METHODS, COMPOSITIONS AND USES RELATING THERETO

Abstract

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

Claims

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

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. A hair care composition comprising a hydroxy-substituted aldehyde.

6. The hair care composition according to claim 5 comprising two or more hydroxy substituted aldehydes.

7. The composition according to claim 5 wherein the aldehyde is an hydroxy aldehyde.

8. The composition according to claim 5 wherein the aldehyde is selected from the group consisting of: 2-hydroxypropanal, 2-hydroxyhexanal, 2-hydroxyoctanal and glyceraldehyde.

9. The composition according to claim 8 wherein the aldehyde is selected from the group consisting of: 2-hydroxypropanal, 2-hydroxyhexanal and 2-hydroxyoctanal.

10. The composition according to claim 6 comprising a first hydroxy-substituted aldehyde having less than 10 carbon atoms and a second hydroxy-substituted aldehyde having 10 or more carbon atoms.

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

12. The composition according to claim 10 wherein the first hydroxy-substituted aldehyde is selected from the group consisting of: 2-hydroxypropanal, 2-hydroxyhexanal and 2-hydroxyoctanal and the second hydroxy-substituted aldehyde is selected from the group consisting of: 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

13. The composition according to claim 5 wherein the composition comprising the aldehyde further comprises an amine salt of a carboxylic acid.

14. The method composition according to claim 5 wherein the composition comprising the aldehyde further comprises a polycarboxylic acid derived chelating agent.

15. The composition according to claim 5 wherein the composition comprising the aldehyde further comprises a succinimidyl ester.

16. The method composition according to claim 5 wherein the composition comprising the 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 composition according to claim 5 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 and or a hair permanent straightening/relaxing composition.

18. The composition according to claim 13 wherein the composition comprising the amine salt further comprises 1 to 30 wt % of one or more surfactants.

19. method according to claim 3 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.

20. The method according to claim 19 wherein the benefit may be temporary, semi-permanent or permanent.

21-25. (canceled)

Description

EXAMPLE 1

[0195] The hydroxy-substituted aldehyde compounds used in the present invention were prepared using the following method:

[0196] 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.

[0197] 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

[0198] The permanent/semi-permanent hair conditioning effect of a composition according to the present invention was assessed as follows:

Method

[0199] 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.

[0200] 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.

[0201] 3. The hair tresses were flat ironed with a Tormaline ceramic hot iron, passing it over the hair tresses slowly five times.

[0202] 4. The hair tresses were washed and rinsed thoroughly to remove non-bound material from the hair.

[0203] 5. The hair tresses were blow dried with combing.

[0204] 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.

Results

[0205] 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

[0206] The permanent/semi-permanent hair straightening effect of a composition according to the present invention was assessed as follows:

Method

[0207] 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.

[0208] 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.

[0209] 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.

[0210] 4. The hair tresses were flat ironed with a Tormaline ceramic hot iron, passing it over the tresses slowly five times.

[0211] 5. The hair tresses were washed and rinsed thoroughly to remove non-bound material from the hair.

[0212] 6. The hair tresses were combed straight, hung vertically, and allow to air dry for six hours under ambient conditions.

[0213] 7. The final length of the hair tresses was measured.

[0214] 8. The degree of straightening was calculated according to the following equation:

[00001]$\%.Math..Math.\mathrm{Straightening}=\frac{L.Math..Math.2-L.Math..Math.1}{L.Math..Math.0-L.Math..Math.1}100.Math.\%$

[0215] Where:

[0216] L0=Total straightened length of hair tress

[0217] L1 =Initial untreated compressed curly length of tress

[0218] L2 =Final length of tress after straightening, wash, and air dry.

Results

[0219] 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.