IP Library Granted Patent US 8,632,612
Granted Patent B2
US 8,632,612 · App. 13/818,317 · Granted Jan 21, 2014

Compositions for dyeing keratin fibers

Inventor: Dorie J. Yontz (Bloomington, MN)
Assignee: Segetis, Inc.
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Quick Facts
Patent No.
US 8,632,612
App. No.
13/818,317
Granted
Jan 21, 2014
Kind
B2
Abstract

Disclosed herein are compositions for dyeing keratin fibers, methods of manufacture thereof and articles comprising the same.

Claims (47)

1. A keratin fiber dyeing composition comprising:

at least one colorant,

at least one solvent, and

a ketal adduct of formula (I)

wherein

R 1 is C 1-6 alkyl,

R 2 is hydrogen or C 1-3 alkyl,

each R 3 , R 4 , and R 5 is independently hydrogen or C 1-6 alkyl,

R 6 is hydrogen or C 1-6 alkyl, or hydroxymethyl,

R 7 is hydrogen, C 1-6 alkyl, C 1-6 alkyl substituted with up to four OR 8 groups wherein R 8 is hydrogen, C 1-6 alkyl, or acetyl,

a is 0-3, and

b is 0-1.

2. The composition of claim 1 , wherein R 1 is C 1-6 straight chain or branched alkyl, R 2 is methyl, each R 3 , R 4 , and R 5 is independently hydrogen or C 1-3 alkyl, R 6 is hydrogen, C 1-3 alkyl, or hydroxymethyl, R 7 is hydrogen, C 1-3 alkyl, or C 1-4 alkyl substituted with up to four —OR 8 groups wherein R 8 is hydrogen or a C 1-3 alkyl group, a is 1-3, and b is 0-1.

3. The composition of claim 1 , wherein each R 1 and R 4 is independently C 1-6 straight chain or branched alkyl, each R 2 and R 3 is independently hydrogen or C 1-3 alkyl, each R 6 , R 7 , R 10 , and R 11 is independently hydrogen, C 1-4 alkyl, C 1-6 hydroxyalkylene, or C 1-6 alkyl substituted with up to four hydroxy groups, each R 8 and R 9 is independently hydrogen, hydroxyl, C 1-4 alkyl, or C 1-4 hydroxyalkyl, a is 1-3, and b is 0-1.

4. The composition of claim 1 , wherein R 1 is C 1-4 alkyl, R 2 is methyl, R 3 is hydrogen, R 6 is hydrogen, C 1-3 alkyl, or hydroxymethyl, R 7 is hydrogen, C 1-3 alkyl, or C 1-4 alkyl substituted with up to four —OR′ groups wherein R 8 is hydrogen or a C 1-3 alkyl group, a is 2-3, and b is 0.

5. The composition of claim 1 , wherein R 1 is C 1-4 alkyl or acetyl, R 2 is methyl, R 3 is hydrogen, R 6 is hydrogen, methyl, ethyl, or —CH 2 OH, R 7 is methyl, ethyl, —CH 2 OH, —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , —CH(OH)CH 2 OH, or —(CH(OH)) 3 CH 2 OH, a is 2, and b is 0.

6. The composition of claim 1 , wherein the ketal adduct is of formula (1a):

wherein R 1 is a C 1-4 alkyl, and R 9 is hydrogen or C 1-4 alkyl.

7. The composition of claim 1 , wherein the ketal adduct is of formula (1b)

wherein R 1 is a C 1-4 alkyl.

8. The composition of claim 1 , wherein the solvent is water, alcohol, glycol, or mixtures thereof.

9. The composition of claim 1 , wherein the solvent is water, ethanol, propanol, butanol, isopropylalcohol, benzyl alcohol, butoxydiglycol, 1,2 propane diol, 1,3 propane diol, ethoxydiglycol, hexylene glycol, and dipropylene glycol, triethylene glycol, hexylene glycol, diethylene glycol, ethylene glycol, 1,3-butylene glycol, or 1,2-butylene glycol.

10. The composition of claim 1 , further comprising a cosolvent.

11. The composition of claim 10 , wherein the cosolvent is different from the solvent and is water, ethanol, propanol, butanol, isopropylalcohol, benzyl alcohol, butoxydiglycol, 1,2 propane diol, 1,3 propane diol, ethoxydiglycol, hexylene glycol, and dipropylene glycol, triethylene glycol, hexylene glycol, diethylene glycol, ethylene glycol, propylene glycol, 1,3-butylene glycol, or 1,2-butylene glycol.

12. The composition of claim 1 , further comprising at least one component selected from at least one oxidizing agent, at least one carbonate ion source, at least one alkalizing agent, at least one pH buffer, at least one radical scavenger, at least one surfactant, at least one gel network thickener, at least one polymer, at least one conditioning agent, at least one chelant, or at least one auxiliary agent.

13. The composition of claim 12 , wherein the at least one auxiliary agent is an amino acid, a protein, a cationic conditioner, a cationic polymer, a wax, an antioxidant, a vitamin, an alpha hydroxy acid, a beta hydroxy acid, an alpha ketoacid, an antibacterial agent, a preservative, a perfume, a sequestering agent, an anti-dandruff agent, a botanical extract, a skin protectant, or mixtures thereof.

14. A keratin fiber dyeing composition comprising:

at least one hair colorant and

a ketal adduct of formula (1)

wherein

R 1 is C 1-6 straight chain or branched alkyl,

R 2 is hydrogen or C 1-3 alkyl,

each R 3 , R 4 , and R 5 is independently hydrogen or C 1-6 straight chain or branched alkyl,

R 6 is hydrogen or C 1-6 straight chain or branched alkyl, or hydroxymethyl,

R 7 is hydrogen, C 1-6 straight chain or branched alkyl, C 1-6 alkyl substituted with up to four OR 8 groups wherein R 8 is hydrogen, C 1-6 straight chain or branched alkyl, or acetyl,

a is 0-3, and

b is 0-1.

15. The composition of claim 14 , wherein R 1 is C 1-6 alkyl, R 2 is methyl, each R 3 , R 4 , and R 5 is independently hydrogen or C 1-3 alkyl R 6 is hydrogen, C 1-3 alkyl, or hydroxymethyl, R 7 is hydrogen, C 1-3 alkyl, or C 1-4 alkyl substituted with up to four —OR 8 groups wherein R 8 is hydrogen or a C 1-3 alkyl group, a is 1-3, and b is 0-1.

16. The composition of claim 14 , wherein each R 1 and R 4 is independently C 1-6 alkyl, each R 2 and R 3 is independently hydrogen or C 1-3 alkyl, each R 6 , R 7 , R 10 , and R 11 is independently hydrogen, C 1-4 alkyl, C 1-6 hydroxyalkylene, or C 1-6 alkyl substituted with up to four hydroxy groups, each R 8 and R 9 is independently hydrogen, hydroxyl, C 1-4 alkyl, or C 1-4 hydroxyalkyl, a is 1-3, and b is 0-1.

17. The composition of claim 14 , wherein R 1 is C 1-4 alkyl, R 2 is methyl, R 3 is hydrogen, R 6 is hydrogen, C 1-3 alkyl, or hydroxymethyl, R 7 is hydrogen, C 1-3 alkyl, or C 1-4 alkyl substituted with up to four —OR′ groups wherein R 8 is hydrogen or a C 1-3 alkyl group, a is 2-3, and b is 0.

18. The composition of claim 14 , wherein R 1 is C 1-4 alkyl or acetyl, R 2 is methyl, R 3 is hydrogen, R 6 is hydrogen, methyl, ethyl, or —CH 2 OH, R 7 is methyl, ethyl, —CH 2 OH, —CH 2 OCH 3 , —CH 2 OCH 2 CH 3 , —CH(OH)CH 2 OH, or —(CH(OH)) 3 CH 2 OH, a is 2, and b is 0.

19. The composition of claim 14 , wherein the ketal adduct is of formula (1a):

wherein R 1 is a C 1-4 alkyl, and R 9 is hydrogen or C 1-4 alkyl.

20. The composition of claim 14 , wherein the ketal adduct is of formula (1b)

wherein R 1 is a C 1-4 alkyl.

21. The composition of claim 14 , further comprising at least one component selected from at least one oxidizing agent, at least one carbonate ion source, at least one alkalizing agent, at least one pH buffer, at least one radical scavenger, at least one surfactant, at least one gel network thickener, at least one polymer, at least one conditioning agent, at least one chelant, or at least one auxiliary agent.

22. The composition of claim 21 , wherein the at least one auxiliary agent is an amino acid, a protein, a cationic conditioner, a cationic polymer, a wax, an antioxidant, a vitamin, an alpha hydroxy acid, a beta hydroxy acid, an alpha ketoacid, an antibacterial agent, a preservative, a perfume, a sequestering agent, an anti-dandruff agent, or mixtures thereof.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 7, 2016
From: SEGETIS, INC.
To: GFBIOCHEMICALS LIMITED
Reel/Frame 038373/0362 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 1, 2013
From: YONTZ, DORIE J.
To: SEGETIS, INC.
Reel/Frame 029902/0096 →
Continuity (2)
Provisional Application 61380518 · Sep 7, 2010
Related Publication 20130156716A1 · Jun 20, 2013