Dye compositions and methods of dyeing keratin fibers

Details Dye compositions and methods of dyeing keratin fibers Dye compositions and methods of dyeing keratin fibers

2000-06-12

2002-04-30

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

Dyeing involving animal-derived natural fiber material ,...

Hair dyeing

C008S423000

Reexamination Certificate

active

06379400

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to compositions and methods for dyeing keratin fibers, especially human hair, and, more particularly, to compositions for dyeing keratin fibers, especially human hair, containing nitrophenylamines.
2. Prior Art
Nitro dyes have achieved a significant importance, especially for dyeing hair. In oxidizing hair dye compositions, they are an important constituent for modifying the dyeing result and for achieving fashionable color nuances. However, by combining yellow, red and blue nitro dyes, dyeing agents can also be produced, which are able to color hair in natural to fashionable shades without the addition of oxidizing agents.
Of particular importance in this connection are yellow nitro dyes, which are taken up directly and dye the hair an intensive lemon yellow, which is to be as free as possible from red portions. Furthermore, nitro dyes must also fulfill a whole series of additional requirements. For example, they must be safe from a toxicological and dermatological point of view and must make it possible to obtain dyed colors of the desired intensity. Among other things, this assumes that they are sufficiently soluble in water. In addition, a good light fastness, rubbing fastness, permanent waving fastness and perspiration resistance is required for the colorings achieved. On the other hand, the dyes should not wash out too easily once again during a subsequent treatment or when the hair is washed. Their use in oxidizing hair dye compositions presupposes furthermore that they are stable in the presence of reducing agents and oxidizing agents and especially in alkaline solution.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide improved dye compositions containing nitrophenylamines, which meet the requirements for dyeing fibers, especially human hair, in an outstanding manner.
It is another object of the present invention to provide improved methods for dyeing keratin fibers, especially human hair, which utilizes the improved dye compositions.
Surprisingly, it has now been found that certain 4-nitrophenylamines have good water solubility and make an intensively luminous, yellow coloration possible. In addition, they have outstanding light fastness, rubbing fastness, permanent waving fastness and perspiration resistance.
The present invention therefore relates to compositions for dyeing fibers, particularly keratin fibers, such as human hair. The dye compositions are characterized in that they contain at least one compound of formula (I)
wherein, independently of one another
R1 represents hydrogen or a linear or branched alkyl group with 1 to 4 carbon atoms and
Y is a heterocyclic ring of formula (II)
with X representing nitrogen or oxygen, m is 1, 2 or 3 and n is 0 or 1; or Y is an amino group NR
2
R
3
, and R
2
and R
3
, independently of one another, each represent hydrogen, a cycloalkyl group with 1 to 6 carbon atoms or a —(CH
2
)OR
4
group, in which z is 1, 2, 3, 4, 5 or 6 with R
4
being a linear or branched alkyl group with 1 to 4 carbon atoms, with the proviso that R
2
and R
3
cannot simultaneously be hydrogen.
The compounds of the general formula (I) preferably are selected from N-(2-methoxyethyl)-4-nitrophenylamine, N-(2-methoxyethyl)-2-methyl-4-nitrophenylamine, 4-(4-nitrophenyl)morpholine, N-(3-methoxypropyl)-4-nitrophenylamine, N-(3-methoxypropyl)-2-methyl-4-nitrophenylamine, 4-(2-methyl-4-nitrophenyl)-morpholine, N-cyclopropyl-4-nitrophenylamine, 4-nitro-N-((tetrahydrofuran-2-yl)methyl)-phenylamine, 2-methyl-4-nitro-N-(tetrahydrofuran-2-yl-methyl)-phenylamine and N-cyclopropyl-2-methyl-4-nitrophenylamine.
The dyes of formula (I) are used in the inventive dye compositions preferably in a total amount of 0.01 to 10% by weight and particularly in a total amount of 0.1% to 5% by weight.
The dyes of formula (I) can easily be synthesized from available precursors and not only have a good water solubility, but also a very good absorption behavior from anionic, cationic, amphoteric or nonionic carrier compositions. The coloring obtained has a very high resistance towards being washed out and towards perspiration and light radiation, as well as towards bases, such as ammonia and acids, such as phosphoric acid or reducing agents, such as ascorbic acid or sodium sulfite, so that their use in oxidative dye compositions is facilitated appreciably. In addition, the inventive dye compositions have a good shelf life and make possible intensively luminous yellow color shades, with possibilities for varying them in all gradations and nuances from a bright lemon yellow to an intensive dark yellow.
The inventive dye compositions can be used with and also without the addition of an oxidizing agent. In the former case, the usual developing and coupling substances are added.
If the dye composition is used without an oxidizing agent, it may contain, aside from the dyes of formula (I), further, known direct-dyeing dyes from the group comprising nitro, azo, anthraquinone and triphenylmethane dyes, either alone or in admixture with one another.
Example of suitable dyes, which are picked up directly, are 1,4-bis[(2-hydroxyethyl)amino]-2-nitrobenzene, 1-(2-hydroxyethyl)amino-2-nitro-4-[di(2-hydroxyethyl)amino]-benzene (HC Blue No. 2), 1-amino-3-methyl-4-[(2-hydroxyethyl)amino]-6-nitrobenzene (HC Violet No. 1), 4-[ethyl-(2-hydroxyethyl)-amino]-1-[(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Blue No. 12), 4-[di-(2-hydroxyethyl)amino]-1-[(2-methoxyethyl)amino]-2-nitrobenzene (HC Blue No. 11), 1-[(2,3-dihydroxypropyl)amino]-4-[methyl-(2-hydroxyethyl)amino]-2-nitrobenzene (HC Blue No. 10), 1-[(2,3-dihydroxypropyl)amino]-4-[ethyl-(2-hydroxyethyl)amino-2-nitrobenzene hydrochloride (HC Blue No. 9), 1-(3-hydroxypropylamino)-4-[di(2-hydroxyethyl)amino]-2-nitrobenzene (HC Violet No. 2), 1-methylamino-4-[methyl-(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Blue No. 6), 2-((4-amino-2-nitrophenyl)amino)-5-dimethylamino-benzoic acid (HC Blue No. 13), 1-amino-4-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Red No. 7), 2-amino-4,6-dinitrophenol, 4-amino-2-nitrodiphenylamine (HC Red No. 1), 1-amino-4-[di(2-hydroxyethyl)amino]-2-nitrobenzene hydrochloride (HC Red No. 13), 1-amino-5-chloro-4-[(2-hydroxyethyl)amino]-2-nitrobenzene, 4-amino-1-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Red No. 3), 4-amino-3-nitrophenol, 4-[(2-hydroxyethyl)amino]-3-nitrophenol, 1-[(2-aminoethyl)amino]-4-(2-hydroxyethoxy)-2-nitrobenzene (HC Orange No. 2), 4-(2,3-dihydroxypropoxy)-1-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Orange No. 3), 1-amino-5-chloro-4-[(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 10), 5-chloro-1,4-[di(2,3-dihydroxypropyl)amino]-2-nitrobenzene (HC Red No. 11), 2-[(2-hydroxyethyl)amino]-4,6-dinitrophenol, 4-ethylamino-3-nitrobenzoic acid, 2-[(4-amino-2-nitrophenyl)amino]-benzoic acid, 2-chloro-6-ethylamino-4-nitrophenol, 2-amino-6-chloro-4-nitrophenol, 4-[(3-hydroxypropyl)amino]-3-nitrophenol, 2,5-diamino-6-nitropyridine, 1,2,3,4-tetrahydro-6-nitroquinoxaline, 7-amino-3,4-dihydro-6-nitro-2H-1,4-benzoxazine (HC Red No. 14), 1-amino-2-[(2-hydroxyethyl)amino]-5-nitrobenzene (HC Yellow No. 5), 1-(2-hydroxyethoxy)-2-[(2-hydroxyethyl)amino]-5-nitrobenzene (HC Yellow No. 4), 1-[(2-hydroxyethyl)amino]-2-nitrobenzene (HC Yellow No. 2), 2-[(2-hydroxyethyl)amino]-1-methoxy-5-nitrobenzene, 2-amino-3-nitrophenol, 1-(2-hydroxyethoxy)-3-methylamino-4-nitrobenzene, 2,3-(dihydroxypropoxy)-3-methylamino-4-nitrobenzene, 2-[(2-hydroxyethyl)amino]-5-nitrophenol (HC Yellow No. 11), 3-[(2-aminoethyl)amino]-1-methoxy-4-nitrobenzene hydrochloride (HC Yellow No. 9), 1-[(2-ureidoethyl)amino]-4-nitrobenzene, 4-[(2,3-dihydroxypropyl)amino]-3-nitro-1-fluoro-methylbenzene (HC Yellow No. 6),

Affiliated with

Also associated with

Rating

Dye compositions and methods of dyeing keratin fibers does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Dye compositions and methods of dyeing keratin fibers, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Dye compositions and methods of dyeing keratin fibers will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2895444