JP7471049B2 - 生分解性樹脂粒子を含む化粧料用組成物 - Google Patents
生分解性樹脂粒子を含む化粧料用組成物 Download PDFInfo
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- JP7471049B2 JP7471049B2 JP2018109689A JP2018109689A JP7471049B2 JP 7471049 B2 JP7471049 B2 JP 7471049B2 JP 2018109689 A JP2018109689 A JP 2018109689A JP 2018109689 A JP2018109689 A JP 2018109689A JP 7471049 B2 JP7471049 B2 JP 7471049B2
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Description
しかし、特許文献1の生分解性粒子は、他の樹脂と共に溶融混練、押出した後、他の樹脂を溶解することによって製造されるため、粒子内部が多孔質化されず、中実構造を有しているものと思われる。中実構造の生分解性粒子は、比表面積が小さいため、生分解性効率が劣り、環境中に長くとどまることが心配される。
[1] 走査透過電子顕微鏡による断面写真において粒子内部に1つ以上の単孔が観察され、粒子長径と粒子短径の合計をD1とし、単孔長径と単孔短径の合計をD2とした時、D2/D1が0.05以上、0.20以下となる単孔の数が粒子1つあたり5個以上であることを特徴とする生分解性樹脂粒子を含む化粧料用組成物。
[2] 体積平均粒子径が1.0~30μmである前記[1]に記載の生分解性樹脂粒子を含む化粧料用組成物。
[3] 前記単孔の長径と短径の合計D2の算術平均値が、0.1~4.5μmである前記[1]又は[2]に記載の生分解性樹脂粒子を含む化粧料用組成物。
[4] 前記生分解性樹脂が、脂肪族ジカルボン酸と脂肪族ジオールとの脱水縮合体、または脂肪族ヒドロキシカルボン酸の脱水縮合体である前記[1]~[3]のいずれかに記載の生分解性樹脂粒子を含む化粧料用組成物。
1-1.成分
本発明で粒子とする生分解性樹脂としては、公知の種々の生分解性樹脂が使用でき、中でも脂肪族ジカルボン酸と脂肪族ジオールとの脱水縮合体、または脂肪族ヒドロキシカルボン酸の脱水縮合体などの生分解性ポリエステル樹脂が好ましい。
前記脂肪族ジカルボン酸としては、シュウ酸、マロン酸、コハク酸、アジピン酸、アゼライン酸、セバシン酸などの炭素数が2~10程度、好ましくは3~8程度のジカルボン酸(特にα,ω-アルカンジカルボン酸)が挙げられ、コハク酸が最も好ましい。これら脂肪族ジカルボン酸は、1種でもよく、2種以上を適宜組み合わせてもよい。
ヒドロキシカルボン酸としては、グリコール酸、乳酸などが挙げられ、ヒドキシカルボン酸は、環状多量化したものであってもよく、例えば、グリコリド(1,4-ジオキサン-2,5-ジオン)、ジラクチド(3,6-ジメチル-1,4-ジオキサン-2,5-ジオン)などであってもよい。好ましいヒドロキシカルボン酸は、乳酸、ジラクチドなどであり、より好ましくは乳酸である。
本発明の生分解性樹脂粒子は、粒子内に適度な大きさの単孔を有している。この単孔は、走査透過電子顕微鏡写真の白色部であり、外縁を特定可能な独立孔(不連続孔)として表示される。そして本発明では、前記単孔(独立孔)が適度な大きさに制御され、かつ適度な数が存在するため、生分解性改善、光散乱性の向上、薬剤の内包効率向上などに効果的である。具体的には、粒子サイズをその長径(L)と短径(S)の合計値D1(=L+S)で表し、単孔(独立孔)サイズをその長径(l)と短径(s)の合計値D2(=l+s)で表した時、D2/D1が0.05以上、0.20以下となる単孔(独立孔)(以下、R0.05-0.20と表すことがある。添字の左側はD2/D1の下限値を、添字の右側はD2/D1の上限値を示す)が適度な大きさの単孔(独立孔)とされ、以下、本明細書では良孔という場合がある。良孔の数は、生分解性樹脂粒子断面1つあたり平均で、5個以上、好ましくは7個以上、より好ましくは9個以上である。良孔が多くなるほど、生分解性改善、光散乱性の向上、薬剤の内包効率向上などに効果的である。良孔の数の上限は、生分解性樹脂粒子の粒径に応じて論理的に設定される上限値と同等であってもよいが、例えば、20以下、好ましくは18以下であってもよい。
所定の大きさの単孔(良孔)を所定の個数有する生分解性樹脂粒子は、例えば、工程1~4を行うことによって製造できる。
工程1:生分解性樹脂を水非混和性有機溶媒に可溶な水溶性高分子(以下、両可溶性高分子という)と共に水非混和性有機溶媒に溶解させる(生分解性樹脂液)。
工程2:分散剤(界面活性剤、水非混和性有機溶媒に難溶な水溶性高分子など)を含有する水と前記生分解性樹脂液とを撹拌し、懸濁液を調製する。
工程3:懸濁液から前記水非混和性有機溶媒を蒸発留去し、水相中に生分解性樹脂粒子を浮遊させる。
工程4:水相と生分解性樹脂粒子とを分離し、生分解性樹脂粒子を必要に応じて洗浄した後、乾燥する。
生分解性樹脂の種類に応じて、両可溶性高分子や分散剤の割合、懸濁強度などを適宜調整することによって、良孔を制御できる。
K=(1.5logηrel-1)/(0.15+0.003c)+(300clogηrel+(c+1.5clogηrel)2)1/2/(0.15c+0.003c2)
[式中、ηrelは、両可溶性高分子水溶液の水に対する相対粘度を示し、cは両可溶性高分子水溶液中の両可溶性高分子濃度(%)を示す]
なおK値は、実測せず、メーカー測定値を採用することもできる。
本発明の化粧料用組成物は、上記生分解性樹脂粒子を含む。上記生分解性樹脂粒子は優れた生分解性を有することから、化粧料用組成物において好適に使用することができる。
各種物性の測定は以下の方法で行った。
生分解性樹脂粒子の断面を倍率10,000倍~30,000倍、加速電圧20kVの条件で走査透過電子顕微鏡により撮影した。撮影して得られた画像は、装置付属のノギス径算出ツールを使用し、粒子断面の長径(L)と短径(S)とそれらの合計D1(D1=L+S)(粒子サイズ)、及び粒子断面の単孔の長径(l)と短径(s)とそれらの合計値D2(単孔サイズ)を算出し、D2/D1が0.05以上、0.20となる良孔(R0.05-0.20)の数を求めた。1種類の生分解性ポリエステル粒子につき、20個の粒子について良孔(R0.05-0.20)を求め、その算術平均値を該生分解性樹脂粒子での良孔(R0.05-0.20)の数とした。
D2/D1の範囲を0.05以上、0.15以下とする以外は、前記良孔(R0.05-0.15)の数と同様にして、粒子断面内の第2の良孔(R0.05-0.15)の数を決定した。
前記<良孔(R0.05-0.20)>の数と同様にして、粒子サイズD1と単孔サイズD2を求め、良孔(R0.05-0.20)を特定し、粒子長径の中央を中心とする直径0.8×(L+S)の円(80%円)内に重心を有する良孔(R0.05-0.20)の数を求めた。1種類の生分解性ポリエステル粒子につき、20個の粒子についてR0.05-0.20を求め、その算術平均値を該生分解性樹脂粒子での80%円内での良孔の数とした。
粒子長径の中央を中心とする直径0.5×(L+S)の円(50%円)内に重心を有する良孔(R0.05-0.20)を数える以外は、前記<80%円内の良孔(R0.05-0.20)の数>と同様にして決定した。
前記<良孔(R0.05-0.20)の数>で測定した20個の粒子に含まれる全単孔で測定したD2を対象として統計処理をしてその算術平均値を求め、単孔サイズとした。
樹脂粒子0.1質量部に、乳化剤であるポリオキシエチレンアルキルエーテル硫酸エステルアンモニウム塩(第一工業製薬株式会社製「ハイテノール(登録商標)N-08」)の1%水溶液20質量部を加え、超音波で10分間分散させた分散液を測定試料として、粒度分布測定装置(ベックマンコールター社製「コールターマルチサイザーIII型」)により30000個の粒子の粒子径(μm)を測定し、体積平均粒子径を求めた。また体積基準での粒子径の標準偏差も求め、下記式に従って粒子径の変動係数(CV値)を算出した。
粒子径の変動係数(%)=100×(粒子径の標準偏差/体積平均粒子径)。
300mLの撹拌装置付きのガラス製反応器に無水コハク酸0.5モル、エチレングリコール0.52モルを仕込み、撹拌下に140℃で生成水を留去し縮合反応を行った。反応開始から3時間後に反応触媒としてチタンテトラブトキシド0.02gを投入し、さらに反応温度は反応開始から5時間後に160℃、8時間後に180℃、9時間後に200℃に変更し、12時間後に反応を終了した。反応開始から5時間後に真空ポンプを接続し、以後は減圧下とした。クロロホルム溶液のGPC測定(条件は下記の通り)によりポリスチレン換算の分子量を求めたところ、数平均分子量Mnは2.9万、重量平均分子量Mwは6.3万であった。
300mLの撹拌装置付きのガラス製反応器に無水コハク酸0.72モル、アジピン酸0.08モル、1,4‐ブタンジオール0.81モルを仕込み、撹拌下に180℃で生成水を留去し縮合反応を行った。反応開始から3時間後に反応触媒としてチタンテトラブトキシド0.05gを投入し、10時間後に末端結合剤としてヘキメチレンジイソシアネートを2.0g投入した。反応温度は反応開始から1時間後に200℃、2時間後に220℃に変更し、12時間後に反応を終了した。反応開始から5時間後に真空ポンプを接続し、以後は減圧下とした。クロロホルム溶液のGPC測定(条件は下記の通り)によりポリスチレン換算の分子量を求めたところ、数平均分子量Mnは5.7万、重量平均分子量Mwは12.8万であった。
測定システム:東ソー社製「GPCシステムHLC-8220」
展開溶媒:クロロホルム(和光純薬工業社製、特級)
溶媒流量:0.6mL/分
標準試料:TSK標準ポリスチレン(東ソー社製「PS-オリゴマーキット」)
測定側カラム構成:ガードカラム(東ソー社製「TSK guardcolumn SuperHZ-L」)、分離カラム(東ソー社製「TSK Gel Super HZM-M」)、2本直列接続
リファレンス側カラム構成:リファレンスカラム(東ソー社製「TSK Gel Super H-RC」)。
製造例1で得られたポリエチレンサクシネート5.0gとポリビニルピロリドン(日本触媒社製、商品名「ポリビニルピロリドンK-30」)0.63gを45.0gの塩化メチレンに加え、撹拌しながら溶解した。この溶液を過剰の1質量%ポリビニルアルコール水溶液200gに撹拌しながら加えることで、一次懸濁液を調製した。一次懸濁液をT.K.ホモジナイザー(プライミクス株式会社(旧社名:特殊機化工業株式会社)製)により8000rpmで7分間撹拌して、二次懸濁液を調製した。二次懸濁液をフラスコに移し、ロータリーエバポレーターを駆動して、温度40℃、圧力30torrの減圧条件下にてフラスコを100rpmの速度で回転させることで塩化メチレンを除去した。分散液を減圧ろ過し、メタノールにて洗浄した。ろ過物を真空乾燥し、生分解性樹脂粒子を得た。
ポリエチレンサクシネート5.0gをポリ乳酸(三井化学社製、商品名「レイシアH440」)5.0gに変更する以外は合成例1と同様にした。
ポリエチレンサクシネート5.0gを製造例2で得られたポリブチレンサクシネート/アジペート5.0gに変更する以外は合成例1と同様にした。
ポリビニルピロリドン0.63gを使用しない以外は、合成例1と同様にした。
下記に記載する基本配合において、表1に示す合成例1~2および比較合成例1の生分解性樹脂粒子を用い、ファンデーションを下記製法によりそれぞれ製造し、化粧仕上がり感、使用感触、持続性について下記評価方法により評価した。
(1) メチコン処理タルク 18.00 質量%
(2) メチコン処理酸化チタン 12.00 質量%
(3) メチコン処理セリサイト 43.00 質量%
(4) 生分解性樹脂粒子 8.00 質量%
(5) メチコン・シリカ処理微粒子酸化チタン 5.00 質量%
(6) ベンガラ 0.50 質量%
(7) 黄酸化鉄 1.00 質量%
(8) 黒酸化鉄 0.10 質量%
(9) ジメチルポリシロキサン 6.00 質量%
(10)イソノナン酸イソトリデシル 3.00 質量%
(11)スクワラン 3.00 質量%
(12)防腐剤 0.30 質量%
(13)抗酸化剤 0.10 質量%
(製法)
上記基本配合に示す粉体成分(1)~(8)を混合粉砕して、これをミキサーに移す。別の容器に油相成分(9)~(13)を混合する。ミキサーを撹拌しながら油相成分を加えて均一になるよう撹拌混合し、その後粉砕した。これをアルミ皿にプレス成型して製品を得た。
得られたファンデーションをパネラーが通常の使用方法にて用い、化粧仕上がり、使用性、持続性について評価したところ、いずれの性能にも優れたファンデーションであった。更に本発明のファンデーションは、仕上がり感が自然なだけ出なく、立体感や明確な陰影を与え、優れた性能を示した。
Claims (3)
- 走査透過電子顕微鏡による断面写真において粒子内部に1つ以上の単孔が観察され、粒子長径と粒子短径の合計をD1とし、単孔長径と単孔短径の合計をD2とした時、D2/D1が0.05以上、0.20以下となる単孔の数が粒子1つあたり5個以上であり、体積平均粒子径が1.0~30μmであることを特徴とする生分解性樹脂粒子を含み、前記生分解性樹脂が、脂肪族ジカルボン酸と脂肪族ジオールとの脱水縮合体である化粧料用組成物。
- 前記単孔の長径と短径の合計D2の算術平均値が、0.1~4.5μmである請求項1に記載の生分解性樹脂粒子を含む、化粧料用組成物。
- 走査透過電子顕微鏡による断面写真において粒子内部に1つ以上の単孔が観察され、粒子長径と粒子短径の合計をD1とし、単孔長径と単孔短径の合計をD2とした時、D2/D1が0.05以上、0.20以下となる単孔の数が粒子1つあたり5個以上であることを特徴とする化粧料に用いる生分解性樹脂粒子の製造方法であって、生分解性樹脂を水非混和性有機溶媒に可溶な水溶性高分子と共に水非混和性有機溶媒に溶解させる工程1と、分散剤を含有する水と前記生分解性樹脂液とを撹拌し懸濁液を調製する工程2を含み、前記水非混和性有機溶媒に可溶な水溶性高分子がポリビニルピロリドンである、化粧料に用いる生分解性樹脂粒子の製造方法。
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