JPH09208525A - Phenyl salicylate derivative and its production - Google Patents
Phenyl salicylate derivative and its productionInfo
- Publication number
- JPH09208525A JPH09208525A JP1334896A JP1334896A JPH09208525A JP H09208525 A JPH09208525 A JP H09208525A JP 1334896 A JP1334896 A JP 1334896A JP 1334896 A JP1334896 A JP 1334896A JP H09208525 A JPH09208525 A JP H09208525A
- Authority
- JP
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- Prior art keywords
- phenyl
- formula
- phenyl salicylate
- salicylate derivative
- compound represented
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、新規なサリチル酸
フェニル誘導体及びその製造法に関する。TECHNICAL FIELD The present invention relates to a novel phenyl salicylate derivative and a method for producing the same.
【０００２】[0002]
【従来の技術】従来、紫外線照射による光開始剤として
機能を有する化合物としては、ベンゾフェノン系化合物
（４−ヒドロキシベンゾフェノン）、ベンゾインアルキ
ルエ−テル系化合物、アントラキノン系化合物、ケタ−
ル系化合物、チオキサントン系化合物、が知られてい
る。しかしながら、これらの化合物は紫外線吸収剤とし
ての機能を有していない。2. Description of the Related Art Conventionally, as a compound having a function as a photoinitiator upon irradiation with ultraviolet rays, a benzophenone compound (4-hydroxybenzophenone), a benzoin alkyl ether compound, an anthraquinone compound, a digitizer
Ru-based compounds and thioxanthone-based compounds are known. However, these compounds do not have a function as an ultraviolet absorber.
【０００３】また、紫外線吸収剤としての機能を有する
化合物としては、サリチル酸エステル系化合物、ベンゾ
フェノン系化合物（２−ヒドロキシベンゾフェノン）、
ベンゾトリアゾ−ル系化合物、ベンゾエ−ト系化合物、
シアノアクリレ−ト系化合物が知られている。しかしな
がら、これらの化合物は紫外線による光開始剤としての
機能を有していない。Compounds having a function as an ultraviolet absorber include salicylic acid ester compounds, benzophenone compounds (2-hydroxybenzophenone),
Benzotriazole compounds, benzoate compounds,
Cyanoacrylate compounds are known. However, these compounds do not function as a photoinitiator by ultraviolet rays.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、新規なサリ
チル酸エステル誘導体及びその製造法、特に紫外線照射
による光開始剤としての機能と紫外線吸収剤としての機
能の２つの機能を発現する物質として有用なサリチル酸
エステル誘導体とその製法を提供することを目的とする
ものである。The present invention is useful as a novel salicylic acid ester derivative and a method for producing the same, particularly as a substance exhibiting two functions: a function as a photoinitiator by ultraviolet irradiation and a function as an ultraviolet absorber. Another object of the invention is to provide a salicylic acid ester derivative and a method for producing the same.
【０００５】[0005]
【課題を解決するための手段】かかる目的を達成するた
め、鋭意研究した結果、本発明を完成させた。 すなわ
ち、本発明のうち請求項１記載の発明は、一般式
（１）：Means for Solving the Problems In order to achieve the above object, as a result of intensive studies, the present invention has been completed. That is, the invention according to claim 1 of the present invention is represented by the general formula (1):
【化３】 （但し、式中、Ｒは水素原子、アルキル基又はアルコキ
シ基を表す）で示されるサリチル酸フェニル誘導体であ
る。ここで、一般式（１）において、Ｒとして用いられ
るアルキル基としては、メチル基、エチル基等が例示で
きる。アルコキシ基としてはメトキシ基、エトキシ基等
が例示できる。Embedded image (However, in the formula, R represents a hydrogen atom, an alkyl group, or an alkoxy group), and is a phenyl salicylate derivative. Here, in the general formula (1), examples of the alkyl group used as R include a methyl group and an ethyl group. Examples of the alkoxy group include a methoxy group and an ethoxy group.
【０００６】本発明の一般式（１）で示されるサリチル
酸フェニル誘導体は、紫外線照射による光開始剤として
の機能と紫外線吸収剤としての機能の２つの機能を有す
る。かかる２機能の発現は、該誘導体が紫外線照射によ
り紫外線を吸収して、一般式（３）：The phenyl salicylate derivative represented by the general formula (1) of the present invention has two functions: a function as a photoinitiator upon irradiation with ultraviolet rays and a function as an ultraviolet absorber. The expression of such two functions is expressed by the formula (3):
【化４】 （但し、式中、Ｒは水素原子、アルキル基又はアルコキ
シ基を表す）で示される化合物及び一般式（４）：Embedded image (Wherein, R represents a hydrogen atom, an alkyl group or an alkoxy group) and the general formula (4):
【化５】 （但し、式中、Ｒは水素原子、アルキル基又はアルコキ
シ基を表す）で示される化合物に光フリ−ス転位して、
前者が光開始剤としての機能をそして後者が紫外線吸収
剤としての機能を夫々発揮することによると考えられ
る。Embedded image (However, in the formula, R represents a hydrogen atom, an alkyl group or an alkoxy group.)
It is considered that the former functions as a photoinitiator and the latter functions as an ultraviolet absorber.
【０００７】加えて、本発明に係るサリチル酸フェニル
誘導体は、種々の重合性オリゴマ−、モノマ−との相溶
性に優れている。その結果、この誘導体は、塗料、成形
材料等の成分として好適に使用でき、光開始剤として作
用すると共に、硬化後は紫外線吸収剤としても作用す
る。In addition, the phenyl salicylate derivative according to the present invention has excellent compatibility with various polymerizable oligomers and monomers. As a result, this derivative can be suitably used as a component of paints, molding materials and the like, and acts as a photoinitiator and also as an ultraviolet absorber after curing.
【０００８】また、請求項２記載の発明は、Ｒが水素原
子である請求項１記載のサリチル酸フェニル誘導体であ
ることを特徴とする。The invention according to claim 2 is the phenyl salicylate derivative according to claim 1, wherein R is a hydrogen atom.
【０００９】これは、請求項１記載のサリチル酸フェニ
ル誘導体のＲが水素原子である場合であり、新規化合物
であると共に、前記光開始剤と紫外線吸収剤の２つの機
能を有する。This is the case where R of the phenyl salicylate derivative according to claim 1 is a hydrogen atom, which is a novel compound and has two functions of the photoinitiator and the ultraviolet absorber.
【００１０】また、請求項３記載の発明は、一般式
（２）：The invention according to claim 3 has the general formula (2):
【化６】 （但し、式中、Ｒは水素原子、アルキル基又はアルコキ
シ基を表す）で示される化合物をアクリル酸ハライドと
反応させることを特徴とする請求項１記載のサリチル酸
フェニル誘導体の製造法である。[Chemical 6] The method for producing a phenyl salicylate derivative according to claim 1, wherein a compound represented by the formula (wherein R represents a hydrogen atom, an alkyl group or an alkoxy group) is reacted with an acrylic acid halide.
【００１１】この発明は、新規なサリチル酸フェニル誘
導体の製造法であり、新規である。ここで、一般式
（２）において、Ｒとして用いられるアルキル基として
は、メチル基、エチル基等が、アルコキシ基としてはメ
トキシ基、エトキシ基等が例示できる。The present invention is a novel method for producing a phenyl salicylate derivative and is novel. Here, in the general formula (2), examples of the alkyl group used as R include a methyl group and an ethyl group, and examples of the alkoxy group include a methoxy group and an ethoxy group.
【００１２】[0012]
【実施の形態】以下、本発明の実施の形態について説明
する。Embodiments of the present invention will be described below.
【００１３】本発明の一般式（１）で示されるサリチル
酸フェニル誘導体としては、フェニル−２−アクリロイ
ルオキシベンゾエ−ト、フェニル−２−アクロリイルオ
キシ−３−メチルベンゾエ−ト、フェニル−２−アクリ
ロイルオキシ−４−メチルベンゾエ−ト、フェニル−２
−アクリロイルオキシ−５−メチルベンゾエ−ト、フェ
ニル−２−アクリロイルオキシ−３−メトキシベンゾエ
−ト等が例示される。本発明に係るこれらのサルチル酸
フェニル誘導体は、フェニル−２−ヒドロキシベンゾエ
−ト、フェニル−２−ヒドロキシ−３−メチルベンゾエ
−ト、フェニル−２−ヒドロキシ−４−メチルベンゾエ
−ト、フェニル−２−ヒドロキシ−５−メチルベンゾエ
−ト、フェニル−２−ヒドロキシ−３−メトキシベンゾ
エ−ト等の一般式（２）で示される化合物のそれぞれ
を、アルカリ又は第３級アミン存在下に、アクリル酸ハ
ライドと反応させることにより得ることができる。Examples of the phenyl salicylate derivative represented by the general formula (1) of the present invention include phenyl-2-acryloyloxybenzoate, phenyl-2-acryloyloxy-3-methylbenzoate and phenyl-2-acryloyl. Oxy-4-methylbenzoate, phenyl-2
-Acryloyloxy-5-methylbenzoate, phenyl-2-acryloyloxy-3-methoxybenzoate and the like are exemplified. These phenyl salicylate derivatives according to the present invention are phenyl-2-hydroxybenzoate, phenyl-2-hydroxy-3-methylbenzoate, phenyl-2-hydroxy-4-methylbenzoate, phenyl-2- Each of the compounds represented by the general formula (2) such as hydroxy-5-methylbenzoate and phenyl-2-hydroxy-3-methoxybenzoate was treated with an acrylic acid halide in the presence of an alkali or a tertiary amine. It can be obtained by reacting.
【００１４】アルカリとしては、水酸化ナトリウム、水
酸化カリウム等が、第３級アミンとしては、トリエチル
アミン、ピリジン等が、アクリル酸ハライドとしてはア
クリル酸クロリド、アクリル酸ブロミド等が例示され
る。Examples of the alkali include sodium hydroxide and potassium hydroxide, examples of the tertiary amine include triethylamine and pyridine, and examples of the acrylic acid halide include acrylic acid chloride and acrylic acid bromide.
【００１５】反応は、前記一般式（２）で示される化合
物とアルカリ水溶液との混合溶液又は該一般式（２）で
示される化合物と第３級アミンと有機溶剤との混合溶液
を０〜５℃に維持しながら、その中にアクリル酸ハライ
ドを滴下して行えばよい。一般式（２）で示される化合
物１モルに対し、アクリル酸ハライドは１〜２モル、ア
ルカリ又は第３級アミンは１〜２モルのモル比で使用さ
れる。有機溶剤としては、トルエン、テトラヒドロフラ
ン等を使用すればよい。In the reaction, a mixed solution of the compound represented by the general formula (2) and an aqueous alkaline solution or a mixed solution of the compound represented by the general formula (2), a tertiary amine and an organic solvent is used in an amount of 0 to 5. Acrylic halide may be added dropwise thereto while maintaining the temperature at ℃. The acrylic acid halide is used in a molar ratio of 1 to 2 mol, and the alkali or tertiary amine is used in a molar ratio of 1 to 2 mol per 1 mol of the compound represented by the general formula (2). As the organic solvent, toluene, tetrahydrofuran or the like may be used.
【００１６】このようにして製造された、フェニル−２
−アクリロイルオキシベンゾエ−ト、フェニル−２−ア
クリロイルオキシ−３−メチルベンゾエ−ト、フェニル
−２−アクリロイルオキシ−４−メチルベンゾエ−ト、
フェニル−２−アクリロイルオキシ−５−メチルベンゾ
エ−ト、フェニル−２−アクリロイルオキシ−３−メト
キシベンゾエ−ト等のサリチル酸フェニル誘導体は、前
記２機能を有すると共に、種々の重合性オリゴマ−、モ
ノマ−等との相溶性にも優れている。Phenyl-2 produced in this way
-Acryloyloxybenzoate, phenyl-2-acryloyloxy-3-methylbenzoate, phenyl-2-acryloyloxy-4-methylbenzoate,
Phenyl salicylate derivatives such as phenyl-2-acryloyloxy-5-methylbenzoate and phenyl-2-acryloyloxy-3-methoxybenzoate have the above-mentioned two functions, and also have various polymerizable oligomers and monomers. Excellent compatibility with etc.
【００１７】したがって、塗料、成形材料等の成分とし
て好適に使用でき、前記２機能を備えた製品を提供でき
る。Therefore, it can be suitably used as a component of paint, molding material, etc., and a product having the above-mentioned two functions can be provided.
【００１８】なお、上記重合性オリゴマ−、モノマ−の
具体例としては、下記の物質を示すことができる。The following substances can be shown as specific examples of the above-mentioned polymerizable oligomer and monomer.
【００１９】１）ウレタンアクリレ−トオリゴマ−：例
えば、ペンタエリスリト−ルトリアクリレ−トとヘキサ
メチレンジイソシアネ−トとの付加反応により得られる
ウレタンアクリレ−トオリゴマ−である。1) Urethane acrylate oligomer: For example, a urethane acrylate oligomer obtained by the addition reaction of pentaerythritol triacrylate and hexamethylene diisocyanate.
【００２０】２）ポリエステルアクリレ−トオリゴマ
−：例えば、アクリル酸とフタル酸、アジピン酸等の多
価カルボン酸とペンタエリスリト−ル、ジエチレングリ
コ−ル等の多価アルコ−ルとを共エステル化して得られ
るポリエステルアクリレ−トオリゴマ−である。2) Polyester acrylate oligomer: For example, a polyvalent carboxylic acid such as acrylic acid and phthalic acid or adipic acid and a polyvalent alcohol such as pentaerythritol or diethylene glycol are co-esterified. It is a polyester acrylate oligomer obtained as a result.
【００２１】３）エポキシアクリレ−トオリゴマ−：例
えば、ビスフェノ−ルＡジグリシジルエ−テルとアクリ
ル酸との付加反応で得られるエポキシアクリレ−トオリ
ゴマ−である。3) Epoxy acrylate oligomer: For example, an epoxy acrylate oligomer obtained by addition reaction of bisphenol A diglycidyl ether and acrylic acid.
【００２２】４）アクリレ−トモノマ−：例えば、アク
リロイルオキシ基を１個以上有するアクリレ−トモノマ
−、即ち、ヒドロキシエチルアクリレ−ト、ヒドロキシ
プロピルアクリレ−ト、１，６−ヘキサンジオ−ルジア
クリレ−ト、ジエチレングリコ−ルジアクリレ−ト、ポ
リアルキレングリコ−ルジアクリレ−ト、ネオペンチル
グリコ−ルジアクリレ−ト、トリメチロ−ルプロパント
リアクリレ−ト、ペンタエリスリト−ルトリアクリレ−
ト、ペンタエリスリト−ルテトラアクリレ−ト、ジペン
タエリスリト−ルヘキサアクリレ−ト等である。4) Acrylate monomer: For example, an acrylate monomer having one or more acryloyloxy groups, that is, hydroxyethyl acrylate, hydroxypropyl acrylate, 1,6-hexanediol diacrylate. , Diethylene glycol diacrylate, polyalkylene glycol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate
And pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, and the like.
【００２３】[0023]
【実施例】次に、実施例をもって、本発明をさらに具体
的に説明する。以下、「部」は「重量部」を意味する。EXAMPLES Next, the present invention will be described more specifically by way of examples. Hereinafter, “part” means “part by weight”.
【００２４】実施例：フェニル−２−アクリロイルオキ
シベンゾエ−トの製造 撹拌機、温度計、均圧管付き滴下ロ−トを備えた１リッ
トル丸底フラスコ内に、フェニル−２−ヒドロキシベン
ゾエ−ト６４．２部、トリエチルアミン３３．３部、及
びトルエン６４２部を仕込み、氷浴中０〜５℃において
撹拌しながらアクリル酸クロライド２９．９部を、滴下
ロ−トより３０分かけて滴下した。滴下後、２時間撹拌
を続けつつ反応させた。反応終了後、反応液を５％炭酸
ナトリウム水溶液５００部で２回洗浄した。静置分液し
たトルエン層に無水硫酸マグネシウムを３０部加え、一
昼夜放置後、無水硫酸マグネシウムを濾過した。続い
て、減圧下、４０〜５０℃でトルエンを除去し、粗反応
生成物７０．５部を得た。次いでシクロヘキサン３００
を加えて再結晶し目的の生成物６４．３部（収率８０
％）を得た。Example: Production of phenyl-2-acryloyloxybenzoate Phenyl-2-hydroxybenzoate was placed in a 1 liter round bottom flask equipped with a stirrer, thermometer and dropping funnel with pressure equalizing tube. 64.2 parts of triethylamine, 33.3 parts of triethylamine, and 642 parts of toluene were charged, and 29.9 parts of acrylic acid chloride was added dropwise from a dropping funnel over 30 minutes while stirring at 0 to 5 ° C. in an ice bath. . After the dropping, the reaction was continued for 2 hours while stirring. After completion of the reaction, the reaction solution was washed twice with 500 parts of a 5% sodium carbonate aqueous solution. 30 parts of anhydrous magnesium sulfate was added to the toluene layer separated by standing, and the mixture was allowed to stand for a day and night, and then anhydrous magnesium sulfate was filtered. Subsequently, toluene was removed under reduced pressure at 40 to 50 ° C. to obtain 70.5 parts of a crude reaction product. Then cyclohexane 300
And recrystallized to give 64.3 parts of the desired product (yield 80
%) Was obtained.
【００２５】該生成物の融点（溶け終り）は１００．５
℃であり、下記の分光学的デ−タより、目的のフェニル
−２−アクリロイルオキシベンゾエ−トであることを確
認した。The melting point (end of melting) of the product is 100.5.
It was determined to be the desired phenyl-2-acryloyloxybenzoate from the following spectroscopic data.
【００２６】1Ｈ−ＮＭＲスペクトル（溶媒ＣＤＣ
ｌ3 、ＴＭＳ内部基準） δ値（ｐｐｍ）：６．００（ｔ，１Ｈ）、６．３９
（ｄ，２Ｈ）、７．００〜７．７６（ｍ，８Ｈ）、８．
１２〜８．２５（ｄｄ，１Ｈ） ＩＲスペクトル（ＫＢｒ） ν（ｃｍ1 ）：３０８０（Ｃ−Ｈ）、１７３６（Ｃ＝
Ｏ）、１６３３、１６０５、１４８３及び１４４６（Ｃ
＝Ｃ）、１２９８、１２４６、１１３６及び１０５１
（Ｃ−Ｏ−Ｃ） 応用例 実施例で得たフェニル−２−アクリロイルオキシベンゾ
エ−ト５部、ＵＡ−３０６Ｈ（共栄社油脂工業（株）製
ウレタンアクリレ−トオリゴマ−）４０部、ＥＢ−１８
３０（ダイセルＵＣＢ（株）製ポリエステルアクリレ−
トオリゴマ−）３０部、Ａ−４００（新中村化学工業
（株）製ポリエチレングリコ−ル＃４００ジアクリレ−
ト）２５部からなる組成物に、イソプロピルアルコ−ル
と酢酸ブチルとエチルセロソルブから成る混合溶剤（溶
剤組成の重量比：４０／４０／２０）１５０部を加え、
不揮発分が４０重量％になるように調整した。その調整
液を２ｍｍの厚さのポリカ−ボネ−トシ−トにバ−Ｎ
ｏ．１６のバ−を使用してバ−コ−トし被膜を形成さ
せ、６０℃で３分間乾燥させた。その後、当該シ−トを
空気中にて高圧水銀灯（アイグラフィックス社製、アイ
キュア−ＵＥ０２１−４０３Ｃ、５００Ｖ、Ｈ０２−Ｌ
４１（２））を用いて１００ｍｍの距離から１２０Ｗ／
ｃｍ，５秒間紫外線を照射した。紫外線照射後の被膜の
硬度（鉛筆硬度）及び耐候性試験結果を表１に示す。 1 H-NMR spectrum (solvent CDC
l 3 , TMS internal standard) δ value (ppm): 6.00 (t, 1H), 6.39
(D, 2H), 7.00 to 7.76 (m, 8H), 8.
12 to 8.25 (dd, 1H) IR spectrum (KBr) ν (cm 1 ): 3080 (C-H), 1736 (C =
O), 1633, 1605, 1483 and 1446 (C
= C), 1298, 1246, 1136 and 1051.
(C-O-C) Application Example 5 parts of phenyl-2-acryloyloxybenzoate obtained in the examples, 40 parts of UA-306H (urethane acrylate oligomer manufactured by Kyoeisha Oil & Fat Co., Ltd.), EB- 18
30 (Polyester acrylate from Daicel UCB Co., Ltd.)
30 parts, A-400 (Shin Nakamura Chemical Co., Ltd. polyethylene glycol # 400 diacryle)
G) To a composition composed of 25 parts, 150 parts of a mixed solvent composed of isopropyl alcohol, butyl acetate and ethyl cellosolve (weight ratio of solvent composition: 40/40/20) is added,
The nonvolatile content was adjusted to 40% by weight. The adjusted solution is burned onto a polycarbonate sheet having a thickness of 2 mm.
o. It was bar-coated using 16 bars to form a film, and dried at 60 ° C. for 3 minutes. After that, the sheet was placed in the air under a high pressure mercury lamp (manufactured by Eye Graphics Co., Ltd., Eye Cure-UE021-403C, 500V, H02-L).
41 (2)) from a distance of 100 mm to 120 W /
It was irradiated with ultraviolet rays for 5 seconds. Table 1 shows the hardness (pencil hardness) of the coating film after ultraviolet irradiation and the result of the weather resistance test.
【００２７】比較応用例１ フェニル−２−アクリロイルオキシベンゾエ−トを加え
なかった以外は応用例と同様にして、被膜を形成し紫外
線照射を行った。その結果を表１に示す。Comparative Application Example 1 A coating film was formed and UV irradiation was performed in the same manner as in the application example except that phenyl-2-acryloyloxybenzoate was not added. Table 1 shows the results.
【００２８】比較応用例２ 応用例で使用したフェニル−２−アクリロイルオキシベ
ンゾエ−トの代わりに光開始剤としてイルガキュア−１
８４（１−ヒドロキシシクロヘキシルフェニルケトン）
を使用した以外は、応用例と同様にして、硬化被膜を形
成し耐候性試験を行った。その結果を表１に示す。Comparative Application Example 2 Irgacure-1 was used as a photoinitiator instead of the phenyl-2-acryloyloxybenzoate used in the application example.
84 (1-hydroxycyclohexyl phenyl ketone)
A cured film was formed and a weather resistance test was conducted in the same manner as in the application example except that the above was used. Table 1 shows the results.
【００２９】[0029]
【表１】 表１の応用例より本発明に係るサリチル酸フェニル誘導
体は紫外線照射により硬化被膜を与えること、すなわ
ち、光開始剤としての機能を有するものであることがわ
かる。また、本発明に係るサリチル酸フェニル誘導体を
使用した応用例の硬化被膜が、比較応用例２の硬化被膜
に比し、耐候性試験による黄変が抑制されていることか
ら、本発明の化合物は紫外線吸収剤としての機能を有す
るものであることがわかる。[Table 1] It can be seen from the application examples in Table 1 that the phenyl salicylate derivative according to the present invention gives a cured film by irradiation with ultraviolet rays, that is, has a function as a photoinitiator. Further, since the cured coating film of the application example using the phenyl salicylate derivative according to the present invention suppresses yellowing due to the weather resistance test as compared with the cured coating film of Comparative Application Example 2, the compound of the present invention is It can be seen that it has a function as an absorbent.
Claims (3)
シ基を表す）で示されるサリチル酸フェニル誘導体。1. General formula (1): (However, in the formula, R represents a hydrogen atom, an alkyl group, or an alkoxy group.) A phenyl salicylate derivative.
チル酸フェニル誘導体。2. The phenyl salicylate derivative according to claim 1, wherein R is a hydrogen atom.
シ基を表す）で示される化合物をアクリル酸ハライドと
反応させることを特徴とする請求項１記載のサリチル酸
フェニル誘導体の製造法。3. General formula (2): The method for producing a phenyl salicylate derivative according to claim 1, wherein a compound represented by the formula (wherein R represents a hydrogen atom, an alkyl group or an alkoxy group) is reacted with an acrylic acid halide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1334896A JPH09208525A (en) | 1996-01-29 | 1996-01-29 | Phenyl salicylate derivative and its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1334896A JPH09208525A (en) | 1996-01-29 | 1996-01-29 | Phenyl salicylate derivative and its production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09208525A true JPH09208525A (en) | 1997-08-12 |
Family
ID=11830614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1334896A Pending JPH09208525A (en) | 1996-01-29 | 1996-01-29 | Phenyl salicylate derivative and its production |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH09208525A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009110496A1 (en) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | (meth)acrylate compound, curable composition using the same, composition for optical nanoimprint, cured product of the curable composition, and method for producing the cured product |
| US20210002396A1 (en) * | 2018-05-04 | 2021-01-07 | Align Technology, Inc. | Polymerizable monomers and method of polymerizing the same |
| US12029623B2 (en) | 2015-07-07 | 2024-07-09 | Align Technology, Inc. | Dental materials using thermoset polymers |
| US12042353B2 (en) | 2018-05-04 | 2024-07-23 | Align Technology, Inc. | Curable composition for use in a high temperature lithography-based photopolymerization process and method of producing crosslinked polymers therefrom |
| US12215223B2 (en) | 2019-10-31 | 2025-02-04 | Align Technology, Inc. | Crystallizable resins |
-
1996
- 1996-01-29 JP JP1334896A patent/JPH09208525A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009110496A1 (en) * | 2008-03-07 | 2009-09-11 | 富士フイルム株式会社 | (meth)acrylate compound, curable composition using the same, composition for optical nanoimprint, cured product of the curable composition, and method for producing the cured product |
| JP2009215179A (en) * | 2008-03-07 | 2009-09-24 | Fujifilm Corp | (meth)acrylate compound, curable composition using the same, composition for optical nano imprinting, and cured products of these curable compositions and its manufacturing method |
| US8282872B2 (en) | 2008-03-07 | 2012-10-09 | Fujifilm Corporation | (Meth)acrylate compound, curable composition using the same, curable composition for photo-nanoimprints, cured product of curable composition and method for manufacturing cured product |
| US12029623B2 (en) | 2015-07-07 | 2024-07-09 | Align Technology, Inc. | Dental materials using thermoset polymers |
| US20210002396A1 (en) * | 2018-05-04 | 2021-01-07 | Align Technology, Inc. | Polymerizable monomers and method of polymerizing the same |
| US12042353B2 (en) | 2018-05-04 | 2024-07-23 | Align Technology, Inc. | Curable composition for use in a high temperature lithography-based photopolymerization process and method of producing crosslinked polymers therefrom |
| US12152092B2 (en) * | 2018-05-04 | 2024-11-26 | Align Technology, Inc. | Polymerizable monomers and method of polymerizing the same |
| US12215223B2 (en) | 2019-10-31 | 2025-02-04 | Align Technology, Inc. | Crystallizable resins |
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