NZ586813A - Emulsifying systems for frozen food products and methods of preparation thereof - Google Patents

Abstract

Disclosed is an emulsifying system comprising a 2-propylene glycol monoester of a fatty acid (2-PGME) and a 1-propylene glycol monoester of a fatty acid (1-PGME), wherein the emulsifying system further comprises monoglycerides and diglycerides and wherein the ratio by weight between the monoglyceride and the diglyceride is at most 50:50. Also disclosed are frozen food products comprising said emulsifying system.

Description

PATENTS FORM NO. 5 Our ref: VIA508417NZPR Divisional Application out of NZ 577808 Antedating requested to 27 November 2006 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION FROZEN FOOD PRODUCTS, EMULSIFYING SYSTEMS, AND RELATED METHODS We, PALSGAARD A/S of Paisgaardvej 10, DK-7130 Juelsminde, Denmark, hereby declare the invention, for which we pray that a patent may be granted to us and the method by which it is to be performed, to be particularly described in and by the following statement: (This page followed by page 1A) 301497150J .DOC: VIAiqakld 301497667:508417 1A FROZEN FOOD PRODUCTS, EMULSIFYING SYSTEMS, AND RELATED METHODS TECHNICAL FIELD OF THE INVENTION The present invention relates to frozen food products, such as ice creams, comprising special emulsifying systems, The emulsifying system preferably contains mono esters of propane-l,2-diol and fatty acids, such as 2-PGME, and it may furthermore contain additional emulsifiers such as 1-PGME and/or diglycerldes. The invention furthermore 10 relates to the emulsifying systems as such as well as methods of preparing the frozen food product.

BACKGROUND OF THE INVENTION Frozen food products, such as ice creams, are particularly appreciated for their creamy and smooth characteristics. The organoleptic characteristics of traditional frozen food products are sensitive to even small temperature variations which is typically observed during storage, distribution, or handling. This is particularly problematic when a consumer 20 purchases a frozen food product and does not consume it quickly. When a longer period of time elapses from the frozen food products is taken from the deep frozen section in the retail store until it is placed in a domestic freezer, a partial thawing of the frozen product takes place before it is refrozen. Such cycles of temperature variation, which is known as "heat shock", is known to reduce the overall organoleptic perception of the frozen food 25 products.

In the prior art some emulsifiers have been applied in the preparation of frozen food products to reduce this problem: In the US patent application US 2005/0,123,666 an ice cream containing a propylene glycol monoester, unsaturated monoglycerides, and sorbitan tri-stearates is disclosed.

The PCT application WO 2005/060,763 a low fat ice cream formulation comprising a propylene glycol monoester and a mono-diglyceride is disclosed.

Received at IPONZ 3 Feb 2011 301497667:508417 2 However, there is stiii an unmet need for frozen food products having an improved quality and an improved robustness towards heat shock.

SUMMARY OF THE INVENTION An object of the present Invention is to provide a frozen food product having improved organoleptic properties, as well as methods of production, emulsifying systems useful for preparing said frozen food product, a packaged emulsifying system and use of an 10 emulsifying system.

Alternatively, it is an object of the present invention to provide a frozen food product having one or more of the characteristics: a reduce melt rate, an improved creaminess, a reduced coolness, an improved smoothness, and combinations thereof.

The above objects are to be read disjunctively and with the alternative object of to at least provide the public with a useful choice.

The inventors have made the surprisingly discovery that 2-PGME used in frozen food 20 products, and particularly in low fat frozen food products, results in improved organoleptic and sensory properties as well a reduced rate of melting.

Thus, one aspect of the invention relates to a frozen food product comprising an emulsifying system comprising a 2-propylene glycol monoester of a fatty acid (2-PGME).

Another aspect of the present invention relates to an emulsifying system comprising a 2-PGME of a fatty acid.

In one embodiment, the present invention relates to an emulsifying system comprising a 30 2-PGME and a 1-propylene glycol monoester of a fatty acid (1-PGME), wherein the emulsifying system further comprises monoglycerides and diglycerides and wherein the ratio by weight between the monoglyceride and the diglyceride is at most 50:50.

In one embodiment, the present Invention relates to a frozen food product comprising said 35 emulsifying system.

Yet another aspect of the present invention is to provide a packaged emulsifying system comprising a container, said container comprising said emulsifying system. 301497667:508417 3 Stili another aspect of the present Invention is the use of said emulsifying system for emulsifying frozen desserts, ice cream, low fat ice cream, ice milk, sherbets, sorbet, frozen fruit juice, frozen yoghurt, frozen water ice, aerated frozen bars, whipped dairy cream, unwhipped dairy cream, whipped imitation creams and unwhipped imitation creams, In general the various aspects of the invention may be combined and coupled in any way possible within the scope of the invention. These and other aspects, features and/or advantages of the invention will be apparent from and elucidated with reference to the embodiments described hereinafter.

BRIEF DESCRIPTION OF THE FIGURES Figure 1 shows a SEM picture of an ice cream containing PGME (approximately 50% 2-15 PGME and 50% 1-PGME) as well as unsaturated diglycerides, Figure 2 shows a SEM picture of an ice cream containing PGME (approximately 50% 2-PGME and 50% 1-PGME) as well as unsaturated monoglycerides and diglycerides, Figure 3 shows a SEM picture of an ice cream containing PGME (approximately 50% 2-PGME and 50% 1-PGME) as well as saturated monoglycerides and diglycerides, Figure 4 shows a SEM picture of an ice cream containing PGME (approximately 33% 2-PGME and 66% 1-PGME) as well as saturated monoglycerides and diglycerides, and Figure 5 shows a SEM picture of an ice cream containing PGME (approximately 22% 2-PGME and 78% 1-PGME) as well as saturated monoglycerides and diglycerides.

The present invention will now be described in more detail in the following.

DETAILED DESCRIPTION OF THE INVENTION An aspect of the invention relates to a frozen food product comprising an emulsifying system comprising a 2-propylene glycol monoester of a fatty acid (2-PGME).

In the context of the present invention, the term "emulsifying system" generally relates to the emulsifier(s) of the frozen food product as well as other useful components, such as Received at IPONZ 3 Feb 2011 301497667:508417 2A Yet another aspect of the present invention is to provide a method of preparing a frozen food product, the method comprising the step of a) mixing a food intermediate with said emulsifying system, b) optionally, heating the mixture to a temperature sufficient for the emulsifying system to melt, and c) freezing the resulting mixture.

In one embodiment, the present invention relates to a frozen food product prepared by 10 said method.

Still another aspect of the present invention is the use of said emulsifying system for emulsifying a frozen food product. 301497667:508417 4 additives and/or solvents. The emulsifying system may comprise one or more emulsifiers, such as 2, 3, 4, 5 or 6 different emulsifiers. The components of the emulsifying system can both be applied to the other ingredients of the frozen food product as a mixture, or separately but at the same time. Alternatively, the components of the emulsifying system 5 can be applied to the other ingredients of the frozen food product separately and at different times during the production of the frozen food product.

In the context of the present Invention, the term "2-propylene glycol monoester of a fatty acid" or "2-PGME" relates to a mono ester of a fatty acid and propane-l,2-diol having the 10 general formula I, (I) 3 wherein R is the hydrocarbon portion of the fatty acid, which fatty acid has been esterified with propane-l,2-diol. The general formula I includes any enatiomers and racemates of the 2-PGME.

In some preferred embodiments of the invention, the emulsifying system additionally comprises a l-propylene glycol monoester of a fatty acid (1-PGME). In the context of the present invention, the term "l-propylene glycol monoester of a fatty acid" or "1-PGME" relates to a mono ester of a fatty acid and propane-l,2-diol having the general formula II (ID V wherein R is the hydrocarbon portion of the fatty acid, which fatty acid has been esterified with propane-l,2-diol. The general formula II includes any enatiomers and racemates of the 1-PGME.

Preparation of the 2-PGME and 1-PGME is well known to the person skilled in the art, e.g. in Martin and Lutton, the contents of which are incorporated herein by reference. The preparation of the 2-PGME and 1-PGME may e.g. involve esterification using protection 301497667:508417 groups to protect either the 1-hydroxy or the 2-hydroxy group. Alternatively, 2-PGME or 1-PGME may be provided by isolating the individual molecular species from a mixture of 2-PGME and 1-PGME by means of chromatography.

The ratio by weight of 2-PGME and 1-PGME may e.g. be at least 1:4, such at least 1:3, or at least 3:7, preferably at least 1:2, such as at least 4:7, and even more preferably at least 4:6, such as at least 1:1. It is envisioned that the ratio by weight of 2-PGME and 1-PGME in the emulsifying system may e.g. be at least 2:1, such as at least 3:1, at least 8:2, or at least 9:1.

In the context of the present Invention, the term "weight ratio" relates to the ratio between the weights of the mentioned components. For example, a mixture comprising 2 g 2-PGME and 6 g 1-PGME wouid have a ratio by weight of 2-PGME and 1-PGME of 2:6 which is equal to 1:3 or 0.333 (that is: 1 divided with 3). Similarly, a mixture comprising 2 g 2-15 PGME and 4 g 1-PGME wouid have a ratio by weight of 2-PGME and 1-PGME of 2:4 which is equal to 1:2 or 0.5 (that is: 1 divided with 2).

The ratio by weight of 2-PGME and 1-PGME is normally in the range of 1:10 to 10:1, such as in the range of 1:8 - 8:1, preferably In the range of 1:6 - 6:1; such as in the range of 20 1:4 - 4:1, and even more preferably in the range of 1:2 - 2:1, such as in the range of 1:1.5 - 1.5:1, and preferably in the range of 4:5 to 5:4 It is also envisioned that the ratio by weight of 2-PGME and 1-PGME may be in the range of 3:7 to 10:1, such as in the range of 3:7 to 8:1, preferably in the range of 3:7 to 6:1 , 25 such as in the range of 3:7 to 4:1, and even more preferably in the range of 3:7 to 2:1, such as in the range of 3:7 to 1:1.

It is also envisioned that the ratio by weight of 2-PGME and 1-PGME may be in the range of 3:7 to 10:1, such as in the range of 1:1 to 10:1, preferably in the range of 2:1 to 10:1 , 30 such as in the range of 4:1 to 10:1, and even more preferably in the range of 6:1 to 10:1, such as in the range of 8:1 to 10:1.

Normally, the 2-PGME is present in an amount of at least 0.01% by weight of the frozen food product. The 2-PGME may for example be present in an amount of at least 0.05% by 35 weight of the frozen food product, such as at least 0.1%, and preferably at least 0.2%, such as at least 0.25%.

In the context of the present invention, mentioned percentages are weight/weight percentages unless stated otherwise. 301497667:508417 6 The 1-PGME may e.g. be present in an amount of at least 0.01% by weight of the frozen food product. The 1-PGME may for example be present in an amount of at least 0.05% by weight of the frozen food product, such as at least 0.1%, and preferably at least 0.15%, 5 such as at least 0.20%.

Typically, the 2-PGME is present in an amount of at least 0.01% by weight of the frozen food product and the 1-PGME is typically present in an amount of at least 0.01% by weight of the frozen food product. The 2-PGME may e.g. be present in an amount of at least 10 0.05% by weight of the frozen food product and the 1-PGME may for example be present in an amount of at least 0.05% by weight of the frozen food product, such as at least 0.1% of 2-PGME and at least 0.1% 1-PGME, and preferably at least 0.2% of the 2-PGME and at least 0.15% of the 1-PGME, such as at least 0.25% of 2-PGME and at least 0.2% of 1-PGME.

The 2-PGME may be present in an amount of 0.01% to 10% by weight of the frozen food product, such as 0.05% to 8%, preferably 0.1% to 6%, such as 0.15% to 5%, and even more preferably 0.2% to 4%, such as 0.2% to 3.5%.

The 1-PGME may be present in an amount of 0.01% to 10% by weight of the frozen food product, such as 0.05% to 8%, preferably 0.1% to 6%, such as 0.1% to 5%, and even more preferably 0.15% to 4%, such as 0.2% to 3.0%.

Normally, the 2-PGME is present in an amount of 0.01% to 10% by weight of the frozen 25 food product and normally, the 1-PGME is present in an amount of 0.01% to 10% by weight of the frozen food product. The 2-PGME may e.g. be present In an amount of 0.05% to 8 by weight of the frozen food product and the 1-PGME may for example be present in an amount of 0.05% to 8% by weight of the frozen food product, such as 0.1% to 6% of 2-PGME and 0.1% to 6% of 1-PGME, preferably 0.15% to 5% 2-PGME and 0.1% 30 to 5% 1-PGME, such as 0.2% to 4% 2-PGME and 0.15% to 4% 1-PGME, and even more preferably 0.2% to 3.5% 2-PGME and 0.2% to 0.3%.

It is also envisioned that the 2-PGME may be present in an amount of 0.05% to 1% by weight of the frozen food product and the 1-PGME is present in an amount of 0.05% to 1% 35 by weight of the frozen food product.

In some embodiments of the present invention the emulsifying system comprises one or more additional emulsifiers, 301497667:508417 7 For example, at least one of the one or more additional emulsifiers may be selected from the group consisting of a carboxylic acid ester of a monoglyceride, a carboxyiic acid ester of a digiyceride, a phospholipid, a phospholipid derivative, a polyglycerol ester of poiyricinoiic acid, a polygiycerol ester of fatty acids, a citric acid ester of mono glycerides 5 (dtrem), sodium stearoyl iactyiates (CSL), calcium stearoyl iactylates (SSL), a polysorbate, an ammonium phosphatide, sorbitan tristearate (STS), lactylated monogiycerides (LACTEM), acetylated monoglycerides (ACETEM), unsaturated monoglycerides, and mixtures thereof.

The additional emulsifier may for example be a digiyceride. A digiyceride is the diester of two fatty acids and glycerol and may e.g. comprise the 1,2-diester and/or 1,3 diester of the fatty acids and glycerol.

The inventors have made the surprisingly discovery that the combination of 2-PGME and 15 digiyceride used in frozen food products, and particularly in low fat frozen food products, results in improved organoleptic properties and melting properties relative to using 1-PGME, or 1-PGME and monoglyceride, In another embodiment of the present invention the additional emulsifier may e.g. be a 20 monoglyceride. A monoglyceride is a monoester of a fatty acid and glycerol.

In still another embodiment the additional emulsifier may for example be a monoglyceride and a digiyceride.

The fatty acid of the monoglyceride may e.g. be a saturated fatty acid.

The fatty acids of the digiyceride may e.g. be saturated fatty acids.

The fatty acid of the monoglyceride may e.g. be an unsaturated fatty acid.

The fatty acids of the digiyceride may e.g. be unsaturated fatty acids.

The unsaturated fatty acids used in the context of the present invention, and particularly in the context of the 1-PGME and 2-PGME, in the context of the digiyceride, or in the context 35 of triglycerides, may e.g. comprise double bonds in the cis configuration or in the trans configuration. It is even envisioned that a fatty acid may both comprise a double bond in the cis configuration and a double bond in the trans configuration. 301497667:508417 8 In preferred embodiments of the invention, a large fraction of double bonds of the fatty acids of the 1-PGME and 2-PGME and/or of the diglycerides are in the cis configuration. For example, at least 75% of the double bonds of the fatty acids of the 1-PGME and 2-PGME and/or of the diglycerides may be in the cis configuration, such as at least 85%, preferably 5 at least 90%, such as at least 95%, and even more preferably at least 97.5% of the double bonds of the fatty acids may be in the cis configuration, such as at least 99%. In some embodiments of the invention substantially none of the fatty acids of the 1-PGME and 2-PGME and/or of the diglycerides are in the trans configuration.

In preferred embodiments of the invention, a large fraction of double bonds of the fatty acids of the triglycerides, e.g. the triglycerides of the used fats, are in the cis configuration. For example, at least 75% of the double bonds of the fatty acids of the triglycerides may be in the cis configuration, such as at least 85%, preferably at least 90%, such as at least 95%, and even more preferably at least 97.5% of the double bonds 15 of the fatty acids may be in the c/'s configuration, such as at least 99%, In some embodiments of the invention substantially none of the fatty acids of the triglycerides are in the trans configuration.

The digiyceride may e.g. be present in an amount of at least 0.01% by weight of the 20 frozen food product, such as at least 0.05% by weight, and preferably at least 0.1%, such as at least 0.15%, and even preferably at least 0.2%, such as at least 0.25%.

The monoglyceride may e.g. be present in an amount of at least 0.01% by weight of the frozen food product, such as at least 0.03%, and preferably at least 0.06%, such as at 25 [east 0.08%.

Normally, the digiyceride is present in an amount of 0.01% to 5.0% by weight of the frozen food product. The digiyceride may for example be present in an amount of 0.02% to 3% of the frozen food product, such as 0.05% to 1%, and preferably 0.01% to 0.75%, 30 such as 0.15% to 0.5%, and even more preferably 0.20% to 0.40%.

Typically, the monoglyceride is present in an amount of 0.01% to 5.0% by weight of the frozen food product. The monoglyceride may for example be present in an amount of 0.02% to 3% of the frozen food product, such as 0.05% to 1%, and preferably 0.01% to 35 0.75%, such as 0.15% to 0.5%, and even more preferably 0.20% to 0.40%.

In some embodiments of the invention, the monoglyceride is present in an amount of 0.01% to 5,0% by weight of the frozen food product and the digiyceride is present in an amount of 0.01% to 5,0% by weight of the frozen food product 301497667:508417 9 In some preferred embodiments of the invention, the monoglyceride is present in an amount of 0.02% to 1.0% by weight of the frozen food product and digiyceride is present in an amount of 0.05% to 2.0% by weight of the frozen food product.

In an even more preferred embodiment of the invention, the monogiyceride is present In an amount of 0,05% to 0.25% by weight of the frozen food product and digiyceride is present in an amount of 0.1% to 0.5% by weight of the frozen food product.

For example, the monoglyceride may be present in an amount of 0.05% to 0.3% by weight and the digiyceride may be present in an amount of 0.15% to 0.5% by weight.

In some preferred embodiments of the invention, the frozen food product comprises 2-PGME in an amount of 0.01% to 10% by weight, 1-PGME in an amount of 0.01% to 10% 15 by weight, monoglyceride in an amount of 0.01% to 5.0% by weight, and digiyceride in an amount of 0.01% to 5.0% by weight.

The frozen food product may e.g. comprise 2-PGME in an amount of 0.05% to 1% by weight, 1-PGME in an amount of 0.02% to 1% by weight, monoglyceride is present in an 20 amount of 0.01% to 1% by weight, and digiyceride is present in an amount of 0,05% to 1% by weight.

The frozen food product may e.g. comprise 2-PGME in an amount of 0.05% to 0.5% by weight, 1-PGME in an amount of 0.05% to 0.5% by weight, monoglyceride in an amount of 25 0.15% to 0.5% by weight, and digiyceride in an amount of 0,05% to 0.5% by weight.

The ratio by weight between the monoglyceride and the digiyceride is typically at most 95:5, such as at most 75:25, preferably at most 50:50, such as at most 40:60, and even more preferably at most 25:75, such as at most 10:90.

In some embodiments of the invention, the ratio by weight between monoglyceride and digiyceride is in range of 2:98 to 98:2, such as 3:97 to 80:20, preferably in the range of 4:96 to 60:40, and even more preferably in the range 5:95 to 40:60, such as 6:94 to 25:75.

In some preferred embodiments of the Invention, the frozen food product additionally comprises one or more stabilizers.

The stabilizer may contain one or more different stabilizers, e.g. 2 different stabilizers, 3 different stabilisers, 4 different stabilisers, or 5 different stabilizers.

The stabilizer may e.g. comprise at least one stabilizer selected from the group of agar, gelatine, gum acacia, pectin, guar gum, locust bean gum, tara gum, gum tragacanth, xanthan, carrageenan, semi-refined carrageenan, eucheuma seaweed, semi-refined seaweed, semi-refined carrageenan, carboxymethyl cellulose, microcrystalline cellulose, sodium alginate, propyleneglycol alginate and its salts, carob gum, guar gum, alginate, starch, and mixtures thereof.

In some preferred embodiments of the invention, the frozen food product additionally comprises one or more anti-freeze proteins.

In some preferred embodiments of the invention, the frozen food product additionally comprises one or more freezing point depressants.

The freezing point depressant may e.g. comprise at least one freezing point depressant selected from the group of an alcohol, a polyol, a sugar, and a mixture thereof.

A useful alcohol is e.g. ethanol.

Useful polyols are e.g. sorbitol, mannitol, lactitol, xylitol, maltitol, glycerol, isomalt, erythritol, or mixtures thereof.

Useful sugars are e.g. sucrose, dextrose, fructose, fructose syrup, oligofructose, glucose syrup, polydextrose, corn syrup, inulin, or mixtures thereof.

In some preferred embodiments of the invention, the frozen food product additionally comprises one or more isomerization inhibitors.

The isomerization inhibitor may e.g. comprise a chelating agent.

The chelating agent may comprise one or more chelating agents selected from the group consisting of an amino acid, an aminocarboxylate, a hydroxycarboxylate, a polyphosphate, and mixtures thereof.

A useful amino acid chelating agent is e.g. glycine.

A useful aminocarboxylate chelating agent is e.g. ETDA. 301497667:508417 11 Useful hydroxycarboxulate chelating agents are e.g. citric acid, tataric acid, or gluconic acid.

Useful polyphosphate chelating agents are e.g. hexametaphoshoric acid, pyrophosphoric acid, disodlumphosphate, tripolyphosphoric acid, or phytic acid.

In some embodiments of the invention, the chelating agent is an at least bidentate chelating agent, such as an at least tridentate chelating agent, such as an at least 10 tetradentate chelating agent, preferably an at [east pentadentate chelating agent, and even more preferably an at least hexadentate chelating agent.

An at least bidentate chelating agent is capable of forming at least 2 co-ordinate bonds with the same metal ion. An at least tridentate chelating agent is capable of forming at 15 least 3 co-ordinate bonds with the same metal ion. An at least tetradentate chelating agent is capable of forming at least 4 co-ordinate bonds with the same metal ion. An at least pentadentate chelating agent is capable of forming at least 5 co-ordinate bonds with the same metal ion. An at least hexadentate chelating agent is capable of forming at least 6 co-ordinate bonds with the same metal ion.

Useful tridentate chelating agents are e.g. di-carboxylic acids such as malonic acid, or e.g glycine.

Useful tridentate chelating agents are e.g. tri-carboxylic acids such as citric acid.

Useful tetradentate chelating agents are e.g. corrole molecules, heme molecules, triethylenetetramine (trien), tris(2-aminoethyl)amine (tren), tris(2-diphenylphosphineethyl)amine, and nitrilotriacetic acid (nta).

A useful pentadentate chelating agents is e.g ethylenediaminetriacetate.

Useful hexadentate chelating agents are e.g. ethylenediaminetetraacetate (EDTA) and l,10-diaza-4,7,13,16,21,24-hexaoxabicyclo[8.8.8]hexacosane (Cryptand [2,2,2]).

In some preferred embodiments of the invention, the chelating agent is EDTA.

The present invention may be employed in a wide range of frozen food products, and is particularly advantageous in aerated frozen food products. 301497667:508417 12 Thus, in some preferred embodiments of the invention, the frozen food product is an aerated frozen food product.

In the context of the present invention, the term "aerated frozen food product" means that 5 the frozen food product contains small air bubbles, typically smaller than 0.5 mm in diameter and sometimes even smaller than 0.1 mm. The degree of aeration is often measured by means of the overrun of the aerated frozen food product.

In the context of the present invention, the term "overrun" relates to the %-increase of 10 the volume of an aerated frozen food product relative to a frozen food product without any air bubbles, which increase can be related to the air bubbles of the aerated frozen food product.

The overrun may e.g. be determined by taking a sample having the volume Va of an 15 aerated frozen food product. The sample of the aerated frozen food product is then melted and the air bubbles are removed, e.g. by degassing. The volume of the melted food product without air bubbles, Vm, is then measured. The overrun, O, can be determined as V -V 0=a '"-100% Vm An aerated frozen food product typically has an overrun of at least 0.5%, such as at least 20 1%.

The frozen food product typically has an overrun of at least 10%, such as at least 10% or at least 50%, preferably at least 100% such as at least 150%, and in some types of frozen food products even more preferably at least 200% such as at least 250%.

The frozen food product may e.g. have an overrun in the range of 10%-300%, such as In the range of 25%-250%, preferably In the range of 50%-200%, and even more preferably in the range of 75%-150%, such as in the range of 100%-125%.

The frozen food product may e.g. comprise at least one frozen food product selected from the group consisting of ice cream, low fat ice cream, ice miik, sherbet, sorbet, frozen fruit juice, frozen yoghurt, frozen water ice, aerated frozen bars, frozen dessert, frozen aerated cream, and a combination thereof.

It is thus envisioned that the frozen food product may be a combination of different types of conventional frozen food product, such as a combination of frozen Ice cream and frozen sorbet; or frozen low fat ice cream and frozen fruit juice. 301497667:508417 13 In some embodiments of the invention, the frozen food product is a iow fat frozen food product. The tow fat frozen food product normally comprises at most 10% fat by weight, such as at most 5% fat, preferably at most 3% fat, such as at most 2% fat by weight, or 5 at most 1% fat by weight.

In the context of the present invention, the term "fat" shouid be interpreted broadly and generally relates to one or more triglycerides independent of their melting temperature. The term "fat" comprises both triglycerides that are in liquid form at 25°C, as well as 10 triglycerides that are in solid or semi-solid form at 25°C.

In some preferred embodiments of the invention, the frozen food product is an ice cream.

The ice cream typically comprises fat in an amount of 0.01-25% by weight, and preferably 15 in an amount of 0.1-18% by weight.

The ice cream typicaily comprises bulking agent in an amount of 1-35% by weight, and preferably in an amount of 5-25% by weight, Typically, the bulking agent comprises at least one bulking agent selected from the group consisting of a sugar, sugar alcohol, potydextrose, maltodextrin, a polyoi, native starch, modified starch, microcrystalline cellulose, and mixtures thereof.

The ice cream typicaily comprises milk solid non-fat in an amount of 0.5-30% by weight, 25 and preferably in an amount of 2-20% by weight, In the context of the present invention, the term "milk solid non-fat" relates to solid materials that can be derived from milk, and which solid material is not fat.

The ice cream typically comprises emulsifying system in an amount of 0.01-10 % by weight, and preferably in an amount of 0.1-2 % by weight, The ice cream typically comprises stabilizer in an amount of 0.01-5% by weight in an amount of 0.1-2% by weight, The ice cream typically comprises water in an amount of 20-90% by weight, and preferably in an amount of 40-80% by weight. 301497667:508417 14 In some embodiments of the invention, the ice cream comprises fat in an amount of 0.1-18% by weight, bulking agent in an amount of 5-25% by weight, miik solid non-fat in an amount of 2-20% by weight, emulsifying system in an amount of 0.01-10 % by weight, stabilizer in an amount of 0.01-5% by weight, and water in an amount of 40-80% by 5 weight.

The present inventors have found that the emulsifying system of the present invention is very useful as an emulsifier for low fat ice cream. Thus, in some preferred embodiments of the invention, the frozen food product is a low fat ice cream.

The low fat ice cream normally comprises at most 10% fat by weight, such as at most 5% fat, preferably at most 3% fat, such as at most 2% fat by weight, or at most 1% fat by weight.

Even lower amounts of fat may be used, thus, the low fat ice cream may comprise at most 3% fat by weight, such as at most 2% fat, preferably at most 1% fat, such as at most 0.5% fat by weight, or at most 0.2% fat by weight.

A low fat ice cream may e.g. comprise fat in an amount of 0.01-10% by weight, such as in 20 an amount of 0.05-8% by weight, preferably in an amount of 0.1-5% by weight, and even more preferably in an amount of 0.25-3% by weight.

The low fat ice cream may comprise fat in an amount of 0.01-10% by weight, bulking agent in an amount of 5-35% by weight, miik solid non-fat in an amount of 5-15% by 25 weight, emulsifying system in an amount of 0.01-10% by weight, stabilizer in an amount of 0.01-15% by weight, and water in an amount of 40-80% by weight.

A low fat ice cream typically comprises fat in an amount of 0.1-5% by weight, bulking agent in an amount of 5-35% by weight, milk solid non-fat in an amount of 5-15% by 30 weight, emulsifying system in an amount of 0.01-10% by weight, stabilizer in an amount of 0.01-15% by weight, and water in an amount of 40-80% by weight.

The frozen food product may e.g. comprise a frozen yoghurt.

The frozen food product may e.g. comprise a sorbet.

The frozen food product may also comprise a sherbet. 301497667:508417 In some embodiments of the invention, the frozen food product comprises or essentially consists of an aerated cream and the emulsifier system. Normally, an aerated cream contains at least 10% fat by weight, such as at least 15% fat by weight, preferably at least 25% fat by weight, such as at least 30% fat by weight, and even more preferably at least 5 40% fat by weight, such as at least at 50% fat by weight. The aerated cream preferably comprises milk fat.

Another aspect of the invention relates to an emulsifying system as described herein, i.e. an emulsifying system comprising a 2-PGME of a fatty acid.

In some preferred embodiments of the invention, the emulsifying system furthermore comprises a 1-PGME of a fatty acid.

The ratio by weight of 2-PGME and 1-PGME in the emulsifying system may e.g. be at least 15 1:4, such at least 1:3, or at least 3:7, preferably at least 1:2, such as at least 4:7, and even more preferably at least 4:6, such as at least 1:1. It is envisioned that the ratio by weight of 2-PGME and 1-PGME in the emulsifying system may e.g. be at least 2:1, such as at least 3:1, at least 8:2, or at least 9:1.

The ratio by weight of 2-PGME and 1-PGME in the emulsifying system is normally in the range of 1:10 to 10:1, such as in the range of 1:8 - 8:1, preferably in the range of 1:6 -6:1; such as in the range of 1:4 - 4:1, and even more preferably in the range of 1:2 -2:1, such as in the range of 1:1.5 - 1.5:1, and preferably in the range of 4:5 to 5:4.

It is also envisioned that the ratio by weight of 2-PGME and 1-PGME in the emulsifying system may be in the range of 3:7 to 10:1, such as in the range of 3:7 to 8:1, preferably in the range of 3:7 to 6:1 , such as in the range of 3:7 to 4:1, and even more preferably in the range of 3:7 to 2:1, such as in the range of 3:7 to 1:1.

Additionally it is envisioned that the ratio by weight of 2-PGME and 1-PGME of the emulsifying system may be in the range of 3:7 to 10:1, such as in the range of 1:1 to 10:1, preferably in the range of 2:1 to 10:1 , such as in the range of 4:1 to 10:1, and even more preferably in the range of 6:1 to 10:1, such as in the range of 8:1 to 10:1.

Emulsifying systems having the above ratios between 2-PGME and 1-PGME have been found to be useful for ice creams and particularly for low fat ice creams. 301497667:508417 16 The emulsifying system typically comprises at least 5% 2-PGME by weight, such as at least 10%, or at least 20%, preferably at least 25%, such as at least 30%, and even more preferably at least 33%, such as at least 35%.

In some preferred embodiments of the invention, the emulsifying system even comprises at least 40% 2-PGME by weight, such as at least 45%, or at least 50%, preferably at least 55%, such as at least 60%, and even more preferably at ieast 65% such as at least 75%.

It is envisioned that the emulsifying system may comprise approximately 100% 2-PGME 10 by weight, i.e. at least 80% by weight of a 2-PGME, such as at ieast 85, preferably at least 90%, such as at least 95%, and even more preferably at ieast 97.5% such as at least 99%.

In some preferred embodiments of the Invention, the emulsifying system comprises at 15 least 35% 2-PGME by weight.

The emulsifying system typicaily comprises at least 5% 1-PGME by weight, such as at least 10%, or at least 20%, preferably at least 25%, such as at least 30%, and even more preferably at least 33%, such as at least 35%.

In some preferred embodiments of the invention, the emulsifying system even comprises at least 40% 1-PGME by weight, such as at least 45%, or at least 50%, preferably at least 55%, such as at least 60%, and even more preferably at least 65% such as at ieast 75%.

In some preferred embodiments of the invention, the emulsifying system comprises 2-PGME in an amount In the range of 5-95% by weight, and 1-PGME in an amount in the range of 2-95% by weight, For example, the emulsifying system may comprise 2-PGME in an amount in the range of 30 20-90% by weight, and 1-PGME In an amount in the range of 5-75% by weight.

Alternatively, the emulsifying system may comprise 2-PGME in an amount in the range of 30-90% by weight, and 1-PGME in an amount in the range of 5-60% by weight.

For example, the emulsifying system may comprise 2-PGME in an amount in the range of 35-95% by weight, and 1-PGME in an amount in the range of 5-65% by weight.

The emulsifying system may e.g. comprise 2-PGME in an amount in the range of 40-90% by weight, and 1-PGME in an amount in the range of 5-60% by weight. 301497667:508417 17 Thus, the emulsifying system may comprise 2-PGME in an amount in the range of 40-70% by weight, and 1-PGME in an amount in the range of 25-60% by weight.

Also, the emulsifying system may comprise 2-PGME in an amount in the range of 40-60% by weight, and 1-PGME in an amount in the range of 40-60% by weight, such as 2-PGME in an amount in the range of 45-55% by weight, and 1-PGME in an amount in the range of 45-55% by weight A number of different fatty acids may be used in 1-PGME and 2-PGME of the emulsifying system.

However, the fatty acids of the 2-PGME and/or the 1-PGME typically comprise one or more fatty acid containing in the range of 4 to 24 carbon atoms, preferably in the range of 14-20 15 carbon atoms, and even more preferably in the range of 16-18 carbon atoms.

The term "and/or" used in the context "X and/or Y" should be interpreted as "X", or "Y", or "X and Y".

The 2-PGME and/or the 1-PGME may comprise a saturated fatty acid.

Alternatively or in addition, the fatty acid of the 2-PGME and/or the 1-PGME may comprise an unsaturated fatty acid, such as a mono-unsaturated fatty acid, or a poly-unsaturated fatty acid.

The emulsifying system may thus comprise a 2-PMGE comprising a saturated fatty acids, and a 2-PMGE comprising an unsaturated fatty acids.

Likewise, the emulsifying system may comprise a 1-PMGE comprising a saturated fatty 30 acids, and a 1-PMGE comprising an unsaturated fatty acids.

Useful fatty acids may be derived from a number of different vegetable and animal fats. In some embodiments of the invention, at least one fatty acid of the 2-PGME or the 1-PGME is derived from a fat or oil selected from the group consisting of sunflower oil, sunflower 35 seed oil, palm oil, palm kerne! oil, coconut oil, rape seed oil, soya bean oil, and a mixture thereof.

In some preferred embodiments of the invention, the emulsifying system comprises one or more additional emulsifiers. 301497667:508417 18 The additional emulsifier may e.g. comprise a digiyceride. Alternatively, or in addition thereto, the additional emulsifier may comprise a monoglyceride, Thus, the additional emulsifier may e.g. comprise a monogiyceride and a digiyceride.

The fatty acid of the monoglyceride may comprise a saturated fatty acid.

In the context of the present invention, when reference is made to one or more fatty acids of a monoglyceride, a digiyceride, a triglyceride, a PGME, or a PDME, it should be 10 understood that the fatty acids are not in their free form, but are bound to glycerol or propylene glycol by means of ester bonds. It is, however, possible to derived the fatty acids from these esters by hydrolysis.

The fatty acids of the digiyceride may comprise saturated fatty acids.

The fatty acid of the monoglyceride may comprise an unsaturated fatty acid, The fatty acids of the digiyceride may comprise unsaturated fatty acids.

The fatty acids of the monoglyceride may comprise a saturated fatty acid and an unsaturated fatty acid, The fatty acids of the digiyceride may comprise saturated fatty acids and unsaturated fatty acids.

In some embodiments of the invention, the emulsifying system comprises of digiyceride in an amount of at least 5% by weight, such as at least 10%, or at least 20%, preferably at least 25%, such as at least 30%, and even more preferably at least 33%, such as at least 35%.

The emulsifying system even comprises at least 40% digiyceride by weight, such as at least 45%, or at least 50%, preferably at least 55%, such as at ieast 60%, and even more preferably at least 65% such as at least 75%.

The additional emulsifier may comprise one or more other emulsifiers described herein.

However, in some embodiments of the invention, the emulsifying system does not contain sorbitan tristearate. 301497667:508417 19 The ratio by weight between the total amount of propylene giyco! monoester and the total amount of monoglyceride and digiyceride may be at least 1:4, such as at least 1:3, preferably at least 1:2, such as at least 1:1, and even more preferably preferably at least 2:1 For example, the ratio by weight between the total amount of propylene glycol monoester and the total amount of monogiyceride and digiyceride may be in the range of 1:4 to 10:1, preferably in the range 1:3-5:1, such as in the range 1:3-3:1, and even more preferably in the range 1:2-2:1 In some embodiments of the invention, the emulsifying system additionally comprises one or more components selected from the group consisting of monoglycerides, diglycerides, triglycerides, glycerol, free fatty acids, and mixtures thereof. The emulsifying system may furthermore comprise diesters of fatty acids and propane-l,2-diol, typically in small 15 amounts if present at all.

As mentioned above, it is envisioned that the emulsifying system may comprise useful additives such as a stabilizer. For example, the emulsifying system may comprise in the range of 1-90% stabilizer by weight, preferably in the range of 10-80% stabilizer by 20 weight, such as in the range of 15-60% stabilizer by weight, and even more preferred in the range of 20%-50% stabilizer by weight.

The present inventors have found that the emulsifying system advantageously may contain one or more stabilisers before the emulsifying system is added to the food product. The 25 presence of the emulsifiers in the emulsifying system eases the dispersion and homogeneous distribution of the emulsifier and the stabiliser in the food product. It is believed that the emulsifiers of the emulsifying system act as wetting agents on the surface of the stabilisers, thus enhancing the wettability and the dispersion of the stabiliser. Without being bound by theory, it is furthermore believed that some of the 30 unique properties of the frozen food products of the invention at least partly are a result of the improved dispersion of the stabiliser in the frozen food product.

The emulsifying system may be formulated in a number of different ways depending on the application in which it has to be used.

The emulsifying system may e.g. be in liquid form, in semi-solid form, or in solid form, e.g. at 25°C. For example, at the emulsifying system may be in the form of a powder, a granulate, or a paste. The powder or granulate is preferably free flowing. 301497667:508417 The emulsifier of the emulsifying system may comprise hydrated emulsifiers, e.g, hydrated in water or in one or more poiyoi, such as propylene glycol (propane-l,2-diol) and/or glycerol. The hydrated emulsifiers may furthermore be hydrated in a mixture of water and propane-l,2-diol, or in a mixture of water glycerol.

Preparation of a hydrated emulsifier can e.g. be done by mixing water and/or polyol and an emulsifier at a temperature below the melting point of the emulsifier and successively increasing the temperature to a point above the melting point, optionally adjusting the pH, and cooling the hydrated emulsifier below the melting point of the emulsifier, e.g. ambient 10 temperature.

For example, at ieast 25% by weight of the total amount of emulsifier of the emulsifying system may be hydrated emulsifiers, preferably at ieast 50% by weight of the total amount of emulsifier, such as at least 75% by weight, and even more preferably at least 15 90% by weight such as at least 95% by weight of the total amount of emulsifiers may be hydrated emulsifiers. Substantially all the emulsifiers of the emulsifying system may be hydrated.

In some embodiments of the invention, the emulsifier of the emulsifying system comprises 20 emulsifiers dissolved or incorporated in fat.

Normally, at least 25% by weight of the total amount of emulsifier of the emulsifying system is dissolved or incorporated in fat, preferably at least 50% by weight of the total amount of emulsifier, such as at least 75% by weight, and even more preferably at least 25 90% by weight such as at least 95% by weight of the total amount of emulsifiers may be dissolved or incorporated in fat. Substantially ail the emulsifiers of the emulsifying system may be hydrated.

The present inventors have found 2-PGME of the emulsifying system is converted to 1-30 PGME under some conditions, possibly due to acyl migration. The inventors have discovered that this problem can be solved by keeping the emulsifying system at low temperature, e.g. during storage and/or during transportation.

Thus, in some preferred embodiments of the invention, the temperature of the emulsifying 35 system is at most 45°C, preferably at most 35°C, such as at most 25°C, and even more preferred at most 5°C, such as at most 0°C. For example, the temperature of the emulsifying system may be at most 45°C during storage and/or during transportation, preferably at most 35°C, such as at most 25°C, and even more preferred at most 5°C, such as at most 0°C during storage and/or during transportation. 301497667:508417 21 In some embodiments of the invention, the temperature of the emulsifying system, e.g. during storage and/or during transportation, is in the range of -30°C to 45°C, such as 0°C -40°C, preferably 5°C - 35°C, and even more preferably in the range 10°C-30°C, such as in 5 the range 15°C-25°C.

Yet another aspect of the invention relates to a packaged emulsifying system comprising a container, said container comprising an emulsifying system as described herein and a container wall, which protects the emulsifying system from the surrounding environment.

The temperature of the emulsifier system of the packaged emulsifier system, e.g. during storage and/or during transportation, is preferably in the range of -30°C to 45°C, such as 0QC - 40°C, preferably 5°C - 35°C, and even more preferably in the range 10°C-30°C, such as in the range 15°C-25°C.

The present emulsifying systems appear to have an acceptable stability, especially when stored or transported in solid form.

Thus, in some embodiments of the invention, the emulsifiers of the emulsifying system is 20 in solid form during storage and/or during transportation.

In some embodiments of the invention, the emulsifying system Is in solid form during storage and/or during transportation.

A further aspect of the Invention relates to a method of preparing a frozen food product comprising the step of a) mixing a food intermediate with an emulsifying system as described herein, thus obtaining the mixture, b) optionally, heating the mixture or the food intermediate to a temperature sufficient for 30 the emulsifying system to soften or melt, and c) freezing the resulting mixture.

In some embodiments of the invention, step b) is not optional, thus the mixture is heated to a temperature sufficient for the emulsifying system to melt. The temperature is typically 35 near the softening point or melting point of the emulsifying system.

The emulsifying system which is added in step a) may e.g, comprise a hydrated emulsifier or an emulsifier dissolved or incorporated in fat. An advantage of an emulsifying system comprising a hydrated emulsifier is that step b) may be omitted. 301497667:508417 "2.2.

Step a) and b) may be performed separately or concurrently, i.e. the food intermediate may be heated to the temperature of step b) when the emulsifying system is added.

As mentioned above, the components of the emulsifying system can both be applied to food intermediate as a mixture, or separately but at the same time. Alternatively, the components of the emuisifying system can be applied to the other ingredients of the frozen food product separately and at different times during the production of the frozen food product.

Normally, 2-PGME is present in an amount of at least 0.01% by weight of the food intermediate, such as at least 0.1% by weight, preferably at least 0.15% by weight, such as at least 0.2% by weight, and even more preferably at least 0.25% by weight of the food intermediate. 2-PGME may for example be present in an amount of 0.01% to 10.0% by weight of the food intermediate, such as in an amount of 0.1% to 1% by weight, preferably in an amount of 0.15% to 0.5% by weight, and even more preferably in an amount of 0.2% to 0.4% by weight, such as in an amount of 0.25% to 0.35% by weight.

Monoglyceride and/or digiyceride may be present in an amount of 0.01% to 5.0% by weight of the food intermediate. The ratio by weight between the total amount of propylene glycol monoester and a total amount of monoglyceride and digiyceride is typically in the range of 1:4 to 10:1.

The method of preparing the frozen food product may furthermore comprising one or more steps selected from the group of: - pasteurizing the mixture, - homogenizing the mixture 30 - sterilizing the mixture, - cooling the mixture, - aging the mixture, - aerating the mixture, - freezing the mixture, and 35 - combinations thereof.

A number of useful features related to the preparation of frozen food products, such as pasteurization, homogenization, aging, aeration, sterilization, and freezing, are e.g. 301497667:508417 23 described in Arbuckle and Marshall and in the PCT application WO 2005/060,763, The contents of both documents are incorporated herein by reference for all purposes.

A preferred method of sterilizing the mixture Is ultra high temperature (UHT) sterilization.

In some preferred embodiments of the invention, the method comprises step a), and the steps of: - homogenize the mixture of step b) - sterilizing the mixture 10 - aging the mixture, - aerating the mixture, and - freezing the mixture.

Yet an aspect of the invention relates to the use of an emulsifying system as described 15 herein as emulsifier in a frozen food product.

The emulsifying system is particularly useful as emulsifier in frozen food products such as frozen desserts, ice cream, low fat Ice cream, ice miik, sherbets, sorbet, frozen fruit juice, frozen yoghurt, frozen water ice, aerated frozen bars, creams, and imitation creams.

It should be noted that embodiments and features described in the context of one of the aspects of the present invention also apply to the other aspects of the invention.

Ail patent and non-patent references cited in the present application, are hereby 25 incorporated by reference in their entirety.

The invention will now be described in further details by the following items: 1. A frozen food product comprising an emulsifying system comprising a 2-propyiene glycol 30 monoester of a fatty acid (2-PGME), 2. The frozen food product according to item 1, wherein the emulsifying system additionally comprises a 1-propyiene glycol monoester of a fatty acid (1-PGME). 3. The frozen food product according to item 2, wherein the ratio by weight of 2-PGME and 1-PGME is at least 1:4 4. The frozen food product according to item 2, wherein the ratio by weight of 2-PGME and 1-PGME is 1:10 to 10:1.

. The frozen food product according to any of the items 1-4, wherein the 2-PGME is present in an amount of at least 0.01% by weight of the frozen food product. 6. The frozen food product according to any of the items 1-5, wherein the 1-PGME is present in an amount of at least 0.01% by weight of the frozen food product. 7. The frozen food product according to any of the items 1-6, wherein the 2-PGME is present in an amount of at least 0.01% by weight of the frozen food product and the 1-PGME is present in an amount of at least 0.01% by weight of the frozen food product. 8. The frozen food product according to any of the items 1-7, wherein the 2-PGME is present In an amount of 0.01% to 10% by weight of the frozen food product. 9. The frozen food product according to any of the items 1-8, wherein the 1-PGME is present in an amount of 0.01% to 10% by weight of the frozen food product.

. The frozen food product according to any of the items 1-9, wherein the 2-PGME is present in an amount of 0.01% to 10% by weight of the frozen food product and the 1-PGME is present in an amount of 0.01% to 10% by weight of the frozen food product. 11. The frozen food product according to any of the items 1-10, wherein the 2-PGME is present in an amount of 0.05% to 1% by weight of the frozen food product and the 1-PGME is present in an amount of 0.05% to 1% by weight of the frozen food product. 12. The frozen food product according to any of the items 1-11, wherein the emulsifying system comprises one or more additional emulsifiers. 13. The frozen food product according to item 12, wherein the additional emulsifier comprises a digiyceride. 14. The frozen food product according to item 12 or 13, wherein the additional emuisifier comprises a monoglyceride.

. The frozen food product according to any of items 12-14, wherein the additional emuisifier comprises a monogiyceride and a digiyceride, 16. The frozen food product according to any of items 14-15, wherein the fatty acid of the monogiyceride comprises a saturated fatty acid. 301497667:508417 17. The frozen food product according to any of items 13-16, wherein the fatty acids of the digiyceride comprise saturated fatty acids. 18, The frozen food product according to any of the items 14-17, wherein the fatty acid of the monogiyceride comprises an unsaturated fatty acid. 19. The frozen food product according to any of the items 13-18, wherein the fatty acids of the digiyceride comprise unsaturated fatty acids, . The frozen food product according to any of the items 13-19 wherein the digiyceride is present in an amount of at least 0.01% by weight. 21. The frozen food product according to any of the items 13-20 wherein the 15 monoglyceride is present in an amount of at least 0,01% by weight. 22. The frozen food product according to any of the items 13-21 wherein the digiyceride is present in an amount of 0.01% to 5.0% by weight. 23. The frozen food product according to any of the items 14-22 wherein the monogiyceride is present in an amount of 0.01% to 5.0% by weight. 24. The frozen food product according to any of the items 14-22, wherein the monoglyceride is present in an amount of 0.01% to 5.0% by weight and digiyceride is present in an amount of 0.01% to 5.0% by weight.

. The frozen food product according to any of the items 14-24, wherein the monoglyceride is present in an amount of 0.02% to 1.0% by weight and digiyceride is present in an amount of 0.05% to 2.0% by weight. 26. The frozen food product according to any of the items 14-25, wherein the monoglyceride is present in an amount of 0.05% to 0.25% by weight and digiyceride is present in an amount of 0.1% to 0.5% by weight. 27. The frozen food product according to any of the items 14-26, wherein the monoglyceride is present in an amount of 0.05% to 0.15% by weight and digiyceride is present in an amount of 0.15% to 0.4% by weight. 28, The frozen food product according to any of the items 14-27, wherein 301497667:508417 26 2-PGME is present in an amount of 0.01% to 10% by weight, 1-PGME is present in an amount of 0.01% to 10% by weight, monoglyceride is present in an amount of 0,01% to 5,0% by weight, and digiyceride is present in an amount of 0.01% to 5.0% by weight. 29. The frozen food product according to any of the items 14-28, wherein 2-PGME is present in an amount of 0,05% to 1% by weight, 1-PGME is present in an amount of 0.02% to 1% by weight, monoglyceride is present in an amount of 0.01% to 1% by weight, and digiyceride is present in an amount of 0.05% to 1% by weight.

. The frozen food product according to any of the items 14-29, wherein 2-PGME is present in an amount of 0.05% to 0.5% by weight, 1-PGME is present in an amount of 0.05% to 0.5% by weight, monogiyceride is present in an amount of 0.1% to 0.5% by weight, and digiyceride is present in an amount of 0.05% to 0.6% by weight. 31. The frozen food product according to any of the items 14-30, wherein the ratio by weight between the monoglyceride and the digiyceride is at most 95:5 32. The frozen food product according to any of the items 14-31, wherein the ratio by weight between monoglyceride and digiyceride is in the range of 2:98 to 95:5. 33. The frozen food product according to any of the preceding items, which additionally 25 comprises one or more stabilizers. 34. The frozen food product according to any of the preceding items, which additionally comprises one or more anti-freeze proteins. 35. The frozen food product according to any of the preceding items, which additionaliy comprises one or more freezing point depressants. 36. The frozen food product according to any of the preceding items, which additionally comprises one or more isomerization inhibitors. 37. The frozen food product according to Item 33, wherein at least one stabilizer is selected from the group of agar, gelatine, gum acacia, pectin, guar gum, locust bean gum, tara gum, gum tragacanth, xanthan, carrageenan, semi-refined carrageenan, eucheuma seaweed, semi-refined seaweed, carboxymethyi cellulose, microcrystalline ceilulose, 301497667:508417 27 sodium alginate, propyieneglycol alginate and its salts, carob gum, guar gum, alginate, starch, and mixtures thereof, 38. The frozen food product according to item 35, wherein at least one freezing point 5 depressant is selected from the group of an alcohol, a polyol, a sugar, and a mixture thereof. 39. The frozen food product according to item 36, wherein the isomerization inhibitor comprises a chelating agent. 40. The frozen food product according to item 39, wherein the chelating agent comprises at least one organic acid selected from the group consisting of citric acid, malonic cid, gluconic acid tartaric acid and phosphoric acid. 41. The frozen food product according to item 39 or 40, wherein the chelating agent comprises glycine. 42. The frozen food product according to any of the preceding items, wherein the frozen food product is an aerated frozen food product. 43. The frozen food product according to item 42, having an overrun of at least 10% 44. The frozen food product according to any of the preceding items, wherein the frozen food product comprises at least one frozen food product selected from the group consisting of ice cream, low fat ice cream, ice miik, sherbet, sorbet, frozen fruit juice, frozen yoghurt, frozen water ice, aerated frozen bars, frozen dessert, frozen aerated cream, unwhipped dairy cream, imitation creams, and a combination thereof. 45. The frozen food product according to item 44, wherein the frozen food product is an ice 30 cream. 46. The frozen food product according to item 45, wherein the ice cream comprises fat in an amount of 0.1-18% by weight, bulking agent in an amount of 5-25% by weight, milk solid non-fat in an amount of 2-20% by weight, emulsifying system in an amount of 0.01- 10 % by weight, stabilizer in an amount of 0,01-5% by weight, and water in an amount of 40-80% by weight. 47. The frozen food product according to item 45 or 46, wherein the frozen food product is a low fat ice cream. 301497667:508417 28 48. The frozen food product according to 47, wherein the low fat ice cream comprises at most 10% fat by weight, such as at most 5% fat, preferably at most 3% fat, such as at most 2% fat by weight, or at most 1% fat by weight. 49. The frozen food product according to 47, wherein the low fat ice cream comprises at most 3% fat by weight, such as at most 2% fat, preferably at most 1% fat, such as at most 0.5% fat by weight, or at most 0.2% fat by weight 50. The frozen food product according to items 45 or 46, wherein the frozen food product is a sorbet. 51. The frozen food product according to items 45 or 46, wherein the frozen food product Is a sherbet. 52. The frozen food product according to any of the items 47-49, wherein the Sow fat ice cream comprises fat in an amount of 0.01-10% by weight, bulking agent in an amount of 5-35% by weight, milk solid non-fat in an amount of 5-12% by weight, emulsifying system in an amount of 0.01-10% by weight, stabilizer in an amount of 0.01-15% by weight, and water in an amount of 40-80% by weight. 53. The frozen food product according to Item 52, wherein the low fat ice cream comprises fat in an amount of 0.1-5% by weight, bulking agent in an amount of 5-35% by weight, miik solid non-fat in an amount of 5-12% by weight, emulsifying system in an amount of 0.01-10% by weight, stabilizer in an amount of 0.01-15% by weight, and water in an amount of 40-80% by weight. 54. The frozen food product according to item 44, wherein the frozen food product is a frozen yoghurt. 55. The frozen food product according to item 44, wherein the frozen food product is aerated cream. 56. The frozen food product according to item 46-55, wherein the bulking agent comprises at least one bulking agent selected from the group consisting of a sugar, sugar alcohol, polydextrose, maltodextrln, a polyol, native starch, modified starch, microcrystalline cellulose, and mixtures thereof. 57. An emulsifying system comprising a 2-PGME of a fatty acid. 301497667:508417 29 58. The emulsifying system according to item 57, furthermore comprising a 1-PGME of a fatty acid, 59. The emulsifying system according to item 58, wherein the ratio by weight of 2-PGME 5 and 1-PGME is at least 1:4. 60. The emulsifying system according to item 58 or 59, wherein the ratio by weight of 2-PGME and 1-PGME is 1:10 - 10:1. 61. The emulsifying system according to any of the items 57-60 comprising at least 5% 2-PGME by weight . 62. The emulsifying system according to any of the items 57-61 comprising at ieast 35% 2-PGME by weight . 63. The emulsifying system according to any of the items 58-62 comprising at least 5% 1-PGME by weight 1-PGME. 64. The emulsifying system according to any of the items 58-63 comprising at least 35% 20 1-PGME by weight. 65. The emulsifying system according to any of the items 58-64 comprising 2-PGME in an amount in the range of 5-95% by weight, and 1-PGME in an amount in the range of 2-95% by weight. 66. The emulsifying system according to any of the items 58-65 comprising 2-PGME in an amount in the range of 20-90% by weight, and 1-PGME in an amount in the range of 5-75% by weight. 67. The emulsifying system according to any of the items 58-66 comprising 2-PGME in an amount in the range of 30-90% by weight, and 1-PGME in an amount in the range of 5-60% by weight. 68. The emulsifying system according to any of the items 58-67 comprising 35 2-PGME in an amount in the range of 35-95% by weight, and 1-PGME in an amount in the range of 5-65% by weight. 69. The emulsifying system according to any of the items 58-68 comprising 2-PGME in an amount in the range of 40-90% by weight, and 301497667:508417 1-PGME in an amount in the range of 5-60% by weight. 70. The emulsifying system according to any of the items 58-69 comprising 2-PGME in an amount in the range of 40-70% by weight, and 5 1-PGME in an amount in the range of 25-60% by weight. 71. The emulsifying system according to any of the preceding items, wherein the 2-PGME and/or the 1-PGME comprises one or more fatty acids containing in the range of 4-24 carbon atoms. 72. The emulsifying system according to item 71, wherein the fatty acid of the 2-PGME and/or the 1-PGME comprises a saturated fatty acid. 73. The emulsifying system according to item 71, wherein the fatty acid of the 2-PGME 15 and/or the 1-PGME comprises an unsaturated fatty acid. 74. The emulsifying system according to item 71, the emulsifying system comprising: - a 2-PMGE comprising a saturated fatty acids, and a 2-PMGE comprising an unsaturated fatty acids. 75. The emulsifying system according to any of the items 71-74, the emuisifying system comprising: - a 1-PMGE comprising a saturated fatty acids, and - a 1-PMGE comprising an unsaturated fatty acids. 76. The emulsifying system according to any one of the items 71-75, wherein the fatty acid contains 14-20 carbon atoms, preferably 16-18 carbon atoms, 77. The emulsifying system according to any one of the Items 71-76, wherein the fatty 30 acid contains 16 or 18 carbon atoms. 78. The emulsifying system according to any one of the items 71-77, wherein the fatty acid Is a unsaturated, e.g, mono-unsaturated, fatty acid. 79. The emulsifying system according to any of the preceding items, wherein at ieast one fatty acid of the 2-PGME or the 1-PGME is derived from a fat or oil selected from the group consisting of sunflower oil, sunflower seed oii, palm oii, palm kernel oil, coconut oil, rape seed oil, soya bean oil, and a mixture thereof. 301497667:508417 31 80. The emulsifying system according to any of the preceding items, which comprises one or more additional emulsifier. 81. The emulsifying system according to item 80, wherein the additional emulsifier 5 comprises a digiyceride. 82. The emulsifying system according to item 80 or 81, wherein the additional emulsifier comprises a monoglyceride. 83. The emuisifying system according to any of items 80-82, wherein the additional emulsifier comprises a monogiyceride and a digiyceride. 84. The emulsifying system according to any of items 82-83, wherein the fatty acid of the monoglyceride comprises a saturated fatty acid. 85. The emulsifying system according to any of items 81-84, wherein the fatty acids of the digiyceride comprise saturated fatty acids. 86. The emulsifying system according to any of the items 82-85, wherein the fatty acid of 20 the monoglyceride comprises an unsaturated fatty acid. 87. The emulsifying system according to any of the items 81-86, wherein the fatty acids of the digiyceride comprise unsaturated fatty acids. 88. The emulsifying system according to any of the items 82-87, wherein the fatty acid of a first monoglyceride comprises a saturated fatty acid and the fatty acid of a second monoglyceride comprises an unsaturated fatty acid. 89. The emulsifying system according to any of the items 81-88, wherein fatty acids of the 30 digiyceride comprise a saturated fatty acid and an unsaturated fatty acid. 90. The emulsifying system according to any of the items 81-89, wherein the emulsifying system comprises of digiyceride in an amount of at least 5% by weight. 91. The emuisifying system according to any of the items 83-90, wherein the ratio by weight between the tota! amount of propylene glycol monoester and the total amount of monoglyceride and digiyceride is at least 1:4. 301497667:508417 32 92. The emulsifying system according to any of the items 83-91, wherein the ratio by weight between total amount of propylene glycol monoester and the total amount of monoglyceride and digiyceride is in the range of 1:4 to 10:1. 93. The emulsifying system according to any of the items 57-92, which additionally comprises one or more components selected from the group consisting of monoglycerides, diglycerides, triglycerides, glycerol, free fatty acids, and mixtures thereof. 94. The emulsifying system according to any of the items 57-93, which further comprises 10 one or more agents selected from the group of a stabilizer, an anti-freeze protein, an isomerisation inhibtor, and mixtures thereof. 95. The emulsifying system according to item 94, wherein the isomerization inhibitor comprises a chelating agent. 96. The emulsifying system according to any of the items 94-95, comprising a stabilizer. 97. The emulsifying system according to any of the items 94-98, comprising in the range of 1-90% stabilizer by weight, preferably in the range of 10-80% stabilizer by weight, such as in the range of 20-60% stabilizer by weight, and even more preferred in the range of 20-50% stabilizer by weight. 98. The emulsifying system according to any of the items 57-97, wherein said emuisifying system is in the form of a powder, a granulate, or a paste. 99. The emulsifying system according to any of the items 94-98, wherein the emulsifier of the emulsifying system comprises hydrated emulsifiers. 100. The emulsifying system according to any of the items 94-99, wherein at ieast 25% by 30 weight of the total amount of emulsifier of the emuisifying system is hydrated emulsifiers. 101. The emulsifying system according to any of the items 94-100, wherein the emulsifier of the emuisifying system comprises emulsifiers dissolved or incorporated in fat. 102. The emulsifying system according to item 101, wherein at ieast 25% by weight of the total amount of emulsifier of the emulsifying system is dissolved or incorporated in fat. 103. The emulsifying system according to any of the items 57-102, where the temperature of the emulsifying system is at most 45°, 301497667:508417 33 104, A packaged emulsifying system comprising a container, said container comprising an emulsifying system according to any of the items 57-103. 105. The packaged emulsifying system according to item 104, wherein the temperature of the emulsifying system is in the range of -30°C to 45°C 106. The packaged emuisifying system according to item 104, wherein the emulsifiers are on solid form. 107. A packaged emulsifying system according to item 104, wherein the emulsifying system is on solid form. 108. Method of preparing a frozen food product comprising the step of a) mixing a food intermediate with an emulsifying system as described herein, thus obtaining the mixture, b) optionally, heating the mixture or the food intermediate to a temperature sufficient for the emulsifying system to soften or melt, and c) freezing the resulting mixture. 109. Method of preparing a frozen food product according to item 108, wherein the emulsifying system of step a) comprises a hydrated emuisifier. 110. Method of preparing a frozen food product according to items 108 or 109, wherein 25 the emulsifying system of step a) comprises an emuisifier dissolved or incorporated in fat, 111. The method according to any of the items 108-110, wherein 2-PGME is present in an amount of at least 0.01% by weight of the food intermediate, 112. The method according to any of the items 108-111, wherein 2-PGME is present in an amount of 0.01% to 10.0% by weight of the food intermediate. 113. The method according to any of the items 108-112, wherein monoglyceride and/or digiyceride Is present in an amount of 0.01% to 5.0% by weight of the food intermediate. 114. The method according to any of the items 108-113, wherein the ratio by weight between the the total amount of propylene glycol monoester and a total amount of monoglyceride and digiyceride Is 1:4 to 10:1. 301497667:508417 34 115. The method of preparing a frozen food product according to any of the items 108-114, the method furthermore comprising one or more steps selected from the group of: - pasteurize the mixture - homogenize the mixture 5 - sterilizing the mixture - cooling the mixture - aging the mixture, - aerating the mixture, - freeze the mixture, - and combinations thereof. 116. The method of preparing a frozen food product according to item 115, the method comprising the steps of: - homogenize the mixture of step b) - sterilizing the mixture - aging the mixture, - aerating the mixture - freeze the mixture. 117. Use of an emulsifying system according to any of the items 57-103 as an emuisifier in a frozen food product.

The invention will now be described in further details in the following non-limiting examples. 301497667:508417 EXAMPLES Example 1 Preparation of 1-PGME The following two basic ice cream recipes % fat ice cream: Vegetable palm kernel fat (Polawar E31) Skim milk powder Whey powder 10 Sucrose Glucose sirup 42DE Guar gum Carrageenan Emulsifiers 15 Water ind 2-PGME were used for the examples mentioned herein: % 6% 6% 11.5% 3.35% 0.169 0.0455% as specified q.s. 2% fat ice cream: Vegetable palm kernel fat (Polawar E31) 2% Skim milk powder 6.25% Whey powder 6.25% Sucrose 12% Glucose sirup 42DE 4% Guar gum 0.195 Carrageenan 0.0525% Emulsifiers as specified Water q.s.

Example 2 Process for preparing ice cream The ice creams to be tested were ail prepared by the same general process. All the ingredient were mixed in the water and heated to 75°C. Then the entire mixture was homogenized at 200 bar followed by pasteurisation at 83°C for approximately 30 seconds. The homogenized ice cream mixture was allowed to rest for 18 hours at 5°C before it was 35 aerated and frozen in a lab scale continuous freezer. When the ice cream reached a temperature of -5.5 to -6°C it was filled in 0.2L paper boxes and frozen to -30°C for 24 36 hours. After this step the temperature was raised to -20°C for minimum 120 hours before the characteristics of the ice cream was tested.

Example 3 Tests for characterising the ice cream The ice creams according to the invention were exposed to the foilowing tests: Sensory test Sensory test is performed In panel of 7 persons. The panel evaluates the Ice cream with respect to its texture, ice crystal size, creaminess, coolness, flavour, sandyness, and visual appearance.

Melt test: The melt test and the determination of the melt figure of the ice cream is performed as follows.

A sample of ice cream having a temperature in the range of -18°C to -20°C is taken out of the freezer its weight is measured. The sample is then placed on a 4 mm mesh in an air circulated incubator at 25°C. Under the mesh a balance Is located for measuring the weight of liquid ice cream that melts off the ice cream sample. During the next 90 minutes, the weight of melted ice is reported by means of data transfer from the balance to a computer.

The melt figure is expressed as the loss of weight in % of the ice cream sample after 90 minutes of incubation at 25°C, The melt figure for each type of ice cream is measure by double determination The melt figure is determined both for ice cream that been exposed to a heat shock and ice cream that has not been exposed to a heat shock.

Heat shock: The some of the ice creams were exposed to a so-called heat shock to observe sensitivity of the ice cream to temperature fluctuations in Its environment. The heat shock was provoked by storing the ice cream for 1 week at -20°C (-19°C to -21°C), then for 4 days at -10°C (- 9°C to -11°C), and finally for 1 week at -20°C (-19°C to -21°C), 301497667:508417 37 After the heat shock the melt-down properties and sensory properties of the ice cream was evaluated.

Example 4 Experiment A Results from tests done in accordance with the above described and using 0.240% propyleneglycolmonoester with different ratio between the 1- and 2-isomer and 0.14% monoglyceride (95% mono, iodine value < 2} as coemulsifier are shown in the Table 1 below Table 1. Results for an ice cream formulation containing 5% fat, 0.24% PGME and 0.143% monoglyceride; HS = after heat shock. 2-PGME relative 1-PGME relative to Melt figure Melt figure Sensory score to total PGME total PGME (HS) 91% 9% 32% 53% 2 78% 22% 32% 50% 3 60.5% 39.5% 28% 45% 4 51.8% 48.2% 28% 45% 33% 66% % 59% 2 % 70% 28% 45% 4 16.9% 83.1% 28% 50% 2 From the test it can be concluded that the ratio between the two isomers of 15 propyleneglycolmonoester giving the best ice cream in terms of sensory score is approximately 1:1, but even 1:3 ratio between 1- and 2-isomer shows a quality improvement in terms of sensory scores. The melting figures shows that this parameter seems to be rather insensible to the changes in the ratio of the propyleneglycolmonoester isomers.

Example 5 Experiment B In addition to the tests done with a saturated (iodine value >2) monoglyceride ice cream preparations with different unsaturated monoglycerides and diglycerides have been done 25 i.e. the ratio between the monogiyceride and the digiyceride have been varied from 95:5 to 20:80. The results for a 5% fat ice cream are shown in the table 2 below 301497667:508417 38 Table 2. Results for an ice cream formulation containing 5% fat, 0.24% of total PGME and varying amount of unsaturated monogiyceride and digiyceride. Unsat. MG = unsaturated monoglyceride; Unsat. DG = unsaturated digiyceride; HS = after heat shock. 2-PGME 1-PGME Unsat. MG Unsat. DG Melt Melt Sensory relative to relative to Figure figure score total PGME total PGME (HS) 52% 48% 0.10% 0.04% <5% 47% 4 52% 48% 0.06% 0.19% <5% 23% 33% 66% 0.10% 0.04% 6% 55% 4 33% 66% 0.06% 0.19% <5% 37% 33% 66% 0.10% 0.30% <5% 48% The melting of the ice creams before heat shock is found to decrease when the saturated monoglyceride is replaced by unsaturated mono- and diglycerides. After heat shock it is found that the 1:1 ratio between the two PGME isomers increase the melting resistance compared to a 1:2 ratio of 2-PGME to 1-PGME. Further it is found that an increase in the ratio of digiyceride to monoglyceride improves the sensory score.

Example 6 Experiment C Resuits from a test done with a 2% fat ice cream is recorded in Table 3 beiow.

Table 3 Results of an ice cream formulation containing 2% fat, 0.24% tota! PGME, and varying amounts of unsaturated monoglyceride and digiyceride. Unsat. MG = unsaturated monogiyceride; Unsat. DG = unsaturated digiyceride; HS = after heat shock, Melt figures after 90 min. 2-PGME relative to total PGME 1-PGME relative to total PGME Unsat. MG Unsat. DG Melt figure Melt figure (HS) Sensory score 52% 48% 0.10% 0.04% 58% 63% 4 52% 48% 0,06% 0.19% 55% 63% It appears that it is possible to produce a 2% fat ice cream with a high sensory score. It was found that an increase in the ratio of digiyceride to monoglyceride improves the sensory score. 39 Example 7 Experiment D A series of various compositions of PGME have been tested together with various compositions of monoglycerides and diglycerides in a 5% fat ice cream formulation. The results are shown in Tables 4 and 6.

Table 4 Results for an ice cream formulation containing 5% fat, 0.24% of total PGME and varying amount of monoglycerides and diglycerides. Sat. MG = saturated monoglyceride Unsat. MG = unsaturated monoglyceride; Unsat. DG = unsaturated digiyceride; HS = after heat shock. Melt figures after 90 min. 2-PGME 1-PGME Sat. MG Unsat. MG Unsat. DG Melt Melt Sensory relative to relative to Figure figure score total PGME total PGME (HS) 33% 66% 0.14% 17 47 3 52% 48% 0.14% 45 4 % 72% 0.14% 29 44 2 52% 48% 0.10% 0.04% 51 3 52% 48% 0.06% 0.19% 3 19 It is observed that the combination of the 2 isomers of PGME in the ratio 1:1 and an unsaturated mono-and digiyceride with high level of digiyceride increase the melting resistance of the ice cream, Same combination gives the highest sensory score especialiy creaminess among the samples in this test run. The sample of ice cream produced with the highest level of 1-PGME is described as cold and less creaminess. From the trials with only saturated monoglyceride added it is observed that increasing ratio of 1-PGME in the mixture decrease the sensory score of the ice cream.

The ice crystal diameters of the samples were measured by means of SEM (Scanning electron microscopy). 301497667:508417 Table 5 Ice crystal diameters 2-PGME relative to total PGME 1-PGME relative to total PGME Sat. MG Unsat. MG Unsat. DG ^50,3 Span3 33% 66% 0.14% 39.24 1.09 52% 48% 0.14% 39.46 1.17 % 72% 0.14% 40.96 1.44 52% 48% 0,10% 0.04% 39.16 1,28 52% 48% 0.06% 0.19% 38.05 0.93 It is observed that smallest ice crystals was obtained with the combination of the 2 isomers of PGME in the ratio of approximately 1:1 and an unsaturated mono-and digiyceride with high level of digiyceride i.e. the same combination as resulted in slowest melt down and highest heat shock stability re. Table 4. The largest ice crystals and widest span of size distribution was found in the sample with high ratio of the 1-PGME isomer.

The structure of the ice creams can be seen from the SEM pictures of Figures 1-5. Figure 1 shows a SEM picture of an ice cream containing approximately 52% 2-PGME and 48% 1-PGME as well as unsaturated diglycerides; Figure 2 shows a SEM picture of an ice cream containing approximately 52% 2-PGME and 48% 1-PGME as well as unsaturated monoglycerides and diglycerides; Figure 3 shows a SEM picture of an ice cream containing approximately 52% 2-PGME and 48% 1-PGME as weli as saturated monoglycerides and diglycerides; Figure 4 shows a SEM picture of an ice cream containing approximately 33% 2-PGME and 66% 1-PGME as well as saturated monoglycerides and diglycerides; and Figure 5 shows a SEM picture of an ice cream containing PGME approximately 22% 2-PGME and 78% 1-PGME as well as saturated monoglycerides and diglycerides, 301497667:508417 41 Table 6 Results of an ice cream formulation containing 5% fat, 0.24% totai PGME, and varying amounts of unsaturated monoglyceride and digiyceride. Unsat. MG = unsaturated monoglyceride; Unsat. DG = unsaturated digiyceride; I2 va!ue= iodine value; HS = after heat shock. Melt figures after 90 min. 2-PGME 1-PGME Unsat. MG Unsat. DG I2 value Melt Melt Sensory relative to relative to figure figure score total PGME total PGME (HS) (HS) 33% 66% 0.07% 0.20% 71 <3% 37% 4 33% 66% 0.01% 0.29% 73 <3% 33% 33% 66% 0.02% 0.37% 73 18% 60% 33% 66% 0,04% 0.21% 86 <3% % 4 33% 66% 0.04% 0.17% 86 <3% 7% 4 The results show that increasing level of unsaturated digiyceride increase the sensory score. It seems like there exists an optimum for addition of diglycerides when taking meit down properties into consideration. Further it is observed that the effect on the meiting properties depends not only on the level of digiyceride but also on the iodine value of the 10 digiyceride.

Example 8 Experiment E A series of various compositions of PGME have been tested together with various 15 compositions of monoglycerides and diglycerides in a 2% fat ice cream formulation. The results are shown in Table 7. 301497667:508417 42 Table 7 Results of an ice cream formulation containing 2% fat, 0.24% PGME and varying amounts of unsaturated monoglyceride and digiyceride, Unsat. MG = unsaturated monoglyceride; Unsat. DG = unsaturated digiyceride; I2 value= iodine value; HS = after heat shock. 2-PGME 1-PGME Unsat. MG Unsat I2 Melt Melt Sensory relative to relative to DG Value figure figure score total total (HS) (HS) PGME PGME 33% 66% 0.07% 0.20% 71 60% 56% 4 33% 66% 0.01% 0.29% 73 59% 54% 33% 66% 0.02% 0.37% 73 54% 51% 33% 66% 0.04% 0.21% 86 51% 50% 4 33% 66% 0.04% 0.17% 86 53% 57% 4 It is observed that the sensory score is influenced by the level of unsaturated diglycerides in the ice cream.

Example 9 Experiment F A series of various compositions of PGME have been tested together with a high level of unsaturated diglycerides in a 5% fat ice cream formulation. The results are shown in Table 8.

Table 8 Results of an ice cream formulation containing 5% fat and 0.24% total PGME. 15 Unsat. MG = unsaturated monoglyceride; Unsat. DG = unsaturated digiyceride; I2 value= iodine value; HS = after heat shock. 2-PGME 1-PGME Unsat. MG Unsat DG h Melt Melt Sensory relative to relative to Value figure figure score total PGME total PGME (HS) (HS) 34% 66% 0.01% 0.29% 73 31% 61% 4 50% 50% 0.01% 0.29% 73 2% 4% 33% 66% 0.02% 0.37% 73 31% 50% 4 It is from above tests concluded that the combination the 1 and 2 isomers of PGME in the ratio 1:1 together with unsaturated digiyceride has a great positive effect on the melting 20 properties of the ice cream compared to a PGME with the two isomers in the proportion 1:2. This is noticed for as well fresh ice cream as for ice cream exposed to heat shock. Increasing the dosage of unsaturated digiyceride improves the melting properties of the ice Received at IPONZ 3 Feb 2011 301497667:508417 43 cream produced with the last mentioned PGME-mixture but not to a level comparable with ice cream produced with the 1:1 ratio of PGME isomers.

It is also concluded that in highest sensory score especially creaminess is obtained when 5 using the PGME with the 1:1 ratio of the 1-PGME and 2-PGME.

Throughout this specification and the claims which follow, unless the context requires otherwise, the words "comprise", "comprising" and the like, are to be construed in an inclusive sense as opposed to an exclusive sense, that is to say, in the sense of "including, 10 but not limited to".

The reference to any prior art in this specification is not, and should not be taken as, an acknowledgment or any form of suggestion that that prior art forms part of the common general knowledge in New Zealand. 301497667:508417 44 REFERENCES Martin and Lutton Martin IB. and Lutton E. S., Jour. Am. Oil Chem. Soc. 1965, 42, 529 Arbuckie and Marshal! Arbuckle W.S. and Marshall R.T. 1996, Ice Cream, 5th ed.

Chapman & Hall US 2005/0,123,666 (US patent application) WO 2005/060,763 (PCT application) Received at IPONZ 3 Feb 2011 301497667:508417 45

Claims (22)

Claims

1. An emulsifying system comprising a 2-propylene glycol monoester of a fatty acid (2-PGME) and a l-propylene glycol monoester of a fatty acid (1-PGME), wherein the 5 emulsifying system further comprises monoglycerides and diglycerides and wherein the ratio by weight between the monoglyceride and the digiyceride is at most 50:50

2. An emulsifying system according to claim 1, wherein the ratio by weight between the monoglyceride and the digiyceride is at most 40:60 10

3. The emulsifying system according to any of the claims 1-2, wherein the ratio by weight between the monogiyceride and the digiyceride is In the range of 4:96 to 40:60,

4. The emulsifying system according to any of the claims 1-3, wherein the fatty acid of the 15 monoglyceride and/or digiyceride comprise an unsaturated fatty acid.

5. The emulsifying system according to any of the claims 1-4, wherein the ratio by weight of 2-PGME and 1-PGME is at least 1:4. 20

6. The emulsifying system according to claims 1-5, wherein the ratio by weight between the total amount of propylene glycol monoester and the total amount of monoglyceride and digiyceride Is at least 1:4,

7. The emulsifying system according to any of claims 1-6, wherein the fatty acid of the 2-25 PGME and/or the 1-PGME comprises an unsaturated fatty acid.

8. The emulsifying system according to any one of the claims 1-7, wherein the fatty acid contains 16 or 18 carbon atoms. 30

9. A frozen food product comprising an emulsifying system according to any of the claims 1-8.

10. The frozen food product according to claim 9, wherein the frozen food product is an aerated frozen food product. 35

11. The frozen food product according to claim 9, wherein the frozen food product comprises at ieast one frozen food product selected from the group consisting of ice cream, low fat ice cream, ice milk, sherbet, sorbet, frozen fruit juice, frozen yoghurt, 301910558:508417 Received at IPONZ on 02-Aug-2011 46 frozen water ice, aerated frozen bars, frozen dessert, frozen aerated cream, unwhipped dairy cream, imitation creams, and a combination thereof,

12. A packaged emulsifying system comprising a container, said container comprising an 5 emuisifying system according to any of the claims 1-8.

13. The packaged emuisifying system according to claim 12, wherein the temperature of the emuisifying system is in the range of -30°C to 45°C. 10

14, Method of preparing a frozen food product comprising the step of a) mixing a food intermediate with an emulsifying system according to claim 1-8, thus obtaining the mixture, b) optionally, heating the mixture or the food intermediate to a temperature sufficient for the emuisifying system to soften or melt, and 15 c) freezing the resulting mixture.

15. Use of an emuisifying system according to any of the claims 1-8 as an emulsifier In a frozen food product. 20

16. An emulsifying system as claimed in claim 1, substantially as hereinbefore described with particular reference to any one or more of the examples.

17. A frozen food product as claimed in claim 9, substantially as hereinbefore described with particular refrerence to any or more of the examples. 25

18. A packaged emulsifying system as claimed in claim 12, substantially as hereinbefore described with particular reference to anyo ne or more fot he examples.

19. A method as claimed in claim 14, substantially as hereinbefore described to any one or 30 more of the examples.

20. A use of an emulsifying system as claimed in claim 15, substantially as hereinbefore described with reference to any one or more of the examples. 35

21. A frozen food product when prepared by the method as claimed in claim 14. Received at IPONZ 3 Feb 2011 301497667:508417 47

22. A frozen food product as claimed in claim 21, substantially as hereinbefore described with reference to any one or more of the examples. 10 PALSGAARD A/S By Its Attorneys BALDWINS INTELLECTUAL PROPERTY