US3567466A

US3567466A - Emulsifier for foodstuff

Info

Publication number: US3567466A
Application number: US735991A
Authority: US
Inventors: Ralph B Fearing; John C Sourby
Original assignee: Stauffer Chemical Co
Current assignee: Stauffer Chemical Co
Priority date: 1968-06-11
Filing date: 1968-06-11
Publication date: 1971-03-02
Anticipated expiration: 1988-03-02

Abstract

AN EMULSIFYING AGENT FOR OIL AND WATER FOODSTUFF COMBINATIONS CONSISTING ESSENTIALLY OF A PHOSPHATE COMPOSITION HAVING THE FOLLOWING FORMULA:

(R-O)N-P(=O)(-OH)M-(O-R1-A)Q

WHEREIN R IS A STRAIGHT CHAIN ALKYL GROUP HAVING FROM 8 TO 24 CARBON ATOMS, R1 IS A POLYOL SELECTED FROM THE GROUP CONSISTING OF MONOGLYCEROL, DIGLYCEROL, TRIGLYCEROL, TETRAGLYCEROL, AND MIXTURES THEREOF; A IS SELECTED FRM THE GROUP CONSISTING OF HYDROGEN, LACTYL, DIHYDROXYPROPIONYL, SACCHARYL, TARTARYL, GLUCONYL, MALYL AND MIXTURES THEREOF; AND N IS 1 OR 2, M IS 0 OR 1 AND Q IS 1 OR 2.

Description

United States Patent O 3,567,466 EMULSIFIER FOR FOODSTUFF Ralph B. Fearing, Bardonia, and John C. Sourby, Hawthorne, N.Y., assignors to Stautfer Chemical Company, New York, N.Y. No Drawing. Filed June 11, 1968, Ser. No. 735,991 Int. Cl. A23g 3/00; A231 N24 US. Cl. 99-139 5 Claims ABSTRACT OF THE DISCLOSURE An emulsifying agent for oil and water foodstuff combinations consisting essentially of a phosphate composition having the following formula:

BACKGROUND OF THE INVENTION In the art of preparing foodstuffs, it is the practice to add thereto a predetermined amount of an emulsifying composition. These emulsifying compositions have more properly been termed surfactants which function to improve palatability, texture and sales appeal in most commercial foodstuffs.

As is well known, the primary function of the surfactants is to increase the volume by stabilizing air incorporation. However, they also improve texture, eating quality and keeping quality. Photomicrographs of various batters show that air bubbles which contribute to volume are enclosed in films of protein in which the fat is dispersed. The role of the surfactant is to improve the ability of the protein film to entrap air in the batter during creaming or mixing. The air bubbles have a leavening effect and help control grain size by serving as foci for gas evolution.

The physical form of the surfactant is important. It must be soft enough to disperse throughout the foodstuff at room temperature but it should not have an excess of the plasticizing unsaturated acids as these have a deleterious effect on the quality of the material. Surfactants based on unsaturated fatty acids have a lower melting point and are liquid at room temperature. Because they are liquified, they over-lubricate the gluten strands resulting in a weakening gluten structure.

The simpler surfactants, chemically, are the glycerol monoesters such as glycerol monostearate. The glycerol monoester is a glyceride in which only one hydroxyl of glycerin has been replaced by fatty acid. The alpha form of the glycerol monostearate has a fatty acid connected or esterified at the end carbon. Replacement of the hydroxyl on the middle carbon yields the beta form. Both alpha and beta monoglycerides function as surfactants. These commercial surfactants must contain some of the unsaturated acids or it would be too hard for proper dispersion at processing temperatures. A good surfactant needs no premixing or preblending with other ingredients, nor does it require any special mixing procedures. Changes in formulation or fermentation should not be required in order to use a good surfactant. Normally, a surfactant that is satisfactory can also be used to preserve any baked material.

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BRIEF DESCRIPTION OF THE INVENTION It has been discovered that unique properties can be provided for oil and water combinations when employing therein as a surface active agent a material having the formulation:

DETAILED DESCRIPTION OF THE INVENTION In the practice of the present invention, the phosphate surface active agent of the present invention can be formulated by first reacting a long chain alcohol with phosphorus oxychloride. This is brought about by intermixing the long chain alcohol and phosphorus oxychloride within a reaction vessel and heating the same. The resultant product will be alkyl dichloro phosphate in essentially quantitative amounts. This reaction product is then reacted with a composition consisting essentially of two moles of glyceryl lactate, dihydroxypropionate, glyceryl saccharate, malate, tartarate, gluconate or mixtures thereof. The end product will be a long chain phosphate having the aforementioned formula.

The amount of phosphate surface active agent that can be employed with the present invention can range between 0.1 to about 10% by weight. By providing this material within an oil and water emulsion, unique properties are provided therein. These emulsions are exceptionally creamy and aerated when admixed together in a conventional manner. The degree of aeration is estimated by comparing the volumes of equal weight emulsions prepared. with the surface active agents of the present invention and with other commercially available emulsifiers. The volumes of emulsions prepared with the surface active agents of the present invention are increased to an unexpected degree.

The following examples exemplify the present invention:

EXAMPLE 1 Hexadecyl bis(lactylglyceryl) phosphate was prepared by first dissolving 240 grams of hexadecyl phosphorodichloridate in 250 milliliters of tetrahydrofuran. Thereafter, 2150 gram of glycerol lactate (1.52 moles) and grams of triethylamine (1.5 moles) was dissolved in 800 milliliters of dry acetone. The hexadecyl phosphorodichloridate solution was added to the glycerol lactate triethylamine solution at between 10 and 20 C. over a period of three hours and then left overnight. After heating the solution for one hour at 40 C., the slurry was filtered. The filtrate wa stripped at 60 C. and 10 millimeters of mercury with the residue being transferred to a separate container with 240 grams of benzene. The mixture Was diluted with 1000 milliliters of hexane to remove all of the triethylamine hydrogen chloride product. The clear one phase liquid was further diluted with 1800 milliliters of hexane producing a two phase system. The upper phase was discarded. The remaining bottom phase yielded 410 grams of hexadecyl bis lactoglyceryl phosphate. Calc. for product 5.05% P, 11% OH; found 4.3% P, 10% OH.

EXAMPLE 2 Glyceryl hexadecyl acid phosphate was made by first dissolving 150 grams of glycerine and 65 grams of triethylamine in 1500 milliliters of acetone. Thereafter, 107

a grams of hexadecyl phosphorodichloridate dissolved in tetrahydrofuran was added thereto over a period of two hours. After a half hour extra stirring, the mixture was allowed to stand four additional hours. After all the acetone was evaporated, 1000 milliliters of benzene was added. A thick bottom layer separated therefrom. The bottom phase was separated by dilution with 200 milliliters of water, causing separation of a little more benzene phase. Centrifugation separated the thic.: phases. The upper phase was identified as glyceryl hexadecyl acid phosphate at a yield of 141 grams.

EXAMPLE 3 The sodium salt of glyceryl hexadecyl phosphate of Example 2 was manufactured by dissolving 110 grams of the acid ester of Example 2 in 250 milliliters of isopropanol and 130 milliliters of ethanol. Sodium hydroxide dissolved in 200 milliliters of ethanol was added thereto. The addition of the sodium hydroxide caused a precipitation. The stoichiometric amount of NaOH for complete neutralization was ascertained from a small sample of reaction medium. After this was added, filtration yielded 62 grams of the sodium salt of the phosphate of Exampie 2. Calc. 7.4%. P, 8.1% hydroxyl, found 8.1% P, 6% hydroxyl.

EXAMPLE 4 The emulsifying effect of the material of Example 1 was tested in a mayonnaise formulation. Thus, a standard mayonnaise formulation was made by adding 18 grams of egg yolk, 15 grams of vinegar, /2 teaspoon salt, A1, teaspoon mustard, A1 teaspoon paprika and /2 teaspoon sugar to a container. Thi mixture was beaten for a short period of time at high speed with a rotary blender. Thereafter, 108 grams of oil were added thereto at 2 cc. increments over a period of 20 minutes. A second sample was formulated in the same manner as the first except 18 grams of the material of Example 1 replaced the egg yolk. Then both amples were beaten with a rotary mixer at high speeds for 20 minutes. The samples had a large volume of air incorporated therein. After standing for 18 hours at room temperature, the contol sample had a firm crust formed thereon, while the sample containing the material of Example 1 still maintained its homogeneous integrity.

EXAMPLE 5 A sample of 450 gram of water was slightly heated and then 45 grams of the emulsifier of Example 1 were added. The material of Example 1 immediately went into solution. The mixture was transferred to a small miXing bowl and mixed for ten minutes on No. speed while intermittently adding 50 cc.s of oil. After ten minutes the mixture changed into a white meringue type consistency and had to be transferred to a large bowl because of the large volume increase. The mixture was beaten for another five minutes and then poured into a larger volumetric cylinder. The volume of the material was measured and indicated to be 2500 cc.s which is a 5 fold increase.

EXAMPLE 6 The procedure as outlined in Example 5 was repeated in its entirety except the material of Example 2 was employed as the emulsifier. The results obtained were comparable to the results obtained in Example 5.

EXAMPLE 7 The procedure as set forth in Example 5 was repeated in its entirety except the composition of Example 3 was employed as the emulsifying agent. The results obtained were comparable to the results obtained in Example 5.

4 EXAMPLE 8 The emulsifying effect of the material of Example 1 was observed in a frosting mixture wherein 335 grams of powdered sugar and 21 grams of non-fat dry milk and 2 grams of salt were placed into a small mixing bowl. Then, grams of water and 0.6 gram of the emulsifier of Example 1 (1% by weight) were mixed for 45 seconds at No. 1 speed. A commercial shortening (88 grams) was added. The frosting mix was then beat at high speed for ten minutes. Then, a commercial frosting was obtained and formulated using the recommended procedure. A comparison between the two frostings indicated that the icing having the emulsifier of Example 1 therein was thicker and peaked much more readily and had more air incorporated therein.

EXAMPLE 9 The procedure as outlined in Example 8 was repeated in its entirety except three percent of the emulsifier of Example 1 was added to the icing instead of 1%. The results obtained were comparable to the results obtained in Example 8.

EXAMPLE 10 The procedure as outlined in Example 8 was repeated in its entirety except the composition of Example 3 was employed as the emulsifier. The results obtained were comparable to those obtained in Example 8.

What is claimed is:

1. In an oil and water foodstuff emulsion containing an emulsifying'agent, the improvement wherein said emulsifying agent is a material having the formula:

(OH)m wherein R is a straight chain alkyl group having from 8 to 24 carbon atoms, R is a polyol selected from the group consisting of monoglycerol, diglycerol, triglycerol, tetraglycerol, and mixtures thereof; A is selected from the group consisting of hydogen, lactyl, dihydroxypropionyl, saccharyl, gluconyl, tartaryl, malyl, and mixtures thereof; and n is l or 2, m is 0 or 1 and q is 1 or 2; said emulsifying agent being present in an amount ranging between 0.1% and 10% by weight.

2. The food composition of claim 1 wherein said emulsifying agent is present in an amount ranging between 0.l% and 10% by weight.

3. The foodstuff emulsion as set forth in claim 1, wherein said emulsifying agent is hexadecyl bis(lactoglyceryl) phosphate.

4. The foodstuff emulsion of claim 1, wherein said emulsifying agent is hexadecyl (glycerol) acid phosphate.

5. The foodstuff emulsion as set forth in claim 4 wherein said emulsifying agent is a sodium salt of said hexadecyl bis (glycerol) phosphate.

References Cited UNITED STATES PATENTS 3,004,056 10/1961 Nunn et al. 260-403 3,208,857 9/1965 Howard et al. 260-403 3,248,229 4/1966 Pader et a1 99-139 RAYMOND N. JONES, Primary Examiner J. M. HUNTER, Assistant Examiner US. 01. X.R. 99-144; 260403