US4504644A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Protein derivative containing grafted ultraviolet-absorbing radicals, the process for its preparation and composition in which it is present
Assignee: L'Oréal SA
•
Filing: 1983-08-16
•
Granted: 1985-03-12
•
Expires: 2003-08-16
Abstract
Abstract The invention describes a protein derivative which has a molecular weight of 500 to 50,000 and has been chemically modified by grafting onto the protein chain radicals which absorb ultraviolet radiation. Also described are a process for the preparation of this protein derivative and compositions, containing this derivative as the active substance, for treating and protecting the skin and hair against photochemical degradation.
Inventors
- 👤 Gerard Lang
- 👤 Alain Malaval
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 22:13
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/72; A61K8/84; A61K8/89; A61K8/896; A61K8/898; A61Q; A61Q17/00; A61Q17/04; C; C08; C08H; C08H1/00; C08H1/06; A61Q5/00; A61Q5/02; Y; Y10; Y10S; Y10S424/00; Y10S424/01
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
359 words
A chemically modified protein derivative which has a molecular weight of about 500 to 50,000 and which corresponds to the following general formula: ##STR16## in which formula: Y is a radical of a molecule--capable of absorbing ultraviolet radiation; P 1 and P 2 are independently chain protein units which are not acylated or chemically modified by nucleophilic addition or substitution; N + (R 2 ) 4 , in M + represents H + , a cation derived from an alkali metal or from half an atom of magnesium, or N + (R 2 ) 4 , in which formula the radicals R 2 are identical or different and represent a hydrogen atom or an alkyl or hydroxyalkyl radical having at most 4 carbon atoms; each Q is independently an alkyl, aryl or aralkyl radical of a constituent aminoacid of the protein; T represents O, NH or, if the protein contains one or more cysteine units, S; Z is: (i) a radical SO 3 --M + , the cation M + being as defined; or (ii) SR 3 , in which formula R 3 represents: ##STR17## in which formulae p is 0 or an integer from 1 to 5, R 4 is a hydrogen atom or an alkyl radical having at most 4 carbon atoms and R 5 represents: ##STR18## in which formulae D is a linear or branched alkylene group containing a total of from 2 to 10 carbon atoms, the cation M.sup.⊕ is as defined above, the radicals R 6 being identical or different and representing a hydrogen atom or an alkyl or hydroxyalkyl radical having at most 4 carbon atoms, and E.sup.⊖ being a halide ion or RCOO.sup.⊖, RSO 3 .sup.⊖ or RSO 4 .sup.⊖, R representing a hydrocarbon rest containing from 1 to 10 carbon atoms; or alternatively (iii) an amino radical originating from a basic aminoacid of the protein, monosubstituted or disubstituted by a radical R 3 ; q is an integer from 1 to 5, with the proviso that, if Z represents a radical SO 3 .sup.⊖ M.sup.⊕ or SR 3 , q is necessarily equal to 1 and the protein contains cystine units;
Claim 2
Dependent Claim
359 words
A chemically modified protein derivative which has a molecular weight of about 500 to 50,000 and which corresponds to the following general formula: ##STR16## in which formula: Y is a radical of a molecule--capable of absorbing ultraviolet radiation; P 1 and P 2 are independently chain protein units which are not acylated or chemically modified by nucleophilic addition or substitution; N + (R 2 ) 4 , in M + represents H + , a cation derived from an alkali metal or from half an atom of magnesium, or N + (R 2 ) 4 , in which formula the radicals R 2 are identical or different and represent a hydrogen atom or an alkyl or hydroxyalkyl radical having at most 4 carbon atoms; each Q is independently an alkyl, aryl or aralkyl radical of a constituent aminoacid of the protein; T represents O, NH or, if the protein contains one or more cysteine units, S; Z is: (i) a radical SO 3 --M + , the cation M + being as defined; or (ii) SR 3 , in which formula R 3 represents: ##STR17## in which formulae p is 0 or an integer from 1 to 5, R 4 is a hydrogen atom or an alkyl radical having at most 4 carbon atoms and R 5 represents: ##STR18## in which formulae D is a linear or branched alkylene group containing a total of from 2 to 10 carbon atoms, the cation M.sup.⊕ is as defined above, the radicals R 6 being identical or different and representing a hydrogen atom or an alkyl or hydroxyalkyl radical having at most 4 carbon atoms, and E.sup.⊖ being a halide ion or RCOO.sup.⊖, RSO 3 .sup.⊖ or RSO 4 .sup.⊖, R representing a hydrocarbon rest containing from 1 to 10 carbon atoms; or alternatively (iii) an amino radical originating from a basic aminoacid of the protein, monosubstituted or disubstituted by a radical R 3 ; q is an integer from 1 to 5, with the proviso that, if Z represents a radical SO 3 .sup.⊖ M.sup.⊕ or SR 3 , q is necessarily equal to 1 and the protein contains cystine units;
Claim 3
Dependent Claim
29 words
the units A represent from 1 to 70% by weight of the protein derivative; and the units B represent from 0 to 15% by weight of the protein derivative.
Claim 4
Dependent Claim
29 words
the units A represent from 1 to 70% by weight of the protein derivative; and the units B represent from 0 to 15% by weight of the protein derivative.
Claim 5
Dependent Claim
31 words
A protein derivative according to claim 1, in which the protein from which it is obtained is a protein originating from keratin, gelatin, egg white albumin, blood albumin, casein or lactalbumin.
Claim 6
Dependent Claim
26 words
A protein derivative according to claim 1, in which the protein from which it is obtained is a protein originating from soya, groundnut or cotton seeds.
Claim 7
Dependent Claim
27 words
A protein derivative according to claim 1, which is derived from a protein hydrolysate which is chemically modified after the hydrolysis by which it has been produced.
Claim 8
Dependent Claim
205 words
A protein derivative according to claim 1, in which the radical Y is one of the following radicals: a cinnamoyl radical optionally substituted by one or more lower alkoxy groups; a para-dialkylaminobenzoyl radical; a salicyloyl radical; an acyl or sulphonyl radical of a carboxylic or sulphonic acid derived from benzylidene-camphor optionally substituted on the aromatic nucleus by one or more alkyl, lower alkoxy or sulpho radicals or by an alkenyl radical carrying one or more alkoxycarbonyl radicals, and/or optionally substituted on the carbon atom in the 10-position of the camphor by a sulpho group; a sulphonyl radical of an optionally substituted isophthalylidene-camphor or terephthalylidene-camphor radical; an acyl or sulphonyl radical of a carboxylic or sulphonic acid derived from a heterocyclic absorber which is a 2-arylbenzimidazole, 2-arylbenzofuran, 2-arylbenzoxazole, 2-arylbenzotriazole or 2-arylindole; an acyl or sulphonyl radical of a carboxylic or sulphonic acid derived from a hydroxybenzophenone absorber; an acyl radical of a carboxylic coumarin absorber, optionally substituted by one or more lower alkyl or alkoxy radicals; an acyl radical of a monophenylcyanoacrylic or diphenylcyanoacrylic absorber, optionally substituted on the aromatic nucleus (or nuclei); or an acyl or sulphonyl radical of a dibenzoylmethane absorber, optionally substituted by one or more hydroxyl or lower alkoxy or alkyl radicals.
Claim 9
Dependent Claim
19 words
A protein derivative according to claim 5, in which the group Y-- is one of the following radicals: ##STR19##
Claim 10
Dependent Claim
16 words
A protein derivative according to claim 1 which has a molecular weight of 5,000 to 30,000.
Claim 11
Dependent Claim
36 words
A protein derivative according to claim 1 in which Z represents SR 3 in which R 3 corresponds to the formula (II) or (IV), R 4 is a hydrogen atom and p is equal to 0.
Claim 12
Dependent Claim
240 words
Process for the preparation of the protein derivative as defined in claim 1 which comprises: firstly, optionally subjecting a protein to acid or enzyme hydrolysis so that the molecular weight of the hydrolysate obtained is from about 500 to 50,000; secondly, grafting one or more radicals absorbing ultraviolet radiation onto the optionally hydrolysed protein by reacting it with one or more compounds corresponding to the following formula: Y-X', in which formula X' represents a halogen atom and Y is as defined in claim 1; optionally, if any amino groups remain after the grafting, reacting the product with an alkylating agent corresponding to one of the following formulae: ##STR20## in which formula X 1 represents a halogen atom, R 4 , R 5 and p are as defined in claim 1 and R 7 denotes a hydrogen atom or an alkyl radical having at most 4 carbon atoms; and optionally, when the protein contains cystine, oxidising all or some of the disulphide bridges of the cystine groups of the treated protein so as to give acid --SO 3 H groups, this oxidation optionally being followed by salification of the abovementioned acid --SO 3 H groups, or reducing all or some of the disulphide bridges of the cystine groups of the treated protein to give thiol groups --SH, this reduction being followed by S-alkylation with an alkylating agent corresponding to one of the formulae (IIa), (IIIa), (IVa) and (IV'a) as defined above.
Claim 13
Dependent Claim
35 words
Process according to claim 9, in which the S-alkylating or N-alkylating agent used corresponds to the formula: X.sub.1 --CH.sub.2 --CO.sub.2.sup.⊖ M.sup.61 , in which formula X 1 and M.sup.⊕ are as defined in claim 9.
Claim 14
Dependent Claim
22 words
Process according to claim 9, in which the oxidation is carried out in an acid medium with hydrogen peroxide or a peracid.
Claim 15
Dependent Claim
32 words
A cosmetic composition suitable for treating the skin which comprises, in the presence of a cosmetically acceptable carrier, an effective amount of at least one protein derivative as claimed in claim 1.
Claim 16
Dependent Claim
32 words
A composition suitable for treating natural or sensitised hair which comprises, in the presence of a suitable carrier, an effective amount of at least one protein derivative as claimed in claim 1.
Claim 17
Dependent Claim
30 words
A composition according to claim 12 in which the protein derivative is present in an amount by weight of 0.5 to 15%, relative to the total weight of the composition.
Claim 18
Dependent Claim
30 words
A composition according to claim 13 in which the protein derivative is present in an amount by weight of 0.5 to 15%, relative to the total weight of the composition.
Claim 19
Dependent Claim
24 words
A composition according to claim 12, in which the protein derivative is solubilised in water, a lower mono-alcohol or polyol or an aqueous-alcoholic solution.
Claim 20
Dependent Claim
29 words
A composition according to claim 12, which contains at least one thickener, softener, humectant, superfatting agent, emollient, wetting agent, surface-active agent, preservative, anti-foam agent, oil, wax, colourant or pigment.
Claim 21
Dependent Claim
36 words
A composition according to claim 12, which is a solution in the form of a lotion, an emulsion in the form of a cream or milk or a gel, or is packaged in an aerosol can.
Claim 22
Dependent Claim
82 words
A composition according to claim 13, which contains at least one non-ionic, anionic, cationic or amphoteric surface-active agent, an animal, mineral, vegetable or synthetic oil or wax, a silicone derivative, fatty alcohol, anionic, cationic, non-ionic or amphoteric resin, emulsifying agent, sun filter compatible with a derivative of formula (I), an organic solvent, thickener, opacifier, preservative, sequestering agent, antioxidant, perfume, agent for imparting pearlescence, colourant, pH modifier, reducing agent, electrolyte, oxidising agent, natural substance, anti-seborrhea agent, anti-grease agent, antidandruff agent or restructuring agent.
Claim 23
Dependent Claim
63 words
A composition according to claim 13, which is in the form of a shampoo, a lotion, gel or emulsion to be rinsed off before or after shampooing, before or after colouring or bleaching the hair or before or after perming, a styling or treatment lotion, a blow-drying or setting lotion, a hair lacquer or a composition for perming, colouring or bleaching the hair.
Claim 24
Dependent Claim
32 words
A composition according to claim 20 which is in the form of a shampoo and contains an anionic, non-ionic or amphoteric surface-active agent in an amount from 2 to 50% by weight.
Claim 25
Dependent Claim
33 words
A composition according to claim 20 which is in the form of a leave-on lotion and contains an anionic, non-ionic, cationic or amphoteric polymer in an amount of 0.1 to 10% by weight.
Claim 26
Dependent Claim
17 words
A composition according to claim 22 which contains 0.1 to 3% by weight of the said polymer.
Claim 27
Dependent Claim
46 words
A composition according to claim 20 which is in the form of a rinse-off lotion and contains, in aqueous, alcoholic or aqueous-alcoholic solution, at least one compound of the formula (I) and, optionally, from 0.1 to 10% by weight of a non-ionic or cationic surface-active agent.
Claim 28
Dependent Claim
30 words
A composition according to claim 20 which is in the form of a rinse-off non-ionic emulsion and contains at least one oil, fatty alcohol or polyoxyethyleneated fatty alcohol and water.
Claim 29
Dependent Claim
22 words
A composition according to claim 20 which is in the form of a rinse-off anionic emulsion and contains at least one soap.
Claim 30
Dependent Claim
24 words
A composition according to claim 20 which is in the form of a gel and contains 0.5 to 30% by weight of a thickener.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-03-11 | 1988-09-10 | 1989-03-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-03-11 | 1992-09-10 | 1993-03-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-03-11 | 1996-09-10 | 1997-03-12 | $7700.00 | Window Closed / Lapsed |