JPWO2013081120A1 - レシチンオルガノゲル形成剤 - Google Patents
レシチンオルガノゲル形成剤 Download PDFInfo
- Publication number
- JPWO2013081120A1 JPWO2013081120A1 JP2013547239A JP2013547239A JPWO2013081120A1 JP WO2013081120 A1 JPWO2013081120 A1 JP WO2013081120A1 JP 2013547239 A JP2013547239 A JP 2013547239A JP 2013547239 A JP2013547239 A JP 2013547239A JP WO2013081120 A1 JPWO2013081120 A1 JP WO2013081120A1
- Authority
- JP
- Japan
- Prior art keywords
- ascorbic acid
- organogel
- composition
- lecithin
- gel
- 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.)
- Granted
Links
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 title claims abstract description 57
- 239000000787 lecithin Substances 0.000 title claims abstract description 56
- 235000010445 lecithin Nutrition 0.000 title claims abstract description 56
- 229940067606 lecithin Drugs 0.000 title claims abstract description 55
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 114
- 239000000203 mixture Substances 0.000 claims abstract description 84
- 239000003921 oil Substances 0.000 claims abstract description 65
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 59
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 58
- 239000000693 micelle Substances 0.000 claims abstract description 56
- 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 55
- 239000011668 ascorbic acid Substances 0.000 claims abstract description 55
- 150000000996 L-ascorbic acids Chemical class 0.000 claims abstract description 38
- 230000008719 thickening Effects 0.000 claims abstract description 28
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- 239000000499 gel Substances 0.000 description 50
- -1 fatty acid esters Chemical class 0.000 description 16
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- 229910001868 water Inorganic materials 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
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- 239000002211 L-ascorbic acid Substances 0.000 description 5
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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
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- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
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- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- ZGSCRDSBTNQPMS-UJURSFKZSA-N 3-O-Ethylascorbic acid Chemical compound CCOC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO ZGSCRDSBTNQPMS-UJURSFKZSA-N 0.000 description 3
- 229940120145 3-o-ethylascorbic acid Drugs 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 150000004665 fatty acids Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
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- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
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- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-SZSCBOSDSA-N 2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one Chemical compound OC[C@H](O)C1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-SZSCBOSDSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- JLPULHDHAOZNQI-JLOPVYAASA-N [(2r)-3-hexadecanoyloxy-2-[(9e,12e)-octadeca-9,12-dienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC JLPULHDHAOZNQI-JLOPVYAASA-N 0.000 description 2
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Abstract
Description
[1] (a)レシチン、(b)アスコルビン酸またはアスコルビン酸誘導体を含有し逆紐状ミセルを形成するオルガノゲル形成剤。
[2] 前記(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体との混合割合として、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体の合計質量に対して、(b)アスコルビン酸またはアスコルビン酸誘導体を0.1質量%から35質量%含有することを特徴とする上記[1]に記載のオルガノゲル形成剤。
[3] 上記[1]または[2]に記載のオルガノゲル形成剤と(c)オイル成分とを少なくとも含み逆紐状ミセルを形成した増粘ゲル状組成物。
[4] 前記増粘ゲル状組成物が、化粧料、医薬品、食品、塗料、インク、潤滑油の少なくともいずれか一つであることを特徴とする上記[3]に記載の増粘ゲル状組成物。
[5] 前記オルガノゲル形成剤と(c)オイル成分との混合割合として、オルガノゲル形成剤を増粘ゲル状組成物に対して1質量%から70質量%含有することを特徴とする上記[3]または[4]に記載の増粘ゲル状組成物。
[6] 逆紐状ミセルを形成するオルガノゲル形成剤の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることを特徴とするオルガノゲル形成剤の製造方法。
[7] 逆紐状ミセルを形成した増粘ゲル状組成物の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることによりオルガノゲル形成剤とし、該オルガノゲル形成剤に(c)オイル成分を添加混合させることを特徴とする逆紐状ミセルを形成した増粘ゲル状組成物の製造方法。
また、本発明の増粘ゲル状組成物は、逆紐状ミセルを形成しているゆえに、増粘又はゲル化されるオイルにもよるが、オイル自体が透明であるならば透明なものである。
ここで、Rcは断面の回転半径である。また、測定範囲の制約のために逆紐状ミセルの正確な長さは算出できなかったが、(3)式を用いた棒状粒子を仮定した理論散乱関数を用いたシミュレーション(図中のCalculated curve)から逆紐状ミセルの長さ(t)は50nmよりも長いことが示された。
ここで、J1は一次のベッセル関数である。また、本発明のオルガノゲル形成剤を用いてオイル成分を増粘又はゲル化させた増粘ゲル状組成物は、そのゲル化の状態、物性からすると、逆紐状ミセルが形成されているといえる。
本発明のオルガノゲル形成剤は、さらに、上記以外の医薬部外品、インキ、塗料、潤滑油や、プラスチック、ゴム、金属等の加工分野のほか、農業、水産業、廃油処理等の分野でも用いることができる。
粘度測定は、コーンプレート(直径が60、35mmでコーン角が1度と4度)とペルチェ温度コントローラを備えた回転レオメーター(RheoStress600、HAAKE社製)を用いて25℃恒温下で行った。なお、溶媒の蒸発を防止するためにソルベントトラップを用いて測定した。具体的には、コーンプレートと試料台の間に試料を挟みこみ、コーンプレートを一定方向に回転させて試料に段階的にずり速度を加えた。それぞれのずり速度ごとにずり応力を求めて、粘度=ずり応力/ずり速度の関係からゼロシアー粘度を算出した。
また、これに基づき、増粘ゲル化の状態を以下のように評価した。
◎ゲル化(ゼロシアー粘度100Pa・s以上のもの):○増粘(ゼロシアー粘度10Pa・s以上100Pa・s未満のもの):×増粘ゲル化が不十分(ゼロシアー粘度10Pa・s未満のもの)
ゲルの透明性は、調製した増粘ゲル状組成物を直径27.5mm、高さ70mmのサンプル瓶に封入し、25℃に設定した恒温槽中に1か月保存した後、目視により観察したもので、◎:透明である、○:半透明である、△:白濁してる、×:二相分離しているとして評価したものである。
(増粘ゲル状組成物の配合)
(a)成分のレシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)、(b)成分のアスコルビン酸(商品名「L-(+)-アスコルビン酸」和光純薬工業(株)製)、(c)成分として、n−デカン(関東化学(株)製 0.774mPa・s(25℃))を、表1に示す配合組成として、増粘ゲル状組成物を調製した。各配合組成に応じて、実施例1〜11とした。
増粘ゲル状組成物の調製は、(a)成分:レシチンと(b)成分:アスコルビン酸をそれぞれ必要量ボトルに封入し、メタノールを加えマグネチックスターラーを用いて攪拌した。完全にレシチンとアスコルビン酸を溶解させた後、減圧乾燥によりメタノールを完全に蒸発させる。(c)オイル成分を必要量加えてさらに一晩撹拌し、ボトルを安定化のために25℃の恒温槽で数日間静置することによって調製した。なお、以下の実施例、比較例においても、増粘ゲル状組成物の調製は、これと同じ調製手段によった。
(増粘ゲル状組成物の配合)
(a)成分のレシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)、(b)成分のアスコルビン酸(商品名「L-(+)-アスコルビン酸」和光純薬工業(株)製)、(c)成分として、ミリスチン酸イソプロピル(和光純薬工業(株)製 4.74mPa・s(25℃))を、表2に示す配合組成として、増粘ゲル状組成物を調製し実施例12〜21とした。
(増粘ゲル状組成物の調製)
増粘ゲル状組成物の調製は、実施例2、4において、(b)成分のL−アスコルビン酸に換えて3−O−エチルアスコルビン酸(純正化学(株)製)を用いたものを実施例22,24とし、また、実施例2において、(b)成分のL−アスコルビン酸に換えて3−O−エチルアスコルビン酸を1.25質量%として実施例23を調製した。表3に示す配合組成として、増粘ゲル状組成物を調製した。
(増粘ゲル状組成物の配合)
(a)成分:レシチンとして、大豆レシチン(商品名「L-α-Phosphatidylcholine (Soy-95%)」Avanti Polar Lipids, Inc.製)10質量%、(c)成分として、n−デカン(関東化学(株)製)90質量%を配合組成として、増粘ゲル状組成物を調製し比較例1とした。(c)成分をミリスチン酸イソプロピル(和光純薬工業(株)製)に変えた以外は比較例1と同じにして、増粘ゲル状組成物を調製し比較例2とした。
Claims (7)
- (a)レシチン、(b)アスコルビン酸またはアスコルビン酸誘導体を含有し逆紐状ミセルを形成するオルガノゲル形成剤。
- 前記(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体との混合割合として、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体の合計質量に対して、(b)アスコルビン酸またはアスコルビン酸誘導体を0.1質量%から35質量%含有することを特徴とする請求項1に記載のオルガノゲル形成剤。
- 上記請求項1または2に記載のオルガノゲル形成剤と(c)オイル成分とを少なくとも含み逆紐状ミセルを形成した増粘ゲル状組成物。
- 前記増粘ゲル状組成物が、化粧料、医薬品、食品、塗料、インク、潤滑油の少なくともいずれか一つであることを特徴とする請求項3に記載の増粘ゲル状組成物。
- 前記オルガノゲル形成剤と(c)オイル成分との混合割合として、オルガノゲル形成剤を増粘ゲル状組成物に対して1質量%から70質量%含有することを特徴とする請求項3または4に記載の増粘ゲル状組成物。
- 逆紐状ミセルを形成するオルガノゲル形成剤の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることを特徴とするオルガノゲル形成剤の製造方法。
- 逆紐状ミセルを形成した増粘ゲル状組成物の製造方法であって、(a)レシチンと(b)アスコルビン酸またはアスコルビン酸誘導体を有機溶媒に溶解後、有機溶媒を蒸発させることによりオルガノゲル形成剤とし、該オルガノゲル形成剤に(c)オイル成分を添加混合させることを特徴とする逆紐状ミセルを形成した増粘ゲル状組成物の製造方法。
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- 2012-11-30 EP EP12852762.9A patent/EP2787050A4/en not_active Withdrawn
- 2012-11-30 US US14/361,491 patent/US20140371333A1/en not_active Abandoned
- 2012-11-30 JP JP2013547239A patent/JP6192047B2/ja not_active Expired - Fee Related
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JP6192047B2 (ja) | 2017-09-06 |
US20140371333A1 (en) | 2014-12-18 |
EP2787050A4 (en) | 2015-03-25 |
WO2013081120A1 (ja) | 2013-06-06 |
EP2787050A1 (en) | 2014-10-08 |
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