JPH0446134A - Readily reactive monomer and production thereof - Google Patents
Readily reactive monomer and production thereofInfo
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000000178 monomer Substances 0.000 title abstract description 11
- GKFAEUUIDLYIQV-UHFFFAOYSA-N 1-ethenoxy-2-iodoethane Chemical compound ICCOC=C GKFAEUUIDLYIQV-UHFFFAOYSA-N 0.000 claims abstract description 16
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910001511 metal iodide Inorganic materials 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- -1 iodide compound Chemical class 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000010521 absorption reaction Methods 0.000 description 14
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 210000003323 beak Anatomy 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- 125000002538 alkyl iodide group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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)
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.
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)
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JP (1) | JPH0446134A (en) |
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1990
- 1990-06-12 JP JP15309690A patent/JPH0446134A/en active Pending
Non-Patent Citations (1)
Title |
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CHEMICAL ABSTRCTS=19706V2 * |
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