CN108567597A - A kind of non-aqueous multiple self-emulsifying systems of Quercetin and its preparation method and application - Google Patents
A kind of non-aqueous multiple self-emulsifying systems of Quercetin and its preparation method and application Download PDFInfo
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- CN108567597A CN108567597A CN201810685980.1A CN201810685980A CN108567597A CN 108567597 A CN108567597 A CN 108567597A CN 201810685980 A CN201810685980 A CN 201810685980A CN 108567597 A CN108567597 A CN 108567597A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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Abstract
A kind of non-aqueous multiple self-emulsifying systems of Quercetin and its preparation method and application, the system load have Quercetin active constituent, by mass fraction, are made of following raw materials according：1 ~ 2 part of Quercetin；8 ~ 18 parts of glycerine；2 ~ 12 parts of dipropylene glycol；46 ~ 63 parts of vegetable oil；4 ~ 8 parts of Solid lipid；4 ~ 14 parts of hydrophobic surfactant；4 ~ 12 parts of hydrophilic surfactant active.The present invention can solve the grease in cosmetics in the prior art and face a difficult choice in place of the dissolubility of soluble bioactive compound, load capacity and the shortcoming and defect such as skin bioavilability is low.
Description
Technical field
The invention belongs to the carrier system technical field in cosmetics technology of preparing, it is related to a kind of the non-aqueous of package Quercetin
Multiple self-emulsifying systems and its preparation method and application.
Background technology
Quercetin（Quercetin）, also referred to as quercetin, molecular weight 302, and molecular formula is C15H10O7, fusing point is about
314 DEG C, CAS:117-39-5, sterling exist with yellow needles, are a kind of natural bioflavonoid compound.
The generation of skin photoage and ultraviolet light（UV）Induction can make the active oxygen radical (ROS) in skin excessive
It generates, so as to cause dermal microvascular endothelial cell damage or apoptosis.And Quercetin is to singlet oxygen, superoxide anion and peroxide
Change the ROS such as oxygen and all has effective scavenging effect.Its scavenging effect major embodiment is in the following areas：First, the chemistry of Quercetin
Containing adjacent two phenolic hydroxyl structures of hydrogen donor in structure, ROS can be directly removed by the transfer of single electron；Second, Quercetin with from
Related enzyme phase separation is generated by base, to remove ROS indirectly；It is generated third, metallic iron, copper etc. are numerous free radicals
The catalyst of process, the catechol structure energy chelated metal ions Fe in quercetin molecule2+And Cu2+, to play its antioxygen
Change acts on.In addition, contain abundant lipid in the cuticula of skin, and lipid would generally face the peroxidation of free radical mediated
It answers, these frequently result in the speckle etc. of skin surface due to the alkyl compound that the peroxidating of lipid generates, and more importantly
These substances also result in the damage of skin tissue cell multiple functions.Quercetin can be by removing ROS and chelated metal ions
Lipid peroxidation chain reaction is blocked, to inhibiting the peroxidating of lipid.
Since quercetin molecule is in plane characteristic, mainly with two dimensional form is overlapped accumulation and forms crystal, lead to its structure
In in spite of hydroxyl（Contain 5）Distribution, is but practically insoluble in water（Solubility is less than 0.5 μ g/g）, while in most oil
Solubility in fat significantly limits it in skin again smaller than 1.0 mg/g just because of its two indissoluble characteristic of unique grease
The absorption in skin field and bioavilability.
Under normal conditions, by dispersed phase（Continuous phase）Classification, common aqueous emulsion includes oil-in-water（O/W）Type, You Bao
Water（W/O）Type, water-water（W/W）Type lotion and relatively more complicated emulsion, while also including nonaqueous emulsion, predominantly oil wraps
Oil（O/O）Type lotion etc., it is also even insufficient for the research of nonaqueous emulsion at present compared with aqueous emulsion, but since it is to oil
Degradable ingredient can play package and protective effect well in two refractory components of water or water, have shown that preferable application
Foreground.In addition, the multiple emulsion generally special construction with " two film three-phases ", the work that on the one hand this structure can make polarity different
Property ingredient is dissolved in respectively in different dispersed phases, to play multi-efficiency；This structure also results in multiphase but then
Have on interface very high interface can, easily occur in foreign minister transmission, rupture and coalescence etc. to cause lotion, thus its
It is thermodynamically very unstable, this also greatly limits its application in actual production.
Self-emulsifying systems（Self-emulsifying drug delivery system, SEDDS）By surfactant,
The compositions such as oil phase and active constituent can form the o/w microemulsion of about 100 nm of grain size, mainly in aqueous medium through gentle agitation
Suitable for the load of oil-soluble ingredients, dermal application intermediate-type can be used as.And combining multiple emulsion and self-emulsifying systems
A kind of new micro-nano carrier technique, i.e., multiple self-emulsifying systems are designed after the advantage of the two（Self-double-
Emulsifying drug delivery system, SDEDDS）, since traditional SDEDDS is Water-In-Oil（W/O）Colostrum and parent
The mixture of water emulsifier, wherein water soluble ingredient are dissolved mainly in inner aqueous phase, therefore tradition SDEDDS can not be directed to oil
Two refractory components of water and loaded.Therefore, it on the basis ofs nonaqueous emulsion, multiple emulsion and tradition SDEDDS etc., will pass
The inner aqueous phase organic solvent of system SDEDDS（Such as glycerine, propylene glycol）Instead of rear, it can design and prepare the non-of different stable forms
The multiple self-emulsifying systems of water（Non-aqueous SDEDDS）, which is oil packet oil（O/O）Colostrum and hydrophilic emulsifier
Mixture, wherein two refractory components of grease may be dissolved in interior oil phase, and therefore, which solves two indissoluble of grease well
Property ingredient load strategy problem, improve two refractory components of grease load capacity and bioavailability, enhance the antioxygen of skin
Change ability and protective effect.Some disadvantages of Quercetin in application process can be improved by non-aqueous multiple self-emulsifying systems, from
And it is made preferably to move towards commercialization process.
This patent carries out package processing using non-aqueous multiple self-emulsifying systems to Quercetin, can be good at solving the above institute
The Quercetin of description is applying upper problem, the present invention next therefrom.
Invention content
The technical issues of solution：The present invention provides a kind of non-aqueous multiple self-emulsifying systems and its system of Quercetin high load amount
Preparation Method and application, a kind of Quercetin applied in skin sparing cosmetics of production solve in cosmetics in the prior art
Grease is faced a difficult choice in place of the dissolubility of soluble bioactive compound, load capacity and the shortcoming and defect such as skin bioavilability is low.
Technical solution：A kind of non-aqueous multiple self-emulsifying systems of Quercetin, the system load have Quercetin active constituent, press
Mass fraction is made of following raw materials according：1 ~ 2 part of Quercetin；8 ~ 18 parts of glycerine；2 ~ 12 parts of dipropylene glycol；It plants
46 ~ 63 parts of object oil；4 ~ 8 parts of Solid lipid；4 ~ 14 parts of hydrophobic surfactant；Hydrophilic surfactant active 4
~ 12 parts.
Above-mentioned vegetable oil is olive oil, coconut oil, peppermint oil, SIMMONDSIA CHINENSIS SEED OIL, grape seed oil, macadimia nut oil, sunflower seeds
At least one of oil, camellia seed oil, evening primrose oil, corn oil.
Above-mentioned Solid lipid is hexadecanol, octadecyl alcolol, cetostearyl alcohol, glyceryl monostearate, glyceryl monolaurate
At least one of.
Above-mentioned hydrophobic surfactant is polyglycerol polyricinoleate, -10/1 diformazan of cetyl polyethylene/polypropylene glycol
Any one in radical siloxane, -30 dimerization hydroxy stearic acid ester of polyethylene glycol.
Above-mentioned hydrophilic surfactant active be polysorbas20, polysorbate40, polysorbate60, Tween 80, ten polyglycereol monolaurates,
Dilute (40) stearic acid of caprylic/capric LABRAFIL M 1944CS, polyoxy second, cetostearyl alcohol and the smooth olive oleate of sorb, sorb
Any one in smooth olive oleate, -6 olive oleate of ceteareth.
The preparation method of the above-mentioned non-aqueous multiple self-emulsifying systems of Quercetin, includes the following steps：（1）By Quercetin, glycerine
It is stirred after mixing with dipropylene glycol to solution to become at room temperature and be clarified, as interior oil phase；（2）By vegetable oil, Solid lipid
It is thoroughly mixed to form homogeneous phase in 65 DEG C ~ 70 DEG C waters bath with thermostatic control with hydrophobic surfactant, obtains outer oil phase；（3）800
Interior oil phase is added dropwise under the stirring of ~ 2000 rpm into above-mentioned outer oil phase, the two quality parts ratio is（54 ~ 85 parts）：
（11 ~ 32 parts）, continuing 10 ~ 20 min of stirring keeps its fully emulsified, obtains oil packet oil（O/O）Colostrum；（4）By hydrophily table
Face activating agent is directly added into the above-mentioned oily colostrum of oil packet, and 10 ~ 15 are stirred in 200 ~ 400 rpm at 48 DEG C ~ 52 DEG C
Min to obtain the final product.
Application of the above-mentioned non-aqueous multiple self-emulsifying systems of Quercetin in preparing skin protection cosmetics
Advantageous effect：（1）The non-aqueous multiple self-emulsifying systems of Quercetin of the present invention are with good stability；（2）Improve oil
The dissolubility of the awkward property ingredient Quercetin of water, to improve its bioavilability；（3）Each component has very high safety in formula
Property, nonirritant to body, non-toxic, can be used as intermediate-type is used in compounding with cosmetic formulations, and compatibility is good, can be extensive
For cosmetic field；（4）The preparation method is simply controllable, reproducible.
Description of the drawings
Fig. 1 is the preparation method flow chart of the non-aqueous multiple self-emulsifying systems of Quercetin of the present invention.
Specific implementation mode
The invention will be further described with reference to embodiments.These embodiments are not limited to for illustrating the present invention
It limits the scope of the invention.The implementation condition used in embodiment can do further adjustment according to the condition of specific producer.
Embodiment 1
1.2 g Quercetins, 8.0 g dipropylene glycols and 12.0 g glycerine are weighed, by Quercetin, dipropylene glycol and glycerine
Magnetic agitation is until solution becomes clarification at room temperature after mixing, as interior oil phase；Weigh 14.0 g polyglycerol polyricinoleates,
10.0 g glyceryl monostearates and 54.8 g grape seed oils, by polyglycerol polyricinoleate, glyceryl monostearate and grape pip
Oil mixing after be thoroughly mixed to form homogeneous phase in 70 DEG C of waters bath with thermostatic control, obtain outer oil phase, then under the stirring of 1200 rpm to
Oil-phase solution in 21.2 g is added dropwise in the outer oil phases of above-mentioned 78.8 g, continuing 15 min of stirring keeps its fully emulsified, obtains oil
The oily colostrum of packet；10.0 g polysorbate60s are added in colostrum, in 250 rpm stirring at low speed, 15 min up to Quercetin at 50 DEG C
The non-aqueous multiple self-emulsifying systems of high load amount.The non-aqueous multiple self-emulsifying systems of 1.0 g Quercetins are added to 100 g deionized waters
In, after evenly dispersed, it is 21.2 to obtain the non-aqueous multiple self-emulsifying systems of Quercetin rear average grain diameter water-dispersed using laser light scattering instrument
± 2.8 μm, and 25 DEG C be placed at room temperature for 1 month after its average grain diameter be 23.7 ± 3.0 μm, change of size is without apparent poor
It is different, show that it has good stability.
Embodiment 2
1.4 g Quercetins, 10.0 g glycerine and 10.0 g dipropylene glycols are weighed, by Quercetin, glycerine and a contracting dipropyl two
Magnetic agitation is until solution becomes clarification at room temperature after alcohol mixing, as interior oil phase；Weigh 8.0 g polyglycerol polyricinoleates,
- 30 dimerization hydroxy stearic acid ester of 6.0 g polyethylene glycol, 6.0 g cetostearyl alcohols and 58.6 g evening primrose oil, by polyglycereol castor-oil plant
After alcohol ester, -30 dimerization hydroxy stearic acid ester of polyethylene glycol, cetostearyl alcohol and evening primrose oil mixing in 65 DEG C of waters bath with thermostatic control fully
It is mixed to form homogeneous phase, obtains outer oil phase, is then added dropwise in oil phase to outside above-mentioned 78.6 g under the stirring of 1200 rpm
Oil-phase solution in 21.4 g, continuing 15 min of stirring keeps its fully emulsified, obtains the oily colostrum of oil packet；By 8.0 g Tween 80s, 1.0
G caprylic/capric LABRAFIL M 1944CSs are added in colostrum, in 250 rpm stirring at low speed, 15 min up to quercitrin at 50 DEG C
The plain non-aqueous multiple self-emulsifying systems of high load amount.The non-aqueous multiple self-emulsifying systems of 1.0 g Quercetins are added to 100 g deionizations
In water, after evenly dispersed, obtaining the non-aqueous multiple self-emulsifying systems of Quercetin rear average grain diameter water-dispersed using laser light scattering instrument is
18.8 ± 3.3 μm, and 25 DEG C be placed at room temperature for 1 month after its average grain diameter be 20.6 ± 3.7 μm, change of size is without bright
Significant difference is different, shows that it has good stability.
Embodiment 3
2.0 g Quercetins, 8.0 g glycerine and 12.0 g dipropylene glycols are weighed, by Quercetin, glycerine and dipropylene glycol
Magnetic agitation is until solution becomes clarification at room temperature after mixing, as interior oil phase；Weigh 14.0 g cetyls polyethylene glycol/poly-
- 10/1 dimethyl siloxane of propylene glycol, 6.0 g cetostearyl alcohols and 58.0 g evening primrose oil, by cetyl polyethylene glycol/poly- third
It is thoroughly mixed to form in 65 DEG C of waters bath with thermostatic control after -10/1 dimethyl siloxane of glycol, cetostearyl alcohol and evening primrose oil mixing
One phase obtains outer oil phase, and oil phase in 22.0 g then is added dropwise in oil phase to outside above-mentioned 78.0 g under the stirring of 1200 rpm
Solution, continuing 15 min of stirring keeps its fully emulsified, obtains the oily colostrum of oil packet；By 7.0 g polysorbas20s, 3.0 g cetostearyl alcohols
- 6 olive oleate of polyethers is added in colostrum, in 250 rpm stirring at low speed, 15 min up to Quercetin high load at 50 DEG C
Measure non-aqueous multiple self-emulsifying systems.The non-aqueous multiple self-emulsifying systems of 1.0 g Quercetins are added in 100 g deionized waters,
After even dispersion, using laser light scattering instrument obtain the non-aqueous multiple self-emulsifying systems of Quercetin it is water-dispersed after average grain diameter be 16.8 ±
2.5 μm, and 25 DEG C be placed at room temperature for 1 month after its average grain diameter be 17.2 ± 2.8 μm, change of size no significant difference,
Show that it has good stability.
The foregoing examples are merely illustrative of the technical concept and features of the invention, its object is to allow professional and technical personnel in the field can
Understand present disclosure and implement according to this, it is not intended to limit the scope of the present invention.It is all real according to spirit of that invention
The changes, modifications, substitutions, combinations, simplifications that matter is done should be equivalent substitute mode, be included in the protection model of the present invention
Within enclosing.
Claims (7)
1. a kind of non-aqueous multiple self-emulsifying systems of Quercetin, the system load has Quercetin active constituent, it is characterised in that presses
Mass fraction is made of following raw materials according：
1 ~ 2 part of Quercetin；8 ~ 18 parts of glycerine；2 ~ 12 parts of dipropylene glycol；
46 ~ 63 parts of vegetable oil；4 ~ 8 parts of Solid lipid；4 ~ 14 parts of hydrophobic surfactant；
4 ~ 12 parts of hydrophilic surfactant active.
2. the non-aqueous multiple self-emulsifying systems of Quercetin according to claim 1, it is characterised in that the vegetable oil be olive oil,
Coconut oil, peppermint oil, SIMMONDSIA CHINENSIS SEED OIL, grape seed oil, macadimia nut oil, sunflower oil, camellia seed oil, evening primrose oil, corn oil
At least one of.
3. the non-aqueous multiple self-emulsifying systems of Quercetin according to claim 1, it is characterised in that the Solid lipid is 16
At least one of alcohol, octadecyl alcolol, cetostearyl alcohol, glyceryl monostearate, glyceryl monolaurate.
4. the non-aqueous multiple self-emulsifying systems of Quercetin according to claim 1, it is characterised in that the hydrophobic surface active
Agent is polyglycerol polyricinoleate, -10/1 dimethyl siloxane of cetyl polyethylene/polypropylene glycol, -30 dimerization hydroxyl of polyethylene glycol
Any one in base stearate.
5. the non-aqueous multiple self-emulsifying systems of Quercetin according to claim 1, it is characterised in that the hydrophilic surfactant
Agent is polysorbas20, polysorbate40, polysorbate60, Tween 80, ten polyglycereol monolaurates, caprylic/capric LABRAFIL M 1944CS, gathers
Dilute (40) stearic acid of oxygen second, cetostearyl alcohol and the smooth olive oleate of sorb, the smooth olive oleate of sorb, cetostearyl alcohol are poly-
Any one in -6 olive oleate of ether.
6. the preparation method of any non-aqueous multiple self-emulsifying systems of Quercetin of claim 1 ~ 5, it is characterised in that including with
Lower step：
（1）It is stirred after Quercetin, glycerine and dipropylene glycol are mixed to solution to become at room temperature and be clarified, as interior oil phase；
（2）Vegetable oil, Solid lipid and hydrophobic surfactant are thoroughly mixed to form in 65 DEG C ~ 70 DEG C waters bath with thermostatic control
Homogeneous phase obtains outer oil phase；
（3）Interior oil phase is added dropwise into above-mentioned outer oil phase under the stirring of 800 ~ 2000 rpm, the two quality parts ratio is
（54 ~ 85 parts）：（11 ~ 32 parts）, continuing 10 ~ 20 min of stirring keeps its fully emulsified, obtains oil packet oil（O/O）Colostrum；
（4）Hydrophilic surfactant active is directly added into the above-mentioned oily colostrum of oil packet, in 200 ~ 400 at 48 DEG C ~ 52 DEG C
Rpm stirs 10 ~ 15 min to obtain the final product.
7. a kind of any non-aqueous multiple self-emulsifying systems answering in preparing skin protection cosmetics of Quercetin of claim 1 ~ 5
With.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109924491A (en) * | 2019-04-01 | 2019-06-25 | 东南大学 | A kind of dihydromyricetin solid-state self-emulsifying material and its preparation method and application |
| CN111264860A (en) * | 2020-01-19 | 2020-06-12 | 上海海洋大学 | Solid self-microemulsion microcapsule containing astaxanthin and quercetin and preparation method and application thereof |
| CN114452227A (en) * | 2022-01-20 | 2022-05-10 | 江南大学 | Method for preparing alcohol-in-water-in-oil-in-water multiple pickering emulsion by anti-solvent recrystallization method |
| CN115462529A (en) * | 2022-09-16 | 2022-12-13 | 华中农业大学 | Quercetin emulsion and preparation method and application thereof |
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| CN107242999A (en) * | 2017-05-04 | 2017-10-13 | 方达医药技术（苏州）有限公司 | A kind of multiple self-emulsifying carrier of solid and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107242999A (en) * | 2017-05-04 | 2017-10-13 | 方达医药技术（苏州）有限公司 | A kind of multiple self-emulsifying carrier of solid and preparation method thereof |
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| QIANG WANG等: "《Evaluation of a new solid non-aqueous self-double-emulsifying drug-deIivery syste m for topical application of quercetin》", 《JOURNAL OF MICROENCAPSULATION》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109924491A (en) * | 2019-04-01 | 2019-06-25 | 东南大学 | A kind of dihydromyricetin solid-state self-emulsifying material and its preparation method and application |
| CN111264860A (en) * | 2020-01-19 | 2020-06-12 | 上海海洋大学 | Solid self-microemulsion microcapsule containing astaxanthin and quercetin and preparation method and application thereof |
| CN114452227A (en) * | 2022-01-20 | 2022-05-10 | 江南大学 | Method for preparing alcohol-in-water-in-oil-in-water multiple pickering emulsion by anti-solvent recrystallization method |
| CN115462529A (en) * | 2022-09-16 | 2022-12-13 | 华中农业大学 | Quercetin emulsion and preparation method and application thereof |
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Application publication date: 20180925 |