JPH01265082A - Oxirane-carboxylic acid ester - Google Patents
Oxirane-carboxylic acid esterInfo
- Publication number
- JPH01265082A JPH01265082A JP9221888A JP9221888A JPH01265082A JP H01265082 A JPH01265082 A JP H01265082A JP 9221888 A JP9221888 A JP 9221888A JP 9221888 A JP9221888 A JP 9221888A JP H01265082 A JPH01265082 A JP H01265082A
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- oxirane
- acid ester
- ester
- 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.)
- Pending
Links
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 229920001477 hydrophilic polymer Polymers 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- 239000003792 electrolyte Substances 0.000 abstract description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract description 3
- 150000004965 peroxy acids Chemical class 0.000 abstract description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 abstract description 3
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 abstract 1
- COORVRSSRBIIFJ-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]-1-methoxyethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(O)COCCOCCO COORVRSSRBIIFJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003906 humectant Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 8
- -1 acrylic ester Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000466 oxiranyl group Chemical group 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 229920001221 xylan Polymers 0.000 description 3
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- ZDTLUUIYCAMIMQ-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.COC(O)COCCO ZDTLUUIYCAMIMQ-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- ZAOJWJAARUYTMA-UHFFFAOYSA-N 4-chloro-2-(5-chloro-2-hydroxy-3-nitrophenyl)sulfanyl-6-nitrophenol Chemical compound C1=C(Cl)C=C([N+]([O-])=O)C(O)=C1SC1=CC(Cl)=CC([N+]([O-])=O)=C1O ZAOJWJAARUYTMA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000218645 Cedrus Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920003174 cellulose-based polymer Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229920003179 starch-based polymer Polymers 0.000 description 1
- 239000004628 starch-based polymer Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 150000004823 xylans Chemical class 0.000 description 1
Landscapes
- Epoxy Compounds (AREA)
- Polyethers (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、オキシランカルボン酸エステルからなる新規
化合物に関する。ざらに詳しくは、親水性に富んだポリ
マーの原料として有用なモノマーに関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel compound consisting of an oxirane carboxylic acid ester. More specifically, the present invention relates to monomers useful as raw materials for highly hydrophilic polymers.
親水性ポリマーは例えば、その吸水性に着目し、生理用
品や紙おむつ、農林用の保水剤などのほか、脱水剤、水
性ゲル基材、結露防止剤、油中の水分除去剤、電解質の
媒体などとして広汎な用途がある。For example, hydrophilic polymers are used for their water absorbing properties, and are used in sanitary products, disposable diapers, water retention agents for agriculture and forestry, as well as dehydrating agents, aqueous gel base materials, anti-condensing agents, agents for removing moisture from oil, and electrolyte media. It has a wide range of uses.
［従来の技術］
従来、吸水性ポリマーとしては、
（１） デンプン系のもの（デンプン−ポリアクリロ
ニトリルグラフト重合加水分解物、デンプン−アクリル
酸グラフト共重合物）、
（２）セルロース系の：しの（カルボキシメチルセルロ
−ス
トリルグラフ１〜体加水分解物）、
（３） 合成樹脂系のもの（ポリアクリル酸ソーダ、
メチルメタクリル酸−酢酸ビニル共重合体加水分解物、
ポリビニルアルコール架橋重合物、ポリアクリロニトリ
ル架橋体加水分解物、ポリエチレンオキシド架橋重合体
）
などが用いられてきた。[Prior art] Conventionally, water-absorbing polymers include (1) starch-based polymers (starch-polyacrylonitrile graft polymerization hydrolyzate, starch-acrylic acid graft copolymer), (2) cellulose-based polymers: (carboxymethylcellulosetril graph 1 ~ body hydrolyzate), (3) Synthetic resin type (sodium polyacrylate,
Methyl methacrylic acid-vinyl acetate copolymer hydrolyzate,
Polyvinyl alcohol crosslinked polymers, polyacrylonitrile crosslinked hydrolysates, polyethylene oxide crosslinked polymers, etc. have been used.
また別の公知例としては、エヂレングリコールエポキシ
アクリレートという下記の化合物をモノマーとするポリ
マーが、保水性材料として知られている（特開昭６０−
１６６２５１号公報）。As another known example, a polymer containing the following compound called ethylene glycol epoxy acrylate as a monomer is known as a water-retentive material (Japanese Patent Application Laid-open No. 1983-1992-1).
166251).
［発明が解決しようとする課題］
しかし、上記ポリマーは吸水力が小さく、これはとくに
電解７１水溶液にとって好ましくない。また吸収速度が
遅いという問題点がおり、さらに製造工程が繁雑である
などの実用上の問題点がある。[Problems to be Solved by the Invention] However, the above-mentioned polymer has low water absorption power, which is particularly unfavorable for the electrolyte 71 aqueous solution. Further, there is a problem that the absorption rate is slow, and furthermore, there are practical problems such as a complicated manufacturing process.
本発明は上記従来技術の問題点を改善するため、新規な
籾水性ポリマー用七ツマ−を提供することにある。The present invention aims to improve the problems of the prior art described above and to provide a novel 7-mer for rice grain water-based polymers.
［課題を解決づるだめの手段１ 上記目的を達成するため本発明は下記の構成からなる。[Means to solve problems 1 In order to achieve the above object, the present invention consists of the following configuration.
「（１） 下記一般式（Ｉ）で表わされることを特徴
とするオキシランカルボン酸エステル。(1) An oxirane carboxylic acid ester represented by the following general formula (I).
＾１
（ただし、式中Ｒ１は水素１京子またはメチル基、Ｒ２
は炭素数１〜４のアルキル基で′必り、ｎは正の整数で
ある。）」
本発明の第１の特徴は、エステル基のすぐ隣にエポキシ
環があることである。（メタ）アクリル酸エステルを酸
化してエポキシ環を形成する場合、条件を選択しないと
かかる位置にエポキシ環を形成することは困難である。^1 (However, in the formula, R1 is hydrogen or methyl group, R2
must be an alkyl group having 1 to 4 carbon atoms, and n is a positive integer. )" The first feature of the present invention is that there is an epoxy ring immediately adjacent to the ester group. When forming an epoxy ring by oxidizing a (meth)acrylic ester, it is difficult to form an epoxy ring at such a position unless conditions are selected.
すなわち、（メタ）アクリル酸エステルは二重結合の電
子密度か低く、非常に重合しやすく、また親水性である
ため酸化条件、および精製条件は慎重に選択する必要が
ある。That is, since (meth)acrylic acid ester has a low double bond electron density, is very easy to polymerize, and is hydrophilic, oxidation conditions and purification conditions must be carefully selected.
本発明の新規オキシランカルボン酸エステルは、例えば
、対応する（メタ）アクリル酸エステルを過酸などで酸
化することにより製造することができる。この場合、過
酸はクロロ過安息香酸、トリフル２口過酢酸などが好ま
しい。The novel oxirane carboxylic acid ester of the present invention can be produced, for example, by oxidizing the corresponding (meth)acrylic acid ester with a peracid or the like. In this case, the peracid is preferably chloroperbenzoic acid, triflic 2-port peracetic acid, or the like.
第２の特徴は、Ｒ２は炭素数１〜４のアルキル基である
ことである。そのため、アルカリに対して反応しにくく
安定性が高い。Ｒ２が水素の場合は、この水素は活性水
素であるのでアルカリに反応しやすくなる。またＲ２の
炭素数が５以上になると親水［生が低下するので好まし
くない。Ｒ２の最も好ましい炭素数は１である。すなわ
ちメトキシ基である。The second feature is that R2 is an alkyl group having 1 to 4 carbon atoms. Therefore, it is less likely to react with alkali and has high stability. When R2 is hydrogen, since this hydrogen is active hydrogen, it tends to react with alkali. Furthermore, if the number of carbon atoms in R2 is 5 or more, the hydrophilicity decreases, which is not preferable. The most preferable carbon number of R2 is 1. That is, it is a methoxy group.
次にエチレングリコールユニットの分子量はいかなる正
の整数でおってもよいが、常温で親水性を発揮させるた
めには、好ましくはｎは１〜１０程度である。ｎが高い
数値であると常温で固体になりやすくなる。Next, the molecular weight of the ethylene glycol unit may be any positive integer, but in order to exhibit hydrophilicity at room temperature, n is preferably about 1 to 10. When n is a high value, it tends to become solid at room temperature.
前記一般式（Ｉ＞で表わされるオキシランカルボン酸エ
ステルとしては、Ａキシランカルボン酸メトキシエチル
エステル、？−メチルＡキシランカルボン酸メトキシエ
ヂルエステル、オキシランカルボン酸工１〜キシエチル
ニスデル、２−メチルオキシランカルボン酸工１〜キシ
エチルエステル、オキシランカルボン酸メトキシジエチ
レングリコール七ノエステル、２−メチルオキシランカ
ルボン酸メトキシジエチレングリコール七ノエステル、
Ａキシランカルボン酸メトキシトリエヂレングリコール
モノエステル、２−メチルオキシランカルボンメトキシ
トリエチレングリコール七ノエステル、オキシランカル
ボン酸メトキシノナエチレングリコールモノエステル
ン酸メトキシノナエチレングリコール七ノエステル等が
ある。Examples of the oxirane carboxylic acid ester represented by the general formula (I>) include A xylan carboxylic acid methoxyethyl ester, ?-methyl A xylan carboxylic acid methoxy ethyl ester, oxirane carboxylic acid 1-xyethylnisder, and 2-methyloxirane. Carboxylic acid 1-xyethyl ester, oxirane carboxylic acid methoxydiethylene glycol 7-ester, 2-methyloxirane carboxylic acid methoxydiethylene glycol 7-ester,
A: xylan carboxylic acid methoxy triethylene glycol monoester, 2-methyloxirane carboxylic acid methoxy triethylene glycol heptanoester, oxirane carboxylic acid methoxy nonaethylene glycol monoester, oxirane carboxylic acid methoxy nonaethylene glycol monoester, and the like.
上記した本発明のオキシランカルボン酸エステルは、重
合すると下記式（ｎ）の繰り返し中位のオキシランカル
ボン酸エステルポリマーとなる。When the above-mentioned oxirane carboxylic acid ester of the present invention is polymerized, it becomes an oxirane carboxylic acid ester polymer with a repeating medium of the following formula (n).
（ただし、式中Ｒ１は水素原子またはメチル阜、Ｒ２は
炭素数１〜４のアルキル基であり、ｍはポリマの繰り返
し数を示し、ｎは正の整数を示す。）すなわち本発明の
七ツマ−のオキシラン環（エポキシ基）を開環したポリ
マーとなる。したがって上記式（ｎ）において、繰り返
し′ｆｉｍはポリマーを示す数であればいかなる数でも
よい。(However, in the formula, R1 is a hydrogen atom or a methyl group, R2 is an alkyl group having 1 to 4 carbon atoms, m indicates the repeating number of the polymer, and n indicates a positive integer.) It becomes a polymer with the oxirane ring (epoxy group) of - opened. Therefore, in the above formula (n), the repeat 'fim may be any number as long as it represents a polymer.
オキシラン環（エポキシ基）の開環反応は、工ポキシ樹
脂の硬化手段としてよく知られている公知のいかなる手
段を採用してもよい。たとえば開環触媒としてアミン類
、酸無水物、各種錯体（たとえばアルミニウムキレート
化合物など）、過塩素酸塩類、ナフテン酸金属塩類、ア
ルキルイミダゾール類などを用い、加熱または常温で開
環させることができる。For the ring-opening reaction of the oxirane ring (epoxy group), any known means that is well known as a means for curing engineered poxy resins may be employed. For example, using amines, acid anhydrides, various complexes (such as aluminum chelate compounds), perchlorates, naphthenic acid metal salts, alkylimidazoles, etc. as a ring-opening catalyst, ring-opening can be carried out by heating or at room temperature.
もちろんこの場合、本発明の七ツマ−は単独で手合して
もよく、エチレンオキ量ナイドのようなエポキシ環を右
する共重合成分上ツマ−と共重合しても目的が達成でき
る。Of course, in this case, the hexamer of the present invention may be prepared alone, or the object can be achieved by copolymerizing it with a copolymer component containing an epoxy ring such as ethylene oxynide.
本発明の七ツマ−を重合して得られる親水性ポリマーは
例えば、その吸水性に着目し、生理用品や紙おむつ、農
林用の保水剤などのほか、脱水剤、水性ゲル基材、結露
防止剤、油中の水分除去剤、電解質の媒体などとして広
汎な用途がある。The hydrophilic polymer obtained by polymerizing the nanatsumer of the present invention is, for example, focused on its water absorbing property, and is used as a sanitary napkin, disposable diaper, water retention agent for agriculture and forestry, as well as a dehydrating agent, an aqueous gel base material, and a dew prevention agent. It has a wide range of uses, including as a water remover in oil and as an electrolyte medium.
［実施例］
以下実施例を用いて具体的に説明する。なお本発明は実
施例の記・戎に限定されるものではない。[Example] The following is a concrete explanation using an example. Note that the present invention is not limited to the description and description of the embodiments.
実施例１
オキシランカルシボン酸メ１へキシトリ玉ヂレングｍ−
クロロ過安息香酸７５Ｑ、４，４°−チオビス（６−ｔ
ｅｒｔ−ブチル−ｍ−クレゾール＞１．ＯＣ］の１．２
−ジクロロエタン３０ｍ１溶液に、アクリル該メトキシ
トリエチレングリコール七ノエステル８０ｑの１，２−
ジクロロエタン５０ｍ１溶液を加え、１６時間加熱環流
した。Example 1 Oxiranecarciboxylic acid melihexytridine m-
Chloroperbenzoic acid 75Q, 4,4°-thiobis(6-t
ert-butyl-m-cresol>1. 1.2 of [OC]
- In 30 ml of dichloroethane solution was added 80 q of 1,2-acrylic methoxytriethylene glycol hetanoester.
A solution of 50 ml of dichloroethane was added, and the mixture was heated under reflux for 16 hours.
反応液を冷却し、析出した結晶を戸別し、；炉液をエバ
ポレーターにて濃縮した。残渣を１０００−の酢酸エチ
ルに溶解し、２０％亜硫酸ナトリウム水溶液、５％重炭
酸水溶液、飽和食塩水の順に洗浄し、無水硫酸マグネシ
ウムにて乾燥した。溶媒をエバポレーターで留去した後
、残渣を蒸溜し、沸点９８〜１３７℃１０．２５ｍｍＨ
ｇの留分２３゜９ｑを１ｑた。さらにこの留分を再蒸溜
し、表題の化合物を得た。The reaction solution was cooled, the precipitated crystals were separated, and the furnace solution was concentrated using an evaporator. The residue was dissolved in 1000-ml ethyl acetate, washed successively with 20% aqueous sodium sulfite solution, 5% aqueous bicarbonate solution, and saturated brine, and dried over anhydrous magnesium sulfate. After the solvent was distilled off using an evaporator, the residue was distilled to give a boiling point of 98 to 137°C, 10.25 mmH.
1q of 23°9q of fraction of g was collected. Further, this fraction was redistilled to obtain the title compound.
沸点 １１４〜１１６℃１０．２ｍｍ１１ｇ赤外スペク
トル（液膜法〉
１７５０ｃｍ’ 、 ８６０ｃｍ−１
質呈分析（ＣＩ法、 ｍ／ｅ ）
２３５（）Ｉ＋１）−＋、１９１，１７５゜１４７．１
１５．１０３
１３Ｃ核磁気共鳴スペクトル（ＣＤＣＱ３．δ）４６．
５．４７．２．５８．９，６４．６゜６８．８，７０．
６．７１．９，１６９．２赤外吸収スペクトルチヤート
については第１図に、１３Ｃ核磁気共鳴スペクトルチヤ
ートについては第２図に示す。Boiling point 114-116℃ 10.2mm 11g Infrared spectrum (liquid film method) 1750cm', 860cm-1 Texture analysis (CI method, m/e) 235()I+1)-+, 191,175°147.1
15.103 13C nuclear magnetic resonance spectrum (CDCQ3.δ)46.
5.47.2.58.9, 64.6°68.8, 70.
6.71.9, 169.2 infrared absorption spectrum chart is shown in FIG. 1, and 13C nuclear magnetic resonance spectrum chart is shown in FIG. 2.
実施例２
オキシランカルボン酸エトキシエチルエステルｍ−クロ
ロ過安息香酸４１．４Ｃ］、４，４°−チオビス（６−
ｔｅｒｔ−ブチル−ｍ−クレゾール＞０．５ｑの１，２
−ジクロロエタン３５０ｍ溶液に、アクリル酸エトキシ
エチルエステル２８．８ｇの１，２−ジクロロエタン３
０ｍ１溶液を加え、以下実施例１と同様の操作により反
応させ、表題の化合物を１ｑた。Example 2 Oxiranecarboxylic acid ethoxyethyl ester m-chloroperbenzoic acid 41.4C], 4,4°-thiobis(6-
tert-butyl-m-cresol>0.5q of 1,2
- In 350 m of dichloroethane solution, 28.8 g of acrylic acid ethoxyethyl ester was added to 1,2-dichloroethane 3
0ml of the solution was added, and the reaction was carried out in the same manner as in Example 1, yielding 1q of the title compound.
この化合物の分析値は下記のとおりで必る。The analytical values for this compound are required as shown below.
沸点：８１°Ｃ〜８６°Ｃ／ ３ ｍｍ１１ｇ赤外スペ
ク１〜ル（液膜法）
１７５５ｃｍ−１，８５５ｃｍ−”
質量分析（ＣＩ法、 ｍ／ｅ ）
１６１（Ｍ＋１） ＋ 、 １１７． ８７．
５９１３Ｃ核磁気共鳴スペクトル（ＣＤＣα３．δ
）１５．１．４６．６，４７．５．６４．０゜６６．８
，６８．６，１６９．５
実施例３
ｍ−クロロ過安息香酸４１．４Ｃ］、４，４°−チオビ
ス（６−ｔｅｒｔ−ブチル−ｍ−クレゾール＞０．５Ｃ
１の１．２−ジクロロエタン３５０ｄ溶液に、メタクリ
ル酸メトキシジエチレングリコール七ノエステル３７．
６ＣＩの１．２−ジクロロエタン３０ｄ溶液を加え、以
下実施例１と同様の操作により反応させ、表題の化合物
を得た。Boiling point: 81°C - 86°C / 3 mm 11 g Infrared spectrometry (liquid film method) 1755 cm - 1,855 cm - "Mass spectrometry (CI method, m/e) 161 (M + 1) +, 117. 87.
5913C nuclear magnetic resonance spectrum (CDCα3.δ
)15.1.46.6,47.5.64.0゜66.8
, 68.6, 169.5 Example 3 m-chloroperbenzoic acid 41.4C], 4,4°-thiobis(6-tert-butyl-m-cresol>0.5C
To a solution of 350d of 1,2-dichloroethane of 1, methoxydiethylene glycol methacrylate 7-ester 37.
A 30d solution of 6CI in 1,2-dichloroethane was added, and the reaction was carried out in the same manner as in Example 1 to obtain the title compound.
この化合物の分析値は下記のとおりである。The analytical values of this compound are as follows.
沸点：９８°Ｃ〜１０３°Ｃ１０，５ｍｍＮ（］赤外ス
ペクトル（液膜法） ′
１７４５ｃｍ’ 、 ８６０ｃｍ−１
？１吊分析（ＣＩ法、 ｍ／ｃ ）
２０５（Ｈ＋１） ＋、 １４７． １１１． ８３
１３Ｃ杉磁気共鳴スペクトル（ＣＤＣα３．δ）１７．
１１．５２．９．５３．５．５８．８６５．４．６９．
０．７０．６．７２．０１７１．０
［発明の効果］
本発明のオキシランカル小ン酸エステルは、エステル基
の隣にオキシラン環を４１し、しかも炭素、数の少ない
アルキル
酸エステル阜を右づ−るため、耐アルカリ性に優れた親
水性ポリマーを冑るための−［ツマ−として有用である
という特別の効果を奏する。Boiling point: 98°C to 103°C 10.5 mmN (] Infrared spectrum (liquid film method) '1745 cm', 860 cm-1?1 Hanging analysis (CI method, m/c) 205 (H+1) +, 147. 111. 83
13C Cedar magnetic resonance spectrum (CDCα3.δ) 17.
11.52.9.53.5.58.865.4.69.
0.70.6.72.0171.0 [Effects of the Invention] The oxirane carboxylic acid ester of the present invention has 41 oxirane rings next to the ester group, and has a small number of carbon atoms on the right side of the alkyl ester group. It has the special effect of being useful as a binder for removing hydrophilic polymers with excellent alkali resistance.
第１図は、本発明の実施例１の化合物の赤外吸収スペク
１ヘルチャ−１−を示し、第２図は、本発明の実施例１
の化合物の１３ｃ核磁気共鳴スペクトルチヤートを示す
。
第１図
第２図FIG. 1 shows the infrared absorption spectrum 1 Hercher-1 of the compound of Example 1 of the present invention, and FIG. 2 shows the infrared absorption spectrum 1 of the compound of Example 1 of the present invention.
13c nuclear magnetic resonance spectrum chart of the compound. Figure 1 Figure 2
Claims (1)
るオキシランカルボン酸エステル。 ▲数式、化学式、表等があります▼（ I ） （ただし、式中Ｒ＾１は水素原子またはメチル基、Ｒ＾
２は炭素数１〜４のアルキル基であり、ｎは正の整数で
ある。）(1) An oxirane carboxylic acid ester represented by the following general formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (However, in the formula, R^1 is a hydrogen atom or a methyl group, R^
2 is an alkyl group having 1 to 4 carbon atoms, and n is a positive integer. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9221888A JPH01265082A (en) | 1988-04-14 | 1988-04-14 | Oxirane-carboxylic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9221888A JPH01265082A (en) | 1988-04-14 | 1988-04-14 | Oxirane-carboxylic acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01265082A true JPH01265082A (en) | 1989-10-23 |
Family
ID=14048304
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9221888A Pending JPH01265082A (en) | 1988-04-14 | 1988-04-14 | Oxirane-carboxylic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01265082A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016531389A (en) * | 2013-07-23 | 2016-10-06 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Oxiranyl acyl derivatives as electrolyte additives for lithium ion batteries |
-
1988
- 1988-04-14 JP JP9221888A patent/JPH01265082A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016531389A (en) * | 2013-07-23 | 2016-10-06 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | Oxiranyl acyl derivatives as electrolyte additives for lithium ion batteries |
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