FR2466492A1 - Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid - Google Patents
Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid Download PDFInfo
- Publication number
- FR2466492A1 FR2466492A1 FR7924627A FR7924627A FR2466492A1 FR 2466492 A1 FR2466492 A1 FR 2466492A1 FR 7924627 A FR7924627 A FR 7924627A FR 7924627 A FR7924627 A FR 7924627A FR 2466492 A1 FR2466492 A1 FR 2466492A1
- Authority
- FR
- France
- Prior art keywords
- coloring
- amino acid
- ketone
- aldehyde
- agent
- 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.)
- Granted
Links
- 239000000126 substance Substances 0.000 title claims abstract description 16
- 210000004209 hair Anatomy 0.000 title claims abstract description 6
- 150000001299 aldehydes Chemical class 0.000 title claims description 14
- 150000002576 ketones Chemical class 0.000 title claims description 11
- 102000011782 Keratins Human genes 0.000 title claims description 4
- 108010076876 Keratins Proteins 0.000 title claims description 4
- 238000004043 dyeing Methods 0.000 title abstract 4
- 150000001413 amino acids Chemical class 0.000 claims abstract description 34
- 235000001014 amino acid Nutrition 0.000 claims abstract description 32
- 238000004040 coloring Methods 0.000 claims abstract description 19
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 6
- -1 sulphoxy Chemical group 0.000 claims abstract description 6
- 210000003746 feather Anatomy 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 24
- QEFRNWWLZKMPFJ-ZXPFJRLXSA-N L-methionine (R)-S-oxide Chemical compound C[S@@](=O)CC[C@H]([NH3+])C([O-])=O QEFRNWWLZKMPFJ-ZXPFJRLXSA-N 0.000 claims description 14
- QEFRNWWLZKMPFJ-UHFFFAOYSA-N L-methionine sulphoxide Natural products CS(=O)CCC(N)C(O)=O QEFRNWWLZKMPFJ-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000003086 colorant Substances 0.000 claims description 7
- 239000006185 dispersion Substances 0.000 claims description 6
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 5
- 229960003067 cystine Drugs 0.000 claims description 5
- 229930182817 methionine Natural products 0.000 claims description 5
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- BHLMCOCHAVMHLD-REOHCLBHSA-N S-oxy-L-cysteine Chemical compound OC(=O)[C@@H](N)CS=O BHLMCOCHAVMHLD-REOHCLBHSA-N 0.000 claims description 3
- 235000018417 cysteine Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 229940083753 renown Drugs 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 3
- 230000035515 penetration Effects 0.000 abstract description 3
- 239000000975 dye Substances 0.000 abstract 3
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000002537 cosmetic Substances 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 20
- 239000006071 cream Substances 0.000 description 17
- 229940120503 dihydroxyacetone Drugs 0.000 description 10
- 210000003491 skin Anatomy 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 210000001519 tissue Anatomy 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- HIMXGTXNXJYFGB-UHFFFAOYSA-N alloxan Chemical compound O=C1NC(=O)C(=O)C(=O)N1 HIMXGTXNXJYFGB-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 150000003462 sulfoxides Chemical class 0.000 description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229960000541 cetyl alcohol Drugs 0.000 description 2
- UQPHVQVXLPRNCX-UHFFFAOYSA-N erythrulose Chemical compound OCC(O)C(=O)CO UQPHVQVXLPRNCX-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 210000002374 sebum Anatomy 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- RXQXJZDPDXVIEN-UHFFFAOYSA-N 2-azaniumyl-3-(2-azaniumyl-2-carboxylatoethyl)sulfonylsulfanylpropanoate Chemical compound OC(=O)C(N)CSS(=O)(=O)CC(N)C(O)=O RXQXJZDPDXVIEN-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 206010040829 Skin discolouration Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 206010047642 Vitiligo Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229960002173 citrulline Drugs 0.000 description 1
- 235000013477 citrulline Nutrition 0.000 description 1
- 230000035614 depigmentation Effects 0.000 description 1
- 210000004207 dermis Anatomy 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 210000000003 hoof Anatomy 0.000 description 1
- 210000003284 horn Anatomy 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
-
- 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
- A61K8/35—Ketones, e.g. benzophenone
-
- 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
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
-
- 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
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
-
- 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
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7924627A FR2466492A1 (en) | 1979-10-03 | 1979-10-03 | Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid |
| GB8031407A GB2062016B (en) | 1979-10-03 | 1980-09-29 | Process and composition for the colouration of keratin-containing substances |
| US06/193,397 US4293543A (en) | 1979-10-03 | 1980-10-02 | Process and composition for the coloration of keratin-containing substances |
| IT25076/80A IT1133801B (it) | 1979-10-03 | 1980-10-02 | Procedimento e composizione per la colorazione di sostanze contenenti cheratina |
| DE19803037497 DE3037497A1 (de) | 1979-10-03 | 1980-10-03 | Verfahren und zusammensetzung zur faerbung von substanzen, die keratin enthalten, sowie deren verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7924627A FR2466492A1 (en) | 1979-10-03 | 1979-10-03 | Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2466492A1 true FR2466492A1 (en) | 1981-04-10 |
| FR2466492B1 FR2466492B1 (OSRAM) | 1983-04-22 |
Family
ID=9230267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7924627A Granted FR2466492A1 (en) | 1979-10-03 | 1979-10-03 | Dyeing keratin substances, e.g. skin, nails, hair, fur - with compsns. contg. ketone or aldehyde dye and sulphoxy-aminoacid |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2466492A1 (OSRAM) |
Cited By (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2591103A1 (fr) * | 1985-12-11 | 1987-06-12 | Oreal | Composition cosmetique pour la coloration de la peau renfermant de l'aldehyde mesotartrique et une ou plusieurs hydroxyquinones et procede de coloration de la peau avec cette composition. |
| EP0547864A1 (en) * | 1991-12-16 | 1993-06-23 | Unilever Plc | Self-tanner cosmetic composition |
| WO1995011002A1 (de) * | 1993-10-19 | 1995-04-27 | Henkel Kommanditgesellschaft Auf Aktien | Ethandione zum färben keratinhaltiger fasern |
| FR2712804A1 (fr) * | 1993-11-25 | 1995-06-02 | Merck Patent Gmbh | Composition provoquant une coloration de la peau. |
| WO1995026179A1 (en) * | 1994-03-29 | 1995-10-05 | The Procter & Gamble Company | Artificial tanning compositions having improved color development |
| FR2719217A1 (fr) * | 1994-04-28 | 1995-11-03 | Merck Patent Gmbh | Préparation pour la coloration de la peau. |
| FR2746391A1 (fr) * | 1996-03-22 | 1997-09-26 | Oreal | Compositions cosmetiques a base de pyrazolin-4,5-diones, nouvelles pyrazolin-4,5 diones, procedes de preparation et utilisations |
| US6165229A (en) * | 1996-03-22 | 2000-12-26 | L'oreal | Imidazoloazole-containing compositions for dyeing keratin fibers; their use in dyeing as couplers; dyeing process |
| US6179882B1 (en) | 1996-03-22 | 2001-01-30 | L'oreal | Keratin fibre dye composition containing pyrazolopyrimidinoxo compounds, use thereof as dye couplers, and dyeing methods |
| US6210447B1 (en) | 1996-03-22 | 2001-04-03 | L'oreal | Compositions containing pyrazolin-3,5-dione couplers for use in keratin fiber dyeing methods and kits |
| US6231623B1 (en) | 1996-03-22 | 2001-05-15 | L'oreal S.A. | Methods of dyeing keratin fibers with compositions containing pyrazolo-azole couplers |
| US6238440B1 (en) | 1996-03-22 | 2001-05-29 | L'oreal S.A. | Keratin fibre dye compositions containing pyrrolo-azole compounds, use thereof as couplers, and dyeing method |
| US6537528B2 (en) | 2000-07-12 | 2003-03-25 | L'oreal S.A. | Composition comprising at least one self-tanning agent chosen from monocarbonyl and polycarbonyl compounds and a flavylium salt compound which is unsubstituted in position 3, for coloring the skin, and uses thereof |
| EP1317920A1 (fr) * | 2001-12-07 | 2003-06-11 | L'oreal | Composition autobronzante contenant un dérivé du 2-hydroxybenzophénone aminosubstitué et un agent autobronzant |
| US6740313B2 (en) | 2001-10-16 | 2004-05-25 | L'oreal S.A. | Compositions for giving the skin a coloration similar to that of a natural tan, based on a pigment of the monascus type, and uses thereof |
| EP1671680A1 (fr) | 2004-12-20 | 2006-06-21 | L'oreal | Produit autobronzant à deux composants, dispositifs multicompartiments, procédé de coloration de la peau |
| EP1754513A2 (fr) | 2005-08-17 | 2007-02-21 | L'oreal | Utilisation de l'acide 8-hexadécène-1,16-dicarboxylique comme agent de soin destiné à favoriser la cohésion de la couche cornée |
| EP2011481A2 (fr) | 2007-07-06 | 2009-01-07 | L'Oreal | Composition de protection solaire contenant l'association d'un polymère semi-cristallin et de particules de latex creuses |
| EP2014277A1 (fr) | 2007-07-12 | 2009-01-14 | L'Oreal | Composition photoprotectrice fluide aqueuse à base d'un polymère polyamide à terminaison amide tertiaire |
| WO2009010686A3 (fr) * | 2007-07-09 | 2009-04-16 | Oreal | Procede de maquillage de la peau, des levres ou des ongles utilisant un colorant obtenu par reaction d'une amine avec l'acide dehydroascorbique ou un derive monomere, polymere ou isomere |
| EP2119429A1 (fr) | 2008-05-14 | 2009-11-18 | L'Oréal | Composition cosmetique contenant un derive de dibenzoylmethane et un derive de pyrrolidinone ; procede de photostabilisation du derive de dibenzoylmethane |
| EP2174644A1 (fr) | 2008-10-08 | 2010-04-14 | L'oreal | Composition cosmétique contenant un dérivé de dibenzoylméthane et un composé dithiolane; procédé de photostabilisation du dérivé de dibenzoylmethane |
| EP2191869A1 (fr) | 2008-12-01 | 2010-06-02 | L'oreal | Procédé de coloration artificielle de la peau utilisant un mélange de caroténoide et de colorant vert lipophile ; nouveau mélange de colorants lipophiles ; composition |
| WO2011023886A2 (fr) | 2009-08-28 | 2011-03-03 | L'oreal | Composition contenant au moins un filtre du type 2- hydroxybenzophenone lipophile et une s-triazine siliciee substituee par au moins deux groupes alkylaminobenzoates |
| WO2011042358A1 (en) | 2009-10-08 | 2011-04-14 | L'oreal | Photoprotective composition based on a 2-alkoxy-4-alkyl ketone phenol compound; use of said compound for increasing the sun protection factor |
| WO2011073279A2 (fr) | 2009-12-18 | 2011-06-23 | L'oreal | Procédé de traitement cosmétique impliquant un composé apte à condenser in situ |
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