CN107739346A - Trithiocyanuric acid triallyl and preparation method thereof - Google Patents
Trithiocyanuric acid triallyl and preparation method thereof Download PDFInfo
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- CN107739346A CN107739346A CN201710984821.7A CN201710984821A CN107739346A CN 107739346 A CN107739346 A CN 107739346A CN 201710984821 A CN201710984821 A CN 201710984821A CN 107739346 A CN107739346 A CN 107739346A
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- trithiocyanuric acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/38—Sulfur atoms
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Abstract
The invention discloses trithiocyanuric acid triallyl and preparation method thereof, the structural formula of the trithiocyanuric acid triallyl is：Preparation method is：The solvent of reaction system is used as using chloropropene, reaction monomers and trithiocyanuric acid trisodium reactant salt generation trithiocyanuric acid triallyl are also served as simultaneously, after the completion of reaction, recycled by the way that the chloropropene of recovery excess is evaporated in vacuo, the trithiocyanuric acid triallyl and sodium chloride mixture of generation, sodium chloride is separated out by slow cooling, then filters or centrifuges by mocromembrane and may separate out sodium chloride, so as to obtain trithiocyanuric acid triallyl.The thioether bond of excellent performance is introduced into Striazine derivative by the present invention, synthesize obtained trithiocyanuric acid triallyl, the crosslink density and heat endurance of resin can be not only improved, the performances such as toughness, water resistance, cementability, oxidation resistance and the refractive index of polymer can also be improved.
Description
Technical field
The invention belongs to compound synthesis field, and in particular to trithiocyanuric acid triallyl and preparation method thereof.
Background technology
TAC (TAC) is a kind of trifunctional olefinic monomer containing triazine ring, is existed simultaneously in monomer steady
Fixed triazine ring structure and active allylic structure, not only significantly improve the crosslink density of product, while it is good to have product
Good heat resistance and dielectric properties.Therefore, TAC is commonly used for the assistant crosslinking agent and crosslinking with radiation auxiliary agent of rubber and plastics.In poly- ammonia
When ester, polyvinyl chloride and EP rubbers etc. are using peroxide as crosslinking agent, TAC is good assistant crosslinking agent；Meanwhile TAC also exists
It is used as the resin such as sensitising agent, modified polymethyl acid resin, polyethylene and polyester in polyolefin, polyvinyl chloride crosslinking with radiation
Heat resistance.
And assign the characteristics of polymer more protrudes relative to oxygen-ether linkage, thioether bond energy：Hydrophobic, high index of refraction, the low moisture absorption
Property, low solvent swell, good caking property, and in radical photopolymerization, there is sulfur-bearing monomer certain resistance to the oxygen inhibiting polymerization to make
With the polymer hydrophobic, refractive index after solidification are high.Therefore by MOLECULE DESIGN, a kind of sulfur-bearing multi-functional olefin list is synthesized
Body --- trithiocyanuric acid triallyl (Triallyl Trithiocyanurate, TTAC), it is more excellent so as to obtain performance
Pyrrolotriazine derivatives.
The content of the invention
It is an object of the invention to provide a kind of Property of Novel Triazine Derivative --- trithiocyanuric acid triallyl, the triazine derivatives
Thing can not only improve the crosslink density and heat endurance of resin, can also improve the toughness of polymer, water resistance, cementability,
The performance such as oxidation resistance and refractive index, while present invention also offers the preparation method of trithiocyanuric acid triallyl.
To achieve the above object, the present invention adopts the following technical scheme that：
Shown in the structural formula of trithiocyanuric acid triallyl such as formula (I)：
The trithiocyanuric acid triallyl (Triallyl Trithiocyanurate, TTAC) that the present invention synthesizes, system life
Entitled 2,4,6- tri- (2- propylene sulfenyl) -1,3,5- triazines (2,4,6-tris (2-propenythio) -1,3,5-
Triazine), the pi-allyl containing high reaction activity, the thioether bond of high-flexibility and high stability simultaneously in its molecular structure
Triazine ring structure, make polymer that there is the superiority such as cementability that more excellent toughness, high index of refraction, low solvent swell becomes reconciled
Energy.Similar to TAC, TTAC is trifunctional vinyl monomer, may be used as the vulcanizing agent of height saturated rubber, unsaturated polyester (UP)
Curing agent, also it can make sensitising agent in polyolefin, polyvinyl chloride crosslinking with radiation, to improve the crosslink density of resin and heat endurance
Etc. performance.On the other hand, the thioether bond in TTAC structures can further improve the toughness of polymer, water resistance, cementability, anti-
The performance such as oxidability and refractive index, further expand the application of Striazine derivative.
Present invention also offers the preparation method of trithiocyanuric acid triallyl, step are as follows：
(1) trithiocyanuric acid triallyl synthesizes：Chloropropene is added in reactor, then stirs and adds three in batches
Polysulfide cyanic acid trisodium salt, the wherein mol ratio of trithiocyanuric acid trisodium salt and chloropropene are 1:3.9~6.0, trithiocyanuric acid three
The feed time of sodium salt is 40~90min, continues 10~40min of stirring reaction after the completion of charging, and above-mentioned whole process control is anti-
It is 3~12 DEG C to answer system temperature；
(2) temperature reaction：After the completion of step (1), 20~100ppm polymerization inhibitor is added in reaction system, then will reaction
System is warming up to 40~45 DEG C, continues 10~40min of stirring reaction；
(3) it is evaporated in vacuo：After the completion of step (2), reacted mixed liquor is evaporated in vacuo at 40~45 DEG C, with recovery
Unreacted chloropropene monomer, the chloropropene of recovery recycle as reactant in system；
(4) isolate and purify：After distillation completely, by the mixed of remaining trithiocyanuric acid triallyl in reactor and sodium chloride
Compound slowly cools to 25~30 DEG C with precipitated sodium chloride, is stirred for 05~1.5h, after sodium chloride in system separates out completely, leads to
Cross mocromembrane filtering or be centrifuged off sodium chloride, that is, obtain described trithiocyanuric acid triallyl.
In the inventive method, chloropropene both solvents as reaction system, while also serve as reaction monomers and three polysulfide cyanogen
Sour trisodium reactant salt, generate trithiocyanuric acid triallyl, after the completion of reaction, by be evaporated in vacuo reclaim excessive chloropropene with
Recycle, the trithiocyanuric acid triallyl and sodium chloride mixture of generation, because trithiocyanuric acid triallyl is liquid,
And sodium chloride is solid and does not dissolve in trithiocyanuric acid triallyl, separate out sodium chloride by slow cooling, then pass through mocromembrane
Filtering or centrifugation may separate out sodium chloride, so as to obtain trithiocyanuric acid triallyl, three polysulfides prepared by the inventive method
For cyanic acid triallyl yield more than 95%, purity is 99.3~99.7%.Formula (II) is present invention synthesis trithiocyanuric acid triolefin
The reaction equation of propyl ester, after above-mentioned steps (1) reaction terminates, conversion ratio is about 90~95%, step (2) heating further reaction
Afterwards, final conversion ratio can reach 95~98.3%,
Preferably, the mol ratio of the trithiocyanuric acid trisodium salt and chloropropene is 1:4.5~5.1.Chloropropene was both made
For solvent, while reaction monomers are also served as, control the amount of chloropropene in reaction system, the generation of side reaction can be reduced.
Preferably, trithiocyanuric acid trisodium salt adds in batches in step (1), per 4~15min of batch interval, and walk
Suddenly the reaction time is no more than 2h in (1), and the reaction time reacts knot to be initially added into trithiocyanuric acid trisodium salt to step (1)
The time of beam.By adding trithiocyanuric acid trisodium salt in batches, the thermal discharge of reaction rate and reaction system is can control, so as to
The generation of side reaction is avoided, while controls total reaction time to reduce unnecessary secondary reaction.
Preferably, 3~5 additions of trithiocyanuric acid trisodium salinity, feed time and every batch interval time summation are
80~100min.
Preferably, step (1) and step (2) total reaction time are 1.5~3.0h, the total reaction time is step
(1) heating-up time, stirring reaction time in feed time, interval time and step (2) in.
Preferably, adding 20~100ppm polymerization inhibitors after the completion of step (1) into reaction system, the polymerization inhibitor is pair
Benzenediol or hydroquinone derivative.Because there is element sulphur certain resistance to the oxygen inhibiting polymerization to make in trithiocyanuric acid triallyl structure
With micro polymerization inhibitor is added before heating up can prevent trithiocyanuric acid triallyl from aoxidizing and polymerizeing, and avoid trithiocyanuric acid
Triallyl turns yellow or viscosity increase.The optional hydroquinone derivative of polymerization inhibitor, preferably hydroquinones, wherein polymerization inhibitor is dense
Degree is calculated on the basis of the theoretical yield of trithiocyanuric acid triallyl.
Preferably, mocromembrane described in step (4) is 0.1~0.5 μm of tetrafluoroethene or vinylidene filter membrane.
Compared with prior art, the present invention has the advantages that：
(1) thioether bond of excellent performance is introduced into Striazine derivative by the present invention, and synthesis obtains trithiocyanuric acid triolefin
Propyl ester, make trithiocyanuric acid triallyl that there is more excellent toughness, water resistance, cementability, oxidation resistance and refractive index
Etc. performance, it both can be used as vulcanizing agent, the curing agent of unsaturated polyester (UP) of height saturated rubber, can also be in polyolefin, polyvinyl chloride
Make sensitising agent in crosslinking with radiation, to improve the performances such as the crosslink density of resin and heat endurance, further expand s-triazine and derive
The application of thing.
(2) the present invention relatively low chloropropene of selection boiling point is reclaimed by vaccum cryogenic distillation as reaction monomers and solvent,
On the one hand, avoid makes the shortcomings of product discoloration is with viscosity increase under high temperature due to aoxidizing or polymerizeing；On the other hand, using chlorine third
Alkene, by recycling, not only contributes to reduce product cost as reaction dissolvent, and without using other solvents, but also
Reduce production stage, saved the energy and resource, reduce the discharge of the three wastes, it is green to realize building-up process.
(3) present invention effectively controls reaction rate and reaction system by adding trithiocyanuric acid trisodium salt in batches
Temperature, reduce the generation of side reaction, improve product yield and purity, trithiocyanuric acid triolefin prepared by the inventive method
For propyl ester yield more than 95%, purity is 99.3~99.7%.
Brief description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum figure of trithiocyanuric acid triallyl product prepared by embodiment 3.
Embodiment
The present invention is described in further detail with reference to specific embodiment.
The chloropropene purity used in the embodiment of the present invention is 99~100%.
Embodiment 1
The preparation method of the present embodiment trithiocyanuric acid triallyl, step are as follows：
(1) in the 1000L enamel reactors with cooling circuit and circulator bath loop, it is pumped into chloropropene 619.8Kg
(8100mol, excessively 80%), stirring and cooling circuit are opened, the chloropropene monomer in reactor is cooled to 0~2 DEG C.So
Afterwards, beginning is slowly added to the trithiocyanuric acid trisodium salt that total amount is 364.8Kg (1500mol) and (is always divided into 3 batches, every batch about in batches
121Kg, every crowd of interval about 10~12min).Trithiocyanuric acid trisodium salt dissolves rapidly, and is reacted with chloropropene and release heat, leads to
Supercooling loop and charging rate control, by reactor temperature control between 3~10 DEG C, the control of total feed time exists
60min, after the completion of charging, continue to react 20min.
(2) in order to realize the complete reaction of raw material, cooling circuit is closed, the hydroquinones for adding 80ppm stablizes three polysulfides
Cyanic acid triallyl, to stablize trithiocyanuric acid triallyl and chloropropene, it is then turned on recirculated water and is heated to 40 DEG C, continue to stir
Mix reaction 15min.Then, start that unreacted chloropropene monomer is evaporated in vacuo at 40 DEG C, and collect in case recycling.
(3) it is after distillation completely, remaining trithiocyanuric acid triallyl and sodium chloride mixture in reactor is slowly cold
But to 30 DEG C or so, it is slowly stirred 1.5 hours, treats that sodium chloride is separated out and is roughened in system.Then, using 0.22 μm of tetrafluoro second
Alkene filter membrane removes sodium chloride in mixture, obtains the filtrate of clear, as product trithiocyanuric acid by vacuum filtration
Triallyl monomer (427.4Kg), yield 95.8%, purity 99.5%.
Embodiment 2
The preparation method of the present embodiment trithiocyanuric acid triallyl, step are as follows：
(1) in the 1000L enamel reactors with cooling circuit and circulator bath loop, it is pumped into chloropropene 516.5Kg
(6750mol, excessively 50%), stirring and cooling circuit are opened, the chloropropene monomer in reactor is cooled to 0~2 DEG C.So
Afterwards, beginning is slowly added to the trithiocyanuric acid trisodium salt that total amount is 364.8Kg (1500mol) and (is always divided into 4 batches, every batch about in batches
91Kg, every crowd of interval about 10~12min).Trithiocyanuric acid trisodium salt dissolves rapidly, and is reacted with chloropropene and release heat, leads to
Supercooling loop and charging rate control, by reactor temperature control between 3~10 DEG C, the control of total feed time exists
65min, after the completion of charging, continue to react 20min.
(2) in order to realize the complete reaction of raw material, cooling circuit is closed, the hydroquinones for adding 60ppm stablizes three polysulfides
Cyanic acid triallyl, to stablize trithiocyanuric acid triallyl and chloropropene, it is then turned on recirculated water and is heated to 40 DEG C, continue to stir
Mix reaction 20min.Then, start that unreacted chloropropene monomer is evaporated in vacuo at 40 DEG C, and collect in case recycling.
(3) after distillation completely, trithiocyanuric acid triallyl and sodium chloride mixture Slow cooling will be left in reactor
To 30 DEG C or so, it is slowly stirred 2 hours, treats that sodium chloride is separated out and is roughened in system.Then, using 0.22 μm of tetrafluoroethene mistake
Filter membrane removes sodium chloride in mixture, obtains the filtrate of clear, as product trithiocyanuric acid triolefin by vacuum filtration
Propyl ester monomer (433.7Kg), yield 98.3%, purity 99.6%.
Embodiment 3
The preparation method of the present embodiment trithiocyanuric acid triallyl, step are as follows：
(1) in the 1000L enamel reactors with cooling circuit and circulator bath loop, it is pumped into chloropropene 516.5Kg
(6750mol, excessively 50%), stirring and cooling circuit are opened, chloropropene in reactor is cooled to 0~2 DEG C.Then, start
The trithiocyanuric acid trisodium salt that total amount is 364.8Kg (1500mol) is slowly added in batches (is always divided into 5 batches, every crowd of about 73Kg, often
Criticize interval about 4~6min).Trithiocyanuric acid trisodium salt dissolves rapidly, and is reacted with chloropropene and release heat, passes through cooling circuit
Controlled with charging rate, by reactor temperature control between 3~10 DEG C, total feed time is controlled in 80min, has been fed
Cheng Hou, continue to react 20min.
(3) in order to realize the complete reaction of raw material, cooling circuit is closed, the hydroquinones for adding 50ppm stablizes three polysulfides
Cyanic acid triallyl, to stablize trithiocyanuric acid triallyl and chloropropene, it is then turned on recirculated water and is heated to 43 DEG C, continue to stir
Mix reaction 25min.Then, start that unreacted chloropropene monomer is evaporated in vacuo at 43 DEG C, and collect in case recycling.
(3) after distillation completely, trithiocyanuric acid triallyl and sodium chloride mixture Slow cooling will be left in reactor
To 30 DEG C or so, it is slowly stirred 2 hours, treats that sodium chloride is separated out and is roughened in system.Then, using 0.22 μm of tetrafluoroethene mistake
Filter membrane removes sodium chloride in mixture, obtains the filtrate of clear, as product trithiocyanuric acid triolefin by vacuum filtration
Propyl ester monomer (435.0Kg), yield 97.5%, purity 99.9%.
Fig. 1 is product manufactured in the present embodiment1H-NMR spectrum, δ=5.94ppm, δ=5.34,5.17ppm and δ in figure
=3.70ppm is corresponded respectively at pi-allyl a and pi-allyl b places and methylene (S-CH2-) proton hydrogen chemical shifts.Wherein,
Product purity is obtained by nuclear magnetic spectrogram by integral and calculating.
Embodiment 4
(1) in the 1000L enamel reactors with cooling circuit and circulator bath loop, it is pumped into chloropropene 447.7Kg
(5850mol, excessively 30%), stirring and cooling circuit are opened, the chloropropene monomer in reactor is cooled to 0~2 DEG C.So
Afterwards, beginning is slowly added to the trithiocyanuric acid trisodium salt that total amount is 364.8Kg (1500mol) and (is always divided into 5 batches, every batch about in batches
73Kg, every crowd of interval about 4~6min).Trithiocyanuric acid trisodium salt dissolves rapidly, and is reacted with chloropropene and release heat, passes through
Cooling circuit and charging rate control, by reactor temperature control between 3~10 DEG C, the control of total feed time exists
80min, after the completion of charging, continue to react 20min.
(2) in order to realize the complete reaction of raw material, cooling circuit is closed, the hydroquinones for adding 50ppm stablizes three polysulfides
Cyanic acid triallyl, to stablize trithiocyanuric acid triallyl and chloropropene, it is then turned on recirculated water and is heated to 43 DEG C, continue to stir
Mix reaction 25min.Then, start that unreacted chloropropene monomer is evaporated in vacuo at 43 DEG C, and collect in case recycling.
(3) after distillation completely, trithiocyanuric acid triallyl and sodium chloride mixture Slow cooling will be left in reactor
To 30 DEG C or so, it is slowly stirred 1.5 hours, treats that sodium chloride is separated out and is roughened in system.Then, using 0.22 μm of tetrafluoroethene
Filter membrane removes sodium chloride in mixture, obtains the filtrate of clear, as product trithiocyanuric acid three by vacuum filtration
Allyl ester monomer (423.4Kg), yield 94.9%, purity 99.8%.
Embodiment 5
The present embodiment is distinguished as with embodiment 3：The addition of chloropropene is 550.9kg (7200mol, mistake in step (1)
60%) amount, after being warming up to 43 DEG C in step (2), continues stirring reaction 40min.
After the completion of distillation, product is waited until using centrifugation, it is 98.7% to obtain 410.9Kg (yield 92.1%) purity
Trithiocyanuric acid triallyl monomeric products.
The above embodiment of the present invention is only example to illustrate the invention, and is not the implementation to the present invention
The restriction of mode.For those of ordinary skill in the field, other can also be made not on the basis of the above description
With the change and variation of form.Here all embodiments can not be exhaustive.It is every to belong to technical scheme
Row of the obvious changes or variations amplified out still in protection scope of the present invention.
Claims (8)
1. trithiocyanuric acid triallyl, it is characterised in that shown in structural formula such as formula (I)：
2. a kind of preparation method of trithiocyanuric acid triallyl, it is characterised in that step is as follows：
(1) trithiocyanuric acid triallyl synthesizes：Chloropropene is added in reactor, then stirs and adds three polysulfides in batches
Cyanic acid trisodium salt, the wherein mol ratio of trithiocyanuric acid trisodium salt and chloropropene are 1:3.9~6.0, trithiocyanuric acid trisodium salt
Feed time be 40~90min, continue stirring reaction 10~40min after the completion of charging, above-mentioned whole process controls reactant
It is that temperature is 3~12 DEG C；
(2) temperature reaction：After the completion of step (1), 20~100ppm polymerization inhibitor is added in reaction system, then by reaction system
40~45 DEG C are warming up to, continues 10~40min of stirring reaction；
(3) it is evaporated in vacuo：After the completion of step (2), reacted mixed liquor is evaporated in vacuo at 40~45 DEG C, with recovery system
In unreacted chloropropene monomer, the chloropropene of recovery recycles as reactant；
(4) isolate and purify：After distillation completely, by the mixture of remaining trithiocyanuric acid triallyl and sodium chloride in reactor
25~30 DEG C are slowly cooled to precipitated sodium chloride, 05~1.5h is stirred for, after sodium chloride in system separates out completely, by micro-
Membrane filtration is centrifuged off sodium chloride, that is, obtains described trithiocyanuric acid triallyl.
3. the preparation method of trithiocyanuric acid triallyl according to claim 2, it is characterised in that the three polysulfides cyanogen
The mol ratio of sour trisodium salt and chloropropene is 1:4.5~5.1.
4. the preparation method of trithiocyanuric acid triallyl according to claim 2, it is characterised in that three in step (1)
Polysulfide cyanic acid trisodium salt adds in batches, per 4~15min of batch interval, and in step (1) reaction time be no more than 2h, it is described
Reaction time is to be initially added into the time that trithiocyanuric acid trisodium salt terminates to step (1) reaction.
5. the preparation method of trithiocyanuric acid triallyl according to claim 4, it is characterised in that trithiocyanuric acid three
3~5 additions of sodium salt point, feed time and every batch interval time summation are 80~100min.
6. the preparation method of trithiocyanuric acid triallyl according to claim 5, it is characterised in that step (1) and step
Suddenly (2) total reaction time is 1.5~3.0h, and the total reaction time is feed time, interval time and step in step (1)
(2) heating-up time, stirring reaction time in.
7. the preparation method of trithiocyanuric acid triallyl according to claim 2, it is characterised in that institute in step (4)
State the tetrafluoroethene filter membrane or vinylidene filter membrane that mocromembrane is 0.22 μm.
8. the preparation method of trithiocyanuric acid triallyl according to claim 2, it is characterised in that the polymerization inhibitor is
Hydroquinones or hydroquinone derivative.
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| CN201710984821.7A CN107739346B (en) | 2017-10-20 | 2017-10-20 | Tripolythiotriallyl cyanurate and preparation method thereof |
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| CN201710984821.7A CN107739346B (en) | 2017-10-20 | 2017-10-20 | Tripolythiotriallyl cyanurate and preparation method thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676151A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
| JP2004090228A (en) * | 2002-08-29 | 2004-03-25 | Fuji Photo Film Co Ltd | Inkjet recording sheet |
| CN102491951A (en) * | 2011-12-02 | 2012-06-13 | 自贡天龙化工有限公司 | Production process of triallyl cyanurate |
| CN105669579A (en) * | 2016-03-18 | 2016-06-15 | 江苏科利新材料有限公司 | Method for preparing triallyl cyanurate |
-
2017
- 2017-10-20 CN CN201710984821.7A patent/CN107739346B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2676151A (en) * | 1952-04-09 | 1954-04-20 | American Cyanamid Co | Corrosion inhibitors for lubricating oils |
| JP2004090228A (en) * | 2002-08-29 | 2004-03-25 | Fuji Photo Film Co Ltd | Inkjet recording sheet |
| CN102491951A (en) * | 2011-12-02 | 2012-06-13 | 自贡天龙化工有限公司 | Production process of triallyl cyanurate |
| CN105669579A (en) * | 2016-03-18 | 2016-06-15 | 江苏科利新材料有限公司 | Method for preparing triallyl cyanurate |
Non-Patent Citations (2)
| Title |
|---|
| KO WAKABAYASHI ET AL.: ""Inhibitory Effects of s-Triazines on the nitrification in Soil (Part 4) : Effects of Hydroxy-s-triazines and Their Derivatives, Miscellaneous s-Triazines and Hydro-s-tirazines"", 《JAPANESE JOURNAL OF SOIL SCIENCE AND PLANT NUTRITION》 * |
| 张亨: ""三聚氰酸三烯丙酯的合成"", 《塑料助剂》 * |
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Effective date of registration: 20211026 Address after: No.99, Kehua North Road, Wuhou District, Chengdu, Sichuan 610041 Patentee after: CHENGDU KEYI POLYMER TECHNOLOGY Co.,Ltd. Address before: 643000 Huidong learning street 180, Zigong, Sichuan Patentee before: Sichuan University of Light Chemical Technology |