CA1168659A - Quaternary dibenzoylmethane derivatives, their application as solar filters; cosmetic compositions therefrom - Google Patents
Quaternary dibenzoylmethane derivatives, their application as solar filters; cosmetic compositions therefromInfo
- Publication number
- CA1168659A CA1168659A CA000383044A CA383044A CA1168659A CA 1168659 A CA1168659 A CA 1168659A CA 000383044 A CA000383044 A CA 000383044A CA 383044 A CA383044 A CA 383044A CA 1168659 A CA1168659 A CA 1168659A
- Authority
- CA
- Canada
- Prior art keywords
- dibenzoylmethane
- fact
- methosulfate
- trimethylammonio
- derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical group C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 title claims abstract 24
- 239000000203 mixture Substances 0.000 title claims 10
- 239000002537 cosmetic Substances 0.000 title claims 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 230000005855 radiation Effects 0.000 claims abstract 4
- 238000001914 filtration Methods 0.000 claims abstract 3
- 150000001450 anions Chemical class 0.000 claims abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract 2
- 239000011707 mineral Substances 0.000 claims abstract 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 claims 9
- 238000000034 method Methods 0.000 claims 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- -1 hydroxyalkyl radical Chemical class 0.000 claims 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000006260 foam Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- RNXKQWUWAZFDIE-UHFFFAOYSA-N O=C(CC(C1=CC=CC=C1)=O)C1=CC=CC=C1.Br Chemical compound O=C(CC(C1=CC=CC=C1)=O)C1=CC=CC=C1.Br RNXKQWUWAZFDIE-UHFFFAOYSA-N 0.000 claims 1
- JXAHPMZPXFJQQX-UHFFFAOYSA-N O=C(CC(C1=CC=CC=C1)=O)C1=CC=CC=C1.Cl Chemical compound O=C(CC(C1=CC=CC=C1)=O)C1=CC=CC=C1.Cl JXAHPMZPXFJQQX-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000003974 emollient agent Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000003925 fat Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 239000003906 humectant Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 239000008267 milk Substances 0.000 claims 1
- 210000004080 milk Anatomy 0.000 claims 1
- 235000013336 milk Nutrition 0.000 claims 1
- 239000003921 oil Substances 0.000 claims 1
- 239000002304 perfume Substances 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000002562 thickening agent Substances 0.000 claims 1
- 238000009827 uniform distribution Methods 0.000 claims 1
- 239000001993 wax Substances 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
L'invention concerne de nouveaux dérivés de dibenzoylméthane quaternaire répondant à la formule générale: <IMG> dans laquelle R1 et R2 représentent un radical alcoyle ou hydroxyalcoyle inférieur, R3 représente le radical alcoyle ou alcoyloxy inférieur, n est un nombre entier de 0 à 3, X- est un anion dérivé d'un acide minéral ou organique. Les composés selon l'invention présentent de bonnes propriétés filtrantes vis-à-vis des rayonnements U.V et, en particulier, vis-à-vis des rayonnements UV.A, et présentent en outre une excellente solubilité en milieu aqueux, une bonne stabilité photochimique et thermique, ainsi qu'une bonne substantivité vis-à-vis de la peau de façon à ne pas être éliminé ou dégradé par la transpiration.The invention relates to new quaternary dibenzoylmethane derivatives corresponding to the general formula: <IMG> in which R1 and R2 represent a lower alkyl or hydroxyalkyl radical, R3 represents the lower alkyl or lower alkyloxy radical, n is an integer from 0 to 3 , X- is an anion derived from a mineral or organic acid. The compounds according to the invention exhibit good filtering properties with respect to UV radiation and, in particular, with respect to UV.A radiation, and also exhibit excellent solubility in aqueous medium, good photochemical stability and thermal, as well as good substantivity vis-à-vis the skin so as not to be eliminated or degraded by perspiration.
Claims (24)
sont définies comme suit: The embodiments of the invention about which a exclusive right of property or privilege is claimed are defined as follows:
(I) ou leur forme tautomère:
(Ia) dans lesquelles;
R1 et R2, identiques ou différents, représentent un radical alcoyle ou hydroxyalcoyle inférieur, R3 représente un radical alcoyle ou alcoyloxy inférieur, n est un nombre entier de 0 à 3, X- est un anion dérivé d'un acide minéral ou organique. 1. The dibenzoylmethane derivatives corresponding to the general formula:
(I) or their tautomeric form:
(Ia) in which;
R1 and R2, identical or different, represent a lower alkyl or hydroxyalkyl radical, R3 represents an alkyl or alkyloxy radical inferior, n is an integer from 0 to 3, X- is an anion derived from a mineral acid or organic.
le méthosulfate de triméthylammonio-4 dibenzoylméthane, le méthosulfate de triméthylammonio-4 méthyl-4' dibenzoyl-méthane, le méthosulfate de triméthylammonio-4 méthoxy-4' dibenzoylméthane, le chlorure de triméthylammonio-4 diben-zoylméthane, le méthosulfate de triméthylammonio-4 butoxy-2' dibenzoylméthane, le bromure de (diméthyl,.beta.-hydroxyéthyl) ammonio-4 dibenzoylméthane, le méthosulfate de triméthyl-ammonio-4, diméthoxy-2', 4' dibenzoylméthane. 6. Dibenzoylmethane derivative according to claim 1, characterized in that it is chosen from:
4-trimethylammonio-dibenzoylmethane methosulfate, trimethylammonio-4-methyl-4 'dibenzoyl- methosulfate methane, 4-trimethylammonio-4-methoxy methosulfate dibenzoylmethane, 4-trimethylammonio chloride diben-zoylmethane, trimethylammonio-4-butoxy-2 'methosulfate dibenzoylmethane, (dimethyl, .beta.-hydroxyethyl) bromide 4-ammonio dibenzoylmethane, trimethyl methosulfate ammonium-4, dimethoxy-2 ', 4' dibenzoylmethane.
en poids par rapport au poids total de la composition. 18. Composition according to claim 14, characterized by the fact that the dibenzoylmethane derivative is present in a proportion between 0.05 and 10%
by weight relative to the total weight of the composition.
par le fait que le dérivé du dibenzoylméthane est tel que défini à la revendication 6. 21. Method according to claim 20, characterized by the fact that the dibenzoylmethane derivative is such as defined in claim 6.
par le fait que le dérivé du dibenzoylméthane est tel que défini à la revendication 6. 24. Method according to claim 23, characterized by the fact that the dibenzoylmethane derivative is such that defined in claim 6.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8017407A FR2488252A1 (en) | 1980-08-06 | 1980-08-06 | QUATERNARY DIBENZOYLMETHANE DERIVATIVES, THEIR USE AS A SOLAR FILTERING AGENT AND COSMETIC COMPOSITION CONTAINING THEM |
| FR8017407 | 1980-08-06 | ||
| FR8113885 | 1981-07-16 | ||
| FR8113885A FR2509723B2 (en) | 1981-07-16 | 1981-07-16 | NOVEL QUATERNARY DIBENZOYLMETHANE DERIVATIVES, THEIR USE AS SOLAR FILTERING AGENT AND COSMETIC COMPOSITION CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1168659A true CA1168659A (en) | 1984-06-05 |
Family
ID=26221938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000383044A Expired CA1168659A (en) | 1980-08-06 | 1981-07-31 | Quaternary dibenzoylmethane derivatives, their application as solar filters; cosmetic compositions therefrom |
Country Status (9)
| Country | Link |
|---|---|
| AU (1) | AU553001B2 (en) |
| CA (1) | CA1168659A (en) |
| CH (1) | CH649987A5 (en) |
| ES (1) | ES504560A0 (en) |
| GB (1) | GB2081716B (en) |
| GR (1) | GR74989B (en) |
| IT (1) | IT1144823B (en) |
| NL (1) | NL8103667A (en) |
| PT (1) | PT73484B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2526658B2 (en) * | 1981-05-20 | 1986-05-23 | Oreal | COSMETIC COMPOSITIONS CONTAINING HYDROXYLATED DIBENZOYLMETHANE DERIVATIVES AND THEIR USE FOR PROTECTING THE HUMAN EPIDERMAL AGAINST ULTRAVIOLET RAYS, NEW HYDROXYLATED DIBENZOYLMETHANE DERIVATIVES AND THEIR PREPARATION PROCESS |
| JPS60190708A (en) * | 1984-03-12 | 1985-09-28 | Kao Corp | Absorbent for ultraviolet radiation having long wavelength |
| LU86703A1 (en) * | 1986-12-08 | 1988-07-14 | Oreal | PHOTOSTABLE COSMETIC COMPOSITION CONTAINING A UV-A FILTER AND A UV-B FILTER, ITS USE FOR PROTECTING THE SKIN AGAINST UV RAYS AND A METHOD OF STABILIZING THE UV-A FILTER WITH THE UV-B FILTER |
| ZA882388B (en) * | 1987-04-09 | 1988-09-22 | Merrell Dow Pharmaceuticals Inc. | Chalcone derivatives and their preparation and use |
| US4863968A (en) * | 1987-04-09 | 1989-09-05 | Merrell Dow Pharmaceuticals Inc. | Methods of treating gout with chalcone derivatives |
| US4753965A (en) * | 1987-04-09 | 1988-06-28 | Merrell Dow Pharmaceuticals, Inc. | Method of treating multiple sclerosis with chalcone derivatives |
| US4904697A (en) * | 1987-04-09 | 1990-02-27 | Merrell Dow Pharmaceuticals Inc. | Controlling the growth of certain tumor tissue with chalcone derivatives |
| DK0773982T3 (en) * | 1994-07-26 | 2001-01-15 | Procter & Gamble | Fabric softener with textile softener compositions containing antioxidants for protecting textiles from the sun |
| WO1996003486A1 (en) * | 1994-07-26 | 1996-02-08 | The Procter & Gamble Company | Rinse added fabric softener compositions containing sunscreens for sun-fade protection for fabrics |
| US5543083A (en) * | 1994-07-26 | 1996-08-06 | The Procter & Gamble Company | Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation |
| US5474691A (en) * | 1994-07-26 | 1995-12-12 | The Procter & Gamble Company | Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics |
| WO2010020668A1 (en) * | 2008-08-22 | 2010-02-25 | Unilever Nv | A cosmetic composition |
-
1981
- 1981-07-31 CA CA000383044A patent/CA1168659A/en not_active Expired
- 1981-08-04 GR GR65736A patent/GR74989B/el unknown
- 1981-08-04 CH CH5036/81A patent/CH649987A5/en not_active IP Right Cessation
- 1981-08-04 NL NL8103667A patent/NL8103667A/en not_active Application Discontinuation
- 1981-08-05 IT IT68095/81A patent/IT1144823B/en active
- 1981-08-05 AU AU73699/81A patent/AU553001B2/en not_active Ceased
- 1981-08-05 GB GB8123918A patent/GB2081716B/en not_active Expired
- 1981-08-05 ES ES504560A patent/ES504560A0/en active Granted
- 1981-08-06 PT PT73484A patent/PT73484B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2081716B (en) | 1984-06-13 |
| GB2081716A (en) | 1982-02-24 |
| PT73484A (en) | 1981-09-01 |
| NL8103667A (en) | 1982-03-01 |
| CH649987A5 (en) | 1985-06-28 |
| GR74989B (en) | 1984-07-12 |
| IT1144823B (en) | 1986-10-29 |
| AU553001B2 (en) | 1986-06-26 |
| AU7369981A (en) | 1982-02-11 |
| ES8306590A1 (en) | 1983-06-01 |
| IT8168095A0 (en) | 1981-08-05 |
| ES504560A0 (en) | 1983-06-01 |
| PT73484B (en) | 1983-04-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |