WO2006066643A1 - Esters of choline and fatty acids with bactericide activity and products containing such esters for cosmetic or dermo-pharmaceutical products - Google Patents

Esters of choline and fatty acids with bactericide activity and products containing such esters for cosmetic or dermo-pharmaceutical products Download PDF

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Publication number
WO2006066643A1
WO2006066643A1 PCT/EP2005/009870 EP2005009870W WO2006066643A1 WO 2006066643 A1 WO2006066643 A1 WO 2006066643A1 EP 2005009870 W EP2005009870 W EP 2005009870W WO 2006066643 A1 WO2006066643 A1 WO 2006066643A1
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WO
WIPO (PCT)
Prior art keywords
dermo
pharmaceutical
cosmetic
esters
substance
Prior art date
Application number
PCT/EP2005/009870
Other languages
French (fr)
Inventor
Giovanni Razzano
Original Assignee
Oro Consulting S.R.L.
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 Oro Consulting S.R.L. filed Critical Oro Consulting S.R.L.
Publication of WO2006066643A1 publication Critical patent/WO2006066643A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
    • A61L2/16—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using chemical substances
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • the present invention concerns a new emulsifying and/or surfactant substance with bactericide activity .
  • the substance is suitable for the preparation of emulsions and of tensides for dermo-pharmaceutical and cosmetic use .
  • the same invention also concerns the emulsions and tensides prepared with this substance and the dermo-pharmaceutical products and cosmetic products obtained with these emulsions and with these tensides .
  • the same invention also concerns other uses of said new substance .
  • the field of application of the invention is that of emulsions and tensides used in the preparation of dermo- pharmaceutical and cosmetic products , in which the dispersion of the fatty matter in water, or vice-versa, is carried out either through suitable emulsifiers , the most common of which are ethylene oxide derivatives and ionic emulsifiers , or by the addition of surfactants , the most widely used of which are LESs (lauryl ether sulphates) , betaines and sulfosuccinates .
  • suitable emulsifiers the most common of which are ethylene oxide derivatives and ionic emulsifiers
  • surfactants the most widely used of which are LESs (lauryl ether sulphates) , betaines and sulfosuccinates .
  • the main purpose of the present invention is that of providing a new emulsifying and/or surfactant substance , suitable for preparing emulsions and tensides for dermo- pharmaceutical and cosmetic use that , unlike known substances of the same type , whilst still offering the desired dispersion and debridement effect , has no secondary action of negative interference with the physiological activities of the skin .
  • Yet another purpose of the invention is that of offering the emulsifying and/or surfactant substance of the aforementioned type , which also includes within itself a bactericide function, without requiring the addition of specific auxiliary active substances , since the action is already covered by the emulsifier and would thus allow the preparation of cosmetics "without preservatives"
  • those according to the invention offer the advantage of being widely dermocompatible and of also offering strong bactericide action, whilst still being without specific components for such a purpose ( I would eliminate the paragraph because we have already said this)
  • the emulsifying and/or surfactant substance with bactericide activity of the invention consists of choline esters having the general formula :
  • - R is a function with lipophile action consisting of aliphatic chains C 6 -C 36 taken individually or in mixture ;
  • - X is a halogen, a nitrate ion, phosphate , tosylate or methanesulfonate .
  • the bactericide action of the substance of formula ( 1 ) derives from the group -N + - (CH 3 ) 3 - of choline .
  • the lipophile action of group R of the same formula ( 1) gives the substance its emulsifying and/or surfactant property, a function of the length of the aliphatic chain and of the composition of the mixture .
  • Cosurf actants that can be foreseen in the substance according to the invention are glyceryl monostearate, cetyl stearyl alcohol, polysorbate 60, sodiumcocoylglutamate .
  • the synthesis reaction of the emulsifying and surfactant substance of the previous formula (1) can either be direct esterif ication between natural fatty acids listed earlier and choline (variously salified - scheme 1 - or else from the natural fatty acids themselves by using a synthesis sequence that allows the choline function to be constructed - scheme II -
  • Cosmetic cream with natural emulsifier Cosmetic cream with natural emulsifier
  • the emulsifying and/or surfactant substance with bactericide activity of the present invention has a much wider scope of application, also being able to be used in the industrial field .
  • the emulsifying and/or surfactant substance of the present invention can be used in the field of textiles and/or the iron and steel industry and/or the metallurgical industry and/or in the field of detergents in general , to give lubricating and/or wetting activity, as well as bactericide activity .

Abstract

An emulsifying and/or surfactant substance with bactericide activity for the preparation of emulsions and of tensides for dermo-pharmaceutical and cosmetic use, consisting of choline esters having the general formula (I) where: R is a function with lipophile action consisting of aliphatic chains C6-C36 taken individually or in mixture; X¯ is a halogen, a nitrate ion, phosphate, tosylate or methanesulfonate. With respect to conventional emulsifiers, the one according to the invention offers the advantage of being widely dermocompatible and of also offering strong bactericide action, whilst still being without specific components for such a purpose.

Description

ESTERS OF CHOLINE AND FATTY ACIDS WITH BACTERICIDE ACTIVITY AND PRODUCTS CONTAINING SUCH ESTERS FOR COSMETIC OR DERMO-PHARMACEUTICAL PRODUCTS
DESCRIPTION
The present invention concerns a new emulsifying and/or surfactant substance with bactericide activity . The substance is suitable for the preparation of emulsions and of tensides for dermo-pharmaceutical and cosmetic use . The same invention also concerns the emulsions and tensides prepared with this substance and the dermo-pharmaceutical products and cosmetic products obtained with these emulsions and with these tensides . The same invention also concerns other uses of said new substance .
The field of application of the invention is that of emulsions and tensides used in the preparation of dermo- pharmaceutical and cosmetic products , in which the dispersion of the fatty matter in water, or vice-versa, is carried out either through suitable emulsifiers , the most common of which are ethylene oxide derivatives and ionic emulsifiers , or by the addition of surfactants , the most widely used of which are LESs (lauryl ether sulphates) , betaines and sulfosuccinates .
Conventional emulsifiers of the aforementioned type , nevertheless , have the drawback of having an allergenic action, due to the low skin compatibility of these products , whereas the surfactants present in the tensides have the disadvantage of delipidizing and irritating the skin .
Known conventional emulsions and tensides for dermo- pharmaceutical and cosmetic use must also be integrated with substances with bactericide action . Conventionally, therefore , the preparation of emulsions and tensides foresees the addition, next to the emulsifiers and the surfactants , also of such antimicrobe substances , with a consequent increase in the preparation costs of the relative dermo- pharmaceutical and cosmetic products and, above all , with a negative overlapping effect of the toxicity of the added components . I would remove the part in brackets
The main purpose of the present invention is that of providing a new emulsifying and/or surfactant substance , suitable for preparing emulsions and tensides for dermo- pharmaceutical and cosmetic use that , unlike known substances of the same type , whilst still offering the desired dispersion and debridement effect , has no secondary action of negative interference with the physiological activities of the skin .
Yet another purpose of the invention is that of offering the emulsifying and/or surfactant substance of the aforementioned type , which also includes within itself a bactericide function, without requiring the addition of specific auxiliary active substances , since the action is already covered by the emulsifier and would thus allow the preparation of cosmetics "without preservatives"
These and other purposes are accomplished with the emulsifying and/or surfactant substance , the emulsion and the tenside according to claims 1 , 5 and 6 respectively . Preferred embodiments of the invention can be seen from the remaining claims .
With respect to conventional emulsions and tensides , those according to the invention offer the advantage of being widely dermocompatible and of also offering strong bactericide action, whilst still being without specific components for such a purpose ( I would eliminate the paragraph because we have already said this)
The emulsifying and/or surfactant substance with bactericide activity of the invention consists of choline esters having the general formula :
0
[R-C-OCH2-CHrN*-(CH3)3] >T (1)
where :
- R is a function with lipophile action consisting of aliphatic chains C6-C36 taken individually or in mixture ;
- X is a halogen, a nitrate ion, phosphate , tosylate or methanesulfonate .
In particular, according to the invention, the bactericide action of the substance of formula ( 1 ) derives from the group -N+- (CH3) 3- of choline . For its part , the lipophile action of group R of the same formula ( 1) gives the substance its emulsifying and/or surfactant property, a function of the length of the aliphatic chain and of the composition of the mixture .
Amongst the preferred aliphatic chains for. the function R, we quote mixtures of fatty acids of natural origin, saturated or unsaturated (from coconut or babassu oil) , with chain Cs— C3S. Other fatty acids that can be used for the invention are those with chain C12-Ci8 (lauric acid and stearic acid) and of equivalent natural origin.
Cosurf actants that can be foreseen in the substance according to the invention are glyceryl monostearate, cetyl stearyl alcohol, polysorbate 60, sodiumcocoylglutamate .
The synthesis reaction of the emulsifying and surfactant substance of the previous formula (1) can either be direct esterif ication between natural fatty acids listed earlier and choline (variously salified - scheme 1 - or else from the natural fatty acids themselves by using a synthesis sequence that allows the choline function to be constructed - scheme II -
(D
R-COOH + HO- (CH2) 2-N- (CH3J3 +X' → R-CO-O- (CH2) 2-N- (CH3) 3 +X~
(ID
R-COOH + HO- (CH2) 2-N- (CH3) 2 → R-CO-O- (CH2) 2-N- (CH3) 2 R-CO-O- (CH2) 2-N- (CH3) 2 + CH3X → R-CO-O- (CH2) 2-N- (CH3) 3 +X" For illustrating and not limiting purposes , hereafter we shall give some examples of product formulations for dermo- pharmaceutical and cosmetic use , prepared with the emulsions and tensides according to the invention . The percentages are by weight .
Cosmetic cream with natural emulsifier
Stearyl choline methanesulfonate 6%
Cetyl stearyl alcohol 3%
Glyceryl monostearate 2.5%
Vegetable oil 10%
Antioxidants 0.05%
WATER the remainder to 100
Dermo-pharmaceutical cream with natural emulsifier
Stearyl choline methanesulfonate 6%
Cetyl stearyl alcohol 3 %
Glyceryl monostearate 2.5%
Vaseline oil 10%
Antioxidants 0.05%
WATER the remainder to 100
Shower cream
Cocamidopropylbetaine 3.5%
Laurylcholine methanesulfonate 5%
Sodiumlaurylsarcosinate 5%
Babassu monoethanolamide 1.5%
Perfume 0.8%
WATER the remainder to 100 Advantageously, it has been found that the emulsifying and/or surfactant substance with bactericide activity of the present invention has a much wider scope of application, also being able to be used in the industrial field .
In particular, the emulsifying and/or surfactant substance of the present invention can be used in the field of textiles and/or the iron and steel industry and/or the metallurgical industry and/or in the field of detergents in general , to give lubricating and/or wetting activity, as well as bactericide activity .

Claims

1. Emulsifying and/or surfactant substance with at least bactericide activity for the preparation of emulsions and of tensides for dermo-pharmaceutical and cosmetic use, characterised in that it consists of esters of fatty acids of choline , by themselves or in mixture .
2. Substance according to claim 1 , characterised in that said esters have the general formula :
0
[R-C-O-CH2-CHrN^-(CHs)3] X" (1)
where :
R is a function with lipophile action consisting of aliphatic chains C6-C3S taken individually or in mixture ; - X is a halogen, a nitrate ion, phosphate, tosylate or methanesulfonate .
3. Substance according to claim 1 or 2 , characterised in that R consists of fatty acids of natural origin, saturated or unsaturated, with chain C6-C36 , by themselves or in mixture .
4. Substance according to claim 3 , characterised in that the quoted fatty acids consist of acids from coconut oil , babassu oil , lauric acid, stearic acid, capric , caprylic , capronic , myristic , palmitic and oleic acid .
5. Emulsion for dermo-pharmaceutical and/or cosmetic use , characterised in that it comprises the substance according to claims 1 to 4 that allows the preparation of dermo- pharmaceutical and cosmetic preparations without the need for the addition of the preservative ingredient .
6. Tenside for dermo-pharmaceutical and/or cosmetic use , characterised in that it comprises the substance according to claims 1 to 4 that allows the preparation of dermo- pharmaceutical and cosmetic preparations without the need for the addition of the preservative ingredient .
7. Tenside according to claim 6 , characterised in that it also comprises cosurfactants , by themselves or in mixture .
8. Tenside according to claim 6 , characterised in that said surfactants consist of glyceryl monostearate , cetyl stearyl alcohol , polysorbate 60 , sodiumcocoylglutamate .
9. Dermo-pharmaceutical product , characterised in that it is prepared with the surfactant and/or the tenside according to one or more of the previous claims .
10. Dermo-pharmaceutical product according to claim 9 , characterised in that it consists of a dermo-pharmaceutical cream made up of :
Stearyl choline methanesulfonate 6%
Cetyl stearyl alcohol 3 %
Glyceryl monostearate 2.5%
Vaseline oil 10%
Antioxidants 0.05%
WATER the remainder to 100
11. Dermo-pharmaceutical product , characterised in that it is prepared with the surfactant and/or the tenside according to one or more of the previous claims .
12. Cosmetic product according to claim 10 , characterised in that it consists of a cosmetic cream made up of :
Stearyl choline methanesulfonate 6%
Cetyl stearyl alcohol 3%
Glyceryl monostearate 2.5%
Vaseline oil 10%
Antioxidants 0.05%
WATER the remainder to 100
13. Product according to claims 9 and 11 , characterised in that it consists of a shower cream made up of : Cocamidopropylbetaine 3.5% Laurylcholine methanesulfonate 5% Sodiumlaurylsarcosinate 5%
Babassu monoethanolamide 1.5%
Perfume 0.8%
WATER the remainder to 100
14. Use of the substance according to one or more of the previous claims , for the preparation of emulsions and tensides with bactericide activity .
15. Use of the substances according to one or more of the previous claims , to also give lubricating and/or wetting activity .
16. Use according to the previous claim in the field of textiles and/or the iron and steel industry and/or the metallurgical industry and/or in the field of detergents in general .
PCT/EP2005/009870 2004-12-24 2005-09-14 Esters of choline and fatty acids with bactericide activity and products containing such esters for cosmetic or dermo-pharmaceutical products WO2006066643A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITMI2004A002505 2004-12-24
IT002505A ITMI20042505A1 (en) 2004-12-24 2004-12-24 EMULSIFYING SUBSTANCE AND-OR TENSIOACTIVE FOR BACTERICIDAL ACTIVITY FOR THE PREPARATION OF EMULSIONS AND TENSIDES FOR DERMOPRARMACEUTICAL AND COSMETIC USE EMULSIONS AND TENSIDES PREPARED WITH THIS SUBSTANCE DERMO-PHARMACEUTICAL PRODUCT AND OTT COSMETIC PRODUCT

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WO2006066643A1 true WO2006066643A1 (en) 2006-06-29

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7053584B2 (en) 2002-10-03 2006-05-30 Japan Servo.Co., Ltd. Motor driving device
DE102006014296A1 (en) * 2006-03-28 2007-10-04 Schill + Seilacher Aktiengesellschaft Acylating choline chloride, useful to prepare fattyacidcholinesaltester, comprises reacting choline chloride, methanesulfonic acid and fatty acid chloride at specific temperature, without adding solvent
FR2934153A1 (en) * 2008-07-23 2010-01-29 Oreal Cosmetic composition, useful for treating keratin materials, and as optionally rinsed after shampoo hair conditioner, comprises cationic surfactant having quaternary ammonium salt structure, polyol and non-silicone polymer thickener
US20110014148A1 (en) * 2008-03-12 2011-01-20 Cognis Ip Management Gmbh Cationic Surfactants Having Improved Properties
WO2011034425A1 (en) 2009-09-17 2011-03-24 Latexfalt B.V. Storage stable emulsions from low penetration grade bituminous binders
WO2011034423A1 (en) 2009-09-17 2011-03-24 Latexfalt B.V. Storage stable, light coloured emulsions from low penetration grade clear binders
WO2011034424A1 (en) 2009-09-17 2011-03-24 Latexfalt B.V. Waterproofing chipless asphalt top seal composition

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US4822773A (en) * 1985-06-28 1989-04-18 Merck & Co., Inc. Enhancement of absorption of drugs from gastrointestinal tract using choline ester salts
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Publication number Priority date Publication date Assignee Title
US4264466A (en) * 1980-02-14 1981-04-28 The Procter & Gamble Company Mulls containing chain structure clay suspension aids
EP0059980A1 (en) * 1981-03-11 1982-09-15 NATEC Institut für naturwissenschaftlich- technische Dienste GmbH Use of an antimicrobial preservative in ophtalmics and the care of contact lenses
US4822773A (en) * 1985-06-28 1989-04-18 Merck & Co., Inc. Enhancement of absorption of drugs from gastrointestinal tract using choline ester salts
EP0331948A2 (en) * 1988-02-22 1989-09-13 Schur Pharmazeutika Gmbh & Co Kg Pharmaceutical composition for the transdermal administration of heparin
US4892737A (en) * 1988-09-22 1990-01-09 University Of Florida Composition and method for enhancing permeability of topical drugs
US5545350A (en) * 1992-05-12 1996-08-13 The Procter & Gamble Company Concentrated fabric softener compositions containing biodegradable fabric softeners
US5536421A (en) * 1992-09-28 1996-07-16 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
WO1999015013A2 (en) * 1997-09-24 1999-04-01 Cognis Deutschland Gmbh Use of quaternary carboxylic acid alkanolamine ester salts as microbicidal agents
US5977174A (en) * 1997-11-26 1999-11-02 Neuromedica, Inc. Cholinergic compositions and uses thereof

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Title
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7053584B2 (en) 2002-10-03 2006-05-30 Japan Servo.Co., Ltd. Motor driving device
DE102006014296A1 (en) * 2006-03-28 2007-10-04 Schill + Seilacher Aktiengesellschaft Acylating choline chloride, useful to prepare fattyacidcholinesaltester, comprises reacting choline chloride, methanesulfonic acid and fatty acid chloride at specific temperature, without adding solvent
US20110014148A1 (en) * 2008-03-12 2011-01-20 Cognis Ip Management Gmbh Cationic Surfactants Having Improved Properties
FR2934153A1 (en) * 2008-07-23 2010-01-29 Oreal Cosmetic composition, useful for treating keratin materials, and as optionally rinsed after shampoo hair conditioner, comprises cationic surfactant having quaternary ammonium salt structure, polyol and non-silicone polymer thickener
WO2011034425A1 (en) 2009-09-17 2011-03-24 Latexfalt B.V. Storage stable emulsions from low penetration grade bituminous binders
WO2011034423A1 (en) 2009-09-17 2011-03-24 Latexfalt B.V. Storage stable, light coloured emulsions from low penetration grade clear binders
WO2011034424A1 (en) 2009-09-17 2011-03-24 Latexfalt B.V. Waterproofing chipless asphalt top seal composition

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