WO1997000851A1 - Composes chimiques et leurs procedes de production - Google Patents

Composes chimiques et leurs procedes de production Download PDF

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Publication number
WO1997000851A1
WO1997000851A1 PCT/GB1996/001481 GB9601481W WO9700851A1 WO 1997000851 A1 WO1997000851 A1 WO 1997000851A1 GB 9601481 W GB9601481 W GB 9601481W WO 9700851 A1 WO9700851 A1 WO 9700851A1
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WO
WIPO (PCT)
Prior art keywords
compound according
compound
substituted
skin
composition
Prior art date
Application number
PCT/GB1996/001481
Other languages
English (en)
Inventor
Peter Samuel James Cheetham
Nigel Eric Banister
Original Assignee
Zylepsis Limited
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 claimed from GBGB9512855.9A external-priority patent/GB9512855D0/en
Priority claimed from GBGB9525162.5A external-priority patent/GB9525162D0/en
Application filed by Zylepsis Limited filed Critical Zylepsis Limited
Priority to AU61327/96A priority Critical patent/AU6132796A/en
Priority to EP96918775A priority patent/EP0833812A1/fr
Priority to JP9503670A priority patent/JPH11507941A/ja
Publication of WO1997000851A1 publication Critical patent/WO1997000851A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/10—Esters; Ether-esters
    • C08K5/101—Esters; Ether-esters of monocarboxylic acids
    • C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols

Definitions

  • the present invention relates to novel compounds having properties which make them useful as sunscreen additives, processes for their preparation and formulations containing them, including formulations of cosmetic products.
  • uvC does not penetrate the earth's atmosphere, being absorbed by the ozone layer.
  • uvB has been identified as the causative agent of skin cancer. Accordingly, the majority of sunscreens currently available concentrate on the reduction of uvB rays contacting the skin.
  • uvA has now been identified as a cause of ageing of skin and hair wrinkling. As such, it is considered preferable to provide sunscreen agents which reduce the harmful effects of both uvA and uvB in sunlight.
  • sunscreens When used in cosmetic preparations there is a desire in the art to produce sunscreens which not only have the primary function of blocking ultraviolet light but also have the secondary function of caring for the skin to which they are applied. Thus many sunscreens also contain moisturisers and antioxidants as skin care additives.
  • sunscreens require new materials with improved uv radiation absorbing properties in order to create improved products with substantially superior protective properties. These products would be advantageous for a variety of applications where uv protection is important, for example in a range of personal care products such as hair shampoos, conditioners and hairsprays, in polymers, inks, colouring materials such as paints and dyes and also to prevent uv induced degradation of other actives and additives formulated or added to a system. Ideally, such materials should exhibit the following properties:
  • R, and R 2 are the same or different and represent H, OH, NH 2 , C0 2 H or OR 6
  • R 4 and R 5 are the same or different and represent H, OH, NH 2 or OR 6
  • R 6 is straight or branched chain C, - C 16 alkyl, alkylene or alkylyne or a substituted or unsubstituted homocyclic or heterocyclic aromatic group
  • R 3 is a substituted or unsubstituted homocyclic or heterocyclic aromatic ring which is in conjugation with a group R 7
  • R 7 is a substituted or unsubstituted homocyclic or heterocyclic aromatic ring, an alkene, or is an alkane substituted with a functional group capable of entering into conjugation with R 3
  • the preferred compounds of this invention may be used in sunscreen preparations that have the ability to absorb uv radiation in both the uvA and uvB region and measurements of this property are expressed by the terms defined below.
  • m.a.v. is the molar absorbance value (E) being the absorbance of one molar solution of a substance, measured in a 1cm path length cell at the given wavelength.
  • E 1% lcm is the specific absorbance of a substance being the absorbance of that substance at 1 % concentration in a 1 cm path length cell at the given wavelength.
  • the total uv absorbance is a representation of the area under the curve of the specific absorbance over the range 290nm to 450nm.
  • the preferred compounds described herein exhibit m.a.v. values > 1 x 10 4 at wavelength maxima and exhibit a total uv absorbance > 4 x 10 4 .
  • an alteration in pH of a solution of the compound results in an advantageous change in uv spectrum with a change in the measured ⁇ max often resulting in two maxima where previously there had been one.
  • This is embodied in the appearance of ⁇ max in the uvA region of the spectrum in addition to a ⁇ max in the uvB region and causes an increase in the total uv absorbance.
  • the nature of the ionic species involved in changing the pH influences the extent of alteration of the UV spectrum. This allows for manipulation and alteration of the uv absorbance characteristics exhibited by the chemical compound.
  • Alteration of the pH as described above can be effected by the use of acids or bases or Lewis acids or bases or solutions of buffer preparation containing these. Solutions of alkaline metal salts such as sodium hydroxide are, for example, of use in this respect. (See Advanced Organic Chemistry; Reactions. Mechanisms and Structure; J. March, McGraw-Hill, New York, 1968.)
  • Preferred embodiments of the present invention include compounds which individually exhibit combined uvA and uvB abso ⁇ tion properties. Accordingly, by using such a compound, rather than using separate compounds each exhibiting only one of either uvA or uvB abso ⁇ tion properties, the manufacture of product formulations is facilitated.
  • Preferred embodiments of the invention also include compounds which exhibit antioxidant activity.
  • the antioxidant activity can be measured by one of two primary methods. One method is based on the protection of lipids from oxidation and is described in Fat Sci. Technol., 1992, 94, 428 by Marinova and Yanishlieva. Another method is based on the measurement of antiradical activity as described in Lebensm. -Wiss. u-Technol , 1995, 28, 25 by Brand-Williams, Cuvelier and Berset.
  • Suitable examples of R 3 include the following or salts thereof:
  • alkene bond can be either cis or trans
  • alkene bond can be either cis or trans and where C0 2 X can represent an acid or ester moiety.
  • alkene bond can be either cis or trans
  • alkene bond can be either cis or trans and where C0 2 X can represent an acid or ester moiety
  • the group C0 2 X mentioned above as an example of R 3 represents an ester moiety.
  • Particularly preferred esters include 2- (ethyl)hexyl esters or 2-ethoxyethyl esters, ie. C,H,
  • X -CH 2 CHC 4 H 9 , or -CH 2 CH,OCH,CH 3
  • X represents a straight or branched chain C, - C 16 alkyl, alkene, or alkylyne optionally inco ⁇ orating a hetero atom replacement of a carbon to give, for example, an ether; also substituted or unsubstituted ring compounds, either homocyclic or hetercyclic including aromatic ring compounds.
  • R 3 will contain functional groups capable of forming salts or polarised associations with other ionic entities such as added acids or bases.
  • the present invention enables a large number of different formulations to be produced so as to cater precisely for particular consumer and product requirements.
  • photochemical energy may be dissipated by reversible trans-cis isomerisation. This is a mechanism that is indicative of good photochemical stability.
  • ester radical R 3 is an aromatic ring further conjugated with a multiple bond or functional group capable of entering into conjugation.
  • the conjugation may be continued through the carbon-carbon double bond to a carbonyl function in the form of a cyclic ester as in Structure I or in the form of an acid as in Structure II above.
  • the carbonyl function may also be in the form of an ester of an acid e.g. the methyl ester of Structure II above.
  • Umbelliferyl 4-methoxycinnamate (Structure III) is a novel molecule that provides very intense absorption, double that of octyl methoxycinnamate, with a ⁇ max. of 321 nms. Upon addition of NaOH, intense and combined uvA and uvB abso ⁇ tion is obtained with ⁇ max. of 376 and 310nms respectively. Such absorption is superior to that exhibited by known mixtures of uvA and uvB absorbing materials.
  • R represents hydroxy.
  • the presence of a 4-hydroxy group appears to allow the UV abso ⁇ tion effect of the molecule to be shifted more into the uvA region by adjusting the pH of a formulation containing the molecule.
  • Ferulic acid esters of especial interest include
  • the 2-ethoxyethyl esters can be prepared in the same ways using 2-ethoxyethanol in place of 2-ethylhexan- l -ol .
  • a further preferred compound of the invention is
  • Methods for the preparation of the compounds embodied herein include methods for the formation of esters.
  • Enzyme catalysed reaction to form an ester may be as described in outline in Enzymes in Synthetic Organic Chemistry. C-H Wong and G M Whitesides. Pergamon, Elsevier Science Ltd, 1994.
  • Methods for coupling the acid functionality of a substituted cinnamic acid, for example caffeic acid, with an alcohol group, for example hydroxycinnamic acid, to form an ester encompassed by structure B are suitable.
  • these methods can include dehydration by azeotropic water removal, as described for example in Vogel's Textbook of Practical Organic Chemistry, A Vogel, revised B Furniss et al, Longman Scientific & Technical Publishing, 1989; mechanical or chemical water removal; conversion of the acid functionality to an activated derivative e.g. acid halide or activated ester followed by reaction with the alcohol; transesterification of a suitable ester derivative; enzyme catalysed ester formation from the acid and alcohol structure; enzyme catalysed transesterification of a suitable structure, e.g. chlorogenic acid. It will be apparent to a skilled person that control of the relative quantities of substrate and reagents used in the protocol for ester formation will determine the extent of ester formation.
  • Umbelliferyl 3.4-dimethoxycinnamate (3.4-Dimethoxycinnamic acid ester with 7-Hydroxycoumarin) synthesis.
  • the unpurified 4-methoxycinnamyl chloride (28 mmole) as prepared in example 2 was resuspended in toluene (40ml) and added to -coumaric acid (4.6g, 28 mmole). The mixture was boiled under reflux for 1 hour and the mauve precipitate which formed upon cooling was filtered and washed with diethyl ether to yield a white solid. This was dried with heating in vacuo to yield the title compound. (8.08g, 75 % purity, 97% yield).
  • the main impurity was the diester as described in example 8.
  • addition of a base such as a Lewis base causes a shift in the ultraviolet spectrum for the compound, often with the appearance of a wavelength maxima in the uvA region of the spectrum in addition to a wavelength maxima in the uvB region of the spectrum and an increase in total ultraviolet absorbance.
  • the compounds of the present invention may be inco ⁇ orated into product formulations such as creams, lotions and emollients either directly as produced above or, alternatively, in the form of a salt or adduct thereof, for example, following addition of a base.
  • Creams, lotions and emollients produced in this way are particularly useful as sun-care products due to their sunscreening effects which may be in both the uvA and uvB regions.
  • such formulations are also useful as health-care and/or cosmetic products because many of the compounds of the present invention have other useful properties such as antioxidant and antimicrobial activities and can help prevent or mitigate wrinkling and/or ageing of the skin and hair.
  • the creams, lotions or emollients into which the compounds of the present invention may be incorporated may be water-based or oil-based many may contain other useful components providing such properties as aroma, skin permeability, moisturisers, antioxidants and antimicrobial components.
  • thermostability and solubility characteristics of these novel compounds together with their uv absorbing properties make them suitable for a variety of applications including inco ⁇ oration into fabrics, dyes, polymers, inks, paints and other chemical compositions to confer protection from light induced decomposition.
  • a sunscreen oil formulation comprises a compound of the invention and an adjuvant as follows:
  • UV absorber 6.0% weight capric/caprylic triglyceride 5.0% weight fragrance 0J % weight isopropyl palmitate 24.0% weight
  • the UV absorber is a compound of the invention.
  • the relative proportion of active UV absorber can be varied to alter the level of protection afforded by the sunscreen oil.
  • a water in oil sunscreen lotion of the invention comprises:
  • Inco ⁇ oration of the compounds of the invention into hair products such as shampoos, conditioners, mousse and colorants is a preferred application.
  • the percentages refer to the weight of he ingredients.
  • UV asborber 1.50% In each case the relative amounts of ingredients can be varied to alter the properties of the product as desired.
  • the UV absorber compound is inco ⁇ orated at 0.5 % w/w into polyolefin material prior to extrusion to form a plastic film which exhibits resistance to light-induced decomposition.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention concerne un composé de formule (B) ainsi que ses sels ou additifs. Dans la formule, R1 et R2 sont identiques ou différents et représentent N, OH, NH2, CO2H ou OR6; R4 et R5 sont identiques ou différents et représentent H, OH, NH2 ou OR6; R6 représente C1-C16 alkyle, alkylène ou alkylyne à chaîne linéaire ou ramifiée ou un groupe aromatique homocyclique ou hétérocyclique substitué ou non substitué; R3 représente un anneau aromatique homocyclique ou hétérocyclique substitué ou non substitué qui est conjugué à un groupe R7; R7 représente un anneau aromatique homocyclique ou hétérocyclique substitué ou non substitué, un alcène ou un alcane substitué par un groupe fonctionnel capable d'entrer en conjugaison avec R3. Ce composé est à même d'absorber les radiations ultraviolettes dans les régions des UVA et des UVB du spectre ultraviolet et possède une activité antioxydante qui lui confère une utilité en tant qu'additif dans une composition de filtre solaire et dans diverses compositions cosmétiques et non cosmétiques telles que des produits de soin pour le cheveux, des encres, des peintures et des colorants.
PCT/GB1996/001481 1995-06-23 1996-06-21 Composes chimiques et leurs procedes de production WO1997000851A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
AU61327/96A AU6132796A (en) 1995-06-23 1996-06-21 Chemical compounds and methods of production thereof
EP96918775A EP0833812A1 (fr) 1995-06-23 1996-06-21 Composes chimiques et leurs procedes de production
JP9503670A JPH11507941A (ja) 1995-06-23 1996-06-21 化学化合物およびその製造方法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9512855.9A GB9512855D0 (en) 1995-06-23 1995-06-23 Chemical compounds and methods of production thereof
GBGB9525162.5A GB9525162D0 (en) 1995-12-08 1995-12-08 Chemical compounds and methods of production thereof
GB9512855.9 1995-12-08
GB9525162.5 1995-12-08

Publications (1)

Publication Number Publication Date
WO1997000851A1 true WO1997000851A1 (fr) 1997-01-09

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EP (1) EP0833812A1 (fr)
JP (1) JPH11507941A (fr)
AU (1) AU6132796A (fr)
WO (1) WO1997000851A1 (fr)

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999013825A1 (fr) * 1997-09-17 1999-03-25 The Procter & Gamble Company Compositions de soins capillaires comprenant des hydroxycoumarines
WO1999047118A1 (fr) * 1998-03-16 1999-09-23 The Procter & Gamble Company Compositions pour modifier l'aspect exterieur de la peau
EP1090952A1 (fr) * 1999-10-06 2001-04-11 Basf Aktiengesellschaft Composition de stabilisateurs
US6235271B1 (en) 1997-07-26 2001-05-22 Ciba Specialty Chemicals Corporation UV-protection formulation
WO2003022246A1 (fr) 2001-09-06 2003-03-20 Synzyme Technologies Llc Traitement des effets des especes reactives de l'oxygene
US6646153B1 (en) * 2000-07-19 2003-11-11 E. I. Du Pont De Nemours And Company Hydroxyl functional urethanes having a tertiary carbamate bond
US6746666B1 (en) 1999-06-18 2004-06-08 Ciba Specialty Chemicals Corporation Micropigment mixture
WO2008062466A2 (fr) * 2006-10-13 2008-05-29 Reliance Life Sciences Pvt. Ltd. Nouveaux agents chimiothérapeutiques contre l'inflammation et le cancer
US7435438B1 (en) 2003-05-16 2008-10-14 Pure Bioscience Disinfectant and method of use
WO2012034932A1 (fr) 2010-09-14 2012-03-22 Basf Se Utilisation de dérivés de bis(biphényl)triazine spécifiques et leurs mélanges comme absorbeurs d'uv
WO2012052499A1 (fr) 2010-10-22 2012-04-26 Basf Se Utilisation de dérivés de silane et de siloxane bis(biphényl)triazine comme absorbeurs uv
WO2013024099A1 (fr) 2011-08-16 2013-02-21 Basf Se Composition comprenant un ingrédient actif, une huile et un liquide ionique
CN103764610A (zh) * 2011-06-30 2014-04-30 Dic株式会社 肉桂酸衍生物及其聚合物、以及由其固化物构成的液晶取向层
EP2743337A1 (fr) 2012-12-14 2014-06-18 Cognis IP Management GmbH Dérivés de polyglycérol tensioactifs
TWI500742B (zh) * 2009-04-14 2015-09-21 Dainippon Ink & Chemicals 含有聚合性化合物之液晶組成物及使用它之液晶顯示元件
US9669243B2 (en) 2008-04-23 2017-06-06 Basf Se Delivery of hydrophobic benefit agents from bodywashes and the like onto a keratinous substrate
US10219990B2 (en) 2014-12-09 2019-03-05 Basf Se Solubilizing agents for UV filters in cosmetic formulations
US10449135B2 (en) 2014-04-09 2019-10-22 Basf Se Solublizing agents for UV filters in cosmetic formulations
CN111057036A (zh) * 2019-12-02 2020-04-24 五邑大学 一种香豆素衍生物及其制备方法与应用
CN111202730A (zh) * 2020-02-19 2020-05-29 五邑大学 一种香豆素衍生物在抑制酪氨酸酶活性中的应用
US11793742B2 (en) 2014-04-11 2023-10-24 Basf Se Mixtures of cosmetic UV absorbers

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KR100547109B1 (ko) * 2002-11-14 2006-01-26 삼성전자주식회사 자외선 흡수 치환기를 포함한 기능성 첨가제 및 이를포함하는잉크 조성물

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Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6235271B1 (en) 1997-07-26 2001-05-22 Ciba Specialty Chemicals Corporation UV-protection formulation
WO1999013825A1 (fr) * 1997-09-17 1999-03-25 The Procter & Gamble Company Compositions de soins capillaires comprenant des hydroxycoumarines
US6235773B1 (en) 1998-03-16 2001-05-22 The Procter & Gamble Company Compositions for regulating skin appearance
US6051602A (en) * 1998-03-16 2000-04-18 The Procter & Gamble Company Methods for regulating skin appearance
US6093411A (en) * 1998-03-16 2000-07-25 The Procter & Gamble Company Compositions for regulating skin appearance
WO1999047119A1 (fr) * 1998-03-16 1999-09-23 The Procter & Gamble Company Procedes pour modifier l'aspect exterieur de la peau
WO1999047118A1 (fr) * 1998-03-16 1999-09-23 The Procter & Gamble Company Compositions pour modifier l'aspect exterieur de la peau
US6746666B1 (en) 1999-06-18 2004-06-08 Ciba Specialty Chemicals Corporation Micropigment mixture
EP1187598B1 (fr) * 1999-06-18 2009-10-21 Basf Se Melanges de micropigments
EP1090952A1 (fr) * 1999-10-06 2001-04-11 Basf Aktiengesellschaft Composition de stabilisateurs
US6646153B1 (en) * 2000-07-19 2003-11-11 E. I. Du Pont De Nemours And Company Hydroxyl functional urethanes having a tertiary carbamate bond
WO2003022246A1 (fr) 2001-09-06 2003-03-20 Synzyme Technologies Llc Traitement des effets des especes reactives de l'oxygene
US7435438B1 (en) 2003-05-16 2008-10-14 Pure Bioscience Disinfectant and method of use
WO2008062466A2 (fr) * 2006-10-13 2008-05-29 Reliance Life Sciences Pvt. Ltd. Nouveaux agents chimiothérapeutiques contre l'inflammation et le cancer
WO2008062466A3 (fr) * 2006-10-13 2008-09-25 Reliance Life Sciences Pvt Ltd Nouveaux agents chimiothérapeutiques contre l'inflammation et le cancer
US9669243B2 (en) 2008-04-23 2017-06-06 Basf Se Delivery of hydrophobic benefit agents from bodywashes and the like onto a keratinous substrate
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EP0833812A1 (fr) 1998-04-08
AU6132796A (en) 1997-01-22

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