JP4053966B2 - 皮膚外用剤および皮膚刺激緩和剤 - Google Patents
皮膚外用剤および皮膚刺激緩和剤 Download PDFInfo
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- JP4053966B2 JP4053966B2 JP2003389433A JP2003389433A JP4053966B2 JP 4053966 B2 JP4053966 B2 JP 4053966B2 JP 2003389433 A JP2003389433 A JP 2003389433A JP 2003389433 A JP2003389433 A JP 2003389433A JP 4053966 B2 JP4053966 B2 JP 4053966B2
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- WZXKPNYMUZGZIA-RMKNXTFCSA-N propyl (e)-3-(4-methoxyphenyl)prop-2-enoate Chemical compound CCCOC(=O)\C=C\C1=CC=C(OC)C=C1 WZXKPNYMUZGZIA-RMKNXTFCSA-N 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000015227 regulation of liquid surface tension Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229960000342 retinol acetate Drugs 0.000 description 1
- QGNJRVVDBSJHIZ-QHLGVNSISA-N retinyl acetate Chemical compound CC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C QGNJRVVDBSJHIZ-QHLGVNSISA-N 0.000 description 1
- 235000019173 retinyl acetate Nutrition 0.000 description 1
- 239000011770 retinyl acetate Substances 0.000 description 1
- 229940108325 retinyl palmitate Drugs 0.000 description 1
- 235000019172 retinyl palmitate Nutrition 0.000 description 1
- 239000011769 retinyl palmitate Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- SJOXEWUZWQYCGL-UHFFFAOYSA-N salicylic acid menthyl ester Natural products CC(C)C1CCC(C)CC1OC(=O)C1=CC=CC=C1O SJOXEWUZWQYCGL-UHFFFAOYSA-N 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 230000035483 skin reaction Effects 0.000 description 1
- 231100000430 skin reaction Toxicity 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- KVSKGMLNBAPGKH-UHFFFAOYSA-N tribromosalicylanilide Chemical compound OC1=C(Br)C=C(Br)C=C1C(=O)NC1=CC=C(Br)C=C1 KVSKGMLNBAPGKH-UHFFFAOYSA-N 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- UUJLHYCIMQOUKC-UHFFFAOYSA-N trimethyl-[oxo(trimethylsilylperoxy)silyl]peroxysilane Chemical compound C[Si](C)(C)OO[Si](=O)OO[Si](C)(C)C UUJLHYCIMQOUKC-UHFFFAOYSA-N 0.000 description 1
- 229960005066 trisodium edetate Drugs 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
このように皮膚外用剤の使用においては、多種多様の刺激の原因が存在し、これまで皮膚への刺激を緩和・予防する方法が種々検討されてきている。
そこで本発明は、製剤の機能や形態に影響を与えず、配合が容易で安全性・安定性に優れ、さらに十分な刺激緩和効果を有する皮膚外用剤を提供することを目的とする。
また、本発明の皮膚刺激緩和剤は、皮膚への刺激原因物質に起因する皮膚刺激の緩和に優れている。
さらに本発明によれば、製剤の機能や形態に影響を与えず、配合が容易で安全性・安定性に優れ、さらに十分な刺激緩和効果を有する皮膚刺激緩和方法を提供することができる。
本発明で使用するベンゾイルアミノジカルボン酸、ベンゼンスルホニルアミノジカルボン酸およびその医薬上許容され得る塩付加体は、前記一般式(I)で表される化合物及びその光学異性体及び医薬上許容され得る塩付加体である。
1.レチノールおよびその誘導体
レチノール(allトランス型、13−シス型)、酢酸レチノール、パルミチン酸レチノール等。
パラアミノ安息香酸(PABAと略す)PABAモノグリセリンエステル、N,N−ジプロピルPABAエチルエステル、N,N−ジエチルPABAエチルエステル、N,N−ジメチルPABAエチルエステル、N,N−ジメチルPABAブチルエステル、ホモメンチル−N−アセチルアントラニレート、アミルサリチレート、メンチルサリチレート、ホモメンチルサリチレート、オクチルサリチレート、フェニルサリチレート、ベンジルサリチレート、p−イソプロパノールフェニルサリチレート、パラメトキシ桂皮酸2−エチルへキシル、ジ−p−メトキシ桂皮酸−モノ−2−エチルヘキサン酸グリセリル、オクチルシンナメート、エチル−4−イソプロピルシンナメート、メチル−2,5−ジイソプロピルシンナメート、エチル−2,4−ジイソプロピルシンナメート、メチル−2,4−ジイソプロピルシンナメート、プロピル−p−メトキシシンナメート、イソプロピル−p−メトキシシンナメート、イソアミル−p−メトキシシンナメート、2−エトキシエチル−p−メトキシシンナメート、シクロヘキシル−p−メトキシシンナメート、エチル−α−シアノ−β−フェニルシンナメート、2−エチルヘキシル−α−シアノ−β−フェニルシンナメート、グリセリルモノ−2−エチルヘキサノイルジパラメトキシシンナメート、3,4,5−トリメトキシ桂皮酸−3−メチル−4−[メチルビス(トリメチルシロキシ)シリル]ブチル、2,4−ジヒドロキシベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン、2,2’−ジヒドロキシ−4.4’−ジメトキシベンゾフェノン、2,2’,4,4’−テトラヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸塩、3−(4’−メチルベンジリデン)−dl−カンファー、3−ベンジリデン−dl−カンファー、2−フェニル−5−メチルベンズオキサゾール、2,2’−ジヒドロキシ−5−メチルフェニルベンズトリアゾール、2−(2’−ヒドロキシ−5’−t−オクチルフェニル)ベンズトリアゾール、2−(2’−ヒドロキシ−5’−メチルフェニルベンズトリアゾール、ジベンザラジン、ジアニソイルメタン、4−t−ブチル−4’−メトキシジベンゾイルメタン、5−(3,3−ジメチル−2−ノルボルニリデン)−3−ペンタン−2−オン等。
フェノキシエタノール、安息香酸及びその塩類、サリチル酸及びその塩類、フェノール、ソルビン酸及びその塩類、デヒドロ酢酸及びその塩類、パラオキシ安息香酸エステル類、クロロクレゾール、ヘキサクロロフェン、レゾルシン、イソプロピルメチルフェノール、オルトフェニルフェノール、塩化ベンザルコニウム、塩酸クロルヘキシジン、グルコン酸クロルヘキシジン、臭化アルキルイソキノリウム、トリクロロカルバニリド、ハロカルバン、感光素201号、トリクロロヒドロキシジフェニルエーテル、メチルクロロイソチアゾリノン。メチルイソチアゾリノン液、ビサボロール、塩酸アルキルジアミノエチルグリシン、トリクロロサリチルアニリド、トリブロモサリチルアニリド等
パラメトキシ桂皮酸2−エチルヘキシル(商品名:パルソールMCX)
4−t−ブチル−4’−メトキシジベンゾイルメタン(商品名:パルソール1789)
トリメトキシケイ皮酸メチルビス(トリメチルシロキシ)シリルイソペンチル(商品名:サンシェルターSP)
パラジメチルアミノ安息香酸メチル(商品名:エスカロール506)
本発明に配合される上記一般式(I)で表される化合物は、皮膚外用剤全量に対して、0.1〜20.0質量%の範囲で配合されることが好ましく、より好ましくは0.5〜10.0質量%の範囲である。これ以下の配合量では所望の効果は得られず、またこれ以上の配合量では皮膚外用剤の効果を損なうものとなる。
本発明にかかる皮膚外用剤には、一般に化粧料、医薬品に配合し得る任意の成分を配合することができる。具体的には紫外線吸収剤、保湿剤、ビタミン類、美白剤、収斂剤、清涼剤、各種の抽出物等の薬効成分、界面活性剤、液体油脂、固体油脂、ロウ類、エステル油、炭化水素油、シリコーン類、ステロール類、水溶性高分子、油溶性高分子、キレート剤、中和剤、pH調整剤、酸化防止剤、抗菌剤、粉末、香料、色素などが挙げられるが、これらに限定されるものではない。
本発明の皮膚外用剤は、皮膚外用剤における刺激物質若しくは製剤により生じる刺激や塗布時に生じる刺激が低減、緩和若しくは予防されたものである。
下記表1に示す組成の試料を常法により調製し、刺激緩和性試験に供した。
表1に記載した実施例1〜4及び比較例1,2を以下に示す試験方法により刺激緩和性を評価した。その結果を下記表2に示す。
刺激原因物質及び刺激緩和剤を配合した各試料0.05mlを被験者(女性25名、男性25名)の上腕内側部に塗布し、パッチテストを行った。
塗布部皮膚の状態(紅斑、浮腫、痂皮などの皮膚反応)を目視にて、また刺激感の有無を被験者の自己申告に基づいて、下記基準により判定した。
◎:紅斑、刺激ともになし。
○:紅斑はほとんど見られなかったが、わずかな刺激若しくはわずかな肌荒れが見られた。
△:わずかな紅斑が見られ、明らかな刺激感があった。
×:明らかな紅斑あるいは浮腫、痂皮が見られ、明らかな刺激感があった。
以下に本発明の刺激緩和剤を配合した皮膚外用剤の処方例を挙げる。
パラメトキシ桂皮酸2−エチルヘキシル 7.5
4−t−ブチル−4’−メトキシジベンゾイルメタン 0.1
二酸化チタン 5.0
デカメチルシクロペンタシロキサン 30.0
POE・メチルポリシロキサン共重合体 3.0
有機変性モンモリロナイト 0.8
1,3−ブチレングリコール 5.0
アルブチン 5.0
N−ベンゾイル−L−グルタミン酸 3.0
水酸化ナトリウム 0.48
防腐剤 適量
香料 適量
精製水 残余
(A)
スクワラン 6.0
ワセリン 5.0
ステアリルアルコール 3.0
ステアリン酸 3.0
グリセリルモノステアレート 3.0
ポリアクリル酸エチル 1.0
4−t−ブチル−4’−メトキシジベンゾイルメタン 7.5
ポリアミド樹脂粉末 5.0
エタノール 40.0
防腐剤 適量
香料 適量
(B)
1,3−ブチレングリコール 7.0
エデト酸三ナトリウム 0.05
カチオン性増粘剤 3.0
乳酸 0.6
N−ベンゼンスルホニル−L−グルタミン酸 3.0
水酸化ナトリウム 0.86
精製水 残余
(製法)
(A)の成分を加熱融解し、(B)を攪拌しながら加える。ホモミキサーで処理し、乳化粒子を細かくした後、攪拌しながら急冷し、クリームを得る。
(A)
パラメトキシ桂皮酸2−エチルヘキシル 2.0
テトラオクタン酸ペンタエリスリチル 1.0
ポリオキシエチレン(20)オレイルアルコールエーテル 0.5
エタノール 60.0
香料 適量
防腐剤 適量
(B)
ソルビット 4.0
ジプロピレングリコール 6.0
乳酸 0.1
クエン酸 0.1
クエン酸ナトリウム 0.05
N−ベンゾイル−L−グルタミン酸 3.0
水酸化ナトリウム 0.51
ヒドロキシメトキシベンゾフェノンスルホン酸ナトリウム 適量
エデト酸三ナトリウム 適量
精製水 残余
(製法)
(B)を調整する。別にエタノールに(A)のほかの成分を溶解して(A)を調整し、これを(B)に加えて可溶化し、ろ過して化粧水を得る。
(A)
ステアリン酸 2.0
セチルアルコール 0.5
流動パラフィン 10.0
ポリオキシエチレン(10)オレイン酸エステル 1.0
ソルビタントリオレート 1.0
パラメトキシ桂皮酸2−エチルヘキシル 3.0
テトラオクタン酸ペンタエリスリチル 1.5
ミリスチン酸イソプロピル 2.0
シリカ 3.0
防腐剤 適量
香料 適量
(B)
ジプレングリコール 5.0
トリエタノールアミン 1.0
ヘクトライト 1.0
クエン酸 0.2
エタノール 55.0
N−ベンゼンスルホニル−L−アスパラギン酸 3.0
水酸化ナトリウム 0.88
精製水 残余
(製法)
(B)を調整し、70℃に保つ。(A)の成分を混合し、加熱融解して70℃に保つ。(B)に(A)を加えてホモミキサーで均一に乳化、攪拌しながら急冷し、乳液を得る。
(A)
カーボポール940 0.6
(B)
N−ベンゾイル−L−グルタミン酸 3.0
水酸化ナトリウム 0.48
精製水 残余
(C)
トリエタノールアミン 0.1
(D)
エタノール 14.0
パラメトキシ桂皮酸2−エチルヘキシル 7.5
アクリル酸メトキシエチル/アクリル酸
ヒドロキシエチル/アクリル酸ブチル共重合体 1.0
ポリエチレングリコール 1.0
ジメチコーン共重合体 4.0
メチルパラベン 0.25
プロピルパラベン 0.05
香料 適量
(製法)
(A)を(B)に攪拌溶解し、(C)を加えた後、分散機にて分散する。これにDを加え、攪拌し、目的のヘアージェルを得る。
(A)
精製水 残余
N−ベンゼンスルホニル−L−グルタミン酸 1.5
1,3−ブチレングリコール 5.0
エタノール 7.0
(B)
タルク 7.0
二酸化チタン 10.0
酸化亜鉛 2.0
無水ケイ酸 2.0
ナイロンパウダー 4.0
着色顔料 2.0
(C)
パラメトキシ桂皮酸2−エチルヘキシル 15.0
オクタメチルシクロテトラシロキサン 10.0
ロジンペンタエリスリットエステル 1.5
ジイソオクタン酸ネオペンチルグリコール 5.0
トリイソオクタン酸グリセリン 2.0
ポリオキシエチレン変性ジメチルポリシロキサン 1.5
トリメチルシロキシケイ酸樹脂 5.0
(製法)
(A)を攪拌後、十分に混合粉砕された(B)を添加し、ホモミキサー処理する。(C)を溶解後これに加えホモミキサー処理し、日焼け止め乳化ファンデーションを得る。
Claims (9)
- 前記一般式(I)中、X1、X2、X3がそれぞれ独立して水素原子、炭素数が1〜4のアルキル基、炭素数が1〜4のアルコキシ基または水酸基であることを特徴とする請求項1記載の皮膚外用剤。
- 前記一般式(I)中、Yがスルホニル基であることを特徴とする請求項1記載の皮膚外用剤。
- 前記一般式(I)で表される化合物がN−ベンゼンスルホニルグルタミン酸、N−ベンゾイルグルタミン酸、N−ベンゼンスルホニルアスパラギン酸またはN−ベンゾイルアスパラギン酸であることを特徴とする請求項1記載の皮膚外用剤。
- 前記一般式(I)で表される化合物と、皮膚への刺激原因物質とを含有することを特徴とする請求項1記載の皮膚外用剤。
- 前記皮膚への刺激原因物質が脂溶性薬剤成分および防腐剤から選ばれる1種または2種以上であることを特徴とする請求項5記載の皮膚外用剤。
- 前記脂溶性薬剤成分が紫外線吸収剤であることを特徴とする請求項6記載の皮膚外用剤。
- 前記一般式(I)で表される化合物がN−ベンゼンスルホニルグルタミン酸、N−ベンゾイルグルタミン酸、N−ベンゼンスルホニルアスパラギン酸またはN−ベンゾイルアスパラギン酸であることを特徴とする請求項8記載の皮膚刺激緩和剤。
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