WO1994007460A1 - Procedes utilises pour ameliorer l'aborbance ultraviolette de composes d'ecrans solaires - Google Patents

Procedes utilises pour ameliorer l'aborbance ultraviolette de composes d'ecrans solaires Download PDF

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Publication number
WO1994007460A1
WO1994007460A1 PCT/US1992/008215 US9208215W WO9407460A1 WO 1994007460 A1 WO1994007460 A1 WO 1994007460A1 US 9208215 W US9208215 W US 9208215W WO 9407460 A1 WO9407460 A1 WO 9407460A1
Authority
WO
WIPO (PCT)
Prior art keywords
ratio
absorbance
integer
emollient system
system comprises
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.)
Ceased
Application number
PCT/US1992/008215
Other languages
English (en)
Inventor
Barry A. Salka
Martin J. Barabash
Robert M. Jablonski
Arturo Valdes
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.)
Henkel Corp
Original Assignee
Henkel Corp
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
Application filed by Henkel Corp filed Critical Henkel Corp
Publication of WO1994007460A1 publication Critical patent/WO1994007460A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/37—Esters of carboxylic 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
    • A61K8/18—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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups

Definitions

  • the present invention relates to methods for increasing the UV absorbance of certain sunscreen agents for topical applications yielding compositions exhibiting improved sun protection factor (SPF). These methods comprise dissolving or suspending octyl methoxycinnamate or benzophenone-3 in certain emollient systems resulting in a 15% increase in UV absorbance.
  • SPF sun protection factor
  • the sun emits energy in a continuous band throughout the electromagnetic spectrum which includes the ultraviolet range (200-400 nm), that part of the spectrum that tans and burns the skin.
  • Prolonged exposure of a person's skin to the sunlight may cause a variety of conditions. For example, it can cause premature aging of the skin. In some cases, it may cause the development of skin cancers such as basal cell cancer, squamous cell cancer and melanoma. See for example, Blum, H.F. "Sunlight As An Environmental Factor in Cancer of the Skin".
  • Military Medicine 117: 202, 1955; Consequently, many products or measures have been marketed to protect the skin from the harmful effects of excessive exposure to the sun.
  • Sunscreen agents such as octyl methoxycinnamate and benzophenone-3 have gained wide acceptance. These agents act by absorbing UV light thereby offering the selective protection against the harmful effects of UV wave bands.
  • the compounds are dissolved or suspended in solvent systems such as ethanol, isopropanol, propylene glycol, and mineral oil, and the resulting compositions applied to the skin.
  • UV properties are: ⁇ max (EA) : 288/325 ⁇ nm max(MO): 288/329 nm
  • U.S. patents 5,075,333 and 5,061,733 discloses the use of Cetiol LC (caprylic/capric acid/coco ester) and Cetiol V (decyl oleate) in creams and gels.
  • UV absorbance of octyl methoxycinnamate is significantly increased when it is dissolved or suspended in certain highly polar type materials, i.e. ethoxylates and more particularly the following compounds: I, II, III, IV, V and VI.
  • R 1 is C 10 -C 18 straight or branched chain alkyl
  • x is an integer of 5 to 10
  • y is an integer of 2 to 6.
  • RCO is a pelargonic acid radical
  • R is an isostearic acid radical and n is an integer of 2 to 5.
  • R 4 is C 8 to C 12 alkyl
  • UV absorbance is significantly increased when it is dissolved or suspended in solvents
  • SPF as used herein means the test used by the FDA which is essentially the ratio of the amount of energy required to produce a minimum erythemal dose (MED) to the amount of energy to produce the same MED without any treatment by the product.
  • the present invention is directed to a method and means whereby there is an increase in UV light absorbance with no significant shift in wavelength of maximum absorbance for the known sunscreen agents, octyl methoxycinnamate and benzophenone-3.
  • the present invention also includes within its scope compositions comprising these compounds exhibiting not only enhanced UV absorbance but also have emollient properties for topical application.
  • the method of the present invention comprises mixing together an effective sunscreen amount of octyl methoxycinnamate and benzophenone-3 in the selected system, i.e. the compounds identified as I to VI above either alone or as a blend as a binary or tertiary system.
  • the results are tabulated in Tables I and II.
  • PPG-2-Ceteareth-9 310. 0 0.444 +28.6 Caprate
  • Triglyceride PPG-2-Ceteareth-9 323.0 0.241 +18.1
  • the above results are obtained by combining the selected sunscreen agent at about 500 ppm in the system as described.
  • the above results also demonstrate the surprising effect of the present invention as not all polar compounds have the positive influence in increasing UV absorbance.
  • Examples of commercially available solvents which fall within I are PPG-5-laureth-5 and PPG-2-ceteareth-9; those which fall within II include pentaerythrityl tetrapelargonate; those which fall within III include polyglycerol-3 diisostearate; those which fall within IV include caprylic/capric triglyceride and those which fall within V include PEG-7-glyceryl cocoate and those which fall within VI include propylene glycol isostearate.
  • PPG-2-ceteareth-9 caprylic/capric triglyceride at an approximate ratio of about 50 : 25 : 25 and glycerol cocoate: propylene glycol isostearate at an approximate ratio of 50 : 50 is advantageous as the resulting composition exhibits a 20% increase in UV absorbance.
  • a combination of PEG-7 -glyceryl cocoate : polyglycerol-3 diisostearate at an approximate ratio of 75 : 25 and a combination of polysorbate 80 : PPG-5-laureth-5 : caprylic/capric triglyceride at an approximate ratio of 50 : 25 : 25 is advantageous as these exhibit a 20% increase in
  • sunscreen composition must be non-toxic and non-irritating to the skin and capable of application to the skin as a uniform continuous film, i . e. an emollient effect.
  • active sunscreen affects must remain chemically stable in the vehicle for topical application.
  • the compositions of sunscreen agents prepared in accordance with the present exhibit these desirable properties in addition to enhanced UV absorbance.
  • the system may include other agents traditionally used in formulating sunscreen products.
  • agents include for example preservatives (such as methyl and propyl paraben) fragrance, anti-oxidants , wetting agents , emulsifiers , emulsion stabilizers and the like.
  • Example 1 In order to further illustrate the practice of the invention, the following examples are included: Example 1
  • Emulsions were prepared as follows :
  • polyglycerol-3 diisostearate (75:25) 13.2
  • polyglycerol-3 diisostearate (75:25) 11.6
  • caprylic/capric triglyceride 50:25:25 13.8
  • caprylic/capric triglyceride 50:25:25 10.5

Landscapes

  • 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)

Abstract

Procédés permettant d'augmenter l'absorbance ultraviolette de certains agents écrans solaires pour produire des compositions d'application topique possédant un facteur de protection solaire (FPS) amélioré. Selon ces procédés on dissout ou on met en suspension du méthoxycinnamate d'octyle ou du benzophénone-3 dans certains systèmes émollients, tels que par exemple des matériaux fortement polaires comme des éthoxylates, pour augmenter de 15 % l'absorption des ultraviolets.
PCT/US1992/008215 1992-09-30 1992-10-02 Procedes utilises pour ameliorer l'aborbance ultraviolette de composes d'ecrans solaires Ceased WO1994007460A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95417792A 1992-09-30 1992-09-30
US954,177 1992-09-30

Publications (1)

Publication Number Publication Date
WO1994007460A1 true WO1994007460A1 (fr) 1994-04-14

Family

ID=25495045

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1992/008215 Ceased WO1994007460A1 (fr) 1992-09-30 1992-10-02 Procedes utilises pour ameliorer l'aborbance ultraviolette de composes d'ecrans solaires

Country Status (2)

Country Link
CA (1) CA2137143A1 (fr)
WO (1) WO1994007460A1 (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996014053A1 (fr) * 1994-11-02 1996-05-17 Cussons (International) Limited Composition filtrant les uv et nettoyant la peau
EP0728470A3 (fr) * 1995-02-21 1996-12-04 Shiseido Co Ltd Composant absorbant de la lumière ultraviolette
GB2309385A (en) * 1994-11-02 1997-07-30 Cussons Int Ltd Skin cleansing-UV screening composition
DE19615036A1 (de) * 1996-04-17 1997-10-23 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und Propylenglycolestern
DE19616926A1 (de) * 1996-04-27 1997-10-30 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und Monoester und Diester aus verzweigten Alkancarbonsäuren und dem Diglycerin oder Triglycerin
DE19645318A1 (de) * 1996-11-04 1998-05-07 Beiersdorf Ag Stabile Lichtschutzzubereitungen mit einem Gehalt an grenzflächenaktiven Glucosederivaten und wasserlöslichen UV-Filtersubstanzen
US5894019A (en) * 1995-03-17 1999-04-13 Gebro Broschek Gesellschaft M.B.H. Topically applied pharmaceutical composition, method of preparing it and its use
EP1000611A1 (fr) * 1998-10-10 2000-05-17 Beiersdorf Aktiengesellschaft Utilisation de cires triglyceridiques pour augmenter l'indice de photoprotection d'une composition photoprotectrice
WO2006013703A1 (fr) * 2004-08-04 2006-02-09 Adeka Corporation Composition d’émulsion stabilisatrice de lumière et composition de revêtement aqueuse contenant ladite composition
US7025758B2 (en) 2000-01-28 2006-04-11 William Cook Europe Aps Endovascular medical device with plurality of wires
US7671096B2 (en) * 2005-02-14 2010-03-02 Adeka Corporation Light stabilizer emulsion composition
US20140170091A1 (en) * 2012-12-12 2014-06-19 Thomas Christopher Balshi Composition for Correcting Skin Pigment Conditions
ITUA20163227A1 (it) * 2016-05-06 2017-11-06 Novamont Spa Composizioni cosmetiche contenenti diglicerolo tetrapelargonato.
CN108348426A (zh) * 2015-09-08 2018-07-31 诺瓦蒙特股份公司 含壬酸酯的水性化妆品组合物
JP2018526400A (ja) * 2015-09-08 2018-09-13 ノバモント・ソシエタ・ペル・アチオニＮｏｖａｍｏｎｔ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ ペラルゴン酸エステルを含む親油性化粧品用組成物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4863411B2 (ja) * 2010-01-29 2012-01-25 株式会社 資生堂 水中油型乳化日焼け止め化粧料

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2340086A1 (fr) * 1976-02-04 1977-09-02 Bayer Ag Preparations antisolaires
US4264581A (en) * 1979-07-02 1981-04-28 Eli Lilly And Company Sunscreen composition
US4384974A (en) * 1979-07-27 1983-05-24 Revlon, Inc. Stable water-in-oil emulsions
EP0165457A2 (fr) * 1984-05-21 1985-12-27 Henkel Kommanditgesellschaft auf Aktien Ingrédient huileux cosmétique
US4940574A (en) * 1988-12-22 1990-07-10 Plough, Inc. Non-aqueous high SPF sunscreen oils
EP0418443A1 (fr) * 1988-04-04 1991-03-27 Neutrogena Corporation Composition formant un écran solaire imperméable
FR2670111A1 (fr) * 1990-12-11 1992-06-12 Bosserelle Micheline Composition de corps gras pour produits cosmetiques.

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2340086A1 (fr) * 1976-02-04 1977-09-02 Bayer Ag Preparations antisolaires
US4264581A (en) * 1979-07-02 1981-04-28 Eli Lilly And Company Sunscreen composition
US4384974A (en) * 1979-07-27 1983-05-24 Revlon, Inc. Stable water-in-oil emulsions
EP0165457A2 (fr) * 1984-05-21 1985-12-27 Henkel Kommanditgesellschaft auf Aktien Ingrédient huileux cosmétique
EP0418443A1 (fr) * 1988-04-04 1991-03-27 Neutrogena Corporation Composition formant un écran solaire imperméable
US4940574A (en) * 1988-12-22 1990-07-10 Plough, Inc. Non-aqueous high SPF sunscreen oils
FR2670111A1 (fr) * 1990-12-11 1992-06-12 Bosserelle Micheline Composition de corps gras pour produits cosmetiques.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
S.T.N., FILE SUPPLIER, KARLSRUHE, DE File Chemical Abstracts, vol 111, an : 219316 *

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2309385A (en) * 1994-11-02 1997-07-30 Cussons Int Ltd Skin cleansing-UV screening composition
WO1996014053A1 (fr) * 1994-11-02 1996-05-17 Cussons (International) Limited Composition filtrant les uv et nettoyant la peau
GB2309385B (en) * 1994-11-02 1998-09-09 Cussons Int Ltd Skin cleansing-UV screening composition
US5716554A (en) * 1995-02-21 1998-02-10 Shiseido Co., Ltd. Ultraviolet light absorbent
EP0728470A3 (fr) * 1995-02-21 1996-12-04 Shiseido Co Ltd Composant absorbant de la lumière ultraviolette
AT408067B (de) * 1995-03-17 2001-08-27 Gebro Pharma Gmbh Pharmazeutische zusammensetzung zur topischen applizierung und verfahren zu ihrer herstellung
US5894019A (en) * 1995-03-17 1999-04-13 Gebro Broschek Gesellschaft M.B.H. Topically applied pharmaceutical composition, method of preparing it and its use
DE19615036A1 (de) * 1996-04-17 1997-10-23 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und Propylenglycolestern
DE19616926A1 (de) * 1996-04-27 1997-10-30 Beiersdorf Ag Kosmetische und dermatologische Lichtschutzformulierungen mit einem Gehalt an Triazinderivaten und Monoester und Diester aus verzweigten Alkancarbonsäuren und dem Diglycerin oder Triglycerin
US5961959A (en) * 1996-04-27 1999-10-05 Beiersdorf Ag Cosmetic and dermatological light protection formulations having a content of triazine derivatives and monoesters and diesters of branched alkanecarboxylic acids and diglycerol or triglycerol
DE19645318A1 (de) * 1996-11-04 1998-05-07 Beiersdorf Ag Stabile Lichtschutzzubereitungen mit einem Gehalt an grenzflächenaktiven Glucosederivaten und wasserlöslichen UV-Filtersubstanzen
EP0845259A3 (fr) * 1996-11-04 2000-05-24 Beiersdorf Aktiengesellschaft Compositions stables de protection solaire contenant des dérivés tensioactifs de glucose et des filtres ultraviolets hydrosolubles
EP1000611A1 (fr) * 1998-10-10 2000-05-17 Beiersdorf Aktiengesellschaft Utilisation de cires triglyceridiques pour augmenter l'indice de photoprotection d'une composition photoprotectrice
US7025758B2 (en) 2000-01-28 2006-04-11 William Cook Europe Aps Endovascular medical device with plurality of wires
US7834084B2 (en) 2004-08-04 2010-11-16 Adeka Corporation Light stabilizer emulsion composition and aqueous coating agent composition containing the same
WO2006013703A1 (fr) * 2004-08-04 2006-02-09 Adeka Corporation Composition d’émulsion stabilisatrice de lumière et composition de revêtement aqueuse contenant ladite composition
JPWO2006013703A1 (ja) * 2004-08-04 2008-05-01 株式会社Adeka 光安定剤乳化組成物、及びそれを含有する水系コーティング剤組成物
US7671096B2 (en) * 2005-02-14 2010-03-02 Adeka Corporation Light stabilizer emulsion composition
US20140170091A1 (en) * 2012-12-12 2014-06-19 Thomas Christopher Balshi Composition for Correcting Skin Pigment Conditions
US9351922B2 (en) * 2012-12-12 2016-05-31 Thomas Christopher Balshi Composition for correcting skin pigment conditions
CN108348426B (zh) * 2015-09-08 2021-10-15 诺瓦蒙特股份公司 含壬酸酯的水性化妆品组合物
CN108348426A (zh) * 2015-09-08 2018-07-31 诺瓦蒙特股份公司 含壬酸酯的水性化妆品组合物
JP2018526402A (ja) * 2015-09-08 2018-09-13 ノバモント・ソシエタ・ペル・アチオニＮｏｖａｍｏｎｔ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ ペラルゴン酸エステルを含有する水性化粧品用組成物
JP2018526400A (ja) * 2015-09-08 2018-09-13 ノバモント・ソシエタ・ペル・アチオニＮｏｖａｍｏｎｔ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ ペラルゴン酸エステルを含む親油性化粧品用組成物
JP2022017525A (ja) * 2015-09-08 2022-01-25 ノバモント・ソシエタ・ペル・アチオニ ペラルゴン酸エステルを含有する水性化粧品用組成物
JP2022017526A (ja) * 2015-09-08 2022-01-25 ノバモント・ソシエタ・ペル・アチオニ ペラルゴン酸エステルを含む親油性化粧品用組成物
US11400036B2 (en) 2015-09-08 2022-08-02 Novamont S.P.A. Aqueous cosmetic compositions containing pelargonic acid esters
US11992545B2 (en) 2015-09-08 2024-05-28 Novamont S.P.A. Aqueous cosmetic compositions containing pelargonic acid esters
WO2017191268A1 (fr) * 2016-05-06 2017-11-09 Novamont S.P.A. Compositions cosmétiques contenant du tétrapélargonate de diglycérol
JP2019514968A (ja) * 2016-05-06 2019-06-06 ノバモント・ソシエタ・ペル・アチオニＮｏｖａｍｏｎｔ Ｓｏｃｉｅｔａ Ｐｅｒ Ａｚｉｏｎｉ テトラペラルゴン酸ジグリセロールを含む化粧組成物
US11123274B2 (en) 2016-05-06 2021-09-21 Novamont S.P.A. Cosmetic compositions containing diglycerol tetrapelargonate
ITUA20163227A1 (it) * 2016-05-06 2017-11-06 Novamont Spa Composizioni cosmetiche contenenti diglicerolo tetrapelargonato.
JP7368941B2 (ja) 2016-05-06 2023-10-25 ノバモント・ソシエタ・ペル・アチオニ テトラペラルゴン酸ジグリセロールを含む化粧組成物

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