WO2010137517A1 - 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 - Google Patents
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 Download PDFInfo
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- WO2010137517A1 WO2010137517A1 PCT/JP2010/058565 JP2010058565W WO2010137517A1 WO 2010137517 A1 WO2010137517 A1 WO 2010137517A1 JP 2010058565 W JP2010058565 W JP 2010058565W WO 2010137517 A1 WO2010137517 A1 WO 2010137517A1
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- Prior art keywords
- chemical formula
- ppm
- taic
- tac
- chlorine atom
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- 0 Cc1c(*)nc(*)nc1C Chemical compound Cc1c(*)nc(*)nc1C 0.000 description 2
- DGBZQPVIQOKMQQ-UHFFFAOYSA-N C=CCOc1nc(OCC=C)nc(Cl)n1 Chemical compound C=CCOc1nc(OCC=C)nc(Cl)n1 DGBZQPVIQOKMQQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
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- 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
- 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
Definitions
- the present invention relates to a method for producing triallyl isocyanurate, triallyl cyanurate and triallyl isocyanurate.
- triallyl isocyanurate triallyl isocyanurate
- TAIC triallyl isocyanurate
- TAIC for example, reacts 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) with allyl alcohol in accordance with the following reaction route to represent triallyl cyanurate (hereinafter referred to as “TAC”).
- TAC triallyl cyanurate
- TAIC is useful as a crosslinking agent having excellent heat resistance and chemical resistance, and is expected to be used in a wide range of fields such as electronic materials, liquid crystals, semiconductors, and solar cells.
- printed circuit boards that is, plate-like or film-like components that make up an electronic circuit by fixing a large number of electronic components such as integrated circuits, resistors, capacitors, etc.
- TAIC is used as a sealing material for preventing substances such as liquids and gases from entering the interior of the component.
- TAIC is used as a liquid sealing material because it is a viscous liquid (melting point: 26 ° C.) at room temperature.
- a silane coupling agent is added to improve the wettability.
- TAIC is also used as a crosslinking agent for crosslinkable polymers (Patent Document 3).
- the present invention has been made in view of the above circumstances, and an object of the present invention is to identify a causative substance from impurities in TAIC and provide a TAIC with a low content of the causative substance.
- Impurities in TAIC are caused by impurities in TAC as a raw material.
- impurity contained in TAC is represented by the following chemical formula (I), (II), and (III).
- R 1 and R 2 in the chemical formula (I) represent a chlorine atom or an allyloxy group, but at least one represents a chlorine atom.
- Any one of R 3 , R 4 and R 5 in the chemical formula (III) represents a chlorine atom, and any two represent an allyloxy group.
- the compounds represented by the chemical formulas (I) and (III) are allyl compounds of chlorinated barbituric acid (2,4,5,6-tetrachloropyrimidine).
- the cause of these generations is considered as follows.
- cyanuric chloride is usually produced by trimerization of chlorocyan obtained by chlorination of hydrocyanic acid, but when impurities such as acetylene are present in the hydrocyanic acid of the raw material, tetrachlorobarbi of the following chemical formula (IV) Generated by the tool.
- the organic chlorine compounds of the aforementioned chemical formulas (I) and (III) are generated as impurities.
- organochlorine compound of formula (II) is presumed to be a reaction byproduct of cyanuric chloride and allyl alcohol.
- Organochlorine compounds of formulas (I) and (II) are gradually hydrolyzed in water to produce chlorine ions, causing corrosion, whereas organochlorine compounds of formula (III) are almost hydrolyzed. Since it is not decomposed, it does not cause corrosion. Therefore, the corrosion-causing substance in TAC is specified as the organic chlorine compounds of the chemical formulas (I) and (II).
- the present invention has been completed on the basis of the above knowledge, and is composed of a plurality of groups of inventions linked to each other.
- the gist of each invention is as follows.
- the first gist of the present invention resides in triallyl isocyanurate characterized by containing an organochlorine compound represented by the following chemical formula (I) and having a content of 100 ppm or less.
- R 1 and R 2 in chemical formula (I) represent a chlorine atom or an allyloxy group, and at least one represents a chlorine atom.
- the second gist of the present invention resides in triallyl cyanurate characterized by containing organochlorine compounds represented by the following chemical formulas (1) and (2) and having a total content of 800 ppm or less. .
- R 1 and R 2 in chemical formula (I) represent a chlorine atom or an allyloxy group, and at least one represents a chlorine atom.
- the third gist of the present invention resides in the above-mentioned method for producing triallyl isocyanurate, characterized by causing the above-mentioned triallyl cyanurate to undergo a transfer reaction.
- the fourth gist of the present invention is that triallyl cyanurate is obtained by reacting cyanuric chloride with allyl alcohol, and the obtained triallyl cyanurate is obtained at 30 to 80 ° C. at 0.5 to 10% by weight.
- the present invention resides in a method for producing triallyl isocyanurate, characterized by carrying out a transfer reaction after stirring in a strong base aqueous solution.
- the triallyl isocyanurate of the present invention is suitable as, for example, a sealing material for a printed wiring board because it does not cause metal corrosion due to impurities contained therein.
- TAC production that is, the reaction between cyanuric chloride and allyl alcohol is performed by heating in the presence of a basic catalyst (for example, sodium hydroxide).
- a basic catalyst for example, sodium hydroxide
- cyanuric chloride is added at room temperature to a solution composed of allyl alcohol in a reaction solvent, a predetermined amount of a basic catalyst, and water, and stirred for a predetermined time to generate TAC.
- the details of the reaction conditions can be referred to the description of Non-Patent Document 1 described above.
- the crude TAC obtained here contains the organochlorine compounds of the aforementioned chemical formulas (I) and (II).
- the content of the organic chlorine compound of the chemical formula (I) is 100 to 250 ppm
- the content of the organic chlorine compound of the chemical formula (II) is 500 to 1,000 ppm.
- the solution is used in a low concentration strong base aqueous solution under relatively low temperature conditions.
- Process the crude TAC Specifically, this is performed as follows.
- the precipitated salt for example, sodium chloride
- the recovered filtrate is concentrated to recover crude TAC as an oil.
- crude TAC the above oily substance
- the treatment time is usually 0.5 to 10 hours, preferably 1 to 6 hours.
- TAIC that is, the transfer reaction of TAC is carried out by heat treatment in the presence of a catalyst, and the details of the reaction conditions can be referred to the description in Patent Document 1 described above.
- the transfer reaction is performed in a reaction solvent (for example, xylene) in the presence of a copper catalyst.
- the reaction temperature is usually 100 to 150 ° C., preferably 120 to 140 ° C.
- the reaction solvent is distilled off under reduced pressure to recover an oily substance.
- the oily substance is distilled under a reduced pressure to obtain TAIC crystals.
- the TAC of the present invention is characterized by containing an organic chlorine compound represented by the following chemical formulas (1) and (2) and having a total content of 800 ppm or less.
- R 1 and R 2 in chemical formula (I) represent a chlorine atom or an allyloxy group, and at least one represents a chlorine atom.
- the total content of the organic chlorine compounds represented by the chemical formulas (1) and (2) in the TAC of the present invention is preferably 500 ppm or less, more preferably 100 ppm or less.
- the TAC of the present invention can be suitably used, for example, as a raw material for TAIC, and a TAIC with a low content of impurities that cause metal corrosion can be produced.
- the TAIC of the present invention contains an organochlorine compound represented by the above chemical formula (1) and the content thereof is 100 ppm or less.
- the content of the organic chlorine compound represented by the chemical formula (1) is preferably 50 ppm or less, more preferably 30 ppm or less.
- the TAIC of the present invention is suitable as a sealing material for printed wiring boards because it contains a small amount of impurities that cause metal corrosion.
- the TAIC of the present invention is mixed with a crosslinkable elastomer, vulcanized by heating, radiation, etc., and used as a sealant for electronic materials, semiconductors, solar cell materials, or mixed with a crosslinkable thermoplastic resin. Vulcanized with an electron beam or the like and suitably used for coating electric wires.
- Comparative Example 1 18.4 g of cyanuric chloride was added to a solution of 100 g of allyl alcohol, 12 g of NaOH and 10 g of water at room temperature. The mixture was stirred at room temperature for 2 hours, the precipitated sodium chloride was filtered, and the collected filtrate was concentrated to obtain an oily substance. The oily product was washed with water and purified by distillation to obtain TAC crystals (yield 85%).
- This TAC includes an organic chlorine compound (2-allyloxy-4,5,6-trichloropyrimidine) in which R 1 is an allyloxy group and R 2 is a chlorine atom in chemical formula (I), R 1 is a chlorine atom, R 1 Mixture with organochlorine compound (4-allyloxy-2,5,6-trichloropyrimidine) in which 2 is an allyloxy group (A) 170 ppm, organochlorine compound of formula (II) (2,6-diallyloxy-4-chlorotriazine) ) 740 ppm was included.
- TAIC contained 120 ppm of the mixture of organochlorine compounds (A) and 10 ppm of the organochlorine compound of the formula (II).
- Example 1 The oily substance obtained in the same manner as in Comparative Example 1 was heated and stirred in a 5 wt% NaOH aqueous solution at 50 ° C. for 2 hours. Subsequently, after neutralizing with hydrochloric acid, the organic layer was separated and purified by distillation to obtain TAC crystals (yield 84%). In the TAC, neither the organic chlorine compound (A) nor the organic chlorine compound of the chemical formula (II) was detected (less than 10 ppm).
- Example 2 The oily substance obtained in the same manner as in Comparative Example 1 was heated and stirred in a 1% by weight aqueous NaOH solution at 50 ° C. for 6 hours. Subsequently, after neutralizing with hydrochloric acid, the organic layer was separated and purified by distillation to obtain TAC crystals (yield 84%).
- This TAC contained 40 ppm of the above-mentioned mixture (A) of the organic chlorine compound and 10 ppm of the organic chlorine compound of the chemical formula (II).
- the TAIC contained 10 ppm of the organochlorine compound (A). No organochlorine compound of formula (II) was detected (less than 10 ppm).
- Test Example 1 (TAIC hydrolysis test): 1 g of TAIC and 20 g of water obtained in the above examples were placed in a Teflon (registered trademark) pressure vessel, heated at 120 ° C. for 200 hours, and then the chloride ion concentration in water was measured. Chlorine ion concentration was measured by an iona chromatograph (column used: “DIONEX Ion Pack AS12A”, eluent: 2.7 mM-Na 2 CO 3 /0.3 mM-NaHCO 3 ). The detection limit is 1 ppm. The results are shown in Table 2.
- Test example 2 hydrolysis of corrosion-causing substances: In accordance with the procedure described below, a corrosion-causing substance was synthesized and then hydrolyzed under accelerated conditions.
- ⁇ Corrosion-causing substance Synthesis of 2-allyloxy-4,5,6-trichloropyrimidine> 2,4,5,6-tetrachloropyrimidine (manufactured by Tokyo Chemical Industry Co., Ltd.) 54.04 g (0.2361 mol), NaOH 12.93 g (0.3070 mol), 1,4-dioxane 280 g in a solution at 40 ° C. 18.01 g (0.3070 mol) of alcohol was reduced over 2 hours. Furthermore, it reacted at 40 degreeC for 2.5 hours, it filtered after cooling, and dioxane was distilled off in vacuum.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
この分析はガスクロマトグラフ(面積百分率法)によって行った。表1に分析条件を示す。なお、検出限界は10ppmである。
アリルアルコール100g、NaOH12g、水10gの溶液に室温で塩化シアヌル18.4gを添加した。室温で2時間攪拌し、析出した塩化ナトリウムを濾過し、回収した濾液を濃縮し、油状物を得た。次いで、この油状物を、水洗した後、蒸留精製し、TACの結晶を得た(収率85%)。このTACには、化学式(I)において、R1がアリルオキシ基、R2が塩素原子である有機塩素化合物(2-アリルオキシー4,5,6-トリクロロピリミジン)と、R1が塩素原子、R2がアリルオキシ基である有機塩素化合物(4-アリルオキシー2,5,6-トリクロロピリミジン)との混合物(A)170ppm、化学式(II)の有機塩素化合物(2,6-ジアリルオキシー4-クロロトリアジン)740ppmが含まれていた。
比較例1と同様して得た油状物を、5重量%NaOH水溶液中、50℃で2時間、加熱攪拌処理した。次いで、塩酸で中和した後、有機層を分離し、蒸留精製し、TACの結晶を得た(収率84%)。このTACには前記の有機塩素化合物(A)及び化学式(II)の有機塩素化合物は、何れも、検出されなかった(10ppm未満)。
比較例1と同様して得た油状物を、1重量%NaOH水溶液中、50℃で6時間、加熱攪拌処理した。次いで、塩酸で中和した後、有機層を分離し、蒸留精製し、TACの結晶を得た(収率84%)。このTACには前記の有機塩素化合物の混合物(A)が40ppm、化学式(II)の有機塩素化合物が10ppm含まれていた。
前記の各例で得られたTAIC1gと水20gとをテフロン(登録商標)製耐圧容器に入れ、120℃で200時間加熱した後、水中の塩素イオン濃度を測定した。塩素イオン濃度の測定はイオナクロマトグラフ(使用カラム:「DIONEX Ion Pack AS12A」、溶離液:2.7mM-Na2CO3/0.3mM-NaHCO3)で行った。検出限界は1ppmである。結果を表2に示す。
以下に記載の要領に従って、腐食原因物質を合成した後、加速条件下で加水分解を行った。
2,4,5,6-テトラクロロピリミジン(東京化成社製)54.04g(0.2361モル)、NaOH12.93g(0.3070モル)、1,4-ジオキサン280gの溶液に40℃でアリルアルコール18.01g(0.3070モル)を2時間かけて適下した。更に、40℃で2.5時間反応し、冷却後、ろ過してジオキサンを真空で留去した。シリカゲルカラムクロマトグラフィ(酢酸エチル/nヘキサン1/1)で精製し、2-アリルオキシー4,5,6-トリクロロピリミジン53.34g(収率93.5重量%)を得た。同定はGC-MS分析によって行った。参考までに、GC-MS分析の測定結果を以下の表3に示す。
上記の腐食原因物質5gと水5gを耐圧容器中で140℃、6日間加熱した。得られた加水分解物の塩素イオン濃度は15重量%であった。
Claims (6)
- トリアリルシアヌレートの転移反応で製造される請求項1に記載のトリアリルイソシアヌレート。
- 請求項3に記載のトリアリルシアヌレートを転移反応させることを特徴とする請求項1に記載のトリアリルイソシアヌレートの製造方法。
- トリアリルシアヌレートが塩化シアヌルとアリルアルコールとの反応で得られたものである請求項4に記載のトリアリルイソシアヌレートの製造方法。
- 塩化シアヌルとアリルアルコールとを反応させてトリアリルシアヌレートを得、得られたトリアリルシアヌレートを、30~80℃、0.5~10重量%の強塩基水溶液中で撹拌処理した後に、転移反応させることを特徴とするトリアリルイソシアヌレートの製造方法。
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10780472A EP2436677A4 (en) | 2009-05-25 | 2010-05-20 | TRIALLYLISOCYANURATE, TRIALLYLCYANURATE AND PROCESS FOR THE PRODUCTION OF TRIALLYLISOCYANURATE |
KR1020167020518A KR101956545B1 (ko) | 2009-05-25 | 2010-05-20 | 트리알릴이소시아누레이트, 트리알릴시아누레이트 및 트리알릴이소시아누레이트의 제조방법 |
CN201080022617.3A CN102438997B (zh) | 2009-05-25 | 2010-05-20 | 异氰尿酸三烯丙酯、氰尿酸三烯丙酯和异氰尿酸三烯丙酯的制造方法 |
US13/287,270 US8431697B2 (en) | 2009-05-25 | 2011-11-02 | Triallyl isocyanurate, triallyl cyanurate and process for producing triallyl isocyanurate |
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JP2009-125333 | 2009-05-25 | ||
JP2009125333 | 2009-05-25 |
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US13/287,270 Continuation-In-Part US8431697B2 (en) | 2009-05-25 | 2011-11-02 | Triallyl isocyanurate, triallyl cyanurate and process for producing triallyl isocyanurate |
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US (1) | US8431697B2 (ja) |
EP (1) | EP2436677A4 (ja) |
JP (2) | JP5870475B2 (ja) |
KR (2) | KR101956545B1 (ja) |
CN (1) | CN102438997B (ja) |
TW (1) | TWI535707B (ja) |
WO (1) | WO2010137517A1 (ja) |
Cited By (2)
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JP2011006389A (ja) * | 2009-05-25 | 2011-01-13 | Nippon Kasei Chem Co Ltd | 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 |
JP2011006390A (ja) * | 2009-05-25 | 2011-01-13 | Nippon Kasei Chem Co Ltd | トリアリルイソシアヌレートの貯蔵方法 |
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EP3034528B1 (de) | 2014-12-19 | 2017-06-21 | Evonik Degussa GmbH | Covernetzersysteme für Verkapselungsfolien umfassend Harnstoffverbindungen |
EP3034527B1 (de) | 2014-12-19 | 2017-05-31 | Evonik Degussa GmbH | Covernetzersysteme für Verkapselungsfolien umfassend Bis-(alkenylamid)-Verbindungen |
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 |
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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 |
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 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2011006389A (ja) * | 2009-05-25 | 2011-01-13 | Nippon Kasei Chem Co Ltd | 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 |
JP2011006390A (ja) * | 2009-05-25 | 2011-01-13 | Nippon Kasei Chem Co Ltd | トリアリルイソシアヌレートの貯蔵方法 |
Also Published As
Publication number | Publication date |
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US8431697B2 (en) | 2013-04-30 |
EP2436677A4 (en) | 2012-10-17 |
CN102438997B (zh) | 2016-05-04 |
JP5870475B2 (ja) | 2016-03-01 |
EP2436677A1 (en) | 2012-04-04 |
JP2011006389A (ja) | 2011-01-13 |
KR101956545B1 (ko) | 2019-03-11 |
TWI535707B (zh) | 2016-06-01 |
JP6048559B2 (ja) | 2016-12-21 |
US20120095223A1 (en) | 2012-04-19 |
JP2016020384A (ja) | 2016-02-04 |
TW201109309A (en) | 2011-03-16 |
CN102438997A (zh) | 2012-05-02 |
KR20160092064A (ko) | 2016-08-03 |
KR20120015309A (ko) | 2012-02-21 |
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