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 keratinous material, the method comprising contacting the keratinous material with a composition comprising an aliphatic aldehyde having a single hydroxyl substitution; wherein the aliphatic aldehyde has at least 3 carbon atoms and the single hydroxyl substitution is at the 2 position.

2. The method according to claim 1 wherein the material is human hair or animal hair.

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

4. The method according to claim 2 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.

5. The method according to claim 4 wherein the benefit may be temporary, semi-permanent or permanent.

6. The method of claim 1 wherein said aliphatic aldehyde having a single hydroxyl substitution is selected from the group consisting of 2-hydroxypropanal, 2-hydroxyhexanal, and 2-hydroxyoctanal.

7. The method of claim 1 wherein the composition comprises said aliphatic aldehyde having a single hydroxyl substitution and less than 10 carbon atoms and a second aliphatic aldehyde having a single hydroxyl substitution and 10 or more carbon atoms.

8. The method of claim 7 wherein the second aliphatic aldehyde having a single hydroxyl substitution is selected from the group consisting of 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

9. The method of claim 7 wherein the first aliphatic aldehyde having a single hydroxyl substitution is selected from the group consisting of 2-hydroxypropanal, 2-hydroxyhexanal or 2-hydroxyoctanal and the second aliphatic aldehyde having a single hydroxyl substitution is selected from the group consisting of 2-hydroxydecanal, 2-hydroxydodecanal and 2-hydroxytetradecanal.

10. The method of claim 1 wherein the composition comprising the aliphatic aldehyde having a single hydroxyl substitution further comprises an amine salt of a carboxylic acid.

11. The method of claim 1 wherein the composition comprising the aliphatic aldehyde having a single hydroxyl substitution further comprises a polycarboxylic acid derived chelating agent.

12. The method of claim 1 wherein the composition comprising the aliphatic aldehyde having a single hydroxyl substitution further comprises a succinimidyl ester.

13. The method of claim 1 wherein the composition comprising the aliphatic aldehyde having a single hydroxyl substitution 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 method according to claim 2 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 selected from the group consisting of a hair permanent waving composition and a hair permanent straightening/relaxing composition.

15. The method according to claim 10 wherein the composition comprising the amine salt of a carboxylic acid further comprises 1 to 30 wt % of one or more surfactants, preferably one or more anionic surfactants.

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:

Method

(5) 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. 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. 3. The hair tresses were flat ironed with a Tormaline ceramic hot iron, passing it over the hair tresses slowly five times. 4. The hair tresses were washed and rinsed thoroughly to remove non-bound material from the hair. 5. The hair tresses were blow dried with combing. 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

(6) 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

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

Method

(8) 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 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:

(9) $\%\mathrm{Straightening}=\frac{L2-L1}{L0-L1}100\%$

(10) Where:

(11) L0=Total straightened length of hair tress

(12) L1=Initial untreated compressed curly length of tress

(13) L2=Final length of tress after straightening, wash, and air dry.

Results

(14) 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.