Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-01-18
2004-06-15
Hardee, John R. (Department: 1751)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S372000, C549S378000, C549S506000, C564S443000, C546S232000
Reexamination Certificate
active
06750355
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to new compounds and compositions containing these compounds as primary intermediates for oxidative coloring of hair fibers.
BACKGROUND OF THE INVENTION
Coloration of hair is a procedure practiced from antiquity employing a variety of means. In modern times, the method most extensively to color hair is an oxidative dyeing process utilizing one or more oxidative hair coloring agents in combination with one or more oxidizing agents.
Most commonly a peroxy oxidizing agent is used in combination with one or more oxidative hair coloring agents, generally small molecules capable of diffusing into hair and comprising one or more primary intermediates and one or more couplers. In this procedure, a peroxide material, such as hydrogen peroxide, is employed to activate the small molecules of primary intermediates so that they react with couplers to form larger sized compounds in the hair shaft to color the hair in a variety of shades and colors.
A wide variety of primary intermediates and couplers have been employed in such oxidative hair coloring systems and compositions. Among the primary intermediates employed there may be mentioned p-phenylenediamine, p-toluenediamine, p-aminophenol, 4-amino-3-methylphenol, N,N-bis(2-hydroxyethyl)-p-phenylene diamine, 1-(2-hydroxyethyl)-4,5-diaminopyrazole and as couplers there may be mentioned resorcinol, 2-methylresorcinol, 3-aminophenol, 2,4-diaminophenoxyethanol, and 5-amino-2-methylphenol.
There are numerous additional requirements for oxidation dye compounds that are used to dye human hair besides the color or the desired intensity. Thus, the dye compounds must be unobjectionable in regard to toxicological and dermatological properties and must provide the desired hair color with a good light fastness, good selectivity, fastness to a permanent wave treatment, acid fastness, and fastness to rubbing. The color of the hair dyed with the dye compounds in each case must be stable for at least 4 to 6 weeks to light, rubbing and chemical agents. Furthermore, an additional requirement is the production of a broad palette of different color shades using different developer and coupler substances. For providing a yellow or orange yellow coloration to hair, resorcinol and 2-methyl resorcinol have been extensively used in combination with p-aminophenol. Coupling of p-aminophenol with 2-methyl resorcinol provides weak orange yellow, while coupling of p-aminophenol with resorcinol gives weak yellow green. 6-Amino-m-cresol (U.S. Pat. No. 4,396,392) as well as direct dye 2-amino-4-nitro-6-chlorophenol is also used in current practices. A combination of tetraaminopyrimidine and 3,4-dimethyl-2,6-dihydroxy pyridine (EP 63736 A2) or a combination of 6-hydroxyindole and p-aminophenol (U.S. Pat. No. 5,279,620) are also used. 6-Hydroxyindole couples with p-aminophenol and p-phenylenediamine to provide golden beige and medium golden brown, respectively. However, these yellow couplers suffer from weak and dull coloration, especially in the presence of primary intermediates and couplers. Therefore, there is a need to provide compounds to impart yellow and orange yellow coloration in oxidative hair coloring without these drawbacks.
SUMMARY OF THE INVENTION
It is therefore an object of this invention to provide new primary intermediate compounds useful for providing yellow or orange yellow color shades with various combinations of primary intermediates and couplers.
It has been discovered that new compounds that are derivatives of 2-aminophenol are suitable primary intermediates for hair coloring compositions and systems for providing good oxidative coloration of hair and for providing acceptable light fastness, good selectivity, fastness to shampooing, fastness to perspiration and permanent wave treatment, and suitable for providing a wide variety of different color shades with various primary intermediate and coupler compounds.
The invention provides new compounds of formula (1):
wherein R
1
and R
2
are each individually selected from hydrogen atoms, C
1
to C
5
alkyl, C
1
to C
5
mono or dihydroxyalkyl, phenyl or benzyl optionally substituted with a hydroxyl, amino or C
1
to C
3
alkoxy group, or R
1
and R
2
together with the nitrogen atom to which they are attached form a C
3
to C
6
, preferably C
4
to C
6
, saturated or unsaturated ring optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms.
These novel primary intermediates are used to provide coloration to hair in which there is good dye uptake by the hair and provides shades or colors which are stable over a relatively long period of time. The novel primary intermediates provide for dyeing of hair to impart color or shades that possess good wash fastness and do not undergo significant changes on exposure to light or shampooing.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of this invention are those of formula (1)
wherein R
1
and R
2
are each individually selected from hydrogen atoms, C
1
to C
5
alkyl, C
1
to C
5
mono or dihydroxyalkyl, phenyl or benzyl optionally substituted with a hydroxyl, amino or C
1
to C
3
alkoxy group, or R
1
and R
2
together with the nitrogen atom to which they are attached form a C
3
to C
6
saturated or unsaturated ring optionally containing in the ring one or more additional hetero atoms selected from O, S and N atoms.
Preferably R
1
and R
2
are each individually selected from a hydrogen atom, a C
1
to C
3
alkyl group, more preferably methyl groups; phenyl or benzyl optionally substituted with an alkoxy group, more preferably a methoxy group, or R
1
and R
2
together with the nitrogen atom to which they are bound form a piperazine, piperidine, imidazole, or morpholine ring.
Especially preferred compounds of formula (1) of this invention are the following compounds:
2-amino-5-phenylaminomethyl-phenol;
2-amino-5-piperidin-1-ylmethyl-phenol; and
2-amino-5-pyridin-3-ylaminomethyl-phenol.
The new 2-aminophenol derivative compounds of formula (1) of this invention can be prepared according to the following reaction sequence wherein R
1
and R
2
are as defined herein before.
In this synthesis procedure the aldehyde compound of formula (2) is subjected to reductive amination with the reagent R
1
R
2
NH using reducing agents such as sodium triacetoxyborohydride, sodium cyanoborohydride, or polymethylhydrosiloxane (PMHS) to produce a compound of formula (3). Catalytic hydrogenation of the compound of formula (3) with Pd/C under hydrogen produces a compound of formula (1).
REFERENCES:
patent: 4958026 (1990-09-01), Schoellkopf et al.
patent: 63-45282 (1988-02-01), None
patent: 99/40093 (1999-08-01), None
Lim Mu'Ill
Pan Yuh-Guo
Bolam Brain M.
Dressman Marianne
Hardee John R.
Rosnell Tara M.
The Procter & Gamble & Company
LandOfFree
Primary intermediates for oxidative coloration of hair does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Primary intermediates for oxidative coloration of hair, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Primary intermediates for oxidative coloration of hair will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3365920