CN102178231A - Preparation method of fish oil microemulsion - Google Patents

Preparation method of fish oil microemulsion Download PDF

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Publication number
CN102178231A
CN102178231A CN2011100991636A CN201110099163A CN102178231A CN 102178231 A CN102178231 A CN 102178231A CN 2011100991636 A CN2011100991636 A CN 2011100991636A CN 201110099163 A CN201110099163 A CN 201110099163A CN 102178231 A CN102178231 A CN 102178231A
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emulsifying agent
fish oil
assistant
microemulsion
oil microemulsion
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李玥
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Huabao Flavours and Fragrances Co Ltd
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Huabao Edible Essence and Spice Shanghai Co Ltd
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Abstract

The invention relates to a preparation method of fish oil microemulsion. In the method, O/W type fish oil microemulsion is obtained by adopting a complex emulsifying agent and an assistant emulsifying agent. The prepared fish oil microemulsion can not only solubilize the fish oil and reduce the fishy smell of the fish oil, but also slow the oxidization of unsaturated fatty acid in the fish oil and protect the nutrient value of the fish oil, therefore the quality of the product is improved, the smell pollution in production is reduced and the cost is lowered, so that the fish oil microemulsion is broadly applied to foods, medicines and nourishments.

Description

A kind of preparation method of fish oil microemulsion
[technical field]
The invention belongs to the micro emulsion preparing technical field.More specifically, the present invention relates to a kind of preparation method of fish oil microemulsion, and the fish oil microemulsion liquid that utilizes described method to prepare.
[background technology]
Unrighted acid is to constitute aliphatic acid body fat, needed by human.Unrighted acid is divided into two kinds of monounsaturated fatty acids and polyunsaturated fatty acids according to the difference of two key numbers.In food fat, monounsaturated fatty acids has oleic acid, and polyunsaturated fatty acid has linoleic acid, leukotrienes, arachidonic acid etc.Human body can not synthesize polyunsaturated fatty acids such as linoleic acid plus linolenic acid, must replenish from meals.
Unrighted acid has a lot of physiological functions, comprises keeping the mobile relatively of cell membrane, to guarantee the normal physiological function of cell; Make the cholesterol esterification, reduce cholesterol and triglycerides in the blood; Be the precursor matter of interior prostaglandin of synthesized human and thromboxane; Reduce blood viscosity, improve blood microcirculation; Improve the activity of brain cell, strengthen memory and thinking ability; Fat-reducing, health-care effect such as anticancer.But unrighted acid is oxidation very easily, loses its original nutritive value.
Fish oil is the byproduct of fish product processing, is the fat of fish animal.Fish and discarded object thereof are through steaming, squeezing and separate and obtain fish oil.The Main Ingredients and Appearance of fish oil is triglyceride, phosphorus glycerin ether, lipoid, liposoluble vitamin, and the protein degradation thing etc.
Contain polyunsaturated fatty acid in the fish oil, " the good fat " that promptly is commonly called as.Why fish oil has special important value, is that it is rich in the serial polyunsaturated fatty acid of ω-3, EPA and DHA because fish oil has special chemical composition.EPA (Eicosapaentaenoic Acid) is an eicosapentaenoic acid, popular name " blood vessel street cleaner ", but reducing blood lipid, prevention of arterial is atherosis, thus the prevention cardiovascular and cerebrovascular disease also has hypotensive effect by the protection to blood vessel and heart; DHA (Docosahexenoic Acid) is a DHA, popular name " brain gold ", the brain that mainly is present in the people, activating brain cell arranged, strengthen memory, delay brain aging, strengthen the effect that cranial nerve sensitivity and information are passed on speed, be another kind of special unrighted acid, have the clever factor of activating brain cell.
Microcapsules technology be utilize natural or synthetic macromolecular material (utricule) with solid, liquid or gas (capsule is tolerant) through packing formed a kind of have pellicle or the sealing cyst membrane the microencapsulation technology.Self has fishy smell fish oil, and easily oxidation can be added in bread and cheese, beverage and the special population food (as baby milk powder), as nutrition fortifier or food additives by processing such as microencapsulations.The technology of utilizing microcapsules technology to be prepared into fish oil micro-capsule in fish oil also has a lot of people's reports, and it had both kept the inherent characteristic of fish oil, had remedied the weak point of liquid fish oil again, had also increased some new characteristics.But traditional microcapsule formulation exists with solid form usually, can not use in liquid food, cosmetics, medicine, in addition, because the particle diameter of microcapsules is bigger, its biological utilisation is not very high, under the less situation of addition, also be unfavorable for being implemented in the even distribution in the product.
Microemulsified can overcome the above-mentioned defective of traditional microcapsules.Micro emulsion is as mixing the spontaneous nanoscale thermodynamic stable system that forms by oil phase, water and mixed surfactant, with respect to common emulsion, appearance transparent, good stability.The loaded down with trivial details production technology of original microcapsules has been simplified in the micro emulsion embedding, and particle diameter also is significantly less than the product of microencapsulation, and the nutritional labeling high degree of dispersion is beneficial to absorption, has improved the biological utilisation of nutriment greatly.
CN201010148866.9 discloses fish oil microemulsion carrier of a kind of food technology field and preparation method thereof.By weight percentage, the component of this micro emulsion carrier comprises non-ionic surface active agent 3-38%, fish oil 0.2-2%, ethyl oleate 1-11%, water 57-95.8%.Its preparation method is with 100 rev/mins of mixing speeds, continuing to add Tween80 behind fish oil and the ethyl oleate mixing under the stirring, adds water at last, obtains described fish oil microemulsion system.
People such as Zheng Minying, Liu Feng is in " preparation of fish oil microemulsion liquid and characteristic research " (" food and medicine " 2011 the 13rd the 01st phases of volume) literary composition, usefulness edible soybean oil and glycerine (glycerine) the oil phase solvent as fish oil has been proposed, select Tween80 and lactose as surfactant, prepared the fish oil microemulsion system.
The microemulsified product is a thermodynamic stable system, by with the Preparation fish microemulsion, reduces the fishy smell of fish oil, the oxidation that slows down unrighted acid in the fish oil, the nutritive value of protection fish oil.Therefore, develop a kind of quality controllable, have the suitable again industrial microemulsion formulation of higher bioavilability and have profound significance.The inventor is through test of many times, and the present invention has been finished in research.
[summary of the invention]
[technical problem that will solve]
The preparation method who the purpose of this invention is to provide a kind of fish oil microemulsion.
Another object of the present invention provides the fish oil microemulsion for preparing according to described method.
[technical scheme]
The present invention is achieved through the following technical solutions.
The present invention relates to a kind of preparation method of fish oil microemulsion.Described method is may further comprise the steps:
(1) emulsification
In mass, get 5-20 part fish oil, 5-10 part compound emulsifying agent and 2-10 part assistant for emulsifying agent, stir and carry out emulsification, obtain emulsion;
(2) mix with water
The emulsion that step (1) obtains mixes with 60-80 mass parts water and stirs, and obtains described fish oil microemulsion.
According to another kind of preferred implementation of the present invention, described compound emulsifying agent is that two or more is selected from Qu Latong, tween, sells the pool, the emulsifying agent of benzyl pool, lecithin, Crodaret, and described emulsifying agent is with mixed in equal amounts.
According to another kind of preferred implementation of the present invention, described assistant for emulsifying agent is one or more assistant for emulsifying agents that are selected from ethanol, propyl alcohol or hexanol, and when using multiple assistant for emulsifying agent, described assistant for emulsifying agent is with mixed in equal amounts.
According to another kind of preferred implementation of the present invention, preferably, in mass, the addition of described compound emulsifying agent is 1-2 a times of fish oil, and the described compound emulsifying agent of use and the mass ratio of assistant for emulsifying agent are 2: 1.
According to another kind of preferred implementation of the present invention, described water is distilled water, and its electrical conductivity is less than 3 μ S cm -1
According to another kind of preferred implementation of the present invention, described component stirred 2 hours with 250-350 rev/min of rotating speed under temperature 20-30 ℃.
The invention still further relates to a kind of fish oil microemulsion that obtains according to above-mentioned preparation method, described fish oil microemulsion is an O/W type micro emulsion, and its envelop rate is 76%, and particle size range is 8-50nm, and average grain diameter is 20nm.
Below the present invention will be described in more detail.
The present invention relates to a kind of preparation method of fish oil microemulsion.This method is in mass, gets 5-20 part fish oil, 5-10 part compound emulsifying agent and 2-10 part assistant for emulsifying agent, stirs and carries out emulsification, obtains emulsion; The gained emulsion mixes with 60-80 mass parts water and stirs, and obtains described fish oil microemulsion.
The fish oil that the present invention uses can be any fish oil of selling on the market, for example by the fast fish oil that reaches the production of marine organisms Products Co., Ltd in Wuxi.
In this application, so-called " compound emulsifying agent " is meant by the composite by a certain percentage emulsifier mixture that makes of two or more emulsifying agent monomer.According to the emulsifying agent preparation principle, adopt two or more the emulsified body of emulsifying agent preparation more more stable than being used alone the emulsified body that emulsifying agent makes.
In the present invention the compound emulsifying agent of Shi Yonging be that two or more is selected from Qu Latong, tween, sells the pool, the emulsifying agent of benzyl pool, lecithin, Crodaret, described emulsifying agent is with mixed in equal amounts.
The Qu Latong of Shi Yonging is Qu Latong X-114 (Triton X-114) in the present invention, is a kind of nonionic surface active agent or title detergent (detergent), has good level dyeing, emulsification, wetting, diffusion, antistatic property.The spendable Qu Latong of the present invention is a product sold on the existing market, for example is that the Triton X-114 that the bio tech ltd company of shaking produces is composed in Shanghai.
Tween (Tween) also be emulsifying agent Tween, is the condensation product of sapn (Span, Span) and oxirane, is a class non-ionic surface active agent.Because sapn is sorbierite and the formed ester of different higher fatty acids, so tween is actually series of products of the same type, in general fine chemistry industry shop or chemical reagents corporation be divided into 20,40,60,80 etc. multiplely, select for use according to different needs in actual applications.The tween that the present invention uses can be food-grade Tween 80 or the polysorbate60 of selling on the existing market, for example is the Tween 80 that Henan Jin Run food additives Co., Ltd produces.
Selling pool (Myrij) is another kind of nonionic emulsifier, is the esters product that is formed by polyoxyethylene glycol and LCFA condensation.Selling the pool is the trade name of polyoxyethylene fatty acid ester.Selling damp class surfactant has different kinds, as sells pool-45, sells the pool-49, sells pool-51 etc.They all are water miscible, and stronger emulsifying capacity is arranged, mainly as solubilizer and oil/water type emulsifier.The pool of selling of Shi Yonging can be the Myrij 51 that sells on the existing market in the present invention, for example is the Myrij 51 that Jiangsu Hai'an Petrochemical Plant produces.
The benzyl pool is another kind of non-ionic surface active agent, and it is the trade name of polyoxyethylene aliphatic alcohol ether class, because of the polyoxyethylene groups degree of polymerization and fatty alcohol different have different kinds.Be commonly used for emulsifying agent or solubilizer on the medicament.Commonly used have cetomacrogol (forming), peregal 0 (condensation product that forms by 15 unit polyethylene and oleyl alcohol), Ai Moerfu by polyethylene glycol and hexadecanol condensation (by 20 more than the unit oxygen ethene and the condensation product of oleyl alcohol) etc.The benzyl pool of using among the present invention can be a product sold on the existing market, for example the Brij 56 of Nanjing WeiEr chemical engineering Co., Ltd's production.
Lecithin is natural amphoteric ionic surfactant, is present in the yolk, is made up of the anionicsite of phosphoric acid fat type and the cationic moiety of quaternary.It is water insoluble, but very strong to the emulsifying capacity of grease, can be made into the very thin emulsion that is difficult for breaking of oil droplet.The lecithin that the present invention uses can be product sold on the existing market, for example the lecithin of Henan Jin Run food additives Co., Ltd production.
In the present invention, the Crodaret of use can be a product sold on the existing market, for example the EL 35 of BASF AG's production.
Assistant for emulsifying agent can be regulated the HLB value of emulsifying agent, and forms littler emulsion droplet.It mainly plays following effect in the formation of micro emulsion: (1) provides micro emulsion to form and the required extremely low interfacial tension of Thermodynamically stable; (2) rely on the curvature that non-polar group is regulated the interface; (3) flowability of increase interfacial film.Assistant for emulsifying agent commonly used should be the nonionic surface active agent of medicinal short chain alcohol or suitable HLB value.In the present invention, described assistant for emulsifying agent is one or more assistant for emulsifying agents that are selected from ethanol, propyl alcohol or hexanol, and when using multiple assistant for emulsifying agent, described assistant for emulsifying agent is with mixed in equal amounts.
The inventor finds that in order to obtain the effect of self-emulsifying microemulsion, the ratio of the ratio of emulsifier type, emulsifying agent and assistant for emulsifying agent and fish oil and emulsifying agent and assistant for emulsifying agent is very crucial.Different types of emulsifying agent has very big difference to the self-emulsifying microemulsion effect of fish oil, is committed step so select emulsifying agent, and finds that the self-emulsifying microemulsion effect of composite emulsifying agent is much better than the self-emulsifying microemulsion effect of single a kind of emulsifying agent.Though a large amount of emulsifying agents helps the effect of self-emulsifying microemulsion, they itself have certain toxicity, and the too much affiliation that adds has side effects.Therefore, preferably, in mass, the addition of described emulsifying agent is 1-2 a times of fish oil, and the described emulsifying agent of use and the mass ratio of assistant for emulsifying agent are 2: 1.
The micro emulsion that obtains is pellucidity, is a kind of O/W type fish oil microemulsion.
In the present invention, term " micro emulsion " is meant that micro emulsion is at spontaneous a kind of transparent or semitransparent, low-viscosity, isotropism that forms of proper proportion and thermodynamically stable profit mixed system by water, oil phase, surfactant and cosurfactant.Micro emulsion has the following advantages as the carrier of nutriment: (1) is transparency liquid, Thermodynamically stable, but and filtration sterilization, be easy to preparation and preservation.(2) water oil-packaging type micro-emulsion can be used as the carrier of nutriment, increases its dissolubility.(3) the protection liposoluble substance is not influenced by outside air, thereby has improved the storage time.(4) character of microemulsion system and composition are easy to control and measure, and therefore have feasibility.
In the present invention, the implication of term " O/W type micro emulsion " is a water oil-packaging type micro-emulsion, is made up of water continuous phase, oil nuclear and interfacial film, and the polar group of emulsifying agent and assistant for emulsifying agent is towards water continuous phase on the interfacial film.
Adopt various analytical methods that the character of micro emulsion is measured to fish oil microemulsion of the present invention.
Adopt static headspace gas chromatography to measure the envelop rate of the O/W fish oil microemulsion that obtains according to the inventive method, the instrument that uses is the 7694E head-space sampler of U.S. Agilent company, records envelop rate and can reach 76%.
Adopt the Nano-Zs90 particle size analyzer that the O/W fish oil microemulsion is carried out particle size determination, the particle size range that records is 8-50nm, and average grain diameter is 20nm.
Stability to fish oil microemulsion is measured, and at room temperature stores 12 months, layering or flocculation phenomenon do not occur.
[beneficial effect]
The inventive method is from the characteristics of fish oil; adopt the self-mciro emulsifying nano technology; fish oil is made the nano-composition of self-microemulsion; directly with after water mixes; the lower fish oil goods of transparent fishy smell have been formed; avoided the stench and water-insoluble of traditional fish oil goods, and the product of preparation can protect the unrighted acid composition in use, improve the quality of product.
The present invention becomes Preparation fish the solubility fish oil microemulsion first.Prepared fish oil microemulsion not only can solubilising fish oil, reduces the fishy smell of fish oil, the oxidation that slows down unrighted acid in the fish oil, and the nutritive value of protection fish oil, and then improved the quality of product, the smell that reduces when producing pollutes, and reduces cost.
[description of drawings]
Accompanying drawing 1 is fish oil phase of the present invention, water, single emulsifying agent and assistant for emulsifying agent three-phase diagram mutually.
Accompanying drawing 2 is particle diameter distribution maps of fish oil microemulsion prepared according to the methods of the invention.
Accompanying drawing 3 is fish oil phase of the present invention, water, compound emulsifying agent and assistant for emulsifying agent three-phase diagram mutually.
[specific embodiment]
Use the research experiment of single emulsifying agent
Select TritonX 114 as single emulsifying agent, select absolute ethyl alcohol as assistant for emulsifying agent, the ratio of emulsifying agent and assistant for emulsifying agent is 2: 1, and the total amount of getting emulsifying agent and assistant for emulsifying agent is 8g, behind the stirring and evenly mixing, adopts the method for dripping to draw the micro emulsion pseudoternary phase diagram.Accurately take by weighing emulsifying agent and fish oil mixing by 9: 1,8: 2,7: 3,6: 4,5: 5,4: 6,3: 7,2: 8,1: 9 (w/w), at 30 ℃ of constant temperature, drip deionized water while stirring, become clarification until solution by muddiness, or become muddiness by clarification, state no longer changes, and writes down critical addition.When system is formed a little into micro emulsion by the point that muddiness becomes clarification, continue to drip water, become muddy point by clarification and be the micro emulsion end point.
By oil, water, mixed surfactant mass fraction in critical point, the drafting ternary phase diagrams.
As shown in Figure 1, ratio according to surfactant and fish oil, the gained microemulsion region is divided into three kinds of dissimilar microemulsion region (W/O, co-continuous phase, O/W), in the process of thin up, the micro emulsion type changes co-continuous phase micro emulsion into by the W/O micro emulsion, continue thin up, change O/W type micro emulsion into.
Use the research experiment of compound emulsifying agent
The TritonX 114 of selection equivalent and polysorbate60 are as compound emulsifying agent, select absolute ethyl alcohol as assistant for emulsifying agent, the ratio of emulsifying agent and assistant for emulsifying agent is 2: 1, and the total amount of getting emulsifying agent and assistant for emulsifying agent is 8g, behind the stirring and evenly mixing, adopt the method for dripping to draw the micro emulsion pseudoternary phase diagram.Accurately take by weighing compound emulsifying agent and fish oil mixing by 9: 1,8: 2,7: 3,6: 4,5: 5,4: 6,3: 7,2: 8,1: 9 (w/w), at 30 ℃ of constant temperature, drip deionized water while stirring, become clarification until solution by muddiness, or become muddiness by clarification, state no longer changes, and writes down critical addition.When system is formed a little into micro emulsion by the point that muddiness becomes clarification, continue to drip water, become muddy point by clarification and be the micro emulsion end point.
By oil, water, emulsifying agent mass fraction in critical point, the drafting ternary phase diagrams.
As shown in Figure 3, similar with the situation of using single emulsifying agent, ratio according to emulsifying agent and fish oil, the gained microemulsion region is divided into three kinds of dissimilar microemulsion region (W/O, co-continuous phase, O/W), in the process of thin up, the micro emulsion type changes co-continuous phase micro emulsion into by the W/O micro emulsion, continues thin up, changes O/W type micro emulsion into.And, the O/W type micro emulsion that uses compound emulsifying agent to obtain, its self-emulsifying microemulsion effect is much better than the self-emulsifying microemulsion effect of single emulsifying agent.Therefore, the present invention selects the interior point of O/W microemulsion region shown in Figure 3 as prescription.
Embodiment 1
Get fish oil 15g, quality TritonX 114 such as selection and Tween 80 are as compound emulsifying agent, assistant for emulsifying agent is selected normal propyl alcohol, the mass ratio of compound emulsifying agent and assistant for emulsifying agent is 2: 1, and the total amount of getting compound emulsifying agent and assistant for emulsifying agent is 25g, behind the stirring and evenly mixing, thin up mixes stand-by, the addition of water is 60g, is sub-packed in the Brown Glass Brown glass bottles and jars only by required dosage, promptly makes O/W type fish oil microemulsion liquid of the present invention.
Adopt the Nano-Zs90 particle size analyzer that the O/W fish oil microemulsion is carried out particle size determination, the particle size range that records is 10-60nm, and average grain diameter is 21nm.
Stability to this fish oil microemulsion is measured, and at room temperature stores the phenomenon that does not occur layering, flocculation after 12 months.
Adopt static headspace gas chromatography to measure the envelop rate of this fish oil microemulsion, recording envelop rate is 78%.
Embodiment 2
Get fish oil 10g, select equivalent TritonX 114 and Brij 56 as compound emulsifying agent, assistant for emulsifying agent is selected n-hexyl alcohol, the ratio of compound emulsifying agent and assistant for emulsifying agent is 4: 1, and the total amount of getting compound emulsifying agent and assistant for emulsifying agent is 20g, behind the stirring and evenly mixing, thin up mixes stand-by, the addition of water is 70g, is sub-packed in the Brown Glass Brown glass bottles and jars only by required dosage, promptly makes fish oil microemulsion liquid of the present invention.
Adopt the Nano-Zs90 particle size analyzer that the O/W fish oil microemulsion is carried out particle size determination, the particle size range that records is 10-50nm, and average grain diameter is 25nm.
Stability to this fish oil microemulsion is measured, and at room temperature stores the phenomenon that does not occur layering, flocculation after 12 months.
Adopt static headspace gas chromatography to measure the envelop rate of this fish oil microemulsion, recording envelop rate is 78%.
Embodiment 3
Get fish oil 10g, select mass ratio 1: 1 PEG 40 and Tween 80 as compound emulsifying agent, assistant for emulsifying agent is selected ethanol, the ratio of compound emulsifying agent and assistant for emulsifying agent is 2: 1, and the total amount of getting compound emulsifying agent and assistant for emulsifying agent is 20g, behind the stirring and evenly mixing, thin up mixes stand-by, the addition of water is 80g, is sub-packed in the Brown Glass Brown glass bottles and jars only by required dosage, promptly makes O/W fish oil microemulsion liquid of the present invention.
The average grain diameter that records fish oil microemulsion liquid is 20nm.
This fish oil microemulsion is at room temperature stored the phenomenon that does not all occur layering, flocculation after 6 months or 12 months.
The envelop rate that records this fish oil microemulsion is 76%.
Embodiment 4
Get fish oil 10g, lecithin 5g, Crodaret 5g, ethanol 10g, water 60g, make O/W fish oil microemulsion liquid by the step of embodiment 2.
Embodiment 5
Get fish oil 5g, lecithin 5g, Crodaret 5g, propyl alcohol 5g, water 65g, make O/W fish oil microemulsion liquid by the step of embodiment 2.
Embodiment 6
Get fish oil 20g, lecithin 5g, benzyl pool 5g, n-hexyl alcohol 10g, water 65g, make O/W fish oil microemulsion liquid by the step of embodiment 2.
Embodiment 7
Get fish oil 20g, Tween 80 2.5g, sell damp 2.5g, ethanol 2g, water 80g, make O/W fish oil microemulsion liquid by the step of embodiment 2.
Embodiment 8
Get fish oil 5g, Tween 80 2.5g, sell damp 2.5g, ethanol 2g, water 80g, make O/W fish oil microemulsion liquid by the step of embodiment 2.

Claims (7)

1. the preparation method of a fish oil microemulsion is characterized in that said method comprising the steps of:
(1) emulsification
In mass, get 5-20 part fish oil, 5-10 part compound emulsifying agent and 2-10 part assistant for emulsifying agent, stir and carry out emulsification, obtain emulsion;
(2) mix with water
The emulsion that step (1) obtains mixes with 60-80 mass parts water and stirs, and obtains described fish oil microemulsion.
2. method according to claim 1 is characterized in that described compound emulsifying agent is that two or more is selected from Qu Latong, tween, sells the pool, the emulsifying agent of benzyl pool, lecithin, Crodaret, and described emulsifying agent is with mixed in equal amounts.
3. method according to claim 1 is characterized in that described assistant for emulsifying agent is one or more assistant for emulsifying agents that are selected from ethanol, propyl alcohol or hexanol, and when using multiple assistant for emulsifying agent, described assistant for emulsifying agent is with mixed in equal amounts.
4. according to the described method of each claim among the claim 1-3, it is characterized in that in mass that the total amount of described compound emulsifying agent and assistant for emulsifying agent is 1-2 a times of fish oil, the mass ratio of described compound emulsifying agent and assistant for emulsifying agent is 2: 1.
5. method according to claim 1 is characterized in that described water is distilled water, and its electrical conductivity is less than 3 μ S cm -1
6. method according to claim 1 is characterized in that component mixing back under temperature 20-30 ℃, with 250-350 rev/min of rotating speed stirring 2 hours.
7. a fish oil microemulsion for preparing according to the described method of each claim among the claim 1-7 is characterized in that described fish oil microemulsion is an O/W type micro emulsion, and its envelop rate is 76%, and particle size range is 8-50nm, and average grain diameter is 20nm.
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CN103525564A (en) * 2013-11-06 2014-01-22 江南大学 Method for eliminating panfasidae catfish oil fishy smell
CN108522767A (en) * 2018-05-15 2018-09-14 西安中粮工程研究设计院有限公司 A kind of soft sweets and preparation method thereof of enhancing memory
CN109354678A (en) * 2018-09-20 2019-02-19 汕头经济特区鮀滨制药厂 The preparation method of cetomacrogol 1000
CN109381439A (en) * 2017-08-08 2019-02-26 陆文捷 A kind of novel fish oil soft capsule and preparation method thereof
CN110236198A (en) * 2019-06-18 2019-09-17 宁波仙健海嘉生物科技有限公司 Orally taken emulsion and preparation method thereof rich in Omega-3 unsaturated fatty acid
CN110720637A (en) * 2019-11-28 2020-01-24 广州大学 Nano-scale fish oil microcapsule and preparation method and application thereof

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CN102511664A (en) * 2012-01-16 2012-06-27 天津农学院 Fish oil feed additive and production method thereof
CN103525564A (en) * 2013-11-06 2014-01-22 江南大学 Method for eliminating panfasidae catfish oil fishy smell
CN103525564B (en) * 2013-11-06 2015-03-18 江南大学 Method for eliminating panfasidae catfish oil fishy smell
CN109381439A (en) * 2017-08-08 2019-02-26 陆文捷 A kind of novel fish oil soft capsule and preparation method thereof
CN108522767A (en) * 2018-05-15 2018-09-14 西安中粮工程研究设计院有限公司 A kind of soft sweets and preparation method thereof of enhancing memory
CN109354678A (en) * 2018-09-20 2019-02-19 汕头经济特区鮀滨制药厂 The preparation method of cetomacrogol 1000
CN110236198A (en) * 2019-06-18 2019-09-17 宁波仙健海嘉生物科技有限公司 Orally taken emulsion and preparation method thereof rich in Omega-3 unsaturated fatty acid
CN110236198B (en) * 2019-06-18 2024-02-09 宁波仙健海嘉生物科技有限公司 Oral emulsion rich in Omega-3 unsaturated fatty acid and preparation method thereof
CN110720637A (en) * 2019-11-28 2020-01-24 广州大学 Nano-scale fish oil microcapsule and preparation method and application thereof

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Application publication date: 20110914