Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2001-06-19
2002-11-26
Gupta, Yogendra N. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S405000, C008S406000, C008S409000, C008S437000, C008S453000
Reexamination Certificate
active
06485529
ABSTRACT:
BACKGROUND OF THE INVENTION
The object of the present invention is an agent for coloring fibers, particularly keratin fibers (such as human hair), the agent containing a combination of a 1-alkyl-methylquinolinium salt of formula (I) or (II) and carbonyl compounds, a method for coloring fibers especially keratin fibers, as well as a multi-component kit for coloring and, later on, decolorizing fibers.
Hair coloring agents are divided mainly into the field of oxidizing dyes or tints, depending on the initial color of the hair that is to be dyed and on the desired end result.
Oxidation dyes are outstandingly suitable for covering higher proportions of gray. As a rule, oxidation dyes, used for a proportion of gray up to 50%, are referred to as oxidative tints, whereas the oxidation dyes, used when the proportion of gray exceeds 50% or for “coloring to a brighter color”, usually are referred to as so-called oxidative dyes.
Direct dyes are contained mainly in non-oxidative coloring agents (so-called tinting agents). Because of their small size, some direct dyes, such as nitro dyes, can penetrate in the hair and dye it directly, at least in the outer regions. Such tints are very gentle of the hair and usually withstand 6 to 8 washings. Direct dyes, especially nitro dyes, are also frequently used in oxidative coloring agents for producing certain nuances or intensification of the color.
It is well known that colored polymers, oxidatively produced in the hair, generally are resistant to external influences, such as water, shampoo or light. Depending on the coloring technique, they are anchored so firmly, that they remain in the hair until it is cut the next time. However, the use of hydrogen peroxide, especially in an alkaline medium, has a disadvantageous effect on the structure of the hair.
From the German Offenlegungsschrift 197 45 292, the use of a combination of malonaldehyde derivatives, such as malonaldehyde bis-dialkylacetals, and amines or compounds containing an acidic CH group for coloring hair without the addition of oxidizing agent, is known. Likewise, from the state of the art, the use of a combination of certain aldehydes (German Offenlegungsschrift 197 17 280), of certain heterocyclic carbonyl compounds (German Offenlegungsschrift 197 17 223), of certain aminovinyl aldehydes (German Offenlegungsschrift 197 17 224), of certain unsaturated, non-aromatic aldehydes(German Offenlegungsschrift 197 45 356), of certain onium aldehydes or onium ketones) and amines or compounds with an acidic CH group is known for coloring hair without the addition of oxidizing agents. However, these dyes fulfill only partly the requirements that have been set.
Therefore, there continues to be a great need for a dye, which makes intensive as well as gentle colorings possible with a wide range of nuances under mild conditions.
SUMMARY OF THE INVENTION
Surprisingly, it has been found that this objective can be accomplished in an outstanding manner through the use of an agent containing a alkanolamine, at least one carbonyl compound, especially an aromatic (not heterocyclic) aldehyde compound, and at least one compound of formula (I) or (II),
in which R1 represents a C1 to C3 alkyl group, a to C1 to C3 alkoxyalkyl group or a C1 to C3 hydroxyalkyl group and R2 represents hydrogen, a hydroxy group, a methoxy group, a halogen atom, an amino group or a dimethylamino group and A
−
represents an anion, such as chloride, bromide, sulfate, hydrogen sulfate, monomethyl sulfate, acetate, lactate or iodide, for coloring fibers, particularly keratin fibers, such as human hair.
The individual components of the inventive coloring agent are kept separate from one another until shortly before their use and mixed only shortly before their use into a ready-for-use coloring agent and then applied on the fibers, which are to be dyed. Several variations are possible here. For example, the compounds of formula (I) and/or (II) can be packaged together with the aldehyde compound and, optionally, direct dyes(=dye carrier composition) and mixed shortly before use with the alkanolamine. It is, however, also possible to produce the inventive coloring agent in the form of a 2-component agent, consisting of a dye carrier composition (a), which contains the compounds of formula (I) and/or (II), as well as the monoalkanolamine and optionally direct dyes, and of a further dye carrier composition (b), which contains the aldehyde compound and, optionally, direct dyes. A further possibility is a 2-component agent, consisting of a dye carrier composition (a), which contains the compounds of formula (I) and/or (II) and optionally direct dyes and of a further dye carrier composition (b), which contains the aldehyde compound, as well as the monoalkanolamine and optionally direct dyes. Of course, it is also possible to produce the three components in the form of a 3-component agent, which consists of a dye carrier composition (a), which contains the compounds of formula (I) and/or (II) and optionally direct dyes, and a further dye carrier composition (b), which contains the aldehyde compound and optionally direct dyes, and a component (c), which contains the alkanolamine.
Of the compounds of formulas (I) and (II), the following are particularly preferred: 1-ethyl-2-methyl-quinolinium iodide, 1-ethyl-2-methyl-quinolinium chloride, 1-ethyl-4-methyl-quinolinium iodide and 1-ethyl-4-methyl-quinolinium chloride.
Some of the compounds of formulas (I) and (II) can be obtained commercially. However, the compounds of formulas (I) and (II) can also be synthesized by conventional methods known from the literature. In this connection, reference is made particularly to the articles of R. Long and K. Schofield in J. Chem. Soc., 3161 (1953), E. Roberts and E. E. Turner in J. Chem. Soc., 1832 (1927), E. A. Fehnel in J. Org. Chem., 31, 2899 (1966) and C.-C. Cheng and S.-J. Yan, “The Friedländer synthesis of quinolines”, in Org. React., 28, 37 (1982), in which the synthesis of quinolines, which are not N-alkylated, is described. A method for the alkylation of the quinoline nitrogen is described, for example, in Houben-Weyl, “Methoden der organischen Chemie (Methods of Organic Chemistry), Hetarenes II—Part 1”, R. Kreher (editor) Georg Thieme-Verlag, vol. E 7a, page 553 (1991).
The following can be used as aldehyde compounds of component (b): vanillin (4-hydroxy-3-methoxy-benzaldehyde), isovanillin (3-hydroxy-4methoxy-benzaldehyde), 3,4-dihydroxy-benzaldehyde, 4-hydroxy-benzaldehyde, 3,5-dimethoxy-4-hydroxy-benzaldehyde, 4-dimethylamino-benzaldehyde, 4-dimethylamino-cinnamaldehyde, 4-hydroxy-2-methoxy-benzaldehyde, 3,5, -dimethyl-4-hydroxybenzaldehyde, 4-dimethylamino-2-methoxybenzaldehyde, 2-hydroxybenzaldehyde, 4-hydroxy-1-naphthaldehyde, 4-methoxy-1-naphthaldehyde, 4-dimethylamino-1-naphthaldehyde, 4′-hydroxy-biphenyl-1-carbaldehyde, 2-hydroxy-3-methoxybenzaldehyde, 2,4-dihydroxy-benzaldehyde, 3,4-dihydroxy-benzaldehyde, 2,5-dihydroxybenzaldehyde, 2,3,4-trihydroxybenzaldehyde, 3,4,5-trihydroxybenzaldehyde, 2,4,6-trihydroxybenzaldehyde, 2,4-dimethoxybenzaldehyde, 2,3-dimethoxy-benzaldehyde, 2,5-dimethoxybenzaldehyde, 3,5-dimethoxy-benzaldehyde, 3,4-dimethoxy-benzaldehyde, benzene-1,4-dicarbaldehyde, 4-ethoxy-benzaldehyde, 2-methyl-1,4-naphthoquinone, 4-carboxybenzaldehyde, 4-hydroxy-3-methoxy-cinnamaldehyde, 3,5-dimethoxy-4-hydroxy-cinnamaldehyde, 3-methoxy-4-(1-pyrrolidinyl)-benzaldehyde, 4-diethylamino-3-methoxy-benzaldehyde, 1,2-phthaldialdehyde, 4-dibutylamino-benzaldehyde, 4-diethylamino-2-hydroxybenzaldehyde, 3,4-dimethoxy-5-hydroxy-benzaldehyde, 5-(4-(diethylamino)phenyl)-2,4-pentadienal, 2-methoxy-1-naphthaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, 2-nitrobenzaldehyde, 3-nitrobenzaldehyde and the 4-nitrobenzaldehyde.
As alkanolamine, monoethanolamine, isopropanolamine and diisopropanolamine come into consideration, isopropanolamine and especially monoethanolamine being preferred. The alkanolamine is added in an amount, which is sufficient in order to adjust the pH of the inventive agent to the desired value.
The compounds of formu
Javet Manuela
Mueller Catherine
Elhilo Eisa
Gupta Yogendra N.
Striker Michael J.
Wella Aktiengesellschaft
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