DERIVATIVES OF 1,3-PROPANEDIOL

Abstract

The present invention relates to products that are derived from renewable biobased 1,3-propanediol (“1,3-PDO”). In this regard, aspects of the present invention involve the use of “green chemistry” in that products of the present invention are capable of being made from a renewable source of raw material.

Claims

1. (canceled)

2. (canceled)

3. (canceled)

4. (canceled)

5. (canceled)

6. (canceled)

7. (canceled)

8. (canceled)

9. A process which can be used to prepare a biobased emulsifying agent which is effective in formulating an oil-in-water emulsion or a water-in-oil emulsion which contains ingredients that have hygienic and/or beautifying properties such that one or more of the ingredients are effective for use in creams, moisturizers, shampoos, hair conditioners body care lotions, including facial and hand-care formulations, sunscreens, make-up removers, and liquid soaps, wherein said emulsifying agent (A) is present in an amount at least effective to form the emulsion and maintain its stability for more than one year, said emulsifying agent (B) has an HLB of about 1 to about 20, said emulsifying agent comprising at least one fatty acid ester in which the source of the acid residue of the ester is a fatty acid having a chain length of about 2 to about 40 carbon atoms (hereafter “a fatty acid”) and the source of the alcohol residue of the ester is one or more of (A) poly(1,3-propanediol)polymer; (B) 1,3-propandiol glycerol; (C) poly(1,3-propanediol glycerol)copolymer; or (D) (1,3-propandiol capped glycerol, where the emulsifying agent includes a mixture of fatty acid esters comprising an ester which has an HLB of less than about 8 and an ester which has an HLB of about 8 to about 13, said esters being present in an amount effective to impart to the emulsions a viscosity within the range of about 2000 cp to about 300.000 cp or about 10.000 cp to about 200.000 cp.

10. A process according to claim 9, in which the mixture comprises poly(1,3-propanediolglycerol) mono-distearate and/or 1,3-propandiol capped triglycerol mono-distearate (each high HLB) and poly(1,3-propanediol) stearate and/or 1,3-propandiol stearate each (low HLB).

11. A process for preparing a personal care composition by formulating it to include the emulsifying agent prepared according to claim 9.

12. A process for preparing a personal care composition by formulating it to include the emulsifying agent prepared according to claim 10.

13. A fatty acid ester in which the source of the acid residue of the ester is a fatty acid having a chain length of about 2 to about 40 carbon atoms (hereafter a fatty acid) and the source of the alcohol residue of the ester is one or more of (A) Poly(1,3)-propanediol) polymer; (B) 1,3-propanediol glycerol; (C) Poly(1,3-propanediolglycerolcopolymer; or (D) 1,3-propanediol capped glycerol.

14. A fatty ester according to claim 13 including a fatty acid selected from the group consisting of stearic acid, coco fatty acid, oleic acid, behenic acid or wherein the source of the alcohol residue is 1,3-propanediol glycerol or wherein the source of the alcohol residue is poly(1,3-propandiolglycerol) copolymer or wherein the source of the alcohol residue is 1,3-propanediol capped glycerol.

15. A biobased emulsifying agent which has an HLB of about 1 to about 20 and which comprises at least one fatty acid ester in which the source of the acid residue of the ester is a fatty acid having a chain length of about 2 to about 40 carbon atoms (hereafter a “fatty acid”) and the source of the alcohol residue of the ester is one or more of (A) poly(1,3-propanediol) polymer; (B) 1,3-propanediol glycerol; (C) poly(1,3-piopanediolglycerol) copolymer; or (D) 1,3-propanediol capped glycerol, which includes a mixture of fatty acid esters, comprising an acid ester which has an HLB of less than about 8 and an ester which has an HLB of about 8 to about 13, said ester being present in an amount effective to impart to the emulsions a viscosity within the range of about 2000 cp to about 300.000 cp or about 10.000 cp to about 200.000 cp.

16. An emulsifying agent according to claim 15, in which the mixture comprises poly(1,3-propanediolglycerol) mono-distearate and/or 1,3-propanediol capped trigglycerol mono-distearate(each high HLB) and poly (1,3-propanediol)stearate and/or 1,3-propanediol stearate (each low HLB).

17. An emulsifying agent according to claim 15, which comprises at least about 50 wt. % water or about 65 to about 85 wt. % water.

18. An ester according to claim 13 wherein the source of the acid residue is that of claim 14 and the source of the alcohol residue is 1,3-propanediol glycerol.

19. An ester according to claim 13 wherein the source of the acid is that of claim 14 and the source of the alcohol residue is poly(1,3-propanediolglycerolcopolymer).

20. An ester according to claim 13 wherein the source of the acid residue is that of claim 14 and the source of the alcohol residue is 1,3-propanediol capped glycerol.

21. An ester according to claim 13 wherein the source of the acid residue is that of claim 14 and the source of the alcohol residue is poly(1,3)-propanediol) polymer.

Description

EXAMPLES

[0065] The Examples below describe the preparation of products according to the present invention and the preparation of compositions in which the products may be used.

[0066] Unless stated otherwise, “%” means—wt. %—and the conditions of reactions described in the examples were carried out at atmospheric pressure.

Example 1

[0067] This example describes the synthesis of a polymer that may be used as an intermediate in the synthesis of a product which can be used as an emulsifying agent (E-additive) according to an embodiment of the present invention.

Synthesis of Poly(1,3-Propanediol)

[0068] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was charged with 1500 g of 1,3-propanediol (ZEMEA, available from DuPont Tate & Lyle Bio Products) and 1.92 g of 70% methane sulfonic acid (MSA). The condenser was cooled with tap water at 55-85° F. The resulting reaction mixture was stirred with nitrogen purge for 30 minutes at room temperature (about 73° F.). The reaction mixture was then heated to 360° F. and maintained at that temperature for 11 hours. The temperature of the reaction mixture was increased to 425° F. and the mixture was heated for an additional 5.5 hours at this temperature before being cooled to room temperature.

[0069] 1192 grams of the resulting liquid poly(1,3-propanediol) product was collected from the reaction. The product had the following properties: gel permeation chromatography (GPC) Mp (peak molecular weight)=405, viscosity @25° C.=125 cp, refractive index=1.45477, and hydroxyl value=539 mg KOH/g.

Example 2

[0070] This example describes the synthesis of a copolymer that may be used as an intermediate in the synthesis of an emulsifying agent according to an embodiments of the present invention.

Synthesis of Poly(1,3-Propanediolglycerol)

[0071] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was first charged with 500 g of poly(1,3-propanediol), produced as described in Example 1, and 344 g triglycerol, followed by 2.54 g of 50% sodium hydroxide. The condenser was cooled with tap water at 55-85° F. The reaction was stirred with nitrogen purge for 30 minutes at room temperature before heating the reaction to 360° F. The reaction was held at 360° F. for 3.5 hours and then was cooled to room temperature.

[0072] 822 grams of a liquid poly(1,3-propanediolglycerol) were collected. The product had the following properties: gel permeation chromatography (GPC) Mp=707, viscosity @25° C.=810 cp, refractive index=1.46998, and hydroxyl value=479 mg KOH/g.

Example 3

[0073] This example describes the synthesis of a fatty acid ester which has a high HLB and which can be used as an E-additive according to an embodiment of the present invention.

[0074] Synthesis of Poly(1,3-Propanediolglycerol) Mono-Distearate

[0075] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was charged with 171 g of poly(1,3-propanediolglycerol), produced as described in Example 2 above, and 112 g of 70% stearic acid. The condenser was cooled with tap water at 55-85° F. The reaction mixture was heated to 180° F. and stirred until all of the stearic acid was in solution. The reaction mixture was then charged with 1.2 g of 50% sodium hydroxide. The reaction mixture was stirred with nitrogen purge for 30 minutes at 180° F. and the temperature of the reaction mixture was raised to 400° F. The mixture was heated at 400° F. for 2 hours and then cooled. After the reaction mixture was cooled to 180° F., the mixture was neutralized to pH=7 with 2.5g 70% methane sulfonic acid (MSA). The reaction mixture was filtered through 25 micron filter paper as 218 grams of the resulting solid poly(1,3-propanediolglycerol) mono-distearate product were collected.

[0076] The product had the following properties: viscosity @50° C.=69 cp, hydroxyl value=296.5 mg KOH/g, saponification value (SAP)=96.3 mg, HBL=9.5, and Gardner Color—2.5.

Example 4

[0077] This example describes the synthesis of a fatty acid ester which has a low HLB and which can be used as an E-additive according to an embodiment of the present invention.

Synthesis of Poly(1,3-Propanediol) Stearate

[0078] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was charged with 200 g of poly(1,3-propanediol), produced as described in Example 1, and 142 g of 70% stearic acid. The condenser was cooled with tap water at 55-85° F. The reaction mixture was heated to 180° F. and stirred until all of the stearic acid was in solution. The reaction mixture was then charged with 0.88 g of 50% sodium hydroxide and 0.2 g of 70% phosphorous acid. The reactor was stirred with nitrogen purge for 30 minutes at 180° F. and the temperature of the reaction mixture was raised to 400° F. for 6.5 hours and then cooled. After the reaction mixture was cooled to 180° F., the reaction mixture was neutralized to pH=7 with 1 g 85% phosphoric acid. The reaction mixture was filtered through a 25 micron filter and 248 g of a solid poly(1,3-propanediol)stearate were collected. This product had the following properties: viscosity @50° C.=31 cp, hydroxyl value=198.3 mg KOH/g, saponification value (SAP)=91.3 mg KOH/g, HLB=2.3, and Gardner Color—1.0.

Example 5

[0079] This example, like Example 4, describes the synthesis of a fatty acid ester which has a low HLB and which can be used as an E-additive according to an embodiment of the present invention.

Synthesis of 1,3-Propanediol Stearate

[0080] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was charged with 76 g of 1,3-propanediol and 284 g 70% stearic acid. The condenser was cooled with tap water at 55-85° F. The reaction mixture was heated to 180° F. and stirred until all of the stearic acid was in solution. The reaction mixture was then charged with 0.63 g of 50% sodium hydroxide and 0.145 g 70% phosphorous acid. The reaction was stirred with nitrogen purge at 180° F. for 30 minutes and the temperature of the reaction mixture was raised to 360° F. The mixture was heated at 360° F. for 11 hours and then cooled to 180° F., Then the reaction mixture was neutralized to pH=7 with 0.5 g 85% phosphoric acid. The reaction mixture was filtered through a 25 micron filter and 297 g of solid poly(1,3-propanediol)stearate were collected. This product had the following properties: viscosity @70C=10 cp, hydroxyl value=321 mg KOH/g, saponification value (SAP)=176.4 mg, HLB=3.0, and Gardner Color—2.

Example 6

[0081] This example describes the synthesis of a 1.3-propanediol capped polyglycerol that can be used as an intermediate in the synthesis of an emulsifying agent according to an embodiment of the present invention.

Synthesis of 1,3-Propanediol Capped Triglycerol

[0082] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was first charged with 108 g of 1,3-propanediol and 375 g triglycerol, followed by 2.47 g of 50% sodium hydroxide. The condenser was cooled with tap water at 55-85° F. The reaction mixture was stirred with nitrogen purge for 20 minutes at room temperature before heating the mixture to 380° F. The mixture was held at 380° F. for 6.5 hours, and then was cooled to room temperature.

[0083] 426 g of liquid 1,3-propanediol capped triglycerol were collected. The product had the following properties: viscosity @25° C.=3683 cp, refractive index=1.48382, hydroxyl value=1171 mg KOH/g.

Example 7

[0084] This example describes the synthesis of a fatty acid ester which has a high HLB and which can be used as an E-additive according to an embodiment of the present invention.

Synthesis of 1,3-Propanediol Capped Triglycerol Mono-Distearate

[0085] A clean, dry 4-necked round bottom flask equipped with a condenser and overhead stirrer was charged with 142 g of 1,3-propanediol capped triglycerol, produced as described in Example 6, and 236 g of 70% stearic acid. The condenser was cooled with tap water at 55-85° F. The reaction mixture was heated to 200° F. and stirred until all of the stearic acid was in solution and was then purged with nitrogen for 20 min. Thereafter, the reaction mixture was charged with 0.7 g of 50% sodium hydroxide and 0.18g 70% phosphorous acid. The temperature of the reaction mixture was raised to 400° F. and heated for 2.5 hours and then cooled.

[0086] 320 g of (solid) unneutralized 1,3-propanediol capped mono-distearate were collected. The product had the following properties: hydroxyl value=272 mg KOH/g, saponification value (SAP)=153 mg KOH/g, HLB=9.5, Gardner Color—3.

[0087] There follows a description of five examples of personal care formulations which comprise oil-in-water emulsions that contain fatty acid esters that are within the scope of the present invention. Each of the five formulations (A through E) contained the following ingredients (weight %): (1) 81.15% DI water; (2) 0.10% Disodium EDTA; (3) 3.00% glycerol; (4) 0.25% xanthan gum; (5) 1.50% cetearyl alcohol (Lipovol® SC); (6) 8.00% Lipocol® MOS-70(blend of tridecyl stearate, neopentyl glycol discaprylate/dicaprate, tridecyl trimellitate at 45%, 45%, 10% respectively; and (7) 1.00% :Liposerve® PP (phenoxyethanol and parabans). In addition to the above ingredients, each of the five formulations contained also the E-additives as identified below. [0088] (i) Formulation (A): 1.50% of the E-additive of Example 3 above and 3.5% poly(1,3-propanediolglycerol) tristearate having the following characteristics: hydroxyl value 208; saponification value 125; viscosity 50% at 50° C.; HLB (estimated)=7.7; Gardner Color 2. Formulation (A) had a pH of 6.27 and a viscosity (TF∜1.5 rpm at room temperature) of 49370 cp. [0089] (ii) Formulation (B): 1.5% of the E-additive of Example 3 above and 3.5% of poly(1,3-propanediolglycerol) tetrastearate having an SAP of 130; Formulation (B) had a 10H of 6.2 and a viscosity (TF@1.5 rpm at room temperature) of 8125 cp. [0090] (iii) Formulation (C): 1.5% of the E-additive of Example 3 above and 3.5% of poly(1,3-propanediolglycerol) tribehenate having an SAP of 68; Formulation (e) had a pH of 6.2 and a viscosity (TF@1.5 rpm at room temperature) of 8750 cp. [0091] (iv) Formulation (D): 1.5% of the E-additive of Example 3 above; and 3.5 wt % of poly(1,3-propanediolglycerol) tricocoate having an SAP of 140; Formulation (D) had a pH of 6.1 and a viscosity (TF@1.5 rpm at room temperature) of 2500 c/p.

[0092] (v) Formulation (E): 1.5% of the E-additive of Example 3 above and 3.5% of sisterna SP30C sucrose distearate having a melting point of 53-61° C. and an HLB of 6; Formulation(s) had a pH of 6.0 and a viscosity (TF@1.5 rpm at r.t) of 190,200 cp.

[0093] There follows a description of four additional examples of personal care formulations (Formulations (F) to (i) which have the same content of ingredients that are present in each of Formulations (A) to (E) above, but which have different E-additives as identified in Table 1 below as (a) to (e). [0094] (a) Poly(1,3-propanediolglycerol) mono-stearate having the following characteristics: SAP=67 and a viscosity@50° C. of 50 cp. [0095] (b) Poly(1,3-propanediol) stearate having the following characteristics: SAP=91 and a viscosity@50° C. of 31 cp. [0096] (c) Poly(1,2-propanediolglycerol) mono-distearate having the following characteristics: SAP=96 and a viscosity@50° C. of 67 cp. [0097] (d) Poly(1,3-propanediol) stearate having the following characteristics: SAP=102 and a viscosity at 50° C. of 26 cp. [0098] (e) 1,3-(propanediol) stearate having the following characteristics=SAP=176 and a viscosity@70° C. of 10 cp.

TABLE-US-00001 TABLE 1 Formulation E-Additives Wt. % pH Viscosity (F) 1.5% of (a) and 3.5% of (b) 5.8 36,250 (G) 1.5% of (c) and 3.5% of (b) 5.8 150,000 (H) 1.5% of (c) and 3.5% of (d) 5.95 156,200 (I) 1.5% of (c) and 3.5% of (e) 4.90 201.800
The viscosity values are those of homogenized emulsions as evaluated by TF@1.5 rpm at room temperature.

[0099] Table 2 below describes an example of a personal care formulation which is in the form of an emulsion and which can be formulated to include a mixture of two E-additives, for example, the fatty acid esters of Examples 3 and 5 above.

TABLE-US-00002 TABLE 2 Weight Ingredient Percent Sequence Deionized Water 69.65 1 Disodium EDTA (119 - Ruger Chemical Co., Inc.) 0.10 1 Glycerin (119) 1.00 1 Butylene Glycol (119) 1.00 1 Xanthan Gum 0.25 1 Sodium Chloride 0.75 1 Microcrystalline Wax 1.00 2 Cetearyl Alcohol, Lipocol ® SC (1 - Lipo 1.00 2 Chemicals, Inc.) Butyrospermum Parkii (Shea Butter), Lipobutter ® 3.00 2 Refined Shea (1) Argania Spinosa Kernel Oil, Lipovol ® ARGAN 2.00 2 (1) Glyceryl Stearate and PEG-100 Stearate, 2.75 2 Lipomulse ® 165 (1) Caprylic/Capric Triglyceride, Liponate ® GC 10.00 2 Dimethicone 1.00 2 Sorbitan Stearate, Liposorb ® S (1) 3.50 2 Lipo ® Stearic Acid (1) 3.00 3 Preservative qs 4

[0100] To the ingredients identified in Table 2 above, there are added the E-additive of Example 3 above in an amount such that its concentration in the Formulation is about 1.4 wt. %; and the E-additive of Example 5 above is added in an amount such that its concentration in the Formulation is about 3.43 wt. %.

[0101] The following procedure can be used to prepare the emulsion which is described in Table 2. [0102] (A) With reference to the ingredients identified in Table 2 by “Sequence 1”, they are added to a main vessel and mixed with a medium speed propeller and heated to 75° C. to provide a mixture. [0103] (B) The ingredients identified in Table 2 by “Sequence 2” and the E-additives are added to a side vessel and mixed as they are heated. [0104] (C) The resulting mixture of “Sequence 2” is added to the mixture of “Sequence 1” when its temperature reaches 75° C. The composition of the combined mixtures is stirred with medium mixing as cooling is begun. [0105] (D) When the temperature of the composition reaches 60° C., the stearic acid of “Sequence 3” is added with continued mixing. [0106] (E) When the temperature of the resulting composition is 45° C., the preservative of

[0107] “Sequence 4” is added with continued mixing. When the involved temperature reaches 32° C., preparation of the emulsion can be considered complete.

[0108] Formulation J below is an example of an all natural body lotion that feels soft and elegant and leaves the skin smooth and moisturized.

TABLE-US-00003 TABLE 3 Formulation J Weight Ingredient Percent Sequence Deionized Water 82.90 1 Disodium EDTA (119 - Ruger Chemical Co., Inc.) 0.10 1 Xanthan Gum (119) 0.25 2 Glycerin 99.7% (119) 2.50 2 Propanediol Stearate, Lipomulse ® ECO L (1 - 2.45 3 Lipo Chemicals, Inc.) Poly (Glycerin/Propandiol) Stearate, Lipomulse ® 1.05 3 ECO H (1) Crambe Abyssinica Seed Oil, Lipovol ® Crambe 2.75 3 (1) Vitis Vinifera (Grape) Seed Oil, Lipovol ® G (1) 4.25 3 Simmondsia Chinensis (Jojoba) Butter, 2.00 3 Iso Jojoba ® 35 (144 - Lipo Chemicals - Desert Whale Jojoba) Cetearyl Alcohol, Lipocol SC (1) 1.75 3 Preservative qs 4

[0109] The following procedure can be used to prepare the emulsion which is described in Table 3. [0110] (A) In a main vessel, the ingredients of “Sequence 1” are stirred with a medium speed propeller to form a mixture. [0111] (B) Slowly add premixed ingredients of “Sequence 2” to the mixture of (A) while mixing and heating to a temperature of 80° C. and maintain the combined mixtures at 80° C. for 30 minutes. [0112] (C) Start heating the ingredients of “Sequence 3” while mixing and heating the mixture to a temperature of 80° C. and add it to the combined mixtures of (A) and (B) in the main vessel while mixing. [0113] (D) After 5-10 minutes, homogenize the composition in the main vessel at 4000 rpm for 3-5 minutes at a temperature of 70 to 80° C. [0114] (E) Thereafter switch to propeller mixing and start to slowly cool the homogenized composition. [0115] (F) When the temperature approaches 45° C., add to the homogenized composition the preservative of Sequence 4 with, continued mixing. [0116] (G) When temperature of the homogenized composition reaches 35° C., the preparation of the homogenized emulsion can be considered complete.

[0117] Formulation K below is an example of a soft all natural cream that conditions and leaves the skin moisturized and vibrant.

TABLE-US-00004 TABLE 4 Formulation K Weight Ingredient Percent Sequence Deionized Water 72.05 1 Disodium EDTA (119 - Ruger Chemical Co., Inc.) 0.10 1 Xantham Gum (119) 0.25 2 Glycerin 99.7% (119) 2.00 2 Polypropanediol Stearate, Lipomulse ® ECO L2 (1- 3.50 3 Lipo Chemicals, Inc.) Poly(Glycerin/Propandiol) Stearates, Lipomulse ® 1.50 3 ECO H (1) Cetyl Esters, Liponate ® SPS-VEG (1) 2.50 3 Cocos Nucifera (Coconut) Oil, Lipovol ® C76 (1) 5.00 3 Olea Europea (Olive) Fruit Oil, Lipovol ® O (1) 4.00 3 Simmondsia Chinensis (Jojoba) Seed Oil, DW 6.00 3 Jojoba Colorless (144 Lipo Chemicals - Desert Whale Jojoba Cetearyl Alcohol, Lipocol ® SC (1) 3.0 3 Tocopherol, Vitamin E 0.10 3 Preservative qs 4

[0118] The following procedure can be used to prepare the emulsion which is described in Table 4. [0119] (A) In a main vessel, the ingredients of “Sequence 1” are stirred with a medium speed propeller to form a mixture. [0120] (B) Slowly add premixed ingredients of “Sequence 2” to the mixture of (A) while mixing and heating to a temperature of 80° C. and maintain the mixture at 80° C. for 30 minutes. [0121] (C) Start heating the ingredients of “Sequence 3” while mixing and heating to a temperature of 80° C. and add the heated mixture to the combined mixtures of (A) and (B) above in the main vessel while mixing. [0122] (D) After 5-10 minutes, homogenize the composition in the main vessel at 4000 rpm for 3-5 minutes at temperature of 70 to 80° C. [0123] (E) Thereafter, switch to propeller mixing and start to slowly cool the homogenized composition. [0124] (F) When its temperature approaches 45° C., add the preservative of “Sequence 4” with continued mixing to the homogenized composition. [0125] (G) When the temperature of the homogenized composition reaches 35° C., preparation of the homogenized emulsion can be considered complete.

[0126] Formulation L below is an example of a rich body butter that pampers the skin leaving it smooth and moisturized.

TABLE-US-00005 TABLE 5 Formulation L Weight Ingredient Percent Sequence Deionized Water 70.05 1 Disodium EDTA (119- Ruger Chemical Co. Inc) 0.10 1 Xantham Gum (119) 0.25 2 Glycerin 99.7% (119) 3.50 2 Polypropanediol Stearate, Lipomulse ® ECO L2 (1- 3.50 3 Lipo Chemicals, Inc.) Poly(Glycerin/Propandiol) Stearates, Lipomulse ® 1.50 3 ECO H (1) Cetyl Esters, Liponate ® SPS-VEG (1) 3.00 3 Persea Gratissima (Avocado) Oil, Lipovol ® A (1) 5.00 3 Vitis Vinifera (Grape) Seed Oil, Lipovol ® G (1) 4.00 3 Orbignya Oleifera Seed Oil, Lipobutter ® Refined 6.00 3 Mango (1) Cetearyl Alcohol, Lipocol ® SC (1) 3.00 3 Tocophearol, Vitamin E 0.10 3 Preservative qs 4

[0127] The following procedure can be used to prepare the emulsion which is described in Table 5. [0128] (A) In a main vessel, the ingredients of “Sequence 1” are stirred with a medium speed propeller to form a mixture. [0129] (B) Slowly add premixed ingredients of “Sequence 2” while mixing and heating to a temperature of 80° C. and maintain the mixture at 80° C. for 30 minutes. [0130] (C) Start heating the ingredients of “Sequence 3” while mixing and heating to a temperature of 80° C. and add the heated mixture to the combined mixtures of (A) and (B) above in the main vessel while mixing. [0131] (D) After 5-10 minutes, homogenize the composition in the main vessel at 4000 rpm for 3-5 minutes at a temperature of 70° C. to 80° C. [0132] (E) Thereafter, switch to propeller mixing and start to slowly cool the homogenized composition. [0133] (F) When its temperature approaches 45° C., add the preservative of “Sequence 4” with continued mixing to the homogenized composition. [0134] (G) When temperature of the homogenized composition reaches 35° C., preparation of the homogenized emulsion can be considered complete.

[0135] Formulation M below is an example of a natural conditioner that leaves hair soft, smooth and manageable.

TABLE-US-00006 TABLE 5 Formulation M Weight Ingredient Percent Sequence Deionized Water 82.90  1 Tetrasodium EDTA (119 - Ruger Chemical Co., 0.10 1 Inc.) Hydroxyethylcellulose, Hatrasol 250HHRCS (119) 0.25 2 Glycerin 99.7% (119) 2.50 3 Cetrimonium Chloride 3.0  3 Propanediol Stearate, Lipomulse ® ECO L (1 - 3.5  4 Lipo Chemicals Inc.) Poly(Glycerin/Propanediol) Stearates, Lipomulse ® 1.50 4 ECO H (1) Cetyl Esters, Liponate ® SPS Veg (1) 1.00 4 Argania Spinoso Kernel Oil, Lipovol ® Argan (1) 1.50% 4 Persea Gratissma Avacado Oil, Lipovol ® AL) 5.00 3 Orbignya Oleifera Seed Oil, Lopibutter ® Refined   1% 4 Mango (1) Cetearyl Alcohol, Lipovol ® SC (1) 3.00 4 Preservative qs 4

[0136] The following procedure can be used to prepare the emulsion which is described in Table 5. [0137] (A) In a main vessel, the ingredients of “Sequence 1” are stirred with a medium speed propeller to form a mixture. [0138] (B) Slowly add premixed ingredients of “Sequence 2” to the mixture of (A) while mixing and heating to a temperature of 80° C. and maintain the mixture at 80° C. for 30 minutes. [0139] (C) Start heating the ingredients of “Sequence 3” while mixing and heating to a temperature of 80° C. and add the heated mixture to the combined mixtures of (A) and (B) in the main vessel while mixing. [0140] (D) After 5-10 minutes, homogenize the composition in the main vessel at 4000 rpm for 3-5 minutes at a temperature of 70 to 80° C. [0141] (E) Thereafter, switch to propeller mixing and start to slowly cool the homogenized composition. [0142] (F) When the temperature approaches 45° C., add the preservative of “Sequence 4” to the homogenized composition with continued mixing. [0143] (G) When temperature reaches 35° C., the preparation of the homogenized emulsion can be considered complete.

[0144] In summary, the present invention provides an emulsifying agent that can be used to environmental advantage in numerous and diversified products.