Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2002-10-21
2004-03-02
Ramsuer, Robert W. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C008S409000, C008S410000, C008S408000, C546S221000, C546S300000, C546S307000, C546S308000, C546S309000, C548S338100, C548S372100, C548S537000, C548S540000, C548S550000, C549S439000, C549S493000, C560S312000, C562S450000, C564S163000
Reexamination Certificate
active
06699990
ABSTRACT:
BACKGROUND OF THE INVENTION
The invention relates to novel 3-(2,5-diaminophenyl)acrylamide derivatives and to dyeing agents for keratin fibers containing these compounds.
In the area of keratin fiber dyeing, particularly hair dyeing, oxidation dyes have attained substantial importance. In this case, the coloration is produced by reaction of certain developers with certain couplers in the presence of an appropriate oxidant. Suitable developers are, in particular, 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol, 1,4-diaminobenzene and 4,5-diamino-1-(2-hydroxyethyl)pyrazole, and suitable couplers are, for example, resorcinol, 2-methylresorcinol, 1-naphthol, 3-aminophenol, m-phenylenediamine, 2-amino-4-(2′-hydroxyethyl)aminoanisole, 1,3-diamino-4-(2′-hydroxyethoxy)benzene and 2,4-diamino-5-fluorotoluene.
To cover the important blond range, direct aromatic nitro dyes, in particular, were heretofore added to the oxidative hair colorants.
The use of substituted p-phenylenediamines as dye components in oxidative hair colorants is known from the literature, for example from German Unexamined Patent Application DE 198 22 041, Unexamined European Patent Applications EP 0 634 163 and EP 0 819 424, German Unexamined Patent Application 39 17 304 and European Unexamined Patent Application 0 007 537. These compounds, however, do not meet the requirements placed on dyes for oxidative colorants for the blond range in all respects. Hence, the need for suitable novel dyes continued to exist.
SUMMARY OF THE INVENTION
We have now found; that certain p-phenylenediamine derivatives together with the usual couplers make it possible to achieve an intense blond coloration of fibers, particularly keratin fibers, for example hair. By use of these p-phenylenediamine derivatives in an oxidizing medium, intense color shades are thus obtained which are unusually light-fast and wash-fast.
Hence, the object of the present invention are 3-(2,5-diaminophenyl)acrylamide derivatives of general formula (I) or their physiologically tolerated, water-soluble salts
wherein
R1, R2, R3 and R4 can be equal or different and independently of each other denote hydrogen, a C
1
-C
6
-alkyl group, a C
2
-C
4
-hydroxyalkyl group or a C
3
-C
4
-dihydroxyalkyl group or R1 and R2 or R3 and R4 form a four-membered to eight-membered aliphatic ring and at least two of the R1 to R4 groups denote hydrogen;
R5 denotes hydrogen, a halogen atom (F, Cl, Br, I), a C
1
-C
4
-alkyl group, a C
1
-C
4
-hydroxyalkyl group or a C
1
-C
4
-alkoxy group;
R6 and R7 can be equal or different and independently of each other denote hydrogen, a C
1
-C
2
-alkoxy, C
1
-C
6
-alkyl, unsaturated C
3
-C
6
-alkyl, C
2
-C
4
-hydroxyalkyl, C
3
-C
4
-dihydroxyalkyl, C
2
-C
4
-aminoalkyl, C
2
-C
4
-dimethylaminoalkyl, C
2
-C
4
-acetylaminoalkyl, C
2
-C
4
-methoxyalkyl, C
2
-C
4
-ethoxyalkyl, C
1
-C
4
-cyanoalkyl, C
1
-C
4
-carboxyalkyl, C
2
-C
4
-aminocarbonylalkyl group, a pyridylmethyl, furfuryl, hydrogenated furfuryl, substituted pyridyl group, a group of formula (II)
a group of formula (III)
or a group of formula (IV)
or R6 and R7 form a ring of formula
R8, R9 and R21 can be equal or different and independently of each other denote hydrogen or a C
1
-C
6
-alkyl group;
R10 denotes hydrogen, a carboxy group or an aminocarbonyl group;
R11 and R12 can be equal or different and independently of each other denote hydrogen, a hydroxyl, aminocarbonyl, methylthiomethyl group, a phenyl- or hydroxyl-substituted phenyl group or a group of formula
R13, R14, R15, R16 and R17 can be equal or different and independently of each other denote hydrogen. a halogen atom (F, Cl, Br, I), a cyano group, a hydroxyl, C
1
-C
4
-alkoxy, C
1
-C
4
-hydroxyalkoxy, C
1
-C
6
-alkyl, C
1
-C
4
-alkyl thioether, mercapto, nitro, amino, alkylamino, hydroxyalkylamino, dialkylamino, di(hydroxyalkyl)amino, (dihydroxyalkyl)amino, (hydroxyalkyl)alkylamino, trifluoromethane, —C(O)H, —C(O)CH
3
, —C(O)CF
3
, —Si(CH
3
)
3
, C
1
-C
4
-hydroxyalkyl or C
2
-C
4
-dihydroxyalkyl group or two adjacent R13 to R17 groups together form an —O—CH
2
—O— bridge;
R18 denotes a C
1
-C
4
-alkyl, benzyl or C
1
-C
4
-hydroxyalkyl group;
R19 denotes hydrogen or a C
1
-C
6
-alkyl group, and
R20 denotes hydrogen, a hydroxyl, carboxy, aminocarbonyl or hydroxymethyl group.
Noteworthy among compounds of formula (I) are, for example:
3-(2,5-diaminophenyl)-N-methylacrylamide, 3-(2,5-diaminophenyl)-N-propylacrylamide, 3-(2,5-diaminophenyl)-1-morpholin-4-ylpropenone, 3-(2,5-diaminophenyl)-N-(1-hydroxymethylpropyl)acrylamide, 3-(2,5-diaminophenyl)-N-furan-2-ylmethylacrylamide, 3-(2,5-diaminophenyl)-N-methoxy-N-methylacrylamide, 3-(2,5-diaminophenyl)-N-(2-hydroxy-1-methylethyl)acrylamide, N-(2-aminoethyl)-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-(tetrahydrofuran-2-ylmethyl)acrylamide, N-cyclopropyl-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-isopropylacrylamide, 3-(2,5-diaminophenyl)-N-(2-methoxyethyl)acrylamide, 3-(2,5-diaminophenyl)-1-(4-hydroxypiperidin-1-yl)propenone, N-(2-acetylaminoethyl)-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-(2-morpholin-4-ylethyl)acrylamide, 3-(2,5-diaminophenyl)-N-[3-(2-ketopyrrolidin-1-yl)propyl]acrylamide, 2-[3-(2,5-diaminophenyl)acryloylamino]-3-methylbutyric acid, [3-(2,5-diaminophenyl)acryloylamino]acetic acid, N-allyl-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-[2-(5-nitropyridin-2-ylamino)ethyl]acrylamide, 3-(2,5-diaminophenyl)-N-(3-imidazol-1-ylpropyl)acrylamide, 3-(2,5-diaminophenyl)-N-[2-(3H-imidazol-4-yl)ethyl]acrylamide, N-(4-aminophenyl)-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-[2-(4-sulfamoylphenyl)ethyl]acrylamide, N-[5-chloro-4-(2-hydroxyethylamino)-2-nitrophenyl]-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-1-pyrrolidin-1-ylpropenone, 3-(2,5-diaminophenyl)-N-pyridin-2-ylacrylamide, N-[3-(2,5-diaminophenyl)-2-propenoyl]-L-glutamic acid trifluoroacetate, N2-[3-(2,5-diaminophenyl)-2-propenoyl]-glutamine trifluoroacetate, N-[4-amino-2-(2-hydroxyethyl)-2H-pyrazol-3-yl]-3-(2,5-diaminophenyl)acrylamide, N-(4-amino-2(3)-methylphenyl)-3-(2,5-diaminophenyl)acrylamide, N-[4-amino-2(3)-(2-hydroxyethyl)phenyl]-3-(2,5-diaminophenyl)acrylamide, N-{4-[bis-(2-hydroxyethyl)amino]phenyl}-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-(4-hydroxyphenyl)acrylamide, 3-(2,5-diaminophenyl)-N-(3-hydroxy-4-methylphenyl)acrylamide, N-(3-aminophenyl)-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridinylmethyl)acrylamide, 3-(2,5-diaminophenyl)-N-(2-hydroxy-5-nitrophenyl)acrylamide, N-(3-chloro-2-hydroxy-5-nitrophenyl)-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-di-aminophenyl)-1-(2-hydroxymethyl-1-pyrrolidinyl)propenone, 3-(2,5-diaminophenyl-1-(3-hydroxy-1-pyrrolidinyl)propenone, 1-[3-(2,5-diaminophenyl)acryloyl]pyrrolidine-2-carboxamide, 3-(2,5-diaminophenyl)-1-(3-hydroxy-1-piperidinyl)propenone, 3-(2,5-diaminophenyl)-N-(2-hydroxy-1-hydroxymethylethyl)acrylamide, N-(1-carbamoyl-2-hydroxyethyl)-3-(2,5-diaminophenyl)acrylamide, N-[3-(2,5-diaminophenyl)-2-propenoyl]-L-aspartic acid, N2-[3-(2,5-diaminophenyl)-2-propenoyl]-L-asparagine, N-[3-(2,5-diaminophenyl)-2-propenoyl]-L-leucine, N-[5-amino-2(4)-2-hydroxyethoxy)phenyl]-3-(2,5-diaminophenyl)acrylamide, 3-(2,5-diaminophenyl)-N-ethylacrylamide, N-benzo[1,3]dioxol-5-yl-3-(2,5-diaminophenyl)acrylamide, 2-[3-(2,5-diaminophenyl)acryloylamino]-4-methylpentanoic acid, 3-(2,5-diaminophenyl)-1-(6,7-dihydroxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl)propenone, N-(4-aminophenyl)-3-(N
2
,N
2
-bis-methyl-2,5-diaminophenyl)acrylamide, N-(4-aminophenyl)-3-(N
5
,N
5
-bis-methyl-2,5-diaminophenyl)acrylamide, N-(4-aminophenyl)-3-[N
2
,N
2
-bis-(2-hydroxyethyl)-2,5-diaminophenyl]acrylamide, N-(4-aminophenyl)-3-[N
5
,N
5
-bis-(2-hydroxyethyl)-2,5-diaminophenyl]acrylamide, N-(4-aminoph
Braun Hans-Juergen
Chassot Laurent
Ramsuer Robert W.
Striker Michael J.
Wella Aktiengesellschaft
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