Hair care polymer

Abstract

The invention relates to a hair care composition comprising at least one cationic film forming polymer selected from the group of Polyquaternium and at least one quaternized hyperbranched polymer having end-groups of formula (I) characterized in that said quaternized hyperbranched polymer is obtainable by preparation of a hyperbranched polymer having dimethylamino end groups by condensation of 2-dodecen-1-ylsuccinic anhydride, diisopropanolamine and N,N-bis[3-(dimethylamino)propyl]amine followed by quaternization of the dimethylamino end-groups to end groups of formula (I). ##STR00001##

Claims

1. A hair care composition comprising: (1) at least one polyquaternium as a cationic film forming polymer, and (2) at least one quaternized hyperbranched polymer having end-groups of formula (I): ##STR00004## wherein the quaternized hyperbranched polymer is: (i) a condensation reaction product of a monomeric mixture consisting of 2-dodecen-1-ylsuccinic anhydride, diisopropanolamine and N,N bis[3-(dimethylamino)propyl]amine to obtain a hyperbranched polymer having dimethylamino end groups followed by (ii) quaternization of the dimethylamino end-groups to end groups of formula (I).

2. The hair composition according to claim 1, wherein the hyperbranched polymer having dimethylamino end-groups is a condensation reaction product of 40-70 wt.-% of 2 dodecen-1-ylsuccinic anhydride, 5-20 wt.-% of diisopropanolamine and 15-45 wt.-% of N,N-bis[3-(dimethylamino)propyl]amine with the proviso that the total amount of 2 dodecen-1-ylsuccinic anhydride, diisopropanolamine and N,N-bis[3-(dimethylamino)propyl]amine sums up to 100 wt.-%.

3. The hair composition according to claim 1, wherein the quaternization of the dimethylamino end-groups is carried out using sodium 2 chloroacetate.

4. The hair composition according to claim 1, wherein the degree of quaternization of the dimethylamino end-groups is in a range of 50 to 100 mol-%.

5. The hair composition according to claim 1, wherein a ratio (w/w) of N,N-bis[3-(dimethylamino)propyl]amine to diisopropanolamine is in a range of 4:1 to 0.5:1.

6. The hair composition according to claim 5, wherein the ratio (w/w) of N,N-bis[3-(dimethylamino)propyl]amine to diisopropanolamine is in the range of 2:5 to 1.2:1.

7. The hair composition according to claim 1, wherein a ratio (w/w) of 2-dodecen-1-ylsuccinic anhydride to the total amount of amines is in a range of 3:1 to 1:3.

8. The hair composition according to claim 1, wherein the hyperbranched polymer having dimethylamino end-groups has an average number molecular weight Mn which is in a range of 1500-5000 g/mol.

9. The hair composition according to claim 1, wherein at least one quaternized hyperbranched polymer is present in an amount within a range of 0.01-20 wt.-%.

10. The hair composition according to claim 1, wherein the at least one cationic film forming polymer is selected from the group consisting of cationic cellulose derivatives, cationic diallyl quaternary ammonium-containing polymers and mixtures thereof.

11. The hair composition according to claim 1, wherein the at least one cationic film forming polymer is present in an amount within a range of 0.01-5 wt. %.

12. The hair care composition according to claim 1, wherein the hair care composition is a shampoo preparation.

13. A method of treating hair, said method comprising the steps of applying a hair care composition according to claim 1 to the hair followed by rinsing the hair with water.

14. The method according to claim 13, wherein the treatment of hair is an improvement of the volume, elasticity, wet feel, wet combing, and style setting of hair.

Description

EXAMPLE 1A

Preparation of a Hyperbranched Polymer According to the Invention (PoE-1a)

(1) 232 g of N,N-bis[3-(dimethylamino)propyl]amine and 109.9 g molten diisopropanolamine were added to a glass reactor equipped with stirrer and condenser, and which can be heated by oil. To this mixture 458.1 g of molten 2-dodecen-1-ylsuccinic anhydride was added. After addition the mixture was slowly heated to 160 C. and 1 h later vacuum was applied to remove the reaction water. After 5 h the mixture was cooled obtaining a hyperbranched polymer having dimethylamine end-groups and a M.sub.n of 2200.

(2) 50 g of the hyperbranched polymer having dimethylamine end groups were subsequently dissolved in 66.3 g water and to this mixture 16.3 g sodium 2-chloroacetate (SMCA) was added. This mixture was reacted at 80 C. for approximately 10 hours while stirring after which the quaternized polymer solution was ready for use (polymer content 50 wt.-%). Calculated level of quaternized dimethylamino end-groups: 90%.

EXAMPLE 1B

Preparation of a Hyperbranched Polymer According to the Invention (PoE-1 b)

(3) 235 g of N,N-bis[3-(dimethylamino)propyl]amine and 160 g molten diisopropanolamine were added to a glass reactor equipped with stirrer and condenser, and which can be heated by oil. To this mixture 639 g of molten 2 dodecen-1-ylsuccinic anhydride was added. After addition the mixture was slowly heated to 160 C. and 1 h later vacuum was applied to remove the reaction water. After 5 h the mixture was cooled obtaining a hyperbranched polymer having dimethylamine end-groups and a Mn of 17400.

(4) 80 g of the hyperbranched polymer having dimethylamine end groups were subsequently dissolved in 99.6 g water and to this mixture 19.6 g sodium 2 chloroacetate (SMCA) was added. This mixture was reacted at 80 C. for approximately 10 hours while stirring after which the quaternized polymer solution was ready for use (polymer content 50 wt.-%). Calculated level of quaternized dimethylamino end-groups: 90%.

EXAMPLE 1C

Preparation of a Reference Hyperbranched Polymer (Methyl Quaternized) (PoE-1c)

(5) 235 g of N,N-bis[3-(dimethylamino)propyl]amine and 160 g molten diisopropanolamine were added to a glass reactor equipped with stirrer and condenser, and which can be heated by oil. To this mixture 639 g of molten 2 dodecen-1-ylsuccinic anhydride was added. After addition the mixture was slowly heated to 160 C. and 1 h later vacuum was applied to remove the reaction water. After 5 h the mixture was cooled obtaining a hyperbranched polymer having dimethylamine end-groups and a Mn of 17400.

(6) 25 g of the hyperbranched polymer having dimethylamine end groups were subsequently dissolved in 50 g water and to this mixture 7.3 g dimethylsulfate was slowly added. After 24 h the the quaternized polymer solution was ready for use (polymer content 33 wt.-%). Calculated level of quaternized dimethylamino end-groups: 95%.

EXAMPLE 2

Wet Combing Properties

(7) A standard shampoo as outlined in table 1 was prepared by dissolving the polymers in water, addition of the surfactants, followed by addition of the preservative. The pH was adjusted with Citric Acid on pH=5.0-5.1 and the viscosity controlled by addition of sodium chloride water solution

(8) TABLE-US-00001 TABLE 1 Standard Shampoo Ingredient (INCI) Wt.-%* Polymer of Example 1a (PoE-1a) See table 2 Polyquaternium-7 (Polyquat-7) See table 2 Hydroxypropyl guar (HPG) (Reference) See table 2 Sodium Laureth Sulfate 28%/Water 72% 35.0% Cocamidopropyl Betaine 40%/Water 60% 5.0% Sodium Benzoate 0.5% Citric acid 0.15% Sodium Chloride 1.5% Water q.a. *all given concentrations are based on the active ingredient

(9) The wet combing properties were done according to SGS Fresenius standardized study setup: 5 hair swatches per shampoo sample (European Hair, weight: 20.3 g, length: 21 cm, color 4/0 medium brown, Kerling International Art.-Nr. 826530) were used for the determination of combing forces. All swatches were defined damaged by professional hair bleach. The hair swatches were pre-conditioned in water and washed with a 14% Sodium Laureth Sulfate (SLES) solution. The wet combing force was measured immediately after washing. The combing force of the hair was measured using a tensile testing machine (Zwick Z 1.0/TN1SSO) resulting in the value for the untreated swatches.

(10) Then the swatches were then treated twice with a test item (shampoo; 0.5 ml/g hair), foamed for 1 min and left to rest for additional 2 min. After each foaming phase the test product was rinsed off for 1 min with water. Again, the wet combing force was measured immediately after washing.

(11) The average work is calculated from the surface below the force-path plot in the measuring interval between 20 and 120 mm. The relative combing force (RCF) is calculated from the value of the untreated swatch W.sub.0, and the value of the treated swatch W.sub.1 according following expression: RCF[%]=(W.sub.0W.sub.1)/W.sub.0. Negative values show a reduction in combing force, positive an increase.

(12) TABLE-US-00002 TABLE 2 Results of the wet combing test RCF RCF PoE-1a Polyquat-7 HPG measured expected * 0.5 wt.-% 7.0% 1.0 wt.-% 7.0% 0.2 wt. % 6.0% 0.5 wt.-% 0.2 wt.-% 28.0% 13% +15% 1.0 wt.-% 0.2 wt.-% 20.0% 13% +7% 0.25 wt.-% 24% 0.5 wt.-% 0.25 wt.-% 26% 31% 5% 1.0 wt.-% 0.25 wt.-% 26% 31% 5% * = [(RCF measured) (RCF expected)]

(13) As can be retrieved from the results outlined above only the inventive combination leads to a synergistic improvement of the wet combing properties, whereas the combination with another film forming polymer (i.e. Hydroxypropyl guar (HPG)) even results in a declined wet combability compared to the untreated swatches.

EXAMPLE 2

Stylist Salon Test

(14) The Stylist Salon Test was done at AR Hair Cosmetics (Impasse du Nouveau-March, CH-1723 Marly). All products were tested with half-head comparison test vs. a reference comprising only the respective Polyquaternium. Test pairs were blinded, order and head side were randomized.

(15) Tested Products

(16) The effect of the combination of the polymer of example 1 with Polyquaternium-10 respectively Polyquaternium-7 was tested in the standard shampoo formulation as outlined in table 3.

(17) TABLE-US-00003 TABLE 3 Shampoo formulations for half side test A A (Ref) B B (Ref) Ingredient (INCI) Wt.-%* Polymer of Example 1 0.5 1.0 Polyquaternium-7 0.2 0.2 Polyquaternium-10 0.4 0.4 Sodium Laureth Sulfate 28%/ 35.0 35.0 35.0 35.0 Water 72% Cocamidopropyl Betaine 40%/ 5.0 5.0 5.0 5.0 Water 60% Sodium Benzoate 0.5 0.5 0.5 0.5 Citric acid 0.15 0.15 0.15 0.15 Sodium Chloride 1.5 1.5 1.5 1.5 Water q.a. q.a. q.a. q.a. *all given concentrations are based on the active ingredient

(18) Definition of Difference in Evaluation

(19) The values given in table 4 are the result of a direct comparison test of A with A and B with B, wherein the references A and B have been set to 0 according to standard practice. similar, 0 no difference slight, +/1 Difference is not detectable without direct comparison. So this is without relevance in daily practice. Consequences are not expected. noticeable, +/2 Difference is so big, that it could also be detected without direct comparison.

(20) TABLE-US-00004 TABLE 4 Results of the half side test Attribute Wet Wet Style Sample Volume Elasticity feel combing setting A 1.5 1.4 1.0 0.9 1.1 B 1.5 2.0 1.6 1.8 1.0

(21) The use of the shampoos comprising the combination of the specific polymers according to the present invention led in both cases to better care properties. Furthermore, the setting of a style with these shampoos was easier because the hair takes the desired shape good and stays better. Furthermore, these shampoos gave to water wave-hair-dos better bounce (elasticity) and more defined curls.

EXAMPLE 4

Comparative Test

(22) A standard shampoo as outlined in table 5 was prepared by dissolving the polymers in water, addition of the surfactants, followed by addition of the preservative. The sodium chloride is dissolved in 4 parts water before adding. The pH was adjusted with Citric Acid on pH=4.8-5.1.

(23) TABLE-US-00005 TABLE 5 Standard Shampoos Ingredient (INCI) Wt.-%* Wt.-%* Polymer of Example 1b (PoE-1b) (Invention) 1.0% Polymer of Example 1c (PoE-1c) (Reference) 1.0% Sodium Laureth Sulfate 28%/Water 72% 35.0% 35.0% Cocamidopropyl Betaine 40%/Water 60% 5.0% 5.0% Sodium Benzoate 0.5% 0.5% Citric acid 0.5% 0.5% Sodium Chloride 1.5% 1.5% Water demin. Ad 100 Ad 100 *all given concentrations are based on the active ingredient

(24) Preparation of Swatches

(25) The tresses (Caucasian, dark blond, virgin hair, 23 cm long, Kerling International Art. No. 826500) are cut in swatches of 2.0 cm width. Before washing, the hair swatches are soaked in 2-Propanol for hour. Afterwards, the swatches were washed with a cleansing shampoo (35 wt.-% Sodium Laureth Sulfate 28%/Water 72%; 4% sodium chloride; 59.8 wt.-% water demin; 0.5 wt.-% sodium benzoate) as outlined below under application of product.

(26) After washing, the hairs were combed, air dried and conditioned overnight in the climate chamber at 20 C. and 60% rel. humidity. The weight of the hair switches is standardized under these conditions for 2.4 g+/0.2 g (representing 2.2 g of hair without rubber coating).

(27) The hair swatches are measured (see below) without product application and assorted to groups with similar average combing force

(28) Application of Product

(29) Each swatch (ca. 2 g of hair) is wetted with warm tap water. 0.5 ml of shampoo according to table 5 (0.25 mL/g hair) is applied with a syringe from the root to the tips, and the shampoo is foamed with the fingers for a period of 30 sec. Then the swatch is rinsed under warm running tap water (38 C., ca. 5 l/min) for 30 sec, during rinsing, the shampoo is stripped-off carefully with the fingers. The procedure is done twice.

(30) Measurement of Dry Combing Properties

(31) The hairs are combed in wet stage and dried hanging without blow-drying for 3 hours in the lab. After that the hairs are stored in a climate chamber at 20 C. and 60% rel. humidity for at least 8 hours. Afterwards the dry combing force is measured using a INSTRON 5542, equipped with a pneumatic clamp. For the combing force measurement a combing rack is attached at the machine. The hair swatch is fixed in the clamp and pulled 10 times through the comb fixed at the rack with a velocity 500 cm/min.

(32) The average work is calculated from the surface below the force-path plot in the measuring interval between 20 and 120 mm. The relative combing force (RCF) is calculated from the value of the untreated swatch W.sub.c, and the value of the treated swatch W.sub.1 according following expression: RCF[%]=(W.sub.0W.sub.1)/W.sub.0. Negative values show a reduction in combing force, positive an increase.

(33) TABLE-US-00006 TABLE 6 PoE-1b Polyquat-7 PoE-1c RCF measured 1.0 wt.-% 10% 1.0 wt.-% 0.4 wt. % 27% 1.0 wt.-% 10% 0.4 wt.-% 1.0 wt.-% 8%

(34) As can be retrieved from the results outlined above only the inventive combination leads to a synergistic improvement of the dry combing properties, whereas the combination with the corresponding methyl quaternized hyperbranched polymer (i.e. PoE-1c) even results in a declined dry combability compared to the untreated swatches.