Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-10-10
2003-05-27
McKane, Joseph K. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C548S311700, C548S414000, C548S453000, C008S405000
Reexamination Certificate
active
06570019
ABSTRACT:
BACKGROUND OF THE INVENTION
The object of the present invention are new cationic pyrrolopyrrole derivatives, a process for producing them and dyes, which are intended for keratin fibers and contain these compounds.
As a rule, two dyeing processes are used for treating keratin-containing fibers, such as human hair, wool or furs, for changing their color. In the first process, the dyeing is carried out with so-called oxidative or permanent dyes, using a mixture of different developing substances and coupling substances and an oxidizing agent. If necessary, for rounding off the dyeing result or for producing special color effects, so-called substantive (non-oxidative) dyes can be added. The second method exclusively uses substantive dyes, which are applied on the fibers in a suitable carrier composition. This method is easily employed, decidedly mild and distinguished by causing only little damage to the keratin fibers. The substantive dyes, used here, must meet a plurality of requirements. They must be safe toxicologically and dermatologically and make it possible to achieve dyeings in the desired intensity. Among other things, this also presupposes an adequate solubility in water. In addition, good light fastness, acid resistance and rubbing fastness for the dyeings achieved are required.
As a rule, a combination of different non-oxidative dyes is required for substantive (non-oxidative) dyes. Since the selection of red and blue dyes, which can be used in coloring agents for keratin fibers, is limited, there is furthermore a need for such dyes.
Water-soluble diketopyrrolo[3,4-c]pyrroles, which contain at least one water-solubilizing anionic group, are known from the German Offenlegungsschrift 40 11 927. These compounds are said to make uniform, brilliant dyeing of nitrogen-containing and cellulosic fibers possible with good fastness properties. Because of their inferior take-up properties on keratin fibers, such compounds usually give satisfactory dyeings only in conjunction with carriers. Furthermore, the EP publication 0 953 343 discloses the use of water-insoluble diketopyrrolo[3,4-c]pyrroles as dyeing pigments in cosmetic materials, such as makeup preparations. Likewise, the German Offenlegungsschrift 44 35 211 discloses dyketopyrroles, which are to find use as electro-chrome materials in display systems.
SUMMARY OF THE INVENTION
It has now been found that, by introducing a cationic group, outstanding, water-soluble diketopyrrolo[3,4-c]pyrroles are obtained, which largely fulfill the aforementioned requirements and, without the addition of carriers, make intensive dyeings with good washing resistance, light stability and sweat resistance possible.
The object of the present invention therefore are, cationic diketopyrrolopyrroles of the general formula 1
wherein, independently of one another, Q
1
and Q
2
represent an optionally substituted, aromatic, isocyclic or heterocyclic group with 5 to 14 atoms in the ring, the heterocyclic group containing at least one oxygen, nitrogen or sulfur atom, preferably an aromatic, monocyclic to tricyclic group, especially an aromatic, monocyclic or bicyclic group with 6 to 10 atoms, and the R1 and R2 groups, independently of one another represent hydrogen or a Y—B
+
A
−
group, with the proviso that at least one of the R1 and R2 groups is not hydrogen; B
+
is an aromatic, aliphatic, alicyclic, aromatic heterocyclic or non-aromatic heterocyclic, quaternary ammonium group or a quaternary phosphonium group; Y is an optionally substituted, linear or branched C
1
to C
6
alkylene group and A
−
is an anion.
In the general formula (I) B
+
preferably represents
(i) an aromatic, heterocyclic, quaternary ammonium compound, especially a quaternary compound of N-methylimidazole, N-allylimidazole, 2-ethylimidazole or 1,2-dimethylimidazole or a quaternary compound of pyridine, 4-dimethylaminopyridine, pyrimidine, pyrazole, N-methyl-pyrazole or quinoline; or
(ii) a non-aromatic, heterocyclic, quaternary ammonium compound, especially a quaternary compound of diazabicyclo[2,2,2]octane, N-methyl-morpholine, N-ethylmorpholine, 1-methylpiperidine, or urotropine; or
(iii) a quaternary, alkylammonium compound, arylammonium compound or arylakylammonium compound of the formula NR
5
R
6
R
7
, in which R
5
, R
6
and R
7
independently of one another represent a benzyl group, a phenyl group, or a C
1
to C
6
alkyl group, especially a methyl group, an ethyl group, a propyl group, an isopropyl group or a butyl group, the aforementioned alkyl group being unsubstituted or substituted with one or more hydroxy group or amino groups;
(iv) a quaternary phosphonium compound, especially a trialkylphosphonium compound or a triarylphosphonium compound. In particular, B
+
represents an N-methylimidazolium compound, a 4-dimethylaminopyridnium compound, a triethylammonium compound or a trimethylammonium compound.
In the general formula (I), Y preferably represents a —CH
2
— group, a —CH
2
—CH
2
— group, a —CH
2
—CH
2
—CH
2
— group, —CH
2
—CH
2
—CH
2
—CH
2
— group or a linear or branched C
2
to C
6
alkylene group, substituted with one or more alkyl groups, hydroxy groups, amino groups, acyl groups or quaternary ammonium groups, especially a substituted —CH
2
—CH
2
— group, —CH
2
—CH
2
—CH
2
— group or —CH
2
—CH
2
—CH
2
—CH
2
— group, such as a —CH
2
—CH(OH)—CH
2
— group, the —CH
2
—CH
2
—CH
2
—CH
2
— group being particularly preferred.
Especially preferred are compounds of formula (I), in which Q
1
and Q
2
independently of one another represent the following: phenyl, biphenyl, 3-pyridyl, 4-pyridyl, C
6
H
4
R3 or C
6
H
3
R3R4, in which R3 and R4 independently of one another are F, Cl, Br, I, CN, NO
2
, CF
3
, C
1
to C
4
alkyl, C
1
to C
4
alkoxy, aryloxy, C
1
to C
4
thioalkyl or NR′R″, in which R′ and R″ independently of one another are hydrogen or a C
1
to C
4
alkyl group, or R′and R″, together with the nitrogen atom, form an aromatic or aliphatic ring with 4 to 6 atoms, which optionally contains a further nitrogen, oxygen or sulfur atom.
Of the compounds of formula (I) named above, especially those are preferred, in which Q
1
and Q
2
independently of one another are phenyl, biphenyl, C
6
H
4
R3 or C
6
H
3
R3R4, in which R3 and R4 independently of one another are F, Cl, Br, CN, C
1
to C
4
alkyl, C
1
to C
4
alkoxy, C
1
to C
4
thioalkyl or NR′R″, in which R′ and R″ independently of one another are hydrogen or a C
1
to C
4
alkyl group, or R′ and R″, together with the nitrogen atom, form an aromatic or aliphatic ring with 4 to 6 atoms, which optionally contains a further nitrogen, oxygen or sulfur atom.
In the general formula (I), A
−
preferably represents a chloride anion, a bromide anion or an iodide anion. It is, however, also possible to use, instead of a halide anion, other anions, which may be univalent as well as multivalent, such as a sulfate anion, a phosphate anion, a hydrogen phosphate anion, a carbonate anion, a bicarbonate anion, an oxalate anion, a formate anion, an acetate anion, a citrate anion, a tartrate anion, a malonate anion or a pyruvate anion, the number of anions, in the case of multivalent anions, having to be divided by the valence of the anion used. The bromide anion and the chloride anion are particularly preferred.
The following can be named as examples of suitable cationic diketo[pyrrolopyrroles of general formula (I): 2,5-bis-(4-trimethylammonium-butyl)-3,6-diphenyl-pyrrolo[3,4-c]pyrrole-1,4-dione dibromide; 2,5-bis(3-trimethyl-ammonium-propyl)-3,6-diphenyl-pyrrolo[3,4-c]pyrrole-1,4-dione dibromide; 2,5-bis(2-trimethylammonium-ethyl)-3,6-diphenyl-pyrrolo[3,4-c]-1,4-dione dibromide; 2,5-bis(2-trimethylammonium-butyl)-3,6-diphenyl-pyrrolo[3,4-c]pyrrole-1,4-dione dichloride; 2,5-bis(3-trimethylammonium-propyl)-3,6-diphenyl-pyrrolo[3,4-c]pyrrole-1,4-dione dichloride; 2,5-bis(2-trimethylammonium-ethyl)-3,6-diphenyl-pyrrolo-&lsqb
Braun Hans-Juergen
Pasquier Cecile
Wyss Patrick
McKane Joseph K.
Small Andrea D.
Striker Michael J.
Wella AG
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