US3177120A - Stable cosmetic preparations containing dihydroxy acetone - Google Patents

Stable cosmetic preparations containing dihydroxy acetone Download PDF

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Publication number
US3177120A
US3177120A US33092A US3309260A US3177120A US 3177120 A US3177120 A US 3177120A US 33092 A US33092 A US 33092A US 3309260 A US3309260 A US 3309260A US 3177120 A US3177120 A US 3177120A
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US
United States
Prior art keywords
dihydroxy acetone
water
stable
acid
mixture
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US33092A
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English (en)
Inventor
Black Archie Scott
Casini Raymond Alfred
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Consumer Care Holdings LLC
Original Assignee
Plough
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to GB21833/57A priority Critical patent/GB828266A/en
Application filed by Plough filed Critical Plough
Priority to US33092A priority patent/US3177120A/en
Priority to DEP27251A priority patent/DE1301983B/de
Priority to FR863433A priority patent/FR1293290A/fr
Priority to BE604430A priority patent/BE604430A/fr
Priority to CH640161A priority patent/CH379694A/de
Priority to GB19839/61A priority patent/GB928266A/en
Application granted granted Critical
Publication of US3177120A publication Critical patent/US3177120A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/04Preparations for care of the skin for chemically tanning the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37Esters of carboxylic acids

Definitions

  • This invention relates to stable cosmetic preparations, either in the form of lotions or creams, containing dihydroxy acetone.
  • Dihydroxy acetone is an industrially important chemical, produced commercially by the dehydrogenation or oxidation of glycerol by certain acetic acid bactena (cf. Industrial Microbiology, Prescott and Dunn, 1940).
  • the fact that dihydroxy acetone reacts with protein to produce browning or tanning, has been observed from time to time (cf. Dreizen, Gilley, Mosny, and Spies, J. Dental Research, vol. 36, pages 23336, 1957) and the tanning effect of dihydroxy acetone on the keratirnzed cells making up the stratum corneum of the skin, has been studied in years past.
  • One of the objects of this invention is to provide a creamy base cosmetic preparation, containing an effective amount of dihydroxy acetone to produce tanning of the human skin, which is stable both as to color and to the effectiveness of the dihydroxy acetone.
  • Another object of this invention is to provide such a creamy base lotion which contains a sunscreening agent.
  • a cosmetic preparation which contains a nontoxic, acid-stable, creamy base and a cosmetically eifective amount of dihydroxy acetone.
  • the preparation has a pH upon compounding and upon six months or more aging, between 2.5 and 6.0.
  • a part, but a very useful and desirable part of this invention, is the incorporation, in the creamy base preparation, of a sunscreening agent free of amino groups.
  • sunscreening agents With the simulated suntanning preparation, so that, if it is at all possible for the user to do so, the user can apply the preparation, and shortly thereafter get into the sunlight as he normally would in the use of a so-called suntan lotion. Under such circumstances, the user will acquire a more lasting and deep-colored tan than with either the suntan lotion or simulated suntan lotion alone, but, at the same time, the uniformity will not be so great as to appear artificial. That is to say, the user will acquire the attractive highlights of a natural tan. It has been found, however, that sunscreening agents now commonly used in suntan lotions react with dihydroxy acetone or, at least, in its presence, to develop a yellow to brown color.
  • sunscreening agents such as salicylates and cinnamates, free of amino groups, in a creamy base containing dihydroxy acetone, and maintaining the pH of the product between 2.5 and 6.0, a cosmetic product is produced which is stable both as to color and as to the effectiveness, as a skin tanning agent, of the dihydroxy acetone.
  • Part I The components of Part I are combined and heated to 175 F. in a steam-jacketed kettle. In a separate kettle, the ingredients of Part II are combined and heated to 175 F. The mixture of Part I is then added to the mixture of Part II, with continuous stirring.
  • the dihydroxy acetone is dissolved in the water, Part III, and added to the mixture of Parts I and II with continuous stirring. The mixture is allowed to cool.
  • the volume is adjusted by the addition of water, and the resultant lotion is mixed Well.
  • Example 2 Percent Carboxypolymethylene (Carbopol 940, Goodrich Chem. Co.) 1.5 Polyethylene glycol 600 5 Dihydroxyacetone 0.5-20 Diisopropanolamine, q.s. ad 1 Perfume, q.s. Water, q.s. to 100%.
  • the diisopropanolarnine is then added and mixed only enough to incorporate it thoroughly.
  • the pH of the mixture, during the addition of the diisopropanolamine should be checked, to insure that the pH does not rise above 5 .5
  • Example 3 Part 1 Percent Polyethylene glycol ether-fatty alcohol complex 3 Polyoxyethylene sorbitan stearate 2.5 Sorbitan, sesquioleate 3 Methyl polysiloxane 0.2 Lanolin l Cetyl alcohol 1 Homomenthyl salicylate 6-12 Part II:
  • Part I pH.initially and upon aging does not exceed The components of Part I are combined and heated to 175 F. in a steam-jacketed kettle. In a separate kettle,
  • Part II the ingredients of Part II are combined and heated to 175 F.
  • the combined components of Part I are then added to the combined components of Part II, with continuous stirring.
  • the dihydroxy acetone is dissolved in the water, Part III, and added to the combined Parts I and II, withcontinuous stirring. The mixture is then allowed to cool.
  • the volume is adjusted by the addition of water, and the resultant lotion is mixed well.
  • Example 4 Part 1 Percent Polyethylene glycol ether-fatty alcohol complex 3 Polyoxyethylene sorbitan stearate 2.5 Sorbitan sesquioleate 3 Methyl polysiloxane 0.2 Lanolin 1 Cetyl alcohol 1 Z-ethoxy ethyl p-methoxy cinnamic acid 0.5-6 Part II: V
  • Example 4 pH--Initially and upon aging does not exceed The manufacturing procedure for the lotion of Example 4 is precisely the same as for that of Example 3.
  • Part Iand Part II The ingredients of Part Iand Part II are mixed separately, and eachrnixture is heated to 180 F.
  • the mixture of Part II is then added to the mixture of Part I, with stirring.
  • the heating is discontinued, and stirring is continued until thertemperature reaches 120 R, at which point the perfume is added.
  • the mixture is stirred until cooled toroom temperature.
  • Example 5 is of the consistency in physical character of What is known in the trade as a cream, as compared with the product of Examples 3 and 4, which is of the character known as a lotion in the trade.
  • Example 6 Another example of a product of this invention,in the formof a cream, is as follows:
  • Part I Percent Polyethylene glycol ether-fatty alcohol complex 12 Lanolin 3 Cetyl alcohol 3 Methyl polysiloxane 1 Homomenthylsalicylate 6 12 Part II:
  • Example 6 The compounding of the product of Example 6 is iden tical with that of Example 5.
  • the chief factors in the present invention appear to be the acid-stable creamy base at a low pH, and the absence, in the sunscreening agent, of amino groups. It may be noted that in the composition of Example 2, diisopropanolamine is used, in the compounding of the creamy base. However, it is to be observed that less than an equivalent amount of diisopropanolamine is reacted with the carboxypolymethylene, so that the composition not only remains on the acid side, but the amine is totally reacted.
  • fatty acids, gel forming materials, organic acid buffers, wetting and dispersing agents, and even sunscreening agents need only meet the requirements that they be acid-stable, unreactive with dihydroxy acetone, free of active amino groups in the final composition, and nontoxic, numerous suitable materials for the compounding of such creamy bases, in addition to those specifically enumerated, will occur to those skilled in the art.
  • acid butters, tartrates, phosphates, acetates, and the like may be substituted for the citric acid or citrates given in the examples.
  • fatty acids gel forming agents, wetting agents and the like, acid stabilized glyceryl monostearate, propylene glycol stearate, modified lanolin derivatives, gums, polyoxyethylene derivatives, and sorbitan derivatives, for example, can be employed.
  • Sunscreens owe their value in suntan products to their ability to absorb ultraviolet light in the range of 2900- 3250 Angstrom units. This is the region of the suns radiation which causes the undesirable and potentially harmful burning when it strikes the unprotected skin. By filtering out this portion of the radiation, it becomes possible to enjoy sunbathing and acquire a tan in comfort and safety.
  • Sunscreening agents other than salicylates or cinnamates may be used, so long as they do not contain amino groups.
  • sunscreening agents which do contain amino groups and which, accordingly, are unsatisfactory are esters of para-amino benzoic acid, such as glyceryl paraamino benzoate, and esters of anthranilic acid.
  • the amounts of the various constituents may also be varied, so long as the product contains an effective amount of dihydroxy acetone, and, in those products in which the sunscreening agent is used, an efiective amount of sunscreening agent.
  • other kinds and other amounts of emollient, viscosity-modifying, preservative and perfuming agents and the like such as are conventionally used in cosmetic creams and lotions, may be included in the formulations, provided they are not harmful for use on human skin and are not conducive to developing pH changes of the final product outside the range of stability, 2.5 to 6.0.
  • a cosmetic preparation comprising a non-toxic, stable, creamy base, a cosmetically effective amount of dihydroxy acetone, and an eifective amount of sunscreening agent characterized in being free from active amino groups, unreactive with dihydroxy acetone, and non-toxic, said preparation having a pH upon compounding and upon six months aging, of between 2.5 and 6.0.
  • the sunscreening agent is selected from the group consisting of homomenthyl salicylate and 2-ethoxy ethyl p-methoxy cinnamic acid.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
US33092A 1957-03-06 1960-06-01 Stable cosmetic preparations containing dihydroxy acetone Expired - Lifetime US3177120A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB21833/57A GB828266A (en) 1957-03-06 1957-07-10 Vibration damper
US33092A US3177120A (en) 1960-06-01 1960-06-01 Stable cosmetic preparations containing dihydroxy acetone
DEP27251A DE1301983B (de) 1957-03-06 1961-05-31 Hautbraeunungsmittel
FR863433A FR1293290A (fr) 1957-03-06 1961-05-31 Préparations cosmétiques stables contenant de la dihydroxy-acétone
BE604430A BE604430A (fr) 1960-06-01 1961-05-31 Préparations cosmétiques stables contenant de la dihydroxy-acétone
CH640161A CH379694A (de) 1957-03-06 1961-06-01 Beständige, Dihydroxyaceton enthaltende kosmetische Präparate
GB19839/61A GB928266A (en) 1957-03-06 1961-06-01 Stable cosmetic preparations containing dihydroxy acetone

Applications Claiming Priority (1)

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US33092A US3177120A (en) 1960-06-01 1960-06-01 Stable cosmetic preparations containing dihydroxy acetone

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US3177120A true US3177120A (en) 1965-04-06

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BE (1) BE604430A (fr)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3320133A (en) * 1962-02-08 1967-05-16 Toyo Koatsu Ind Inc Preparation of a face lotion with a pearly luster
US3541205A (en) * 1965-08-19 1970-11-17 Dow Corning Wash resistant lotion containing organosilicon resins
US3624221A (en) * 1965-05-04 1971-11-30 Ciba Geigy Corp Method of distributing the sebaceous secretions of the skin
US3862951A (en) * 1971-09-02 1975-01-28 Syva Co 2{40 Quinoldinyl glycerol compounds
US4454112A (en) * 1977-12-27 1984-06-12 Henkel Corporation Sunscreen composition containing tocopherol acetylsalicylate
US4708865A (en) * 1986-08-21 1987-11-24 Turner Janet N Method and composition for artificially tanning the human epidermis
US5268166A (en) * 1991-07-15 1993-12-07 Elizabeth Arden Company, Division Of Conopco, Inc. Cosmetic application system
US5318774A (en) * 1992-02-28 1994-06-07 Richardson-Vicks Inc. Composition and method for imparting an artificial tan to human skin
WO1994012146A1 (fr) * 1992-11-23 1994-06-09 Estee Lauder, Inc. Compositions cosmetiques autobronzantes et procede d'utilisation desdites compositions
WO1995015742A1 (fr) * 1993-12-09 1995-06-15 Estee Lauder Inc. Compositions autobronzantes
US5514437A (en) * 1994-03-29 1996-05-07 The Procter & Gamble Company Artificial tanning compositions having improved stability
US5603923A (en) * 1994-03-29 1997-02-18 The Procter & Gamble Company Artificial tanning compositions having improved color development
US5645822A (en) * 1992-12-16 1997-07-08 Schering-Plough Healthcare Products, Inc. Method and apparatus for sunless tanning
US5700452A (en) * 1993-04-16 1997-12-23 The Procter & Gamble Company Compositions for imparting an artificial tan and protecting the skin from ultra-violet radiation
US5705145A (en) * 1996-08-21 1998-01-06 E-L Management Corp. Skin tanning compositions and method
US5750092A (en) * 1996-03-14 1998-05-12 Schering-Plough Healthcare Products, Inc. Sunless tanning composition and method
US5756075A (en) * 1992-08-24 1998-05-26 Schering-Plough Healthcare Products, Inc. Apparatus and method for sunless tanning
US5827506A (en) * 1993-03-31 1998-10-27 Schering-Plough Healthcare Products, Inc. Sunless tanning method and apparatus
FR2779958A1 (fr) * 1998-06-18 1999-12-24 Oreal Procede pour ameliorer la coloration de la peau induite par la dha, nouvelles compositions et utilisations
US20020195119A1 (en) * 1997-10-08 2002-12-26 Laughlin Thomas J. Automated system for coating the human body
US20030000539A1 (en) * 1997-10-08 2003-01-02 Laughlin Products, Inc. Method of and apparatus for automatically coating the human body
US20030094510A1 (en) * 1997-10-08 2003-05-22 Laughlin Thomas J. Automated system for coating the human body: virtual motion
US20040241106A1 (en) * 1997-10-08 2004-12-02 Laughlin Products, Inc. Method and apparatus for automatically coating the human body
US20050049544A1 (en) * 2000-06-16 2005-03-03 Brandon Shaw Chemically tanning human skin
US6881417B1 (en) 1997-10-08 2005-04-19 Laughlin Products, Inc. Method, apparatus, and composition for automatically coating the human body with plural components
US20070041917A1 (en) * 2005-08-17 2007-02-22 Isaac Thomas Sunless tanning compositions
US20090092566A1 (en) * 2007-10-09 2009-04-09 Lentini Peter J Self-tanning cosmetic compositions and methods
US20100183688A1 (en) * 2006-07-24 2010-07-22 Amcol International Corporation Delivery System and Method of Manufacturing the Same
WO2012145638A2 (fr) 2011-04-20 2012-10-26 Kao Corporation Compositions d'auto-bronzage présentant une atténuation de la mauvaise odeur due à la réaction de maillard
WO2015003095A1 (fr) 2013-07-03 2015-01-08 Regents Of The University Of Minnesota Composés et compositions de bronzage sans soleil
IT202200025305A1 (it) 2022-12-09 2024-06-09 Massimo Carraro Derivati del glicerolo con effetto autoabbronzante

Citations (3)

* 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
US2412535A (en) * 1944-11-29 1946-12-10 Colgate Palmolive Peet Co Antiperspirant preparation
US2949403A (en) * 1959-03-09 1960-08-16 Andreadis Dihydroxyacetone compositions for tanning the human epidermis

Patent Citations (3)

* 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
US2412535A (en) * 1944-11-29 1946-12-10 Colgate Palmolive Peet Co Antiperspirant preparation
US2949403A (en) * 1959-03-09 1960-08-16 Andreadis Dihydroxyacetone compositions for tanning the human epidermis

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3320133A (en) * 1962-02-08 1967-05-16 Toyo Koatsu Ind Inc Preparation of a face lotion with a pearly luster
US3624221A (en) * 1965-05-04 1971-11-30 Ciba Geigy Corp Method of distributing the sebaceous secretions of the skin
US3541205A (en) * 1965-08-19 1970-11-17 Dow Corning Wash resistant lotion containing organosilicon resins
US3862951A (en) * 1971-09-02 1975-01-28 Syva Co 2{40 Quinoldinyl glycerol compounds
US4454112A (en) * 1977-12-27 1984-06-12 Henkel Corporation Sunscreen composition containing tocopherol acetylsalicylate
US4708865A (en) * 1986-08-21 1987-11-24 Turner Janet N Method and composition for artificially tanning the human epidermis
US5268166A (en) * 1991-07-15 1993-12-07 Elizabeth Arden Company, Division Of Conopco, Inc. Cosmetic application system
US5318774A (en) * 1992-02-28 1994-06-07 Richardson-Vicks Inc. Composition and method for imparting an artificial tan to human skin
US5756075A (en) * 1992-08-24 1998-05-26 Schering-Plough Healthcare Products, Inc. Apparatus and method for sunless tanning
WO1994012146A1 (fr) * 1992-11-23 1994-06-09 Estee Lauder, Inc. Compositions cosmetiques autobronzantes et procede d'utilisation desdites compositions
US5662890A (en) * 1992-11-23 1997-09-02 Estee Lauder, Inc. Self-tanning cosmetic compositions and methods of using the same
US5645822A (en) * 1992-12-16 1997-07-08 Schering-Plough Healthcare Products, Inc. Method and apparatus for sunless tanning
US5827506A (en) * 1993-03-31 1998-10-27 Schering-Plough Healthcare Products, Inc. Sunless tanning method and apparatus
US5700452A (en) * 1993-04-16 1997-12-23 The Procter & Gamble Company Compositions for imparting an artificial tan and protecting the skin from ultra-violet radiation
US5503824A (en) * 1993-12-09 1996-04-02 Lentini; Peter Skin tanning compositions
WO1995015742A1 (fr) * 1993-12-09 1995-06-15 Estee Lauder Inc. Compositions autobronzantes
US5603923A (en) * 1994-03-29 1997-02-18 The Procter & Gamble Company Artificial tanning compositions having improved color development
US5514437A (en) * 1994-03-29 1996-05-07 The Procter & Gamble Company Artificial tanning compositions having improved stability
US5750092A (en) * 1996-03-14 1998-05-12 Schering-Plough Healthcare Products, Inc. Sunless tanning composition and method
US5705145A (en) * 1996-08-21 1998-01-06 E-L Management Corp. Skin tanning compositions and method
US20030000539A1 (en) * 1997-10-08 2003-01-02 Laughlin Products, Inc. Method of and apparatus for automatically coating the human body
US7041089B2 (en) * 1997-10-08 2006-05-09 Laughlin Products, Inc. Automated system for coating the human body: virtual motion
US20030094510A1 (en) * 1997-10-08 2003-05-22 Laughlin Thomas J. Automated system for coating the human body: virtual motion
US20040089315A1 (en) * 1997-10-08 2004-05-13 Laughlin Products, Inc. Method of and apparatus for automatically coating the human body
US20040241106A1 (en) * 1997-10-08 2004-12-02 Laughlin Products, Inc. Method and apparatus for automatically coating the human body
US20050022807A1 (en) * 1997-10-08 2005-02-03 Laughlin Product, Inc. Automated system for coating the human body
US20020195119A1 (en) * 1997-10-08 2002-12-26 Laughlin Thomas J. Automated system for coating the human body
US6881417B1 (en) 1997-10-08 2005-04-19 Laughlin Products, Inc. Method, apparatus, and composition for automatically coating the human body with plural components
US7082948B2 (en) 1997-10-08 2006-08-01 Laughlin Products, Inc. Method of and apparatus for automatically coating the human body
US6899108B2 (en) 1997-10-08 2005-05-31 Laughlin Products, Inc. Automated system for coating the human body
FR2779958A1 (fr) * 1998-06-18 1999-12-24 Oreal Procede pour ameliorer la coloration de la peau induite par la dha, nouvelles compositions et utilisations
US8137328B2 (en) 2000-06-16 2012-03-20 Safe Tan Chemically tanning human skin
US20050049544A1 (en) * 2000-06-16 2005-03-03 Brandon Shaw Chemically tanning human skin
US9409004B2 (en) 2000-06-16 2016-08-09 Safe Tan, Llc Chemically tanning human skin
US7537584B2 (en) 2000-06-16 2009-05-26 Safe Tan Chemically tanning human skin
US20090211592A1 (en) * 2000-06-16 2009-08-27 Drew Waters Chemically tanning human skin
US7699822B2 (en) 2000-06-16 2010-04-20 Brandon Shaw Chemically tanning human skin
US20050113769A1 (en) * 2000-06-16 2005-05-26 Drew Waters Chemically tanning human skin
US20070041917A1 (en) * 2005-08-17 2007-02-22 Isaac Thomas Sunless tanning compositions
US20100183688A1 (en) * 2006-07-24 2010-07-22 Amcol International Corporation Delivery System and Method of Manufacturing the Same
US20090092566A1 (en) * 2007-10-09 2009-04-09 Lentini Peter J Self-tanning cosmetic compositions and methods
WO2012145638A2 (fr) 2011-04-20 2012-10-26 Kao Corporation Compositions d'auto-bronzage présentant une atténuation de la mauvaise odeur due à la réaction de maillard
US9452125B2 (en) 2011-04-20 2016-09-27 Kao Usa Inc. Self-tanning compositions having reduced maillard reaction malodor
WO2015003095A1 (fr) 2013-07-03 2015-01-08 Regents Of The University Of Minnesota Composés et compositions de bronzage sans soleil
US9987211B2 (en) 2013-07-03 2018-06-05 Regents Of The University Of Minnesota Sunless tanning compounds and compositions
IT202200025305A1 (it) 2022-12-09 2024-06-09 Massimo Carraro Derivati del glicerolo con effetto autoabbronzante

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Publication number Publication date
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