic emulsion preparation for the skin comprising an aqueous hydrophilic phase, with a lipophilic phase and an emulsifier to maintain said phases in stable emulsion form, the hydrophilic phase being at a pH above 3 and containing a minor proportion, in combination less than about 10% of the lotion,
  • gluconic acid and soluble metallic gluconate salt have greater neutralizing effect in such lotions with soaps, detergents, and other alkaline materials.
  • the gluconic acid is readily soluble in the aqueous phase of aqueous emulsions, is odorless and practicallly tasteless, is compatible with perfumes for cosmetics, its sequestration of traces of heavy metals also aiding in stabilizing the perfumes and cos metic ingredients, and-perhaps most important, it isstable in a wide variety of cosmetic emulsions.
  • gluconic acid in the present hand 10- tion enables that lotion to exert a considerable neutralizing effect on skin that has become basic due to contact
  • a major function of these hand lotions is to counteract alkalinity, but the cosmetic preparation should also be of effect against excess acidity.
  • a lotion which resists pH change in either direction there. is present in the invented compositions acombination of gluconic acid and water-soluble metallic gluconic acid salt.
  • the latter term describes a metal salt of gluconic acid, usually alkali metal, preferably sodium or potassium.
  • the salt maybe added directly or may be made by neutralization of gluconic acid with an alkaline agent, such as a strong base.
  • the neutralizing material is preferably a metallic alkaline compound, most preferably of an alkali metal, such as sodium or potassium, usually added as the hydroxide, carbonate or bicarbonate.
  • the gluconic acid may be added as its lactone, preferably glucono-delta-lactone, which hydrolyzes in aqueous media to produce an equilibrium mixture of gluconic acid and lactone.
  • a mixture of lactone, gluconic acid and metallic gluconate can also be made by admixing the lactone and a salt-forming base with the other hand lotion ingredients.
  • Cosmetic emulsions are generally aqueous emulsions of either the oil-in-water or water-in-oil types, the formerusually being the relatively thin lotions and the latter classification usually describing the physical nature of cosmetic creams. In both types of emulsions there is found a hydrophilic phase mixed with a lipophilic phase. In the oil-in-water emulsions, as indicated by the name, the lipophilic material is in the dispersed phase while the hydrophilic or aqueous substances comprise the continuous phase. The'converse is true for water-in oil preparations.
  • gluconic acid constituent is useful in both creams and lotions, its stability is most valuable in the lotion compositions because, being relatively fluid, these products are most susceptible to separation and reactions of ingredients which might promote separation.
  • acid creams other than those acidified with the compounds employed in this invention also can deteriorate or otherwise become unattractive on storage, their lack of mobility often hinders separation.
  • the lipophilic phase of cosmetic hand lotions usually constitutes a minor proportion of the lotion, generally from 1 to 10% by weight thereof.
  • the conventional oleaginous base materials such as mineral oil, higher fatty alcohol, partial esters of polyhydric alcohol, e.g., glyceryl' monostearate, propylene glycol monolaurate, diglycerides, to name only? a few, triglycerides, higher fatty acid esters or waxes, and other lipophiles.
  • Some of these so-called lipophilic materials posses-s hydrophilic functional groups which make them compatible with the continuous aqueousmedium.
  • the partial esters are also used as emulsifiers for oleaginous ingredients.
  • the continuous aqueous phase is composed substantially of water although it will also contain those ingredients of the lotion which are preferentially soluble in water.
  • the common solvents such as the lower alcohols, including ethanol, lower polyhydric alcohols, propylene glycol, water soluble salts, both inorganic and organic water soluble acids, dyes, germicides, surface active agents and emulsifiers.
  • the lower alcohols including ethanol, lower polyhydric alcohols, propylene glycol, water soluble salts, both inorganic and organic water soluble acids, dyes, germicides, surface active agents and emulsifiers.
  • the lower alcohols including ethanol, lower polyhydric alcohols, propylene glycol, water soluble salts, both inorganic and organic water soluble acids, dyes, germicides, surface active agents and emulsifiers.
  • the lower alcohols including ethanol, lower polyhydric alcohols, propylene glycol, water soluble salts, both inorganic and organic water soluble acids, dye
  • an emulsifying agent such as the partial esters of higher fatty acids with polyhydric alcohols, previously mentioned, long chain polyoxyalkylene polymers containing hydrophobic and hydrophilic groups in balance, the so-called self-emulsifying waxes and other suitable surface active agents, such as the polyoxyethylene esters and others of higher fatty alcohols or alkyl phenols, the block copolymers of different lower alkylene oxides (the Pluronics), sugar esters and others and so forth.
  • nonionic emulsifiers such as the partial esters of higher fatty acids with polyhydric alcohols, previously mentioned, long chain polyoxyalkylene polymers containing hydrophobic and hydrophilic groups in balance, the so-called self-emulsifying waxes and other suitable surface active agents, such as the polyoxyethylene esters and others of higher fatty alcohols or alkyl phenols, the block copolymers of different lower alkylene oxides (the Pluronics), sugar esters and others and so forth.
  • non-ionic emulsifiers and so-called selfemulsifying waxes are highly preferred emulsifying agents for the present cosmetic lotions
  • anionic or cationic surface active com-pounds may also be usefully employed if they are chosen with care for resistance to decomposition in acidic media.
  • lotions that are of only relatively slight acidity there may be employed, as emulsifiers, monoglyceride sulfates and sulfonates, the alkyl ether sulfates and sulfonates, the di-alkyl sulfosuccinates, higher fatty alcohol sulfates and other well known acid-resistant surfactants.
  • Cationic agents having surface activity are also elfective emulsifiers in hand lotions.
  • the cationic compounds are usually employed in conjunction with non-ionics and the presence of anionic materials is generally avoided when cationic materials are used because of the interaction of these two types of emulsifiers, usually accompanied by the production of an insoluble precipitate of low or negligible dispersing power.
  • the cationic emulsifiers of the quaternary ammonium type possess strong anti-bacterial power and therefore are of additional desirable utility in hand lotions.
  • N-lauroyl colamino formylmethyl pyridinium chloride cetyl trimethyl ammonium bromide and diisobutyl cresoxy ethoxy ethyl dimethyl benzyl ammonium chloride.
  • cetyl trimethyl ammonium bromide diisobutyl cresoxy ethoxy ethyl dimethyl benzyl ammonium chloride.
  • Gluconic acid which is the major acidifying agent of these hand lotions, is soluble in water but not in alcohol, ether or most other organic solvents. Gluconic acid may be added directly to the aqueous phase of the hand lotions or to the emulsion after it is formed, although the latter course is generally considered to be preferable.
  • the easily handled crystalline lactone of gluconic acid gluconodelta-lactone, may be employed. The lactone hydrolyzes in aqueous solution with formation of the acid and establishment of an equilibrium between the acid and the deltaand gamma-lactones.
  • Hand lotions containing either the gluconic acid ingredient or the equilibrium mixture referred to are resistant to an increase in pH and even when subjected to alkaline agents tend to maintain their original pH or else to allow it to be increased only slightly.
  • a small quantity of lotion lowers the skin pH to a point near the pH of the lotion itself, restoring the protective acid condition of the skin.
  • the presence of the gluconic acid also tends to stabilize the acid pH of the lotion by minimizing the effect of alkaline materials, whether they are in the lotion formula or contact the lotion or develop Within it during manufacture or storage.
  • These compounds also sequester metal ions which otherwise might tend to react to form unwanted colored compounds or which might catalyze decomposition of lotion components and breaking of the emulsion.
  • the pH at which it is desired to maintain the hand lotion and the buffering activity of the lotion can be adjusted by varying the quantities and proportions of gluconic acid and water-soluble metallic gluconate salt in the formula.
  • gluconate such as the sodium or potassium compound tends to establish a new equilibrium pH, higher than that of the gluconic acid alone. It also gives the lotion increased resistance to alteration of pH by acid.
  • gluconate as its salt it can be made by neutralization of gluconic acid or the lactone by any suitable alkaline salt-forming material such as sodium hydroxide, sodium carbonate, alkali metal bicarbonate and so forth.
  • emulsifiers and other adjuvant materials In cosmetic lotions it is preferred to keep the amounts of emulsifiers and other adjuvant materials to the neces sary minimum so as to limit their elfects on the skin and prevent deposition of relatively large amounts of insoluble substances on the epidermis. Such limitation also allows the oil, emollient and aqueous ingredients to better perform their own designed functions on the skin.
  • Gluconic acid and its salts may be used in cosmetic emulsions up to a limit of about 10% of the said compositions. Above that concentration the salt and acid content tends to be too great to be compatible with many cosmetic lotions and interferes with the desired properties of the lotion.
  • the lower limit of gluconic acid and gluconate content may be as little as 1/ of 1%, so long as that proportion has an acidifying effect on the lotion.
  • On a hand lotion basis it is preferred to employ from 1 to 7% of a combination of gluconic acid and soluble inorganic gluconate and/or glucono-lactone.
  • the amount of gluconic acid, salt, and/ or lactone should be such as to result in a lotion pH above 3. Below that pH the acid lotion tends to irritate rather than soothe the skin.
  • the skin itself contains bufiering agents and the normal, small amounts of lotion employed usually will not lower the pH all the way to that of the lotion itself, it is considered that as a protection against application of excessive amounts of lotion the pH thereof must be kept above 3.
  • Most formulations for general cosmetic use will have a pH above about 3.5 and one of the pH 4 to 6 will closely match that of the average human skin.
  • a lotion of pH 4 will conform to skin pH and will also be of considerable effectiveness against alka
  • a lotion of a pH below 4, even below 3.5 may be useful for application to the hands after subjecting them to highly alkaline solutions, such as solutions of some harsh detergent compositions.
  • the lotion will acidify the skin but the final skin pH will be higher than that of the cosmetic, and nearer to that of normal skin.
  • Such lotions are also suitable for ordinary cosmetic use on the hands in many instances because the natural buffering agents deposited by perspiration on the skin, will tend to limit the extent to which the lotion can lower the skin acidity.
  • the amount of metallic gluconate should be less than that of the gluconic acid or sum of gluconic acid and lactone.
  • the preferred oil-in-Water skin lotions should comprise a major proportion of continuous aqueous hydrophilic 6 phase and a minor proportion of lipophilic phase.
  • the gluconic acid, inorganic gluconate and lactone, Polymethyl s loxane 1.0 if present, are in the aqueous phase and preferably are Self-emulsifying waxy condensation product of less than 10% of that phase of the hand lotion. They h1gher fatty alcohol and ethylene ox1de 1.0 are present in sufficient quantity to desirably adjust the 10 Part C: acidity of the aqueous phase although they have limited Water 5.0 effect on the pH of the dispersed phase.
  • part C at room temperature, was admixed
  • A+B only about 5 minutes after the making of Q heat the components of the aqueous and lipophilic phases Aflsr Gosling to 0 R the emulsion was perfumed and separately to an elevated temperature, usually above 150 CO1 cred by addition of part D
  • the Complete lotion was at which the Phases are homogeneous- At such a then cooled to 80 F.
  • the skin pH was may be added as 50011 as the gluconic mpound has deter-mined immediately after drying and 5, 15, 30 and 60 been incorporated in the emulsion or after a ditional minutes later after subsequent application of lotion.
  • Minor amounts of heat-sensitive adjuvants such following table summarizes results of these tests:
  • Table 1 Total Total hands Initial pH, Abnormal pH, Lotion Skin i igli c tiiin h i foi r i after sublects tested beforesoakius altersoaking applied (avg.) (drops/hand) as perfumes, antibiotics, germicides and colorants may be added at lower temperatures, e.g., room temperature.
  • the above lotion was formulated primarily to be effective against alkali on the skin, it also had an appreciable action against excess acidity, which action could be increased by raising the amount of sodium gluconate in the formula and increasing the ratio of gluconate to gluconic acid present.
  • EXAMPLE II A cosmetic lotion for counteracting alkalinity of skin surfaces to which it is applied was'made of essentially the same formula as that of Example I except that 6% glucono-delta-lactone and 0.5% sodium hydroxide were included, the water content of the lotion being decreased to compensate for the additional amounts of lactone and hydroxide. No perfume or colorant was added.
  • the lotion was manufactured according to the process of Example I with the omission of the addition of the part D ingredients at 95 F.
  • the product was a stable acidic lotion of high alkali neutralizing activity.
  • 10 ml. of lotion initially at pH 3.7 was increased to a pH of only 4.7 after treatment with 150 ml. of 0.01 N NaOH.
  • EXAMPLE III A hand lotion was made according to a formula essentially the same as that of Example II except that 6.5% of gluconic acid was employed instead of the 6.0% of glucono-delta-lactone. The manufacturing process was the same. The product made was a lotion of acceptable stability and excellent neutralizing effect against alkali.
  • Various compatible adjuvants may be added to the invented lotions for their special effects or properties. Their addition may be made at any suitable stage of the processing and the manufacturing procedure may be adjusted, if desirable, to better effect admixing of adjuvant and to maintain stability of the lotion.
  • bactericides e.g., hexachlorophene
  • preservatives to combat mold and bacterial growth, e.g., methyl and propyl para-hydroxybenzoate, skin restoratives; e.g., allantoin; skin rejuvenators, e.g., steroids; deodorants; thickening agents, e.g., hydroxy alkyl celluloses; humectants, e.g., sorbitol; and opacifiers, e.g., behenic acid.
  • a stable acidic cosmetic emulsion lotion for the skin comprising an aqueous hydrophilic phase, a lipophilic phase and an emulsifier to maintain said phases in stable emulsion form, the hydrophilic phase being at a pH above 3 and containing a minor proportion, in combination less than about 10% of the lotion, of gluconic acid and soluble metallic gluconate salt.
  • a stable acidic hand lotion comprising an oil-inwater emulsion having a major proportion of a continuous aqueous hydrophilic phase, a minor proportion of dispersed lipophilic phase and a nonionic emulsifier distributed between the phases and maintaining them in stable emulsion form, the hydrophilic phase being at a pH above 3 and containing a minor proportion, less than 10% of the lotion, of a mixture of gluconic acid, soluble alkali metal gluconate and lactone of gluconic acid.
  • a stable acidic hand lotion comprising an oil-inwater emulsion having a major proportion, over 75%, of a continuous aqueous hydrophilic phase, a minor proportion, less than of a lipophilic phase and a nonionic emulsifier distributed between the phases and maintaining them in stable emulsion form, the hydrophilic phase being at a pH of about 4 to 6 and containing a minor proportion, less than 10% of the hand lotion, of an equilibrium mixture of gluconic acid, soluble alkali metal gluconate salt and lactone of gluconic acid, in which mixture the alkali metal gluconate salt is a minor constituent.
  • a stable acidic hand lotion comprising an oil-inwater emulsion containing to water and minor proportions of oleaginous base, lanolin, and non-ionic emulsifier distributed between the phases and maintaining them in stable emulsion form, the continuous aqueous hydrophilic phase of the emulsion being at a pH of about 4 to 6 and containing a minor proportion, less than 10% of the hand lotion, of an equilibrium mixture of gluconic acid, soluble alkali metal gluconate salt and lactone of gluconic acid, the amount of gluconate being less than the sum of gluconic acid and lactone of gluconic acid.
  • a process for manufacturing a stable acidic cosmetic emulsion which comprises admixing and emulsifying water, oleaginous base and nonionic emulsifier, adding substantially unhydrolyzed glucono-delta-lactone as a source of hydrogen ions, the lactone hydrolyzing to form gluconic acid in situ, after formation of the emulsion, in suiiicient amount to produce a stable acidic product.
  • a process for manufacturing a stable acidic cosmetic emulsion of aqueous hydrophilic phase and lipophilic phase which comprises mixing and emulsifying aqueous hydrophilic and lipophilic phases with nonionic emulsifier at a temperature at which the lipophilic phase is liquid and is emulsifiable with the aqueous phase, making an aqueous solution of glucono-delta-lactone and admixing lactone solution and emulsion at a temperature at which the solution is emulsified, before the lactone has hydro lyzed sufliciently to gluconic acid to decrease stability of the emulsion.
  • a process for manufacturing a stable acidic cosmetic oil-in-water emulsion hand lotion which comprises mixing substantially all the lipophilic and hydrophilic constituents of such a lotion in separate lipophilic and hydrophilic phases, mixing and emulsifying these phases with nonionic emulsifier at a temperature above F making an aqueous solution of glucono-delta-lactone and soluble salt forming metallic neutralizing agent for gluconic acid, cooling the emulsion below 150 F. and adding the solution thereto before the lactone has been substantially hydrolyzed to gluconic acid.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
US826923A 1959-07-14 1959-07-14 Cosmetic preparation and process for manufacture thereof Expired - Lifetime US3060096A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US826923A US3060096A (en) 1959-07-14 1959-07-14 Cosmetic preparation and process for manufacture thereof
DEC21890A DE1201951B (de) 1959-07-14 1960-07-11 Stabile saure Hauptpflegeemulsion
GB24221/60A GB915816A (en) 1959-07-14 1960-07-12 Acidic cosmetic preparations and processes for their manufacture
BE592913A BE592913A (fr) 1959-07-14 1960-07-13 Emulsion cosmétique et procédé pour son obtention.

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BE (1) BE592913A (fr)
DE (1) DE1201951B (fr)
GB (1) GB915816A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4766153A (en) * 1986-04-30 1988-08-23 Sandoz Ltd. Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same
US5371287A (en) * 1993-01-27 1994-12-06 Bp Chemicals Limited Releasably bound hydroxycarboxylic acids
USRE41883E1 (en) * 1999-05-03 2010-10-26 Georgia-Pacific Consumer Products Lp Lotionized tissue products containing a pH balance compound for the skin
US20120142738A1 (en) * 2009-04-15 2012-06-07 Stephan Guenter Pharmaceutical composition for treating dermatological autoimmune diseases

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4069347A (en) * 1976-08-02 1978-01-17 Emery Industries, Inc. Compositions of quaternary ammonium derivatives of lanolin acids
ATE396697T1 (de) 2004-03-08 2008-06-15 Unilever Nv Zuckerlacton enthaltende zusammensetzung zur haarbehandlung
CN100528128C (zh) 2004-03-08 2009-08-19 荷兰联合利华有限公司 含有糖内酯的头发处理组合物
DE602008003101D1 (de) 2007-03-14 2010-12-02 Unilever Nv Verfahren zur behandlung von haaren mit einer zuckerzusammensetzung
EP2194961B1 (fr) 2007-10-10 2011-08-03 Unilever PLC Procédé de traitement des cheveux
MX2010010726A (es) 2008-03-28 2010-10-25 Unilever Nv Composicion de estilizado de cabello.
BR112021017173B1 (pt) 2019-03-07 2023-11-07 Inolex Investment Corporation Composições catiônicas à base de aminoácidos autonutralizantes e formulação aquosa

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2491452A (en) * 1948-08-20 1949-12-13 American Home Prod Stabilized vitamin preparation
US2658078A (en) * 1950-09-19 1953-11-03 Pfizer & Co C Solvent extraction of oxytetracycline
US2732326A (en) * 1956-01-24 nnaoh

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2118566A (en) * 1935-08-29 1938-05-24 Miles Gilbert De Wayne Buffered cosmetic
DE921282C (de) * 1952-05-10 1954-12-13 Karl Hans Schuster Dr Med Verfahren zur Herstellung von Hautcremes mit durchblutungsfoerdernder Wirkung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2732326A (en) * 1956-01-24 nnaoh
US2491452A (en) * 1948-08-20 1949-12-13 American Home Prod Stabilized vitamin preparation
US2658078A (en) * 1950-09-19 1953-11-03 Pfizer & Co C Solvent extraction of oxytetracycline

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4766153A (en) * 1986-04-30 1988-08-23 Sandoz Ltd. Alkyl polyoxyalkylene carboxylate esters and skin care compositions containing the same
US5371287A (en) * 1993-01-27 1994-12-06 Bp Chemicals Limited Releasably bound hydroxycarboxylic acids
USRE41883E1 (en) * 1999-05-03 2010-10-26 Georgia-Pacific Consumer Products Lp Lotionized tissue products containing a pH balance compound for the skin
US20120142738A1 (en) * 2009-04-15 2012-06-07 Stephan Guenter Pharmaceutical composition for treating dermatological autoimmune diseases

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BE592913A (fr) 1961-01-13
GB915816A (en) 1963-01-16
DE1201951B (de) 1965-09-30

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