IP Library Granted Patent US 7,776,106
Granted Patent B2
US 7,776,106 · App. 12/279,003 · Granted Aug 17, 2010

Dyestuffs and hair dye compositions

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Quick Facts
Patent No.
US 7,776,106
App. No.
12/279,003
Granted
Aug 17, 2010
Kind
B2
Abstract

The present invention refers to dyestuffs of the general Formula (I) wherein R, X, Y and Z are defined as given in claim 1, dyestuff mixtures and hair dye compositions comprising them, as well as a process for coloring hair.

Claims (34)

1. A mixture comprising one or more dyestuffs of of formula (I)

wherein

R is hydrogen, alkyl, alkyl substituted by Q, aryl, Q-aryl, —OR 2 , —SR 3 or —NR 5 R 4 , hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl, cycloalkyl substituted by Q, aryl substituted by R 10 , Q, R 11 O-alkyl, —OR 12 , —SR 13 , —NR 14 R 15 , —CONR 15 R 16 , —C(O)OR 17 , —SO 2 —NR 18 R 19 , —SO 2 OR 20 , —C(O)R 21 or —SO 2 R 22 , —C(O)R 6 , —SO 2 NR 7 R 8 or —SO 2 R 9 ;

X is hydrogen, —OR 23 , —SR 24 , —NR 25 R 26 , —SO 2 NR 27 R 28 , —CONR 29 R 30 , —SO 2 R 31 , —C(O)OR 32 , —C(O)R 33 , —SO 2 R 34 , alkyl, alkyl substituted by —OR 200 , —SR 300 or —NR 500 R 400 , aryl substituted by R 100 , R 110 O-alkyl, —OR 120 , —SR 130 , —NR 140 R 150 , —CONR 150 R 160 , —C(O)OR 170 , —SO 2 —NR 180 R 190 , —SO 2 OR 201 , —C(O)R 210 or —SO 2 R 220 ,

—NHSO 2 R 37 , —CHO, —CH═NR 35 or NO 2 ;

Y is hydrogen, —NR 51 R 52 , —OR 53 , —SR 54 , —SO 2 NHR 55 , —NHC(O)R 56 , —SO 2 OR 57 , —NHSO 2 R 58 , —SO 2 R 59 , —NHSO 2 NR 60 R 61 , halogen or NO 2 ;

Z is hydrogen, —NR 51 R 52 , —OR 53 , —SR 54 , —SO 2 NHR 55 , —NHC(O)R 56 , —SO 2 OR 57 , —NHSO 2 R 58 , —SO 2 R 59 , —NHSO 2 NR 60 R 61 , halogen or NO 2 ;

each of R 2 to R 8 R 60 and R 61 , independently, is hydrogen, alkyl, alkyl substituted by Q, aryl, aryl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl substituted by Q;

R 9 is alkyl, alkyl substituted by Q, aryl, aryl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl substituted by Q;

each of R 10 to R 16 , R 18 , R 19 and R 21 , independently, is hydrogen, alkyl, alkyl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl substituted by Q;

each of R 17 , R 20 and R 22 , independently, is alkyl, alkyl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl substituted by Q;

each of R 23 to R 30 and R 35 , independently, is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, cycloalkyl or cycloalkyl substituted by —C(O)R 6 , —SO 2 R 9 , or aryl substituted by R 10′ , R 11′ O-alkyl, —OR 12′ , —SR 13′ , —NR 14′ R 15′ , —CONR 15′ R 16′ , —C(O)OR 17′ , SO 2 —NR 18′ R 19′ , —SO 2 OR 20′ , —C(O)R 21′ or —SO 2 R 22′ ;

R 6 is hydrogen, alkyl, aryl, hydroxyalkyl, polyhydroxyalkyl or cycloalkyl;

R 9 is alkyl, aryl, hydroxyalkyl, polyhydroxyalkyl or cycloalkyl;

each of R 10′ to R 16′ , R 18′ , R 19′ and R 21′ , independently, is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl or cycloalkyl;

each of R 17′ , R 20′ and R 22′ , independently, is alkyl, hydroxyalkyl, polyhydroxyalkyl or cycloalkyl;

each of R 36 and R 37 , independently, is alkyl, aryl, hydroxyalkyl, polyhydroxyalkyl or cycloalkyl and one of R 36 and R 37 can additionally be hydrogen; each of R 51 to R 54 , independently, is hydrogen, alkyl, alkyl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl

substituted by Q, —C(O)R 6 , —SO 2 R 9 or aryl substituted by R 10 , R 11 O-alkyl, —OR 12 , SR 13 , —NR 14 R 15 , —CONR 15 R 16 , —C(O)OR 17 , —SO 2 —NR 18 R 19 , —SO 2 OR 20 , —C(O)R 21 or —SO 2 R 22 ;

each of R 31 to R 33 , independently, is alkyl, hydroxyalkyl, polyhydroxyalkyl, cycloalkyl or aryl substituted by R 10′ , R 11′ O-alkyl, —OR 12′ , —SR 13′ , —NR 14′ R 15′ , —CONR 15′ R 16′ , —C(O)OR 17′ , —SO 2 —NR 18′ R 19′ , —SO 2 R 20′ , —C(O)R 21′ or —SO 2 R 22′ , and R 33 can additionally be hydrogen;

R 34 is alkyl, hydroxyalkyl, polyhydroxyalkyl, cycloalkyl or aryl substituted by R 10′ , R 11′ O-alkyl, —OR 12′ , —SR 13′ , —NR 14′ R 15′ , —CONR 15′ R 16′ , —C(O)OR 17′ , SO 2 —NR 18′ R 19′ , —SO 2 OR 20′ , —C(O)R 21′ or —SO 2 R 22′ ;

each of R 55 to R 57 , independently, is hydrogen, alkyl, alkyl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl substituted by Q or aryl substituted by R 10 , R 11 O-alkyl, —OR 12 , —SR 13 , —NR 14 R 15 , —CONR 15 R 16 , —C(O)OR 17 , —SO 2 —NR 18 R 19 , —SO 2 OR 20 , —C(O)R 21 or —SO 2 R 22 , and R 55 and R 56 can additionally be hydrogen;

each of R 58 and R 59 , independently, is alkyl, alkyl substituted by Q, hydroxyalkyl, hydroxyalkyl substituted in the alkyl group by Q, polyhydroxyalkyl, polyhydroxyalkyl substituted in the alkyl group by Q, cycloalkyl or cycloalkyl substituted by Q or aryl substituted by R 10 , R 11 O-alkyl, —OR 12 , —SR 13 , —NR 14 R 15 , —CONR 15 R 16 , —C(O)OR 17 , —SO 2 —NR 18 R 19 , —SO 2 OR 20 , —C(O)R 21 or —SO 2 R 22 ;

each of R 200 , R 300 R 400 and R 500 , independently, is hydrogen, alkyl, aryl, hydroxyalkyl, polyhydroxyalkyl or cycloalkyl; each of R 100 , R 110 , R 120 , R 130 , R 140 , R 150 , R 150 , R 180 , R 190 and R 210 independently, is hydrogen, alkyl, hydroxyalkyl, polyhydroxyalkyl, or cycloalkyl;

each of R 170 , R 201 , and R 220 , independently, is alkyl, hydroxyalkyl, polyhydroxyalkyl, or cycloalkyl; and

Q is a group of formula (II)

wherein each of R′, R″ and R′″, independently, is (C 1 -C 6 )-alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, heteroaryl, heteroarylalkyl, heterocycloalkyl, heterocycloalkyl-alkyl, either of which can be substituted by a heteroatom comprising groups or R′ and R″ form together with the nitrogen to which they are bonded a 5- or 6- membered satureated heterocyclic ring; and

A − is a cosmetically acceptable, water solubilizing anion, and does not comprise arylsulfonate, phosponate and alkylphosphonate;

whereby the dyestuff of the formula (I) comprises exactly one group Q;

whereby at least two of the groups X, Y and Z are groups other than hydrogen; and whereby in case R and X are both hydrogen and Y is —NR 51 R 52 or —OR 23 , wherein R 51 , R 52 and R 23 are hydrogen, Z is not —NR 25 R 26 , wherein one of R 25 and R 26 is hydrogen and the other is alkyl substituted by Q.

2. A hair dye composition comprising one or more dyestuffs of formulae (I) according to claim 1 or a mixture comprising one or more dyestuffs of formula (I) and one or more direct or oxidation dyestuff.

3. The hair dye composition according to claim 2 which further comprises at least one oxidative dye precursor, at least one coupling compound, or a combination thereof.

4. The hair dye composition according to claim 2 which comprises an oxidizing agent.

5. The hair dye composition according to claim 2 which has a pH value in the range of 2 to 11.

6. A process for colouring hair comprising: (1) applying the hair dye composition according to claim 2 onto hair for 1 to 45 minutes, and (2) rinsing off said hair dye composition from said hair.

Assignments (3)
MERGER Recorded Jun 26, 2012
From: DYSTAR COLOURS DEUTSCHLAND GMBH
To: DYSTAR COLOURS DISTRIBUTION GMBH
Reel/Frame 028440/0305 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 16, 2010
From: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG
To: DYSTAR COLOURS DEUTSCHLAND GMBH
Reel/Frame 024990/0859 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 8, 2008
From: BARBIERU, ROXANA; RUSS, WERNER; PRATT, DOMINIC; MOEHRING, HARTMUT
To: DYSTAR TEXTILFARBEN GMBH & CO. DEUTSCHLAND KG; KAO CORPORATION
Reel/Frame 021938/0928 →