JPS584542B2 - Sorbin Sanno Kendaku Ekimoshiku Hapaestono Seizouhou - Google Patents

Sorbin Sanno Kendaku Ekimoshiku Hapaestono Seizouhou

Info

Publication number
JPS584542B2
JPS584542B2 JP6668875A JP6668875A JPS584542B2 JP S584542 B2 JPS584542 B2 JP S584542B2 JP 6668875 A JP6668875 A JP 6668875A JP 6668875 A JP6668875 A JP 6668875A JP S584542 B2 JPS584542 B2 JP S584542B2
Authority
JP
Japan
Prior art keywords
sorbic acid
water
suspension
paste
present
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP6668875A
Other languages
Japanese (ja)
Other versions
JPS51142533A (en
Inventor
高野正明
中島正弘
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JNC Corp
Original Assignee
Chisso Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chisso Corp filed Critical Chisso Corp
Priority to JP6668875A priority Critical patent/JPS584542B2/en
Priority to DE19762623682 priority patent/DE2623682C3/en
Publication of JPS51142533A publication Critical patent/JPS51142533A/en
Publication of JPS584542B2 publication Critical patent/JPS584542B2/en
Expired legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/02Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C07C57/03Monocarboxylic acids
    • C07C57/10Sorbic acid

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

【発明の詳細な説明】 本発明は、ソルビン酸の新規な懸濁液、若しくはペース
トの製造法に関し、更に詳しくは、特殊な製法で製造し
たソルビン酸の微粒子と水からなる懸濁液若しくはペー
ストの製造法に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing a suspension or paste of sorbic acid, and more specifically, a suspension or paste consisting of fine particles of sorbic acid produced by a special production method and water. Concerning the manufacturing method.

ソルビン酸は、食品添加物として、ソルビン酸カリと共
に多種多数の食品に穂用され、その毒性が極めて少いこ
とまた食品に異味異臭、にごり等を与えることが少い為
もあつて食品加工業界に於て賞用されている。
Sorbic acid is used in a wide variety of foods as a food additive, along with potassium sorbate, and is used in the food processing industry because its toxicity is extremely low and it rarely imparts off-flavors, odor, or cloudiness to foods. It has been awarded in the.

そして現用のソルビン酸の使用形態は、結晶性粉末であ
つて、対象食品が粉末、粒状物、液体等の場合は、ソル
ビン酸の粉末を混合するのに比較的に支障が少いが対象
食品が固形物、ねり製品等である場合は、均一な塗布又
は分散がやゝ困難であり、分散をよくするためソルビン
酸の微粉末を使用しようとすれば、取扱いの際飛散しや
すいとか、保存安定性が不良であるとかの問題を生じる
The current usage form of sorbic acid is crystalline powder, and if the target food is powder, granules, liquid, etc., there is relatively little difficulty in mixing sorbic acid powder, but the target food is When sorbic acid is a solid substance, paste product, etc., it is difficult to uniformly apply or disperse it, and if you try to use fine powder of sorbic acid to improve dispersion, it may easily scatter during handling or may be difficult to store. This causes problems such as poor stability.

かゝる目的に使用する為のソルビン酸の分散液の製法と
して特公昭46−34409号の方法が提案されている
Japanese Patent Publication No. 46-34409 has proposed a method for producing a dispersion of sorbic acid for use in such a purpose.

この方法は、界面活性剤を含むソルビン酸アルカリ金属
塩の溶液を当量にやゝ満たない量の塩酸又は硫酸水溶液
中に添加して、ソルビン酸の分散液を製造するが、該分
散液が安定である点は好ましいが、該分散液中に、界面
活性剤ならびに多量の塩酸又は硫酸のアルカリ塩を含ん
でいるから、該分散液を使用した食品の味、色、透明性
などに微妙な影響を与えるおそれがある。
In this method, a solution of an alkali metal sorbic acid salt containing a surfactant is added to an aqueous solution of hydrochloric acid or sulfuric acid in an amount slightly less than the equivalent amount to produce a dispersion of sorbic acid, but the dispersion is stable. However, since the dispersion contains a surfactant and a large amount of alkali salts of hydrochloric acid or sulfuric acid, it may have a subtle effect on the taste, color, transparency, etc. of foods using the dispersion. There is a risk of giving.

また、ソルビン酸を原料とせず、ソルビン酸アルカリ塩
を原料とする場合は、ソルビン酸→ソルビン酸塩→ソル
ビン酸の工程が無駄となり、またソルビン酸アルカリ塩
に代えて、ソルビン酸+アルカリ+水を用いる場合は生
成したソルビン酸アルカリ塩の水溶液が着色する傾向が
強い。
In addition, if sorbic acid is not used as the raw material but instead sorbic acid alkali salt is used as the raw material, the process of sorbic acid → sorbate → sorbic acid is wasted, and instead of sorbic acid alkali salt, sorbic acid + alkali + water is used. When using sorbate, there is a strong tendency for the aqueous solution of alkali sorbate to be colored.

また、ソルビン酸を微粉化して界面活性剤水溶液と混合
攪拌すると50%程度のソルビン酸の懸濁液が得ちれる
ことも知られている。
It is also known that if sorbic acid is pulverized and mixed and stirred with an aqueous surfactant solution, a suspension of about 50% sorbic acid can be obtained.

(特公昭47−37547号)。(Special Publication No. 47-37547).

この方法による懸濁液は、塩酸又は硫酸塩を含まない点
で、前記特公昭46i−344.09号の方法のソルビ
ン酸の分散液よりすぐれてしるが、分散状態を維持する
ため相当量の界面活性剤が混合使用されており、かつ使
用時には、水で2倍以上に希釈しなければならない。
The suspension produced by this method is superior to the sorbic acid dispersion produced by the method of Japanese Patent Publication No. 46i-344.09 in that it does not contain hydrochloric acid or sulfate; however, in order to maintain the dispersed state, a considerable amount of A mixture of surfactants is used, and when used, it must be diluted at least twice with water.

本発明は、前記公知方法における欠点の全くないソルビ
ン酸の懸濁液若しくはソルビン酸のペーストを提供する
ことを目的とする。
The object of the present invention is to provide a sorbic acid suspension or a sorbic acid paste that does not have any of the disadvantages of the known methods.

更に詳細には、本発明は、水とソルビン酸以外の成分を
全く含まない高濃度のソルビン酸の懸濁液若しくは、ソ
ルビン酸のペーストを提供することならびにそのような
懸濁液若しくはペーストを簡単な方法で製造する方汰を
提供することを目的とする。
More specifically, the present invention provides a highly concentrated sorbic acid suspension or sorbic acid paste that does not contain any components other than water and sorbic acid, and also provides a method for easily preparing such a suspension or paste. The purpose is to provide a method for manufacturing by a method.

本発明は第2に、前記懸濁液若しくはペーストに適量の
好ましい界面活剤を加えて、分散安定性良好な分散懸濁
液若しくはペースト状分散懸濁物を製造する方法を提供
することを目的とする。
A second object of the present invention is to provide a method for producing a dispersion suspension or paste-like dispersion suspension with good dispersion stability by adding an appropriate amount of a preferred surfactant to the suspension or paste. shall be.

本発明者等は、前記目的達成の為に適当なソルビン酸の
微粉化につき苦心研究の結果本発明に到達した。
The present inventors have arrived at the present invention as a result of painstaking research into suitable pulverization of sorbic acid in order to achieve the above object.

前記研究過程で明らかにされたことは、ソルビン酸の結
晶性又は無定形の粉末を乾式・湿式いづれの方法を問わ
ず機械的松砕により懸濁液又は乳濁液に適する粒度まで
微粉砕することは、「■粒度の均一な粉砕が困難であり
(従って粉砕工程が複雑化若しくは精密化し易い)、■
必要以上に微粉化されたもの(例えば粒度0. 2 μ
以下)は品質的に不安定で劣化着色し易い」為に、本発
明の目的とする適度かつ均一な粒度の微粉末を工業的に
簡単な方法で得ることが困難であることである。
What was revealed in the above research process is that crystalline or amorphous powder of sorbic acid can be pulverized to a particle size suitable for suspension or emulsion by mechanical crushing using either dry or wet methods. This means that it is difficult to grind to a uniform particle size (therefore, the grinding process tends to become more complicated or precise),
Items that are more finely divided than necessary (e.g. particle size 0.2μ)
The following) are unstable in quality and easily deteriorate and become discolored, making it difficult to obtain fine powder with a suitable and uniform particle size, which is the object of the present invention, by an industrially simple method.

従つて、本発明者等は、機械的粉砕方法を断念し、溶液
から析出させる方法について詳細検討した。
Therefore, the present inventors abandoned the mechanical pulverization method and conducted detailed studies on a method of precipitation from a solution.

しかし、ソルビン酸アルカリ塩水溶液からの加酸による
如き方法(前記特公昭46−34409号)は、不純物
(塩酸塩、硫酸楊)が残存する欠点があり また有機溶
剤溶雇から析出させる方法は有機溶剤の回収が必要であ
るほか、得られたソルビン酸の微粉末に微量付着してい
る該溶剤の除去が困難である。
However, the method of adding acid from an aqueous solution of alkali sorbic acid (Japanese Patent Publication No. 46-34409) has the disadvantage that impurities (hydrochloride, sulfuric acid) remain, and the method of precipitating from an organic solvent solution has the disadvantage that impurities (hydrochloride, sulfuric acid) remain. In addition to the need to recover the solvent, it is difficult to remove a small amount of the solvent that is attached to the obtained fine powder of sorbic acid.

従って、本発明者等は本発明に使用する溶剤として、水
又は水と低沸点水溶性有機溶剤の混合物を使用し、微粉
末析出方法としては、ソルビン酸の熱水(又は水と水溶
性有機溶剤の混合物)溶液をノズルから噴出させること
により、本発明の目的を達成するに必要な粒度のソルビ
ン酸の微粉末を得ることに成功して、本発明に到達した
Therefore, the present inventors used water or a mixture of water and a low-boiling water-soluble organic solvent as the solvent used in the present invention, and used sorbic acid in hot water (or water and a water-soluble organic solvent) as a method for fine powder precipitation. The present invention was achieved by successfully obtaining a fine powder of sorbic acid having a particle size necessary to achieve the object of the present invention by jetting a solution of a mixture of solvents from a nozzle.

即ち、本発明は、ソルビン酸の熱水溶液若しくはソルビ
ン酸の水と水溶性低沸点有機溶剤混合物の熱溶液なノズ
ルから噴出させ、急速に冷却させ、該冷却と同時に若し
くは冷却後に過剰の水又は水と有機溶痢とを分離するこ
とを特徴とする沈降性のソルビン酸の微粒子と水からな
る懸濁液又はぺーストの製造法である。
That is, the present invention involves jetting a hot aqueous solution of sorbic acid or a mixture of water of sorbic acid and a water-soluble low-boiling organic solvent from a nozzle, rapidly cooling it, and removing excess water or water at the same time or after the cooling. This is a method for producing a suspension or paste consisting of precipitable sorbic acid fine particles and water, which is characterized by separating sorbic acid and organic dysentery.

以下、本発明の構成につき詳細に説
明する。
Hereinafter, the configuration of the present invention will be explained in detail.

先づ、本発明に使用するイルビン酸は、公知方法で製造
されたソルビン酸の結晶性若しくは無定形の粉末若しく
はこれらの粒状物、塊状物であって、その精製の程度は
、本発明の懸濁液若しくはペーストが、食品添加物とし
て支障なく使用し得る程度であればよい。
First, the irvic acid used in the present invention is a crystalline or amorphous powder of sorbic acid produced by a known method, or a granular or agglomerated product thereof, and the degree of purification thereof depends on the concerns of the present invention. It is sufficient that the suspension or paste can be used as a food additive without any problem.

従って、極めて少量の安定剤(酸化防止剤)若しくは少
量のソルビン酸カリを含有する場合も含まれる。
Therefore, it also includes cases where a very small amount of stabilizer (antioxidant) or a small amount of potassium sorbate is contained.

併し、本発明(特に本発明の第1)の目的上、相当量の
界面活性剤、糊料等を含むものは之等が必然的に本発明
の方法になるソルビン酸の懸濁液若しくはソルビン酸の
ペースト(以下本発明のソルビン酸の懸濁液等というこ
とがある)中に含まれることになるので好ましくない。
However, for the purpose of the present invention (particularly the first aspect of the present invention), suspensions of sorbic acid or suspensions containing a considerable amount of surfactants, thickening agents, etc., are necessarily included in the method of the present invention. This is not preferable because it will be included in the sorbic acid paste (hereinafter sometimes referred to as the sorbic acid suspension of the present invention).

また、本発明に使用する水は、不純物を含まない純水若
しくは蒸溜水が坦ましいが、少量の炭酸ガス、空気等を
溶解していても差支ない。
Further, the water used in the present invention is preferably pure water or distilled water that does not contain impurities, but it may also have a small amount of carbon dioxide gas, air, etc. dissolved therein.

また、本発明に使用する水溶性低沸点有機溶剤とは、沸
点100℃以下好ましくは80℃以下で、熱水に5%以
上好ましくは10%以上溶解しうる溶剤であって、水、
空気、200℃以下の温度、通常の室内光線若しくは之
等の組合せに対して安定なものをいい、好ましくは水と
共沸混合物を形成して、通常の蒸溜で溜出容易なもので
あり、具体的には、メタノール、エタノールのようなア
ルコーノ瓢酢酸メチル、酢酸エチルのような有機酸エス
テル、アセトンのような低級脂肪族ケトン、其他、ベン
ゼン、シクロヘキサン等の環状化合物があげられる。
Furthermore, the water-soluble low-boiling organic solvent used in the present invention is a solvent having a boiling point of 100° C. or lower, preferably 80° C. or lower, and that can be dissolved in hot water by 5% or more, preferably 10% or more, and which is soluble in water,
It refers to a substance that is stable against air, a temperature of 200°C or less, normal indoor light, or a combination thereof, preferably forms an azeotrope with water, and is easily distilled by normal distillation. Specifically, examples thereof include alkone methyl acetate such as methanol and ethanol, organic acid esters such as ethyl acetate, lower aliphatic ketones such as acetone, and cyclic compounds such as benzene and cyclohexane.

有機溶剤の併用は、本発明に於て使用するソルビン酸の
熱水溶液中に於けるソルビン酸の濃度を上昇させ、後述
のノズルから噴出させた後の過剰の水の分離を容易にす
る点で好ましい。
The combined use of an organic solvent increases the concentration of sorbic acid in the hot aqueous solution of sorbic acid used in the present invention, and facilitates the separation of excess water after it is ejected from the nozzle described below. preferable.

しかし一方、溶剤回収の必要があり、また、該溶剤が本
発明ノ製品即ち、ソルビン酸の懸濁液若しくはペースト
に微量であっても残存することは好ましくないので、前
記ノズルからの噴出後水一有機溶剤一ソルビン酸混合系
から例えば減圧蒸溜等により充分に除去しなければなら
ないので工程が複雑化する傾向があり、この点で好まし
くない。
However, on the other hand, it is necessary to recover the solvent, and it is undesirable for the solvent to remain in the product of the present invention, ie, the suspension or paste of sorbic acid, even in a small amount. Since the one-organic solvent-one-sorbic acid mixed system must be sufficiently removed by, for example, vacuum distillation, the process tends to become complicated, which is undesirable.

本発明に使用する溶剤として水のみを使用する場合は前
記の問題を生じないが、熱水の温度を充分に高く(例え
ば90℃)しないと適当な濃度のソルビン酸の溶液が得
られないおそれがある。
When using only water as the solvent used in the present invention, the above problem does not occur, but unless the temperature of the hot water is sufficiently high (for example, 90°C), there is a risk that a solution of sorbic acid with an appropriate concentration cannot be obtained. There is.

本発明に使用するソルビン酸の熱水溶液若しくは水と低
沸点有機溶剤混合物の熱溶液の製造は次のように行う。
The hot aqueous solution of sorbic acid or the hot solution of a mixture of water and a low-boiling organic solvent used in the present invention is produced as follows.

即ち、使用する前記水の一部若しくは全部を常圧若しく
は加圧可能の溶解器中に入れ、攪拌下に前記ソルビン酸
を一時に若しくは徐徐に投入し、加温して該ソルビン酸
を完全に溶解させる。
That is, a part or all of the water to be used is placed in a dissolver capable of normal pressure or pressurization, and the sorbic acid is added all at once or gradually while stirring, and heated to completely dissolve the sorbic acid. Dissolve.

溶剤として水一有機溶剤系を使用する場合は加温により
容易に共沸温度に達するので、加圧下に前記溶解を行う
ことが望ましい。
When a water-organic solvent system is used as the solvent, the azeotropic temperature is easily reached by heating, so it is desirable to carry out the above-mentioned dissolution under pressure.

前記水又は水と有機溶剤のソルビン酸に対する使用比率
は、■かゝる溶媒の加熱時におけるソルビン酸に対する
溶解力と、■後の工程であるノズルから噴出時の冷却析
出速度によって規制される。
The usage ratio of the water or water and organic solvent to sorbic acid is regulated by (1) the dissolving power of the solvent for sorbic acid during heating, and (2) the rate of cooling precipitation during jetting from the nozzle in the subsequent step.

即ち例えば、ソルピン酸の熱水溶液は、100℃以下で
は5%以上とすることは困難であり(註.相当量のソル
ビン酸カリを併用するものはこの限りでないが、本発明
の目的外である)、また例えば120℃以下では10%
以上とすることは困難である。
That is, for example, it is difficult to maintain a hot aqueous solution of sorbic acid at a concentration of 5% or more at temperatures below 100°C (Note: This does not apply to solutions in which a considerable amount of potassium sorbate is also used, but this is outside the scope of the present invention. ), or, for example, 10% below 120°C.
It is difficult to do more than that.

(註一般に溶解度の限度までソルビン酸を溶解させるこ
とは困難であり、またその必要もない)またノズルから
のソルビン酸の熱水溶液の噴出により、瞬時(少くとも
数秒以内に)に該噴出物の温度は数十度℃以上低下する
がこの際、該溶液中のソルビン酸の温度が濃すぎると、
目的の懸濁物中のンルビン酸の粒子径が微小となって分
散性は良いが沈降性不良となり、後述の懸濁液若しくは
ペーストの製造が困難(濃縮困難)となるほか、製品の
貯蔵安定性が不安定であるという欠点が生じ、逆に該溶
液中のソルビン酸の濃度が薄すぎると、目的の懸濁物中
のソルビン酸の粒子径が粗大となって分散性不良となり
、たとえ界面活性剤を添加しても乳濁せず、該懸濁物の
濃縮物はペーストとしての展着性、流動性に欠けること
になる。
(Note: Generally, it is difficult to dissolve sorbic acid to the limit of solubility, and it is not necessary.) Also, by spouting a hot aqueous solution of sorbic acid from a nozzle, the spouted product can be instantly (at least within a few seconds) The temperature drops by several tens of degrees Celsius or more, but at this time, if the temperature of the sorbic acid in the solution is too high,
The particle size of undruvic acid in the target suspension becomes minute, resulting in good dispersibility but poor sedimentation, which makes it difficult to manufacture suspensions or pastes (difficult to concentrate) as described below, and also makes it difficult to store the product. On the other hand, if the concentration of sorbic acid in the solution is too low, the particle size of sorbic acid in the target suspension will become coarse, resulting in poor dispersibility. Even when an active agent is added, no emulsion occurs, and the concentrated suspension lacks spreadability and fluidity as a paste.

従って、使用するソルビン酸と水又は水と有機溶剤との
混合物の使用比率は、重量で1:200ないし1:5好
ましくは1:50ないし1:10である(以下凡て重量
比)。
Therefore, the ratio of the mixture of sorbic acid and water or water and organic solvent used is 1:200 to 1:5 by weight, preferably 1:50 to 1:10 (hereinafter referred to as weight ratio).

また、水と有機溶剤の混合物における有機溶剤の比率は
、■該有機溶剤の存在が種類により著しくソルビン酸の
溶解度を上昇させること、■後述のノズル噴出時の水一
有機溶剤共沸組成物の蒸発による噴出物の液温度低下が
水単独の場合に比し極めて急速であることから、多量の
使用は好ましくなく、重量で水100部に対し、1ない
し30部好ましくは2ないし15部である。
In addition, the ratio of the organic solvent in the mixture of water and organic solvent is such that: (1) the presence of the organic solvent significantly increases the solubility of sorbic acid depending on the type; Since the liquid temperature of the ejected material decreases more rapidly due to evaporation than when water is used alone, it is not preferable to use a large amount, and the amount is 1 to 30 parts, preferably 2 to 15 parts, per 100 parts of water by weight. .

以上のように製造したソルビン酸の熱水溶液又はソルビ
ン酸の水と水溶性低沸点有機溶剤混合物の熱溶液(以下
ソルビン酸の熱水溶液等という)の温度は、80℃以上
好ましくは90℃以上120℃以下で120℃を超え例
えば150℃のような温度にすることは、該溶液のノズ
ルからの噴出時の圧力を高める以外格別の利点がない。
The temperature of the hot aqueous solution of sorbic acid or the hot solution of water of sorbic acid and a water-soluble low-boiling organic solvent mixture (hereinafter referred to as a hot aqueous solution of sorbic acid, etc.) produced as described above is 80°C or higher, preferably 90°C or higher, and 120°C or higher. ℃ or lower and higher than 120° C., such as 150° C., there is no particular advantage other than increasing the pressure when the solution is ejected from the nozzle.

本発明のソルビン酸の熱水溶液等の噴出と急速冷却は以
下に述べるように行う。
The spouting and rapid cooling of the hot aqueous solution of sorbic acid of the present invention is carried out as described below.

先づ使用するノズルは、公知の低粘度液を噴霧若しくは
微細な液滴に分散させるスプレーノズル若しくは、同等
の機能を有する機械又は装置であればよく、ノズル以外
のかゝる装置としては、例えば急速回転円板に被処理液
を滴下し、飛散させる装置などがあげられる。
The nozzle used first may be a known spray nozzle that sprays or disperses a low-viscosity liquid into fine droplets, or a machine or device having an equivalent function. Examples include a device that drops the liquid to be treated on a rotating disk and scatters it.

噴出物は、広範囲に飛散する間に水分若しくは水分一有
機溶剤の共沸混合物の一部が被噴出物の液滴から気化蒸
発し、急激に該液滴の温度が低下する。
While the ejected material is scattered over a wide area, part of the water or the azeotropic mixture of water and organic solvent evaporates from the droplets of the ejected material, and the temperature of the droplets rapidly decreases.

かゝる気化蒸発を容易にする為に、本発明に使用する噴
出物受器(噴出装置)は相当の空間を有し、かつ前記蒸
発物を該受器外に急速にとり出して受器外で凝縮させ、
一方該受器内温度を50℃以下若しくは30℃以下(例
えば室温)、該受器内圧力を常圧以下好ましくは、該受
器内温度における水の飽和蒸気圧程度( 100mmH
g以下)に保つようにする。
In order to facilitate such vaporization, the ejecta receiver (ejector device) used in the present invention has a considerable space, and the ejecta is rapidly taken out of the receiver. Condensed with
On the other hand, the temperature inside the receiver is 50°C or lower or 30°C or lower (for example, room temperature), and the pressure inside the receiver is preferably normal pressure or lower, preferably around the saturated vapor pressure of water (100 mmH) at the temperature inside the receiver.
g or less).

本発明に使用する噴出物受器内に噴出されたソルビン酸
の熱水溶液等は、前記のように一旦微細な液滴となり、
この間該液滴を構成する一部の水又は水と有機溶剤が蒸
発して、急速に温度低下(例えば90℃から40℃)す
る間に該液滴内に溶解していたソルビン酸が急速に析出
して本発明の懸濁液等を構成するソルビン酸の微粒子を
形成する。
As mentioned above, the hot aqueous solution of sorbic acid etc. ejected into the ejecta receiver used in the present invention becomes fine droplets, and
During this time, some of the water or water and organic solvent constituting the droplets evaporate, and while the temperature rapidly decreases (e.g. from 90°C to 40°C), the sorbic acid dissolved in the droplets rapidly evaporates. Fine particles of sorbic acid are precipitated and constitute the suspension of the present invention.

その平均的な粒径は0.5μないし1μであって、分散
粒子としては極めて微少であるが、一般の乳濁粒子より
は充分に大きい。
The average particle size is 0.5 μ to 1 μ, which is extremely small for a dispersed particle, but is sufficiently larger than a general emulsion particle.

またこれを前記特公昭46−34409号発明のソルビ
ン酸カリ溶液への酸添加による析出ソルビン酸の微粒子
(概ね2μ以下)と比較すると充分に小さい。
Moreover, this is sufficiently small when compared with the fine particles (approximately 2 μm or less) of sorbic acid precipitated by adding acid to a potassium sorbate solution according to the invention of Japanese Patent Publication No. 46-34409.

(一般に前記酸添加の方法では使用溶液の希釈酸添加時
の攪拌の強さにも実用的限界があるため、平均粒径2μ
以下の微粒子をつくることは困難である。
(Generally, in the above acid addition method, there is a practical limit to the strength of stirring when adding diluted acid to the solution used, so the average particle size is 2 μm.
It is difficult to make the following fine particles.

)杓、前記のように生成したソルビン酸の微粒子と水又
は水と未蒸発の有機溶剤からなる懸濁物は、噴出物受器
底に滞溜するので、これを間歇的又は連続的にとり出す
) The suspension consisting of fine particles of sorbic acid and water or water and unevaporated organic solvent generated as described above accumulates at the bottom of the ejecta receiver, so it is taken out intermittently or continuously. .

例えば、3%のソルビン酸の熱水溶液を本発明の方法に
よって噴出させた場合噴出物受器内での水の蒸発量は1
0%ないし20%程度で充分であり、その後の濃縮は後
述の方法でなされる。
For example, when a hot aqueous solution of 3% sorbic acid is ejected by the method of the present invention, the amount of water evaporated in the ejecta receiver is 1
A concentration of about 0% to 20% is sufficient, and subsequent concentration is performed by the method described below.

本発明の方法における噴出物受器内懸濁物は、次の組成
と性質を有する。
The suspension in the ejecta receiver in the method of the present invention has the following composition and properties.

即ち、重量比で水(又は水と有機溶剤)99ないし80
に対しソルビン酸の前記微粉末1ないし20で好ましく
は97ないし90に対し3ないし10である。
That is, water (or water and organic solvent) in a weight ratio of 99 to 80
The ratio of the fine powder of sorbic acid is 1 to 20, preferably 3 to 10 to 97 to 90.

受器から取出された該懸濁物がなお有機溶剤を含む場合
は、被加熱物の温度50℃以下好ましくは40℃以下で
減圧蒸溜して、該有機溶剤を水との共沸混合物として完
全に除去する必要がある。
If the suspension taken out from the receiver still contains an organic solvent, it is distilled under reduced pressure at a temperature of 50°C or lower, preferably 40°C or lower, to completely remove the organic solvent as an azeotrope with water. need to be removed.

有機溶剤を除去した前記懸濁物内の個々のソルビン酸の
微粒子は前述の平均粒径を有するが相互に凝集してかな
り大きな粒子を形成しているので放置すると沈降するが
、振盪すると容易に分散し、保存中固結することがない
The individual sorbic acid fine particles in the suspension from which the organic solvent has been removed have the above-mentioned average particle size, but since they coagulate with each other to form quite large particles, they will settle if left to stand, but will easily settle if shaken. Disperses and does not clump during storage.

従って、このままでも水性懸濁液として使用可能である
が、過剰の水分を有することは、使用上若しくは運搬上
不便であるから、該水分を静置分離又は、濾過若しくは
遠心分離して、ソルビン酸濃度20%以上30%程度の
ソルビン酸懸濁液又はソルビン酸濃度40%ないし55
%程度のペースト状物とすることがテキる。
Therefore, it can be used as it is as an aqueous suspension, but since having excess water is inconvenient for use or transportation, the water is separated by standing, filtered, or centrifuged to obtain sorbic acid. Sorbic acid suspension with a concentration of 20% or more and about 30% or a sorbic acid concentration of 40% to 55%
% of the paste.

前記静置分離(デカンテーション)ではソルビン酸濃度
30%程度まで可能であり、濾過では同じく40%ない
し55%程度まで、遠心分離では10%以下まで脱水可
能であるが、本発明の目的物であるペーストを取得する
為には、ソルビン酸として55%以下好ましくは50%
以下がよい。
The above-mentioned static separation (decantation) can dehydrate the sorbic acid up to a concentration of about 30%, filtration can similarly dehydrate it to around 40% to 55%, and centrifugation can dehydrate it to 10% or less. In order to obtain a certain paste, less than 55% as sorbic acid, preferably 50%
The following is good.

本発明の懸濁物の特徴は前記静置分離、濾過、遠心分離
等による脱水が極めて容易かつ円滑なことである。
A feature of the suspension of the present invention is that dehydration by the above-mentioned static separation, filtration, centrifugation, etc. is extremely easy and smooth.

このことは、前記濾過等を困難にするような極微細なソ
ルビン酸の粒子が単独では殆んど含まれていないことを
意味する、何故ならかゝる極微細粒子が相当量含まれた
懸濁液は、該懸濁液を静置した際の沈降に長時間を要し
、かっ濾過に際して濾布又はろ紙等のろ材の目つまりを
ひきおこし易いからである。
This means that there are hardly any ultrafine particles of sorbic acid that would make the filtration difficult. This is because it takes a long time for the suspension to settle when it is left to stand, and it tends to clog filter media such as filter cloth or filter paper during filtration.

これに対し、公知の他の方法例えば、ソルビン酸の粉末
を微粉砕機で粉砕することも不可能ではないが、その取
扱い、操作が複雑化し易く、品質の点では、後述の方法
同様の問題があり、また、特公昭46−34409号の
方法のようにソルビン酸カリの水溶液に酸を加えてソル
ビン酸の微粒子を析出させたものは、粒度が、微細にす
ぎたりあるいは、微細粒子を多量に含むため、濾過等が
困難であり、遠心分離による脱水では、脱水は可能であ
るが、懸濁物中の微細粒子部分に水分が集中する傾向を
生じ、懸濁物の場合は、長時間放置したことによる沈降
部分が固結し易い傾向を生じ、またペースト状物(水分
50%内外まで脱水したもの)の場合は、使用時の試料
採取、水等による円滑希釈がやゝ困難であり、特にソル
ビン酸濃度30%以上の懸濁液若しくは40%以上55
%以下のペースト状物の製造用として適当でない。
On the other hand, it is not impossible to use other known methods, such as pulverizing sorbic acid powder using a pulverizer, but the handling and operation tend to be complicated, and in terms of quality, there are problems similar to those of the method described below. In addition, in the method disclosed in Japanese Patent Publication No. 46-34409, in which fine particles of sorbic acid are precipitated by adding acid to an aqueous solution of potassium sorbate, the particle size may be too fine or a large amount of fine particles may be deposited. However, dehydration by centrifugation is possible, but water tends to concentrate in the fine particles of suspended matter, and in the case of suspended matter, filtration etc. are difficult. Sedimented parts tend to solidify when left unattended, and in the case of paste-like materials (dehydrated to around 50% water content), it is difficult to collect samples during use and to dilute them smoothly with water, etc. , especially suspensions with a sorbic acid concentration of 30% or more or 40% or more55
% or less is not suitable for producing paste-like products.

以上の本発明の構成の詳細な説明から明らかにされたよ
うに、本発明の方法になるソルビン酸の懸濁液若しくは
ペーストは、水とソルビン酸以外不純物若しくは添加剤
を含まず、また製法が極めて簡単である点で、公知の如
何なる方法よりもすぐれている。
As has been made clear from the above detailed explanation of the structure of the present invention, the sorbic acid suspension or paste used in the method of the present invention does not contain any impurities or additives other than water and sorbic acid, and the manufacturing method is It is superior to any known method in that it is extremely simple.

また、本発明の方法になる懸濁液若しくはペーストは、
使用上目的に適当な乳化剤、分散剤、分散安定剤等の少
量を添加混合することにより、容易に均一かつ安定な分
散液若しくはペースト状分散物(以下分散液等という)
とすることができる。
Further, the suspension or paste used in the method of the present invention is
By adding and mixing small amounts of emulsifiers, dispersants, dispersion stabilizers, etc. appropriate for the purpose of use, a uniform and stable dispersion or paste dispersion (hereinafter referred to as dispersion, etc.) can be easily created.
It can be done.

かゝる分散液等は安定で容易にソルビン酸微粒子が沈降
分離せず、また流動性ならびに被稀釈性が良好であるの
で、食品に塗布し、ねり込み若しくは稀釈して広い面積
に散布するのに極めて便利である。
Such a dispersion liquid is stable and the sorbic acid fine particles do not easily settle and separate, and has good fluidity and dilutability, so it can be applied to foods, mixed in or diluted, and then spread over a wide area. It is extremely convenient.

そしてかゝる乳化剤、分散剤、分散安定剤等の種類と使
用量については、本発明のソルビン酸の懸濁液若しくは
ペーストが使用される食品の種類、形状、加工段階、保
存期間等に応じて、該懸濁液等の使用者において、望ま
しいものを自由に選ぶことが出来る。
The type and amount of such emulsifiers, dispersants, dispersion stabilizers, etc. to be used will depend on the type, shape, processing stage, storage period, etc. of the food to which the sorbic acid suspension or paste of the present invention is used. Therefore, the user of the suspension etc. can freely select the desired one.

また、公知方法で製造された懸濁液を分散させる場合に
較べ使用する乳化剤等の量が著しく節約できる長所があ
る。
Furthermore, it has the advantage that the amount of emulsifier used can be significantly reduced compared to when dispersing a suspension prepared by a known method.

以下実施例によって本発明の構成と効果を説明する。The structure and effects of the present invention will be explained below with reference to Examples.

実施例 1 精製したソルビン酸の結晶30gを熱水に溶解させて溶
液量1000gとし、該液を98℃でノズルから、圧4
0〜5 0 mmHgに保った攪拌機付の噴出物受器へ
噴出させた。
Example 1 30 g of purified sorbic acid crystals were dissolved in hot water to make a solution amount of 1000 g, and the solution was heated at 98° C. through a nozzle under a pressure of 4
It was ejected into a ejecta receiver with a stirrer maintained at 0-50 mmHg.

噴出時の水分蒸発で約90gの水が溜出し、噴出終了後
の内容物(懸濁液)の温度は45℃、収量は905gで
あった。
Approximately 90 g of water was distilled out due to water evaporation during ejection, and the temperature of the contents (suspension) after ejection was 45° C., and the yield was 905 g.

該懸濁液をとり出し、吸引濾過(P紙使用)して過剰の
水分を分離し、やゝ固いクリーム状のソルビン酸と水か
らなるペースト49グを得た。
The suspension was taken out and subjected to suction filtration (using P paper) to separate excess water, yielding 49 g of a slightly hard creamy paste consisting of sorbic acid and water.

該ペースト中の水分は46%(ソルビン酸分54%)で
ソルビン酸の収率は88%であった。
The water content in the paste was 46% (sorbic acid content 54%), and the yield of sorbic acid was 88%.

なお濾液約850g中にソルビン酸が約3.5g含まれ
これは、回収可能であった。
Approximately 3.5 g of sorbic acid was contained in approximately 850 g of the filtrate, and this was recoverable.

ついで、前記取得物(ペースト46g)に、HLB1
5の庶糖脂肪酸エステル(商品名DKエステルF160
)0.2gを添加し、ホモジナイザ(商品名、日本精機
製)を用いて強く攪拌することにより滑らかな感触のペ
ースト状物(ペースト状乳濁液)を得た。
Then, HLB1 was added to the obtained material (46 g of paste).
5 sucrose fatty acid ester (product name DK ester F160
) was added and strongly stirred using a homogenizer (trade name, manufactured by Nippon Seiki) to obtain a paste-like material (paste-like emulsion) with a smooth texture.

このペースト状物は、水で数倍に希釈しても乳濁液とし
て安定であり、懸濁粒子の粒径を顕微鏡で調べたところ
大半のものが粒径1μ以下0.5μ以上の範囲内にある
ことが確認できた。
This paste-like material is stable as an emulsion even if diluted several times with water, and when the particle size of the suspended particles was examined using a microscope, most of them were within the range of 1 μm or less and 0.5 μm or more. It was confirmed that there is.

実施例 2 精製したソルビン酸の結晶50gを熱水に溶解させて溶
液量2000gとし該液を95℃でノズルから、器内に
10℃の水200gを攪拌状態に保ち、器内圧を40〜
5 0 mmHgに保った噴出物受器へ噴出させた。
Example 2 50g of purified sorbic acid crystals were dissolved in hot water to make a solution volume of 2000g, and the solution was heated to 95°C through a nozzle.200g of water at 10°C was kept stirring in a vessel, and the internal pressure was increased to 40~40°C.
The ejecta was ejected into an ejecta receiver maintained at 50 mmHg.

噴出終了後の液温は45℃、噴出所要時間は30分、溜
出凝縮させた水量は180gであった。
After the ejection was completed, the liquid temperature was 45° C., the ejection time was 30 minutes, and the amount of distilled and condensed water was 180 g.

次に、この受器内で攪拌下液温度40℃、減圧度40〜
50mmHgに保ち、ソルビン酸の析出した該受器内の
懸濁液を2時間で濃縮して250gとした。
Next, in this receiver, under stirring, the liquid temperature was 40°C, and the degree of vacuum was 40~40°C.
While maintaining the temperature at 50 mmHg, the suspension in which sorbic acid was precipitated was concentrated in 2 hours to 250 g.

この懸濁液は、振盪により均一に分散し、暫く静置する
と上澄部と沈澱部に明確に分離した。
This suspension was uniformly dispersed by shaking, and when left to stand for a while, it was clearly separated into a supernatant and a precipitate.

次テ、該懸濁液にHLB16.7のソルビタンモノラウ
レートポリエチレングリコールエーテル0.5g及びC
MC0.5gを溶解した水溶液50gを前記ホモジナイ
サーを使用して混合し、ソルビン酸の分散液を得た。
Next, add 0.5 g of sorbitan monolaurate polyethylene glycol ether of HLB 16.7 and C.
50 g of an aqueous solution in which 0.5 g of MC was dissolved was mixed using the homogenizer described above to obtain a dispersion of sorbic acid.

しかし、一部にソルビン酸の比較的大きな粒子(1.5
μないし5μ)が混在し、(5〜6時間程度静置すると
)前記粒子が沈降分離するのが認められた。
However, some relatively large particles of sorbic acid (1.5
It was observed that particles (μ to 5 μ) were present, and that the particles were sedimented and separated (when left standing for about 5 to 6 hours).

しかし、かゝる分離物は、全体をふりまぜることにより
、均一に分散し、(2〜3時間静置した程度では)再分
離することはなかった。
However, such a separated product was uniformly dispersed by shaking the whole product, and did not separate again (even after being left standing for 2 to 3 hours).

本実施例2と実施例1との比較から明らかなように、本
発明における噴出物は、たとえ40℃のような比較的低
い温度であっても、液量を数分の一のように濃縮するこ
とは、一部のソルビン酸の微粒子の結晶生長をもたらす
ので好ましくないが、濃縮程度2倍以内、濃縮温度40
℃以下であれば、殆んど不利な影響はない。
As is clear from the comparison between Example 2 and Example 1, the ejecta in the present invention can be concentrated to a fraction of the liquid volume even at a relatively low temperature such as 40°C. However, it is not preferable to do so because it causes crystal growth of some sorbic acid particles.
If the temperature is below ℃, there is almost no adverse effect.

しかし、濃縮でなく静置分離(デカンテーション)若し
くは濾過によって、過剰の水分を分離し、該水中に溶解
している微量のソルビン酸は別途回収し、若しくは、分
離水を再度ソルビン酸の熱水溶解に使用する方が望まし
い。
However, excess water is separated by decantation or filtration rather than concentration, and the trace amount of sorbic acid dissolved in the water is separately recovered, or the separated water is reused in hot water containing sorbic acid. It is preferable to use it for dissolution.

実施例 3 粗製ソルビン酸結晶65gを熱水に溶解させて溶液量2
000gとし、さらに粉末活性炭2gを加えて1時間攪
拌処理後加熱溶液状態のまゝ濾過して活性炭粉末を除去
した。
Example 3 65g of crude sorbic acid crystals were dissolved in hot water to give a solution volume of 2
000 g, and 2 g of powdered activated carbon was added thereto, stirred for 1 hour, and then filtered while still in the heated solution state to remove the activated carbon powder.

このソルビン酸の熱溶液を99℃に保ち、内圧を30〜
4 0 mmHgに保った攪拌機付噴出物受器に噴出さ
せ、噴出終了後に32℃の懸濁液1750gを得た。
This hot solution of sorbic acid is kept at 99℃ and the internal pressure is kept at 30~30℃.
The mixture was ejected into a ejecta receiver equipped with a stirrer maintained at 40 mmHg, and after the ejection was completed, 1750 g of a suspension at 32°C was obtained.

この懸濁液を濾紙を使用して吸引濾別し、水分含有率4
9%のペースト状物120gを得た。
This suspension was filtered by suction using filter paper, and the water content was 4.
120 g of a 9% paste was obtained.

次いでこのペースト状物に室温で10時間乾燥した窒素
を通気し、水分25%の砕け易い塊状物を得た。
The paste was then bubbled with dry nitrogen for 10 hours at room temperature, resulting in a friable mass with a moisture content of 25%.

このものにHLB1 1の庶糖脂肪酸エステルを前記塊
状物中のソルビン酸純分に対し、1重量%となるよう添
加し、混練すると次第に流動性が増加し、前記混練によ
り、庶糖脂肪酸エステルが均一に混合されたと考えられ
る状態になったとき該塊状物をホモジナイザーに移し、
該機で、短時間強力に攪拌することにより極めて滑らか
な感触のクリーム状ペーストが得られた。
To this, sucrose fatty acid ester with HLB1 1 was added to the amount of 1% by weight based on the pure sorbic acid content in the above lump, and when kneaded, the fluidity gradually increased, and by the kneading, the sucrose fatty acid ester became uniform. transferring the mass to a homogenizer when it is considered mixed;
A creamy paste with an extremely smooth texture was obtained by vigorous stirring for a short period of time in the machine.

該ペーストは、水によって容易に自由な割合に稀釈され
て安定な分散懸濁液をつくることができ、また、該ペー
スト中のソルビン酸の個々の微粒子の径は、1μ以下0
.5μ以上であった。
The paste can be easily diluted with water to any proportion to form a stable dispersion suspension, and the diameter of each individual particle of sorbic acid in the paste is 1 μm or less.
.. It was 5μ or more.

比較例 1 精製ソルビン酸30gを熱水に溶解させて溶液量100
0gとし、ついで当初98℃に維持し、強力に攪拌しな
がら外部冷却により、5分以内に60℃、15分以内に
40℃以下に冷却することにより、微細なソルビン酸の
粉末を有する懸濁液とした。
Comparative Example 1 30g of purified sorbic acid was dissolved in hot water to give a solution volume of 100g.
0g and then initially maintained at 98°C and externally cooled with vigorous stirring to 60°C within 5 minutes and below 40°C within 15 minutes to form a suspension with fine sorbic acid powder. It was made into a liquid.

ついで該懸濁液中のソルビン酸の微粒子を濾別して後、
該濾過物に少量の水を加えて濾過物中の水分を70%に
調整した後HLB15の庶糖酸エステルをソルビン酸純
分に対して10重量%添加して攪拌混合して得られた懸
濁液は分散安定性悪く沈降物はざくざくした感触を有し
ていた、このことは、ソルビン酸の熱水溶液から、通常
の冷却析出方法では、本発明の目的とするソルビン酸の
懸濁液若しくはペーストの製造は不可能であることを示
す。
Then, after filtering off the fine particles of sorbic acid in the suspension,
A small amount of water was added to the filtrate to adjust the water content in the filtrate to 70%, and then 10% by weight of HLB15 sucrose acid ester based on the pure sorbic acid was added and mixed with stirring to obtain a suspension. The liquid had poor dispersion stability and the precipitate had a gritty feel. This means that the normal cooling precipitation method from a hot aqueous solution of sorbic acid cannot produce the sorbic acid suspension or paste that is the object of the present invention. This shows that it is impossible to manufacture.

比較例 2 精製ソルビン酸30gをHLB15の庶糖脂肪酸エステ
ル0.3P敵含有する熱水に溶解させて溶液量1000
gとし、該液を98℃に維持しつつ、ノズルから減圧4
0〜5 0 mmHgに保った攪拌機付の噴出物受器へ
噴出させた。
Comparative Example 2 30g of purified sorbic acid was dissolved in hot water containing 0.3P sucrose fatty acid ester of HLB15 to make a solution volume of 1000
g, and while maintaining the liquid at 98°C, reduce the pressure from the nozzle to 4
It was ejected into a ejecta receiver with a stirrer maintained at 0-50 mmHg.

以後実施例1と同様に操作し、ソルビン酸の乳濁液ない
し分散懸濁液(以下乳化分散液)907gを得た。
Thereafter, the same procedure as in Example 1 was carried out to obtain 907 g of an emulsion or dispersion of sorbic acid (hereinafter referred to as emulsified dispersion).

この乳化分散液中のソルビン酸の濃度は約3%であり、
濾過によりソルビン酸の微粒子を分離することは(濾材
目つまり若しくは乳濁液のまゝ濾過される等の理由によ
り)全く不能であった。
The concentration of sorbic acid in this emulsified dispersion is about 3%,
It was completely impossible to separate the fine particles of sorbic acid by filtration (due to clogging of the filter material or the emulsion being filtered).

また、この乳化分散液を40℃に保持しつつ減圧濃縮し
、水分70%としたところ乳化分散液中の分散物(ソル
ビン酸)の分散安定性不良となり、微粒子の中比較的粒
子径の大きいものが相当量沈降した。
Furthermore, when this emulsified dispersion was concentrated under reduced pressure while being maintained at 40°C to bring the moisture content to 70%, the dispersion stability of the dispersion (sorbic acid) in the emulsified dispersion was poor, and the particle size among the fine particles was relatively large. A considerable amount of material settled.

該沈降物の径は顕微鏡観察によると直径1.2μ以上殊
に1.5μ以上のものが大部分を占めていた。
According to microscopic observation, most of the precipitates had a diameter of 1.2 μm or more, especially 1.5 μm or more.

上記から明らかなように最初の熱水中に冷却析出後の該
ソルビン酸粒子が乳化分散液となる程度の乳化剤を存在
させた場合には、その後本発明方法と同一のノズル噴出
.急速冷却を行っても、本発明方法と同様の性質を有す
る高濃度のソルビン酸の懸濁液さらにはペーストを得る
ことができない。
As is clear from the above, when an emulsifier is present in the initial hot water to the extent that the sorbic acid particles become an emulsified dispersion after being cooled and precipitated, then the same nozzle jetting as in the method of the present invention is performed. Even with rapid cooling, it is not possible to obtain highly concentrated suspensions or even pastes of sorbic acid with properties similar to those of the process according to the invention.

これは、熱溶液のノズル噴出時の噴出された液滴の大き
さならびに、該液滴の温度低下に伴って析出するソルビ
ン酸の結晶の凝集状態が界面活性剤の存在によって大巾
に異る為であろうと推察される。
This is because the size of the ejected droplets when a hot solution is ejected from the nozzle and the state of aggregation of the sorbic acid crystals that precipitate as the temperature of the droplets decreases vary widely depending on the presence of the surfactant. It is speculated that this is because of this.

比較例 3 精製ソルビン酸(結晶)20部を磁製乳鉢で充分に粉砕
し、粉砕後200メツシ篩で粗粒を除去した。
Comparative Example 3 20 parts of purified sorbic acid (crystals) was thoroughly ground in a porcelain mortar, and after the grinding, coarse particles were removed using a 200 mesh sieve.

この微粉末ソルビン酸10部と0.5部のソルビンタン
モノラウレートポリエチレングリコールエーテルに対し
、0.5%のCMCを溶解した水を加えてホモジナイザ
ーで高速攪拌混合を行い、ソルビン酸濃度50重量%の
ペースト状懸濁物を得た。
To 10 parts of this finely powdered sorbic acid and 0.5 parts of sorbitan monolaurate polyethylene glycol ether, water in which 0.5% CMC was dissolved was added and mixed at high speed with a homogenizer, and the sorbic acid concentration was 50% by weight. % pasty suspension was obtained.

この懸濁物を水で種々の倍率に稀釈(2、5、10倍)
したところ、該稀釈は容易で、懸濁物の水への分散性も
比較的良好であったが、該稀釈後の分散安定性は不良で
あり、いづれも短時間(30分ないし2時間)放置する
ことによって、懸濁物の大部分が沈降し、分離した。
Dilute this suspension with water to various ratios (2, 5, 10 times).
As a result, the dilution was easy and the dispersibility of the suspension in water was relatively good, but the dispersion stability after the dilution was poor, and in both cases the dilution was short (30 minutes to 2 hours). Upon standing, most of the suspension settled and separated.

また、前記ペースト状態濁物の感触は硬く、顕微鏡観察
の結果該ペースト状物中のソルビン酸の微粒子の径は、
大部分10〜50μであった。
In addition, the paste-like turbidity has a hard feel, and as a result of microscopic observation, the diameter of the fine particles of sorbic acid in the paste-like substance is:
Most were 10-50μ.

実施例 4 精製したソルビン酸の結晶45gを熱水に溶解させて溶
液量1000gとし該液を115℃に保ってノズルから
、減圧1 0 0 mmHgに保った攪拌機付の噴出物
受器であって、10℃の水1000gを該器内で攪拌状
態で保持しているものの内部へ噴出させた。
Example 4 45 g of purified sorbic acid crystals were dissolved in hot water to make a solution volume of 1000 g, and the solution was kept at 115° C. and passed from a nozzle into a ejecta receiver equipped with a stirrer and maintained at a reduced pressure of 100 mmHg. , 1,000 g of water at 10° C. was jetted into the vessel, which was kept in an agitated state.

噴出時の水分蒸発で約130gの水が溜出し、噴出終了
後の内容物(懸濁液)の温度は30℃、収量は1850
gであった。
Approximately 130g of water was distilled out due to water evaporation during the spouting, and the temperature of the contents (suspension) after the spouting was 30℃, and the yield was 1850g.
It was g.

該懸濁液をとり出し、吸引濾過して、やゝ硬いクリーム
状のソルビン酸と水からなるペースト75gを得た。
The suspension was taken out and filtered with suction to obtain 75 g of a slightly hard creamy paste consisting of sorbic acid and water.

該ペースト中の水分は50%(ソルビン酸分50%)で
ソルビン酸の収率は83%であった。
The water content in the paste was 50% (sorbic acid content 50%), and the yield of sorbic acid was 83%.

なお濾液約1760g中にソルビン酸約7gが含まれこ
れは回収可能であった。
Approximately 7 g of sorbic acid was contained in approximately 1,760 g of the filtrate and could be recovered.

ついで、前記取得物(ペースト75P)にHLB15の
庶糖脂肪酸エステルO.3gを添加し、ホモジナイザー
を用いて強く攪拌することにより、滑らかな感触のペー
スト状物を得た。
Next, the obtained product (paste 75P) was added with HLB15 sucrose fatty acid ester O. By adding 3 g and stirring strongly using a homogenizer, a paste-like material with a smooth texture was obtained.

このペースト状物は、実施例10ペースト状物と同等の
被稀釈性、稀釈液の分散安定性、分散粒子の粒径の大き
さとその分布を示した。
This paste-like material exhibited dilutability, dispersion stability of the diluent, and particle size and distribution of dispersed particles equivalent to those of the paste-like material of Example 10.

Claims (1)

【特許請求の範囲】[Claims] 1 ソルビン酸の熱水溶液若しくはソルビン酸の水と水
溶性低沸点有機溶剤混合物の熱溶液をノズルから噴出さ
せ、急速に冷却させ、該冷却と同時に若しくは冷却後に
過剰の水又は水と有機溶剤とを分離することを特徴とす
る沈降性のソルビン酸の微粒子と水からなる懸濁液若し
くはペーストの製造法。
1. A hot aqueous solution of sorbic acid or a hot solution of water of sorbic acid and a water-soluble low-boiling organic solvent mixture is spouted from a nozzle and rapidly cooled, and at the same time or after cooling, excess water or water and an organic solvent are removed. A method for producing a suspension or paste consisting of precipitable sorbic acid fine particles and water, which is characterized by separation.
JP6668875A 1975-06-03 1975-06-03 Sorbin Sanno Kendaku Ekimoshiku Hapaestono Seizouhou Expired JPS584542B2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP6668875A JPS584542B2 (en) 1975-06-03 1975-06-03 Sorbin Sanno Kendaku Ekimoshiku Hapaestono Seizouhou
DE19762623682 DE2623682C3 (en) 1975-06-03 1976-05-26 Process for the preparation of an aqueous dispersion containing sorbic acid as fine particles in a high concentration

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP6668875A JPS584542B2 (en) 1975-06-03 1975-06-03 Sorbin Sanno Kendaku Ekimoshiku Hapaestono Seizouhou

Publications (2)

Publication Number Publication Date
JPS51142533A JPS51142533A (en) 1976-12-08
JPS584542B2 true JPS584542B2 (en) 1983-01-26

Family

ID=13323111

Family Applications (1)

Application Number Title Priority Date Filing Date
JP6668875A Expired JPS584542B2 (en) 1975-06-03 1975-06-03 Sorbin Sanno Kendaku Ekimoshiku Hapaestono Seizouhou

Country Status (2)

Country Link
JP (1) JPS584542B2 (en)
DE (1) DE2623682C3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021075663A1 (en) * 2019-10-14 2021-04-22 주식회사 종근당바이오 Composition for preventing, ameliorating or treating non-alcoholic fatty liver disease comprising lactobacillus helvetica and bifidobacterium strains

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DE102004045622A1 (en) * 2004-09-17 2006-03-30 Aquanova German Solubilisate Technologies (Agt) Gmbh Preservative compositions
DE102006010809B4 (en) * 2006-03-07 2009-10-22 Aquanova Ag Solubilisate of a preservative
ES2334849T3 (en) 2006-03-07 2010-03-16 DRITTE PATENTPORTFOLIO BETEILIGUNGSGESELLSCHAFT MBH & CO. KG SOLUBILIZED OF PRESERVANTS AND METHOD FOR MANUFACTURING.
US8563062B2 (en) 2011-02-24 2013-10-22 Pepsico, Inc. Reduction of sorbic acid precipitation by volume control
US8697163B2 (en) * 2011-02-24 2014-04-15 Pepsico, Inc. Reduction of sorbic acid precipitation by forming microemulsion
US8414942B2 (en) 2011-02-24 2013-04-09 Pepsico, Inc. Reduction of sorbic acid precipitation in beverages
US8691309B2 (en) 2011-02-24 2014-04-08 Pepsico, Inc. Reduction of sorbic acid precipitation
WO2012154245A1 (en) * 2011-02-24 2012-11-15 Pepsico, Inc. Reduction of sorbic acid precipitation
US11944111B2 (en) 2015-02-20 2024-04-02 Pepsico., Inc. Stabilizing sorbic acid in beverage syrup

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021075663A1 (en) * 2019-10-14 2021-04-22 주식회사 종근당바이오 Composition for preventing, ameliorating or treating non-alcoholic fatty liver disease comprising lactobacillus helvetica and bifidobacterium strains

Also Published As

Publication number Publication date
DE2623682C3 (en) 1979-10-25
JPS51142533A (en) 1976-12-08
DE2623682A1 (en) 1976-12-09
DE2623682B2 (en) 1979-03-08

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