JP2013049011A - Agent making dissolvable into oil - Google Patents
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- 239000000203 mixture Substances 0.000 claims abstract description 66
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 64
- 229930195729 fatty acid Natural products 0.000 claims abstract description 64
- 239000000194 fatty acid Substances 0.000 claims abstract description 64
- -1 fatty acid ester Chemical class 0.000 claims abstract description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 20
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 14
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 14
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims abstract description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims abstract description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims abstract description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005642 Oleic acid Substances 0.000 claims abstract description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 44
- 235000019198 oils Nutrition 0.000 description 43
- 229960003656 ricinoleic acid Drugs 0.000 description 14
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 14
- 229940057995 liquid paraffin Drugs 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 6
- 238000002834 transmittance Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000005063 solubilization Methods 0.000 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005639 Lauric acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 229940105990 diglycerin Drugs 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical group OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 229940056211 paraffin Drugs 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Abstract
Description
本発明は、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油に水を分散させることができる油溶化剤、及びそれを含有する油溶化組成物に関するものである。 The present invention relates to an oil solubilizer capable of dispersing water in a hydrocarbon oil having a viscosity at 25 ° C. of 5 to 100 mPa · s, and an oil-solubilized composition containing the same.
水を油相中に分散させる場合、一般に界面活性剤等を用いて油中水型のエマルションを作成し、均一な分散状態とする。油中水型エマルションは、単一相では得られない機能を有することから、様々な産業分野で広く使用されているが、外観に大きな濁度を有していること、また、水相と油相が分離することが課題となっている。そのため、外観の透明性、及び安定性の程度により、使用用途が制限されるという欠点がある。 When water is dispersed in an oil phase, a water-in-oil emulsion is generally prepared using a surfactant or the like to obtain a uniform dispersion state. Water-in-oil emulsions are widely used in various industrial fields because they have a function that cannot be obtained with a single phase. The problem is that the phases are separated. Therefore, there exists a fault that a use application is restrict | limited by the transparency of an external appearance, and the degree of stability.
水を分散させた油の外観、及び安定性を向上させるためには、水を油相中に油溶化することが必要である。油溶化とは、水を油相中に透明に可溶化させた状態、もしくはマイクロエマルションと呼ばれる状態を指す。一般に、水と油が透明に混合するか否かは、油、水、界面活性剤、及びその他の添加剤の組み合わせと、温度、圧力によって決まることが知られている。また、油溶化により得られる溶液は、熱力学的に安定な１液相であるため、極めて経時安定性に優れている。 In order to improve the appearance and stability of the oil in which water is dispersed, it is necessary to dissolve water in the oil phase. Oil-solubilization refers to a state in which water is solubilized transparently in an oil phase, or a state called a microemulsion. In general, it is known that whether or not water and oil are mixed transparently depends on a combination of oil, water, surfactant, and other additives, temperature, and pressure. In addition, since the solution obtained by oil solubilization is a thermodynamically stable one-liquid phase, it is extremely excellent in stability over time.
これまで、水を油相中に分散させる方法としては、界面活性剤にポリグリセリン縮合リシノール酸エステル、ＨＬＢが６〜１４の乳化剤、酵素分解レシチンの３種を併用する方法（特許文献１）、ポリグリセリン脂肪酸エステルの他に、助剤としてショ糖脂肪酸エステルを併用する方法（特許文献２）、縮合度の異なるポリグリセリン縮合リシノール酸エステルを併用する方法（特許文献３）等が開示されている。しかしながら、何れの方法においても、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油に水を透明に分散させることは困難であった。 Until now, as a method of dispersing water in an oil phase, a method of using a surfactant together with three types of polyglycerin condensed ricinoleic acid ester, an emulsifier having an HLB of 6 to 14, and an enzymatically decomposed lecithin (Patent Document 1), In addition to polyglycerin fatty acid ester, a method of using sucrose fatty acid ester in combination as an auxiliary agent (Patent Document 2), a method of using polyglycerin condensed ricinoleic acid ester having a different condensation degree (Patent Document 3), etc. are disclosed. . However, in any method, it has been difficult to disperse water transparently in a hydrocarbon oil having a viscosity at 25 ° C. of 5 to 100 mPa · s.
本発明は、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油中に水を分散させ、且つ経時的に安定な油溶化組成物を製造できる油溶化剤、及びそれを用いた油溶化組成物を提供することを目的とする。 The present invention relates to an oil solubilizing agent capable of producing a stable oil-solubilized composition over time by dispersing water in a hydrocarbon oil having a viscosity of 5 to 100 mPa · s at 25 ° C., and an oil-solubilizing composition using the same. The purpose is to provide goods.
本発明者らは、鋭意研究した結果、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油に水を分散させる油溶化剤として、請求項１から３に記載のポリグリセリン脂肪酸エステルを１種、又は２種以上併用することにより、上記課題を解決できる油溶化組成物を提供できることを見出し、本発明を完成するに至った。 As a result of intensive studies, the present inventors have found that the polyglycerin fatty acid ester according to any one of claims 1 to 3 is used as an oil solubilizer for dispersing water in a hydrocarbon oil having a viscosity at 25 ° C of 5 to 100 mPa · s. Or it discovered that the oil-solubilized composition which can solve the said subject can be provided by using together 2 or more types, and came to complete this invention.
本発明の油溶化剤を使用することにより、透明性、経時安定性に優れた油溶化組成物を製造することができる。 By using the oil-solubilizing agent of the present invention, an oil-solubilized composition having excellent transparency and stability over time can be produced.
以下、実施形態に基づいて本発明を説明するが、本発明の範囲はこの実施形態に限定されるものではなく、本発明の趣旨を損なわない範囲で変更が加えられた形態も本発明に属する。 Hereinafter, the present invention will be described based on an embodiment. However, the scope of the present invention is not limited to this embodiment, and a mode in which changes are made without departing from the spirit of the present invention also belongs to the present invention. .
本発明における油溶化剤は、ポリグリセリンと脂肪酸をエステル化反応させて得られるポリグリセリン脂肪酸エステルである。このポリグリセリン脂肪酸エステルは、単独で使用しても、ポリグリセリンの重合度やエステル化度の異なるものを２種以上併用してもよいが、２種以上を併用することが好ましい。 The oil-solubilizing agent in the present invention is a polyglycerin fatty acid ester obtained by esterifying polyglycerin and a fatty acid. These polyglycerin fatty acid esters may be used alone or in combination of two or more polyglycerols having different degrees of polymerization and esterification, but it is preferable to use two or more kinds in combination.
本発明で使用されるポリグリセリン脂肪酸エステルのポリグリセリンは、水酸基価から算出される平均重合度が２〜１５、好ましくは４〜１５のものを使用する。本明細書において水酸基価から算出される平均重合度（ｎ）とは、末端分析法によって算出される値であり、次式（式１）及び（式２）から算出される。
（式１）分子量＝７４ｎ＋１８
（式２）水酸基価＝５６１１０（ｎ＋２）／分子量
前記水酸基価とは、エステル化物中に含まれる水酸基数の大小の指標となる数値であり、１ｇのエステル化物に含まれる遊離のヒドロキシル基をアセチル化するために必要な酢酸を中和するのに要する水酸化カリウムのミリグラム数をいい、水酸化カリウムのミリグラム数は、社団法人日本油化学会編纂、「日本油化学会制定、基準油脂分析試験法（Ｉ）、１９９６年度版」に準じて算出される。
The polyglycerin of the polyglycerin fatty acid ester used in the present invention has an average degree of polymerization calculated from the hydroxyl value of 2 to 15, preferably 4 to 15. In this specification, the average degree of polymerization (n) calculated from the hydroxyl value is a value calculated by terminal analysis, and is calculated from the following formulas (formula 1) and (formula 2).
(Formula 1) Molecular weight = 74n + 18
(Formula 2) Hydroxyl value = 56110 (n + 2) / Molecular weight The hydroxyl value is a numerical value indicating the size of the number of hydroxyl groups contained in the esterified product, and the free hydroxyl group contained in 1 g of the esterified product is acetylated. This refers to the number of milligrams of potassium hydroxide required to neutralize the acetic acid required for conversion to the amount of potassium hydroxide. The number of milligrams of potassium hydroxide is compiled by the Japan Oil Chemists 'Society, “Established by the Japan Oil Chemists' Society, Standard Oil Analysis Test. law (I), is calculated in accordance with the 1996 version ".
本発明で使用されるポリグリセリン脂肪酸エステルの構成脂肪酸は、通常、炭素数が８〜２４の飽和または不飽和脂肪酸であり、その構造は直鎖であっても分岐状であってもよい。例えば、カプリン酸、２−エチルヘキサン酸、カプリル酸、ラウリン酸、ミリスチン酸、パルミチン酸、パルミトレイン酸、ステアリン酸、イソステアリン酸、オレイン酸、ベヘン酸、エルカ酸等が挙げられ、中でも、オレイン酸、イソステアリン酸が好ましい。これらの脂肪酸は単独で使用しても、２種以上を併用してもよい。 The constituent fatty acid of the polyglycerol fatty acid ester used in the present invention is usually a saturated or unsaturated fatty acid having 8 to 24 carbon atoms, and the structure thereof may be linear or branched. For example, capric acid, 2-ethylhexanoic acid, caprylic acid, lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, behenic acid, erucic acid, etc., among which oleic acid, Isostearic acid is preferred. These fatty acids may be used alone or in combination of two or more.
本発明で使用されるポリグリセリン脂肪酸エステルのＨＬＢは、油溶化物の透明性、及び経時安定性の観点から、９〜１３が好ましく、より好ましくは１０〜１２である。また、この範囲外のＨＬＢを有するポリグルセリン脂肪酸エステルにおいても、２種以上併用した場合、それらの加重平均ＨＬＢが上記範囲内であれば、優れた油溶化効果が発揮される。ここで用いるＨＬＢとは、通常、界面活性剤の分野で使用される親水性−疎水性のバランスを示す指標であり、（式３）に示すグリフィンの式より算出される値である。
（式３）ＨＬＢ＝２０（１−Ｓ／Ａ）
ここで、Ｓはポリグリセリン脂肪酸エステルのケン化価、Ａは脂肪酸の中和価である。
The HLB of the polyglycerin fatty acid ester used in the present invention is preferably 9 to 13 and more preferably 10 to 12 from the viewpoint of the transparency of the oil-solubilized product and the stability over time. In addition, when two or more polyglycerol fatty acid esters having HLB outside this range are used in combination, if the weighted average HLB is within the above range, an excellent oil solubilizing effect is exhibited. The HLB used here is an index indicating the balance between hydrophilicity and hydrophobicity that is usually used in the field of surfactants, and is a value calculated from the Griffin equation shown in (Equation 3).
(Formula 3) HLB = 20 (1-S / A)
Here, S is the saponification value of the polyglycerol fatty acid ester, and A is the neutralization value of the fatty acid.
本発明における油溶化組成物とは、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油、水、油溶化剤を含む均一溶液において、波長６００ｎｍにおける透過率が５０％以上となるものをいう。 The oil-solubilized composition in the present invention is a homogeneous solution containing hydrocarbon oil having a viscosity at 25 ° C. of 5 to 100 mPa · s, water, and an oil solubilizer, and having a transmittance of 50% or more at a wavelength of 600 nm. .
本発明で使用される２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油としては、特に限定されないが、例えば、流動パラフィン、合成パラフィン、スクワラン、スクワレン等が挙げられる。 The hydrocarbon oil having a viscosity of 5 to 100 mPa · s at 25 ° C. used in the present invention is not particularly limited, and examples thereof include liquid paraffin, synthetic paraffin, squalane and squalene.
本発明の油溶化組成物における水の含有量は、油溶化組成物中、１〜２０重量％が好ましい。また、水と油溶化剤の重量比は、水／油溶化剤＝１／２〜２／１が好ましい。水の含有量、及び水と油溶化剤の比率がこの範囲内である場合、より透明性、経時安定性に優れた油溶化組成物が得られる。 The content of water in the oil-solubilized composition of the present invention is preferably 1 to 20% by weight in the oil-solubilized composition. The weight ratio of water to the oil solubilizer is preferably water / oil solubilizer = 1/2 to 2/1. When the water content and the ratio of water to the oil solubilizer are within this range, an oil-solubilized composition having more transparency and stability over time can be obtained.
本発明の油溶化組成物は、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油、水、油溶化剤を混合して得られる。調製方法としては、特に限定されず、各成分を一度に混合して製造することもできるが、あらかじめ油溶化剤と水を混合した後、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油を添加して製造することもできる。 The oil-solubilized composition of the present invention is obtained by mixing hydrocarbon oil having a viscosity of 5 to 100 mPa · s at 25 ° C., water, and an oil solubilizer. The preparation method is not particularly limited, and each component can be mixed and produced at the same time. However, after previously mixing the oil solubilizer and water, the hydrocarbon oil having a viscosity of 5 to 100 mPa · s at 25 ° C. Can also be produced.
以下、実施例に基づき、本発明を具体的に示すが、本発明はこれらの実施例に限定されるものではない。尚、今回使用したポリグリセリンはジグリセリン、テトラグリセリン、ヘキサグリセリン、デカグリセリンであり、水酸基価から算出した平均重合度は各々２、４、６、１０である。以下、本発明の実施例、及び比較例を示す。 EXAMPLES Hereinafter, although this invention is shown concretely based on an Example, this invention is not limited to these Examples. The polyglycerin used this time is diglycerin, tetraglycerin, hexaglycerin, and decaglycerin, and the average degree of polymerization calculated from the hydroxyl value is 2, 4, 6, and 10, respectively. Examples of the present invention and comparative examples are shown below.
（ポリグリセリン脂肪酸エステルの合成）
ジグリセリンを３３３．９ｇとラウリン酸４０２．３ｇを反応容器に入れ、水酸化ナトリウムを添加し、窒素気流下にて２３０℃で反応させ、ＨＬＢが７であるポリグリセリン脂肪酸エステル（ＰＧＦＥ１）を得た。以下同様に、ポリグリセリンの平均重合度、脂肪酸の種類、ポリグリセリンに対する脂肪酸のモル比率を変化させてＰＧＦＥ２〜１６を調製し、表１に示した。
(Synthesis of polyglycerol fatty acid ester)
333.9 g of diglycerin and 402.3 g of lauric acid are placed in a reaction vessel, sodium hydroxide is added and reacted at 230 ° C. under a nitrogen stream to obtain a polyglycerin fatty acid ester (PGFE1) having an HLB of 7. It was. Similarly, PGFE 2 to 16 were prepared by changing the average degree of polymerization of polyglycerol, the type of fatty acid, and the molar ratio of fatty acid to polyglycerol, and are shown in Table 1.
（ポリグリセリン縮合リシノール酸エステルの合成）
リシノール酸に水酸化ナトリウムを添加し、１８０℃〜２２０℃で縮合反応を行った。エステル化は、重量比がデカグリセリン：縮合リシノール酸＝１：３となるように調製し、１８０℃〜２２０℃で反応を行い、リシノール酸の縮合度が２であるポリグリセリン縮合リシノール酸エステル（ＰＧＰＲ１）を調製した。また、デカグリセリンと縮合リシノール酸の重量比をデカグリセリン：縮合リシノール酸＝１：６に変更し、リシノール酸の縮合度が４であるポリグリセリン縮合リシノール酸エステル（ＰＧＰＲ２）を同様に調製した。
(Synthesis of polyglycerin condensed ricinoleic acid ester)
Sodium hydroxide was added to ricinoleic acid, and a condensation reaction was performed at 180 ° C to 220 ° C. Esterification is carried out so that the weight ratio is decaglycerin: condensed ricinoleic acid = 1: 3, the reaction is performed at 180 ° C. to 220 ° C., and the degree of condensation of ricinoleic acid is 2, which is a polyglycerin condensed ricinoleic acid ester ( PGPR1) was prepared. Moreover, the weight ratio of decaglycerin and condensed ricinoleic acid was changed to decaglycerin: condensed ricinoleic acid = 1: 6, and a polyglycerin condensed ricinoleic acid ester (PGPR2) having a degree of condensation of ricinoleic acid of 4 was similarly prepared.
（試験方法）
油溶化組成物の透明性は、紫外可視分光光度計（Ｕ−２９００、(株)日立製作所製）を用い、室温にて保存した試料の１日後、７日後の透過率を測定した。測定波長は６００ｎｍとした。
(Test method)
Transparency of the oil-solubilized composition was measured by using a UV-visible spectrophotometer (U-2900, manufactured by Hitachi, Ltd.), and the transmittance after 1 day and 7 days after the sample stored at room temperature. The measurement wavelength was 600 nm.
（実施例１）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１）１５重量％と水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）７５重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、前記の方法により評価した。この油溶化組成物の組成、及び結果を表２に示す。表中の数字の単位は重量％であり、記号◎は油溶化組成物の透過率が９０％以上、記号○は油溶化組成物の透過率が５０％以上９０％未満、記号△は油溶化組成物の透過率が５０％未満、記号×は油溶化組成物が均一でなく、沈殿が生じた状態をそれぞれ表している。
Example 1
15% by weight of polyglycerol fatty acid ester (PGFE1) and 10% by weight of water were uniformly mixed at room temperature. Thereafter, 75% by weight of liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) was gradually added with stirring to obtain an oil-solubilized composition. Using this sample, it was evaluated by the method described above. The composition of the oil-solubilized composition and the results are shown in Table 2. The unit of the numbers in the table is% by weight, the symbol ◎ indicates the transmittance of the oil-solubilized composition is 90% or more, the symbol ○ indicates the transmittance of the oil-solubilized composition is 50% or more and less than 90%, and the symbol Δ indicates oil-solubilization. The transmittance of the composition is less than 50%, and the symbol x represents a state where the oil-solubilized composition is not uniform and precipitation occurs.
（実施例２〜１２）
実施例１において使用したポリグリセリン脂肪酸エステル（ＰＧＦＥ１）の代わりにポリグリセリン脂肪酸エステル（ＰＧＦＥ２〜１２）を使用した以外は、実施例１と同様にして油溶化組成物を調製し、評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Examples 2 to 12)
An oil-solubilized composition was prepared and evaluated in the same manner as in Example 1 except that the polyglycerin fatty acid ester (PGFE2 to 12) was used instead of the polyglycerin fatty acid ester (PGFE1) used in Example 1. The composition of the oil-solubilized composition and the results are shown in Table 2.
（実施例１３）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ５）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ６）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 13)
Polyglycerin fatty acid ester (PGFE5) 5% by weight, polyglycerol fatty acid ester (PGFE6) 5% by weight, and water 10% by weight were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) 80% by weight was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition and the results are shown in Table 2.
（実施例１４）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ６）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１３）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 14)
Polyglycerin fatty acid ester (PGFE6) 5% by weight, polyglycerol fatty acid ester (PGFE13) 5% by weight, and water 10% by weight were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) 80% by weight was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition, and the results shown in Table 2.
（実施例１５）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１３）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１４）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 15)
Polyglycerin fatty acid ester (PGFE13) 5% by weight, polyglycerol fatty acid ester (PGFE14) 5% by weight, and water 10% by weight were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) 80% by weight was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition and the results are shown in Table 2.
（実施例１６）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１５）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１６）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 16)
Polyglycerin fatty acid ester (PGFE15) 5% by weight, polyglycerin fatty acid ester (PGFE16) 5% by weight, and water 10% by weight were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) 80% by weight was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition, and the results shown in Table 2.
（実施例１７）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１０）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１１）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 17)
Polyglycerin fatty acid ester (PGFE10) 5 wt%, polyglycerin fatty acid ester (PGFE11) 5 wt%, and water 10 wt% were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) 80% by weight was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition and the results are shown in Table 2.
（実施例１８）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１０）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１１）５重量％、水２０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）７０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 18)
Polyglycerin fatty acid ester (PGFE10) 5% by weight, polyglycerin fatty acid ester (PGFE11) 5% by weight, and water 20% by weight were uniformly mixed at room temperature. Thereafter, 70% by weight of liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition and the results are shown in Table 2.
（実施例１９）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１０）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１１）５重量％、水２５重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）６５重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 19)
Polyglycerin fatty acid ester (PGFE10) 5% by weight, polyglycerin fatty acid ester (PGFE11) 5% by weight, and water 25% by weight were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) 65% by weight was gradually added with stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition, and the results shown in Table 2.
（実施例２０）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１０）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１１）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：８０ｍＰａ・ｓ／２５℃）８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Example 20)
Polyglycerin fatty acid ester (PGFE10) 5 wt%, polyglycerin fatty acid ester (PGFE11) 5 wt%, and water 10 wt% were uniformly mixed at room temperature. Thereafter, liquid paraffin (viscosity: 80 mPa · s / 25 ° C.) 80% by weight was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition, and the results shown in Table 2.
（比較例１）
水１０重量％中に、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）９０重量％を撹拌しながら徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Comparative Example 1)
In 10% by weight of water, 90% by weight of liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) was gradually added with stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition and the results are shown in Table 2.
（比較例２）
ポリグリセリン縮合リシノール酸エステル（ＰＧＰＲ１）５重量％、ポリグリセリン縮合リシノール酸エステル（ＰＧＰＲ２）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、流動パラフィン（粘度：１１ｍＰａ・ｓ／２５℃）７５重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Comparative Example 2)
Polyglycerin condensed ricinoleic acid ester (PGPR1) 5% by weight, polyglycerol condensed ricinoleic acid ester (PGPR2) 5% by weight, and water 10% by weight were uniformly mixed at room temperature. Thereafter, 75% by weight of liquid paraffin (viscosity: 11 mPa · s / 25 ° C.) was gradually added with stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition, and the results shown in Table 2.
（比較例３）
ポリグリセリン脂肪酸エステル（ＰＧＦＥ１０）５重量％、ポリグリセリン脂肪酸エステル（ＰＧＦＥ１１）５重量％、水１０重量％を室温で均一に混合した。その後、撹拌しながら、大豆油８０重量％を徐々に添加し、油溶化組成物を得た。この試料を用いて、実施例１と同様に評価した。この油溶化組成物の組成、及び結果を表２に示す。
(Comparative Example 3)
Polyglycerin fatty acid ester (PGFE10) 5 wt%, polyglycerin fatty acid ester (PGFE11) 5 wt%, and water 10 wt% were uniformly mixed at room temperature. Thereafter, 80% by weight of soybean oil was gradually added while stirring to obtain an oil-solubilized composition. Evaluation was performed in the same manner as in Example 1 using this sample. The composition of the oil-solubilized composition, and the results shown in Table 2.
表２の結果より、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油に水を分散させる油溶化剤として、本発明のポリグリセリン脂肪酸エステルを用いた実施例１〜２０では、油溶化剤を添加していない比較例１や油溶化剤としてポリグリセリン縮合リシノール酸エステルを使用した比較例２に比べて、油溶化組成物の透明性は高く、安定に保持された。このことから、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油に水を分散させる油溶化剤として、ポリグリセリン脂肪酸エステルを用いることにより、透明性、及び経時安定性の高い油溶化組成物が製造できることが示される。 From the results of Table 2, in Examples 1 to 20 using the polyglycerin fatty acid ester of the present invention as an oil solubilizer for dispersing water in a hydrocarbon oil having a viscosity at 25 ° C. of 5 to 100 mPa · s, an oil solubilizer is used. Compared with Comparative Example 1 in which no oil was added and Comparative Example 2 in which polyglycerin-condensed ricinoleic acid ester was used as an oil solubilizer, the oil-solubilized composition was high in transparency and maintained stably. From this, by using a polyglycerin fatty acid ester as an oil solubilizer for dispersing water in a hydrocarbon oil having a viscosity at 25 ° C. of 5 to 100 mPa · s, an oil-solubilized composition having high transparency and stability over time. Is shown to be manufacturable.
また、ポリグリセリン脂肪酸エステルのＨＬＢが９〜１３である実施例７〜１２では、実施例１〜６と比較して油溶化組成物の透明性は良好であった。中でも、ポリグリセリン脂肪酸エステルを構成する脂肪酸がオレイン酸、又はイソステアリン酸である、実施例９〜１１、及びオレイン酸とイソステアリン酸の混合脂肪酸である実施例１２では、特に優れた透明性を示した。 Moreover, in Examples 7-12 whose HLB of polyglyceryl fatty acid ester is 9-13, the transparency of the oil-solubilized composition was good compared with Examples 1-6. Among them, the fatty acids constituting the polyglycerin fatty acid ester are oleic acid or isostearic acid, Examples 9 to 11 and Example 12 which is a mixed fatty acid of oleic acid and isostearic acid showed particularly excellent transparency. .
さらに、ポリグリセリンオレイン酸エステル、及びイソステアリン酸エステルを２種併用した実施例１３〜２０では、添加量が減少しても、ポリグリセリン脂肪酸エステルを単独で使用した場合と同量以上の水を油中に分散させることが可能であり、油溶化剤としてポリグリセリン脂肪酸エステルを併用することが好ましいことが示される。また、使用したポリグリセリン脂肪酸エステルのＨＬＢが９〜１３以外のものを併用した場合であっても、それらの加重平均ＨＬＢが９〜１３となる場合、透明性の高い油溶化組成物が得られた。従って、油溶化剤として、平均ＨＬＢが９〜１３であり、構成脂肪酸がオレイン酸、且つ／又はイソステアリン酸である、ポリグリセリン脂肪酸エステルを使用することにより、より透明性、経時安定性に優れた油溶化組成物が製造できることは明らかである。 Furthermore, in Examples 13 to 20 in which two types of polyglycerin oleate and isostearic acid ester were used in combination, even when the addition amount was reduced, the same amount or more of water as in the case where polyglycerin fatty acid ester was used alone was oiled. It can be dispersed therein, and it is indicated that it is preferable to use a polyglycerol fatty acid ester in combination as an oil solubilizer. In addition, even when the polyglycerin fatty acid ester used has an HLB other than 9-13, when the weighted average HLB is 9-13, a highly transparent oil-solubilized composition is obtained. It was. Therefore, by using a polyglycerin fatty acid ester having an average HLB of 9 to 13 and a constituent fatty acid of oleic acid and / or isostearic acid as an oil solubilizer, the transparency and stability over time are more excellent. Obviously, an oil-solubilized composition can be produced.
実施例１７〜１９を比較すると、油溶化組成物中の含水量が２５％である実施例１９では、油溶化組成物の透過率は、実施例１７、１８より低い。この結果より、油溶化組成物における含水量は２０％以下が好ましいことが示される。 When Examples 17 to 19 are compared, in Example 19 in which the water content in the oil-solubilized composition is 25%, the transmittance of the oil-solubilized composition is lower than those in Examples 17 and 18. From this result, it is shown that the water content in the oil-solubilized composition is preferably 20% or less.
一方、油として、２５℃における粘度が５〜１００ｍＰａ・ｓの炭化水素油以外の油を使用した比較例３では、油溶化剤としてポリグリセリン脂肪酸エステルを用いた場合においても、透明性のある油溶化物は得られなかった。 On the other hand, in Comparative Example 3 in which an oil other than a hydrocarbon oil having a viscosity at 25 ° C. of 5 to 100 mPa · s is used as the oil, even when a polyglycerin fatty acid ester is used as an oil solubilizer, a transparent oil No lysate was obtained.
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| JPH09208443A (en) * | 1996-02-05 | 1997-08-12 | Daicel Chem Ind Ltd | W/o-type emulsified cosmetic |
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