JP2000119260A - New reactive ultraviolet absorbing compound having antioxidative function - Google Patents
New reactive ultraviolet absorbing compound having antioxidative functionInfo
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- JP2000119260A JP2000119260A JP10288338A JP28833898A JP2000119260A JP 2000119260 A JP2000119260 A JP 2000119260A JP 10288338 A JP10288338 A JP 10288338A JP 28833898 A JP28833898 A JP 28833898A JP 2000119260 A JP2000119260 A JP 2000119260A
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、酸化防止機能を有
する反応型紫外線吸収剤化合物に関する。特に、本発明
は、新規な光安定剤および酸化防止剤としての機能を兼
ね備えた、反応性を有するベンゾトリアゾール系化合物
に関する。TECHNICAL FIELD The present invention relates to a reactive ultraviolet absorber compound having an antioxidant function. In particular, the present invention relates to a reactive benzotriazole-based compound having functions as both a novel light stabilizer and an antioxidant.
【０００２】[0002]
【従来の技術】有機材料の安定化剤としては、２−ヒド
ロキシフェニルベンゾトリアゾール化合物が光安定化剤
として知られ、またヒンダードフェノール類が酸化防止
剤として知られている。これらの化合物は、本発明の化
合物と比べると、低分子量であるために樹脂の加工の間
における揮散や経時的な揮散等により、有機材料を長期
間にわたり安定化させることができなかった。2. Description of the Related Art As stabilizers for organic materials, 2-hydroxyphenylbenzotriazole compounds are known as light stabilizers, and hindered phenols are known as antioxidants. Since these compounds have a lower molecular weight than the compounds of the present invention, the organic materials could not be stabilized for a long period of time due to volatilization during processing of the resin or volatilization over time.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、酸化
防止剤かつ紫外線吸収剤として有用であり、長期間にわ
たり有機材料を安定化させることのできる化合物を提供
することにある。SUMMARY OF THE INVENTION An object of the present invention is to provide a compound which is useful as an antioxidant and an ultraviolet absorber and can stabilize an organic material for a long period of time.
【０００４】[0004]
【課題を解決するための手段】本発明は、上記課題を解
決するため、下記一般式（１）で示される化合物を提供
する。The present invention provides a compound represented by the following general formula (1) in order to solve the above-mentioned problems.
【０００５】[0005]
【化２】 Embedded image
【０００６】〔式中、Ｘは水素、ハロゲンまたは炭素数
１〜３のアルコキシもしくはアルキルを表し、Ｒ1 は直
鎖または枝分かれ鎖の炭素数２〜１０のアルキレンを表
し、Ｒ 2 はＨ，−ＣＨ3 または−ＣＨ2 Ｘを表し、ここ
でＸはハロゲンであり、Ｒ3 は水素、アルキルまたはア
リールを表わし、Ｒ4 およびＲ5 は同一であっても相異
なっていてもよく、それぞれ炭素数１〜８のアルキルを
表わす〕[Wherein X is hydrogen, halogen or carbon number
Represents 1-3 alkoxy or alkyl;1Is straight
Represents an alkylene having 2 to 10 carbon atoms in a chain or a branched chain.
Then R TwoIs H, -CHThreeOr -CHTwoRepresents X and here
X is halogen, and RThreeIs hydrogen, alkyl or
Represents a reel, RFourAnd RFiveAre the same but different
And each may be an alkyl having 1 to 8 carbon atoms.
Express)
【０００７】[0007]
【発明の実施の形態】本発明に係る上記化合物は、ベン
ゾトリアゾリル−アルキレンビスフェノール系紫外線吸
収剤の骨格を分子内に有し、かつ、重合可能な不飽和二
重結合を有することを特徴とする。これらの化合物は、
特に波長３００〜４００ｎｍの近紫外領域での紫外線吸
収能に優れるとともに、酸化防止能にも優れている。BEST MODE FOR CARRYING OUT THE INVENTION The compound according to the present invention is characterized in that it has a benzotriazolyl-alkylenebisphenol-based UV absorber skeleton in the molecule and has a polymerizable unsaturated double bond. And These compounds are
In particular, it has excellent ultraviolet absorbing ability in the near ultraviolet region having a wavelength of 300 to 400 nm and also has excellent antioxidant ability.
【０００８】上記本発明の化合物は、２−ヒドロキシ−
５−ヒドロキシアルキルフェニルベンゾトリアゾール類
と２，４−置換フェノール類を塩基性触媒およびアミン
化合物の存在下にアルデヒドと反応させ、得られた化合
物をさらにメタクリル酸と反応させることにより得るこ
とができる。すなわち、本発明の化合物は、下記一般式
（２）The compound of the present invention is 2-hydroxy-
It can be obtained by reacting a 5-hydroxyalkylphenylbenzotriazole with a 2,4-substituted phenol with an aldehyde in the presence of a basic catalyst and an amine compound, and further reacting the obtained compound with methacrylic acid. That is, the compound of the present invention has the following general formula (2)
【０００９】[0009]
【化３】 Embedded image
【００１０】〔式中、ＸおよびＲ1 は前記規定に同一の
ものを表す〕で表される化合物と下記一般式（３）Wherein X and R 1 are the same as defined above, and a compound represented by the following general formula (3):
【００１１】[0011]
【化４】 Embedded image
【００１２】〔式中Ｒ4 およびＲ5 は前記規定に同一の
ものを表す〕で表される２，４−置換フェノール類を、
塩基性触媒およびアミン化合物の存在下に、ホルムアル
デヒド、パラホルムアルデヒド、トリオキサン、テトラ
オキシメチレン、アルキルアルデヒドおよびアリールア
ルデヒドからなる群から選ばれるアルデヒドと反応させ
ることにより下記一般式（４）Wherein R 4 and R 5 are the same as defined above,
By reacting with an aldehyde selected from the group consisting of formaldehyde, paraformaldehyde, trioxane, tetraoxymethylene, alkyl aldehyde and aryl aldehyde in the presence of a basic catalyst and an amine compound, the following general formula (4)
【００１３】[0013]
【化５】 Embedded image
【００１４】〔式中、Ｘ，Ｒ1 ，Ｒ3 ，Ｒ4 およびＲ5
は前記規定に同一のものを表わす〕で表わされる化合物
を得、次いでこれを下記一般式（５）Wherein X, R 1 , R 3 , R 4 and R 5
Represents the same as defined above] to obtain a compound represented by the following general formula (5)
【００１５】[0015]
【化６】 Embedded image
【００１６】〔Ｒ2 は前記規定に同一のものを表わす〕
で示されるアクリル酸とエステル化反応させることによ
り、製造することができる。本発明の化合物は、重合可
能な不飽和二重結合を有するから、用いる有機材料によ
っては、この材料中に結合されて耐久性のある安定化材
料を与えることができる。[R 2 represents the same as defined above]
Can be produced by an esterification reaction with acrylic acid represented by Since the compound of the present invention has a polymerizable unsaturated double bond, depending on the organic material used, it can be bonded into this material to provide a durable stabilizing material.
【００１７】[0017]
【実施例】以下、実施例により本発明をさらに説明す
る。 実施例１ 中間体６−（２−ベンゾトリアゾリル）−４−ヒドロキ
シエチル−６′−ｔ−ブチル−４′−メチル−２，２′
−メチレンビスフェノールの製造 撹拌機、還流冷却管、温度計および滴下ロートを備える
５００ｍｌの４ツ口フラスコに、４−メチル−２−ｔ−
ブチルフェノール６４．３ｇ（０．３９モル）、２−
（２′−ヒドロキシ−５′−ヒドロキシエチルフェニ
ル）−２Ｈ−ベンゾトリアゾール１０１ｇ（０．３９モ
ル）、パラホルムアルデヒド１３．６ｇ（０．３９モ
ル）、モノエタノールアミン３１．１ｇ（０．５１モ
ル）、ｎ−ブタノール２５ｇおよび苛性ソーダ３．２ｇ
（０．０８モル）を添加し、加熱した。The present invention will be further described with reference to the following examples. Example 1 Intermediate 6- (2-benzotriazolyl) -4-hydroxyethyl-6'-t-butyl-4'-methyl-2,2 '
-Production of methylene bisphenol 4-methyl-2-t- was placed in a 500 ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a dropping funnel.
64.3 g (0.39 mol) of butylphenol, 2-
101 g (0.39 mol) of (2'-hydroxy-5'-hydroxyethylphenyl) -2H-benzotriazole, 13.6 g (0.39 mol) of paraformaldehyde, 31.1 g (0.51 mol) of monoethanolamine , N-butanol 25 g and caustic soda 3.2 g
(0.08 mol) was added and heated.
【００１８】内部温度を８０〜９０℃に保持した後、１
２０℃まで上げ、還流冷却管でｎ−ブタノールを還流さ
せながら、約６ｇの水を分離した。その後、ｎ−ブタノ
ールおよびモノエタノールアミンを回収した。反応器内
残留物に溶剤としてキシロールを添加し、加熱溶解後、
希硫酸で中和処理し、水洗した。得られた結晶をトルエ
ンにより再結晶精製した。乾燥物として融点１４６〜１
４９℃の白色結晶を得た。元素分析結果は、炭素、水
素、窒素および酸素含有量が理論値にほぼ一致した。After maintaining the internal temperature at 80 to 90 ° C.,
The temperature was raised to 20 ° C., and about 6 g of water was separated while refluxing n-butanol with a reflux condenser. Thereafter, n-butanol and monoethanolamine were recovered. Add xylol as a solvent to the residue in the reactor, heat and dissolve,
It was neutralized with dilute sulfuric acid and washed with water. The obtained crystals were recrystallized and purified with toluene. 146-1 as melting point
49 ° C. white crystals were obtained. Elemental analysis results showed that the contents of carbon, hydrogen, nitrogen and oxygen almost coincided with the theoretical values.
【００１９】 元素分析結果 炭素％ 水素％ 窒素％ 酸素％ 理論値 ７２．３７ ６．７７ ９．７４ １１．１２ 実測値 ７１．９ ６．７ ９．７ １１．５ 実施例２ ６−（２−ベンゾトリアゾリル）−４−メタクリロキシ
エチル−６′−ｔ−ブチル−４′−メチル−２，２′−
メチレンビスフェノールの製造 撹拌機、還流冷却管、温度計および滴下ロートを備えた
５００mlの４ツ口フラスコに、実施例１で得られた中間
体６−（２−ベンゾトリアゾリル）−４−ヒドロキシエ
チル−６′−ｔ−ブチル−４′−メチル−２，２′−メ
チレンビスフェノール４４ｇ（０．１０２モル）ととも
に、メタクリル酸９．５ｇ（０．１１モル）、ハイドロ
キノン０．５ｇ，ｐ−トルエンスルホン酸水和物０．６
ｇおよびトルエン３００ｇを添加し、昇温後、還流させ
ながら、発生する水を分離した。反応物を１００℃以下
に冷却して、炭酸水素ナトリウム水溶液、３％塩酸水お
よび水で順次に洗浄した。Elemental analysis result Carbon% Hydrogen% Nitrogen% Oxygen% Theoretical value 72.37 6.77 9.74 11.12 Actual value 71.9 6.7 9.7 11.5 Example 2 6- (2- Benzotriazolyl) -4-methacryloxyethyl-6'-t-butyl-4'-methyl-2,2'-
Preparation of methylene bisphenol The intermediate 6- (2-benzotriazolyl) -4-hydroxy obtained in Example 1 was placed in a 500 ml four-necked flask equipped with a stirrer, a reflux condenser, a thermometer and a dropping funnel. Ethyl-6'-tert-butyl-4'-methyl-2,2'-methylenebisphenol (44 g, 0.102 mol), methacrylic acid 9.5 g (0.11 mol), hydroquinone 0.5 g, p-toluene Sulfonic acid hydrate 0.6
g and 300 g of toluene were added, and after raising the temperature, generated water was separated while refluxing. The reaction was cooled to below 100 ° C. and washed sequentially with aqueous sodium bicarbonate, 3% aqueous hydrochloric acid and water.
【００２０】溶剤を濃縮後、メタノール中で晶析した。
晶析物をトルエンにより再結晶精製した。得られた精製
物は、赤外線吸収スペクトルにより：１，６４０ｃｍ-1
付近にＣ＝Ｃ、１，７１０ｃｍ-1付近にＣ＝Ｏのメタク
リル酸化合物特有の吸収が認められた。融点は１３８〜
１４１℃であった。分光光度計による紫外線吸収曲線図
を図１に示す。最大吸収波長は３３７．０ｎｍである。After concentrating the solvent, it was crystallized in methanol.
The crystallized product was purified by recrystallization with toluene. The obtained purified product was analyzed by infrared absorption spectrum at 1,640 cm -1.
The absorption characteristic of a methacrylic acid compound having C ＝ C and C ＝ O was observed near and at 1,710 cm −1 , respectively. Melting point is 138 ~
141 ° C. FIG. 1 shows an ultraviolet absorption curve obtained by a spectrophotometer. The maximum absorption wavelength is 337.0 nm.
【００２１】また、元素分析結果は、炭素、水素、窒素
および酸素含有量が理論値にほぼ一致した。 元素分析結果 炭素％ 水素％ 窒素％ 酸素％ 理論値 ７２．１２ ６．６６ ８．４１ １２．８１ 実測値 ７１．９ ６．６ ８．３ １３．０ 実施例３ 中間体６−（５−クロロ−２−ベンゾトリアゾリル）−
４−ヒドロキシエチル−６′−ｔ−ブチル−４′−メチ
ル−２，２′−メチレンビスフェノールの製造 ２−（２′−ヒドロキシ−５′−ヒドロキシエチルフェ
ニル）−２Ｈ−ベンゾトリアゾール１０１ｇを２−
（２′−ヒドロキシ−５′−ヒドロキシエチルフェニ
ル）−５−クロロ−ベンゾトリアゾール１１３．５ｇ
（０．３９２モル）に代えた以外は、実施例１と同じ操
作を繰り返した。粗生成物をトルエンにより再結晶精製
した。The results of elemental analysis showed that the contents of carbon, hydrogen, nitrogen and oxygen almost coincided with the theoretical values. Elemental analysis results Carbon% Hydrogen% Nitrogen% Oxygen% Theoretical 72.12 6.66 8.41 12.81 Found 71.9 6.6 8.3 13.0 Example 3 Intermediate 6- (5-chloro) -2-benzotriazolyl)-
Production of 4-hydroxyethyl-6'-tert-butyl-4'-methyl-2,2'-methylenebisphenol 2- (2'-hydroxy-5'-hydroxyethylphenyl) -2H-benzotriazole 101 g
(2'-hydroxy-5'-hydroxyethylphenyl) -5-chloro-benzotriazole 113.5 g
(0.392 mol), except that the same operation as in Example 1 was repeated. The crude product was purified by recrystallization with toluene.
【００２２】乾燥物の融点は１４６〜１４９℃であっ
た。元素分析結果は、炭素、水素、窒素、塩素および酸
素含有量が理論値にほぼ一致した。 元素分析結果 炭素％ 水素％ 窒素％ 酸素％ 塩素％ 理論値 ６７．０２ ６．０６ ９．０２ １０．３０ ７．６１ 実測値 ６６．９ ５．９ ９．０ １０．２ ７．５ 実施例４ ６−（５−クロロ−２−ベンゾトリアゾリル）−４−メ
タクリロキシエチル−６′−ｔ−ブチル−４′−メチル
−２，２′−メチレンビスフェノールの製造 中間体６−（２−ベンゾトリアゾリル）−４−ヒドロキ
シエチル−６′−ｔ−ブチル−４′−メチル−２，２′
−メチレンビスフェノール４４ｇを実施例３で得られた
中間体６−（５−クロロ−２−ベンゾトリアゾリル）−
４−ヒドロキシエチル−６′−ｔ−ブチル−４′−メチ
ル−２，２′−メチレンビスフェノール４７．５ｇ
（０．１０２モル）に代えた以外は、実施例２と同じ操
作を繰り返した。The melting point of the dried product was 146 to 149 ° C. The elemental analysis results showed that the contents of carbon, hydrogen, nitrogen, chlorine and oxygen almost coincided with the theoretical values. Elemental analysis result Carbon% Hydrogen% Nitrogen% Oxygen% Chlorine% Theoretical value 67.02 6.06 9.02 10.30 7.61 Actual value 66.9 5.9 9.0 10.2 7.5 Example 4 Preparation of 6- (5-chloro-2-benzotriazolyl) -4-methacryloxyethyl-6'-t-butyl-4'-methyl-2,2'-methylenebisphenol Intermediate 6- (2-benzo Triazolyl) -4-hydroxyethyl-6'-tert-butyl-4'-methyl-2,2 '
-44 g of methylene bisphenol was used as the intermediate 6- (5-chloro-2-benzotriazolyl) obtained in Example 3.
47.5 g of 4-hydroxyethyl-6'-tert-butyl-4'-methyl-2,2'-methylenebisphenol
(0.102 mol), except that the same operation as in Example 2 was repeated.
【００２３】再結晶精製後の乾燥物の融点は１３４〜１
３５℃であった。得られた精製物は、赤外線吸収スペク
トルにより、１，６４０ｃｍ-1付近にＣ＝Ｃ、１，７１
０ｃｍ-1付近にＣ＝Ｏのメタクリル酸化合物特有の吸収
が認められた。分光光度計による紫外線吸収曲線図を図
２に示す。最大吸収波長は３４３．８ｎｍである。ま
た、元素分析結果は、炭素、水素、窒素、塩素および酸
素含有量が理論値にほぼ一致した。The melting point of the dried product after recrystallization purification is 134-1.
35 ° C. According to the infrared absorption spectrum, the obtained purified product had a C = C of about 1,640 cm -1 and a 1,71
The absorption characteristic of the methacrylic acid compound of C ＝ O was observed around 0 cm −1 . FIG. 2 shows an ultraviolet absorption curve obtained by a spectrophotometer. The maximum absorption wavelength is 343.8 nm. The elemental analysis results showed that the contents of carbon, hydrogen, nitrogen, chlorine and oxygen almost coincided with the theoretical values.
【００２４】 元素分析結果 炭素％ 水素％ 窒素％ 酸素％ 塩素％ 理論値 ６７．４７ ６．０４ ７．８７ １１．９８ ６．６４ 実測値 ６７．２ ６．０ ７．７ １２．４ ６．６ 実施例５ 中間体６−（５−メチル−２−ベンゾトリアゾリル）−
４−ヒドロキシエチル−６′−ｔ−ブチル−４′−メチ
ル−２，２′−メチレンビスフェノールの製造 ２−（２′−ヒドロキシ−５′−ヒドロキシエチルフェ
ニル）−２Ｈ−ベンゾトリアゾール１０１ｇを２−
（２′−ヒドロキシ−５′−ヒドロキシエチルフェニ
ル）−５−メチル−ベンゾトリアゾール１０５ｇ（０．
３９モル）に代えた以外は、実施例１と同じ操作を繰り
返した。粗生成物をトルエンにより再結晶精製した。Elemental Analysis Results Carbon% Hydrogen% Nitrogen% Oxygen% Chlorine% Theoretical 67.47 6.04 7.87 11.98 6.64 Found 67.2 6.0 7.7 12.4 6.6 Example 5 Intermediate 6- (5-methyl-2-benzotriazolyl)-
Production of 4-hydroxyethyl-6'-tert-butyl-4'-methyl-2,2'-methylenebisphenol 2- (2'-hydroxy-5'-hydroxyethylphenyl) -2H-benzotriazole 101 g
105 g of (2'-hydroxy-5'-hydroxyethylphenyl) -5-methyl-benzotriazole (0.
39 mol), and the same operation as in Example 1 was repeated. The crude product was purified by recrystallization with toluene.
【００２５】乾燥物の融点は１８８〜１８９℃あった。
元素分析結果は、炭素、水素、窒素および酸素含有量が
理論値にほぼ一致した。 元素分析結果 炭素％ 水素％ 窒素％ 酸素％ 理論値 ７２．７８ ７．０１ ９．４３ １０．７７ 実測値 ７２．６ ７．０ ９．４ １０．７ 実施例６ ６−（５−メチル−２−ベンゾトリアゾリル）−４−メ
タクリロキシエチル−６′−ｔ−ブチル−４′−メチル
−２，２′−メチレンビスフェノールの製造 中間体６−（２−ベンゾトリアゾリル）−４−ヒドロキ
シエチル−６′−ｔ−ブチル−４′−メチル−２，２′
−メチレンビスフェノール４４ｇを実施例５で得られた
中間体６−（５−メチル−２−ベンゾトリアゾリル）−
４−ヒドロキシエチル−６′−ｔ−ブチル−４′−メチ
ル−２，２′−メチレンビスフェノール４５ｇ（０．１
０２モル）に代えた以外は、実施例２と同じ操作を繰り
返した。粗生成物をトルエンにより再結晶精製した。The melting point of the dried product was 188 to 189 ° C.
Elemental analysis results showed that the contents of carbon, hydrogen, nitrogen and oxygen almost coincided with the theoretical values. Elemental analysis results Carbon% Hydrogen% Nitrogen% Oxygen% Theoretical value 72.78 7.01 9.43 10.77 Actual value 72.6 7.0 9.4 10.7 Example 6 6- (5-methyl-2) Preparation of -benzotriazolyl) -4-methacryloxyethyl-6'-t-butyl-4'-methyl-2,2'-methylenebisphenol Intermediate 6- (2-benzotriazolyl) -4-hydroxy Ethyl-6'-t-butyl-4'-methyl-2,2 '
-44 g of methylene bisphenol was used as the intermediate 6- (5-methyl-2-benzotriazolyl) obtained in Example 5.
45 g of 4-hydroxyethyl-6'-t-butyl-4'-methyl-2,2'-methylenebisphenol (0.1
02 mol), and the same operation as in Example 2 was repeated. The crude product was purified by recrystallization with toluene.
【００２６】乾燥物の融点は１２０〜１２３℃であっ
た。得られた精製物は、赤外線吸収スペクトルにより、
１，６４０ｃｍ-1付近にＣ＝Ｃ、１，７１０ｃｍ-1付近
にＣ＝Ｏのメタクリル酸化合物特有の吸収が認められ
た。分光光度計による紫外線吸収曲線図を図３に示す。
最大吸収波長は３４０．２ｎｍである。また、元素分析
結果は、炭素、水素、窒素および酸素含有量が理論値に
ほぼ一致した。The melting point of the dried product was 120-123 ° C. The resulting purified product is identified by infrared absorption spectrum
1,640Cm -1 around the C = C, C = O methacrylate compound-specific absorption was observed in the vicinity of 1,710cm -1. FIG. 3 shows an ultraviolet absorption curve diagram by a spectrophotometer.
The maximum absorption wavelength is 340.2 nm. In addition, the results of elemental analysis showed that the contents of carbon, hydrogen, nitrogen and oxygen almost coincided with the theoretical values.
【００２７】 元素分析結果 炭素％ 水素％ 窒素％ 酸素％ 理論値 ７２．４９ ６．８７ ８．１８ １２．４６ 実測値 ７２．４ ６．９ ８．２ １２．４Elemental analysis results Carbon% Hydrogen% Nitrogen% Oxygen% Theoretical value 72.49 6.87 8.18 12.46 Actual value 72.4 6.9 8.2 12.4
【００２８】[0028]
【発明の効果】本発明によれば、波長３００〜４００ｎ
ｍの近紫外領域での紫外線吸収能に優れるとともに酸化
防止能にも優れ、かつ、重合可能な不飽和二重結合を分
子内に有する、新規なベンゾトリアゾール化合物が提供
される。According to the present invention, the wavelength is 300 to 400 n.
A novel benzotriazole compound having excellent ultraviolet absorbing ability in the near ultraviolet region of m, excellent antioxidant ability, and having a polymerizable unsaturated double bond in the molecule is provided.
【図面の簡単な説明】[Brief description of the drawings]
【図１】実施例２で得られた化合物の紫外線吸収曲線
図。FIG. 1 is an ultraviolet absorption curve of the compound obtained in Example 2.
【図２】実施例４で得られた化合物の紫外線吸収曲線
図。FIG. 2 is an ultraviolet absorption curve of the compound obtained in Example 4.
【図３】実施例６で得られた化合物の紫外線吸収曲線
図。FIG. 3 is an ultraviolet absorption curve of the compound obtained in Example 6.
Claims (1)
アゾール化合物。 【化１】 〔式中、Ｘは水素、ハロゲンまたは炭素数１〜３のアル
コキシもしくはアルキルを表し、Ｒ1 は直鎖または枝分
かれ鎖の炭素数２〜１０のアルキレンを表し、Ｒ 2 は
Ｈ，−ＣＨ3 または−ＣＨ2 Ｘを表し、ここでＸはハロ
ゲンであり、Ｒ3 は水素、アルキルまたはアリールを表
わし、Ｒ4 およびＲ5 は同一であっても相異なっていて
もよく、それぞれ炭素数１〜８のアルキルを表わす〕1. A benzotri compound represented by the following general formula (1):
Azole compounds. Embedded image[Wherein X is hydrogen, halogen or an alkyl having 1 to 3 carbon atoms.
Represents xy or alkyl;1Is linear or branched
Represents an alkylene having 2 to 10 carbon atoms in the chain, TwoIs
H, -CHThreeOr -CHTwoRepresents X, where X is halo
Gen and RThreeRepresents hydrogen, alkyl or aryl
I, RFourAnd RFiveAre the same but different
And each represents an alkyl having 1 to 8 carbon atoms.]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10288338A JP2000119260A (en) | 1998-10-09 | 1998-10-09 | New reactive ultraviolet absorbing compound having antioxidative function |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10288338A JP2000119260A (en) | 1998-10-09 | 1998-10-09 | New reactive ultraviolet absorbing compound having antioxidative function |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2000119260A true JP2000119260A (en) | 2000-04-25 |
Family
ID=17728912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10288338A Pending JP2000119260A (en) | 1998-10-09 | 1998-10-09 | New reactive ultraviolet absorbing compound having antioxidative function |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2000119260A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329445B1 (en) | 1999-03-02 | 2001-12-11 | Menicon Co., Ltd | Ocular lens material |
| US6559311B1 (en) * | 2001-10-30 | 2003-05-06 | Council Of Scientific And Industrial Research | Process for the synthesis of a photo-stabilizer |
| US6936717B2 (en) | 2001-10-30 | 2005-08-30 | Council Of Scientific & Industrial Research | Tinuvin P-hindred amine light stabilizer and derivatives thereof |
| WO2020218609A1 (en) * | 2019-04-26 | 2020-10-29 | ミヨシ油脂株式会社 | Ultraviolet absorber having excellent heat resistance and long-wavelength absorption |
| CN117264147A (en) * | 2023-11-22 | 2023-12-22 | 建滔(广州)电子材料制造有限公司 | Phenolic resin with UV shielding effect and preparation process thereof |
-
1998
- 1998-10-09 JP JP10288338A patent/JP2000119260A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329445B1 (en) | 1999-03-02 | 2001-12-11 | Menicon Co., Ltd | Ocular lens material |
| US6559311B1 (en) * | 2001-10-30 | 2003-05-06 | Council Of Scientific And Industrial Research | Process for the synthesis of a photo-stabilizer |
| US6936717B2 (en) | 2001-10-30 | 2005-08-30 | Council Of Scientific & Industrial Research | Tinuvin P-hindred amine light stabilizer and derivatives thereof |
| WO2020218609A1 (en) * | 2019-04-26 | 2020-10-29 | ミヨシ油脂株式会社 | Ultraviolet absorber having excellent heat resistance and long-wavelength absorption |
| CN113728070A (en) * | 2019-04-26 | 2021-11-30 | 三吉油脂株式会社 | Ultraviolet absorber having excellent heat resistance and excellent long-wavelength absorption |
| CN113728070B (en) * | 2019-04-26 | 2024-03-08 | 三吉油脂株式会社 | Ultraviolet absorber excellent in heat resistance and long-wavelength absorption |
| JP7506663B2 (en) | 2019-04-26 | 2024-06-26 | ミヨシ油脂株式会社 | UV absorber with excellent heat resistance and long wavelength absorption |
| CN117264147A (en) * | 2023-11-22 | 2023-12-22 | 建滔(广州)电子材料制造有限公司 | Phenolic resin with UV shielding effect and preparation process thereof |
| CN117264147B (en) * | 2023-11-22 | 2024-02-09 | 建滔(广州)电子材料制造有限公司 | Phenolic resin with UV shielding effect and preparation process thereof |
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