KR101956545B1 - 트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 - Google Patents
트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 Download PDFInfo
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- KR101956545B1 KR101956545B1 KR1020167020518A KR20167020518A KR101956545B1 KR 101956545 B1 KR101956545 B1 KR 101956545B1 KR 1020167020518 A KR1020167020518 A KR 1020167020518A KR 20167020518 A KR20167020518 A KR 20167020518A KR 101956545 B1 KR101956545 B1 KR 101956545B1
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- South Korea
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- chlorine atom
- reaction
- taic
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000004045 organic chlorine compounds Chemical class 0.000 claims abstract description 51
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 21
- 125000005336 allyloxy group Chemical group 0.000 claims abstract description 12
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 claims description 14
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 230000007704 transition Effects 0.000 claims description 5
- 238000006276 transfer reaction Methods 0.000 claims description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 20
- 239000012535 impurity Substances 0.000 abstract description 12
- 208000004605 Persistent Truncus Arteriosus Diseases 0.000 description 30
- 208000037258 Truncus arteriosus Diseases 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 7
- 230000007797 corrosion Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000003566 sealing material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- -1 allyl compound Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 0 *c(nc(*)nc1Cl)c1Cl Chemical compound *c(nc(*)nc1Cl)c1Cl 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- 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
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPJP-P-2009-125333 | 2009-05-25 | ||
| JP2009125333 | 2009-05-25 | ||
| PCT/JP2010/058565 WO2010137517A1 (ja) | 2009-05-25 | 2010-05-20 | トリアリルイソシアヌレート、トリアリルシアヌレート及びトリアリルイソシアヌレートの製造方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117025328A Division KR20120015309A (ko) | 2009-05-25 | 2010-05-20 | 트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20160092064A KR20160092064A (ko) | 2016-08-03 |
| KR101956545B1 true KR101956545B1 (ko) | 2019-03-11 |
Family
ID=43222627
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020167020518A Active KR101956545B1 (ko) | 2009-05-25 | 2010-05-20 | 트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 |
| KR1020117025328A Ceased KR20120015309A (ko) | 2009-05-25 | 2010-05-20 | 트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020117025328A Ceased KR20120015309A (ko) | 2009-05-25 | 2010-05-20 | 트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8431697B2 (enExample) |
| EP (1) | EP2436677B1 (enExample) |
| JP (2) | JP5870475B2 (enExample) |
| KR (2) | KR101956545B1 (enExample) |
| CN (1) | CN102438997B (enExample) |
| TW (1) | TWI535707B (enExample) |
| WO (1) | WO2010137517A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5870475B2 (ja) * | 2009-05-25 | 2016-03-01 | 日本化成株式会社 | トリアリルイソシアヌレート、トリアリルシアヌレート及びトリアリルイソシアヌレートの製造方法 |
| KR101774225B1 (ko) * | 2009-05-25 | 2017-09-04 | 니폰 가세이 가부시키가이샤 | 트리알릴 이소시아누레이트의 저장방법 |
| ES2632783T3 (es) | 2014-12-19 | 2017-09-15 | Evonik Degussa Gmbh | Sistemas de redes de cubierta para láminas de encapsulación que comprenden compuestos de bis-(alquenilamidas) |
| ES2635260T3 (es) | 2014-12-19 | 2017-10-03 | Evonik Degussa Gmbh | Sistemas correticulantes para láminas de encapsulado que comprenden compuestos de urea |
| CN105669579B (zh) * | 2016-03-18 | 2018-01-16 | 江苏科利新材料有限公司 | 一种三聚氰酸三烯丙酯的制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537816A (en) * | 1951-01-09 | Method-of preparing tjnsaturated | ||
| US3322761A (en) * | 1965-07-14 | 1967-05-30 | Allied Chem | Purification of triallyl isocyanurate |
| JPS4722588B1 (enExample) * | 1970-03-02 | 1972-06-24 | ||
| JPS4826022B1 (enExample) * | 1970-05-03 | 1973-08-03 | ||
| JPS4826022A (enExample) | 1971-08-04 | 1973-04-05 | ||
| ATE20744T1 (de) | 1981-11-04 | 1986-08-15 | Akzo Nv | Verfahren zur herstellung von isocyansaeureesters. |
| JPH11255753A (ja) * | 1998-03-10 | 1999-09-21 | Nissei Kagaku Kogyo Kk | 高品位トリアリルイソシアヌレートとその製造方法 |
| JP4544496B2 (ja) * | 2000-12-14 | 2010-09-15 | 日本化薬株式会社 | エポキシ樹脂、エポキシ樹脂組成物及びその硬化物 |
| JP4826022B2 (ja) | 2001-04-05 | 2011-11-30 | ソニー株式会社 | 画像処理回路および画像処理システム |
| JP2006036876A (ja) | 2004-07-26 | 2006-02-09 | Du Pont Mitsui Polychem Co Ltd | 太陽電池封止材及びそれを用いた太陽電池モジュール |
| JP4722588B2 (ja) | 2005-06-30 | 2011-07-13 | 本田技研工業株式会社 | 回転電機のステータおよびその製造方法 |
| JP2007115840A (ja) | 2005-10-19 | 2007-05-10 | Kyocera Corp | 配線基板および配線基板の製造方法 |
| DE102006032167B4 (de) * | 2006-07-12 | 2014-11-27 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Triallylisocyanurat (TAIC) |
| JP5130728B2 (ja) * | 2007-01-31 | 2013-01-30 | Ｄｉｃ株式会社 | エポキシ樹脂の精製方法 |
| JP5870475B2 (ja) * | 2009-05-25 | 2016-03-01 | 日本化成株式会社 | トリアリルイソシアヌレート、トリアリルシアヌレート及びトリアリルイソシアヌレートの製造方法 |
| KR101774225B1 (ko) * | 2009-05-25 | 2017-09-04 | 니폰 가세이 가부시키가이샤 | 트리알릴 이소시아누레이트의 저장방법 |
| JP5509674B2 (ja) * | 2009-05-25 | 2014-06-04 | 日本化成株式会社 | トリアリルイソシアヌレート及びその製造方法 |
-
2010
- 2010-05-20 JP JP2010116163A patent/JP5870475B2/ja active Active
- 2010-05-20 EP EP10780472.6A patent/EP2436677B1/en active Active
- 2010-05-20 WO PCT/JP2010/058565 patent/WO2010137517A1/ja not_active Ceased
- 2010-05-20 KR KR1020167020518A patent/KR101956545B1/ko active Active
- 2010-05-20 CN CN201080022617.3A patent/CN102438997B/zh active Active
- 2010-05-20 KR KR1020117025328A patent/KR20120015309A/ko not_active Ceased
- 2010-05-24 TW TW099116521A patent/TWI535707B/zh active
-
2011
- 2011-11-02 US US13/287,270 patent/US8431697B2/en active Active
-
2015
- 2015-10-15 JP JP2015203741A patent/JP6048559B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2436677A1 (en) | 2012-04-04 |
| TWI535707B (zh) | 2016-06-01 |
| US8431697B2 (en) | 2013-04-30 |
| KR20120015309A (ko) | 2012-02-21 |
| JP2011006389A (ja) | 2011-01-13 |
| US20120095223A1 (en) | 2012-04-19 |
| CN102438997A (zh) | 2012-05-02 |
| WO2010137517A1 (ja) | 2010-12-02 |
| JP5870475B2 (ja) | 2016-03-01 |
| EP2436677A4 (en) | 2012-10-17 |
| JP6048559B2 (ja) | 2016-12-21 |
| EP2436677B1 (en) | 2025-02-12 |
| CN102438997B (zh) | 2016-05-04 |
| TW201109309A (en) | 2011-03-16 |
| JP2016020384A (ja) | 2016-02-04 |
| KR20160092064A (ko) | 2016-08-03 |
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