CN107522728A - A kind of N phenyl maleimides derivative and preparation method thereof - Google Patents
A kind of N phenyl maleimides derivative and preparation method thereof Download PDFInfo
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- CN107522728A CN107522728A CN201710749084.2A CN201710749084A CN107522728A CN 107522728 A CN107522728 A CN 107522728A CN 201710749084 A CN201710749084 A CN 201710749084A CN 107522728 A CN107522728 A CN 107522728A
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- cpmi
- cpma
- phenylmaleimide derivative
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- 238000002360 preparation method Methods 0.000 title claims description 11
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical class O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 title abstract 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical class O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 13
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 229940040526 anhydrous sodium acetate Drugs 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000005208 1,4-dihydroxybenzenes Chemical group 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 2
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- ZMPYMKAWMBVPQE-UHFFFAOYSA-N 2-[(6-chloropyridin-3-yl)methyl-ethylamino]-2-methyliminoacetic acid Chemical compound CCN(CC1=CN=C(C=C1)Cl)C(=NC)C(=O)O ZMPYMKAWMBVPQE-UHFFFAOYSA-N 0.000 claims 3
- 229920002292 Nylon 6 Polymers 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000010813 municipal solid waste Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- -1 acyl Imine Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of N phenyl maleimides derivative, it is characterised in that：Its structural formula is：CPMI‑KH550.The present invention is prepared for a kind of new N phenyl maleimide derivatives, and the material can greatly improve the heat resisting temperature of nylon 6, the problem of overcoming the heat resisting temperature of nylon 6 low.The heat distortion temperature of nylon 6 is increased to 75 DEG C by 56 DEG C, and significantly increase nylon 6 uses field.
Description
Technical field
The present invention relates to a kind of N-phenylmaleimide derivative and preparation method thereof, belongs to resin raw material, medical agriculture
The synthesis field of medicine intermediate.
Background technology
Maleimide and its derivative are a kind of useful compounds as raw materials such as resin raw material, medical agricultural chemicals, special
Be not, in order to improve the phenylethylene resin series of ABS resin, AS resins, AB resins, ACS resins, AES resins, AAS resin etc., with
And the heat resistance of Corvic, plexiglass, phenolic resin etc., mostly as one of copolymer composition and
Used.Wherein, due to N-phenylmaleimide in terms of reactivity and heat resistance it is excellent, therefore especially made extensively
With.
Manufacture method about N-phenylmaleimide and its derivative, it is known from the prior art to have many methods.
Literature review and Patents have been reported that more：One-step method, acid anhydrides method, depickling method, esterification process and azeotropic method etc..
Copolymer about N-phenylmaleimide and its derivative has text more as the preparation of heat-resistant agent and using also
Offer report.But it is limited to improve polymer heat-resistant temperature, the application especially in nylon 6, such as patent CN104356297A report
Road.
The content of the invention
The technical problem to be solved in the present invention is：A kind of N-phenylmaleimide derivative and preparation method thereof is provided,
To solve finiteness of the heat-resistant agent of the prior art on the heat resisting temperature of nylon 6 is improved.
The technical scheme is that：A kind of N-phenylmaleimide derivative,：Its structural formula is：
A kind of preparation method of N-phenylmaleimide derivative, (1) is using maleic anhydride and p-aminobenzoic acid as original
Material, DMF is solvent, is reacted at room temperature, obtains intermediate product CPMA；(2) CPMA is dissolved in DMF, by dehydrating agent, catalyst,
Polymerization inhibitor is reacted to obtain CPMI；(3) by CPMA and thionyl chloride chloride, CPMIC is obtained；(4) by CPMIC and KH550
Reacted, finally give final product CPMI-KH550；(5) reaction system is concentrated under vacuum, then column chromatography purifies.
Described step (1) maleic anhydride and the rate of charge of p-aminobenzoic acid are 1-1.3:1mol/mol, solvent for use
For DMF, dimethylbenzene or DMF and the mixed solvent of dimethylbenzene.
Dehydrating agent in described second step is acetic anhydride, and catalyst is anhydrous sodium acetate；Polymerization inhibitor is hydroquinones.
In the 3rd described step, reaction temperature is 50-80 DEG C.
It is described in the 4th step, for KH550 dropping temperature below 5 DEG C, reaction temperature is room temperature；In reaction system
Drier is inorganic sodium sulphate and magnesium sulfate；Acid binding agent is inorganic sodium acid carbonate and organic pyridine.
Beneficial effects of the present invention：In order to solve the problems, such as the above, the present invention is prepared for a kind of new N- phenyl Malaysia acyl
Imine derivative, the material can greatly improve the heat resisting temperature of nylon 6, the problem of overcoming the heat resisting temperature of nylon 6 low.The heat of nylon 6
Deformation temperature is increased to 75 DEG C by 56 DEG C, and significantly increase nylon 6 uses field.
Brief description of the drawings
Fig. 1 is CPMI-KH550 prepared by present invention hydrogen nuclear magnetic spectrum.
Embodiment
The present invention is further illustrated below by instantiation, but example is not intended to limit protection scope of the present invention.
Embodiment 1
CPMA synthesis step：1.078g MAH are dissolved in 10mL DMF；1.51g p-aminobenzoic acid is dissolved in
10mL DMF, then solution is added drop-wise in MAH DMF solution in 15-30min；6h is reacted under 40 degree；Reaction terminates
Afterwards, reaction system is cooled to room temperature, then extracted with trash ice；Reaction solution is poured on trash ice, 3-5min is placed, takes advantage of cold
Filter；It is placed in 40 DEG C of baking ovens and dries CPMA.
N- (4- carboxyl phenyls) maleamic acid (CPMA) of 2.17g first steps synthesis is weighed, is dissolved in DMF.Add
Enter 0.2g catalyst anhydrous sodium acetate, 2mL dehydrating agents acetic anhydride, 0.2g hydroquinone of polymerization retarder, heat up, temperature control is existed
Between 50-55 DEG C, 2h is reacted, solution is changed into pale yellow transparent shape, after being cooled to room temperature, stands, solution is poured into trash ice and sunk
Form sediment and a large amount of yellow needle-like crystals occur, then filtered, washed, dried, obtain pure light yellow crystal-N- (4- carboxyl benzene
Base) maleimide (CPMI).
By 1.085g CPMI and thionyl chloride solution in three-necked flask 80 DEG C of backflow 2h；Then by unnecessary protochloride
Sulfone distills, and obtains CPMIC.
0.235gCPMIC is dissolved in chloroform, meanwhile, 0.23g sodium sulphate is put in the solution, then by KH550 by
It is added dropwise in solution, secondly, is purified with sodium acid carbonate, finally, use chloroform：Methanol=10:1 eluent chromatography carries
It is pure, reduced under vacuum liquid, finally give oil dress thick liquid.
Embodiment 2
CPMA synthesis step:10.78g MAH are dissolved in 10mL DMF；15.1g p-aminobenzoic acid is dissolved in
100mL DMF, then solution is added drop-wise in MAH DMF solution in 15-30min；6h is reacted under 40 degree；Reaction terminates
Afterwards, reaction system is cooled to room temperature, then extracted with trash ice；Reaction solution is poured on trash ice, 3-5min is placed, takes advantage of cold
Filter；It is placed in 40 DEG C of baking ovens and dries CPMA.
N- (4- carboxyl phenyls) maleamic acid (CPMA) of 21.7g first steps synthesis is weighed, is dissolved in DMF.Add
Enter 2g catalyst anhydrous sodium acetate, 20mL dehydrating agents acetic anhydride, 2g hydroquinone of polymerization retarder, heat up, by temperature control in 50-
Between 55 DEG C, 2h is reacted, solution is changed into pale yellow transparent shape, after being cooled to room temperature, stands, solution is poured into trash ice and is settled out
Now a large amount of yellow needle-like crystals, then filtered, washed, dried, obtain pure light yellow crystal-N- (4- carboxyl phenyls)
Maleimide (CPMI).
By 10.85g CPMI and thionyl chloride solution in three-necked flask 80 DEG C of backflow 2h；Then by unnecessary protochloride
Sulfone distills, and obtains CPMIC.
10.85gCPMIC is dissolved in chloroform, meanwhile, 2.3g sodium sulphate is put in the solution, then by KH550 dropwise
It is added in solution, finally, is purified with sodium acid carbonate, finally use chloroform：Methanol=10:1 eluent Chromatographic purification, very
The lower concentrated liquid of sky, finally gives oil dress thick liquid, its proton magnetic is as shown in the figure.
By the product obtained in example 2 be added to PA6 carry out improve nylon 6 heat resistance, it is as a result as shown in the table：
Note：No. 1 is to be not added with CPMI-KH550 in table, and No. 2 with the addition of 5 parts of CPMI-KH550, and No. 3 with the addition of 10 parts, No. 4
It with the addition of 15 parts.
Claims (6)
- A kind of 1. N-phenylmaleimide derivative, it is characterised in that：Its structural formula is：CPMI-KH550。
- A kind of 2. preparation method of N-phenylmaleimide derivative as claimed in claim 1, it is characterised in that：(1) with Maleic anhydride and p-aminobenzoic acid are raw material, and DMF is solvent, is reacted at room temperature, obtains intermediate product CPMA；(2) will CPMA is dissolved in DMF, and dehydrating agent, catalyst, polymerization inhibitor are reacted to obtain CPMI；(3) by CPMA and thionyl chloride chloride, Obtain CPMIC；(4) CPMIC and KH550 are reacted, finally gives final product CPMI-KH550；(5) by reaction system It is concentrated under vacuum, then column chromatography purifies.
- A kind of 3. preparation method of N-phenylmaleimide derivative according to claim 2, it is characterised in that：Step (1) rate of charge of maleic anhydride and p-aminobenzoic acid is 1-1.3:1mol/mol, solvent for use DMF, dimethylbenzene or DMF with The mixed solvent of dimethylbenzene.
- A kind of 4. preparation method of N-phenylmaleimide derivative according to claim 2, it is characterised in that：Second Dehydrating agent in step is acetic anhydride, and catalyst is anhydrous sodium acetate；Polymerization inhibitor is hydroquinones.
- A kind of 5. preparation method of N-phenylmaleimide derivative according to claim 2, it is characterised in that：3rd In step, reaction temperature is 50-80 DEG C.
- A kind of 6. preparation method of N-phenylmaleimide derivative according to claim 2, it is characterised in that： In four steps, for KH550 dropping temperature below 5 DEG C, reaction temperature is room temperature；Drier in reaction system is inorganic sodium sulphate And magnesium sulfate；Acid binding agent is inorganic sodium acid carbonate and organic pyridine.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710749084.2A CN107522728B (en) | 2017-08-28 | 2017-08-28 | A kind of N-phenylmaleimide derivative and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710749084.2A CN107522728B (en) | 2017-08-28 | 2017-08-28 | A kind of N-phenylmaleimide derivative and preparation method thereof |
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| Publication Number | Publication Date |
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| CN107522728A true CN107522728A (en) | 2017-12-29 |
| CN107522728B CN107522728B (en) | 2019-05-07 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109081799A (en) * | 2018-08-27 | 2018-12-25 | 连云港锐巴化工有限公司 | A kind of rubber special type vulcanizing agent 4- carboxyl phenyl maleimide preparation method |
| CN110452377A (en) * | 2019-08-31 | 2019-11-15 | 贵州大学 | A kind of 2- allyl -6- methyl-6-tert-butylphenol and ethylenediamine copolymerization macromolecular antioxidant and its application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447849A (en) * | 2014-12-26 | 2015-03-25 | 上海爱默金山药业有限公司 | Synthesis method of siloxane-substituted maleimide |
| CN104910451A (en) * | 2015-06-29 | 2015-09-16 | 大冢材料科技（上海）有限公司 | Rubber composition containing multifunctional maleimide compound |
| CN105131027A (en) * | 2015-07-10 | 2015-12-09 | 南京工业大学 | Synthesis of maleimide triethoxy silane series compounds and preparation method of self-assembled film |
-
2017
- 2017-08-28 CN CN201710749084.2A patent/CN107522728B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447849A (en) * | 2014-12-26 | 2015-03-25 | 上海爱默金山药业有限公司 | Synthesis method of siloxane-substituted maleimide |
| CN104910451A (en) * | 2015-06-29 | 2015-09-16 | 大冢材料科技（上海）有限公司 | Rubber composition containing multifunctional maleimide compound |
| CN105131027A (en) * | 2015-07-10 | 2015-12-09 | 南京工业大学 | Synthesis of maleimide triethoxy silane series compounds and preparation method of self-assembled film |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109081799A (en) * | 2018-08-27 | 2018-12-25 | 连云港锐巴化工有限公司 | A kind of rubber special type vulcanizing agent 4- carboxyl phenyl maleimide preparation method |
| CN110452377A (en) * | 2019-08-31 | 2019-11-15 | 贵州大学 | A kind of 2- allyl -6- methyl-6-tert-butylphenol and ethylenediamine copolymerization macromolecular antioxidant and its application |
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| CN107522728B (en) | 2019-05-07 |
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