JPS59134776A - Novel thioester compound - Google Patents
Novel thioester compoundInfo
- Publication number
- JPS59134776A JPS59134776A JP964883A JP964883A JPS59134776A JP S59134776 A JPS59134776 A JP S59134776A JP 964883 A JP964883 A JP 964883A JP 964883 A JP964883 A JP 964883A JP S59134776 A JPS59134776 A JP S59134776A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- triphenylmethyl
- thioester compound
- mercaptan
- equimolar
- 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
- -1 thioester compound Chemical class 0.000 title claims abstract description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 3
- 238000003797 solvolysis reaction Methods 0.000 abstract description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 3
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 229920001002 functional polymer Polymers 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 abstract description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- MTAHZRMCRJONNA-UHFFFAOYSA-N trityl prop-2-enoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OC(=O)C=C)C1=CC=CC=C1 MTAHZRMCRJONNA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000004304 visual acuity 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】
本発明は新規なチオエステル化合物に関する０即ち、本
発明は一般式
（式中、ＲはＨ又はＯＨ，である）
で表わされる新規なチオエステル化合物を提供するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel thioester compound.That is, the present invention provides a novel thioester compound represented by the general formula (wherein R is H or OH).
本発明の化合物はビニル基を有するため重合及び共重合
が可能で有用な重合体を与えうるものである。Since the compound of the present invention has a vinyl group, it can be polymerized and copolymerized to give a useful polymer.
本発明の化合物は、通常のチオエステルの合成法を適用
することによシ合成することができる。例えば、トリフ
ェニルメチルメルカプタンをジエチルエーテル、テトラ
ヒドロフラン等の溶媒に溶解させ、これ忙等モルか若干
過剰の水素化ナトリウムを加えて反応させた後、トリフ
ェニルメチルメルカプタンに対して等モルか若干過剰の
メタクリル酸クロリド又は、アクリル酸クロリドを添加
することによシ、本発明の化合物であるチオメタクリル
酸ｓ−ｈリフェニルメチル又はチオアクリル酸Ｓ−）リ
フェニルメチルが容易に得られる。The compound of the present invention can be synthesized by applying a conventional thioester synthesis method. For example, triphenylmethyl mercaptan is dissolved in a solvent such as diethyl ether or tetrahydrofuran, and then an equimolar or slightly excess amount of sodium hydride is added and reacted. By adding methacrylic acid chloride or acrylic acid chloride, the compound of the present invention, s-hliphenylmethyl thiomethacrylate or S-)liphenylmethyl thioacrylate, can be easily obtained.
本発明の化合物は、メタクリル酸トリノエニルメチル又
はアクリル酸トリフェニルメチルのようなエステル化合
物と比較して、酸性および中性条件下での加水分解速度
ならびにアルコールによる加溶媒分解速度が遅く、本発
明の化合物を重合して得られた高分子物質も耐加水分解
性、耐加溶媒分解性に富むことが期待される。The compounds of the present invention have a lower rate of hydrolysis under acidic and neutral conditions and a slower rate of solvolysis with alcohol than ester compounds such as trinoenylmethyl methacrylate or triphenylmethyl acrylate, and the present invention It is expected that the polymeric substance obtained by polymerizing the compound will also have high hydrolysis resistance and solvolysis resistance.
本発明の化合物は、例えば光学活性なアニオン重合開始
剤を用いてイオン重合を行うと、光学活性な重合体を与
える。また、同様の方法でコモノマーとしてメタクリル
酸トリフェニル等のメタクリル酸エステルやアクリル酸
エステル化合物と任意の割合で共重合できる。さらにス
チレン誘導体、共役ジエン類等とはブロック共重合体、
グラフト共重合体を合成することが可能である。When the compound of the present invention is subjected to ionic polymerization using, for example, an optically active anionic polymerization initiator, an optically active polymer is obtained. Further, in a similar manner, it can be copolymerized with a methacrylic acid ester such as triphenyl methacrylate or an acrylic acid ester compound as a comonomer in any ratio. Furthermore, styrene derivatives, conjugated dienes, etc. are block copolymers,
It is possible to synthesize graft copolymers.
得られた光学活性な高分子物質は、光学分割能を持つ機
能性ポリマーとして有用である０次に本発明の化合物を
実施例に沿って詳述する○
実施例１
トリフェニルメチルメルカプタン５りを、ジエチルエー
テル６ｒ３ｍｔに溶かし、これに水素イヒナ） ＩＪウ
ム０．４８ ＷをＯＣで加えた。生成ｊ７たナトリウム
塩にメタクリル酸クロリド２ｖを添加し、７５分反応さ
せた後、反応液に飽ａ炭酸ナトリウム水溶液を加えてエ
ーテルで抽出した。The obtained optically active polymeric substance is useful as a functional polymer having optical resolving power. , dissolved in 6r3mt of diethyl ether, and 0.48 W of hydrogen was added thereto under OC. After adding 2v of methacrylic acid chloride to the sodium salt produced and reacting for 75 minutes, a saturated aqueous sodium carbonate solution was added to the reaction solution, and the mixture was extracted with ether.
エーテル層を硫酸マグネシウムで乾燥し、溶媒を留去し
た後、残渣をエタノールで抽出し、不溶部を除いた。エ
タノールを留去して得た粗生成物をエーテルより再結晶
した。収率１．５り（２４％）、融点１２０〜１２１
ｃ０チオメタクリル酸ｓ−トリフェニルメチルであるこ
との確認は’Ｈ−ＮＭ、Ｒ、ＩＲスペクトルおよび元素
分析で行った。The ether layer was dried over magnesium sulfate, the solvent was distilled off, and the residue was extracted with ethanol to remove the insoluble portion. The crude product obtained by distilling off the ethanol was recrystallized from ether. Yield 1.5 liters (24%), melting point 120-121
It was confirmed that it was c0 s-triphenylmethyl thiomethacrylate by 'H-NM, R, IR spectra and elemental analysis.
１Ｈ−Ｎ Ｍ Ｒ（１００ＭＨｚ！ ０Ｃ１ｌｌ中、５
５ｒ）α−ＣＨ，δｔ ａ ５（ｐｐｍ）
二ａｎ２５．４５ 、５．９８
壜
７．１５
・工Ｒ測定
＼０−０ １６７０ｏｎ’
０−０ １６２５
・元素分析
測定値 計算値（Ｃ，Ｈ，、ｏＯ８）
０ ： ８０．２１％ Ｂ ０．２０多Ｈ： ５
．７９ ５．８５
ｓ：９５１ ９．５１
出願人代理人 古 谷 馨1H-NMR (100MHz! 0C1ll, 5
5r) α-CH, δt a 5 (ppm) 2 an25.45, 5.98 Bottle 7.15 ・Eng R measurement＼0-0 1670on' 0-0 1625 ・Elemental analysis measured value Calculated value (C, H, , oO8) 0: 80.21% B 0.20% H: 5
．． 79 5.85 s:951 9.51 Applicant's agent Kaoru Furuya
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP964883A JPS59134776A (en) | 1983-01-24 | 1983-01-24 | Novel thioester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP964883A JPS59134776A (en) | 1983-01-24 | 1983-01-24 | Novel thioester compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59134776A true JPS59134776A (en) | 1984-08-02 |
| JPH0357893B2 JPH0357893B2 (en) | 1991-09-03 |
Family
ID=11726030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP964883A Granted JPS59134776A (en) | 1983-01-24 | 1983-01-24 | Novel thioester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59134776A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002067283A1 (en) * | 2001-02-22 | 2002-08-29 | Siemens Aktiengesellschaft | Electromechanical component |
| US20130035414A1 (en) * | 2010-03-01 | 2013-02-07 | Contamac Limited | High refractive index polymer composition for opthalmic applications |
| US10155879B2 (en) | 2015-12-21 | 2018-12-18 | AZ Electronic Materials (Luxembourg) S.à.r.l. | Compositions and use thereof for modification of substrate surfaces |
-
1983
- 1983-01-24 JP JP964883A patent/JPS59134776A/en active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002067283A1 (en) * | 2001-02-22 | 2002-08-29 | Siemens Aktiengesellschaft | Electromechanical component |
| US20130035414A1 (en) * | 2010-03-01 | 2013-02-07 | Contamac Limited | High refractive index polymer composition for opthalmic applications |
| US10155879B2 (en) | 2015-12-21 | 2018-12-18 | AZ Electronic Materials (Luxembourg) S.à.r.l. | Compositions and use thereof for modification of substrate surfaces |
| JP2019505650A (en) * | 2015-12-21 | 2019-02-28 | アーゼッド・エレクトロニック・マテリアルズ（ルクセンブルグ）ソシエテ・ア・レスポンサビリテ・リミテ | Novel composition and its use for modification of substrate surface |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0357893B2 (en) | 1991-09-03 |
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