JP2009023955A - Ultraviolet light absorber-including minute capsule excellent in light stability - Google Patents
Ultraviolet light absorber-including minute capsule excellent in light stability Download PDFInfo
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Abstract
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本発明は紫外線吸収剤を内包する微小カプセルに関する。さらに詳しくは、特定のヒドロキシシランを縮重合したオルガノポリシロキサンを壁膜とし、光安定性が優れた紫外線吸収剤内包微小カプセルに関するものである。 The present invention relates to a microcapsule containing an ultraviolet absorber. More specifically, the present invention relates to a microcapsule encapsulating an ultraviolet absorber having a wall film of an organopolysiloxane obtained by condensation polymerization of a specific hydroxysilane and having excellent light stability.
オルガノポリシロキサンは、熱的、機械的安定である、耐光性を有する、生体不活性であるなどの優れた特性を有することから、広い分野で利用され、かつさらなる応用が期待されている。マイクロカプセルやナノカプセルなどの微小カプセルの分野においても、オルガノポリシロキサンまたはそれに類する材料を壁膜として用い微小カプセルを製造することが試みられている。例えば、本発明者らも、オルガノポリシロキサンとシリル化ペプチドの重合物を壁膜に用い、紫外線吸収剤を内包した微小カプセルを提案している（特許文献１）。 Organopolysiloxane has excellent properties such as thermal and mechanical stability, light resistance, and biological inertness, and thus is used in a wide range of fields and is expected to be further applied. Also in the field of microcapsules such as microcapsules and nanocapsules, attempts have been made to produce microcapsules using organopolysiloxane or a similar material as a wall film. For example, the present inventors have also proposed a microcapsule using a polymer of an organopolysiloxane and a silylated peptide as a wall film and encapsulating an ultraviolet absorber (Patent Document 1).
化粧品に紫外線防御剤が配合される際には、一般に、ＵＶＢ吸収剤とＵＶＡ吸収剤を併用して配合され、ＵＶＢ吸収剤としてパラメトキシケイヒ酸−２−エチルヘキシル、ＵＶＡ吸収剤として４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンの組み合わせがよく使用されていて、上記特許文献１でも同じ組み合わせの紫外線吸収剤が使用されている。 When a UV protection agent is blended in cosmetics, it is generally blended using a UVB absorber and a UVA absorber in combination, paramethoxycinnamic acid-2-ethylhexyl as a UVB absorber, and 4-tert- as a UVA absorber. A combination of butyl-4'-methoxydibenzoylmethane is often used, and the same combination of ultraviolet absorbers is also used in Patent Document 1.
しかしながら、紫外線吸収剤である４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンとパラメトキシケイヒ酸−２−エチルヘキシルを内包させた微小カプセルの光安定性は不十分であり、紫外線によって紫外線防御効果が低くなる問題があった。
従って、本発明は、特定のオルガノポリシロキサンとシリル化ペプチドとの重合物を壁膜とする微小カプセルにおいて、光安定性が高く、紫外線防御効果が低下しない微小カプセルを提供することを課題とする。 Accordingly, an object of the present invention is to provide a microcapsule having a wall film of a polymer of a specific organopolysiloxane and a silylated peptide, which has high photostability and does not deteriorate the UV protection effect. .
本発明者は、上記課題を解決するために研究を重ねた結果、オルガノポリシロキサンとシリル化ペプチドとの重合物を壁膜とする微小カプセルにおいて、紫外線吸収剤として２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルとパラメトキシケイヒ酸−２−エチルヘキシルを使用するときには、該微小カプセルの光安定性が高く、紫外線防御効果が低下しないことを見出し、本発明を完成するに到った。 As a result of repeated researches to solve the above-mentioned problems, the present inventors have found that 2- (4-diethylamino-2) is used as an ultraviolet absorber in a microcapsule having a wall film made of a polymer of an organopolysiloxane and a silylated peptide. -Hydroxybenzoyl) When using hexyl benzoate and 2-methoxyhexyl paramethoxycinnamate, the present inventors have found that the light stability of the microcapsules is high and the UV protection effect is not lowered, and the present invention has been completed. .
そして、微小カプセルに内包される２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルの量は、微小カプセルに内包される紫外線吸収剤全質量の１〜３６％であるのが望ましい。 The amount of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate encapsulated in the microcapsule is preferably 1 to 36% of the total mass of the ultraviolet absorber encapsulated in the microcapsule.
本発明の２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルとパラメトキシケイヒ酸−２−エチルヘキシルを紫外線吸収剤として内包する微小カプセルは、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンとパラメトキシケイヒ酸−２−エチルヘキシルとを紫外線吸収剤として用いている従来品と比べ、光安定性が優れていて紫外線防御効果が低下しない。 The microcapsules encapsulating 2- (4-diethylamino-2-hydroxybenzoyl) benzoate hexyl and paramethoxycinnamate-2-ethylhexyl of the present invention as UV absorbers are 4-tert-butyl-4′-methoxydibenzoyl. Compared to conventional products using methane and paramethoxycinnamic acid-2-ethylhexyl as an ultraviolet absorber, the light stability is excellent and the ultraviolet protection effect is not lowered.
本発明において、紫外線吸収剤内包微小カプセルとは、オルガノポリシロキサンとシリル化ペプチドとの重合物を壁膜とする内包済み微小カプセルであり、この微小カプセルは、前記特許文献１に記載の方法で製造することができる。 In the present invention, the ultraviolet absorber-encapsulated microcapsule is an encapsulated microcapsule having a wall membrane made of a polymer of an organopolysiloxane and a silylated peptide, and this microcapsule is obtained by the method described in Patent Document 1. Can be manufactured.
微小カプセルの壁膜となるオルガノポリシロキサンの原料としては、例えば、メチルトリエトキシシラン、ジメチルジエトキシシラン、オクチルトリエトキシシラン、トリメチルクロロシラン、フェニルトリクロロシランなどが挙げられる。また、シリル化ペプチドとしては、例えば、Ｎ−〔２−ヒドロキシ−３−（３’−トリヒドロキシシリル）プロポキシ〕プロピル加水分解タンパク、Ｎ−〔２−ヒドロキシ−３−（３’−ジヒドロキシメチルシリル）プロポキシ〕プロピル加水分解タンパクなどが挙げられる。 Examples of the raw material of the organopolysiloxane that becomes the wall film of the microcapsule include methyltriethoxysilane, dimethyldiethoxysilane, octyltriethoxysilane, trimethylchlorosilane, and phenyltrichlorosilane. Examples of silylated peptides include N- [2-hydroxy-3- (3′-trihydroxysilyl) propoxy] propyl hydrolyzed protein, N- [2-hydroxy-3- (3′-dihydroxymethylsilyl). ) Propoxy] propyl hydrolyzed protein.
上記のオルガノポリシロキサンの原料と上記のシリル化ペプチドとを用いて前記の特許文献１の方法で微小カプセルを製造する場合、紫外線吸収剤は微小カプセル全質量に対して０．０１〜９９質量％の範囲で内包させることができるが、微小カプセルの調製のしやすさや、調製した微小カプセルの紫外線吸収効果を考慮すると、紫外線吸収剤の内包率は微小カプセル全質量の８０〜９５％が好ましい。すなわち、内包させる紫外線吸収剤の量が少ない場合は微小カプセルの紫外線吸収剤効果が低くなり、従って化粧品に配合し、一定の効果を得るためには多量に配合する必要が生じる。また、紫外線吸収剤の内包率を極端に上げると、微小カプセル全量に占める壁膜部分の割合が減少し、微小カプセルの安定性が減少するおそれがある。 When producing the microcapsules by the method of Patent Document 1 using the organopolysiloxane raw material and the silylated peptide, the ultraviolet absorber is 0.01 to 99% by mass with respect to the total mass of the microcapsules. However, considering the ease of preparation of the microcapsules and the ultraviolet absorption effect of the prepared microcapsules, the encapsulation rate of the ultraviolet absorber is preferably 80 to 95% of the total mass of the microcapsules. That is, when the amount of the ultraviolet absorber to be encapsulated is small, the ultraviolet absorber effect of the microcapsules is lowered, so that it is necessary to add a large amount in order to obtain a certain effect when it is added to cosmetics. Moreover, when the encapsulation rate of the ultraviolet absorber is extremely increased, the ratio of the wall film portion to the total amount of the microcapsules is decreased, and the stability of the microcapsules may be decreased.
内包させる紫外線吸収剤は、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルとパラメトキシケイヒ酸−２−エチルヘキシルの混合物であるが、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルの量は、紫外線吸収剤全質量の１〜３６％以下であることが好ましい。すなわち、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルの量が上記範囲以上では、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルがパラメトキシケイヒ酸−２−エチルヘキシルに溶解されずに析出するおそれがあり、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルの量が上記範囲以下になると、紫外線防御効果を発揮できないおそれがある。 The ultraviolet absorber to be encapsulated is a mixture of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate and 2-methoxyhexyl paramethoxycinnamate, but 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid. The amount of hexyl acid is preferably 1 to 36% or less of the total mass of the UV absorber. That is, when the amount of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate is not less than the above range, hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate is converted to 2-ethylhexyl paramethoxycinnamate. If the amount of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate falls below the above range, the UV protection effect may not be exhibited.
次に、実施例を挙げて本発明を具体的に説明するが、本発明はそれらの実施例のみにより制約を受けるものではない。なお、実施例に先立ち、実施例で使用する紫外線吸収剤内包マイクロカプセルの合成例、比較合成例を示す。また、以下の合成例や実施例で用いる％は質量％である。 Next, the present invention will be specifically described by way of examples. However, the present invention is not limited only by these examples. Prior to the examples, synthesis examples and comparative synthesis examples of the ultraviolet absorber-containing microcapsules used in the examples are shown. Moreover,% used in the following synthesis examples and examples is mass%.
合成例１：
Ｎ−〔２−ヒドロキシ−３−（３’−トリヒドロキシシリル）プロポキシ〕プロピル加水分解セリシン、メチルトリエトキシシランおよびオクチルトリエトキシシランの加水分解物共縮重合体からなるポリシロキンを壁膜とする２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルとパラメトキシケイヒ酸−２−エチルヘキシルを内包する微小カプセルの製造
１）カプセル壁膜のプレポリマーの調製
上蓋に滴下ロートと還流冷却器を備え、メカニカルスターラを備えた内径１２ｃｍ、容量２リットルの丸底円筒形ガラス製反応容器に、あらかじめ水１８０ｇとＮ−〔２−ヒドロキシ−３−（３’−トリヒドロキシシリル）プロポキシ〕プロピル加水分解セリシン（加水分解セリシンの分子量は数平均分子量で約２０００）２０ｇおよび１８％塩酸９．２ｇを入れておき、５０℃で攪拌しながらメチルトリエトキシシラン（信越シリコーン社製ＫＢＥ−１３）３２．４ｇとオクチルトリエトキシシラン（東レ・ダウコーニング社製Ａ−１３７）１０．１ｇの混合物を滴下ロートから滴下した。滴下終了後、さらに、５０℃で３時間攪拌した後、攪拌しながら２０％水酸化ナトリウム水溶液１１．０ｇを滴下し、ｐＨを６．０にした。
Synthesis example 1:
N- [2-hydroxy-3- (3′-trihydroxysilyl) propoxy] propyl hydrolyzed sericin, methyltriethoxysilane and octyltriethoxysilane hydrolyzate copolycondensation polymer is used as a wall film 2 -Manufacture of microcapsules containing hexyl (4-diethylamino-2-hydroxybenzoyl) benzoate and 2-ethylhexyl paramethoxycinnamate 1) Preparation of prepolymer for capsule wall membrane A dropping funnel and reflux condenser are provided on the top lid. In a round bottom cylindrical glass reaction vessel equipped with a mechanical stirrer and having an inner diameter of 12 cm and a capacity of 2 liters, water 180 g and N- [2-hydroxy-3- (3′-trihydroxysilyl) propoxy] propyl hydrolyzed sericin (The molecular weight of hydrolyzed sericin is about 2000 in terms of number average molecular weight) 0 g and 9.2 g of 18% hydrochloric acid were added, and 32.4 g of methyltriethoxysilane (KBE-13 manufactured by Shin-Etsu Silicone) and octyltriethoxysilane (A-137 manufactured by Toray Dow Corning Co., Ltd.) were stirred at 50 ° C. ) 10.1 g of the mixture was dropped from the dropping funnel. After completion of the addition, the mixture was further stirred at 50 ° C. for 3 hours, and then 11.0 g of a 20% aqueous sodium hydroxide solution was added dropwise with stirring to adjust the pH to 6.0.
２）芯物質の添加と乳化
１）で調製した反応液を６００ｒｐｍで攪拌しながら２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシル（ＢＡＳＦ社製ユビナールＡ Ｐｌｕｓ）１４７．１ｇパラメトキシケイヒ酸−２−エチルヘキシル（ＢＡＳＦ社製ユビナールＭＣ８０Ｎ）２６１．５ｇとテトラエトキシシラン（信越シリコーン社製ＫＢＥ−０４）４．１ｇの混合物を加え、さらに、６００ｒｐｍで３時間攪拌し続けた。
2) Addition and emulsification of core substance While stirring the reaction solution prepared in 1) at 600 rpm, 147.1 g of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate (Ubinal A Plus manufactured by BASF) A mixture of 261.5 g of acid-2-ethylhexyl (Ubinal MC80N manufactured by BASF) and 4.1 g of tetraethoxysilane (KBE-04 manufactured by Shin-Etsu Silicone) was added, and stirring was continued at 600 rpm for 3 hours.
３）微粒化
２）で調製した反応液をホモミキサーの容器に移して、５０℃、１０，０００ｒｐｍで９０分間ホモミキサーにかけて、微粒化した。
3) Atomization The reaction solution prepared in 2) was transferred to a homomixer container and atomized by applying the homomixer at 50 ° C. and 10,000 rpm for 90 minutes.
４）壁膜のオーバーコート処理
３）で調製した反応液を元の反応容器で５０℃、５００ｒｐｍで撹拌しながらメチルトリクロロシラン（信越シリコーン社製ＬＳ−４０）１．４ｇとメチルトリエトキシシラン（信越シリコーン社製ＫＢＥ−１３）６．５ｇの混合物を加え、さらに、５００ｒｐｍで１時間撹拌した後、５％水酸化ナトリウム水溶液２１．６ｇを加え中和した。
4) Overcoat treatment of wall membrane While stirring the reaction solution prepared in 3) at 50 ° C. and 500 rpm in the original reaction vessel, 1.4 g of methyltrichlorosilane (LS-40 manufactured by Shin-Etsu Silicone) and methyltriethoxysilane ( After adding 6.5 g of a mixture of Shin-Etsu Silicone KBE-13) and stirring at 500 rpm for 1 hour, 21.6 g of 5% aqueous sodium hydroxide solution was added for neutralization.
５）凝集防止と壁膜の硬化処理
４）で調製した反応液を５０℃、５００ｒｐｍで攪拌しながらトリメチルクロロシラン（信越シリコーン社製ＫＡ−３１）４．０ｇを加えた、さらに、５００ｒｐｍで１時間撹拌した後、５％水酸化ナトリウム水溶液２８．７ｇを加え中和した。反応液の温度を徐々に上げ、アルコールを含む蒸気を留去し、さらに１５０ｒｐｍで攪拌しながら２時間加熱した。この反応液を室温で１５０ｒｐｍで攪拌しながら冷却し、固型分濃度を６０％に調整した内包済み微小カプセルの水分散液を７２８ｇ得た。
5) Prevention of aggregation and hardening treatment of wall film While stirring the reaction solution prepared in 4) at 50 ° C. and 500 rpm, 4.0 g of trimethylchlorosilane (KA-31 manufactured by Shin-Etsu Silicone) was added, and further at 500 rpm for 1 hour. After stirring, 28.7 g of 5% aqueous sodium hydroxide solution was added for neutralization. The temperature of the reaction solution was gradually raised, the alcohol-containing vapor was distilled off, and the mixture was further heated for 2 hours with stirring at 150 rpm. This reaction liquid was cooled while stirring at 150 rpm at room temperature, and 728 g of an aqueous dispersion of encapsulated microcapsules having a solid content concentration adjusted to 60% was obtained.
比較合成例１：
Ｎ−〔２−ヒドロキシ−３−（３’−トリヒドロキシシリル）プロポキシ〕プロピル加水分解セリシン、メチルトリエトキシシランおよびオクチルトリエトキシシランの加水分解物共縮重合体からなるポリシロキンを壁膜とする４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンとパラメトキシケイヒ酸−２−エチルヘキシルを内包する微小カプセルの製造
２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルに代えて４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンを同量用いた他は合成例１と同様にして、紫外線吸収剤として４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンとパラメトキシケイヒ酸−２−エチルヘキシルを内包する固型分濃度６０％に調整した微小カプセルの水分散液を７２０ｇを得た。
Comparative synthesis example 1:
N- [2-hydroxy-3- (3'-trihydroxysilyl) propoxy] propyl hydrolyzed sericin, methyltriethoxysilane and octyltriethoxysilane hydrolyzate copolycondensate polysilokine as a wall film 4 -Production of microcapsules containing tert-butyl-4'-methoxydibenzoylmethane and 2-methoxyhexyl paramethoxycinnamate 4-tert- in place of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate 4-tert-Butyl-4'-methoxydibenzoylmethane and 2-methoxyhexyl paramethoxycinnamate as UV absorbers in the same manner as in Synthesis Example 1 except that the same amount of butyl-4'-methoxydibenzoylmethane was used. An aqueous dispersion of microcapsules adjusted to a solid content concentration of 60% containing 7 20 g was obtained.
実施例１および比較例１
合成例１および比較合成例１で製造した紫外線吸収剤内包微小カプセルをそれぞれ実施例１および比較例１とし、それぞれの微小カプセルの光安定性を下記の［光安定性評価法］で評価した。
Example 1 and Comparative Example 1
The ultraviolet absorber-encapsulated microcapsules produced in Synthesis Example 1 and Comparative Synthesis Example 1 were respectively Example 1 and Comparative Example 1, and the light stability of each microcapsule was evaluated by the following [Photostability Evaluation Method].
［光安定性評価法］
２×２ｃｍのすりガラスに、得られた内包済み微小カプセルを約４ｍｇを正確に秤量し、上から透明な石英ガラスを乗せ、試料をすりガラスと石英ガラスで挟み込む。石英ガラス面を上にして、ＳＵＮＴＥＳＴ ＣＰＳ＋（ＡＴＬＡＳ Ｍａｔｅｒｉａｌ Ｔｅｓｔｉｎｇ Ｔｅｃｈｎｏｌｏｇｙ社製）内に設置し、紫外線量が５３１３ｋＪ／ｍ２、１０，６９２ｋＪ／ｍ２になるように照射する。照射後、酢酸エチルにて紫外線吸収剤を抽出し、下記の条件での液体クロマトグラフィーによって内包済み微小カプセル約４ｍｇに含まれる紫外線吸収剤の量を求める。紫外線を照射しない微小カプセルに含まれる紫外線吸収剤量を１００％として、紫外線照射による紫外線吸収剤量の残存率（％）を算出する。
[Photostability evaluation method]
About 4 mg of the obtained encapsulated microcapsule is accurately weighed on a 2 × 2 cm ground glass, and a transparent quartz glass is placed on the top, and the sample is sandwiched between the ground glass and the quartz glass. Placed in SUNTEST CPS + (manufactured by ATLAS Material Testing Technology) with the quartz glass surface facing up, irradiation is performed so that the amount of ultraviolet rays is 5313 kJ / m 2 and 10,692 kJ / m 2 . After irradiation, the ultraviolet absorber is extracted with ethyl acetate, and the amount of the ultraviolet absorber contained in about 4 mg of the encapsulated microcapsules is determined by liquid chromatography under the following conditions. The remaining amount (%) of the amount of ultraviolet absorbent by ultraviolet irradiation is calculated with the amount of ultraviolet absorbent contained in the microcapsules not irradiated with ultraviolet light being 100%.
液体クロマトグラフィーの測定条件
カラム ：ＴＳＫ−ＧＥＬ ＯＤＳ−１２０Ｔ ４．６ｍｍ×１５０ｍｍ〔東ソー（株）〕
移動相 ：メタノール：水＝９：１
流速 ：０．８ｍＬ／ｍｉｎ
検出波長：２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシル ３５４ｎｍ、パラメトキシケイヒ酸−２−エチルヘキシル ３１０ｎｍ、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ３５８ｎｍ
Measurement condition column for liquid chromatography : TSK-GEL ODS-120T 4.6 mm × 150 mm [Tosoh Corporation]
Mobile phase: methanol: water = 9: 1
Flow rate: 0.8 mL / min
Detection wavelength: hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate 354 nm, 2-ethylhexyl paramethoxycinnamate 310 nm, 4-tert-butyl-4′-methoxydibenzoylmethane 358 nm
上記の評価法で算出した、それぞれの微小カプセル中の紫外線吸収剤の残存率を表１に示す。 Table 1 shows the residual ratio of the UV absorber in each microcapsule calculated by the above evaluation method.
表１に示したように、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルとパラメトキシケイヒ酸−２−エチルヘキシルを内包する実施例１の微小カプセルは、１０，６９２ｋＪ／ｍ２の紫外線照射後も、ＵＶ−Ａ吸収剤の２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルは全く影響を受けていず、ＵＶ−Ｂ吸収剤のパラメトキシケイヒ酸−２−エチルヘキシルも５０％以上残存していた。これに対し、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンとパラメトキシケイヒ酸−２−エチルヘキシルを内包する比較例１の微小カプセルでは、５３１３ｋＪ／ｍ２の紫外線照射で、ＵＶ−Ａ吸収剤である４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンはすべて分解し、ＵＶ−Ｂ吸収剤のパラメトキシケイヒ酸−２−エチルヘキシルも３０％程度しか残存していなかった。すなわち、２−（４−ジエチルアミノ−２−ヒドロキシベンゾイル）安息香酸ヘキシルとパラメトキシケイヒ酸−２−エチルヘキシルを内包する微小カプセルは、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタンとパラメトキシケイヒ酸−２−エチルヘキシルを内包する微小カプセルに比べて、光安定性が優れていることが明らかであった。
As shown in Table 1, the microcapsules of Example 1 containing hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate and 2-ethylhexyl paramethoxycinnamate were 10,692 kJ / m 2 . Even after UV irradiation, the UV-A absorber hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate was not affected at all, and the UV-B absorber para-methoxycinnamate-2-ethylhexyl was also 50. % Or more remained. On the other hand, in the microcapsule of Comparative Example 1 containing 4-tert-butyl-4′-methoxydibenzoylmethane and paramethoxycinnamic acid-2-ethylhexyl, UV-A absorption is obtained by ultraviolet irradiation of 5313 kJ / m 2. 4-tert-Butyl-4′-methoxydibenzoylmethane, which is an agent, was all decomposed, and only about 30% of para-methoxycinnamate-2-ethylhexyl, a UV-B absorber, remained. That is, a microcapsule enclosing 2- (4-diethylamino-2-hydroxybenzoyl) benzoic acid hexyl and paramethoxycinnamic acid-2-ethylhexyl is composed of 4-tert-butyl-4′-methoxydibenzoylmethane and paramethoxy It was clear that the photostability was superior to the microcapsules encapsulating acid-2-ethylhexyl.
Claims (2)
The content of hexyl 2- (4-diethylamino-2-hydroxybenzoyl) benzoate encapsulated in a microcapsule is 1 to 36% of the total mass of the encapsulated ultraviolet absorber. Microcapsules.
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| JP2007189217A JP2009023955A (en) | 2007-07-20 | 2007-07-20 | Ultraviolet light absorber-including minute capsule excellent in light stability |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9549891B2 (en) | 2012-03-19 | 2017-01-24 | The Procter & Gamble Company | Superabsorbent polymers and sunscreen actives for use in skin care compositions |
| CN104799278B (en) * | 2015-03-31 | 2019-01-15 | 武汉天天好生物制品有限公司 | A kind of krill oil microcapsule and preparation method thereof enhancing effect for reducing blood fat |
| CN109310618A (en) * | 2016-06-03 | 2019-02-05 | 株式会社成和化成 | Cosmetics substrate and cosmetics containing the cosmetics substrate |
| US10285926B2 (en) | 2015-06-29 | 2019-05-14 | The Procter & Gamble Company | Superabsorbent polymers and starch powders for use in skin care compositions |
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2007
- 2007-07-20 JP JP2007189217A patent/JP2009023955A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9549891B2 (en) | 2012-03-19 | 2017-01-24 | The Procter & Gamble Company | Superabsorbent polymers and sunscreen actives for use in skin care compositions |
| US9839598B2 (en) | 2012-03-19 | 2017-12-12 | The Procter & Gamble Company | Superabsorbent polymers and sunscreen actives for use in skin care compositions |
| CN104799278B (en) * | 2015-03-31 | 2019-01-15 | 武汉天天好生物制品有限公司 | A kind of krill oil microcapsule and preparation method thereof enhancing effect for reducing blood fat |
| US10285926B2 (en) | 2015-06-29 | 2019-05-14 | The Procter & Gamble Company | Superabsorbent polymers and starch powders for use in skin care compositions |
| CN109310618A (en) * | 2016-06-03 | 2019-02-05 | 株式会社成和化成 | Cosmetics substrate and cosmetics containing the cosmetics substrate |
| CN109310618B (en) * | 2016-06-03 | 2021-07-30 | 株式会社成和化成 | Cosmetic base material and cosmetic containing the same |
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