Hair color compositions for mitigating color loss

Patent metadata

Field	Value
Publication number	US-2024252419-A1
Application number	US-202218562028-A
Country	US
Kind code	A1
Filing date	May 17, 2022
Priority date	May 17, 2021
Publication date	Aug 1, 2024
Grant date	—

Abstract

Hair coloring compositions for mitigating color fade and wash-out are disclosed. The composition includes at least one hair coloring agent and at least one polyurethane having tethered tertiary amino groups which are optionally partially or fully neutralized and/or quaternized. Permanent, semi-permanent, and temporary hair coloring compositions may be formulated according to the disclosed technology.

First claim

1 . A composition for coloring hair and retaining color in colored hair, said composition comprising:
a) at least one hair coloring agent; and b) at least one polyurethane comprising a polyurethane backbone with one or more tethered tertiary amino groups laterally attached to said polyurethane backbone, wherein said tethered tertiary amino groups are situated away from said polyurethane backbone by a tethering moiety containing at least two intervening atoms, and wherein said tethered tertiary amino group(s) are optionally partially or fully neutralized and/or quaternized; and wherein the at least one polyurethane comprises the reaction product of: (i) at least one polyisocyanate; (ii) at least one main chain polyamine, polyol, polythiols, and mixtures thereof having about two isocyanate reactive hydrogens; and (iii) at least one compound containing a tertiary nitrogen having two isocyanate reactive hydrogen-containing substituents and at least one tethered tertiary amino group substituent(s), wherein said tertiary amino group subtituent(s) are situated away from said tertiary nitrogen by a tethering moiety containing at least two intervening atoms.

2 . (canceled)

3 . A composition of claim 1 , wherein said reaction product is partially or fully neutralized and/or quaternized.

4 . A composition of claim 2 , wherein said partially or fully neutralized and/or quaternized reaction product is dispersed in water to form a polyurethane prepolymer dispersion, and wherein said partially or fully neutralized and/or quaternized prepolymer dispersion is chain extended with a chain extender selected from water, an inorganic or organic polyamine and/or low molecular weight polyols, and mixtures thereof.

5 . (canceled)

6 . A composition of claim 1 , wherein said a least one polyisocyanate (i) is selected from an aliphatic diisocyanate, an aromatic diisocyanate, an araliphatic diisocyanate, and mixtures thereof.

7 . A composition of claim 1 , wherein said at least one main chain polyol (ii) is selected from a polycarbonate polyol, a polyester polyol, a polyether polyol, and mixtures thereof.

8 . A composition of claim 1 , wherein said at least one compound containing a tertiary nitrogen (iii) is selected from 2,2′-((3-dimethylamino)propyl)azanediyl)bis(ethan-1-ol) and 1,1′-((3-dimethylamino)propyl)azanediyl)bis(propan-2-ol), and mixtures thereof.

9 . A composition of claim 1 , wherein the at least one polyurethane comprises the reaction product of:
(i) at least one aliphatic polyisocyanate; (ii) at least one main chain polyol having about two isocyanate reactive hydrogens selected from a polyether; and (iii) at least one compound containing a tertiary nitrogen having two isocyanate reactive hydrogen-containing substituents and at least one tethered tertiary amino group substituent, wherein said tertiary amino group is situated away from said tertiary nitrogen by a tethering moiety containing at least three intervening atoms.

10 . A composition of claim 1 , wherein said at least one polyisocyanate is an aliphatic polyisocyanate is selected from hexamethylene-1,6-diisocyanate, 1,12-dodecane diisocyanate, 2,2,4-trimethyl-hexamethylene diisocyanate, 2,4,4-trimethyl-hexamethylene diisocyanate, 2-methyl-1,5-pentamethylene diisocyanate, lysine diisocyanate, dicyclohexylmethane diisocyanate, isophorone diisocyanate, cyclohexane diisocyanate, bis-(isocyanatomethyl) cyclohexane, methylcyclohexane diisocyanate, cyclohexane triisocyanate, and mixtures thereof.

11 . A composition of claim 1 , wherein said at least one main chain polyol is selected from polytetrahydrofuran, poly(propylene glycol) derived from 1,2-propane diol, poly(propylene glycol derived from 1,3-propane diol, and mixtures thereof.

12 . (canceled)

13 . A composition of claim 1 , wherein said tethered tertiary amino groups are quaternized with a quaternizing agent selected from alkyl halides, aralkyl halides, dialkyl carbonates, dialkyl sulphates, and epoxides.

14 . A composition of claim 1 , wherein at least 25% of said tethered tertiary amino groups are neutralized and/or quaternized.

15 . A composition of claim 1 , wherein the at least one polyurethane comprises the reaction product of at least one cycloaliphtic diisocyanate, at least one polyether polyol, and at least one tethered tertiary amino group monomer containing two active hydrogen groups, wherein said tertiary amino groups are neutralized with an acid.

16 . A composition of claim 1 , wherein the at least one polyurethane comprises the reaction product of a first cycloaliphtic diisocyanate, a second cycloaliphatic diisocyanate different from the first cycloaliphatic diisocyanate, at least one polyether polyol, and at least one tethered tertiary amino group containing two active hydrogen groups, wherein said tertiary amino groups are neutralized with an acid.

17 . A composition of claim 1 , wherein the at least one polyurethane comprises the reaction product of dicyclohexylmethane diisocyanate (H 12 MDI) and isophorone diisocyanate (IPDI), polytetrahydrofuran, at least one tethered tertiary amino group selected from 2,2′-((3-dimethylamino)propyl)azanediyl)bis(ethan-1-ol) and 1,1′-((3-dimethylamino)propyl)azanediyl)bis(propan-2-ol), and mixtures thereof, wherein said tertiary amino groups are neutralized with an acid.

18 . (canceled)

19 . A composition of claim 1 , wherein said at least one polyurethane is a polyurethane dispersion (PUD).

20 . A composition of claim 1 , wherein said hair coloring agent is a temporary hair dye.

21 . A composition of claim 1 , wherein said hair coloring agent is a semi-permanent hair dye.

22 . A composition of claim 1 , wherein said hair coloring agent comprises at least one permanent hair dye component in an amount ranging from about 0.0005 to about 20 wt. %.

23 . (canceled)

24 . A composition of claim 22 , wherein said permanent hair dye component comprises at least one oxidative dye precursor.

25 . A composition of claim 22 , wherein said permanent hair dye component comprises a dye coupler in an amount ranging from about 0.0001 to about 15 wt. % based on the total weight of the composition.

26 . (canceled)

27 . A composition of claim 22 , wherein said permanent hair dye component comprises at least one direct dye in an amount ranging from about 0.0001 to about 20 wt. % based on the total weight of the composition.

28 . (canceled)

29 . A composition of claim 22 , wherein said permanent hair dye component comprises at least one alkalizing agent in an amount sufficient to maintain a pH ranging from about 7 to about 12.

30 . (canceled)

31 . A composition of claim 22 , wherein said permanent hair dye component comprises at least one reducing agent in an amount ranging from about 0.0005 to about 6 wt. % based on the total weight of the composition.

32 . (canceled)

33 . A composition of claim 22 , wherein said permanent hair dye component is mixed with at least one oxidizing agent, wherein said at least one oxidizing agent is present in an amount ranging from about 0.0001 to about 25 wt. % based on the total weight of the composition.

34 . (canceled)

35 . (canceled)

36 . A composition of claim 1 , comprising at least one a

Assignees

• Lubrizol Advanced Mat Inc

Inventors

• Askar Narjis A
• Lubnin Alexander V
• Dame Tina R
• Xavier Jean H

Classifications

• A61Q5/065

  Preparations for temporary colouring the hair, e.g. direct dyes · CPC title

• A61K8/86

  Polyethers · CPC title

• A61K8/87 Primary

  Polyurethanes · CPC title

• A61K2800/48

  Thickener, Thickening system · CPC title

• A61K2800/5426

  cationic · CPC title