Polymeric dye compounds and compositions and methods for...

Details Polymeric dye compounds and compositions and methods for... Polymeric dye compounds and compositions and methods for...

2000-03-10

2001-10-23

Page, Thurman K. (Department: 1615)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S405000, C008S587000, C008S647000, C424S070100, C424S070110, C424S070122, C424S070170, C424S070210, C424S070220, C424S070270, C424S070600, C424S070900

Reexamination Certificate

active

06306182

ABSTRACT:

TECHNICAL FIELD
The invention is in the field of compounds capable of providing color to hair, and the related compositions and methods.
BACKGROUND OF THE INVENTION
A large majority of women color their hair, either to cover gray or change hair color. There are generally three types of hair color: permanent, semi-permanent, and temporary. The term “permanent” generally refers to oxidative dyes, which provide hair color that lasts about four to six weeks. Oxidative hair dyes are usually sold in the form of a two component kit. In one container is an aqueous alkaline composition in the liquid, gel, or creme form that contains oxidative dyes in addition to other ingredients. In the other container is a developer composition that contains an oxidizing agent, usually hydrogen peroxide. The two components are mixed immediately prior to use and applied to hair. The relatively high pH of the composition causes the hair shaft to swell, permitting the dye precursors in the lotion to penetrate the hair shaft. The oxidizing agent then oxidizes the dye precursors, which then combine to form large color molecules within the hair shaft. The mixture is left on the hair for an appropriate period of time, generally 20 to 60 minutes, then rinsed off with water. While consumers who use oxidative dyes appreciate that oxidative dyes provide permanent color, there are certain drawbacks to oxidative dyes that consumers find less than desirable. For example, the peroxide necessary to make the oxidative dye process operable sometimes causes sensitive hair to become dry and brittle. In addition, oxidatively colored hair may undergo further chemical change after two to three weeks, causing the color to fade or exhibit a hue different from the original color. The degree of change varies, with red shades being most susceptible.
Semi-permanent hair color differs in that the dye molecules are preformed prior to application to the hair, and the size of the molecules does not change during the dye process. Semi-permanent dyes will wash out of the hair after about six to twelve shampoos. Semi-permanent hair color is perceived to be gentler to hair because peroxide is not used, as in oxidative hair color.
Temporary hair color is color applied to the hair surface, which is removed with one shampoo. Temporary haircolor is most often used when a unique effect is desired for one day.
Accordingly, the gold standard for haircolor is to provide a composition which does not utilize oxidizing agents such as hydrogen peroxide. The haircolor should provide the same intensity and duration of color as found in oxidative dyes, yet at the same time be gentle and non-drying to the hair.
The object of the invention is to provide a novel class of compounds for use in coloring the hair.
Another object of the invention is to provide a class of polymeric compounds for use in coloring hair, which can be used in hair color systems which are free of oxidizing agents, or contain them in substantially reduced amounts.
Another object of the invention is to provide a method for coloring hair with a haircolor composition containing these polymeric compounds.
SUMMARY OF THE INVENTION
The invention comprises a compound of the formula (“Formula I”):
wherein:
n, y, and z are each independently integers ranging from 1 to 100,000;
R
1
through R
6
, and R
8
are each independently H, C
1-6
alkyl, hydroxyalkyl, substituted or unsubstituted aminoalkyl; or R
4
and R
5
together form a substituted or unsubstituted heterocyclic 5 to 6 membered ring; wherein the substituents are selected from C
1-6
alkyl, hydroxyalkyl, or aminoalkyl;
R
7
is H, SR
1
; or S—R
7
together in the above formula form an isothiouronium salt or Bunte salt;
X is a linking group; and
D is a chromophore that absorbs visible light, and
the terminal groups on the polymer may be alkyl, hydroxyl, hydrogen, or substituted alkyl, where the substituents are selected from hydrogen, hydroxyl, halogen, or alkyl.
The invention is further directed to a hair dye composition comprising, by weight of the total composition:
0.01-40% of a polymeric dye compound of Formula I,
0.01-25% of a reducing agent; and
0.1-99% water.
The invention further comprises a method for coloring hair comprising applying an aqueous based hair dye composition containing a polymeric dye compound of Formula I and a reducing agent, to the hair for a period of time sufficient to cause coloration of the hair.
DETAILED DESCRIPTION
The invention comprises a polymeric dye compound capable of causing coloration of hair, a hair dye composition containing the polymeric dye compound, and a method for coloring hair.
I. THE POLYMERIC DYE COMPOUND
The polymeric dye compound of the invention has the following general formula:
wherein:
n, y, and z are each independently integers ranging from 1 to 100,000;
R
1
through R
6
and R
8
are each independently H, C
1-6
alkyl, hydroxyalkyl, substituted or unsubstituted aminoalkyl; or R
4
and R
5
together form a substituted or unsubstituted heterocyclic 5 to 6 membered ring; wherein the substituents are C
1-6
alkyl, hydroxyalkyl, or aminoalkyl;
R
7
is H, SR
1
, or S—R
7
together in the above formula form an isothiouronium salt or Bunte salt;
X is a linking group; and
D is a chromophore that absorbs visible light, and, preferably, the terminal groups on the polymer may be alkyl, hydroxyl, hydrogen, or substituted alkyl, where the substituents are selected from hydrogen, hydroxyl, halogen, or alkyl.
Preferably, in the polymeric dye compound the ratio of n:y:z ranges from 20-70 n units to 30-80 y units, to 1-20 z units. More preferably n, y, and z are each independently integers ranging from 1 to 1,000; most preferably 1 to 100. Where the polymer contains a plurality of any of the three types of units (or mers), it is not required that all of the same type units be strung together as in a block or graft copolymer. The three types of units can be intermingled and can be located anyplace in the polymer chain. It is intended that the above generic formula be so construed.
A variety of linking groups are suitable including the groups —C
m
H
2m
NR′—, —NR′—, —NR′C(O)—, —C(O)NR′—, —NR′SO
2
—, —SO
2
NR′—, —C
m
H
2m
NR′CO
2
—, or —C
m
H
2m
CO
2
—, wherein: R′ is H, C
1-6
alkyl, C
1-6
hydroxyalkyl, or C
1-6
aminoalkyl; and m is an integer from 0 to 1,000, preferably 1 to 500. As suitable examples of —C
m
H
2m
NR′— may be mentioned —CH
2
NH—, —C
4
H
8
NH—, and —C
12
C
24
NH—. As suitable examples of —NR′— groups may be mentioned —NH— and NCH
3
—. As suitable examples of —NR′C(O)— groups may be mentioned NC
3
H
7
C(O)— and NCH
3
C(O)—. As examples of suitable —C(O)NR′— groups may be mentioned —C(O)NC
2
H
5
— and —C(O)NC
3
H
7
—. As examples of suitable —NR′SO
2
groups may be mentioned —NC
3
H
8
SO
2
— and —NC
12
H
25
SO
2
. As examples of suitable —SO
2
NR′— groups are —SO
2
NC
3
H
7
— and —SO
2
NC
12
H
25
—. As examples of suitable —C
m
H
2m
NR′CO
2
— groups may be mentioned —C
2
H
4
NCH
3
CO— and —C
12
H
24
NCH
3
CO—. As examples of suitable —C
m
H
2m
CO
2
— groups may be mentioned —CH
2
CH
2
CO
2
— and —CH
2
CH
2
CO
2
—.
In the preferred compound, S—R
7
together forms an isothiouronium salt; and X is a linking group —C
m
H
2m
NR′CO
2
— or —(CH
3
)
2
CNHCO
2
—. Most preferably R
1
through R
6
, and R
8
are methyl; and m=2. Most preferred is a polymeric dye compound of the formula:
wherein X is —C
m
H
2m
NHCO
2
— and n, y, and z are each independently 1-100.
The chromophore, D, that may be used is any chromophore that is suitable for use in dyeing hair or textile fibers, and which is capable of absorbing visible light, e.g. light in the fluorescent wavelength range. Examples of these chromophores include radicals of monoazo, diazo, polyazo dyes or metallic derivatives thereof. Further examples include anthroquinones, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthene, nitroaryl, naphthoquinone, pyrenequionone, and the like. P

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