Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-11-22
2002-09-24
Killos, Paul J. (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S048000, C564S123000
Reexamination Certificate
active
06455737
ABSTRACT:
The invention relates to novel cationic 2-acylaminophenols of formula (I) comprising at least one cationic group, to their use as couplers for the oxidation dyeing of keratin fibres, and in particular of human keratin fibres such as the hair, to oxidation dye compositions containing them in combination with at least one oxidation base, and to oxidation dyeing processes using them.
It is known practice to dye keratin fibres, and in particular human hair, with dye compositions containing oxidation dye precursors, in particular ortho-phenylenediamines, para-phenylenediamines, ortho-aminophenols or para-aminophenols and heterocyclic compounds such as diaminopyrazole derivatives, which are generally referred to as oxidation bases. The oxidation dye precursors, or oxidation bases, are colourless or weakly coloured compounds which, when combined with oxidizing products, can give rise to coloured compounds and dyes by a process of oxidative condensation.
It is also known that the shades obtained with these oxidation bases can be varied by combining them with couplers or coloration modifiers, the latter being chosen in particular from aromatic meta-diamines, meta-aminophenols, meta-diphenols and certain heterocyclic compounds.
The variety of molecules used as oxidation bases and couplers makes it possible to obtain a wide range of colours.
The so-called “permanent” coloration obtained by means of these oxidation dyes must moreover satisfy a certain number of requirements. Thus, it must have no toxicological drawbacks and it must allow shades of the desired intensity to be obtained and have good resistance to external agents (light, bad weather, washing, permanent-waving, perspiration and friction).
The dyes must also allow white hairs to be covered, and, lastly, they must be as unselective as possible, i.e. they must allow the smallest possible differences in coloration to be produced over the entire length of the same keratin fibre, which may indeed be differently sensitized (i.e. damaged) between its tip and its root.
4-Aminophenol is generally used to obtain red shades, alone or as a mixture with other bases, and in combination with suitable couplers, and para-phenylenediamines are usually used to obtain blue shades. The use of meta-phenylenediamine-based couplers, in combination with para-phenylenediamine-based couplers usually leads to blue shades whose fastness is generally mediocre.
It has already been proposed, in particular in patent FR-A-1 596 879, to use, for the oxidation dyeing of keratin fibres, phenolic derivatives substituted in position 2 with a ureinyl or thioureinyl radical, in combination with para-phenylenediamine derivatives, in order to obtain shades close to those obtained with meta-phenylenediamine-based couplers. However, dye compositions containing the compounds cited in that patent generally lead on the hair to colours that are too selective and that lack intensity.
Moreover, it has already been proposed, in particular in patent BE 816 674, to use, for the dyeing of keratin fibres, in combination with para-phenylenediamine derivatives, phenolic derivatives substituted in position 2 with an acetyl or ureic radical and in position 5 with a halogen atom, in order to obtain dyeing results ranging from green to green-blue. The light-fastness of the shades obtained on the hair using these compositions are generally better than those obtained with dye compositions containing one or more meta-phenylenediamines as couplers. However, the fastness with respect to bad weather and washing, and the intensities of the colorations obtained are still too low and in these respects constitute major drawbacks for those skilled in the art.
In addition, it has already been proposed, in particular in patent application EP 0 579 204, to use, for the dyeing of keratin fibres, non-cationic phenolic derivatives substituted in position 2 with an acylamino, carbamoyl or ureyl radical, and in position 5 with a C
1
-C
4
alkyl radical, in combination with para-phenylenediamine derivatives. However, the use of the phenolic derivatives cited in that European patent application does not make it possible to obtain a wide range of colours, and furthermore the blue shades generally obtained are not entirely satisfactory as regards their resistance to washing and to the action of light.
The Applicant has now discovered, entirely surprisingly and unexpectedly, that novel 2-acylaminophenols of formula (I) defined below comprising at least one cationic group of formula (II) defined below are not only suitable for use as couplers, but also make it possible to obtain dye compositions which give intense colorations with a wide range of colours, and having excellent properties of resistance with respect to the various treatments to which keratin fibres may be subjected.
These discoveries form the basis of the present invention.
A first subject of the invention is thus novel cationic 2-acylaminophenols of formula (I) below, and the addition salts thereof with an acid:
in which:
the group A represents a group represented by the group D as defined below;
B
1
and B
2
, independently of each other, represent a group represented by the group B as defined below;
k, l and m are integers which can take, independently of each other, the value 0 or 1; the sum k+l+m being non-zero;
W
1
and W
2
represent, independently of each other, a group W represented by formula (II) below:
in which formula (II):
R
1
represents a hydrogen atom; a group Z as defined below; a linear or branched radical containing from 1 to 15 carbon atoms (it being possible for the branch(es) to form one or more 3- to 7-membered carbon-based rings) which can contain one or more double bonds and/or one or more triple bonds (the said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and the carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms; it being understood that the said SO
2
group is not directly linked to the nitrogen atom in position 7 bearing the radical R
1
; the said radical R
1
comprising no peroxide linkages or diazo, nitro or nitroso radicals; it being understood that the radical R
1
does not represent a hydroxyl, amino, thio, alkoxy or alkylthio radical;
R
2
represents a hydrogen atom; a group Z as defined below; a linear or branched radical containing from 1 to 20 carbon atoms (it being possible for the branch(es) to form one or more 3- to 7-membered carbon-based rings) which can contain one or more double bonds and/or one or more triple bonds (the said double bonds optionally leading to aromatic groups), and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and the carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms; the said radical R
2
comprising no peroxide linkages or diazo, nitro or nitroso radicals; and it being understood that R
2
cannot represent a hydroxyl or thio radical;
the radicals R
1
and R
2
can also be linked to form a saturated or unsaturated 5- to 7-membered ring consisting of carbon, nitrogen, oxygen, sulphur and/or of C═O group, each ring member being unsubstituted or substituted with 1 or 2 radicals R, which may be identical or different, R being a linear or branched C
1
-C
6
alkyl radical (it then being possible for the branch(es) to form one or more 3- to 6-membered rings), which can contain one or more double bonds and/or one or more triple bonds (the said double bonds possibly leading to aromatic groups), and one or more carbon atoms of which can be replaced with an oxygen, nitrogen or sulphur atom or with an SO
2
group, and the carbon atoms of which can, independently of each other, be substituted with one or more halogen atoms; the said radical R comprising no peroxide linkages or diazo, nitro or nitroso radicals;
R
3
, R
4
and R
5
, which may be identical or different, represent a hyd
Saunier Jean-Baptiste
Vidal Laurent
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Killos Paul J.
L'Oreal (S.A.)
Reyes Hector M
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