Hair care polymer

Abstract

The invention relates to specific quaternized hyperbranched polymers 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). Furthermore, the invention is directed to clear shampoo preparations comprising such quaternized hyperbranched polymers. ##STR00001##

Claims

1. A quaternized hyperbranched polymer having end-groups of formula (I): ##STR00004## wherein the quaternized hyperbranched polymer is a condensation reaction product of a reaction mixture consisting of: (i) 2-dodecen-1-ylsuccinic anhydride, (ii) diisopropanolamine, and (iii) N,N bis[3-(dimethylamino)propyl]amine, to obtain a hyperbranched polymer having dimethylamino end groups followed by quaternization of the dimethylamino end-groups to end groups of formula (I).

2. The quaternized hyperbranched polymer according to claim 1, wherein the quaternized hyperbranched polymer having dimethylamino end-groups is the condensation reaction product of a reaction mixture consisting of: (i) 40-70 wt.-% of 2 dodecen-1-ylsuccinic anhydride, (ii) 5-20 wt.-% of diisopropanolamine, and (iii) 15-45 wt.-% of N,N-bis[3-(dimethylamino)propyl]amine, wherein the 2 dodecen-1-ylsuccinic anhydride, the diisopropanolamine and the N,N-bis[3-(dimethylamino)propyl]amine are present in a total amount which sums to 100 wt.-%.

3. The quaternized hyperbranched polymer according to claim 1, wherein the dimethylamino end-groups are quaternized with sodium 2 chloroacetate.

4. The quaternized hyperbranched polymer 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 quaternized hyperbranched polymer 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 quaternized hyperbranched polymer 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 quaternized hyperbranched polymer 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 quaternized hyperbranched polymer 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 1,000 to 150,000 g/mol.

9. The quaternized hyperbranched polymer according to claim 1, wherein the quaternized hyperbranched polymer is in the form of an aqueous solution comprising 30-50 wt.-% of the quaternized hyperbranched polymer, based on polymer content in the aqueous solution.

10. A clear shampoo preparation comprising a hyperbranched polymer according to claim 1.

11. The clear shampoo preparation according to claim 10, wherein the hyperbranched polymer is present in an amount within a range of 0.01-20 wt. %, based on total weight of the shampoo preparation.

12. The clear shampoo preparation according to claim 10, which further comprises water, an anionic surfactant and an amphoteric or zwitterionic surfactant.

13. The clear shampoo preparation according to claim 12, wherein the anionic surfactant is selected from the group consisting of sodium lauryl sulfate, ammonium lauryl sulfate, sodium lauryl ether sulfate, ammonium lauryl ether sulfate and mixtures thereof, and wherein the amphoteric or zwitterionic surfactant is selected from the group consisting of cocamidopropyl betaine, disodium cocoamphodiacetate and mixtures thereof.

14. The clear shampoo preparation according to claim 12, wherein the anionic surfactant and the amphoteric or zwitterionic surfactant are present in a total amount in the range of 1 to 50 wt. %, based on the total weight of the shampoo preparation.

15. The clear shampoo preparation according to claim 12, wherein the anionic surfactant and the hyperbranched polymer are present in a ratio of the anionic surfactant to the hyperbranched polymer in a range of 10 to 1 to 5 to 1.

16. A process for the preparation of a hyperbranched polymer having end-groups of formula (I): ##STR00005## wherein the process comprises the steps of: (a) subjecting a reaction mixture consisting of (i) 2 dodecen-1-ylsuccinic anhydride, (ii) diisopropanolamine, and (iii) N,N bis[3-(dimethylamino)propyl]amine to condensation reaction conditions to form a hyperbranched polymer having dimethylamino end-groups, followed by (b) quaternization of the dimethylamino end-groups of the hyperbranched polymer to obtain a hyperbranched polymer with the end groups of formula (I).

Description

EXAMPLE 1

Preparation of Polymer Samples

(1) A. Hyperbranched Polymer Having Dimethylamine End-Groups

(2) 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 and a viscous polymer was obtained.

EXAMPLE A1

Methyl-Quaternised Hyperbranched Polymer (Reference)

(3) 50 g of the hyperbranched polymer having dimethylamine endgroups of example 1 was dissolved in 67.6 g water and at room temperature 17.6 g of dimethyl sulfate (DMS) was slowly added. First the mixture was turbid but within 10 min the temperature raised to about 50 C. and the mixture became clear. After 24 h the quaternized polymer solution was ready for use. Calculated level of quaternized dimethylamino end-groups: 90%.

EXAMPLE A2

Protonised Hyperbranched Polymer (Reference)

(4) 50 g of the hyperbranched polymer having dimethylamine endgroups of example 1 was dissolved in 63.4 g water and at room temperature 13.4 g of methane sulfonic acid (MeSA) was slowly added and completely mixed with the polymer-water mixture after which the protonised polymer solution was ready for use. Calculated level of protonisation of dimethylamino end-groups: 90%.

EXAMPLE A3

Hyperbranched Polymer According to the Present Invention

(5) 50 g of the hyperbranched polymer having dimethylamine endgroups of example 1 was 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. Calculated level of quaternized dimethylamino end-groups: 90%. Color: slightly yellowish.

(6) In analogy to Example 1 further hyperbranched polymers have been prepared exhibiting different M.sub.n. The respective quaternized samples have also been prepared in analogy to the methods described in examples A1, A2 and A3. The respective amounts of raw materials used are given in table 1.

(7) TABLE-US-00001 TABLE 1 Summary of hyperbranched polymers prepared Mn.sup.# BDMAPA DiPA DDSA HHPA DMS MeSA SMCA Example No. [g/mol] [g]* [g]** A1 (Ref.) 2200 232 109.9 458.1 17.6 A2 (Ref) 2200 232 109.9 458.1 13.4 A3 (Inv) 2200 232 109.9 458.1 16.3 B1 (Ref) 17000 181.8 123.7 494.5 13.9 B2 (Ref) 17000 181.8 123.7 494.5 10.6 B3 (Inv) 17000 181.8 123.7 494.5 12.8 C1 (Ref) 33000 176.7 125.9 497.4 13.6 C2 (Ref) 33000 176.7 125.9 497.4 10.3 C3 (Inv) 33000 176.7 125.9 497.4 12.5 D1 (Ref) 121000 172.4 127.9 499.7 13.0 D2 (Ref) 121000 172.4 127.9 499.7 9.9 D3 (Inv) 121000 172.4 127.9 499.7 12.0 E1 (Ref) 1700 305.4 145.0 0 349.7 21.3 E2 (Ref) 1700 305.4 145.0 0 349.7 16.2 E3 (Ref) 1700 305.4 145.0 0 349.7 19.7 BDMAPA: N,N-bis[3-(dimethylamino)propyl]amine DiPA = Diisopropanolamine DDSA = 2-Dodecen-1-ylsuccinic anhydride HHPA = Hexahydrophthalic anhydride SMCA = Sodium 2-chloroacetate DMS = Dimethylsulfate MeSA = Methylsulfonic acid .sup.#calculated Mn of the non-quaternized hyperbranched polymer having dimethylamino end-groups *weight based on 800 g reactor filling **weights based on 50 g hyperbranched polymer having dimethylamine endgroups.

EXAMPLE 2

Influence of Polymer on the Turbidity of a Shampoo Preparation

(8) A standard shampoo preparation as outlined in table 1 was prepared using different polymer samples of Example 1. Afterwards the turbidity of the shampoo was assessed visually. The results are illustrated in table 3.

(9) TABLE-US-00002 TABLE 2 Standard Shampoo preparation Ingredient (INCI) Wt.-% Polymer See table 3 Sodium Laureth Sulfate 28%/Water 72% 35.0% Cocamidopropyl Betaine 40%/Water 60% 5.0% Sodium Benzoate 0.5% Citric acid 0.1% Sodium Chloride See table 3 Water Ad 100 The pH of the shampoos was in the range of 4.5-5.5

(10) TABLE-US-00003 TABLE 3 Results of the turbidity assessment of the shampoo preparations Polymer NaCl Visual appearance of respective Polymer [wt.-%] [wt.-%] shampoo preparation A3 0.5 1.5 clear A3 1.0 1.5 clear A3 2.0 1.5 clear B3 1.0 1.0 clear B2 (Ref) 1.0 1.0 turbid B1 (Ref) 1.0 1.0 turbid C3 1.0 1.5 clear C3 0.50 1.5 clear C2 (Ref) 1.0 1.2 turbid C2 (Ref) 0.5 1.5 turbid C1 (Ref) 1.0 1.0 turbid C1 (Ref) 0.5 1.5 turbid D3 0.5 1.5 clear D2 (Ref) 0.5 1.5 turbid D1 (Ref) 0.5 1.5 turbid

(11) As can be retrieved from table 3 only the polymers quaternized with sodium 2-chloroacetate resulted in clear shampoo preparations in a broad concentration range whereas the polymers quaternized with dimethylsulfate or protonated resulted in turbid shampoo preparations.

EXAMPLE 3

Influence of Polymer on the Viscosity of a Shampoo Preparation

(12) The polymers A1, A3, E2 and E3 of example 1 built up from different anhydride building blocks and quaternized either with SMCA, DMS or protonated with MeSAP have been incorporated into a standard shampoo formulation outlined in table 4, in the amounts indicated in table 5. The viscosities of the respective shampoos were determined with a Brookfield Rheometer RVT, Spindle 4 at 10 rpm at 22 C. For shampoos exhibiting already a low viscosity at low concentrations of polymer higher concentrations have not always been tested as an increased amount of polymer anyway results in a further decrease of the viscosity.

(13) TABLE-US-00004 TABLE 4 Standard Shampoo Ingredient (INCI) Wt.-% Polymer See table 5 Sodium Laureth Sulfate 28%/Water 72% 35.0 Cocamidopropyl Betaine 40%/Water 60% 5.0 Sodium Benzoate 0.5 Citric acid 0.1 Sodium Chloride 1.5 Water q.a. The pH of the formulation was in the range of 3.5-5

(14) TABLE-US-00005 TABLE 5 Results of the viscosity assessment of the shampoo preparations Quater- Anhydride Amount Viscosity Product Polymer nisation building block [wt.-%] [mPas] form A3 SMCA DDSA 5 16000 Good (inventive) A3 SMCA DDSA 2 18000 Good (inventive) A3 SMCA DDSA 1 19000 Good (inventive) A1 DMS DDSA 2 840 Too liquid (Reference) A1 DMS DDSA 0.5 1080 Too liquid (Reference) E2 MeSAP HHPA 2 1020 Too liquid (Reference) E2 MeSAP HHPA 0.5 1280 Too liquid (Reference) E3 SMCA HHPA 5 200 Too liquid (Reference) E3 SMCA HHPA 2 500 Too liquid (Reference) E3 SMCA HHPA 1 700 Too liquid (Reference)

(15) As can be retrieved from the results of the examples presented in table 3 and 5 only the use of polymers according to the present invention built up with 2-dodecen-1-ylsuccinic anhydride as anhydride building block and which are quaternized with sodium 2-chloroacetate result in clear shampoo formulation with acceptable viscosities.