JP5720998B2 - Cosmetic base and cosmetic comprising the same - Google Patents
Cosmetic base and cosmetic comprising the same Download PDFInfo
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- JP5720998B2 JP5720998B2 JP2011075270A JP2011075270A JP5720998B2 JP 5720998 B2 JP5720998 B2 JP 5720998B2 JP 2011075270 A JP2011075270 A JP 2011075270A JP 2011075270 A JP2011075270 A JP 2011075270A JP 5720998 B2 JP5720998 B2 JP 5720998B2
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- 239000000344 soap Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 239000000600 sorbitol 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
- 238000003860 storage Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-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
- 239000002562 thickening agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- 230000005068 transpiration Effects 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 238000009489 vacuum treatment Methods 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
Description
本発明は、ポリアルキレングリコール誘導体からなる化粧料用基剤及びそれを配合してなる化粧料に関する。 The present invention relates to a cosmetic base comprising a polyalkylene glycol derivative and a cosmetic comprising the same.
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性基剤が汎用されている。油性基剤としては、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特に汎用され、これらと水を安定配合するために、水中油型及び油中水型(以下、それぞれO/W型及びW/O型と略記する場合がある)など様々な乳化形態がある。
その中でも、W/O型乳化化粧料は、水分の蒸散の防止、肌を乾燥から保護など優れた機能を有しており、消費者のニーズも高まっている。しかし、このような機能があるものの、外相が油相であるために、油っぽさが残るといった使用感での欠点があった。さらに、O/W型乳化化粧料に比べて、乳化の安定性を保持するのが困難であった。その理由の一つとして、油相(連続相)の粘度低下が挙げられる。粘度低下は、ストークスの法則より、粒子移動速度の上昇をもたらし、結果的に、粒子の凝集やクリーミングを促進すると考えられている。したがって、従来から、固形・半固形油分を配合することで油相に粘性を付与し安定性の高い乳化物を得る提案があるが、べたつき感を生じてしまい使用感には十分に満足いくものではなかった。
Oily bases are widely used in cosmetics in order to impart smoothness and moist feeling to the skin and hair. Oily bases include hydrocarbon oils such as liquid paraffin and squalane, oils and triglycerides such as vegetable oils, ester oils with ester bonds, and silicone oils such as dimethylsiloxane. For this purpose, there are various emulsified forms such as an oil-in-water type and a water-in-oil type (hereinafter sometimes abbreviated as O / W type and W / O type, respectively).
Among these, W / O type emulsified cosmetics have excellent functions such as prevention of moisture transpiration and protecting the skin from drying, and consumer needs are also increasing. However, although there is such a function, since the outer phase is an oil phase, there is a drawback in the feeling of use that oiliness remains. Furthermore, it was difficult to maintain the stability of emulsification as compared with O / W type emulsified cosmetics. One reason for this is a decrease in the viscosity of the oil phase (continuous phase). It is believed that the decrease in viscosity results in an increase in particle movement speed and, as a result, promotes particle aggregation and creaming according to Stokes' law. Therefore, there has been a proposal to obtain a highly stable emulsion by adding viscosity to the oil phase by blending solid and semi-solid oils, but it is sticky and sufficiently satisfactory for use. It wasn't.
使用感を改善する方法としては、内水相比を高めてみずみずしい使用感とする提案がある(例えば特許文献1)。この提案では、モノオレイン酸グリセリン、モノイソステアリン酸グリセリン、ポリオキシエチレングリセリルモノイソステアレートから選ばれる乳化剤を用いることで乳化安定性を保っているが、塗布時の滑らかさ、肌へのなじみについて、十分満足いくものではなかった。
さらに、使用感を改善する方法として、油相に揮発性油分を配合する提案がある(例えば特許文献2)。この提案では、鎖状シリコーン油又は炭化水素油からなる高揮発性油分、ポリオキシアルキレン−オルガノポリシロキサン交互ブロック共重合体を含有することを特徴としている。しかし、揮発速度が速い揮発性油分を主成分として配合した場合、塗布後の肌なじみや、乳化安定性に十分満足いくものではなかった。
さらに、直鎖ブロック型アルキレンオキシド誘導体を用いたゲル状組成物の提案もなされている(例えば特許文献3)。この提案では、適度な粘性を付与でき、使用感が良好であるが、乳化安定性は十分に満足のいくものではなかった。
このため、塗布時の滑らかさ、肌へのなじみなど使用感が良好で、乳化安定性が良好なW/O型乳化化粧料の開発が望まれていた。
As a method for improving the feeling of use, there is a proposal for increasing the internal water phase ratio to provide a fresh feeling of use (for example, Patent Document 1). In this proposal, emulsification stability is maintained by using an emulsifier selected from glyceryl monooleate, glyceryl monoisostearate, polyoxyethylene glyceryl monoisostearate, but smoothness during application and familiarity with the skin It was not satisfactory enough.
Furthermore, as a method for improving the feeling of use, there is a proposal of blending a volatile oil component in the oil phase (for example, Patent Document 2). This proposal is characterized by containing a highly volatile oil component composed of a chain silicone oil or a hydrocarbon oil and a polyoxyalkylene-organopolysiloxane alternating block copolymer. However, when a volatile oil component having a high volatilization rate is blended as a main component, skin conformity after application and emulsification stability are not satisfactory.
Furthermore, the proposal of the gel-like composition using a linear block type alkylene oxide derivative is also made | formed (for example, patent document 3). In this proposal, moderate viscosity can be imparted and the feeling in use is good, but the emulsion stability is not sufficiently satisfactory.
For this reason, it has been desired to develop a W / O type emulsified cosmetic having good usability such as smoothness at the time of application and familiarity with the skin and good emulsification stability.
本発明が解決しようとする課題は、塗布時の滑らかさ、肌へのなじみなど使用感が良好で、しかも乳化安定性にも優れる化粧料用基剤を提供することである。さらに、優れた感触及び乳化安定性を有する化粧料、特に、油中水型乳化化粧料を提供することである。 The problem to be solved by the present invention is to provide a cosmetic base having good usability such as smoothness at the time of application and familiarity with the skin, and also excellent in emulsion stability. Furthermore, it is to provide a cosmetic having excellent feel and emulsion stability, in particular, a water-in-oil emulsion cosmetic.
本発明者らは、上記課題を解決するために鋭意検討した結果、特定のポリアルキレングリコール誘導体を化粧料用基剤として配合することで、本発明の課題を達成することを見出した。
すなわち、本発明は以下に示されるものである。
(1)下記式(I)により示されるポリアルキレングリコール誘導体からなる化粧料用基剤である。
Z−{O−(AO)a−(EO)k−(AO)b−R}m (I)
(式中、Zは、水酸基を3〜6個有する水溶性多価アルコールから水酸基を除いた残基、mは3〜6、EOはオキシエチレン基、AOは炭素数4〜8のオキシアルキレン基を示し、EOとAOはブロック状に結合している。
a及びbはAOの平均付加モル数、kはEOの平均付加モル数を示し、aは0、bは1〜50、a+bは1〜50、kは10〜45、(a+b+k)×mは120〜250である。また、EOとAOの合計量100質量部に対し、EOの質量割合は40〜75質量部である。
Rは、水素原子又は炭素数12〜24の脂肪酸残基を示す。)
(2)AOが、1,2−オキシブチレン基である、前記(1)記載の化粧料用基剤。
(3)前記(1)又は(2)に記載の化粧料用基剤を含有する化粧料。
(4)下記の成分(ア)、(イ)、(ウ)、(エ)を含有し、全質量に対する成分(ア)の含有量が0.01〜30質量%、成分(イ)と成分(ウ)の合計量が10〜95質量%、成分(エ)の含有量が1〜70質量%、かつ、成分(イ)と成分(ウ)の合計量100質量部に対する成分(イ)の量が10質量部以上である、油中水型乳化化粧料。
(ア)前記(1)又は(2)に記載の化粧料用基剤
(イ)エステル油又はトリグリセリドから選ばれる1種以上の極性油
(ウ)炭化水素油
(エ)水As a result of intensive studies to solve the above problems, the present inventors have found that the problems of the present invention can be achieved by blending a specific polyalkylene glycol derivative as a cosmetic base.
That is, the present invention is as follows.
(1) A cosmetic base comprising a polyalkylene glycol derivative represented by the following formula (I).
Z- {O- (AO) a- (EO) k- (AO) b -R} m (I)
(In the formula, Z is a residue obtained by removing a hydroxyl group from a water-soluble polyhydric alcohol having 3 to 6 hydroxyl groups, m is 3 to 6, EO is an oxyethylene group, and AO is an oxyalkylene group having 4 to 8 carbon atoms. EO and AO are bonded in a block form.
a and b are the average addition mole number of AO, k is the average addition mole number of EO, a is 0 , b is 1 to 50, a + b is 1 to 50, k is 10 to 45 , (a + b + k) × m is it is 120-250. Further, the total amount of 100 parts by mass of the EO and AO, the mass ratio of EO is 40-75 parts by weight.
R represents a hydrogen atom or a fatty acid residue having 12 to 24 carbon atoms. )
(2) The cosmetic base according to (1) , wherein AO is a 1,2-oxybutylene group.
(3) A cosmetic comprising the cosmetic base according to (1) or (2).
(4) Contains the following components (A), (I), (U), (E), the content of component (A) relative to the total mass is 0.01 to 30% by mass, component (A) and component The total amount of (U) is 10 to 95% by mass, the content of component (D) is 1 to 70% by mass, and the amount of component (A) is 100 parts by mass with respect to the total amount of component (A) and component (U). A water-in-oil emulsified cosmetic, the amount of which is 10 parts by mass or more.
(A) Base for cosmetics as described in (1) or (2) (I) One or more polar oils selected from ester oils or triglycerides (U) Hydrocarbon oils (E) Water
本発明の化粧料用基剤は、特に、油性成分とのなじみ性がよく、これを配合した化粧料は、乳化安定性に優れる。特に、これを配合した油中水型乳化化粧料は、肌に塗布したときに滑らかでのびがよいなど、塗布感に優れ、肌へのなじみがよく、塗布後に皮膜感が少なく、突っ張り感や油っぽさがないなど、使用感に優れる。すなわち、本発明は、乳化安定性と使用感をともに充足する優れた化粧料用基剤、及びこれを含有する油中水型乳化化粧料を提供した点で顕著な効果を奏する。 The base for cosmetics of the present invention has particularly good compatibility with oily components, and cosmetics formulated with these are excellent in emulsion stability. In particular, water-in-oil emulsified cosmetics formulated with this are excellent when applied to the skin, such as smooth and stretchy, have a good feeling on the skin, are well-familiar with the skin, have less film feeling after application, There is no oiliness and it is excellent in the feeling of use. That is, the present invention has a remarkable effect in that it provides an excellent cosmetic base that satisfies both the emulsion stability and the feeling in use, and a water-in-oil emulsified cosmetic containing the same.
[化粧料用基剤]
本発明に係る化粧料用基剤は、下記式(I)で表されるポリアルキレングリコール誘導体である。
Z−{O−(AO)a−(EO)k−(AO)b−R}m (I)
式中、Zは、水酸基を3〜6個有する水溶性多価アルコールから水酸基を除いた残基を示す。水溶性多価アルコールとしては、水酸基が3個の、グリセリン、トリメチロールプロパン、水酸基が4個の、ジグリセリン、エリスリトール、ペンタエリスリトール、ソルビタン、メチルグルコシド、水酸基が5個のキシリトール、トリグリセリン、水酸基が6個のソルビトール、イノシトール、ジペンタエリスリトールが例示される。好ましくは、水酸基を4個以上持つアルコールから水酸基を除いた残基であり、さらに好ましくは、乳化安定性と使用感の両面から、水酸基が4個のジグリセリン、ペンタエリスリトールである。
mは3〜6、好ましくは4〜6、より好ましくは4である。mが2以下では、W/O型乳化化粧料に配合した場合、求める乳化安定性が得られない。mが7以上では、塗布の時の滑らかさを損なうことがあり好ましくない。
EOはオキシエチレン基であり、本発明のポリアルキレングリコール誘導体の親水基となる。kはEOの平均付加モル数であり、k×mは、式(I)の全EO付加モル数である。kは、1〜50、好ましくは10〜45である。kが1より小さいと十分な親水性が得られず、W/O型乳化剤として使用したときに、水を内包する効果に劣る場合があり好ましくない。また、kが50より大きいと、べたつき感を生じるばかりか、油剤との相溶性に劣る場合があり好ましくない。
[Cosmetic base]
The cosmetic base according to the present invention is a polyalkylene glycol derivative represented by the following formula (I).
Z- {O- (AO) a - (EO) k - (AO) b -R} m (I)
In formula, Z shows the residue remove | excluding the hydroxyl group from the water-soluble polyhydric alcohol which has 3-6 hydroxyl groups. The water-soluble polyhydric alcohol includes three hydroxyl groups, glycerin, trimethylolpropane, four hydroxyl groups, diglycerin, erythritol, pentaerythritol, sorbitan, methyl glucoside, five hydroxyl groups xylitol, triglycerin, hydroxyl group Are 6 sorbitol, inositol and dipentaerythritol. A residue obtained by removing a hydroxyl group from an alcohol having 4 or more hydroxyl groups is preferable, and diglycerin and pentaerythritol having 4 hydroxyl groups are more preferable from the viewpoints of emulsion stability and usability.
m is 3-6, preferably 4-6, more preferably 4. When m is 2 or less, the desired emulsion stability cannot be obtained when blended in a W / O emulsion cosmetic. When m is 7 or more, the smoothness at the time of application may be impaired, which is not preferable.
EO is an oxyethylene group and is a hydrophilic group of the polyalkylene glycol derivative of the present invention. k is the average number of moles of EO added, and k × m is the total number of moles of EO added in formula (I). k is 1 to 50, preferably 10 to 45. When k is less than 1, sufficient hydrophilicity cannot be obtained, and when used as a W / O type emulsifier, the effect of enclosing water may be inferior. Moreover, when k is larger than 50, not only a sticky feeling is produced, but also the compatibility with the oil agent may be inferior.
AOは炭素数4〜8のオキシアルキレン基であり、本発明のポリアルキレングルコール誘導体の親油基となる。炭素数4の1,2−オキシブチレン基、炭素数5の1,2−オキシペンチレン基、炭素数6の1,2−オキシヘキシレン基、炭素数7の1,2−オキシへプチレン基、炭素数8の1,2−オキシオクチレン基が例示されるが、好ましくは、1,2−オキシブチレン基又は1,2−オキシオクチレン基であり、より好ましくは、1,2−オキシブチレン基である。
AOは1種でも2種以上でも構わないが、2種以上の場合、付加形態は、ランダム状、ブロック状のどちらでもよい。
a及びbはAOの平均付加モル数であり、aは0〜50、bは0〜50、a+bは1〜50であり、好ましくは、5〜30である。a+bが1より小さいと、Rが脂肪酸残基であっても、十分な親油性が得られず、乳化安定性に劣る。また、50より大きくなると、肌へのなじみ性に劣る場合があり好ましくない。(a+b)×mは、式(I)の全AO付加モル数である。
さらに、Zに対して、親水基−親油基の配列である場合、すなわち、a=0の場合がより効果的である。
(a+b+k)×mは、100〜300であり、好ましくは120〜250である。100より小さいと、求める乳化安定性が得られない。また、300より大きいと塗布時の滑らかさや肌へのなじみを損なうことがあり好ましくない。
EOとAOの合計量を100質量部としたとき、EOの質量比は10〜75質量部であり、好ましくは20〜75質量部、より好ましくは40〜75質量部である。10質量部より小さいと十分な親油性が得られず、乳化安定性に劣る。また、75質量部より大きいと、W/O型乳化剤として、水を内包させる効果に劣る場合があり好ましくない。
EOとAOはブロック状に結合している。ランダム状では、十分な乳化可溶化力が得られない。
AO is an oxyalkylene group having 4 to 8 carbon atoms and serves as a lipophilic group of the polyalkylene glycol derivative of the present invention. 1,2-oxybutylene group having 4 carbon atoms, 1,2-oxypentylene group having 5 carbon atoms, 1,2-oxyhexylene group having 6 carbon atoms, 1,2-oxyheptylene group having 7 carbon atoms And a 1,2-oxyoctylene group having 8 carbon atoms is preferable, and a 1,2-oxybutylene group or a 1,2-oxyoctylene group is preferable, and a 1,2-oxyoctylene group is more preferable. It is a butylene group.
AO may be one type or two or more types, but in the case of two or more types, the addition form may be either random or block.
a and b are average addition mole number of AO, a is 0-50, b is 0-50, a + b is 1-50, Preferably, it is 5-30. When a + b is smaller than 1, even if R is a fatty acid residue, sufficient lipophilicity cannot be obtained and the emulsion stability is poor. On the other hand, if it exceeds 50, the conformability to the skin may be inferior. (A + b) × m is the total number of added AO moles of formula (I).
Furthermore, when Z is a hydrophilic group-lipophilic group arrangement, that is, a = 0, it is more effective.
(A + b + k) × m is 100 to 300, preferably 120 to 250. If it is less than 100, the desired emulsion stability cannot be obtained. On the other hand, if it is larger than 300, the smoothness during application and the familiarity with the skin may be impaired.
When the total amount of EO and AO is 100 parts by mass, the mass ratio of EO is 10 to 75 parts by mass, preferably 20 to 75 parts by mass, and more preferably 40 to 75 parts by mass. When it is less than 10 parts by mass, sufficient lipophilicity cannot be obtained and the emulsion stability is poor. On the other hand, if it is larger than 75 parts by mass, the effect of encapsulating water as a W / O type emulsifier may be inferior.
EO and AO are combined in a block shape. In a random state, sufficient emulsification solubilization power cannot be obtained.
Rは、水素原子又は炭素数12〜24の脂肪酸残基を示す。
式(I)のポリアルキレングリコール誘導体は、W/O型乳化剤として用いる場合、親油性である(AO)b−Rの部分を油相側に配向すると考えられる。
Rが脂肪酸残基の場合、エステル化前の全水酸基に対してエステル化される水酸基数の割合をエステル化率とすると、エステル化率は85%以下、好ましくは70%以下である。85%より高いと塗布時の滑らかさに劣る場合があり好ましくない。脂肪酸残基の炭素数としては、好ましくは16〜22である。炭素数が12より小さいと、乳化安定性の向上には寄与しない。24より大きいと、塗布時の滑らかさに劣り好ましくない。
炭素数12〜24の脂肪酸残基としては、飽和脂肪酸、不飽和脂肪酸あるいは分岐脂肪酸でもよく、さらには、ヒドロキシル基置換脂肪酸でもよい。このような脂肪酸としては、ラウリン酸、トリデカン酸、イソトリデカン酸、ミリスチン酸、パルミチン酸、イソパルミチン酸、ステアリン酸、イソステアリン酸、エイコサン酸、べへン酸、テトラコサン酸、ミリストレン酸、パルミトレン酸、オレイン酸、エライジン酸、エルカ酸、リノール酸、リノレン酸、アラキドン酸、ヒドロキシステアリン酸、ヤシ油脂肪酸、パーム核油脂肪酸、硬化パーム核油脂肪酸、パーム油脂肪酸、牛脂脂肪酸、硬化牛脂脂肪酸、豚脂脂肪酸、ヒマシ油脂肪酸、硬化ヒマシ油脂肪酸などの脂肪酸が挙げられ、これらの混合物でもよい。好ましくは、ラウリン酸、パルミチン酸、ステアリン酸、イソステアリン酸、オレイン酸、ヒマシ油脂肪酸、硬化ヒマシ油脂肪酸、より好ましくは、ヒマシ油脂肪酸、硬化ヒマシ油脂肪酸である。
R represents a hydrogen atom or a fatty acid residue having 12 to 24 carbon atoms.
When the polyalkylene glycol derivative of the formula (I) is used as a W / O type emulsifier, it is considered that the (AO) b -R portion that is lipophilic is oriented toward the oil phase.
When R is a fatty acid residue, the esterification rate is 85% or less, preferably 70% or less, assuming that the ratio of the number of hydroxyl groups esterified to the total hydroxyl groups before esterification is the esterification rate. If it is higher than 85%, the smoothness during application may be inferior, which is not preferable. The number of carbon atoms of the fatty acid residue is preferably 16-22. If the carbon number is less than 12, it does not contribute to the improvement of the emulsion stability. When it is larger than 24, the smoothness at the time of application is inferior, which is not preferable.
The fatty acid residue having 12 to 24 carbon atoms may be a saturated fatty acid, an unsaturated fatty acid or a branched fatty acid, and may further be a hydroxyl group-substituted fatty acid. Such fatty acids include lauric acid, tridecanoic acid, isotridecanoic acid, myristic acid, palmitic acid, isopalmitic acid, stearic acid, isostearic acid, eicosanoic acid, behenic acid, tetracosanoic acid, myristolenic acid, palmitoleic acid, olein Acid, elaidic acid, erucic acid, linoleic acid, linolenic acid, arachidonic acid, hydroxystearic acid, coconut oil fatty acid, palm kernel oil fatty acid, hardened palm kernel oil fatty acid, palm oil fatty acid, beef tallow fatty acid, hardened tallow fatty acid, pork tallow fatty acid And fatty acids such as castor oil fatty acid and hydrogenated castor oil fatty acid, and a mixture thereof may be used. Preferred are lauric acid, palmitic acid, stearic acid, isostearic acid, oleic acid, castor oil fatty acid, hardened castor oil fatty acid, and more preferred are castor oil fatty acid and hardened castor oil fatty acid.
本発明の式(I)で示されるポリオキシアルキレングリコール誘導体は、公知の方法で製造することができる。例えば、水酸基を3〜6個有する水溶性多価アルコールに、アルカリもしくは酸触媒下、オキシエチレン、炭素数4〜8のオキシアルキレン、オキシエチレンの順に付加重合した後に、必要に応じて脂肪酸とのエステル化反応や低級アルコールの脂肪酸エステルとのエステル交換反応で得ることができる。
また、a=0のとき、式(I)は、式(II)によって表すこともできる。
Z−{O−(EO)k−(AO)b−R}m (II)
式(II)のポリアルキレングリコール誘導体は、Zにオキシエチレンを付加重合させた下記式(III)のポリアルキレングリコール誘導体に、AOを付加重合し、必要に応じて脂肪酸とエステル化反応させることで得ることができる。
Z−{O−(EO)k−H}m (III)
式(III)のポリアルキレングリコール誘導体は、ゲル浸透クロマトグラフィー(以下、GPCと略記する場合がある)において、溶出開始点から溶出終了点までの全ピークにおける多分散度Mw/Mnが1.04以下 であることが好ましい。多分散度が1に近いものは、分子量分布が狭い物質である。
本発明の式(I)において、a=0のとき、EO付加反応終了時点の多分散度が、1.04以下で分布が狭ければ、より効果的に油相と水相の界面に配向することができ、乳化安定性が高くなる。
The polyoxyalkylene glycol derivative represented by the formula (I) of the present invention can be produced by a known method. For example, after addition polymerization of water-soluble polyhydric alcohol having 3 to 6 hydroxyl groups in the order of oxyethylene, oxyalkylene having 4 to 8 carbon atoms, and oxyethylene in the order of an alkali or acid catalyst, if necessary, with a fatty acid. It can be obtained by an esterification reaction or a transesterification reaction with a fatty acid ester of a lower alcohol.
When a = 0, the formula (I) can also be expressed by the formula (II).
Z- {O- (EO) k- (AO) b -R} m (II)
The polyalkylene glycol derivative of the formula (II) is obtained by adding AO to the polyalkylene glycol derivative of the following formula (III) obtained by addition polymerization of oxyethylene to Z and esterifying with a fatty acid as necessary. Can be obtained.
Z- {O- (EO) k -H} m (III)
The polyalkylene glycol derivative of the formula (III) has a polydispersity Mw / Mn of 1.04 in all peaks from the elution start point to the elution end point in gel permeation chromatography (hereinafter sometimes abbreviated as GPC). It is preferable that Those having a polydispersity close to 1 are substances having a narrow molecular weight distribution.
In the formula (I) of the present invention, when a = 0, the polydispersity at the end of the EO addition reaction is 1.04 or less and the distribution is narrow. And the emulsification stability is increased.
本発明の化粧料用基剤は、油剤に対して、適度な粘性を付与することで乳化安定性を高める効果もあることから、W/O型乳化剤の他に、油剤の粘性制御剤として使用することもできる。 The cosmetic base of the present invention also has an effect of improving the emulsion stability by imparting an appropriate viscosity to the oil agent. Therefore, it is used as a viscosity control agent for oil agents in addition to the W / O type emulsifier. You can also
[化粧料]
本発明の化粧料は、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、高級脂肪酸及びこれらのトリグリセリド、エステル油、ロウ類、動植物油脂、シリコーン油、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、水などが挙げられる。
本発明の化粧料は、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。W/O型乳化化粧料として用いる場合、エステル油、トリグリセリド及び/又は炭化水素油からなる油相を用いることが効果的である。
例えば、下記の成分(ア)、(イ)、(ウ)、(エ)を含有し、全質量に対する成分(ア)の含有量が0.01〜30質量%、成分(イ)と成分(ウ)の合計量が10〜95質量%、成分(エ)の含有量が1〜70質量%、かつ、成分(イ)と成分(ウ)の合計量100質量部に対する成分(イ)の量が10質量部以上である、油中水型乳化化粧料が好適である。
[Cosmetics]
The cosmetic of the present invention can be blended with various components that are generally used in cosmetics, pharmaceuticals, and the like 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, waxes, animal and vegetable oils, silicone oils, vitamins, UV absorbers, water-soluble polymers, antioxidants, cationic surfactants, Examples include anionic surfactants, amphoteric surfactants, nonionic surfactants, sequestering agents, ethanol, thickeners, preservatives, dyes, pigments, fragrances, and water.
The cosmetic of the present invention can be suitably used particularly as a W / O type emulsified cosmetic. When used as a W / O emulsified cosmetic, it is effective to use an oil phase composed of ester oil, triglyceride and / or hydrocarbon oil.
For example, it contains the following components (A), (I), (U), (D), the content of the component (A) is 0.01 to 30% by mass relative to the total mass, the component (A) and the component ( The total amount of c) is 10 to 95% by mass, the content of component (d) is 1 to 70% by mass, and the amount of component (a) relative to 100 parts by mass of the total amount of components (b) and (c) Is a water-in-oil emulsified cosmetic composition having a mass of 10 parts by mass or more.
成分(イ)のうち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、トリデカン酸、イソトリデカン酸、ミリスチン酸、パルミチン酸、イソパルミチン酸、ステアリン酸、イソステアリン酸、エイコサン酸、べへン酸、テトラコサン酸、ミリストレン酸、パルミトレン酸、オレイン酸、エライジン酸、エルカ酸、リノール酸、リノレン酸、アラキドン酸、ヒドロキシステアリン酸、ヤシ油脂肪酸、パーム核油脂肪酸、硬化パーム核油脂肪酸、パーム油脂肪酸、牛脂脂肪酸、硬化牛脂脂肪酸、豚脂脂肪酸、ヒマシ油脂肪酸、硬化ヒマシ油脂肪酸など、炭素数6以上の高級脂肪酸のトリグリセリド、オリーブ油、ヒマワリ油、パーム油、パーム核油、サフラワー油、ヒマシ油、硬化ヒマシ油、ヤシ油、ツバキ油、カカオ脂、シア脂などの動植物油脂類などが例示できる。エステル油としては、オレイン酸エチル、リノール酸エチル、ミリスチン酸イソプロピル、パルミチン酸イソプロピル、イソステアリン酸イソプロピル、ラノリン脂肪酸イソプロピル、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、2−エチルへキサン酸ステアリル、2−エチルへキサン酸イソステアリル、パルミチン酸セチル、パルミチン酸2−エチルヘキシル、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、ミリスチン酸ミリスチル、ミリスチン酸セチル、ミリスチン酸オクチルドデシル、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、オレイン酸デシル、オレイン酸オクチルドデシル、ピバリン酸イソステアリル、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、オレイン酸ジヒドロコレステリル、オレイン酸フィトステリル、ジペンタエリトリット脂肪酸エステル、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、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、ステアリン酸コレステリル、ラノリン脂肪酸コレステリル、リシノレイン酸セチル、コハク酸ジオクチル、乳酸セチル、ジカプリル酸プロピレングリコール、ジカプリン酸プロピレングリコール、ジノナン酸プロピレングリコール、ジ(カプリル・カプリン酸)プロピレングリコール、ジステアリン酸プロピレングリコール、ジイソステアリン酸プロピレングリコール、ジオレイン酸プロピレングリコールなどが例示できる。また、ミツロウ、モクロウ、カルナバロウ、ラノリン、キャンデリラロウ、ホホバ油などロウ類も使用できる。これらを1種もしくは2種以上用いることができる。好ましくは、炭素数6以上の高級脂肪酸のトリグリセリド、動植物油脂類、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、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、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、ミツロウ、モクロウなどロウ類である。 Among the components (I), triglycerides include caproic acid, caprylic acid, capric acid, 2-ethylhexanoic acid, lauric acid, tridecanoic acid, isotridecanoic acid, myristic acid, palmitic acid, isopalmitic acid, stearic acid, isostearic acid, Eicosanoic acid, behenic acid, tetracosanoic acid, myristolenic acid, palmitoleic acid, oleic acid, elaidic acid, erucic acid, linoleic acid, linolenic acid, arachidonic acid, hydroxystearic acid, palm oil fatty acid, palm kernel oil fatty acid, hardened palm Triglycerides of higher fatty acids having 6 or more carbon atoms such as nuclear oil fatty acid, palm oil fatty acid, beef tallow fatty acid, hardened beef tallow fatty acid, pork tallow fatty acid, castor oil fatty acid, hardened castor oil fatty acid, olive oil, sunflower oil, palm oil, palm kernel oil , Safflower oil, castor oil, hydrogenated castor oil, Shea oil, camellia oil, cacao butter, animal and vegetable fats and oils such as shea butter can be exemplified. As ester oils, ethyl oleate, ethyl linoleate, isopropyl myristate, isopropyl palmitate, isopropyl isostearate, lanolin fatty acid isopropyl, cetyl 2-ethylhexanoate, isocetyl 2-ethylhexanoate, stearyl 2-ethylhexanoate , 2-ethylhexanoate isostearyl, cetyl palmitate, 2-ethylhexyl palmitate, 2-hexyldecyl isostearate, isostearyl isostearate, trimethylolpropane triisostearate, myristyl myristate, cetyl myristate, octyl myristate Dodecyl, isostearyl myristate, isocetyl myristate, hexyl laurate, decyl oleate, octyldodecyl oleate, isos pivalate Allyl, isopropyl isostearate, isononyl isononanoate, 2-ethylhexyl isononanoate, isodecyl isononanoate, isotridecyl isononanoate, octyldodecyl erucate, neopentyl glycol didecanoate, pentaerythrityl tetraethylhexanoate, diisostearyl malate, triethylhexane Acid trimethylolpropane didecyl adipate, didecyl adipate, (adipic acid, 2-ethylhexanoic acid, stearic acid) glyceryl oligoester, glyceryl isostearate, isostearic acid hydrogenated castor oil, cholesteryl isostearate, batyl isostearate, isostearic acid Phytosteryl, octyl oxystearate, dihydrocholesteryl oleate, phytosteryl oleate, di Teratrit fatty acid ester, coconut oil fatty acid pentaerythritol, stearic acid hydrogenated castor oil, soft lanolin fatty acid cholesteryl, hydroxy stearic acid cholesteryl, hexahydroxystearic acid dipentaerythritol, monohydroxy stearic acid hydrogenated castor oil, lanolin fatty acid isostearyl, lanolin Fatty acid isopropyl, lanolin fatty acid octyldodecyl, cholesteryl stearate, lanolin fatty acid cholesteryl, cetyl ricinoleate, dioctyl succinate, cetyl lactate, propylene glycol dicaprylate, propylene glycol dicaprate, propylene glycol dinonanoate, di (capryl / caprate) propylene Glycol, propylene glycol distearate, propylene glycol diisostearate And propylene glycol dioleate. In addition, waxes such as beeswax, mole, carnauba wax, lanolin, candelilla wax, jojoba oil can be used. One or more of these can be used. Preferably, triglycerides of higher fatty acids having 6 or more carbon atoms, animal and vegetable oils and fats, cetyl 2-ethylhexanoate, isocetyl 2-ethylhexanoate, isopropyl palmitate, 2-ethylhexyl palmitate, isopropyl isostearate, 2-hexyl isostearate Examples thereof include decyl, octyldodecyl myristate, isopropyl myristate, isostearyl myristate, isocetyl myristate, isononyl isononanoate, 2-ethylhexyl isononanoate, isodecyl isononanoate, isotridecyl isononanoate, beeswax, and mole.
成分(ウ)の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、マイクロクリスタリンワックスである。これらを1種又は2種以上、用いることができる。 As the component (c) hydrocarbon oil, liquid paraffin, polybutene, hydrogenated polyisobutene, hydrogenated polydecene, squalane, squalene, pristane, light isoparaffin, light liquid isoparaffin, heavy liquid isoparaffin, liquid isoparaffin, tetradecene, isohexadecane, Examples thereof include isododecane, α-olefin oligomer, petrolatum, microcrystalline wax, paraffin, polyethylene, and ceresin. Preferred are liquid paraffin, hydrogenated polyisobutene, squalane, petroleum jelly and microcrystalline wax. One or more of these can be used.
成分(イ)と成分(ウ)の合計量を100重量部としたときに、成分(イ)の量は10質量部以上であり、好ましくは、10〜90質量部である。10質量部以下であると、成分(ア)と油相との相溶性に劣り、乳化安定性に劣る場合があり好ましくない。
成分(エ)の水は、一般にW/O乳化化粧料の水相として用いられるものであれば、特には限定されず、例えば、蒸留水やイオン交換水などの精製水、生理食塩水、リン酸緩衝水溶液等を用いることができる。水は、1〜70質量%用いる。70質量%を超えると、水相として内包することが困難となり安定な乳化化粧料が得られない。
When the total amount of component (I) and component (U) is 100 parts by weight, the amount of component (I) is 10 parts by mass or more, and preferably 10 to 90 parts by mass. When the amount is 10 parts by mass or less, the compatibility between the component (a) and the oil phase is inferior, and the emulsion stability may be inferior.
The water of component (d) is not particularly limited as long as it is generally used as the water phase of W / O emulsified cosmetics. For example, purified water such as distilled water or ion exchange water, physiological saline, phosphorus An acid buffer aqueous solution or the like can be used. Water is used in an amount of 1 to 70% by mass. When it exceeds 70 mass%, it becomes difficult to encapsulate as a water phase, and a stable emulsified cosmetic cannot be obtained.
さらに、本発明の油中水型乳化化粧料の形態は常温において液状、半固体、固体の何れかの形態をとることができる。他の成分を本発明の性能を損なわない範囲で含有することも可能である。例えば、低級アルコール、シリコーン油、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、陽イオン性界面活性剤、半極性界面活性剤、水溶性高分子、有機又は無機塩類、pH調整剤、殺菌剤、キレート剤、抗酸化剤、紫外線吸収剤、ビタミン類、動植物由来の天然エキス、色素、顔料、香料などが挙げられる。
また、本発明の化粧料用基剤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、皮膚外用剤であることが好ましい。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;ボディー化粧料;芳香化粧料;クレンジングオイルなどのメーク落とし、ボディーシャンプー、ハンドソープ等の皮膚化粧料;ヘアリキッド、ヘアオイル、ヘアトニック、育毛剤等の毛髪化粧料;軟膏等が例示できる。
Furthermore, the form of the water-in-oil emulsified cosmetic of the present invention can take any form of liquid, semi-solid, and solid at room temperature. It is also possible to contain other components as long as the performance of the present invention is not impaired. For example, lower alcohols, silicone oils, anionic surfactants, amphoteric surfactants, nonionic surfactants, cationic surfactants, semipolar surfactants, water-soluble polymers, organic or inorganic salts, Examples include pH adjusters, bactericides, chelating agents, antioxidants, ultraviolet absorbers, vitamins, natural extracts derived from animals and plants, pigments, pigments, and fragrances.
Moreover, the product form of the cosmetic formed by blending the cosmetic base of the present invention is not particularly limited to the above-described form, but is preferably a skin external preparation. 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; body cosmetics; aromatic cosmetics; cleansing oils, etc. Skin cosmetics such as make-up removers, body shampoos, hand soaps; hair cosmetics such as hair liquids, hair oils, hair tonics, hair restorers; ointments and the like.
以下、実施例により本発明をさらに詳しく説明するが、本発明はこれに限定されるものではない。
本発明に係る化粧料用基剤の合成例を示す。各合成例において、水酸基価は、JISK1557
6.4に準じて測定した。
GPCにおける多分散度は、下記のシステムにて測定した。
分析機器 :SHODEX GPC SYSTEM−11(昭和電工社製)
標準物質 :ポリエチレングリコール
サンプルサイズ :10%×100×0.001mL
溶離液 :THF
流速 :1.0mL/min
カラム :SHODEX KF804L(昭和電工社製)
カラムサイズ :I.D.8mm×30cm×3
カラム温度 :40℃
検出器 :RI×8
EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to this.
The synthesis example of the base for cosmetics which concerns on this invention is shown. In each synthesis example, the hydroxyl value is JISK1557.
Measured according to 6.4.
The polydispersity in GPC was measured by the following system.
Analytical instrument: SHODEX GPC SYSTEM-11 (manufactured by Showa Denko)
Standard substance: Polyethylene glycol Sample size: 10% x 100 x 0.001 mL
Eluent: THF
Flow rate: 1.0 mL / min
Column: SHODEX KF804L (manufactured by Showa Denko)
Column size: I.D. D. 8mm x 30cm x 3
Column temperature: 40 ° C
Detector: RI x 8
[合成例]
合成例1:ポリオキシブチレン(48モル)ポリオキシエチレン(88モル)ペンタエリスリトールエーテル(化合物1)
ペンタエリスリトール45g、トルエン50g、水酸化カリウム8.0gをオートクレーブ中に仕込み、オートクレーブ中の空気を乾燥窒素で置換した後、撹拌しながら、110℃にて、滴下装置より、エチレンオキシド1292gを滴下して2時間撹拌した。引き続き、110℃にて1,2−ブチレンオキシド1160gを滴下し、2時間撹拌した。その後、オートクレーブ内から、反応物を取り出し、塩酸で中和して、pH6〜7とし、含有するトルエン及び水分を除去するため、115℃、1時間、減圧処理を行い、最後に濾過をして塩を除去して、2345gの化合物1を得た。水酸基価は、エチレンオキシド反応後が56.0mgKOH/g、1,2−ブチレンオキシド反応後が30.0mgKOH/gであった。また、エチレンオキシド反応後のGPCの結果、多分散度は、1.025であった。
[Synthesis example]
Synthesis Example 1: Polyoxybutylene (48 mol) Polyoxyethylene (88 mol) Pentaerythritol ether (Compound 1)
After charging 45 g of pentaerythritol, 50 g of toluene, and 8.0 g of potassium hydroxide into the autoclave and replacing the air in the autoclave with dry nitrogen, 1292 g of ethylene oxide was dropped from a dropping device at 110 ° C. with stirring. Stir for 2 hours. Subsequently, 1160 g of 1,2-butylene oxide was added dropwise at 110 ° C. and stirred for 2 hours. Thereafter, the reaction product is taken out from the autoclave, neutralized with hydrochloric acid to pH 6-7, and subjected to vacuum treatment at 115 ° C. for 1 hour to remove contained toluene and moisture, and finally filtered. The salt was removed to give 2345 g of compound 1. The hydroxyl value was 56.0 mgKOH / g after the ethylene oxide reaction and 30.0 mgKOH / g after the 1,2-butylene oxide reaction. Moreover, the polydispersity was 1.025 as a result of GPC after the ethylene oxide reaction.
合成例2:トリヒマシ硬化油脂肪酸ポリオキシブチレン(30モル)ポリオキシエチレン(60モル)グリセリル(化合物2)
グリセリン31g、水酸化カリウム5.0gをオートクレーブ中に仕込み、オートクレーブ中の空気を乾燥窒素で置換した後、撹拌しながら、140℃にて滴下装置より、エチレンオキシド885gを滴下して2時間撹拌した。引き続き、140℃にて、1,2−ブチレンオキシド725gを滴下し、2時間撹拌した。その後、オートクレーブ内から、反応物を取り出し、塩酸で中和して、pH6〜7とし、含有する水分を除去するため、100℃にて1時間、減圧処理を行い、最後に濾過をして塩を除去して、1550gのポリオキシブチレン(30モル)ポリオキシエチレン(60モル)グリセリルエーテル(化合物3a)を得た。水酸基価は、エチレンオキシド反応後が62.1mgKOH/g、1,2−ブチレンオキシド反応後が35.0mgKOH/gであった。
得られた化合物3a1223gとヒマシ硬化油脂肪酸150gとを200℃にて10時間反応させ、化合物2を得た。水酸基価は、11.5mgKOH/gであることから、エステル化率は、67%であった。また、エチレンオキシド反応後のGPCの結果、多分散度は、1.028であった。
上記合成例1〜2に準じて、下記表1に示す組成のポリアルキレングリコール誘導体を合成した。
Synthesis Example 2: Tricastor oil fatty acid polyoxybutylene (30 mol) polyoxyethylene (60 mol) glyceryl (compound 2)
After charging 31 g of glycerin and 5.0 g of potassium hydroxide into the autoclave and replacing the air in the autoclave with dry nitrogen, 885 g of ethylene oxide was added dropwise from a dropping device at 140 ° C. with stirring and stirred for 2 hours. Subsequently, 725 g of 1,2-butylene oxide was added dropwise at 140 ° C. and stirred for 2 hours. Thereafter, the reaction product is taken out from the autoclave, neutralized with hydrochloric acid to pH 6-7, and subjected to reduced pressure treatment at 100 ° C. for 1 hour to remove the contained water, and finally filtered to obtain a salt. Then, 1550 g of polyoxybutylene (30 mol) polyoxyethylene (60 mol) glyceryl ether (compound 3a) was obtained. The hydroxyl value was 62.1 mgKOH / g after the ethylene oxide reaction and 35.0 mgKOH / g after the 1,2-butylene oxide reaction.
The compound 3a1223g obtained and the castor oil hardened fatty acid 150g were made to react at 200 degreeC for 10 hours, and the compound 2 was obtained. Since the hydroxyl value was 11.5 mgKOH / g, the esterification rate was 67%. In addition, as a result of GPC after the ethylene oxide reaction, the polydispersity was 1.028.
According to the synthesis examples 1 and 2, polyalkylene glycol derivatives having the compositions shown in Table 1 below were synthesized.
<実施例1〜7、比較例1〜7>
表2に示す組成にて、W/O型乳液を調製し、使用感及び乳化安定性の評価を行った。調製方法
[油相]
(ア)又は(ア’)成分
(イ)成分
(ウ)成分
モノオレイン酸ソルビタン
ポリオキシエチレン(20モル)モノオレイン酸ソルビタン
モノオレイン酸グリセリン
ポリオキシエチレン(5モル)グリセリルモノイソステアレート
防腐剤
香料
[水相]
(エ)成分
1,3−ブチレングリコール
ジプロピレングリコール
グリセリン<Example 1-7, Comparative Examples 1-7>
A W / O type emulsion was prepared with the composition shown in Table 2, and the feeling of use and the emulsion stability were evaluated. Preparation method [oil phase]
(A) or (A ') component (I) component (U) component sorbitan monooleate polyoxyethylene (20 mol) sorbitan monooleate monoglycerin polyoxyethylene (5 mol) glyceryl monoisostearate preservative Fragrance [Aqueous phase]
(D) Component 1,3-butylene glycol dipropylene glycol glycerin
油相と水相をそれぞれ70〜80℃にて加熱溶解させる。同温度にて、ホモジナイザーを用いて、5000rpmで攪拌しながら、油相に水相を徐々に加えて、5000rpmにて10分間攪拌した。その後、40℃以下に急冷して、乳液を得た。 The oil phase and the aqueous phase are dissolved by heating at 70 to 80 ° C., respectively. While stirring at 5000 rpm using a homogenizer at the same temperature, the water phase was gradually added to the oil phase and stirred at 5000 rpm for 10 minutes. Then, it cooled rapidly to 40 degrees C or less, and obtained the emulsion.
使用感の評価方法
20名の専門女性パネラーに、得られた乳液の[塗布時の滑らかさ]と[塗布後の肌へのなじみ]について、以下の基準にて評価してもらった。3.5点以上を合格基準とした。評価結果を表2に併せて示す。
[塗布時の滑らかさ]
25℃、相対湿度50%の環境下にて、調製直後の乳液を前腕内側部に塗布し、塗布時の使用感について以下の基準にて評価した。
5:のびが非常によく、非常に軽い感触
4:のびがよく、軽い感触
3:のびがやや悪く、少しひっかかる感触
2:のびが悪く、重い感触
1:のびが非常に悪く、べたべたする感触
[肌へのなじみ]
[塗布時の滑らかさ]の評価に引き続き、25℃、相対湿度50%の環境下にて1時間経過後の肌へのなじみについて、以下の基準にて評価した。
5:皮膜感が良好で、皮膚を柔らかくしている感触
4:適度な皮膜感があり、皮膚を柔らかくしている感触
3:皮膜感がやや強いが、皮膚を柔らかくしている感触
2:皮膜感がやや強く、皮膚がわずかに柔らかくなる感触
1:皮膜感が強く、皮膚がつっぱっている感触
Usability Evaluation Method Twenty professional female panelists evaluated the obtained emulsion for [smoothness during application] and [familiarity to the skin after application] according to the following criteria. An acceptance criterion of 3.5 points or more was used. The evaluation results are also shown in Table 2.
[Smoothness during application]
Under the environment of 25 ° C. and 50% relative humidity, the emulsion immediately after the preparation was applied to the inner side of the forearm, and the usability during application was evaluated according to the following criteria.
5: Very good and very light touch 4: Good and light feel 3: Slightly poor, slightly squeezed feel 2: Slightly poor and heavy feel 1: Very poor and sticky feel [ Familiarity to skin]
Subsequent to the evaluation of [Smoothness during application], conformity to the skin after 1 hour in an environment of 25 ° C. and 50% relative humidity was evaluated according to the following criteria.
5: Feeling of the skin is good and the skin is softening 4: Feeling of the skin is moderate and the skin is softening 3: The skin feeling is slightly strong, but the skin is softening 2: The film Feels slightly strong and feels slightly softer on the skin 1: Feels strong and the skin feels tight
乳化安定性の評価方法
乳化直後、室温及び40℃にて1ヶ月間保管した状態を目視した。
○○:乳化状態を維持。
○:下部にわずかに離水しているが、全体的に安定。
×:上部に油相、中層部に界面活性剤相、下部に水相が発現。
××:分離
Evaluation Method of Emulsification Stability Immediately after emulsification, the state of storage at room temperature and 40 ° C. for 1 month was visually observed.
◯: Maintain the emulsified state.
○: Slightly separated at the bottom, but stable overall.
X: An oil phase appears in the upper part, a surfactant phase in the middle part, and an aqueous phase in the lower part.
XX: Separation
本発明の処方例を以下に挙げる。何れの処方例も、「塗布時の滑らかさ」、「肌へのなじみ」、「乳化安定性」が良好であった。
<処方例1 W/O型マッサージクリーム>
[油相]
(ア)化合物1 3.5質量%
(イ)トリ(カプリル/カプリン酸)グリセリド 3.0質量%
(イ)ミツロウ 5.0質量%
(ウ)パラフィン 3.0質量%
(ウ)マイクロクリスタリンワックス 5.0質量%
(ウ)ワセリン 15.0質量%
(ウ)流動パラフィン 40.0質量%
モノステアリン酸ソルビタン 0.5質量%
ポリオキシエチレン(20モル)モノステアリン酸ソルビタン 0.5質量%
モノステアリン酸ポリオキシエチレン(75モル) 1.0質量%
香料 適量
[水相]
(エ)水 19.1質量%
1,2−ヘキシレングリコール 1.0質量%
1,3−ブチレングリコール
4.0質量%
調製方法
油相と水相をそれぞれ70〜80℃にて加熱溶解させる。同温度にて、ホモジナイザーを用いて、5000rpmで攪拌しながら、油相に水相を徐々に加えて、5000rpmにて10分間攪拌した。その後、40℃以下に急冷して、乳液を得た。
Examples of the formulation of the present invention are given below. In all the formulation examples, “smoothness during application”, “familiarity with skin”, and “emulsification stability” were good.
<Prescription Example 1 W / O Massage Cream>
[Oil phase]
(A) Compound 1 3.5% by mass
(I) Tri (capryl / capric acid) glyceride 3.0% by mass
(I) Beeswax 5.0% by mass
(U) Paraffin 3.0% by mass
(C) Microcrystalline wax 5.0% by mass
(U) Vaseline 15.0% by mass
(U) Liquid paraffin 40.0% by mass
Sorbitan monostearate 0.5% by mass
Polyoxyethylene (20 mol) sorbitan monostearate 0.5% by mass
Polyoxyethylene monostearate (75 mol) 1.0% by mass
Perfume appropriate amount [water phase]
(D) Water 19.1% by mass
1,2-hexylene glycol 1.0% by mass
1,3-butylene glycol
4.0% by mass
Preparation method An oil phase and an aqueous phase are dissolved by heating at 70 to 80 ° C, respectively. While stirring at 5000 rpm using a homogenizer at the same temperature, the water phase was gradually added to the oil phase and stirred at 5000 rpm for 10 minutes. Then, it cooled rapidly to 40 degrees C or less, and obtained the emulsion.
<処方例2 W/O型エモリエントクリーム>
[油相]
(ア)化合物2 2.0質量%
(イ)2−エチルへキサン酸セチル 3.0質量%
(イ)オリーブ油 5.0質量%
(イ)ラノリン 6.0質量%
(イ)ミツロウ 2.0質量%
(ウ)パラフィン 2.0質量%
(ウ)マイクロクリスタリンワックス 7.0質量%
(ウ)ワセリン 3.0質量%
(ウ)スクワラン 35.0質量%
親油型モノステアリン酸酸グリセリン 0.5質量%
トリイソステアリン酸ポリグリセリル−2 0.5質量%
ポリオキシエチレン(20モル)モノステアリン酸ソルビタン1.0質量%
防腐剤
適量
香料 適量
[水相]
(エ)水 26.8質量%
PEG#1500 3.0質量%
プロピレングリコール 3.0質量%
調製方法
油相と水相をそれぞれ70〜80℃にて加熱溶解させる。同温度にて、ホモジナイザーを用いて、5000rpmで攪拌しながら、油相に水相を徐々に加えて、5000rpmにて10分間攪拌した。その後、40℃以下に急冷して、乳液を得た。
<Prescription Example 2 W / O Emollient Cream>
[Oil phase]
(A) Compound 2 2.0% by mass
(I) Cetyl 2-ethylhexanoate 3.0% by mass
(I) Olive oil 5.0% by mass
(I) Lanolin 6.0% by mass
(I) Beeswax 2.0% by mass
(U) Paraffin 2.0% by mass
(C) Microcrystalline wax 7.0% by mass
(U) Vaseline 3.0% by mass
(U) Squalane 35.0% by mass
Lipophilic glyceryl monostearate 0.5% by mass
Polyglyceryl-2 triisostearate 0.5% by mass
Polyoxyethylene (20 mol) sorbitan monostearate 1.0% by mass
Preservative
Appropriate amount Perfume Appropriate amount [Aqueous phase]
(D) 26.8% by mass of water
PEG # 1500 3.0% by mass
Propylene glycol 3.0% by mass
Preparation method An oil phase and an aqueous phase are dissolved by heating at 70 to 80 ° C, respectively. While stirring at 5000 rpm using a homogenizer at the same temperature, the water phase was gradually added to the oil phase and stirred at 5000 rpm for 10 minutes. Then, it cooled rapidly to 40 degrees C or less, and obtained the emulsion.
<処方例3 W/O型サンスクリーンクリーム>
[油相]
(ア)化合物1 3.0質量%
(イ)トリ(カプリル/カプリン酸)グリセリド 8.0質量%
(ウ)スクワラン 30.0質量%
(ウ)水添ポリイソブテン 2.5質量%
パラメトキシケイ皮酸オクチル 5.0質量%
疎水化処理酸化チタン 3.0質量%
有機変性モンモリロナイト 2.0質量%
防腐剤 適量
香料 適量
[水相]
(エ)水 42.2質量%
1,3−ブチレングリコール 4.0質量%
調製方法
油相と水相をそれぞれ70〜80℃にて加熱溶解させる。同温度にて、ホモジナイザーを用いて、10000rpmで攪拌しながら、油相に水相を徐々に加えて、10000rpmにて30分間攪拌した。その後、40℃以下に急冷して、乳液を得た。
<Prescription Example 3 W / O Sunscreen Cream>
[Oil phase]
(A) Compound 1 3.0% by mass
(I) Tri (capryl / capric acid) glyceride 8.0% by mass
(U) Squalane 30.0% by mass
(C) Hydrogenated polyisobutene 2.5% by mass
Octyl paramethoxycinnamate 5.0% by mass
Hydrophobized titanium oxide 3.0% by mass
Organically modified montmorillonite 2.0% by mass
Preservative appropriate amount perfume appropriate amount [aqueous phase]
(D) Water 42.2% by mass
1,3-butylene glycol 4.0% by mass
Preparation method An oil phase and an aqueous phase are dissolved by heating at 70 to 80 ° C, respectively. While stirring at 10,000 rpm using a homogenizer at the same temperature, the water phase was gradually added to the oil phase and stirred at 10000 rpm for 30 minutes. Then, it cooled rapidly to 40 degrees C or less, and obtained the emulsion.
<処方例4 エモリエントオイルジェル>
[油相]
(ア)化合物5 10.0質量%
(イ)トリ(2−エチルヘキサン酸)グリセリド 70.0質量%
(ウ)流動パラフィン 5.0質量%
(ウ)水添ポリイソブテン 5.0質量%
ジイソステアリン酸ポリエチレングリコール(8モル) 5.0質量%
防腐剤
適量
香料 適量
[水相]
(エ)水 3.8質量%
ジプロピレングリコール 1.0質量%
調製方法
油相と水相をそれぞれ70〜80℃にて加熱溶解させる。同温度にて、攪拌しながら、油相に水相を徐々に加えて均一になるまで攪拌した。その後、冷却してエモリエントオイルジェルを得た。
処方例4の25℃での粘度を、E型粘度計RE105U(ロータコードNo.1、100rpm:東機産業株式会社製)にて測定したところ、4550mPa・sであった。
<Prescription Example 4 Emollient Oil Gel>
[Oil phase]
(A) Compound 5 10.0% by mass
(I) Tri (2-ethylhexanoic acid) glyceride 70.0% by mass
(U) Liquid paraffin 5.0% by mass
(C) Hydrogenated polyisobutene 5.0% by mass
Polyethylene glycol diisostearate (8 mol) 5.0% by mass
Preservative
Appropriate amount Perfume Appropriate amount [Aqueous phase]
(D) 3.8% by mass of water
Dipropylene glycol 1.0% by mass
Preparation method An oil phase and an aqueous phase are dissolved by heating at 70 to 80 ° C, respectively. While stirring at the same temperature, the aqueous phase was gradually added to the oil phase and stirred until uniform. Thereafter, it was cooled to obtain an emollient oil gel.
It was 4550 mPa * s when the viscosity in 25 degreeC of the formulation example 4 was measured with the E-type viscosity meter RE105U (rotor code No. 1, 100 rpm: Toki Sangyo Co., Ltd. product).
Claims (4)
Z−{O−(AO)a−(EO)k−(AO)b−R}m (I)
(式中、Zは、水酸基を3〜6個有する水溶性多価アルコールから水酸基を除いた残基、mは3〜6、EOはオキシエチレン基、AOは炭素数4〜8のオキシアルキレン基を示し、EOとAOはブロック状に結合している。
a及びbはAOの平均付加モル数、kはEOの平均付加モル数を示し、aは0、bは1〜50、a+bは1〜50、kは10〜45、(a+b+k)×mは120〜250である。また、EOとAOの合計量100質量部に対し、EOの質量割合は40〜75質量部である。
Rは、水素原子又は炭素数12〜24の脂肪酸残基を示す。)A cosmetic base comprising a polyalkylene glycol derivative represented by the following formula (I).
Z- {O- (AO) a- (EO) k- (AO) b -R} m (I)
(In the formula, Z is a residue obtained by removing a hydroxyl group from a water-soluble polyhydric alcohol having 3 to 6 hydroxyl groups, m is 3 to 6, EO is an oxyethylene group, and AO is an oxyalkylene group having 4 to 8 carbon atoms. EO and AO are bonded in a block form.
a and b are the average addition mole number of AO, k is the average addition mole number of EO, a is 0 , b is 1 to 50, a + b is 1 to 50, k is 10 to 45 , (a + b + k) × m is it is 120-250. Further, the total amount of 100 parts by mass of the EO and AO, the mass ratio of EO is 40-75 parts by weight.
R represents a hydrogen atom or a fatty acid residue having 12 to 24 carbon atoms. )
(ア)請求項1又は2に記載の化粧料用基剤
(イ)エステル油又はトリグリセリドから選ばれる1種以上の極性油
(ウ)炭化水素油
(エ)水Contains the following components (A), (I), (U), (E), the content of the component (A) relative to the total mass is 0.01 to 30% by mass, the components (A) and (U) The total amount of the component (a) is 10 to 95% by mass, the content of the component (e) is 1 to 70% by mass, and the amount of the component (a) is 10 parts by mass with respect to 100 parts by mass of the total amount of the components (a) and (c). A water-in-oil emulsified cosmetic that is at least part by mass.
(A) Base for cosmetics according to claim 1 or 2 (I) One or more polar oils selected from ester oils or triglycerides (U) Hydrocarbon oils (E) Water
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US9655821B2 (en) | 2013-04-05 | 2017-05-23 | The Procter & Gamble Company | Personal care composition comprising a pre-emulsified formulation |
EP3130398B1 (en) * | 2014-04-11 | 2019-07-24 | JFE Engineering Corporation | Temperature-sensitive absorbent, water treatment method, and water treatment apparatus |
US10806688B2 (en) | 2014-10-03 | 2020-10-20 | The Procter And Gamble Company | Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation |
US9993404B2 (en) | 2015-01-15 | 2018-06-12 | The Procter & Gamble Company | Translucent hair conditioning composition |
JP6893758B2 (en) * | 2015-09-02 | 2021-06-23 | ライオン株式会社 | W / O type emulsified composition |
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