CN105506013B - A kind of method preparing duck oil diacylglycerol - Google Patents
A kind of method preparing duck oil diacylglycerol Download PDFInfo
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- CN105506013B CN105506013B CN201610061434.1A CN201610061434A CN105506013B CN 105506013 B CN105506013 B CN 105506013B CN 201610061434 A CN201610061434 A CN 201610061434A CN 105506013 B CN105506013 B CN 105506013B
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
Abstract
A kind of method that the present invention relates to fixed lipase catalyzed preparation duck oil diacylglycerol, the method first with basic hydrolysis prepares fatty acid mixed, is then mixed with glycerol by fatty acid mixed, utilizes immobilized lipase to carry out catalytic reaction.Show that immobilized lipase prepares the optimum condition of duck oil diacylglycerol by the method for enzyme concentration, substrate ratio, hydrolysis temperature, four single factor experiments of enzymolysis time and response surface analysis.Using fixed lipase catalyzed duck oil to prepare diglyceride, enzyme can be completely separated with glycerol production diester, makes product without the residual of enzyme, and product purity is high, has ensured food safety.It addition, the recyclable recycling of immobilized enzyme selected, reduce production cost, decrease environmental pollution.The method of the present invention is that the comprehensive utilization of duck oil side-product opens a new approach, it is possible to is greatly improved the added value of duck oil, is a green innovative project with important Development volue.
Description
Technical field
The invention belongs to technical field prepared by diglyceride, be specifically related to a kind of fixed lipase catalyzed system
The method of standby duck oil diacylglycerol.
Background technology:
Polyunsaturated fatty acid (PUFA) content of duck oil is higher, and monounsaturated fatty acid (MUFA)
Content higher than Adeps Sus domestica, Oleum Arachidis hypogaeae semen, Oleum Glycines, Semen Maydis oil, close to olive oil.The current research for duck oil is relatively
Few, major part duck oil uses as feedstuff, and economic worth is relatively low.The present invention intends using using duck oil as fat
Diglyceride is prepared in acid donors catalysis, to widen the utilization ways of duck oil, improves generation in the duck course of processing
Fat added value.
Diglyceride is by the product obtained after glycerol (glycerol) and two fatty acid esterifications.It is divided into 1,3-
Diglyceride and the two kinds of isomers of 1,2-diglyceride.Research shows, diglyceride (DG) blood fat reducing,
Reduce the aspect such as interior fat, suppression body weight increase and have critical function.This function is mainly by suppression glycerol
Three esters (TG) accumulate realization in vivo.TG is in intestinal, and two ends fatty acid is due to lipase effect, quilt
Enzymolysis is 2-monoglyceride (MG) and free fatty (FA), and is absorbed at intestinal epithelial cell.Little
In enterocyte, FA Yu 2-MG is synthesized rapidly TG (neutral fat) again, as neutral in blood
Fat is in all-around exercises, and those are not just accumulated as body fat by the neutral fat as Energy harvesting.
And DG be the most all broken down into can not the 1-MG of resynthesis fat and fatty acid because 1-MG and 2-MG
The position that middle fatty acid combines from glycerol is different, therefore has very big difference as neutral fat synthesis material,
It is the slowest again to synthesize to neutral fat in small intestinal.Endocellular liberation fatty acid concentration uprises, and by β-
Oxidative pathway is finally broken down into water and carbon dioxide release, and therefore DG is in small intestinal lipolytic and energy profit
Improve by rate.After making edible DG, the neutral fat in blood is difficult to rise, so, if persistently eating simultaneously
DG, just can reduce body fat accumulation.Thus inferring, on the one hand diglyceride remains triglyceride is had
Some trophic functions；On the other hand, owing to diglyceride and triglyceride are in the difference of human body metabolism, with
And the pancreatic lipase in human body is 1,3 specificity enzymes, therefore, diglyceride has some triglyceride institutes not
The physicochemical property having and health-care effect.Additionally, due to diglyceride has some physics and the biochemistry of uniqueness
Characteristic so that it is have wide exploitation prospect at aspects such as food, cosmetics, medicine.
Up to now, the method preparing diglyceride that domestic and international domain expert explores has following several: 1) change
Method: it produces diglyceride and has low cost, economical operation, the advantage easily realizing large-scale production.Early
Phase people this method multiplex produces diglyceride.Yet with reaction lack specificity, products obtained therefrom is 1,2-glycerol
Diester, the mixture of 1,3-DAG, ratio is usually 7:3～6:4.Therefore, this method is generally not capable of prediction
Fatty acid binding site in finished product.Although it is special also can to produce structure by special chemical reaction
1,3-DG, but need protective agent, reactions steps is numerous and diverse tediously long, and needs substantial amounts of chemical reagent or organic solvent,
Seriously polluted, this is that food, pharmaceuticals industry are less desirable, produces from cleaning, from the point of view of the requirement of environmental protection
Also it is unaccommodated.2) Hydrolyze method: presently disclosed hydrolyzed fat produces in the method for diglyceride, greatly
All carry out (patent CN101768076A) under conditions of high temperature, high pressure, easily make unsaturated fatty acid send out
Raw oxidation, and energy consumption is many, and production cost is higher, and easily evaporation pollutes, and is unfavorable for extensive raw
Produce.3) enzymatic isolation method: lipase-catalyzed ester exchange reaction, including transesterification, glycerol rhizolomy, acidolysis reaction.
Natural lipase is utilized to synthesize DAG, because have employed as catalyst grease hydrolysis or glycerolysis
Efficient biocatalyzer and become the preparation method of most industrial prospect；But, this enzyme can not be with product
(diglyceride) is completely separated, and product purity is low, it is impossible to ensure food safety；It addition, this technique can not
Enzyme is made to recycle and reuse.
Therefore, a kind of safe and environment-friendly, efficient, economic duck oil diacylglycerol preparation method is invented, finally
Reaching catalyzing enzyme to be completely separated with product (diglyceride), product remains without enzyme, recyclable heavy
The multiple target utilized, significant to duck fat ecological use and raising value-added content of product.
Summary of the invention:
It is an object of the invention to provide the preparation method of a kind of duck oil diacylglycerol, i.e. use immobilized-lipase
Diglyceride prepared by catalysis duck oil.
Applicant determines enzymolysis in long-term research and prepares the optimum preparating condition of duck oil diacylglycerol, logical
Cross and enzyme concentration, substrate ratio (glycerol: duck oil fatty acid mixed), temperature, the screening of time are determined most preferably
Preparation condition, and the preparation to immobilized enzyme is optimized, thus facilitates the present invention.
The method of the preparation duck oil diacylglycerol of the present invention, comprises the steps:
1) preparation of fatty acid mixed:
By duck oil solution 1.5h in 87 DEG C of thermostat water baths, be then transferred to separatory funnel remove lower floor molten
Liquid, adds the NaOH solution of 1mol/L, 87 DEG C of constant temperature hydrolysis in lower floor's solution, removes with NaCI washing
Remove glycerol, then be acidified to pH2～3, the fatty acid that release is free with the HCl of 10%；
2) preparation of diglyceride:
By above-mentioned steps 1) in fatty acid mixed mix with glycerol, add immobilized-lipase, be placed on perseverance
Temperature shaking table carries out enzyme digestion reaction, and enzyme-to-substrate is separated after terminating by reaction by centrifugal, obtains duck Phyllanthus emblica L. oil two
Ester.
Above-mentioned steps 2) in the mass ratio of glycerol and fatty acid mixed be 1:2.02, hydrolysis temperature is 44 DEG C, enzyme
The solution time is 9.1h, and under the conditions of this, enzyme digestion reaction is the most abundant, and product purity is high, decreases raw material and energy
The waste in source, is advantageously implemented green production.
Wherein immobilized-lipase, its preparation method is as follows:
1) FeC1 is weighed in the ratio of 1.5:13、FeCl2, add in the starch milk that concentration is 40%, put
Heating up in 65 DEG C of water-baths, being adjusted to pH value is 10, ultrasonic mixing in 65 DEG C of water-baths；Again by the liquid after mixing
Body is placed in 60 DEG C of stirred in water bath 2h, then standing is cooled to room temperature, adjusts pH the most neutral, by reacted liquid
Body 95% washing with alcohol 3 times, carries out solid-liquid separation with Magnet, and incline supernatant, vacuum lyophilization,
Cross 100 mesh sieves, obtain magnetic starch microcapsule；
2) weigh 1 part of magnetic starch carrier, the genipin solution of the 1% of 20 times of volumes of addition, cross-link 6h,
Product carries out solid-liquid separation, vacuum lyophilization, obtains the magnetic starch microcapsule of activation；
3) by magnetic starch microcapsule 1 part, the lipase solution 3 parts of 1% of activation, it is the buffering of 4 with pH
Liquid is settled to 25 times of volumes, in 30 DEG C, under rotating speed 200r/min in shaking table oscillating reactions 8h, vacuum is cold
Lyophilizing is dry, i.e. obtains immobilized-lipase.
The present invention uses fixed lipase catalyzed duck oil to prepare diglyceride, it is possible to product (diglyceride)
Being completely separated, product purity is high, and enzyme is capable of repeatedly recycling and reusing；Ensured food safety,
Decrease environmental pollution, reduce production cost.
Accompanying drawing illustrates:
In Fig. 1 present invention substrate than with enzyme concentration interaction response face figure
Hydrolysis temperature and enzyme concentration interaction response face figure in Fig. 2 present invention
Enzymolysis time and enzyme concentration interaction response face figure in Fig. 3 present invention
In Fig. 4 present invention, hydrolysis temperature and substrate are than interaction response face figure
In Fig. 5 present invention, enzymolysis time and substrate are than interaction response face figure
Enzymolysis time and hydrolysis temperature interaction response face figure in Fig. 6 present invention
Detailed description of the invention:
The present invention uses alkali process hydrolysis duck oil to prepare duck oil fatty acid mixed, then is pressed with fatty acid mixed by glycerol
Mix according to certain proportion, be subsequently adding a certain amount of immobilized-lipase and react.Life with diglyceride
One-tenth rate is index, and substrate ratio, enzyme concentration, response time and reaction temperature are factor, designs response surface experiments,
Filter out enzymolysis duck oil and prepare the optimum process condition of diglyceride.
In the present invention, diglyceride method prepared by enzymolysis duck oil, includes the steps:
1) preparation of fatty acid mixed: 200g duck oil is put into the beaker of 1000mL, adds distilled water to 440mL,
It is placed on 1.5h in 87 DEG C of thermostat water baths.It is then transferred to separatory funnel and removes lower floor, repeat above operation.
It is subsequently adding the NaOH solution of a certain amount of 1mol/L, 87 DEG C of constant temperature hydrolysis, removes sweet with NaCI washing
Oil, is acidified to pH2～3, the fatty acid that release is free with the HCl of 10%.
2) preparation of duck oil diacylglycerol: glycerol and duck oil fatty acid mixed are put according to the ratio of 1:0.5～3
Enter in conical flask, add the immobilized candida antarctica lipase B of 0.5%～3%, be then placed into shaking
On bed, design temperature is 30 DEG C～70 DEG C, and arranging the response time is 2～12h, after reaction terminates, by above-mentioned
Reactant liquor is centrifugal 20min in the high speed centrifuge of 4000r/min, just can be separated by enzyme, the supernatant obtained
For highly purified diglyceride mixt.The diglyceride mixt high effective liquid chromatography for measuring obtained its
Content.
Below in conjunction with specific embodiment, the method for the present invention is described in detail.
Embodiment 1: the preparation of duck oil diacylglycerol
Glycerol and duck oil fatty acid mixed are put in conical flask according to the ratio of 1:0.5～3, adds
The immobilized candida antarctica lipase B of 0.5%～3%, is then placed on shaking table, and design temperature is
30 DEG C～70 DEG C, arranging the response time is 2～12h, after reaction terminates, by above-mentioned reactant liquor in 4000r/min
High speed centrifuge in centrifugal 20min, just enzyme can be separated, the supernatant obtained is highly purified diglyceride
Mixture.Its content of diglyceride mixt high effective liquid chromatography for measuring obtained.
The optimization step of above-mentioned reaction condition is as follows:
(1) screening of enzyme concentration: substrate ratio (glycerol: fatty acid mixed) is set to 1:2, and reaction temperature is
50 DEG C, the response time is 10h, and enzyme concentration is respectively 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, so
Rear test respectively, carry out the Preliminary screening of enzyme concentration by measuring the production rate of diglyceride.
(2) screening of substrate ratio: arranging enzyme concentration is 2%, and reaction temperature is 50 DEG C, and the response time is 10h,
Glycerol: fatty acid mixed is respectively 1:0.5,1:1,1:1.5,1:2,1:2.5,1:3, tests respectively,
The Preliminary screening of substrate ratio is carried out by measuring the production rate of diglyceride.
(3) screening of hydrolysis temperature: arranging enzyme concentration is 2%, and the response time is 10h, substrate than for 1:2,
Reaction temperature is respectively 30 DEG C, 40 DEG C, 50 DEG C, 60 DEG C, 70 DEG C, tests respectively, sweet by measuring
The production rate of oil diester carries out the Preliminary screening of hydrolysis temperature.
(4) screening of enzymolysis time: arranging enzyme concentration is 2%, substrate is than for 1:2, and reaction temperature is 50 DEG C,
Enzymolysis time is respectively 2h, 4h, 6h, 8h, 10h, 12h, tests respectively, by measuring glycerol
The production rate of diester carries out the Preliminary screening of enzymolysis time.
(5) response surface experiments factor level design
Table 1 response surface experiments factor level
(6) response surface experiments and result thereof:
Table 2 response surface scheme and result
(7) foundation of response surface regression equation and analysis: by response surface analysis software design expert 8.0.5
Show after result of the test is analyzed that its equation of linear regression is as follows:
Y=93.27+2.33A-0.15B+2.11C+0.74D-1.07AB+0.97AC-1.48AD+1.8 8BC-0.52BD+0
.12CD-4.38A2-3.63B2-3.00C2-2.56D2
In formula, Y represents the production rate of diglyceride, and A represents that enzyme concentration, B represent substrate ratio, and C represents enzymolysis temperature
Degree, D represents enzymolysis time.The above-mentioned response surface is carried out variance analysis, result such as table 3
Table 3 response surface variance analysis
As can be seen from Table 3, regression model presents extremely notable (P<0.01), and it is 0.0643>0.05 that model loses plan item,
Affecting without significance, illustrate that the fitting degree of equation is preferable, residual error is caused by random error, and model regulation is suitable
When, available regression equation replaces the true point of test to be analyzed result of the test, and its correction coefficient of determination is
0.9110, there is the variability of the test data of 91.10% can explain with this regression model.Therefore, recurrence side
Journey can preferably describe the relation between each factor and response value, each concrete test factor shadow to response face amount
Sound is not simple linear relationship.A, C, A in each factor2、B2、C2、D2Result of the test is had the most aobvious
The impact (P < 0.01) write, result of the test is had a significant impact (P < 0.05) by BC, and the size of 4 factor impacts is closed
System is: A > C > D > B.
Using design expert8.0.5 software data processing and analysis, duck oil diacylglycerol optimum condition is: add
Enzyme amount 1.65%, substrate ratio (glycerol: fatty acid mixed) is 1:2.02, and hydrolysis temperature is 54 DEG C, during enzymolysis
Between be 9.1h, the production rate of diglyceride is 94.08% with this understanding.
Embodiment 2: diglyceride optimum process condition screening Orthogonal Rotational Regressive Tests prepared by enzymolysis duck oil
In the ratio of substrate ratio (glycerol: fatty acid mixed) 1:2.02, fatty acid mixed and glycerol are added taper
In Ping, it is placed in constant-temperature table, and sets reaction temperature as 44 DEG C, and it is false to add the 1.65% immobilization South Pole
Silk Yeast-lipase B, the response time is 9.1h, after reaction terminates, is centrifuged by enzymolysis solution in high speed centrifuge
10min, separates enzyme, and supernatant is high diglyceride mixt, and intermediate layer is immobilized-lipase, liquid
Phase chromatography measures the production rate of diglyceride.
Found by 5 checking tests, under this condition gained diglyceride production rate be followed successively by 93.25%,
94.09%, 93.88%, 94.22%, 94.17%, average recoveries is 93.92%, with the knot of case study on implementation 1
The most basically identical；The above results shows that the technique of the present invention has well repeatability and stability.
Embodiment 3: the preparation of immobilized-lipase
(1) pretreatment of fixation support: by HPD-800 macroporous resin soaked in absolute ethyl alcohol 12h, sucking filtration,
It is washed till neutrality with distilled water, is dried under vacuum to constant weight.5%HCl pickling 12h, 5%NaOH alkali cleaning 12h,
It is washed till neutrality, drying for standby.24h, dried for standby is soaked with pH7.5 phosphate buffer solution.
(2) fat enzyme immobilizatio: weigh carrier and lipase according to the ratio of 15.3:1, be placed in conical flask,
Add the distilled water of 30mL, (rotating speed 150r/min) absorption 3h in the constant-temperature table of 34 DEG C.Adsorb
After one-tenth add 1% genipin crosslinking 3.2h, postlyophilization, obtain immobilized lipase.
The candida antarctica lipase B enzyme activity using the method fixing is 92.3% before fixing, and should
It is still 80.3% that immobilized lipase reuses 4 relative enzyme work.And use genipin is as cross-linking agent,
Field of food it is more suitable for compared with glutaraldehyde.
(3) immobilized-lipase Stability Determination
1) heat stability of immobilized enzyme: immobilized lipase and the most immobilized lipase are positioned over
30 DEG C, 35 DEG C, 40 DEG C, 45 DEG C, 50 DEG C, 55 DEG C, 60 DEG C, 65 DEG C, 70 DEG C, 75 DEG C, the perseverance of 80 DEG C
1h in warm water bath, is immediately placed in the refrigerator of 4 DEG C cooling afterwards, measures enzyme and lives.Result shows: not solid
Lipase and the immobilized lipase of fixedization are more or less the same at 40 DEG C of thermostabilitys, the most immobilized lipase
After 40 DEG C, enzyme is lived and is begun to decline, and immobilized lipase is lived at 50 DEG C of enzymes and just begun to decline, and shows immobilization
Lipase there is compared with the most immobilized preferable heat stability.
2) storage stability of immobilized enzyme: immobilized and the most immobilized lipase is placed on 4 DEG C of refrigerators
Middle storage, measures the enzyme after storing 2d, 4d, 6d, 8d, 10d, 12d, 14d and lives, over time
Extending, resolvase vigor is decreased obviously, but immobilized lipase enzyme after storing 14d is lived and still kept 87.5%,
Illustrate that immobilized lipase has good storage stability.
3) operational stability measures: in order to detect the operational stability of immobilized-lipase, after every secondary response,
Enzyme is all filtered, is used for measuring enzyme after organic solvent cleaning-drying again and lives.The work of primary enzyme is 100%,
Hereafter enzyme is lived compared with enzyme is lived for the first time every time, obtains relative enzyme and lives；Testing result shows, immobilized enzyme
When reusing 6 times, the work of relative enzyme is 55%, illustrates that immobilized enzyme has good operational stability.
Embodiment 4: the most immobilized lipase-catalyzed preparation duck oil diacylglycerol
The most immobilized candida antarctica lipase B catalyzing glycerol and duck oil fatty acid mixed is used to carry out directly
Connect esterification.With enzyme concentration 1.65%, substrate ratio (glycerol: fatty acid mixed) is 1:2.02, enzymolysis temperature
Degree is 54 DEG C, and enzymolysis time is 9.1h, 5 result of the tests be the yield of diglyceride be 93.28%, 94.05%,
95.02%, 92.81%, 93.33%, its reaction result is the yield of diglyceride compared with immobilized fat
Difference with insignificance；Testing result shows, the most immobilized lipase contains the residual of 2%～3% in the product,
And immobilized lipase can reach 100% separation in the product, noresidue.Containing a certain amount of in product
Lipase can affect the stability of diglyceride, shortens its shelf life, and affects Product quality and safety.
The method of the present invention, on the basis of tradition enzymolysis, first carries out alkali process hydrolysis preparation mixing fat to duck oil
Fat acid, is subsequently adding glycerol and immobilized lipase reacts, and not only makes reaction more abundant, reduces
Waste of raw materials, shortens the response time the most to a certain extent, improves production efficiency and diglyceride
Production rate.Meanwhile, technique avoids the energy waste using high temperature, high-pressure process to cause, it is to avoid
Chemical method uses the environment and the pollution of food that reagent brings in a large number, it is achieved enzyme separates with product, repeats profit
With, belong to energy-conservation, reduce discharging and the innovation of safe technology.May be directly applied to the further of duck oil new product
Exploitation, the scientific utilization for duck fat provides a new approach, and the popularization and application of this technology will have
Great society generalization is worth.
Claims (3)
1. the method preparing duck oil diacylglycerol, it is characterised in that described method comprises the steps:
1) preparation of fatty acid mixed:
Duck oil solution is processed in 87 DEG C of thermostat water baths 1.5h, is then transferred under separatory funnel removing
Layer solution, adds the NaOH solution of 1mol/L, 87 DEG C of constant temperature hydrolysis in remaining solution, uses NaCI
Washing deglycerizin, then it is acidified to pH2～3, the fatty acid that release is free with the HCl of 10%；
2) preparation of diglyceride:
By above-mentioned steps 1) in fatty acid mixed mix for 1:2.02 in mass ratio with glycerol, add solid
Immobilized lipase, is placed on constant-temperature table and carries out enzyme digestion reaction, and the temperature of enzyme digestion reaction is 44 DEG C, during enzymolysis
Between be 9.1h；Enzyme-to-substrate is separated after terminating by reaction by centrifugal, obtains duck oil diacylglycerol；
Described step 2) in immobilized-lipase, its preparation method is as follows:
1) pretreatment of fixation support: by HPD-800 macroporous resin soaked in absolute ethyl alcohol 12h, sucking filtration,
It is washed till neutrality, vacuum drying with distilled water；Again with 5%HCl pickling 12h, 5%NaOH alkali cleaning 12h, wash
To neutral, it is dried；24h, dried for standby is soaked with pH7.5 phosphate buffer solution；
2) fat enzyme immobilizatio: weigh macroporous resin and antarctic candida fat according to the ratio of 15.3:1
Enzyme B, is placed in conical flask, adds the distilled water of 30mL, adsorbs 3h in the constant-temperature table of 34 DEG C；Inhale
Attached complete after add 1% genipin cross-link, postlyophilization, obtain immobilized lipase.
2. the method for claim 1, it is characterised in that described step 2) in macroporous resin and
The mass ratio of candida antarctica lipase B is 15.3:1.
3. the method for claim 1, it is characterised in that described step 2) in 1% genipin
Crosslinking time is 3.2h.
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| CN110331139B (en) * | 2019-05-24 | 2021-08-24 | 浙江工业大学 | Immobilization method of candida antarctica lipase B |
| CN110151771B (en) * | 2019-07-06 | 2021-05-11 | 青岛农业大学 | High-rheological-property 25-hydroxy vitamin D for repairing colitis3Preparation |
| CN110278995A (en) * | 2019-07-30 | 2019-09-27 | 青岛农业大学 | A kind of low fat natural anticorrosion beef paste and preparation method thereof |
| CN111235190B (en) * | 2020-01-22 | 2023-11-07 | 新疆农业大学 | Horse oil rich in diglyceride and preparation method thereof |
| CN113826821B (en) * | 2021-09-24 | 2023-04-25 | 青岛农业大学 | High-stretchability low-fat non-fried instant rice noodles and preparation method thereof |
| CN114480360B (en) * | 2021-12-14 | 2024-03-12 | 山东省农业科学院 | Method for preparing diglyceride by immobilized Sn-2 lipase |
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| CB03 | Change of inventor or designer information | ||
| CB03 | Change of inventor or designer information |
Inventor after: Wang Baowei Inventor after: He Kelin Inventor after: Ge Wenhua Inventor after: Zhang Mingai Inventor after: Yue Bin Inventor after: Zhang Huajun Inventor after: Cui Baojun Inventor after: Song Jiuhai Inventor before: Wang Baowei Inventor before: He Kelin Inventor before: Ge Wenhua Inventor before: Zhang Mingai Inventor before: Yue Bin |
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| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20170731 Address after: 266200, Qingdao environmental protection industrial park, Jimo, Shandong, Qingdao province (No. 20 Longshan Road) Patentee after: Qingdao day food Limited by Share Ltd Address before: 266100 Qingdao Road, Chengyang District, Shandong, No. 700 the Great Wall Patentee before: Qingdao Agricultural University |