AU648796B2 - Creación de Inventos y Patentes con Inteligencia Artificial

AU648796B2 – Process for dyeing keratinous fibres with 2,6-dimethyl- 1,4-diaminobenzene and/or 2,3-dimethyl-1,4-diaminobenzene and/or 2,6-diethyl-1,4-diaminobenzene in an acid medium and compositions employed
– Google Patents
Process for dyeing keratinous fibres with 2,6-dimethyl- 1,4-diaminobenzene and/or 2,3-dimethyl-1,4-diaminobenzene and/or 2,6-diethyl-1,4-diaminobenzene in an acid medium and compositions employed

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Publication number
AU648796B2

AU648796B2
AU78015/91A
AU7801591A
AU648796B2
AU 648796 B2
AU648796 B2
AU 648796B2
AU 78015/91 A
AU78015/91 A
AU 78015/91A
AU 7801591 A
AU7801591 A
AU 7801591A
AU 648796 B2
AU648796 B2
AU 648796B2
Authority
AU
Australia
Prior art keywords
diaminobenzene
composition
dyeing
dimethyl
component
Prior art date
1990-05-31
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.)

Ceased

Application number
AU78015/91A
Other versions

AU7801591A
(en

Inventor
Jean Cotteret
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

LOreal SA

Original Assignee
LOreal SA
Priority date (The priority date 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 date listed.)
1990-05-31
Filing date
1991-05-30
Publication date
1994-05-05
Family has litigation

First worldwide family litigation filed
litigation
Critical
https://patents.darts-ip.com/?family=9397158&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AU648796(B2)
«Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1991-05-30
Application filed by LOreal SA
filed
Critical
LOreal SA

1991-12-05
Publication of AU7801591A
publication
Critical
patent/AU7801591A/en

1994-05-05
Application granted
granted
Critical

1994-05-05
Publication of AU648796B2
publication
Critical
patent/AU648796B2/en

2011-05-30
Anticipated expiration
legal-status
Critical

Status
Ceased
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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mixture
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abstract
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Ammonium hydroxide
Chemical compound

[NH4+].[OH-]
VHUUQVKOLVNVRT-UHFFFAOYSA-N
0.000
description
1

GAWIXWVDTYZWAW-UHFFFAOYSA-N
C[CH]O
Chemical group

C[CH]O
GAWIXWVDTYZWAW-UHFFFAOYSA-N
0.000
description
1

229920002134
Carboxymethyl cellulose
Polymers

0.000
description
1

241001070941
Castanea
Species

0.000
description
1

235000014036
Castanea
Nutrition

0.000
description
1

FEWJPZIEWOKRBE-JCYAYHJZSA-N
Dextrotartaric acid
Chemical compound

OC(=O)[C@H](O)[C@@H](O)C(O)=O
FEWJPZIEWOKRBE-JCYAYHJZSA-N
0.000
description
1

229920000084
Gum arabic
Chemical class

0.000
description
1

CPELXLSAUQHCOX-UHFFFAOYSA-N
Hydrogen bromide
Chemical class

Br
CPELXLSAUQHCOX-UHFFFAOYSA-N
0.000
description
1

239000004354
Hydroxyethyl cellulose
Substances

0.000
description
1

229920000663
Hydroxyethyl cellulose
Polymers

0.000
description
1

229920002153
Hydroxypropyl cellulose
Polymers

0.000
description
1

240000007817
Olea europaea
Species

0.000
description
1

DWAQJAXMDSEUJJ-UHFFFAOYSA-M
Sodium bisulfite
Chemical compound

[Na+].OS([O-])=O
DWAQJAXMDSEUJJ-UHFFFAOYSA-M
0.000
description
1

229920002125
Sokalan®
Polymers

0.000
description
1

FEWJPZIEWOKRBE-UHFFFAOYSA-N
Tartaric acid
Natural products

[H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O
FEWJPZIEWOKRBE-UHFFFAOYSA-N
0.000
description
1

GSEJCLTVZPLZKY-UHFFFAOYSA-N
Triethanolamine
Chemical class

OCCN(CCO)CCO
GSEJCLTVZPLZKY-UHFFFAOYSA-N
0.000
description
1

IEWOZEKVLKMCKC-UHFFFAOYSA-N
[Na].COCC(C)O.CC(COC(C)CO)O
Chemical compound

[Na].COCC(C)O.CC(COC(C)CO)O
IEWOZEKVLKMCKC-UHFFFAOYSA-N
0.000
description
1

239000000205
acacia gum
Chemical class

0.000
description
1

235000010489
acacia gum
Nutrition

0.000
description
1

230000002411
adverse
Effects

0.000
description
1

229910000288
alkali metal carbonate
Inorganic materials

0.000
description
1

150000008041
alkali metal carbonates
Chemical class

0.000
description
1

150000001412
amines
Chemical class

0.000
description
1

235000019257
ammonium acetate
Nutrition

0.000
description
1

229940043376
ammonium acetate
Drugs

0.000
description
1

235000011114
ammonium hydroxide
Nutrition

0.000
description
1

125000003118
aryl group
Chemical group

0.000
description
1

235000010323
ascorbic acid
Nutrition

0.000
description
1

239000011668
ascorbic acid
Substances

0.000
description
1

229960005070
ascorbic acid
Drugs

0.000
description
1

VHFSMDHANDABQK-UHFFFAOYSA-N
azane;2-sulfanylpropanoic acid
Chemical compound

[NH4+].CC(S)C([O-])=O
VHFSMDHANDABQK-UHFFFAOYSA-N
0.000
description
1

VBNHVAULMDZKRS-UHFFFAOYSA-N
azanium dodecyl sulfate oxirane
Chemical compound

S(=O)(=O)(OCCCCCCCCCCCC)[O-].[NH4+].C1CO1
VBNHVAULMDZKRS-UHFFFAOYSA-N
0.000
description
1

239000000440
bentonite
Substances

0.000
description
1

229910000278
bentonite
Inorganic materials

0.000
description
1

SVPXDRXYRYOSEX-UHFFFAOYSA-N
bentoquatam
Chemical compound

O.O=[Si]=O.O=[Al]O[Al]=O
SVPXDRXYRYOSEX-UHFFFAOYSA-N
0.000
description
1

235000019445
benzyl alcohol
Nutrition

0.000
description
1

239000000872
buffer
Substances

0.000
description
1

239000001768
carboxy methyl cellulose
Substances

0.000
description
1

235000010948
carboxy methyl cellulose
Nutrition

0.000
description
1

239000008112
carboxymethyl-cellulose
Substances

0.000
description
1

230000015556
catabolic process
Effects

0.000
description
1

239000001913
cellulose
Chemical class

0.000
description
1

229920002678
cellulose
Chemical class

0.000
description
1

235000010980
cellulose
Nutrition

0.000
description
1

238000006243
chemical reaction
Methods

0.000
description
1

238000006731
degradation reaction
Methods

0.000
description
1

230000006866
deterioration
Effects

0.000
description
1

235000014113
dietary fatty acids
Nutrition

0.000
description
1

230000007613
environmental effect
Effects

0.000
description
1

239000000194
fatty acid
Substances

0.000
description
1

229930195729
fatty acid
Natural products

0.000
description
1

150000004665
fatty acids
Chemical class

0.000
description
1

239000003205
fragrance
Substances

0.000
description
1

150000003840
hydrochlorides
Chemical class

0.000
description
1

235000019447
hydroxyethyl cellulose
Nutrition

0.000
description
1

229920003063
hydroxymethyl cellulose
Polymers

0.000
description
1

229940031574
hydroxymethyl cellulose
Drugs

0.000
description
1

239000001863
hydroxypropyl cellulose
Substances

0.000
description
1

235000010977
hydroxypropyl cellulose
Nutrition

0.000
description
1

229920000609
methyl cellulose
Polymers

0.000
description
1

239000001923
methylcellulose
Substances

0.000
description
1

235000010981
methylcellulose
Nutrition

0.000
description
1

235000013336
milk
Nutrition

0.000
description
1

210000004080
milk
Anatomy

0.000
description
1

239000003607
modifier
Substances

0.000
description
1

239000003960
organic solvent
Substances

0.000
description
1

238000004806
packaging method and process
Methods

0.000
description
1

230000000149
penetrating effect
Effects

0.000
description
1

JRKICGRDRMAZLK-UHFFFAOYSA-L
persulfate group
Chemical group

S(=O)(=O)([O-])OOS(=O)(=O)[O-]
JRKICGRDRMAZLK-UHFFFAOYSA-L
0.000
description
1

150000002989
phenols
Chemical class

0.000
description
1

150000003016
phosphoric acids
Chemical class

0.000
description
1

239000003755
preservative agent
Substances

0.000
description
1

JXBALDNEJGEZHV-UHFFFAOYSA-M
sodium [4-[3-(diethylamino)propoxy]-3-(dodecylamino)-4-oxobutanoyl]azanide
Chemical compound

[Na+].C(CCCCCCCCCCC)NC(C(=O)OCCCN(CC)CC)CC(=O)[NH-]
JXBALDNEJGEZHV-UHFFFAOYSA-M
0.000
description
1

235000010413
sodium alginate
Nutrition

0.000
description
1

239000000661
sodium alginate
Substances

0.000
description
1

229940005550
sodium alginate
Drugs

0.000
description
1

HRZFUMHJMZEROT-UHFFFAOYSA-L
sodium disulfite
Chemical compound

[Na+].[Na+].[O-]S(=O)S([O-])(=O)=O
HRZFUMHJMZEROT-UHFFFAOYSA-L
0.000
description
1

239000004289
sodium hydrogen sulphite
Substances

0.000
description
1

235000010267
sodium hydrogen sulphite
Nutrition

0.000
description
1

235000010265
sodium sulphite
Nutrition

0.000
description
1

239000000126
substance
Substances

0.000
description
1

150000003467
sulfuric acid derivatives
Chemical class

0.000
description
1

239000011975
tartaric acid
Substances

0.000
description
1

150000003892
tartrate salts
Chemical class

0.000
description
1

238000011282
treatment
Methods

0.000
description
1

238000005406
washing
Methods

0.000
description
1

239000000230
xanthan gum
Substances

0.000
description
1

235000010493
xanthan gum
Nutrition

0.000
description
1

229920001285
xanthan gum
Polymers

0.000
description
1

229940082509
xanthan gum
Drugs

0.000
description
1

Classifications

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

A61K8/411—Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus

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

A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients

A61K8/20—Halogens; Compounds thereof

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

A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients

A61K8/22—Peroxides; Oxygen; Ozone

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

A61Q5/10—Preparations for permanently dyeing the hair

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

A61K2800/42—Colour properties

A61K2800/43—Pigments; Dyes

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

A61K2800/54—Polymers characterized by specific structures/properties

A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge

Abstract

Process for dyeing keratinous fibres, especially human keratinous fibres such as hair, which consists in applying on these fibres a composition containing, in a medium suitable for dyeing, at least 2,6-dimethyl-1,4-diaminobenzene and/or 2,3-dimethyl-1,4-diaminobenzene and/or 2,6-diethyl-1,4-diaminobenzene, as well as its salts and an oxidising agent, the pH of the composition applied on the fibres being below 7 and the aforementioned composition not containing iodide ions in sufficient amounts to oxidise the oxidation dye precursor.

Description

COMMONWEALTH OF AUSTRALIAFom1 PATENTS ACT 1952-69 COMPLETE SPECIFICATION
(ORIGINAL)
Class I t. Class Application Number: Lodged: Complete Specification Lodged: Accepted: Published: .Priority: ;Related Art: Name of Applicant: L’OREAL n~dress of Applicant *’Aptual Inventor Address for Service *So- 14, rue Royale F-75008 Paris, France JEAN COYITERET WATERMARK PATENT TRADEMARK ATTORNEYS.
LOOKED BAG NO. 5, HAWTHORN, VICTORIA 3122, AUSTRALIA omplete Specification for the invention entitled; PROCESS FOR DYEING KERATINOUS FIBRES WITH 2,6-DIMETHYL-1,4- DIAMINOBENZENE AND/OR 2,3-DIME,riYL-1,4-DIAMINOBENZENE AND/OR 2,6- DIETHYL-1,4-DIAMINOBENZENE IN AN ACID MEDIUM AND COMPOSITIONS EMIPLOYED The following statement is a full description of this invention, including the best method of performing it known to u 1 Process for dyeing keratinous fibres with 2,6-dimethyl- 1,4-diaminobenzene and/or 2, 3-dimethyl-l, 4-diaminobenzene and/or 2,6-diethyl-l,4-diaminobenzene in an acid medium and compositions employed.
ge The present invention relates to a new process for dyeing keratinous fibres, especially human keratinous fibres, employing 2,6-dimethyl-1,4-diaminobenzene and/or 2,3-dimethyl-l,4-diaminobenzene and/or 2,6-diethyl- 1,4-diaminobenzene in combination with an oxidising agent in an acid medium, and to the compositions employed during this process.
It is known to dye keratinous fibres, and especially human hair, with dyeing compositions containing oxidation dye precursors, especially ortho- or paraphenylenediamines or ortho- or para-aminophenols, generally referred to as «oxidation bases».
It is also known that the hues obtained with these oxidation bases may be varied by combining them with couplers, referred to as colour modifiers, selected, in particular, from aromatic meta-diamines, metaaminophenols and meta-diphenols.
The dyer of keratinous fibres generally seeks to obtain colorations having good resistance to light, 25 washing, perspiration and adverse weather, in particular by the choice of oxidation bases enabling such results to be obtained.
Under the conditions used at the present time, the media of the oxidising composition and of the dyeing composition are alkaline. In point of fact, this alkalinity generally leads to a deterioration of the keratinous fibres.
To avoid or reduce this degradation of the keratinous fibres, it has been recommended more recently to apply to the fibres a mixture, prepared at the time of use, of the oxidising agent and certain oxidation dye precursors such as 1,4-diaminobenzene at an acid pH.
However, the Applicant found, in particular in 0 a 0 0
C
2 a as
S
the case of 1,4-diaminobenzene, that such a dyeing process led to profound changes in the kinetics of the reaction and in the dyeing of the fibres compared with the same dyeing process performed in an alkaline medium, and no longer satisfied the demands of the dyer.
The Applicant has just discovered that the use of 2,6-dimethyl-1,4-diaminobenzene and/or 2,3-dimethyl- 1, 4-diaminobenzene and/or 2, 6-diethyl-1, 4-diaminobenzene, in the presence of an oxidising agent in an acid medium, leads to colorations practically identical to those obtained under the usual conditions of use, and displays, moreover, surprisingly, greater resistance to the i tion of perspiration, shampoos, chemical treatments or environmental agents such as light.
The subject of the present invention is hence a process for dyeing keratinous fibres, especially human keratinous fibres such as the hair, comprising the Sapplication to these fibres of a composition containing at least one oxidation dye precursor, also known as an «oxidation base», selected from 2,6-dimethyl- 1,4-diaminobenzene,, 2,3-dimethyl-1,4-diaminobenzene or 2,6-diethyl-1,4-diaminobenzene, and at least one oxidising agent, at an acid pH.
The subject of the invention is also a dyeing 25 agent containing two components, one of which components comprises the oxidation dye precursor and the other the oxidising agent at an acid pH, and in such quantities that the mixture has an acid pH.
The subject of the invention is also the readyto-use composition containing the different agents used for dyeing the hair in an acid medium.
Other subjects of the invention will become apparent on reading the description of the examples which follow.
The process for dyeing keratinous fibres, and especially human keratinous fibres such as the hair, according to the invention, is essentially characterised in that at least one composition comprising, in a medium suitable for dyeing, an oxidation dye precursor selected e
S*
S. S
S
5 3 0 *a *a *o .2.:i from 2,6-dimethyl-l,4-diaminobenzene and/or 2,3-dimethyl- 1,4-diaminobenzene or 2,6-diethyl-1,4-diaminobenzene, as well as the salts of these compounds and an oxidising agent, is applied to these fibres; the pH of the composition applied to the fibres is less than 7, and the said composition does not contain iodide ions in a sufficient quantity to oxidise the said oxidation dye precursor.
The oxidation dye precursors according to the present invention may be introduced into the dyeing composition either in the form of free bases or in the form of salts, for example in the form of hydrochlorides, hydrobromides, sulphates or tartrates.
The oxidising agent is preferably selected from hydrogen peroxide, urea peroxide, alkali metal bromates and persalts such as perborates and persulphates. Hydrogen peroxide is especially preferred.
The pH of the composition applied to the keratinous fibres, especially the hair, has a value of less than 7, and is preferably between 3 and 6.9. This pH is 20 adjusted by the use of acidifying agents which are well known in the field of dyeing of keratinous fibres, and especially human hair, such as inorganic or organic acids, for example hydrochloric acid, phosphoric acid, carboxylic acids such as tartaric acid and citric acid, and sulphonic acids.
The compositions defined above, applied in the dyeing of keratinous fibres, can also contain, in addition, other oxidation dye precursors, either of the para type or of the ortho type, such as, for example: paraaminophenol, 2,5-diaminopyridine, dine, 2,4,5,6-tetraaminopyrimidine, para-phenylenediamrine, 2-chloro-para-phenylenediamine, ortho-aminophenols and ortho-phenylenediamines.
The dyeing compositions according to the present iinvention can also contain couplers which are known per se, such as meta-diphenols, meta-aminophenols, metaphenylenediamines, meta-(N-acylamino)phenols, metaureidophencls, meta-carbalkoxyaminophenols, a-naphthol, ortho-diphenols and couplers possessing an active a a a ar aa aa a a a -4 methylene group such as diketo compounds and pyrazolones.
Among these, there may be mentioned, in particular, 2,4-diaxnino-1,3-dimethoxybenzene, 2 ,4-dihydroxyphenoxyethanol, 2, 4-dihydroxyanisole, meta-aminophenol, resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, (p-mesyJlaminoethyl) amino] phenol, 6-hydroxybenzomorpholine, 2, 4-diaminoanisole, 2, 4-diaminophenoxyethanol, 6-aminobenzomiorpholine, 2- [N- (pl-hydroxyethyl)amino]-4-aminophenoxyethanol, 2-amino- 4-[N.-(p-hydroxyethyl)amino]anisole, 2,4-diaminophenyl -y,-dihydroxypropyl ether, 2, 4-diaminophenoxyethylamine, 2, 6-dimethyl-3-axninophenol, 3, 4-methylenedioxyphenol, 3, 4-methylenedioxyaniline and their salts. 2,6-Dimethoxy-1,3-diaminobenzene, metaaminophenol, 2-methyl-5- 1 -hydroxyethyl) amino ]phenol and a-naphthol are preferably used.
These compositions can also contain anionic, cationic, nonionic or amphoteric surf actants or mixtures 20 thereof.
0*0, se 4 to.
to.
C.
C
C..
C
9S*S** 0 S. C, S C C. C *e S S CSC e.g.
C
0* CC C
C
Among these surfactants, there may be mentioned alkylbenzenesulphonates, fatty alcohol sulphates, ether sulphates and.. suiphonates, quaternary ammoniumi salts such as trimethylcetylarunoniuim 25 bromide and cetylpyridiiiun bromide, fatty acid ethanolainides, optionally oxyethylenated, polyoxyethylenated acids, alcohols or amines, polyglycerolated alcohols, polyoxyethylenated or polyglycerolated alkylphenols and also polyoxyethylenated alkyl sulphates.
The dyeing compositions are generally aqueous, but they can also contain organic solvents to solubilise compounds which might not be sufficiently water-soluble.
Among these solv ents, there m’ay be mentioned, by way of example, C 2
-C
4 lower alkanols such as ethanol and isopropanol, glycerol, glycols or glycol ethers such as 2-butoxyethanol, ethylene glycol, propylene glycol and diethylene glycol monoethyl ether and monomethyl ether, and also aromatic alcohols such as benzyl alcohol or phenoxyethanol, or mixtures of these solvents.
5 The compositions applied to the keratinous fibres according to the present invention can also contain thickening agents selected, in particular, from sodium alginate, gum arabic, cellulose derivatives such as methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxymethylcellulose and carboxymethylcellulose, acrylic acid polymers, optionally crosslinked, and xanthan gum. Inorganic thickening agents such as bentonite can also be used.
The composition can also contain antioxidants selected, in particular, from sodium sulphite, thioglycolic acid, sodium bisulphite, ascorbic acid and hydroquinone, as well as other cosmetically acceptable adjuvants when it is intended that the composition be used for dyeing human keratinous fibres, such as penetrating agents, sequestering agents, preservatives, buffers, fragrances, and the like.
The composition applied to the hair can take various forms, such as the form of liquids, creams or 20 gels or any other form suitable for carrying out hair dyeing. It may be packaged in an aerosol can in the presence of a propellant.
The subject of the invention is also the readyto-use composition used in the process defined above.
25 According to a preferred embodiment, the process comprises a preliminary step consisting in storing separately, on the one hand the composition containing, in a medium suitable for dyeing, 2,6-dimethyl-l,4-diaminobenzene and/or 2,3-dimethyl-1,4-diaminobenzene and/or 2,6-diethyl-l,4-diaminobenzene, in the form of a component and on the other hand a composition containing the oxidising agent as defined above, in the form of a component and in mixing them at the time of use before applying this mixture to the keratinous fibres, as described above. The component does not contain iodide ions in a sufficient quantity to oxidise the said oxidation dye precursor.
The composition applied to the keratinous fibres results, in particular, from a mixture of 10 to 90% of 6 0
S.
a’~
S..
the component with 90 to 10% of the component (B) containing an oxidising agent.
The subject of the invention is also an agent for dyeing keratinous fibres, especially the hair, essentially characterised in that it contains at least two components, one consisting of the component defined above and the other consisting of the component also defined above, the pH of the components and being such that, after mixing in proportions of 90 to 10% for the component and 10 to 90% for the component the resulting composition has a pH of less than 7.
In this embodiment, the component which contains at least the oxidation dye precursor, has a pH of between 3 and 10.5, and may be adjusted to the chosen value by means of alkalinising agents customarily used in the dyeing of keratinous fibres, such as ammonia solution, alkali metal carbonates, alkanolamines such as mono-, di- and triethanolamines and also their derivatives, or conventional acidifying agents such as 20 inorganic or organic acids, for example hydrochloric and phosphoric acids, carboxylic acids such as tartaric and citric acids, and sulphonic acids.
This composition can contain the various other adjuvants mentioned above, in particular ortho or para oxidation dye precursors or couplers.
The oxidation dye precursors of the para or ortho type, other than 2,6-dimethyl-l,4 4diaminobenzene, 2,3-dimethyl-l,4-diaminobenzene and 2,6-diethyl-1,4-diaminobenzene, are present in proportions of between 0.02 and 10% by weight, and preferably between 0.05 and 5% by weight, relative to the total weight of the component
S
S.
a a eas The couplers such as are mentioned above are present in concentrations of between 0.02 and 10% by weight, and preferably between 0.05 and 5% by weight, relative to the total weight of the component The concentration of 2,6-dimethyl-1,4-diaminobenzene and/or 2,3-dimethyl-l,4-diaminobenzene and/or 2,6-diethyl-1,4-diaminobenzene is between 0.02 and 10% by 7 *r S
S
BOB
V
weight, and preferably between 0.05 and 5% by weight, relative to the total weight of the component The surfactants are present in the component (A) in proportions of 0.1 to 55% by weight.
The solvents optionally present in addition to water are present in proportions of between 0.5 and by weight, and especially between 5 and 30% by weight, relative to the total weight of the component The thickening agents are preferably present in proportions of between 0.1 and and especially between 0.2 and by weight.
The antioxidants mentioned above are preferably present in the component in proportions of between 0.02 and 1.5% by weight relative to the total weight of the component The component according to the invention can take various forms, such as the form of liquids, creams or gels or any other form suitable for carrying out hair dyeing. It may be packaged in an aerosol can in the 20 presence of a propellant.
The component containing the oxidising agent as defined above has a pH of less than 7. This pH can have a minimum value of 1, and is preferably between and 3.5. This component may be acidified with the same type of acidifying agents as those used for the component It can take the form of liquids, more or less thickened, milks or gels.
The two-component dyeing agent according to the present invention may be packaged in a multi-compartment device or dyeing kit, or any other multi-compartment packaging system in which one of the compartments contains the component and the second compartment contains the component it being possible for these devices to be equipped with a means enabling the desired mixture to be delivered on the hair, such as the device described in the Applicant’s Patent US-A-4,823,985.
According to the invention, the dyeing process consists in applying the mixture obtained to the hair, in 60W50 0 s B a 8 leaving it in place for 3 to 40 minutes and then in rinsing the hair and optionally shampooing.
The examples which follow are intended as illustrations of the invention, no limitation being implied.
EXAMPLES 1 to Hair dyeing is performed by applying a mixture, prepared at the time of use, of the dyeing composition and the oxidising composition to permanent-waved grey hair which is 90% white.
This mixture has the pH shown in the table of examples which follow.
This mixture is left to act for 30 minutes and the hair is then rinsed and shampooed.
After drying, the hair is dyed in the hue specified at the bottom of the table.
0 0 j*O.
6 20 *0 S 40
C
3 30
C
35 in g 1 2 3 4 5 6 A) Dyeing composition 2,6-Dimethyl-1,4-diaminobenzene.2 HCI 0.627 0.657 0.657 2,3-Dimethyl-1,4-diaminobenzene.2 HCI 0.627 0.627 0.627 hydroxyethyl)amino]phenol 0.501 0.417 0.417 a-Naphthol 0.327 0.327 0.327 Monoethanolamine qs pH 9.8 9.8 9.8 8.8 8.8 8.9 Vehicle 1 X X X Vehicle 2 X X X Water qs 100 100 100 100 100 100 -9 fo 1 2 3 4 5 6 B) xdsn comosition Hydrogen peroxide solution, «120 volumes» Phosphoric acid qs pH 13 1.5 1.5 1,5 1,5 pH w/w mixture A B 5.5 5.5 5.5 6.0 6.4 Hues obtained: light irides- matt deep greyish deep blond cent ashen greyish olive purple blond light purple iridesblond cent 0 0 o 066 0 10 9 11 a e A) Dyeing composition 2,6-Dimethyl-1,4-diaminobenzene.2 HNd 0.438 (,.876 0.583 2, 3-Dimethyl-1,4-di-I aminobenzerxe.2 H1-i 0.627 (fihydroxyethyl) amino]phenol 0.324 0.216 meta-Aminophenol 0.576 0.192 a-Naphthol 0,327 Monoe thano lamine qs pH 8.8 9.1 8.8 8.9 Vehicle 2 X X X X Water qs 100 100 100 100 *a 6 505 00-b bOIS .0 11 20 los e 7 8 9 B) Oxidising compositi on Hydrogen peroxide solution, 1120 volumes» Phosphoric acid qs pH, 1.5 1.1 1.5 1.1 pH. w/w mi~xture A +B 6 1 6.6 pH mixture 1/3 A 2/3 B 5,8 Hues obtained: greyish deep blueish slightly yellowish purple deep ashen blond irrides- grey dark cent auburn eggEXAMPLES 11 and 12 gee. ge C C eeC g
CC
Ce C C Se C C eec e bee C e e e.g.
Cg Ce g e e C S
COMPOSITION
Dye Nonyiphenol containing 4 moles of ethylene oxide, sold by the company HENKEL under the name «SINNOPAL NP411 30 Nonyiphenol containing 9 moles of ethylene oxide, sold by the company HENKEL under the name I’SINNOPAL NP 9» Ethylene glycol butyl ether Propylene glycol 35 Ethyl alcohol Monoethanolamine 1 auryl ether sulphate sold by the company LEVER at a concentration of 28%& AS under the name «SACTIPON 2 OM 29″1 Sodium acetate Antioxidant, sequestering agent qs Demineralised water as 17.5 11.0 17 .9 0.8 X g 25.5 g 100.0 g 12
PROCEDURE
The composition described above is mixed, weight for weight, with «20 volumes’ hydrogen peroxide and adjusted to pH 6.7 with orthophosphoric acid.
The preparation is applied to grey hair which is white, on the basis of 28 g of the mixture per 3 g of hair, for 30 minutes. The locks are then rinsed, washed with a shampoo, rinsed and thereafter dried.
The hair is dyed in the hue specified at the bottom of the table: o g *0 20 *.o in g Example 11 Example 12 2,6-Diethyl-l,4-diaminobenzene 0.711 0.711 6-Hydroxybenzomorpholine 0.453 2,4-Diaminophenoxyethanol.2 HC1 0.723 Hues obtained: matt blueish yellow medium grey EXAMPLES 13 and 14 Hair dyeing is performed by applying a mixture, prepared at the time of use, of the dyeing composition and the oxidising composition to permanent-waved grey hair which is 90% white.
This mixture has the pH shown in the table of examples which follow.
This mixture is left to act for 30 minutes and the hair is then rinsed and shampooed. After drying, the hair is dyed in the hue specified at the bottom of the table below: 25 00 0 G 0 3 30 S. OS 13 *.*15 OGGf f G. f fee :25 OGG ft in g 13 14 A) Dyeing composition 2 ,6-Dimethyl-1 ,4-diaminobenzene. 2 i{Cl 0.836 0.836 2 -Iethylresorc inol 0 .248 (p-hydroDxyethyl)amino]phenol 0.19 2 -Chioro-para-phenlylenediamine sulphate 0.48 6-Hydroxybenzomorpholine 0,464 Monoethanolanine qs pH 9.9 9.8 Vehicle 3 X X Water qs 100 100 B) Oxidising composition Hydrogen peroxide solution, «120 volumies» Orthophosphoric acid qs pH 1.2 1.2 pH w/w mixture of A B 6.6 6.3 Hues obtained: slightly irridesmatt cent golden golden ‘Light deep chestnut blond ft. ft ft ft ft ft…
ft. ft~ ft ft ft ft ft DYEING VEHICLE 1 Nonyiphenol containing 4 moles of ethylene oxide, sold by the company HENKEL under the name IISINNOPAL NP4″1 Nonyiphenol containing 9 moles oil ethylene oxide, sold by the company HENKEL under the name «ISINNOPAJ NP 91 Ethylene glycol butyl ether Propylene glycol Ethyl alcohol 25.5 g 17. 5 g 7.0 g 11.0 g 2.0 g 14 15 0 0* *0 00 20 25 g 30 Monoethanolamine lauryl ether sulphate sold by the company LEVER at a concentration of 28% AS under the name «SACTIPON 2 OM 29» Sodium metabisulphite in aqueous solution containing 35% AS Sodium acetate Antioxidant, sequestering agent qs DYEING VEHICLE 2 Polyglycerolated oleyl alcohol containing 2 moles of glycerol Polyglycerolated oleyl alcohol containing 4 moles of glycerol at a concentration of 78% AS Oleic acid Oleylamine containing 2 moles of ethylene oxide, sold by the company AKZO under the name «ETHOMEEN O 12» Diethylaminopropyl laurylaminosuccinamate sodium salt containing 55% AS Oleyl alcohol Oleic acid diethanolamide Propylene glycol Ethyl alcohol Dipropylene glycol Propylene glycol monomethyl ether Sodium metabisulphite in aqueous solution containing 35% AS Ammonium acetate Antioxidant, sequestering agent qs DYEING VEHICLE 3 Cetyl/stearyl alcohol 2-Octyldodecanol Oxyethylenated cetyl/stearyl alcohol containing 15 moles of ethylene oxide Ammonium lauryl sulphate containing
AS
Ammonium thiolactate containing 50% AS 5.0 g AS 0.45 0.8 g AS g 4.0 g 5.69 3.0 g AS g 7.0 g 3.0 5.0 12.0 3.5 7.0 0.5 9.0 0.45 0.8 18.0 3.0 g AS g g g g g g g AS g g g 3.0 g 3.6 g AS 0.4 g AS

Claims (13)

1. Process for dyeing keratinous fibres, especially human keratinous fibres such as the hair, characterised in that a composition containing, in a medium suitable for dyeing: at least one oxidation dye precursor selected from 2,6-dimethyl-1,4-diaminobenzene and/or 2,3-dimethyl- 1,4-diaminobenzene and/or 2, 6-diethyl-1,4-diaminobenzene, as well as their salts; and at least one oxidising agent; is applied to these fibres, the pH of the composition applied to the fibres being less than 7 and the said composition not containing iodide ions in a sufficient quantity to oxidise the oxidation dye precursor.

2. Dyeing process according to Claim 1, charac- terised in that the oxidising agent is selected from hydrogen peroxide, urea peroxide, alkali metal bromates and persalts.

3. Process according to Claim 1 or 2, characterised in that the pH of the composition applied to the kera- tinous fibres is between 3 and 6.9.

4. Process according to any one of Claims 1 to 3, characterised in that the composition used for dyeing the keratinous fibres contains, in addition, other oxidation 25 dye precursors of the para or ortho type. Process according to Claim 4, characterised in that the oxidation dye precursors are selected from p-aminophenol, 2,5-diaminopyridine, pyridine, 2,4,5,6-tetraaminopyrimidine, para-phenylene- 30 diamine, 2-chloro-para-phenylenediamine, ortho-amino- phenols and ortho-phenylenediamines.

6. Process according to any one of Claims 1 to characterised in that the composition comprises, in addition, couplers selected from meta-diphenols, meta- aminophenols, meta-ureidophenols, meta-phenylenediamines, meta-acylaminophenols, meta-carbalkoxyaminophenols, a-naphthol, ortho-diphenols and couplers possessing an active methylene group selected from diketo compounds and pyrazolones. o S 0 .55. S. 55 *S i 16

7. Process according to Claim 6, characterised in that the couplers are selected from 2,4-diamino-1,3-di- methoxybenzene, 2,4-dihydroxyphenoxyethanol, 2,4-di- hydroxyanisole, meta-aminophenol, resorcinol, resorcinol monomethyl ether, 2-methylresorcinol, (-hydroxyethyl)amino]phenol, aminoethyl)amino]phenol, 6-hydroxybenzomorpholine, 2,4-diaminoanisole, 2,4-diaminophenoxyethanol, 6-amino- benzomorpholine, 2-[N-(p-hydroxyethyl)amino]-4-amino- phenoxyethanol, 2-amino-4-[N-(pB-hydroxyethyl)amino)- anisole, 2,4-diaminophenyl f,,-dihydroxypropyl ether, 2,4-diaminophenoxyethylamine, 2,6-dimethyl-3-aminophenol, 3,4-methylenedioxyphenol, 3,4-methylenedioxyaniline and their salts. *9 see15 8. Process according to any one of Claims 1 to 7, characterised in that the composition contains anionic, cationic, nonionic or amphoteric surfactants or mixtures **ee .thereof, antioxidants, thickening agents and/or any other cosmetically acceptable adjuvant. see 20 9. Process according to any one of Claims 1 to 8, characterised in that the medium suitable for dyeing consists of water or a mixture of water and a solvent selected from C 2 -C 4 lower alkanols, glycerol, glycols or *glycol ethers, diethylene glycol monoethyl ether and 25 monomethyl ether, aromatic alcohols or mixtures thereof. -AgeaR for dyeing keratinous fibres, especially the hair, characterised in that it contains at least two components: a component consisting of a composition eec. 30 containing, in a medium suitable for dyeing, 2,6-di- methyl-1,4-diaminobenzene and/or 2,3-dimethyl-1,4-di- aminobenzene and/or 2,6-diethyl-1 ,4-diaminobenzene, the said component not containing iodide ions in a sufficient quantity to oxidise the oxidation dye precur- sor; and a component consisting of a composition containing an oxidising agent in a medium suitable for dyeing; S the pH of the components and being such that, 17 after mixing in proportions of 90 to 10% for the component and 10 to 90% for the component the resulting composition has a pH of less than 7.

11. Composition according to Claim 10, characterised in that the component has a pH of between 3 and 10.5.

12. Composition according to claim 10 or 11, characterised in that the component contains, in addition, oxidation dye precursors of the para or ortho type in proportions of between 0.02 and 10% by weight and/or couplers in proportions of between 0.02 and 10% by weight.

13. Composition according to any one of claims 10 to 12, characterised in that the concentration of 2,6-dimethyl-1,4-diaminobenzene and/or 2,3-dimethyl-1, 4-diaminobenzene and/or 2,6-diethyl-1, 4-diaminobenzene is between 0.02 and 10% by weight relative to the total weight of the component

14. Composition according to any one of Claims 10 to 13, characterised in that the component contains, in addition, surfactants in proportions of 0.1 to 55% by weight, solvents in addition to water in proportions of 0.5 to 40%, thickening agents in proportions of 0.1 to 5% by weight, antioxidants in proportions of 0.02 to 1.5% by weight and/or any other cosmetically acceptable adjuvant.

15. Composition according to any one of Claims 10 to 14, characterised in that the component has a pH which has a minimum value of 1 and less than 7.

16. Process for dyeing keratinous fibres, and especially the hair, characterised in that it comprises a first step consisting in storing separately the components of the dyeing composition as defined in any one of Clairn~ 10 to 14, and in mixing the compositions and in proportions of 10 to 90% for the component and 90 to 10% for the component before application so as to obtain a composition having a pH of less than 7, and applying this mixture immediately after preparation to the keratinous fibres.

17. Dyeing process according to any one of Claims 1 to 9, characterised in that the composition is applied to the hair and in that it is left in place for 3 to 40 minutes, in that the hair is rinsed and in that it is optionally shampooed before a further rinse and drying. DATED this 11th day of February, 1994. L’OREAL WATERMARK PATENT TRADEMARK ATTORNEYS THE ATRIUM 290 BURWOOD ROAD HAWTHORN VICTORIA 3122 AUSTRALIA *C Mx DoC 04S AU780151.WPC (CC) e T k 1 922/90 GD/LM/DD ABSTRACT EXT 526 Process for dyeing keratinous fibres with 2,6-dimethyl- 1,4-diaminobenzeneand/or 2,3-dimethyl-, 4-diaminobenzene and/or 2,6-diethyl-l,4-diaminobenzene in an acid medium and compositions employed. Process for dyeing keratinous fibres, especially human keratinous fibres such as the hair, consisting in applying to these fibres a composition con:aining, in a medium suitable for dyeing, at least 2,6-dimethyl-l,4-di- aminobenzene and/or 2,3-dimethyl-l,4-diaminobenzene and/or 2,6-diethyl-l,4-diaminobenzene, as well as its salts, and an oxidising agent, the pH of the composition applied to the fibres being less than 7 and the said composition not containing iodide ions in a sufficient quantity to oxidise-the oxidation dye precursor. *O *e

AU78015/91A
1990-05-31
1991-05-30
Process for dyeing keratinous fibres with 2,6-dimethyl- 1,4-diaminobenzene and/or 2,3-dimethyl-1,4-diaminobenzene and/or 2,6-diethyl-1,4-diaminobenzene in an acid medium and compositions employed

Ceased

AU648796B2
(en)

Applications Claiming Priority (2)

Application Number
Priority Date
Filing Date
Title

FR9006802

1990-05-31

FR9006802A

FR2662715B1
(en)

1990-05-31
1990-05-31

PROCESS FOR DYEING KERATINIC FIBERS WITH 2,6-DIMETHYL 1,4-DIAMINO BENZENE AND / OR 2,3-DIMETHYL 1,4-DIAMINO BENZENE AND AN ACID OXIDIZING AGENT AND COMPOSITIONS USED THEREOF.

Publications (2)

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Publication Date

AU7801591A

AU7801591A
(en)

1991-12-05

AU648796B2
true

AU648796B2
(en)

1994-05-05

Family
ID=9397158
Family Applications (1)

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Priority Date
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AU78015/91A
Ceased

AU648796B2
(en)

1990-05-31
1991-05-30
Process for dyeing keratinous fibres with 2,6-dimethyl- 1,4-diaminobenzene and/or 2,3-dimethyl-1,4-diaminobenzene and/or 2,6-diethyl-1,4-diaminobenzene in an acid medium and compositions employed

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(en)

JP
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JP3380562B2
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KR
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KR910019594A
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ATE131380T1
(en)

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AU648796B2
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CA2043623A1
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DE69115358T2
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DK0459901T3
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ES2080269T3
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FR2684296B1
(en)

1991-12-03
1995-04-21
Oreal

PROCESS FOR DYEING KERATINIC FIBERS WITH AN ACID PH ALCOXYMETAPHENYLENEDIAMINE AND COMPOSITIONS IMPLEMENTED.

FR2706297B1
(en)

1993-06-16
1995-08-18
Oreal

Keratin fiber oxidation dye composition comprising a paraaminophenol, a meta-aminophenol and an ortho-aminophenol, and dyeing process using such a composition.

FR2707489B1
(en)

1993-07-13
1995-09-22
Oreal

Keratin fiber oxidation dye composition comprising a para-aminophenol, 2-methyl 5-aminophenol and a paraphenylenediamine and / or a bis-phenylalkylenediamine.

FR2707488B1
(en)

1993-07-13
1995-09-22
Oreal

Keratin fiber oxidation dye composition comprising a para-aminophenol, a meta-aminophenol and a paraphenylenediamine and / or a bis-phenylalkylenediamine.

DE4342009C2
(en)

1993-12-09
1996-05-23
Goldwell Gmbh

Hair Dye

FR2725368B1
(en)

1994-10-07
1997-04-04
Oreal

KERATINIC FIBER OXIDIZING DYE COMPOSITIONS CONTAINING A COMBINATION OF AT LEAST TWO PARTICULAR PARAPHENYLENEDIAMINE DERIVATIVES, AND USE

FR2726185B1
(en)

1994-11-02
1997-04-25
Oreal

TINCTORIAL COMPOSITION BASED ON OXIDATION DYES AND DYEING METHOD USING THE SAME

FR2730923B1
(en)

1995-02-27
1997-04-04
Oreal

COMPOSITION FOR OXIDATION DYEING OF KERATINIC FIBERS COMPRISING AN OXIDATION BASE, AN INDOLIC COUPLER AND AN ADDITIONAL HETEROCYCLIC COUPLER, AND DYEING METHOD

US6309426B1
(en)

1996-12-23
2001-10-30
The Procter & Gamble Company
Hair coloring compositions

US6432147B1
(en)

1996-12-23
2002-08-13
The Procter & Gamble Company
Hair coloring compositions

GB9626675D0
(en)

1996-12-23
1997-02-12
Procter & Gamble
Hair coloring compositions

GB9626713D0
(en)

1996-12-23
1997-02-12
Procter & Gamble
Hair colouring compositions

US6398821B1
(en)

1996-12-23
2002-06-04
The Procter & Gamble Company
Hair coloring compositions

GB9626711D0
(en)

1996-12-23
1997-02-12
Procter & Gamble
Hair colouring compositions

GB9626712D0
(en)

1996-12-23
1997-02-12
Procter & Gamble
Hair colouring compositions

MX364254B
(en)

2012-03-27
2019-04-17
Noxell Corp
Hair colorant compositions comprising 3-amino 2,6 dimethylphenol, methods, and kits comprising the compositions.

WO2013148804A2
(en)

2012-03-27
2013-10-03
The Procter & Gamble Company
Hair colorant compositions comprising amino -2,6- dimethylphenol and 1,4- phenylenediamine-type developers, methods, and kits comprising the compositions

JP6734575B2
(en)

2019-10-17
2020-08-05
株式会社Ｍｃｙ

Hair treatment replenisher, hair treatment, and hair setting method

WO2023275193A1
(en)

2021-06-30
2023-01-05
L’oreal
Composition comprising at least one oxidation dye, 1,3-propanediol, at least one alkaline agent and at least one fatty substance

FR3124710A1
(en)

2021-06-30
2023-01-06
L’oreal

Composition comprising at least one particular coupler, propane-1,3-diol, at least one alkaline agent and at least one fatty substance.

WO2023275197A1
(en)

2021-06-30
2023-01-05
L’oreal
Composition comprising at least one oxidation dye, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol

FR3124720A1
(en)

2021-06-30
2023-01-06
L’oreal

Composition comprising at least one particular coupler, at least one alkaline agent and at least one liquid fatty alcohol and at least one solid fatty alcohol.

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(en)

1978-04-06
1979-11-02
Oreal

TWO-STAGE KERATINIC FIBER DYING PROCESS

FR2421607A1
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TWO-STAGE KERATINIC FIBER DYING PROCESS BY PH VARIATION

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1978-07-27
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LYOPHILISATES OF REACTION MIXTURES IN ANAEROBIC MEDIA OF POLHYDROXYBENZENES AND PARA OXIDATION DYE PRECURSORS, THEIR PREPARATION PROCESS AND THEIR USE IN TINCTORIAL COMPOSITIONS FOR HAIR

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1980-01-09
1981-07-17
Oreal

NOVEL METAPHENYLENEDIAMINES, TINCTORIAL COMPOSITIONS FOR KERATIN FIBERS CONTAINING THEM AND DYEING METHOD THEREOF

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(en)

1987-05-25
1989-01-19
Oreal

PROCESS FOR DYEING KERATINIC FIBERS WITH OXIDATION DYES ASSOCIATED WITH IODIDE AND TINCTORIAL COMPOSITION USED

LU86903A1
(en)

1987-05-29
1989-01-19
Oreal

USE AS A COUPLER OF 2,4-DIAMINO-1,3-DIMETHOXYBENZENE OR ONE OF ITS SALTS, IN ASSOCIATION WITH OXIDATION DYE PRECURSORS, FOR DYEING HUMAN HAIR, HAIR DYE COMPOSITION CONTAINING SAID COUPLER AND METHOD FOR PREPARING THE COUPLER

1990

1990-05-31
FR
FR9006802A
patent/FR2662715B1/en
not_active
Expired – Fee Related

1991

1991-05-30
DK
DK91401398.2T
patent/DK0459901T3/en
active

1991-05-30
AU
AU78015/91A
patent/AU648796B2/en
not_active
Ceased

1991-05-30
DE
DE69115358T
patent/DE69115358T2/en
not_active
Expired – Fee Related

1991-05-30
EP
EP91401398A
patent/EP0459901B1/en
not_active
Expired – Lifetime

1991-05-30
KR
KR1019910008862A
patent/KR910019594A/en
not_active
Application Discontinuation

1991-05-30
ZA
ZA914147A
patent/ZA914147B/en
unknown

1991-05-30
AT
AT91401398T
patent/ATE131380T1/en
active

1991-05-30
ES
ES91401398T
patent/ES2080269T3/en
not_active
Expired – Lifetime

1991-05-31
CA
CA002043623A
patent/CA2043623A1/en
not_active
Abandoned

1991-05-31
JP
JP12939991A
patent/JP3380562B2/en
not_active
Expired – Fee Related

1995

1995-04-13
US
US08/421,739
patent/US5500022A/en
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Expired – Fee Related

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1996-01-17
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GR960400089T
patent/GR3018688T3/en
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AU7801591A
(en)

1991-12-05

FR2662715B1
(en)

1994-04-08

US5500022A
(en)

1996-03-19

FR2662715A1
(en)

1991-12-06

GR3018688T3
(en)

1996-04-30

ZA914147B
(en)

1992-03-25

CA2043623A1
(en)

1991-12-01

ATE131380T1
(en)

1995-12-15

JP3380562B2
(en)

2003-02-24

DE69115358T2
(en)

1996-05-09

JPH04235910A
(en)

1992-08-25

EP0459901A1
(en)

1991-12-04

DK0459901T3
(en)

1996-04-09

EP0459901B1
(en)

1995-12-13

KR910019594A
(en)

1991-12-19

DE69115358D1
(en)

1996-01-25

ES2080269T3
(en)

1996-02-01

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