WO2001091584A1

WO2001091584A1 - Process for depositing an intensive sweetener on an edible support material

Info

Publication number: WO2001091584A1
Application number: PCT/NL2001/000409
Authority: WO
Inventors: Carina Sacha Snijder; Frank Thomas Kuehn; Leopold Franciscus Wijnandus Vleugels; Annette Catherina Hoek
Original assignee: Holland Sweeter Company V.O.F.
Priority date: 2000-05-31
Filing date: 2001-05-28
Publication date: 2001-12-06
Also published as: AU6439101A; NL1015370C2

Abstract

The invention relates to a process for depositing on an edible supporting material intensive sweetener with a particle size that is substantially smaller than 100 νm by mixing it in dry form with a supporting material, wherein a salt of α -L-aspartyl-L-phenylalanine-methyl ester and acesulfamic acid (APM.Ace) being used which has been obtained at least partially by reduction of primary particles of APM.Ace, has a d90 of less than 60 νm and substantially consists of non-primary particles, and is brought into contact under mixing conditions with particles of the edible supporting material in a weight ratio APM.Ace to supporting material of at most 1.1:1. The invention also relates to the depositing of such a sweetener on the outside of chewing gum.

Description

PROCESS FOR DEPOSITING AN INTENSIVE SWEETENER ON AN EDIBLE SUPPORT MATERIAL

5 The invention relates to a process for depositing on an edible supporting material α-L-aspartyl-L-phenylalanine-methyl ester containing intensive sweetener with a particle size that is substantially smaller than 100 μm by mixing that intensive sweetener and supporting material in dry form. The invention also relates to depositing such a sweetener on the outside of chewing gum.

10 Such a process is known from EP-A-0800774. Said patent describes that aspartame (a-L-aspartyl-L-phenylalanine-methyl ester; which will hereinafter also be referred to as AP ) with particles smaller than 100 μm by mixing in dry form, also in quantities clearly above 10 wt %, can be deposited on an edible supporting material if the APM has a free bulk density of 350 kg/m³ or

15 lower, and has been obtained by successive crystallisation from an aqueous medium under forced convection, granulation and subsequent mechanical reduction, the mixing taking place in a weight ratio between APM and supporting material of at least 1:1, but not less than 1 :30.

Although the compositions thus obtained have positively

20 improved properties relative to the compositions from the then existing prior art as regards dissolution time of the contained APM and as regards handling properties, those properties, in particular the lumping behaviour and the homogeneity of the way the sweetener is mixed in, as well as the stability of the mixture after mixing (sensitivity to segregation), certainly leave room for improvement.

25 For suitable application of the compositions it is further also important that they show a restricted dusting behaviour. The user and/or the processor will usually assess the compositions and the products in which those compositions have been processed also according to their appearance as more or less suitable (both via assessment with the naked eye and for example via

30 microscopic evaluation). The compositions known until now often leave room for improvement in that respect.

Assessment on the basis of appearance is particularly of importance when the compositions are mixed with coloured edible support materials such as cocoa. Thus the APM particles in the known mixtures with other

35 components often have the tendency to form lumps with the formation of agglomerated APM-particles, which are also perceptible with the naked eye in those compositions, which is undesirable. The mixtures formed also show insufficient stability in terms of segregation, i.e. segregation occurs too easily, so that the homogeneity of the composition can no longer be guaranteed.

It is furthermore a disadvantage of the process from EP-A- 800774 that one is limited to the use of APM obtained via crystallisation under forced convection. Because much of the APM traded on the world market is obtained via static crystallisation it is unsuitable for those applications. α-L-Aspartyl-L-phenylalanine-methyl ester (aspartame; APM) is a dipeptide sweetener with a sweetening power that is about 200x that of sugar. APM is widely used as a sweetener in a wide diversity of edible products, soft drinks, confectionery, medicines and in tabletop sweeteners and the like. APM is often used in the form of dry blends, such as instant powdered drinks and instant dessert products and the like. Blends of APM are also often used with other sweeteners, for example with acesulfame-K. Such blends are, amongst other things on account of the differences in particle size of the constituent components, less suitable for being mixed in other edible components due to insufficient stability in terms of segregation.

Also, APM-containing intensive sweeteners have been know for some time, and more in particular salts of APM with corresponding acids of another intensive sweetener, for example acesulfamic acid. In these salts the good properties of APM appear to be combined with a number of other favourable properties such as low hygroscopicity and better stability at elevated temperature. On this point the reader is referred to for example EP-A-0768041. Of such APM- containing intensive sweeteners it has already been described that they can be provided with a coating, in order to bring out their special taste effects. It is however not known and also not evident that those APM-containing intensive sweeteners, and particularly the salt of APM and acesulfamic acid, can themselves also be deposited on a supporting material. The salt of APM with acesulfamic acid will hereinafter be referred to as APM.Ace and has a completely different crystal structure and composition compared with APM. There is therefore still a need for APM-containing compositions with good properties as regards dissolution time of the APM contained in them and with improved handling properties of the composition. By 'improved handling properties' is understood in this context in particular understood that at the same time there is limited dusting behaviour, very little or no lump formation and very little or no segregation. Lump formation is usually the result of the formation of agglomerates under the influence of the occurrence of van der Waals forces, which are especially large in the case of interactions between very small particles. Furthermore, as indicated earlier in this application, the appearance of the obtained compositions and of the products into which those compositions are processed is also of importance. This is especially the case with compositions with coloured products, such as for example cocoa. There is therefore a need for compositions with a suitable appearance.

Surprisingly it has now been found that an intensive sweetener containing an α-L-aspartyl-L-phenylalanine-methyl ester and having a particle size that is substantially smaller than 100 μm can very suitably be deposited on an edible supporting material by mixing this with the support in dry form, if as intensive sweetener containing α-L-aspartyl-L-phenylalanine-methyl ester a salt of α-L-aspartyl-L-phenylalanine-methyl ester and acesulfamic acid (APM.Ace) is used, which has been obtained at least partially by reduction of primary particles of APM.Ace, has a d₉₀ of less than 60 μm and substantially, that is to say at least 60%, consists of non-primary particles, the APM.Ace being brought into contact in a weight ratio relative to the supporting material of at most 1.1 : 1 under mixing conditions with particles of the edible supporting material. In general bringing into contact for at most 15 minutes under mild mixing conditions is sufficient. By 'mild mixing conditions' is understood that the relevant mixing only brings about very little of change or none at all in the particle size of the separate, loose components themselves, but only depositing of particles of the one component (APM.Ace) on particles of the other (the supporting material) takes place. Through a suitable choice of the mixing apparatus and the settings thereof the degree of mildness of the mixing can be adapted. Depositing on an edible supporting (support) in the framework of this application means that the APM.Ace entirely or almost entirely, that is to say at least 85 wt %, is bound to the support material. Morphological research, for example with the use of microscopic techniques, can easily establish whether the APM.Ace is entirely or almost entirely bound to the supporting material. The adhesion of the APM.Ace to the support is, with the application of the process according to the invention, so good that the adhesion is not broken when the product is kept under normal conditions of use and/or is subjected to a mild segregation test (careful shaking). Only with extremely long mixing (i.e. clearly longer than 15 minutes) and/or in case of subjecting to very violent shaking or similar actions can segregation (settling) occur. A dgo-value is understood to mean that 90 wt % of the particles of the relevant product (in this case APM.Ace) has a particle size that is smaller than the stated value. The person skilled in the art can easily determine that value with the aid of special techniques available for that purpose. For products with a dgo-value of approximately 80 μm or higher this can be done for example through determination with the aid of sieving techniques known to the person skilled in the art. For products with lower d90-values use will generally be made of optical techniques, for example of laser diffraction.

Primary particles of APM.Ace are understood in the framework of this application to be solid, intact, particles (of APM.Ace) which have formed through crystallisation, that is to say via formation from primary crystals. Primary particles of APM.Ace also remain if after separation of those crystals from the medium in which they have been prepared and a possible subsequent drying stage, the crystals are not or hardly broken in those treatments. Through reduction of APM.Ace consisting substantially of primary particles APM.Ace is obtained which consists substantially, that is to say at least 60%, of non-primary particles, for example broken crystals, splinters and the like.

Upon reduction of primary particles of APM.Ace, as indicated above, non-primary particles are formed. Such reduction can take place in various ways, for example through grinding, for example in a pin mill, jet mill or ball mill. The reduction can however also occur already when drying, sifting or sieving the formed primary material under the influence of mechanical forces. Whether a reduction occurs can easily be established from the presence of non-intact particles (identifiable as splinters, fragments and broken crystals) in the APM.Ace- product. The reduction should in any case lead to an APM.Ace-product with

APM. Ace-particles having a particle size that is substantially smaller than 100 μm or, more exactly, with a dg₀ that is smaller than 60 μm, with at least 60% of the particles consisting of non-primary particles, i.e. having been formed by reduction. For that purpose, substantially APM.Ace consisting of primary particles with a particle size on average higher than 100 μm can be started from, but also from APM.Ace substantially consisting of primary particles with a particle size smaller than 100 μm.

The APM.Ace meeting the above-mentioned criteria and the supporting material are -under mixing conditions- brought into contact with each other in a weight ratio of at at most 1.1 : 1 , preferably in a mutual weight ratio of 1:3 to 1:30, more in particular of 1:5 to 1:25, and so mixed with each other. The mixing can mostly be carried out already with mild mixing conditions, that is to say under conditions and in equipment where only very little change or no change at all occurs in the particle size of the separate, loose components themselves (which for example results in a downward shift of the d₅o of not more than 5-10%).

The type of mixer to be used is not critical here. For example, tumblers can be used. Preferably convective ribbon mixers (also known as ribbon blenders) are used. In such mixers the mixing in general takes place under mild conditions. No or hardly any reduction of particles with formation of dust occurs, and the APM.Ace remains well attached to the supporting material after the mixing process. On laboratory scale such a mixing process can easily be simulated by stirring the APM.Ace and the supporting material with a spatula, for example for 5 minutes.

The lower limit of the quantity of APM.Ace relative to the support is not critical in this connection and also ratios of for example 1 :100 are possible with good results. The mixing will in general become somewhat more critical as the average particle size of the APM.Ace is larger, or as the percentage of non- primary particles in it is lower. As the average particle size of the APM.Ace is smaller, or as the percentage of non-primary particles in it is higher, it is generally easier to deposit the APM.Ace on the supporting material and there is less risk of subsequent occurrence of segregation. There is then also less danger of "overmixing".

Thus APM-containing compositions are obtained with excellent properties as regards dissolution time of the contained APM, good handling properties and suitable appearance of the obtained compositions. They can contain, according to the chosen supporting material, up to a maximum of approximately 53 wt% of the APM-containing intensive sweetener on the supporting material. This is all the more surprising because the sweetener acesulfame-K (the potassium salt of acesulfamic acid; Ace-K), even when used in a finely ground state, cannot be deposited either in a high degree of loading, for example of more than 25 wt%, on edible supporting materials. Here it can furthermore be observed that Ace-K itself is also difficult to grind, that is to say that the required energy input for reducing Ace-K is significantly higher than for reducing other products, such as for example APM or APM.Ace, and that for that purpose therefore if desired a more intensive grinding device, for example a jet mill, will be used. Equally it appears in practice difficult to attach APM obtained via static crystallisation adequately to a supporting material via mixing under mild conditions.

The APM-containing compositions according to the invention show no or only a very small tendency to segregation. The homogeneity of the compositions obtained, particularly also as regards the distribution of the sweetener therein, makes the compositions well applicable as reproducible product with, at a given composition, very small fluctuations in properties of samples taken from that composition in different places.

Although in the framework of the invention segregation naturally refers in the first instance to segregation between the sweetening component and the edible supporting material, it may be stated here, be it superfluously, that - in contrast to products for which a blend or mixture of sweeteners is used - segregation of the constituents of the sweetener does not occur either.

Preferably APM.Ace used in the framework of the invention has a d₉₀ of less than 40 μm, still more preferably less than 25 μm, in particular less than 15 μm.

Very suitable results are obtained when at least 80% of the APM.Ace consists of non-primary particles.

Preferably such APM.Ace is brought under mild mixing conditions in contact with particles of the edible supporting material for less than 10, in particular less than 5 minutes.

It is a special advantage of the present process that also under very dry conditions, for example in case of low relative humidity (for example < 70% or even at 40% or lower) or with use of non- or slightly hygroscopic supporting materials, it results in excellent compositions, with high contents of APM-containing intensive sweetener, in particular APM.Ace, being bound entirely or almost entirely to the supporting material.

A further advantage of the present process to be mentioned is that the mixing operation according to the invention, on account of the mild conditions applied, entails few risks of so-called overmixing, provided the mixing time chosen is not much longer than for example 15 minutes. Overmixing is understood to be the phenomenon that segregation occurs again in an already well mixed composition if the real mixing time for one reason or another would be longer than strictly necessary for the mixing. Powder compositions that show the tendency to segregate again at longer mixing times are also known as segregation powders. If no segregation takes place the powders are also known as cohesive powders. The compositions obtained according to the process of the invention can be considered to be cohesive powders. For further information about the behaviour of cohesive and segregation powders the reader is also referred to N. Harnby et al., in "Mixing in the Process Industries ", 2^nd Ed. 1992, pages 10-16, Butterworth & Heinemann Ltd, Oxford.

In the process according to the invention the salt of APM and acesulfamic acid is used (APM.Ace) as the APM-containing intensive sweetener. This salt can both be obtained starting from APM, recovered via static crystallisation as a solid product, and starting from APM that has been recovered via stirred crystallisation as a solid product. Suitable processes of manufacturing for the salt of APM and acesulfamic acid have been described in detail in for example EP-A-786041 and EP-A-986575. Particularly suitable in the framework of the present invention is APM.Ace that has been obtained via crystallisation in an aqueous environment. As supporting material to be used for the process according to the invention it is possible to use a wide group of known, solid, food ingredients or mixtures thereof, for example in the form of so-called masterbatches, that are applied, for example as bulk material, in combination with intensive sweeteners. Examples of suitable edible supporting materials in the framework of this invention are monosaccharides, such as glucose, also known as dextrose, and fructose; disaccharides, as for example saccharose, that in addition to sucrose are also known as cane or beet sugar, lactose and maltose; oligosaccharides such as for example stachyose or raffinose; polysaccharides, such as for example starch, maltodextrins, cyclodextrins, fructans, including for example inulin (polyfructose), and polydextrose; sugar alcohols, such as for example sorbitol, mannitol, maltitol, lactitol, xylitol and isomalt; as well as other carbohydrates and polyols; various of the stated products are also available in hydrated form, for example dextrose monohydrate; food acids such as lactic acid, citric acid, ascorbic acid or malic acid can also be used as supporting material, or salts of such food acids, or protein hydrolysates and other dry nutrients such as vanilla, cocoa and the like.

The solid supporting material which is used in the process according to the invention in general has a surface that is adequate to include the concentration of intensive sweetener to be applied thereon. Usually the supporting material will have a relatively narrow spread in particle size, for example a maximum difference between the d™ and d₉₀ of approximately 500 μm, within a total range of 20 to 2000 μm. Supporting material where at least 90 wt % of the product falls in the range from 20 to 700 μm has most preference. Products with such a particle size, depending on the nature of the supporting material, are already obtainable as such in commercially available products, or can readily be separated from commercially available products, using processes known to the person skilled in the art, as a particle size fraction, for example by sieving, optionally preceded by a grinding treatment, or composed as a particle size fraction. However, in the case of various supporting materials, for example for maltodextrins or citric acid, it is also possible to use the supporting material with a particle size larger than 500 μm, for example approximately 1200 to approximately 2000 μm.

It is also possible to use a blend of different supporting materials as supporting material. The supporting material, before being used in the process according to the invention, can already have been mixed with the whole or part of one or more colouring agents or flavourings which should be present in a desjred end product sweetened with the APM-containing intensive sweetener. Depending on the chosen supporting material, for example as regards the hygroscopicity thereof, and the additives to be used such as colouring agents and flavourings, minor recipe adaptations may be necessary in the process to produce APM- containing intensive sweetener deposited on supporting material. For the person skilled in the art it is easy to determine such minor adaptations through a correct choice of ingredients and the order of metering thereof, but also process conditions and equipment can have some influence. The classification and testing method proposed in Pharmeuropa, Vol. 4 (3), pp. 228-230, 1992, provides adequate insight into the hygroscopicity of the supporting materials used. According to that classification materials which upon exposure at 25°C to air with 79% relative humidity ("relative humidity"; "r.h.") show a moisture absorption of more than 15% (wt) are referred to as highly hygroscopic materials. Such materials can be used in the framework of the present invention as a supporting material, but it is assumed that in such cases adhesion to the supporting material to an important extent takes place under the influence of moisture, that is to say in fact comparable with the processes known from the prior art where wetting is applied. The materials that absorb between 2 and 15% moisture are called hygroscopic; those that absorb less than 0.2% moisture are called non- hygroscopic. Materials that absorb 0.2-2% moisture (at 25°C, 79% r.h.) are classified as having a slightly hygroscopic character. The advantages of the invention are most apparent when the supporting material is less hygroscopic and/or when the ambient r.h. is relatively low, for example lower than 70%. Particularly hygroscopic supporting materials are in fact usually less suitable for so-called "dry-substance" applications, for example in instant-powder drinks, etc., so, in practice, not using such materials will not impose any real limitations on the invention's applicability. Suitable supporting materials are in every case materials with a hygroscopicity such as that of citric acid, sorbitol or lower, such as for example, but certainly not limited to, xylitol, maltitol, saccharose, isomalt, and lactitol.

As a further advantage of the process of the invention, it has been found that the (originally) obtained compositions with relatively high contents of APM-containing intensive sweetener (APM.Ace) bound to the supporting material can be converted further in a simple way, via one or more-further simple and low-energy mixing operation(s), with extra supporting material- whether or not in the presence of additional colouring agents, flavourings and/or other ingredients that are required for specific desired end products - into homogeneous compositions with lower, or even very low - for example 0,5 to 5 wt.% - contents of APM-containing intensive sweetener, with the sweetener being bound to the supporting material and having no negative effects on the properties of the composition in terms of flow and dissolving behaviour, as well as in terms of dust- and dusting-free character, and the like. In said subsequent treatments the originally obtained compositions with relatively high contents of APM-containing intensive sweetener bound to supporting material can be considered, as it were, to be a sort of "master batch" or "pre-mix" of sweetener-on-support. The weight ratio between the composition originally obtained and the further supporting material is preferably between 1 : 1 and 1 : 20.

It has also been found by the inventors that the APM.Ace which has at least partially been obtained by reduction of primary particles of APM.Ace, has a d₉₀ of less than 60 μm and consists substantially, that is to say at least 60%, of non-primary particles, can also be suitably deposited on the outside of chewing gum, in particular of strips of chewing gum, by spraying it - whether or not together with other components - onto the chewing gum. That APM.Ace adheres well to the surface of the chewing gum. Naturally the person skilled in the art will choose the concentration of APM.Ace deposited on the outside of chewing gum in such a way that the consumer of the chewing gum will experience a good taste.

The invention will hereinafter be elucidated with reference to some examples and comparative experiments, without being in any way whatsoever limited thereby. Where relevant, use was made of the following techniques, methods and equipment:

Mixing methods For the examples and comparative experiments APM.Ace and supporting material were mixed with each other in mixing ratios (w/w) as indicated. This was done at a room temperature and a r.h. of 40-50%, by (a) stirring for 5 minutes (or for 1 minute for mixtures with cocoa) with a spatula in a polyethylene sampling bottle, or (b) mixing for 5 or 15 minutes in a 2-litre laboratory ribbon mixer (Pfleiderer) at 40 rpm.

With these mixing methods the properties of the mixtures formed showed no significant differences attributable to the method of mixing.

Visual assessments

Estimation of the results obtained as regards depositing the APM.Ace on supporting material, also as regards the appearance of the compositions obtained, was done by means morphological analysis under a Moritex inspection microscope (a video microscope with a stepwise adjustable zoom lens and a monitor). The compositions obtained were investigated with magnifications of respectively 100x and 210x; the samples were studied with the aid of obliquely incident halogen light. The records at 100x and 210x give a good detailed picture and an impression of the smallest particles, respectively. On the basis of such records it is possible to make a good estimate as to whether more than approximately 85% of the APM.Ace is bound on the supporting material, or to what extent loose APM.Ace-particles are still present. By comparing the starting materials, it was thus also possible to determine, whether, and to what extent, a change of particle size occurred during the mixing operation.

With the "Particle Visibility Tests", in all cases done on compositions with cocoa as the supporting material, the assessment took place visually each time, with the naked eye and/or under a microscope. It is usually possible to detect already with the naked eye whether lumping has occurred. In this case the particles APM or APM.Ace are visible as white particles in cocoa. Examination under a microscope also provides a good indication of the extent of lumping can be obtained.

Determination of dissolution time

Determination of the dissolution time of APM (as present in the composition) took place with the aid of a Beckman UV-spectrophotometer: The change in UV-absorption at 254 nm was followed in time until a stable level was reached. The samples of the composition were in each case added to stirred (400 r.p.m.), dust- and particle-free dimineralised water (pH = 7; temperature 23°C) in such a quantity that the resulting solution contained 0.1% (w/w) APM derived from the APM.Ace. The dissolution time was determined in minutes (up to the moment of reaching the level of maximum absorption). As simple alternative to this test the dissolution time was also visually assessed in a number of cases by determining the moment at which less than 5 particles in 500 ml of the solution to be prepared are visible. At that moment the relevant sample is considered to be completely dissolved.

For comparison of the dissolution times of different samples one of above-mentioned methods was used in each case.

Results of the dissolving tests and the visual assessments can be found in table 1.

Determination of segregation; variation coefficients Segregation tests were carried out via two methods, so that different forms of segregation could be investigated:

(a) "vibrating cylinder" method for determination of the segregation under influence of vibrations on a vibrating plate. In each case samples were taken after 15 minutes (for the determination of the composition) at six previously fixed, different heights in the cylinder (500 ml; diameter 50 mm; degree of filling at start of 600 ml; subjected to a vibration frequency of 50 Hz at a vertical amplitude of 1 mm); this test gives for example a good indication of segregation during transport;

(b) "Mosby-test" via a 2-dimensional segregation tester (see page 67-69 from the dissertation of J. Mosby, Telemark College Department of Technology,

13-9-1996: "Investigations of the Segregation of Particulate Solids With Emphasis on the Use of Segregation Testers) for determination of the effect of segregation as a consequence of pouring out (a homogeneous mixture) on a heap. This is also known as "rolling segregation". In this test 9 samples were taken from the various segments of a mixture flowing along a sloping surface and confined between two side walls.

In both cases the degree of segregation per component can thus be expressed in a so-called "variation coefficient" (VC) The VC (in %) indicates the ratio between the calculated standard deviation in the concentration of such a component (in the various samples taken from material subjected to one segregation test) and the concentration of that component in the (homogeneous) initial mixture.

The results of the VC measurements have been summarised in table 2.

Materials

In the examples and comparative experiments the following starting materials were used

[A] APM.Ace, obtained through crystallisation from an aqueous environment, dried and ground, at 18,000 r.p.m., in an Alpine 100 UPZ pin mill to a product with a d₉₀ of 22 μm; this product comprised at least 85% of non- primary particles. [B1] APM.Ace, obtained through crystallisation from an aqueous environment, dried and then separated as a sieve fraction (smaller than 100 μm) with a dg₀ of 94 μm; this product comprised less than 50% non-primary particles. [B2] APM.Ace, obtained through crystallisation from an aqueous environment, dried and then separated as a 0-250 μm sieve fraction, with a d_go of 163 μm; this product also comprised less than 50% non-primary particles. [B3] APM.Ace, obtained through crystallisation from an aqueous environment, dried and then separated as a 100-250 μm sieve fraction, with a dg₀ of 204 μm; this product also comprised less than 50% non-primary particles.

[C] Maltodextrin (Cerestar MD 1910), with a particle size distribution of 63 to 400 μm.

[D] Cocoa powder (low-fat ADM D11 Asol grade; alkalized grade with lecithin), with a particle size distribution of 1 to 25 μm. [E1] Citric acid (Roche), with a particle size distribution of 125 to 400 μm. [E2] Citric acid (Roche), with a particle size distribution of 300 to 800 μm. [F] Citric acid (Jungbunzlauer), with a particle size distribution of 125 to

600 μm. [G1] Mix for a lemon soft drink with [E1] and [C]; [E1] content 47 wt %; rest [C] [G2] Mix for a lemon soft drink with [F] and [C]; [F] content 47 wt %; rest [C] [G3] Mix for a lemon soft drink with [E2] and [C]; [E2] content 47 wt%; rest [C] [H] Mix for a lemon tea with [E2] and [C]; [E2] content 11 wt%, rest [C] and a small quantity of quantity of "tea flavour" [X] APM obtained through stirred crystallisation from an aqueous environment, dried and ground in a pin mill to a product with a dg₀ of 20 μm

[Y] Acesulfame-K, ground in a pin mill to a product with a d₉₀ of 54 μm (and a d₅₀ of 21 μm) [Z] Blend of Acesulfame-K (d₅₀ = 310 μm; d₉₀ = 700 μm) and APM obtained through static crystallisation (d₅₀ = 15 μm; d_go = 57 μm)

The results of a number of representative examples and comparative experiments are shown in table 1. In table 1 the meanings of some of the ratings are as follows:

* dissolving behaviour

++ dissolution time of APM in the composition is much shorter (0.5x or less) than for APM [X]; no lumping + dissolution time of APM in the composition is shorter (0.5-0.9x) than for APM [X]; hardly any lumping +/- dissolution time of APM in the composition is equal to (0.9-1.1x)

APM [X]; perceptible lumping dissolution time of APM in the composition is longer (1.1-2x) than for APM [X]; clearly perceptible lumping dissolution time of APM in the composition is much longer (2x or more) than for APM [X]; much lumping

* particle visibility

++ in the composition no lumped particles of the sweetener used are visible with the naked eye + in the composition no lumped particles of the sweetener used are visible with the naked eye, but the colour of the composition becomes a bit lighter +/- in the composition small lumped particles of the sweetener used are visible with the naked eye in the composition relatively large lumped particles of the sweetener used are visible with the naked eye in the composition many large lumped particles of the sweetener used are visible with the naked eye.

In Table 2 presents the Variation Coefficients found (partly determined via the vibrating cylinder method and partly via the Mosby test) are given. According as a comparison of the VC values (determined according to one of the methods) in this table shows lower values, it can be concluded that segregation occurs to a lesser extent. Inversely, higher values point to stronger segregation.

Table 1

(n.a. = not available) Table 2 Variation coefficient (in %)

(determination with vibrating cylinder, or according to Mosby)

(* ) In this comparative experiment (without >85% adhesion on the surface of the support), incidentally, hardly any segregation appears to occur. From all these results it may be concluded that only with the aid of the process according to the invention are mixtures obtained that meet all the requirements specified as regards their properties.

It has been found to be abundantly clear that in none of the compositions according to the invention segregation occurs, while in the comparative experiments segregation occurs in almost all cases in a significant measure, which is undesirable.

Claims

1. Process for depositing on an edible supporting material an α-L-aspartyl-

L-phenylalanine-methyl ester containing intensive sweetener with a particle sizie that is substantially smaller than 100 μm by mixing it with the supporting material in dry form, characterised in that as intensive sweetener containing α-L-aspartyl-L-phenylalanine-methyl ester a salt of- L-aspartyl-L-phenylalanine-methyl ester and acesulfamic acid (APM.Ace) is used, which at least partially has been obtained through reduction of primary particles of APM.Ace, has a d₉₀ of less than 60 μm and substantially, that is to say at least 60%, consists of non-primary particles, the APM.Ace being brought into contact with particles of the edible supporting material in a weight ratio relative to the supporting material of at most 1.1:1 under mixing conditions.

2. Process according to claim 1, characterised in that the APM.Ace applied has a dgo of less than 40 μm, more in particular less than 25 μm and most in particular less than 15 μm.

3. Process according to any one of the claims 1 or 2, characterised in that the APM.Ace comprises at least 80% non-primary particles.

4. Process according to one of the claims 1-3, characterised in that the

APM.Ace and the supporting material are brought into contact with each other in a weight ratio of 1:3 to 1:30, more in particular of 1:5 to 1:25.

5. Process according to one of the claims 1-4, characterised in that the APM.Ace for less than 15, in particular for less than 5 minutes, is brought into contact with particles of the edible supporting material under mild mixing conditions.

6. Process according to one of the claims 1-5, characterised in that the APM.Ace has been obtained via crystallisation in an aqueous environment.

7. Process according to one of the claims 1-6,characterised in that a supporting material is applied with at least 90 wt% of the supporting material having a particle size in the range 20 to 700 μm.

8. Process according to one of the claims 1-7, characterised in that the supporting material has a hygroscopicity that is lower than or corresponds to that of citric acid or sorbitol.

9. Process according to one of the claims 1-8, characterised in that the obtained product containing APM.Ace on an edible supporting material is further converted in one or more further mixing operations with extra supporting material into homogeneous compositions with lower, or even with very low, for example 0,5 to 5 wt%, contents of intensive sweetener containing APM.

10. Process according to claim 9, characterised in that the weight ratio of the composition obtained in the first instance to the further supporting material is 1 : 1 and 1 : is 20.

11. Process for depositing on an edible supporting material an α-L-aspartyl- L-phenylalanine-methyl ester containing intensive sweetener with a particle size that is substantially smaller than 100 μm, characterised in that the edible supporting material is a chewing gum or strip of chewing gum and that onto the (strip of) chewing gum a suitable quantity of a salt of-L-aspartyl-L-phenylalanine-methyl ester and acesulfamic acid

(APM.Ace) is sprayed, which has been obtained at least partially by reduction of primary particles of APM.Ace, has a d₉₀ of less than 60 μm and substantially consists of non-primary particles.