Methods, compositions and uses relating thereto

Abstract

A method of treating a material, the method comprising contacting the material with a composition comprising an alpha-substituted aldehyde.

Claims

1. A method of treating hair, the method comprising contacting the hair with a composition comprising an alpha-substituted aldehyde of formula II: ##STR00006## wherein X is selected from OH, O(CH.sub.2).sub.nA, Cl, Br or F, wherein n is from 1-6 and A is H or OH, and wherein R is an unsubstituted alkyl or alkenyl group having 1-30 carbon atoms.

2. The method according to claim 1 wherein the hair is selected from the group consisting of a human hair or an animal hair.

3. The method according to claim 2 wherein the hair is selected from the group consisting of a growing human hair or a growing animal hair.

4. The method of claim 1 in which said composition comprises two or more alpha substituted aldehydes of formula II.

5. The method of claim 1 wherein the alpha-substituted aldehyde of formula II is an α-hydroxy aldehyde.

6. The method of claim 1 wherein the aldehyde of formula II is selected from the group consisting of: 2-hydroxypropanal, 2-hydroxyhexanal, and 2-hydroxyoctanal.

7. The method of claim 4 in which 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.

8. The method of claim 7 in which the second alpha-substituted aldehyde of formula II is selected from the group consisting of: 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

9. The method of claim 7 in which the first alpha-substituted aldehyde of formula II is selected from the group consisting of: 2-hydroxypropanal, 2-hydroxyhexanal, and 2-hydroxyoctanal and the second alpha-substituted aldehyde of formula II is selected from the group consisting of: 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

10. The method of claim 1 wherein the composition further comprises an amine salt of a carboxylic acid.

11. The method of claim 1 wherein the composition further comprises a chelating agent from the group consisting of glutamic acid, N, N-diacetic acid (GLDA), diethylene triamine pentaacetic acid (DTPA), imido disuccinic acid (IDS), ethylene diamine tetraacetic acid (EDTA), ethylene diamine disuccinic acid (EDDS), hydroxyethyl ethylenediaminetriacetic acid (HEDTA), citric acid and mixtures thereof.

12. The method of claim 1 wherein the composition further comprises a succinimidyl ester.

13. The method of claim 1 wherein the composition is selected from the group consisting of: a shampoo composition, a conditioning composition, a hair dyeing/colouring composition and a hair styling composition comprising a hair permanent waving composition or a hair straightening/relaxing composition.

14. The method of claim 10 wherein the composition further comprises 1-30 wt % of one or more surfactants.

15. The method according to claim 2 in which the composition 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.

16. The method according to claim 15 wherein the benefit is temporary, semi-permanent or permanent.

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.

EXAMPLE 2

(4) The permanent/semi-permanent hair conditioning effect of a composition according to the present invention was assessed as follows:

(5) Method

(6) 1. 15.2 cm/3 g bleached straight hair tresses were pre-washed with a standard commercial non-conditioning shampoo and blow dried. Using a Dia-Stron® MTT175 miniature tensile tester fitted with the combing accessory, the ‘total combing work’ of each tress was measured.

(7) 2. 2 ml of an aqueous solution containing 1% w/w of 2-hydroxydodecanal and 1% w/w of SLES was applied to the hair tresses, combed through, and left to stand for 5 minutes.

(8) 3. The hair tresses were flat ironed with a Tormaline® ceramic hot iron, passing it over the hair tresses slowly five times.

(9) 4. The hair tresses were washed and rinsed thoroughly to remove non-bound material from the hair.

(10) 5. The hair tresses were blow dried with combing.

(11) 6. Again, using a Dia-Stron® MTT175 miniature tensile tester fitted with the combing accessory, the ‘total combing work’ of each treated hair tress was measured.

(12) Results

(13) After treatment of the tresses according to the invention, the ‘total combing work’ was reduced by 36.5 (±3.5)% (average of two hair tress replicates) compared to the initial value before treatment. This indicates a permanent/semi-permanent hair conditioning effect was conferred. This is believed to be due to reaction of the hair with the 2-hydroxydodecanal.

EXAMPLE 3

(14) The permanent/semi-permanent hair straightening effect of a composition according to the present invention was assessed as follows:

(15) Method

(16) 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.

(17) 2. For the ‘treated’ hair tresses, 2 ml of an aqueous solution containing 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.

(18) 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.

(19) 4. The hair tresses were flat ironed with a Tormaline® ceramic hot iron, passing it over the tresses slowly five times.

(20) 5. The hair tresses were washed and rinsed thoroughly to remove non-bound material from the hair.

(21) 6. The hair tresses were combed straight, hung vertically, and allow to air dry for six hours under ambient conditions.

(22) 7. The final length of the hair tresses was measured.

(23) 8. The degree of straightening was calculated according to the following equation:

(24) $\%\mathrm{Straightening}=\frac{L2-L1}{L0-L1}\times 100\%$$\mathrm{Where}\text{:}$$L0=\mathrm{Total}\mathrm{straightened}\mathrm{length}\mathrm{of}\mathrm{hair}\mathrm{tress}$$L1=\mathrm{Initial}\mathrm{untreated}\mathrm{compressed}\mathrm{curly}\mathrm{length}\mathrm{of}\mathrm{tress}$$L2=\mathrm{Final}\mathrm{length}\mathrm{of}\mathrm{trees}\mathrm{after}\mathrm{straightening},\mathrm{wash},\mathrm{and}\mathrm{air}\mathrm{dry}.$
Results

(25) After treatment of the tresses according to the invention, the degree of straightening was 79.2 (±5.9)% (average of three hair tress replicates) 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 2-hydroxyoctanal.