JP4887207B2 - Ultraviolet absorber and skin external preparation composition containing the same - Google Patents
Ultraviolet absorber and skin external preparation composition containing the same Download PDFInfo
- Publication number
- JP4887207B2 JP4887207B2 JP2007118998A JP2007118998A JP4887207B2 JP 4887207 B2 JP4887207 B2 JP 4887207B2 JP 2007118998 A JP2007118998 A JP 2007118998A JP 2007118998 A JP2007118998 A JP 2007118998A JP 4887207 B2 JP4887207 B2 JP 4887207B2
- Authority
- JP
- Japan
- Prior art keywords
- oxide
- phase
- ultraviolet
- dimethylaminopyridine
- external preparation
- 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.)
- Expired - Fee Related
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- YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 description 1
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- 229940089020 evening primrose oil Drugs 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- JCDAAXRCMMPNBO-UHFFFAOYSA-N iron(3+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Ti+4].[Fe+3].[Fe+3] JCDAAXRCMMPNBO-UHFFFAOYSA-N 0.000 description 1
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 238000006386 neutralization reaction Methods 0.000 description 1
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- 239000002736 nonionic surfactant Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 229940078498 peg-5 glyceryl stearate Drugs 0.000 description 1
- 229910052628 phlogopite Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
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- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical class OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
本発明はピリジン化合物に関し、特に紫外線吸収剤としてのピリジン化合物及びそれを配合した皮膚外用剤組成物に関する。 The present invention relates to a pyridine compound, and more particularly to a pyridine compound as an ultraviolet absorber and a skin external preparation composition containing the pyridine compound.
太陽光に含まれる紫外線のうち、２９０ｎｍ以下の波長の紫外線はオゾン層によって吸収され地表に到達しないが、２９０〜４００ｎｍの紫外線は地表に到達し、様々な影響を及ぼす。皮膚科学的には、２９０〜３２０ｎｍの中波長紫外線は紅班や水泡の形成、メラニン形成亢進、色素沈着等を引き起こすことが知られている。また、３２０〜４００ｎｍの長波長紫外線は照射直後に皮膚を黒化させる即時黒化作用を有し、また、そのエネルギーが真皮にまで達するため、血管壁や結合組織中の弾性繊維にも影響を及ぼすとされる。これらの中〜長波長紫外線の作用は、皮膚の老化を促進し、しみ、そばかす、しわ等の形成の一因であると考えられている。
このような紫外線から皮膚を保護するために、従来からベンゾトリアゾール誘導体、ベンゾフェノン誘導体、サリチル酸誘導体、パラアミノ安息香酸誘導体、桂皮酸誘導体、ウロカニン酸誘導体等の紫外線吸収剤が利用されてきた。
Among ultraviolet rays contained in sunlight, ultraviolet rays having a wavelength of 290 nm or less are absorbed by the ozone layer and do not reach the ground surface, but ultraviolet rays of 290 to 400 nm reach the ground surface and have various effects. Dermatologically, it is known that medium wavelength ultraviolet rays of 290 to 320 nm cause formation of erythema and water bubbles, increased melanogenesis, pigmentation and the like. In addition, 320-400 nm long-wavelength ultraviolet rays have an immediate darkening effect that darkens the skin immediately after irradiation, and the energy reaches the dermis, affecting the vascular wall and elastic fibers in the connective tissue. It is said to affect. These effects of medium to long wavelength ultraviolet rays are considered to promote skin aging and contribute to the formation of spots, freckles, wrinkles and the like.
In order to protect the skin from such ultraviolet rays, ultraviolet absorbers such as benzotriazole derivatives, benzophenone derivatives, salicylic acid derivatives, paraaminobenzoic acid derivatives, cinnamic acid derivatives, and urocanic acid derivatives have been conventionally used.
しかしながら、これらの紫外線吸収剤は一般に油溶性であり、水性ベースの製品に配合することはできなかった。最近では夏の水浴や冬のスキー場などの使用に限らず、日常生活においても紫外線防御が重要と考えられており、通常のスキンケア化粧品においても紫外線防止効果のあるものが求められている。したがって、化粧水等の水系のスキンケア化粧品にも十分量配合できる水溶性紫外線吸収剤の開発が望まれている。
また、紫外線吸収剤として皮膚外用剤組成物に配合するに際し、皮膚刺激性がないことはもちろん、日光曝露によって紫外線吸収剤が分解されないことが要求されることは言うまでもない。
However, these UV absorbers are generally oil soluble and could not be incorporated into aqueous based products. Recently, UV protection is considered important not only in summer bathing and winter skiing, but also in everyday life, and ordinary skin care cosmetics are also required to have UV protection effects. Therefore, it is desired to develop a water-soluble ultraviolet absorber that can be blended in a sufficient amount even in water-based skin care cosmetics such as lotion.
In addition, when blended in an external preparation for skin as an ultraviolet absorber, it is needless to say that the ultraviolet absorber is not decomposed by exposure to sunlight, as well as being non-irritating to the skin.
これまで水溶性紫外線吸収剤はほとんどなく、現在使用されているものとしては２−ヒドロキシ−４−メトキシ−５−スルフォキソニウムベンゾフェノンナトリウムが知られている。しかしながら、前記物質はスルホン酸塩であるために、配合系のｐＨに影響を与え、また、配合系のｐＨにより紫外線吸収領域が変化するという問題があった。また、前記物質は水溶性ではあるものの、その溶解度は２５℃で約６％に過ぎず、製品中に高濃度に配合すると低温で析出するという問題があった。さらに、前記物質は可視光領域においても吸収を有するため淡黄色に着色しており、製品の色調に影響を与えるという欠点があった。 Until now, there is almost no water-soluble ultraviolet absorber, and 2-hydroxy-4-methoxy-5-sulfoxonium benzophenone sodium is known as a currently used one. However, since the substance is a sulfonate, there is a problem that the pH of the blending system is affected, and the ultraviolet absorption region changes depending on the pH of the blending system. Further, although the substance is water-soluble, its solubility is only about 6% at 25 ° C., and there is a problem that it precipitates at a low temperature when blended in a high concentration in the product. Furthermore, since the substance has absorption in the visible light region, it is colored pale yellow, which has the disadvantage of affecting the color tone of the product.
また、特開平１０−１２０６９８には２−デオキシヘキソース残基を有するｐ−アミノ安息香酸アミド誘導体が、特開２００２−３６３１９５には２−デオキシヘキソース残基を有する桂皮酸アミドがそれぞれ開示されているが、水への溶解性が低く不十分であり、必ずしも満足できるものではなかった。
さらに、紫外線吸収剤は医薬品や化粧料以外の分野でも使用されており、例えば、塗料、染料、顔料、各種樹脂、合成ゴム、ラテックス、フィルム、繊維等の各種材料に添加して紫外線吸収能を付与し、製品自体を、あるいはその塗膜やフィルムで被覆された製品を紫外線から保護し、紫外線による劣化、変質等を防止して、品質を維持するために用いられている。しかし、従来の紫外線吸収剤では、塗膜の焼き付け時や樹脂の成型時等に加熱によって昇華して揮散したり、加熱しなくとも経時的に徐々に揮散して効果が低下するという問題もあった。
本発明は、前記従来技術に鑑みなされたものであり、その目的は、水溶性が高く、紫外線波長領域において優れた吸収能を有し、可視領域には吸収がなく、しかも安定性、安全性の高い紫外線吸収剤及びそれを配合した皮膚外用剤組成物を提供することにある。
JP-A-10-120698 discloses a p-aminobenzoic acid amide derivative having a 2-deoxyhexose residue, and JP-A-2002-363195 discloses a cinnamic acid amide having a 2-deoxyhexose residue. However, the solubility in water was low and insufficient, and it was not always satisfactory.
Furthermore, UV absorbers are used in fields other than pharmaceuticals and cosmetics. For example, UV absorbers can be added to various materials such as paints, dyes, pigments, various resins, synthetic rubbers, latexes, films, fibers, etc. It is used to protect the product itself, or the product coated with the coating film or film from ultraviolet rays, prevent deterioration and alteration due to ultraviolet rays, and maintain the quality. However, conventional ultraviolet absorbers also have the problem that they sublimate and volatilize by heating during baking of the coating film or resin molding, or gradually evaporate over time without heating. It was.
The present invention has been made in view of the above prior art, and its purpose is high water solubility, excellent absorption in the ultraviolet wavelength region, no absorption in the visible region, and stability and safety. It is providing the ultraviolet absorber of high and the skin external preparation composition which mix | blended it.
前記目的を達成するために、本発明者らが鋭意検討を重ねた結果、特定のピリジン化合物が上記の性質を備え、紫外線吸収剤として非常に優れたものであることを見出し、本発明を完成するに至った。
すなわち、本発明は下記式（Ｉ）で表されるピリジン化合物及び／またはその塩からなる紫外線吸収剤を提供するものである。
（化１）
また、本発明は前記ピリジン化合物及び／またはその塩を含有する皮膚外用剤組成物を提供するものである。
本発明の皮膚外用剤組成物においては、さらに無機粉末を含有することが好適である。
In order to achieve the above object, as a result of intensive studies by the present inventors, it has been found that a specific pyridine compound has the above properties and is extremely excellent as an ultraviolet absorber, and the present invention has been completed. It came to do.
That is, the present invention provides an ultraviolet absorber comprising a pyridine compound represented by the following formula (I) and / or a salt thereof.
(Chemical formula 1)
Moreover, this invention provides the skin external preparation composition containing the said pyridine compound and / or its salt.
The skin external preparation composition of the present invention preferably further contains an inorganic powder.
本発明によれば、水溶性が高く、紫外線波長領域において優れた吸収能を有し、可視領域には吸収がなく、しかも安定性、安全性の高い紫外線吸収剤を得ることができる。また、前記紫外線吸収剤を配合することにより、紫外線吸収効果に優れた皮膚外用剤組成物を得ることができる。 According to the present invention, it is possible to obtain an ultraviolet absorber having high water solubility, excellent absorption in the ultraviolet wavelength region, no absorption in the visible region, and high stability and safety. Moreover, the skin external preparation composition excellent in the ultraviolet-ray absorption effect can be obtained by mix | blending the said ultraviolet absorber.
以下、本発明について詳細に説明する。
本発明にかかる紫外線吸収剤は下記式（１）で表されるピリジン化合物からなり、該ピリジン化合物は「４−ジメチルアミノピリジン Ｎ−オキシド」と表記することができる。
（化２）
また、本発明において、前記ピリジン化合物は公知の方法により無機塩または有機塩としてもよい。本発明に適用可能な塩に限定はないが、無機塩としては、例えば、塩酸塩、硫酸塩、リン酸塩、臭化水素酸塩、ナトリウム塩、カリウム塩、マグネシウム塩、カルシウム塩、アンモニウム塩等を挙げることができる。同様に有機塩としては、例えば、酢酸塩、乳酸塩、マレイン酸塩、フマル酸塩、酒石酸塩、クエン酸塩、メタンスルホン酸塩、ｐ−トルエンスルホン酸塩、トリエタノールアミン塩、ジエタノールアミン塩、アミノ酸塩等を挙げることができる。
Hereinafter, the present invention will be described in detail.
The ultraviolet absorber according to the present invention comprises a pyridine compound represented by the following formula (1), and the pyridine compound can be represented as “4-dimethylaminopyridine N-oxide”.
(Chemical formula 2)
In the present invention, the pyridine compound may be converted to an inorganic salt or an organic salt by a known method. The salt applicable to the present invention is not limited. Examples of the inorganic salt include hydrochloride, sulfate, phosphate, hydrobromide, sodium salt, potassium salt, magnesium salt, calcium salt, and ammonium salt. Etc. Similarly, as an organic salt, for example, acetate, lactate, maleate, fumarate, tartrate, citrate, methanesulfonate, p-toluenesulfonate, triethanolamine salt, diethanolamine salt, Examples include amino acid salts.
前記ピリジン化合物及び／またはその塩は、種々の製品へ配合してその優れた紫外線吸収作用を対象へ付与し、紫外線吸収性組成物とすることができる。特に、本発明のピリジン化合物及び／またはその塩は、自身の安定性に優れるだけでなく、光分解性を有する他の化合物の光安定性を高め、光分解を防ぐことも可能とする。これにより製品自体に高い安定性を与えることができると考えられる。
本発明にかかるピリジン化合物及び／またはその塩を配合し得る製品としては、例えば、化粧品、塗料、染料、顔料、各種樹脂、合成ゴム、ラテックス、フィルム、繊維等が挙げられる。特に、本発明にかかるピリジン化合物及び／またはその塩は人体に対して極めて高い安全性を有することから、皮膚外用剤組成物へ好適に配合することができる。
本発明のピリジン化合物及び／またはその塩はその効果を発揮し得る範囲で配合することが可能であるが、通常、各製品中に０．００１〜２０質量％配合することが好ましく、０．０１〜１０質量％の配合がさらに好適である。
The pyridine compound and / or a salt thereof can be blended into various products to impart an excellent ultraviolet absorbing action to the target, thereby obtaining an ultraviolet absorbing composition. In particular, the pyridine compound and / or salt thereof of the present invention not only has excellent stability, but also enhances the light stability of other compounds having photodegradability, thereby preventing photolysis. This is considered to give high stability to the product itself.
Examples of products that can be blended with the pyridine compound and / or salt thereof according to the present invention include cosmetics, paints, dyes, pigments, various resins, synthetic rubbers, latexes, films, fibers, and the like. In particular, since the pyridine compound and / or salt thereof according to the present invention has extremely high safety for the human body, it can be suitably blended into a skin external preparation composition.
The pyridine compound and / or salt thereof of the present invention can be blended within a range in which the effect can be exerted, but usually 0.001 to 20% by mass is preferably blended in each product. A blending ratio of 10 to 10% by mass is more preferable.
次に、本発明にかかるピリジン化合物及び／またはその塩を配合した皮膚外用剤組成物について説明する。
上記した本発明のピリジン化合物及び／またはその塩を皮膚外用剤組成物へ適宜配合することにより、優れた紫外線吸収作用を発揮する皮膚外用剤組成物を得ることができる。また、前記化合物は高い光安定性を有し、日光曝露下においても分解されないため、本発明の皮膚外用剤組成物の紫外線防止効果は長時間に亘って安定に発揮される。
さらに、本発明にかかる皮膚外用剤組成物は安全性も高く、その使用において皮膚トラブルを生じない。以上のことから、本発明にかかる皮膚外用剤組成物は、サンスクリーン用として好適に使用することができる。
Next, the skin external preparation composition which mix | blended the pyridine compound and / or its salt concerning this invention is demonstrated.
By appropriately blending the pyridine compound and / or salt thereof of the present invention described above into the skin external preparation composition, a skin external preparation composition exhibiting an excellent ultraviolet absorbing action can be obtained. Moreover, since the said compound has high light stability and is not decomposed | disassembled even if exposed to sunlight, the ultraviolet-ray prevention effect of the skin external preparation composition of this invention is exhibited stably over a long time.
Furthermore, the skin external preparation composition according to the present invention has high safety and does not cause skin troubles in its use. From the above, the skin external preparation composition according to the present invention can be suitably used for sunscreen.
通常、サンスクリーン用の皮膚外用剤組成物においては、紫外線遮蔽効果を高めるために、有機化合物系紫外線吸収剤とともに無機系粉体系紫外線遮蔽剤を併用することが望ましいとされる。また、一般のメーキャップ化粧料においても、無機粉体が配合されることは多い。しかしながら、従来、有機系紫外線吸収剤と無機粉体とを併用すると変色が起こることがあった。一方、本発明の紫外線吸収剤はこのような変色を起こすことなく、好適に無機粉体を併用することが可能であり、この併用によって皮膚外用剤組成物の紫外線遮蔽効果をより高めることができる。 Usually, in a skin external preparation composition for sunscreen, in order to enhance the ultraviolet shielding effect, it is desirable to use an inorganic powder ultraviolet shielding agent together with an organic compound ultraviolet absorber. Also, in general makeup cosmetics, inorganic powder is often blended. Conventionally, however, discoloration sometimes occurs when an organic ultraviolet absorber and an inorganic powder are used in combination. On the other hand, the ultraviolet absorbent according to the present invention can be preferably used in combination with inorganic powder without causing such discoloration, and this combined use can further enhance the ultraviolet shielding effect of the external preparation for skin. .
本発明にかかる皮膚外用剤組成物に適用し得る無機粉体は、通常化粧品や医薬品に配合されるものであれば特に限定されない。このような無機粉体としては、例えば、タルク、カオリン、窒化ホウ素、雲母、絹雲母（セリサイト）、白雲母、黒雲母、金雲母、合成雲母、合成マイカ、パーミキュライト、炭酸マグネシウム、炭酸カルシウム、無水ケイ酸、ケイ酸アルミニウム、酸化アルミニウム、ケイ酸バリウム、ケイ酸カルシウム、ケイ酸マグネシウム、タングステン酸金属塩、マグネシウム、シリカ、ゼオライト、硫酸バリウム、焼成硫酸カルシウム、焼セッコウ、リン酸カルシウム、フッ素アパタイト、ヒドロキシアパタイト、セラミックパウダー、金属石鹸（ミリスチン酸亜鉛、パルミチン酸カルシウム、ステアリン酸アルミニウム等）等の無機粉末の他、二酸化チタン、酸化亜鉛、酸化鉄、チタン酸鉄、カーボン、低次酸化チタン、マンゴバイオレット、コバルトバイオレット、酸化クロム、水酸化クロム、チタン酸コバルト、群青、紺青、酸化チタン被覆マイカ、酸化チタン被覆オキシ塩化ビスマス、酸化チタン被覆タルク、着色酸化チタン被覆マイカ、オキシ塩化ビスマス、魚鱗箔等の無機顔料が挙げられる。 The inorganic powder that can be applied to the external preparation for skin according to the present invention is not particularly limited as long as it is usually blended in cosmetics and pharmaceuticals. Examples of such inorganic powder include talc, kaolin, boron nitride, mica, sericite (sericite), muscovite, biotite, phlogopite, synthetic mica, synthetic mica, permiculite, magnesium carbonate, calcium carbonate, Anhydrous silicic acid, aluminum silicate, aluminum oxide, barium silicate, calcium silicate, magnesium silicate, metal tungstate, magnesium, silica, zeolite, barium sulfate, calcined calcium sulfate, calcined gypsum, calcium phosphate, fluorapatite, hydroxy In addition to inorganic powders such as apatite, ceramic powder, metal soap (such as zinc myristate, calcium palmitate, aluminum stearate), titanium dioxide, zinc oxide, iron oxide, iron titanate, carbon, low-order titanium oxide, mango violet , Inorganic, such as violet, chromium oxide, chromium hydroxide, cobalt titanate, ultramarine, bitumen, titanium oxide coated mica, titanium oxide coated bismuth oxychloride, titanium oxide coated talc, colored titanium oxide coated mica, bismuth oxychloride, fish scale foil Pigments.
本発明にかかる皮膚外用剤組成物は、上記成分の他に、通常化粧品や医薬品に配合可能な成分、例えば、液体油脂、固体油脂、ロウ、炭化水素、高級脂肪酸、高級アルコール、エステル類、シリコーン、アニオン界面活性剤、カチオン界面活性剤、両性界面活性剤、非イオン性界面活性剤、保湿剤、水溶性高分子化合物、増粘剤、被膜剤、金属イオン封鎖剤、低級アルコール、多価アルコール、糖類、アミノ酸類、有機アミン類、ｐＨ調整剤、皮膚栄養剤、ビタミン類、酸化防止剤、香料、粉末、色材、水等を必要に応じて適宜配合することができる。
また、本発明にかかる皮膚外用剤組成物には、本発明のピリジン化合物及び／またはその塩以外の紫外線吸収剤を配合してもよい。本発明のピリジン化合物及び／またはその塩の有する安定性は、皮膚外用剤組成物に配合された他の成分、特に光分解しやすい紫外線吸収剤をも安定化すると考えられる。したがって、皮膚外用剤組成物そのものの安定性を向上させるという点で、本発明のピリジン化合物及び／またはその塩以外を他の紫外線吸収剤と併用することが好ましい。
In addition to the above-mentioned components, the external preparation composition for skin according to the present invention is usually a component that can be blended in cosmetics and pharmaceuticals, such as liquid oils, solid oils, waxes, hydrocarbons, higher fatty acids, higher alcohols, esters, silicones. , Anionic surfactant, cationic surfactant, amphoteric surfactant, nonionic surfactant, moisturizer, water-soluble polymer compound, thickener, coating agent, sequestering agent, lower alcohol, polyhydric alcohol , Sugars, amino acids, organic amines, pH adjusters, skin nutrients, vitamins, antioxidants, fragrances, powders, coloring materials, water, and the like can be appropriately blended as necessary.
Moreover, you may mix | blend ultraviolet absorbers other than the pyridine compound and / or its salt of this invention with the skin external preparation composition concerning this invention. The stability of the pyridine compound and / or salt thereof of the present invention is considered to stabilize other components blended in the skin external preparation composition, particularly an ultraviolet absorber that is easily photodegradable. Therefore, in terms of improving the stability of the external preparation for skin itself, it is preferable to use other than the pyridine compound and / or salt thereof of the present invention in combination with other ultraviolet absorbers.
本発明にかかる皮膚外用剤組成物におけるピリジン化合物及び／またはその塩の配合量は、０．００１〜２０質量％が好ましく、０．０１〜１０質量％の配合がさらに好適である。配合量が０．００１質量％以下であると十分な紫外線吸収効果が発揮されないことがある。また、本発明ピリジン化合物は２０質量％を超えても組成物中によく溶解するが、これより配合量を増加しても一定以上の紫外線吸収効果は得られない。 0.001-20 mass% is preferable, and, as for the compounding quantity of the pyridine compound and / or its salt in the skin external preparation composition concerning this invention, the compounding of 0.01-10 mass% is more suitable. If the blending amount is 0.001% by mass or less, a sufficient ultraviolet absorption effect may not be exhibited. In addition, the pyridine compound of the present invention dissolves well in the composition even if it exceeds 20% by mass, but even if the blending amount is increased from this, a certain level of ultraviolet absorption effect cannot be obtained.
本発明にかかる皮膚外用剤組成物は、本発明の効果を発揮し得るものであれば特に制限されず、その使用目的に応じて化粧料、医薬品、医薬部外品等に適用することができる。また、本発明の紫外線吸収剤は高い水溶性を有するため、水性ベースの皮膚外用剤組成物へ適用することも可能である。このような皮膚外用剤組成物の形態としては、例えば、化粧水、乳液、クリーム、美容液、セルフタニング剤等のスキンケア化粧料の他、下地用化粧料、ファンデーション、口紅、フェイスカラー、アイライナー等のメーキャップ化粧料、ヘアスプレー、ヘアトニック、ヘアリキッド等の頭髪用、頭皮用化粧料等が挙げられる。
以下、実施例を挙げて本発明を具体的に説明する。なお、本発明はこれらに限定されるものではない。配合量は特に記載のない限り、質量％で示す。
The skin external preparation composition according to the present invention is not particularly limited as long as it can exert the effects of the present invention, and can be applied to cosmetics, pharmaceuticals, quasi drugs and the like according to the purpose of use. . Moreover, since the ultraviolet absorber of this invention has high water solubility, it is also possible to apply to the aqueous-based skin external preparation composition. Examples of the form of such a skin external preparation composition include skin care cosmetics such as skin lotions, emulsions, creams, cosmetics, self-tanning agents, foundation cosmetics, foundations, lipsticks, face colors, eyeliners, etc. Makeup cosmetics, hair sprays, hair tonics, hair liquids and the like, and scalp cosmetics.
Hereinafter, the present invention will be specifically described with reference to examples. The present invention is not limited to these. Unless otherwise specified, the amount is shown in mass%.
まず、本発明にかかる紫外線吸収剤について、以下の試験を行った。
＜吸光度の測定＞
（１）本発明にかかる紫外線吸収剤である４−ジメチルアミノピリジン Ｎ−オキシドの紫外線吸収スペクトル（溶媒：水、濃度１０ｐｐｍ、光路長１ｃｍ）を分光光度計（日本分光株式会社製Ｖ−５６０）にて測定した。結果を下記表１に示す。
（表１）
紫外線吸収剤 最大吸収波長 吸光度
４−ジメチルアミノピリジン Ｎ−オキシド ２９３ １．７
First, the following tests were performed on the ultraviolet absorbent according to the present invention.
<Measurement of absorbance>
(1) A spectrophotometer (V-560 manufactured by JASCO Corporation) is used to measure the ultraviolet absorption spectrum (solvent: water, concentration 10 ppm, optical path length 1 cm) of 4-dimethylaminopyridine N-oxide which is an ultraviolet absorber according to the present invention. Measured with The results are shown in Table 1 below.
(Table 1)
UV absorber Maximum absorption wavelength Absorbance
4-Dimethylaminopyridine N-oxide 293 1.7
（２）本発明にかかる紫外線吸収剤である４−ジメチルアミノピリジン Ｎ−オキシドの４０５ｎｍの可視光の吸光度（溶媒：水、光路長１ｃｍ）を分光光度計（日本分光株式会社製Ｖ−５６０）にて測定した。また、比較例として、従来の水溶性紫外線吸収剤である２−ヒドロキシ−メトキシ−５−スルフォキソニウムベンゾフェノンナトリウムも同様に測定した。結果を下記表２に示す。
（表２）
紫外線吸収剤 濃度（質量％） 吸光度
４−ジメチルアミノピリジン Ｎ−オキシド １０．０ ０
比較例 ６．０ １．９９
１．０ ０．３２
０．１ ０．０６
(2) A spectrophotometer (V-560 manufactured by JASCO Corporation) is used to measure the visible light absorbance (solvent: water, optical path length 1 cm) of 4-dimethylaminopyridine N-oxide, which is an ultraviolet absorber according to the present invention, at 405 nm. Measured with As a comparative example, 2-hydroxy-methoxy-5-sulfoxonium benzophenone sodium, which is a conventional water-soluble ultraviolet absorber, was also measured in the same manner. The results are shown in Table 2 below.
(Table 2)
Ultraviolet absorber concentration (mass%) Absorbance
4-Dimethylaminopyridine N-oxide 10.0
Comparative Example 6.0 1.99
1.0 0.32
0.1 0.06
表１及び表２より明らかなように、本発明の紫外線吸収剤である４−ジメチルアミノピリジン Ｎ−オキシドは、紫外線波長領域においては優れた吸収能を示し、４００ｎｍより長波長側の可視領域においては吸収を示さなかった。そのため、該化合物の結晶は白色であり、その水溶液は無色透明であった。一方、比較例は可視領域において吸収を示し、その結晶は淡黄色、水溶液は黄色にそれぞれ着色していた。したがって、比較例の紫外線吸収剤は、配合の際に製品を着色することを考慮して配合量を制限する必要が生じ、製品に十分な紫外線吸収効果を付与することができないと考えられる。
以上の結果より、本発明にかかる紫外線吸収剤は、可視光領域に吸収を持たないため、製品に配合しても着色することなく、紫外線に対してのみ優れた吸収能を発揮することが認められた。よって、本発明の紫外線吸収剤は着色によって配合製品及び配合量が制限されることはないと思料される。
As is apparent from Tables 1 and 2, 4-dimethylaminopyridine N-oxide, which is the ultraviolet absorbent according to the present invention, exhibits excellent absorption in the ultraviolet wavelength region, and in the visible region longer than 400 nm. Showed no absorption. Therefore, the crystals of the compound were white and the aqueous solution was colorless and transparent. On the other hand, the comparative example showed absorption in the visible region, and the crystals were colored yellow and the aqueous solution was colored yellow. Therefore, it is considered that the ultraviolet absorber of the comparative example needs to be limited in amount in consideration of coloring the product at the time of blending, and it is considered that a sufficient ultraviolet absorbing effect cannot be imparted to the product.
From the above results, the ultraviolet absorbent according to the present invention has no absorption in the visible light region, and therefore, it is recognized that it exhibits excellent absorption ability only for ultraviolet rays without coloring even when blended in a product. It was. Therefore, it is thought that the ultraviolet absorber of this invention does not restrict | limit a mixing | blending product and a compounding quantity by coloring.
＜水への溶解性＞
本発明にかかる紫外線吸収剤である４−ジメチルアミノピリジン Ｎ−オキシドの室温における水への溶解性を測定した。比較例として、従来の水溶性紫外線吸収剤である２−ヒドロキシ−メトキシ−５−スルフォキソニウムベンゾフェノンナトリウムも同様に測定した。結果を下記表３に示す。
（表３）
紫外線吸収剤 溶解性（質量％）
４−ジメチルアミノピリジン Ｎ−オキシド ３０以上
比較例 ６
<Solubility in water>
The solubility of 4-dimethylaminopyridine N-oxide, which is an ultraviolet absorbent according to the present invention, in water at room temperature was measured. As a comparative example, 2-hydroxy-methoxy-5-sulfoxonium benzophenone sodium, which is a conventional water-soluble UV absorber, was also measured in the same manner. The results are shown in Table 3 below.
(Table 3)
UV absorber solubility (% by mass)
4-dimethylaminopyridine N-oxide 30 or more
Comparative Example 6
表３によれば、比較例の化合物は水への溶解性が低く、高濃度に溶解させると低温下で析出してしまうことがあった。したがって、比較例の化合物は、配合製品の安定性の観点からも、その使用が制限されると考えられる。一方、４−ジメチルアミノピリジン Ｎ−オキシドは水への溶解性が極めて高く、前記のような析出も認められなかった。
したがって、本発明にかかる紫外線吸収剤は、水系製剤に高濃度で配合することが可能であり、その配合製品は製品安定性に優れていることが認められた。
According to Table 3, the compound of the comparative example has low solubility in water, and when dissolved at a high concentration, it sometimes precipitated at a low temperature. Therefore, the use of the compound of the comparative example is considered to be limited from the viewpoint of the stability of the blended product. On the other hand, 4-dimethylaminopyridine N-oxide has extremely high solubility in water, and no such precipitation was observed.
Therefore, it was confirmed that the ultraviolet absorber according to the present invention can be blended in a high concentration in an aqueous preparation, and the blended product is excellent in product stability.
＜光安定性試験＞
本発明の４−ジメチルアミノピリジン Ｎ−オキシドの水溶液を日光に２週間曝露（日射被曝量８０ＭＪ／ｍ２）後、残存率及び外観の変化を調べると共に紫外線吸収スペクトル（溶媒：水、濃度１０ｐｐｍ、光路長１ｃｍ）を分光光度計にて測定し、紫外線吸収スペクトルの２９０ｎｍ〜４００ｎｍの範囲を積分処理して面積値を求め、日光曝露前と比較した。また、比較例として、従来の水溶性紫外線吸収剤である２−ヒドロキシ−メトキシ−５−スルフォキソニウムベンゾフェノンナトリウムに関しても同様に試験を行った。結果を表４に示す。
<Light stability test>
After exposing the aqueous solution of 4-dimethylaminopyridine N-oxide of the present invention to sunlight for 2 weeks (irradiation dose 80 MJ / m 2 ), the residual rate and appearance change were examined, and an ultraviolet absorption spectrum (solvent: water, concentration 10 ppm, An optical path length of 1 cm) was measured with a spectrophotometer, and an area value was obtained by integrating the range of 290 nm to 400 nm of the ultraviolet absorption spectrum, and compared with that before exposure to sunlight. As a comparative example, the same test was conducted for 2-hydroxy-methoxy-5-sulfoxonium benzophenone sodium, which is a conventional water-soluble UV absorber. The results are shown in Table 4.
（判定）
残存率及び紫外線吸収スペクトルの面積値の変化は次の基準で判定した。
◎：日光曝露前の９５％以上。
○：日光曝露前の９０％以上９５％未満。
△：日光曝露前の７０％以上９０％未満。
×：日光曝露前の７０％未満。
(Judgment)
Changes in the residual ratio and the area value of the ultraviolet absorption spectrum were determined according to the following criteria.
A: 95% or more before sun exposure.
○: 90% or more and less than 95% before sun exposure.
Δ: 70% or more and less than 90% before sun exposure.
X: Less than 70% before sun exposure.
（表４）
紫外線吸収剤 残存率 外観 紫外線吸収スペクトルの
面積値の変化
４−ジメチルアミノピリジン ◎ 無色透明 ◎
Ｎ−オキシド
比較例 ○ 黄色透明 ○
(Table 4)
UV absorber remaining rate Appearance of UV absorption spectrum
Change in area value
4-dimethylaminopyridine ◎ colorless and transparent ◎
N-oxide
Comparative example ○ Transparent yellow ○
表４に示すように、４−ジメチルアミノピリジン Ｎ−オキシドは比較例に比べ、長時間の直射日光曝露によっても分解されず、非常に高い残存率を示した。また、紫外線吸収スペクトルの形状や面積にも変化はなく、外観においても着色や析出などは見られなかった。
以上の結果より、本発明にかかる紫外線吸収剤は優れた光安定性を有し、劣化することなく長期間にわたって紫外線吸収能を保持し得ることが認められた。
As shown in Table 4, 4-dimethylaminopyridine N-oxide was not decomposed by exposure to direct sunlight for a long time as compared with the comparative example, and showed a very high residual rate. Further, there was no change in the shape and area of the ultraviolet absorption spectrum, and no coloring or precipitation was observed in the appearance.
From the above results, it was confirmed that the ultraviolet absorbent according to the present invention has excellent light stability and can retain ultraviolet absorbing ability over a long period of time without deterioration.
続いて、本発明にかかる皮膚外用剤組成物について以下の試験を行った。
＜紫外線防止効果＞
本発明の紫外線吸収剤を配合した皮膚外用剤組成物の紫外線防止効果を検討するため、該皮膚外用剤組成物として下記表５の処方によりローション、表６の処方によりクリームを調製した。調製した各試料について下記の試験方法により紫外線防止効果を評価し、また、目視により外観を観察した。結果を表５及び表６に示す。
Then, the following tests were done about the skin external preparation composition concerning this invention.
<UV prevention effect>
In order to examine the ultraviolet protection effect of the skin external preparation composition containing the ultraviolet absorbent of the present invention, a lotion was prepared according to the formulation shown in Table 5 below, and a cream was prepared according to the formulation shown in Table 6 as the skin external preparation composition. For each of the prepared samples, the ultraviolet ray prevention effect was evaluated by the following test method, and the appearance was visually observed. The results are shown in Tables 5 and 6.
（ｉ）試験方法
夏期の海辺で実使用テストを行った。パネルの背中の左右半分ずつに試料を等量ずつ塗布した。直射日光曝露後の日焼けの程度を以下の判定基準にしたがって評価した。なお、パネルは１群１０名で行った。
(I) Test method An actual use test was conducted at the beach in summer. An equal amount of sample was applied to each of the left and right halves of the back of the panel. The degree of sunburn after exposure to direct sunlight was evaluated according to the following criteria. The panel was performed by 10 people per group.
（判定基準）
著効：全くあるいはほとんど日焼け症状が認められなかった。
有効：軽度の日焼け症状が認められた。
無効：強度の日焼け症状が認められた。
(Criteria)
Remarkable: No or almost no sunburn symptoms were observed.
Effective: Mild sunburn was observed.
Invalid: Severe sunburn was observed.
（判定）
◎：著効又は有効の被験者が８０％以上。
○：著効又は有効の被験者が５０％以上８０％未満。
△：著効又は有効の被験者が３０％以上５０％未満。
×：著効又は有効の被験者が３０％未満。
(Judgment)
A: Remarkable or effective subjects are 80% or more.
○: Remarkable or effective subjects are 50% or more and less than 80%.
Δ: Remarkable or effective subjects are 30% or more and less than 50%.
X: Remarkable or effective subjects are less than 30%.
（ｉｉ）試料の調製
（ａ）ローション
下記表５の各処方に従い、水相、アルコール相をそれぞれ調製後、混合してローションを得た。
(Ii) Preparation of Sample (a) Lotion According to each formulation shown in Table 5 below, a water phase and an alcohol phase were prepared and mixed to obtain a lotion.
（ｂ）クリーム
成分及び配合量は下記表６の処方に従った。製法は次のとおりである。
イオン交換水にプロピレングリコールと紫外線吸収剤を加えて溶解し、加熱して７０℃に保った（水相）。他の成分を混合し、加熱融解して７０℃に保った（油相）。水相に油相を加え、予備乳化を行い、ホモミキサーで均一に乳化した後、よくかき混ぜながら３０℃まで冷却してクリームを得た。
(B) Cream Ingredients and blending amounts were in accordance with the formulations shown in Table 6 below. The manufacturing method is as follows.
Propylene glycol and an ultraviolet absorber were added to ion-exchanged water and dissolved, and heated to 70 ° C. (water phase). The other components were mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well to obtain a cream.
（表５）
＊＊低温保存で結晶析出。
(Table 5)
** Crystals precipitate when stored at low temperature.
（表６）
＊＊低温保存で結晶析出。
(Table 6)
** Crystals precipitate when stored at low temperature.
表５及び表６に示すように、紫外線吸収剤として４−ジメチルアミノピリジン Ｎ−オキシドを配合したローション（試験例１〜３）及びクリーム（試験例４〜６）は実使用において優れた紫外線防止効果を示した。また、その配合による組成物の着色は認められず、無配合の比較例４及び８と同様の外観を呈していた。さらに、４−ジメチルアミノピリジン Ｎ−オキシドは水溶性が非常に高く、試験例３及び６のような高配合の試験例においても経時的な結晶析出は見られなかった。なお、配合系のｐＨにも影響は見られなかった。
一方、従来の紫外線吸収剤である２−ヒドロキシ−４−メトキシ−５−スルフォキソニウムベンゾフェノンナトリウムを配合した比較例１〜３及び５〜７においては、組成物が黄色く着色し外観に劣っていた。また、前記化合物は水溶性が低く、５．０質量％の配合で低温において結晶の析出が認められた。
As shown in Tables 5 and 6, lotions (Test Examples 1 to 3) and creams (Test Examples 4 to 6) containing 4-dimethylaminopyridine N-oxide as an ultraviolet absorber are excellent in preventing UV rays in actual use. Showed the effect. Moreover, the coloring of the composition by the mixing | blending was not recognized, but the external appearance similar to the non-blending comparative examples 4 and 8 was exhibited. Furthermore, 4-dimethylaminopyridine N-oxide has very high water solubility, and even in highly blended test examples such as Test Examples 3 and 6, no crystallization was observed over time. In addition, there was no effect on the pH of the blended system.
On the other hand, in Comparative Examples 1-3 and 5-7 in which 2-hydroxy-4-methoxy-5-sulfoxonium benzophenone sodium, which is a conventional ultraviolet absorber, was blended, the composition was colored yellow and inferior in appearance. It was. Moreover, the said compound was low in water solubility, and the precipitation of the crystal | crystallization was recognized by low temperature with the mixture of 5.0 mass%.
以上の結果により、本発明にかかる皮膚外用剤組成物は、本発明のピリジン化合物及び／またはその塩によって着色することなく、高い紫外線防止効果を発揮することが認められた。また、該ピリジン化合物は水溶性が極めて高いことから、水性ベースの皮膚外用剤組成物へ高濃度に配合することが可能である。 From the above results, it was confirmed that the skin external preparation composition according to the present invention exhibits a high ultraviolet ray preventing effect without being colored by the pyridine compound and / or salt thereof of the present invention. In addition, since the pyridine compound is extremely water-soluble, it can be blended in a high concentration in an aqueous-based external skin composition.
＜皮膚刺激性試験＞
上記試験例３及び比較例４のローション、試験例６及び比較例８のクリームを用い、本発明の皮膚外用剤組成物の皮膚刺激性試験を行った。試験方法は次のパッチテストによる。
（試験方法）
健常な男性及び女性志願者の前腕屈折部にフィンチャンバーを用いて２４時間閉塞パッチテストを１群２０名で行い、次の判定基準で判定した。結果を下記表７に示す。
<Skin irritation test>
Using the lotions of Test Example 3 and Comparative Example 4 and the creams of Test Example 6 and Comparative Example 8, the skin irritation test of the skin external preparation composition of the present invention was conducted. The test method is based on the following patch test.
(Test method)
A 24-hour occlusion patch test was conducted with 20 people per group using a fin chamber in the forearm refracted part of healthy male and female volunteers, and judged according to the following criteria. The results are shown in Table 7 below.
（判定基準）
皮膚反応の程度 スコア
反応なし（陰性） ０
軽い紅班（疑陰性） １
紅班（弱陽性） ２
紅班＋浮腫（中等度陽性） ３
紅班＋浮腫＋丘疹（強陽性） ４
大水泡（最強度陽性） ５
(Criteria)
Degree of skin reaction Score
No reaction (negative) 0
Light red spot (negative false) 1
Red spot (weak positive) 2
Erythema + edema (moderately positive) 3
Erythema + edema + papules (strongly positive) 4
Large water bubbles (strongest positive) 5
（判定）
上記判定基準に沿って平均スコアを求め、次の基準で判定した。
◎：平均スコアが０。
○：平均スコアが０より大きく１未満。
△：平均スコアが１以上２未満。
×：平均スコアが２以上。
(Judgment)
An average score was determined according to the above criteria and judged according to the following criteria.
A: The average score is 0.
○: The average score is greater than 0 and less than 1.
Δ: The average score is 1 or more and less than 2.
X: The average score is 2 or more.
（表７）
試験例３ 比較例４ 試験例６ 比較例８
パッチテスト判定 ◎ ◎ ◎ ◎
(Table 7)
Test Example 3 Comparative Example 4 Test Example 6 Comparative Example 8
Patch test judgment ◎ ◎ ◎ ◎
表７に示すとおり、本発明の紫外線吸収剤を配合した試験例３及び試験例６の試料は、紫外線吸収剤が無配合である比較例と同様、皮膚刺激性は認められなかった。この結果より、本発明にかかる皮膚外用剤組成物は、いずれの剤形においても皮膚刺激性を有さず、安全性の高いものであることが確認された。 As shown in Table 7, skin irritation was not observed in the samples of Test Example 3 and Test Example 6 in which the ultraviolet absorbent according to the present invention was blended, as in the comparative example in which the ultraviolet absorbent was not blended. From these results, it was confirmed that the external preparation composition for skin according to the present invention has no skin irritation in any dosage form and is highly safe.
＜無機粉体との併用時の安定性試験＞
本発明にかかる皮膚外用剤組成物を無機粉体系紫外線遮蔽剤と併用した際の安定性を検討するため、下記表８に示す処方のサンスクリーンクリームを製造し、これらを５０℃で２ヶ月間保存した後、目視により変色を観察した。結果を表８に示す。
<Stability test when used in combination with inorganic powder>
In order to study the stability when the skin external preparation composition according to the present invention is used in combination with an inorganic powder-based ultraviolet shielding agent, sunscreen creams having the formulations shown in Table 8 below are produced, and these are prepared at 50 ° C. for 2 months. After storage, the discoloration was visually observed. The results are shown in Table 8.
（表８）
（１）に（２）を加え十分に膨潤させた後、（３）〜（１２）を加え加熱混合し、十分に分散及び溶解した。この分散液を７０℃に保ち、（１３）〜（１６）を混合した溶液を徐々に加えながらホモミキサーで均一に乳化した後、よくかき混ぜながら３０℃まで冷却し、サンスクリーンクリームを得た。
(Table 8)
After (2) was added to (1) and sufficiently swollen, (3) to (12) were added and mixed by heating to sufficiently disperse and dissolve. The dispersion was kept at 70 ° C., and after uniformly emulsifying with a homomixer while gradually adding the solution obtained by mixing (13) to (16), the mixture was cooled to 30 ° C. while stirring well to obtain a sunscreen cream.
表８から明らかなように、紫外線吸収剤として２−ヒドロキシ−４−メトキシ−５−スルフォキソニウムベンゾフェノンナトリウムを配合した比較例９のサンスクリーンクリームは、無機粉体を併用すると黄色が濃く変色した。一方、４−ジメチルアミノピリジン Ｎ−オキシドを配合した試験例７においては、無機粉体の併用によって変色は生じなかった。
したがって、本発明にかかるピリジン化合物及び／またはその塩を配合した皮膚外用剤組成物は、無機粉体との併用が可能であることが認められた。
As is clear from Table 8, the sunscreen cream of Comparative Example 9 in which 2-hydroxy-4-methoxy-5-sulfoxonium benzophenone sodium was blended as an ultraviolet absorber had a deep yellow color when inorganic powder was used in combination. did. On the other hand, in Test Example 7 in which 4-dimethylaminopyridine N-oxide was blended, no discoloration occurred due to the combined use of inorganic powder.
Therefore, it was recognized that the skin external preparation composition containing the pyridine compound and / or salt thereof according to the present invention can be used in combination with the inorganic powder.
以上の試験結果により、特定のピリジン化合物からなる本発明の紫外線吸収剤は優れた紫外線吸収能に加え、皮膚刺激性がなく及び高い光安定性を有し、さらに無機粉体と併用により変色を生じないことから、非常に有用であることが認められた。さらに、前記ピリジン化合物及び／またはその塩を皮膚外用剤組成物に配合することにより、サンスクリーン効果に優れた皮膚外用剤組成物が得られることが明らかになった。 Based on the above test results, the UV absorber of the present invention comprising a specific pyridine compound has excellent UV absorbing ability, has no skin irritation and high light stability, and further discolors when used in combination with inorganic powder. Since it does not occur, it was found to be very useful. Furthermore, it became clear that the skin external preparation composition excellent in the sunscreen effect can be obtained by mix | blending the said pyridine compound and / or its salt with a skin external preparation composition.
以下、本発明の皮膚外用剤組成物の処方例を挙げるが、本発明はこれらに限定されるものではない。なお、配合量は全て質量％で示す。
＜処方例１ 化粧水＞
（アルコール相）
エタノール １０．０
オレイルアルコール ０．１
ＰＯＥ（２０）ソルビタンモノラウリン酸エステル ０．５
ＰＯＥ（１５）ラウリルエーテル ０．５
防腐剤 適 量
香料 適 量
（水相）
４−ジメチルアミノピリジン Ｎ−オキシド １０．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
水酸化ナトリウム ０．４
１，３−ブチレングリコール ６．０
グリセリン ４．０
４，５−ジモルホリノ−３−ヒドロキシピリダジン ０．３
イオン交換水 残 余
（製法）
水相、アルコール相をそれぞれ調製後、混合した。
Hereinafter, although the formulation example of the skin external preparation composition of this invention is given, this invention is not limited to these. In addition, all compounding quantities are shown by the mass%.
<Prescription example 1 lotion>
(Alcohol phase)
Ethanol 10.0
Oleyl alcohol 0.1
POE (20) sorbitan monolaurate 0.5
POE (15) lauryl ether 0.5
Preservative appropriate amount Fragrance appropriate amount (aqueous phase)
4-Dimethylaminopyridine N-oxide 10.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Sodium hydroxide 0.4
1,3-butylene glycol 6.0
Glycerin 4.0
4,5-Dimorpholino-3-hydroxypyridazine 0.3
Ion-exchanged water residue (production method)
An aqueous phase and an alcohol phase were prepared and mixed.
＜処方例２ 化粧水＞
（アルコール相）
エタノール １０．０
オレイルアルコール ０．１
ＰＯＥ（２０）ソルビタンモノラウリン酸エステル ０．５
ＰＯＥ（１５）ラウリルエーテル ０．５
防腐剤 適 量
香料 適 量
（水相）
４−ジメチルアミノピリジン Ｎ−オキシド ５．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
水酸化ナトリウム ０．４
１，３−ブチレングリコール ６．０
グリセリン ４．０
テレフタリリデンジカンフルスルホン酸 １．０
４，５−ジモルホリノ−３−ヒドロキシピリダジン ０．３
イオン交換水 残 余
（製法）
水相、アルコール相をそれぞれ調製後、混合した。
<Prescription example 2 lotion>
(Alcohol phase)
Ethanol 10.0
Oleyl alcohol 0.1
POE (20) sorbitan monolaurate 0.5
POE (15) lauryl ether 0.5
Preservative appropriate amount Fragrance appropriate amount (aqueous phase)
4-Dimethylaminopyridine N-oxide 5.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Sodium hydroxide 0.4
1,3-butylene glycol 6.0
Glycerin 4.0
Terephthalylidene dicamphulsulfonic acid 1.0
4,5-Dimorpholino-3-hydroxypyridazine 0.3
Ion-exchanged water residue (production method)
An aqueous phase and an alcohol phase were prepared and mixed.
＜処方例３ 化粧水＞
（アルコール相）
エタノール １０．０
パラメトキシ桂皮酸２−エチルヘキシルエステル ０．５
２−ヒドロキシ−４−メトキシベンゾフェノン ０．５
４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ０．５
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
０．５
ＰＯＥ（２０）オレイルエーテル ０．５
防腐剤 適 量
香料 適 量
（水相）
ジプロピレングリコール ６．０
ソルビット ４．０
ＰＥＧ１５００ ５．０
４−ジメチルアミノピリジン Ｎ−オキシド ２０．０
テレフタリリデンジカンフルスルホン酸 １．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
トリエタノールアミン １．８
メチルセルロース ０．２
クインスシード ０．１
イオン交換水 残 余
（製法）
イオン交換水の一部にメチルセルロース及びクインスシードを混合、攪拌し、粘稠液を調製した。イオン交換水の残部と他の水相成分を混合溶解し、これに前記の粘稠液を加えて、均一な水相を得た。アルコール相を調製後、水相に添加し、混合した。
<Prescription example 3 lotion>
(Alcohol phase)
Ethanol 10.0
Paramethoxycinnamic acid 2-ethylhexyl ester 0.5
2-Hydroxy-4-methoxybenzophenone 0.5
4-tert-butyl-4'-methoxydibenzoylmethane 0.5
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
0.5
POE (20) oleyl ether 0.5
Preservative appropriate amount Fragrance appropriate amount (aqueous phase)
Dipropylene glycol 6.0
Sorbit 4.0
PEG 1500 5.0
4-Dimethylaminopyridine N-oxide 20.0
Terephthalylidene dicamphulsulfonic acid 1.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Triethanolamine 1.8
Methylcellulose 0.2
Quince Seed 0.1
Ion-exchanged water residue (production method)
Methyl cellulose and quince seeds were mixed and stirred in a portion of ion-exchanged water to prepare a viscous liquid. The remainder of the ion exchange water and the other aqueous phase components were mixed and dissolved, and the viscous liquid was added thereto to obtain a uniform aqueous phase. After the alcohol phase was prepared, it was added to the aqueous phase and mixed.
＜処方例４ 化粧水＞
（アルコール相）
エタノール １０．０
パラメトキシ桂皮酸２−エチルヘキシルエステル ０．５
２−ヒドロキシ−４−メトキシベンゾフェノン ０．５
４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ０．５
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
０．５
ＰＯＥ（２０）オレイルエーテル ０．５
防腐剤 適 量
香料 適 量
（水相）
ジプロピレングリコール ６．０
ソルビット ４．０
ＰＥＧ１５００ ５．０
４−ジメチルアミノピリジン Ｎ−オキシド ７．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
トリエタノールアミン １．８
メチルセルロース ０．２
クインスシード ０．１
イオン交換水 残 余
（製法）
イオン交換水の一部にメチルセルロース及びクインスシードを混合、攪拌し、粘稠液を調製した。イオン交換水の残部と他の水相成分を混合溶解し、これに前記の粘稠液を加えて、均一な水相を得た。アルコール相を調製後、水相に添加し、混合した。
<Formulation example 4 lotion>
(Alcohol phase)
Ethanol 10.0
Paramethoxycinnamic acid 2-ethylhexyl ester 0.5
2-Hydroxy-4-methoxybenzophenone 0.5
4-tert-butyl-4'-methoxydibenzoylmethane 0.5
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
0.5
POE (20) oleyl ether 0.5
Preservative appropriate amount Fragrance appropriate amount (aqueous phase)
Dipropylene glycol 6.0
Sorbit 4.0
PEG 1500 5.0
4-Dimethylaminopyridine N-oxide 7.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Triethanolamine 1.8
Methylcellulose 0.2
Quince Seed 0.1
Ion-exchanged water residue (production method)
Methyl cellulose and quince seeds were mixed and stirred in a portion of ion-exchanged water to prepare a viscous liquid. The remainder of the ion exchange water and the other aqueous phase components were mixed and dissolved, and the viscous liquid was added thereto to obtain a uniform aqueous phase. After the alcohol phase was prepared, it was added to the aqueous phase and mixed.
＜処方例５ クリーム＞
ステアリン酸 ５．０
ステアリルアルコール ４．０
イソプロピルミリステート １８．０
グリセリンモノステアリン酸エステル ３．０
パラメトキシ桂皮酸２−エチルヘキシルエステル １０．０
２−ヒドロキシ−４−メトキシベンゾフェノン ５．０
４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ３．０
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
プロピレングリコール １０．０
4-ジメチルアミノピリジン N-オキシド ５．０
テレフタリリデンジカンフルスルホン酸 ０．５
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
トリエタノールアミン １．８
４，５−ジモルホリノ−３−ヒドロキシピリダジン ０．２
水酸化カリウム ０．２
亜硫酸水素ナトリウム ０．０１
防腐剤 適 量
香料 適 量
イオン交換水 残 余
（製法）
イオン交換水に水相成分を加えて溶解し、加熱して７０℃に保った（水相）。他の成分を混合し、加熱融解して７０℃に保った（油相）。水相に油相を徐々に加えて予備乳化し、ホモミキサーで均一に乳化後、よくかきまぜながら３０℃まで冷却した。
<Prescription Example 5 Cream>
Stearic acid 5.0
Stearyl alcohol 4.0
Isopropyl myristate 18.0
Glycerol monostearate 3.0
Paramethoxycinnamic acid 2-ethylhexyl ester 10.0
2-Hydroxy-4-methoxybenzophenone 5.0
4-tert-Butyl-4'-methoxydibenzoylmethane 3.0
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
Propylene glycol 10.0
4-Dimethylaminopyridine N-oxide 5.0
Terephthalylidene dicamphulsulfonic acid 0.5
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Triethanolamine 1.8
4,5-Dimorpholino-3-hydroxypyridazine 0.2
Potassium hydroxide 0.2
Sodium bisulfite 0.01
Preservative appropriate amount Fragrance appropriate amount Ion-exchange water Residue
An aqueous phase component was added to ion-exchanged water to dissolve it, and the mixture was heated and maintained at 70 ° C. (aqueous phase). The other components were mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase to pre-emulsify it, and the mixture was uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
＜処方例６ クリーム＞
ステアリン酸 ６．０
ソルビタンモノステアリン酸エステル ２．０
ＰＯＥ（２０）ソルビタンモノステアリン酸エステル １．５
プロピレングリコール １０．０
４−ジメチルアミノピリジン Ｎ−オキシド １０．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
水酸化ナトリウム ０．４
グリセリントリオクタノエート １０．０
スクワレン ５．０
亜硫酸水素ナトリウム ０．０１
エチルパラベン ０．３
香料 適 量
イオン交換水 残 余
（製法）
イオン交換水にプロピレングリコール、４−ジメチルアミノピリジン Ｎ−オキシド、２−フェニルベンズイミダゾール−５−スルホン酸、水酸化ナトリウムを加えて溶解し、加熱して７０℃に保った（水相）。他の成分を混合し、加熱融解して７０℃に保った（油相）。水相に油相を徐々に加え、予備乳化を行い、ホモミキサーで均一に乳化した後、よくかきまぜながら３０℃まで冷却した。
<Prescription Example 6 Cream>
Stearic acid 6.0
Sorbitan monostearate ester 2.0
POE (20) sorbitan monostearate ester 1.5
Propylene glycol 10.0
4-Dimethylaminopyridine N-oxide 10.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Sodium hydroxide 0.4
Glycerin trioctanoate 10.0
Squalene 5.0
Sodium bisulfite 0.01
Ethylparaben 0.3
Perfume Appropriate amount Ion exchange water Residue (Production method)
Propylene glycol, 4-dimethylaminopyridine N-oxide, 2-phenylbenzimidazole-5-sulfonic acid and sodium hydroxide were added to ion-exchanged water and dissolved, and heated to 70 ° C. (aqueous phase). The other components were mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
＜処方例７ クリーム＞
ステアリン酸 ６．０
ソルビタンモノステアリン酸エステル ２．０
ＰＯＥ（２０）ソルビタンモノステアリン酸エステル １．５
プロピレングリコール １０．０
４−ジメチルアミノピリジン Ｎ−オキシド ５．０
グリセリントリオクタノエート １０．０
スクワレン ５．０
亜硫酸水素ナトリウム ０．０１
エチルパラベン ０．３
香料 適 量
イオン交換水 残 余
（製法）
イオン交換水にプロピレングリコール及び４−ジメチルアミノピリジン Ｎ−オキシドを加えて溶解し、加熱して７０℃に保った（水相）。他の成分を混合し、加熱融解して７０℃に保った（油相）。水相に油相を徐々に加え、予備乳化を行い、ホモミキサーで均一に乳化した後、よくかきまぜながら３０℃まで冷却した。
<Prescription Example 7 Cream>
Stearic acid 6.0
Sorbitan monostearate ester 2.0
POE (20) sorbitan monostearate ester 1.5
Propylene glycol 10.0
4-Dimethylaminopyridine N-oxide 5.0
Glycerin trioctanoate 10.0
Squalene 5.0
Sodium bisulfite 0.01
Ethylparaben 0.3
Perfume Appropriate amount Ion exchange water Residue (Production method)
Propylene glycol and 4-dimethylaminopyridine N-oxide were added to ion-exchanged water and dissolved, and heated to 70 ° C. (aqueous phase). The other components were mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase was gradually added to the aqueous phase, pre-emulsified, and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
＜処方例８ 乳液＞
ステアリン酸 ２．５
セチルアルコール １．５
ワセリン ５．０
流動パラフィン １０．０
ＰＯＥ（１０）モノオレイン酸エステル ２．０
パラメトキシ桂皮酸２−エチルヘキシルエステル ３．０
２−ヒドロキシ−４−メトキシベンゾフェノン ２．０
４−ｔｅｒｔ−ブチル−４'−メトキシジベンゾイルメタン ２．０
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
ＰＥＧ１５００ ３．０
トリエタノールアミン １．０
４−ジメチルアミノピリジン Ｎ−オキシド ５．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
水酸化ナトリウム ０．４
テレフタリリデンジカンフルスルホン酸 ０．５
４，５−ジモルホリノ−３−ヒドロキシピリダジン ０．１
亜硫酸水素ナトリウム ０．０１
エチルパラベン ０．３
カルボキシビニルポリマー ０．０５
香料 適 量
イオン交換水 残 余
（製法）
少量のイオン交換水にカルボキシビニルポリマーを溶解した（Ａ相）。イオン交換水の残部に水相成分を加え、加熱溶解して７０℃に保った（水相）。他の成分を混合し、加熱融解して７０℃に保った（油相）。水相に油相を加えて予備乳化を行い、Ａ相を加えてホモミキサーで均一に乳化した後、よくかきまぜながら３０℃まで冷却した。
<Prescription Example 8 Latex>
Stearic acid 2.5
Cetyl alcohol 1.5
Vaseline 5.0
Liquid paraffin 10.0
POE (10) monooleate 2.0
Paramethoxycinnamic acid 2-ethylhexyl ester 3.0
2-Hydroxy-4-methoxybenzophenone 2.0
4-tert-butyl-4'-methoxydibenzoylmethane 2.0
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
PEG 1500 3.0
Triethanolamine 1.0
4-Dimethylaminopyridine N-oxide 5.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Sodium hydroxide 0.4
Terephthalylidene dicamphulsulfonic acid 0.5
4,5-Dimorpholino-3-hydroxypyridazine 0.1
Sodium bisulfite 0.01
Ethylparaben 0.3
Carboxyvinyl polymer 0.05
Perfume Appropriate amount Ion exchange water Residue (Production method)
Carboxyvinyl polymer was dissolved in a small amount of ion-exchanged water (A phase). The aqueous phase component was added to the remainder of the ion exchange water, dissolved by heating and maintained at 70 ° C. (aqueous phase). The other components were mixed, heated and melted and kept at 70 ° C. (oil phase). The oil phase was added to the aqueous phase for pre-emulsification, and the A phase was added and uniformly emulsified with a homomixer, and then cooled to 30 ° C. while stirring well.
＜処方例９ ジェル＞
９５％エタノール １０．０
ジプロピレングリコール １５．０
ＰＯＥ（５０）オレイルエーテル ２．０
カルボキシビニルポリマー １．０
水酸化ナトリウム ０．５５
４−ジメチルアミノピリジン Ｎ−オキシド １．０
２−フェニルベンズイミダゾール−５−スルホン酸 １．０
メチルパラベン ０．１
香料 適 量
イオン交換水 残 余
（製法）
イオン交換水にカルボキシビニルポリマーを均一に溶解した（Ａ相）。９５％エタノールにPOE(50)オレイルエーテルを溶解し、Ａ相に添加した。水酸化ナトリウム以外の成分を添加後、水酸化ナトリウムを添加して中和増粘させた。
<Prescription Example 9 Gel>
95% ethanol 10.0
Dipropylene glycol 15.0
POE (50) oleyl ether 2.0
Carboxyvinyl polymer 1.0
Sodium hydroxide 0.55
4-Dimethylaminopyridine N-oxide 1.0
2-Phenylbenzimidazole-5-sulfonic acid 1.0
Methylparaben 0.1
Perfume Appropriate amount Ion exchange water Residue (Production method)
The carboxyvinyl polymer was uniformly dissolved in ion-exchanged water (A phase). POE (50) oleyl ether was dissolved in 95% ethanol and added to Phase A. After adding components other than sodium hydroxide, sodium hydroxide was added to increase the neutralization and viscosity.
＜処方例１０ 美容液＞
（Ａ相）
９５％エタノール １０．０
パラメトキシ桂皮酸２−エチルヘキシルエステル １．０
２−ヒドロキシ−４−メトキシベンゾフェノン ０．５
４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ０．５
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
０．５
ＰＯＥ（２０）オクチルドデカノール １．０
メチルパラベン ０．１５
パントテニルエチルエーテル ０．１
（Ｂ相）
水酸化カリウム ０．１
（Ｃ相）
４−ジメチルアミノピリジン Ｎ−オキシド １０．０
２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
水酸化ナトリウム ０．４
グリセリン ５．０
ジプロピレングリコール １０．０
テレフタリリデンジカンフルスルホン酸 ２．０
亜硫酸水素ナトリウム ０．０３
カルボキシビニルポリマー ０．２
イオン交換水 残 余
（製法）
Ａ相、Ｃ相をそれぞれ均一に溶解し、Ｃ相にＡ相を加えて可溶化した。次いでＢ相を加えて混合した。
<Prescription Example 10 Essence>
(Phase A)
95% ethanol 10.0
Paramethoxycinnamic acid 2-ethylhexyl ester 1.0
2-Hydroxy-4-methoxybenzophenone 0.5
4-tert-butyl-4'-methoxydibenzoylmethane 0.5
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
0.5
POE (20) Octyldodecanol 1.0
Methylparaben 0.15
Pantothenyl ethyl ether 0.1
(Phase B)
Potassium hydroxide 0.1
(Phase C)
4-Dimethylaminopyridine N-oxide 10.0
2-Phenylbenzimidazole-5-sulfonic acid 3.0
Sodium hydroxide 0.4
Glycerin 5.0
Dipropylene glycol 10.0
Terephthalylidene dican full sulfonic acid 2.0
Sodium bisulfite 0.03
Carboxyvinyl polymer 0.2
Ion-exchanged water residue (production method)
The A phase and the C phase were uniformly dissolved, and the A phase was added to the C phase and solubilized. Then phase B was added and mixed.
＜処方例１１ セルフタニングエマルション＞
（パーツＩ）
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
ステアリン酸ＰＥＧ−５グリセリン １．０
ステアリン酸ＰＥＧ−６０グリセリン ２．０
シクロメチコン ５．０
セバシン酸ジイソプロピル ５．０
ベヘニルアルコール ２．０
ステアリルアルコール １．０
水添パーム油 ２．０
香料 適 量
（パーツＩＩ）
４−ジメチルアミノピリジン Ｎ−オキシド ５．０
ジヒドロキシアセトン ５．０
グリチルリチン酸ジカリウム ０．０１
エタノール ５．０
１，３ブチレングリコール ５．０
ＥＤＴＡ−３Ｎａ ０．１
ピロ亜硫酸ナトリウム ０．１
パラベン 適 量
イオン交換水 残 余
（製法）
６０℃で均一溶解したパーツＩＩに７０℃で均一溶解したパーツＩを添加して乳化処理を行う。その後、冷却してセルフタニングエマルションを得る。
<Prescription Example 11 Self-tanning Emulsion>
(Parts I)
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
PEG-5 glyceryl stearate 1.0
PEG-60 glycerin stearate 2.0
Cyclomethicone 5.0
Diisopropyl sebacate 5.0
Behenyl alcohol 2.0
Stearyl alcohol 1.0
Hydrogenated palm oil 2.0
Perfume proper amount (Part II)
4-Dimethylaminopyridine N-oxide 5.0
Dihydroxyacetone 5.0
Dipotassium glycyrrhizinate 0.01
Ethanol 5.0
1,3 Butylene glycol 5.0
EDTA-3Na 0.1
Sodium pyrosulfite 0.1
Paraben appropriate amount Ion exchange water Residue
Part I uniformly dissolved at 70 ° C. is added to part II uniformly dissolved at 60 ° C., and emulsification is performed. Thereafter, it is cooled to obtain a self-tanning emulsion.
＜処方例１２ パック＞
（Ａ相）
ジプロピレングリコール ５．０
ＰＯＥ（６０）硬化ヒマシ油 ５．０
（Ｂ相）
オリーブ油 ５．０
酢酸トコフェロール ０．２
エチルパラベン ０．２
香料 ０．２
（Ｃ相）
４−ジメチルアミノピリジン Ｎ−オキシド ０．１
亜硫酸水素ナトリウム ０．０３
ポリビニルアルコール
（ケン化度９０，重合度２０００） １３．０
エタノール ７．０
イオン交換水 残 余
（製法）
Ａ相、Ｂ相、Ｃ相をそれぞれ均一に溶解し、Ａ相にＢ相を加えて可溶化した。次いでこれをＣ相に加えて混合した。
<Prescription Example 12 Pack>
(Phase A)
Dipropylene glycol 5.0
POE (60) hydrogenated castor oil 5.0
(Phase B)
Olive oil 5.0
Tocopherol acetate 0.2
Ethylparaben 0.2
Fragrance 0.2
(Phase C)
4-Dimethylaminopyridine N-oxide 0.1
Sodium bisulfite 0.03
Polyvinyl alcohol (saponification degree 90, polymerization degree 2000) 13.0
Ethanol 7.0
Ion-exchanged water residue (production method)
A phase, B phase, and C phase were uniformly dissolved, and B phase was added to A phase to solubilize. This was then added to Phase C and mixed.
＜処方例１３ パック＞
（Ａ相）
ジプロピレングリコール ５．０
ＰＯＥ（６０）硬化ヒマシ油 ５．０
（Ｂ相）
オリーブ油 ５．０
酢酸トコフェロール ０．２
エチルパラベン ０．２
香料 ０．２
（Ｃ相）
４−ジメチルアミノピリジン Ｎ−オキシド ０．１
２−フェニルベンズイミダゾール−５−スルホン酸 ０．３
トリエタノールアミン ０．１８
亜硫酸水素ナトリウム ０．０３
ポリビニルアルコール
（ケン化度９０，重合度２０００） １３．０
エタノール ７．０
イオン交換水 残 余
（製法）
Ａ相、Ｂ相、Ｃ相をそれぞれ均一に溶解し、Ａ相にＢ相を加えて可溶化した。次いでこれをＣ相に加えて混合した。
<Prescription Example 13 Pack>
(Phase A)
Dipropylene glycol 5.0
POE (60) hydrogenated castor oil 5.0
(Phase B)
Olive oil 5.0
Tocopherol acetate 0.2
Ethylparaben 0.2
Fragrance 0.2
(Phase C)
4-Dimethylaminopyridine N-oxide 0.1
2-Phenylbenzimidazole-5-sulfonic acid 0.3
Triethanolamine 0.18
Sodium bisulfite 0.03
Polyvinyl alcohol (saponification degree 90, polymerization degree 2000) 13.0
Ethanol 7.0
Ion-exchanged water residue (production method)
A phase, B phase, and C phase were uniformly dissolved, and B phase was added to A phase to solubilize. This was then added to Phase C and mixed.
上記処方例１〜１１は何れも優れた紫外線防止効果を有していた。また、実施例１〜１３に皮膚トラブルは全く認められなかった。 Each of the above Formulation Examples 1 to 11 had an excellent ultraviolet ray preventing effect. Moreover, skin trouble was not recognized at all in Examples 1-13.
＜処方例１４ 乳液＞
（油相）
ステアリルアルコール １．５
スクワレン ２．０
ワセリン ２．５
脱臭液状ラノリン １．５
月見草油 ２．０
ミリスチン酸イソプロピル ５．０
グリセリンモノオレート ２．０
２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
ＰＯＥ（６０）硬化ヒマシ油 ２．０
酢酸トコフェロール ０．０５
エチルパラベン ０．２
ブチルパラベン ０．１
香料 適 量
（水相）
４−ジメチルアミノピリジン Ｎ−オキシド ５．０
４，５−ジモルホリノ−３−ヒドロキシピリダジン ０．０５
亜硫酸水素ナトリウム ０．０１
グリセリン ５．０
ヒアルロン酸ナトリウム ０．０１
カルボキシビニルポリマー ０．２
水酸化カリウム ０．２
イオン交換水 残 余
（製法）
油相、水相をそれぞれ７０℃にて溶解し、水相に油相を混合し、乳化機で乳化後、熱交換機で３０℃まで冷却した。
<Prescription Example 14 Latex>
(Oil phase)
Stearyl alcohol 1.5
Squalene 2.0
Vaseline 2.5
Deodorized liquid lanolin 1.5
Evening primrose oil 2.0
Isopropyl myristate 5.0
Glycerol monooleate 2.0
2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
POE (60) hydrogenated castor oil 2.0
Tocopherol acetate 0.05
Ethylparaben 0.2
Butylparaben 0.1
Perfume appropriate amount (water phase)
4-Dimethylaminopyridine N-oxide 5.0
4,5-Dimorpholino-3-hydroxypyridazine 0.05
Sodium bisulfite 0.01
Glycerin 5.0
Sodium hyaluronate 0.01
Carboxyvinyl polymer 0.2
Potassium hydroxide 0.2
Ion-exchanged water residue (production method)
The oil phase and the aqueous phase were each dissolved at 70 ° C., the oil phase was mixed with the aqueous phase, emulsified with an emulsifier, and then cooled to 30 ° C. with a heat exchanger.
上記処方例１４の乳液も優れた紫外線防止効果を有し、皮膚トラブルは全く認められなかった。 The emulsion of the above Formulation Example 14 also had an excellent UV protection effect, and no skin trouble was observed.
＜処方例１５ 固形パウダリ−ファンデ−ション＞
（１）タルク １５．０
（２）セリサイト １０．０
（３）球状ナイロン粉末 １０．０
（４）多孔性無水ケイ酸粉末 １５．０
（５）窒化ホウ素 ５．０
（６）二酸化チタン ５．０
（７）酸化鉄 ３．０
（８）ステアリン酸亜鉛 ５．０
（９）４−ジメチルアミノピリジン Ｎ−オキシド １．０
（１０）流動パラフィン 残 余
（１１）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
１．０
（１２）トリイソオクタン酸グリセリン １５．０
（１３）セスキオレイン酸ソルビタン １．５
（１４）防腐剤 適 量
（１５）香料 適 量
（製法）
（１）〜（８）の各成分を混合粉砕したところへ、（９）〜（１５）の各成分を混合したものを加えて攪拌混合し、容器に成型して固形ファンデ−ションを得た。
<Prescription Example 15 Solid Powdery Foundation>
(1) Talc 15.0
(2) Sericite 10.0
(3) Spherical nylon powder 10.0
(4) Porous silicic acid powder 15.0
(5) Boron nitride 5.0
(6) Titanium dioxide 5.0
(7) Iron oxide 3.0
(8) Zinc stearate 5.0
(9) 4-Dimethylaminopyridine N-oxide 1.0
(10) Liquid paraffin residue (11) 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
1.0
(12) Triisooctanoic acid glycerin 15.0
(13) Sorbitan sesquioleate 1.5
(14) Preservative appropriate amount (15) Fragrance appropriate amount
(Manufacturing method)
The components (1) to (8) were mixed and pulverized, and the components (9) to (15) were mixed and mixed with stirring. The resulting mixture was molded into a container to obtain a solid foundation. .
＜処方例１６ 固形パウダリ−ファンデ−ション＞
（１）タルク １５．０
（２）セリサイト １０．０
（３）球状ナイロン粉末 １０．０
（４）多孔性無水ケイ酸粉末 １５．０
（５）窒化ホウ素 ５．０
（６）二酸化チタン ５．０
（７）酸化鉄 ３．０
（８）ステアリン酸亜鉛 ５．０
（９）４−ジメチルアミノピリジン Ｎ−オキシド １．０
（１０）流動パラフィン 残 余
（１１）トリイソオクタン酸グリセリン １５．０
（１２）セスキオレイン酸ソルビタン １．５
（１３）防腐剤 適 量
（１４）香料 適 量
（製法）
（１）〜（８）の各成分を混合粉砕したところへ、（９）〜（１５）の各成分を混合したものを加えて攪拌混合し、容器に成型して固形ファンデ−ションを得た。
<Formulation Example 16: Solid powder foundation>
(1) Talc 15.0
(2) Sericite 10.0
(3) Spherical nylon powder 10.0
(4) Porous silicic acid powder 15.0
(5) Boron nitride 5.0
(6) Titanium dioxide 5.0
(7) Iron oxide 3.0
(8) Zinc stearate 5.0
(9) 4-Dimethylaminopyridine N-oxide 1.0
(10) Liquid paraffin residue (11) glycerin triisooctanoate 15.0
(12) Sorbitan sesquioleate 1.5
(13) Preservative appropriate amount (14) Fragrance appropriate amount (production method)
The components (1) to (8) were mixed and pulverized, and the components (9) to (15) were mixed and mixed with stirring. The resulting mixture was molded into a container to obtain a solid foundation. .
＜処方例１７ 油中水型乳化ファンデ−ション＞
（１）球状ナイロン １０．０
（２）多孔性無水ケイ酸粉末 ８．０
（３）雲母チタン ２．０
（４）シリコーン処理セリサイト ２．０
（５）シリコーン処理マイカ １２．０
（６）シリコーン処理二酸化チタン ５．０
（７）シリコーン処理酸化鉄 ２．０
（８）イオン交換水 残 余
（９）４−ジメチルアミノピリジン Ｎ−オキシド ５．０
（１０）デカメチルシクロペンタンシロキサン １８．０
（１１）ジメチルポリシロキサン ５．０
（１２）スクワラン １．０
（１３）ポリオキシエチレン変性ジメチルポリシロキサン ２．０
（１４）パラメトキシ桂皮酸２−エチルヘキシルエステル ３．０
（１５）２−ヒドロキシ−４−メトキシベンゾフェノン 1．０
（１６）４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ０．５
（１７）テレフタリリデンジカンフルスルホン酸 ０．５
（１８）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
０．５
（１９）防腐剤 適 量
（２０）香料 適 量
（製法）
（１０）〜（２０）の各成分を均一に混合溶解したものに、混合粉砕した（１）〜（７）を加えて分散させた。この分散液に、（９）を（８）に溶解したものを加えて乳化し、容器に充填して油中水型乳化ファンデ−ションを得た。
<Prescription Example 17 Water-in-oil emulsification foundation>
(1) Spherical nylon 10.0
(2) Porous silicic acid powder 8.0
(3) Mica titanium 2.0
(4) Silicone-treated sericite 2.0
(5) Silicone-treated mica 12.0
(6) Silicone-treated titanium dioxide 5.0
(7) Silicone-treated iron oxide 2.0
(8) Ion exchange water Residue (9) 4-Dimethylaminopyridine N-oxide 5.0
(10) Decamethylcyclopentanesiloxane 18.0
(11) Dimethylpolysiloxane 5.0
(12) Squalane 1.0
(13) Polyoxyethylene-modified dimethylpolysiloxane 2.0
(14) Paramethoxycinnamic acid 2-ethylhexyl ester 3.0
(15) 2-Hydroxy-4-methoxybenzophenone 1.0
(16) 4-tert-butyl-4′-methoxydibenzoylmethane 0.5
(17) Terephthalylidene dicamphorsulfonic acid 0.5
(18) 2-Ethylhexyl 2-cyano-3,3-diphenyl acrylate
0.5
(19) Preservative appropriate amount (20) Fragrance appropriate amount (Production method)
The components (10) to (20) were uniformly mixed and dissolved, and then mixed and ground (1) to (7) were added and dispersed. To this dispersion, (9) dissolved in (8) was added and emulsified, and filled into a container to obtain a water-in-oil emulsified foundation.
＜処方例１８ 白粉＞
（１）タルク 残 余
（２）セリサイト １０．０
（３）球状ナイロン粉末 １０．０
（４）窒化ホウ素 ５．０
（５）酸化鉄 ３．０
（６）炭酸マグネシウム ５．０
（７）スクワラン ３．０
（８）トリイソオクタン酸グリセリン ２．０
（９）セスキオレイン酸ソルビタン ２．０
（１０）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
０．５
（１１）４−ジメチルアミノピリジン Ｎ−オキシド ０．５
（１２）防腐剤 適 量
（１３）香料 適 量
（製法）
（１）〜（６）の各成分を混合粉砕したところへ、（７）〜（１３）の各成分を混合したものを加えて攪拌混合し、白粉を得た。
<Prescription Example 18 White powder>
(1) Remaining talc (2) Sericite 10.0
(3) Spherical nylon powder 10.0
(4) Boron nitride 5.0
(5) Iron oxide 3.0
(6) Magnesium carbonate 5.0
(7) Squalane 3.0
(8) Glycerin triisooctanoate 2.0
(9) Sorbitan sesquioleate 2.0
(10) 2-Ethylhexyl 2-cyano-3,3-diphenyl acrylate
0.5
(11) 4-Dimethylaminopyridine N-oxide 0.5
(12) Preservative appropriate amount (13) Fragrance appropriate amount (Manufacturing method)
What mixed each component of (7)-(13) was added to the place which mixed and grind | pulverized each component of (1)-(6), and was stirred and mixed, and white powder was obtained.
＜処方例１９ アイシャドー＞
（１）タルク 残 余
（２）マイカ １５．０
（３）球状ナイロン粉末 １０．０
（４）窒化ホウ素 ５．０
（５）酸化鉄 ３．０
（６）酸化チタン被覆マイカ ５．０
（７）スクワラン ３．０
（８）トリイソオクタン酸グリセリン ２．０
（９）セスキオレイン酸ソルビタン ２．０
（１０）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
１．０
（１１）４−ジメチルアミノピリジン Ｎ−オキシド ０．３
（１２）防腐剤 適 量
（１３）香料 適 量
（製法）
（１）〜（６）の各成分を混合粉砕したところへ、（７）〜（１３）の各成分を混合したものを加えて攪拌混合し、アイシャド−を得た。
<Prescription Example 19 Eye Shadow>
(1) Remaining talc (2) Mica 15.0
(3) Spherical nylon powder 10.0
(4) Boron nitride 5.0
(5) Iron oxide 3.0
(6) Titanium oxide coated mica 5.0
(7) Squalane 3.0
(8) Glycerin triisooctanoate 2.0
(9) Sorbitan sesquioleate 2.0
(10) 2-Ethylhexyl 2-cyano-3,3-diphenyl acrylate
1.0
(11) 4-Dimethylaminopyridine N-oxide 0.3
(12) Preservative appropriate amount (13) Fragrance appropriate amount (Manufacturing method)
To each of the components (1) to (6) mixed and pulverized, a mixture of the components (7) to (13) was added and stirred and mixed to obtain an eye shadow.
＜処方例２０ 口紅＞
（１）カルナバロウ ０．５
（２）キャンデリラロウ ５．０
（３）セレシン １０．０
（４）スクワラン 残 余
（５）トリイソステアリン酸グリセリン １０．０
（６）ジイソステアリン酸グリセリン ２０．０
（７）テレフタリリデンジカンフルスルホン酸 ０．５
（８）パラメトキシ桂皮酸２−エチルヘキシルエステル ３．０
（９）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
（１０）４−ジメチルアミノピリジン Ｎ−オキシド ３．０
（１１）マカデミアナッツ油脂肪酸フィトステリル ４．０
（１２）合成ケイ酸ナトリウム−マグネシウム ０．５
（１３）疎水性シリカ ０．５
（１４）イオン交換水 ２．０
（１５）色剤 適 量
（１６）防腐剤 適 量
（１７）香料 適 量
（製法）
６０℃に加熱した（１１）に（１２）、（１３）を分散させ、これに（１０）（１４）を加えて十分攪拌した。別に加熱溶解しておいた（１）〜（９）にこれを加えて十分攪拌し、さらに（１５）〜（１７）を加えて分散攪拌し、その後成型して口紅を得た。
<Prescription Example 20 Lipstick>
(1) Carnauba 0.5
(2) Candelilla wax 5.0
(3) Ceresin 10.0
(4) Squalane residue (5) Glycerol triisostearate 10.0
(6) Glycerin diisostearate 20.0
(7) Terephthalylidene dicamphorsulfonic acid 0.5
(8) Paramethoxycinnamic acid 2-ethylhexyl ester 3.0
(9) 2-Ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
(10) 4-Dimethylaminopyridine N-oxide 3.0
(11) Macadamia nut oil fatty acid phytosteryl 4.0
(12) Synthetic sodium silicate-magnesium 0.5
(13) Hydrophobic silica 0.5
(14) Ion exchange water 2.0
(15) Colorant appropriate amount (16) Preservative appropriate amount (17) Fragrance appropriate amount (Manufacturing method)
(12) and (13) were dispersed in (11) heated to 60 ° C., and (10) and (14) were added thereto, followed by thorough stirring. Separately, this was added to (1) to (9), which had been heated and dissolved, and stirred well. Further, (15) to (17) were added, dispersed and stirred, and then molded to obtain a lipstick.
＜処方例２１ 口紅＞
（１）カルナバロウ ０．５
（２）キャンデリラロウ ５．０
（３）セレシン １０．０
（４）スクワラン 残 余
（５）トリイソステアリン酸グリセリン １０．０
（６）ジイソステアリン酸グリセリン ２０．０
（７）テレフタリリデンジカンフルスルホン酸 ０．５
（８）パラメトキシ桂皮酸２−エチルヘキシルエステル ３．０
（９）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
（１０）４−ジメチルアミノピリジン Ｎ−オキシド ２．０
（１１）２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
（１２）水酸化ナトリウム ０．４
（１３）マカデミアナッツ油脂肪酸フィトステリル ４．０
（１４）合成ケイ酸ナトリウム−マグネシウム ０．５
（１５）疎水性シリカ ０．５
（１６）イオン交換水 ２．０
（１７）色剤 適 量
（１８）防腐剤 適 量
（１９）香料 適 量
（製法）
６０℃に加熱した（１３）に（１４）、（１５）を分散させ、これに（１０）（１１）、（１２）、（１６）を加えて十分攪拌した。別に加熱溶解しておいた（１）〜（９）にこれを加えて十分攪拌し、さらに（１７）〜（１９）を加えて分散攪拌し、その後成型して口紅を得た。
<Prescription Example 21 Lipstick>
(1) Carnauba 0.5
(2) Candelilla wax 5.0
(3) Ceresin 10.0
(4) Squalane residue (5) Glycerol triisostearate 10.0
(6) Glycerin diisostearate 20.0
(7) Terephthalylidene dicamphorsulfonic acid 0.5
(8) Paramethoxycinnamic acid 2-ethylhexyl ester 3.0
(9) 2-Ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
(10) 4-Dimethylaminopyridine N-oxide 2.0
(11) 2-Phenylbenzimidazole-5-sulfonic acid 3.0
(12) Sodium hydroxide 0.4
(13) Macadamia nut oil fatty acid phytosteryl 4.0
(14) Synthetic sodium silicate-magnesium 0.5
(15) Hydrophobic silica 0.5
(16) Ion exchange water 2.0
(17) Coloring agent appropriate amount (18) Preservative appropriate amount (19) Fragrance appropriate amount (Manufacturing method)
(14) and (15) were dispersed in (13) heated to 60 ° C., and (10), (11), (12), and (16) were added thereto and stirred sufficiently. Separately, this was added to (1) to (9), which had been heated and dissolved, and stirred sufficiently. Further, (17) to (19) were added and dispersed and stirred, and then molded to obtain a lipstick.
処方例１５〜２１のメーキャップ化粧料は何れも優れた紫外線防止効果を有し、また、皮膚トラブルや、経時的な変色等は認められなかった。 The makeup cosmetics of Formulation Examples 15 to 21 all had excellent UV protection effects, and skin troubles and discoloration over time were not observed.
＜処方例２２ ヘアフォーム＞
（原液処方）
（１）アクリル樹脂アルカノールアミン液（５０％） ８．０
（２）ポリオキシエチレン硬化ヒマシ油 適 量
（３）流動パラフィン ５．０
（４）グリセリン ３．０
（５）香料 適 量
（６）防腐剤 適 量
（７）エタノール １５．０
（８）４−ジメチルアミノピリジン Ｎ−オキシド ７．０
（９）イオン交換水 残 余
（充填処方）
（１）原液 ９０．０
（２）液化石油ガス １０．０
（製法）
流動パラフィンをグリセリンとポリオキシエチレン硬化ヒマシ油の溶解物に添加し、ホモミキサーで均一に乳化した。これを他の成分の溶液に添加した。充填は缶に原液を充填し、バルブ装着後、ガスを充填した。
<Prescription Example 22 Hair Foam>
(Stock solution formulation)
(1) Acrylic resin alkanolamine liquid (50%) 8.0
(2) Polyoxyethylene hydrogenated castor oil appropriate amount (3) Liquid paraffin 5.0
(4) Glycerin 3.0
(5) Perfume appropriate amount (6) Preservative appropriate amount (7) Ethanol 15.0
(8) 4-Dimethylaminopyridine N-oxide 7.0
(9) Ion exchange water residue (filling formula)
(1) Stock solution 90.0
(2) Liquefied petroleum gas 10.0
(Manufacturing method)
Liquid paraffin was added to a glycerin and polyoxyethylene hydrogenated castor oil solution and uniformly emulsified with a homomixer. This was added to the solution of the other ingredients. For filling, the stock solution was filled in the can, and after the valve was mounted, the gas was filled.
＜処方例２３ ヘアフォーム＞
（原液処方）
（１）アクリル樹脂アルカノールアミン液（５０％） ８．０
（２）ポリオキシエチレン硬化ヒマシ油 適 量
（３）流動パラフィン ５．０
（４）グリセリン ３．０
（５）香料 適 量
（６）防腐剤 適 量
（７）エタノール １５．０
（８）４−ジメチルアミノピリジン Ｎ−オキシド ３．０
（９）イオン交換水 残 余
（充填処方）
（１）原液 ９０．０
（２）液化石油ガス １０．０
（製法）
流動パラフィンをグリセリンとポリオキシエチレン硬化ヒマシ油の溶解物に添加し、ホモミキサーで均一に乳化した。これを他の成分の溶液に添加した。充填は缶に原液を充填し、バルブ装着後、ガスを充填した。
<Prescription Example 23 Hair Foam>
(Stock solution formulation)
(1) Acrylic resin alkanolamine liquid (50%) 8.0
(2) Polyoxyethylene hydrogenated castor oil appropriate amount (3) Liquid paraffin 5.0
(4) Glycerin 3.0
(5) Perfume appropriate amount (6) Preservative appropriate amount (7) Ethanol 15.0
(8) 4-Dimethylaminopyridine N-oxide 3.0
(9) Ion exchange water residue (filling formula)
(1) Stock solution 90.0
(2) Liquefied petroleum gas 10.0
(Manufacturing method)
Liquid paraffin was added to a glycerin and polyoxyethylene hydrogenated castor oil solution and uniformly emulsified with a homomixer. This was added to the solution of the other ingredients. For filling, the stock solution was filled in the can, and after the valve was mounted, the gas was filled.
＜処方例２４ ヘアリキッド＞
（１）ポリオキシプロピレン（４０）ブチルエーテル ２０．０
（２）ポリオキシエチレン硬化ヒマシ油 １．０
（３）エタノール ５０．０
（４）香料 適 量
（５）防腐剤 適 量
（６）パラメトキシ桂皮酸２−エチルヘキシルエステル ２．０
（７）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
（８）染料 適 量
（９）４−ジメチルアミノピリジン Ｎ−オキシド ２．０
（１０）イオン交換水 残 余
（製法）
エタノールにポリオキシプロピレン（４０）ブチルエーテル、ポリオキシエチレン硬化ヒマシ油、香料、防腐剤、パラメトキシ桂皮酸２−エチルヘキシルエステル、２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレートを溶解した。イオン交換水に４−ジメチルアミノピリジン Ｎ−オキシド、染料を溶解した。エタノール相に水相を添加し、ろ紙でろ過した。
<Prescription Example 24 Hair Liquid>
(1) Polyoxypropylene (40) butyl ether 20.0
(2) Polyoxyethylene hydrogenated castor oil 1.0
(3) Ethanol 50.0
(4) Perfume appropriate amount (5) Preservative appropriate amount (6) Paramethoxycinnamic acid 2-ethylhexyl ester 2.0
(7) 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
(8) Dye proper amount (9) 4-dimethylaminopyridine N-oxide 2.0
(10) Residual ion exchange water (Production method)
Polyoxypropylene (40) butyl ether, polyoxyethylene hydrogenated castor oil, fragrance, preservative, paramethoxycinnamic acid 2-ethylhexyl ester, 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate were dissolved in ethanol. 4-dimethylaminopyridine N-oxide and dye were dissolved in ion-exchanged water. The aqueous phase was added to the ethanol phase and filtered through filter paper.
＜処方例２５ ヘアスプレー＞
（原液処方）
（１）アクリル樹脂アルカノールアミン液（５０％） ７．０
（２）セチルアルコール ０．１
（３）シリコーン油 ０．３
（４）エタノール 残 余
（５）香料 適 量
（６）４−ジメチルアミノピリジン Ｎ−オキシド １．０
（７）イオン交換水 ３．０
（充填処方）
（１）原液 ５０．０
（２）液化石油ガス ５０．０
（製法）
エタノールに他の成分を加え溶解し、ろ過した。充填は缶に原液を充填し、バルブ装着後、ガスを充填した。
<Prescription Example 25 Hair Spray>
(Stock solution formulation)
(1) Acrylic resin alkanolamine liquid (50%) 7.0
(2) Cetyl alcohol 0.1
(3) Silicone oil 0.3
(4) Ethanol residue (5) Fragrance appropriate amount (6) 4-Dimethylaminopyridine N-oxide 1.0
(7) Ion exchange water 3.0
(Filling prescription)
(1) Stock solution 50.0
(2) Liquefied petroleum gas 50.0
(Manufacturing method)
Other components were added to ethanol, dissolved, and filtered. For filling, the stock solution was filled in the can, and after the valve was mounted, the gas was filled.
＜処方例２６ ヘアトニック＞
（１）４−ジメチルアミノピリジン Ｎ−オキシド ３．０
（２）硬化ヒマシ油エチレンオキシド（４０モル）付加物 ２．０
（３）パラメトキシ桂皮酸２−エチルヘキシルエステル ３．０
（４）２−ヒドロキシ−４−メトキシベンゾフェノン ３．０
（５）４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ３．０
（６）テレフタリリデンジカンフルスルホン酸 １．０
（７）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
（８）２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
（９）トリエタノールアミン １．８
（１０）エタノール ６０．０
（１１）香料 適 量
（１２）イオン交換水 残 余
（製法）
エタノールに硬化ヒマシ油エチレンオキシド（４０モル）付加物、パラメトキシ桂皮酸２−エチルヘキシルエステル、２−ヒドロキシ−４−メトキシベンゾフェノン、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン、テレフタリリデンジカンフルスルホン酸、及び２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレートを溶解した。イオン交換水に４−ジメチルアミノピリジン Ｎ−オキシド、２−フェニルベンズイミダゾール−５−スルホン酸、トリエタノールアミンを溶解した。エタノール相及び水相を混合し、香料を加えた。
<Prescription Example 26 Hair Tonic>
(1) 4-Dimethylaminopyridine N-oxide 3.0
(2) Hardened castor oil ethylene oxide (40 mol) adduct 2.0
(3) Paramethoxycinnamic acid 2-ethylhexyl ester 3.0
(4) 2-hydroxy-4-methoxybenzophenone 3.0
(5) 4-tert-butyl-4′-methoxydibenzoylmethane 3.0
(6) Terephthalylidene dicamphorsulfonic acid 1.0
(7) 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
(8) 2-Phenylbenzimidazole-5-sulfonic acid 3.0
(9) Triethanolamine 1.8
(10) Ethanol 60.0
(11) Fragrance appropriate amount (12) Residue of ion-exchanged water (Production method)
Hardened castor oil ethylene oxide (40 mol) adduct in ethanol, paramethoxycinnamic acid 2-ethylhexyl ester, 2-hydroxy-4-methoxybenzophenone, 4-tert-butyl-4'-methoxydibenzoylmethane, terephthalylidene dicanful sulfone The acid and 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate were dissolved. 4-dimethylaminopyridine N-oxide, 2-phenylbenzimidazole-5-sulfonic acid, and triethanolamine were dissolved in ion-exchanged water. The ethanol phase and the aqueous phase were mixed and the fragrance was added.
＜処方例２７ ヘアトニック＞
（１）４−ジメチルアミノピリジン Ｎ−オキシド ２．０
（２）２−フェニルベンズイミダゾール−５−スルホン酸 ３．０
（３）水酸化ナトリウム ０．４
（４）硬化ヒマシ油エチレンオキシド（４０モル）付加物 ２．０
（５）パラメトキシ桂皮酸２−エチルヘキシルエステル ３．０
（６）２−ヒドロキシ−４−メトキシベンゾフェノン ３．０
（７）４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン ３．０
（８）２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレート
５．０
（９）エタノール ６０．０
（１０）香料 適 量
（１１）イオン交換水 残 余
（製法）
エタノールに硬化ヒマシ油エチレンオキシド（４０モル）付加物、パラメトキシ桂皮酸２−エチルヘキシルエステル、２−ヒドロキシ−４−メトキシベンゾフェノン、４−ｔｅｒｔ−ブチル−４’−メトキシジベンゾイルメタン、及び２−エチルヘキシル ２−シアノ−３，３−ジフェニルアクリレートを溶解した。イオン交換水に４−ジメチルアミノピリジン Ｎ−オキシドを溶解した。エタノール相及び水相を混合し、香料を加えた。
<Prescription Example 27 Hair Tonic>
(1) 4-Dimethylaminopyridine N-oxide 2.0
(2) 2-Phenylbenzimidazole-5-sulfonic acid 3.0
(3) Sodium hydroxide 0.4
(4) Hardened castor oil ethylene oxide (40 mol) adduct 2.0
(5) Paramethoxycinnamic acid 2-ethylhexyl ester 3.0
(6) 2-hydroxy-4-methoxybenzophenone 3.0
(7) 4-tert-butyl-4′-methoxydibenzoylmethane 3.0
(8) 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate
5.0
(9) Ethanol 60.0
(10) Perfume appropriate amount (11) Ion-exchanged water residue (Process)
Hydrogenated castor oil ethylene oxide (40 mol) adduct in ethanol, paramethoxycinnamic acid 2-ethylhexyl ester, 2-hydroxy-4-methoxybenzophenone, 4-tert-butyl-4'-methoxydibenzoylmethane, and 2-ethylhexyl 2- Cyano-3,3-diphenyl acrylate was dissolved. 4-dimethylaminopyridine N-oxide was dissolved in ion-exchanged water. The ethanol phase and the aqueous phase were mixed and the fragrance was added.
処方例２２〜２７の毛髪用及び頭皮用化粧料は何れも優れた紫外線防止効果を有し、また、頭皮トラブルや、経時的な変色等は認められなかった。 The cosmetics for hair and scalp of Formulation Examples 22 to 27 all had an excellent UV protection effect, and no scalp trouble or discoloration over time was observed.
Claims (4)
（化１）
(Chemical formula 1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007118998A JP4887207B2 (en) | 2007-04-27 | 2007-04-27 | Ultraviolet absorber and skin external preparation composition containing the same |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2007118998A JP4887207B2 (en) | 2007-04-27 | 2007-04-27 | Ultraviolet absorber and skin external preparation composition containing the same |
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| Publication Number | Publication Date |
|---|---|
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| KR100572942B1 (en) * | 2001-05-17 | 2006-04-25 | 다이킨 고교 가부시키가이샤 | Nonlinear Optical Materials Including Fluorine-Containing Polymers |
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