DK174832B1 - Emulsifier, and a procedure for the production thereof - Google Patents

Abstract

A partial poly glycerol fatty-acid ester emulsifier involving poly glycerol, which is predominantly mono and /or di ester in composition with fatty acid components, and usually monomer glycerol, which is predominantly mono and /or di ester in composition with fatty acid components as the fatty acid components are chosen so that the average number of carbon atoms therein lies in an area between 13.0 and 16.5, is produced by replacing a poly glycerol, usually containing monomer glycerol, with a fatty acid, or a mixture of fatty acids, or with a fatty acid glyceride, or a mixture of fatty acid glycerides, as the number of carbon atoms in the fatty acid, or fatty acid components in the glyceride, or the average number of carbon atoms in the fatty acids, or the glycerides' fatty acid components, are in the area between 13.0 and 16.5. It is usually expedient for the emulsifier to be introduced to a container consisting of a stiffener, or flour, via a special extrusion procedure. The emulsifier offers especially good whipping properties in, for example, cake mixtures.

Description

in DK 174832 B1

The present invention relates to a polyglycerol partial fatty acid ester emulsifier, a process for its preparation and a product containing such an emulsifier applied to a particulate carrier.

In the present context, the term "polyglycerol" refers to condensed glycerol molecules such as dimer glycerol (diglycerol), trimer glycerol (triglycerol), etc. Commercial glycerol condensate products or polyglycerol products useful for the preparation of the emulsifiers of the present invention, such as the major site, such as products, consisting of dimer glycerol (diglycerol), are usually mixtures containing glycerol in varying degrees of polymerization, from monomeric glycerol up to tetramer or higher glycerol condensates Important examples of such polyglycerol products are products containing, for example, a maximum of 30% monomeric glycerol, and very interesting polyglycerol -15 products are products containing a maximum of 25%, such as a maximum of 20%, monomer glycerol and about 60% dimer glycerol (diglycerol), with the remainder being higher condensates of glycerol, but the composition of polyglycerol products may vary over a wide range.

Polyglycerol partial fatty acid ester emulsifiers comprising polyglycerol which is predominantly mono- and / or diesterified with saturated fatty acid moieties, and optionally monomeric glycerol, which is predominantly mono- and / or diesterified with saturated fatty acid moieties, are usually used, for example, as emulsifiers or " "air incorporating agent" ("air incorporating agent" ("whipping agent" or "aerating agent") is a term used in the food industry for an emulsifier used for whipping purposes, in other words, for making emulsions where air constitutes the disperse phase). foods, for example, for the manufacture of cake mixes or as emulsifiers in ice or fine foods.

Such polyglycerol partial fatty acid ester emulsifiers are usually prepared by reaction of a polyglycerol product with a fatty acid or a mixture of fatty acids or with a fatty acid glyceride or a mixture of fatty acid glycerides. the fatty acids or fatty acid moieties in the fatty acid glycerides are saturated acids or moieties having a mean number of> carbon atoms on the order of 17-18, such as stearic acid or tallow fatty acids.

It has now surprisingly been found that the emulsifier properties or the air-incorporating properties of polyglycerol partial fatty acid ester emulsifiers, especially emulsifiers in which the majority of the polyglycerol is diglycerol, are significantly improved when the fatty acid moieties, with which the polyglycerol is present, the monomeric glycerol, which is esterified, is chosen such that the mean number of 45 carbon atoms in the acid moieties is on the order of 13.0 to 16.5.

2 DK 174832 B1 In this context, the term "mean number of carbon atoms in the acid moieties" shall mean the mean obtained when the total number of carbon atoms in the acid moieties present as esterifying moieties on the polyglycerol and monomeric glycerol molecules is divided by the total number. of these esterifying parts. As discussed above, products containing a predominant amount of diglycerol may, for example, typically contain an amount of monomeric glycerol and an amount of higher glycerol condensates (or higher glycerol condensates may be formed by condensation during the esterification process). In the normal preparation of the emulsifier product, both the monomeric glycerol and glycerol condensates will be esterified, usually mono- and / or diesterified on terminal hydroxy groups.

In practice, there will be essentially agreement between the average carbon atom number in the acid moieties with which the diglycerol is esterified and the average carbon atom number in the acids or acid moieties in the acid or glyceride starting material used in the esterification at which the diglycerol partial fatty acid ester emulsifiers are formed. Therefore, the average carbon atom number in the acid moieties of the esterified diglycerol molecules will be essentially identical to the average carbon atom number in the acid moieties of the starting material used.

Preferred polyglycerol partial fatty acid ester emulsifiers of the present invention are emulsifiers in which at most 30% of the emulsifier consists of partial fatty acid esters of monomer glycerol. Particularly preferred emulsifiers of the invention are emulsifiers in which at least 50%, preferably at least 60%, of the emulsifier consists of diglycerol partial fatty acid esters and at most 25%, such as not more than 20%, consists of partial fatty acid esters of monomer glycerol. These products are very interesting products such as air incorporating agents for cake mixes.

It is preferred that at least 60%, especially at least 80%, especially preferably at least 90%, of the fatty acid moieties in the emulsifier contain at least 12 carbon atoms. The fatty acid moieties are saturated. A small percentage of unsaturated acid moieties may be present, but should preferably be less than 3% by weight, especially preferably less than 2% by weight and most preferably less than 1% by weight.

40

Very interesting products of the invention are polyglycerol partial fatty acid ester emulsifiers, such as predominantly diglycerol partial fatty acid ester emulsifiers, in which the average carbon atom number in the acid moieties is on the order of 14.0 to 16.0, especially on the order of 45 between 14.0 and 15. 8, such as, for example, on the order of 14.0 to 15.5.

3 DK 174832 B1

Acids which will either be useful in themselves or in combination with each other to obtain the average carbon atom number of the invention are, for example, lauric acid, myristic acid, palmitic acid and stearic acid. In practice 5, it has been found that a very useful emulsifier or air incorporating agent is one in which 40-60%, preferably approx.

50%, of the fatty acid moieties are lauric acid moieties, and 25-50% are stearic acid moieties, 10-20% are palmitic moiety moieties, and 0-3% are myristic moiety moieties. Such a combination is obtained by esterification with a ca. equal mixture of 10 lauric acid and tallow fatty acids. A particular acid composition which can be obtained in this way is one in which 40-60%, preferably approx. 50%, of the fatty acid moieties are lauric acid moieties, and 25-35% are stearic moiety moieties, 10-20% are palmitic moiety moieties and 0-3% are myristic moiety moieties.

Although the desired mean carbon atom number in the acid moieties can result (when more than one type of acid moiety is involved), both from mixing polyglyceride partial fatty acid esters containing a low mean carbon atom in their acid moieties with polyglyceride partial fatty acid esters containing a high mean carbon atom moiety in their acid moieties as well as from preparation 20 polyglyceride partial fatty acid esters directly by esterification of a polyglycerol product with the appropriate acid mixture or triglyceride mixture to obtain the desired mean carbon atom number, the latter being preferred, such co-reaction having been found to result in much better properties of emulsifier air incorporation. A preferred method for preparing the emulsifiers of the invention is therefore to react a polyglycerol optionally containing monomeric glycerol with a fatty acid or a mixture of fatty acids or with a fatty acid glyceride or a mixture of fatty acid glycerides, wherein the number of carbon atoms in the fatty acid or in the fatty acid moieties. in the glyceride or average number of carbon atoms in the fatty acids or in the fatty acid moieties in the glycerides are on the order of 13.0 to 16.5.

The reaction can be carried out in a manner known per se, usually by heating the polyglycerol product with the fatty acid or the mixture of fatty acids or the fatty acid glyceride or the mixture of fatty acid glycerides at a relatively high temperature, such as a temperature of the order of 200-270 ° C, in the presence of a amount of a basic catalyst. Another special process for preparing polyglycerol partial fatty acid esters which can also be used to prepare the emulsifiers of the invention is a process by which the esterification is carried out by reacting a polyglycerol product with fatty acid glycerides in tertiary butyl alcohol as solvent. This process is described in European Patent Specification No. 0.038,347.

45 4 DK 174832 B1

The ratio of the starting materials of the process according to the invention is suitably chosen such that the resulting emulsifier product will be one in which the glycerol or polyglycerol moieties are predominantly mono- or diesterified and where only few or no higher esterified glycerol or polyglycerol molecules are formed. In practice, an appropriate weight ratio of the fatty acid component to the polyglycerol product component may be predicted on the basis of the composition of the fatty acid component and the polyglycerol product component, based on the assumption that the degree of esterification will substantially correspond to the stoichiometric ratios of the starting reaction mixture. For most combinations of polyglycerol product and fatty acids, for example, the weight ratio of fatty acids to polyglycerol product will be on the order of less 7: 3, preferably less than 6: 4, with a preferred ratio often being on the order of 5.5: 4.5. After the reaction, an excess of unreacted diglycerol can be removed in a manner known per se, if desired. If desired, it is also possible to add monomer glycerol to the product to adjust the viscosity of the product.

The emulsifier according to the invention is used in the same way as known emulsifiers for the same purposes. Thus, for example, it can be added to products or mixtures to be emulsified or having air incorporated, in an amount of approx. 1-4% by weight, such as 1.5-3% by weight, e.g. 2% by weight, based on the weight of the emulsifier in relation to the weight of 25 dry components in the products or mixtures (ie, for example, egg-water-free cake mixes added immediately before mixing). The emulsifier can be added to such cake mixes and similar mixtures on it. time when the mixtures are mixed with eggs and water or it can be added to the dry mixture.

30

The invention also relates to a food product, in particular a cake mix or a cake product made therefrom, containing an emulsifier as defined above, especially in an amount of 1-4% by weight calculated as indicated above.

35

A preferred application of the emulsifier is as a free-flowing powder product.

It is known to produce such free-flowing powder products by spray drying or by applying the emulsifier to sucrose particles as a carrier. A known method for preparing such powders is to spray-dry an emulsion made from skim milk or whey and the emulsifier. However, a preferred use of the emulsifier is as a substantially free-flowing emulsifier product in which the emulsifier is disposed on a particulate carrier, preferably in an amount of at least 10% by weight based on the weight of the product. The carrier is preferably of vegetable origin, and interesting carriers are carriers selected from flour varieties, starches, mono- and disaccharides and pentosans and mixtures thereof, optionally with the addition of a vegetable fiber material.

Such a type of product and a method for its preparation are described in the applicants' older pending Danish patent application no.

1487/84 (International Patent Application No. PCT / DK85 / 00018, Publication No. W085 / 03846, European Patent Application published under No. 0153870).

It is generally preferred that the carrier be one containing or consisting of starch.

15

Examples of such carriers which are of great interest in surfactants for use in the food industry can be mentioned starch or flour of tubers such as potato starch, sweet potato starch and yam starch, sago starch, bean flour and pea flour, cereal starches or flour such as rice starch, wheat starch, rye starch, barley starch, oat starch, rice flour, wheat flour, rye flour, barley flour, oatmeal · and corn starch, maltodextrins, dextrose, fructose and mixtures thereof.

The particulate carriers are usually carriers whose particles have a particle size distribution with a predominant fraction having a size in the range of about 1-20 Jim, especially 1-10 pm. It is often preferred that the carriers have very small particle sizes, for example with predominantly particle size fractions in the range of 1-5 microns or less.

In the emulsifier products of the invention, the percentage of the emulsifier is usually in the range of 10-60%, such as 10-50% and often preferably 15-50%, especially 15-40%, based on the total weight of the emulsifier and carrier.

The substantially free-flowing powder product having the above-described characteristics may be prepared by mixing the emulsifier with one or more particulate carriers and subjecting the resulting mixture to extrusion or equivalent treatment to form a substantially free-flowing powder.

When the emulsifier and a suitable particulate carrier, in particular a carrier capable of being "wetted" or "sorbed" (adsorbed and / or absorbed) the emulsifier under the given conditions, are subjected to extrusion, it is possible obtaining an extrudate which, instead of having an extruded strand of the mixture, immediately disintegrates into a powder product having highly desirable properties.

Suitable carriers are those mentioned above, especially particulate carriers which are starches or flour types. Although these preferred carriers can be used as they are (with particle size distributions which often have a predominant fraction having a size in the range of about 1-20 microns and preferably 1-10 microns, but which may also be somewhat larger, e.g. fractions of up to 20-50 µm or even 50-100 µm), it is anticipated that it may be advantageous to ensure a very fine particle size of the carriers, such as 1-5 µm or finer, by subjecting the carriers to a further comminution in addition to the comminution which such products (e.g. flour or starch) have usually been subjected to. Such additional comminution may, for example, take place in an air mill ("circular chamber 15 jet mill") or a blender type mill.

Blaine value for wheat starch which can be used as a carrier is approx. 2500 cm2 / g and for rice starch approx. 6000 cm 2 / g. When the emulsifier is placed on such carriers, the Blaine values drop somewhat, typically to e.g. 1100 cm 2 / g for a product containing 22.5% by weight emulsifier and 77.5% by weight wheat starch, and to approx. 1700 cm 2 / g for a product containing 35% by weight emulsifier and 65% by weight rice starch.

The vegetable flour or starch carriers can be combined with fiber materials, if desired, to obtain a starch or 25 flour / fiber combination carrier, provided that the fiber materials in the final product have approx. the same "particle" size (e.g., fiber length) as the flour or starch particles, such as a size in the range of 1-100 µm, especially ΙΣΟ µm or less, as explained above. The fiber materials can be comminuted to such small sizes before being added to the mixture or they may be fibrous materials of such brittle or weak nature as to be comminuted to the said small particle sizes during the mixing process Examples of suitable fibrous materials for this purpose are bran, such as wheat bran, rye bran, pea bran or bean bran. it is preferred that they constitute 35 not more than 50% by weight of the carrier, preferably not more than 20% by weight of the carrier and most preferably not more than 5% by weight of the carrier.

The mixing of the components is conveniently carried out immediately prior to extrusion into the mixing / transporting portion of the extruder equipment. This transport part is typically a screw mixer such as a double screw mixer. The temperature of the last part of the screw mixer (and thus about the temperature of the mixture subjected to extrusion) is usually in the range of 100-180 ° C, typically 110-150 ° C and often preferably 120-140 ° C.

The orifice or each orifice through which the mixture is extruded will normally have a diameter of from approx. 1/2 to approx. 8 mm; often a diameter of approx. 1-4 mm, such as approx. 2 mm, very suitable.

The mixture subjected to extrusion will usually have a free water content (water that is not chemically bound} of 1-30% by weight, especially 5-25% by weight. In some cases it has been found advantageous to add a small percentage of water , such as 0.1-5% by weight, especially 0.1-3% by weight, for the mixer together with the surfactant and carrier.

EXAMPLE 1

An emulsifier product was prepared by heating 202.5 g of glycerol condensate mixture (comprising 15% monomeric glycerol, 60% diglycerol, the remainder being higher glycerol condensates), 247.5 g of stearic acid product (containing about 70% by weight stearic acid, 25% by weight palmitic acid, and 5% weight percent myristic acid, the average carbon atom number in the product: 17.2) and 2 g of sodium hydroxide to 20 230 ° C and keep the mixture at 230 ° C for 20 minutes, after which the mixture was rapidly cooled to just below 100 ° C. The resulting homogeneous clear product was allowed to cool to give a yellow to light brown fat-like emulsifier product (hereinafter referred to as stearic acid diglycerol partial ester).

25

Using exactly the same conditions and exactly the same amounts, but using myristic acid (99% by weight myristic acid, carbon atom number: 14) instead of the stearic acid product, another yellow to light brown fat-like emulsifier product (hereinafter referred to as myristic acid) was obtained. diglycerol-partielester). The saponification number of the product was 135-140.

The stearic acid diglycero.1 partial ester was mixed with the myristic acid diglycerol partial ester by weight ratios 90:10 and 80:20 respectively (by melting and mixing), and both the resulting mixtures as well as the stearic acid diglycerol partial ester and myristic acid diglycerol itself. The batch ester was placed on rice starch as follows: In a BC 45 extruder supplied by Creusot-Loire, France, and 40 comprising a twin screw rotating at a speed of 200 rpm and two nozzles having a diameter of 2 mm, when a portion of the double screw length is cooled by means of a water jacket, and the portion of the double screw adjacent to the nozzles is heated by means of an induction heat jacket, rice starch was poured through a feed funnel 45 comprising two screws carrying the starch, and The diglycerol partial ester or diglycerol partial ester mixture was melted in the molten state through a rudder. Through another tube, 1.5% water (calculated on the same percentage basis as the diglycerol partial ester or mixture and rice starch) was added to the extruder.

The weight ratio of the diglycerol partial ester feed or mixture added to the rice starch feed was 35% diglycerol partial ester or 65% rice starch mixture. The total amount added per hour was 45 kg.

The temperature of the screw part was thermostated to 130 ° C.

To boot, an excess of the diglycerol partial ester or mixture and water was added and the product appeared as a semi-liquid or dough-like liquid or dough-like strand. When the added water and diglycerol partial ester feed or mixture had been adjusted to the amounts indicated above, the product changed to a particulate free flowing powder.

The product of the extrusion was a free-flowing powder comprising the 20 starch particles (or small agglomerates of particles) carrying the diglycerol partial ester or mixture.

Three additional emulsifier products were prepared by esterification of the same glycerol condensate mixture in exactly the same manner as described above, except that mixtures of the stearic acid product and myristic acid were used in the weight ratios of 90:10, 80:20 and 70:30, respectively. The resulting "co-reacted" products were applied to rice starch in exactly the same manner as described above.

30 57 g of each of the resulting rice starch-borne products were tested in a whipping test in a layer cake mixture of the following composition: 405 g of powdered milk 270 g of wheat flour 35 188 g of wheat starch 30 g of baking powder 50 g of milk powder 350 g of whole egg 350 g of water.

40

The dry ingredients (i.e. all ingredients except eggs and water) were mixed and sieved. The eggs and water were stirred into the dry mixture with a Hobart-type planetary mixer for 1 minute at the lowest speed followed by 264 rpm whipping for 3, 5 or 10 minutes after which the room weight was specific. The results are shown in Table 1.

Table 1 5

Cake mix volume, g / liter

Stearic acid ratio: Whisk time myristic acid product Comments 3 min. 5 min. 10 min.

10 0: 100 1030 1010 755 100: 0 335 335 360 15 90:10 mixed 380 345 350 B0: 20 mixed 470 400 365 90:10 co-reacted 360 365 345 80:20 c: o-reacted 320 315 335 70: 30 Co-reacted 350 335 335 20_______

It can be seen from Table 1 that the emulsifier produced with the stearic acid product has poor whipping properties, whereas the emulsifier made with myristic acid provides excellent whipping. Also, the mixture of 90% of the emulsifier made with myristic acid and 10% of the emulsifier made with the stearic acid product results in good whipping properties, whereas the whipping properties are somewhat inferior when the stearic acid emulsifier portion of the mixture is increased to 20%. It also appears that the co-reaction tends to result in better whipping properties.

Thus, the product co-reacted with 80% of the myristic acid and 20% of the stearic acid product has much better whipping properties than the 80:20 mixture. It will also be noted that although the blend product starts to give poor whipping results already at the 80:20 ratio, the co-reacted product provides excellent whipping properties at the 70:30 ratio.

EXAMPLE 2 In the same manner as described in Example 1, mixtures of myristic acid 40 and the stearic acid product were reacted with diglycerol to produce co-reacted products. After the reaction, unesterified glycerol and glycerol condensate were removed from the reaction mixture. Each of the resulting emulsifiers was placed on icing in an amount of 10% emulsifier of 90% of the sugar by melting the emulsifier and adding the sugar. Subsequently, each of the resulting coarse powder products was passed through a screen to obtain a free flowing powder. After standing for about 24 hours, each product was again passed through a sieve and then subjected to the same whipping test in the same layer cake mixture as described in Example 1. The results are shown in Table 2.

5

Table 2

Cake mixture room weight, g / liter 10 Myristic acid ratio: stearic acid product, Whip time co-reacted 3 min. 5 inin. 10 min.

15 100: 0 360 315 355 90:10 335 305 305 80:20 335 295 300 70:30 320 295 285 20 60:40 360 315 285 50:50 350 305 275 40:60 330 315 285 20:80 565 415 300 10:90 630 440 285 25 Similarly, a co-reacted 50:50 myristic acid: completely cured tallow fatty acid product was prepared and tested. The whipping results were: 3 30 minutes: 350 g / liter, 5 minutes: 305 g / liter, and 10 minutes: 280 g / liter, in other words almost identical to the results given above, although with the tallow fatty acids product introduced, small extra amount of glycerol.

EXAMPLE 3

In the same way as described in Example 2, co-reaction emulsifiers were prepared with mixtures of the myristic acid and 99% palmitic acid. After the reaction, unesterified glycerol and glycerol condensate were removed from the reaction mixture. The resulting products were applied to sugar as described in Example 2 and subjected to the whipping test in the same manner as described in Example 1. The results are shown in Table 3.

45 Table 3 11 DK 174832 B1

Cake mix volume, g / liter

Myristic acid ratio: Whipping time 5 palmitic acid, co-reacted 3 min. 5 min. 10 min.

100: 0 350 310 355 90:10 335 305 345 10 80:20 330 305 330 70:30 340 305 315 60:40 325 320 305 50:50 335 315 305 40:60 330 335 305 15 30:70 325 320 290 20:80 330 335 315 10:90 330 335 305 20 EXAMPLE 4

An emulsified product was prepared by heating 19.92 kg of the same glycerol condensate mixture as in Example 1, 0.33 kg of glycerol, 12.38 kg of lauric acid (99%) and 12.38 kg of the same stearic acid product. as in Example 1 at 225-230 ° C for 40 minutes. During the heating, 1.4 kg of reaction water was removed. (The reaction was obtained without the addition of catalyst; the amount of catalyst present in the glycerol condensate mixture). The mixture was then rapidly cooled to just below 100 ° C. The resulting homogeneous clear product was allowed to cool, whereupon a yellow light brown fat-like emulsified product was obtained. The saponification value for the product was 141.7, the acid number was 2.7, and the pH was 7.2. A melting point determination in capillary tubes gave the following results: Clearance point 38.5 ° C, rise point 61 ° C.

The co-reacted emulsifier product was placed on rice starch in an extruder in the same manner as described in Example 1. In one experiment, 35% of the emulsifier was placed on 65% rice starch with 1.5% water added. In another experiment, 35% of the emulsifier was placed on 65% rice starch without the addition of water. In a third experiment, 39.2% of the emulsifier was placed on 60.8% rice starch without the addition of water.

Each of the rice starch-borne products was subjected to the same 45 whipping test in the same layer cake mixture as described in Example 1. Each product was mixed with the other ingredients and a portion of the resulting mixture was immediately whipped. Another portion of the emulsifier-containing mixture (dry) was stored for 3 months at room temperature, after which it was whipped. The results of the whipping experiments 5 are shown in Table 4.

Table 4

The volume of the cake mixture, g / liter 10

Co-reacted 50:50 lauric acid: stearic acid- Whipping product 3 min. 5 min. 10 min.

15 _ _________ 35% emulsifier, 65% rice starch, prepared with 1.5% water 20 freshly prepared mixture 335 335 355 after 3 months 340 355 380 25 35% emulsifier, 65% rice starch, prepared without water freshly prepared mixture 325 330 345 30 after 3 months 345 350 360 39.2% emulsifier, 60.8% rice starch, 35 prepared without water freshly prepared mixture 350 330 340 after 3 months 335 340 365 40

The results show that the emulsifier has excellent whipping properties and that these excellent whipping properties are retained even when the emulsifier, mixed with the cake mixture, is stored for a long period of time at room temperature.

EXAMPLE 5 In the same way as described in Example 4, a series of large-scale emulsifiers were prepared with four different acid reactants: 991 lauric acid; the stearic acid product described in Example 1; 99% myristic acid; and 99% palmitic acid. The glycerol condensate mixture was the same as in Example 1. The weight ratio of the acid reactant to the glycerol condensate mixture was 55:45. As a catalyst, 0.44% sodium hydroxide was used, calculated on the reactants.

Each of the resulting emulsifier products was placed in an amount of 35% on 65% rice starch in the same manner as described in Example 1 using 1.5% water and without water respectively. The results of the whipping experiments are shown in Table 5.

Table 5

whipping

Emulsifier product 3 min. 5 min. 10 min.

25

Lauric acid product, placed on rice starch, with water 665 730 710 30 placed on rice starch, without water 525 630 695

Stearic acid product, 35 placed on rice starch, with water 900 750 475 placed on rice starch, 40 without water 910 7 35 4 90

Myristinic acid product, placed on rice starch, 45 with water, 14 DK 174832 B1 fresh, mixture 335 335 360 after 3 months storage 5 in the cake mixture 420 390 365

Palmitic acid, applied to rice starch, 10 with water, fresh mixture 395 365 330 after 3 months 530 430 355 15 EXAMPLE 6 20

An emulsifier product was prepared by heating 57.8% of a glycerol condensate mixture having a viscosity of 1000 cps at 60 ° C and having the following average composition: 25 Monomer glycerol 21.5%

Diglycerol 26.3%

Trim condensate 19.1%

Tetramed condensate 12.1%

Pentamere condensate 7.4% 30 Higher condensates 13.6%

The above product was esterified with myristic acid.

The weight ratio of the glycerol condensate product to the myristic acid was 57.8: 42.2. No catalyst was added (the small amount of catalyst present in the polyglycerol product was sufficient). The mixture was kept at 265 ° C for 20 minutes, then rapidly cooled to just below 100 ° C. The resulting homogeneous clear product was allowed to cool, whereupon a yellow to light brown fat-like emulsifier product was obtained. Unesterified glycerol and glycerol condensate were removed from the product. The data for the product were as follows: Prior to removal of unreacted glycerol and glycerol condensate: Saponification value 111.5, acid number 0.9; pH 7.6. After removal of unreacted glycerol and glycerol condensate: Saponification value 150.5, acid number 9.2.

Similarly, another product was prepared using the same glycerol condensate mixture except that an 80:20 mixture of myristic acid (99%) and the stearic acid product described in Example 1 was used as an acid reactant. Data for the resulting emulsifier product 5 were as follows: Prior to removal of unesterified glycerol and glycerol condensate: Saponification value 134.8; acid number 2.9; pH 8.5.

After removal of unesterified glycerol and glycerol condensate:

Saponification value 163.3; acid number 10.9.

Each of these emulsifier products (from which unreacted glycerol and glycerol condensate had been removed) was placed in an amount of 10% of 90% icing as described in Example 2, and the sugar-borne products were subjected to the same whipping tests in the same layer cake mixture. as described in Example 1. The results are shown in Table 6.

15

Table 6

Cake mix room weight, g / liter 20 Whipping time

Product 3 min. 5 min. 10 min.

Prepared with myristic acid 500 465 465 25

Prepared with 80:20 mixture of myristic acid and stearic acid product 650 560 410 30 ____ _ ____

These results are much better than results obtained with the same glycerol condensate reacted in the same manner with the stearic acid product alone.

Claims (17)

A polyglycerol partial fatty acid ester emulsifier, characterized in that it comprises polyglycerol which is predominantly mono- and diesterified with saturated fatty acid moieties and optionally monomeric glycerol, which is predominantly mono- and diesterified with saturated fatty acid moieties, the fatty acid moieties being selected as such. that the mean number of carbon atoms in the acid moieties is in the range of 13.0 to 16.5, and so that at least 50% of the emulsifier consists of diglycerol partial fatty acid ester and at most 25% consists of partial fatty acid esters of monomer glycerol. Polyglycerol partial fatty acid ester emulsifier according to claim 1, characterized in that at least 60% of the emulsifier consists of 15 diglycerol partial fatty acid ester and at most 20% consists of partial fatty acid esters of monomer glycerol. Polyglycerol partial fatty acid ester emulsifier according to claim 1 or 2, characterized in that at least 60%, especially at least 80%, preferably at least 90%, of the fatty acid moieties contain at least 12 carbon atoms. Polyglycerol partial fatty acid ester emulsifier according to any one of claims 1-3, characterized in that the average number of carbon atoms in the acid moieties is on the order of 14.0 to 16.0. Polyglycerol partial fatty acid ester emulsifier according to any one of claims 1-4, characterized in that the largest proportion of the fatty acid moieties is selected from lauric, myristic, moiety and stearic moiety. Polyglycerol partial fatty acid ester emulsifier according to claim 5, characterized in that 40-60%, preferably approx. 50%, of the fatty acid moieties are lauric acid moieties, and 25-50%, such as 25-35%, are stearic acid moieties, 10-20% are palmitic moiety moieties, and 0-3% are myristic moiety moieties. 5 Process for the preparation of a polyglycerol partial fatty acid ester emulsifier, characterized in that a polyglycerol, optionally containing monomeric glycerol, is reacted with a fatty acid or a mixture of fatty acids or with a fatty acid glyceride or a mixture of fatty acid glycerides, the number of carbon atoms. in the fatty acid or glyceride fatty acid moieties or the average number of carbon atoms in the fatty acids or glyceride fatty acid moieties are on the order of between 13.0 and 16.5, and wherein at least 50% of the emulsifier consists of diglycerol partial fatty acid esters and not more than 25% consists of partial fatty acid esters of monomer glycerol. Process according to claim 7, characterized in that at least 60% of the polyglycerol product 20 consists of diglycerol molecules and at most 20% consists of partial fatty acid esters of monomer glycerol. Process according to claim 7 or 8, characterized in that at least 60%, especially at least 80%, preferably at least 90%, of the fatty acid moieties contain at least 12 carbon atoms. Process according to any one of claims 7-9, characterized in that the mean number of carbon atoms in the acid moieties is in the order of 14.0 to 16.0. > Process according to any one of claims 7-10, characterized in that the largest proportion of the fatty acid moieties is selected from lauric acid moieties, myristic acid moieties, palmitic acid moieties 35 and stearic moiety moieties. 18 DK 174832 B1 Process according to claim 11, characterized in that 40-60%, preferably approx. 50%, of the fatty acid moieties are lauric acid moieties, 25-50% such as 25-35% are stearic moiety moieties, 10-20% are palmitic moiety moieties and 0-3% are 5 myristic moiety moieties. Essentially free-flowing emulsifier product, characterized in that it comprises an emulsifier according to any one of claims 1-6 disposed on a particulate 10 carrier, preferably in an amount of at least 10% by weight, based on the weight of the product. Product according to claim 13, characterized in that the carrier is selected from flour types, 15 starches, mono- and disaccharides and pentosans and mixtures thereof, optionally with the addition of a fiber material of vegetable origin. Process for preparing an emulsifier product according to claim 13 or 14, characterized in that the emulsifier is mixed with one or more particulate carriers and the resulting mixture is subjected to extrusion or similar treatment. Process according to claim 15, characterized in that the temperature of the mixture subjected to extrusion is in the order of 100-180 ° C, especially 110-150 ° C, preferably 120-140 ° C. 30 Food product, in particular a cake mix or cake product made therefrom, characterized in that it contains an emulsifier according to any one of claims 1-6 or an emulsifier product according to claims 13 or 14, preferably in an amount of 1-4. % by weight, based on the weight of the emulsifier relative to the weight of the dry ingredients in the food product.