Bleaching and dyeing; fluid treatment and chemical modification – Dyeing involving animal-derived natural fiber material ,... – Hair dyeing
Reexamination Certificate
2000-12-18
2002-06-04
Douyon, Lorna M. (Department: 1751)
Bleaching and dyeing; fluid treatment and chemical modification
Dyeing involving animal-derived natural fiber material ,...
Hair dyeing
C008S543000, C008S549000, C008S642000, C008S685000, C008S918000, C540S126000, C544S180000, C544S224000, C544S242000, C534S634000, C534S637000, C534S638000
Reexamination Certificate
active
06398822
ABSTRACT:
TECHNICAL FIELD
This invention relates to a packaged hair colouring composition comprising a reactive dye compound comprising a chromophore and a nitrogen-containing heterocycle comprising at least one thio-substituent.
BACKGROUND OF THE INVENTION
The desire to alter the color of human hair is not a facet of modern times. Since the days of the Roman Empire the color of human hair has been routinely altered to accommodate the changes of fashion and style. However the attainment of precise initial colors which are retained by the hair for a desirable period has remained a more elusive goal. The difficulties in the development of hair coloring compositions which can deliver precise long-lasting colors are in part due to the inherent structure of the hair itself and in part due to the necessary conditions of effective hair coloration processes.
In general, the condition and structure of human hair is not regular along the length of the hair shaft. Human hair is subject to various chemical and mechanical treatments such as combing, brushing, shampooing, heating, perming as well as exposure to the sun. As such, the hair at the ends of the hair shaft will generally exhibit greater signs of damage relative to the new growth close to the scalp. This damage can lead to inconsistent coloration when the hair is dyed due to irregular uptake of the hair coloring agents along the length of the hair shaft.
Once the hair has been colored there is a desire for the color to be resistant to fading, as occasioned by the actions of washing (also known as wash fastness), perspiration, hair spray and other exterior factors such as the action of the sun, and further that the color be retained in a consistent manner for a predictable period of time. Additionally damage to the hair that can lead to irregular dye uptake as discussed above, can lead to increased fading of the damaged portions of the hair and consequently, irregular levels of color fade over time. An additional difficulty commonly associated with the dyeing of human hair is the need for dye systems which avoid any adverse effect on the hair and skin of the user, such as brittle hair, or, irritation of the skin, or, staining (coloring) of the skin.
Thus, it would be desirable to develop a hair coloring composition which exhibits reduced fade, provides improved resistance to wash out during a regular cleansing regimen, can deliver substantially consistent hair color results throughout the hair, which has reduced irritant effect on the skin, which has reduced staining on the skin, which has reduced adverse effects on the hair of the user and also to develop a convenient and easy-to-use method for the delivery of such a hair coloring composition to the hair.
Over the years significant effort has been directed towards the elimination of many of the problems associated with the dyeing of human hair. Various approaches to hair dyeing have been developed, these include, oxidative dyes, direct action dyes, natural dyes, metallic dyes and reactive dyes.
GB-A-0,951,021 (Turner-Hall Corporation) relates to methods and compositions for dyeing keratinous fibres by attaching a dyestuff molecule to a particular site thereof through true covalent bonds. The method comprises reducing some of the disulfide linkages of the cystine in the fibers to sulfhydryl groups while breaking hydrogen bonds by applying to the fibers in alkaline aqueous solution a reducing agent for breaking disulfide linkages of keratinous fibres and a hydrogen bond breaker for keratinous fibres and bonding a water-soluble fibre reactive dye compound such as a dichlorotriazine dye to the sulfhydryl groups by applying an aqueous solution of the fibre reactive dye. Thioglycolic acid is disclosed as a reducing agent.
U.S. Pat. No. 3,415,606 discloses a method for dyeing human hair comprising the steps of treating said hair with an effective amount of mercaptan and then treating the hair with a dichlorotriazine fibre reactive dye.
“The Reaction Mechanism of Fibre Reactive Dyestuffs with Hair Keratin”, Albert Shansky, American Perfumer and Cosmetics, November 1966, and “Dyeing of Human Hair with Fibre Reactive Dyestuffs”, Albert Shansky, Cosmetics and Toiletries, November 1976, disclose a method of coloring hair comprising treating the hair for five minutes with a reducing-H bond breaking solution (containing thioglycolate, alkali, lithium bromide and urea) followed by rinsing the hair and then treating the hair with a dichlorotriazine fibre reactive dye.
Dyes and Pigments 14, 1990, pages 239-263, “Synthesis and Application of Reactive Dyes with Heterocyclic Reactive Systems” discloses fibre reactive dyes containing chlorotriazine heterocycles with thio substituents.
Reactive dye hair coloring agents can be used to deliver a variety of hair colors to the hair. However substantial improvement is needed in the areas of color saturation, color development, precise initial color consistency, improved wash fastness, improved hair condition and levels of hair damage.
Thus there is a need for reactive dye hair coloring compounds and compositions which effectively dye the hair but avoid or reduce damage to the hair, which can color the hair effectively and avoid or reduce irritation and/or staining to the skin of the user.
It has surprisingly been found that the packaged hair colouring compositions of the present invention comprising a nitrogen-containing heterocycle selected from pyrimidine or triazine, substituted with at least one thio-derivative, provides improvements in colour saturation, colour development, colour consistence, wash fastness, hair condition, and reduction in hair damage and skin irritation.
In addition, conventional, reactive dye hair coloring compositions typically comprise at least two separately packaged components, which are generally, reducing agent and reactive dye hair coloring agents. These separately packaged components are admixed just prior to application to the hair. Such an admixing step can be messy and inconvenient to the user. Typically, such coloring compositions need to be used soon after admixing due to degradation of the resulting coloring composition. As such, excess admixed coloring composition is disposed of after application of the required amount to the hair. It has been found that the reactive dyes of the present invention can be incorporated in a singly packaged mixture with improved stability versus conventional reactive dye systems. The singly packaged coloring compositions of the present invention are suitable for use in a multi-application format (i.e. the consumer can use a single package for several color applications over a period of time). It has also been found that the reactive dye compounds and compositions herein are stable over time, and can be stored as such.
All percentages are by weight of the final compositions in the form intended to be used unless specified otherwise.
SUMMARY OF THE INVENTION
According to the present invention there is provided packaged hair colouring composition comprising a stable aqueous hair colouring composition comprising a compound of formula (I):
wherein D is a chromophore;
X and Y are independently selected from halogen and —SR′, provided that at least one of X and Y is —SR′, wherein R′ is selected from H, C
1
-C
4
alkyl, (CH
2
)
n
COOH, (CH
2
)
n
CONH
2
, (CH
2
)
n
SO
3
H, (CH
2
)
n
COOM, (CH
2
)
n
PO
3
H, (CH
2
)
n
OH, (CH
2
)
n
SSO
3
−
, (CH
2
)
n
NR″
2
, (CH
2
)
n
N
+
R″
3
, PhSSO
3
−
, PhSO
3
H, PhPO
3
H, PhNR″
2
, PhN
+
R″
3
, —CN, SO
3
−
, (CH
2
)
2
CH(SH)R″(CH
2
)
3
COOH, —CH
2
CHOHCH
2
SH, and
—CH
2
CH
2
NH
2
n is an integer in the range of 1 to 4 wherein within the same molecule n is not necessarily the same integer; and M is a cation of alkaline earth metal, alkali metal, NH
4
+
or NR″
3
+
;
L is a linking moiety;
Z is selected from pyrimidine or triazine;
R″ is C1-C4 alkyl;
and a package for said hair colouring composition.
The packaged hair colouring compositions of the present invention provid
Brock Earl David
Harper Heather Holden
Yousaf Taher Iqbal
Corstanje Brahm J.
Douyon Lorna M.
Koss Ann-Marie
Peebles Brent M.
Rosnell Tara M.
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