JP2017160128A - Cosmetic base containing polyalkyleneimine derivative - Google Patents
Cosmetic base containing polyalkyleneimine derivative Download PDFInfo
- Publication number
- JP2017160128A JP2017160128A JP2016043285A JP2016043285A JP2017160128A JP 2017160128 A JP2017160128 A JP 2017160128A JP 2016043285 A JP2016043285 A JP 2016043285A JP 2016043285 A JP2016043285 A JP 2016043285A JP 2017160128 A JP2017160128 A JP 2017160128A
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- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- acid
- polyalkyleneimine
- cosmetic
- 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.)
- Pending
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 63
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229920002873 Polyethylenimine Polymers 0.000 claims description 9
- 125000001165 hydrophobic group Chemical group 0.000 abstract description 23
- 239000000839 emulsion Substances 0.000 abstract description 22
- 239000000843 powder Substances 0.000 abstract description 10
- 238000002156 mixing Methods 0.000 abstract description 6
- 125000006736 (C6-C20) aryl group Chemical group 0.000 abstract 2
- 150000002466 imines Chemical class 0.000 abstract 1
- 229920001281 polyalkylene Polymers 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 19
- 235000014113 dietary fatty acids Nutrition 0.000 description 19
- 239000000194 fatty acid Substances 0.000 description 19
- 229930195729 fatty acid Natural products 0.000 description 19
- -1 dimethylsiloxane Chemical class 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 11
- 238000004945 emulsification Methods 0.000 description 10
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000007259 addition reaction Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 8
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 8
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 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 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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- 239000000203 mixture Substances 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
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- 125000001033 ether group Chemical group 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
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- 125000001302 tertiary amino group Chemical group 0.000 description 5
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 4
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
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- 239000004593 Epoxy Substances 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 229920006007 hydrogenated polyisobutylene Polymers 0.000 description 3
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 229920001515 polyalkylene glycol Polymers 0.000 description 3
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- 239000003760 tallow Substances 0.000 description 3
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 2
- 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
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- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
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- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 description 2
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- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
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- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
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- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
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- 229920001083 polybutene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001944 prunus armeniaca kernel oil Substances 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
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- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 238000006561 solvent free reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 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
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明はポリアルキレンイミン誘導体を含む化粧料用基材およびそれを配合してなる化粧料に関する。より詳しくは、疎水基を導入したポリアルキレンイミン誘導体であって、窒素原子と疎水基の間に水酸基とエーテル基を有するポリアルキレンイミン誘導体を用いた化粧料用基材に関する。 The present invention relates to a cosmetic base material containing a polyalkyleneimine derivative and a cosmetic comprising the same. More specifically, the present invention relates to a cosmetic base material using a polyalkyleneimine derivative having a hydrophobic group and having a hydroxyl group and an ether group between a nitrogen atom and a hydrophobic group.
化粧品には、皮膚や毛髪に滑らかさやしっとり感を付与するために油剤が使用されている。油剤としては、流動パラフィン、スクワランなどの炭化水素油、植物油に代表される油脂やトリグリセリド、エステル結合を有するエステル油、ジメチルシロキサンなどといったシリコーン油などが使用される。これらの油剤は、互いの長所を生かし短所を補い合うために化粧料の処方中で併用される場合が多いが、さらに水を配合することにより、感触面や水分補給による肌ケアなどの点から化粧料としての価値が高まる。これは、水の効果によって油性感が抑制され、水を配合しない場合と比べるとさっぱりした肌感覚が得られやすい事にも起因する。 Oils are used in cosmetics to impart a smooth and moist feeling to the skin and hair. As the oil agent, hydrocarbon oils such as liquid paraffin and squalane, fats and oils such as vegetable oils and triglycerides, ester oils having ester bonds, silicone oils such as dimethylsiloxane, and the like are used. These oils are often used in cosmetic formulations in order to make use of each other's strengths and make up for the weaknesses. The value as a fee increases. This is because the oily feeling is suppressed by the effect of water, and a refreshing skin sensation is easily obtained as compared with the case where water is not blended.
油剤と水とを化粧料中に安定に配合するために、通常は界面活性剤を用いた乳化が行われる。一般的にはエチレンオキシドやプロピレンオキシドなどから誘導されるポリアルキレングリコール誘導体( 例えば特許文献1 )やポリエーテル基を有するポリオルガノシロキサン( 例えば特許文献2 )などが使用される。 In order to stably mix the oil agent and water in the cosmetic, emulsification using a surfactant is usually performed. In general, polyalkylene glycol derivatives derived from ethylene oxide, propylene oxide, etc. (for example, Patent Document 1), polyorganosiloxane having a polyether group (for example, Patent Document 2), and the like are used.
また、化粧品には、紫外線など外的要因から皮膚を保護するために、酸化チタンや酸化亜鉛といった無機粉体が汎用され、ファンデーションやサンスクリーン剤には不可欠な原料となっている。無機粉体の分散安定性を高めることは、化粧品の商品価値を保持するための必須技術であるが、そのためにも界面活性剤は必要不可欠な成分である。 In cosmetics, inorganic powders such as titanium oxide and zinc oxide are widely used to protect the skin from external factors such as ultraviolet rays, and are essential materials for foundations and sunscreen agents. Increasing the dispersion stability of the inorganic powder is an essential technique for maintaining the commercial value of cosmetics, but a surfactant is also an indispensable component for that purpose.
しかしながら、ポリアルキレングリコール誘導体は、使用量が多くなると、疎水性の発現が不十分となり、界面活性剤としての特長や乳化安定性が低下し、のびや肌へのなじみといった製剤の使用感が悪化してしまうという課題がある。ここで、乳化安定性とは、成分中の油分と水分が分離・転相することなく、安定的に存在できる程度を指す。また、ポリオルガノシロキサンは、乳化安定性が悪く、そのため化粧料に通常用いられる他の添加剤とは相溶せず、ポリオルガノシロキサンを化粧料に多量に配合した場合には、安定な化粧料を得ることが困難という課題がある。 However, as polyalkylene glycol derivatives are used in large quantities, the expression of hydrophobicity becomes insufficient, the surfactant characteristics and emulsification stability decrease, and the feeling of use of preparations such as spread and familiarity to the skin deteriorates. There is a problem of doing it. Here, the emulsification stability refers to the extent that oil and water in the component can stably exist without separation and phase inversion. In addition, polyorganosiloxane has poor emulsion stability, so it is incompatible with other additives usually used in cosmetics, and when polyorganosiloxane is incorporated in cosmetics in large quantities, it is a stable cosmetic. There is a problem that it is difficult to obtain.
一方、無機粉体の分散のような固−液界面において、界面活性剤の親水基は酸化チタンなど固体表面への吸着性基として働くことが知られているが、ポリアルキレングリコール誘導体などに含まれるオキシエチレン基では、固体表面への吸着能に課題が有り、無機紛体の分散性が悪い。ここで、無機紛体の分散性とは、無機紛体と液相の固−液界面において、無機紛体が液相中に均一に分散できる程度を指す。 On the other hand, at the solid-liquid interface such as dispersion of inorganic powder, the hydrophilic group of the surfactant is known to act as an adsorbing group on the solid surface such as titanium oxide, but it is included in polyalkylene glycol derivatives and the like. In the oxyethylene group, there is a problem in the adsorptivity to the solid surface, and the dispersibility of the inorganic powder is poor. Here, the dispersibility of the inorganic powder refers to the degree to which the inorganic powder can be uniformly dispersed in the liquid phase at the solid-liquid interface between the inorganic powder and the liquid phase.
したがって、本発明は、上記の従来技術の問題点に鑑みてなされたものであり、配合安定性、すなわち乳化安定性および/または無機紛体の分散性に優れ、配合後長期間にわたり安定に保存できる化粧料を提供することを目的とする。 Therefore, the present invention has been made in view of the above-mentioned problems of the prior art, and is excellent in blending stability, that is, emulsion stability and / or dispersibility of inorganic powder, and can be stably stored for a long period after blending. The purpose is to provide cosmetics.
本発明者らは、化粧料の上記の様な問題点に鑑み、鋭意検討を重ねた結果、ポリアルキレンイミンの窒素原子に疎水基を導入し、かつ当該窒素原子と疎水基との間に水酸基及びエーテル基を存在させた化粧料用基材を用いることによって、乳化安定性と、無機紛体の分散性能が良好であり、さらに配合後長期間にわたって安定に保存できることを見出し、本発明を完成させた。 In view of the above problems of cosmetics, the present inventors have conducted extensive studies, and as a result, introduced a hydrophobic group into the nitrogen atom of polyalkyleneimine, and a hydroxyl group between the nitrogen atom and the hydrophobic group. And found that the emulsification stability and the dispersion performance of the inorganic powder are good by using a cosmetic base material in which an ether group is present, and can be stably stored for a long period of time after blending. It was.
すなわち、上記目的は、疎水基を導入したポリアルキレンイミン誘導体を用いた化粧料であって、ポリアルキレンイミンの窒素原子に下記式(1)の構造の疎水基を有する置換基が付加してなるポリアルキレンイミン誘導体を含む化粧料用基材によって達成できる。 That is, the above object is a cosmetic using a polyalkyleneimine derivative having a hydrophobic group introduced therein, wherein a substituent having a hydrophobic group having the structure of the following formula (1) is added to the nitrogen atom of the polyalkyleneimine. This can be achieved by a cosmetic base material containing a polyalkyleneimine derivative.
本発明のポリアルキレンイミン誘導体を含む化粧料用基材は、皮膚や毛髪用の化粧料に配合することができ、本発明の化粧料用基材を含む化粧料は優れた乳化安定性と無機粒子の分散安定性を示し、さらにポリアルキレンイミン誘導体が抗菌性及び消臭性能を有するため、雑菌の増殖を長期間抑制できる化粧料を提供することが可能となる。 The cosmetic base material containing the polyalkyleneimine derivative of the present invention can be blended in cosmetics for skin and hair, and the cosmetic material containing the cosmetic base material of the present invention has excellent emulsion stability and inorganic properties. Since the dispersion stability of the particles is exhibited and the polyalkyleneimine derivative has antibacterial properties and deodorizing performance, it is possible to provide a cosmetic that can suppress the growth of various bacteria for a long period of time.
以下、本発明を実施するための形態について説明する。しかしながら、本発明はこの実
施形態に限定はされない。
Hereinafter, modes for carrying out the present invention will be described. However, the present invention is not limited to this embodiment.
なお、本明細書において、範囲を示す「X〜Y」は「X以上Y以下」を意味する。また、特記しない限り、操作および物性等の測定は室温(20〜25℃)/相対湿度40〜50%の条件で実施する。
本発明は、ポリアルキレンイミンの窒素原子に下記式(1)の構造を有する置換基が付
加してなるポリアルキレンイミン誘導体を含む化粧料用基材を提供する。なお、本明細書において、ポリアルキレンイミンの窒素原子に下記式(1)の構造を有する置換基が付加してなるポリアルキレンイミン誘導体を、単に「ポリアルキレンイミン誘導体」または「本発明に係るポリアルキレンイミン誘導体」とも称する。
In this specification, “X to Y” indicating a range means “X or more and Y or less”. Unless otherwise specified, measurement of operation, physical properties, and the like is performed under conditions of room temperature (20 to 25 ° C.) / Relative humidity of 40 to 50%.
The present invention provides a cosmetic base material comprising a polyalkyleneimine derivative obtained by adding a substituent having the structure of the following formula (1) to a nitrogen atom of polyalkyleneimine. In this specification, a polyalkyleneimine derivative obtained by adding a substituent having the structure of the following formula (1) to the nitrogen atom of polyalkyleneimine is simply referred to as “polyalkyleneimine derivative” or “polyalkyleneimine derivative according to the present invention”. Also referred to as “alkyleneimine derivative”.
本発明に係るポリアルキレンイミン誘導体は、ポリアルキレンイミンの窒素原子に疎水基(上記式(1)中のR1)を導入し、かつポリアルキレンイミンの窒素原子と疎水基との間に水酸基とエーテル基が存在する点に特徴を有する。
ポリアルキレンイミン誘導体の1級、2級、3級のアミノ基は親水基として水との相溶性を向上させ、さらに無機粒子の表面への吸着基としても作用する。一方、疎水基は油剤との相溶性を向上させ、さらに無機粒子の凝集抑制材としても作用する。
The polyalkyleneimine derivative according to the present invention introduces a hydrophobic group (R 1 in the above formula (1)) into the nitrogen atom of the polyalkyleneimine, and a hydroxyl group between the nitrogen atom and the hydrophobic group of the polyalkyleneimine. It is characterized by the presence of an ether group.
The primary, secondary, and tertiary amino groups of the polyalkyleneimine derivative improve the compatibility with water as a hydrophilic group, and also act as an adsorbing group on the surface of the inorganic particles. On the other hand, the hydrophobic group improves the compatibility with the oil agent, and also acts as a material for suppressing aggregation of inorganic particles.
本発明のポリアルキレンイミン誘導体では、1級、2級、3級のアミノ基だけでなくエーテル基、水酸基を複合して親水基として用いることによって効果がさらに向上する。非イオン性の親水基であるエーテル基および水酸基が液―液界面での乳化安定能を向上させ、また1級、2級、3級のアミノ基が固−液表面での固体表面への吸着部位として機能し、そのため乳化安定性及び分散安定性が優れるものと考えられる。但し、これらは推定であって、本発明はこれらのメカニズムに限定されない。
本発明に係る疎水基を導入したポリアルキレンイミン誘導体におけるポリアルキレンイミンとは、主鎖がアルキレン基とアミノ基からなる繰返し単位であり、下記式(A)および/または式(B)の構造の繰返し単位を有するポリマーである。
In the polyalkyleneimine derivative of the present invention, the effect is further improved by using not only primary, secondary, and tertiary amino groups but also ether groups and hydroxyl groups in combination as hydrophilic groups. Nonionic hydrophilic groups such as ether groups and hydroxyl groups improve the emulsion stability at the liquid-liquid interface, and primary, secondary, and tertiary amino groups adsorb on the solid surface at the solid-liquid surface. It functions as a site and is therefore considered to have excellent emulsification stability and dispersion stability. However, these are estimations, and the present invention is not limited to these mechanisms.
The polyalkyleneimine in the polyalkyleneimine derivative introduced with a hydrophobic group according to the present invention is a repeating unit having a main chain composed of an alkylene group and an amino group, and has a structure of the following formula (A) and / or formula (B): A polymer having a repeating unit.
上記式(1)の構造を有する置換基における疎水基であるR1としては、炭素数6〜20のアルキル基、炭素数6〜20のアルケニル基、炭素数6〜20のアリール基、または−(CH2CH2O)n−R2を表す。式:−(CH2CH2O)n−R2の置換基において、R2は炭素数6〜20のアルキル基、炭素数6〜20のアルケニル基、炭素数6〜20のアリール基を表す。nは1〜50の整数を表す。乳化安定性や分散安定性を考慮すると、nは、1〜20であることが好ましい。このような疎水基であると、疎水性と親水性のバランスが良く、乳化安定性や分散安定性が良い。ここで、アルキル基、アルケニル基、または式:−(CH2CH2O)n−R2の置換基中のアルキル基若しくはアルケニル基の炭素数が5以下であると、乳化安定性や分散安定性が低下する。逆に、アルキル基、アルケニル基、または式:−(CH2CH2O)n−R2の置換基中のアルキル基若しくはアルケニル基の炭素数が21以上であると、他の成分との相溶性が低下し、乳化安定性が低下したり、疎水基同士が凝集し、分散安定性が低下する。 As R 1 which is a hydrophobic group in the substituent having the structure of the above formula (1), an alkyl group having 6 to 20 carbon atoms, an alkenyl group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or — It represents a (CH 2 CH 2 O) n -R 2. In substituent of the formula :-( CH 2 CH 2 O) n -R 2, R 2 represents an alkyl group, an alkenyl group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms having from 6 to 20 carbon atoms . n represents an integer of 1 to 50. In consideration of emulsification stability and dispersion stability, n is preferably 1-20. Such a hydrophobic group has a good balance between hydrophobicity and hydrophilicity and good emulsification stability and dispersion stability. Here, when the alkyl group, the alkenyl group, or the alkyl group or the alkenyl group in the substituent of the formula: — (CH 2 CH 2 O) n —R 2 has 5 or less carbon atoms, emulsion stability and dispersion stability Sex is reduced. On the other hand, when the alkyl group or alkenyl group or the alkyl group or alkenyl group in the substituent of the formula: — (CH 2 CH 2 O) n —R 2 has 21 or more carbon atoms, the phase with other components Solubility decreases, emulsion stability decreases, and hydrophobic groups aggregate to disperse dispersion stability.
ここで、炭素数6〜20のアルキル基は、特に制限されず、炭素数6〜20の直鎖または分岐鎖のアルキル基でありうる。具体的には、ヘキシル基、イソヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基(ラウリル基)、2−エチルヘキシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、エイコシル基などが挙げられる。 Here, the alkyl group having 6 to 20 carbon atoms is not particularly limited, and may be a linear or branched alkyl group having 6 to 20 carbon atoms. Specifically, hexyl group, isohexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group (lauryl group), 2-ethylhexyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, A heptadecyl group, an octadecyl group, a nonadecyl group, an eicosyl group, etc. are mentioned.
炭素数6〜20のアルケニル基は、特に制限されず、炭素数6〜20の直鎖または分岐鎖のアルケニル基でありうる。具体的には、1−ヘキセニル基、2−ヘキセニル基、3−ヘキセニル基、1−ヘプテニル基、2−ヘプテニル基、3−ヘプテニル基などが挙げられる。 The alkenyl group having 6 to 20 carbon atoms is not particularly limited, and may be a linear or branched alkenyl group having 6 to 20 carbon atoms. Specific examples include 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 1-heptenyl group, 2-heptenyl group, 3-heptenyl group and the like.
炭素数6〜20のアリール基は、特に制限されず、例えば、フェニル基、ベンジル基、フェネチル基、o−,m−若しくはp−トリル基、2,3−若しくは2,4−キシリル基、メシチル基、ナフチル基、アントリル基、フェナントリル基、ビフェニリル基、ベンズヒドリル基、トリチル基、ピレニル基などが挙げられる。 The aryl group having 6 to 20 carbon atoms is not particularly limited, and examples thereof include phenyl group, benzyl group, phenethyl group, o-, m- or p-tolyl group, 2,3- or 2,4-xylyl group, mesityl. Group, naphthyl group, anthryl group, phenanthryl group, biphenylyl group, benzhydryl group, trityl group, pyrenyl group and the like.
これらのうち、炭素数6〜16のアルキル基が好ましく、炭素数6〜12のアルキル基がより好ましく、炭素数6〜10のアルキル基がさらにより好ましく、炭素数6〜8のアルキル基が特に好ましい。R2としては炭素数6〜16のアルキル基が好ましく、炭素数6〜12のアルキル基がより好ましい。R1およびR2の炭素数が16以下であると、疎水性と親水性のバランスが良く、必要かつ十分な疎水性を示し、乳化安定性及び分散安定性が発揮される。 Among these, an alkyl group having 6 to 16 carbon atoms is preferable, an alkyl group having 6 to 12 carbon atoms is more preferable, an alkyl group having 6 to 10 carbon atoms is still more preferable, and an alkyl group having 6 to 8 carbon atoms is particularly preferable. preferable. R 2 is preferably an alkyl group having 6 to 16 carbon atoms, and more preferably an alkyl group having 6 to 12 carbon atoms. When the carbon number of R 1 and R 2 is 16 or less, the balance between hydrophobicity and hydrophilicity is good, the necessary and sufficient hydrophobicity is exhibited, and emulsion stability and dispersion stability are exhibited.
ポリアルキレンイミンの窒素原子に上記式(1)の構造の置換基を導入する割合は、全窒素原子の5モル%以上が好ましく、10モル%以上がより好ましく、12モル%以上が特に好ましい。また、70モル%以下が好ましく、60モル%以下がより好ましく、50モル%以下がさらに好ましく、30モル%以下が特に好ましい。この範囲であると、アミノ基の固−液界面での固体への吸着性を維持したまま、疎水性も発揮できるため、乳化安定性や分散安定性が高くなる。 The ratio of introducing the substituent having the structure of the above formula (1) to the nitrogen atom of the polyalkyleneimine is preferably 5 mol% or more, more preferably 10 mol% or more, and particularly preferably 12 mol% or more of all nitrogen atoms. Moreover, 70 mol% or less is preferable, 60 mol% or less is more preferable, 50 mol% or less is more preferable, 30 mol% or less is especially preferable. Within this range, the hydrophobicity can be exhibited while maintaining the adsorptivity to the solid at the solid-liquid interface of the amino group, so that the emulsion stability and the dispersion stability are enhanced.
本発明の疎水基を導入したポリアルキレンイミン誘導体の乳化安定性や分散安定性は原料となるポリアルキレンイミンの重量平均分子量(Mw)による。原料となるポリアルキレンイミンの重量平均分子量としては、400以上が好ましく、500以上がより好ましい。また、重量平均分子量の上限としては、70,000以下が好ましく、10,000以下がより好ましく、5,000以下がさらに好ましく、3,000以下が特に好ましい。重量平均分子量は、GPC法によって求められ、具体的には実施例に記載の方法により測定した値を用いる。 The emulsion stability and dispersion stability of the polyalkyleneimine derivative having a hydrophobic group introduced according to the present invention depend on the weight average molecular weight (Mw) of the polyalkyleneimine used as a raw material. As a weight average molecular weight of the polyalkyleneimine used as a raw material, 400 or more are preferable and 500 or more are more preferable. The upper limit of the weight average molecular weight is preferably 70,000 or less, more preferably 10,000 or less, further preferably 5,000 or less, and particularly preferably 3,000 or less. A weight average molecular weight is calculated | required by GPC method, and uses the value measured by the method as described in an Example specifically ,.
本発明における疎水基を導入したポリアルキレンイミン誘導体は、ポリアルキレンイミンの下記式(2)のグリシジルエーテルによる付加反応により得られる。グリシジルエーテルはエポキシ樹脂の原料等にも使用され、工業的にも入手しやすく好ましい。 The polyalkyleneimine derivative introduced with a hydrophobic group in the present invention is obtained by addition reaction of polyalkyleneimine with glycidyl ether of the following formula (2). Glycidyl ether is also used as a raw material for epoxy resins and is preferred because it is easily available industrially.
上記式(2)における、R3およびR4の好ましい形態は、前記R1およびR2と同じである。また、上記式(2)におけるmの好ましい形態は、前記nと同じである。 In the above formula (2), preferred forms of R 3 and R 4 are the same as those of R 1 and R 2 . Moreover, the preferable form of m in the said Formula (2) is the same as said n.
原料となるポリアルキレンイミンは、ポリエチレンイミン、ポリプロピレンイミン、ポリブチレンイミンなどが挙げられ、中でもポリエチレンイミンが好ましい。ポリアルキレンイミン中に存在する第1級アミノ基、第2級アミノ基、第3級アミノ基のうち、第1級アミノ基と第2級アミノ基を合わせた割合が、好ましくは30モル%以上、より好ましくは40モル%以上、特に好ましくは50モル%以上である。第1級アミノ基と第2級アミノ基を合わせた割合が30モル%よりも少ないと、導入される疎水基の量が少なくなり凝集しやすくなったり、疎水基導入後の第2級アミノ基の割合が少なくなって塩基性が弱くなり、固−液界面中の固体への吸着能が低下して分散安定性が低下する。なお、ポリアルキレンイミン中の第1級アミノ基、第2級アミノ基、第3級アミノ基の割合はNMR分析や滴定等により測定することができる。 Examples of the polyalkyleneimine used as a raw material include polyethyleneimine, polypropyleneimine, and polybutyleneimine, and among these, polyethyleneimine is preferable. The ratio of the primary amino group and the secondary amino group in the primary amino group, secondary amino group, and tertiary amino group present in the polyalkyleneimine is preferably 30 mol% or more More preferably, it is 40 mol% or more, and particularly preferably 50 mol% or more. If the ratio of the primary amino group and the secondary amino group is less than 30 mol%, the amount of the introduced hydrophobic group is reduced and aggregation is likely to occur, or the secondary amino group after introduction of the hydrophobic group. When the ratio is low, the basicity is weakened, the adsorption ability to the solid in the solid-liquid interface is lowered, and the dispersion stability is lowered. In addition, the ratio of the primary amino group, the secondary amino group, and the tertiary amino group in the polyalkyleneimine can be measured by NMR analysis or titration.
本発明のポリアルキレンイミン誘導体の重量平均分子量(Mw)としては、乳化安定性、分散安定性、保存安定性の観点から、400以上が好ましく、700以上がより好ましく、800以上がさらに好ましい。また、重量平均分子量の上限としては、特に制限されないが、乳化安定性、分散安定性、保存安定性の観点から、100,000以下であり、70,000以下が好ましく、20,000以下がより好ましく、5,000以下がさらに好ましく、3,000以下が特に好ましい。重量平均分子量はGPC法によって求められ、具体的には実施例に記載の方法により測定した値を用いる。 The weight average molecular weight (Mw) of the polyalkyleneimine derivative of the present invention is preferably 400 or more, more preferably 700 or more, and still more preferably 800 or more, from the viewpoints of emulsion stability, dispersion stability, and storage stability. The upper limit of the weight average molecular weight is not particularly limited, but is 100,000 or less, preferably 70,000 or less, more preferably 20,000 or less from the viewpoints of emulsion stability, dispersion stability, and storage stability. Preferably, 5,000 or less is more preferable, and 3,000 or less is particularly preferable. A weight average molecular weight is calculated | required by GPC method, and the value measured by the method as described in an Example is specifically used.
ポリアルキレンイミン(PAI)に対するグリシジルエーテル(GE)の反応の仕込み比(GE/PAI)は、好ましくは0.7以下、より好ましくは0.6以下、さらに好ましくは0.5以下であり、特に好ましくは0.3以下である。なお、ポリアルキレンイミン(PAI)に対するグリシジルエーテル(GE)の反応の仕込み比(GE/PAI)の下限は、特に制限されないが、好ましくは0.05以上、より好ましくは0.1以上である。かかる範囲であれば、十分な乳化安定性を得ることができる。ここで、ポリアルキレンイミンとグリシジルエーテルの反応の仕込み比は、ポリアルキレンイミンのアミン価とグリシジルエーテルのエポキシ当量を用いて以下のように表される。 The charge ratio (GE / PAI) of the reaction of glycidyl ether (GE) with respect to polyalkyleneimine (PAI) is preferably 0.7 or less, more preferably 0.6 or less, and further preferably 0.5 or less, particularly Preferably it is 0.3 or less. In addition, the lower limit of the charging ratio (GE / PAI) of the reaction of glycidyl ether (GE) with respect to polyalkyleneimine (PAI) is not particularly limited, but is preferably 0.05 or more, more preferably 0.1 or more. If it is this range, sufficient emulsification stability can be obtained. Here, the preparation ratio of the reaction between polyalkyleneimine and glycidyl ether is expressed as follows using the amine value of polyalkyleneimine and the epoxy equivalent of glycidyl ether.
付加反応は溶媒の存在下であっても、無溶媒下であっても、特に限定されないが、無溶媒反応、水または有機溶媒を溶媒とした反応が好ましい。より好ましくは無溶媒反応である。また、撹拌は、撹拌下、静置下の何れでもよいが、撹拌下で実施することが好ましい。 The addition reaction is not particularly limited in the presence of a solvent or in the absence of a solvent, but a solventless reaction or a reaction using water or an organic solvent as a solvent is preferred. More preferred is a solvent-free reaction. Moreover, although stirring may be any of stirring and standing, it is preferable to implement under stirring.
付加反応に使用できる溶媒は、水;メタノール、エタノール、イソプロピルアルコールなどの低級アルコール;ジメチルホルムアミド等のアミド類;ジエチルエーテル、テトラヒドロフラン、ジオキサン等のエーテル類;等から1種または2種以上を適宜選択して用いることができる。 The solvent that can be used for the addition reaction is appropriately selected from water, lower alcohols such as methanol, ethanol, and isopropyl alcohol; amides such as dimethylformamide; ethers such as diethyl ether, tetrahydrofuran, and dioxane; Can be used.
前記溶媒を用いる際の原料濃度は、特に限定されないが、ポリアルキレンイミンとグリシジルエーテルの合計量が好ましくは10重量%以上、より好ましくは20重量%以上、さらに好ましくは30重量%以上である。原料濃度が10重量%より少ないと、反応時間が長くなり好ましくない。 The raw material concentration when using the solvent is not particularly limited, but the total amount of polyalkyleneimine and glycidyl ether is preferably 10% by weight or more, more preferably 20% by weight or more, and further preferably 30% by weight or more. When the concentration of the raw material is less than 10% by weight, the reaction time becomes long, which is not preferable.
化粧料用基材として用いる際は、溶媒の残存量は30重量%以下、より好ましくは20重量%以下、さらに好ましくは10重量%以下である。溶媒の残存量が30重量%より多いと、他の化粧料成分との相溶性や乳化安定性に影響し、また配合後の使用時に人体に影響を与える恐れがあり、好ましくない。溶媒の残存量が多い場合は、蒸留、真空乾燥等既存の方法で必要な程度まで除去することができる。 When used as a cosmetic base material, the residual amount of the solvent is 30% by weight or less, more preferably 20% by weight or less, and still more preferably 10% by weight or less. If the residual amount of the solvent is more than 30% by weight, it is not preferable because it affects the compatibility with other cosmetic ingredients and the emulsion stability, and may affect the human body during use after blending. When the residual amount of the solvent is large, it can be removed to a necessary level by existing methods such as distillation and vacuum drying.
前記付加反応は、ポリアルキレンイミンとグリシジルエーテルを全て一括に仕込んでも良いし、いずれかを初期に仕込み残りを滴下しても良いが、ポリアルキレンイミンを初期に仕込み、これにグリシジルエーテルを滴下する方法が好ましい。 In the addition reaction, all of the polyalkyleneimine and glycidyl ether may be charged all at once, or one of them may be initially charged and the remainder may be dropped, but the polyalkyleneimine is initially charged and glycidyl ether is dropped into this. The method is preferred.
付加反応は、触媒は基本的には不要であるが、必要に応じて反応に悪影響を及ぼさないものであれば適宜使用しても良く、3級アミンが好ましい。酸を触媒に用いると、4級化が生じる場合があるので好ましくない。 In the addition reaction, a catalyst is basically unnecessary, but may be appropriately used as long as it does not adversely influence the reaction, and a tertiary amine is preferable. If an acid is used for the catalyst, quaternization may occur, which is not preferable.
付加反応の反応温度は、特に限定されないが、30℃以上が好ましく、40℃以上がより好ましく、50℃以上が特に好ましい。反応温度が30℃より低いと反応時間が長くなったり、未反応のグリシジルエーテルが増えたりするため、好ましくない。また反応温度は100℃以下が好ましく、90℃以下がより好ましく、80℃以下が特に好ましい。反応温度が高いとグリシジルエーテルの重合反応といった副反応が生じ好ましくない。また、付加反応の反応時間もまた、特に限定されず、反応温度、反応スケールなどによって適宜調節できる。 Although the reaction temperature of addition reaction is not specifically limited, 30 degreeC or more is preferable, 40 degreeC or more is more preferable, and 50 degreeC or more is especially preferable. If the reaction temperature is lower than 30 ° C., the reaction time becomes longer or unreacted glycidyl ether increases, which is not preferable. The reaction temperature is preferably 100 ° C. or lower, more preferably 90 ° C. or lower, and particularly preferably 80 ° C. or lower. If the reaction temperature is high, a side reaction such as a polymerization reaction of glycidyl ether occurs, which is not preferable. The reaction time for the addition reaction is also not particularly limited, and can be appropriately adjusted depending on the reaction temperature, reaction scale, and the like.
前記付加反応を実施する際は、得られる誘導体の着色を抑えるためには窒素雰囲気下で反応を行うことが好ましく、付加反応の際の雰囲気は得られる誘導体の使用目的に応じて適宜設定すればよい。なお、反応は、常圧(大気圧)、加圧、減圧のいずれで行ってもよい。 When carrying out the addition reaction, it is preferable to carry out the reaction under a nitrogen atmosphere in order to suppress the coloring of the resulting derivative, and the atmosphere during the addition reaction may be appropriately set according to the intended use of the resulting derivative. Good. The reaction may be performed at normal pressure (atmospheric pressure), pressurization, or reduced pressure.
本発明の疎水基を導入したポリアルキレンイミン誘導体中の未反応のグリシジルエーテルの量は5重量%以下が好ましく、3重量%以下がより好ましく、1重量%以下がさらに好ましい。未反応のグリシジルエーテルの量が5重量%より多いと、製品に配合した際に予期せぬ副反応が生じる可能性があり好ましくない。 The amount of unreacted glycidyl ether in the polyalkyleneimine derivative having a hydrophobic group introduced therein is preferably 5% by weight or less, more preferably 3% by weight or less, and further preferably 1% by weight or less. When the amount of unreacted glycidyl ether is more than 5% by weight, an unexpected side reaction may occur when blended in a product, which is not preferable.
化粧料用基材は、ポリアルキレンイミン誘導体のほかに、ポリアルキレンイミン誘導体合成時に用いた溶媒を含んでいてもよい。溶媒としては、水、イソプロピルアルコール、ブチレングリコール、プロピレングリコール、エタンジオール等が挙げられ、好ましくは水である。 The base material for cosmetics may contain the solvent used at the time of polyalkyleneimine derivative synthesis in addition to the polyalkyleneimine derivative. Examples of the solvent include water, isopropyl alcohol, butylene glycol, propylene glycol, ethanediol, and the like, preferably water.
本発明の化粧料用基剤は、乳化安定化剤、分散剤として特に良好であるが、用途はそれらに限定されるものではない。用途としては例えば、乳化剤、可溶化剤、分散剤、消泡剤、潤滑剤、浸透剤、洗浄剤、抗菌剤、消臭剤等に用いることできる。 The cosmetic base of the present invention is particularly good as an emulsion stabilizer and a dispersant, but the application is not limited thereto. Applications can be used for emulsifiers, solubilizers, dispersants, antifoaming agents, lubricants, penetrants, cleaning agents, antibacterial agents, deodorants, and the like.
本発明は前記ポリアルキレンイミン誘導体からなる化粧料用基材を含む化粧料でもある。本発明の化粧料に含まれる化粧料用基剤の配合量は特には限定されないが、通常0.001〜50質量%、好ましくは0.01〜30質量%配合される。 This invention is also cosmetics containing the base material for cosmetics consisting of the said polyalkyleneimine derivative. Although the compounding quantity of the base for cosmetics contained in the cosmetics of this invention is not specifically limited, Usually 0.001-50 mass%, Preferably 0.01-30 mass% is mix | blended.
本発明の化粧料の形態は、特に限定されず、W/O型乳化化粧料、O/W型乳化化粧料、W/O/W乳化化粧料、油水両連続相からなる化粧料、油性化粧料などいずれでもよいが、特にW/O型乳化化粧料として好適に用いることができる。 The form of the cosmetic of the present invention is not particularly limited, and is a W / O type emulsified cosmetic, an O / W type emulsified cosmetic, a W / O / W emulsified cosmetic, a cosmetic comprising both continuous phases of oil and water, and an oily cosmetic. However, it can be suitably used as a W / O emulsified cosmetic.
化粧料には、本発明の化粧料用基材以外に、油剤を5〜95質量%含有するが、10〜90質量%を含有することが好ましい。 In addition to the cosmetic base material of the present invention, the cosmetic contains 5 to 95% by mass of an oil agent, but preferably 10 to 90% by mass.
化粧料に使用できる油剤としては、炭化水素油、高級アルコール、高級脂肪酸、エステル油、油脂を含むトリグリセリド、シリコーン油を併用することが好ましい。炭化水素油としては、流動パラフィン、ポリブテン、水添ポリイソブテン、水添ポリデセン、スクワラン、スクワレン、プリスタン、軽質イソパラフィン、軽質流動イソパラフィン、重質流動イソパラフィン、流動イソパラフィン、テトラデセン、イソヘキサデカン、イソドデカン、α―オレフィンオリゴマー、ワセリン、マイクロクリスタリンワックス、パラフィン、ポリエチレン、セレシン等を挙げることができる。好ましくは、流動パラフィン、水添ポリイソブテン、スクワラン、ワセリンである。これらを1種類もしくは2種類以上、用いることができる。 As oil agents that can be used in cosmetics, it is preferable to use hydrocarbon oils, higher alcohols, higher fatty acids, ester oils, triglycerides including fats and oils, and silicone oils in combination. Hydrocarbon oils include liquid paraffin, polybutene, hydrogenated polyisobutene, hydrogenated polydecene, squalane, squalene, pristane, light isoparaffin, light liquid isoparaffin, heavy liquid isoparaffin, liquid isoparaffin, tetradecene, isohexadecane, isododecane, α-olefin. Examples include oligomers, petrolatum, microcrystalline wax, paraffin, polyethylene, and ceresin. Preferred are liquid paraffin, hydrogenated polyisobutene, squalane and petrolatum. One or more of these can be used.
高級アルコールは、直鎖型、分岐型、飽和型、不飽和型のいずれでもよい。このような高級アルコールとしては、オクチルアルコール、ノニルアルコール、デシルアルコール、ウンデシルアルコール、ラウリルアルコール、ミリスチルアルコール、セチルアルコール、セトステアリルアルコール、イソセチルアルコール、ステアリルアルコール、オレイルアルコール、イソステアリルアルコール、アラキルアルコール、ベヘニルアルコール、ホホバアルコールなどが炭素数8以上の高級アルコールが例示できる。これらを1種類もしくは2種類以上用いることもできる。 The higher alcohol may be linear, branched, saturated, or unsaturated. Such higher alcohols include octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, lauryl alcohol, myristyl alcohol, cetyl alcohol, cetostearyl alcohol, isocetyl alcohol, stearyl alcohol, oleyl alcohol, isostearyl alcohol, aralkyl. Alcohol, behenyl alcohol, jojoba alcohol and the like can be exemplified by higher alcohols having 8 or more carbon atoms. These can be used alone or in combination of two or more.
高級脂肪酸は、直鎖型、分岐型、飽和型、不飽和型、水酸基含有型のいずれでもよい。このような高級脂肪酸としては、カプリル酸、カプリン酸、2−エチルへキサン酸、ラウリン酸、ミリスチン酸、ミリストレイン酸、ヤシ油脂肪酸、牛脂脂肪酸、パーム油脂肪酸、パルミチン酸、パルミトレン酸、ステアリン酸、オレイン酸、イソステアリン酸、リシノール酸、リノール酸、リノレン酸、アラキジン酸、ベヘン酸、アラキドン酸、エルカ酸などの炭素数8以上の高級脂肪酸が例示できる。これらを1種類もしくは2種類以上用いることもできる。 The higher fatty acid may be any of linear, branched, saturated, unsaturated, and hydroxyl group-containing types. Such higher fatty acids include caprylic acid, capric acid, 2-ethylhexanoic acid, lauric acid, myristic acid, myristoleic acid, coconut oil fatty acid, beef tallow fatty acid, palm oil fatty acid, palmitic acid, palmitoleic acid, stearic acid And higher fatty acids having 8 or more carbon atoms such as oleic acid, isostearic acid, ricinoleic acid, linoleic acid, linolenic acid, arachidic acid, behenic acid, arachidonic acid and erucic acid. These can be used alone or in combination of two or more.
エステル油としては、セバシン酸ジエチル、2−エチルヘキサン酸セチル、2−エチルヘキサン酸イソセチル、パルミチン酸イソプロピル、パルミチン酸オクチル、パルミチン酸2−エチルヘキシル、イソステアリン酸イソプロピル、イソステアリン酸2−ヘキシルデシル、イソステアリン酸イソステアリル、トリイソステアリン酸トリメチロールプロパン、ミリスチン酸オクチルドデシル、ミリスチン酸イソプロピル、ミリスチン酸イソステアリル、ミリスチン酸イソセチル、ラウリン酸ヘキシル、オレイン酸エチル、オレイン酸デシル、ピバリン酸イソステアリル、ステアリン酸ブチル、ステアリン酸オクチル、ステアリン酸ステアリル、イソステアリン酸イソプロピル、イソノナン酸イソノニル、イソノナン酸2−エチルヘキシル、イソノナン酸イソデシル、イソノナン酸イソトリデシル、エルカ酸オクチルドデシル、ジデカン酸ネオペンチルグリコール、テトラエチルヘキサン酸ペンタエリスリチル、リンゴ酸ジイソステアリル、トリエチルヘキサン酸トリメチロールプロパンアジピン酸ジデシル、アジピン酸ジデシル、(アジピン酸・2−エチルへキサン酸・ステアリン酸)グリセリルオリゴエステル、イソステアリン酸グリセリル、イソステアリン酸硬化ヒマシ油、イソステアリン酸コレステリル、イソステアリン酸バチル、イソステアリン酸フィトステリル、オキシステアリン酸オクチル、オレイン酸グリセリル、オレイン酸ジグリセリル、オレイン酸ジヒドロコレステリル、オレイン酸フィトステリル、ジヤシ油脂肪酸ペンタエリスリット、ステアリン酸硬化ヒマシ油、ステアリン酸ジグリセリル、軟質ラノリン脂肪酸コレステリル、ヒドロキシステアリン酸コレステリル、ヘキサオキシステアリン酸ジペンタエリトリット、モノヒドロキシステアリン酸硬化ヒマシ油、ラノリン脂肪酸イソステアリル、ラノリン脂肪酸イソプロピル、ラノリン脂肪酸オクチルドデシル、ラノリン脂肪酸コレステリル、リシノレイン酸グリセリル、リシノレイン酸セチルなどが例示できる。これらを1種類もしくは2種類以上用いることができる。油脂を含むトリグリセリドとしては、カプロン酸、カプリル酸、カプリン酸、2−エチルヘキサン酸、ラウリン酸、ミリスチン酸、ミリストレイン酸、ヤシ油脂肪酸、牛脂脂肪酸、パーム油脂肪酸、パルミチン酸、パルミトレイン酸、ステアリン酸、オレイン酸、イソステアリン酸、リノール酸、リノレン酸、アラキジン酸、べヘン酸、アラキドン酸、エルカ酸などの炭素数6以上の高級脂肪酸のトリグリセリド、トリオキシステアリン酸グリセリル、トリ(カプリル・カプリン・ミリスチン・ステアリン酸)グリセリド、トリラノリン脂肪酸グリセリル、オリーブ油、トウモロコシ油、落花生油、菜種油、ゴマ油、大豆油、ヤシ油、パーム油、パーム核油、ヒマシ油、アマニ油、ホホバ油、つばき油、ひまわり油、マカデミアナッツ油、茶実油、綿実油、シソ油、サフワラー油、キョウニン油、牛脂、豚脂などの動植物油脂などが例示できる。これらを1種類もしくは2種類以上用いることができる。 Ester oils include diethyl sebacate, cetyl 2-ethylhexanoate, isocetyl 2-ethylhexanoate, isopropyl palmitate, octyl palmitate, 2-ethylhexyl palmitate, isopropyl isostearate, 2-hexyldecyl isostearate, isostearic acid Isostearyl, trimethylolpropane triisostearate, octyldodecyl myristate, isopropyl myristate, isostearyl myristate, isocetyl myristate, hexyl laurate, ethyl oleate, decyl oleate, isostearyl pivalate, butyl stearate, stearin Octyl acid, stearyl stearate, isopropyl isostearate, isononyl isononanoate, 2-ethylhexyl isononanoate, Isodecyl nonanoate, isotridecyl isononanoate, octyldodecyl erucate, neopentyl glycol didecanoate, pentaerythrityl tetraethylhexanoate, diisostearyl malate, trimethylolpropane triethylhexanoate didecyl adipate, didecyl adipate (adipic acid 2-ethylhexanoic acid / stearic acid) glyceryl oligoester, glyceryl isostearate, isostearic acid hydrogenated castor oil, cholesteryl isostearate, batyl isostearate, phytosteryl isostearate, octyl oxystearate, glyceryl oleate, diglyceryl oleate, Dihydrocholesteryl oleate, phytosteryl oleate, coconut oil fatty acid pentaerythritol, stearic acid cured castor Oil, diglyceryl stearate, soft lanolin fatty acid cholesteryl, cholesteryl hydroxystearate, dipentaerythritol hexaoxystearate, monohydroxystearic acid hydrogenated castor oil, lanolin fatty acid isostearyl, lanolin fatty acid isopropyl, lanolin fatty acid octyldodecyl, lanolin fatty acid Examples thereof include cholesteryl, glyceryl ricinoleate, cetyl ricinoleate and the like. One or more of these can be used. Examples of triglycerides containing fats and oils include caproic acid, caprylic acid, capric acid, 2-ethylhexanoic acid, lauric acid, myristic acid, myristoleic acid, coconut oil fatty acid, beef tallow fatty acid, palm oil fatty acid, palmitic acid, palmitoleic acid, stearin Triglycerides of higher fatty acids having 6 or more carbon atoms such as acid, oleic acid, isostearic acid, linoleic acid, linolenic acid, arachidic acid, behenic acid, arachidonic acid, erucic acid, glyceryl trioxystearate, tri (capryl-caprin, (Myristin / stearic acid) glycerides, trilanolin fatty acid glyceryl, olive oil, corn oil, peanut oil, rapeseed oil, sesame oil, soybean oil, palm oil, palm oil, palm kernel oil, castor oil, flaxseed oil, jojoba oil, camellia oil, sunflower oil , Macadamia nut oil, tea Oil, cottonseed oil, perilla oil, Safuwara oil, apricot kernel oil, beef tallow, animal and vegetable fats and oils such as lard can be exemplified. One or more of these can be used.
シリコーン油としては、ジメチルポリシロキサン、メチルフェニルポリシロキサン、メチルハイドロジェンポリシロキサン等の鎖状ポリシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサシロキサン、テトラヒドロテトラメチルシクロテトラシロキサンなどの環状ポリシロキサン、ポリオキシエチレンポリアルキルシロキサンが例示できる。これらを1種類もしくは2種類以上、用いることができる。これら油剤のうち、炭化水素油、エステル油、シリコーン油が特に好ましい。 Silicone oils include linear polysiloxanes such as dimethylpolysiloxane, methylphenylpolysiloxane, and methylhydrogenpolysiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, and tetrahydrotetramethylcyclotetrasiloxane. Examples thereof include cyclic polysiloxanes such as polyoxyethylene polyalkylsiloxane. One or more of these can be used. Of these oils, hydrocarbon oils, ester oils, and silicone oils are particularly preferable.
本発明の化粧料においてはさらに必要に応じて、本発明の効果を損なわない範囲で、化粧料、医薬品などに一般的に用いられている各種成分を配合することが可能である。例えば、炭化水素、高級アルコール、高級脂肪酸およびこれらのトリグリセリド、エステル油、動植物油脂、シリコーン、ビタミン類、紫外線吸収剤、水溶性高分子、酸化防止剤、陽イオン性界面活性剤、陰イオン性界面活性剤、両性界面活性剤、非イオン性界面活性剤、金属イオン封鎖剤、エタノール、増粘剤、防腐剤、色素、顔料、香料などが挙げられる。 In the cosmetics of the present invention, various components generally used in cosmetics, pharmaceuticals and the like can be blended as needed, as long as the effects of the present invention are not impaired. For example, hydrocarbons, higher alcohols, higher fatty acids and their triglycerides, ester oils, animal and vegetable oils, silicones, vitamins, UV absorbers, water-soluble polymers, antioxidants, cationic surfactants, anionic interfaces Examples include activators, amphoteric surfactants, nonionic surfactants, sequestering agents, ethanol, thickeners, preservatives, dyes, pigments, and fragrances.
また、本発明のポリアルキレンイミン誘導体を配合してなる化粧料の製品形態は、前述の形態に特に限定されるものではないが、例えば、皮膚外用剤が挙げられる。皮膚外用剤としては、化粧水、乳液、クリーム、パック等のスキンケア化粧料;ファンデーション、口紅、アイシャドー等のメークアップ化粧料;日焼け止め化粧料(サンスクリーン剤);ボディー化粧料;芳香化粧料;メーク落とし、ボディーシャンプー等の皮膚化粧料;ヘアリキッド、ヘアトニック、ヘアコンディショナー、ヘアシャンプー、リンス、育毛剤等の毛髪化粧料;制汗剤、軟膏等が例示できる。特に毛髪化粧料や制汗剤等については抗菌・消臭作用によって臭いを防止する効果が期待できるため、望ましい。 Moreover, the product form of the cosmetic formed by blending the polyalkyleneimine derivative of the present invention is not particularly limited to the above-mentioned form, and examples thereof include an external preparation for skin. Skin external preparations include skin care cosmetics such as lotions, emulsions, creams and packs; makeup cosmetics such as foundations, lipsticks and eye shadows; sunscreen cosmetics (sunscreen agents); body cosmetics; aromatic cosmetics Skin cosmetics such as make-up removers and body shampoos; hair cosmetics such as hair liquids, hair tonics, hair conditioners, hair shampoos, rinses, hair restorers; antiperspirants and ointments. In particular, hair cosmetics and antiperspirants are desirable because they can be expected to prevent odors by antibacterial and deodorant actions.
以下に、実施例および比較例によって本発明をより具体的に説明するが、本発明はこれらに限定されるものではない。
[アミン価の測定法]
アミン価とは樹脂1g中にふくまれるアミノ基のモル数(mmol)のことである。ポリエチレンイミンのアミン価は、メタノール溶液中で、0.5mol/Lのp−トルエンスルホン酸標準溶液を用いた電位差滴定により算出した。
[エポキシ当量]
エポキシ当量とは、1当量のエポキシ基を含む物質の質量である。これは分子構造より計算することも可能であるし、秤量した試料をクロロホルムに溶解させ、酢酸と臭化テトラエチルアンモニウム酢酸溶液を加えた後、過塩素酸酢酸標準液を滴下して電位差滴定をすることによっても測定可能である。ここでは、デナコール(登録商標)のカタログ値を採用した。
[グリシジルエーテルの転化率]
グリシジルエーテルの転化率は、反応液中に残存するグリシジルエーテルの量を検出器にFIDを備えるガスクロマトグラフィー((株)島津製作所製;GC−2010)を用いて、内部標準法で定量することにより算出した。
Hereinafter, the present invention will be described more specifically with reference to Examples and Comparative Examples, but the present invention is not limited to these.
[Measurement method of amine value]
The amine value is the number of moles (mmol) of amino groups contained in 1 g of resin. The amine value of polyethyleneimine was calculated by potentiometric titration using a 0.5 mol / L p-toluenesulfonic acid standard solution in a methanol solution.
[Epoxy equivalent]
The epoxy equivalent is the mass of a substance containing 1 equivalent of an epoxy group. This can also be calculated from the molecular structure. Dissolve the weighed sample in chloroform, add acetic acid and tetraethylammonium bromide acetic acid solution, then drop the perchloric acid acetic acid standard solution and perform potentiometric titration. Can also be measured. Here, the catalog value of Denacol (registered trademark) was adopted.
[Conversion rate of glycidyl ether]
The conversion rate of glycidyl ether is quantified by an internal standard method using a gas chromatography (manufactured by Shimadzu Corporation; GC-2010) equipped with FID as a detector for the amount of glycidyl ether remaining in the reaction solution. Calculated by
[窒素原子あたりの疎水基の導入量]
ポリアルキレンイミン誘導体の窒素原子あたりの疎水基の導入量(モル%)は以下の式から算出される。
[Introduction amount of hydrophobic group per nitrogen atom]
The introduction amount (mol%) of the hydrophobic group per nitrogen atom of the polyalkyleneimine derivative is calculated from the following formula.
[重量平均分子量および数平均分子量の測定方法]
ゲル浸透クロマトグラフィー(GPC)による重量平均分子量および数平均分子量の測定は、HLC−8320GPC EcoSEC(東ソー株式会社製)を用いて以下の条件で行った。
[Method for measuring weight average molecular weight and number average molecular weight]
The weight average molecular weight and the number average molecular weight were measured by gel permeation chromatography (GPC) using HLC-8320GPC EcoSEC (manufactured by Tosoh Corporation) under the following conditions.
カラム:SHODEX OHpak SB−802.5HQ、SB−803HQ
カラム温度:40℃
溶離液:0.5M酢酸+0.2M硝酸ナトリウム水溶液/アセトニトリル=50/50(体積比)
検出器:RI
検量線:標準ポリエチレングリコール(アジレントテクノロジー(株)社製)。
Column: SHODEX OHpak SB-802.5HQ, SB-803HQ
Column temperature: 40 ° C
Eluent: 0.5M acetic acid + 0.2M sodium nitrate aqueous solution / acetonitrile = 50/50 (volume ratio)
Detector: RI
Calibration curve: Standard polyethylene glycol (manufactured by Agilent Technologies).
(製造例1〜6)
表1に示される重合体1〜6を下記の手順で合成した。なお、原料は以下の原料を用いた。
(Production Examples 1-6)
Polymers 1 to 6 shown in Table 1 were synthesized by the following procedure. The following raw materials were used as raw materials.
ポリエチレンイミン
・エポミン(登録商標)SP−006(重合体1,2,4〜6;数平均分子量:600[カタログ値]、重量平均分子量:760)、SP−018(重合体3;数平均分子量:1,800[カタログ値]、重量平均分子量:1,310)((株)日本触媒製)
グリシジルエーテル
・2−エチルヘキシルグリシジルエーテル(デナコール(登録商標)EX−121;ナガセケムテックス(株)製)
・ラウリルグリシジルエーテル(デナコール(登録商標)EX−192;ナガセケムテックス(株)製)
・ラウリル(EO)15グリシジルエーテル(デナコール(登録商標)EX−171;ナガセケムテックス(株)製)
温度計、還流冷却器、撹拌装置を備えた500mLの四つ口フラスコに、下記表1に示される種類及び量のポリエチレンイミン(PEI)を仕込み、撹拌しながら下記表1に示される種類及び量のグリシジルエーテル(GE)を添加した。この重合体混合物を55℃に昇温して8時間反応し、重合体を得た。ガスクロマトグラフィーで未反応のグリシジルエーテルを分析し、グリシジルエーテルの転化率を算出して、下記表1に「GE転化率(%)」として示す。また、ポリエチレンイミンの窒素原子あたりの疎水基の導入量を算出して、下記表1に「疎水基の導入量(モル%)」として示す。
Polyethyleneimine Epomin (registered trademark) SP-006 (polymers 1, 2, 4 to 6; number average molecular weight: 600 [catalog value], weight average molecular weight: 760), SP-018 (polymer 3; number average molecular weight) : 1,800 [catalog value], weight average molecular weight: 1,310) (manufactured by Nippon Shokubai Co., Ltd.)
Glycidyl ether 2-ethylhexyl glycidyl ether (Denacol (registered trademark) EX-121; manufactured by Nagase ChemteX Corporation)
Lauryl glycidyl ether (Denacol (registered trademark) EX-192; manufactured by Nagase ChemteX Corporation)
Lauryl (EO) 15 glycidyl ether (Denacol (registered trademark) EX-171; manufactured by Nagase ChemteX Corporation)
A 500 mL four-necked flask equipped with a thermometer, a reflux condenser, and a stirrer is charged with the type and amount of polyethyleneimine (PEI) shown in Table 1 below, and the type and amount shown in Table 1 below while stirring. Of glycidyl ether (GE) was added. This polymer mixture was heated to 55 ° C. and reacted for 8 hours to obtain a polymer. Unreacted glycidyl ether was analyzed by gas chromatography, the conversion rate of glycidyl ether was calculated, and is shown as “GE conversion rate (%)” in Table 1 below. In addition, the amount of introduced hydrophobic groups per nitrogen atom of polyethyleneimine was calculated and shown in Table 1 as “introduced amount of hydrophobic groups (mol%)”.
<乳化安定性の評価>
[調製方法]
流動パラフィン 30.0 質量%
化粧料用基材 5.0 質量%
水 65.0 質量%
流動パラフィン(モレスコ製モレスコホワイトP−70)と化粧料用基材を、70℃にて均一に撹拌し、さらに同温度にて水をゆっくり添加して予備溶解した。これをホモミキサーにて撹拌して(5000rpm×5分間)、W/O型乳化剤組成物を得た。
[評価基準]
作成した化粧料用基材組成物を乳化直後および40℃で1ヶ月間保管した後の乳化状態を下記の基準により、目視で判断した。結果を表2に示す。
○:安定なエマルジョン状態。
×:わずかに油浮きが見られる状態。
××:完全にクリーミングまたは分離している状態。
<Evaluation of emulsion stability>
[Preparation method]
Liquid paraffin 30.0% by mass
Base material for cosmetics 5.0% by mass
Water 65.0% by mass
Liquid paraffin (Molesco White P-70 manufactured by Moresco) and a cosmetic base material were uniformly stirred at 70 ° C., and water was slowly added at the same temperature to be preliminarily dissolved. This was stirred with a homomixer (5000 rpm × 5 minutes) to obtain a W / O type emulsifier composition.
[Evaluation criteria]
The emulsified state of the prepared cosmetic base composition immediately after emulsification and after storage at 40 ° C. for 1 month was visually judged according to the following criteria. The results are shown in Table 2.
○: Stable emulsion state.
X: A state in which oil floating is slightly observed.
XX: completely creamed or separated.
<W/O型乳液の安定性評価>
本発明の化粧品用基剤を使用してW/O型乳液を調製した。以下の組成からなる基剤のうち油相および水相をそれぞれ70℃にて加温溶解して均一に溶解した後に、撹拌しながら油相に、水相を同温度にゆっくり添加して、室温まで冷却した。
油相:
流動パラフィン 25.0質量%
ラノリン 2.0質量%
ミツロウ 2.0質量%
水添ポリイソブテン 20.0質量%
化粧料用基材 5.0質量%
香料 適量
水相:
グリセリン 5.0質量%
水 残部
乳化直後と、40℃で1ヶ月間保管した後の乳化状態を下記の基準により、目視で判断した。結果を表3に示す。
○:安定なエマルジョン状態。
×:わずかに油浮きが見られる状態。
××:完全にクリーミングまたは分離している状態。
<Stability evaluation of W / O type emulsion>
A W / O emulsion was prepared using the cosmetic base of the present invention. Of the base comprising the following composition, the oil phase and the water phase were each dissolved by heating at 70 ° C. to dissolve uniformly, and then the water phase was slowly added to the oil phase while stirring to the room temperature. Until cooled.
Oil phase:
Liquid paraffin 25.0% by mass
Lanolin 2.0% by mass
Beeswax 2.0% by mass
Hydrogenated polyisobutene 20.0% by mass
Cosmetic base material 5.0% by mass
Perfume appropriate amount water phase:
Glycerin 5.0% by mass
The emulsified state immediately after emulsification of the remainder of the water and after storage at 40 ° C. for 1 month was determined visually according to the following criteria. The results are shown in Table 3.
○: Stable emulsion state.
X: A state in which oil floating is slightly observed.
XX: completely creamed or separated.
<抗菌性能評価>
上記実施例7〜12で調製したW/O型乳液を50gミルクボトルに移し、蓋の空いた状態で実験室内で1日静置した。その後、蓋を締めて1か月35℃で保管した。保管後のエマルジョンを1g取得し、生理食塩水5gで懸濁し、そのうちの0.1mlをマイクロピペッターで取得してミューラーヒントン寒天培地に塗布し、35℃で72時間培養を行った。出現したコロニー数によって抗菌性能を下記の基準で判断した。結果を表4に示す。
○ :コロニーの出現なし
× :1〜100個のコロニーが出現
××:100個以上のコロニーが出現
<Antimicrobial performance evaluation>
The W / O type emulsion prepared in Examples 7 to 12 above was transferred to a 50 g milk bottle and allowed to stand in the laboratory for one day with the lid open. Then, the lid was closed and stored at 35 ° C. for one month. 1 g of the emulsion after storage was obtained, suspended in 5 g of physiological saline, 0.1 ml of the suspension was obtained with a micropipette, applied to Mueller Hinton agar medium, and cultured at 35 ° C. for 72 hours. The antibacterial performance was judged according to the following criteria based on the number of colonies that appeared. The results are shown in Table 4.
○: No appearance of colonies ×: Appearance of 1 to 100 colonies XX: Appearance of 100 or more colonies
本発明のポリアルキレンイミン誘導体を用いた化粧料用基材は、皮膚や毛髪用の化粧料に配合することができる。 The base material for cosmetics using the polyalkyleneimine derivative of the present invention can be blended in cosmetics for skin and hair.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6164324A (en) * | 1984-09-05 | 1986-04-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | Modified polyamine |
JP2014141458A (en) * | 2012-12-26 | 2014-08-07 | Kao Corp | Gelatinous hair cosmetic |
JP2014141459A (en) * | 2012-12-26 | 2014-08-07 | Kao Corp | Hair detergent |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6164324A (en) * | 1984-09-05 | 1986-04-02 | Nippon Shokubai Kagaku Kogyo Co Ltd | Modified polyamine |
JP2014141458A (en) * | 2012-12-26 | 2014-08-07 | Kao Corp | Gelatinous hair cosmetic |
JP2014141459A (en) * | 2012-12-26 | 2014-08-07 | Kao Corp | Hair detergent |
Non-Patent Citations (1)
Title |
---|
日光ケミカルズ株式会社、日本サーファクタント工業株式会社、東色ピグメント株式会社, 化粧品ハンドブック, JPN6019041599, 1 November 1996 (1996-11-01), pages 126 - 155, ISSN: 0004279054 * |
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