JPS62230759A - Novel acryl or methacrylamide derivative - Google Patents
Novel acryl or methacrylamide derivativeInfo
- Publication number
- JPS62230759A JPS62230759A JP7251886A JP7251886A JPS62230759A JP S62230759 A JPS62230759 A JP S62230759A JP 7251886 A JP7251886 A JP 7251886A JP 7251886 A JP7251886 A JP 7251886A JP S62230759 A JPS62230759 A JP S62230759A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- aminobenzophenone
- acid chloride
- formula
- itself
- 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
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 title claims 2
- -1 acryl Chemical group 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 6
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 9
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 abstract description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 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
- 230000006866 deterioration Effects 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JTORJVFELQADEA-UHFFFAOYSA-N n-(2-benzoylphenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 JTORJVFELQADEA-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- UEGIWSXVFSRYKY-UHFFFAOYSA-N n-(2-benzoylphenyl)prop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1C(=O)C1=CC=CC=C1 UEGIWSXVFSRYKY-UHFFFAOYSA-N 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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〉 本発明は次式（１）で示される新規な化合物に関する。[Detailed description of the invention] <Industrial application field> The present invention relates to a novel compound represented by the following formula (1).
蓼
本発明によって提供される上記式（１１で示される新規
な化合物はそれ自体で重合させるかまだは各種のオレフ
ィン性二重結合を有する化合物と共重合させることによ
って高分子劣化防止剤または高分子紫外線吸収剤として
の応用が期待される。The novel compound represented by the above formula (11) provided by the present invention can be polymerized by itself or copolymerized with various compounds having an olefinic double bond to form a polymer deterioration inhibitor or a polymer. It is expected to be used as an ultraviolet absorber.
〈従来の技術〉
下記式（１）で示される化合物については文献等にそれ
を特定する物性等の記載がない。<Prior Art> Regarding the compound represented by the following formula (1), there is no description of physical properties that specify it in the literature.
〈本発明が解決しようとする問題点〉
本発明の目的はそれ自体が高機能を有するモノマーで機
能性高分子の原料モノマーとして期待されるきわめて有
用な新規な化合物を提供することにある。<Problems to be Solved by the Present Invention> An object of the present invention is to provide a novel compound which is itself a highly functional monomer and is expected to be used as a raw material monomer for functional polymers.
〈問題点を解決するための手段および作用〉本発明者ら
はＮ−アクリロイルまたはＮ−メタクリロイル−２−ア
ミノベンゾフェノン（以下、Ｎ−（メタ）アクリロイル
−２−アミノベンゾフェノンとする）（式りを合成すべ
く鋭意検討した結果、２−アミノベンゾフェノンとアク
リル酸クロライドまたはメタクリル酸クロライドとの反
応によって容易に製造できることを見出した。<Means and effects for solving the problems> The present inventors have prepared N-acryloyl or N-methacryloyl-2-aminobenzophenone (hereinafter referred to as N-(meth)acryloyl-2-aminobenzophenone) (the formula: As a result of intensive studies to synthesize it, we found that it can be easily produced by reacting 2-aminobenzophenone with acrylic acid chloride or methacrylic acid chloride.
なお、本発明化合物（１）の製造方法が上記のものに限
定されないことは勿論である。It goes without saying that the method for producing the compound (1) of the present invention is not limited to the above method.
以下、本発明における新規物質の製造方法を実施例によ
り具体的に説明し、得られた新規物質を構造決定するた
めの分析結果をも同時に示す。Hereinafter, the method for producing the novel substance according to the present invention will be specifically explained using Examples, and the analysis results for determining the structure of the obtained novel substance will also be shown at the same time.
実施例１
撹拌機、温度計および滴下ロードを備えた３００−のフ
ラスコに、クロロホルム１２０Ｗｌｌ、２−アミノベン
ゾフェノン１０．０．Ｆ（５０，７ミリモル）、水１５
ｒｎｌおよび炭酸水素ナトリウム５．５４．９（６６，
０ミリモル）を仕込み、反応系内の温度を２〜４°Ｃに
保ちながらメタクリル酸クロライド６．７２１１（６４
，３ミＩＪモル）を７５分かけて滴下した。滴下終了後
、反応系中の温度を４〜７℃に保ちながら３時間撹拌を
続は反応を完結させた。反応終了後、反応系に水３５ｍ
／を加え撹拌し、次いで分液した。反応液の有機層を１
．６％炭酸ナトリウム水溶液５Ｑｍ／で２回洗浄後、水
１００−で２回洗浄した。この有機層の溶媒を減圧留去
した後、減圧乾燥させ、Ｎ−メタクリロイル−２−アミ
ノ−ベンゾフェノン１２．５．１４７．１ミリモル）を
得た。Example 1 In a 300-liter flask equipped with a stirrer, a thermometer, and a dropping load, 120 liters of chloroform and 10.0 liters of 2-aminobenzophenone were added. F (50,7 mmol), water 15
rnl and sodium bicarbonate 5.54.9 (66,
methacrylic acid chloride 6.7211 (64
, 3 mmol) was added dropwise over 75 minutes. After the dropwise addition was completed, the reaction system was stirred for 3 hours while maintaining the temperature in the reaction system at 4 to 7°C to complete the reaction. After the reaction is complete, add 35 m of water to the reaction system.
/ was added and stirred, and then the liquid was separated. The organic layer of the reaction solution is 1
．． It was washed twice with 5 Qm of a 6% aqueous sodium carbonate solution, and then twice with 100 m of water. After the solvent of this organic layer was distilled off under reduced pressure, it was dried under reduced pressure to obtain 12.5.147.1 mmol of N-methacryloyl-2-amino-benzophenone.
収率は仕込みの２−アミノベンゾフェノンに対シ９２、
９ ％であった。高速液体クロマトグラフィー（ＯＤＳ
系カシカラム使用よシ純度を求めたところ９９．６％で
あった。The yield is 92% compared to the starting 2-aminobenzophenone.
It was 9%. High performance liquid chromatography (ODS)
The purity was determined using a Kashi column and was 99.6%.
次に得られたこの新規物質の構造決定のための分析結果
を示す。Next, we will show the analysis results for determining the structure of this new substance.
Ｏ融 点 ４４．８℃
Ｏ元素分析値
Ｃ（％） Ｈ（％） Ｎ（チ）理論値
７６．９６ ５．７０ ５．２８分析値
７７．３４ ５．８８ ５．３３Ｏ’
Ｈ−ＮＭＲ（溶媒：ｄ、−ＤＭＳＯ、内部標準物質：Ｔ
ＭＳ）δ １．８５１ ｐｐｍ （ｓｉｎｇｌｅｔ
３Ｈ） −ＣＨ５δ １０．５３９ ｐｐｍ
（ｓｉｎｇｌｅｔ ＩＨ） −ＮＨ−０質量分析ス
ペクトル
ＥＩ ｍ／ｅ＝２６５（Ｍ”）
Ｏ赤外線吸収スペクトル（ＫＢｒ錠剤）３２００ｃｍ−
’ （Ｖ Ｎ−Ｈ）
３０８０．３０５５ｍ−’ （芳香族νＣ−Ｈ）なお、
この赤外線吸収スペクトルを第１図に示す。O melting point 44.8℃ O elemental analysis value C (%) H (%) N (chi) theoretical value
76.96 5.70 5.28 Analysis value
77.34 5.88 5.33O'
H-NMR (solvent: d, -DMSO, internal standard: T
MS) δ 1.851 ppm (singlet
3H) -CH5δ 10.539 ppm
(singlet IH) -NH-0 mass spectrometry spectrum EI m/e=265 (M”) O infrared absorption spectrum (KBr tablet) 3200 cm-
' (V N-H) 3080.3055m-' (aromatic νC-H)
This infrared absorption spectrum is shown in FIG.
実施例２
実施例１と同様の反応装置を用い、クロロポルム１２０
ｍ７，２−アミノベンゾフェノン１０． ＯＦ（５０，
７ミリモル）、水１！ＭＡ’及び炭酸水素ナトリウム５
．５４．９（６６，０ミリモル）を仕込み反応系内の温
度を２〜７°ＧＫ保ちながらアクリル酸クロライド５．
８２，１６４．３ミリモル）を７５分かけて滴下した。Example 2 Using the same reaction apparatus as in Example 1, chloroporm 120
m7,2-aminobenzophenone 10. OF(50,
7 mmol), water 1! MA' and sodium bicarbonate 5
．． acrylic acid chloride 5.54.9 (66.0 mmol) was charged while maintaining the temperature in the reaction system from 2 to 7°GK.
82,164.3 mmol) was added dropwise over 75 minutes.
滴下終了後、反応系中の温度を４〜７°Ｃに保ちながら
１時間撹拌を続は反応を完結させた。反応終了後、反応
系に水３５ｄを加え撹拌し、次いで分液した。反応液の
有機層を１．６％炭酸ナトリウム水溶液５０ｄで２回洗
浄後、水１００ｍで２回洗浄した。この有機層の溶媒を
減圧留去した後減圧乾燥させ、Ｎ−アクリロイル−２−
アミノベンゾフェノン１１．８Ｎ（４７，０ミリモル）
を得た。収率は仕込みの２−アミノベンゾフェノンに対
し９２．７％であった。高速液体クロマトグラフィー（
ＯＤＳ系カシカラム使用より純度を求めたところ９９．
４％であった。After completion of the dropwise addition, stirring was continued for 1 hour while maintaining the temperature in the reaction system at 4 to 7°C, and the reaction was then completed. After the reaction was completed, 35 d of water was added to the reaction system and stirred, followed by liquid separation. The organic layer of the reaction solution was washed twice with 50 ml of a 1.6% aqueous sodium carbonate solution, and then twice with 100 ml of water. After the solvent of this organic layer was distilled off under reduced pressure, it was dried under reduced pressure, and N-acryloyl-2-
Aminobenzophenone 11.8N (47.0 mmol)
I got it. The yield was 92.7% based on the starting 2-aminobenzophenone. High performance liquid chromatography (
The purity was determined using an ODS Kashi column and was 99.
It was 4%.
次に得られたこの新規物質の構造決定のための分析結果
を示す。Next, we will show the analysis results for determining the structure of this new substance.
Ｏ融 点 ８７．１°Ｃ
Ｏ元素分析値
Ｃ（チ） Ｈ（チ） Ｎ（チ）理論値 ７
６．４８ ５．２１ ５．５７分析値
７６．０９ ５．２０ ５．６２０ ’）
（−ＮＭＲ（溶媒：ｄ、−ＤＭＳＯ１内部標準物質：Ｔ
ＭＳ）δ ５．６５ ｐｐｍ （ｄｏｕｂｌｅｔ
ＩＨ）＝ＣＨδ ６．０８〜６．３４ ｐｐｍ
（ｍｕｌ ｔｉｐｌｅｔ ２Ｈ） ＝ ＣＨ。O melting point 87.1°C O elemental analysis value C (chi) H (chi) N (chi) theoretical value 7
6.48 5.21 5.57 Analysis value
76.09 5.20 5.620')
(-NMR (solvent: d, -DMSO1 internal standard substance: T
MS) δ 5.65 ppm (double
IH)=CHδ 6.08-6.34 ppm
(mul tiplet 2H) = CH.
δ １０．３４３ ｐｐｍ （ｓｉｎｇｌｅｔ Ｉ
Ｈ） ＞ＮＨｏＩｘ量分析スペクトル
ＥＩ ｍ／ｅ ＝ ２５１ （Ｍ”）０赤外線
吸収スペクトル（ＫＢｒ錠剤）３２００ｃｍ−’
（シＮ−Ｈ）
３１００．３０５５ｃｍ−’ （芳香族νＣ−Ｈ）３０
２５ｃＷＬ−’ （＝ＣＨ−のシｃ−Ｈ）なお、この
赤外線吸収スペクトルを第２図に示す。δ 10.343 ppm (singlet I
H)>NHoIx amount analysis spectrum EI m/e = 251 (M”)0 Infrared absorption spectrum (KBr tablet) 3200 cm-'
(SiN-H) 3100.3055cm-' (aromatic νC-H) 30
25cWL-' (=CH-c-H) This infrared absorption spectrum is shown in FIG.
第１図は本発明にがかるＮ−メタクリロイル−２−アミ
ノ−ベンゾフェノン、第２図は本発明にがかるＮ−アク
リロイル−２−アミノベンゾフェノンの赤外線吸収スペ
クトルをそれぞれ示す図である。FIG. 1 is a diagram showing infrared absorption spectra of N-methacryloyl-2-amino-benzophenone according to the present invention, and FIG. 2 is a diagram showing infrared absorption spectra of N-acryloyl-2-aminobenzophenone according to the present invention.
Claims (1)
クリルアミド誘導体。 ▲数式、化学式、表等があります▼（ I ） （式中Ｒは水素原子またはメチル基を表わす）(1) A novel acrylic or methacrylamide derivative represented by the following formula (I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) (R in the formula represents a hydrogen atom or a methyl group)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7251886A JPS62230759A (en) | 1986-04-01 | 1986-04-01 | Novel acryl or methacrylamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7251886A JPS62230759A (en) | 1986-04-01 | 1986-04-01 | Novel acryl or methacrylamide derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62230759A true JPS62230759A (en) | 1987-10-09 |
Family
ID=13491626
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7251886A Pending JPS62230759A (en) | 1986-04-01 | 1986-04-01 | Novel acryl or methacrylamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62230759A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002187868A (en) * | 2000-12-18 | 2002-07-05 | Daicel Chem Ind Ltd | High-purity methacrylic acid halide, method for producing the same, and method for producing high-purity methacrylic acid derivative |
| WO2017145022A1 (en) * | 2016-02-22 | 2017-08-31 | Novartis Ag | Uv/visible-absorbing vinylic monomers and uses thereof |
| US10254567B2 (en) | 2016-02-22 | 2019-04-09 | Novartis Ag | UV-absorbing vinylic monomers and uses thereof |
-
1986
- 1986-04-01 JP JP7251886A patent/JPS62230759A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002187868A (en) * | 2000-12-18 | 2002-07-05 | Daicel Chem Ind Ltd | High-purity methacrylic acid halide, method for producing the same, and method for producing high-purity methacrylic acid derivative |
| WO2017145022A1 (en) * | 2016-02-22 | 2017-08-31 | Novartis Ag | Uv/visible-absorbing vinylic monomers and uses thereof |
| JP2019504168A (en) * | 2016-02-22 | 2019-02-14 | ノバルティス アーゲー | UV / visible absorbing vinyl monomers and uses thereof |
| US10254567B2 (en) | 2016-02-22 | 2019-04-09 | Novartis Ag | UV-absorbing vinylic monomers and uses thereof |
| US10268053B2 (en) | 2016-02-22 | 2019-04-23 | Novartis Ag | UV/visible-absorbing vinylic monomers and uses thereof |
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