1,3-PROPYLENE ETHER DERIVED COMPOUNDS FOR PERSONAL CARE

Abstract

A compound has the structure of formula (1): X(OCH.sub.2CH.sub.2CH.sub.2).sub.nOR (1) in which n is an integer from 2 to 15, R is a C.sub.6 to C.sub.36 hydrocarbyl group, X is R or R.sub.1C(O) and R.sub.1 is a C.sub.2 to C.sub.36 hydrocarbyl group. A personal care product contains the compound of formula (1). A method of producing the compound and the use of the compound as a sensory agent and/or pigment wetting agent in a cosmetic or personal care product are also disclosed.

Claims

1. A compound of the following formula 1:
X(OCH.sub.2CH.sub.2CH.sub.2).sub.nOR (1) wherein: n is an integer from 2 to 15, R is a C.sub.6 to C.sub.36 hydrocarbyl group, X is R or R.sub.1C(O), and R.sub.1 is a C.sub.2 to C.sub.36 hydrocarbyl group.

2. The compound according to claim 1, wherein the R group is a C.sub.10 to C.sub.20 hydrocarbyl group.

3. The compound or composition according to claim 1, wherein the R.sub.1 group is a C.sub.10 to C.sub.22 hydrocarbyl group.

4. The compound according to claim 1, wherein the R and/or R.sub.1 groups are alkyl groups.

5. The compound according to claim 1, wherein the value of n is in the range from 3 to 7.

6. The compound according to claim 1, being caprylate/caprate-(OCH.sub.2CH.sub.2CH.sub.2).sub.5-isostearyl, wherein in formula (1) X is R.sub.1C(O) with R.sub.1 being C.sub.7-10, n is 5, and R is an isostearyl group.

7. A composition comprising a mixture of compounds of claim 1.

8. A composition according to claim 7, wherein the mixture comprises at least: (i) the compound(s): R(OCH.sub.2CH.sub.2CH.sub.2).sub.nOR, (1a); and (ii) the compound(s): R.sub.1C(O)(OCH.sub.2CH.sub.2CH.sub.2).sub.nOR (1b).

9. The composition according to claim 7, wherein the ratio by weight, based on the total weight of the composition, between compound(s) of formula (1a) and compound(s) of formula (1b) is greater than 2:1.

10. The composition according to claim 7, further comprising at least a compound of formula (1c):
R.sub.1C(O)(OCH.sub.2CH.sub.2CH.sub.2).sub.mOR.sub.2CO (1c), wherein: m is an integer from 2 to 15, R.sub.1 and R.sub.2 are independently a C.sub.2 to C.sub.36 hydrocarbyl group.

11. The composition according to claim 10, wherein the R.sub.1 and R.sub.2 groups are C.sub.10 to C.sub.22 alkyl groups.

12. The composition according to claim 11, wherein the R.sub.1 and R.sub.2 are identical groups.

13. The composition according to claim 10, wherein the value of m is in the range from 3 to 7.

14. The composition according to claim 10, wherein the value of n and m are identical.

15. The composition according to claim 10, comprising less than 30% by weight of compound(s) of formula (1c) with regard to the total weight of the mixture composition.

16. The composition according to claim 7 comprising (i) greater than 50% by weight of compound(s) of formula (1a): R.sub.1CO(OCH.sub.2CH.sub.2CH.sub.2).sub.nOR, and (ii) less than 30% by weight of compound(s) of formula (1b): R(OCH.sub.2CH.sub.2CH.sub.2).sub.nOR, all % by weight based on the total weight of the composition.

17. A personal care product comprising the compound according to claim 1.

18. The personal care product of claim 17 wherein the product comprises the compound as a rheology modifier.

19. The personal care product of claim 17, wherein the personal care product further comprises a personal care and/or cosmetic active ingredient comprising an active agent selected from a sunscreen agent, an anti-perspirant agent, an anti-aging agent, a moisturizing agent, a hair or scalp care agent, and a coloring or pigment agent.

20. Use of the compound according to claim 1 as a sensory agent and/or pigment wetting agent in a cosmetic or personal care product.

21. A method of producing a compound according to claim 1, the method comprising: a first step of preparing an etherified-polytrimethylene ether glycol mixture by reacting polytrimethylene ether glycol and an alcohol having the formula ROH in the presence of a strong acid catalyst; and a second step of esterifying the reaction product obtained in the first step with a fatty carboxylic acid of formula R.sub.1COON, in the presence of a strong acid catalyst.

Description

EXAMPLES

[0126] The invention is illustrated by the following non-limiting examples. All parts and percentages are given by weight unless otherwise stated.

[0127] It will be understood that all tests and physical properties listed have been determined at atmospheric pressure and ambient temperature (i.e. about 23 C.), unless otherwise stated herein, or unless otherwise stated in the referenced test methods and procedures.

Test Methods

[0128] In this specification the following test methods have been used:

[0129] (i) Emulsion stability was assessed by observing the emulsions after storage for 3 months at ambient temperature (23 C.), cold at 5 C. or under elevated temperature storage at 40 C., 45 C. and 50 C. Measuring storage stability at 50 C. is a severe test. The emulsions were also assessed for their freeze-thaw stability using a cycling oven (10 C. to 40 C. in 24 hours). The composition was stable if no visible separation of the emulsion occurred. The stability of the emulsions was also assessed by monitoring the size of the dispersed phase water particles over a three month period. The particle size was measured using a Malvern Mastersizer 2000 that measures the size of the dispersed phase particles using laser diffraction.

[0130] (ii) Emulsion viscosity was measured at 23 C. with a Brookfield LVT viscometer using an appropriate spindle (LV1, LV2, LV3, or LV4) depending on the viscosity of the emulsion. The emulsion was tested at 10 rpm (0.1 Hz), 1 day after making the emulsion and results are quoted in mPa.Math.s.

[0131] (iii) The hydroxyl value is defined as the number of mg of potassium hydroxide equivalent to the hydroxyl content of 1 g of sample, and was measured by acetylation followed by hydrolysation of excess acetic anhydride. The acetic acid formed was subsequently titrated with an ethanolic potassium hydroxide solution.

[0132] (iv) The acid value is defined as the number of mg of potassium hydroxide required to neutralize the free acids in 1 g of sample, and was measured by direct titration with a standard potassium hydroxide solution.

[0133] (v) The particle size was determined according to ASTM method D1210 -05(2014) Standard Test Method for Fineness of Dispersion of Pigment-Vehicle Systems by Hegman-Type Guage.

[0134] Where mentioned herein, concentrations are given by weight based on the total weight of the compound/composition/formulation.

Preparation Examples

Example 1: General Method of Preparation of a Mixture Composition of the Invention Comprising the R.SUB.1.C(O)(OCH.SUB.2.CH.SUB.2.CH.SUB.2.)nOR Compound of the Invention

First Step of Preparation of a Precursor Mixture Composition Comprising the R(OCH.SUB.2.CH.SUB.2.CH.SUB.2.)nOH Compound

[0135] 3-10 moles of vegetable derived 1,3-propanediol, 1 mole of fatty alcohol of formula ROH and concentrated sulfuric acid catalyst were added to a reaction flask with nitrogen inlet, mechanical stirrer and a distillation head. The mixture was heated to 150-170 C. with a nitrogen sparge and held for 2.5 hours. The temperature was then increased to 175-250 C. and held for up to 24 hours. At this point, the temperature was lowered to 75 C. and a 45% KOH solution and de-ionized water were added. The resulting aqueous mixture was held at 75 C. and stirred for 2-4 hours under nitrogen to hydrolyze the acid ester formed during the acid catalyzed polycondensation and to neutralize the residual acid. The reaction mixture was then allowed to stand for phase-separation with the bottom layer being the aqueous phase and the top layer being the organic phase. After the aqueous phase was removed, the organic phase was dried under vacuum and filtered.

[0136] This step resulted in the preparation of a mixture composition comprising mostly the monocapped ether compound H(OCH.sub.2CH.sub.2CH.sub.2)nOR (in weight with regard to the total weight of the composition).

The composition obtained also comprises in minor amount the dicapped compound R(OCH.sub.2CH.sub.2CH.sub.2)nOR.

Second Step of Esterification of the Precursor Mixture Composition

[0137] 1 mole of the product mixture prepared in the first step, 1 mole of fatty acid of formula R.sup.1COOH and 0.1 w/w % of tin II oxalate catalyst were added to a clean, dry flask with nitrogen inlet, mechanical stirrer and a distillation head. The reaction mixture was heated to and held at between 180-220 C. while being tracked by acid value drop. Once an acid value of <2 was achieved, the batch was cooled to 90 C., dried and filtered.

[0138] This step resulted in the preparation of a composition mostly comprising the monocapped compound of the invention R.sup.1C(O)(OCH.sub.2CH.sub.2CH.sub.2)nOR and in minor amounts the dicapped compound of the invention R(OCH.sub.2CH.sub.2CH.sub.2)nOR formed in the first step, and the diester compound R.sup.1C(O)(OCH.sub.2CH.sub.2CH.sub.2)nO(CO)R.sup.1.

[0139] No residual polypropane diol or free alcohol was detected.

Preparation of Isostearate-PPDS-Istearyl According to This Method

[0140] First step: the procedure was conducted using 894 g of vegetable derived 1,3-propanediol, 657 g of isostearyl alcohol and 4.7 g concentrated sulfuric acid were added to a 3 L four-neck round bottom flask. After the reaction, 4.4 g of a 45% KOH solution and 320 g of de-ionized water were added and the resulting aqueous mixture was held at 75 C. and stirred for 4 hours under nitrogen.

[0141] Second step: 439 g of the product PPD-5 isostearyl alcohol prepared in the first step, 237 g of isostearic acid and 0.8 g tin II oxalate catalyst were added to a clean, dry 1 L four-neck round bottom flask with nitrogen inlet, mechanical stirrer and a distillation head. The reaction mixture was heated to and held at between 180-220 C. while being tracked by acid value drop.

Example 2: Distribution

[0142] The following table 1 outlines results of NMR data used to determine distribution for different products prepared according to the above mentioned first step of the method with different length PPD chains and fatty alcohol used for capping selected from Cetearyl alcohol (sold under the tradename Crodacal 1618 supplied by Croda Inc., comprising a distribution of cetyl (C16) and stearyl (C18) alcohols) and myristyl alcohol (sold under the tradename Crodacol M95 supplied by Croda Inc., consisting of C14 alcohol).

TABLE-US-00001 monocaped ether dicaped ether PPD % compound % compound % (n H(OCH.sub.2CH.sub.2CH.sub.2)nOR R(OCH.sub.2CH.sub.2CH2)nOR repeating Free (n repeating units) (n repeating units) units) Alcohol PPD3- 52.4 (~3) 10.9 (~1) 27 (~7) 9.7 Myristyl PPD3- 66.7 (~3) 15.7 (~1) 3.5 (~7) 14.1 Myristyl PPD3- 60.6 (~3) 14.4 (~3) 6.2 (~3) 18.9 Cetearyl PPD5- 61.2 (~4) 7.5 (~1) 23.6 (~7) 7.8 Myristyl PPD5- 75.0 (~5) 11.3 (~5) 8.2 (~5) 5.6 Myristyl PPD5- 71.1 (~5) 11.3 (~5) 9.0 (~5) 8.7 Cetearyl PPD10- 56.9 (~10) 7.8 (~10) 31.6 (~10) 3.6 Cetearyl
The method of example 1 was applied to prepare a mixture composition comprising the cetearyl-PPD5-caprylate/caprate compound of the invention (from a mixture of caprylic (CS) and capric (C10) acids reacted with the PPD5-cetearyl alcohol mixture mentioned above)the distribution of the different compounds of the mixture was determined by NMR analysis (Standard 1H and 13C NMR experiments) and is shown in the following table 2.

TABLE-US-00002 TABLE 2 Weight %/total weight Compound of the composition caprylate/caprate-PPD5-cetearyl 81.15 cetearyl-PPD5-cetearyl 10.54 caprylate/caprate-PPD5-caprylate/caprate 8.31

Application Examples

[0143] In the following examples, the mixture composition of the invention is used which comprises the ester-PPDn-ether compound as the major component. However, for simplification, the name ester-PPDn-ether is used in the text to designate the mixture.

Example 3: Evaluation of Caprate/Caprylate-PPD5-Isostearyl in Color Cosmetic Products of the Dispersing Properties of Inorganic Solid Pigments/Dyes

[0144] The objective was to evaluate the pigment wetting capacity of the caprate/caprylate-PPD5-isostearyl of the invention compared to most commonly used dispersion emollient media in colour cosmetics namely: [0145] Cromollient DP3A, a di-ester of propoxylated myristyl alcohol and adipic acid, marketed by Croda (INCI name: DI-PPG-3 Myristyl Ether Adipate); [0146] Crodamor GTCC, a caprate/caprylate triglyceride (INCI name: Caprylic/Capric Triglyceride); and [0147] Castor oil (INCI name: Ricinus Communis (Castor) Seed Oil).

[0148] A red pigment (Red 7 Calcium LakeINCI name: Cl 15850) at a ratio media/pigment of 55:45 was tested. Each emollient/media was mixed with this pigment and the dispersion formed was mixed with an overhead stirrer for hour, followed by three passes through a three roll mill.

Viscosity Test

[0149] Measurements of viscosity after stabilization (after 24hours) of the dispersions were taken with a Brookfield viscometer and are reported in the following table 3.

TABLE-US-00003 TABLE 3 Viscosity in cps of the dispersions Viscosity Emollient (cps) Caprate/caprylate-PPD5-isostearyl of the invention 30,000 Cromollient DP3A 25,000 Crodamol GTCC 5,000 Castor oil 250,000

Particle Size Test

[0150] The standardized test of Hegman Gauge and Fineness of Grind was used to approximate the particle size. It consists of placing a small volume of product on the deep end and drawing it with a straight scraper toward the shallow end. The position on the scale where oversize particle and their tracks appear is rated for determination of dispersion. The results are reported in the following table 4.

TABLE-US-00004 TABLE 4 Particle size approximation in m in the dispersions Emollient Hegman Gauge Caprate/capryiate-PPD5-isostearyl of the invention 4.25 m Cromollient DP3A 7.00 m Crodamol GTCC 11.00 m Castor oil 5.75 m

[0151] Lower viscosity is not directly proportional to better pigment dispersion. This is shown by the results above for the Crodamol GTCC exhibiting the lowest viscosity (5,000cps) but the highest particle size (11.00 m) in the dispersion.

[0152] In fact, dispersion mixture needs to be optimal and requires that pigmentary particle size is significantly reduced to prevent any agglomeration or re-agglomeration. A typical pigment dispersion particle size is 5 m. Below 5 m depicts superiority in the dispersion. A synergy between low particle size dispersion and a satisfactory viscosity is more favorable than a low viscosity evaluation alone.

[0153] The caprate/caprylate-PPD5-isostearyl of the invention exhibits a particle size below 5 pm together with a satisfactory viscosity level comparable to conventional used emollient like the CromollientiDP3A.

Color Intensity via Colorimetry

[0154] The color intensity was performed by evaluating the L* and a* values of each dispersion.

[0155] Defined by the Commission Internationale de l'Eclairage (CIE), the L*a*b* color space was modeled after a color-opponent theory stating that two colors cannot be red and green at the same time or yellow and blue at the same time.

[0156] L* indicates lightness/darkness of the sample.

[0157] a* is the red/green coordinate.

[0158] b* is the yellow/blue coordinate.

[0159] The following table 6 shows the results.

TABLE-US-00005 TABLE 6 Emollient L* a* b* c* h* Caprate/caprylate-PPD5-isostearyl 32.35 33.60 15.68 37.10 25.10 of the invention Cromollient DP3A 32.45 32.13 15.58 35.71 25.87 Crodamol GTCC 32.45 35.33 16.96 39.19 25.64 Castor oil 31.30 36.78 12.78 38.97 19.31

[0160] Cromollient DP3A and Crodamol GTCC exhibit the lightest sample tested and the highest red coordinate belongs to castor oil. Overall, the lightness result of the compound of the invention (32.35) is only 0.10% different than its counterparts Cromollient DP3A and Crodamol GTCC (32.45), and the redness/red color intensity for the caprate/caprylate-PPD5-isostearyl of the invention (33.60) is 8.00% different than the emollient that exhibits the highest color vibrancy. It can be concluded, therefore, that the color intensity of pigment dispersions with the compound of the invention is comparable to conventional used emollients.

Example 4: Personal Care or Cosmetic Products According to the Invention

[0161] The compounds of the invention have very good compatibility with many different types of skin care systems ranging from sticks, waxes, pigments, lotions, sunscreens, with excellent stability as for example shown by the following test.

Stability Test

[0162] A wax system was made for a simple lip balm chassis. The system consisted of waxes and super sterol ester. Two systems were made, one with the Cromollient DP3A, and another with the caprate/caprylate-PPD5-isostearyl of the invention using 12% of each. Both were placed in 50 C. oven for 24hours. The lip balm with the Cromollient DP3A experienced significant sweating while the system with the compound of the invention was completely intact and unchanged.

[0163] Examples of other personal care and cosmetic products according to the invention are given below.

As shown in Tables 7-15 below, weights are collective for all Parts. For example, as shown in Table 7, the sum of the weights in Parts A-C is 100%.

[0164] The ester-PPDn-ether compound of the invention mentioned in these formulations is present either alone or as part of a mixture composition according to the invention comprising the named compound as the major component (w/w) compared to the corresponding ether-PPDn-ether and ester-PPDn-ester components.

TABLE-US-00006 TABLE 7 Sprayable Sunscreen Lotion Ingredients Weight % Part A: Deionized Water 61.20 Xanthan Gum 0.20 CRODAFOS CS-20 ACID (Cetearyl Alcohol, Ceteth-20 4.00 Phosphate, Dicetyl Phosphate) Glycerin 5.00 Triethanolamine (TEA, 98%) 0.10 Part B: CRODAMOL AB (C12-C15 Alkyl Benzoate) 3.00 Caprate/caprylate-PPD5-isostearyl of the invention 5.00 Octinoate 7.50 Octisalate 5.00 Oxybenzone 5.00 CHROMAVEIL (Cas# 1030827-59-8) 3.00 Part C: Propylene Glycol, Diazolidinyl Urea, Methyl Paraben, 1.00 Propyl Paraben

[0165] The sprayable sunscreen disclosed in Table 7 was formed by heating deionized water to a temperature between about 75 C. to about 80 C., then adding the xanthan gum, and allowing the xanthan gum to completely hydrate. The remaining ingredients of Part A in Table 7 were added one at a time, each ingredient being allowed to fully dissolve before adding the next ingredient. Separately, Part B was prepared by combining the ingredients of Part B in Table 7 and heating to about 75 C. Once Part A and Part B were prepared, Parts A and B were combined and maintained at a temperature between about 75 C. to about 80 C. for about 15 minutes. The mixture of Parts A and B was then cooled to about 45 C. Once cooled, Part C was added to the mixture of Parts A and B. The combined mixture was then be cooled and packaged.

TABLE-US-00007 TABLE 8 Acid cream Ingredients Weight % Part A: CRODAFOS CS-20 ACID (Cetearyl Alcohol, Ceteth-20 8.0 Phosphate, Dicetyl Phosphate) CRODACOL C-70 (Cetyl Alcohol) 2.0 Mineral Oil 14.50 CRODAMOL STS (PPG-3 Benzyl Myristate) 3.00 SUPER STEROL ESTER (C10-C30 Cholesterol/Lanosterol 5.00 Esters) Ethylhexylmethoxy Cinnamate 5.00 Part B: Salicylic Acid 2.00 Caprate/Caprilate-PPD5-isostearyl of the invention 3.00 Part C: Deionized water 52.20 Glycerin 5.00 Sodium Hydroxide (pellets, 97%+) 0.30

[0166] The acid cream disclosed in Table 8 was formed by combining and heating the components of Part A to about 80 C. Part B added to Part A, and the acid crystals were allowed to dissolve. Separately, the components of Part C were combined and heated to about 80 C. Then, Part C was added to the existing mixture of Parts A and B while mixing. The combined mixture of Parts A, B and C were maintained at about 80 C. for about 20 minutes, and then cooled to room temperature without using a water bath.

TABLE-US-00008 TABLE 9 Microemulsion Styling Gel Ingredients Weight % Part A: INCROCAS 30 (PEG-30 Castor Oil) 10.00 Mineral Oil 10.00 Brij O10 (Oleth-10) 10.00 Brij O20 (Oleth-20) 11.00 INCROQUAT BEHENYL 18-MEA (Behentrimonium 2.00 Methosulfate, Quaternium-33, Cetearyl Alcohol) Propyl Paraben 0.20 Part B: Deionized water 40.60 Glycerin 7.00 Polypropylene Glycol 5.00 Behenate-PPD4-isostearyl of the invention 4.00 Methyl Paraben 0.20

[0167] The styling gel disclosed in Table 9 was formed by combining the ingredients of Part A while mixing and heating at a temperature between about 90 C. to about 95 C. Separately, the ingredients of Part B were combined while mixing and heating at a temperature between about 90 C. to about 95 C. Then, Part B was added to Part A while rapidly mixing and maintaining the temperature for about 15 minutes. Then, the mixture of Parts A and B was cooled to about 60 C. and poured into molds before the mixture reached a set point of about 50 to about 55 C., pH: 6.000.50.

TABLE-US-00009 TABLE 10 Cationic Skin Moisturizing Lotion Ingredients Weight % Part A: Deionized water 76.98 Laurate-PPD5-behenyl of the invention 10.00 Glycerin 5.00 CRODACOL S-70 (Stearyl Alcohol) 2.52 INCROQUAT BEHENYL TMS-50 (Behentrimonium 2.50 Methosulfate, Butylene Glycol, Cetearyl Alcohol) Part B: Cyclomethicone 2.00 Polypropylene Glycol, Diazolidinyl Urea, Methyl Paraben, 1.00 Propyl Paraben

[0168] The moisturizing lotion disclosed in Table 10 was formed by combining the ingredients of Part A while mixing and heating at a temperature between about 75 C. to about 80 C. The heating temperature of Part A was maintained for about 15 minutes, and then the mixture of Part A was cooled to about 50 C. The ingredients of Part B were then added individually to Part A while mixing. The lotion was then be cooled and packaged.

TABLE-US-00010 TABLE 11 Conditioning Shampoo with UV Protection Ingredients Weight % Part A: Deionized Water 29.22 Glycerin 1.00 Disodium EDTA 0.20 PEG 7M 0.20 Part B: Ammonium Lauryl Sulfate (ALS), 28% 14.00 Ammonium Lauryl Ether Sulfate (ALES), 25% 40.00 INCRONAM 30 (Cocamidopropyl Betaine) 6.60 LUSTREPLEX (Polyquaterium-70 (and) 1.42 Dipropylene Glycol) Glycol Distearate 0.80 CHROMAVEIL (cas# 1030827-59-8) 2.50 Silicone 0.50 Caprate/Caprilate-PPDS-isostearyl of the invention 2.00 Part C: CRODASONE W (Hydrolyzed Wheat Protein PG-Propyl 1.00 Silanetriol) CROSILK LIQUID (Silk Amino Acids) 0.20 Methylisothiazolinone 0.10 Part D: CROTHIX LIQUID (PEG-150 Pentaerythrityl 0.26 Tetrastearate (and) PEG-6 Caprylic/Capric Glycerides (and) Water)

[0169] The conditioning shampoo disclosed in Table 11 was formed by combining the initial three ingredients of Part A and mixing until the solid had dissolved. Then, the remaining ingredient, PEG 7M was added and mixed until hydrated. Then, the ingredients of Part B were added to the mixture of Part A at temperatures up to about 75 C. and mixed until solids had dissolved. The Part A/Part B mixture was cooled to about 40 C., and then the ingredients of Part C were added. Once the ingredients of Part C had been dissolved in the Part A/Part B mixture, the pH of the combined Part A/Part B/Part C mixture was be determined. If the pH was outside a range of about 5.5 to about 7.0, the pH was adjusted to be within that range. Then, the ingredients of Part D were added while slowly mixing between about 100 to about 300 rotations per minute (rpm).

TABLE-US-00011 TABLE 12 Hair Conditioning Rinse with UV Protection Ingredients Weight % Part A: Crodazozosoft DBQ (Quaternium 91 (and) Cetrimonium 2.50 Methosulfate (and) Cetearyl Alcohol Dimethicone 5.00 CRODACOL S-70 (Stearyl Alcohol) 2.50 Wheat Germ Oil 1.00 BHT 0.10 CHROMAVEIL (cas# 1030827-59-8) 2.00 Isostearate-PPDS-isostearyl of the invention 2.00 Part B: Deionized Water 80.90 Part C: Propylene Glycol (and) Diazolidinyl Urea (and) 1.00 Methylparaben (and) Propylparaben Part D: HYDROTRITICUM WAA (Wheat Amino Acids) 3.00

[0170] The hair conditioning rinse disclosed in Table 12 was formed by combining the ingredients of Part A while mixing and heating at a temperature between about 80 C. to about 85 C. Separately, the ingredients of Part B were heated at a temperature between about 80 C. to about 85 C. Then, Part B was added to Part A while mixing and maintaining the temperature for about 15 minutes. Then, the mixture of Parts A and B was cooled to about 50 C. After cooling, the ingredients of Part C were added while mixing, followed by the ingredients of Part D.

TABLE-US-00012 TABLE 13 Anti-Perspirant Ingredients Weight % Part A: Behenate-PPD3-behenyl of the invention 47.00 ARLAMOL PM3 (PPG-3 Myristyl Ether) 3.00 ARLAMOL PB14 (PPG-14 Butyl Ether) 2.00 ARLAMOL PC10 (PPG-10 Cetyl Ether) 2.00 BRIJ S10 (Steareth-10) 1.00 Part B: CRODACOL S95 (Stearyl Alcohol) 16.00 Hydrogenated Castor Oil 3.50 Corn Starch Modified 3.00 Fumed Silica 0.50 Part C: Aluminum Zirconium Tetrachlorohydrex GLY 22.00

[0171] The anti-perspirant disclosed in Table 13 was formed by combining the ingredients of Part A while mixing and heating at a temperature are then added to the mixture. Once the first two ingredients of Part A were dissolved, then the remaining ingredients of Part B were added. Each remaining ingredient of Part B was added individually. The mixture of Parts A and B was mixed until it was homogeneous. Then, the mixture is cooled to a temperature between about 60 C. to about 65 C. While maintaining that temperature, the ingredients of Part C were added while mixing and the mixture was mixed until it was homogeneous. Then, the mixture is cooled to a temperature of about 50 C., and poured into molds to form a solid anti-perspirant.

TABLE-US-00013 TABLE 14 Hair Color Crme Ingredients Weight % Part A: Deionized Water 58.65 Sodium Sulfite 0.30 EDTA 0.20 Sodium Isoascorbate 0.30 incromidE CDEA (Cocamide DEA) 3.00 Glycerin 0.50 Incromectant AMEA 100 (Acetamide MEA) 0.50 p-Phenylenediamine 0.05 4-amino-2-hydroxytoluene 0.80 Resorcinol 0.20 1-Napthol 0.20 p-aminophenol 0.80 Part B: KeraTint EZ (Cetyl Alcohol (and) Stearyl Alcohol 19.00 (and) PPG-5 Ceteth-20 & Dicetyl Phosphate (and) Ceteth-10 Phosphate (and) Behentrimonium Methosulfate) Oleate-PPD5-isostearyl of the invention 2.00 Part C: CRODASONE W (Hydrolyzed Wheat Protein PG-Propyl 2.00 Silanetriol) CROSILKQUAT (Cocamidopropyl Hydroxypropyl Silk 0.50 Amino Acids) CRODATERIC CAS 50 (Cocamidopropyl 1.00 Hydroxysultaine) Part D: Ammonia 10.00

[0172] The hair color crme disclosed in Table 14 was formed by combining the ingredients of Part A while mixing and heating to a temperature of up to about 70 C., and until the ingredients were dissolved. Separately, the ingredients of Part B were heated up to about 70 C. Then, Part B was added to Part A while mixing and maintaining the temperature for about 15 minutes. Then, the mixture of Parts A and B were cooled to at temperature of about 45 C. After cooling, the ingredients of Part C were added while mixing. After further cooling or at a temperature of about 35 C., the ingredients of Part D were added to Parts A/B/C and the mixture mixed for about 1 hour. The mixture may then be mixed with a hydrogen peroxide developer at a weight ratio of about 1:1, at the time of application to hair.

TABLE-US-00014 TABLE 15 Lip Stick Ingredients Weight % Part A: Syncrowax OSW (Tribehenin (and) Sorbitol/Sebacic 3.50 Acid Coploymer Behenate) Castor Oil 23.55 Crodamol PTIS (Pentaerythrityl Tetraisostearate) 16.50 Isostearate-PPD5-cetearyl of the invention 11.00 Super Sterol Ester (C10-30 Cholesterol/Lanosterol Esters) 5.00 Microcrystalline Wax 2.00 Ozokerite 1.50 Carnauba Wax 1.25 Candelilla Wax (refined) 5.00 Part B: Castor Oil 18.20 C19-7711 Red 7 Lake (Sun Chemical Corp.) 1.50 C19-7712 Red 6 Lake (Sun Chemical Corp,) 3.00 C39-4433 Blue 1 Lake(Sun Chemical Corp,) 0.95 C33-8073 Cosmetic Yellow (Sun Chemical Corp.) 1.00 Part C: Mica (Mearlmica MMCF) 4.00 Titanium Dioxide (and) Mica (and) Silica (Mearlmica MMCF) 2.00 Acorbyl Palmitate 0.05

[0173] The lip stick disclosed in Table 15 was formed by combining the ingredients of Part A while mixing and heating between a temperature of about 85 C. to about 90 C., and until the mixture was clear. Separately, ingredients of Part B were mixed until particle size was less than about 25 microns. In some embodiments, a three-roll mill was utilized to achieve the desired particle size. Then, Part B was added to Part A while continuing to mix until the mixture of Parts A and B was homogeneous. Then, the mixture of Parts A and B was cooled to about 75 C. After cooling, the ingredients of Part C were added while mixing and then the mixture was poured into molds at a temperature of about 70 C.

TABLE-US-00015 TABLE 16 Make-Up Remover Ingredients Weight % Part A: Deionized Water 63.0 Propylene Glycol 5.0 Part B: Caprate/Caprilate-PPDS-isostearyl of the invention 25.00 Incroquat TMS -50 (Behentrimonium Methosulfate (and) 4.00 Cetyl Alcohol (and) Butylene Glycol) Crodacol C-70 (Cetyl Alcohol) 2.00 Part C Propylene Glycol (and) Diazolidinyl Urea (and) 1.00 Methylparaben (and) Propylparaben

[0174] The Make-up remover disclosed in Table 16 was formed by combining the ingredients of Part A while mixing and heating to a temperature of about 80 C. Separately, ingredients of Part B were mixed and heated to a temperature of about 80 C. Part B was then added to Part A while continuing to mix and maintain heat at about 80C for 10 minutes. The mixture of Parts A and B was cooled to about 40 C., and then Part C was added and the resulting formulation cooled to room temperature.

[0175] Although the invention herein has been described with reference to particular embodiments, it is to be understood that these embodiments are merely illustrative of the principles and applications of the present invention, it is therefore to be understood that numerous modifications may be made to the illustrative embodiments and that other arrangements may be devised without departing from the spirit and scope of the present invention as defined by the appended claims.