JPH0446134A - Readily reactive monomer and production thereof - Google Patents

Readily reactive monomer and production thereof

Info

Publication number
JPH0446134A
JPH0446134A JP15309690A JP15309690A JPH0446134A JP H0446134 A JPH0446134 A JP H0446134A JP 15309690 A JP15309690 A JP 15309690A JP 15309690 A JP15309690 A JP 15309690A JP H0446134 A JPH0446134 A JP H0446134A
Authority
JP
Japan
Prior art keywords
vinyl ether
formula
iodoethyl
reactive monomer
chloroethyl
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.)
Pending
Application number
JP15309690A
Other languages
Japanese (ja)
Inventor
Shoji Watanabe
渡辺 庄司
Okihiko Hirasa
平佐 興彦
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
National Institute of Advanced Industrial Science and Technology AIST
Original Assignee
Agency of Industrial Science and Technology
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Agency of Industrial Science and Technology filed Critical Agency of Industrial Science and Technology
Priority to JP15309690A priority Critical patent/JPH0446134A/en
Publication of JPH0446134A publication Critical patent/JPH0446134A/en
Pending legal-status Critical Current

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  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

NEW MATERIAL:2-Iodoethyl vinyl ether expressed by formula I. USE:A monomer, having high reactivity and capable of readily introducing functional groups such as amino, alkyl, aryl or alkoxy group in polymerization thereof. PREPARATION:2-Chloroethyl vinyl ether expressed by formula II is reacted with a metallic iodide compound expressed by formula III (M is alkali metallic atom) to afford the objective 2-iodoethyl vinyl ether expressed by formula I.

Description

【発明の詳細な説明】 (産業上の利用分野) 本発明は易反応性単量体及びその製造方法に関するもの
である。さらに詳しくいえば、本発明は容易に反応する
ヨウ化アルキル基を有する2−ヨードエチルビニルエー
テル及びこのものを製造する方法に関するものである。
DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to a highly reactive monomer and a method for producing the same. More particularly, the present invention relates to 2-iodoethyl vinyl ether having an easily reactable alkyl iodide group and a process for making the same.

ビニルエーテル基を有する単量体を重合して得られる高
分子化合物は接着剤、ラッカー及びエナメル、紙及び繊
維製品、ラテックス、感光性樹脂、などを利用する産業
分野において広く利用されているところである。
BACKGROUND ART Polymer compounds obtained by polymerizing monomers having vinyl ether groups are widely used in industrial fields that utilize adhesives, lacquers and enamels, paper and textile products, latex, photosensitive resins, and the like.

(従来の技術) これまで、ビニルエーテル基を有する化合物は数多く知
られているが、技術の進歩に対応するべく、機能を有す
る単量体が求められている。このような要求に対処する
ために、2−クロルエチルビニルエーテルを出発原料と
して色々な機能性単量体が合成されている。しかしなが
ら2−クロルエチルビニルエーテルはそのクロルエチル
基の反応性が低いため、これを用いての機能性単量体の
合成はエステル化するなど、ごく限られた合成方法だけ
であった。
(Prior Art) Many compounds having vinyl ether groups have been known so far, but in order to keep up with technological progress, functional monomers are being sought. In order to meet these demands, various functional monomers have been synthesized using 2-chloroethyl vinyl ether as a starting material. However, since the reactivity of the chloroethyl group in 2-chloroethyl vinyl ether is low, the synthesis of functional monomers using 2-chloroethyl vinyl ether has been limited to only a limited number of synthesis methods, such as esterification.

(発明が解決しようとする課題) 本発明は重合体としたときに、アミノ基、アルキル基、
アリール基、アルコキシ基、等の官能基を容易に導入し
つる反応性の高い単量体を得ることを目的としてなされ
たものである。
(Problems to be Solved by the Invention) The present invention provides that when a polymer is formed, an amino group, an alkyl group,
This was done for the purpose of obtaining a highly reactive monomer into which functional groups such as aryl groups and alkoxy groups can be easily introduced.

(課題を解決するための手段) 本発明者らは、このような従来の低い反応性の単量体の
もつ欠点を克服すべく鋭意研究を重ねた結果、式(1)
で表される単量体が高い反応性を示すことを見いだし、
かつこの化合物を簡便に合成することに成功し、本発明
をなすに至った。
(Means for Solving the Problem) As a result of intensive research to overcome the drawbacks of such conventional monomers with low reactivity, the present inventors have developed the formula (1).
It was discovered that the monomer represented by shows high reactivity,
Moreover, the inventors succeeded in easily synthesizing this compound, leading to the present invention.

すなわち、本発明は 式 %式%(1) で表される2−ヨードエチルビニルエーテル及び CH2=CH0CH2CH2C1−−(2)で表される
2−クロルエチルビニルエーテルに式 %式%(3) (式中のMはアルカリ金属原子である)で表されるヨウ
化金属化合物を反応させることを特徴とする 式 %式%(4) で表される2−ヨードエチルビニルエーテルの製造方法
を提供するものである。
That is, the present invention provides 2-iodoethyl vinyl ether represented by the formula % formula % (1) and 2-chloroethyl vinyl ether represented by CH2=CH0CH2CH2C1--(2) with the formula % formula % (3) (in the formula This invention provides a method for producing 2-iodoethyl vinyl ether represented by the formula % (4), which is characterized by reacting a metal iodide compound represented by (M is an alkali metal atom). .

本発明に於いて用いられるヨウ化金属化合物としてはヨ
ウ化ナトリウム、ヨウ化カリウム、ヨウ化リチウムなど
を挙げることが出来る6反応溶媒はヨウ化金属化合物を
多少なりとも溶解し、2クロルエチルビニルエーテルに
不活性なものが望ましい、そのような例としては、アセ
トン、メチルエチルケトン、N、N−ジメチルアセトア
ミド、N、N−ジメチルホルムアミド、ジメチルスルホ
ニ4シト、ヘキサメチルホスホリックトリアミドなどを
挙げることが出来るがこれに限定されるものではない1
尺応温度は20℃から90℃の範囲が望ましいがこれに
限定されるものではない、また反応時間は5時間から5
0時間の範囲が望ましいがこれに限定されるものではな
い。
Examples of the metal iodide compound used in the present invention include sodium iodide, potassium iodide, lithium iodide, etc.6 The reaction solvent dissolves the metal iodide compound to some extent and converts it into 2-chloroethyl vinyl ether. Inert substances are preferable; examples include acetone, methyl ethyl ketone, N,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfonyl triamide, hexamethylphosphoric triamide, and the like. is not limited to this.1
The reaction temperature is preferably in the range of 20°C to 90°C, but is not limited thereto, and the reaction time is 5 hours to 5 hours.
A range of 0 hours is desirable, but is not limited thereto.

本発明の製造方法においては 式 %式%(2) で表される2−クロルエチルビニルエーテルと式 %式%(3) (式中のMはアルカリ金属原子である)で表されるヨウ
化金属化合物のいずれか1つを反応溶媒中に溶解もしく
は分散させ、所定の時間、温度において反応させた後、
溶媒を除去し、分別蒸留することにより 式 %式%(4) で表される2−ヨードエチルビニルエーテルを容易に得
ることが出来る。
In the production method of the present invention, 2-chloroethyl vinyl ether represented by the formula % (2) and metal iodide represented by the formula % (3) (M in the formula is an alkali metal atom) are used. After dissolving or dispersing any one of the compounds in a reaction solvent and reacting at a predetermined time and temperature,
By removing the solvent and performing fractional distillation, 2-iodoethyl vinyl ether represented by the formula % (4) can be easily obtained.

(発明の効果) 本発明によって提供される易反応性単量体はアルキル化
やアミノ化などを容易に施すことが出来るため、接着剤
、ラッカー及びエナメル、紙及び繊維製品、ラテックス
、感光性樹脂、などを利用する産業分野はもちろんのこ
と薬剤の徐放用材料、高分子作用素子、感熱性高分子な
どの合成原料として好適である。
(Effect of the invention) The easily reactive monomer provided by the present invention can be easily subjected to alkylation, amination, etc., so it can be used in adhesives, lacquers and enamels, paper and textile products, latex, photosensitive resins, etc. It is suitable not only for industrial fields where it is used, but also as a raw material for the synthesis of materials for sustained release of drugs, polymeric active elements, heat-sensitive polymers, etc.

(実施例) 次に本発明を実施例により詳細に説明する。(Example) Next, the present invention will be explained in detail with reference to examples.

実施例 1 ヨウ化ナトリウム111gと2−クロルエチルビニルエ
ーテル53gを乾燥したアセトン500m1に溶解させ
、この溶液を52時間還流する。
Example 1 111 g of sodium iodide and 53 g of 2-chloroethyl vinyl ether are dissolved in 500 ml of dry acetone and the solution is refluxed for 52 hours.

この溶液を冷却後、析出した固形物をろ過により除去し
、アセトンをロータリーエバポレーターで留去する。得
られた残渣を減圧蒸留し、58−59℃(46mmHg
)の沸点留分を捕集すると2ヨ一ドエチルビニルエーテ
ル118gが得られる、赤外線吸収スペクトルにより6
37.579.522cm−’にC−I結合に基づく吸
収、955゜827cm−’にビニル基に基づく吸収、
1640゜1620cm−’に二重結合に基づく吸収を
確認した。またプロトン核磁気共鳴吸収によりδ=3゜
31及び3.97にエチレン基に基づく吸収、δ4.0
8,4.22及び6.45に二重結合のプロトンに基づ
く吸収を確認した。
After cooling this solution, the precipitated solid matter is removed by filtration, and the acetone is distilled off using a rotary evaporator. The resulting residue was distilled under reduced pressure at 58-59°C (46mmHg
) was collected to obtain 118 g of 2-iodoethyl vinyl ether. According to the infrared absorption spectrum, 6
Absorption based on C-I bond at 37.579.522 cm-', absorption based on vinyl group at 955°827 cm-',
Absorption based on double bonds was confirmed at 1640° and 1620 cm-'. In addition, by proton nuclear magnetic resonance absorption, absorption based on ethylene group at δ = 3°31 and 3.97, δ4.0
Absorption based on double bond protons was confirmed at 8, 4.22 and 6.45.

また質量分析法により質量数197.85に分子イオン
ビークを確認した。
Furthermore, a molecular ion beak was confirmed at a mass number of 197.85 by mass spectrometry.

実施例 2 2−クロルエチルビニルエーテル11.5gを乾燥した
アセトン500 m lに溶解させ、この溶液にヨウ化
カリウム20gを分散させ52時間還流する。この溶液
を冷却後、析出した固形物をろ過により除去し、アセト
ンをロータリーエバポレターで留去する。得られた残渣
を減圧蒸留し、沸点留分58−59℃(46m m H
g )を捕集すると2−ヨードエチルビニルエーテル1
7gが得られる。赤外線吸収スペクトルにより637.
579.522crn−’にC−I結合に基づく吸収、
955.827cm−’にビニル基に基づく吸収、16
40.1620cm−’に二重結合に基づく吸収を確認
した。またプロトン核磁気共鳴吸収によりδ=3.31
及び3.97にエチレン基に基づく吸収、δ=4.08
,4.22及び6.45に二重結合のプロトンに基づく
吸収を確認した。カボン13核磁気共鳴吸収によりδ−
1,68゜5.87.6,150.8に炭素による吸収
を確認した。
Example 2 11.5 g of 2-chloroethyl vinyl ether is dissolved in 500 ml of dry acetone, 20 g of potassium iodide is dispersed in this solution, and the mixture is refluxed for 52 hours. After cooling this solution, the precipitated solid matter is removed by filtration, and the acetone is distilled off using a rotary evaporator. The obtained residue was distilled under reduced pressure to obtain a boiling point fraction of 58-59°C (46 mm H
g) is collected, 2-iodoethyl vinyl ether 1
7g is obtained. 637. by infrared absorption spectrum.
Absorption based on C-I bond at 579.522crn-',
Absorption based on vinyl group at 955.827 cm-', 16
Absorption based on double bonds was confirmed at 40.1620 cm-'. Also, by proton nuclear magnetic resonance absorption, δ=3.31
and absorption based on ethylene group at 3.97, δ = 4.08
, 4.22 and 6.45, absorption based on double bond protons was confirmed. By carbon-13 nuclear magnetic resonance absorption, δ-
Absorption by carbon was confirmed at 1,68°5.87.6,150.8.

また質量分析法により質量数197.85に分子イオン
ビークを確認した。
Furthermore, a molecular ion beak was confirmed at a mass number of 197.85 by mass spectrometry.

実施例 3 2−クロルエチルビニルエーテル3.45gを乾燥した
メチルエチルケトン200 m lに溶解させ、この溶
液にヨウ化カリウム6gを分散させ50時間還流する。
Example 3 3.45 g of 2-chloroethyl vinyl ether is dissolved in 200 ml of dry methyl ethyl ketone, 6 g of potassium iodide is dispersed in this solution, and the mixture is refluxed for 50 hours.

この溶液を冷却後、析出した固形物をろ過により除去し
、メチルエチルケトンをロータリーエバポレーターで留
去する。得られた残渣を減圧蒸留し、沸点留分58−5
9℃(46m m Hg )を捕集すると2−ヨードエ
チルビニルエーテル4.8gが得られる。
After cooling this solution, the precipitated solid matter is removed by filtration, and methyl ethyl ketone is distilled off using a rotary evaporator. The obtained residue was distilled under reduced pressure to obtain boiling point fraction 58-5.
Collecting at 9°C (46 mm Hg) yields 4.8 g of 2-iodoethyl vinyl ether.

得られた化合物は実施例2と同様の方法により2−ヨー
ドエチルビニルエーテルであることを確認した。
The obtained compound was confirmed to be 2-iodoethyl vinyl ether in the same manner as in Example 2.

実施例 4 2−クロルエチルビニルエーテル18.3gとヨウ化リ
チウム25.7gを乾燥したアセトン250m1に溶解
させ、この溶液を40時間還流する。この溶液を冷却後
、析出した固形物をろ過により除去し、アセトンをロー
タリーエバポレーターで留去する。得られた残渣を減圧
蒸留し、沸点留分58−59℃(46m m Hg )
を捕集して2−ヨードエチルビニルエーテル29gを得
た。得られた化合物は実施例2と同様の方法により2ヨ
ードエチルビニルエーテルであることを確認した。
Example 4 18.3 g of 2-chloroethyl vinyl ether and 25.7 g of lithium iodide are dissolved in 250 ml of dry acetone and the solution is refluxed for 40 hours. After cooling this solution, the precipitated solid matter is removed by filtration, and the acetone is distilled off using a rotary evaporator. The obtained residue was distilled under reduced pressure to obtain a boiling point fraction of 58-59°C (46 mm Hg).
was collected to obtain 29 g of 2-iodoethyl vinyl ether. The obtained compound was confirmed to be 2-iodoethyl vinyl ether in the same manner as in Example 2.

実施例 5 2−クロルエチルビニルエーテル9.54gとヨウ化カ
リウム16.6gを乾燥したN、N−ジメチルアセトア
ミドl OOm lに溶解させ、この溶液を90℃にて
40時間加熱する。この溶液を冷却後、過剰の飽和炭酸
水素ナトリウム水溶液に注油し、水層をジエチルエーテ
ルで抽出し、炭酸ナトリウム上で乾燥する。乾燥剤を除
去後、エテルを留去し、残漬を減圧蒸留し、沸点留分5
859℃(46m m Hg )を捕集して2−ヨード
エチルビニルエーテル13.4gを得た。得られた化合
物は実施例2と同様の方法により2−ヨドエチルビニル
エーテルであることを確認した。
Example 5 9.54 g of 2-chloroethyl vinyl ether and 16.6 g of potassium iodide are dissolved in lOOml of dry N,N-dimethylacetamide and the solution is heated at 90°C for 40 hours. After cooling the solution, it is poured into excess saturated aqueous sodium bicarbonate solution, and the aqueous layer is extracted with diethyl ether and dried over sodium carbonate. After removing the desiccant, ether is distilled off, and the residue is distilled under reduced pressure to obtain boiling point fraction 5.
859° C. (46 mm Hg) was collected to obtain 13.4 g of 2-iodoethyl vinyl ether. The obtained compound was confirmed to be 2-iodoethyl vinyl ether in the same manner as in Example 2.

Claims (1)

【特許請求の範囲】 1 式 CH_2=CHOCH_2CH_2I−−−(1) で表される2−ヨードエチルビニルエーテル。 2 式 CH_2=CHOCH_2CH_2Cl−−(2) で表される2−クロルエチルビニルエーテルに式 MI−−−−−−(3) (式中のMはアルカリ金属原子である) で表されるヨウ化金属化合物を反応させることを特徴と
する式 CH_2=CHOCH_2CH_2I−−−(4) で表される2−ヨードエチルビニルエーテルの製造方法
[Claims] 1 2-iodoethyl vinyl ether represented by the formula CH_2=CHOCH_2CH_2I---(1). 2 2-chloroethyl vinyl ether represented by the formula CH_2=CHOCH_2CH_2Cl--(2) and metal iodide represented by the formula MI---(3) (M in the formula is an alkali metal atom) A method for producing 2-iodoethyl vinyl ether represented by the formula CH_2=CHOCH_2CH_2I---(4), which comprises reacting a compound.
JP15309690A 1990-06-12 1990-06-12 Readily reactive monomer and production thereof Pending JPH0446134A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP15309690A JPH0446134A (en) 1990-06-12 1990-06-12 Readily reactive monomer and production thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP15309690A JPH0446134A (en) 1990-06-12 1990-06-12 Readily reactive monomer and production thereof

Publications (1)

Publication Number Publication Date
JPH0446134A true JPH0446134A (en) 1992-02-17

Family

ID=15554887

Family Applications (1)

Application Number Title Priority Date Filing Date
JP15309690A Pending JPH0446134A (en) 1990-06-12 1990-06-12 Readily reactive monomer and production thereof

Country Status (1)

Country Link
JP (1) JPH0446134A (en)

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRCTS=19706V2 *

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