JPH026838A - Method for emulsifying fats and oils - Google Patents
Method for emulsifying fats and oilsInfo
- Publication number
- JPH026838A JPH026838A JP62129243A JP12924387A JPH026838A JP H026838 A JPH026838 A JP H026838A JP 62129243 A JP62129243 A JP 62129243A JP 12924387 A JP12924387 A JP 12924387A JP H026838 A JPH026838 A JP H026838A
- Authority
- JP
- Japan
- Prior art keywords
- oils
- fats
- gas
- dispersed
- fat
- 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.)
- Granted
Links
- 239000003925 fat Substances 0.000 title claims abstract description 21
- 239000003921 oil Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims description 9
- 230000001804 emulsifying effect Effects 0.000 title description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000006185 dispersion Substances 0.000 claims abstract description 16
- 239000002612 dispersion medium Substances 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 11
- 239000007787 solid Substances 0.000 claims abstract description 10
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 9
- 229930195729 fatty acid Natural products 0.000 claims abstract description 9
- 239000000194 fatty acid Substances 0.000 claims abstract description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 8
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 8
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 7
- 238000004945 emulsification Methods 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 abstract description 7
- 239000002609 medium Substances 0.000 abstract description 4
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 23
- 235000014593 oils and fats Nutrition 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 239000007962 solid dispersion Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- -1 fatty acid esters Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OMPIYDSYGYKWSG-UHFFFAOYSA-N 2-(2-ethoxy-2-oxoethyl)-2-hydroxybutanedioic acid Chemical compound CCOC(=O)CC(O)(C(O)=O)CC(O)=O OMPIYDSYGYKWSG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000269851 Sarda sarda Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010635 coffee oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/04—Specific aggregation state of one or more of the phases to be mixed
- B01F23/043—Mixing fluids or with fluids in a supercritical state, in supercritical conditions or variable density fluids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F23/00—Mixing according to the phases to be mixed, e.g. dispersing or emulsifying
- B01F23/40—Mixing liquids with liquids; Emulsifying
- B01F23/41—Emulsifying
- B01F23/4105—Methods of emulsifying
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Preparation And Processing Of Foods (AREA)
- Colloid Chemistry (AREA)
Abstract
Description
【発明の詳細な説明】
童呈上ｑ剋■分団
本発明は、超臨界ガスを用いて油脂、脂肪酸もしくはそ
れらの誘導体、さらには脂溶性物質を乳化する方法に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for emulsifying fats and oils, fatty acids or their derivatives, and also fat-soluble substances using supercritical gas.
校五煎豊員
近年、超臨界二酸化炭素などの超臨界状態ガスが種々の
物質に対して溶解能力を有する特性を有することから、
この特性を抽出分離技術に利用することが色々と提案さ
れている。In recent years, since supercritical gases such as supercritical carbon dioxide have the ability to dissolve various substances,
Various proposals have been made to utilize this property in extraction and separation techniques.
例えば、超臨界二酸化炭素を用いてコーヒーからアロマ
成分を含むコーヒー油を抽出する方法（特公昭５１−３
３１８５号）、かつお節等を超臨界状態の二酸化炭素で
処理して香気成分を抽出する方法（特開昭５９−２３２
０６４号）、コレステロールを含有する乾燥状物質を超
臨界二酸化炭素と接触させてコレステロール含有量の多
い油脂を抽出する方法（特開昭５９−１４０２９９号）
等が提案されている。For example, a method for extracting coffee oil containing aroma components from coffee using supercritical carbon dioxide (Special Publication No. 51-3
3185), a method of extracting aroma components by treating bonito flakes, etc. with supercritical carbon dioxide (Japanese Patent Laid-Open No. 59-232)
064), a method for extracting fats and oils with a high cholesterol content by bringing a dry substance containing cholesterol into contact with supercritical carbon dioxide (Japanese Unexamined Patent Publication No. 140299/1982)
etc. have been proposed.
すなわち、超臨界状態ガスは、従来、主として特定な成
分の抽出に利用されているものであって、該ガスを油脂
類の乳化に利用する技術については未だ報告されていな
い。That is, supercritical state gas has conventionally been used mainly for the extraction of specific components, and no technology has been reported yet for using the gas for emulsifying oils and fats.
発明が解決しようとする課題
本発明は、超臨界ガスを油脂類の乳化に利用することに
より、乳化分散系に高剪断力をかけることなく、かつ界
面°活性剤を使用することなく、油脂類を水溶液、半固
体状乃至固体状の分散媒体中に安定に乳化するための乳
化方法を提供することを課題とする。Problems to be Solved by the Invention The present invention utilizes supercritical gas to emulsify oils and fats without applying high shear force to the emulsified dispersion system and without using surfactants. An object of the present invention is to provide an emulsification method for stably emulsifying the compound into an aqueous solution, semi-solid or solid dispersion medium.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
発明の構成
本発明の特徴は、油脂、脂肪酸もしくはそれらの誘導体
或は脂溶性物質を、超臨界状態のガス中に溶解して水溶
液或は半固体形態乃至固体形態の分散媒体中に分散させ
ることにある。Structure of the Invention The present invention is characterized in that fats, oils, fatty acids, their derivatives, or fat-soluble substances are dissolved in a gas in a supercritical state and dispersed in an aqueous solution or a semi-solid or solid dispersion medium. It is in.
課題を解決するための−
本発明では、油脂、脂肪酸もしくはそれらの誘導体、成
は脂溶性物質、例えば脂肪酸エステル類等の乳化すべき
油脂類と、その分散媒体とを耐圧性容器に充填し、これ
に超臨界ガスを供給して、油脂類を該ガス中に溶解させ
、次いで撹拌などの機械的手段により、油脂類を溶解し
たガスを分散媒体中に分散させた後、容器を冷却して内
容物を凍結、固化または冷却、減圧させる。To solve the problems - In the present invention, fats and oils to be emulsified such as fats and oils, fatty acids or derivatives thereof, or fat-soluble substances such as fatty acid esters, and a dispersion medium thereof are filled in a pressure-resistant container, A supercritical gas is supplied to this to dissolve the oils and fats in the gas, and then the gas containing the dissolved oils and fats is dispersed into the dispersion medium by mechanical means such as stirring, and then the container is cooled. Freeze, solidify or cool the contents and reduce the pressure.
この凍結、固化酸は冷却、減圧により、超臨界ガスの分
散小胞中に溶解した油脂類は、温度降下に伴って不溶化
し、超臨界ガス物質の固相中に微細に分散する。次いで
、上記凍結、固化酸は冷却、減圧後、容器の内圧を減少
させて固化又は液化したガスを昇華又は気化させると、
分散媒体中に油脂類が乳化、分散した液状或は多孔質状
の乳化物が得られる。The frozen and solidified acid is cooled and depressurized, so that the fats and oils dissolved in the dispersed vesicles of the supercritical gas become insolubilized as the temperature falls, and are finely dispersed in the solid phase of the supercritical gas substance. Next, the frozen and solidified acid is cooled and depressurized, and the internal pressure of the container is reduced to sublimate or vaporize the solidified or liquefied gas.
A liquid or porous emulsion in which fats and oils are emulsified and dispersed in a dispersion medium is obtained.
本発明においては、上述の操作を連続方式で行うことも
できる。In the present invention, the above-mentioned operations can also be carried out in a continuous manner.
すなわち、油脂類を溶解させた超臨界ガスと、分散媒体
とを、乳化・分散装置内に連続的に供給して機械的に乳
化、分散させ、該装置の出口部で凍結、固化酸は冷却、
減圧させて装置外に取り出すと、固化または液化したガ
スが気化して、分散媒体中に油脂類を乳化、分散した乳
化物が連続的に得られる。That is, a supercritical gas in which fats and oils are dissolved and a dispersion medium are continuously supplied into an emulsification/dispersion device, where they are mechanically emulsified and dispersed, and then frozen at the outlet of the device, and the solidified acid is cooled. ,
When the pressure is reduced and the gas is taken out of the apparatus, the solidified or liquefied gas is vaporized, and an emulsion in which fats and oils are emulsified and dispersed in a dispersion medium is continuously obtained.
本発明で用いる超臨界ガスとしては、超臨界二酸化炭素
が最も実用的であるが、例えば亜酸化窒素のようなその
他の超臨界ガスも利用し得る。The most practical supercritical gas used in the present invention is supercritical carbon dioxide, but other supercritical gases such as nitrous oxide may also be used.
乳化に利用される油脂類としては、各種の動物性油脂、
各種脂肪酸並びに脂肪酸エステルのような誘導体及び脂
溶性物質が挙げられ、また、分散媒体としては、食品、
化粧品並びに医薬品等の基材としての水溶液或は半固体
状乃至固体状物質が用いられる。Fats and oils used for emulsification include various animal fats and oils,
Examples of the dispersion medium include various fatty acids, derivatives such as fatty acid esters, and fat-soluble substances.
Aqueous solutions or semi-solid to solid substances are used as base materials for cosmetics, pharmaceuticals, and the like.
本発明において、製品として得られる乳化物中の油脂類
の分散滴径（ｄｏ）を制御するには、攪拌などの機械的
条件を選択することにより超臨界ガスの小胞径（ｄ、ｃ
ｃ）を変化させるか、もしくは温度、容器内圧力の条件
を設定して油脂類の溶解度（ｃ）を変化させることによ
り行うとよい。In the present invention, in order to control the dispersed droplet diameter (do) of oils and fats in the emulsion obtained as a product, the vesicle diameter (d, c) of the supercritical gas can be controlled by selecting mechanical conditions such as stirring.
This may be carried out by changing c) or by changing the solubility (c) of the oil or fat by setting conditions such as temperature and pressure inside the container.
因に、乳化、分散後の乳化製品中の分散質である油脂類
の乳化・分散滴径（ｄｏ）には次の関係式が成立する。Incidentally, the following relational expression holds true for the emulsion/dispersion droplet diameter (do) of oils and fats, which are dispersoids in the emulsified product after emulsification and dispersion.
（式中、ｄｉｃｅ及びＣは上記の意味を表わし、ρ。は
製品の温度、圧力条件下における分散質の密度を表わす
）
なお、上記乳化に際して、超臨界ガスの粘性が低いこと
は、分散媒体中に分散する超臨界ガス小胞の径を小さい
剪断力の作用によって減少させることを可能にする。ま
た、超臨界ガス中の溶質の溶解度Ｃが−Ｓ的に言って大
きくないことは、多量の分散質を分散させる目的には不
利であるが、乳化・分散滴径ｄ０を小さくする点では有
利となる。(In the formula, dice and C represent the above meanings, and ρ represents the density of the dispersoid under the temperature and pressure conditions of the product.) In the above emulsification, the low viscosity of the supercritical gas means that the dispersion medium It is possible to reduce the diameter of the supercritical gas vesicles dispersed therein by the action of small shear forces. Furthermore, the fact that the solubility C of the solute in the supercritical gas is not large in terms of -S is disadvantageous for the purpose of dispersing a large amount of dispersoids, but it is advantageous for reducing the emulsification/dispersion droplet diameter d0. becomes.
更に、超臨界ガスの表面張力が小さく、拡散係数が大き
いという性質は、分散質を多孔質体中に迅速に分散・乳
化させるのに役立つものである。Furthermore, the properties of supercritical gas having a small surface tension and a large diffusion coefficient are useful for rapidly dispersing and emulsifying dispersoids in a porous body.
本発明によると、流動性を有しない半固体乃至固体形態
の乳化製品を調製する場合には、界面活性剤を使用する
ことなく、安定な乳化・分散物が得られる。According to the present invention, when preparing a semi-solid or solid emulsion product that does not have fluidity, a stable emulsion/dispersion can be obtained without using a surfactant.
また、本発明で用いる超臨界ガスは、乳化・分散を行っ
た後、昇華、気化して除去されるため、乳化製品中に溶
存した分を除き、その残留分は僅少であり、特に、二酸
化炭素は人体への安全性の点で問題もない。In addition, the supercritical gas used in the present invention is removed by sublimation and vaporization after emulsification and dispersion, so the residual amount is small except for the amount dissolved in the emulsified product. Carbon has no problems in terms of safety to the human body.
以上述べたごとく、本発明は、油脂類を、高剪断作用を
与えたり、界面活性剤を用いたりすることなく、水溶液
、半固体状乃至固体状の分散媒体中に安定に乳化・分散
させることができるので、乳化製品の製造上非常に有益
であると言える。As described above, the present invention is capable of stably emulsifying and dispersing oils and fats in an aqueous solution, semi-solid or solid dispersion medium without applying high shear action or using surfactants. It can be said that it is very useful in the production of emulsified products.
以下に実施例を示して本発明を具体的に説明する。EXAMPLES The present invention will be specifically described below with reference to Examples.
実施例
エンコサペンクエン酸エチルエステル（以下ＥＰＡと略
記する）２５０ｍ／とゼラチンゲル（ゼラチン５ｇと水
２０ｍ Ｉｌを用いて調製）とを、内容物４ｋ １）の
ステンレス製耐圧容器に仕込み、５０℃の温度において
、マクネチックスターラーを用いて攪拌しながら、超臨
界二酸化炭素を供給し、１００ｋｇ／−並びに３００ｋ
ｇ／ｃＩ１）の加圧下に１０分間、乳化・分散を行った
。乳化後、各内容分散物について、ゼラチンゲル中のＥ
ＰＡの分散滴径を顕微鏡写真（第１図及び第２図参照）
により測定した。Example 250ml of encosapene citrate ethyl ester (hereinafter abbreviated as EPA) and gelatin gel (prepared using 5g of gelatin and 20ml of water) were placed in a stainless steel pressure-resistant container with contents of 4k 1). At a temperature of 100 kg/- and 300 k
Emulsification and dispersion were performed for 10 minutes under pressure of g/cI1). After emulsification, for each content dispersion, E in the gelatin gel
Micrograph of dispersed droplet diameter of PA (see Figures 1 and 2)
It was measured by
その結果、１００ｋｇ／ｃ＋４の加圧下での乳化・分散
物の上記ＥＰＡの分散滴径は６．１±４．９μ齢であり
、３００ｋｇ／ｃ＋Ｊの加圧下での乳化・分散物の上記
ＥＰＡの分散滴径は３．２±０．７μ−であった。この
測定結果から、５０℃、ｌｏｏｋｇ／ｃｄの乳化条件で
はＥＰＡの添加量（仕込量）が溶解度以上であったと考
えられ、未溶解のままにゼラチンゲル中に分散したと考
えられる大きい分散滴径が観測された。一方、５０°Ｃ
２３００ｋｇ／ｃｄの乳化条件では、添加したＥＰＡは
超臨界二酸化炭素中に完全に溶解したものと考えられ、
その分散滴径は均一であり、かつ微小であった。As a result, the dispersed droplet size of the above EPA in the emulsified/dispersed product under a pressure of 100 kg/c+4 was 6.1±4.9μ, and the droplet size of the above EPA in the emulsified/dispersed product under a pressure of 300 kg/c+J was 6.1±4.9μ. The dispersed droplet diameter was 3.2±0.7μ. From this measurement result, it is considered that the amount of EPA added (prepared amount) was higher than the solubility under the emulsification conditions of 50°C and look/cd, and the diameter of the dispersed droplets was large, indicating that the EPA was dispersed in the gelatin gel without being dissolved. was observed. On the other hand, 50°C
Under the emulsification conditions of 2300 kg/cd, it is thought that the added EPA was completely dissolved in supercritical carbon dioxide,
The diameter of the dispersed droplets was uniform and minute.
第１図は、５０℃の温度、１００ｋｇ／ｃｄの加圧下に
乳化、分散させて得られるＥＰＡの分散溝の状態を、第
２図は、５０℃の温度、３００ｋｇ／ ｃ＋４の加圧下
に乳化、分散させて得られるＥＰＡの分散溝の状態をそ
れぞれ示す１ｍ鏡写真である。
第４図Figure 1 shows the state of the EPA dispersion groove obtained by emulsifying and dispersing it at a temperature of 50°C and a pressure of 100 kg/cd, and Figure 2 shows the state of the EPA dispersion groove obtained by emulsifying and dispersing it at a temperature of 50°C and a pressure of 300 kg/c+4. , 1m mirror photographs showing the state of dispersion grooves of EPA obtained by dispersion. Figure 4
Claims (3)
物質を、超臨界状態のガス中に溶解して水溶液或は半固
体形態もしくは固体形態の分散媒体中に分散させること
を特徴とする油脂類の乳化方法。(1) Fats and oils characterized in that fats and oils, fatty acids, derivatives thereof, or fat-soluble substances are dissolved in a gas in a supercritical state and dispersed in an aqueous solution, semi-solid form, or solid form dispersion medium. emulsification method.
請求の範囲第（１）項記載の乳化方法。(2) The emulsification method according to claim (1), wherein the gas in a supercritical state is supercritical carbon dioxide.
しくは冷却、減圧し、次いで固化もしくは液化したガス
を昇華または気化させる特許請求の範囲第（１）項記載
の乳化方法。(3) The emulsification method according to claim (1), wherein the dispersion obtained by the above dispersion is frozen, solidified, or cooled, and the pressure is reduced, and then the solidified or liquefied gas is sublimed or vaporized.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62129243A JPH0716598B2 (en) | 1987-05-26 | 1987-05-26 | Method of emulsifying oils and fats |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62129243A JPH0716598B2 (en) | 1987-05-26 | 1987-05-26 | Method of emulsifying oils and fats |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH026838A true JPH026838A (en) | 1990-01-11 |
| JPH0716598B2 JPH0716598B2 (en) | 1995-03-01 |
Family
ID=15004734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62129243A Expired - Fee Related JPH0716598B2 (en) | 1987-05-26 | 1987-05-26 | Method of emulsifying oils and fats |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0716598B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004513759A (en) * | 2000-06-08 | 2004-05-13 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | Method for producing nanoparticle suspension |
| JP2008206517A (en) * | 2007-01-31 | 2008-09-11 | Fancl Corp | Method for producing oil and fat-coated composite particle by using supercritical fluid, and composite particle |
| WO2013027465A1 (en) * | 2011-08-19 | 2013-02-28 | 独立行政法人海洋研究開発機構 | Method for producing emulsion |
| EP2894007A1 (en) * | 2014-01-14 | 2015-07-15 | Steffen Nitschke | Method and mixing device for generating a multiphase cooling and/or lubricant material for cooling and/or lubricating a processing device |
| JP2016503303A (en) * | 2012-11-28 | 2016-02-04 | ディーエスエム アイピー アセッツ ビー．ブイ． | Powder formulation |
-
1987
- 1987-05-26 JP JP62129243A patent/JPH0716598B2/en not_active Expired - Fee Related
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004513759A (en) * | 2000-06-08 | 2004-05-13 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | Method for producing nanoparticle suspension |
| JP2008206517A (en) * | 2007-01-31 | 2008-09-11 | Fancl Corp | Method for producing oil and fat-coated composite particle by using supercritical fluid, and composite particle |
| WO2013027465A1 (en) * | 2011-08-19 | 2013-02-28 | 独立行政法人海洋研究開発機構 | Method for producing emulsion |
| JP2013039547A (en) * | 2011-08-19 | 2013-02-28 | Japan Agengy For Marine-Earth Science & Technology | Method of producing emulsion |
| US10058827B2 (en) | 2011-08-19 | 2018-08-28 | Japan Agency For Marine-Earth Science And Technology | Method for manufacturing emulsion |
| US10967336B2 (en) | 2011-08-19 | 2021-04-06 | Japan Agency For Marine-Earth Science And Technology | Method for producing emulsion |
| JP2016503303A (en) * | 2012-11-28 | 2016-02-04 | ディーエスエム アイピー アセッツ ビー．ブイ． | Powder formulation |
| EP2894007A1 (en) * | 2014-01-14 | 2015-07-15 | Steffen Nitschke | Method and mixing device for generating a multiphase cooling and/or lubricant material for cooling and/or lubricating a processing device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0716598B2 (en) | 1995-03-01 |
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