JP2005097151A - Skin cosmetic - Google Patents
Skin cosmetic Download PDFInfo
- Publication number
- JP2005097151A JP2005097151A JP2003331467A JP2003331467A JP2005097151A JP 2005097151 A JP2005097151 A JP 2005097151A JP 2003331467 A JP2003331467 A JP 2003331467A JP 2003331467 A JP2003331467 A JP 2003331467A JP 2005097151 A JP2005097151 A JP 2005097151A
- Authority
- JP
- Japan
- Prior art keywords
- group
- branched
- branched polyglycerol
- silicone
- bonded
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002537 cosmetic Substances 0.000 title claims abstract description 38
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 84
- 229920000223 polyglycerol Polymers 0.000 claims abstract description 46
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 27
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 15
- 125000005647 linker group Chemical group 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical group OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 4
- 239000003021 water soluble solvent Substances 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000013329 compounding Methods 0.000 abstract description 2
- -1 oxyphenylene group Chemical group 0.000 description 41
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
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- 229910052786 argon Inorganic materials 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- UIVPNOBLHXUKDX-UHFFFAOYSA-N 3,5,5-trimethylhexyl 3,5,5-trimethylhexanoate Chemical compound CC(C)(C)CC(C)CCOC(=O)CC(C)CC(C)(C)C UIVPNOBLHXUKDX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
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Landscapes
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Abstract
Description
本発明は、皮膚用化粧料に関する。 The present invention relates to a skin cosmetic.
皮膚への塗布感触や、塗布後の肌感触を向上させる目的で、皮膚用化粧料に各種シリコーン類が配合されている。例えば、特許文献１及び特許文献２にはポリエーテル変性シリコーンをシリコーン油の乳化剤として用いた皮膚用化粧料が開示されている。しかし、高い配合安定性と塗布時および塗布後の良好な感触を両立させるのは困難で、シリコーンが本来有する効果が十分活かされているとはいいがたい。 Various silicones are blended in skin cosmetics for the purpose of improving the skin feel after application and the skin feel after application. For example, Patent Document 1 and Patent Document 2 disclose skin cosmetics using polyether-modified silicone as an emulsifier for silicone oil. However, it is difficult to achieve both high blending stability and a good feel at the time of application and after application, and it is difficult to say that the effects inherent in silicone are fully utilized.
また、特許文献３には、直鎖グリセロール変性シリコーン、もしくは３個のグリセロール基からなる分岐グリセロール変性シリコーンを用いた低刺激性化粧料が開示されているが、塗布後の感触が十分でなく、塗布後の良好な感触を有する皮膚用化粧料が求められている。
本発明の課題は、配合安定性に優れ、塗布後の肌感触が良好な皮膚用化粧料を提供することである。 The subject of this invention is providing the skin cosmetics which are excellent in mixing | blending stability and the skin feel after application | coating is favorable.
本発明者らは、特定の分岐ポリグリセロール基を有する分岐ポリグリセロール変性シリコーンを用いることで、上記課題を解決できる皮膚用化粧料が得られることを見出した。 The present inventors have found that a skin cosmetic that can solve the above problems can be obtained by using a branched polyglycerol-modified silicone having a specific branched polyglycerol group.
すなわち、本発明は、下記構造式（１）、（２）、（３）、（４）又は（５）で表されるグリセロール基又はグリシドール基が同一又は異なって平均４個以上結合し、且つ構造式（１）又は（５）で表される基を少なくとも１つ以上含む分岐ポリグリセロール鎖が、シリコーンのケイ素原子に連結基を介して少なくとも１つ結合した、分岐ポリグリセロール変性シリコーン（以下成分（ａ）という）を含む皮膚用化粧料、並びに更に水溶性溶剤（以下成分（ｂ）という）を含む皮膚用化粧料を提供する。 That is, in the present invention, the glycerol group or glycidol group represented by the following structural formula (1), (2), (3), (4) or (5) is the same or different, and an average of 4 or more bonds. Branched polyglycerol-modified silicone (hereinafter referred to as component) in which at least one branched polyglycerol chain containing at least one group represented by structural formula (1) or (5) is bonded to the silicon atom of silicone via a linking group A skin cosmetic comprising (a)) and a skin cosmetic further comprising a water-soluble solvent (hereinafter referred to as component (b)) are provided.
尚、上記構造式（１）の２つの酸素原子には、同一又は異なって上記構造式（１）、（２）、（３）、（４）又は（５）で表されるグリセロール基又はグリシドール基が結合し、構造式（２）の酸素原子には、上記構造式（１）、（２）、（３）、（４）又は（５）で表されるグリセロール基又はグリシドール基が結合し、構造式（３）の酸素原子には、上記構造式（１）、（２）、（３）、（４）又は（５）で表されるグリセロール基又はグリシドール基が結合し、構造式（５）の２つの酸素原子には、同一又は異なって上記構造式（１）、（２）、（３）、（４）又は（５）で表されるグリセロール基又はグリシドール基が結合する。 The two oxygen atoms in the structural formula (1) may be the same or different from each other and may be a glycerol group or glycidol represented by the structural formula (1), (2), (3), (4) or (5). A glycerol group or a glycidol group represented by the structural formula (1), (2), (3), (4) or (5) is bonded to the oxygen atom of the structural formula (2). The glycerol group or glycidol group represented by the structural formula (1), (2), (3), (4) or (5) is bonded to the oxygen atom of the structural formula (3), and the structural formula ( A glycerol group or a glycidol group represented by the structural formula (1), (2), (3), (4) or (5) is bonded to the two oxygen atoms of 5), which are the same or different.
この分岐ポリグリセロール鎖は分岐構造を有しているため、単独もしくは直鎖状のポリグリセロール鎖よりも多数の末端ヒドロキシ基を有し、高い親水性を示すため、好感触の化粧料を得ることができると考えられる。
この分岐ポリグリセロール変性シリコーンは、疎水的かつシリコーン由来の感触発現の源となるシリコーン部位と、親水的な分岐ポリグリセロール部位の割合を、様々な処方系に対し最適となるよう自由に設計することが可能である。
Since this branched polyglycerol chain has a branched structure, it has a larger number of terminal hydroxy groups than a single or linear polyglycerol chain, and exhibits high hydrophilicity, so that a cosmetic with a pleasant feel can be obtained. It is thought that you can.
This branched polyglycerol-modified silicone can be freely designed so that the ratio of the hydrophobic silicone-derived feeler-derived silicone sites and the hydrophilic branched polyglycerol sites is optimal for various formulation systems. Is possible.
本発明の皮膚用化粧料は、成分（ａ）の分岐ポリグリセロール変性シリコーンを配合することにより、配合安定性に優れ、皮膚への塗布感触、塗布後の肌感触が良好で、さらに皮膚保護効果を付与することができる。 The skin cosmetic of the present invention is blended with the branched polyglycerol-modified silicone of component (a), so that it has excellent blending stability, good skin feel after application, and good skin feel after application, and further has a skin protective effect. Can be granted.
［成分（ａ）］
成分（ａ）の分岐ポリグリセロール変性シリコーンは、シリコーン主鎖に分岐ポリグリセロール鎖が結合していることを特徴とする。
[Component (a)]
The branched polyglycerol-modified silicone of component (a) is characterized in that a branched polyglycerol chain is bonded to the silicone main chain.
この分岐ポリグリセロール鎖は、ａ個の構造式（１）で表される分岐グリセロール基（以下、基（１）という）、ｂ個の構造式（２）で表されるグリシドール基（以下、基（２）という）、ｃ個の構造式（３）で表されるグリセロール基（以下、基（３）という）、ｄ個の構造式（４）で表されるグリセロール基（以下、基（４）という）、ｅ個の構造式（５）で表される分岐グリセロール基（以下、基（５）という）が結合してなるものである。分岐ポリグリセロール鎖中において、基（１）、（２）、（３）及び（５）は、任意の配列で相互に結合していてもよい。基（１）及び／又は基（５）の数が多いほど分岐構造が発達しており、各分岐鎖の末端に基（４）が存在する。 This branched polyglycerol chain has a branched glycerol group represented by a structural formula (1) (hereinafter referred to as group (1)) and a glycidol group represented by b structural formula (2) (hereinafter referred to as group). (Referred to as (2)), c glycerol groups represented by structural formula (3) (hereinafter referred to as group (3)), glycerol groups represented as d structural formula (4) (hereinafter referred to as group (4) )), And e branched branched glycerol groups (hereinafter referred to as groups (5)) represented by the structural formula (5). In the branched polyglycerol chain, the groups (1), (2), (3) and (5) may be bonded to each other in any sequence. As the number of groups (1) and / or groups (5) increases, the branched structure develops, and the group (4) is present at the end of each branched chain.
分岐ポリグリセロール鎖中の、基（１）、（２）、（３）、（４）及び（５）の平均結合総数（ａ＋ｂ＋ｃ＋ｄ＋ｅ）は、ＮＭＲ解析ないし前駆体シリコーンとの分子量比較により求められ、その数は好ましくは４以上であり、４〜２０１がより好ましく、４〜１０１であることがさらに好ましく、４〜５１であることが特に好ましく、４〜２１であることが最も好ましい。分岐ポリグリセロール鎖中の分岐の割合［（ａ＋ｅ）／（ａ＋ｂ＋ｃ＋ｄ＋ｅ）］は、１／２０以上が好ましく、１／１０以上が更に好ましく、１／６以上が特に好ましく、１／２未満が好ましい。
分岐ポリグリセロール鎖中において、基（１）、（２）、（３）、（４）及び（５）は任意に結合していてもよい。
The average total number of bonds (a + b + c + d + e) of the groups (1), (2), (3), (4) and (5) in the branched polyglycerol chain is determined by NMR analysis or molecular weight comparison with the precursor silicone, The number is preferably 4 or more, more preferably 4 to 201, still more preferably 4 to 101, particularly preferably 4 to 51, and most preferably 4 to 21. The branching ratio [(a + e) / (a + b + c + d + e)] in the branched polyglycerol chain is preferably 1/20 or more, more preferably 1/10 or more, particularly preferably 1/6 or more, and preferably less than 1/2.
In the branched polyglycerol chain, the groups (1), (2), (3), (4) and (5) may be arbitrarily bonded.
基（１）の数（すなわち、ａ）は、分岐ポリグリセロール鎖中、０〜１００個存在することが好ましく、１〜１００個存在することがより好ましく、２〜１００個存在することがさらに好ましく、２〜５０個存在することが特に好ましく、２〜２５個存在することがとりわけ好ましく、２〜１０個存在することが最も好ましい。 The number of groups (1) (that is, a) is preferably 0 to 100, more preferably 1 to 100, and even more preferably 2 to 100 in the branched polyglycerol chain. 2 to 50 are particularly preferable, 2 to 25 are particularly preferable, and 2 to 10 are most preferable.
基（４）の数（すなわち、ｄ）は、１〜１０１個存在することが好ましく、２〜１０１個存在することがより好ましく、３〜１０１個存在することがさらに好ましく、３〜５１個存在することが特に好ましく、３〜２６個存在することがとりわけ好ましく、３〜１１個存在することが最も好ましい。 The number of groups (4) (that is, d) is preferably 1 to 101, more preferably 2 to 101, still more preferably 3 to 101, and 3 to 51. It is particularly preferable that 3 to 26 are present, particularly preferably 3 to 11 are present.
基（２）の数（すなわち、ｂ）、基（３）の数（すなわち、ｃ）は、同一又は異なって、０〜１９９個存在することが好ましく、０〜１９８個存在することがより好ましく、０〜１９６個存在することがさらに好ましく、０〜９６個存在することが特に好ましく、０〜４６個存在することがとりわけ好ましく、０〜１６個存在することが最も好ましい。 The number of groups (2) (ie, b) and the number of groups (3) (ie, c) are the same or different and are preferably 0 to 199, more preferably 0 to 198. 0 to 196 is more preferable, 0 to 96 is particularly preferable, 0 to 46 is particularly preferable, and 0 to 16 is most preferable.
基（５）の数（すなわち、ｅ）は、ａが０のときは１個であり、ａが１以上のときは、０又は１個が好ましい。ａが１以上で、ｅが０である、シリコーンのケイ素原子に、連結基を介して、下記記構造式（１）で表される分岐グリセロール基を１個以上含有する分岐ポリグリセロール鎖が少なくとも１つ結合した、分岐ポリグリセロール変性シリコーンが更に好ましい。 The number of groups (5) (ie, e) is preferably 1 when a is 0, and is preferably 0 or 1 when a is 1 or more. A branched polyglycerol chain containing at least one branched glycerol group represented by the following structural formula (1) via a linking group to a silicon silicon atom, wherein a is 1 or more and e is 0, One bonded, branched polyglycerol-modified silicone is more preferred.
（式中、２つの酸素原子には、同一又は異なって、上記構造式（１）、下記構造式（２）、（３）又は（４）で表されるグリセロール基又はグリシドール基が結合する。 (In the formula, a glycerol group or a glycidol group represented by the above structural formula (1), the following structural formula (2), (3) or (4) is bonded to the two oxygen atoms, which are the same or different.
この場合、構造式（１）の２つの酸素原子には、同一又は異なって上記構造式（１）、（２）、（３）又は（４）で表されるグリセロール基又はグリシドール基が結合し、構造式（２）の酸素原子には、上記構造式（１）、（２）、（３）又は（４）で表されるグリセロール基又はグリシドール基が結合し、構造式（３）の酸素原子には、上記構造式（１）、（２）、（３）又は（４）で表されるグリセロール基又はグリシドール基が結合する。）
分岐ポリグリセロール変性シリコーンにおける、シリコーンのケイ素原子と、前述の分岐ポリグリセロール鎖を結合する連結基は、エーテル基又はエステル基を有する２価の基であることが好ましく、さらには皮膚用化粧料中における化学的安定性等の点から、エーテル基を有する２価の基であることが好ましい。
In this case, the glycerol group or glycidol group represented by the structural formula (1), (2), (3) or (4) is bonded to the two oxygen atoms of the structural formula (1), which are the same or different. A glycerol group or a glycidol group represented by the structural formula (1), (2), (3) or (4) is bonded to the oxygen atom of the structural formula (2), and the oxygen of the structural formula (3) A glycerol group or glycidol group represented by the structural formula (1), (2), (3) or (4) is bonded to the atom. )
The branched polyglycerol-modified silicone preferably has a divalent group having an ether group or an ester group as the linking group for bonding the silicon atom of the silicone and the aforementioned branched polyglycerol chain. From the viewpoints of chemical stability and the like, it is preferably a divalent group having an ether group.
エーテル基を有する２価の基としては、一般式（７）で表される基（以下、連結基（７）という）が好ましい。なお、連結基（７）は、（Ｒ9）p側がシリコーン鎖のケイ素原子に結合し、（ＡＯ）q側が分岐ポリグリセロール鎖に結合する。 The divalent group having an ether group is preferably a group represented by the general formula (7) (hereinafter referred to as a linking group (7)). In the linking group (7), the (R 9 ) p side is bonded to the silicon atom of the silicone chain, and the (AO) q side is bonded to the branched polyglycerol chain.
−（Ｒ9）p−Ｏ−（ＡＯ）q− （７）
（式中、Ｒ9は、置換基を有していてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基、アルケニレン基又は炭素数６〜２８のアリーレン基、好ましくは炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基又はアルケニレン基、ＡＯは炭素数１〜４のアルキレンオキシ基（オキシアルキレン基ともいう）又は炭素数６〜１０のアリーレンオキシ基（オキシアリーレン基ともいう）、好ましくは炭素数１〜４のアルキレンオキシ基、ｐは０又は１の数、ｑは０〜３０の数を示し、ｑ個のＡＯは同一でも異なっていてもよい。）
エステル基を有する２価の基としては、一般式（８）で表される基（以下、連結基（８）という）が好ましい。なお、連結基（８）は、Ｒ10側がシリコーン鎖のケイ素原子に結合し、（ＡＯ）r側が分岐ポリグリセロール鎖に結合する。
- (R 9) p -O- ( AO) q - (7)
(Wherein R 9 may have a substituent, a linear or branched alkylene group having 1 to 22 carbon atoms, an alkenylene group or an arylene group having 6 to 28 carbon atoms, preferably 1 carbon atom) -22 linear or branched alkylene group or alkenylene group, AO is an alkyleneoxy group having 1 to 4 carbon atoms (also referred to as an oxyalkylene group) or an aryleneoxy group having 6 to 10 carbon atoms (also referred to as an oxyarylene group). Preferably an alkyleneoxy group having 1 to 4 carbon atoms, p is a number of 0 or 1, q is a number of 0 to 30, and q AOs may be the same or different.)
The divalent group having an ester group is preferably a group represented by the general formula (8) (hereinafter referred to as a linking group (8)). In the linking group (8), the R 10 side is bonded to the silicon atom of the silicone chain, and the (AO) r side is bonded to the branched polyglycerol chain.
−Ｒ10−ＣＯＯ−（ＡＯ）r− （８）
（式中、Ｒ10は、置換基を有していてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基、アルケニレン基又は炭素数６〜２８のアリーレン基、好ましくは炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基又はアルケニレン基、ｒは０〜３０の数、ＡＯは前記の意味を示し、ｒ個のＡＯは同一でも異なっていてもよい。）
連結基（７）及び（８）において、ＡＯのアルキレンオキシ基又はアリーレンオキシ基の酸素側で分岐ポリグリセロール基に結合し、アルキレンオキシ基又はアリーレンオキシ基のアルキレン又はアリーレン側で、連結基が含有するエーテル基又はエステル基に結合する。
—R 10 —COO— (AO) r − (8)
(In the formula, R 10 may have a substituent, a linear or branched alkylene group having 1 to 22 carbon atoms, an alkenylene group, or an arylene group having 6 to 28 carbon atoms, preferably 1 carbon atom. -22 linear or branched alkylene group or alkenylene group, r is a number from 0 to 30, AO is as defined above, and r AOs may be the same or different.
In the linking groups (7) and (8), bonded to the branched polyglycerol group on the oxygen side of the alkyleneoxy group or aryleneoxy group of AO, and the linking group contains on the alkylene or arylene side of the alkyleneoxy group or aryleneoxy group To an ether group or an ester group.
Ｒ9及びＲ10中の置換基として、ヒドロキシ基、アミノ基（炭素数１〜２２）、イミノ基（炭素数１〜２２）、カルボキシ基、アルコキシ基（炭素数１〜２２）、アシル基（炭素数１〜２２）等が挙げられる。 As substituents in R 9 and R 10 , a hydroxy group, an amino group (1 to 22 carbon atoms), an imino group (1 to 22 carbon atoms), a carboxy group, an alkoxy group (1 to 22 carbon atoms), an acyl group ( C1-C22) etc. are mentioned.
最も好ましい連結基は、下記一般式（９）で表される連結基（以下、連結基（９）という）である。なお、連結基（９）では、トリメチレン側がシリコーン鎖のケイ素原子に結合し、酸素原子側が分岐ポリグリセロール鎖に結合する。 The most preferred linking group is a linking group represented by the following general formula (9) (hereinafter referred to as linking group (9)). In the linking group (9), the trimethylene side is bonded to the silicon atom of the silicone chain, and the oxygen atom side is bonded to the branched polyglycerol chain.
−ＣＨ2ＣＨ2ＣＨ2−Ｏ−ＣＨ2ＣＨ2Ｏ− （９）
また、好ましい他の連結基は、オキシフェニレン基を含有する連結基である。そのような連結基の中では、下記一般式（１０）で表される基（以下、連結基（１０）という）又は一般式（１１）で表される基（以下、連結基（１１）という）が好ましい。なお、連結基（１０）では、（Ｒ11）u側がシリコーン鎖のケイ素原子に結合し、（ＡＯ）v側が分岐ポリグリセロール鎖に結合する。また、連結基（１１）では、（Ｒ12）z側がシリコーン鎖のケイ素原子に結合し、（ＡＯ）x及び（ＡＯ）y側が分岐ポリグリセロール鎖に結合する。
—CH 2 CH 2 CH 2 —O—CH 2 CH 2 O— (9)
Another preferred linking group is a linking group containing an oxyphenylene group. Among such linking groups, a group represented by the following general formula (10) (hereinafter referred to as linking group (10)) or a group represented by the general formula (11) (hereinafter referred to as linking group (11)). ) Is preferred. In the linking group (10), the (R 11 ) u side is bonded to the silicon atom of the silicone chain, and the (AO) v side is bonded to the branched polyglycerol chain. In the linking group (11), the (R 12 ) z side is bonded to the silicon atom of the silicone chain, and the (AO) x and (AO) y sides are bonded to the branched polyglycerol chain.
（式中、Ｒ11は、置換基を有していてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基又はアルケニレン基、ｕは０又は１の数、ｖは０〜３０の数、ＡＯは前記の意味を示し、ｖ個のＡＯは同一でも異なっていてもよい。） (In the formula, R 11 is an optionally substituted linear or branched alkylene group or alkenylene group having 1 to 22 carbon atoms, u is 0 or 1, and v is 0 to 30. Number, AO indicates the above meaning, and v AOs may be the same or different.)
（式中、Ｒ12は、置換基を有していてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基又はアルケニレン基、ｚは０又は１の数、ｘは０〜３０の数、ｙは０〜３０の数、ＡＯは前記の意味を示し、ｘ個及びｙ個のＡＯは同一でも異なっていてもよい。）
連結基（１０）及び連結基（１１）において、（Ｒ11）u及び（Ｒ12）zは、シリコーン鎖のケイ素原子と、連結基が含有するオキシフェニレン基のフェニレン基とを結ぶ基であるが、Ｒ11及びＲ12は、好ましくは、炭素数１〜１６，特に好ましくは１〜１２のアルキレン基又はアルケニレン基であり、エチレン、プロピレン、トリメチレン、テトラメチレン、ペンタメチレン、ヘキサメチレン、ヘプタメチレン、オクタメチレン、ノナメチレン、デカメチレン、ウンデカメチレン、ドデカメチレン、トリデカメチレン、テトラデカメチレン、ペンタデカメチレン、ヘキサデカメチレン基等が挙げられる。これらの中では、エチレン、プロピレン又はトリメチレン基がさらに好ましく、エチレン又はトリメチレン基が特に好ましい。
(In the formula, R 12 is an optionally substituted linear or branched alkylene group or alkenylene group having 1 to 22 carbon atoms, z is a number of 0 or 1, and x is 0 to 30. Number, y is a number from 0 to 30, AO is as defined above, and x and y AOs may be the same or different.)
In the linking group (10) and the linking group (11), (R 11 ) u and (R 12 ) z are groups linking the silicon atom of the silicone chain and the phenylene group of the oxyphenylene group contained in the linking group. R 11 and R 12 are preferably an alkylene group or alkenylene group having 1 to 16 carbon atoms, particularly preferably 1 to 12, and are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene. , Octamethylene, nonamethylene, decamethylene, undecamethylene, dodecamethylene, tridecamethylene, tetradecamethylene, pentadecamethylene, hexadecamethylene group and the like. Among these, an ethylene, propylene or trimethylene group is more preferable, and an ethylene or trimethylene group is particularly preferable.
Ｒ11及びＲ12中に存在していてもよい置換基として、ヒドロキシ基、アミノ基（炭素数１〜２２）、イミノ基（炭素数１〜２２）、カルボキシ基、アルコキシ基（炭素数１〜２２）、アシル基（炭素数１〜２２）等が挙げられる。
ｕ及びｚは、０又は１であるが、１がより好ましい。
As a substituent which may be present in R 11 and R 12 , a hydroxy group, an amino group (C1 to C22), an imino group (C1 to C22), a carboxy group, an alkoxy group (C1 to C1). 22), an acyl group (C1-C22), etc. are mentioned.
u and z are 0 or 1, but 1 is more preferable.
連結基（１０）及び連結基（１１）において、ＡＯは、分岐ポリグリセロール鎖と、連結基が含有するオキシフェニレン基の酸素原子とを結ぶオキシアルキレン基又はオキシアリーレン基であり、オキシアルキレン基又はオキシアリーレン基の酸素側で分岐ポリグリセロール鎖に結合し、オキシアルキレン基又はオキシアリーレン基のアルキレン又はアリーレン側でオキシフェニレン基の酸素原子に結合する。ＡＯとして、オキシエチレン基、オキシプロピレン基又はオキシフェニレン基が好ましく、これらの中ではオキシエチレン基が特に好ましい。 In the linking group (10) and the linking group (11), AO is an oxyalkylene group or an oxyarylene group that connects the branched polyglycerol chain and the oxygen atom of the oxyphenylene group contained in the linking group, Bonded to the branched polyglycerol chain on the oxygen side of the oxyarylene group, and bonded to the oxygen atom of the oxyphenylene group on the alkylene or arylene side of the oxyalkylene group or oxyarylene group. As AO, an oxyethylene group, an oxypropylene group or an oxyphenylene group is preferable, and among these, an oxyethylene group is particularly preferable.
ｖ、ｘ及びｙはそれぞれ、０〜３０の数であるが、０〜１５が好ましく、０〜５がさらに好ましく、０が最も好ましい。ｖ、ｘならびにｙが０以外の数である場合、ｖ個のＡＯ、ｘ個のＡＯ、ｙ個のＡＯは、同一又は異なっていてもよく、異なる場合、それらＡＯの相互の結合様式は、交互型、ブロック型あるいはこれら以外の周期配列であってもよいし、又はランダム型であってもよい。 v, x and y are each a number of 0 to 30, preferably 0 to 15, more preferably 0 to 5, and most preferably 0. When v, x, and y are non-zero numbers, v AOs, x AOs, and y AOs may be the same or different. It may be an alternating type, a block type, a periodic arrangement other than these, or a random type.
連結基（１０）において、オキシフェニレン基のフェニレン基に結合した、酸素原子と（Ｒ11）u基（ｕが０の場合はシリコーン鎖上のケイ素原子）の結合様式は、互いにオルト位、メタ位、パラ位のいずれであってもよく、またこれらの混合であってもよい。また連結基（１１）において、オキシフェニレン基のフェニレン基に結合した、２個の酸素原子と（Ｒ12）z基（ｚが０の場合はシリコーン鎖上のケイ素原子）のうちいずれの２個についても、その結合様式は、互いにオルト位、メタ位、パラ位のいずれであってもよく、またこれらの混合であってもよい。 In the linking group (10), the bonding mode of the oxygen atom and the (R 11 ) u group (the silicon atom on the silicone chain when u is 0) bonded to the phenylene group of the oxyphenylene group is the ortho position, the meta Either the position or the para position may be used, or a mixture thereof may be used. Further, in the linking group (11), any two of the two oxygen atoms bonded to the phenylene group of the oxyphenylene group and the (R 12 ) z group (a silicon atom on the silicone chain when z is 0) In addition, the bonding mode may be any of the ortho position, the meta position, and the para position, or a mixture thereof.
オキシフェニレン基含有連結基の中で、最も好ましいものは、下記一般式（１２）で表される連結基（以下、連結基（１２）という）である。なお、連結基（１２）では、トリメチレン側がシリコーン鎖のケイ素原子に結合し、酸素原子側が分岐ポリグリセロール鎖に結合する。 Among the oxyphenylene group-containing linking groups, the most preferable one is a linking group represented by the following general formula (12) (hereinafter referred to as linking group (12)). In the linking group (12), the trimethylene side is bonded to the silicon atom of the silicone chain, and the oxygen atom side is bonded to the branched polyglycerol chain.
連結基（１２）において、オキシフェニレン基のフェニレン基に結合した、酸素原子とトリメチレン基の結合様式は、オルト位、メタ位、パラ位のいずれであってもよく、またこれらの混合であってもよいが、オルト位、パラ位又はこれらの混合物であることがより好ましい。 In the linking group (12), the bonding mode of the oxygen atom and trimethylene group bonded to the phenylene group of the oxyphenylene group may be any of ortho, meta, and para positions, and a mixture thereof. However, the ortho position, the para position, or a mixture thereof is more preferable.
成分（ａ）を形成するシリコーンは、ケイ素原子を２つ以上有するポリシロキサンから誘導されるものであり、ポリシロキサンの形状は直鎖状、分岐鎖状、環状のいずれであってもよい。また、ポリシロキサンの数平均分子量は、好ましくは３００〜７０万、より好ましくは３００〜２０万、さらに好ましくは１０００〜２万である。数平均分子量は、ゲル・パーミエーション・クロマトグラフィー（以下、ＧＰＣ）法等により求めることができる。 The silicone forming component (a) is derived from a polysiloxane having two or more silicon atoms, and the polysiloxane may be linear, branched or cyclic. Moreover, the number average molecular weight of polysiloxane becomes like this. Preferably it is 300-700,000, More preferably, it is 300-200,000, More preferably, it is 1000-20,000. The number average molecular weight can be determined by gel permeation chromatography (hereinafter, GPC) method or the like.
成分（ａ）としては、一般式（６）で表される直鎖状シリコーン（以下、シリコーン（６）という）が好ましい。 As the component (a), a linear silicone represented by the general formula (6) (hereinafter referred to as silicone (6)) is preferable.
（式中、Ｒ1、Ｒ2、Ｒ3、ｔ個のＲ4、ｔ個のＲ5、Ｒ6、Ｒ7、Ｒ8は、同一又は異なって、分岐ポリグリセロール鎖が結合した連結基、置換基を有していてもよく、フッ素原子で置換されていてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキル基、アルケニル基又はアルコシキ基、あるいは炭素数６〜２２のアリール基を示し、Ｒ1、Ｒ2、Ｒ3、ｔ個のＲ4、ｔ個のＲ5、Ｒ6、Ｒ7、Ｒ8のうち少なくとも１つは分岐ポリグリセロール鎖が結合した連結基である。ｔは０〜１０，０００の数を示す。）
シリコーン（６）において、Ｒ1、Ｒ2、Ｒ3、ｔ個のＲ4、ｔ個のＲ5、Ｒ6、Ｒ7、Ｒ8のうち分岐ポリグリセロール鎖が結合した連結基以外の基は、同一又は異なって、置換基を有していてもよく、フッ素原子で置換されていてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキル基、アルケニル基又はアルコキシ基、あるいは炭素数６〜２２のアリール基であり、炭素数１〜２２のアルキル基としては、例えばメチル、エチル、プロピル、イソプロピル、ブチル、ｔ−ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、トリフルオロプロピル等が挙げられ、炭素数１〜２２のアルケニル基としては、ビニル基やアリル基が挙げられ、炭素数１〜２２のアルコキシ基としては、例えばメトキシ、エトキシ、プロポキシ、ブトキシ、ペンチルオキシ、ヘキシルオキシ、ヘプチルオキシ、オクチルオキシ、フェノキシ基等が挙げられる。これらの中では、炭素数１〜１２の直鎖もしくは分岐鎖のアルキル基、ビニル基、アリル基、又は炭素数６〜１２のアリール基が好ましく、炭素数１〜３のアルキル基又はフェニル基がさらに好ましく、メチル基、プロピル基又はフェニル基が特に好ましく、メチル基、フェニル基が最も好ましい。
Wherein R 1 , R 2 , R 3 , t R 4 , t R 5 , R 6 , R 7 , R 8 are the same or different and are a linking group to which a branched polyglycerol chain is bonded, A linear or branched alkyl group, alkenyl group or alkoxy group having 1 to 22 carbon atoms, or an aryl group having 6 to 22 carbon atoms, which may have a substituent and may be substituted with a fluorine atom Wherein at least one of R 1 , R 2 , R 3 , t R 4 , t R 5 , R 6 , R 7 , R 8 is a linking group to which a branched polyglycerol chain is bonded. t represents a number from 0 to 10,000.)
In silicone (6), R 1 , R 2 , R 3 , t R 4 , t R 5 , R 6 , R 7 , R 8 other than the linking group to which the branched polyglycerol chain is bonded are A linear or branched alkyl group, alkenyl group or alkoxy group having 1 to 22 carbon atoms which may have a substituent and may be substituted with a fluorine atom, or the number of carbon atoms Examples of the alkyl group having 6 to 22 carbon atoms and having 1 to 22 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, nonyl, trifluoropropyl and the like. Examples of the alkenyl group having 1 to 22 carbon atoms include a vinyl group and an allyl group. Examples of the alkoxy group having 1 to 22 carbon atoms include methoxy, ethoxy, propoxy, Butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and a phenoxy group. In these, a C1-C12 linear or branched alkyl group, a vinyl group, an allyl group, or a C6-C12 aryl group is preferable, and a C1-C3 alkyl group or a phenyl group is preferable. More preferably, a methyl group, a propyl group or a phenyl group is particularly preferable, and a methyl group or a phenyl group is most preferable.
シリコーン（６）において、Ｒ1〜Ｒ8が有していてもよい置換基として、フェニル基、ヒドロキシフェニル基、ヒドロキシ基、カルボキシ基、アミノ基（炭素数０〜１４）、イミノ基、（アミノエチル）アミノ基、（ジメチルアミノエチル）アミノ基、ポリオキシアルキレン基、メルカプト基、及びエポキシ基等が挙げられる。これらの置換基を有する場合、Ｒ1〜Ｒ8としてプロピル基が特に好ましい。 In the silicone (6), the substituents that R 1 to R 8 may have include a phenyl group, a hydroxyphenyl group, a hydroxy group, a carboxy group, an amino group (0 to 14 carbon atoms), an imino group, (amino And ethyl) amino group, (dimethylaminoethyl) amino group, polyoxyalkylene group, mercapto group, and epoxy group. When it has these substituents, a propyl group is particularly preferable as R 1 to R 8 .
シリコーン（６）において、Ｒ1、Ｒ2、Ｒ3、ｔ個のＲ4、ｔ個のＲ5、Ｒ6、Ｒ7、Ｒ8のうち少なくとも１つ、好ましくは１〜１０個、さらに好ましくは１〜５個、特に好ましくは１〜２個は、分岐ポリグリセロール鎖が結合した連結基である。この連結基は、シリコーン（６）の側鎖、片末端及び／又は両末端のいずれに位置していてもよいし、またその混合物でもよい。 In the silicone (6), at least one of R 1 , R 2 , R 3 , t R 4 , t R 5 , R 6 , R 7 , R 8 , preferably 1 to 10, more preferably 1 to 5, particularly preferably 1 to 2, are a linking group to which a branched polyglycerol chain is bonded. This linking group may be located at any of the side chain, one end and / or both ends of the silicone (6), or may be a mixture thereof.
Ｒ1〜Ｒ3からなる群から選ばれる１個と、Ｒ6〜Ｒ8からなる群から選ばれる１個が、分岐ポリグリセロール鎖が結合した連結基を示し、残余のＲ1〜Ｒ3及びＲ6〜Ｒ8、ｔ個のＲ4，ｔ個のＲ5は、メチル基であることが特に好ましい。 One selected from the group consisting of R 1 to R 3 and one selected from the group consisting of R 6 to R 8 represent a linking group to which a branched polyglycerol chain is bonded, and the remaining R 1 to R 3 and R 6 to R 8 , t R 4 , and t R 5 are particularly preferably methyl groups.
また、分岐ポリグリセロール鎖が結合した連結基が、ｔ個のＲ4，及びｔ個のＲ5から選ばれる３個以上に存在する場合も、側鎖多置換型の分岐ポリグリセロール変性シリコーンとなり好ましい。 Further, when the linking group to which the branched polyglycerol chain is bonded is present in three or more selected from t R 4 and t R 5 , it is preferable to be a side-chain multi-substituted branched polyglycerol-modified silicone. .
シリコーン（６）中のｔは、０〜１０，０００の数を示し、好ましくは１〜３，０００の数を、さらに好ましくは５〜５００の数を、特に好ましくは１０〜１５０の数を示す。 T in the silicone (6) represents a number of 0 to 10,000, preferably a number of 1 to 3,000, more preferably a number of 5 to 500, and particularly preferably a number of 10 to 150. .
成分（ａ）の数平均分子量は、好ましくは５００〜５０万、さらに好ましくは７５０〜２０万、特に好ましくは１０００〜１０万である。この数平均分子量の測定は、ＧＰＣ法（標準ポリスチレン又はポリエチレングリコール換算）による。 The number average molecular weight of component (a) is preferably 500 to 500,000, more preferably 750 to 200,000, and particularly preferably 1,000 to 100,000. The number average molecular weight is measured by GPC method (standard polystyrene or polyethylene glycol conversion).
成分（ａ）は、シリコーン中のケイ素原子数（Ｓｉ）と分岐ポリグリセロール鎖中の基（１）、（２）、（３）、（４）及び（５）の合計数（以下、グリセロール基数という）（Ｇ）の比（Ｇ／Ｓｉ）が、０．００１〜５０が好ましく、０．０５〜１０がより好ましく、０．１〜３がさらに好ましく、０．１５〜１が特に好ましい。 Component (a) is a total number of silicon atoms (Si) in the silicone and groups (1), (2), (3), (4) and (5) in the branched polyglycerol chain (hereinafter referred to as the number of glycerol groups). The ratio (G / Si) of (G) is preferably 0.001 to 50, more preferably 0.05 to 10, still more preferably 0.1 to 3, and particularly preferably 0.15 to 1.
成分（ａ）において、本発明の効果を著しく阻害しない限りにおいて、分岐ポリグリセロール鎖中に、少量のエチレンオキシ基及び／又はプロピレンオキシ基が存在していてもよい。エチレンオキシ基及び／又はプロピレンオキシ基が分岐ポリグリセロール鎖中にランダムに存在していてもよいし、複数のエチレンオキシ基及び／又はプロピレンオキシ基が連鎖をなして分岐ポリグリセロール鎖中にブロック的に存在していてもよい。この際、複数のエチレンオキシ基及び／又はプロピレンオキシ基からなるブロックは、分岐ポリグリセロール鎖の連結基の近傍に存在してもよいし、末端に存在してもよいし、あるいは中程に存在していてもよい。エチレンオキシ基及び／又はプロピレンオキシ基は０．００１〜０．５モル当量存在することが好ましく、０．０２〜０．２モル当量存在することがさらに好ましい。 In the component (a), a small amount of ethyleneoxy groups and / or propyleneoxy groups may be present in the branched polyglycerol chain as long as the effects of the present invention are not significantly inhibited. Ethyleneoxy groups and / or propyleneoxy groups may be present randomly in the branched polyglycerol chain, or a plurality of ethyleneoxy groups and / or propyleneoxy groups form a chain and block in the branched polyglycerol chain May be present. In this case, the block composed of a plurality of ethyleneoxy groups and / or propyleneoxy groups may be present in the vicinity of the linking group of the branched polyglycerol chain, may be present at the terminal, or may be present in the middle. You may do it. The ethyleneoxy group and / or propyleneoxy group is preferably present in an amount of 0.001 to 0.5 molar equivalent, more preferably 0.02 to 0.2 molar equivalent.
成分（ａ）は、反応性不飽和基を有する分岐ポリグリセロールと、シリコーン鎖中のケイ素原子の一部に水素原子が結合した、いわゆるオルガノハイドロジェンシリコーンを、白金系触媒存在下でヒドロシリル化反応させる方法により得ることができる。反応性不飽和基を有する分岐ポリグリセロールは、反応性不飽和基と官能基（好ましくはヒドロキシ基又はカルボキシ基）を有する化合物に、酸性触媒又は塩基性触媒存在下、グリシドール（２，３−エポキシ−１−プロパノール）を、添加速度をコントロールしながら、添加して反応させることにより得ることができる。添加速度を、遅くすることで、分岐度の高い反応性不飽和基を有する分岐ポリグリセロールを製造することが出来る。 Component (a) is a hydrosilylation reaction between a branched polyglycerol having a reactive unsaturated group and a so-called organohydrogen silicone in which a hydrogen atom is bonded to a part of a silicon atom in a silicone chain in the presence of a platinum-based catalyst. It can obtain by the method of making it. A branched polyglycerol having a reactive unsaturated group is obtained by adding glycidol (2,3-epoxy) to a compound having a reactive unsaturated group and a functional group (preferably a hydroxy group or a carboxy group) in the presence of an acidic catalyst or a basic catalyst. -1-propanol) can be obtained by adding and reacting while controlling the addition rate. A branched polyglycerol having a reactive unsaturated group having a high degree of branching can be produced by slowing the addition rate.
また、反応性基としてヒドロキシ基、カルボキシ基、アミノ基、イミノ基、メルカプト基及びエポキシ基からなる群から選ばれる１つ以上の官能基を有するシリコーンに、酸性又はカリウム等の塩基性触媒の存在下、グリシドールを添加し、グラフト重合させる方法等によっても成分（ａ）を製造することができる。 In addition, presence of a basic catalyst such as acidic or potassium in silicone having one or more functional groups selected from the group consisting of a hydroxy group, a carboxy group, an amino group, an imino group, a mercapto group and an epoxy group as a reactive group The component (a) can also be produced by a method of adding glycidol and graft polymerization.
成分（ａ）の分岐ポリグリセロール変性シリコーンは、２種類以上を同時に用いてもよい。また、本発明の化粧料中における成分（ａ）の含有量は、化粧料の配合安定性と、得られる塗布時から乾燥後にわたるべたつき、すべり感等の感触の点から、０．０１〜６０重量％が好ましく、さらには０．０２〜３０重量％、特には０．０５〜２０重量％が好ましい。 Two or more kinds of the branched polyglycerol-modified silicone of component (a) may be used simultaneously. In addition, the content of the component (a) in the cosmetic of the present invention is 0.01 to 60 from the viewpoints of blending stability of the cosmetic and the feel such as stickiness and slipperiness from the time of application to drying. % By weight is preferable, more preferably 0.02 to 30% by weight, and particularly preferably 0.05 to 20% by weight.
［成分（ｂ）］
本発明の皮膚用化粧料には、配合成分の溶解、防腐、使用時の清涼感付与、皮膚の保湿性向上等の目的で、さらに成分（ｂ）として水溶性溶剤を含むことができる。
[Component (b)]
The cosmetic for skin of the present invention may further contain a water-soluble solvent as the component (b) for the purpose of dissolving the blended components, preserving, imparting a refreshing feeling during use, and improving the moisture retention of the skin.
本発明で用いられる成分（ｂ）の水溶性溶剤としては、２０℃における水に対する溶解度が５重量％以上のものであれば特に制限されず、例えば低級アルコール、多価アルコール、グリコールエーテルが挙げられる。低級アルコールとしては、例えばエタノール、イソプロパノール等の炭素数１〜３の１価アルコールが挙げられ、多価アルコールとしては、例えばエチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール、１，３−ブチレングリコール、１，４−ブチレングリコール、イソプレングリコール等のグリコール類及びこれらのアルキルエーテル類；グリセリン、ジグリセリン、トリグリセリン等のグリセリン類；マルトース、マルチトール、ショ糖、フラクトース、キシリトール、ソルビトール、マルトトリオース、スレイトール、エリスリトール、グルコース等の糖類；ポリエチレングリコール、ポリオキシエチレンメチルグルコシド等が挙げられる。グリコールエーテルとしては、例えばエチレングリコールモノエチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテル等が挙げられる。 The water-soluble solvent of component (b) used in the present invention is not particularly limited as long as the solubility in water at 20 ° C. is 5% by weight or more, and examples thereof include lower alcohols, polyhydric alcohols, and glycol ethers. . Examples of the lower alcohol include monohydric alcohols having 1 to 3 carbon atoms such as ethanol and isopropanol. Examples of the polyhydric alcohol include ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,3-butylene glycol, Glycols such as 1,4-butylene glycol and isoprene glycol and alkyl ethers thereof; glycerols such as glycerin, diglycerin and triglycerin; maltose, maltitol, sucrose, fructose, xylitol, sorbitol, maltotriose, Examples include saccharides such as threitol, erythritol, and glucose; polyethylene glycol, polyoxyethylene methyl glucoside, and the like. Examples of the glycol ether include ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monoethyl ether, and the like.
成分（ｂ）としては、低級アルコール、多価アルコールが好ましく、特にエタノール、グリセリンが好ましい。
成分（ｂ）は、１種以上を用いることができ、本発明の化粧料中に０．０１〜９５重量％、特に０．１〜６５重量％、さらに１〜６０重量％配合するのが、溶解性、安定性の点で好ましい。
As the component (b), lower alcohols and polyhydric alcohols are preferable, and ethanol and glycerin are particularly preferable.
One or more kinds of component (b) can be used, and it is blended in the cosmetic of the present invention in an amount of 0.01 to 95% by weight, particularly 0.1 to 65% by weight, and further 1 to 60% by weight. It is preferable in terms of solubility and stability.
［皮膚用化粧料］
本発明の皮膚用化粧料は、さらに通常の皮膚用化粧料に用いられるアニオン性界面活性剤、カチオン性界面活性剤、ノニオン性界面活性剤、両性界面活性剤を含むことができる。
[Skin cosmetic]
The skin cosmetic of the present invention can further contain an anionic surfactant, a cationic surfactant, a nonionic surfactant, and an amphoteric surfactant that are used in ordinary skin cosmetics.
本発明の皮膚用化粧料は、さらに塗布時および乾燥後の感触向上、組成物の粘度調整を目的に、水溶性高分子を含むことができる。水溶性高分子の例としては、ペクチン、カッパーカラギーナン、ローカストビーンガム、グアーガム、キサンタンガム、カラヤガム、タマリンド種子多糖、アラビアガム、トラガカントガム、ヒアルロン酸ナトリウム、コンドロイチン硫酸ナトリウム、アルギン酸ナトリウム等の多糖類、ゼラチン、カゼイン、アルブミン、メチル化コラーゲン等のタンパク質、カルボキシビニルポリマー、ポリアクリル酸ナトリウム、ポリビニルアルコール等の合成高分子、カルボキシメチルセルロース、ヒドロキシエチルセルロース、カチオン化セルロース等の天然高分子誘導体等が挙げられ、これらの内、特にペクチン（ビストップＤ４０２）、カッパーカラギーナン（ＣＳ−４４）（いずれも三栄化学社製）が使用感良好で好ましい。これら水溶性高分子は、塗布時および乾燥後の感触を向上させ、またべたつきを抑える観点から、本発明の化粧料中に０．０１〜１．０重量％、特に０．０３〜０．３重量％配合することが好ましい。 The cosmetic for skin of the present invention can further contain a water-soluble polymer for the purpose of improving the feel during application and after drying and adjusting the viscosity of the composition. Examples of water-soluble polymers include pectin, copper carrageenan, locust bean gum, guar gum, xanthan gum, karaya gum, tamarind seed polysaccharide, gum arabic, tragacanth gum, sodium hyaluronate, sodium chondroitin sulfate, sodium alginate, gelatin, Examples include proteins such as casein, albumin, methylated collagen, synthetic polymers such as carboxyvinyl polymer, sodium polyacrylate, polyvinyl alcohol, natural polymer derivatives such as carboxymethylcellulose, hydroxyethylcellulose, and cationized cellulose. Among them, pectin (Bistop D402) and copper carrageenan (CS-44) (both manufactured by Sanei Chemical Co., Ltd.) are preferable because of good feeling in use. These water-soluble polymers improve the feel at the time of application and after drying, and from the viewpoint of suppressing stickiness, 0.01 to 1.0% by weight, particularly 0.03 to 0.3% in the cosmetic of the present invention. It is preferable to blend by weight%.
本発明の皮膚用化粧料は、さらに化粧料用粉体を含むことができる。化粧料用粉体の例としては、タルク、セリサイト、カオリン、マイカ、炭酸マグネシウム、炭酸カルシウム、ケイ酸マグネシウム、ケイ酸アルミニウムマグネシウム、シリカ、合成マイカ等の体質顔料；酸化チタン、酸化亜鉛、硫酸バリウム等の白色顔料；ベンガラ、黄酸化鉄、黒酸化鉄、グンジョウ、コンジョウ等の無機着色顔料；タール色素、天然色素等の有機着色剤；雲母チタン、酸化鉄雲母チタン、オキシ塩化ビスマス等のパール顔料；ナイロンパウダー、シルクパウダー、スチレンパウダー、結晶セルロース等の有機粉体；これらの粉体に油剤処理やシリコン処理、フッ素処理等の疎水化処理を施した疎水化処理粉体；シリコーン樹脂粉末、シリコーンゴム粉末、トリメチルシロキシケイ酸等が挙げられる。疎水化処理は、例えばシリコーン油、脂肪酸金属塩、アルキルリン酸、アルキルリン酸のアルカリ金属塩又はアミン塩、Ｎ−モノ長鎖（炭素数８〜２２）脂肪族アシル塩基性アミノ酸、パーフルオロアルキル基を有するフッ素化合物等の疎水化処理剤を用いて常法により行われる。これらの中から適宜必要に応じて、２種以上を併用してもよい。 The cosmetic for skin of the present invention may further contain a cosmetic powder. Examples of cosmetic powders include body pigments such as talc, sericite, kaolin, mica, magnesium carbonate, calcium carbonate, magnesium silicate, magnesium aluminum silicate, silica, and synthetic mica; titanium oxide, zinc oxide, sulfuric acid White pigments such as barium; inorganic color pigments such as bengara, yellow iron oxide, black iron oxide, gunjo, and conger; organic colorants such as tar dyes and natural dyes; pearls such as mica titanium, iron oxide mica titanium, and bismuth oxychloride Pigment: Organic powder such as nylon powder, silk powder, styrene powder, crystalline cellulose, etc .; Hydrophobized powder obtained by subjecting these powders to hydrophobizing treatment such as oil treatment, silicon treatment, fluorine treatment; silicone resin powder, Examples thereof include silicone rubber powder and trimethylsiloxysilicic acid. Hydrophobizing treatment includes, for example, silicone oil, fatty acid metal salt, alkyl phosphoric acid, alkali metal salt or amine salt of alkyl phosphoric acid, N-mono long chain (carbon number 8 to 22) aliphatic acyl basic amino acid, perfluoroalkyl This is carried out by a conventional method using a hydrophobizing agent such as a fluorine compound having a group. Two or more of these may be used in combination as necessary.
本発明の皮膚用化粧料は、成分（ａ）以外のシリコーン類や油剤を油性成分として含むことができる。成分（ａ）以外のシリコーン類としては、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、アミノ変性シリコーン、ポリエーテル変性シリコーン、エポキシ変性シリコーン、フッ素変性シリコーン、環状シリコーン、アルキル変性シリコーン、オキサゾリン変性シリコーン等が挙げられ、なかでも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、アミノ変性シリコーン、ポリエーテル変性シリコーン、オキサゾリン変性シリコーン、環状シリコーンが好ましい。 The cosmetic for skin of this invention can contain silicones and oil agents other than a component (a) as an oil-based component. Examples of silicones other than component (a) include dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, polyether-modified silicone, epoxy-modified silicone, fluorine-modified silicone, cyclic silicone, alkyl-modified silicone, and oxazoline-modified silicone. Of these, dimethylpolysiloxane, methylphenylpolysiloxane, amino-modified silicone, polyether-modified silicone, oxazoline-modified silicone, and cyclic silicone are preferable.
油剤とは、シリコーン類を除く油性物質を指し、例えば、スクワレン、スクワラン、ワセリン、ラノリン、セレシン、流動パラフィン、流動イソパラフィン、シクロパラフィン、マイクロクリスタリンワックス等の炭化水素類；ヒマシ油、カカオ油、ミンク油、アボガド油、オリーブ油、ホホバ油、ヒマシ油等のグリセリド類；ミツロウ、鯨ロウ、ラノリン、カルナウバロウ等のロウ類；セチルアルコール、オレイルアルコール、ステアリルアルコール、イソステアリルアルコール、２−オクチルドデカノール、グリセリン等のアルコール類；パルミチン酸イソプロピル、ミリスチン酸イソプロピル、ミリスチン酸オクチルドデシル、ラウリン酸ヘキシル、乳酸セチル、モノステアリン酸プロピレングリコール、オレイン酸オレイル、２−エチルヘキサン酸ヘキサデシル、イソノナン酸イソノニル、イソノナン酸トリデシル、トリメチロールプロパントリイソステアレート、リンゴ酸ジイソステアリル等のエステル類；カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘニン酸、オレイン酸、ヤシ油脂肪酸、イソステアリン酸、イソパルミチン酸等の高級脂肪酸類；セラミド類、擬似型セラミドに代表される両親媒性物質；その他イソステアリルグリセリルエーテル、ポリオキシプロピレンブチルエーテル等が挙げられる。また、パーフルオロポリエーテル、ポリテトラフルオロエチレン等のフッ素系油も挙げられる。これらのうち、エステル類が好ましく、特に２−エチルヘキサン酸ヘキサデシル、イソノナン酸イソノニル、パルミチン酸イソプロピル等が好ましい。 Oil refers to oily substances excluding silicones, for example, hydrocarbons such as squalene, squalane, petrolatum, lanolin, ceresin, liquid paraffin, liquid isoparaffin, cycloparaffin, microcrystalline wax; castor oil, cocoa oil, mink Glycerides such as oil, avocado oil, olive oil, jojoba oil, castor oil; waxes such as beeswax, whale wax, lanolin, carnauba wax; cetyl alcohol, oleyl alcohol, stearyl alcohol, isostearyl alcohol, 2-octyldodecanol, glycerin Alcohols such as isopropyl palmitate, isopropyl myristate, octyldodecyl myristate, hexyl laurate, cetyl lactate, propylene glycol monostearate, oleyl oleate, 2-ethyl Esters such as hexadecyl hexanoate, isononyl isononanoate, tridecyl isononanoate, trimethylolpropane triisostearate, diisostearyl malate; capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid Higher fatty acids such as coconut oil fatty acid, isostearic acid and isopalmitic acid; amphiphiles typified by ceramides and pseudo-ceramides; other isostearyl glyceryl ethers and polyoxypropylene butyl ethers. Moreover, fluorine-type oils, such as perfluoropolyether and polytetrafluoroethylene, are also mentioned. Of these, esters are preferable, and hexadecyl 2-ethylhexanoate, isononyl isononanoate, isopropyl palmitate, and the like are particularly preferable.
これら油性成分は２種類以上を併用してもよく、またその含有量は、塗布時の滑らかさの点から、本発明の化粧料中０．００５〜１０重量％が好ましく、さらには０．０７〜５重量％、特には０．１〜２重量％が好ましい。 Two or more kinds of these oily components may be used in combination, and the content thereof is preferably 0.005 to 10% by weight in the cosmetic of the present invention from the viewpoint of smoothness during application, and more preferably 0.07. -5% by weight, particularly 0.1-2% by weight is preferred.
本発明の皮膚用化粧料には、上記成分のほか、通常の皮膚用化粧料に用いられる成分を目的に応じて適宜配合できる。このような成分としては、例えば抗フケ剤；ビタミン剤；殺菌剤；抗炎症剤；防腐剤；美白剤；デオドラント剤；キレート剤；ソルビトール、パンテノール等の保湿剤；染料、顔料等の着色剤；ヒドロキシエチルセルロース、メチルセルロース、ポリエチレングリコール、粘土鉱物等の粘度調整剤；乳化剤；クエン酸、水酸化カリウム等のｐＨ調整剤；植物エキス類；香料；紫外線吸収剤；紫外線防御剤；酸化防止剤；パール化剤等が挙げられる。 In addition to the above-described components, the skin cosmetic of the present invention can be appropriately blended with components used in normal skin cosmetics depending on the purpose. Such components include, for example, anti-dandruff agents; vitamins; bactericides; anti-inflammatory agents; antiseptics; whitening agents; deodorants; chelating agents; moisturizers such as sorbitol and panthenol; ; Viscosity modifiers such as hydroxyethylcellulose, methylcellulose, polyethylene glycol, clay minerals; emulsifiers; pH adjusters such as citric acid and potassium hydroxide; plant extracts; fragrances; UV absorbers; UV protection agents; And the like.
また、本発明の皮膚用化粧料は、乳液、クリーム、化粧水、フェイスローション、ボディローション等の皮膚保護用化粧料；液状ファンデーション、シェービング剤、頬紅、口紅、アイライナー、マスカラ、アイシャドウ等のメイク用化粧料；その他、アフターシェーブローション、化粧下地、サンケア剤、サンスクリーン剤、デオドラント剤等の皮膚用化粧料全般に利用できる。 The skin cosmetic of the present invention is a cosmetic for skin protection such as emulsion, cream, lotion, face lotion, body lotion; liquid foundation, shaving agent, blusher, lipstick, eyeliner, mascara, eye shadow, etc. Cosmetics for makeup; In addition, it can be used for all skin cosmetics such as after-shave lotion, makeup base, sun care agent, sunscreen agent, deodorant agent and the like.
以下の合成例で得られる分岐ポリグリセロール変性シリコーンの1Ｈ−ＮＭＲスペクトル中の各ピークの帰属は、溶媒により多少シフトするが、概ね以下の通りである。 The assignment of each peak in the 1 H-NMR spectrum of the branched polyglycerol-modified silicone obtained in the following synthesis example is somewhat shifted depending on the solvent, but is generally as follows.
０.０−０.２ｐｐｍ：Ｓｉ−ＣＨ 3
０.６−０.７ｐｐｍ：Ｓｉ−ＣＨ 2 −ＣＨ2−（４Ｈ）
１.５−１.７ｐｐｍ：Ｓｉ−ＣＨ2−ＣＨ 2 −（４Ｈ）
２.４−２.７ｐｐｍ：Ｓｉ−ＣＨ2−ＣＨ2−ＣＨ 2 −（４Ｈ）
３.３−４.０ｐｐｍ：分岐ポリグリセロール鎖のＨ（末端ヒドロキシ基除く、５Ｈ×グリセロール基の数）
６.７−７.２ｐｐｍ：フェノール（８Ｈ）
また、13Ｃ−ＮＭＲスペクトル中、分岐ポリグリセロール鎖を形成する基（１）〜（５）の各炭素由来のピークの帰属は、Macromolecules，１９９９，３２，４２４０記載の値を参考にした。
0.0-0.2 ppm: Si—C H 3
0.6-0.7 ppm: Si—C H 2 —CH 2 — (4H)
1.5-1.7ppm: Si-CH 2 -C H 2 - (4H)
2.4-2.7ppm: Si-CH 2 -CH 2 -C H 2 - (4H)
3.3-4.0 ppm: H of branched polyglycerol chain (excluding terminal hydroxy groups, 5H × number of glycerol groups)
6.7-7.2 ppm: phenol (8H)
In addition, in the 13 C-NMR spectrum, the assignment of the peak derived from each carbon of the groups (1) to (5) forming the branched polyglycerol chain was referred to the values described in Macromolecules, 1999, 32, 4240.
平均グリセロール鎖数は、1Ｈ−ＮＭＲスペクトルにより、分岐ポリグリセロール鎖のＨ数／（５×連結基の数）により、求めることが出来る。 The average number of glycerol chains can be determined by 1 H-NMR spectrum as follows: H number of branched polyglycerol chains / (5 × number of linking groups).
合成例１：分岐ポリグリセロール変性シリコーンＡ（連結基；−ＣＨ2ＣＨ2ＣＨ2−Ｃ6Ｈ4−Ｏ−）の合成例
フェノール変性シリコーン（東レ・ダウコーニング（株）製、商品名；ＢＹ１６−７５２、水酸基当量；１５００）１５０ｇをフラスコに取り、カリウムメトキシド（３０％メタノール溶液）５．６１ｇを加え、撹拌しながら減圧下に６０℃まで加温し、メタノールを全て留去し、黄色油状物としてカリウム化フェノール変性シリコーンを得た。９５℃まで昇温し、激しく撹拌しながらアルゴン気流下にグリシドール３９．９ｇ（５．４当量）を、定量送液ポンプを用いて３．５時間かけて添加した。２０分間さらに加熱撹拌後、室温まで冷却すると、淡黄白色固体状生成物が得られた。得られた分岐ポリグリセロール変性シリコーンにエタノール５００ｍＬを加え、カチオン交換樹脂によりカリウムを除去、濃縮し、微黄色油状物として分岐ポリグリセロール変性シリコーンＡを得た。（収率９８％）
得られた分岐ポリグリセロール変性シリコーンＡは、13Ｃ−ＮＭＲスペクトルの解析により、基（１）のメチン炭素由来のシグナル（７８．０〜８１．０ｐｐｍ）の存在から、基（１）を有する分岐ポリグリセロール変性シリコーンであることを確認した。また1Ｈ−ＮＭＲスペクトルの解析により、平均グリセロール基数（Ｇ）＝１０．９（片側５．５）、平均ケイ素原子数（Ｓｉ）＝３１．９、Ｇ／Ｓｉ比は０．３４であり、ＧＰＣ解析（カラム：ＫＦ−８０４Ｌ（×２）、脂肪族アミン／クロロホルム溶液、４０℃、ポリスチレン換算）に依れば、数平均分子量（Ｍｎ）は、４１００であった。
Synthesis Example 1: Synthesis Example of Branched Polyglycerol-Modified Silicone A (Linking Group: —CH 2 CH 2 CH 2 —C 6 H 4 —O—) Phenol-modified silicone (trade name; BY16 manufactured by Toray Dow Corning Co., Ltd.) -752, Hydroxyl equivalent: 1500) 150 g was taken in a flask, added with 5.61 g of potassium methoxide (30% methanol solution), heated to 60 ° C. under reduced pressure with stirring, all the methanol was distilled off, A potassiumated phenol-modified silicone was obtained as an oil. The temperature was raised to 95 ° C., and 39.9 g (5.4 equivalents) of glycidol was added over 3.5 hours under a stream of argon with vigorous stirring over a period of 3.5 hours. After further heating and stirring for 20 minutes and cooling to room temperature, a pale yellowish white solid product was obtained. Ethanol (500 mL) was added to the obtained branched polyglycerol-modified silicone, potassium was removed and concentrated using a cation exchange resin, and branched polyglycerol-modified silicone A was obtained as a slightly yellow oily substance. (Yield 98%)
The obtained branched polyglycerol-modified silicone A has a branch having the group (1) from the presence of a signal (78.0 to 81.0 ppm) derived from the methine carbon of the group (1) by analysis of 13 C-NMR spectrum. It was confirmed that it was a polyglycerol-modified silicone. Further, by analysis of the 1 H-NMR spectrum, the average number of glycerol groups (G) = 10.9 (one side 5.5), the average number of silicon atoms (Si) = 31.9, and the G / Si ratio is 0.34, According to GPC analysis (column: KF-804L (× 2), aliphatic amine / chloroform solution, 40 ° C., polystyrene conversion), the number average molecular weight (Mn) was 4100.
合成例２：分岐ポリグリセロール変性シリコーンＢ（連結基；−ＣＨ2ＣＨ2ＣＨ2−Ｃ6Ｈ4−Ｏ−）の合成例
フェノール変性シリコーン（東レ・ダウコーニング（株）製、商品名；ＢＹ１６−７９９、水酸基当量；７５０）３００．０ｇをフラスコに取り、水酸化カリウム（１Ｍエタノール溶液）２０．０ｍＬを加え、撹拌しながら減圧下に６０℃まで加温し、メタノールを全て留去し、黄色油状物としてカリウム化フェノール変性シリコーンを得た。９５℃まで昇温し、激しく撹拌しながらアルゴン気流下にグリシドール６６．７ｇ（２．２５当量）を定量送液ポンプを用いて３．５時間かけて添加した。２０分間さらに加熱撹拌後、室温まで冷却すると、淡黄白色固体状生成物が得られた。得られた分岐ポリグリセロール変性シリコーンにエタノール１０００ｍＬを加え、カチオン交換樹脂によりカリウムを除去、濃縮し、微黄色油状物として分岐ポリグリセロール変性シリコーンＢを得た（収率９８％）。
Synthesis Example 2: Synthesis Example of Branched Polyglycerol-modified Silicone B (Linking Group: —CH 2 CH 2 CH 2 —C 6 H 4 —O—) Phenol-modified silicone (trade name; BY16 manufactured by Toray Dow Corning Co., Ltd.) -799, hydroxyl equivalent: 750) Take 300.0 g in a flask, add 20.0 mL of potassium hydroxide (1M ethanol solution), heat to 60 ° C. under reduced pressure with stirring, all the methanol is distilled off, A potassiumated phenol-modified silicone was obtained as a yellow oil. The temperature was raised to 95 ° C., and 66.7 g (2.25 equivalents) of glycidol was added over 3.5 hours under a stream of argon with vigorous stirring using a quantitative liquid feeding pump. After further heating and stirring for 20 minutes and cooling to room temperature, a pale yellowish white solid product was obtained. To the resulting branched polyglycerol-modified silicone, 1000 mL of ethanol was added, potassium was removed with a cation exchange resin and concentrated to obtain branched polyglycerol-modified silicone B as a slightly yellow oil (yield 98%).
得られた分岐ポリグリセロール変性シリコーンＢは、13Ｃ−ＮＭＲスペクトルの解析により、基（１）のメチン炭素由来のシグナル（７８．０〜８１．０ｐｐｍ）の存在から、基（１）を有する分岐ポリグリセロール変性シリコーンであることを確認した。また1Ｈ−ＮＭＲスペクトルの解析により、平均グリセロール基数（Ｇ）＝４．６（片側２．３）、平均ケイ素原子数（Ｓｉ）＝３１．９、Ｇ／Ｓｉ比は０．１４であり、ＧＰＣ解析（カラム：ＫＦ−８０４Ｌ（×２）、脂肪族アミン／クロロホルム溶液、４０℃、ポリスチレン換算）に依れば、数平均分子量（Ｍｎ）は、３５００であった。 The obtained branched polyglycerol-modified silicone B has a branched group (1) from the presence of a signal (78.0 to 81.0 ppm) derived from the methine carbon of the group (1) by analysis of 13 C-NMR spectrum. It was confirmed that it was a polyglycerol-modified silicone. Moreover, by analysis of 1 H-NMR spectrum, average glycerol group number (G) = 4.6 (one side 2.3), average number of silicon atoms (Si) = 31.9, G / Si ratio is 0.14, According to GPC analysis (column: KF-804L (× 2), aliphatic amine / chloroform solution, 40 ° C., polystyrene conversion), the number average molecular weight (Mn) was 3500.
合成例３：分岐ポリグリセロール変性シリコーンＣ（連結基；−ＣＨ2ＣＨ2ＣＨ2−Ｏ−ＣＨ2ＣＨ2−Ｏ−）の合成例
特公平６−８９１４７号公報記載の方法に従い、下記構造式で示されるアリル化ジイソプロピリデントリグリセリンを得た。
Synthesis Example 3: Synthesis Example of Branched Polyglycerol-Modified Silicone C (Linking Group: —CH 2 CH 2 CH 2 —O—CH 2 CH 2 —O—) According to the method described in JP-B-6-89147, the following structural formula An allylated diisopropylidenetriglycerin represented by the formula:
市販のオルガノハイドロジェンポリシロキサン（チッソ製、商品名；ＩＣ−８４６１−１Ｆ２０−ＢＬ、水酸基当量；３０００）３０．０ｇ、前記のアリル化ジイソプロピリデントリグリセリン１４．４ｇ、イソプロピルアルコール１５０ｇ、塩化白金酸（２％イソプロピルアルコール溶液）０．４ｇ、酢酸カリウム（１０％エタノール溶液）０．４ｇをフラスコに入れ、溶媒還流温度にて５時間反応させ、さらに１−ヘキセン２０．５ｇを加えて２時間反応させた。０．０１Ｍ塩酸１００ｇを加え、イソプロピルアルコール還流温度にて５時間反応させた。そのまま減圧にして溶媒等を留去し、トリグリセリン変性シリコーンを得た。 30.0 g of a commercially available organohydrogenpolysiloxane (manufactured by Chisso, trade name: IC-8461-1F20-BL, hydroxyl equivalent: 3000), 14.4 g of the allylated diisopropylidene triglycerin, 150 g of isopropyl alcohol, platinum chloride 0.4 g of acid (2% isopropyl alcohol solution) and 0.4 g of potassium acetate (10% ethanol solution) were placed in a flask and reacted at the solvent reflux temperature for 5 hours. Further, 20.5 g of 1-hexene was added for 2 hours. Reacted. 100 g of 0.01M hydrochloric acid was added, and the mixture was reacted at isopropyl alcohol reflux temperature for 5 hours. The solvent was distilled off under reduced pressure as it was to obtain triglycerin-modified silicone.
この得られたトリグリセリン変性シリコーン４０．０ｇをフラスコに取り、カリウムメトキシド（３０％メタノール溶液）１．４ｇを加え、撹拌しながら減圧下に６０℃まで加温し、メタノールを全て留去し、黄色油状物としてカリウム化トリグリセリン変性シリコーンを得た。９５℃まで昇温し、激しく撹拌しながらアルゴン気流下にグリシドール５．０ｇを定量送液ポンプを用いて３．５時間かけて添加した。２０分間さらに加熱撹拌後、室温まで冷却すると、淡黄白色固体状生成物が得られた。得られた分岐ポリグリセロール変性シリコーンにエタノール１５０ｍＬを加え、カチオン交換樹脂によりカリウムを除去、濃縮し、微黄色油状物として分岐ポリグリセロール変性シリコーンＣを得た。 40.0 g of the obtained triglycerin-modified silicone was placed in a flask, 1.4 g of potassium methoxide (30% methanol solution) was added, and the mixture was heated to 60 ° C. under reduced pressure while stirring to distill off all the methanol. The potassium triglycerin-modified silicone was obtained as a yellow oil. The temperature was raised to 95 ° C., and 5.0 g of glycidol was added over 3.5 hours under a stream of argon with vigorous stirring using a quantitative liquid feeding pump. After further heating and stirring for 20 minutes and cooling to room temperature, a pale yellowish white solid product was obtained. Ethanol 150mL was added to the obtained branched polyglycerol modified silicone, potassium was removed and concentrated by cation exchange resin, and branched polyglycerol modified silicone C was obtained as a slightly yellow oily substance.
ＩＲ、1Ｈ−ＮＭＲスペクトル、13Ｃ−ＮＭＲスペクトルの測定より、得られた化合物は基（１）〜（５）を含む分岐ポリグリセロール変性シリコーンであることを確認した。 From the measurement of IR, 1 H-NMR spectrum and 13 C-NMR spectrum, it was confirmed that the obtained compound was a branched polyglycerol-modified silicone containing groups (1) to (5).
実施例１
表１に示す組成の化粧水を調製し、下記方法で配合安定性及び感触に関する官能評価を行った。結果を表１に示す。
Example 1
A lotion having the composition shown in Table 1 was prepared and subjected to sensory evaluation regarding blending stability and feel by the following methods. The results are shown in Table 1.
＜配合安定性評価法＞
化粧水を５０℃で１週間保存し、目視で外観の変化（成分の分離・分層、濁り等）を観察し、下記基準で評価した。
○：成分の分離・分層、及び濁りが見られない
×：成分の分離・分層、あるいは濁りが見られる
＜感触に関する官能評価法＞
専門のパネラーが汎用の石鹸で手を洗浄し、洗浄後の手（皮膚）に化粧水を適量塗布し、塗布後の感触に関する官能評価を行った。官能評価は下記の判定基準に従って行った。
・評価基準
べたつき感
○：べたつき感が全くない
△：べたつき感がほとんどない
×：べたつき感がある
すべり感
○：すべり感が非常にある
△：すべり感がややある
×：すべり感がない
しっとり感
○：しっとり感が非常にある
△：しっとり感がややある
×：しっとり感がない
<Compounding stability evaluation method>
The lotion was stored at 50 ° C. for 1 week, and changes in appearance (separation / separation of components, turbidity, etc.) were visually observed and evaluated according to the following criteria.
○: Separation / layering of components and turbidity are not observed ×: Separation / layering of components or turbidity is observed <Sensory evaluation method for touch>
A specialized panelist washed hands with general-purpose soap, applied an appropriate amount of lotion to the washed hands (skin), and performed sensory evaluation on the feel after application. Sensory evaluation was performed according to the following criteria.
Evaluation criteria Sticky feeling ○: No sticky feeling △: Little sticky feeling ×: Sticky feeling slipping feeling ○: Very slippery feeling △: Slight feeling slightly X: No slipping feeling Moist feeling ○: Very moist △: Slightly moist x: No moist
表１の結果が示すように、本実施例の化粧水は、配合安定性を損なうことなく、非常に良好な使用感を認知できた。 As shown in the results of Table 1, the lotion of this example could recognize a very good feeling of use without impairing the blending stability.
以下、本発明の効果を得るのに適した処方例を挙げる。 Hereinafter, formulation examples suitable for obtaining the effects of the present invention will be given.
処方例１
表２に示す組成の化粧水
Formulation Example 1
Lotions with compositions shown in Table 2
処方例２
表３に示す組成の化粧水
Formulation Example 2
Lotions with compositions shown in Table 3
処方例３
表４に示す組成のクリーム
Formulation Example 3
Cream with composition shown in Table 4
処方例４
表５に示す組成のクリーム
Formulation Example 4
Cream with composition shown in Table 5
処方例５
表６に示す組成のサンスクリーン乳液
Formulation Example 5
Sunscreen emulsion with composition shown in Table 6
Claims (4)
−（Ｒ9）p−Ｏ−（ＡＯ）q− （７）
（式中、Ｒ9は、置換基を有していてもよい、炭素数１〜２２の直鎖もしくは分岐鎖のアルキレン基、アルケニレン基又は炭素数６〜２８のアリーレン基、ＡＯは炭素数１〜４のアルキレンオキシ基（オキシアルキレン基ともいう）又は炭素数６〜１０のアリーレンオキシ基（オキシアリーレン基ともいう）、ｐは０又は１の数、ｑは０〜３０の数を示し、ｑ個のＡＯは同一でも異なっていてもよい。）
The cosmetic for skin according to any one of claims 1 to 3, wherein the linking group of the component (a) is a divalent group represented by the following formula (7).
- (R 9) p -O- ( AO) q - (7)
(In the formula, R 9 may have a substituent, a linear or branched alkylene group having 1 to 22 carbon atoms, an alkenylene group, or an arylene group having 6 to 28 carbon atoms, and AO has 1 carbon atom. -4 alkyleneoxy group (also referred to as oxyalkylene group) or aryleneoxy group having 6 to 10 carbon atoms (also referred to as oxyarylene group), p represents the number of 0 or 1, q represents the number of 0-30, q Each AO may be the same or different.)
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006031152A1 (en) * | 2006-07-04 | 2008-01-10 | Byk-Chemie Gmbh | Polyhydroxy-functional polysiloxanes as anti-adhesive and dirt-repellent additives in coatings, polymeric molding compounds and thermoplastics, process for their preparation and their use |
| JP2008143823A (en) * | 2006-12-08 | 2008-06-26 | Kao Corp | Skin cosmetic |
| JP2008143822A (en) * | 2006-12-08 | 2008-06-26 | Kao Corp | Skin cosmetic |
| EP2103301A1 (en) | 2008-03-21 | 2009-09-23 | Shin-Etsu Chemical Co., Ltd. | Polyglycerin-modified silicone and a cosmetic comprising the same |
| US9023969B2 (en) | 2008-04-03 | 2015-05-05 | Shin-Etsu Chemical Co., Ltd. | Powder surface-treated with an organopolysiloxane having carboxyl groups, a dispersion of the same, and a cosmetic comprising the same |
| EP3492064A1 (en) | 2017-11-29 | 2019-06-05 | Shin-Etsu Chemical Co., Ltd. | Bicontinuous microemulsion composition and cosmetic |
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2003
- 2003-09-24 JP JP2003331467A patent/JP3946680B2/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006031152A1 (en) * | 2006-07-04 | 2008-01-10 | Byk-Chemie Gmbh | Polyhydroxy-functional polysiloxanes as anti-adhesive and dirt-repellent additives in coatings, polymeric molding compounds and thermoplastics, process for their preparation and their use |
| JP2008143823A (en) * | 2006-12-08 | 2008-06-26 | Kao Corp | Skin cosmetic |
| JP2008143822A (en) * | 2006-12-08 | 2008-06-26 | Kao Corp | Skin cosmetic |
| EP2103301A1 (en) | 2008-03-21 | 2009-09-23 | Shin-Etsu Chemical Co., Ltd. | Polyglycerin-modified silicone and a cosmetic comprising the same |
| US9023969B2 (en) | 2008-04-03 | 2015-05-05 | Shin-Etsu Chemical Co., Ltd. | Powder surface-treated with an organopolysiloxane having carboxyl groups, a dispersion of the same, and a cosmetic comprising the same |
| EP3492064A1 (en) | 2017-11-29 | 2019-06-05 | Shin-Etsu Chemical Co., Ltd. | Bicontinuous microemulsion composition and cosmetic |
| KR20190063435A (en) | 2017-11-29 | 2019-06-07 | 신에쓰 가가꾸 고교 가부시끼가이샤 | Bicontinuous Microemulsion Composition and Cosmetic |
| CN110013444A (en) * | 2017-11-29 | 2019-07-16 | 信越化学工业株式会社 | Bicontinuous microemulsion shape liquid composition and cosmetics |
| US11007127B2 (en) | 2017-11-29 | 2021-05-18 | Shin-Etsu Chemical Co., Ltd. | Bicontinuous microemulsion composition and cosmetic |
| CN110013444B (en) * | 2017-11-29 | 2023-03-28 | 信越化学工业株式会社 | Bicontinuous microemulsion composition and cosmetic |
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