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US5244497A
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Process for the preparation of a melanic pigment by an enzyme route and its use in cosmetics
Assignee: L'Oréal SA
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Filing: 1991-02-05
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Granted: 1993-09-14
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Expires: 2011-02-05
Abstract
Abstract The invention relates to a process for the preparation of a melanic pigment, comprising the polymerisation of a compound corresponding to the formula: <IMAGE> (I) in which: R denotes a hydrogen atom, an alkyl, alkoxy, hydroxyalkyl, SiR4R5R6 or aminoalkyl radical, or an aryl radical which is unsubstituted or substituted by OH, NH2, alkyl, alkoxy or NO2; R1 and R2 denote alkyl groups or together form a methylene or ethylene group which is optionally substituted by one or more alkyl groups, and R2 denotes hydrogen or COOH, in the presence of an oxidizing medium and of an enzyme with (per)oxidizing activity or of a compound which has a similar activity, and to powders which make use of them and to their cosmetic use.
Inventors
- 👤 Alex Junino
- 👤 Herve Andrean
- 👤 Remi Tuloup
- 👤 Irwing J. Higgins
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 11:50
CPC Classifications
A; A61; A61K; A61K8/00; A61K8/18; A61K8/72; A61K8/30; A61K8/49; A61K8/4906; A61K8/4913; A61K8/492; A61Q; A61Q5/00; A61Q5/10; C; C09; C09B; C09B69/00; C09B69/10; C09B69/104; C12; C12P; C12P17/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
142 words
A process for the preparation of a melanic pigment comprising polymerizing in a polymerization medium a compound having the formula ##STR3## wherein R represents hydrogen, alkyl, alkoxy, hydroxyalkyl, aminoalkyl or SiR 4 R 5 R 6 wherein R 4 , R 5 and R 6 represent alkyl containing 1-8 carbon atoms or aryl unsubstituted or substituted by OH, NH 2 , alkyl, alkoxy or NO 2 , R 1 and R 2 , each independently, represent lower alkyl, or R 1 and R 2 taken together form a methylene or ethylene group optionally substituted by one or more lower alkyl groups, and R 3 represents hydrogen or COOH, said polymerization medium comprising (i) hydrogen peroxide or oxone as an oxidizing medium and (ii) horseradish peroxidase as an enzyme having (per) oxidizing activity or haemoglobin as a compound having a (per) oxidizing activity.
Claim 2
Dependent Claim
142 words
A process for the preparation of a melanic pigment comprising polymerizing in a polymerization medium a compound having the formula ##STR3## wherein R represents hydrogen, alkyl, alkoxy, hydroxyalkyl, aminoalkyl or SiR 4 R 5 R 6 wherein R 4 , R 5 and R 6 represent alkyl containing 1-8 carbon atoms or aryl unsubstituted or substituted by OH, NH 2 , alkyl, alkoxy or NO 2 , R 1 and R 2 , each independently, represent lower alkyl, or R 1 and R 2 taken together form a methylene or ethylene group optionally substituted by one or more lower alkyl groups, and R 3 represents hydrogen or COOH, said polymerization medium comprising (i) hydrogen peroxide or oxone as an oxidizing medium and (ii) horseradish peroxidase as an enzyme having (per) oxidizing activity or haemoglobin as a compound having a (per) oxidizing activity.
Claim 3
Dependent Claim
185 words
A process for the preparation of a melanic pigment comprising polymerizing in a polymerization medium a compound having the formula ##STR4## wherein R represents hydrogen, alkyl, alkoxy, hydroxyalkyl, aminoalkyl or SiR 4 R 5 R 6 wherein R 4 , R 5 and R 6 represent alkyl containing 1-8 carbon atoms or aryl unsubstituted or substituted by OH, NH 2 , alkyl, alkoxy or NO 2 , R 1 and R 2 , each independently, represent lower alkyl, or R 1 and R 2 taken together form a methylene or ethylene group optionally substituted by one or more lower alkyl groups, and R 3 represents hydrogen or COOH, said polymerization medium comprising (i) an oxidizing medium and (ii) at least one of (1) an enzyme having (per)oxidizing activity and selected from the group consisting of horseradish peroxidase, chloroperoxidase, milk peroxidase, cytochrome C peroxidase and microperoxidase, (2) a compound having (per)oxidizing activity and selected from the group consisting of haemoglobin, myoglobin, methaemoglobin and metmyoglobin and (3) an enzyme having oxidizing activity and selected from the group consisting of an alcohol-oxidase, a polyphenol-oxidase and a dealkylating monooxygenase.
Claim 4
Dependent Claim
185 words
A process for the preparation of a melanic pigment comprising polymerizing in a polymerization medium a compound having the formula ##STR4## wherein R represents hydrogen, alkyl, alkoxy, hydroxyalkyl, aminoalkyl or SiR 4 R 5 R 6 wherein R 4 , R 5 and R 6 represent alkyl containing 1-8 carbon atoms or aryl unsubstituted or substituted by OH, NH 2 , alkyl, alkoxy or NO 2 , R 1 and R 2 , each independently, represent lower alkyl, or R 1 and R 2 taken together form a methylene or ethylene group optionally substituted by one or more lower alkyl groups, and R 3 represents hydrogen or COOH, said polymerization medium comprising (i) an oxidizing medium and (ii) at least one of (1) an enzyme having (per)oxidizing activity and selected from the group consisting of horseradish peroxidase, chloroperoxidase, milk peroxidase, cytochrome C peroxidase and microperoxidase, (2) a compound having (per)oxidizing activity and selected from the group consisting of haemoglobin, myoglobin, methaemoglobin and metmyoglobin and (3) an enzyme having oxidizing activity and selected from the group consisting of an alcohol-oxidase, a polyphenol-oxidase and a dealkylating monooxygenase.
Claim 5
Dependent Claim
40 words
The process of claim 2 wherein the weight relationship between said compound of formula (I) and said enzyme having (per)oxidizing activity or a compound having (per)oxidizing activity or an enzyme having oxidizing activity is between 1 and 10 6 .
Claim 6
Dependent Claim
23 words
The process of claim 1 wherein said compound of formula (I) is selected from the group consisting of 5,6-dimethoxyindole, 5,6-methylenedioxyindole and 1-methyl 5,6-dimethoxyindole.
Claim 7
Dependent Claim
15 words
The process of claim 2 wherein said oxidizing medium contains hydrogen peroxide or a persalt.
Claim 8
Dependent Claim
11 words
The process of claim 2 wherein said alcohol-oxidase is a methanol-oxidase.
Claim 9
Dependent Claim
52 words
The process of claim 2 wherein said polymerization medium also contains a reaction medium consisting of water or a mixture of water and an organic solvent and the concentration of hydrogen peroxide in said polymerization medium is lower than 5 percent by weight relative to the total weight of said reaction medium.
Claim 10
Dependent Claim
30 words
The process of claim 7 which includes maintaining the pH of said reaction medium at a value ranging from 2 to 11 using a buffer appropriate to the enzyme employed.
Claim 11
Dependent Claim
15 words
The process of claim 1 wherein the polymerization temperature ranges from 10° to 50° C.
Claim 12
Dependent Claim
15 words
The process of claim 1 wherein the polymerization temperature ranges from 20° to 45° C.
Claim 13
Dependent Claim
16 words
The process of claim 1 which includes immobilizing said enzyme on the surface of a support.
Claim 14
Dependent Claim
12 words
A melanic pigment made in accordance with the process of claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1996-09-13 | 1997-03-15 | 1997-09-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-09-13 | 2001-03-15 | 2001-09-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-09-13 | 2005-03-15 | 2005-09-14 | $7700.00 | Window Closed / Lapsed |