Methods, compositions and uses relating thereto

Abstract

A method of treating a material, the method comprising the steps of: (1) contacting the material with a composition comprising an electrophilic species selected from aldehydes, succinimidyl esters, and mixtures thereof; (2) contacting the material with a composition comprising a chelating agent and/or a salt of an amine and/or a carboxylic acid.

Claims

1. A hair care composition comprising an electrophilic species selected from the group consisting of aldehydes, succinimidyl esters and mixtures thereof; and a chelating agent and/or a salt of an amine and a carboxylic acid; wherein the aldehyde is a hydroxyl aldehyde having a single hydroxyl substituent, said single hydroxyl substituent located at a 2, 3 or 4 position of said aldehyde, and wherein the succinimidyl ester is a compound of formula (IV): ##STR00017## wherein R is phenyl or CH.sub.3(CH.sub.2).sub.n wherein n is 5 to 10; and R.sup.1 is hydrogen or a sulfonate moiety.

2. The composition according to claim 1 wherein the aldehyde is an alpha-substituted aldehyde.

3. The composition according to claim 1 wherein the aldehyde is selected from the group consisting of 2-hydroxypropanal, 2-hydroxyhexanal, and 2-hydroxyoctanal.

4. The composition according to claim 1 comprising a first aldehyde having less than 10 carbon atoms and a second aldehyde having 10 or more carbon atoms.

5. The composition according to claim 4 wherein the second aldehyde is selected from the group consisting of 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

6. The composition according to claim 4 wherein the first aldehyde is selected from the group consisting of 2-hydroxyhexanal, 2-hydroxyoctanal, 2-hydroxypropanal, glyceraldehyde, 2-hydroxybutanal, 3-hydroxybutanal, 4-hydroxybutanal, bromomalonaldehyde, 2-(2-hydroxyethoxy)acetaldehyde, 2-chloro octanal, 2-fluoro octanal, 2-bromo octanal, 6-hydroxyhexanal, 3-hydroxypropanal and 4-hydroxy-but-2-enal and the second aldehyde is selected from the group consisting of 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

7. The composition according to claim 1 wherein the chelating agent is a polycarboxylic acid derived chelating agent.

8. The composition according to claim 1 wherein the chelating agent is selected from the group consisting of diethylene triamine pentaacetic acid (DTPA), glutamic acid N, N-diacetic acid (GLDA) and mixtures thereof.

9. The composition according to claim 1 wherein the amine salt of a carboxylic acid is an amine salt of a carboxylic acid wherein the carboxylic acid has 4 to 10 carbon atoms.

10. The composition according to claim 9 wherein the amine salt is the diethanolamine salt or triethanolamine salt of octanoic acid or hexanoic acid.

11. The composition according to claim 1 which is selected from 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.

12. The composition according to claim 1 which further comprises 1 to 30 wt % surfactants.

13. The composition according to claim 1 which further comprises a crosslinking agent comprising two or more maleic acid derived reactive moieties and a linker having two or more amino groups.

14. The composition according to claim 1 which provides one or more benefits selected from the group consisting of increased gloss or shine, improved combability, improved strength, increased softness, reduced protein loss, improved thermal durability, increased chemical resistance, increased waviness and increased straightness.

15. The composition according to claim 14 wherein the benefit may be temporary, semi-permanent or permanent.

16. A packaged hair colouring product comprising one or more compositions wherein the one or more compositions comprise at least one dye compound and/or one dye precursor compound; and the hair care composition of claim 1.

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.
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.

EXAMPLE 2

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

(4) ##STR00016##
The dyed swatches were immersed in an aqueous solution comprising the test compounds listed in table 1 in the specified amounts 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. The reading of the colour intensity of the resultant cloth was measured using standard reflectometry and compared with a deionised water control (containing 0.1 wt % SLES). In this case the difference in reflectance of light having a wavelength of 457 nm was measured.
The results in table 1 are the absolute values of ΔR457 wherein ΔR457 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.

(5) TABLE-US-00001 TABLE 1 Amount in wt % Composition 2-hydroxyoctanal GLDA** Amine salt* ΔR457 1 0.00 0.00 0.00 6.1 2 0.00 1.25 0.50 3.6 3 0.50 1.18 0.54 2.1 4 1.00 1.27 0.24 2.3 5 0.50 1.25 0.00 4 6 0.82 0.04 0.50 3.7 *The amine salt used in the examples was the triethanolamine salt of octanoic acid. **The amount refers to the amount as free acid.

EXAMPLE 3

(6) The tests of example 2 were repeated except the components were added to an aqueous composition comprising 10 wt % of a commercial shampoo formulation rather than 0.1 wt % SLES.

(7) The results in table 2 are the absolute values of ΔR457 wherein ΔR457 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.

(8) TABLE-US-00002 TABLE 2 Amount in wt % Composition 2-hydroxyoctanal GLDA** Amine salt* ΔR457 1 0.00 0.00 0.00 5.9 2 0.00 1.25 0.50 3.8 3 0.00 2.50 0.50 2.4 4 0.26 0.00 0.49 4.9 5 0.50 1.25 0.00 2.5 6 0.50 2.50 0.50 1.2 7 0.54 1.18 0.54 3.3 8 1.00 1.25 0.80 0.5 9 1.00 1.27 0.24 2.2 10 1.00 2.50 0.00 1.4 11 1.00 2.50 1.00 0 *The amine salt used in the examples was the triethanolamine salt of octanoic acid. **The amount refers to the amount as free acid.

EXAMPLE 4

(9) The permanent/semi-permanent hair straightening effect of compositions comprising 2-hydroxyoctanal or the triethanolamine salt of octanoic acid was assessed as follows:

(10) Method

(11) 1. 15.2 cm/3 g bleached straight hair tresses were pre-washed with a standard commercial non-conditioning shampoo, combed, hung vertically and allowed to air dry for six hours under ambient conditions, then their initial lengths were measured. 2. For the ‘treated’ hair tresses, 2 ml of an aqueous solution containing (a) 2% w/w of the triethanolamine salt of octanoic acid and 1% w/w of SLES; or (b) 2% w/w of 2-hydroxyoctanal and 1% w/w of SLES; was applied to the hair tresses, combed through and left to stand for 5 minutes. 3. For the control hair tresses, 2 ml of an aqueous solution containing 1% w/w of SLES was applied to the hair tresses, combed through and left to stand for 5 minutes. 4. The hair tresses were flat ironed with a Tormaline® ceramic hot iron, passing it over the tresses slowly five times. 5. The hair tresses were washed and rinsed thoroughly to remove non-bound material from the hair. 6. The hair tresses were combed straight, hung vertically, and allow to air dry for six hours under ambient conditions. 7. The final length of the hair tresses was measured. 8. The degree of straightening was calculated according to the following equation:

(12) $\%\mathrm{Straightening}=\frac{L2-L1}{L0-L1}\times 100\%$ Where: L0=Total straightened length of hair tress L1=Initial untreated compressed curly length of tress L2=Final length of tress after straightening, wash, and air dry.
Results
After treatment of the tresses, the degree of straightening was as follows:

(13) (a) 64.2 (±8.8)% (average of three hair tress replicates)

(14) (b) 79.2 (±5.9)% (average of three hair tress replicates)

(15) compared to 21.2 (±9.5)% (average of three hair tress replicates) of that of the control tresses. This indicates a permanent/semi-permanent hair straightening effect was conferred. This is believed to be due to reaction of the hair with the triethanolamine salt of octanoic acid (a) or 2-hydroxyoctanal (b).