WO2011136355A1 - 1,1-ビス[(エテニロキシ)メチル]シクロヘキサン及びその製造方法 - Google Patents
1,1-ビス[(エテニロキシ)メチル]シクロヘキサン及びその製造方法 Download PDFInfo
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- WO2011136355A1 WO2011136355A1 PCT/JP2011/060433 JP2011060433W WO2011136355A1 WO 2011136355 A1 WO2011136355 A1 WO 2011136355A1 JP 2011060433 W JP2011060433 W JP 2011060433W WO 2011136355 A1 WO2011136355 A1 WO 2011136355A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/162—Unsaturated ethers containing rings other than six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
Definitions
- the present invention relates to a novel vinyl ether 1,1-bis [(ethenyloxy) methyl] cyclohexane and a method for producing the same.
- the 1,1-bis [(ethenyloxy) methyl] cyclohexane (also known as 1,1-cyclohexanedimethanol divinyl ether) according to the present invention has not been reported so far and is considered to be a novel compound.
- the object of the present invention is low odor, low volatility, low skin irritation, low toxicity, excellent curability, adhesion, transparency in the ultraviolet region, etc. And 1,1-bis [(ethenyloxy) methyl] cyclohexane and a method for producing the same.
- the 1,1-bis [(ethenyloxy) methyl] cyclohexane of the present invention is excellent in curability, adhesion, transparency in the ultraviolet region, and rigidity, so that it is a raw material for the polymerization composition, a crosslinking agent, and various synthetic reagents Useful as.
- the 1,1-bis [(ethenyloxy) methyl] cyclohexane of the present invention can be used for applications such as inks, paints, resists, color filters, adhesives, platemaking materials, sealants, and image forming agents. Is possible.
- the formula (II) Is reacted with 1,1-cyclohexanedimethanol represented by the formula (I) in an aprotic polar solvent:
- the compound 1,1-bis [(ethenyloxy) methyl] cyclohexane according to the present invention has low odor, low volatility and low skin irritation, low toxicity, and is also curable, adhesive and in the ultraviolet region.
- FIG. 2 is a 1 H-NMR chart of 1,1-bis [(ethenyloxy) methyl] cyclohexane produced in Example 1.
- FIG. 2 is a 13 C-NMR chart of 1,1-bis [(ethenyloxy) methyl] cyclohexane produced in Example 1.
- FIG. 2 is a 1 H-NMR chart of 1,1-bis [(ethenyloxy) methyl] cyclohexane produced in Example 1.
- the vinyl ether (I) according to the present invention can be produced according to the following reaction formula.
- an aprotic polar solvent such as dimethyl sulfoxide, N-methylpyrrolidone, N, N′-dimethylethyleneurea, N, N′-dimethyl is used.
- a reaction catalyst for example, water
- An alkaline compound such as an alkali metal hydroxide such as potassium oxide or sodium hydroxide is added.
- the amount of the aprotic polar solvent used is not particularly limited, but the amount of the aprotic polar solvent used is preferably 100 to 1,000 per 100 parts by weight of 1,1-cyclohexanedimethanol. Part by weight, more preferably 200 to 700 parts by weight.
- the amount of the aprotic polar solvent used is less than 100 parts by weight with respect to 100 parts by weight of 1,1-cyclohexanedimethanol, the selectivity of the reaction may decrease, which is not preferable.
- the amount of the aprotic polar solvent used exceeds 1000 parts by weight with respect to 100 parts by weight of 1,1-cyclohexanedimethanol, it is not preferable because the solvent removal after the completion of the reaction becomes complicated.
- the amount of the alkaline compound used as the reaction catalyst is not particularly limited, but the amount of the alkaline compound used is preferably at least 2 parts by weight with respect to 100 parts by weight of 1,1-cyclohexanedimethanol. More preferably, it is 4 to 50 parts by weight.
- the inside of the reaction vessel is replaced with an inert gas such as nitrogen gas, and then the reaction vessel is sealed, and the reaction is carried out by raising the temperature while pressing in acetylene.
- an inert gas such as nitrogen gas
- the atmosphere in the reaction vessel may be acetylene alone, but an inert gas such as nitrogen, helium or argon may be used in combination with acetylene.
- the pressure of acetylene is preferably 0.01 MPa or more in terms of gauge pressure, and productivity and side reaction suppression are suppressed. From the viewpoint of safety, more preferably, the acetylene pressure is a gauge pressure of 0.15 MPa or more and 1.0 MPa or less.
- the reaction temperature is preferably 80 to 140 ° C., preferably 100 ° C. or higher from the viewpoint of reaction rate, and preferably 130 ° C. or lower from the viewpoint of economy and side reaction suppression.
- 1,1-cyclohexanedimethanol (II) which is a raw material of the compound of the present invention, can be produced by a conventionally known method.
- the method described in WO 2005/005456 can be used.
- Production Example 1 A four-necked flask having a capacity of 2000 ml equipped with a stirrer and a thermometer was charged with 200 ml of tetrahydrofuran and 1300 ml of lithium diisopropylamide solution (about 2.0 mol / l, about 2.6 mol) and cooled to ⁇ 70 ° C. under an argon atmosphere. . Under stirring, a mixture of methyl cyclohexanecarboxylate (100.3 g, 0.691 mol) and 100 ml of tetrahydrofuran was added dropwise over 1 hour and 30 minutes while maintaining the temperature of the reaction mixture at ⁇ 70 ° C. or lower. Stir at temperature for about 2 hours 30 minutes.
- the NMR measurement result of the obtained 1,1-cyclohexanedimethanol was as follows. 1 H-NMR (CDCl 3 , TMS, 400 MHz): ⁇ ppm 1.34-1.36 (m, 4H), 1.43-1.47 (m, 6H), 2.54 (s, 2H), 3 .62 (s, 4H) 13 C-NMR (CDCl 3 , 100 MHz): ⁇ ppm 21.4, 26.5, 29.6, 38.3, 70.4
- Example 1 In a pressure resistant reaction vessel made of SUS having a capacity of 300 ml equipped with a stirrer, pressure gauge, thermometer, gas introduction pipe and gas purge line, 102.2 g of dimethyl sulfoxide, 1,1- having a purity of 99.1% obtained in Production Example 1 was obtained. Charge 15.2 g (0.10 mol) of cyclohexanedimethanol and 2.14 g (0.036 mol) of potassium hydroxide with a purity of 95.0%, flow nitrogen gas for about 60 minutes with stirring, and replace the inside with nitrogen. did. Next, the reaction vessel was sealed, and acetylene gas was injected into the vessel at a pressure of 1.8 kg / cm 2 .
- the temperature was gradually raised while maintaining the gauge pressure at 1.8 kg / cm 2 , and the reaction vessel internal temperature was controlled so as not to exceed 100 ° C., and the reaction was carried out for about 2 hours and 30 minutes.
- acetylene gas was successively replenished to keep the pressure in the reaction vessel constantly at 1.8 kg / cm 2 .
- the remaining acetylene gas was purged to obtain 118.8 g of a reaction solution.
- the reaction solvent was removed from the reaction solution, distilled under reduced pressure (0.2 kPa), and 16.9 g of a fraction distilled at 75 to 76 ° C. was collected.
- the obtained fraction was 1,1-bis [(ethenyloxy) methyl] cyclohexane represented by the following formula (purity of 98.9% by gas chromatography, yield: 81. 5%).
- Example 1 Polymerization was carried out as follows using 1,1-bis [(ethenyloxy) methyl] cyclohexane obtained in Example 1.
- HCl / ZnCl 2 was used as a polymerization initiator and Lewis acid, and 4.0 mL of 1,1-bis [(ethenyloxy) methyl] cyclohexane solution, 0.5 mL of 0.18% HCl solution, and 0.1 mL of ZnCl 2 solution were added to a Schlenk tube. Polymerization was started by injecting 5 mL in this order with a syringe.
- the reaction was carried out in methylene chloride at ⁇ 30 ° C., a monomer concentration of 0.15 mol / L, an HCl concentration of 5.0 mmol / L, and a ZnCl 2 concentration of 2.0 mmol / L.
- the polymerization reached a polymerization rate of 100% in 20 minutes, and was stopped by adding methanol with a small amount of aqueous ammonia to the polymerization system.
- the solution in which the polymerization was stopped was transferred to a separating funnel, diluted with methylene chloride, and washed three times with a saturated aqueous sodium chloride solution. Next, the solvent was removed from the organic layer by an evaporator and dried under reduced pressure to obtain a produced polymer.
- the polymer was further purified by decantation with methanol.
- the number average molecular weight of the obtained polymer: M n was 3800, and the molecular weight distribution: M w / M n was 1.65.
- the divinyl ether homopolymer obtained in Use Example 1 When the divinyl ether homopolymer obtained in Use Example 1 is used as a raw material for electronic materials, it has low odor, low volatility, low skin irritation, and low toxicity, and further has a high glass transition temperature. Indicated.
- the 1,1-bis [(ethenyloxy) methyl] cyclohexane of the present invention is polymerized to give a divinyl ether homopolymer, thereby exhibiting excellent performance such as a high glass transition temperature.
- ink materials such as inks and paints, as well as resists, color filters, adhesives, plate-making materials, sealants, and electronic devices typically used for image formation Useful as a raw material for materials.
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
本発明に係るビニルエーテル(I)は次のような反応式に従って製造することができる。
攪拌器及び温度計を備えた容量2000mlの四ツ口フラスコに、テトラヒドロフラン200ml及びリチウムジイソプロピルアミド溶液1300ml(約2.0mol/l、約2.6mol)を仕込み、アルゴン雰囲気下-70℃に冷却した。攪拌下、シクロヘキサンカルボン酸メチル(100.3g、0.691mol)とテトラヒドロフラン100mlの混合液を、反応混合物の温度を-70℃以下に保ちながら、1時間30分にわたり滴下し、-70℃以下の温度で約2時間30分攪拌した。引き続いて、得られた反応液にクロル炭酸メチル(100.0g、1.04mol)とテトラヒドロフラン250mlの混合液を同じ温度で3時間にわたり滴下し、-78℃~室温にて終夜反応させた。その後、減圧下に反応容器中の溶媒を留去し、残渣を飽和塩化アンモニウム水溶液1000ml中に投入し、酢酸エチルにて抽出し、有機層を水洗した後、無水硫酸マグネシウムで乾燥させた。乾燥剤を濾別後、溶媒を減圧下に留去し、反応混合物215.4gを得た。続いて、別の3000mlの4ツ口フラスコに、テトラヒドロフラン900mlと水素化リチウムアルミニウム溶液600ml(約2.0mol/l、約1.2mol)を仕込み、アルゴン雰囲気下、0℃に冷却し、攪拌下に、得られた反応混合物160.2gとテトラヒドロフラン400mlの混合液を、0℃以下に保ちながら、約2時間にわたって滴下し、0℃以下で撹拌しながら終夜放置した。その後、この反応液中に水を滴下、約6Nの塩酸で中和し、反応液から不溶塩を濾別後、減圧下に濃縮した。続いて残渣を水1000ml中に投入し、酢酸エチルで抽出し、無水硫酸マグネシウムで乾燥させた。乾燥剤を濾別後、減圧下に溶媒を留去し、残渣をn-ヘキサン中に投入した。析出した結晶をn-ヘキサンによるデカンテーションを繰返して洗浄後、減圧下に乾燥させ20.8gの結晶性粉末を得た。この結晶性粉末は、NMRによる分析の結果、1,1-シクロヘキサンジメタノールであった(ガスグロマトグラフィーによる純度99.1%)。
1H-NMR(CDCl3、TMS、400MHz):δppm 1.34-1.36(m,4H),1.43-1.47(m,6H),2.54(s,2H),3.62(s,4H)
13C-NMR(CDCl3、100MHz):δppm 21.4,26.5,29.6,38.3,70.4
攪拌器、圧力ゲージ、温度計、ガス導入管及びガスパージラインを備えた容量300mlのSUS製耐圧反応容器に、ジメチルスルホキシド102.2g、製造例1で得た純度99.1%の1,1-シクロヘキサンジメタノール15.2g(0.10mol)及び純度95.0%の水酸化カリウム2.14g(0.036mol)を仕込み、攪拌下に約60分間窒素ガスを流し、容器内を窒素にて置換した。次いで、反応容器を密封し、容器内にアセチレンガスを1.8kg/cm2の圧力で圧入した。次いで、ゲージ圧力を1.8kg/cm2に保ちながら徐々に昇温し、反応容器内温が100℃を越えないように制御し、約2時間30分反応させた。この間、逐次アセチレンガスを補充して反応容器内の圧力は常に1.8kg/cm2に保った。反応終了後、残留するアセチレンガスをパージして、反応液118.8gを得た。この反応液のガスクロ分析の結果、1,1-シクロヘキサンジメタノールの転化は定量的に進行し、所望の1,1-ビス[(エテニロキシ)メチル]シクロヘキサンの選択率は98.2%であった。
1H-NMR(CDCl3、TMS、400MHz):δppm 1.45(s,10H;e,f,g),3.57(s,4H;c),3.94(dd,2H,J=6.8,1.9Hz;Ha1),4.17(dd,2H,J=14.3,1.9Hz;Ha2),6.46(dd,2H,J=14.3,6.8Hz;Hb)
13C-NMR(CDCl3、100MHz):δppm 21.4(e or f),26.2(g),29.8(e又はf),37.6(d),70.9(c),85.9(a),152.4(b)
実施例1で得た1,1-ビス[(エテニロキシ)メチル]シクロヘキサンを用いて以下の通り重合させた。
重合開始剤およびルイス酸として、HCl/ZnCl2を用い、シュレンク管に1,1-ビス[(エテニロキシ)メチル]シクロヘキサン溶液4.0mL、0.18%HCl溶液0.5mL、ZnCl2溶液0.5mLをこの順に注射器で注入し重合を開始した。塩化メチレン中,-30℃、モノマー濃度0.15mol/L、HCl濃度5.0mmol/L、ZnCl2濃度2.0mmol/Lで行った。重合は、20分で重合率100%に達し、重合系にアンモニア水を少量加えたメタノールを加えて停止した。
Claims (4)
- 前記非プロトン性極性溶媒がジメチルスルホキシド、N-メチルピロリドン、N,N’-ジメチルエチレン尿素、N,N’-ジメチルプロピレン尿素、N,N’-ジエチルエチレン尿素、N,N’-ジイソプロピルエチレン尿素、N,N,N’,N’,N’’,N’’-ヘキサメチルリン酸トリアミド、1,3,4-トリメチル-2-イミダゾリジノン、ジエチレングリコールジメチルエーテル、トリエチレングリコールジメチルエーテル、テトラエチレングリコールジメチルエーテル、ポリエチレングリコールジメチルエーテルから選ばれる請求項2に記載の方法。
- 前記反応を、温度80℃~180℃で、アセチレン圧(ゲージ圧)0.01MPa以上で実施する請求項2又は3に記載の方法。
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JP2012512916A JP5726178B2 (ja) | 2010-04-28 | 2011-04-28 | 1,1−ビス[(エテニロキシ)メチル]シクロヘキサン及びその製造方法 |
US13/643,931 US9096506B2 (en) | 2010-04-28 | 2011-04-28 | 1,1-BIS[(ethenyloxy)methyl]cyclohexane and method of production of same |
DE112011101482.1T DE112011101482B4 (de) | 2010-04-28 | 2011-04-28 | 1,1-Bis[(ethenyloxy)methyl]cyclohexan und Verfahren zu dessen Herstellung |
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WO2012147511A1 (ja) * | 2011-04-28 | 2012-11-01 | 日本カーバイド工業株式会社 | 4,4-ビス[(エテニロキシ)メチル]シクロヘキセンおよびその製造方法 |
JP2012233068A (ja) * | 2011-04-28 | 2012-11-29 | Univ Of Fukui | ジビニルエーテルホモポリマー、その製造方法およびその用途 |
JP2013237840A (ja) * | 2012-04-18 | 2013-11-28 | Univ Of Fukui | ビニルエーテル誘導体ポリマー並びにその製造方法及び用途 |
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WO2012147511A1 (ja) * | 2011-04-28 | 2012-11-01 | 日本カーバイド工業株式会社 | 4,4-ビス[(エテニロキシ)メチル]シクロヘキセンおよびその製造方法 |
JP2012233068A (ja) * | 2011-04-28 | 2012-11-29 | Univ Of Fukui | ジビニルエーテルホモポリマー、その製造方法およびその用途 |
US9156762B2 (en) | 2011-04-28 | 2015-10-13 | Nippon Carbide Industries Co., Inc. | 4,4-bis[(ethenyloxy)methyl]cyclohexene and method for producing same |
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JP2013237840A (ja) * | 2012-04-18 | 2013-11-28 | Univ Of Fukui | ビニルエーテル誘導体ポリマー並びにその製造方法及び用途 |
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US20130041184A1 (en) | 2013-02-14 |
JP5726178B2 (ja) | 2015-05-27 |
DE112011101482T5 (de) | 2013-05-29 |
JPWO2011136355A1 (ja) | 2013-07-22 |
DE112011101482B4 (de) | 2023-03-16 |
US9096506B2 (en) | 2015-08-04 |
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