JP2006248836A - Glass sheet chemically bonded with chromene - Google Patents

Glass sheet chemically bonded with chromene Download PDF

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JP2006248836A
JP2006248836A JP2005066592A JP2005066592A JP2006248836A JP 2006248836 A JP2006248836 A JP 2006248836A JP 2005066592 A JP2005066592 A JP 2005066592A JP 2005066592 A JP2005066592 A JP 2005066592A JP 2006248836 A JP2006248836 A JP 2006248836A
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chromene
containing silane
carbon atoms
alkyl group
glass
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JP4362630B2 (en
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Masako Sakuragi
雅子 桜木
Yuji Kawanishi
祐司 川西
Yasuzo Suzuki
靖三 鈴木
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National Institute of Advanced Industrial Science and Technology AIST
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Abstract

<P>PROBLEM TO BE SOLVED: To provide a chromene-containing silane-treating agent which satisfies both of photosensitivity and strength, and to provide a glass sheet surface-treated with the chromene-containing silane-treating agent. <P>SOLUTION: The chromene-containing silane-treating agent is applied on the surface of glass for forming a photosensitive coating on the surface and is expressed by general formula (I) (wherein, one to all of R<SP>1</SP>, R<SP>2</SP>, and R<SP>3</SP>are each a 1-5C alkyloxy group and remaining two or one of them are each a 1-5C alkyl group; R<SP>4</SP>is one kind selected from an amide bond, an ester bond, and an ether bond; R<SP>5</SP>and R<SP>6</SP>are each one kind selected from a phenyl group, an alkylphenyl group having 1-5C alkyl group, a 1-5C alkyl group, and hydrogen atom; n<SB>1</SB>is an integer of 1-5; and n<SB>2</SB>is an integer of 0-5). The glass whose surface is chemically treated with the agent is also provided. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

本発明は、ガラスの表面処理、より詳しくは、ガラス表面に感光性の被膜を設ける技術に関する。   The present invention relates to glass surface treatment, and more particularly to a technique for providing a photosensitive coating on a glass surface.

従来、図１に示すように、ガラスの表面をシランカップリング剤系の薬剤で処理し、ガラス表面のOH基と結合させ、脱水や脱アルコール反応を起こさせて、架橋を進め、強度の高い被膜を形成させることが知られている（非特許文献１）。   Conventionally, as shown in FIG. 1, the glass surface is treated with a silane coupling agent-based agent, bonded with OH groups on the glass surface, causing dehydration and dealcoholization reaction to proceed with crosslinking and high strength. It is known to form a film (Non-Patent Document 1).

また、シランカップリング剤の典型的な物質であるトリアルコキシシランの合成は、図２に示される。
また、アゾベンゼンを含有したトリエトキシシランを合成し、石英板を処理した例（非特許文献２）、α−ヒドラゾノ−β−ケトエステルを含有したトリエトキシシランを合成し、石英板を処理した例（非特許文献３）が知られている。
しかし、感光性とくに光開始の反応性を付与する観点から、シラン処理剤が研究された例はない。
近藤洋文 月刊マテリアルステージvol.1,No.1,p90(2001) Thin Solid Films,219(1992)226-230 CHEMISTRY LETTERS,pp.543-546,1992. Further, the synthesis of trialkoxysilane, which is a typical material of the silane coupling agent, is shown in FIG.
Moreover, the example which synthesize | combined the triethoxysilane containing azobenzene and processed the quartz board (nonpatent literature 2), the example which synthesize | combined the triethoxysilane containing the alpha-hydrazono-beta-ketoester, and processed the quartz board ( Non-patent document 3) is known.
However, there has been no study of silane treating agents from the viewpoint of imparting photosensitivity, particularly photoinitiating reactivity.
Hirofumi Kondo Monthly Material Stage vol.1, No.1, p90 (2001) Thin Solid Films, 219 (1992) 226-230 CHEMISTRY LETTERS, pp.543-546,1992.

本発明は、ガラス表面に、機能性とくに感光性を付与する観点から、クロメンを導入し、感光性と同時に強度的にも満足できる被膜を形成することを目的としている。   The object of the present invention is to introduce a chromene from the viewpoint of imparting functionality, particularly photosensitivity, to the glass surface, and to form a film that is satisfactory in terms of strength as well as photosensitivity.

本発明は、上記目的を達成するため、クロメン誘導体とエステル化剤を反応させることにより、クロメン誘導体含有の活性エステルを作成し、さらに、アルコキシシランと反応させて、クロメン含有のシラン処理剤を得、これを用いてガラス表面と反応させ、クロメン含有のシラン処理剤で表面処理したガラスを提供するものである。
すなわち、本発明は、ガラス表面に一般式（I）
（式中、Ｒ１、Ｒ２、Ｒ３のうち１〜３個は炭素数１〜５のアルキルオキシ基、残りの２〜０個は炭素数１〜５のアルキル基、Ｒ４はアミド結合、エステル結合、エーテル結合から選ばれる1種であり、Ｒ５、Ｒ６は、フェニル基、炭素数１〜５のアルキル基が導入されたアルキルフェニル基、炭素数１〜５のアルキル基、水素原子から選ばれる1種であり、n1は１〜５の整数、n2は０〜５の整数である。）
で表わされるクロメン含有のシラン処理剤で表面処理したガラスである。
また、本発明は、クロメン含有のシラン処理剤が化学式（II）
とすることができる。
さらに、本発明は、ガラス板に結合したクロメン含有のシラン処理剤に、光照射し、アミンを付加したクロメン含有のシラン処理剤で表面処理したガラスとすることができる。
クロメン化合物は、光を照射した部分のみにアミンが付加する特性を有する。 In order to achieve the above object, the present invention creates a chromene derivative-containing active ester by reacting a chromene derivative with an esterifying agent, and further reacts with an alkoxysilane to obtain a chromene-containing silane treating agent. This is used to react with the glass surface to provide a glass surface-treated with a chromene-containing silane treating agent.
That is, the present invention provides the general formula (I) on the glass surface.
(In the formula, 1 to 3 of R 1 , R 2 and R 3 are alkyloxy groups having 1 to 5 carbon atoms, the remaining 2 to 0 are alkyl groups having 1 to 5 carbon atoms, and R 4 is an amide bond. R 5 and R 6 are a phenyl group, an alkylphenyl group into which an alkyl group having 1 to 5 carbon atoms is introduced, an alkyl group having 1 to 5 carbon atoms, hydrogen, 1 type selected from atoms, n 1 is an integer of 1 to 5, and n 2 is an integer of 0 to 5.)
It is a glass surface-treated with a chromene-containing silane treating agent represented by:
In the present invention, the chromene-containing silane treating agent is represented by the chemical formula (II)
It can be.
Furthermore, this invention can be set as the glass surface-treated with the chromene containing silane processing agent which irradiated the light to the chromene containing silane processing agent couple | bonded with the glass plate, and added the amine.
The chromene compound has a property that an amine is added only to a portion irradiated with light.

本発明のクロメン含有のシラン処理剤で表面処理したガラスは、紫外線を照射すると開環して、開環体はピンク色を呈するので、感光体として有用である。さらに、クロメン化合物は、光を照射した部分のみにアミンが付加する特性を有するので、光を照射した部分のみをアミンと反応させることにより、保存することもでき、記録体としても有用である。
The glass surface-treated with the chromene-containing silane treating agent of the present invention is useful as a photoreceptor because it is opened when irradiated with ultraviolet rays and the ring-opened body exhibits a pink color. Further, since the chromene compound has a property that an amine is added only to a portion irradiated with light, it can be stored by reacting only the portion irradiated with light with an amine, and is useful as a recording material.

本発明で用いるクロメン含有化合物としては、クロメン構造（ベンゾピラン）を有していれば、どのようなものでも良い。例えば、2,2-ジフェニル-2H-クロメン、2-フェニル-2H-クロメン、2-フェニル-2-メチル-2H-クロメン、2-フェニル-2-エチル-2H-クロメン、2,2-ジメチル-2H-クロメン、2-エチル-2-メチルフェニル-2H-クロメン、2-メチル-2-エチルフェニル-2H-クロメン等を挙げることが出来る。
入手しやすいものとしては、次式（III）で示される
2,2-ジフェニル-2H-クロメンがある。
また、本発明で用いられるアルコキシシランと反応する化合物としては、例えば、5-(2-(p-ニトロフェノキシカルボニル)エチル) -2,2-ジフェニル-2H-クロメン、8-(3-(p-ニトロフェノキシカルボニル) プロピル)-2-フェニル-2-メチル-2H-クロメン、6-(2-(ペンタクロロフェノキシカルボニル)エチル) -2,2-ジフェニル-2H-クロメン、７-(ペンタクロロフェノキシカルボキニルメチル)-2-フェニル-2H-クロメン、6-(3-カルボキシプロピル)-2,2-ジメチル-2H-クロメンN-ヒドロキシスクシンイミドエステル、7-(4-カルボキシブチル)-2-フェニル-2-プロピル-2H-クロメンN-ヒドロキシスクシンイミドエステル等を挙げることが出来る。
好適には、式（III）のクロメン化合物のカルボン酸とp-ニトロフェノールを反応させて、次式（IＶ）で示される

6-(2-(p-ニトロフェノキシカルボニル)エチル) -2,2-ジフェニル-2H-クロメンを得る。
さらに、本発明ではアルコキシシラン化合物を反応させる。本発明で用いることが出来るアルコキシシラン化合物としては、例えば、5-アミノペンチルトリメトキシシラン、4-アミノブチルエチルジエトキシシラン、3-アミノプロピルジメチルエトキシシラン、2-アミノエチルメチルエチルプロピルオキシシラン
等を挙げることが出来る。
好適には、式（IＶ）の6-(2-(p-ニトロフェノキシカルボニル)エチル) -2,2-ジフェニル-2H-クロメンと、3-アミノプロピルトリエトキシシランを反応させて、次式（II）で示される
6-(2-(3-(トリエトキシシリル)プロピルアミノカルボニル)エチル) -2,2-ジフェニル-2H-クロメンを得ることが出来る。
ここで、示したのは、一例であり、同様な反応により、種々のクロメン含有のシラン処理剤を得ることが出来る。 The chromene-containing compound used in the present invention may be any compound as long as it has a chromene structure (benzopyran). For example, 2,2-diphenyl-2H-chromene, 2-phenyl-2H-chromene, 2-phenyl-2-methyl-2H-chromene, 2-phenyl-2-ethyl-2H-chromene, 2,2-dimethyl- Examples include 2H-chromene, 2-ethyl-2-methylphenyl-2H-chromene, 2-methyl-2-ethylphenyl-2H-chromene.
As what is easily available, it is shown by the following formula (III)
There is 2,2-diphenyl-2H-chromene.
Examples of the compound that reacts with the alkoxysilane used in the present invention include, for example, 5- (2- (p-nitrophenoxycarbonyl) ethyl) -2,2-diphenyl-2H-chromene, 8- (3- (p -Nitrophenoxycarbonyl) propyl) -2-phenyl-2-methyl-2H-chromene, 6- (2- (pentachlorophenoxycarbonyl) ethyl) -2,2-diphenyl-2H-chromene, 7- (pentachlorophenoxy) Carboquinylmethyl) -2-phenyl-2H-chromene, 6- (3-carboxypropyl) -2,2-dimethyl-2H-chromene N-hydroxysuccinimide ester, 7- (4-carboxybutyl) -2-phenyl- Examples include 2-propyl-2H-chromene N-hydroxysuccinimide ester.
Preferably, the carboxylic acid of the chromene compound of formula (III) is reacted with p-nitrophenol, and is represented by the following formula (IV)

6- (2- (p-nitrophenoxycarbonyl) ethyl) -2,2-diphenyl-2H-chromene is obtained.
Furthermore, in the present invention, an alkoxysilane compound is reacted. Examples of the alkoxysilane compound that can be used in the present invention include 5-aminopentyltrimethoxysilane, 4-aminobutylethyldiethoxysilane, 3-aminopropyldimethylethoxysilane, 2-aminoethylmethylethylpropyloxysilane, and the like. Can be mentioned.
Preferably, 6- (2- (p-nitrophenoxycarbonyl) ethyl) -2,2-diphenyl-2H-chromene of formula (IV) is reacted with 3-aminopropyltriethoxysilane to give the following formula ( II)
6- (2- (3- (triethoxysilyl) propylaminocarbonyl) ethyl) -2,2-diphenyl-2H-chromene can be obtained.
Here, what is shown is an example, and various chromene-containing silane treating agents can be obtained by the same reaction.

本発明で用いるガラスは、アルコキシシランと反応できる通常のものなら何でも良く、市販されているガラスが適用できる。とくに石英ガラスが好ましく用いられる。
本発明では、シランカプラーとクロメンの活性エステルとを反応させて、それを用いて石英板の表面にクロメン誘導体を結合させることができる。
石英板に結合したクロメン誘導体に紫外光を照射すると活性なカルボニル誘導体を生成する。
アミン溶液中でクロメン誘導体を結合した石英板に紫外光を照射すると、アミンが付加する。又は、クロメン誘導体を結合した石英板を紫外光照射後、アミン溶液に浸漬するとアミンが付加する。
本発明で用いる光照射時あるいは光照射後に付加するアミンとしては、脂肪族の第1級及び第2級のアルキルアミン又は芳香族アミンがある。 The glass used in the present invention may be any ordinary glass that can react with alkoxysilane, and commercially available glass can be applied. In particular, quartz glass is preferably used.
In the present invention, a silane coupler is reacted with an active ester of chromene, and the chromene derivative can be bonded to the surface of the quartz plate by using it.
When the chromene derivative bonded to the quartz plate is irradiated with ultraviolet light, an active carbonyl derivative is produced.
When a quartz plate bonded with a chromene derivative in an amine solution is irradiated with ultraviolet light, an amine is added. Alternatively, when a quartz plate bonded with a chromene derivative is irradiated with ultraviolet light and then immersed in an amine solution, amine is added.
The amine added during or after light irradiation used in the present invention includes aliphatic primary and secondary alkyl amines or aromatic amines.

本発明について実施例を用いてさらに詳しく説明するが、本発明はこれら実施例に限定されるものではない。
（実施例１）
ジフェニルクロメンを化学的に結合した石英板の調製
アミノプロピルトリエトキシシラン24 mg（0.1ミリモル）と6-(2-(p-ニトロフェノキシカルボニル)エチル) -2,2-ジフェニル-2H-クロメン104 mg（0.2ミリモル）のジクロロメタン0.5 ml溶液を、室温で22時間攪拌して、ジフェニルクロメン残基を有するトリエトキシシランを合成した。
それにエチルアルコール8 ml を加えた。
サンプルビンに上記溶液4mlをとり、アルカリ洗浄石英板（9x25mm）を2枚いれ、室温で30分または1時間浸漬した。
石英板を溶液から取り出し、３０分室温で乾燥した後、電気炉中で１２０度に１時間加熱した。
ジクロロメタン中で１０分間超音波洗浄してジフェニルクロメンを化学的に結合した石英板を得た。 The present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
Example 1
Preparation of quartz plates chemically bonded with diphenylchromene Aminopropyltriethoxysilane 24 mg (0.1 mmol) and 6- (2- (p-nitrophenoxycarbonyl) ethyl) -2,2-diphenyl-2H-chromene 104 mg A solution of (0.2 mmol) in dichloromethane 0.5 ml was stirred at room temperature for 22 hours to synthesize triethoxysilane having a diphenylchromene residue.
To it was added 8 ml of ethyl alcohol.
4 ml of the above solution was placed in a sample bottle, and two alkali-washed quartz plates (9 × 25 mm) were placed and immersed for 30 minutes or 1 hour at room temperature.
The quartz plate was taken out of the solution, dried at room temperature for 30 minutes, and then heated at 120 ° C. for 1 hour in an electric furnace.
A quartz plate chemically bonded with diphenylchromene was obtained by ultrasonic cleaning in dichloromethane for 10 minutes.

（確認）
ジフェニルクロメンが石英板に結合していることは溶液中のジフェニルクロメンと類似の紫外可視吸収スペクトルを275 nm、320 nm付近に示すことより確認した。
ジフェニルクロメンのジオキサン溶液の310nmのモル吸光係数は3900M-1cm-1であるので、それを元に計算すると、シラン処理剤溶液浸漬30分の板は310nmの吸光度が 0.003であるので、石英板の片面に100Å２あたり2.4ヶのクロメン誘導体がついている計算になる。
シラン処理剤溶液浸漬1時間の板では310nmの吸光度が 0.004であるので、石英板の片面に100Å２あたり3.2ヶのクロメン誘導体がついている計算になる。 (Confirmation)
The binding of diphenylchromene to the quartz plate was confirmed by showing UV-visible absorption spectra similar to those of diphenylchromene in the solution at 275 nm and 320 nm.
Since the 310 nm molar extinction coefficient of diphenylchromene dioxane solution is 3900M -1 cm -1 and calculated based on that, the silane treatment solution soaked plate for 30 minutes has an absorbance of 310 nm of 0.003. consisting of one side in the calculation that with a chromene derivative of 100Å 2 per 2.4 months.
Since absorbance 310nm in a plate of silane treatment agent solution immersion 1 h is 0.004, the calculations that are attached chromene derivative one surface of 100 Å 2 per 3.2 months of quartz plate.

（クロメンを化学的に結合した石英板の光反応挙動）
クロメンを化学的に結合した石英板に313nm光を１０秒照射すると260 nm 〜 600 nm に開環体の幅広の紫外可視吸収スペクトルが現れる。
クロメンを化学的に結合した石英板にアミノアントラキノンのジクロロメタン溶液（6.5mg / 5ml）中で313nm光を120秒照射した後、ジクロロメタン中で3分間超音波洗浄した後、アミノアントラキノンの紫外可視吸収（吸収帯 450 〜 550nm）が検出され、付加が確認できた。
クロメンを化学的に結合した石英板に313nm光を２０秒照射後直ちにアミノアントラキノンのジクロロメタン溶液（50mg / 5ml）に1分間浸漬した後、ジクロロメタン中で３回洗浄し、ジクロロメタン中で3分間超音波洗浄した後、アミノアントラキノンの紫外可視吸収（吸収帯 450 〜 550nm）が検出され、付加が確認できた。 (Photoreaction behavior of quartz plate chemically bonded with chromene)
When a quartz plate chemically bonded with chromene is irradiated with 313 nm light for 10 seconds, a broad UV-visible absorption spectrum of the ring-opened product appears at 260 nm to 600 nm.
A quartz plate chemically bonded with chromene was irradiated with 313nm light in dichloromethane solution (6.5mg / 5ml) of aminoanthraquinone for 120 seconds, then ultrasonically washed in dichloromethane for 3 minutes, and then UV-visible absorption of aminoanthraquinone ( Absorption band 450 to 550 nm) was detected, confirming the addition.
Immediately after irradiating a quartz plate chemically bonded with chromene with 313nm light for 20 seconds, it was immersed in a solution of aminoanthraquinone in dichloromethane (50mg / 5ml) for 1 minute, washed 3 times in dichloromethane, and ultrasonicated in dichloromethane for 3 minutes. After washing, UV-visible absorption (absorption band 450 to 550 nm) of aminoanthraquinone was detected, confirming the addition.

本発明のクロメン含有のシラン処理剤で表面処理したガラスは、感光性があり、感光した部分を保存することが出来るため、記録材として有用である。   The glass surface-treated with the chromene-containing silane treating agent of the present invention is photosensitive and can be used as a recording material because it can preserve the exposed portion.

従来のガラス表面の処理方法Conventional glass surface treatment method 従来のアルコキシシランの製造方法Conventional production method of alkoxysilane 本発明のガラス表面の処理方法の一例An example of the glass surface treatment method of the present invention

Claims (5)

一般式（I）
（式中、Ｒ１、Ｒ２、Ｒ３のうち１〜３個は炭素数１〜５のアルキルオキシ基、残りの２〜０個は炭素数１〜５のアルキル基、Ｒ４はアミド結合、エステル結合、エーテル結合から選ばれる1種であり、Ｒ５、Ｒ６は、フェニル基、炭素数１〜５のアルキル基が導入されたアルキルフェニル基、炭素数１〜５のアルキル基、水素原子から選ばれる1種であり、n1は１〜５の整数、n2は０〜５の整数である。）
で表わされるクロメン含有のシラン処理剤。 Formula (I)
(In the formula, 1 to 3 of R 1 , R 2 and R 3 are alkyloxy groups having 1 to 5 carbon atoms, the remaining 2 to 0 are alkyl groups having 1 to 5 carbon atoms, and R 4 is an amide bond. R 5 and R 6 are a phenyl group, an alkylphenyl group into which an alkyl group having 1 to 5 carbon atoms is introduced, an alkyl group having 1 to 5 carbon atoms, hydrogen, 1 type selected from atoms, n 1 is an integer of 1 to 5, and n 2 is an integer of 0 to 5.)
A silane-containing silane treatment agent represented by: ガラス表面に一般式（I）
（式中、Ｒ１、Ｒ２、Ｒ３のうち１〜３個は炭素数１〜５のアルキルオキシ基、残りの２〜０個は炭素数１〜５のアルキル基、Ｒ４はアミド結合、エステル結合、エーテル結合から選ばれる1種であり、Ｒ５、Ｒ６は、フェニル基、炭素数１〜５のアルキル基が導入されたアルキルフェニル基、炭素数１〜５のアルキル基、水素原子から選ばれる1種であり、n1は１〜５の整数、n2は０〜５の整数である。）で表わされるクロメン含有のシラン処理剤で表面処理したガラス。 General formula (I) on the glass surface
(In the formula, 1 to 3 of R 1 , R 2 and R 3 are alkyloxy groups having 1 to 5 carbon atoms, the remaining 2 to 0 are alkyl groups having 1 to 5 carbon atoms, and R 4 is an amide bond. R 5 and R 6 are a phenyl group, an alkylphenyl group into which an alkyl group having 1 to 5 carbon atoms is introduced, an alkyl group having 1 to 5 carbon atoms, hydrogen, 1 is a kind selected from atoms, n 1 is an integer of 1 to 5, and n 2 is an integer of 0 to 5. The glass is surface-treated with a chromene-containing silane treating agent represented by: クロメン含有のシラン処理剤が化学式（II）
である請求項１に記載したクロメン含有のシラン処理剤。 A chromene-containing silane treatment agent is represented by the chemical formula (II)
The chromene-containing silane treatment agent according to claim 1. クロメン含有のシラン処理剤が化学式（II）
である請求項２に記載したクロメン含有のシラン処理剤で表面処理したガラス。 A chromene-containing silane treatment agent is represented by the chemical formula (II)
The glass surface-treated with the chromene-containing silane treating agent according to claim 2. ガラス板に結合したクロメン含有のシラン処理剤に、光照射し、アミンを付加した請求項２又は請求項４に記載したクロメン含有のシラン処理剤で表面処理したガラス。
The glass surface-treated with the chromene containing silane processing agent of Claim 2 or Claim 4 which added the amine to the chromene containing silane processing agent couple | bonded with the glass plate by light irradiation.
JP2005066592A 2005-03-10 2005-03-10 Glass plate with chemically bonded chromene Expired - Fee Related JP4362630B2 (en)

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