JPH01180854A - Acrylic acid ester for optical use - Google Patents
Acrylic acid ester for optical useInfo
- Publication number
- JPH01180854A JPH01180854A JP480888A JP480888A JPH01180854A JP H01180854 A JPH01180854 A JP H01180854A JP 480888 A JP480888 A JP 480888A JP 480888 A JP480888 A JP 480888A JP H01180854 A JPH01180854 A JP H01180854A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- polymerization
- cured
- acrylic acid
- optical
- 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
- 230000003287 optical effect Effects 0.000 title claims abstract description 13
- 125000005396 acrylic acid ester group Chemical group 0.000 title abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 3
- -1 acrylic ester Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 8
- 238000002844 melting Methods 0.000 abstract description 6
- 230000008018 melting Effects 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 239000003505 polymerization initiator Substances 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical group OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000012768 molten material Substances 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000012719 thermal polymerization Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 238000005266 casting Methods 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- SYFOAKAXGNMQAX-UHFFFAOYSA-N bis(prop-2-enyl) carbonate;2-(2-hydroxyethoxy)ethanol Chemical compound OCCOCCO.C=CCOC(=O)OCC=C SYFOAKAXGNMQAX-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- QDLRJEPPCTUXSM-UHFFFAOYSA-N 4-(2-methoxyphenyl)phenol Chemical compound COC1=CC=CC=C1C1=CC=C(O)C=C1 QDLRJEPPCTUXSM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DMJDEZUEYXVYNO-UHFFFAOYSA-N 3-(4-phenylphenyl)prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1C1=CC=CC=C1 DMJDEZUEYXVYNO-UHFFFAOYSA-N 0.000 description 1
- YHAIWSIWRGOXDL-UHFFFAOYSA-N 4-(2-methylphenyl)phenol Chemical compound CC1=CC=CC=C1C1=CC=C(O)C=C1 YHAIWSIWRGOXDL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000003518 norbornenyl group Chemical class C12(C=CC(CC1)C2)* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/38—Esters containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/12—Esters of monohydric alcohols or phenols
- C08F20/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F20/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、低吸湿率であり且つ透明性に優れた光学用高
分子材料を提供する新規な光学用アクリル酸エステルに
関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel optical acrylic ester that provides an optical polymer material with low moisture absorption and excellent transparency.
従来、プラスチックレンズ用のモノマー材料としてジエ
チレングリコールビスアリルカーボネート（ＤＧＢＣ）
が市販されており、眼鏡レンズを中心とした用途に使用
されている。しかしながら、ＤＧＢＣの重合硬化物は吸
湿率が２％と犬きく、湿度変化による光学定数への影響
が大きいため、粒密な光学用部品としての用途には適し
ていない。また屈折率も１．５と低いため、レンズの肉
厚が厚くなるという制約もある。Conventionally, diethylene glycol bisallyl carbonate (DGBC) has been used as a monomer material for plastic lenses.
is commercially available and is used mainly for eyeglass lenses. However, the polymerized cured product of DGBC has a moisture absorption rate as low as 2%, and the optical constants are greatly affected by changes in humidity, so it is not suitable for use as a particulate optical component. Furthermore, since the refractive index is as low as 1.5, there is also a restriction that the lens must be thick.
そのため、吸湿率の低いモノマーとしてシクロヘキシル
基、シクロペンタジェン誘導体やノルボルネン誘導体な
どの脂環式構造を有するアクリル酸エステルが開発され
ており、これらの注型重合硬化物では吸湿率は０．３％
程度とＤＧＢＣに比べると低い値であるが、なお充分と
は言えずさらに低いものが望まれていた。他のモノマー
の例として、次式で示されるアクリル酸エステルがある
（例えば特開昭６１−１２７７１２号公報）。Therefore, acrylic acid esters having alicyclic structures such as cyclohexyl groups, cyclopentadiene derivatives, and norbornene derivatives have been developed as monomers with low moisture absorption rates, and the moisture absorption rate of these cast-polymerized products is 0.3%.
Although this value is low compared to the average and DGBC, it is still not sufficient and an even lower value has been desired. Examples of other monomers include acrylic esters represented by the following formula (for example, JP-A-61-127712).
このモノマーの注型重合硬化物は吸湿率か０．１〜０゜
２％程度と低く、また屈折率も１．６と高いため前記し
た点に関して望ましいものである。The cast-polymerized cured product of this monomer has a low moisture absorption rate of about 0.1 to 0.2% and a high refractive index of 1.6, making it desirable in the above-mentioned respects.
しかしながら、その硬化物は半透明であり光学材料とし
て好ましくない。これは重合した高分子鎖が配向した結
果で、例えば ＥｕｒｏｐｅａｎＰｏｌｙｍｅｒ Ｊ
ｏｕｒｎａｌ １０巻５８５〜５９１ページに重合体
の性質として示されている。However, the cured product is translucent and is not preferred as an optical material. This is the result of orientation of polymerized polymer chains, for example, European Polymer J
The properties of the polymer are shown in Vol. 10, pages 585 to 591 of Vol. 10.
本発明は上記のような問題点を解決すべくなされたもの
で、重合後の硬化物の吸湿率が小さく、かつ透明性に優
れ、注型成形が可能なアクリル酸エステルモノマーを提
供することを目的とする。The present invention has been made in order to solve the above-mentioned problems, and aims to provide an acrylic acid ester monomer that has a low moisture absorption rate of a cured product after polymerization, has excellent transparency, and can be cast. purpose.
すなわち、本発明は次式で示される光学用アクリル酸エ
ステルに関する。That is, the present invention relates to an optical acrylic ester represented by the following formula.
（式中、Ｘは−ＣＨ３、−ＯＲ，−３Ｒ１−３ＯＲ９−
３ｏ２Ｒを表わし、Ｒは炭素数１〜１８の脂肪族または
芳香族炭化水素基、ｎは１〜３の整数を表わす。）
上記のアクリル酸エステルは、対応するヒドロキシヒフ
ェニル誘導体とアクリル酸クロライドとの反応により得
られる。この反応は、通常ピリジン、トリエチルアミン
、水酸化ナトリウム、炭酸ナトリウムなどの塩酸捕獲剤
の共存下で行なわれる。反応溶媒は炭化水素系、ケトン
系、ハロゲン化炭化水素系などが使用される。また水酸
化ナトリウム水溶液と上記の有機溶媒とを併用する等の
２相系でも反応が行なえる。(wherein, X is -CH3, -OR, -3R1-3OR9-
3o2R, R is an aliphatic or aromatic hydrocarbon group having 1 to 18 carbon atoms, and n is an integer of 1 to 3. ) The above acrylic esters can be obtained by reacting the corresponding hydroxyhyphenyl derivatives with acrylic acid chloride. This reaction is usually carried out in the presence of a hydrochloric acid scavenger such as pyridine, triethylamine, sodium hydroxide, or sodium carbonate. As the reaction solvent, a hydrocarbon type, a ketone type, a halogenated hydrocarbon type, etc. are used. The reaction can also be carried out in a two-phase system, such as by using a sodium hydroxide aqueous solution and the above-mentioned organic solvent in combination.
上記のアクリル酸エステルの具体例としては、Ｃ２Ｈ５ 等が挙げられる。Specific examples of the above acrylic ester include C2H5 etc.
これらのアクリル酸エステルは、通常室温で固体で得ら
れるため、その融点が低い場合には加熱して溶融させ、
重合開始剤を添加混合した後、加熱重合・光重合等公知
の方法で硬化可能であり、融点か高い場合には他の液状
アクリル酸エステル系モノマーやスチレン系モノマー等
に混合溶解させ、上記と同様にして重合硬化させること
ができる。These acrylic esters are usually obtained as a solid at room temperature, so if their melting point is low, they can be melted by heating.
After adding and mixing a polymerization initiator, it can be cured by a known method such as heat polymerization or photopolymerization.If the melting point is high, it can be mixed and dissolved in other liquid acrylic ester monomers or styrene monomers, etc. Polymerization and curing can be carried out in the same manner.
以下、実施例により本発明を具体的に説明する。Hereinafter, the present invention will be specifically explained with reference to Examples.
実施例１
４− （２’−メトキシフェニル）−フェノール２０ｇ
、水酸化ナトリウム１６ｇ、水１００ｍｆｔを３００ｍ
！：ｌの三ツロフラスコに入れ、室温で３０分間攪拌し
た。次に、硫酸水素テトラｎ−ブチルアンモニウム１．
７ｇ、テトラヒドロフラン１００ｍＪ２を添加し、系内
を７〜８℃に保ちながら、アクリル酸クロライド１２．
６ｇを１時間で滴下した。滴下終了後、室温でさらに１
時間攪拌を続けた後、水層を除去し、有機層を５％水酸
化ナトリウム水溶液、次いで水で２回洗浄し、硫酸マグ
ネシウムで乾燥した。乾燥剤を 濾別後、溶媒を留去し
た残漬をメタノールで再結晶することにより、４−２”
−メトキシビフェニルアクリレート（１）１６ｇを得た
。第１表に融点９元素分析、 ’Ｈ−ＮＭＲの各分析
結果を示す。Example 1 20 g of 4-(2'-methoxyphenyl)-phenol
, 16g of sodium hydroxide, 100mft of water for 300m
! The mixture was placed in a 1:1 Mitsuro flask and stirred at room temperature for 30 minutes. Next, hydrogen sulfate tetra-n-butylammonium 1.
7g of acrylic acid chloride and 100mJ2 of tetrahydrofuran were added, and while keeping the inside of the system at 7 to 8°C, acrylic acid chloride 12.
6 g was added dropwise over 1 hour. After dropping, add another 1 at room temperature.
After continued stirring for an hour, the aqueous layer was removed, and the organic layer was washed twice with a 5% aqueous sodium hydroxide solution and then with water, and dried over magnesium sulfate. After removing the desiccant by filtration, the solvent was distilled off and the residue was recrystallized with methanol to obtain 4-2"
-16 g of methoxybiphenylacrylate (1) was obtained. Table 1 shows the melting point nine element analysis and 'H-NMR analysis results.
ＣＩ）を６０℃に加熱し、光重合開始剤としてベンゾイ
ンインプロピルエーテルを０．５ｇ量％の割合で添加混
合し、透明な石英ガラス板とシリコン樹脂製のガスケッ
トよりなる型内に注入し、ガラス板の両面より２０ｃｍ
の距離から４０Ｗ／ｃｍの高圧水銀灯で１０分間照射を
行なって、厚さ２ ｍ ｍの注型板を作成した。この注
型板を縦横共に３０ｍｍに切り、６０℃、０．５Ｔｏｒ
ｒの減圧下で７２時間保持して脱水した後、温度４５℃
、相対湿度９５％に保った恒温恒湿室内に入れ、５００
時間後の吸湿率変化を重量増加率として測定した。結果
を第２表に示す。CI) was heated to 60°C, benzoin propyl ether was added and mixed as a photopolymerization initiator at a ratio of 0.5 g%, and the mixture was poured into a mold made of a transparent quartz glass plate and a silicone resin gasket. 20cm from both sides of the glass plate
Irradiation was performed for 10 minutes from a distance of 40 W/cm using a high-pressure mercury lamp to create a casting plate with a thickness of 2 mm. This casting plate was cut into 30 mm length and width, and heated at 60℃ and 0.5 Torr.
After dehydration by holding for 72 hours under reduced pressure of R, the temperature was 45℃.
, placed in a constant temperature and humidity chamber maintained at a relative humidity of 95%, and
The change in moisture absorption rate over time was measured as a weight increase rate. The results are shown in Table 2.
また、作成した注型板の厚み方向の分光透過率を測定し
た結果を第１図に示す。Further, the results of measuring the spectral transmittance in the thickness direction of the prepared casting plate are shown in FIG.
実施例２
４−（２“−メトキシフェニル）−フェノールの代わり
に４− （２’−メチルチオフェニル）−フェノール２
１．７ｇを用いた他は、実施例１と同様の操作を行ない
、４−２゛−メチルチオビフェニルアクリレート（ＩＩ
）１７ｇを得た。第１表に分析結果を示す。（ＩＩ）よ
り実施例１と同様の方法で注型板を作成し、同様の方法
で吸湿率変化・透過率を測定した結果をそれぞれ第２表
・第１図に示す。Example 2 4-(2'-methylthiophenyl)-phenol 2 instead of 4-(2"-methoxyphenyl)-phenol
The same operation as in Example 1 was carried out except that 1.7 g was used, and 4-2'-methylthiobiphenyl acrylate (II
) 17g was obtained. Table 1 shows the analysis results. (II) A casting plate was prepared in the same manner as in Example 1, and the changes in moisture absorption and transmittance were measured in the same manner, and the results are shown in Table 2 and FIG. 1, respectively.
実施例３
１− （２’−メトキシフェニル）−フェノールの代わ
りに４− （２’−メチルフェニル）−フェノール１８
．３ｇを用いた他は、実施例１と同様にして、４−２′
−メチルビフェニルアクリレ−） （ＩＩＩ） １６ｇ
を得た。第１表に分析結果を示す。実施例１と同様の方
法で注型板を作成し、吸湿率変化・透過率を測定した結
果を第２表・第１図に示す。Example 3 4-(2'-methylphenyl)-phenol 18 instead of 1-(2'-methoxyphenyl)-phenol
．． 4-2' in the same manner as in Example 1 except that 3g was used.
-methylbiphenylacryle-) (III) 16g
I got it. Table 1 shows the analysis results. A casting plate was prepared in the same manner as in Example 1, and the changes in moisture absorption and transmittance were measured. The results are shown in Table 2 and Figure 1.
実施例４
４− （２’−メトキシフェニル）−フェノールの代わ
りに４− （２” 、４’ 、６“−トリメチルフェニ
ル）−フェノール２１．３ｇを用いたイ也は、実施例１
と同様にして、４−２”、４′。Example 4 Example 1 was performed using 21.3 g of 4-(2'',4',6''-trimethylphenyl)-phenol instead of 4-(2'-methoxyphenyl)-phenol.
Similarly, 4-2", 4'.
６′ −トリメチルビフェニルアクリレート（ｒＶ）１
８ｇを得た。第１表に分析結果を示す。実施例１と同様
の方法で注型板を作成し、吸湿率変化・透過率を測定し
た結果を第２表・第１図に示す。6'-trimethylbiphenylacrylate (rV)1
8g was obtained. Table 1 shows the analysis results. A casting plate was prepared in the same manner as in Example 1, and the changes in moisture absorption and transmittance were measured. The results are shown in Table 2 and Figure 1.
比較例１
４−フェニルフェノールより実施例１と同様の操作によ
り４−ビフェニルアクリレート（Ｖ）を得た。Comparative Example 1 4-biphenylacrylate (V) was obtained from 4-phenylphenol in the same manner as in Example 1.
（Ｖ）より実施例１と同様の方法で注型板を作成し、吸
湿率変化・透過率を測定した結果をそれぞれ第２表・第
１図に示す。A casting plate was prepared from (V) in the same manner as in Example 1, and the changes in moisture absorption and transmittance were measured, and the results are shown in Table 2 and Figure 1, respectively.
第２表
〔発明の効果〕
以上説明したように、本発明の光学用アクリル酸エステ
ルは吸湿率が小さく、透明性に優れた硬化物を与え、光
学材料として極めて優れた特性を示す。Table 2 [Effects of the Invention] As explained above, the optical acrylic ester of the present invention has a low moisture absorption rate, provides a cured product with excellent transparency, and exhibits extremely excellent properties as an optical material.
第１図は光学用アクリル酸エステルから作成した注型板
の分光透過率測定結果を示す図である。
１：実施例１，３
２：実施例２，４
３：比較例１
特許出願人 キャノン株式会社FIG. 1 is a diagram showing the results of measuring the spectral transmittance of a casting plate made from optical grade acrylic ester. 1: Examples 1 and 3 2: Examples 2 and 4 3: Comparative example 1 Patent applicant Canon Co., Ltd.
Claims (1)
−ＳＯ＿２Ｒを表わし、Ｒは炭素数１〜１８の脂肪族ま
たは芳香族炭化水素基、ｎは１〜３の整数を表わす。） で示される光学用アクリル酸エステル。[Claims] 1. The following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X is -CH_3, -OR, -SR, -SOR,
-SO_2R is represented, R represents an aliphatic or aromatic hydrocarbon group having 1 to 18 carbon atoms, and n represents an integer of 1 to 3. ) Optical acrylic ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP480888A JPH01180854A (en) | 1988-01-14 | 1988-01-14 | Acrylic acid ester for optical use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP480888A JPH01180854A (en) | 1988-01-14 | 1988-01-14 | Acrylic acid ester for optical use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH01180854A true JPH01180854A (en) | 1989-07-18 |
Family
ID=11594058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP480888A Pending JPH01180854A (en) | 1988-01-14 | 1988-01-14 | Acrylic acid ester for optical use |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01180854A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005044882A1 (en) * | 2003-11-07 | 2005-05-19 | Toagosei Co., Ltd. | Actinic-energy-ray-curable composition for optical material |
| CN100384895C (en) * | 2003-11-07 | 2008-04-30 | 东亚合成株式会社 | Actinic-energy-ray-curable composition for optical material |
| JP2021080464A (en) * | 2015-06-09 | 2021-05-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Polymerizable compound and use of the same in liquid crystal display |
-
1988
- 1988-01-14 JP JP480888A patent/JPH01180854A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005044882A1 (en) * | 2003-11-07 | 2005-05-19 | Toagosei Co., Ltd. | Actinic-energy-ray-curable composition for optical material |
| CN100384895C (en) * | 2003-11-07 | 2008-04-30 | 东亚合成株式会社 | Actinic-energy-ray-curable composition for optical material |
| US7799844B2 (en) | 2003-11-07 | 2010-09-21 | Toagosei Co., Ltd. | Active energy beam-curable composition for optical material |
| JP4892974B2 (en) * | 2003-11-07 | 2012-03-07 | 東亞合成株式会社 | Active energy ray-curable optical material composition |
| JP2021080464A (en) * | 2015-06-09 | 2021-05-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Polymerizable compound and use of the same in liquid crystal display |
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