JPS6245560A - New acrylate and its manufacturing method - Google Patents
New acrylate and its manufacturing methodInfo
- Publication number
- JPS6245560A JPS6245560A JP18478985A JP18478985A JPS6245560A JP S6245560 A JPS6245560 A JP S6245560A JP 18478985 A JP18478985 A JP 18478985A JP 18478985 A JP18478985 A JP 18478985A JP S6245560 A JPS6245560 A JP S6245560A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acrylic acid
- compound
- compound expressed
- expressed
- Prior art date
- 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.)
- Granted
Links
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 description 14
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- -1 acrylate compound Chemical class 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000000976 ink Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- LQRBQCZFSHTUOF-UHFFFAOYSA-N (4-hydroxycyclooctyl) prop-2-enoate Chemical compound OC1CCCCC(OC(=O)C=C)CC1 LQRBQCZFSHTUOF-UHFFFAOYSA-N 0.000 description 2
- MNCACNWCFAACTP-UHFFFAOYSA-N (4-prop-2-enoyloxycyclooctyl) prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC(OC(=O)C=C)CC1 MNCACNWCFAACTP-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- DOFIAZGYBIBEGI-UHFFFAOYSA-N 3-sulfanylphenol Chemical compound OC1=CC=CC(S)=C1 DOFIAZGYBIBEGI-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical group OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- RHLICVJGDZNMDZ-UHFFFAOYSA-N C(C=C)(=O)OC1(CCCCCCC1)OC(C=C)=O Chemical compound C(C=C)(=O)OC1(CCCCCCC1)OC(C=C)=O RHLICVJGDZNMDZ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
Ａ、産業上の利用分野
本発明は下記の一般式（Ｉ）式で表わされる新規なアク
リレート化合物およびそのジノ進法に関づ−るものであ
る。DETAILED DESCRIPTION OF THE INVENTION A. Industrial Application Field The present invention relates to a novel acrylate compound represented by the following general formula (I) and its dino radical.
（式中Ｒは−０１−１またはＣＨ２＝ＣＨＣＯ−を表わ
ず）
＜Ｉ）式で表わされる化合物は、熱、紫外ＩＱ、イオン
化放射線、ラジカル重合開始剤の存在下で容易に単独ｍ
合または仙の不飽和基含有化合物と共重合を行なうこと
ができる。(In the formula, R does not represent -01-1 or CH2=CHCO-) <I) The compound represented by the formula can be easily monomerized in the presence of heat, ultraviolet IQ, ionizing radiation, or a radical polymerization initiator.
Polymerization or copolymerization with compounds containing unsaturated groups can be carried out.
Ｂ、従来の技術 従来より各種のアクリル酸エステル類が知られている。B. Conventional technology Various acrylic esters have been known so far.
例えばアクリル酸メチル、アクリル酸エチル、アクリル
酸２−エチルヘキシル等の単官能モノマーおよびトリメ
チロールプロパントリアクリレ−１−、ペンタエリスリ
トールトリアクリレート等の多官能七ツマ−が一般的に
知られている。For example, monofunctional monomers such as methyl acrylate, ethyl acrylate, and 2-ethylhexyl acrylate, and polyfunctional monomers such as trimethylolpropane triacrylate-1- and pentaerythritol triacrylate are generally known.
Ｃ１発明が解決しようとする問題点
しかしながら、単官能モノマーは、印刷インキおよび塗
料に用いた場合には、硬化後の未反応モノマーの臭気が
はなはだしく問題となる。C1 Problems to be Solved by the Invention However, when monofunctional monomers are used in printing inks and paints, the odor of unreacted monomers after curing poses a significant problem.
また多官能モノマーは、塗料および印刷インキの希釈剤
として用いる場合には、樹脂に対して多債に使用する必
要があり、したがって樹脂のもつ特性が失われるという
欠点を有している。Furthermore, when polyfunctional monomers are used as diluents for paints and printing inks, they have to be used in multiple amounts with respect to resins, and therefore have the disadvantage that the properties of the resins are lost.
Ｄ９問題を解決するだめの手段、作用および効果本発明
者らは、鋭意研究の結果、低粘度かつ低臭気で広範囲に
わたる樹脂への溶解性をイｊ”ｊ’る新規なアクリル酸
エステルを得るに芋った。As a result of intensive research, the present inventors have obtained a novel acrylic ester that has low viscosity, low odor, and has solubility in a wide range of resins. I had potatoes.
このものは、インキ、塗料、接着剤、被覆剤、成型用樹
脂の原料あるいは改質剤として有用である。This product is useful as a raw material or modifier for inks, paints, adhesives, coatings, and molding resins.
木弁明の化合物（Ｉ＞は、（ＩＩ＞式で表わされる１、
４−シクロオクタンジオールをアクリル酪アクリル酸エ
ステルによってエステル化することによって容易に１１
１られるものである。化合１め（ＩＩ）は市販の１，５
−シクロオクタジエンを水和することによって調製でき
る。化合物（ＩＩ ）に対し、エステル化反応を行なう
と（ＩＩＩ）で表わされる４−ヒドロキシシクロオクチ
ル２−プロペノエート
と（ＩＶ ）式で表わされる１、４−シクロオクタンジ
イル ジー２−プロペノエートの混合物を得ることかで
きる。Kibenmei's compound (I> is (II> 1 represented by the formula
11 can be easily obtained by esterifying 4-cyclooctanediol with acrylic butyric acid ester.
1. Compound 1 (II) is commercially available 1,5
- Can be prepared by hydrating cyclooctadiene. When compound (II) is subjected to an esterification reaction, a mixture of 4-hydroxycyclooctyl 2-propenoate represented by (III) and 1,4-cyclooctanediyl di-2-propenoate represented by formula (IV) is obtained. I can do it.
また、（ＩＶ ）式で表わされる１、４−シクロオクタ
ンジイルジー２−プロペノエートは、（Ｉ［Ｉ）で表わ
される４−ヒドロキシシクロオクチル２−プロペノエー
トをアクリル酸またはアクリル酸エステルでエステル化
することによっても得ることかできる。In addition, 1,4-cyclooctanediyl di-2-propenoate represented by formula (IV) can be obtained by esterifying 4-hydroxycyclooctyl 2-propenoate represented by (I[I) with acrylic acid or acrylic acid ester. You can also get it by
アクリル酸を用いてエステル化を行なう場合には触媒を
使用し、生成する水を連続的に系外へ取り出すことによ
り反応は促進される。ここで使用する触媒は、Ｉ酸、ｐ
−１−ルエンスルホン酸、三フッ化ホウ素等のエステル
化触媒として公知のものから任意に選択して使用するこ
とができる。反応により生成した水を分離するには例え
ばトルエンのような共沸溶剤を用いるのが有利である。When esterification is carried out using acrylic acid, the reaction is promoted by using a catalyst and continuously removing the produced water from the system. The catalyst used here is I acid, p
Any known esterification catalyst can be used, such as -1-luenesulfonic acid and boron trifluoride. Advantageously, an azeotropic solvent, such as toluene, is used to separate off the water produced by the reaction.
反応温度は、反応時間の１’Ｊ ｆｉｌと重合防止の点
から７５〜１２０℃で行なわれるのが有利である。アク
リル酸の熱重合を防止づるために重合禁止剤を添加する
。このような重合禁止剤には、ハイドロキノン、ｐ−メ
トキシフェノール、２，４−ジメチル−６−シーブチル
フェノール、３−ヒドロキシチオフェノール、α−ニト
ロソ−β−ナフ１〜−ル、ｐ−ベンゾキノン、２，５−
ジヒドロキシ−〇−キノン、銅塩等が挙げられろ。The reaction temperature is preferably 75 to 120°C from the viewpoint of 1'J fil of reaction time and prevention of polymerization. A polymerization inhibitor is added to prevent thermal polymerization of acrylic acid. Such polymerization inhibitors include hydroquinone, p-methoxyphenol, 2,4-dimethyl-6-shebutylphenol, 3-hydroxythiophenol, α-nitrosol-β-naph1--, p-benzoquinone, ,5-
Examples include dihydroxy-〇-quinone and copper salts.
化合物（１）はアクリル酸エステルと化合１勿（Ｕ）と
のエステル交換反応によって製造することも可能である
。この場合にはアクリル酸のメチル、エチル、ブヂル、
ｎ−プロピル、１ＳＯ−プロピルなど公知のアクリル酸
エステルと化合１℃（ＩＩ）を重合禁止剤と触媒の存在
下でｆｉｌ熱し、生成する該低級アルコールを系外へ取
り出すことによりエステル交換反応を行なう。Compound (1) can also be produced by a transesterification reaction between an acrylic acid ester and Compound 1 (U). In this case, acrylic acid methyl, ethyl, butyl,
Compounding with known acrylic esters such as n-propyl and 1SO-propyl A transesterification reaction is carried out by heating the mixture at 1°C (II) in the presence of a polymerization inhibitor and catalyst, and taking out the resulting lower alcohol from the system. .
この場合にお１プる重合禁止剤どしてはエステル交換反
応の触媒どして硫酸あるいはｐ−トルエンスルホン酸を
用いる場合にはハイドロキノン、ｐ−メトキシフェノー
ルなどを使用するが、金属ナトリウム、ナトリウムアル
コラード、アルミニウムアルコラード、テトラブトキシ
チタンなどアルカリ性の触媒を用いるときにはアルカリ
性のｍ合禁止剤、例えばｐ−フェニレンジアミン、フェ
ニル−β−ナフヂルアミンが使用される。In this case, when using sulfuric acid or p-toluenesulfonic acid as a catalyst for the transesterification reaction, hydroquinone, p-methoxyphenol, etc. are used as the polymerization inhibitor, but metallic sodium, sodium When using alkaline catalysts such as alcolade, aluminum alcolade, and tetrabutoxytitanium, alkaline polymerization inhibitors such as p-phenylenediamine and phenyl-β-naphdylamine are used.
Ｅ、実施例 以下本発明を実施例によって説明する。E. Example The present invention will be explained below with reference to Examples.
〔実施例１〕
還流冷却器、水分離器、撹拌機を備えた反応容器にＤｅ
ｇｇｕｓａ （社）製の化合物（ＩＩ ） １４４９
、アクリルｆｌ １８０ｇ、ｐ−トルエンスルホンｇ１
０ｇ、ｐ−メトキシフェノール５ｇにトルエン４００ｇ
を加え、撹拌しながら３時間加熱した。留出した１−ル
エンー水留分は水分離器において水を分離した後、トル
エンは連続的に反応容器へ返却した。反応後、室温まで
冷部し、飽和炭酸ナトリウム水溶液５００ｍ１で３回洗
浄し、ついで飽和食ｊｎ水によってアルカリ性を示さな
くなるまで洗浄をくり返した。このものに１．１′ −
ビー２−ナフトール５３を加え、真空蒸留を行なって沸
点が１３４℃／ １ ｍｍ ｌ−１ｇの留分（ＩＩＩ
） ５２９と沸点が１４０℃／ １ ｔｒｖｎ Ｈｇの
留分ＣＩＶ） １２２ｇを得た。[Example 1] De was added to a reaction vessel equipped with a reflux condenser, a water separator, and a stirrer.
Compound (II) 1449 manufactured by Ggusa (Inc.)
, acrylic fl 180g, p-toluenesulfone g1
0g, p-methoxyphenol 5g and toluene 400g
was added and heated for 3 hours while stirring. After water was separated from the distilled 1-luene-water fraction in a water separator, toluene was continuously returned to the reaction vessel. After the reaction, the reactor was cooled to room temperature, washed three times with 500 ml of a saturated aqueous sodium carbonate solution, and then washed repeatedly with saturated sodium chloride water until it no longer showed alkalinity. This one has 1.1′ −
Add B-2-naphthol 53 and perform vacuum distillation to obtain a fraction (III
) 122 g of a fraction CIV) having a boiling point of 140° C./1 trvn Hg were obtained.
〔実施例２〕
ヴイグリュー型の分留管、撹拌器、温度計をつけた反応
容器に化合物（ＩＩ ） １４４ｇ、アクリル酸メチ
ルエステル２５８！？、ｌ）−メトキシフェノール５ｇ
、ｐ−トルエンスルホン１１８ｇを加える。[Example 2] 144 g of compound (II) and 258 g of acrylic acid methyl ester were placed in a reaction vessel equipped with a Vigreux-type fractionating tube, a stirrer, and a thermometer. ? , l)-methoxyphenol 5g
, 118 g of p-toluenesulfone are added.
これを油浴中で沸騰するまで加熱し還流を続ける。生成
したメタノールはアクリル酸メチルエステルと共沸混合
物を形成して留出させる。Heat this in an oil bath until it boils and continue to reflux. The generated methanol forms an azeotrope with acrylic acid methyl ester and is distilled off.
５時間反応後過剰のアクリル酸メチルエステルを留出さ
せて室温まで冷却した。このものを飽和炭酸ナトリウム
水溶液５００ｄで３回洗浄し、ついで飽和食塩水によっ
てアルカリ性を示さなくなるまで洗浄した。このものに
１．１′ −ビー２−ナフトール１０ｇを加え、真空蒸
留を行なって、沸点が１３４℃／１ｍＨ９の留分（Ｉ［
［＞６２９と沸点が１４０℃／ １ ｍａｒ Ｈ’Ｊの
留分（ＩＶ） １３２ｇを得た。After 5 hours of reaction, excess acrylic acid methyl ester was distilled off and the mixture was cooled to room temperature. This product was washed three times with 500 d of saturated aqueous sodium carbonate solution, and then washed with saturated saline until it no longer showed alkalinity. 10 g of 1.1'-bi-2-naphthol was added to this and vacuum distillation was carried out to obtain a fraction (I[
132 g of fraction (IV) with a boiling point of 140°C/1 mar H'J was obtained.
〔実施例３〕
実施例２における化合物（ｌｒ）のかわりに化合物（Ｉ
［［） １９８ｇを用いる以外は、実施例２に記載し
たのと同様に操作して、化合物（ＩＶ ）、すなわち１
，４−シクロオクタンジイル ジー２−プロペノエート
２５１ｇを得た。[Example 3] In place of compound (lr) in Example 2, compound (I
Compound (IV), i.e., 1
, 251 g of 4-cyclooctanediyl di-2-propenoate were obtained.
実施例で得られた液体化合物（Ｉ［ｌ）と（［Ｖ ）は
、共に低い臭気であり、下記の性質を有する。Both liquid compounds (I[l) and ([V 2 ) obtained in the examples have low odor and have the following properties.
赤外線吸収スペクトル（Ｋ Ｂ ｒ、ｆｉｌｍ）化合物
波数（ｃｍ−’） 吸収の種類３４２０
水酸基○Ｈ伸縮振動２９６０ ＣＨ伸縮振
動
１７２０ アクリル酸エステルのＣ−〇伸縮振
動
（［［［）１６２８．１６１５ アクリル酸エステル
のＣ）−１２−ＣＨ−伸縮振動
１４００ アクリル酸エステルのＣＨ２＝ＣＨ
−面内変角振動
１１８０ アクリル酸エステルのＣ−〇＝伸縮
振動
２９６０ ＣＨ伸縮振動
１７２０ アクリル酸エステルのＣ＝Ｏ伸縮振
動
１６２８、１６１５ アクリル酸エステルの（ＩＶ
） ＣＨ２＝ ＣＨ−伸縮振動１４００
アクリル酸エステルのＣｌ−１２＝ ＣＨ−
面内変角振動
１１８０ アクリル酸エステルのＣ−〇−伸縮
振動
核磁気共鳴スペクトル
（Ｃ−ＮＭＲ，ＣＤＣＪ２３． 日本電子ＦＸ−６００
）化合物 記号 δ（ｐｐｍ）ａ
１３０．３
ｅ ２７．１．２６．９
ｆ ２２，５
（１２９，８，２９，ｆ３
ｈ ７０．５
化合物
記号 δ（ｐｐｍ）
ａ １３０．２
ｂ １２８．９
ｃ １６５，１
ｄ ７４．Ｏ
ｅ ２７．１
ｆ ２２．４
ｇ３０．０
− へ−Infrared absorption spectrum (K B r, film) Compound Wave number (cm-') Absorption type 3420
Hydroxyl group○H stretching vibration 2960 CH stretching vibration 1720 C-○ stretching vibration of acrylic ester ([[[)1628.1615 C)-12-CH-stretching vibration of acrylic ester 1400 CH2=CH of acrylic ester
- In-plane bending vibration 1180 C of acrylic ester = stretching vibration 2960 CH stretching vibration 1720 C=O stretching vibration of acrylic ester 1628, 1615 (IV
) CH2= CH-Stretching vibration 1400
Acrylic acid ester Cl-12= CH-
In-plane bending vibration 1180 C-〇-stretching vibrational nuclear magnetic resonance spectrum of acrylic acid ester (C-NMR, CDCJ23. JEOL FX-600
) Compound Symbol δ(ppm)a
130.3 e 27.1.26.9 f 22,5 (129,8,29,f3 h 70.5 Compound symbol δ (ppm) a 130.2 b 128.9 c 165,1 d 74.O e 27.1 f 22.4 g30.0 - to
Claims (3)
化合物。 ▲数式、化学式、表等があります▼（ I ） （式中Ｒは−ＯＨまたは▲数式、化学式、表等がありま
す▼ を表わす）(1) An acrylate compound represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R represents -OH or ▲There are mathematical formulas, chemical formulas, tables, etc.▼)
たはアクリル酸エステルを反応させることを特徴とする
下記の一般式（ I ）で表わされるアクリレート化合物
の製造法。 ▲数式、化学式、表等があります▼（ I ） （式中Ｒは−ＯＨまたは▲数式、化学式、表等がありま
す▼ を表わす）(2) A method for producing an acrylate compound represented by the following general formula (I), which comprises reacting 1,4-cyclooctanediol with acrylic acid or an acrylic ester. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) (In the formula, R represents -OH or ▲There are mathematical formulas, chemical formulas, tables, etc.▼)
トにアクリル酸またはアクリル酸エステルを反応させる
ことを特徴とする１，４−シクロオクタンジイルジ−２
−プロペノエートの製造法。(3) 1,4-cyclooctanediyldi-2 characterized by reacting 4-hydroxycyclooctyl 2-propenoate with acrylic acid or an acrylic acid ester
- A method for producing propenoate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18478985A JPS6245560A (en) | 1985-08-22 | 1985-08-22 | New acrylate and its manufacturing method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18478985A JPS6245560A (en) | 1985-08-22 | 1985-08-22 | New acrylate and its manufacturing method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6245560A true JPS6245560A (en) | 1987-02-27 |
| JPH0517898B2 JPH0517898B2 (en) | 1993-03-10 |
Family
ID=16159318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18478985A Granted JPS6245560A (en) | 1985-08-22 | 1985-08-22 | New acrylate and its manufacturing method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6245560A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5326256A (en) * | 1990-11-30 | 1994-07-05 | Tokai Corporation | Igniting device |
-
1985
- 1985-08-22 JP JP18478985A patent/JPS6245560A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5326256A (en) * | 1990-11-30 | 1994-07-05 | Tokai Corporation | Igniting device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0517898B2 (en) | 1993-03-10 |
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