Hair care formulation

Abstract

A hair care formulation comprises a diester of a C8-C26 Guerbet alcohol and a C4-C40 dicarboxylic acid. The diester can function as an active ingredient, particularly as a conditioning agent, especially on dry hair. Silicone-free hair care compositions can be produced with effective conditioning properties on both wet and dry hair.

Claims

1. A hair care formulation comprising a diester of a C8-C26 Guerbet alcohol and a C4-C40 dicarboxylic acid and at least one additional hair care ingredient.

2. The hair care formulation of claim 1 which is silicone-free.

3. A method of conditioning hair which comprises applying a hair care formulation comprising a diester of a C8-C26 Guerbet alcohol and a C4-C40 dicarboxylic acid to hair, and optionally rinsing the hair.

4. The method according to claim 3 wherein the diester is a hair conditioning agent.

5. The method according to claim 3, comprising applying the hair care formulation to dry hair.

6. The method according to claim 3, comprising applying the hair care formulation to wet hair.

7. The method according to claim 3 wherein the total work required for wet hair is less than 3.5?10.sup.?2 Joules.

8. The method according to claim 3 wherein the combined amount of total work required for both dry hair and wet hair is less than 8?10.sup.?2 Joules.

9. The method according to claim 3 wherein the hair care formulation is silicone-free.

10. The method according to claim 3 wherein the hair care formulation comprises a hair conditioning active consisting of at least one diester.

11. The method according to claim 3 wherein the diester comprises dioctyldodecyl dodecanedioate.

12. The method according to claim 3 wherein wherein the total work required for dry hair is less than 4.5?10.sup.?2 Joules.

13. The method according to claim 3, wherein the C4-C40 dicarboxylic acid comprises a C12 or C18 dicarboxylic acid.

14. The method according to claim 3, wherein the C4-C40 dicarboxylic acid is a dimer acid.

15. A pre-emulsion consisting of a diester of a C8-C26 Guerbet alcohol and a C4-C40 dicarboxylic acid, and water, and optionally an emulsifier, wherein the diester is present in an amount of up to 65% by weight relative to the total weight of the pre-emulsion, the water is present in an amount up to 60% by weight relative to the total weight of the pre-emulsion, and the emulsifier, if present, is present in an amount up to 20% by weight relative to the total weight of the pre-emulsion.

Description

EXAMPLE 1

(1) Dioctyldodecyl dodecanedioate was produced by reacting commercially available 2-octyldodecanol (606 g, 2.0 mol) and dodecanedioic acid (230 g, 1.0 mol) in a suitable reaction vessel by heating, with stirring under a nitrogen atmosphere, to a temperature high enough to effect esterification (>100? C.). Reaction progress was monitored by the decline in acid value, with reaction deemed complete when the acid value was <5 mgKOH/g. If required, the rate of reaction can be increased by use of a suitable esterification catalyst* and/or application of vacuum. The resultant crude ester can be utilised as is or may be refined with suitable post-treatments (e.g. steam-stripping, distillation, water-washing, earth treatment, etc.). *Examples include: p-toluenesulfonic acid, methanesulfonic acid, organotitanates, organotin compounds; inorganic acids such as sulphuric, orthophosphoric and hypophosphorous acids, zeolites and biological agents such as enzymes and microorganisms.

EXAMPLE 2

(2) Dioctyldodecyl azelate was produced by reacting commercially available 2-octyldodecanol (144.1 g, 0.48 mol) and nonanedioic acid (45.0 g, 0.24 mol) using the general method described in Example 1.

EXAMPLE 3

(3) The diesters produced in Examples 1 and 2, and a range of other diesters produced according to a similar synthetic method described in Examples 1 and 2, were subjected to the wet combing and dry friction tests described herein. The results are shown in Table 1.

(4) TABLE-US-00001 TABLE 1 Dry Wet Friction Combing Conditioning Active Alcohol Di-acid (Joules) (Joules) None (Blank) 5.98E?02 5.04E?02 Dioctyldodecyl C20 C12 3.83E?02 3.10E?02 dodecanedioate Dioctyldodecyl azelate C20 C9 4.10E?02 3.98E?02 Dioctyldodecyl octadecanoate C20 C18 4.14E?02 3.01E?02 Dioctyldecyl/hexyldecyl C18/C16 C12 4.40E?02 3.64E?02 dodecanoate Dioctyldodecyl sebacate C20 C8 4.63E?02 4.71E?02 Dihexyldecyl dodecanoate C16 C12 4.66E?02 3.74E?02

EXAMPLE 4

(5) A blind experiment was conducted on hair tresses treated with either 1,000 ppm Silicone DC1785 (ex Dow Corning) (Comparative Example), or 1,000 ppm or 2,000 ppm dioctyldodecy dodecanedioate produced in Example 1. Tresses were ranked on a scale of 1 to 3 by 18 assessors in order of preference of smoothness. The results are shown in Table 2 below.

(6) TABLE-US-00002 TABLE 2 Silicone DC1785 (1,000 ppm) Dioctyldodecyl Dioctyldodecyl (Comparative Dodecanedioate Dodecanedioate Assessor Example) (1,000 ppm) (2,000 ppm) 1 3 1 2 2 3 2 1 3 2 1 3 4 1 2 3 5 1 2 3 6 2 1 3 7 3 2 1 8 1 3 2 9 2 3 1 10 2 3 1 11 1 3 2 12 1 3 2 13 1 3 2 14 1 2 2 15 1 1 1 16 2 1 3 17 1 3 2 18 3 1 2 TOTAL 31 37 36

(7) The table value for the Friedman test using n=18 results is 6.333. The calculated test value in this experiment was 1.30. As the test value is below the table value, the results show no significant difference in smoothness between silicone treated hair tresses, or those treated with dioctyldodecyl dodecanedioate at either of the treatment levels tested.

EXAMPLE 5

(8) A shampoo formulation was made of the following composition;

(9) TABLE-US-00003 Ingredients (INCI Name) % w/w Deionised water (Aqua) to 100 Crodateric? CAS 50 (Aqua (and) 10.0 Cocamidopropyl Hydroxysultaine (ex Croda) Arlasilk? EFA (Linoleamidopropyl PG- 0.5 Dimonium Chloride Phosphate (and) Aqua (and) Propylene Glycol) (ex Croda) Terraquat? BD (Bis-(Ethyl PPG-3 Behenate) 1.5 Dimonium Methosulphate (and) Behenamidopropyl Dimethylamine) (ex Croda) Crodafos? HCE (Oleth-5 Phosphate (and) 1.0 Dioleyl Phosphate) (ex Croda) Dioctyldodecyl Dodecanedioate (produced in 2.5 Example 1) Sodium Benzoate 0.25 Sodium Citrate 0.25 Disodium EDTA 0.2 Sodium Lauryl Sulphate 10.0 Sodium Laureth Sulphate 20.0 Ethylene Glycol Distearate 0.5 Preservative qs Fragrance qs

(10) In normal use, the shampoo results in conditioning of both wet and dry hair.

EXAMPLE 6

(11) A rinse-off conditioner formulation was made of the following composition;

(12) TABLE-US-00004 Ingredients (INCI Name) % w/w Part A Crodazosoft? DBQ (Quaternium-91 (and) Cetrimonium 2.25 Methosulfate (and) Cetearyl Alcohol) (ex Croda) Crodacol? CS90 (Cetearyl Alcohol) (ex Croda) 2.0 Crodacol? C90 (Cetyl Alcohol) (ex Croda) 0.5 Super Sterol Ester? (C.sub.10-C.sub.30 Cholesterol/Lanosterol Esters) 1.0 (ex Croda) Dioctyldodecyl Dodecanedioate (produced in Example 1) 4.5 Crodacel? QS (PG-Hydroxyethyl Cellulose Steardimonium 0.2 Chloride) (ex Croda) Deionized Water 85.25 Part B Crosilk? 10,000 (Hydrolyzed Silk) (ex Croda) 1.0 Hydrotriticum? 2000 (Hydrolyzed Wheat Protein) 1.0 (ex Croda) Keravis? (Hydrolyzed Vegetable Protein PG-Propyl 1.0 Silantriol) (ex Croda) Crodarom Phytexcell Green Tea? (Glycerin (and) Butylene 0.15 Glycol (and) Water (and) Camellia Sinensis Leaf Extract) (ex Croda) Crodarom Phytexcell Chamomile? (Glycerin (and) 0.15 Butylene Glycol (and) Water (and) Chamomilla Recutita Matricaria) Extract) (ex Croda) Part C Phenova (Phenoxyethanol (and) Methyl Paraben (and) 1.0 Ethyl Paraben (and) Butyl Paraben (and) Propyl Paraben (and) Isobutylparaben) pH: 4.5 Viscosity: 11,200 cps (RVT Spindle TC @ 10 RPM @ RT) Procedure: The components of Part A were combined, heated to 75?-80? C., and allowed to cool to 40? C. The components of Part B were added individually. Part C was added, and the pH adjusted to 4.5 with triethylamine.

(13) In normal use, the rinse-off conditioner results in conditioning of both wet and dry hair.

EXAMPLE 7

(14) A silicone-free hair oil formulation was made of the following composition;

(15) TABLE-US-00005 Product (INCI Name) Functionality % w/w Crodamol? STS (PPG-3 Benzyl ether Base oil to 100 myristate) (ex Croda) Dioctyldodecyl Dodecanedioate (produced in Conditioning 20.0 Example 1) Crodamol? GTCC (Caprylic/Capric Light 5.0 triglycerides) (ex Croda) Emollient Crodamol? CAP (Cetearyl Ethylhexanoate Hair gloss 5.0 (and) Isopropyl Myristate) (ex Croda) Jojoba Oil (Buxus Chinensis) (ex Croda) Plant extract 1.0 BHT Anti-oxidant 0.05 Procedure: All the components were added together and mixed until homogenous.

(16) In normal use, the silicone-free hair oil formulation results in conditioning of both wet and dry hair.

(17) The above examples illustrate the improved properties of the hair care formulation and use thereof according to the present invention.