Methods, compositions and uses relating thereto

Abstract

A method of combatting colour loss from a dyed material, the method comprising contacting the material with a composition comprising an alpha-substituted aldehyde.

Claims

1. A method of inhibiting or preventing solvent-mediated leaching of dye from a dyed material, the method comprising contacting the material with a composition comprising an alpha-substituted aldehyde of formula (II): ##STR00007## wherein X is selected from the group consisting of OH, O(CH.sub.2).sub.nA, Cl, Br, and F wherein n is from 1-6; A is H or OH; and R is an unsubstituted alkyl or alkenyl group having 1-30 carbon atoms.

2. The method according to claim 1 wherein the material is a keratinous material.

3. The method according to claim 2 wherein the material is human hair or animal hair.

4. The method according to claim 3 wherein the material is growing human hair or animal hair.

5. The method or composition according to claim 1 wherein the composition comprising the alpha-substituted aldehyde is selected from the group consisting of a shampoo composition, a conditioning composition, a hair styling composition, a hair permanent waving composition, a hair relaxing composition, a hair permanent straightening composition and a hair colouring composition.

6. The method according to claim 1 wherein the composition comprising the alpha-substituted aldehyde further comprises 1 to 30 wt % of one or more surfactants.

7. The method according to claim 1 wherein the alpha-substituted aldehyde is an alpha-hydroxy aldehyde.

8. The method according to claim 1 wherein the alpha-substituted aldehyde is selected from the group consisting of 2-hydroxypropanal, 2-hydroxyhexanal, 2-hydroxyoctanal, and 2-(2-hydroxyethoxy)acetaldehyde.

9. The method according to claim 1 wherein the alpha-substituted aldehyde is selected from the group consisting of 2-hydroxypropanal, 2-hydroxyhexanal, 2-hydroxyoctanal, and 2-(2-hydroxyethoxy)acetaldehyde.

10. The method according to claim 1 wherein said composition comprises a first alpha-substituted aldehyde of formula II having less than 10 carbon atoms and a second alpha-substituted aldehyde of formula II having 10 or more carbon atoms.

11. The method according to claim 10 wherein the second alpha-substituted aldehyde is selected from the group consisting of 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

12. The method according to claim 10 wherein the first alpha-substituted aldehyde is selected from the group consisting of 2-hydroxypropanal, 2-hydroxyhexanal, 2-hydroxyoctanal, and 2-(2-hydroxyethoxy)acetaldehyde and the second alpha-substituted aldehyde is selected from the group consisting of 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

13. The method according to claim 1 wherein the composition comprising the alpha-substituted aldehyde further comprises an amine salt of a carboxylic acid.

14. The method according to claim 1 wherein the composition comprising the alpha-substituted aldehyde further comprises a polycarboxylic acid derived chelating agent.

15. The method according to claim 1 wherein the composition comprising the alpha-substituted aldehyde further comprises a succinimidyl ester.

16. The method according to claim 1 wherein the composition comprising the alpha-substituted aldehyde further comprises a crosslinking agent comprising two or more maleic acid derived reactive moieties and a linker having two or more amino groups.

17. The method according to claim 3 which reduces colour loss from said hair by at least 20% after three washes compared with hair dyed by an equivalent method excluding the alpha-substituted aldehyde.

18. The method according to claim 1 wherein the dyed material is a textile material.

19. The method according to claim 18 which inhibits or prevents solvent-mediated leaching of dye resulting from washing a dyed textile material in a laundry washing process.

20. The method of claim 1, wherein R is an unsubstituted alkyl group having 4-16 carbon atoms.

21. The method according to claim 4 wherein the material is growing human hair.

Description

EXAMPLE 1

(1) The hydroxy-substituted aldehyde compounds used in the present invention were prepared using the following method:

(2) These are formed from corresponding 1,2-diol compounds by selective oxidation of the alpha alcohol. In a three necked flask, a copper catalyst in a high temperature oil were weighed. The flask was then fitted with side arm, a receiving flask and a water cooled condenser. The reaction was heated with stirring to the correct temperature under a flow of nitrogen and/or vacuum.

(3) The required alcohol was added continuously at a constant rate. The product was collected by distillation from the reaction mixture. The vacuum or nitrogen was adjusted to ensure the aldehyde was distilled over rapidly to reduce the chance of further oxidation. The exact conditions depend on aldehyde being produced. A yield of greater than 75% is typical.

(4) Other aldehydes tested were commercially available or prepared according to known methods.

EXAMPLE 2

(5) Wool swatches were dyed with an oxidative red dye formed as follows:

(6) ##STR00006##

(7) The dyed swatches were immersed in a solution comprising the test compounds listed in table 1 at 2 wt % (except compounds 5, 8, 9 and 10) and 0.1 wt % SLES buffered to pH 5.5 with sodium acetate buffer for 30 minutes at 40 C. The swatches were then rinsed in water for 2 minutes and then dried. A visual assessment was made of the cloth and this was rated on a scale of 1-5, as follows: 1 Colour significantly more intense than control and close to original colour 2 Colour visibly more intense than control 3 Colour not visibly more intense than control 4 Colour visibly less intense than control 5 Colour significantly less intense than control or colour hue change (eg, blue) or cloth greasy or spotted (reasons recorded)

(8) For cloths visually assessed as more intense than the control (Score 1 or 2), then the actual reading of the colour intensity was measured using standard reflectometry and compared with a deionised water control (containing 0.1 wt % SLES). 100% is the amount of dye removed by the control and a number<100% shows less dye removal than the control and 0% is the colour of the original cloth. In this case the difference in reflectance of light having a wavelength of 457 nm was measured.

(9) Table 1 details the compounds tested and the results obtained. Compounds 1 to 7 are of the invention. Compounds 11 to 18 are comparative examples.

(10) TABLE-US-00001 TABLE 1 Compound Score Result 1 2-hydroxypropanal 1 16% 2 2-hydroxybutanal 2 64% 3 2-hydroxyhexanal 1 2% 4 2-hydroxyoctanal 1 0% 5 D-Glyceraldehyde 1 @1 wt % = 15% 6 Bromomalonaldehyde 2 22% 7 2-(2-hydroxyethoxy)acetaldehyde 2 46% 8 2-hydroxydecanal 2 @1 wt % = 37% 9 2-hydroxydodecanal 2 @1 wt % = 68% 10 2-hydroxytetradecanal 2 @1 wt % = 56% 11 Acetaldehyde 3 12 Propyl aldehyde 3 13 Valeraldehyde 4 14 Hexanal 3 15 Octanal 5 16 Decanal 3 17 3-cyclohexene-1-carboxaldehyde 3 18 2-Deoxy-D-ribose 3

EXAMPLE 3

(11) The wash fastness of the dyeings according to the invention was assessed according to the following method.

(12) Wool swatch samples were initially treated as in example 2. They were then treated washed with a deionized water composition comprising 0.1% SLES for wetting for 15 minutes, rinsed and dried. The reflectance at 457 nm (R457) was measured. A further two washing steps with deionized water comprising 0.1% SLES were carried out for 30 minutes each.

(13) The results in table 2 are the absolute values of R457 wherein R457 is the difference in reflectance at 457 nm between the initially dyed wool swatches and the swatches that have been treated as detailed in the table.

(14) TABLE-US-00002 TABLE 2 30 min % colour treatment Wash Wash loss with Wash 45 min 75 min compared Composition Aldehyde Aldehyde 15 min (total) (total) to control 1 Glyceraldehyde 0.2 1.9 4.9 7.0 33 2 2-hydroxy propanal 1.2 3.1 6.3 8.5 40 3 2-hydroxy octanal 1.5 2.5 7.3 10.3 48.5 4 0.1% SLES (control) 4.9 6.9 13.3 21.2 100

(15) The results in table 2 and the FIGURE clearly show that the present invention provides a benefit in terms of reducing subsequent leaching of dye relative to the control.

EXAMPLE 4

(16) The wash fastness of dyeings treated according to the method of the present invention using bromomalonaldehyde were tested using a method analogous to that described in example 3. The results are shown in table 3.

(17) TABLE-US-00003 TABLE 3 30 min % colour treatment Wash Wash loss with Wash 30 min 45 min compared Composition Aldehyde Aldehyde 15 min (total) (total) to control 5 Control (deionised 4.7 6.9 10.3 13.4 100 water) 6 bromomalonaldehyde 1.5 3.4 5.0 6.7 50

EXAMPLE 5

(18) A study of the use of shampoo compositions comprising 2-hydroxy octanal to achieve wash fastness was carried out according to the following method.

(19) Wool swatch samples were treated as in example 2 using 2.5 wt % solutions of 2-hydroxy octanal or deionised water control and 10% of a basic shampoo formula (12.5 wt % SLES, 2.5 wt % CAPB in water). The results in Table 4 are the absolute values of R457 wherein R457 is the difference in reflectance at 457 nm between the initially dyed wool swatches and the swatches that have been treated with the inventive composition or the control.

(20) TABLE-US-00004 TABLE 4 Composition R457 Shampoo + 2.5 wt % 2-hydroxy octanal 0.4 Shampoo control 7.4