CA1105307A

CA1105307A - Sorbic acid-containing powder or granules

Info

Publication number: CA1105307A
Application number: CA299,107A
Authority: CA
Inventors: Ryuzo Ueno; Toshio Matsuda; Shigeo Inamine
Original assignee: Ueno Seiyaku Oyo Kenkyujo KK
Current assignee: Ueno Seiyaku Oyo Kenkyujo KK
Priority date: 1977-03-17
Filing date: 1978-03-16
Publication date: 1981-07-21
Also published as: JPS53116315A; DE2749751A1; DE2749751C3; NL180560C; US4172897A; NL178838B; BE860793A; DE2749750C2; GB1566973A; FR2383610B1; GB1570836A; AU509963B2; DE2749751B2; FR2383610A1; NL7713074A; CA1096692A; FR2383615B1; NL180560B; BE860794A; FR2383615A1

Abstract

ABSTRACT OF THE DISCLOSURE

Sorbic acid-containing powder or granules free from scatterability and rapidly soluble in water consisting of 5-90% by weight of finely divided sorbic acid with particle diameter of 50 ? or less, 10-95% by weight of an easily water-soluble substance which is a solid at normal temperature and 0-2% by weight of hydrophilic surface active agent, characterized by having particle diameter of 300 ?, or more. The above sorbic acid-containing powder or granules can be obtained by drying after making powder or granules having particle diameter of 300 ?
or more from a mixture consisting of finely divided sorbic acid with particle diameter of 50 ? or less, an easily water-soluble substance which is solid at normal temperature, water and/or an aqueous organic solvent and optionally, a hydrophilic surface active agent, or by making powder or granules having particle diameter of 300 ? or more from the dry mixture after drying said mixture.

Description

ll(;~S3~7 This invention relates to sorbic acid-containing powder or granules free from scatterability and rapidly dissolvable in water, as well as to a process for the pro-duction and usage thereof.
Since sorbic acid shows a s~rong antibacterial force in low toxicity, it is widely used as a preservative agent for drinks and foods, feeds and so on ~hereinafter may be called foods for short). Many studies were made of anti-bacterial force and physical properties of sorbic acid and explanations are given in detail in the "New Food Industry", Vol. 7, No. 10, p.p. 48-75, for instance.
Sorbic acid is sparingly soluble in water and solu-bility for water is in the order of 0.16 g/100 ml at normal temperature, but it dissolves more in water of which the PH
value is high by formation of salts. Sorbic acid, however, shows antibacterial action in a form of a free acid and in the ,l case of using as a preservative agent it is preferred to lower:~ the pH value of foods as much as possible. The amount of sorbic `:~ acid added varies according to the kind of foods, but in general, is about 0.05 - 0.3% by weight. This addition amount is close to .~ , the saturated solubility for water of sorbic acid and it is ex-tremely difficult to perfectly dissolve in foods at low PH values.
As a means for improving the solubility of sorbic acid it is considered to divide it finely. Powdered sorbic acid, however, shows a strong irritating action on the mucous membranes of human beings and it will worsen working environ-ment to make sorbic acid into finely divided powder high in dusty powder, hereinafter termed scatterability. In some cases, therefore, -, . , ~ - . . . . . . .

11~53~7 there may be used coarse grained sorbic acid having some-what greater particle diameter falling within given limits by removing off fine particles so as not to scatter. In this case, the solution rate of sorbic acid is of course lowered and it becomes necessar~ to take such means as ex-tension of heating and stirrin$ time, which is not pre-ferred in terms of working efficiency.
In many cases, on the other hand, salts of sorbic acid are used for improving the solubilityO The mucous membrane irritating action can be simultaneously avoided by use of salts, but the antibacterial action in-herent in sorbic acid cannot exhibit itself as it is kept in a salt condition. Sorbates somewhat enhance the PH
value of foods in which they were incorporated. In order, therefore, to conform t~le PH value when adding sorbates to foods to the PH value when adding sorbic acid, vi~, to make sorbates exhibit the equivalent antibacterial action to that of sorbic acid it is required to counteract the weak alkalinity of sorbates and add other acids in the amount corresponding to the acidity of sorbic acid~ In addition, sorbates are greater in the molecular weight than sorbic acid and it is ~ o~
L~ necessary to ~ add~by that amount, which is not econo-micalO
Proposals have been made for ~arious processes designed to improve the defecis with sorbic acid while main-taining the efficacy of sorbic acid~ Of these some pro-cesses succeeded in a tentative way, but under present situations, are not put to practical use in food plantsO
For instance, a proposal is made for a process which , , .
,: ~ , . ~

llas3~7 comprises using sorbic acid as alcohol solution, and according to this process, the solubility and mucous membrane irritative property of sorbic acid are improved, and added to this, there can be obtained equivalent antibacterial effect to that in the case of using sorbic acid in the form of solids in various foods.
This process, however, because of using alcohol unnecessary for foods, becomes high in manufacture costs and is not economical as ., is the case with the process involving the using of alkali salts.
The instant inventors studied in various ways with the purpose of improving the defectsJ in consequence of which it was ~ ;
found that sorbic acid preparations free from scatterability (with-out irritating the mucous membrane accordingly) and capable of showing the inherent antibacterial force with sorbic acid contained ;~ ~
rapidly dissolving in water could be obtained by a simple and econ- ~ -omical means of making finely divided sorbic acid into powder or granules having relatively great particle diameter by using, as a carrier or diluent or binder, an easily water-soluble substance i which was a solid at normal temperature.
~'~ Thus, the instant invention provides sorbic acid-containing powder or granules, free from scatterability and fast soluble in water, comprising 5-90% by weight, preferably i 10-80% by weight, of finely divided sorbic acid having particle diameter of 50 ~ or lessJ 10-95% by weight, preferably 20-90%
by weight, of an easily water-soluble substance selected from the group consisting of sugars, sugar-alcohols, organic acids, salts of organic acid and phosphates which is a solid at normal temperature and ~_2% by weight, preferably 0.05-1% by weight, of a hydrophilic ,:

r 11~53~7 surface~active agent, characterized by having particle diameter of 300 ~l or more, preferably 500-1500 ~lo Such sorbic acid-containing powder or granules, according to the instant invention, are obtained by dry- :-ing after making powder or granules having particle dia-meter of 300 ~ or more from a mix~ure consisting of finely divided sorbic acid with particle diameter of 50 ~ or less, an easily water-soluble substance which is solid ht normal temperature, water andJor an aqueous organic sol-vent and optionally, a hydrophilic surface active agent, orby making powder or granules ha~ing particle diameter of 300 ~ or more from the dry mixture after drying said mixture.
The easily water-soluble substance which is a solid at normal temperature is preferably selected from among additives indispensable for the manufacture of foodsO
Of these those ones which are capable of addition at the same time as sorbic acid is added can all be used in the instant invention. As substances of this kind mention is made of sugars, such as cane sugar, grape sugar, fruit su~ar and so on; sugar alcohols, such as sorbitol, malbitol and so on; organic acids, such as citric acid, ~alic acid, tartaric acid~ fumaric acid and so on; salts of organic acids, such as the respecti~e sodium salts or potassium salts of acetic acid, citric acid, malic acid, tartaric acid, fumaric acid and sorbic acid, monosodium glutamate, sodium inosinate and so on, as well as sodium primary phosphate, sodium secondary phosphate, sodium tertiary phosphate, sodium pyrophosphate, acid sodium pyrophosphate, sodium metaphosphate and sodium polyphosphate or their 1~53~7 corresponding potassium salts. These substances are pre-ferably selected according to the kind of foods and can be used alone or as a mixture of 2 members or more.
Sorbic acid is used as finely divided one with particle diameter of 50 ~ or less so as to be able to im-mediately dissolve when added to foods.
Powder or granules of the instant invention may contain, as desired, a small amount of a hydrophilic sur-face active agent to improve the wetting for water of sorbic acid. As the hydrophilic surface active agent, for instance, cane sugar fatty acid esters, preferably those ones which are 11 or more in the HLB, lecithins, preferably high purity lecithins, fatty acid esters of sorbitan ~SPAh-20, for instance), reaction products between sorbitan fatty acid esters and polyoxyethylenes (TWEEN-20, for in-stance) and so forth are used alone or as a mixture of two -members or more. In the case of using salts as the easily water-soluble substance, in some cases, no surface active ~-agents are required. This is considered ascribable to salts showing the action forimproving the wetting for water of sorbic acid particles.
The sorbic acid-containing powder or granules of `~
the instant invention contain 5-90% by weight, preferably 20-80% by weight, of finely divided sorbic acid having particle diameter of 50 ~ or less, preferably 30 ~ or less and 10-95% by weight, preferably 20-80% by weight, of an easily water-soluble substance which is a solid at normal temperature, and besides, may also contain 2% by weight or less, preferably 1% by weight or less, of a hydrophilic *Trademark - 6 -il~S-3~ ~

surface active agentO '~lhen the amount of sorbic acid i~
less than 5% by weight, the solubility is good, but more than necessary easily water-soluble substances will be added to foods, which is not desirable. 1~hen it is in excess of 90/0 by weight, the amount of the easily water-soluble substanre will become relatively small and the solubility will be lowered. The sorbic acid content is preferably determined according to the kind of foods in which it would be added~
The sorbic acid-containing powder or granules of the instant invention have particle diameter of 300 or more, preferably up to about 1500 I~ so as not to scatter and irritate the mucous membraneO ~`
The powder or granules of the instant invention can further contain ordinary additives or assistants such for instance as a ~r^a~ promotor or binder. As the decay promotor, for instance, glycerine, propylene glycol, starch and so forth are added generally in the amount of 0.5-10%
by weight with regard to powder or granules. As the binder, 20- for instance, ~-starch, gum arabic, carboxymethyl cellulose, methyl cellulose, guagum and other paste, sugars and the like are added generally in the amount of 0~1-5% by weight with regard to powder or granules.
The sorbic acid-containing powder or granules f the instant invention can be prepared by usual means for preparing powder or granules~ ~referably, the afore-said respective components are added in a relatively small amount of water and/or organic solvent to first make a dispersed substance. ~.fter that, the dispersed 11~53~7 substance is pulveri~ed and dried, or granules are made from said dispersed substance and dried, or said dis-persed substance is dried and then pulverized. The afore-said respective components could also be added in a re-latively large amount of water andSor organic solvent tofirst ~ake a suspension and then powder or granules are directly prepared from the suspension by spray-drying or vacuum-drying. In the case of using the surface active agent it is preferred to dissolve the surface active agent in water and then add the remaining components. In the case of using, as the easily water-solub~e substance, those sub-stances of low melting temperatures, such as sorbitol, it will suffice to admix finely divided sorbic acid (and sur-face active agent) to the melt of the easily water-soluble substance, followed by cooling and milling~ The dry step could be omitted~
As the organic solvent, for instance, methanol, ethanol, propanol, isopropanol, acetone and so forth can be used alone or as a mixture, and ethanol is particularly preferred.
The powder or granules of the instant invention ~-can be used by adding as the preservative agent in the usual way to general drinks and foods or feeds. The powder or granules will immediately disperse and dissolve when added to foods, and the effect as the preservative agent after addition remains the sa~e as t~at of the known sorbic acid preparations.
The amount of sorbic acid contained in the powder or granules and the kind of the easily water-soluble ~ S3~17 ~ ~ ~

substance, as mentioned ea~lier, are determine~ according to foods in which they are incorporated. The following will be illustratedO In the case of adding to pickles, since primzrily organic acids are well used in the pickles, a combination of sorbic zcid and ma'ic acid or citric acid is preferred. In the case of adding to wine, it is a combination of sorbic acid and tartaric acid or citric acid that is preferred. ~owever, since the indispens- ~
able addition amount of sorbic acid with respect to wine - -is small (in ~eneral, 0.02% or less), it is preferred to use powder or granules less in the sorbic acid content.
Xn the case of adding to jam or soft moist type dog foods, since a great deal of sugar is primarily used as an in~
dispensable additive therein, it is a combination of sorbic acid and sugar that is suitableO In the case of cat food where the PH is relatively lo~ and hardly any sugars are used combinations of sorbic acid with organic acids such as citric acid, malic acid and so on are recommended. Mention can be made of mayonnaise, margarin, fish sausage, meat sausage and so on as other foods for subject~
In the case of adding at the time of preparing the foods powder or granules of the instant invention con-sisting of the aforesaid combinations of sorbic acid ~ith the specified easily water-soluble substances (organic acids, tartaric acid or sugars~, additives (organic acids, tartaric acid or sugars) to be primarily added to the foods can be less used hy the a~ount of the easily water-soluble substances contained in the powder or granules of the in-stant in~entionO Therefore, tne increase in the costs 1105~7 resulting from excess additives can be avoided~
The instant invention will be specifically ex- -~
plained by way of non-limitative Examples as follows.
Example 1 S 4 g of cane sugar fatty acid ester (~LB 15) and 20 g of glycerine were added to 150 ml of water and dissolved by heating at 80C~. The aqueous solution ob~
tained was cooled at about 50Co~ On the other hand, 1000 g of finely divided sorbic acid (average particle diameter 30 Il) and 976 g of DL-malic acid were ~laced in a kneader and uniformly mixed together~ While adding the aforesaid aqueous solution the mixture was kneaded for 30 minutes by means of kneaderO Then, columnar granules 1 mm in diameter were fabricated from this kneaded sub- , ;
stance by means of extrusion type granulator and dried in ~ ;
hot air at 70C
The sorbic acid-containing ~r`anulated product so obtained was suitable as one for picklesO
Exa~ple 2:
60o g of finely divided sorbic acid (average particle diameter 30 ~) and 388 g of citric acid were placed in the kneader. Then the mixture was Xneaded for 30 minutes -~
with addition of aqueous solution prepared by dissolving

2 g of cane sugar fatty acid ester (HLB 15) and 10 g of !
glycerine in 100 ml of water. The resultant kneaded sub-stance was milled by means of pulverizer into granules ta~ing unfixed forms 0~3-1 ~n in partic~e diameter~ The granules were dried in hot air at 70C
The sorbic acid-containing granules which took ~ - 10 -53~7 unfixed forms Mere suitable as onas for pickles or for wine.
Example 3:
R~ueous solution prepared by dissolving 28 g of sugar and 2 g of cane su~ar fatty acid ester (HLB 11) in ;~
300 ml of water was added to a mixture of 700 g of finely divided sorbic acid (average particle diameter 20 Il) and 270 g of acid sodium pyrophosphate powder and kneaded for 30 minutes in the kneaderQ Then, this kneaded substance was milled by means of pulverizer and powder 003-0.7 mm in par-ticle diameter was sieved and dried in hot air at 70C~o The sorbic acid-containing powder so obtained was suitable as one for fish and meat sausagesO
Example 4:
100 ml of water was added to 600 g of sorbitol powder and dissolved by heating at 80C.. 1 g of high purity lecithin was added to the solution obtained and dis-solvedO With addition of 200 S of finely divided sorbic acid (average part~cle diameter 20 ~) the mixture was stirred and homogenized by means of homomixer. The suspension ob-tained was cooled at 70 C0O 'Jhile mixing in the kneader with addition of 199 g of sorbitol powder as seed crystals, it was cooled down to room temperature. ~ereby there were formed small massed sorbitol particles containing sorbic acid particlesO ~.fter pulveri~ation particles 003 0.7 mm in particle diameter were sieved and driedO
This product was applied to drinks and foods using sorbitol and sorbic acid, such as pickles, jam, mayonnaise and so onO

`` ~ 11~53(~7 Example 5:
449.5 g of po.~dered sugar (prepared by pulveriz-ing cane sugar) and 50 g of finely divided sorbic acid (average particle diameter 30 )~ were mixed toget~er.
With addition of mixed solution consisting of 0O5 g of ''SPAN-20'~,_7u5 ml of ethanol and 27 ml of ~ater the mixture was kneaded for 30 minutes in the kneader, Columnar gra-nules 0.8 mm in diameter were fabricated from this kneaded substance by means of extrusion type granular and then dried.
This product was suitably used for jam, mayonnaise and dog food.
Example 6: :
350 g of sodium secondary phosphateOdodecahydrate ~as placed in the kneader ~th a jacXet and melted by heat-ing at 40C.... 100 g of finely divided sorbic acid with average particle diameter of 25 !I was added to this melt and stirred to bring to uniformly suspended condition.
After that, with addition of 50 g of anhydrous sodium secondary pho~phate the mixture was cooled down to 30C.
for solidification with further continued stirringO Solids ...
were further left to st-and for 2 hours at 20C~o Then, they were pulveri~ed to sieve powder 0u3~0o7 ~n in particle diameterO
Example 7:
770 g of sodium citrate and 200 g of finely divided sorbic acid (average particle diameter 20 ~) were placed in the kneader and uniformly mixed together. ~fter that, aqueous solution prepared by dissolving ?.0 g of cane sugar and 10 g of glycerlne in 100 ml of water was added S3~7 to the resultant mixture and further kneaded for 30 minutes.
The kneaded substance was dried and then pulverized to ~-sieve particles 0.3-0.7 mm in particle diameter.
Sorbic acid-containing powder so obtained was suited to cat food.
Example ~:
600 g of finely divided sorbic acid (average particla diameter 30 ~I) and 3~9 g of citric acid powder were placed in the kneader7 Then, with addition of aqueous solution prepared by dissolving 1 g of "TWEEN-20i' and 10 g of glycerine in 100 ml of water the mixture was kneaded for 30 minutesQ The kneaded substance was pulverized to sieve particles 0~3-0.7 mm in particle diameter D
Example 9: -100 ml of water was added to 600 g of sorbitol powder and dissolved by heating at 80C~ 0.5 g of "T~EEN-Z0" and then 200 g of finely divided sorbic acid (average particle diameter 30 ~) were added to the solution obtained and homogenized by stirring in the homomixerO The suspension obtained was cooled do~n to 70co~ ~fter that, while mix-ing in the kneader with addition of 199~5 g of sorbitol powder as seed crystals the mixture was cooled down to room temperature. Whereby there were formed small massed sorbitol particles containing sorbic acid particlesO These particles were dried and then pulverized to sieve particles 0~3~0~7 mm in particle diameter Example 10 50 ml of water, 378 g of citric acid (mono.~ydrate), 10 g of cane sugar, 10 g of glycerine and 2 g of cane sugar ll~S307 fatty acid ester (HLB 15) were mixed together and made into solution by heating at 80C~O On the other hand, 600 g of finely divided sorbic acid (avera~e particle dia~
meter 20 ~ was placed in the kneader and kneaded with addition of said solution7 Columnar granules O.o mm in diameter were fabricated from this kneaded substance by means of extrusion type granulator and dried to make pro-ducts.
Example 11~
~hile mixin$ in the kneader 500 g of finely divided ~ :
sorbic acid (average particle diameter 20 ~) and 500 g of potassium citrate ~owder were kneaded for 30 minutes with addition of 2.00 ml of waterO Columnar granu.les 0.8 mm in diameter were fabricated from thls kneaded substance by means of extrusion type granulator and dried to make pro- .- :
ductso Example 12:
239 g of powdered sugar (ground cane sugar) and 750 g of finely divided sorbic acid (average particle diameter 30 ~) were thoroughly mixed togetherO ~fter that, solution in which 10 ~ of glycerine and 1 g of high purity soybean lecithin were dissolved in 100 ml of water was added on to the mixture obtained and kneaded together in the kneader for 20 minutesO Columnar granules OD 8 mm in diameter were formed from this kneaded substance by means of the extrusion type granulating machine, folloed by dryingO
The product so obtained was preferable as one for :.
dog food.
Exa~ple 13:

_ 14 -ll~S3~7 ~ 49 g of powdered potassiu~n sorbate was thoroughly mixed l~th 75 S Of finely divided sorbic acid ~average particle diameter ~0 ~ So~ution in ~ich high purity soybean 'ecithin was dissolved in 100 ml of water was added on to the mixture obtained and Xneaded together by means of kneader for 20 minutesO Columnar granules 0~ mm in diameter were formed fro~l this l~neaded substance by means of the extrusion type granulating machine.
The product so obtained was suited to margarine~
Example 14:
5 kg of water-washed material cucumbers (about 5-10 cm lon~) an~ 5 ~ of salt water (10 B~) were placed in a tub. The tub was covered and a light weight stone was laid thereon to pickle at 30 C.0 Two days later common table salt was further added to maintain 10 B~o It was fermented for three weeks in such condition and check-ing was made of the condition where the mernbrane-producing yeast occurred during the feralentation. The occurrence of the membrane-producing yeast is not desl~ble because it -becomes the cause of spoiling flavor and of putrefactionO
The preparation to add was indicated in Table-l below, but it was added by dissolving in advance in the aforesaid salt water.
~s is indicated in Table-17 obviously excellent results could be obtained in the run of the instant invention in comparison with control.

: ..

l~S3~,7 Table 1 - _ Number of days for preservation (30C.) Test Run PH 3 7 ~ 14 18 21 Non-addition 6.5 _ + ++ +++ +++++ not (control) measured _ Potassium 6.7 _ _ _ + ++
sorbate (control) _ Example 2 4.1 _ _ _ _ (instant invention) -; indicates no changing.
+ rJ +++++; indicates the degree to which putrefaction occurred.

Example 15:
As dog food materials minced poultry by-product, ox liver and ox tongue were placed in the kneader with a jacket and mixed by applica-tion of heat for 5 minutes. After that, cane sugar, soybean powder, propylene glycol, sorbitol, water and preparations as indicated in Table-2 were added and mixed by application of heat for another 10 min-utes. Further, water held at 85C. was flowed down the jacket of knead-er to heat the dog food material. The dog food so obtained was wrapped in plastic film and cooled down to room temperature (25C.). It was placed in aseptic Schale and covered. It was preserved at 30C. and antiseptic tests were conducted.
Furthermore, the composition of the dog food 5~7 material above was as follows.
Poultry by-products 35.0 ox liver 5.0 ox tongue 5.0 cane sugar 5.0 soybean powder 45.0 propylene glycol 2.0 70% sorbitol solution 1.5 water 1.5 Table 2 .
Water Number of days for preservation rest Run PH content ~30 C-) (%) - .
- _ 7 14 2128 3542 49 Non-addition of preparation 6.55 32.1 _ _ + + ++ +++ ++++
~control) ., _ _ __ _ Potassium sor-bate 0.26% 6;59 32.5 _ _ _ + ++ ++
(control) ~ _ Sorbic acid 0.2% 6.37 32.1 _ _ _ _ _+ +
(control) Product of Example 12 0.26% 6.36 32.0 _ _ _ _ __ _ invention) _ -; indicates no changing.
+ ~ +++++; indicates the degree to which putrefaction occurred.
As is clear from Table-2, the product of the instant invention shows the best result in the antiseptic ,,~ ~, .

11(~`53~7 effect. With the composition of dog food putrefaction by bacteria hardly occurs since it is low in the water content and high in the su~ar concentrationO Putre- -faction by ~olds and yeasts, however, occurs. In general, potassium sorbate is used for preventing putrefaction by molds and yeastsO Eor its reason sorbic acid is effective for lowering the PH a~d increasing the antiseptic effect, but in the dog food which is low in the water content and high in the sugar concentration it is very bard to completely dissolve. This imbalance leads to the imbalance in the anti~
septic effect. On the contrary, in the case of potassium sorbate, it is inferior in the antiseptic effect because of its high solubility, but it can be perfectly dissolved and it is possible to insure preservation for a given period of time. The product of the instant invention improved the defect of sorbic acid being hardly dissolvable while making the most of merits with sorbic acid that it should be high in the antiseptic effect. Whereby the prcservability of dog food could be further improved Example 16 ~
Observations were made of the condition where the ~-sorbic acid-containing granules of the instant invention obtained in Example 1, sorbic acid-containing powder of the instant invention obtained in Example 6, finely divided sorbic acid (average particle dia~eter 30 )l) and coarse powdered sorbic acid (particle diameter ~oo-600 )1) were dissolved in water, and measurements wera made of the amounts of sorbic acid dissolvedO ~ -Experiments and ~easurements were conducted as ~lQ53(~7 , .

follows. The respective specimens were added to 500 ml of water held at 30Co in ~uch amounts as to reach 0.5 g ~0.l%~ as sorbic acid stirred under given conditions by means of electro-~agnetic stirrerO I~mediately after, l minute after, 5 minutes after, lO minutes after and 20 minutes after the specimen was added observations were made of the solution conditionO At the same time, 2-3 ml of solution was taken by pipettes attached with filter paper. It was d~luted with water and by measuring the ultraviolet re~ion absorbance the amount of sorbic acid dissolved in water WAS determined. ;~
The results were tabulated in Table-30 T~e ~ranules and powder of the instant invention dissolved in the amount of 90% or more one mi~ute after addition and dissolved perfectly lO minutes later~ On the other hand, sorbic acid powder dissolved only in the a~ount of 6503% or 62.4% oven 20 minutes after addition.

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Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A process for the production of sorbic acid-containing powder or granules free from scatterability and rapidly soluble in water consisting of 5-90% by weight of finely divided sorbic acid with particle diameter of 50µ or less, 10-95% by weight of an easily water-soluble substance selected from the group consisting of sugars, sugar alcohols, organic acids, salts of organic acids and phosphates which is a solid at normal temperature, and 0-2% by weight of a hydrophilic surface active agent, said powder or granules having particle diameter of 300µ or more, which comprises preparing a mixture consisting of finely divided sorbic acid with particle diameter of 50µ or less, a said easily water-soluble substance which is a solid at normal temperature, water and/or an organic solvent and optionally, a hydrophilic surface active agent and forming powder or granules having particle diameter of 300µ or more from said mixture, followed by drying, or drying said mixture, followed by forming powder or granules having particle diameter of 300µ or more from said dried mixture.

2. Sorbic acid-containing powder or granules free from scatterability and rapidly soluble in water consisting of 5-90% by weight of finely divided sorbic acid with particle diameter of 50µ or less, 10-95% by weight of an easily water-soluble substance selected from the group consisting of sugars, sugar-alcohols, organic acids, salts of organic acids and phosphates which is a solid at normal temperature and 0-2% by weight of a hydrophilic surface active agent, characterized by having particle diameter of 300µ or more.

3. A process for preserving drinks and foods or feeds which comprises adding the sorbic acid-containing powder or granules according to claim 2 to pickels, wine, fish sausage, meat sausage, jam, mayonnaise, margarine, dog food or cat food.