Agent for dyeing fibers comprising an indoline/indolium...

Details Agent for dyeing fibers comprising an indoline/indolium... Agent for dyeing fibers comprising an indoline/indolium...

2001-10-17

2003-11-25

Einsmann, Margaret (Department: 1751)

Bleaching and dyeing; fluid treatment and chemical modification

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

Hair dyeing

C008S426000, C008S102000, C008S110000, C008S917000, C008S918000, C008S587000, C008S607000, C008S608000, C008S404000

Reexamination Certificate

active

06652601

ABSTRACT:

The object of the present invention is an agent for dyeing fibers, particularly keratin fibers (for example human hair), said agent containing an indole derivative and a carbonyl compound, and to a multicomponent kit for dyeing and subsequently decolorizing fibers, said kit containing both an agent for producing a coloration on the fibers and an agent for the reductive removal of the coloration.
Depending on the starting color of the hair to be dyed and the desired end result, hair colorants fall mainly into the domain of oxidative hair dyes and tinting agents. Oxidative dyes lend themselves eminently to the covering of large gray areas. The oxidative dyes used when the gray area amounts to up to 50% are usually referred to as oxidative tinting agents, whereas the oxidative dyes used when the gray area exceeds 50% or the dyes used for “bright coloring” are usually referred to as oxidative dyes. Direct dyes are contained mainly in non-oxidative colorants (tinting agents). Some direct dyes, for example the nitro dyes, can, because of their small size, penetrate into the hair and—at least in the outer regions—bring about direct dyeing. Such tinting agents are very gentle to the hair, they can usually withstand 6 to 8 hair washings and they allow a gray coverage of about 20%.
In general, direct dyes and oxidative tints are washed out of the hair after a few hair washings. Their durability depends among other things on the hair structure and the color shade used. Oxidative dyes can fade somewhat with time, but as a rule remain on the hair until the next haircut. When it is desired to wear a particular color only for a certain length of time or if the user dislikes a color, however, it may be desirable to be able to remove the hair coloring at any time. Also, when a person's hair is dyed for the first time, a gentle and complete removal of the coloration can reduce the fear of an excessively drastic color change (“test dyeing”).
European Patent EP 0 847 749 discloses a combination of diiminoisoindoline or 3-aminoisoindolone derivatives and compounds with primary or secondary amino groups for coloring keratin fibers without the addition of an oxidant. It is also known from German Unexamined Patent Application DE-OS 43 35 623 to use for the dyeing of keratin fibers a combination of indolinone derivatives and compounds with primary or secondary amino groups, heterocycles or aromatic hydroxy compounds. Moreover, DE-OS 44 09 143 describes the use of isatin derivatives for the dyeing of keratin fibers. DE-OS 197 45 292 discloses the use of a combination of malonaldehyde derivatives, for example malonaldehyde-bis-dialkyl acetals, and amines or CH-acidic compounds for dyeing hair without the addition of oxidants. Also, DE-OS 197 17 280 discloses the use of a combination of certain heterocyclic aldehydes and amines or CH-acidic compounds for dyeing hair without the addition of oxidants.
A great demand, however, continues to exist for colorants which under mild conditions give intense as well as gentle colorations in a wide range of shades and which—if desired—can subsequently be removed at any time.
The object of the present invention is therefore to provide a dyeing system which without the addition of an oxidant (for example hydrogen peroxide) gives a gentle, intense coloration on fibers in the yellow, brown, green and purple range with good fastness properties (light fastness, wash fastness, abrasion resistance) and at the same time permits gentle and complete removal of said coloration at any point in time.
Surprisingly, we have now found that dyes containing an indoline derivative of formula (I) or a 3H-indolium derivative of formula (Ia) as well as a carbonyl compound give in gentle manner intense colorations which can be removed completely at any desired subsequent point in time.
Hence, the object of the present invention is an agent for dyeing fibers, for example wool, silk, cotton or hair, and particularly keratinic fibers, for example human hair, said agent being obtained by mixing two components—if necessary with addition of an alkalinizing agent or an acid—and being characterized in that one component (component A2) contains at least one carbonyl compound, particularly an aromatic aldehyde compound, and the other component (component A1) contains at least one indoline derivative of formula (I) or a 3H-indolium derivative of formula (Ia)
the R1 to R8 and A
−
groups in formulas (I) and (Ia) having the following meaning:
R1 denotes a straight-chain or branched C1-C8 alkyl group, C1-C8 monohydroxyalkyl group, C2-C8 polyhydroxyalkyl group, C1-C8 alkoxy-(C1-C8)-alkyl group or a thio-(C1-C8)-alkyl group, a —(CH
2
)
m
—X—(CH
2
)
n
—Y—(CH
2
)
p
—R
a
group, a —(CH
2
)
n
—X—R
a
group, a —(CH
2
)
m
—Y—(CH
2
)
n
—X—(CH
2
)
p
—R
a
group, a —(CH
2
)
m
—CO—(CH
2
)
p
—X—R
a
group, a —(CH
2
)
p
—R
a
group, a —(CH
2
)
m
—X—(CH
2
)
p
—CO—Y—R
a
group or
 wherein
X and Y independently of each other denote an oxygen atom, a sulfur atom or an NR
b
group, R
a
and R
b
independently of each other denote a hydrogen atom, an, optionally substituted, aromatic carbocycle or heterocycle or a straight-chain or branched C1-C8 alkyl group, m and n independently of each other denote an integer from 1 to 6 and p denotes an integer from 0 to 6;
R2 is a hydrogen atom or a straight-chain C1 to C6-alkyl group,
R3 and R4 independently of each other denote a straight-chain or branched C1-C4-alkyl group (particularly a methyl group), a (CH
2
)
n
—R
c
group, a —(CH
2
)
m
—CHR
c
—X—(CH
2
)
n
—R
c
group, a —(CH
2
)
n
—CO—R
c
group, a —(CH
2
)
n
—CO—XR
c
group, a (CH
2
)
n
—CN group, a —(CH
2
)
n
—CH═C(CH
3
)
2
group, a —(CH
2
)
m
—X—CHR
c
—(CH
2
)
n
—R
c
group or a —(CH
2
)
n
CH═CH group, X standing for an oxygen atom, a sulfur atom or an NR
b
group, m and n independently of each other denoting 1 to 6 and R
c
standing for a hydrogen atom, an, optionally substituted, aromatic carbocycle or heterocycle or a straight-chain or branched C1-C6-alkyl group, providing that the R3 and R4 groups, together, linked through a (CH
2
)
n
group (with n=1-3) can also form a spiro compound with the 3H carbon;
R5, R6, R7 and R8 independently of each other denote a straight-chain or branched C1-C4-alkyl group or a C1-C4-hydroxyalkyl group, a hydroxyl group, a methoxy group, a benzyl group, a halogen atom (F, Cl, Br, I), a nitro group, a nitroso group, a cyano group, a trifluoromethyl group, a —CHO group, a —COR
d
group, a —COOH group, a —CO
2
R
d
group, an —OCOR
d
group, an —OCH
2
-aryl group, an —SO
2
NH
2
group, an —NH
2
group, an —NH
3
+
group, an —NHR
d
group, an —NH
2
R
d+
group, an —N(R
d
)
2
group, an —N(R
d
)
3
+
group, an —NHCOR
d
group, an —NHCOOR
d
group, a —CH
2
NH
2
group, a —CH
2
NHR
d
group, a —CH
2
N(R
d
)
2
group, a —CO
2
CF
3
group, a —PO(OR
d
)
2
group, —SO
2
CHF
2
group, an —SO
2
CF
3
group an —SO
2
R
d
group or an —SR
d
group, wherein R
d
denotes a hydrogen atom, an, optionally substituted, aromatic carbocycle or a heterocycle or a C1-C6-alkyl group, providing that at least one of the R5 to R8 groups is different from hydrogen; and
A
−
denotes an anion of an organic or inorganic acid.
A
−
is preferably a chloride, bromide, iodide, hydrogen sulfate, sulfate, toluenesulfonate, benzenesulfonate, monomethyl sulfate, hexafluorophosphate, hexafluoroantimonate, tetrafluoroborate, tetraphenylborate, formate, acetate or propionate ion. The chloride ion, tetrafluoroborate ion, acetate ion and hydrogen sulfate ion are particularly preferred.
Among the compounds of formulas (I) and (Ia), the following are preferred:
1,3,3,4-tetramethyl-2-methyleneindoline and the salts thereof,
1,3,3,5-tetramethyl-2-methyleneindoline and the salts thereof,
1,3,3,6-tetramethyl-2-methyleneindoline and the salts thereof,
1,3,3,7-tetramethyl-2-methyleneindoline and the salts thereof,
1,3,3,6,7-pentamethyl-2-methyleneindoline and the salts thereof,
1,3,3,5,7-pentamethyl-2-methyleneindoline and the salts thereof,
1,3,3,4,7-pentamethyl-2-methyleneindoline

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