BIO-BASED POLYURETHANE DISPERSIONS FOR DECORATIVE COSMETIC APPLICATIONS

Abstract

The invention relates to decorative cosmetic compositions containing specific polyurethanes or aqueous dispersions thereof and containing constituents that produce decorative effects.

Claims

1. A decorative cosmetic composition, comprising at least one polyurethane obtained by reacting one or more water-insoluble, non-water-dispersible, isocyanate-functional polyurethane prepolymers A with one or more amino-functional compounds B), wherein the polyurethane prepolymer A) is obtained by reacting one or more polyester polyols having a glass transition temperature T.sub.G of at least −50° C. and one or more polyisocyanates.

2. The decorative cosmetic composition as claimed in claim 1, wherein one or more isocyanate-functional polyurethane prepolymers A) essentially have neither ionic nor ionogenic groups.

3. The decorative cosmetic composition as claimed in claim 1, wherein the amino-functional compounds B) are selected from primary amines, secondary amines, diamines, and combinations thereof.

4. The decorative cosmetic composition as claimed in claim 1, wherein the amino-functional compounds B) comprise at least one diamine.

5. The decorative cosmetic composition as claimed in claim 1, wherein the amino-functional compounds B) are selected from amino-functional compounds B2) that have ionic and/or ionogenic groups, and amino-functional compounds B1) that do not have any ionic and/or ionogenic groups.

6. The decorative cosmetic composition as claimed in claim 1, wherein the amino-functional compounds B) comprise at least one amino-functional compound B2) that has ionic and/or ionogenic groups.

7. The decorative cosmetic composition as claimed in claim 1, wherein the amino-functional compounds B) comprise at least one amino-functional compound B1) that does not have any ionic and/or ionogenic groups.

8. The decorative cosmetic composition as claimed in claim 1, wherein the amino-functional compounds B) comprise both amino-functional compounds B2) that have ionic and/or ionogenic groups, and amino-functional compounds B1) that do not have any ionic and/or ionogenic groups.

9. The decorative cosmetic composition as claimed in claim 1, wherein the polyurethane comprises at least one sulfonic acid and/or sulfonate group.

10. The decorative cosmetic composition as claimed in claim 1, further comprising one or more constituents that produce a decorative effects.

11. (canceled)

12. A polyurethane obtained by reacting one or more water-insoluble, non-water-dispersible, isocyanate-functional polyurethane prepolymers A with one or more amino-functional compounds B), wherein the polyurethane prepolymer A) is obtained by reacting one or more polyester polyols having a glass transition temperature T.sub.G of at least −50° C. and one or more polyisocyanates.

13. A cosmetic method for producing a decorative effect on the skin and/or hair, comprising applying a composition to the skin and/or hair, the composition comprising at least one polyurethane obtained by reacting one or more water-insoluble, non-water-dispersible, isocyanate-functional polyurethane prepolymers A) with one or more amino-functional compounds B), wherein the polyurethane prepolymer A) is obtained by reacting one or more polyester polyols having a glass transition temperature T.sub.G of at least −50° C. and one or more polyisocyanates.

14. The cosmetic method as claimed in claim 13, wherein the composition remains on the skin at least to some extent after it has been applied thereto.

15. The decorative cosmetic composition as claimed in claim 6, wherein the at least one amino-functional compound B2) comprises 2-(2-aminoethylamino)ethanesulfonic acid and/or salts thereof.

16. The decorative cosmetic composition as claimed in claim 7, wherein the at least one amino-functional compound B1) comprises a diamine that does not have any ionic and/or ionogenic groups.

Description

EXAMPLES

[0266] Materials Used:

[0267] PUD 1 (comparative): Polyurethane dispersion (solids content 40% by weight) based on synthetically produced polyester polyol 1, dicyclohexylmethane diisocyanate, ethylenediamine and aminoethanesulfonic acid sodium salt, polyurethane is 100 mol % synthetic.

[0268] PUD 2 (according to the invention): Polyurethane dispersion (solids content 30% by weight) based on bio-based polyester polyol 2, isophorone diisocyanate, isophoronediamine and aminoethanesulfonic acid sodium salt, polyurethane is 55 mol % bio-based. The polyurethane present in PUD 2 corresponds to Polyurethane-93 according to INCI nomenclature.

[0269] PUD 3 (according to the invention): Polyurethane dispersion (solids content 40% by weight) based on bio-based polyester polyol 2, dicyclohexylmethane diisocyanate, ethylenediamine and aminoethanesulfonic acid sodium salt, polyurethane is 60 mol % bio-based. The polyurethane present in PUD 3 corresponds to Polyurethane-99 according to INCI nomenclature.

[0270] Polyester polyol 1 (comparative): synthetically produced from adipic acid, neopentyl glycol and hexane-1,6-diol

[0271] Polyester polyol 2: (according to the invention): bio-based polyester polyol formed from succinic acid, butane-1,4-diol and neopentyl glycol

[0272] DSC Measurements:

[0273] The glass transition temperatures Tg of the comparative polyester polyol 1 and of the polyester polyol 2 according to the invention, and also of the comparative polyurethane dispersions PUD 1 and of the polyurethane dispersions PUD 2 and PUD 3 according to the invention, in each case as a dried film, were measured by the following method:

[0274] Physical transformations such as melting points or glass transition temperatures T.sub.g are determined by measuring the heat capacity as a function of temperature using a DSC3+e calorimeter from Mettler-Toledo. The temperature and the enthalpy of fusion are calibrated using n-heptane, indium, lead and zinc. The purge gas used is nitrogen at a flow rate of 20 ml/min. Cooling is effected by means of liquid nitrogen. The temperature gradient is 20 K/min. Measurements are taken in the temperature range between −70 and +150° C. (2 heating runs).

[0275] The measurements are taken on the form as supplied, i.e. directly on the aqueous polyurethane dispersions, without preconditioning. The sample weights are between 10 and 12 mg of sample mass in a hermetically sealable perforated aluminum standard crucible.

[0276] Evaluation: the glass transition temperature T.sub.g was determined as the temperature at half height of the glass transition on the second heating run.

[0277] The results of the measurements are shown in table 1.

TABLE-US-00001 TABLE 1 DSC results No. Name Tg [° C.] C1 Polyester polyol 1 −60.1 2 Polyester polyol 2 −38.6 C3 PUD 1 −44.1 4 PUD 2 −16.5 5 PUD 3 −21.0 C Comparative

[0278] Use in Mascara:

[0279] The composition of the test mascara is given in table 2:

TABLE-US-00002 TABLE 2 Test mascara formulation Amount Phase Component (INCI name) [% by weight] A Water to 100 Hydroxyethylcellulose 0.70 Triethanolamine (99%) 2.30 Nylon-66 1.50 B Iron Oxide Black 8.00 C Glyceryl stearate 2.30 Stearic acid 5.60 Beeswax 7.00 Carnauba wax 7.00 Dimethicone 0.50 D Phenoxyethanol 0.80 Polyurethane (as solid) 4.00 Sum total 100.00

[0280] The test mascara was prepared according to the following method: [0281] 1. Dissolve ingredients of phase A in water and heat to 80° C. [0282] 2. Once phase A was homogeneous, the pigment was added with stirring, the whole mixture was homogenized. [0283] 3. In a separate vessel, the ingredients of phase C were mixed and heated to 80° C. [0284] 4. Once phase C was homogeneous, phase C was slowly added to phase A/B. The emulsion was homogenized. [0285] 5. Phase D was added during cooling. [0286] 6. After checking the pH, this was adjusted to pH 6.5 to 7.0 where necessary.

[0287] The water resistance of the mascara was tested by the following method:

[0288] Two cotton pads were moistened with water heated to 37° C. The mascara formulation was applied 10 times in a zigzag pattern to false eyelashes made from human hair. After drying, the eyelashes were placed between the two cotton pads and pulled from the root to the tip with gentle pressure. The residues on the cotton pads were assessed using the scale in table 3.

TABLE-US-00003 TABLE 3 Assessment of water resistance Degree of water resistance Value No residue on cotton pads 5 Residue area on cotton pads 0 to 1 cm.sup.2 4 Residue area on cotton pads 1 to 2 cm.sup.2 3 Residue area on cotton pads 2 to 4 cm.sup.2 2 Residue area on cotton pads more than 4 cm.sup.2 1

[0289] The results of the water resistance test are shown in table 4. The higher the value, the better the water resistance.

TABLE-US-00004 TABLE 4 Results of water resistance test Test PUD 1 PUD 2 PUD 3 Value 4 5 5

[0290] Use in an Eyeliner:

[0291] The eyeliner formulation shown in table 5 was prepared according to the method presented below.

[0292] All constituents of phase A were added to a vessel at room temperature with stirring. Once phase A was homogeneous, phase B was added. This mixture was homogenized. Phase C was then added with stirring.

TABLE-US-00005 TABLE 5 Eyeliner formulation: Amount Phase Component (INCI name) [% by weight] A Water to 100 Xanthan 0.50 Microcrystalline (and) Algin 0.30 B Iron Oxide (Black) 10.00 Sorbitan Laurate (and) Polyglyceryl-4 1.50 Laurate (and) Dilauryl Citrate C Propylene glycol 2.00 Polyurethane (solid) 5.00 Methylpropanediol (and) Caprylyl Glycol 1.50 (and) Phenylpropanol Sum total 100.00

[0293] Method for Assessing Abrasion Resistance:

[0294] The corresponding eyeliner formulation was applied as a line to the skin. Once the formulation was dry, the eyeliner line was rubbed 10 times with a foldback clip. The quality of the eyeliner film is assessed as shown in table 6. The higher the value, the better the abrasion resistance.

TABLE-US-00006 TABLE 6 Assessment of abrasion resistance Assessment of film quality Value no change in the film 5 slight scratches on the film 4 scratches on the film 3 film partially rubbed off 2 film (almost completely) rubbed off 1

[0295] The results of the abrasion resistance test are shown in table 7:

TABLE-US-00007 TABLE 7 Results of abrasion resistance test Polyurethane PUD 1 PUD 2 Value 3 5

[0296] Use in a Foundation:

[0297] A test foundation was prepared with the components shown in table 8 according to the following method. [0298] 1. Phase A was predispersed at RT, the thickeners being dispersed individually; [0299] 2. The TiO.sub.2 from phase B was added to phase A, then stirred; [0300] 3. Phase C was heated to 75° C., the remaining constituents of phase B, i.e. pigment and mica, were added to phase C, and the mixture was homogenized for 10 minutes; [0301] 4. The mixture of phases A and B was heated to 75° C., then the mixture of phases C and B was added to the mixture of phases A and B at 75° C., the resulting mixture was stirred and homogenized for 10 min; [0302] 5. Phase E was added at 45° C.

TABLE-US-00008 TABLE 8 Foundation formulation Amount Phase Component (INCI name) [% by weight] A Water to 100.00 Sodium Carboxymethyl cellulose 0.30 Magnesium Aluminum Silicate 0.35 Polysorbate 20 0.40 Triethanolamine (10%) 1.25 Butylene Glycol 6.00 B Titanium Dioxide 4.00 Red Iron Oxide 0.27 Yellow Iron Oxide 0.54 Black Iron Oxide 0.09 Mica 1.00 C Isoeicosane 9.00 Isostearic Acid 1.00 Stearic Acid 0.50 Glyceryl Stearate 0.50 Cetyl Stearyl Alcohol 3.50 Glyceryl Stearate SE 2.00 D Cyclosiloxane 2.00 Polymethylsilsesquioxane 1.00 E Polyurethane (solid) 2.00 Phenoxyethanol (and) Ethylhexylglycerin 0.80 Sum total 100.00

[0303] 0.02 g of the foundation formulation was applied to a defined area of skin using a pipette. The formulation was distributed homogeneously on the skin in a circle (30 circles). 2 subjects evaluated the formulation properties. The evaluation grades were between 0 and 5 for the properties: distribution, stickiness, powdery skin feel, color distribution, roll formation; 5 meaning that the property was fully present.

[0304] The results of the sensory evaluation are shown in FIG. 1. The references in the figure have the following meanings: [0305] 1 before drying [0306] 2 after drying [0307] 3 distribution [0308] 4 stickiness [0309] 5 powdery skin feel [0310] 6 color distribution [0311] 7 roll formation [0312] 8 without polyurethane [0313] 9 with PUD 1 [0314] 10 with PUD 2