JP6614642B2 - メイクアップ化粧料用組成物 - Google Patents
メイクアップ化粧料用組成物 Download PDFInfo
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- JP6614642B2 JP6614642B2 JP2015146060A JP2015146060A JP6614642B2 JP 6614642 B2 JP6614642 B2 JP 6614642B2 JP 2015146060 A JP2015146060 A JP 2015146060A JP 2015146060 A JP2015146060 A JP 2015146060A JP 6614642 B2 JP6614642 B2 JP 6614642B2
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- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 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
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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Description
(A):組成物全量の0.1〜20重量%
(B):組成物全量の0.1〜95重量%
(C):組成物全量の0.01〜99重量%
本発明における変性ポリシロキサン化合物は、下記式(1)で表される。式中、R1〜R9は、同一又は異なって、炭素数1〜20の直鎖状アルキル基、炭素数3〜6の分岐鎖状アルキル基、及び炭素数3〜6の環状アルキル基から選択される炭化水素基を示す。p、qは、それぞれ括弧内に示されるシロキサン単位の数の平均値を示し、pは1以上の数、qは2以上の数である。pが2以上の場合、2個以上のR7、R8は、それぞれ同一であってもよく、異なっていてもよい。また、2個以上のR9は、同一であってもよく、異なっていてもよい。
p、(q-1)、(q-2)の合計に占めるpの割合は、例えば10〜90mol%、より好ましくは30〜60mol%、さらに好ましくは45〜55mol%である。
p、(q-1)、(q-2)の合計に占める(q-1)の割合は、例えば10〜90mol%、より好ましくは20〜50mol%、さらに好ましくは35〜45mol%である。
p、(q-1)、(q-2)の合計に占める(q-2)の割合は、例えば1〜20mol%、より好ましくは5〜15mol%、さらに好ましくは5〜10mol%である。
油相成分(B)としては、上記変性ポリシロキサン(A)のポリジアルキルシロキサン主鎖及び/又は側鎖アルキル基と親和性が高いものを使用することが好ましく、シリコーン油、高極性オイル、低極性オイル、高級脂肪酸、脂溶性ビタミン類、及び油溶性増粘剤等を挙げることができる。これらは1種を単独で、又は2種以上を組み合わせて使用することができる。
粉体(C)としては、例えば、顔料、紫外線防御剤等を挙げることができる。これらは1種を単独で、又は2種以上を組み合わせて使用することができる。
本発明のメイクアップ化粧料用組成物は、上記変性ポリシロキサン化合物(A)、油相成分(B)、及び粉体(C)を含有する。
(3−[N−メチル(10−ウンデセノイルアミド)]プロパン−1,2−ジオールの合成)
還流管、3方コック付き窒素導入口、3方コック付きベント、減圧シール付き撹拌翼、温度計を備えた容量1Lの5ツ口フラスコに10−ウンデセン酸メチル 317.29g(1.60mol)、3−アミノプロパン−1,2−ジオール 173.27g(1.65mol)、24%ナトリウムメトキサイドメタノール溶液 3.78g(16.0mmol)を添加し、500hPa〜50hPaで減圧しつつ108℃〜117℃で加熱撹拌して、生成するメタノールを留去しながら24.5時間反応し、室温に冷却し、エタノール 290gを加えて撹拌、希釈したのち、無機合成吸着剤(商品名「キョーワード700」、協和化学工業(株)製)を50g添加して75℃で2時間加熱撹拌し、ろ過した。得られたろ液をロータリーエバポレーターで濃縮して減圧デシケーター中で恒量値まで乾燥して、白色ペーストとして3−[N−メチル(10−ウンデセノイルアミド)]プロパン−1,2−ジオール 382.80g(収率:77.5%)を得た。尚、得られた反応生成物の構造は、1H−NMRスペクトル、及びIRスペクトルにより確認した。
3方コック付き水素導入口付きの還流管、3方コック付き窒素導入口、温度計、撹拌用回転子を備えた容量1Lの5ツ口フラスコに、ジメチルシロキサン−メチルヒドロシロキサンコポリマー(商品名「KF−9901」、信越化学(株)製)176.03g、1−デセン 134.66g(0.96mol)、酢酸ブチル(和光純薬工業(株)製)310.68gを入れ、内部を窒素置換した。0.2%塩化白金酸6水和物(和光純薬工業(株)製)の酢酸ブチル溶液 1.2432g(塩化白金酸6水和物4.8μmol)を入れ、徐々に70℃に昇温して3時間撹拌した。
次に、上記で得られた3−[N−メチル(10−ウンデセノイルアミド)]プロパン−1,2−ジオール 64.90g(0.24mol)および0.2%塩化白金酸6水和物(和光純薬工業(株)製)の酢酸ブチル溶液 4.9718g(塩化白金酸6水和物19.2μmol)を入れ、徐々に70℃に昇温して16時間後に1−デセン 67.32g(0.48mol)、さらにその10時間後に1−デセン 33.66g(0.24mol)を追加して、10時間撹拌した。
反応溶液をサンプリングして1H−NMR(重クロロホルム溶液)でδ4.65ppm〜δ4.70ppmに観測されるメチルヒドロシロキサン単位のSi−Hプロトン由来のシグナルが消失したことを確認の上、冷却した。
得られた反応混合物をロータリーエバポレーターで濃縮乾燥したのち、分液ロートに移して上層液中に含まれる1−デセンが10ppm以下となるまでアセトンで分液洗浄操作を繰り返した後、下層液をロータリーエバポレーターで恒量値まで濃縮乾燥して、下記式で表されるシロキサン単位を有する、淡黄褐色透明オイル状の変性ポリシロキサン化合物(1)286.72gを得た。1H−NMRシグナルの積分値より、各シロキサン単位の導入比[pmol%:(q−1)mol%:(q−2)mol%]は、52.1:40.5:7.4であることが計算により求められた。
(変性ポリシロキサン化合物の合成)
3−[N−メチル(10−ウンデセノイルアミド)]プロパン−1,2−ジオールに代えて、特開平7−53431号公報に記載の方法に従って合成して得られた1−(10−ウンデセニルオキシ)プロパン−2,3−ジオールを用いた以外は調製例1と同様にして、下記式で表されるシロキサン単位を有する変性ポリシロキサン化合物(2)を得た。1H−NMRシグナルの積分値より、各シロキサン単位の導入比[pmol%:(q−1)mol%:(q−2)mol%]は、52.0:41.1:6.9であることが計算により求められた。
下記表1〜3に記載の処方(単位:重量部)に従って各成分をタイル上に秤取し、スパチュラでよく混練して組成物を得た。得られた組成物について、粉体の分散性を下記方法で評価した。
組成物をスライドグラスに乗せ、その上にカバーグラスを置いて作成した観察用試料を、顕微鏡((株)ニコン製光学顕微鏡「Nikon ECLIPSE 50i」、倍率20倍又は40倍)を用いて観察し、下記基準で分散性を評価した。
評価基準
◎:凝集塊が全く認められない
○:直径5μm以下の凝集塊は存在するものの、大半の粒子は一次粒子である
△:直径5μm以上の凝集塊が存在し、一次粒子は少ない
×:殆どが直径5μm以上の凝集塊となっている
酸化チタン:水性アルミナ表面処理酸化チタン、平均一次粒子径250nm、商品名「CR−50」、石原産業(株)製
赤色202号:平均一次粒子径50nm、商品名「Unipure Red LC 3079」、Sensient Cosmetic Technologies製
トリエチルヘキサノイン:商品名「T.I.O.」、日清オイリオグループ(株)製
ジカプリン酸ネオペンチルグリコール:商品名「エステモールN−01」、日清オイリオグループ(株)製
α−オレフィンオリゴマー:商品名「ノムコートHP−30」、日清オイリオグループ(株)製
ポリジメチルシロキサン:商品名「SH−200 Fluid 1.5cs」、東レ・ダウコーニング(株)製
両親媒性高分子化合物として、調製例1で得られた変性ポリシロキサン化合物(1)((1)とする)、調製例2で得られた変性ポリシロキサン化合物(2)((2)とする)、グリセリルエーテル変性シリコーン(商品名「ペネトールSI−U」、花王(株)製:GEとする)、又はポリエーテル変性シリコーン(商品名「KF−6015」、信越化学工業(株)製:PEとする)を用い、両親媒性高分子化合物と純水を90:10(両親媒性高分子化合物:純水(重量比))の割合で、全量1.0gになるように混合して、試料を調製した。
より詳細には、まず2.0mLマイクロチューブ中に両親媒性高分子化合物をそれぞれ秤取り、純水を所定の配合量まで少量ずつ添加しながら、均一になるまでスパーテルを用いて撹拌を行って試料を得た。なお、撹拌時間は全工程で30分間となる様に実施した。
皮膚モデルとして手芸用豚皮レザーを水で湿潤させたものを用い、各試料を0.05g秤取り、1枚の手芸用豚皮レザーの試料塗布面に塗布し、その上にもう1枚の手芸用豚皮レザーを重ね、2kgの重しをのせて1分間接着させた後、剥離試験に供した(図1参照)。
2枚の手芸用豚皮レザーのアタッチメント面部分をデジタルフォースゲージのクリップで挟んで固定し、引きはがし速度50mm/minでの引きはがし応力を測定した。結果を図2に示す。
尚、剥離試験は、日本工業規格(JIS)の[6]T型はく離を参考に、接着層を180°方向に引きはがした際の引きはがし応力をデジタルフォースゲージ(商品名「ZP−5N」、(株)イマダ製)を使用して測定した。
図2より、両親媒性高分子化合物として変性ポリシロキサン化合物(1)を用いた場合の剥離強度が最も高く、変性ポリシロキサン化合物(2)、グリセリルエーテル変性シリコーン(GE)、ポリエーテル変性シリコーン(PE)を用いた場合の剥離強度を上回っていることより、変性ポリシロキサン化合物(A)を含有する本発明のメイクアップ化粧料用組成物が、皮膚密着性が優れていることは明らかである。
顔料等の粉体の分散の良否はメイクアップ化粧料向け固形配合物の外観を左右する重要な因子であることより、調製例1で得られた変性ポリシロキサン化合物(1)を用いて、口紅を模した固形配合組成物(1)〜(3)を調製して外観を評価した。
まず、調製例1で得られた変性ポリシロキサン化合物(1)70重量%とラウロイルグルタミン酸ジ(フィトステリル/オクチルドデシル)(商品名「エルデュウPS−203」、味の素ヘルシーサプライ(株)製)30重量%の混合物(「MDU−P30」とする)を調製した。
下記表4に記載の処方(単位:重量部)に従って各成分を秤量し、100℃にて加熱混合した後、10分間ヘラで混合し、さらに100℃で5分間加熱混合して型に流し込み25℃に冷却し、十分に固化させて固形配合組成物を得た。得られた固形配合組成物の外観を下記基準で評価した。
評価基準
◎:顔料の凝集が全くなく、発色は良好(鮮やか)である。
○:目視では顔料の凝集は認められないものの、発色はやや不良である。
△:顔料は概ね分散しているが部分的に凝集が認められ、発色は不良である。
×:全体的に顔料の凝集が認められる。
酸化鉄:ベンガラ・シリカ混合物、平均一次粒子径100nm、商品名「Unipure Red LC 381」、Sensient Cosmetic Technologies製
酸化チタン:水性アルミナ表面処理酸化チタン、平均一次粒子径250nm、商品名「CR−50」、石原産業(株)製
赤色202号:平均一次粒子径50nm、商品名「Unipure Red LC 3079」、Sensient Cosmetic Technologies製
分岐パラフィンワックス:商品名「パラフィンワックスMW」、日本精鑞(株)製
直鎖パラフィンワックス:商品名「パラフィンワックスHNP−9」、日本精鑞(株)製
イソノナン酸イソトリデシル:商品名「サラコス913」、日清オイリオグループ(株)製
ジカプリン酸ネオペンチルグリコール:商品名「エステモールN−01」、日清オイリオグループ(株)製
α−オレフィンオリゴマー:商品名「ノムコートHP−30」、日清オイリオグループ(株)製
ワセリン:商品名「ノムコートW」、日清オイリオグループ(株)製
表5に示す成分を50℃で混合した後、プレスして、チーク(ほお紅)を得た。無機粉体成分はすべて有機表面処理されていないものを用いたが、得られたチークは、発色が良好で、皮膚に付着した化粧料皮膜は、長時間剥がれ落ちることなく残留し、良好な発色を持続した。
表6に示す成分を50℃で混合した後、プレスして、アイシャドウを得た。無機粉体成分はすべて有機表面処理されていないものを用いたが、得られたアイシャドウは、発色が良好で、塗布の感触が軽いものであった。
表7に示す成分を撹拌混合することにより、マスカラを得た。無機粉体成分(顔料)はすべて有機表面処理されていないものを用いたが、得られたマスカラは粉体成分の分散性が良好で、ダマになりくいものであった。
表8に示す成分をハンマーミルを使用して混合することにより、ファンデーションを得た。無機粉体成分はすべて有機表面処理されていないものを用いたが、得られたファンデーションは発色が良好で、粉散りをおこしにくいものであった。
2 アタッチメント面
3 湿潤させた手芸用豚皮レザー
Claims (4)
- 下記式(1)で表される変性ポリシロキサン化合物(A)、油相成分(B)、及び粉体(C)を下記範囲で含有し、且つ前記(A)の含有量が、前記(C)1重量部に対して、0.01〜3重量部の範囲であるメイクアップ化粧料用組成物。
(A):組成物全量の0.1〜20重量%
(B):組成物全量の0.1〜95重量%
(C):組成物全量の0.01〜99重量%
- 油相成分(B)として、シリコーン油、高極性オイル、低極性オイル、高級脂肪酸、脂溶性ビタミン、及び油溶性増粘剤からなる群より選択される少なくとも1種の化合物を含み、粉体(C)として顔料及び/又は紫外線防御剤を含む請求項1に記載のメイクアップ化粧料用組成物。
- 粉体(C)が粉体(有機表面処理された粉体を除く)(C)である請求項1又は2に記載のメイクアップ化粧料用組成物。
- メイクアップ化粧料が、口紅、リップグロス、ファンデーション、チーク、マスカラ、アイライナー、又はアイシャドウである請求項1〜3の何れか1項に記載のメイクアップ化粧料用組成物。
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