FR2504530A1 - Substd. alkyl 4-methoxy-cinnamic acid ester derivs. - useful as sunscreening agents - Google Patents
Substd. alkyl 4-methoxy-cinnamic acid ester derivs. - useful as sunscreening agents Download PDFInfo
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- FR2504530A1 FR2504530A1 FR8108429A FR8108429A FR2504530A1 FR 2504530 A1 FR2504530 A1 FR 2504530A1 FR 8108429 A FR8108429 A FR 8108429A FR 8108429 A FR8108429 A FR 8108429A FR 2504530 A1 FR2504530 A1 FR 2504530A1
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Abstract
Description
La présente invention concerne des composés chimiques nouveaux utiles notamment en cosmétologie, par exemple comme filtre solaire. The present invention relates to new chemical compounds useful in particular in cosmetology, for example as a sunscreen.
La présente invention concerne des composés chimiques nouveaux de formule I
dans laquelle n est un nombre entier supérieur ou gal à 1, et R est un radical organique lié au radical alcoylène par un atome d'azote, de soufre ou d'oxygene ; ainsi queles sels de ces composés.The present invention relates to new chemical compounds of formula I
wherein n is an integer greater than or equal to 1, and R is an organic radical linked to the alkylene radical by a nitrogen, sulfur or oxygen atom; as well as the salts of these compounds.
Parmi les significations de R, à titre de radical organique il faut mentionner plus particulibrement les radicaux amino, substitués ou non, et les sels d'ammonium quaternaire correspondants de formule (a) ou (b) :
dans lesquelles R1 et R2 sont l'hydrogene ou des radicaux aliphatiques, aryliques, aralcoyles, cycloaliphatiques, cycloaliphatiques-alcoyles, hétérocycliques ou hetérocycliques-alcoyles, substitués ou non, ou bien R1 et R2 pris ensemble forment un radical hétérocyclique azoté, substitué ou non substitué ; R3 est l'hydrogène ou un radical alcoyle inférieur et X est l'anion d'un acide pharmaceutiquement acceptable.Among the meanings of R, as organic radical, it is necessary to mention more particularly the amino radicals, substituted or not, and the corresponding quaternary ammonium salts of formula (a) or (b):
in which R1 and R2 are hydrogen or aliphatic, aryl, aralkyl, cycloaliphatic, cycloaliphatic-alkyl, heterocyclic or heterocyclic-alkyl radicals, substituted or not, or else R1 and R2 taken together form a nitrogen heterocyclic radical, substituted or unsubstituted substituted; R3 is hydrogen or a lower alkyl radical and X is the anion of a pharmaceutically acceptable acid.
Dans un autre mode de réalisation, le radical
R peut être un radical de formule (c)
(c) (x)mR1 dans laquelle X est un atome de soufre ou d'oxygène, m est un nombre entier supérieur ou égal a 1 et R1 a l'une des significations précédentes ou bien représente le radical
c'est-à-dire que dans ce cas on obtient, en particulier, des sulfures et des polysulfures symétriques.In another embodiment, the radical
R can be a radical of formula (c)
(c) (x) mR1 in which X is a sulfur or oxygen atom, m is an integer greater than or equal to 1 and R1 has one of the preceding meanings or else represents the radical
that is to say, in this case, symmetrical sulfides and polysulfides are obtained in particular.
Parmi les radicaux aliphatiques, il faut citer plus particulièrement les radicaux alcoyles, alcényles ou alcinyles substitués ou non substitués. Among the aliphatic radicals, mention should be made more particularly of substituted or unsubstituted alkyl, alkenyl or alkinyl radicals.
Par radicaux alcoyles, on entend désigner plus particulièrement des radicaux alcoyles inférieurs en C1-C5, droits ou ramifiés, tels que méthyle, éthyle, isopropyle, n-propyle ou t-butyle par exemple. The term “alkyl radicals” is intended to denote more particularly lower C1-C5 alkyl radicals, straight or branched, such as methyl, ethyl, isopropyl, n-propyl or t-butyl for example.
Par radicaux alcényles, on entend désigner plus particulièrement des radicaux alcényles, droits ou ramifiés, en C2-C5 tels que vinyle et allyle par exemple. The term “alkenyl radicals” is intended to denote more particularly alkenyl radicals, straight or branched, of C2-C5 such as vinyl and allyl for example.
Par radicaux alcinyles, on entend désigner plus particulièrement des radicaux alcinyles, droits ou ramifiés, en C2-C5 tels que propargyle par exemple. By alkynyl radicals is meant more particularly denote alkynyl radicals, straight or branched, C2-C5 such as propargyl for example.
Par radicaux cycloaliphatiques, on entend désigner un radical monocyclique comportant de 3 à 6 atomes de carbone saturé, c'est-à-dire cyclopropyle, cyclobutyle, cyclopentyle et cyclohexyle, ou insaturé comportant une ou plusieurs insaturations, en particulier éthylénique, par exemple cyclobutényle, cyclopentényle, cyclohexényle, cyclohexadiényle, mais, il peut s'agir également d'un radical bicyclique ou polycyclique qui peut être ponté, c'est-à-dire que les cycles ont au moins 2 atomes de carbone en commun, ou spirannique, c'est-à-dire que les cycles n'ont qu'un atome de carbone en commun. The term “cycloaliphatic radicals” is intended to denote a monocyclic radical comprising from 3 to 6 saturated carbon atoms, that is to say cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, or unsaturated comprising one or more unsaturations, in particular ethylenic, for example cyclobutenyl , cyclopentenyl, cyclohexenyl, cyclohexadienyl, but, it can also be a bicyclic or polycyclic radical which can be bridged, that is to say that the rings have at least 2 carbon atoms in common, or spirannic, that is, the cycles have only one carbon atom in common.
Par radicaux aryles, on entend désigner essentiellement les radicaux phényle et naphtyle. The term “aryl radicals” is intended to denote essentially the phenyl and naphthyl radicals.
Un radical aryle peut être également une combinaison de cycles aromatiques et non aromatiques, de préférence d'un cycle phényle et d'un cycle non aromatique en C5 ou C6 tel que tetrahydro-1,2,3,4 naphtyle ou indanyle.An aryl radical can also be a combination of aromatic and non-aromatic rings, preferably a phenyl ring and a non-aromatic C5 or C6 ring such as tetrahydro-1,2,3,4 naphthyl or indanyl.
Par radicaux hétérocycliques, on entend désigner un radical hétérocyclique comportant de préférence de 3 à 10 atomes cycliques avec de 1 à 5, de préférence 1 ou 2, hétéroatomes choisisparmi ltoxygane, le soufre et l'azote. Ces radicaux hétéro- cyliques peuvent être saturés ou non et comporter un ou plusieurs, de préférence deux, cycles, par exemple un cycle phényle. The term “heterocyclic radicals” is intended to denote a heterocyclic radical preferably comprising from 3 to 10 cyclic atoms with from 1 to 5, preferably 1 or 2, heteroatoms chosen from among the oxygane, sulfur and nitrogen. These heterocyclic radicals can be saturated or unsaturated and comprise one or more, preferably two, rings, for example a phenyl ring.
Parmi les radicaux hétérocycliques a un seul cycle, il faut citer, par exemple, les radicaux furyle, tetrahydrofuryle, pyrannyle, tetrahydropyrannyle, dioxolannyle, thiényle, pyrrolyle, pyrrolidinyle, imidazolyle, pyrazolyle, pyridyle, pyrazinyle, pyrimidinyle, pyridazinyle, pipéridyle, pipérazinyle, morpholino, pyrazolidinyle, imidazolidinyle, pyrrolinyle, thiazolyle, oxazolyle. Among the heterocyclic radicals with a single ring, mention should be made, for example, of the furyl, tetrahydrofuryl, pyrannyl, tetrahydropyrannyl, dioxolannyl, thienyl, pyrrolyl, pyrrolidinyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridinyl radicals morpholino, pyrazolidinyle, imidazolidinyle, pyrrolinyle, thiazolyle, oxazolyle.
Parmi les radicaux hétérocycliques a plusieurs cycles, de préférence à deux cycles, il faut citer en particulier les radicaux obtenus par fusion des cycles précédents entre eux ou avec un radical phényle, tels que benzofurannyle, chromanyle, indolyle, quinolyle, benzothiényle, indolinyle, benzodioxannyle. Among the heterocyclic radicals with several rings, preferably with two rings, mention should be made in particular of the radicals obtained by fusion of the preceding cycles with each other or with a phenyl radical, such as benzofurannyl, chromanyl, indolyl, quinolyl, benzothienyl, indolinyl, benzodioxannyl .
Ces radicaux peuvent être non substitués ou substitués, de préférence par un trois radicaux choisis parmi le fluor, le chlore, le brome ou l'iode, les halogènes, les radicaux alcoyle, alcoxy, aryle1 aryloxy, aralcoxy, nitro ou acyle. These radicals can be unsubstituted or substituted, preferably by one of three radicals chosen from fluorine, chlorine, bromine or iodine, halogens, alkyl, alkoxy, aryl-aryloxy, aralkoxy, nitro or acyl radicals.
Par radical alcoxy on entend désigner de préférence les radicaux alcoxy correspondant aux radicaux alcoyles précédents. The term “alkoxy radical” is intended to denote preferably the alkoxy radicals corresponding to the preceding alkyl radicals.
Par radical aralcoyle, cycloaliphatiquealcoyle ou hétérocyclique-alcoyle, on entend désigner les radicaux comportant de préférence de 1 à 4 atomes de carbone dans la partie aliphatique, la partie aryle, cycloaliphatique ou hétérocyclique étant telle que définie précédemment. The term “aralkyl, cycloaliphatic alkyl or heterocyclic-alkyl radical” is intended to denote the radicals preferably having from 1 to 4 carbon atoms in the aliphatic part, the aryl, cycloaliphatic or heterocyclic part being as defined above.
Les radicaux aryloxy et aralcoxy sont les radicaux correspondant aux radicaux aryle et aralcoyle précédents. The aryloxy and aralcoxy radicals are the radicals corresponding to the preceding aryl and aralkyl radicals.
Par radical acyle, on entend désigner plus particulièrement un radical correspondant I un acide carboxylique, de préférence un acide carboxylique aliphatique tel que acétyle. The term “acyl radical” is intended to denote more particularly a radical corresponding to a carboxylic acid, preferably an aliphatic carboxylic acid such as acetyl.
Parmi les composés selon la présente invention, il faut citer plus particulièrement les composés de formule la
dans laquelle n est compris entre 1 et 4 inclus et
R1 et R2 sont des radicaux alcoyles en C1 à C3, ou bien R1 et R2 pris ensemble représentent un monocycle azoté à 5 ou 6 chainons ne comportant que 1 ou 2 hétéroatomes ; ainsi que les sels d'ammonium quaternaire méthylé de ces composes. Among the compounds according to the present invention, mention should be made more particularly of the compounds of formula la
in which n is between 1 and 4 inclusive and
R1 and R2 are C1 to C3 alkyl radicals, or else R1 and R2 taken together represent a nitrogen monocycle with 5 or 6 links comprising only 1 or 2 heteroatoms; as well as the methylated quaternary ammonium salts of these compounds.
I1 faut également citer les composés de formule Ib :
dans laquelle n est compris entre 1 et 4 inclus et m est 1 ou 2 et R est l'hydrogène, un radical alcoyle en
C1 à C3 ou benzyle ainsi que le disulfure
où n est compris entre 1 et 4 inclus. The compounds of formula Ib must also be mentioned:
in which n is between 1 and 4 inclusive and m is 1 or 2 and R is hydrogen, an alkyl radical in
C1 to C3 or benzyl as well as disulfide
where n is between 1 and 4 inclusive.
Les produits selon la présente invention peuvent être préparés par des procédés d'estérification connus, en particulier par estérification de l'acide p-méthoxycinnamique libre ou sous forme de dérivés réactifs tels que chlorure ou anhydride en présence d'un alcool de formule
HO - (CH2)n - R dans un solvant anhydre tel que le benzène.The products according to the present invention can be prepared by known esterification methods, in particular by esterification of free p-methoxycinnamic acid or in the form of reactive derivatives such as chloride or anhydride in the presence of an alcohol of formula
HO - (CH2) n - R in an anhydrous solvent such as benzene.
Pour la préparation des sulfures qu polysulfures symétriques, on utilise dans les mêmes conditions un diol de formule HO - (CH2)n - (S)m (C (CH2)n - OH
La quaternisation des amines tertiaires s'effectue par des procédés connus tels que l'action de l'iodure de méthyle en milieu anhydre.For the preparation of symmetrical sulfides and polysulfides, a diol of the formula HO - (CH2) n - (S) m (C (CH2) n - OH) is used under the same conditions.
The quaternization of tertiary amines is carried out by known methods such as the action of methyl iodide in an anhydrous medium.
On illustrera, ci-après, la présente invention en mentionnant la préparation de quelques exemples non limitatifs de dérivés représentatifs répondant à la formule générale I. The present invention will be illustrated below by mentioning the preparation of a few nonlimiting examples of representative derivatives corresponding to the general formula I.
Exemple 1
Préparation d'iodomethylate de- p-méthoxycinnamate de diméthylaminoéthanol
Preparation of dimethylaminoethanol p-methoxycinnamate iodomethylate
Dans un tricol, on mélange 0,10 mole de chlorure de l'acide p-méthoxycinnamique, 200 ml de benzène anhydre et 0,10 mole de diméthylaminoéthanol. In a three-necked flask, 0.10 mole of p-methoxycinnamic acid chloride, 200 ml of anhydrous benzene and 0.10 mole of dimethylaminoethanol are mixed.
On agite pendant une heure. On observe la formation d'un précipité qui est filtré et séché. The mixture is stirred for one hour. The formation of a precipitate is observed, which is filtered and dried.
Le précipité est repris par l'eau et additionné d'ammoniaque jusqu'd pH alcalin. Le mélange est extrait deux fois par du chloroforme. The precipitate is taken up in water and added with ammonia up to alkaline pH. The mixture is extracted twice with chloroform.
La phase chloroformique est séchée sur sulfate de sodium anhydre, filtrée et évaporée à sec.The chloroform phase is dried over anhydrous sodium sulfate, filtered and evaporated to dryness.
On obtient une huile. An oil is obtained.
O,lmole de l'huile obtenue est dissoute dans 40 ml d'acétone et on ajoute 0,1 mole d'iodure de méthyle. 0.1 mol of the oil obtained is dissolved in 40 ml of acetone and 0.1 mol of methyl iodide is added.
Après évaporation de l'acétone, on obtient des cristaux qui sont lavés par un peu d'acétone et séchés pour obtenir le produit du titre. After evaporation of the acetone, crystals are obtained which are washed with a little acetone and dried to obtain the title product.
Propriétés
Formule brute : C15 H22 0 3 N I
Masse moléculaire : 391,237
Ces cristaux ont un point de fusion instantané de 211,60C + 0,50C et présentent une molaire de 23500 315 nm.Properties
Gross formula: C15 H22 0 3 NI
Molecular mass: 391,237
These crystals have an instant melting point of 211.60C + 0.50C and have a molar of 23500 315 nm.
Exemple 2
Préparation du dérivé disulfure de formule
Preparation of the disulfide derivative of formula
Dans un tricol on ajoute 0,1 mole de chlorure de l'acide p-méthoxycinnamique, 200 ml de benzène anhydre et 0,05 mole de [HO - CH2 - CH2 - S]. 0.1 mole of p-methoxycinnamic acid chloride, 200 ml of anhydrous benzene and 0.05 mole of [HO - CH2 - CH2 - S] are added to a three-necked flask.
2
On chauffe I reflux pendant une heure. Le mélange réactionnel évaporé I sec est recristallisé deux fois dans l'alcool absolu pour obtenir le produit du titre.2
The reflux is heated for one hour. The dry evaporated reaction mixture I is recrystallized twice from absolute alcohol to obtain the title product.
Propriétés Formule brute : C24 H26 6 S2
Masse moléculaire : 474,45 molaire = 47080 313 nm
Point de fusion = 81,50C.Properties Raw formula: C24 H26 6 S2
Molecular mass: 474.45 molar = 47080 313 nm
Melting point = 81.50C.
Exemple 3
Préparation du dérivé de formule :
Preparation of the derivative of formula:
Dans un tricol, on ajoute 0,1 mole du chlorure de l'acide p-methoxycinnamique, 300 ml de benzène anhydre et 0,1 mole de t
On chauffe à reflux pendant une heure, on filtre et on sèche le mélange réactionnel. Ce mélange est repris par l'eau et on ajoute de l'ammoniaque jusqu't pH alcalin. Après extraction par CH C13, les phases chloroformiques sont séchées sur sulfate de sodium anhydre et évaporées I sec. The mixture is refluxed for one hour, filtered and the reaction mixture is dried. This mixture is taken up in water and ammonia is added until the pH is alkaline. After extraction with CH C13, the chloroform phases are dried over anhydrous sodium sulfate and evaporated I dry.
On reprend 0,1 mole du dérivé par 20 ml d'acétone auxquels on ajoute 0,1 mole d'iodure de méthyle. Après évaporation de l'acétone et recristallisation deux fois par l'alcool absolu on obtient le produit du titre. 0.1 mole of the derivative is taken up in 20 ml of acetone to which 0.1 mole of methyl iodide is added. After evaporation of the acetone and recrystallization twice from absolute alcohol, the title product is obtained.
ProPriétés
Formule brute : C17 H24 04 N I
Masse moléculaire : 433,27
E molaire = 23100 à 315 nm
Point de fusion (decomposition) = 1860C
Exemple 4
Préparation du dérivé de formule
Gross formula: C17 H24 04 NI
Molecular mass: 433.27
E molar = 23100 at 315 nm
Melting point (decomposition) = 1860C
Example 4
Preparation of the derivative of formula
Dans un tricol on ajoute 0,1 mole du chlorure de l'acide p-methoxycinnamique, 500 ml de benzène anhydre et O,l mole de :
On chauffe I reflux pendant une heure, on reprend par de l'eau et on ajoute de l'ammoniaque jusqu'a pH alcalin. Le mélange est extrait par de l'éther éthylique, la phase éthérée est séchée par
Na2 S04 anhydre et évaporée I sec.The mixture is refluxed for one hour, taken up in water and ammonia is added until the pH is alkaline. The mixture is extracted with ethyl ether, the ethereal phase is dried with
Na2 S04 anhydrous and evaporated I dry.
On reprend le résidu par 20 mld'acétone et on ajoute 0,1 mole d'iodure de méthyle. Par évaporation de l'acétone et lavage du précipité par un peu d'acétone, on obtient le produit du titre. The residue is taken up in 20 ml of acetone and 0.1 mol of methyl iodide is added. By evaporation of the acetone and washing of the precipitate with a little acetone, the title product is obtained.
Propriétés
Formule brute : C18 H26 3 N I
Masse moléculaire : 431,30
E molaire = 23400 I 315 nm
Point de fusion : 1900C. Properties
Gross formula: C18 H26 3 NI
Molecular mass: 431.30
E molar = 23400 I 315 nm
Melting point: 1900C.
La présente invention concerne également des compositions cosmétiques contenant au moins un compose de formule (I) avec des excipients utilisables en cosmétologie. The present invention also relates to cosmetic compositions containing at least one compound of formula (I) with excipients which can be used in cosmetology.
En effet, les composés de formule (I), associés I un excipient choisi, donnent des compositions à usage externe, particulièrement utiles pour la protection de la peau vis I vis des rayonnements et pour la prévention du vieillissement cutané. In fact, the compounds of formula (I), combined with a chosen excipient, give compositions for external use, which are particularly useful for protecting the skin from radiation and for preventing skin aging.
L'important pour les composés objets de l'invention, provient du fait que la structure même de ces dérivés possède une partie présentant une affinité particulière pour la keratine de la couche cornée. The important for the compounds which are the subject of the invention comes from the fact that the very structure of these derivatives has a part having a particular affinity for keratin of the stratum corneum.
Compte tenu de leur parfaite tolérance, de leur bon pouvoir filtrant et de leur remanence au niveau de la peau, les molécules objet de l'invention sont particulièrement utiles comme principe actif cosmétologique et plus particulièrement dans la prévention des effets nocifs du rayonnement solaire et du vieillissement cutané. Given their perfect tolerance, their good filtering power and their remanence in the skin, the molecules object of the invention are particularly useful as a cosmetic active ingredient and more particularly in the prevention of the harmful effects of solar radiation and skin aging.
Les compositions cosmétiques selon la présente invention sont de préférence des crèmes ou des huiles contenant, outre une phase grasse, d'autres excipients tels que parfum, antioxydant et conservateur par exemple. Ces compositions peuvent évidemment contenir d'autres principes actifs en cosmétologie. The cosmetic compositions according to the present invention are preferably creams or oils containing, in addition to a fatty phase, other excipients such as perfume, antioxidant and preservative for example. These compositions can obviously contain other active ingredients in cosmetology.
A titre indicatif, on donne ci-après des exemples de formulations selon la présente invention. By way of indication, examples of formulations according to the present invention are given below.
Crème protectrice t phase aqueuse continue - molécule de l'exemple 2 ............... 3 g - monostéarate de glycérol .............. 10 g - alkylsulfate de sodium ................ 3 g - huile de vaseline ..................... 10 g - huile de palmiste hydrogénée .......... 5 g - parfum, q.s.Protective cream t continuous aqueous phase - molecule of Example 2 ............... 3 g - glycerol monostearate .............. 10 g - sodium alkyl sulphate ................ 3 g - vaseline oil ..................... 10 g - hydrogenated palm kernel oil .......... 5 g - perfume, qs
- conservateur, q.s.- curator, q.s.
- eau, q.s.p. ........................... 100 g
Crème protectrice 9 phase huileuse continue - molécule de l'exemple 1 ............... 2,5 g - isostéarate de glycérol ................ 5 g - huile de vaseline épaisse ............. 16 g - glycérol ............................. 3 g - sulfate de magnésium .................. 0,5 g - parfum, q.s.- water, qs ........................... 100 g
Protective cream 9 continuous oily phase - molecule of example 1 ............... 2.5 g - glycerol isostearate .............. .. 5 g - thick petrolatum oil ............. 16 g - glycerol ........................ ..... 3 g - magnesium sulfate .................. 0.5 g - perfume, qs
- antioxydant, q.s.- antioxidant, q.s.
- conservateur, q.s.- curator, q.s.
- eau, q.s.p. ........................... 100 g
Crème écran total - molécule de l'exemple 3 ............... 3 g - paraméthoxycinnamate d'ethyle-hexyle - 1 g - isostéarate de glycérol ............... 5 g - huile de vaseline ..................... 14 g - glycérol ........................... 3 g - sulfate de magnésium .................. 0,5 g - oxyde de titane ....................... 1 g - antioxydant, q.s.- water, qs ........................... 100 g
Total sunscreen - molecule from Example 3 ............... 3 g - ethylhexyl paramethoxycinnamate - 1 g - glycerol isostearate ......... ...... 5 g - petrolatum oil ..................... 14 g - glycerol ............. .............. 3 g - magnesium sulfate .................. 0.5 g - titanium oxide .... ................... 1 g - antioxidant, qs
- conservateur, q.s.- curator, q.s.
- parfum, q.s.- perfume, q.s.
- eau, q.s.p. .......................... 100 g - water, q.s.p. .......................... 100 g
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8108429A FR2504530A1 (en) | 1981-04-28 | 1981-04-28 | Substd. alkyl 4-methoxy-cinnamic acid ester derivs. - useful as sunscreening agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8108429A FR2504530A1 (en) | 1981-04-28 | 1981-04-28 | Substd. alkyl 4-methoxy-cinnamic acid ester derivs. - useful as sunscreening agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2504530A1 true FR2504530A1 (en) | 1982-10-29 |
| FR2504530B1 FR2504530B1 (en) | 1984-03-16 |
Family
ID=9257857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8108429A Granted FR2504530A1 (en) | 1981-04-28 | 1981-04-28 | Substd. alkyl 4-methoxy-cinnamic acid ester derivs. - useful as sunscreening agents |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2504530A1 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2566400A1 (en) * | 1984-06-22 | 1985-12-27 | Univ Pasteur | SULFUR DERIVATIVES OF PARA-METHOXYCINNAMIC ACID, PROCESSES FOR OBTAINING SAME, DERMO-PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM AND APPLICATIONS. |
| EP0165710A1 (en) * | 1984-06-21 | 1985-12-27 | VAN DYK & COMPANY, INC. | Benzene sulfonate quaternary ammonium salts of organic sunscreen carboxylic acids |
| US4613499A (en) * | 1982-08-03 | 1986-09-23 | Van Dyk & Company Inc. | Substituted cinnamal dialkyl malonates in sunscreening, skin care compositions |
| US4680144A (en) * | 1984-06-21 | 1987-07-14 | Mallinckrodt, Inc. | Benzene sulfonate quaternary ammonium salts of organic sunscreen carboxylic acids |
| EP0272576A1 (en) * | 1986-12-23 | 1988-06-29 | L. GIVAUDAN & CIE Société Anonyme | Quaternary ammonium halide salts of cinnamate esters as sunscreen agents and compositions containing same |
| US4791217A (en) * | 1984-06-22 | 1988-12-13 | Universite Louis Pasteur | Sulphur derivatives of para-methoxycinnamic acid, processes for their production, dermo-pharmaceutical and cosmetic compositions containing them and applications |
| EP0902009A2 (en) * | 1997-09-04 | 1999-03-17 | Henkel Kommanditgesellschaft auf Aktien | Esterquats based on cinnamic acid |
| US6607735B2 (en) | 2000-12-21 | 2003-08-19 | Johnson & Johnson Consumer Companies, Inc. | Method for reducing the appearance of dark circles under the eyes |
| US7396526B1 (en) | 1998-11-12 | 2008-07-08 | Johnson & Johnson Consumer Companies, Inc. | Skin care composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957162C (en) * | 1955-02-11 | 1957-01-31 | Thomae Gmbh Dr K | Light protection preparation |
| FR1233336A (en) * | 1958-10-10 | 1960-10-12 | Givaudan & Cie Sa | Process for the preparation of new alkoxy-alkyl esters of p-methoxycinnamic acid |
| US3879443A (en) * | 1974-04-29 | 1975-04-22 | Gaf Corp | Sun-screening compounds III |
| GB2018988A (en) * | 1978-04-17 | 1979-10-24 | Kyowa Hakko Kogyo Kk | Determining cholinestenase activity |
-
1981
- 1981-04-28 FR FR8108429A patent/FR2504530A1/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE957162C (en) * | 1955-02-11 | 1957-01-31 | Thomae Gmbh Dr K | Light protection preparation |
| FR1233336A (en) * | 1958-10-10 | 1960-10-12 | Givaudan & Cie Sa | Process for the preparation of new alkoxy-alkyl esters of p-methoxycinnamic acid |
| US3879443A (en) * | 1974-04-29 | 1975-04-22 | Gaf Corp | Sun-screening compounds III |
| GB2018988A (en) * | 1978-04-17 | 1979-10-24 | Kyowa Hakko Kogyo Kk | Determining cholinestenase activity |
Non-Patent Citations (1)
| Title |
|---|
| CA1979 * |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4613499A (en) * | 1982-08-03 | 1986-09-23 | Van Dyk & Company Inc. | Substituted cinnamal dialkyl malonates in sunscreening, skin care compositions |
| EP0165710A1 (en) * | 1984-06-21 | 1985-12-27 | VAN DYK & COMPANY, INC. | Benzene sulfonate quaternary ammonium salts of organic sunscreen carboxylic acids |
| US4680144A (en) * | 1984-06-21 | 1987-07-14 | Mallinckrodt, Inc. | Benzene sulfonate quaternary ammonium salts of organic sunscreen carboxylic acids |
| FR2566400A1 (en) * | 1984-06-22 | 1985-12-27 | Univ Pasteur | SULFUR DERIVATIVES OF PARA-METHOXYCINNAMIC ACID, PROCESSES FOR OBTAINING SAME, DERMO-PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM AND APPLICATIONS. |
| WO1986000304A1 (en) * | 1984-06-22 | 1986-01-16 | Universite Louis Pasteur (Strasbourg I) | Sulphur-containing derivatives of para-methoxycinnamic acid, production processes thereof, dermo-pharmaceutical and cosmetic compositions containing them and applications |
| US4791217A (en) * | 1984-06-22 | 1988-12-13 | Universite Louis Pasteur | Sulphur derivatives of para-methoxycinnamic acid, processes for their production, dermo-pharmaceutical and cosmetic compositions containing them and applications |
| JPH0629237B2 (en) * | 1984-06-22 | 1994-04-20 | ユニヴェルシテ・ルイ・パスツ−ル（ストラマブ−ル・プルミエ） | Sulfurized derivative of paral methoxycinnamic acid, method for producing the same, and sunscreen composition containing the same |
| EP0272576A1 (en) * | 1986-12-23 | 1988-06-29 | L. GIVAUDAN & CIE Société Anonyme | Quaternary ammonium halide salts of cinnamate esters as sunscreen agents and compositions containing same |
| EP0902009A2 (en) * | 1997-09-04 | 1999-03-17 | Henkel Kommanditgesellschaft auf Aktien | Esterquats based on cinnamic acid |
| EP0902009A3 (en) * | 1997-09-04 | 2000-10-04 | Henkel Kommanditgesellschaft auf Aktien | Esterquats based on cinnamic acid |
| US7396526B1 (en) | 1998-11-12 | 2008-07-08 | Johnson & Johnson Consumer Companies, Inc. | Skin care composition |
| US6607735B2 (en) | 2000-12-21 | 2003-08-19 | Johnson & Johnson Consumer Companies, Inc. | Method for reducing the appearance of dark circles under the eyes |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2504530B1 (en) | 1984-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |