JPH0368874B2 - - Google Patents
Info
- Publication number
- JPH0368874B2 JPH0368874B2 JP58194359A JP19435983A JPH0368874B2 JP H0368874 B2 JPH0368874 B2 JP H0368874B2 JP 58194359 A JP58194359 A JP 58194359A JP 19435983 A JP19435983 A JP 19435983A JP H0368874 B2 JPH0368874 B2 JP H0368874B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- formula
- solvent
- ethylenically unsaturated
- acid
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000009102 absorption Effects 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000000976 ink Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- UZUODNWWWUQRIR-UHFFFAOYSA-L disodium;3-aminonaphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C1=CC=C(S([O-])(=O)=O)C2=CC(N)=CC(S([O-])(=O)=O)=C21 UZUODNWWWUQRIR-UHFFFAOYSA-L 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YXAOOTNFFAQIPZ-UHFFFAOYSA-N 1-nitrosonaphthalen-2-ol Chemical compound C1=CC=CC2=C(N=O)C(O)=CC=C21 YXAOOTNFFAQIPZ-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- QFSYADJLNBHAKO-UHFFFAOYSA-N 2,5-dihydroxy-1,4-benzoquinone Chemical compound OC1=CC(=O)C(O)=CC1=O QFSYADJLNBHAKO-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UBUCNCOMADRQHX-UHFFFAOYSA-N N-Nitrosodiphenylamine Chemical compound C=1C=CC=CC=1N(N=O)C1=CC=CC=C1 UBUCNCOMADRQHX-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Description
【発明の詳細な説明】
本発明は、新規なエチレン性不飽和化合物およ
びその製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel ethylenically unsaturated compound and a method for producing the same.
近年紫外線硬化型印刷インキ及び塗料等が普及
してきている。これらの印刷インキ及び塗料には
ビヒクルとして多くの種類のアクリル酸エステル
が使用されている。 In recent years, ultraviolet curable printing inks, paints, etc. have become popular. Many types of acrylic esters are used as vehicles in these printing inks and paints.
本発明者らは鋭意研究の結果、紫外線硬化型印
刷インキ及び塗料のビヒクルとして有用な新規な
エチレン性不飽和化合物を得るに至つた。 As a result of intensive research, the present inventors have obtained a novel ethylenically unsaturated compound useful as a vehicle for ultraviolet curable printing inks and paints.
すなわち本発明は (1) 一般式 （式中、R1はＨ、又はCH3を示す。） で表わされるエチレン性不飽和化合物。 That is, the present invention is based on (1) general formula (In the formula, R 1 represents H or CH 3. ) An ethylenically unsaturated compound represented by:
(2) 下記式〔〕
で表わされる化合物をアクリル酸もしくはメタク
リル酸でエステル化する事を特徴とする下記一般
式〔〕で表わされるエチレン性不飽和化合物の
製造法である。(2) The following formula [] This is a method for producing an ethylenically unsaturated compound represented by the following general formula [], which is characterized by esterifying the compound represented by acrylic acid or methacrylic acid.
（但し、式〔〕中、R1はＨ、又はCH3を示
す。）
更に詳しく説明するならば、本発明に用いる前
記式〔〕を有する化合物は、２，２−ジメチル
−３−オキシプロパナールとペンタエリスリトー
ルとの縮合によつて得られたものである。 (However, in formula [], R 1 represents H or CH 3. ) To explain in more detail, the compound having the above formula [] used in the present invention is 2,2-dimethyl-3-oxypropylene. It is obtained by condensation of Panhard and pentaerythritol.
またアクリル酸またはメタクリル酸は化学量論
比以上に使用されるのが通常である。一般にアル
コールに対するカルボン酸のモル比は1.0〜2.0で
あるが好ましくは1.1〜1.5である。 Further, acrylic acid or methacrylic acid is usually used in an amount greater than the stoichiometric ratio. Generally, the molar ratio of carboxylic acid to alcohol is 1.0 to 2.0, preferably 1.1 to 1.5.
反応は触媒を使用し生成する水は蒸留する事に
よつて促進される。この様な触媒は、硫酸、Ｐ−
トルエンスルホン酸等の酸性触媒であり、その使
用量はアクリル酸またはメタクリル酸に対して
0.1〜10モル％、好ましくは１〜５モル％使用さ
れる。 The reaction is accelerated by using a catalyst and by distilling the water produced. Such catalysts include sulfuric acid, P-
It is an acidic catalyst such as toluenesulfonic acid, and the amount used is relative to acrylic acid or methacrylic acid.
It is used in an amount of 0.1 to 10 mol%, preferably 1 to 5 mol%.
反応により生成した水を蒸留するのには共沸溶
剤を用いるのが有利である。このような共沸溶剤
は60℃〜130℃の沸点を有し、水と分離し易いも
のなら使用できるが、ｎ−ヘキサン、ｎ−ヘプタ
ンのような脂肪族炭化水素、ベンゼン、トルエン
のような芳香族炭化水素、シクロヘキサンのよう
な脂環式炭化水素が適している。 Advantageously, an azeotropic solvent is used to distill the water produced by the reaction. Such azeotropic solvents can be used as long as they have a boiling point of 60℃ to 130℃ and can be easily separated from water, but aliphatic hydrocarbons such as n-hexane and n-heptane, benzene, and toluene can be used. Aromatic hydrocarbons and cycloaliphatic hydrocarbons such as cyclohexane are suitable.
その使用量は、通常、反応混合物の５〜70重量
パーセントである。反応温度は、60〜130℃の範
囲でよいが、反応時間の短縮と重合防止の点か
ら、75〜120℃で行われるのが有利である。 The amount used is usually 5 to 70 percent by weight of the reaction mixture. The reaction temperature may range from 60 to 130°C, but from the viewpoint of shortening the reaction time and preventing polymerization, it is advantageous to carry out the reaction at a temperature of 75 to 120°C.
アクリル酸またはメタクリル酸には既に重合防
止剤が添加されているのが普通であるが、反応時
に改めて重合防止剤を添加してもよい。そのよう
な重合防止剤には、ハイドロキノン、Ｐ−メトキ
シフエノール、２，４−ジメチル−６−ｔ−ブチ
ルフエノール、３−ヒドロキシチオフエノール、
α−ニトロソ−β−ナフトール、ｐ−ベンゾキノ
ン、２，５−ジヒドロキシ−ｐ−キノン、フエノ
チアジン、Ｎ−ニトロソジフエニルアミン、銅塩
等が挙げられる。その使用量は通常反応混合物に
対して0.01〜１重量％である。 Although a polymerization inhibitor is usually already added to acrylic acid or methacrylic acid, the polymerization inhibitor may be added again during the reaction. Such polymerization inhibitors include hydroquinone, P-methoxyphenol, 2,4-dimethyl-6-t-butylphenol, 3-hydroxythiophenol,
Examples include α-nitroso-β-naphthol, p-benzoquinone, 2,5-dihydroxy-p-quinone, phenothiazine, N-nitrosodiphenylamine, copper salt, and the like. The amount used is usually 0.01 to 1% by weight based on the reaction mixture.
本発明のエチレン性不飽和化合物は、必要なら
ば水若しくはアルカリ水溶液等で洗浄したり、減
圧蒸留のような方法で溶剤と分離する事によつ
て、工業的用途に使用される。このエチレン性不
飽和化合物〔〕は、塗料及びインキ組成物のビ
ヒクルとして有用であり、それらは適当な重合開
始方法、紫外線又は電子線の照射等により、又は
有機過酸化物の添加によりホモリムマー又はコポ
リマーを生成可能である。 The ethylenically unsaturated compound of the present invention can be used for industrial purposes by washing it with water or an aqueous alkali solution, if necessary, or by separating it from the solvent by a method such as vacuum distillation. These ethylenically unsaturated compounds are useful as vehicles for coating and ink compositions, and they can be prepared into homolimmers or copolymers by suitable polymerization initiation methods, such as by irradiation with ultraviolet or electron beams, or by the addition of organic peroxides. It is possible to generate
以下実施例を以つて説明する。例中、部とは重
量部を示す。 Examples will be described below. In the examples, parts indicate parts by weight.
実施例 １
撹拌機、温度調節装置、温度計、凝縮器及び分
離器を備えた2l反応器に、２，２−ジメチル−３
−オキシプロパナールとペンタエリスリトールの
縮合体である下記の構造を有する化合物
220部、アクリル酸259.4部、ｐ−トルエンスル
ホン酸25部、ハイドロキノン２部、ベンゼン320
部、シクロヘキサン80部を仕込み、加熱し、生成
水は溶剤と共に蒸留、凝縮させ分離器で水のみ系
外に取り除き、溶剤は反応器に戻す。水が54部生
成した時点で冷却した。反応温度は80℃〜87℃で
あつた。反応混合物をベンゼン400部、シクロヘ
キサン100部に溶解し、20％苛性ソーダ水溶液で
中和した後、20％食塩水200部で３回洗浄する。
溶剤を減圧留去して下記の構造を有する淡黄色の
固体367部を得た。Example 1 In a 2 l reactor equipped with a stirrer, temperature regulator, thermometer, condenser and separator, 2,2-dimethyl-3
-A compound having the following structure that is a condensate of oxypropanal and pentaerythritol 220 parts, acrylic acid 259.4 parts, p-toluenesulfonic acid 25 parts, hydroquinone 2 parts, benzene 320 parts
1 part and 80 parts of cyclohexane are charged, heated, and the produced water is distilled and condensed together with the solvent. Only the water is removed from the system in a separator, and the solvent is returned to the reactor. Cooling occurred when 54 parts of water had been produced. The reaction temperature was 80°C to 87°C. The reaction mixture was dissolved in 400 parts of benzene and 100 parts of cyclohexane, neutralized with 20% aqueous sodium hydroxide solution, and washed three times with 200 parts of 20% brine.
The solvent was distilled off under reduced pressure to obtain 367 parts of a pale yellow solid having the following structure.
このものは、下記の性質を有する。 This material has the following properties.
融 点 70〜76℃
酸 価 （mgKOH／ｇ） 0.02
ケン化価 （mgKOH／ｇ） 438.5
元素分析 Ｃ（％） Ｈ（％）
59.27 6.82
得られた生成物の高分解核磁気共鳴（NMR）
による吸収周波数の測定を行つた結果を下記に示
す。 Melting point 70-76℃ Acid value (mgKOH/g) 0.02 Saponification value (mgKOH/g) 438.5 Elemental analysis C (%) H (%) 59.27 6.82 High resolution nuclear magnetic resonance (NMR) of the obtained product
The results of absorption frequency measurements are shown below.
No. 吸収周波数（Hz）
１ 11281.2
２ 11259.2
３ 11250.4
４ 8945.7
５ 8939.1
６ 8917.0
７ 8906.0
８ 8864.2
９ 8859.7
10 8732.0
11 8701.1
12 8694.5
13 8681.3
14 8672.5
15 7132.3
16 7121.3
17 5272.7
18 5239.6
19 5206.6
20 4796.7
21 4763.7
22 4732.8
23 4710.8
24 4706.4
25 4702.0
26 4334.0
27 4307.6
28 4252.5
29 4245.9
30 4217.2
31 4131.3
32 2630.8
33 2533.9
34 1330.8
35 1324.2
36 1313.2
37 0.0
猶上記測定には基準物質としてテトラメチルシ
ランを用い、溶媒としてクロロホルムを用いH′，
C13−Ｈのカツプリングさせた測定をして最終的
にC13のＤカツプルの同定結果を示した。上記吸
収のうち、No.17，18，19は溶媒の吸収のピーク位
置を示す。 No. Absorption frequency (Hz) 1 11281.2 2 11259.2 3 11250.4 4 8945.7 5 8939.1 6 8917.0 7 8906.0 8 8864.2 9 8859.7 10 8732.0 11 8701.1 12 8694.5 1 3 8681.3 14 8672.5 15 7132.3 16 7121.3 17 5272.7 18 5239.6 19 5206.6 20 4796.7 21 4763.7 22 4732.8 23 4710.8 24 4706.4 25 4702.0 26 4334.0 27 4307.6 28 4252.5 29 4245.9 30 4217.2 31 4131.3 32 2630.8 33 2533.9 34 133 0.8 35 1324.2 36 1313.2 37 0.0 In the above measurements, tetramethylsilane was used as the reference material and chloroform was used as the solvent. H′,
A coupled measurement of C 13 -H was performed, and the results finally showed the identification of the D couple of C 13 . Among the above absorptions, Nos. 17, 18, and 19 indicate the absorption peak positions of the solvent.
実施例 ２
撹拌機、温度調節装置、温度計、凝縮器及び分
離器を備えた2l反応器に、２，２−ジメチル−３
−オキシプロパナールとペンタエリスリトールの
縮合体である下記の構造を有する化合物
220部、メタクリル酸309.6部、Ｐ−トルエンス
ルホン酸25部、ハイドロキノン２部、トルエン
400部を仕込み、加熱し、生成水は溶剤と共に蒸
留、凝縮させ分離器で水のみ系外に取り除き、溶
剤は反応器に戻す。水が54部生成した時点で冷却
した。反応温度は110℃〜117℃であつた。反応混
合物をトルエン500部に溶解し、20％苛性ソーダ
水溶液で中和した後、20％食塩水200部で３回洗
浄する。溶剤を減圧留去して下記の構造を有する
淡黄色の固体350部を得た。Example 2 In a 2 l reactor equipped with a stirrer, temperature controller, thermometer, condenser and separator, 2,2-dimethyl-3
-A compound having the following structure that is a condensate of oxypropanal and pentaerythritol 220 parts, 309.6 parts of methacrylic acid, 25 parts of P-toluenesulfonic acid, 2 parts of hydroquinone, toluene
400 parts are charged and heated, the produced water is distilled and condensed together with the solvent, only the water is removed from the system in a separator, and the solvent is returned to the reactor. Cooling occurred when 54 parts of water had been produced. The reaction temperature was 110°C to 117°C. The reaction mixture is dissolved in 500 parts of toluene, neutralized with 20% aqueous sodium hydroxide solution, and washed three times with 200 parts of 20% brine. The solvent was distilled off under reduced pressure to obtain 350 parts of a pale yellow solid having the following structure.
このものは、下記の性質を有する。 This material has the following properties.
融 点 55〜60℃
酸 価 （mgKOH／ｇ） 0.03
ケン化価（mgKOH／ｇ） 394.7
元素分析 Ｃ（％） Ｈ（％）
62.10 7.78
得られた生成物の高分解核磁気共鳴（NMR）
による吸収周波数の測定を行つた結果を下記に示
す。 Melting point 55-60℃ Acid value (mgKOH/g) 0.03 Saponification value (mgKOH/g) 394.7 Elemental analysis C (%) H (%) 62.10 7.78 High resolution nuclear magnetic resonance (NMR) of the obtained product
The results of absorption frequency measurements are shown below.
No. 吸収周波数（Hz）
１ 11358.4
２ 11336.3
３ 11329.7
４ 9274.0
５ 9243.1
６ 9221.1
７ 8582.1
８ 8577.7
９ 8573.3
10 8544.7
11 8502.8
12 7134.5
13 5270.5
14 5237.4
15 5206.6
16 4801.1
17 4768.1
18 4739.4
19 4724.0
20 4719.6
21 4715.2
22 4706.4
23 4699.8
24 4318.6
25 4272.3
26 4265.7
27 2635.2
28 2547.1
29 1328.6
30 1319.8
31 1242.7
32 1238.3
上記吸収ピークの内、No.13，14，15は溶媒の吸
収ピークの位置を示す。 No. Absorption frequency (Hz) 1 11358.4 2 11336.3 3 11329.7 4 9274.0 5 9243.1 6 9221.1 7 8582.1 8 8577.7 9 8573.3 10 8544.7 11 8502.8 12 7134.5 1 3 5270.5 14 5237.4 15 5206.6 16 4801.1 17 4768.1 18 4739.4 19 4724.0 20 4719.6 21 4715.2 22 4706.4 23 4699.8 24 4318.6 25 4272.3 26 4265.7 27 2635.2 28 2547.1 29 1328.6 30 1319.8 31 1242.7 32 1238.3 Among the above absorption peaks, Nos. 13, 14, and 15 are The position of the absorption peak of the solvent is shown.
Claims (1)
れるエチレン性不飽和化合物。 ２ 下記式〔〕 で表わされる化合物をアクリル酸もしくはメタク
リル酸でエステル化する事を特徴とする下記一般
式〔〕で表わされるエチレン性不飽和化合物の
製造法。 （但し、式〔〕中、R1はＨ、又はCH3を示
す。）[Claims] 1. General formula (In the formula, R 1 represents H or CH 3. ) An ethylenically unsaturated compound represented by the formula: 2 The following formula [] A method for producing an ethylenically unsaturated compound represented by the following general formula [], which comprises esterifying the compound represented by acrylic acid or methacrylic acid. (However, in formula [], R 1 represents H or CH 3. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58194359A JPS6087280A (en) | 1983-10-19 | 1983-10-19 | Ethylenic unsaturated compound and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58194359A JPS6087280A (en) | 1983-10-19 | 1983-10-19 | Ethylenic unsaturated compound and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6087280A JPS6087280A (en) | 1985-05-16 |
| JPH0368874B2 true JPH0368874B2 (en) | 1991-10-30 |
Family
ID=16323262
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58194359A Granted JPS6087280A (en) | 1983-10-19 | 1983-10-19 | Ethylenic unsaturated compound and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6087280A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5490588B2 (en) * | 2010-03-23 | 2014-05-14 | 三洋化成工業株式会社 | Polymerizable compound and ink composition for ink jet printing ink |
-
1983
- 1983-10-19 JP JP58194359A patent/JPS6087280A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6087280A (en) | 1985-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4187383A (en) | Process for producing low color residue acrylate esters | |
| US3487101A (en) | Preparation of methacrylic compounds by dehydration of alpha - hydroxybutyric acid compounds | |
| US4187382A (en) | Process for producing low color residue acrylate ester monomers | |
| US4076727A (en) | Cyclic acetal acrylates or methacrylates and processes for preparing same | |
| JP4092740B2 (en) | Method for esterifying (meth) acrylic acid | |
| JP2001508076A (en) | Esterification method of (meth) acrylic acid and alkanol | |
| US4458088A (en) | Continuous process for the extraction and esterification of carboxylic acid | |
| US6187946B1 (en) | Jasmonic acid compounds and process for the preparation thereof | |
| EP0465853B1 (en) | Method for producing 4-hydroxybutyl (meth)acrylate | |
| JPH0368874B2 (en) | ||
| JPH11100375A (en) | Production of (meth) acryloylmorpholine | |
| EP0103684B1 (en) | Acryloyloxy groups containing 1,3-dioxane derivatives, and process for producing them | |
| JPS5978193A (en) | Ethylenically unsaturated compounds and their production method | |
| JPH0239495B2 (en) | ||
| JPH0368870B2 (en) | ||
| JPH0372219B2 (en) | ||
| JPH0376312B2 (en) | ||
| JP3443780B2 (en) | Method for producing phenoxy polyalkylene glycol acrylate | |
| JPH03120263A (en) | Preparation of (meth)acrylate compound | |
| JPH0368872B2 (en) | ||
| JPH0368871B2 (en) | ||
| JPH10175918A (en) | Production of tetrahydrobenzyl (meth)acrylate | |
| JPS626699B2 (en) | ||
| JPH034076B2 (en) | ||
| JPH0145470B2 (en) |