FR2601365A1 - New acrylamide derivatives, their preparation and their use in the production of polymers which absorb ultraviolet radiation - Google Patents
New acrylamide derivatives, their preparation and their use in the production of polymers which absorb ultraviolet radiation Download PDFInfo
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- FR2601365A1 FR2601365A1 FR8610021A FR8610021A FR2601365A1 FR 2601365 A1 FR2601365 A1 FR 2601365A1 FR 8610021 A FR8610021 A FR 8610021A FR 8610021 A FR8610021 A FR 8610021A FR 2601365 A1 FR2601365 A1 FR 2601365A1
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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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
- C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
Description
La présente invention a pour objet de nouveaux dérivés d'acrylamide substitués par des composés absorbant les radiations ultra-violettes. The present invention relates to new acrylamide derivatives substituted with compounds absorbing ultraviolet radiation.
Ces nouveaux dérivés peuvent être utilisés dans la préparation de polymères qui sont eux-mêmes applicables notamment dans la réalisation de compositions cosmétiques destinées à protéger la peau contre les effets indésirés des radiations ultraviolettes, et en particulier contre les effets non désirés de l'exposition au soleil (brûlures et éventuellement brunissement de la peau). These new derivatives can be used in the preparation of polymers which are themselves applicable in particular in the production of cosmetic compositions intended to protect the skin against the undesired effects of ultraviolet radiation, and in particular against the undesired effects of exposure to sun (burns and possibly browning of the skin).
On sait que les radiations ultra-violettes ayant une longueur d'onde dans la zone allant de 280 à 315 nm environ, sont responsables des inflammations ou érythèmes de la peau observés lorsque le corps humain est soumis aux rayons solaires sans protection. Cette zone de longueurs d'onde est parfois appelée "zone érythémateuse". It is known that ultraviolet radiation having a wavelength in the region ranging from 280 to 315 nm approximately, are responsible for the inflammations or erythemas of the skin observed when the human body is subjected to the sun rays without protection. This area of wavelengths is sometimes called "erythematous area".
On sait également que les radiations ultra-violettes responsables du bronzage de la peau ont une longueur d'onde allant de 315 à 400 nm environ. We also know that the ultraviolet radiation responsible for tanning the skin has a wavelength ranging from 315 to 400 nm approximately.
On connais des composés qui ont la propriété d'absorber l'ultra-violet dans la zone érythémateuse tout en laissant passer les radiations responsables du bronzage et on a déjà proposé l'utilisation de tels composés comme "filtres" solaires dans des compositions cosmétiques favorisant l'acquisition du bronzage de la peau en évitant les brûlures et les irritations de la peau. We know of compounds which have the property of absorbing the ultraviolet in the erythematous zone while letting through the radiation responsible for tanning and we have already proposed the use of such compounds as solar "filters" in cosmetic compositions favoring the acquisition of skin tanning, avoiding burns and skin irritations.
D'autre part, certains utilisateurs souhaitent éviter le brunissement et on a donc proposé l'emploi, dans des compositions cosmétiques, de "filtres" formant un écran plus ou moins important aux radiations ultra-violettes dans la zone de longueurs d'onde 315-400 nm éventuellement en association avec des composés filtrant les rayons U.V. dans la zone érythémateuse, de façon à éviter à la fois le bronzage et les brûlures de la peau. On the other hand, some users wish to avoid browning and we have therefore proposed the use, in cosmetic compositions, of "filters" forming a more or less important screen for ultraviolet radiation in the wavelength region 315 -400 nm possibly in combination with compounds filtering UV rays in the erythematous area, so as to avoid both tanning and burns of the skin.
On a préconisé, notamment dans les brevets français NO 73.23254 et 76.23174, l'utilisation de filtres solaires liés par covalence à des polymères. La présentation sous forme de polymères présente l'avantage de réduire ou de supprimer la pénétration du composé-filtre dans l'organisme par traversée de l'épiderme, ce qui permet d'éviter tout risque d'effets secondaires toxiques. It has been recommended, in particular in French patents NO 73.23254 and 76.23174, the use of sun filters covalently linked to polymers. The presentation in the form of polymers has the advantage of reducing or eliminating the penetration of the filter compound into the body by crossing the epidermis, which makes it possible to avoid any risk of toxic side effects.
La présente invention a pour objet de nouveaux dérivés d'acrylamide de formule I
CH2 = CH - CO - NH - CH2 - X (I) dans laquelle X représente un groupement de formule
dans laquelle R est un groupement tert-octyle ou de formule
dans laquelle Z est un groupement tert-butyle.The present invention relates to new acrylamide derivatives of formula I
CH2 = CH - CO - NH - CH2 - X (I) in which X represents a group of formula
in which R is a tert-octyl group or of formula
in which Z is a tert-butyl group.
Les dérivés de formule I peuvent être préparés selon les méthodes connues décrites par exemple dans les brevets français 73.23254 et 76.23174. The derivatives of formula I can be prepared according to the known methods described for example in French patents 73.23254 and 76.23174.
Les dérivés de formule I peuvent être utilisés notamment comme monomères dans la préparation de polymères de formule II.
dans laquelle X est défini comme précédemment.in which X is defined as above.
On peut utiliser les monomères de formule I, éventuellement en association avec des comonomères hydrophiles à insaturation éthylénique. The monomers of formula I can be used, optionally in combination with hydrophilic ethylenically unsaturated comonomers.
Lorsque des motifs dérivés de comonomères hydrophiles sont présents, les motifs de formule II peuvent représenter par exemple de 10 à 99% en poids du polymère. When units derived from hydrophilic comonomers are present, the units of formula II can represent, for example, from 10 to 99% by weight of the polymer.
Les polymères obtenus avec les monomères de formule I sont donc notamment des polymères contenant uniquement des motifs de formule II, étant entendu que dans une même molécule polymérique, plusieurs motifs différents, correspondant à des groupements X différents, peuvent être présents. The polymers obtained with the monomers of formula I are therefore in particular polymers containing only units of formula II, it being understood that in the same polymer molecule, several different units, corresponding to different X groups, may be present.
On sait que les filtres solaires sont présents dans les compositions cosmétiques soit sous forme de solutions huileuses, soit sous forme de solutions aqueuses ou hydroalcooliques, soit encore sous forme de solutions aqueuses et/ou huileuses dans des compositions sous forme d'émulsions. It is known that sunscreens are present in cosmetic compositions either in the form of oily solutions, or in the form of aqueous or hydroalcoholic solutions, or also in the form of aqueous and / or oily solutions in compositions in the form of emulsions.
Les compositions polymériques qui contiennent uniquement des motifs de formule II sont suffisamment solubles dans les huiles, et la préparation de compositions cosmétiques huileuses ne présente pas de difficultés particulières. Polymeric compositions which contain only units of formula II are sufficiently soluble in oils, and the preparation of oily cosmetic compositions does not present any particular difficulties.
Par contre, si on veut obtenir une composition polymérique soluble dans l'eau, il est nécessaire de copolymériser les "monomères-filtres" de formule I avec des comonomères hydrophiles. On the other hand, if a water-soluble polymer composition is to be obtained, it is necessary to copolymerize the "filter monomers" of formula I with hydrophilic comonomers.
Les comonomères hydrophiles sont, en particulier, choisis parmi la
N-vinylpyrrolidone, le N,N-diméthyl-acrylamide, l'acide acrylique, l'acide méthacrylique et les monomères de formule générale
dans laquelle M représente -O- ou -NH-, x est un nombre égal à 2 ou 3,
R1 représente -H ou -CH3 et
R2 représente -CH3 ou -C2H5 étant entendu que les groupements amine présents peuvent être quaternisés ou salifiés avant ou après la polymérisation.Hydrophilic comonomers are, in particular, chosen from the
N-vinylpyrrolidone, N, N-dimethyl-acrylamide, acrylic acid, methacrylic acid and the monomers of general formula
in which M represents -O- or -NH-, x is a number equal to 2 or 3,
R1 represents -H or -CH3 and
R2 represents -CH3 or -C2H5, it being understood that the amine groups present can be quaternized or salified before or after the polymerization.
Parmi les comonomères de formule générale (III) on peut citer à titre d'exemples, le méthacrylate de N,N-diméthylamino-2 éthyle, le
N,N-diéthylamino-3 propyl méthacrylamide, etc...Mention may be made, among the comonomers of general formula (III), of N, N-2-dimethylaminoethyl methacrylate,
N, N-3-diethylamino propyl methacrylamide, etc ...
Les groupements amine peuvent être salifiés avec un acide minéral comme par exemple l'acide chlorhydrique ou un acide organique comme l'acide lactique. Ils peuvent aussi être quaternisés par un agent classique de quaternisation comme le sulfate de diméthyle, le chlorure de méthyle, l'acide chloroacétique etc... The amine groups can be salified with a mineral acid such as for example hydrochloric acid or an organic acid such as lactic acid. They can also be quaternized by a conventional quaternization agent such as dimethyl sulfate, methyl chloride, chloroacetic acid, etc.
Le procédé de préparation des polymères tels que définis ci-dessus est principalement caractérisé par le fait que l'on polymérise en solution au moins un monomère de formule I
CH2 = CH- CO-NH-CH2-X (I) dans laquelle X est défini comme précédemment, éventuellement en présence de comonomères hydrophiles à insaturation éthylénique, en présence d'un initiateur de polymérisation.The process for the preparation of polymers as defined above is mainly characterized by the fact that at least one monomer of formula I is polymerized in solution
CH2 = CH-CO-NH-CH2-X (I) in which X is defined as above, optionally in the presence of hydrophilic comonomers with ethylenic unsaturation, in the presence of a polymerization initiator.
Les compositions cosmétiques destinées à protéger la peau contre les effets indésirés des radiations ultraviolettes, contenant, en tant qu'ingrédient actif filtrant les rayons ultraviolets, au moins un polymère tel que défini précédemment, se présentent sous la forme de solutions aqueuses, hydroalcooliques ou huileuses, d'émulsions aqueuses, de lotions, de crèmes, de laits, de gels, de sticks ou sous forme de compositions pour aérosols. Cosmetic compositions intended to protect the skin against the undesired effects of ultraviolet radiation, containing, as active ingredient filtering ultraviolet rays, at least one polymer as defined above, are in the form of aqueous, hydroalcoholic or oily solutions , aqueous emulsions, lotions, creams, milks, gels, sticks or in the form of aerosol compositions.
Ces compositions cosmétiques contiennent en outre les adjuvants usuels généralement présents dans de telles compositions, et éventuellement d'autres substances capables d'absorbeur l'ultraviolet. These cosmetic compositions also contain the usual adjuvants generally present in such compositions, and possibly other substances capable of absorbing the ultraviolet.
Dans ces compositions cosmétiques, la concentration en polymère antisolaire est variable car elle dépend du degré de protection que l'on souhaite obtenir. Généralement, la concentration du polymère peut varier de 1 à 20% en poids par rapport au poids total de la composition. In these cosmetic compositions, the concentration of sunscreen polymer is variable because it depends on the degree of protection which it is desired to obtain. Generally, the concentration of the polymer can vary from 1 to 20% by weight relative to the total weight of the composition.
Précédemment, la puissance absorbante du filtre était exprimée à l'aide de la valeur de Ksp (K spécifique), qui est une fonction de la quantité de substances filtrantes contenue dans l'échantillon, de la densité optique mesurée et d'une constante dépendant de l'appareil. Previously, the absorbent power of the filter was expressed using the value of Ksp (specific K), which is a function of the quantity of filtering substances contained in the sample, of the measured optical density and of a dependent constant. of the device.
La définition de Ksp est donnée dans l'ouvrage "Introduction to electronic absorption Spectroscopy in organic chemistry" par Gillian and
Stern, Arnold Ed., London 1954, page 10.The definition of Ksp is given in the book "Introduction to electronic absorption Spectroscopy in organic chemistry" by Gillian and
Stern, Arnold Ed., London 1954, page 10.
Ksp = K
c
d
avec K
d = densité optique mesurée
c = concentration de la solution (g/ml)
1 = épaisseur de la cellule en cm
Actuellement la puissance absorbante est définie par le terme "absorbance spécifique, a ", défini par la Norme Française T.01030 (Janvier 1972) reliée au Ksp pa la relation
Ksp = 1000
a
s
Dans la présente demande la puissance absorbante est exprimée au moyen de l'absorbance spécifique.Ksp = K
vs
d
with K
d = measured optical density
c = concentration of the solution (g / ml)
1 = cell thickness in cm
Currently the absorbent power is defined by the term "specific absorbance, a", defined by French Standard T.01030 (January 1972) linked to the Ksp pa
Ksp = 1000
at
s
In the present application the absorbent power is expressed by means of the specific absorbance.
Les exemples suivants illustrent l'invention sans toutefois la limiter. The following examples illustrate the invention without, however, limiting it.
Exemples de préparation des polymères
EXEMPLE 1
Préparation de l'Chydroxy-2' acrylamidométhyl-3' t-octyl-5' phényl)-2H benzotriazole.Examples of polymer preparation
EXAMPLE 1
Preparation of hydroxy-2 'acrylamidomethyl-3' t-octyl-5 'phenyl) -2H benzotriazole.
On introduit dans un réacteur
- 600g d'acide sulfurique
- 163g d'hydroxy-2' t-octyl-5' phényl)- 2H benzotriazole
Cette mise en solution est exothermique, la température du mélange atteint 35"C. Après dissolution complète, on refroidit le mélange réactionnel à OOC, puis introduit par portions, en 30minutes, 60,6g d'hydroxyméthyl acrylamide et on cesse alors le refroidissement. La température atteint et se maintient à 300C pendant toute la durée de la réaction.Introduced into a reactor
- 600g of sulfuric acid
- 163g of hydroxy-2 't-octyl-5' phenyl) - 2H benzotriazole
This dissolution is exothermic, the temperature of the mixture reaches 35 "C. After complete dissolution, the reaction mixture is cooled to OOC, then introduced in portions, in 30 minutes, 60.6 g of hydroxymethyl acrylamide and then cooling is stopped. The temperature reaches and is maintained at 300C throughout the duration of the reaction.
Après 24 h de réaction, on dilue par 500ml d'éthanol, puis verse lentement dans 5 litres d'un mélange eau + glace sous vive agitation ; la poudre blanche obtenue est filtrée puis lavée par l'eau jusqu'à pH 5 ; après filtration, le produit brut est dissous dans 3 litres de chloroforme. L'eau résiduelle est éliminée par décantation ; après séchage sur sulfate de sodium, la phase organique est concentrée à 250g et le résidu huileux est dissous dans 2 litres de cyclohexane au reflux. La solution est filtrée puis refroidie : après cristallisation le produit attendu est filtré et séché. After 24 h of reaction, diluted with 500 ml of ethanol, then poured slowly into 5 liters of a water + ice mixture with vigorous stirring; the white powder obtained is filtered and then washed with water until pH 5; after filtration, the crude product is dissolved in 3 liters of chloroform. The residual water is removed by decantation; after drying over sodium sulfate, the organic phase is concentrated to 250g and the oily residue is dissolved in 2 liters of cyclohexane at reflux. The solution is filtered and then cooled: after crystallization the expected product is filtered and dried.
On obtient 153g du produit attendu, soit un rendement de 75%. 153g of the expected product are obtained, ie a yield of 75%.
ANALYSES
F. = 1560C
C.C.M. : support de gel de silice LS 254
solvant chloroforme
éluant
- acétate d'éthyle 90
- chloroforme 10
révélation W Rf = 0,66 (produit de départ Rf = 0,96)
Spectre U.V. à 1 mg/iOOml dans le chloroforme max.1 = 305nm ; aS1 = 40,8
tmax.2 340nm ; aS2 = 37,9
EXEMPLE 2 :Préparation du t-butyl-4 acrylamidométhyl-3' méthoxy-4' dibenzoylméthane
On introduit dans un réacteur
- 600g d'acide sulfurique
- 93g de t-butyl-4 méthoxy-4' dibenzoyl méthane
Ce mélange est agité pendant 15 minutes afin de dissoudre le solide ; après dissolution complète on refroidit le mélange réactionnel à OOC puis introduit par portions, en 30 minutes, 30,3g d'hydroxyméthyl acrylamide et on cesse alors le refroidissement. La coloration est passée de l'orangé au rouge.ANALYZES
F. = 1560C
TLC: LS 254 silica gel support
chloroform solvent
eluting
- ethyl acetate 90
- chloroform 10
revelation W Rf = 0.66 (starting material Rf = 0.96)
UV spectrum at 1 mg / 100 ml in chloroform max. 1 = 305 nm; aS1 = 40.8
tmax.2 340nm; aS2 = 37.9
EXAMPLE 2 Preparation of t-butyl-4 acrylamidomethyl-3 'methoxy-4' dibenzoylmethane
Introduced into a reactor
- 600g of sulfuric acid
- 93g of t-butyl-4-methoxy-4 'dibenzoyl methane
This mixture is stirred for 15 minutes in order to dissolve the solid; after complete dissolution, the reaction mixture is cooled to OOC and then introduced in portions, over 30 minutes, 30.3 g of hydroxymethyl acrylamide and then cooling is stopped. The color changed from orange to red.
Après 24 heures de réaction, on verse lentement dans 4 litres d'un mélange eau + glace sous vive agitation. Le précipité est lavé à l'eau et filtré, puis dissous dans 500ml de dichloréthane. La phase organique est lavée à l'eau jusqu a neutralité, puis concentrée à sec. Le résidu est recristallisé-dans 1 litre de toluène en présence de noir animal. After 24 hours of reaction, pour slowly into 4 liters of a water + ice mixture with vigorous stirring. The precipitate is washed with water and filtered, then dissolved in 500 ml of dichloroethane. The organic phase is washed with water until neutral, then concentrated to dryness. The residue is recrystallized from 1 liter of toluene in the presence of animal black.
On obtient 100g du produit attendu (Rendement = 85%)
ANALYSES
F. = 1640C
- C.C.M.100 g of the expected product are obtained (Yield = 85%)
ANALYZES
F. = 1640C
- CCM
support gel de silice LS 254
solvant chloroforme
éluant : éther éthylique
révélation UV : produit principal Rf : 0,33
produit secondaire Rf : 0,08
produit de départ Rf : 0,86
- spectre UV-à lmg/lOOml dans le chloroforme
= = 357nm a = 86
max. s silica gel support LS 254
chloroform solvent
eluent: ethyl ether
UV exposure: main product Rf: 0.33
secondary product Rf: 0.08
starting material Rf: 0.86
- UV-spectrum at lmg / lOOml in chloroform
= = 357nm a = 86
max. s
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8610021A FR2601365B1 (en) | 1986-01-10 | 1986-07-09 | NOVEL ACRYLAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE PRODUCTION OF POLYMERS ABSORBING ULTRAVIOLET RADIATION. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR868600274A FR2597336B1 (en) | 1986-01-10 | 1986-01-10 | NOVEL COMPOSITIONS OF POLYMERS DERIVED FROM ACRYLAMIDE SUBSTITUTED BY COMPOUNDS ABSORBING ULTRAVIOLET RADIATIONS, AND THEIR APPLICATION IN PARTICULAR IN THE PRODUCTION OF COSMETIC COMPOSITIONS FOR PROTECTING THE SKIN AGAINST THE SIDE EFFECTS OF ULTRAVIOLET RADIATION. |
| FR8610021A FR2601365B1 (en) | 1986-01-10 | 1986-07-09 | NOVEL ACRYLAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE PRODUCTION OF POLYMERS ABSORBING ULTRAVIOLET RADIATION. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2601365A1 true FR2601365A1 (en) | 1988-01-15 |
| FR2601365B1 FR2601365B1 (en) | 1988-10-21 |
Family
ID=26224948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8610021A Expired FR2601365B1 (en) | 1986-01-10 | 1986-07-09 | NOVEL ACRYLAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR USE IN THE PRODUCTION OF POLYMERS ABSORBING ULTRAVIOLET RADIATION. |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2601365B1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2642968A1 (en) * | 1989-02-15 | 1990-08-17 | Oreal | USE IN COSMETICS OF BENZOTRIAZOLE-FUNCTION DIORGANOPOLYSILOXANES AND NOVEL COSMETIC COMPOSITIONS CONTAINING THESE COMPOUNDS FOR THE PROTECTION OF SKIN AND HAIR |
| FR2680683A1 (en) * | 1991-08-29 | 1993-03-05 | Oreal | Cosmetic screening composition containing a screening polymer having a hydrocarbon structure and a screening silicone |
| EP0652210A1 (en) * | 1993-11-10 | 1995-05-10 | L'oreal | Solar filters containing a fluorohydrocarbon group, process for their preparation, and their use in cosmetic compositions |
| FR2714827A1 (en) * | 1994-01-10 | 1995-07-13 | Oreal | Cosmetic or dermatological composition containing a pseudo-latex consisting of particles of a homopolymer-filter U.V. |
| EP0722938A3 (en) * | 1994-10-28 | 1997-01-22 | Roehm Gmbh | Process for preparation of a radically polymerizable UV absorber based on benztriazolyl phenols |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3399173A (en) * | 1961-06-16 | 1968-08-27 | Geigy Ag J R | Light-stable polyaddition compounds |
| EP0010518A1 (en) * | 1978-10-13 | 1980-04-30 | Ciba-Geigy Ag | Acrylic copolymers bearing N-heterocyclic side rings, their use, and process for their preparation |
| EP0015230A1 (en) * | 1979-01-25 | 1980-09-03 | Ciba-Geigy Ag | Stabilized organic Polymer comprising 2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole as a light-stabilizer |
-
1986
- 1986-07-09 FR FR8610021A patent/FR2601365B1/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3399173A (en) * | 1961-06-16 | 1968-08-27 | Geigy Ag J R | Light-stable polyaddition compounds |
| EP0010518A1 (en) * | 1978-10-13 | 1980-04-30 | Ciba-Geigy Ag | Acrylic copolymers bearing N-heterocyclic side rings, their use, and process for their preparation |
| EP0015230A1 (en) * | 1979-01-25 | 1980-09-03 | Ciba-Geigy Ag | Stabilized organic Polymer comprising 2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole as a light-stabilizer |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS SERVICE, REGISTRY HANDBOOK, NUMBER SECTION, 1974 supplement, 1976, résumé nos. 43226-08-0 through 51771-99-4, American Chemical Society, Columbus, Ohio, US * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2642968A1 (en) * | 1989-02-15 | 1990-08-17 | Oreal | USE IN COSMETICS OF BENZOTRIAZOLE-FUNCTION DIORGANOPOLYSILOXANES AND NOVEL COSMETIC COMPOSITIONS CONTAINING THESE COMPOUNDS FOR THE PROTECTION OF SKIN AND HAIR |
| EP0392883A1 (en) * | 1989-02-15 | 1990-10-17 | L'oreal | Cosmetic use and compositions containing diorganopolysiloxanes with a benzotriazole function for skin and hair protection |
| FR2680683A1 (en) * | 1991-08-29 | 1993-03-05 | Oreal | Cosmetic screening composition containing a screening polymer having a hydrocarbon structure and a screening silicone |
| WO1993004665A1 (en) * | 1991-08-29 | 1993-03-18 | L'oreal | Filtering cosmetic composition containing a liposoluble filter polymer with hydrocarbonated structure and a filter silicone |
| EP0652210A1 (en) * | 1993-11-10 | 1995-05-10 | L'oreal | Solar filters containing a fluorohydrocarbon group, process for their preparation, and their use in cosmetic compositions |
| FR2712287A1 (en) * | 1993-11-10 | 1995-05-19 | Oreal | Novel hydrocarbon fluorinated sunscreens, process for their preparation and their use in cosmetic compositions |
| FR2714827A1 (en) * | 1994-01-10 | 1995-07-13 | Oreal | Cosmetic or dermatological composition containing a pseudo-latex consisting of particles of a homopolymer-filter U.V. |
| EP0666075A1 (en) * | 1994-01-10 | 1995-08-09 | L'oreal | Cosmetic or dermatologic composition containing an aqueous dispersion of solid particles of an U.V. screen homopolymer |
| EP0722938A3 (en) * | 1994-10-28 | 1997-01-22 | Roehm Gmbh | Process for preparation of a radically polymerizable UV absorber based on benztriazolyl phenols |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2601365B1 (en) | 1988-10-21 |
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