JP2011246706A - 新規なオルガノポリシロキサン、それを含む界面活性剤、エマルジョン組成物、粉体処理剤、油性原料の増粘剤、ゲル化剤、ゲル状組成物、化粧料用原料並びに、これらを含む外用剤及び化粧料 - Google Patents
新規なオルガノポリシロキサン、それを含む界面活性剤、エマルジョン組成物、粉体処理剤、油性原料の増粘剤、ゲル化剤、ゲル状組成物、化粧料用原料並びに、これらを含む外用剤及び化粧料 Download PDFInfo
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- JP2011246706A JP2011246706A JP2011102363A JP2011102363A JP2011246706A JP 2011246706 A JP2011246706 A JP 2011246706A JP 2011102363 A JP2011102363 A JP 2011102363A JP 2011102363 A JP2011102363 A JP 2011102363A JP 2011246706 A JP2011246706 A JP 2011246706A
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- oil
- silicone
- modified organopolysiloxane
- powder
- Prior art date
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 420
- 239000000843 powder Substances 0.000 title claims abstract description 173
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 97
- 238000011282 treatment Methods 0.000 title claims abstract description 69
- 239000002994 raw material Substances 0.000 title claims abstract description 40
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 37
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- 239000000203 mixture Substances 0.000 title claims description 131
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- 239000002562 thickening agent Substances 0.000 title claims description 21
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- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 82
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 44
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- 125000005353 silylalkyl group Chemical group 0.000 claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 97
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
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- 239000007788 liquid Substances 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
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- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 229940126062 Compound A Drugs 0.000 claims 1
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- 238000007334 copolymerization reaction Methods 0.000 claims 1
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- 238000002156 mixing Methods 0.000 description 43
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- 150000004665 fatty acids Chemical class 0.000 description 26
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 26
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 24
- 210000004209 hair Anatomy 0.000 description 24
- 239000001993 wax Substances 0.000 description 24
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 23
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 22
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 21
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 16
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
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- 238000004945 emulsification Methods 0.000 description 15
- 238000011156 evaluation Methods 0.000 description 15
- 229920000591 gum Polymers 0.000 description 15
- ONLRKTIYOMZEJM-UHFFFAOYSA-N n-methylmethanamine oxide Chemical compound C[NH+](C)[O-] ONLRKTIYOMZEJM-UHFFFAOYSA-N 0.000 description 15
- 239000000049 pigment Substances 0.000 description 15
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- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 14
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- 235000019437 butane-1,3-diol Nutrition 0.000 description 12
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 11
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- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 9
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- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- UNZSHUCNBUBSGW-IFNWOZJISA-M sodium;(9z,12z,15z)-octadeca-9,12,15-trienoate Chemical compound [Na+].CC\C=C/C\C=C/C\C=C/CCCCCCCC([O-])=O UNZSHUCNBUBSGW-IFNWOZJISA-M 0.000 description 1
- 235000020712 soy bean extract Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray 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
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 229910052917 strontium silicate Inorganic materials 0.000 description 1
- QSQXISIULMTHLV-UHFFFAOYSA-N strontium;dioxido(oxo)silane Chemical compound [Sr+2].[O-][Si]([O-])=O QSQXISIULMTHLV-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 108010041266 surfactin peptide Proteins 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000001845 taraxacum officinale leaf extract Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 108010021724 tonin Proteins 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 229940117985 trimethyl pentaphenyl trisiloxane Drugs 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- STYCVOUVPXOARC-UHFFFAOYSA-M trimethyl(octyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(C)C STYCVOUVPXOARC-UHFFFAOYSA-M 0.000 description 1
- SCRSFLUHMDMRFP-UHFFFAOYSA-N trimethyl-(methyl-octyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C SCRSFLUHMDMRFP-UHFFFAOYSA-N 0.000 description 1
- CIAZJIQGPOGZDS-UHFFFAOYSA-N trimethyl-(methyl-tetradecyl-trimethylsilyloxysilyl)oxysilane Chemical compound CCCCCCCCCCCCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C CIAZJIQGPOGZDS-UHFFFAOYSA-N 0.000 description 1
- UUJLHYCIMQOUKC-UHFFFAOYSA-N trimethyl-[oxo(trimethylsilylperoxy)silyl]peroxysilane Chemical compound C[Si](C)(C)OO[Si](=O)OO[Si](C)(C)C UUJLHYCIMQOUKC-UHFFFAOYSA-N 0.000 description 1
- SVTUWEUXLNHYPF-UHFFFAOYSA-N trimethyl-[propyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C SVTUWEUXLNHYPF-UHFFFAOYSA-N 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- HFMRLLVZHLGNAO-UHFFFAOYSA-N trimethylsilyloxysilicon Chemical compound C[Si](C)(C)O[Si] HFMRLLVZHLGNAO-UHFFFAOYSA-N 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
- 229940117972 triolein Drugs 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 235000020240 turmeric extract Nutrition 0.000 description 1
- 239000008513 turmeric extract Substances 0.000 description 1
- 229940052016 turmeric extract Drugs 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000011912 vitamin B7 Nutrition 0.000 description 1
- 239000011735 vitamin B7 Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- KUPGJMJHAFGISS-UHFFFAOYSA-L zinc;hexadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O KUPGJMJHAFGISS-UHFFFAOYSA-L 0.000 description 1
- OJYLAHXKWMRDGS-UHFFFAOYSA-N zingerone Chemical compound COC1=CC(CCC(C)=O)=CC=C1O OJYLAHXKWMRDGS-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/0241—Containing particulates characterized by their shape and/or structure
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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Abstract
【解決手段】糖アルコール変性基とシロキサンデンドロン構造を有するシリルアルキル基、更に、任意に、長鎖炭化水素基、を同一分子中に備える、特定の化学構造を有する共変性オルガノポリシロキサンを調製し、当該共変性オルガノポリシロキサンを界面活性剤、粉体処理剤、ゲル化剤等として、適宜、粉体、油剤等と共に、化粧料用原料として外用剤、特に化粧料に配合する。
【選択図】なし
Description
R1は一価有機基(但し、R2、L1及びQを除く)を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基、又は、下記一般式(2−1);
L1はi=1のときの下記一般式(3);
R3は炭素原子数1〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
R4はそれぞれ独立して炭素原子数1〜6のアルキル基又はフェニル基を表し、
Zは二価有機基を表し、
iはLiで示されるシリルアルキル基の階層を表し、該シリルアルキル基の繰り返し数である階層数がkのとき1〜kの整数であり、階層数kは1〜10の整数であり、Li+1はiがk未満のときは該シリルアルキル基であり、i=kのときはR4であり、hiは0〜3の範囲の数である)で表される、シロキサンデンドロン構造を有するシリルアルキル基を表し、
Qは糖アルコール基含有有機基を表し、
a 、b 、c及びdは、それぞれ、1.0≦a≦2.5、0≦b≦1.5、0.0001≦c≦1.5、0.0001≦d≦1.5の範囲にある数である}で表される共変性オルガノポリシロキサンによって達成される。
Rは二価有機基を表し、
eは1又は2である)、又h、下記一般式(4−2):
Rは上記のとおりであり、
e’は0又は1である)で表される糖アルコール基含有有機基であることが好ましい。
R3、R4及びZは上記のとおりであり、
h1及びh2は、それぞれ独立して、0〜3の範囲の数である)で表される官能基であることが好ましい。
R2、L1及びQは上記のとおりであり、
Xはメチル基、R2、L1及びQからなる群から選択される基であり、
n1、n2、n3及びn4は、それぞれ独立して、0〜2,000の範囲の数であり、n1+n2+n3+n4は0〜2,000の範囲の数である。但し、n3=0のとき、Xの少なくとも一方はL1であり、また、n4=0のとき、Xの少なくとも一方はQである)で表されるものが好ましい。
R2、Q、X、Z、n1、n2、n3及びn4は上記のとおりである)又は下記構造式(1−1−2):
R2、Q、X、Z、n1、n2、n3及びn4は上記のとおりである)
で表されるものがより好ましい。
R7は、それぞれ独立して、置換若しくは非置換の、直鎖状若しくは分岐鎖状の、炭素原子数2〜22のアルキレン基若しくはアルケニレン基、又は、炭素原子数6〜22のアリーレン基を表し、
R8は、下記
(a)珪素原子結合水素原子を有するオルガノポリシロキサン
(b)反応性不飽和基を1分子中に1つ有する有機化合物
(c)反応性不飽和基を1分子中に1つ有するシロキサンデンドロン化合物、及び、
(d)反応性不飽和基を1分子中に1つ有する糖アルコール官能性有機化合物
を反応させて得ることができる。
R3及びR4は上記のとおりであり、
Z´は二価有機基を表し、
h1は0〜3の範囲の数であり、
L´1は、R4、又は、j=1のときの下記一般式(3’’):
Zは二価有機基を表し、
jはLjで示されるシリルアルキル基の階層を表し、該シリルアルキル基の繰り返し数である階層数がk´のとき1〜k´の整数であり、階層数k´は1〜9の整数であり、Lj+1はjがk´未満のときは該シリルアルキル基であり、j=k´のときはR4である。hjは0〜3の範囲の数である)で表されるシリルアルキル基を表す}で表される分子鎖末端に1個の炭素−炭素二重結合を有するシロキサンデンドロン構造を有する化合物であることが好ましい。
R1は一価有機基(但し、R2、L1及びQを除く)を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基、又は、下記一般式(2−1);
L1はi=1のときの下記一般式(3);
R3は炭素原子数1〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
R4はそれぞれ独立して炭素原子数1〜6のアルキル基又はフェニル基を表し、
Zは二価有機基を表し、
iはLiで示されるシリルアルキル基の階層を表し、該シリルアルキル基の繰り返し数である階層数がkのとき1〜kの整数であり、階層数kは1〜10の整数であり、Li+1はiがk未満のときは該シリルアルキル基であり、i=kのときはR4であり、hiは0〜3の範囲の数である)で表される、シロキサンデンドロン構造を有するシリルアルキル基を表し、
Qは糖アルコール基含有有機基を表し、
a 、b 、c及びdは、それぞれ、1.0≦a≦2.5、0≦b≦1.5、0.0001≦c≦1.5、0.0001≦d≦1.5の範囲にある数である}で表されるものである。
Rは二価有機基を表し、
eは1又は2である)、又h、下記一般式(4−2):
Rは上記のとおりであり、
e’は0又は1である)で表される。
R2、L1及びQは上記のとおりであり、
Xはメチル基、R2、L1及びQからなる群から選択される基であり、
n1、n2、n3及びn4は、それぞれ独立して、0〜2,000の範囲の数であり、n1+n2+n3+n4は0〜2,000の範囲の数である。但し、n3=0のとき、Xの少なくとも一方はL1であり、また、n4=0のとき、Xの少なくとも一方はQである)で表される直鎖状のポリシロキサン構造を有する共変性オルガノポリシロキサンであることが好ましい。
R2、Q、X、Z、n1、n2、n3及びn4は上記のとおりである)、又は、下記構造式(1−1−2):
R2、Q、X、Z、n1、n2、n3及びn4は上記のとおりである)で表される共変性オルガノポリシロキサンがより好ましい。
変性率(モル%)=(1分子あたりの珪素原子に結合した糖アルコール含有有機基の数)/{6+2×(a+b+c)}×100
で示される。例えば、1つの糖アルコール含有有機基を有するトリシロキサンからなる共変性オルガノポリシロキサンの場合には、8個の珪素原子結合官能基のうち、1個が糖アルコール含有有機基により変性されているから、糖アルコール含有有機基による変性率は、12.5モル%である。
R1、a 、b及びcは上記のとおりである)で表される(a’)オルガノハイドロジェンシロキサンと、(c)反応性不飽和基を1分子中に1つ有するシロキサンデンドロン化合物と、(d)反応性不飽和基を1分子中に1つ有する糖アルコール官能性有機化合物を少なくとも反応させて得ることができる。(e)反応性不飽和基を1分子中に1つ有する炭化水素化合物又は反応性不飽和基を1分子中に1つ有する鎖状オルガノポリシロキサンを更に反応させることが好ましい。
R1は、各々独立に、上記のとおりであり、
X’はR1又は水素原子から選択される基であり、
n1、n2及びn3は上記のとおりである。但し、n2+n3=0のとき、X’の少なくとも一方は水素原子である)で表されるオルガノハイドロジェンシロキサンが好ましい。
R3及びR4は上記のとおりであり、
Z´は二価有機基を表し、
h1は0〜3の範囲の数であり、
L´1は、R4、又は、j=1のときの下記一般式(3’’):
Zは二価有機基を表し、
jはLjで示されるシリルアルキル基の階層を表し、該シリルアルキル基の繰り返し数である階層数がk´のとき1〜k´の整数であり、階層数k´は1〜9の整数であり、Lj+1はjがk´未満のときは該シリルアルキル基であり、j=k´のときはR4である。hjは0〜3の範囲の数である)で表されるシリルアルキル基を表す}で表される分子鎖末端に1個の炭素−炭素二重結合を有するシロキサンデンドロン構造を有する化合物が好ましい。
R’は不飽和有機基を表し、
eは1又は2であり、好ましくは1である)、又は、下記一般式(4’−2):
R’は不飽和有機基を表し、
e’は0又は1であり、好ましくは0である)で表される糖アルコールのモノ不飽和エーテル化合物が好ましい。
R2’は炭素原子数7〜28の、置換若しくは非置換の、直鎖状又は分岐状の一価炭化水素基又は下記一般式(2−1);
本発明の共変性オルガノポリシロキサンは、各種粉体の親水性表面に配向して適度な撥水性を付与できるため、粉体処理剤、特に、粉体表面処理剤として好適に用いることができる。本発明の粉体処理剤中の前記共変性オルガノポリシロキサンの配合量は、粉体処理効果、特に、粉体表面処理効果、を発揮する限り特に限定されるものではないが、例えば、50〜100重量(質量)%とすることができ、70〜100重量(質量)%が好ましく、90〜100重量(質量)%がより好ましい。
本発明における「粉体」は、化粧料の成分として一般に使用されるものであり、白色及び着色顔料、並びに、体質顔料を含む。白色及び着色顔料は化粧料の着色等に使用され、一方、体質顔料は、化粧料の感触改良等に使用される。本発明における「粉体」としては、化粧料に通常使用される白色及び着色顔料、並びに、体質顔料を特に制限なく使用することができる。1種類又は2種類以上の粉体を配合することが好ましい。
本発明における「油剤」は、化粧料の成分として一般に使用されるものであり、特に限定されるものではない。油剤は、通常は室温で液体であるが、ワックスのような固形であってもよく、後述する高粘度且つ粘稠なガム状或いはペースト状であってもよい。
R9は、水素原子、水酸基、或いは、炭素原子数1〜30の、一価の非置換又はフッ素若しくはアミノ置換アルキル基、アリール基、アルコキシ基及び(CH3)3SiO{(CH3)2SiO}lSi(CH3)2CH2CH2-(lは0〜1000の整数)で示される基から選択される基であり、
fは、0〜3の整数であり、
g´は、0〜1000の整数であり、l´は、0〜1000の整数であり、但し、1≦g´+l´≦2000である)
R9は、上記と同様であり、
mは、0〜8の整数であり、
nは、0〜8の整数であり、但し、3≦m+n≦8である)
R9は、上記と同様であり、
pは1〜4の整数であり、
qは0〜500の整数である)
で表されるオルガノポリシロキサンを使用することができる。
本発明の共変性オルガノポリシロキサンは、親水性の糖アルコール含有有機基と疎水性の長鎖炭化水素基を同一分子中に備えるので、界面活性剤として好適に用いることができる。本発明の界面活性剤中の前記共変性オルガノポリシロキサンの配合量は、界面活性効果を発揮する限り特に限定されるものではないが、例えば、50〜100重量(質量)%とすることができ、70〜100重量(質量)%が好ましく、90〜100重量(質量)%がより好ましい。
本発明の共変性オルガノポリシロキサンは、増粘剤又はゲル化剤、特に油剤の増粘剤又はゲル化剤として使用することもできる。本発明の増粘剤又はゲル化剤中の前記共変性オルガノポリシロキサンの配合量は、増粘効果又はゲル化効果を発揮する限り特に限定されるものではないが、例えば、50〜100重量(質量)%とすることができ、70〜100重量(質量)%が好ましく、90〜100重量(質量)%がより好ましい。
反応器に平均組成式:MD72DH 12M で表されるメチルハイドロジェンポリシロキサン 159.5g、平均組成式:CH2=CH−Si(OSi(CH3)3)3で表されるビニルトリストリメチルシロキシシラン 81.9g、キシリトールモノアリルエーテル 19.8g、イソプロピルアルコール(IPA) 75gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒30mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*1 3DR*2 9Mで表されるシロキサンデンドロン構造を有する新規なキシリトール共変性シリコーンを得た。ここで、R*1及びR*2は下記を示す。
R*1= キシリトール残基
R*2= −C2H4Si(OSiMe3)3
収量は 222.0g(85%)であった。生成物の25℃における動粘度は298,900mm2/sec、屈折率は1.416、性状は淡黄色の不透明均一な粘稠液体であった。
反応器に1,3−ジヒドロジシロキサン 97.3gを加え、75℃まで加熱し、平均組成式:CH2=CH−Si(OSi(CH3)3)3で表されるビニルトリストリメチルシロキシシラン 46.8gと白金触媒4mgの混合物を3時間かけて滴下した。1時間エージングした後、ガスクロマトグラフィーによりビニルトリストリメチルシロキシシランの消失を確認した。余剰の1,3−ジヒドロジシロキサンを、減圧下で除き、続いて、キシリトールモノアリルエーテル 33.8gとイソプロピルアルコール(IPA)30gを加えて攪拌しながら80℃まで加温した。白金触媒8mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MR*1MR*2で表されるシロキサンデンドロン構造を有する新規なキシリトール共変性シリコーンを得た。ここで、R*1及びR*2は下記を示す。
R*1= キシリトール残基
R*2= −C2H4Si(OSiMe3)3
収量は 86.0g(86%)であった。生成物の25℃における動粘度は117,300mm2/sec、屈折率は1.442、性状は淡黄色の半透明均一な粘稠液体であった。
反応器に平均組成式:MD72DH 12Mで表されるメチルハイドロジェンポリシロキサン 168.1g、平均組成式:CH2=CH−Si(OSi(CH3)3)3で表されるビニルトリストリメチルシロキシシラン 28.8g、キシリトールモノアリルエーテル 18.9g、1−ヘキサデセン 42.9g、イソプロピルアルコール(IPA) 75gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒30mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*1 3DR*2 3DR*3 6Mで表されるシロキサンデンドロン構造を有する新規なキシリトール共変性シリコーンを得た。ここで、R*1、R*2及びR*3は下記を示す。
R*1= キシリトール残基
R*2= −C2H4Si(OSiMe3)3
R*3= −C16H33
収量は 225.1g(87%)であった。生成物の25℃における動粘度は141,000mm2/sec、屈折率は1.424、性状は淡黄色の不透明均一な粘稠液体であった。
反応器に平均組成式:MD45DH 2Mで表されるメチルハイドロジェンポリシロキサン 226.5g、平均組成式:CH2=CH−Si(OSi(CH3)3)3で表されるビニルトリストリメチルシロキシシラン 20.2g、キシリトールモノアリルエーテル 16.3g、イソプロピルアルコール(IPA) 78gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒31mgを添加し、80℃で3時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD45DR*1 1DR*2 1Mで表されるシロキサンデンドロン構造を有する新規なキシリトール共変性シリコーンを得た。ここで、R*1及びR*2は下記を示す。
R*1= キシリトール残基
R*2= −C2H4Si(OSiMe3)3
収量は 234.9g(89%)であった。生成物の25℃における動粘度は4,600mm2/sec、屈折率は1.410、性状は淡黄色の半透明均一な液体であった。
反応器に平均組成式:MD72DH 12M で表されるメチルハイドロジェンポリシロキサン 116.6g、平均組成式:CH2=CH−Si(OSi(CH3)3)3で表されるビニルトリストリメチルシロキシシラン 12.1g、キシリトールモノアリルエーテル 13.5g、1−ヘキサデセン 29.7g、平均構造式:CH2=CHSi(CH3)2[OSi(CH3)2]25OSi(CH3)3で表される片末端ビニル変性ジメチルポリシロキサン 38.1g、イソプロピルアルコール(IPA) 63gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒24mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*1 3DR*2 2DR*3 6DR*4 1Mで表されるシロキサンデンドロン構造を有する新規なキシリトール共変性シリコーンを得た。ここで、R*1、R*2、R*3及びR*4は下記を示す。
R*1= キシリトール残基
R*2= −C2H4Si(OSiMe3)3
R*3= −C16H33
R*4= −C2H4Si(CH3)2[OSi(CH3)2]25OSi(CH3)3
収量は 181.2g(86%)であった。生成物の25℃における動粘度は198,000mm2/sec、屈折率は1.422、性状は淡黄色の不透明均一な液体であった。
反応器に平均組成式:MD72DH 3Mで表されるメチルハイドロジェンポリシロキサン 168.9g、テトラグリセリンモノアリルエーテル 41.1g、IPA 63.0gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒24mgを添加し、80℃で3時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*5 3Mで表されるテトラグリセリン変性シリコーン1を得た。ここで、R*5は−C3H6O−X(Xはテトラグリセリン部分)を表す。収量は180.6g(86%)であった。生成物の25℃における動粘度は750,000mm2/sec以上、屈折率は1.429、性状は乳白色の不透明均一な粘稠液体であった。
反応器に平均組成式:MD72DH 12Mで表されるメチルハイドロジェンポリシロキサン 172.6g、キシリトールモノアリルエーテル 19.4g、1−ヘキサデセン 66.1g、イソプロピルアルコール(IPA) 75.2gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒30mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*1 3DR*2 9Mで表されるキシリトール変性シリコーンを得た。ここで、R*1及びR*2は下記を示す。
R*1= キシリトール残基
R*2= −C16H33
収量は216.8g(84%)であった。生成物の25℃における動粘度は750,000mm2/sec以上、屈折率は1.429、性状は淡褐色の不透明均一な粘稠液体であった。
反応器に平均組成式:MD72DH 12Mで表されるメチルハイドロジェンポリシロキサン 69.5g、テトラグリセリンモノアリルエーテル 15.5g、1−オクテン 6.0g、平均構造式:CH2=CHSi(CH3)2[OSi(CH3)2]25OSi(CH3)3で表される片末端ビニル変性ジメチルポリシロキサン 119.4g、IPA 63.0gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒24mgを添加し、80℃で3時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*6 3DR*4 5DR*7 4Mで表されるテトラグリセリン変性シリコーン2を得た。
ここで、R*6は下記を示す。
R*6= −C3H6O−X(Xはテトラグリセリン部分を表す)
R*4= −C2H4Si(CH3)2[OSi(CH3)2]25OSi(CH3)3
R*7= −C8H17
収量は183.1g(87%)であった。生成物の25℃における動粘度は237,000mm2/sec以上、屈折率は1.416、性状は乳白色の不透明均一な粘稠液体であった。
実施例1で得られた「シリコーン化合物No.1」、実施例2で得られた「シリコーン化合物No.2」、実施例3で得られた「シリコーン化合物No.3」、実施例4で得られた「シリコーン化合物No.4」、及び、実施例5で得られた「シリコーン化合物No.5」を用いて表1に示す組成の油中水型乳化組成物を下記に示す方法によって調製し、以下の評価基準により、油剤との相溶性、乳化安定性、及び、官能性(感触・使用感)を評価した。結果を表1及び表2に併せて示す。なお、表中、数値は重量(質量)部を示す。
参考例1で得られた「テトラグリセリン変性シリコーン1」、参考例2で得られた「キシリトール変性シリコーン」、及び、参考例3で得られた「テトラグリセリン変性シリコーン2」を用いて、表2に示す組成の油中水型乳化組成物を実施例6〜20の場合と同様に調製し、実施例6〜20の場合と同様に、油剤との相溶性、乳化安定性、及び、官能性(感触・使用感)を評価した。結果を表2に併せて示す。なお、表中、数値は重量(質量)部を示す。
1. 容量150mlの容器に、表1及び表2に示される油剤、及び、界面活性剤(乳化剤)としての各変性シリコーンを仕込んだ。
2. 加温と撹拌を行い、各変性シリコーンを油剤中に均一分散又は溶解させた(油相A)。
3. 別の容器に食塩とイオン交換水とを仕込み、スパチュラで混合して溶解させた。更に、1,3−ブチレングリコールを混合して溶解させた(水相B)。
4. ホモディスパーの鋸歯を油相Aに浸し、容器を固定したのち1000rpmで攪拌しながら、水相Bをほぼ定速で約40秒かけて油相A中に注ぎ込んだ。
5. ホモディスパーの回転数を3000rpmに上げ、攪拌を更に1分間継続して油中水型乳化組成物を得た。
油相Aを室温に戻した時の外観を、以下の基準により評価した。
○: 半透明に溶解又は均一分散している。
△: 分散が粗く、変性シリコーンの粒子が確認できる。
×: 変性シリコーンが分散せず、沈降分離している。
各組成の油中水型乳化組成物を40℃において1ヶ月間静置し、静置前後の乳化状態の変化を、以下の基準により評価した。
◎: 粘度変化≦±5% 且つ、外観は変化なく均一。
○: ±5%<粘度変化≦±10% 且つ、外観も均一。
△: ±10%<粘度変化≦±20%、又は乳化物の表面がやや不均一化。
×: ±20%<粘度変化、又は、水滴や水相の分離あり。
各組成の油中水型乳化組成物0.10gを指にとって、前腕部に軽くすべらせるように塗布した。乳化物が均一に広がるよう、何度か皮膚(塗布部位)を指で軽くなぞる動作を繰り返し、このときの感触及び使用感を塗布初期と後期に分けて以下の基準により評価した。但し、同じ油剤を使用した乳化物同士を相対比較した。
◎: しっとりした水性感があり、滑らかに良く伸び、べとつきも無い。さらっとしたすべり感
○: しっとりした水性感があり、滑らかに良く伸び、べとつきも無い。とろっとしたすべり感
△: しっとりした感触で普通に伸び、べとつきも無いが、ややすべり感が不足している。
○: 軽く非常によいすべり感が持続するため、油性感が少ない。
△: 若干重くぬるっとしたすべり感が持続する。やや油っぽい感覚がある。
×: すべりが悪くねっとりした抵抗感がある。又は油っぽい感覚が強い。
実施例1〜実施例5で得られた「シリコーン化合物No.1」〜「シリコーン化合物No.5」を用いて表3に示す組成のリキッドファンデーションを調製し、以下の評価基準により、伸び広がり性、仕上がりの美しさ、密着感、違和感のない自然な肌感覚、及び、安定性を評価した。結果を表3に併せて示す。なお、表中、数値は重量(質量)部を示す。
参考例1で得られた「テトラグリセリン変性シリコーン1」、参考例2で得られた「キシリトール変性シリコーン」、及び、参考例3で得られた「テトラグリセリン変性シリコーン2」を用いて、表4に示す組成のリキッドファンデーションを調製し、実施例21〜25の場合と同様に、伸び広がり性、仕上がりの美しさ、密着感、違和感のない自然な肌感覚、及び、安定性を評価した。結果を表4に併せて示す。なお、表中、数値は重量(質量)部を示す。
1. 得られたリキッドファンデーション0.15gを、予め産毛を剃り落とした清浄な皮膚上(前腕部)に、パフを用いて直径約5cmの円形に均一に塗布し、肌への伸び広がり性を評価した。
2. 塗布10分後(初期)、4時間後、及び、9時間後の時点で、「仕上がりの美しさ」、「密着感」、及び、「違和感のない自然な肌感覚」について、目視及び触感にて官能評価を行った。
3. 得られたリキッドファンデーションを40℃で2ヶ月静置させた後、外観及び性状の安定性を評価した。
各項目について、以下の基準により評価した。
◎ 滑らかによく伸び広がった。
○ 普通に伸び広がった。
△ 伸び広げるのに通常よりも力を要した。
◎ 緊密にカバーされ、非常に美しい仕上がりであった。
○ 緊密にカバーされてはいるが、小皺による溝が僅かにあった。
× 塗布表面の均一感がやや不足し、きめの粗さが目立ってきた。
◎ 密着感をはっきりと感じた。
○ 密着感はあるが、意識しないと気づかないレベルだった。
× 密着感を全く感じなかった。
◎ 違和感の無い自然な皮膚感覚であった。
○ 皮膚感覚に僅かの違和感があった。
△ 少し不自然な皮膚感覚があった。
○ 分離や粉の沈降が無く、均一な外観・性状を維持していた。
△ 粉の沈降が若干認められたが、振り混ぜると容易に均一に再分散できた。
× 粉が沈降し、振り混ぜても均一な再分散ができなかった。
A: 成分1)及び成分6)〜18)を室温で混合した後、ホモミキサーで撹拌しながら溶解させる。
B: 成分19)〜21)を混合し、完全に溶解させる。
C:その後、Aをホモミキサーで撹拌しながらBを添加する。
D:これに成分2〜5を加え、ホモミキサーで混合分散後、脱気し、容器へ充填して液状ファンデーションを得た。
本処方例にかかる日焼け止め化粧料の調製に先立ち、実施例4で得られた「シリコーン化合物No.4」を用いて、化粧料原料である酸化チタンスラリーを調製した。具体的には、微粒子酸化チタン(商品名:MTY−100SAS(テイカ社製)) 20g、シリコーン化合物No.4 5g、及び、デカメチルシクロペンタシロキサン 25gを混合し、ジルコニアビーズ(0.8 mm Φ) 200gを加え、ペイントシェイカーにて1時間混合してスラリー状の分散体を作成した。
本実施例26にかかる日焼け止め化粧料の調製に先立ち、実施例4で得られた「シリコーン化合物No.4」を用いて、化粧料原料である酸化亜鉛スラリーを調製した。具体的には、微粒子酸化亜鉛(商品名:微粒子酸化亜鉛(テイカ製、MZY-505S)) 30g、シリコーン化合物No.4 2.5g、及び、デカメチルシクロペンタシロキサン 17.5gを混合し、ジルコニアビーズ(0.8 mm Φ) 200gを加え、ペイントシェイカーにて1時間混合してスラリー状の分散体を作成した。
1. ポリエーテル変性シリコーン(注1) 1.5部
2. ジメチルシリコーン(6mm2/s) 5部
3. デカメチルシクロペンタシロキサン 3.5部
4. パラメトキシ桂皮酸オクチル 2部
5. トリメチルシロキシケイ酸 2部
6. イソノナン酸イソデシル 4部
7. 酸化チタンスラリー(注2) 2.0部
8. 酸化亜鉛スラリー(注3) 10.0部
9. 1,3−ブチレングリコール 8部
10.塩化ナトリウム 0・5部
11.精製水 残量
12.防腐剤 適量
注1:東レ・ダウコーニング社製、SS−2910を使用した。
注2:上記の方法に従って、調製したサンプルを使用した。
注3:上記の方法に従って、調製したサンプルを使用した。
成分1〜6を混合撹拌して得られた油相に成分9〜12を混合撹拌して得られた水相を添加し、撹拌して乳化した。乳化物に成分7及び8のスラリーを加えて混合撹拌し、日焼け止め化粧料を得た。
(成分)
1. デカメチルシクロペンタシロキサン 9.0部
2. ポリエーテル変性シリコーン(注1) 3.0部
3. フェニルトリメチコン 12.49部
4. シリコーン化合物No.1 1.5部
5. 天然ビタミンE 0.2部
6. スクワラン 3.0部
7. トリオクタノイン 2部
8. シリコーン処理酸化チタン 1部
9. シリコーン処理酸化鉄 0.01部
10.香料 0.04部
11.硫酸マグネシウム 0.2部
12.精製水 残量
13.グリセリン 3.0部
14.1,3−ブチレングリコール 5.0部
15.ポリビニルアルコール 0.2部
16.防腐剤 適量
注1)東レ・ダウコーニング社製SS−2910を使用した。
成分1〜7を均一に混合した。この混合物に、更に、成分8及び9を分散した後、成分10〜16の混合物を加えて乳化した。脱気後、所定の容器に充填して化粧下地を得た。
(成分)
1. ジメチコン(2mm2/s) 3部
2. イソドデカン 7.0部
3. シリコーン化合物No.3 1.5部
4. ポリエーテル変性シリコーン(注1) 3.0部
5. 流動パラフィン 5部
6. カプリルメチコン 5部
7. 天然ビタミンE 0.2部
8. スクワラン 3.0部
9. オクチルシラン処理酸化チタン 0.8部
10.香料 適量
11.硫酸マグネシウム 0.2部
12.精製水 残量
13.グリセリン 3.0部
14.1,3−ブチレングリコール 5.0部
15.ポリビニルアルコール 0.1部
16.防腐剤 適量
注1)ダウコーニング社製、DC5200formulation aidを使用した。
成分1〜8を均一に混合した。この混合物に、更に、成分9を分散した後、成分10〜16の混合物を加えて乳化した。
(成分)
1. フェニルトリメチコン 3.0部
2. ミリスチン酸イソプロピル 3.5部
3. マイクロクリスタリンワックス 0.5部
4. デカメチルシクロペンタシロキサン 6.0部
5. 1,3−ブチレングリコール 3.0部
6. シリコーン化合物No.4 0.8部
7. ポリエーテル変性シリコーン(注1) 0.7部
8. ポリエチレングリコール−150 1.0部
9. エタノール 6.0部
10.ジメチコン/ビニルジメチコンクロスポリマー/シリカ(注2) 6.0部
11.シリコーン処理雲母チタン 0.5部
12.フェノキシエタノール 0.4部
13.グリシルグリシン 5.0部
14.香料 適量
15.精製水 残余
注1)ダウコーニング社製、DC5225Formulation aidを使用した。
注2)東レ・ダウコーニング社製9701Cosmetic Powderを使用した。
成分1〜11を混合し、これに、成分12〜15の混合物を添加し、乳化してクリームを得た。
(成分)
1. ジメチルポリシロキサン(2mm2/s) 10.0部
2. イソステアリン酸 3.0部
3. シクロペンタシロキサン/(アクリレーツ/メタクリル酸ポリトリメチルシロキシ)コポリマー(注1) 1.0部
4. ポリエーテル変性シリコーン(注2) 2.0部
5. シリコーン化合物No.5 1.0部
6. プロピレングリコール 2.5部
7. エタノール 6.0部
8. パラベン 0.1部
9. ジメチコン/ビニルジメチコンクロスポリマー 6.0部
10.オクチルシラン処理雲母チタン 0.8部
11.シリコーン処理酸化チタン 2.5部
12.シリコーン処理マイカ 2.5部
13.シリコーン処理タルク 1.5部
14.シリコーン処理酸化鉄 4.5部
15.酸化防止剤 適量
16.グリシルグリシン 3.0部
17.香料 0.05部
18.精製水 残余
注1)東レ・ダウコーニング社製、FA4001CM Silicone Acrylateを使用した。
注2)東レ・ダウコーニング社製、BY11-030を使用した。
成分1〜14を混合し、これに、成分15〜18の混合物を添加し、乳化した。
(成分)
1. フェニルトリメチコン 2.0部
2. デカメチルシクロペンタシロキサン 25.0部
3. イソノナン酸イソデシル 4.0部
4. グリセリン 4.0部
5. 1,3−ブチレングリコール 0.5部
6. ポリシリコーン13 0.5部
7. シリコーン化合物No.1 1.0部
8. エタノール 9.0部
9. ジメチコン/ビニルジメチコンクロスポリマー 10.0部
10.シリコーン処理処雲母チタン 1.5部
11.微粒子酸化チタン 5.0部
12.パラメトキシケイ皮酸オクチル 5.0部
13.グリシルグリシン 1.0部
14.香料 0.1部
15.精製水 残余
成分1〜12を混合し、これに、成分13〜15の混合物を添加し、乳化した。
(成分)
油相
1.デカメチルシクロペンタシロキサン 10部
2.ジメチルポリシロキサン 5部
3.酢酸トコフェロール 0.1部
4.シリコーン化合物No.1 0.5部
5.高分子ポリエーテル変性シリコーン(注1) 2部
水相
6.イオン交換水 残余
7.グリセリン 5部
8.1,3−ブチレングリコール 5部
9.マルチトール 2部
10.ポリオキシエチレンメチルグルコシド(10EO) 2部
11.サリチル酸 0.3部
12.トリメチルグリシン 0.5部
13.エリスリトール 0.5部
14.ヒアルロン酸ナトリウム 0.01部
15.塩化ナトリウム 1部
16.乳酸 0.1部
17.乳酸ナトリウム 0.05部
18.EDTA 0.1部
19.フェノキシエタノール 0.1部
20.香料 適量
注1) 東レ・ダウコーニング社製、BY22−008Mを使用した。
前記油相及び水相の各成分をそれぞれ均一に溶解分散し、ホモジナイザーを用いて、油相に水相を添加して、均一なクリームを得た。
Claims (26)
- 下記一般式(1):
R1は一価有機基(但し、R2、L1及びQを除く)を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基、又は、下記一般式(2−1);
L1はi=1のときの下記一般式(3);
R3は炭素原子数1〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
R4はそれぞれ独立して炭素原子数1〜6のアルキル基又はフェニル基を表し、
Zは二価有機基を表し、
iはLiで示されるシリルアルキル基の階層を表し、該シリルアルキル基の繰り返し数である階層数がkのとき1〜kの整数であり、階層数kは1〜10の整数であり、Li+1はiがk未満のときは該シリルアルキル基であり、i=kのときはR4であり、hiは0〜3の範囲の数である)で表される、シロキサンデンドロン構造を有するシリルアルキル基を表し、
Qは糖アルコール基含有有機基を表し、
a 、b 、c及びdは、それぞれ、1.0≦a≦2.5、0≦b≦1.5、0.0001≦c≦1.5、0.0001≦d≦1.5の範囲にある数である}で表される共変性オルガノポリシロキサン。 - 前記一般式(1)において、R1である一価有機基が、炭素原子数1〜8の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基、−R5O(AO)nR6(式中、AOは炭素原子数2〜4のオキシアルキレン基を表し、R5は炭素原子数3〜5の、置換若しくは非置換の、直鎖状若しくは分岐状の二価炭化水素基を表し、R6は水素原子、炭素原子数1〜24の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基、又は、炭素原子数2〜24の、置換若しくは非置換の、直鎖状若しくは分岐状のアシル基を表し、n=1〜100である)で表されるポリオキシアルキレン基、アルコキシ基、水酸基又は水素原子(但し、R1が全て水酸基、水素原子、前記アルコキシ基又は前記ポリオキシアルキレン基になることはない)である、請求項1記載の共変性オルガノポリシロキサン。
- 上記一般式(4−1)又は(4−2)において、Rである二価有機基が炭素原子数3〜5の、置換若しくは非置換の、直鎖状若しくは分岐状の二価炭化水素基である、請求項1乃至3のいずれかに記載の共変性オルガノポリシロキサン。
- 請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサンを含む界面活性剤。
- (A)請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサン、(B)水、及び、(C)シリコーン油、非極性有機化合物及び低極性有機化合物からなる群から選択される5〜100℃で液状の少なくとも1種の油剤を含むエマルジョン組成物。
- 請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサンを含む粉体処理剤。
- 粉体表面処理剤である、請求項11記載の粉体処理剤。
- 請求項12記載の粉体処理剤で表面処理された粉体。
- (A)請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサン、及び、(D)粉体を含む化粧料用原料。
- 更に、(C)シリコーン油、非極性有機化合物及び低極性有機化合物からなる群から選択される5〜100℃で液状の少なくとも1種の油剤を含む請求項14記載の化粧料用原料。
- 請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサンを含む増粘剤又はゲル化剤。
- (A)請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサン、及び、(C)シリコーン油、非極性有機化合物及び低極性有機化合物からなる群から選択される5〜100℃で液状の少なくとも1種の油剤を含むゲル状組成物。
- 請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサンを含む外用剤。
- 請求項10記載のエマルジョン組成物を含む外用剤。
- 請求項13に記載の粉体を含む化粧料。
- 請求項14又は15記載の化粧料用原料を含む化粧料。
- 請求項17に記載のゲル状組成物を含む外用剤。
- 化粧料である、請求項18、19又は22記載の外用剤。
- ヒドロシリル化反応触媒の存在下において、
(a)珪素原子結合水素原子を有するオルガノポリシロキサン
(b)反応性不飽和基を1分子中に1つ有する有機化合物
(c)反応性不飽和基を1分子中に1つ有するシロキサンデンドロン化合物、及び、
(d)反応性不飽和基を1分子中に1つ有する糖アルコール官能性有機化合物
を反応させて得られることを特徴とする、請求項1乃至8のいずれかに記載の共変性オルガノポリシロキサンの製造方法。 - 更に、(e)反応性不飽和基を1分子中に1つ有する炭化水素化合物又は反応性不飽和基を1分子中に1つ有する鎖状オルガノポリシロキサンを反応させる、請求項24記載の共変性オルガノポリシロキサンの製造方法。
- (c)反応性不飽和基を1分子中に1つ有するシロキサンデンドロン化合物が、下記一般式(3’):
R3及びR4は上記のとおりであり、
Z´は二価有機基を表し、
h1は0〜3の範囲の数であり、
L´1は、R4、又は、j=1のときの下記一般式(3’’):
Zは二価有機基を表し、
jはLjで示されるシリルアルキル基の階層を表し、該シリルアルキル基の繰り返し数である階層数がk´のとき1〜k´の整数であり、階層数k´は1〜9の整数であり、Lj+1はjがk´未満のときは該シリルアルキル基であり、j=k´のときはR4である。hjは0〜3の範囲の数である)で表されるシリルアルキル基を表す}で表される分子鎖末端に1個の炭素−炭素二重結合を有するシロキサンデンドロン構造を有する化合物である、請求項24又は25記載の共変性オルガノポリシロキサンの製造方法。
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CN102947369B (zh) | 2015-01-28 |
JP5841348B2 (ja) | 2016-01-13 |
WO2011136393A1 (en) | 2011-11-03 |
US9475828B2 (en) | 2016-10-25 |
EP2563844A1 (en) | 2013-03-06 |
KR20130058702A (ko) | 2013-06-04 |
CN102947369A (zh) | 2013-02-27 |
US20130210930A1 (en) | 2013-08-15 |
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