IP Library Granted Patent US 7,553,336
Granted Patent B2
US 7,553,336 · App. 10/585,032 · Granted Jun 30, 2009

Brightening direct dyes for keratin fibers and colorants containing these compounds

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Quick Facts
Patent No.
US 7,553,336
App. No.
10/585,032
Granted
Jun 30, 2009
Kind
B2
Abstract

The present invention has for an object brightening cationic naphthalene dyes of formula (I) and colorants for keratin fibers, particularly human hair, containing these compounds

Claims (11)

1. A cationic naphthalene derivative selected from the group consisting of 4-{(E)-[(1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-(2-hydroxyethyl)pyridinium bromide, 4-{[(E)-[2-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-(1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-methylpyridinium methylsulfate, 1-(2-hydroxyethyl)-4-{(E)-(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)iminomethyl}pyridinium bromide, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}pyridinium methylsulfate, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}quinolinium methylsulfate, 4-[(E)-({2-[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}imino)methylpyridinium methylsulfate, 4-((E)-{[2-(3,4-dichlorophenyl)-1,3-diketo-2,3-dihydro-1 H-benzo[de]isoquinolin-6-yl]imino}methyl)-1-(2-hydroxyethyl)pyridinium bromide and 2-[(E)-({2-[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}imino)methyl]-3-methyl-1,3-thiazol-3-ium methylsulfate.

2. The cationic naphthalene derivative as defined in claim 1 , selected from the group consisting of 4-{[(E)-[1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-(2-hydroxyethyl)pyridinium bromide, 1-(2-hydroxyethyl)-4{(E)-[2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)iminomethyl}pyridinium bromide, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}pyridinium methylsulfate and 1-methyl-4-{(E)-[2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}quinolinium methylsulfate.

3. An agent for coloring keratin fibers, comprising at least one cationic naphthalene derivative selected from the group consisting of 4-{(E)-[(1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-(2-hydroxyethyl)pyridinium bromide, 4-{[(E)-[2-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-( 1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-methylpyridinium methylsulfate, 1-(2-hydroxyethyl)-4-{(E)-(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)iminomethyl}pyridinium bromide, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}pyridinium methylsulfate, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}quinolinium methylsulfate, 4-[(E)-({2-[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}imino)methylpyridinium methylsulfate, 4-((E)-{2-(3,4-dichlorophenyl)-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-y]imino}methyl)-1-(2-hydroxyethyl)pyridinium bromide, and 2-[(E)-({2-[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}imino)methyl]-3-methyl-1,3-thiazol-3-ium methylsulfate.

4. An agent for brightening and coloring keratin fibers, comprising at least one cationic naphthalene derivative selected from the group consisting of 4-{(E)-[(1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-(2-hydroxyethyl)pyridinium bromide, 4-{[(E)-[2-{4-[ethyl(2-hydroxyethyl)amino]phenyl}-(1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}-1-methylpyridinium methylsulfate, 1-(2-hydroxyethyl)-4-{(E)-(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)iminomethyl}pyridinium bromide, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}pyridinium methylsulfate, 1-methyl-4-{(E)-[(2-methyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl)imino]methyl}quinolinium methylsulfate, 4-[(E)-({2-[2-hydroxy-1-(hydroxymethyl)ethyl-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}imino)methylpyridinium methylsulfate, 4-((E)-}[2-(3,4-dichlorophenyl)-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl]imino}methyl)-1-(2-hydroxyethyl)pyridinium bromide, and 2-[(E)-({2-[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-diketo-2,3-dihydro-1H-benzo[de]isoquinolin-6-yl}imino)methyl]-1,3-methyl-1,3-thiazol-3-ium methylsulfate.

5. The agent as defined in claim 3 , wherein the agent contains the cationic naphthalene derivative in an amount from 0.01 to 10 weight percent.

6. The agent as defined in claim 3 , further comprising at least one synthetic polymer or a modified polymer of natural origin commonly used in cosmetic agents.

7. The agent as defined in claim 6 , wherein the agent contains the polymer in an amount from 1 to 5 weight percent.

8. The agent as defined in claim 3 , wherein the agent is a hair colorant.

9. The agent as defined in claim 4 , wherein the agent contains the cationic naphthalene derivative in an amount from 0.01 to 10 weight percent.

10. The agent as defined in claim 4 , and further comprising at least one synthetic polymer or a modified polymer of natural origin commonly used in cosmetic agents.

11. The agent as defined in claim 10 , wherein the agent contains the polymer in an amount from 1 to 5 weight percent.

Assignments (6)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE EXECUTION DATE PREVIOUSLY RECORDED AT REEL: 055344 FRAME: 0422. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 29, 2021
From: HFC PRESTIGE INTERNATIONAL HOLDING SWITZERLAND SÀRL
To: HFC PRESTIGE INTERNATIONAL OPERATIONS SWITZERLAND SÀRL
Reel/Frame 056712/0333 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 26, 2021
From: HFC PRESTIGE INTERNATIONAL OPERATIONS SWITZERLAND SARL
To: WELLA INTERNATIONAL OPERATIONS SWITZERLAND SARL
Reel/Frame 055428/0174 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 19, 2021
From: HFC PRESTIGE INTERNATIONAL HOLDING SWITZERLAND SÀRL
To: HFC PRESTIGE INTERNATIONAL OPERATIONS SWITZERLAND SÀRL
Reel/Frame 055344/0422 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 19, 2016
From: WELLA GMBH
To: HFC PRESTIGE INTERNATIONAL HOLDING SWITZERLAND S.A.R.L
Reel/Frame 040420/0478 →
CHANGE OF NAME Recorded Nov 16, 2011
From: WELLA AG
To: WELLA GMBH
Reel/Frame 027240/0338 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 29, 2006
From: SPECKBACHER, MARKUS; BRAUN, HANS-JUERGEN
To: WELLA AG
Reel/Frame 018035/0386 →