JPH0234934B2 - - Google Patents
Info
- Publication number
- JPH0234934B2 JPH0234934B2 JP56130587A JP13058781A JPH0234934B2 JP H0234934 B2 JPH0234934 B2 JP H0234934B2 JP 56130587 A JP56130587 A JP 56130587A JP 13058781 A JP13058781 A JP 13058781A JP H0234934 B2 JPH0234934 B2 JP H0234934B2
- Authority
- JP
- Japan
- Prior art keywords
- sorbic acid
- double salt
- ester
- sorbitan
- acid
- 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 - Lifetime
Links
- 150000003839 salts Chemical class 0.000 claims description 18
- 235000010199 sorbic acid Nutrition 0.000 claims description 18
- 239000004334 sorbic acid Substances 0.000 claims description 18
- 229940075582 sorbic acid Drugs 0.000 claims description 18
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 17
- -1 sorbitan fatty acid ester Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
- 239000000194 fatty acid Substances 0.000 claims description 9
- 229930195729 fatty acid Natural products 0.000 claims description 9
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 claims description 7
- 235000010241 potassium sorbate Nutrition 0.000 claims description 7
- 239000004302 potassium sorbate Substances 0.000 claims description 7
- 229940069338 potassium sorbate Drugs 0.000 claims description 7
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 9
- 230000000903 blocking effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000011126 aluminium potassium sulphate Nutrition 0.000 description 1
- 230000002362 anti-crystal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229940050271 potassium alum Drugs 0.000 description 1
- GRLPQNLYRHEGIJ-UHFFFAOYSA-J potassium aluminium sulfate Chemical compound [Al+3].[K+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GRLPQNLYRHEGIJ-UHFFFAOYSA-J 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 235000020991 processed meat Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 235000011008 sodium phosphates Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
Description
【発明の詳細な説明】
ソルビン酸・ソルビン酸カリウム複塩等のソル
ビン酸複塩は畜肉加工品、水産練製品等の防腐
剤、防黴剤として有用である。かかる用途におい
て該複塩は添加対象物の蛋白質変性をほとんどお
こす恐れがなく弾力性のある製品を与えると同時
に強力な防腐効果を発揮する点に他の防腐剤を使
用する場合には見られない大きな特色がある。し
かして、該複塩は例えば、媒体中でソルビン酸と
ソルビン酸カリウムを反応させて得られる針状結
晶であり、単なるソルビン酸とソルビン酸カリウ
ムとの混合物とはその結晶形、性状等に著しい違
いがある。[Detailed Description of the Invention] Sorbic acid double salts such as sorbic acid/potassium sorbate double salts are useful as preservatives and antifungal agents for processed meat products, fish paste products, etc. In such applications, the double salt has the advantage that there is almost no risk of protein denaturation in the target product, and it provides a resilient product while at the same time exhibiting a strong preservative effect, which is not seen when other preservatives are used. It has great characteristics. However, the double salt is, for example, a needle-like crystal obtained by reacting sorbic acid and potassium sorbate in a medium, and is different from a simple mixture of sorbic acid and potassium sorbate in terms of its crystal shape, properties, etc. There is a difference.
しかしながらかかるソルビン酸複塩は結晶がブ
ロツク化する傾向があり、袋詰あるいは缶詰した
製品を長期にわたつて輸送したり、貯蔵したりす
ると全体が固化、ブロツク化し製品の取出しに不
便となつたり又、一旦ブロツク化すると容易に再
粉末化が出来ずその取扱に支障がおこる等その解
決が必要とされる。 However, the crystals of such sorbic acid double salts tend to form blocks, and when a packaged or canned product is transported or stored for a long period of time, the entire product solidifies and becomes blocked, making it inconvenient to take out the product. However, once it is turned into blocks, it cannot be easily re-pulverized, which poses a problem in its handling.There is a need to solve this problem.
しかるに本発明者等はかかる問題を解決すべく
鋭意研究を重ねた結果、ソルビン酸複塩にソルビ
タン脂肪酸エステルを配合してなる組成物は、全
くブロツキングがおこらないという顕著な効果が
得られることを見出し本発明を完成するに至つ
た。 However, as a result of extensive research aimed at solving this problem, the present inventors have found that a composition containing a sorbic acid double salt and a sorbitan fatty acid ester has the remarkable effect of not causing any blocking. Heading: The present invention has been completed.
本発明で対象とするソルビン酸・ソルビン酸カ
リウム複塩は例えばソルビン酸を90％エタノール
に加熱溶解し、これに等モル量のソルビン酸カリ
ウムを加えて加熱反応させ、液を冷却して得られ
る結晶をエタノールで再結晶する方法、ソルビン
酸を90％エタノール溶媒に加熱溶解しこれに1/2
モル当量程度の水酸化カリウムを加えて加熱反応
させ、液を冷却して得られる結晶をエタノールで
再結晶する等任意の方法で製造されるものであ
る。又本発明では上記以外の複塩としてソルビン
酸と、コハク酸、クエン酸、酒石酸、プロピオン
酸、酢酸等のナトリウム塩、カリウム塩の如き有
機酸塩、あるいはソルビン酸とリン酸ナトリウ
ム、リン酸カリウム、カリ明バンの如き無機酸塩
との複塩もいずれも使用可能である。 The sorbic acid/potassium sorbate double salt targeted by the present invention can be obtained, for example, by heating and dissolving sorbic acid in 90% ethanol, adding an equimolar amount of potassium sorbate to the solution, causing a heating reaction, and cooling the liquid. Method of recrystallizing crystals with ethanol: dissolve sorbic acid by heating in 90% ethanol solvent and add 1/2
It can be produced by any method such as adding about a molar equivalent of potassium hydroxide, causing a heating reaction, cooling the liquid, and recrystallizing the resulting crystals from ethanol. In addition, in the present invention, double salts other than the above include sorbic acid and organic acid salts such as sodium salts and potassium salts of succinic acid, citric acid, tartaric acid, propionic acid, acetic acid, etc., or sorbic acid and sodium phosphate, potassium phosphate, etc. , and double salts with inorganic acid salts such as potassium alum can also be used.
本発明では、ブロツキング防止剤としてソルビ
タン脂肪酸エステルを用いることが必須要件であ
る。結晶のブロツキング防止剤として種々の化合
物が提案されているが、ソルビン酸複塩等の食品
添加剤に使用するものはおのずと制限がある。 In the present invention, it is essential to use sorbitan fatty acid ester as an antiblocking agent. Although various compounds have been proposed as anti-crystal blocking agents, there are naturally limitations on what can be used in food additives such as sorbic acid double salt.
本発明者等は食品に添加されても無害な化合物
でありしかもブロツキング防止効果のある種々の
化合物を検討したが、その中でソルビタン脂肪酸
エステルが特異な効果を発揮しブロツキング防止
にすぐれていることを見出した。 The present inventors have investigated various compounds that are harmless even when added to foods and have an anti-blocking effect, and among them, sorbitan fatty acid ester exhibits a unique effect and is excellent in preventing blocking. I found out.
ソルビタン脂肪酸エステルとしては任意のもの
が使用可能であるが、高級脂肪酸エステルが有効
であり、就中、ソルビタンモノラウリルエステ
ル、ソルビタンモノオレイルエステル、ソルビタ
ントリオレイルエステル等が好ましい。 Although any sorbitan fatty acid ester can be used, higher fatty acid esters are effective, and sorbitan monolauryl ester, sorbitan monooleyl ester, sorbitan trioleyl ester, etc. are particularly preferred.
ソルビタン脂肪酸エステルの添加量は10ppm〜
2000ppm好ましくは50〜200ppmの範囲から選ば
れる。10ppm以下ではブロツキング防止効果が得
難く、一方2000ppm以上では製品の流動性に支障
をきたす。 Addition amount of sorbitan fatty acid ester is 10ppm~
2000ppm, preferably selected from the range of 50 to 200ppm. If it is less than 10 ppm, it is difficult to obtain an anti-blocking effect, while if it is more than 2000 ppm, the fluidity of the product will be affected.
本発明の組成物はエタノール等、のソルビタン
脂肪酸エステルは溶解するが、複塩は溶解しない
適当な溶媒にソルビタン脂肪酸エステルを溶解
し、この溶液と複塩を噴霧法、浸漬法等により混
合し、充分撹拌後、乾燥することによつて調製さ
れる。又乾燥は複塩の変質を防止するために、減
圧下で10〜40℃程度の低温で実施するのが有利で
ある。 The composition of the present invention is prepared by dissolving the sorbitan fatty acid ester in a suitable solvent such as ethanol that dissolves the sorbitan fatty acid ester but not the double salt, and mixing this solution and the double salt by a spraying method, dipping method, etc. It is prepared by thoroughly stirring and then drying. Further, in order to prevent deterioration of the double salt, it is advantageous to carry out the drying under reduced pressure at a low temperature of about 10 to 40°C.
尚、本願の組成物には必要に応じてソルビン酸
用の公知の添加剤、例えば、着色防止剤、酸化防
止剤等あるいは各種界面活性剤等任意に混合し得
る。 Note that, if necessary, known additives for sorbic acid such as coloring inhibitors, antioxidants, various surfactants, etc. may be mixed into the composition of the present application.
かくして得られる組成物はカビの発生、微生物
の発生を予防する必要のあるいずれの分野でも使
用可能である。即ち、食品、医薬品、化粧品、工
業用品、繊維製品等の微生物による腐敗、変質を
防止する目的で使用されたり、あるいは農薬等と
しても利用可能である。 The composition thus obtained can be used in any field where it is necessary to prevent the growth of mold and microorganisms. That is, it can be used for the purpose of preventing food, medicine, cosmetics, industrial goods, textile products, etc. from rotting or deteriorating due to microorganisms, or it can also be used as an agricultural chemical.
次に実例を挙げて本発明の組成物を更に詳しく
説明する。 Next, the composition of the present invention will be explained in more detail by giving examples.
実例 １
500容のナウターミキサーに、ソルビン酸・
ソルビン酸カリウム複塩100Kgを仕込み、撹拌下
に、ソルビタンモノラウリルエステル10ｇ（２
のエタノール溶液として）をスプレーガンにて噴
霧した。その後、約40分間撹拌をつづけ得られる
組成物を流動層乾燥機で乾燥した。Example 1 In a 500-volume Nauta mixer, add sorbic acid and
Charge 100 kg of potassium sorbate double salt, and add 10 g (2 kg) of sorbitan monolauryl ester while stirring.
(as an ethanol solution) was sprayed with a spray gun. Thereafter, stirring was continued for about 40 minutes, and the resulting composition was dried in a fluidized bed dryer.
得られた製品を10Kgポリ袋包装丸蓋押し缶につ
め室温で放置した。２ケ月放置してもブロツク現
象は全く認められなかつた。 The obtained product was packed in a 10 kg plastic bag and a press can with a round lid and left at room temperature. No blocking phenomenon was observed even after leaving it for two months.
対照例としてソルビタンモノラウリルエステル
の使用を省略した以外は同例と同一の実験を行つ
たところ、組成物はブロツク化し缶の形に固化し
た。 As a control example, the same experiment as in the same example was conducted except that the use of sorbitan monolauryl ester was omitted, and the composition solidified into a block and into the shape of a can.
実例 ２〜３
実例１においてソルビタンモノラウリルエステ
ルの使用量を20ｇ及び５ｇに代えた以外は同様の
実験を行つた。いずれの場合もブロツキングは全
く認められなかつた。Examples 2 to 3 The same experiments as in Example 1 were conducted except that the amount of sorbitan monolauryl ester used was changed to 20 g and 5 g. No blocking was observed in any case.
実例 ４〜５
実例１におけるソルビタンモノラウリルエステ
ルに代えて、ソルビタンモノオレイルエステル
（実例４）、ソルビタントリオレイルエステル（実
例５）を用いた以外は同様の実験を行つた。いず
れの場合もブロツキングは全く認められなかつ
た。Examples 4 to 5 Similar experiments were conducted except that sorbitan monooleyl ester (Example 4) and sorbitan trioleyl ester (Example 5) were used in place of sorbitan monolauryl ester in Example 1. No blocking was observed in any case.
Claims (1)
とからなる品質の改善されたソルビン酸複塩組成
物。 ２ ソルビン酸複塩がソルビン酸・ソルビン酸カ
リウム複塩である特許請求の範囲第１項記載の組
成物。[Claims] 1. A sorbic acid double salt composition with improved quality comprising a sorbic acid double salt and a sorbitan fatty acid ester. 2. The composition according to claim 1, wherein the sorbic acid double salt is a sorbic acid/potassium sorbate double salt.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13058781A JPS5832842A (en) | 1981-08-19 | 1981-08-19 | Sorbic acid double salt composition having improved quality |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13058781A JPS5832842A (en) | 1981-08-19 | 1981-08-19 | Sorbic acid double salt composition having improved quality |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5832842A JPS5832842A (en) | 1983-02-25 |
| JPH0234934B2 true JPH0234934B2 (en) | 1990-08-07 |
Family
ID=15037768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13058781A Granted JPS5832842A (en) | 1981-08-19 | 1981-08-19 | Sorbic acid double salt composition having improved quality |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5832842A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248619A (en) * | 1975-10-16 | 1977-04-18 | Chisso Corp | Process for preparation of granular sorbic acid |
| JPS52125118A (en) * | 1976-04-09 | 1977-10-20 | Chisso Corp | Manufacture of sorbic acid granules |
-
1981
- 1981-08-19 JP JP13058781A patent/JPS5832842A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5248619A (en) * | 1975-10-16 | 1977-04-18 | Chisso Corp | Process for preparation of granular sorbic acid |
| JPS52125118A (en) * | 1976-04-09 | 1977-10-20 | Chisso Corp | Manufacture of sorbic acid granules |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5832842A (en) | 1983-02-25 |
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