JP4219855B2 - Lip composition - Google Patents
Lip composition Download PDFInfo
- Publication number
- JP4219855B2 JP4219855B2 JP2004170207A JP2004170207A JP4219855B2 JP 4219855 B2 JP4219855 B2 JP 4219855B2 JP 2004170207 A JP2004170207 A JP 2004170207A JP 2004170207 A JP2004170207 A JP 2004170207A JP 4219855 B2 JP4219855 B2 JP 4219855B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- general formula
- group
- integer
- monomer
- 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.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 56
- 239000000178 monomer Substances 0.000 claims description 95
- 229920001577 copolymer Polymers 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 46
- 150000002430 hydrocarbons Chemical class 0.000 claims description 39
- 229920001296 polysiloxane Polymers 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- -1 2-methoxyhexyl paramethoxycinnamate Chemical compound 0.000 claims description 21
- 239000000470 constituent Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 229920002545 silicone oil Polymers 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000003906 humectant Substances 0.000 claims description 7
- 239000000346 nonvolatile oil Substances 0.000 claims description 7
- 239000000341 volatile oil Substances 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 claims description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 238000012360 testing method Methods 0.000 description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000011248 coating agent Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- 238000011156 evaluation Methods 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000005702 oxyalkylene group Chemical group 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 229910002012 Aerosil® Inorganic materials 0.000 description 5
- 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 5
- 238000009472 formulation Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 239000004200 microcrystalline wax Substances 0.000 description 5
- 235000019808 microcrystalline wax Nutrition 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002304 perfume Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 229940094522 laponite Drugs 0.000 description 4
- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 0 CCC(C*C)C(CCC1)CC1C(C)C Chemical compound CCC(C*C)C(CCC1)CC1C(C)C 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001553290 Euphorbia antisyphilitica Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LAQFLZHBVPULPL-UHFFFAOYSA-N methyl(phenyl)silicon Chemical class C[Si]C1=CC=CC=C1 LAQFLZHBVPULPL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 2
- 229940017219 methyl propionate Drugs 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000005386 organosiloxy group Chemical group 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QPQANCNBWQXGTQ-UHFFFAOYSA-N trihydroxy(trimethylsilylperoxy)silane Chemical compound C[Si](C)(C)OO[Si](O)(O)O QPQANCNBWQXGTQ-UHFFFAOYSA-N 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (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-carboxylic acid Chemical compound 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 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OWQCUVRSJUABCB-UHFFFAOYSA-N 16-methylheptadecyl 2-methylprop-2-enoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C(C)=C OWQCUVRSJUABCB-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- VBZBISQOWJYWCC-UHFFFAOYSA-N 2-(2-carboxypropan-2-yldiazenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)N=NC(C)(C)C(O)=O VBZBISQOWJYWCC-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- KFTHUBZIEMOORC-UHFFFAOYSA-N 2-methylbut-2-enamide Chemical compound CC=C(C)C(N)=O KFTHUBZIEMOORC-UHFFFAOYSA-N 0.000 description 1
- LPNSCOVIJFIXTJ-UHFFFAOYSA-N 2-methylidenebutanamide Chemical compound CCC(=C)C(N)=O LPNSCOVIJFIXTJ-UHFFFAOYSA-N 0.000 description 1
- PGTISPYIJZXZSE-UHFFFAOYSA-N 2-methylpent-2-enamide Chemical compound CCC=C(C)C(N)=O PGTISPYIJZXZSE-UHFFFAOYSA-N 0.000 description 1
- MSPJNHHBNOLHOC-UHFFFAOYSA-N 3,3-dimethylcyclopropane-1,2-dicarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1C(O)=O MSPJNHHBNOLHOC-UHFFFAOYSA-N 0.000 description 1
- SDNHWPVAYKOIGU-UHFFFAOYSA-N 3-ethyl-2-methylpent-2-enamide Chemical compound CCC(CC)=C(C)C(N)=O SDNHWPVAYKOIGU-UHFFFAOYSA-N 0.000 description 1
- XPFCZYUVICHKDS-UHFFFAOYSA-N 3-methylbutane-1,3-diol Chemical compound CC(C)(O)CCO XPFCZYUVICHKDS-UHFFFAOYSA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001287 Chondroitin sulfate Polymers 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silicon Polymers (AREA)
Description
本発明は***用組成物、特に化粧持ちの向上、及び***上での被膜感の改善に関する。 The present invention relates to a composition for lips, in particular, improvement of makeup retention and improvement of the coating feeling on the lips.
従来、通常の油性口紅は、各種の油分、ワックス、色材等から構成されており、唇に塗布した場合、つやは良好であるが、コーヒーカップや衣料等に色移りしてしまったり、経時で色落ちしてしまい、化粧持ちが悪いという問題点があった。 Conventionally, normal oily lipsticks are composed of various oils, waxes, coloring materials, etc., and when applied to the lips, the gloss is good, but the color may transfer to coffee cups, clothing, etc. There was a problem that the color faded and the makeup lasting was bad.
このような化粧持ちの問題点を改善するため、従来より種々の検討がなされてきた。例えば、アルキルメチルポリシロキサン、ポリオキシアルキレン変性オルガノポリシロキサン、トリメチルシロキシケイ酸のような各種シリコーンや、非水系ポリマーディスパージョン等を被膜形成成分として用いた口紅が提案されている(例えば、特許文献1〜6参照)。 Various studies have been made in the past in order to improve such problems with makeup. For example, lipsticks using various silicones such as alkylmethylpolysiloxane, polyoxyalkylene-modified organopolysiloxane, trimethylsiloxysilicic acid, and non-aqueous polymer dispersion as a film forming component have been proposed (for example, patent documents) 1-6).
しかしながら、これらの被膜形成成分を配合した口紅は、つやや化粧持ちの点ではある程度の機能を有してはいるものの、原料の被膜形成成分に起因する***上での被膜感を生じてしまうため、使用感触の点で問題があった。一方で、被膜形成成分の配合量を減らした場合には、***上の被膜感は良好であるものの、化粧持ちの向上効果が十分に得られず、両者の機能を同時に果たすことは非常に難しい問題であった。 However, lipsticks formulated with these film-forming components have a certain level of function in terms of gloss and makeup, but may cause a feeling of film on the lips due to the film-forming components of the raw material. There was a problem in terms of use feeling. On the other hand, when the blending amount of the film forming component is reduced, the film feeling on the lips is good, but the effect of improving the longevity cannot be obtained sufficiently, and it is very difficult to perform both functions at the same time. It was a problem.
本発明は前述の課題に鑑み行われたものであり、化粧持ちに優れるとともに、***上の被膜感が改善された***用組成物を提供することを目的とする。 The present invention has been made in view of the above-described problems, and an object of the present invention is to provide a composition for lips that is excellent in long-lasting makeup and has an improved coating feeling on the lips.
本発明者らが、前述の課題に鑑み鋭意研究を行った結果、アクリル酸系モノマーと、ポリオキシアルキレン基含有モノマーと、オルガノポリシロキサン含有モノマーとを特定の割合で含有した共重合体高分子を、被膜形成成分として***用組成物中に配合することによって、化粧持ちに極めて優れているとともに、従来の被膜形成成分を用いた場合と比較して、***上の被膜感が著しく改善されていることを見出し、本発明を完成するに至った。 As a result of intensive studies conducted by the present inventors in view of the above-mentioned problems, a copolymer polymer containing an acrylic acid monomer, a polyoxyalkylene group-containing monomer, and an organopolysiloxane-containing monomer in a specific ratio is obtained. By blending in the lip composition as a film-forming component, it has excellent makeup durability and the coating feeling on the lips is remarkably improved as compared with the case where a conventional film-forming component is used. As a result, the present invention has been completed.
すなわち、本発明にかかる***用組成物は、下記一般式(1)で示されるモノマー(A)と、下記一般式(2)で示されるモノマー(B)と、下記一般式(3)で示されるモノマー(C)とを構成モノマーとして含有し、前記モノマー(A)の含有量が構成モノマー全量に対して20質量%以上である共重合体高分子を含有することを特徴とする。
また、前記***用組成物において、さらに下記一般式(4)で示される直鎖シリコーン油、下記一般式(5)で示される環状シリコーン油、下記一般式(6)で示されるアルキル変性シリコーン油、イソパラフィンの中から選択される1種又は2種以上の揮発性油分を含有することが好適である。
また、前記***用組成物において、さらに下記一般式(7)で示されるフッ素変性ジメチルシリコーン、下記一般式(8)で示されるフッ素変性フェニルシリコーン、下記一般式(9)で示されるアルコキシ変性シリコーン、下記一般式(10)で示されるアルキル変性シリコーン、トリ(水添ロジン・イソステアリン酸)グリセリル、パラメトキシケイ皮酸2−エチルヘキシルの中から選択される1種又は2種以上の不揮発性油分を含有することが好適である。
また、前記***用組成物において、さらに水及び/又は保湿剤を含有することが好適である。
In the lip composition, the fluorine-modified dimethyl silicone represented by the following general formula (7), the fluorine-modified phenyl silicone represented by the following general formula (8), and the alkoxy-modified silicone represented by the following general formula (9) One or more non-volatile oils selected from alkyl-modified silicones represented by the following general formula (10), tri (hydrogenated rosin / isostearic acid) glyceryl, and 2-methoxyhexyl paramethoxycinnamate It is preferable to contain.
The lip composition preferably further contains water and / or a humectant.
本発明にかかる***用組成物は、特定構造の共重合体高分子が配合されていることによって、従来の***用組成物と比較して、化粧持ちに極めて優れているとともに、***上の被膜感が著しく改善されているものである。 The composition for lips according to the present invention is extremely superior in makeup lasting as compared with conventional lip compositions, and has a coating feeling on the lips, by incorporating a copolymer polymer having a specific structure. Is significantly improved.
以下、本発明の好適な実施の形態について詳述する。
本発明にかかる***用組成物に用いられる共重合体高分子は、下記一般式(1)で示されるモノマー(A)と、下記一般式(2)で示されるモノマー(B)と、下記一般式(3)で示されるモノマー(C)とを構成モノマーとして含有し、前記モノマー(A)の含有量が構成モノマー全量に対して20質量%以上であるように調整されているものである。
The copolymer polymer used in the lip composition according to the present invention includes a monomer (A) represented by the following general formula (1), a monomer (B) represented by the following general formula (2), and the following general formula: The monomer (C) represented by (3) is contained as a constituent monomer, and the content of the monomer (A) is adjusted so as to be 20% by mass or more based on the total amount of the constituent monomers.
前記一般式(1)に示されるモノマー(A)は、アクリル酸、又はメタクリル酸のようなアルキル置換アクリル酸、又はそのアルキルエステルである。一般式(1)において、アクリル酸α炭素の置換基であるR1は水素、又は炭素数1〜3の炭化水素基である。炭化水素基としては、例えば、アルキル基、アルケニル基等が挙げられ、直鎖状、分岐状いずれのものでも良い。R1としては、特に好ましくは水素、メチル基である。また、一般式(1)において、アクリル酸の末端置換基であるR2は水素、又は炭素数1〜24の炭化水素基である。炭化水素基としては、アルキル基、アルケニル基等が挙げられ、直鎖状、分岐状いずれのものでも良く、また、水酸基あるいはフッ素原子が一部置換されていても良い。R2としては、例えば、水素原子、メチル基、エチル基、プロピル基、ブチル基、ヘキシル基、2−エチルヘキシル基、デシル基、トリデシル基、ステアリル基、イソステアリル基、2−ヒドロキシエチル基、2−ヒドロキシプロピル基、トリフルオロメチル基、トリフルオロエチル基等が挙げられる。特に好ましくは、水素原子、メチル基、ブチル基、2−エチルヘキシル基、トリデシル基、ステアリル基、イソステアリル基である。 The monomer (A) represented by the general formula (1) is an alkyl-substituted acrylic acid such as acrylic acid or methacrylic acid, or an alkyl ester thereof. In the general formula (1), R 1 is a substituent of acrylic acid α carbon is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R 1 is particularly preferably hydrogen or a methyl group. In the general formula (1), R 2 is a terminal substituent of acrylic acid is hydrogen or a hydrocarbon group having 1 to 24 carbon atoms. Examples of the hydrocarbon group include an alkyl group and an alkenyl group, which may be linear or branched and may be partially substituted with a hydroxyl group or a fluorine atom. Examples of R 2 include a hydrogen atom, methyl group, ethyl group, propyl group, butyl group, hexyl group, 2-ethylhexyl group, decyl group, tridecyl group, stearyl group, isostearyl group, 2-hydroxyethyl group, 2 -A hydroxypropyl group, a trifluoromethyl group, a trifluoroethyl group, etc. are mentioned. Particularly preferred are a hydrogen atom, a methyl group, a butyl group, a 2-ethylhexyl group, a tridecyl group, a stearyl group, and an isostearyl group.
本発明に用いられるモノマー(A)としては、例えば、アクリル酸、アクリル酸メチル、アクリル酸エチル、アクリル酸ブチル、アクリル酸ヘキシル、アクリル酸2−エチルヘキシル、アクリル酸オクチル、アクリル酸デシル、アクリル酸ラウリル、アクリル酸ステアリル等のアクリル酸アルキルエステル、メタクリル酸、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸ブチル、メタクリル酸ヘキシル、メタクリル酸2−エチルヘキシル、メタクリル酸オクチル、メタクリル酸デシル、メタクリル酸ドデシル、メタクリル酸トリデシル、メタクリル酸ステアリル、メタクリル酸イソステアリル等のメタクリル酸アルキルエステル等が挙げられる。
なお、本発明に用いられる共重合体高分子においては、前記モノマー(A)の1種又は2種以上を構成モノマーとすることができる。
Examples of the monomer (A) used in the present invention include acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, decyl acrylate, and lauryl acrylate. , Alkyl acrylates such as stearyl acrylate, methacrylic acid, methyl methacrylate, ethyl methacrylate, butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, decyl methacrylate, dodecyl methacrylate, methacrylic acid Examples include methacrylic acid alkyl esters such as tridecyl, stearyl methacrylate, and isostearyl methacrylate.
In the copolymer polymer used in the present invention, one or more of the monomers (A) can be used as a constituent monomer.
また、本発明に用いられる共重合体において、前記モノマー(A)の含有量が構成モノマー全量に対して20質量%以上である必要がある。モノマー(A)の含有量が構成モノマー全量に対して20質量%未満である場合には、被膜形成能が低くなる場合がある。また、モノマー(A)の含有量が20〜60質量%であることが好適であり、特に好ましくは25〜50質量%である。 In the copolymer used in the present invention, the content of the monomer (A) needs to be 20% by mass or more based on the total amount of the constituent monomers. When the content of the monomer (A) is less than 20% by mass with respect to the total amount of the constituent monomers, the film forming ability may be lowered. Moreover, it is suitable that content of a monomer (A) is 20-60 mass%, Most preferably, it is 25-50 mass%.
前記一般式(2)に示されるモノマー(B)は、アクリル酸、又はメタクリル酸のようなアルキル置換アクリル酸においてオキシアルキレン部位を有する化合物であり、例えば、アクリル酸又はアルキル置換アクリル酸のアルキレングリコールエステル、あるいはそのアルキルエーテルである。一般式(2)において、アクリル酸α炭素の置換基であるR3は水素、又は炭素数1〜3の炭化水素基である。炭化水素基としては、例えば、アルキル基、アルケニル基等が挙げられ、直鎖状、分岐状いずれのものでも良い。R3としては、特に好ましくは水素、メチル基である。また、一般式(2)において、オキシアルキレン基における炭化水素部位であるR4は、炭素数1〜4の2価炭化水素基である。2価炭化水素基としては、例えば、アルキレン基が挙げられ、直鎖状、分岐状いずれのものでも良い。なお、R4は同一であっても異なっていてもよく、例えば、オキシアルキレン部位が、炭素数の異なるR4を有する2以上のオキシアルキレン基からなるブロック状又はランダム状の繰り返し構造であっても良い。R4としては、エチレン基であることが特に好ましい。また、一般式(2)において、オキシアルキレン基の末端置換基であるR5は水素、又は炭素数1〜24の炭化水素基である。炭化水素基としては、例えば、アルキル基、アルケニル基等が挙げられ、直鎖状、分岐状いずれのものでも良い。R5は水素、メチル基であることが特に好ましい。また、一般式(2)において、オキシアルキレン基の繰り返し単位数を表すlは1〜50の整数である。lは1〜20であることが特に好ましい。 The monomer (B) represented by the general formula (2) is a compound having an oxyalkylene moiety in an alkyl-substituted acrylic acid such as acrylic acid or methacrylic acid. For example, an alkylene glycol of acrylic acid or alkyl-substituted acrylic acid Esters or their alkyl ethers. In general formula (2), R 3 are substituents of acrylic acid α carbon is hydrogen or a hydrocarbon group having 1 to 3 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R 3 is particularly preferably hydrogen or a methyl group. In the general formula (2), R 4 is a hydrocarbon moiety in the oxyalkylene group is a divalent hydrocarbon group having 1 to 4 carbon atoms. Examples of the divalent hydrocarbon group include an alkylene group, which may be linear or branched. R 4 may be the same or different. For example, the oxyalkylene moiety is a block-like or random repeating structure composed of two or more oxyalkylene groups having R 4 having different carbon numbers. Also good. R 4 is particularly preferably an ethylene group. In the general formula (2), R 5 is a terminal substituent of the oxyalkylene group is hydrogen or a hydrocarbon group having 1 to 24 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R 5 is particularly preferably hydrogen or a methyl group. Moreover, in General formula (2), l showing the number of repeating units of an oxyalkylene group is an integer of 1-50. l is particularly preferably 1-20.
本発明に用いられるモノマー(B)としては、例えば、CH2=C(CH3)COO(C2H4O)6H、CH2=C(CH3)COO(C2H4O)8H、CH2=C(CH3)COO(C2H4O)10H、CH2=C(CH3)COO(C2H4O)15H、CH2=C(CH3)COO(C2H4O)6CH3、CH2=C(CH3)COO(C2H4O)8CH3、CH2=C(CH3)COO(C2H4O)10CH3、CH2=C(CH3)COO(C2H4O)15C4H9、CH2=CHCOO(C2H4O)6H、CH2=CHCOO(C2H4O)8H、CH2=CHCOO(C2H4O)10H、CH2=CHCOO(C2H4O)15H、CH2=CHCOO(C2H4O)6CH3、CH2=CHCOO(C2H4O)8CH3、CH2=CHCOO(C2H4O)10CH3、CH2=CHCOO(C2H4O)15C4H9、CH2=CHCOO(C2H4O)10(C3H6O)10C12H25、CH2=C(CH3)COO(C2H4O)30(C3H6O)10C18H37等が挙げられる。
なお、本発明に用いられる共重合体高分子においては、前記モノマー(B)の1種又は2種以上を構成モノマーとすることができる。
Examples of the monomer (B) used in the present invention, for example, CH 2 = C (CH 3 ) COO (C 2 H 4 O) 6 H, CH 2 = C (CH 3) COO (C 2 H 4 O) 8 H, CH 2 = C (CH 3) COO (C 2 H 4 O) 10 H, CH 2 = C (CH 3) COO (C 2 H 4 O) 15 H, CH 2 = C (CH 3) COO ( C 2 H 4 O) 6 CH 3, CH 2 = C (CH 3) COO (C 2 H 4 O) 8 CH 3, CH 2 = C (CH 3) COO (C 2 H 4 O) 10 CH 3, CH 2 = C (CH 3) COO (C 2 H 4 O) 15 C 4 H 9, CH 2 = CHCOO (C 2 H 4 O) 6 H, CH 2 = CHCOO (C 2 H 4 O) 8 H, CH 2 = CHCOO (C 2 H 4 O) 10 H, CH 2 = CHCOO (C 2 H O) 15 H, CH 2 = CHCOO (C 2 H 4 O) 6 CH 3, CH 2 = CHCOO (C 2 H 4 O) 8 CH 3, CH 2 = CHCOO (C 2 H 4 O) 10 CH 3, CH 2 = CHCOO (C 2 H 4 O) 15 C 4 H 9, CH 2 = CHCOO (C 2 H 4 O) 10 (C 3 H 6 O) 10 C 12 H 25, CH 2 = C (CH 3) COO (C 2 H 4 O) 30 (C 3 H 6 O) 10 C 18 H 37 and the like.
In the copolymer polymer used in the present invention, one or more of the monomers (B) can be used as a constituent monomer.
また、本発明に用いられる共重合体において、前記モノマー(B)の含有量は特に制限されるものではないが、構成モノマー全量に対して0.1〜50質量%であることが好適である。モノマー(B)の含有量が構成モノマー全量に対して0.1質量%未満であると、被膜感が強くなる場合があり、50質量%を超えると、被膜形成能が低くなる場合がある。また、モノマー(B)の含有量が、1〜40質量%であることが、特に好適である。 In the copolymer used in the present invention, the content of the monomer (B) is not particularly limited, but is preferably 0.1 to 50% by mass with respect to the total amount of the constituent monomers. . When the content of the monomer (B) is less than 0.1% by mass with respect to the total amount of the constituent monomers, the film feeling may become strong, and when it exceeds 50% by mass, the film forming ability may be lowered. Moreover, it is especially suitable that content of a monomer (B) is 1-40 mass%.
前記一般式(1)に示されるモノマー(C)は、アクリル酸、又はメタクリル酸のようなアルキル置換アクリル酸において、オルガノポリシロキサン部位を有する化合物であり、例えば、アクリル酸又はアルキル置換アクリル酸に、2価炭化水素基を介してオルガノポリシロキサンを連結したエステルである。一般式(3)において、アクリル酸α炭素の置換基を表すR6は水素、又は炭素数1〜3の炭化水素基である。炭化水素基としては、例えば、アルキル基、アルケニル基等が挙げられ、直鎖状、分岐状いずれのものでも良い。R6としては、特に好ましくは水素、メチル基である。また、一般式(3)において、アクリル酸部位とオルガノポリシロキサン部位とを連結する炭化水素基であるR7は、炭素数1〜4の2価炭化水素基である。2価炭化水素基としては、例えば、アルキレン基が挙げられ、直鎖状、分岐状いずれのものでも良い。R7としては、プロピレン基であることが特に好ましい。また、一般式(3)において、オルガノポリシロキサン基の側鎖置換基であるR8は炭素数1〜6の炭化水素基である。炭化水素基としては、例えば、アルキル基、アルケニル基、あるいはフロロアルキル基等が挙げられ、直鎖状、分岐状いずれのものでも良い。なお、R8は同一であっても異なっていてもよく、例えば末端のR8の一部のみが炭素数の異なる炭化水素基であってもよい。R8はメチル基、フェニル基、あるいはトリフロロプロピル基であることが特に好ましい。また、一般式(3)において、オルガノシロキシ基の繰り返し単位数を表すmは0〜500の整数である。mは0〜200であることが特に好ましい。また、一般式(3)において、オルガノシロキシ基の置換度数を表すnは1〜3の整数である。 The monomer (C) represented by the general formula (1) is a compound having an organopolysiloxane moiety in alkyl-substituted acrylic acid such as acrylic acid or methacrylic acid. For example, acrylic acid or alkyl-substituted acrylic acid An ester in which an organopolysiloxane is linked via a divalent hydrocarbon group. In General formula (3), R < 6 > which represents the substituent of (alpha) acrylic acid carbon is hydrogen or a C1-C3 hydrocarbon group. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and the like, and may be either linear or branched. R 6 is particularly preferably hydrogen or a methyl group. In the general formula (3), R 7 is a hydrocarbon group linking sites acrylic acid and organopolysiloxane site is a divalent hydrocarbon group having 1 to 4 carbon atoms. Examples of the divalent hydrocarbon group include an alkylene group, which may be linear or branched. R 7 is particularly preferably a propylene group. In the general formula (3), R 8 is the side chain substituent groups of the organopolysiloxane group is a hydrocarbon group having 1 to 6 carbon atoms. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, a fluoroalkyl group, and the like, and may be either linear or branched. R 8 may be the same or different. For example, only a part of terminal R 8 may be a hydrocarbon group having a different carbon number. R 8 is particularly preferably a methyl group, a phenyl group, or a trifluoropropyl group. Moreover, in General formula (3), m showing the repeating unit number of an organosiloxy group is an integer of 0-500. m is particularly preferably 0 to 200. Moreover, in General formula (3), n showing the substitution frequency of an organosiloxy group is an integer of 1-3.
本発明に用いられるモノマー(C)としては、例えば、CH2=C(CH3)COOC3H6Si{OSi(CH3)3}3、CH2=C(CH3)COOC3H6{Si(CH3)2O}20Si(CH3)3、CH2=C(CH3)COOC3H6{Si(CH3)2O}40Si(CH3)2C4H9、CH2=C(CH3)COOC3H6{Si(CH3)2O}100Si(CH3)2C4H9、CH2=C(CH3)COOC3H6{Si(CH3)2O}100{Si(C6H5)2O}20Si(CH3)2C4H9、CH2=C(CH3)COOC3H6{Si(CH3)2O}150{Si(CH3)(C2H4CF3)O}50Si(CH3)2C4H9等が挙げられる。
なお、本発明に用いられる共重合体高分子においては、前記モノマー(C)の1種又は2種以上を構成モノマーとすることができる。
As the monomer (C) used in the present invention, for example, CH 2 = C (CH 3 ) COOC 3 H 6 Si {OSi (CH 3) 3} 3, CH 2 = C (CH 3) COOC 3 H 6 { Si (CH 3) 2 O} 20 Si (CH 3) 3, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) 2 O} 40 Si (CH 3) 2 C 4 H 9, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) 2 O} 100 Si (CH 3) 2 C 4 H 9, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) 2 O} 100 {Si (C 6 H 5) 2 O} 20 Si (CH 3) 2 C 4 H 9, CH 2 = C (CH 3) COOC 3 H 6 {Si (CH 3) 2 O} 150 { Si (CH 3) (C 2 H 4 CF 3) O 50 Si (CH 3) 2 C 4 H 9 and the like.
In the copolymer polymer used in the present invention, one or more of the monomers (C) can be used as a constituent monomer.
また、本発明に用いられる共重合体において、前記モノマー(C)の含有量は特に制限されるものではないが、構成モノマー全量に対して30〜80質量%であることが好適である。モノマー(C)の含有量が構成モノマー全量に対して30質量%未満であると、処方中でシリコーン成分との溶解性が悪くなる場合があり、80質量%を超えると、被膜形成能が低くなる場合がある。また、モノマー(C)の含有量が、40〜70質量%であることが、特に好適である。 In the copolymer used in the present invention, the content of the monomer (C) is not particularly limited, but is preferably 30 to 80% by mass with respect to the total amount of the constituent monomers. When the content of the monomer (C) is less than 30% by mass relative to the total amount of the constituent monomers, the solubility with the silicone component may deteriorate in the formulation, and when it exceeds 80% by mass, the film forming ability is low. There is a case. Moreover, it is especially suitable that content of a monomer (C) is 40-70 mass%.
また、本発明の効果を損なわない範囲であれば、上記(A)〜(C)以外のモノマーを構成モノマーとして含有することもできる。含有量は、構成モノマー総量の50質量%以下の範囲であればよく、例えば、0.0001〜10質量%程度含有することができる。このようなモノマーとしては、例えば、エチレン、プロピレン、ブタジエン、スチレン、塩化ビニル、塩化ビニリデン、ビニルアルコール、酢酸ビニル、無水マレイン酸、アクリロニトリル、アクリルアミド、メタクリルアミド、メチルアクリルアミド、メチルメタクリルアミド、ジメチルメタクリルアミド、エチルアクリルアミド、エチルメタクリルアミド、ジエチルメタクリルアミド、N−イソプロピルアクリルアミド、N−ビニルピロリドン、ε―カプロラクタム、N,N’−ジメチルアミノエチルメタクリル酸、ジアリルジメチルアンモニウムクロライド、2−アクリルアミド−2−メチルプロパンスルホン酸ナトリウム等が挙げられる。 Moreover, if it is a range which does not impair the effect of this invention, monomers other than said (A)-(C) can also be contained as a constituent monomer. Content should just be the range of 50 mass% or less of a constituent monomer total amount, for example, can contain about 0.0001-10 mass%. Examples of such monomers include ethylene, propylene, butadiene, styrene, vinyl chloride, vinylidene chloride, vinyl alcohol, vinyl acetate, maleic anhydride, acrylonitrile, acrylamide, methacrylamide, methyl acrylamide, methyl methacrylamide, dimethyl methacrylamide. , Ethylacrylamide, ethylmethacrylamide, diethylmethacrylamide, N-isopropylacrylamide, N-vinylpyrrolidone, ε-caprolactam, N, N′-dimethylaminoethylmethacrylic acid, diallyldimethylammonium chloride, 2-acrylamido-2-methylpropane Examples thereof include sodium sulfonate.
本発明に用いられる共重合体は、上記モノマー(A)〜(C)を用い、公知の重合方法を用いて重合することにより得ることができる。重合方法として、例えば、均一溶液重合法、不均一溶液重合法、乳化重合法、逆相乳化重合法、塊状重合法、懸濁重合法、沈殿重合法等を用いることができる。例えば、均一溶液重合法の場合には、モノマー(A)〜(C)を適当なモノマー組成にて溶媒に溶解し、窒素雰囲気下、ラジカル重合開始剤を添加して加熱撹拌することにより本発明の共重合体を得ることができる。また、ポリアクリル酸を用い、後から適当な官能基を付加させるポストモディフィケーション法によって、共重合体を得ることもできる。 The copolymer used for this invention can be obtained by superposing | polymerizing using the said monomer (A)-(C) using a well-known polymerization method. As the polymerization method, for example, a homogeneous solution polymerization method, a heterogeneous solution polymerization method, an emulsion polymerization method, a reverse phase emulsion polymerization method, a bulk polymerization method, a suspension polymerization method, a precipitation polymerization method and the like can be used. For example, in the case of homogeneous solution polymerization, the monomers (A) to (C) are dissolved in a solvent with an appropriate monomer composition, and a radical polymerization initiator is added and stirred under heating in a nitrogen atmosphere. Can be obtained. A copolymer can also be obtained by a post-modification method using polyacrylic acid and adding an appropriate functional group later.
重合の際に用いられる溶媒としては、各モノマーを溶解又は懸濁し得る溶媒であればいずれの溶媒を用いることも可能であり、例えば、メタノール、エタノール、プロピルアルコール、イソプロピルアルコール、ブチルアルコール等のアルコール系溶媒、ヘキサン、ヘプタン、オクタン、イソオクタン、デカン、流動パラフィンなどの炭化水素系溶媒、ジメチルエーテル、ジエチルエーテル、テトラヒドロフラン等のエーテル系溶媒、アセトン、メチルエチルケトン等のケトン系溶媒、酢酸メチル、酢酸エチル、酢酸ブチル等のエステル系溶媒、塩化メチレン、クロロホルム、四塩化炭素等の塩化物系溶媒などの他、ジメチルホルムアミド、ジエチルホルムアミド、ジメチルスルホキシド、ジオキサン等が挙げられる。これら溶媒は2種以上混合して用いてもよい。通常、用いる重合開始剤の開始温度よりも沸点が高い溶媒を選択することが好適である。 As the solvent used in the polymerization, any solvent can be used as long as it can dissolve or suspend each monomer. For example, alcohols such as methanol, ethanol, propyl alcohol, isopropyl alcohol, and butyl alcohol can be used. Solvents, hexane, heptane, octane, isooctane, decane, liquid solvents such as liquid paraffin, ether solvents such as dimethyl ether, diethyl ether, tetrahydrofuran, ketone solvents such as acetone, methyl ethyl ketone, methyl acetate, ethyl acetate, acetic acid In addition to ester solvents such as butyl and chloride solvents such as methylene chloride, chloroform and carbon tetrachloride, dimethylformamide, diethylformamide, dimethylsulfoxide, dioxane and the like can be mentioned. Two or more of these solvents may be mixed and used. Usually, it is suitable to select a solvent having a boiling point higher than the starting temperature of the polymerization initiator to be used.
重合開始剤としては、ラジカル重合を開始する能力を有するものであれば特に制限はなく、例えば、過酸化ベンゾイル等の過酸化物、アゾビスイソブチロニトリル(AIBN)、2,2’−アゾビス(イソ酪酸)ジメチル等のアゾ系化合物の他、過硫酸カリウム、過硫酸アンモニウム等の過硫酸系重合開始剤が挙げられる。なお、これらの重合開始剤によらずとも、光化学反応や、放射線照射等によっても重合を行なうことができる。重合温度は各重合開始剤の重合開始温度以上とする。例えば、過酸化物系重合開始剤では、通常70℃程度とすればよい。 The polymerization initiator is not particularly limited as long as it has the ability to initiate radical polymerization. For example, peroxide such as benzoyl peroxide, azobisisobutyronitrile (AIBN), 2,2′-azobis (Isobutyric acid) In addition to azo compounds such as dimethyl, persulfuric acid polymerization initiators such as potassium persulfate and ammonium persulfate may be mentioned. In addition, it can superpose | polymerize also by photochemical reaction, radiation irradiation, etc. irrespective of these polymerization initiators. The polymerization temperature is not less than the polymerization start temperature of each polymerization initiator. For example, in the case of a peroxide-based polymerization initiator, it may be usually about 70 ° C.
重合時間は特に制限されないが、通常2〜24時間である。比較的高分子量のポリマーを得たい場合には、1日程度反応させることが望ましい。反応時間が短すぎると未反応のモノマーが残存し、分子量も比較的小さくなることがある。本発明に用いられる共重合体の平均分子量は特に制限されるものではないが、特に平均分子量1万〜20万程度であることが好ましい。また、本発明に用いられる共重合体分子においては、モノマー(A)〜(C)の付加する順序は特に指定されるものではなく、ブロック状に付加していてもランダム状に付加していてもよいが、通常はモノマー(A)〜(C)がランダム状に付加された共重合体が得られる。 The polymerization time is not particularly limited, but is usually 2 to 24 hours. When it is desired to obtain a relatively high molecular weight polymer, it is desirable to react for about one day. If the reaction time is too short, unreacted monomers may remain and the molecular weight may be relatively small. The average molecular weight of the copolymer used in the present invention is not particularly limited, but in particular, the average molecular weight is preferably about 10,000 to 200,000. In addition, in the copolymer molecule used in the present invention, the order in which the monomers (A) to (C) are added is not particularly specified, and even if they are added in blocks, they are added randomly. However, usually, a copolymer in which the monomers (A) to (C) are randomly added can be obtained.
本発明に用いられる代表的な共重合体の一例を、下記一般式(11)に示す。
なお、上記一般式(11)中、R1〜R8,l,m,nは前述した定義の通りである。a,b,cは、構成モノマー全量中のモノマー(A)、モノマー(B)、モノマー(C)のそれぞれの質量割合を表す。なお、上記一般式(11)中、構成モノマー全量に対するモノマー(A)の質量割合を表すaは、20質量%以上となるように調整される。 In the general formula (11), R 1 to R 8 , l, m, and n are as defined above. a, b, and c represent the mass proportions of the monomer (A), monomer (B), and monomer (C) in the total amount of the constituent monomers. In the general formula (11), “a” representing the mass ratio of the monomer (A) to the total amount of the constituent monomers is adjusted to 20% by mass or more.
本発明にかかる***用組成物においては、前記共重合体高分子の配合量は、特に制限されるものではなく、使用目的に合わせ適宜配合量を調整して用いることができるが、組成物の総量に対して0.1〜20質量%、さらには0.5〜15質量%であることが好適である。共重合体の配合量が0.1質量%より少ない場合には化粧持ち向上効果が認められない場合があり、一方で20質量%より多い場合には、***上に著しい被膜感を感じるようになる場合がある。 In the composition for lips according to the present invention, the blending amount of the copolymer polymer is not particularly limited and can be used by appropriately adjusting the blending amount according to the purpose of use, but the total amount of the composition The content is preferably 0.1 to 20% by mass, and more preferably 0.5 to 15% by mass. When the amount of the copolymer is less than 0.1% by mass, the effect of improving the longevity of the makeup may not be recognized. On the other hand, when it is more than 20% by mass, a remarkable film feeling is felt on the lips. There is a case.
本発明は、前述のようにして製造された共重合体高分子を***用組成物に配合することによって、当該***用組成物の化粧持ちを向上するとともに、***上の被膜感を改善するというものである。
本発明にかかる***用組成物においては、必須成分である前記共重合体高分子の他に、通常化粧料や医薬品に用いられる成分を、本発明の効果を損なわない範囲で配合することができる。
The present invention improves the cosmetic durability of the lip composition and improves the coating feeling on the lip by blending the copolymer polymer produced as described above into the lip composition. It is.
In the composition for lips according to the present invention, in addition to the copolymer polymer which is an essential component, components usually used in cosmetics and pharmaceuticals can be blended within a range not impairing the effects of the present invention.
例えば、本発明にかかる***用組成物において、前記共重合体とともに揮発性油分を好適に配合することができる。本発明に用いられる揮発性油分としては、下記一般式(4)で示される直鎖シリコーン油、下記一般式(5)で示される環状シリコーン油、下記一般式(6)で示されるアルキル変性シリコーン油、イソパラフィンが挙げられる。
本発明にかかる***用組成物においては、前記揮発性油分の1種又は2種以上を選択して配合してもよい。前記揮発性油分の配合量は、特に制限されるものではないが、組成物中10〜90質量%、さらには20〜80質量%であることが好適である。揮発性油分の配合量が少なすぎると、化粧もちが悪くなる場合があり、多すぎると、口紅の形態安定性が悪くなる場合がある。 In the composition for lips according to the present invention, one or more volatile oil components may be selected and blended. The blending amount of the volatile oil is not particularly limited, but is preferably 10 to 90% by mass, and more preferably 20 to 80% by mass in the composition. If the blending amount of the volatile oil is too small, makeup may be deteriorated, and if it is too much, the shape stability of the lipstick may be deteriorated.
また、本発明にかかる***用組成物において、不揮発性油分を好適に配合することができる。本発明に用いられる不揮発性油分としては、下記一般式(7)で示されるフッ素変性ジメチルシリコーン、下記一般式(8)で示されるフッ素変性フェニルシリコーン、下記一般式(9)で示されるアルコキシ変性シリコーン、下記一般式(10)で示されるアルキル変性シリコーン、トリ(水添ロジン・イソステアリン酸)グリセリル、パラメトキシケイ皮酸2−エチルヘキシルが挙げられる。
本発明にかかる***用組成物においては、前記不揮発性油分の1種又は2種以上を選択して配合してもよい。前記不揮発性油分の配合量は、組成物中0.1〜50質量%、さらには0.5〜40質量%であることが好適である。不揮発性油分の配合量が少なすぎると、使用感触が悪い場合があり、多すぎると、化粧もちが悪くなる場合がある。 In the composition for lips according to the present invention, one or more of the non-volatile oils may be selected and blended. The compounding amount of the non-volatile oil component is preferably 0.1 to 50% by mass, more preferably 0.5 to 40% by mass in the composition. If the blended amount of the non-volatile oil is too small, the feeling of use may be poor, and if it is too large, the makeup may be deteriorated.
また、本発明にかかる***用組成物において、水、あるいは保湿剤を好適に配合することができる。本発明に用いられる保湿剤としては、例えば、エチレングリコール、ジエチレングリコール、1,3−ブチレングリコール、グリセリン、ヘキサメチレングリコール、イソプレングリコール、ポリエチレングリコール、ヒアルロン酸、コンドロイチン硫酸、キチン、キトサン、キシリトール、ソルビトール、マルチトール、ムコイチン硫酸、カロニン酸、アテロコラーゲン、コレステリル-12-ヒドロキシステアレート、乳酸ナトリウム、dl−ピロリドンカルボン酸塩、短鎖可溶性コラーゲン、ジグリセリン(EO)PO付加物、イザヨイバラ抽出物、セイヨウノコギリソウ抽出物、メリロート抽出物、ジプロピレングリコール等が挙げられる。 In the lip composition according to the present invention, water or a humectant can be suitably blended. Examples of the humectant used in the present invention include ethylene glycol, diethylene glycol, 1,3-butylene glycol, glycerin, hexamethylene glycol, isoprene glycol, polyethylene glycol, hyaluronic acid, chondroitin sulfate, chitin, chitosan, xylitol, sorbitol, Maltitol, mucoitin sulfate, caronic acid, atelocollagen, cholesteryl-12-hydroxystearate, sodium lactate, dl-pyrrolidone carboxylate, short-chain soluble collagen, diglycerin (EO) PO adduct, Izayoi rose extract, yarrow extract Products, merryrot extract, dipropylene glycol and the like.
本発明にかかる***用組成物においては、前記保湿剤の1種又は2種以上を選択して配合してもよい。水又は保湿剤の配合量は、組成物中0.01〜20質量%、さらには0.1〜10質量%であることが好適である。水又は保湿剤の配合量が少なすぎると、保湿効果に劣る場合があり、多すぎると、製剤の安定性が悪い場合がある。 In the composition for lips according to the present invention, one or more of the humectants may be selected and blended. The amount of water or humectant is preferably 0.01 to 20% by mass, more preferably 0.1 to 10% by mass in the composition. If the amount of water or humectant is too small, the moisturizing effect may be inferior, and if too much, the stability of the formulation may be poor.
本発明において、***用組成物とは、例えば、口紅やリップグロスのように***に適用することを目的とした組成物であれば、特に制限されるものではなく、スティック状、ペンシル状、軟膏状、液状、ジェル状等の具体的形態を問わず用いることができる。本発明の***用組成物は、例えば、上記必須成分を含有した混合物を加熱融解し、スティックや中皿内に流し込んで冷却固化して製造することができる。また、本発明の***用組成物は、メーキャップ化粧料である口紅、リップグロスの他、色剤を配合しないリップクリーム等に応用することも可能である。 In the present invention, the lip composition is not particularly limited as long as it is a composition intended to be applied to the lips, such as lipstick and lip gloss, and is not limited to a stick, pencil or ointment. It can be used regardless of a specific form such as a liquid, gel or gel. The lip composition of the present invention can be produced, for example, by heating and melting a mixture containing the above essential components, pouring the mixture into a stick or an inner dish, and solidifying by cooling. Further, the lip composition of the present invention can be applied to lipsticks and lip glosses that are makeup cosmetics, as well as lip creams and the like that do not contain colorants.
以下に本発明の実施例を挙げてさらに詳しい説明を行なうが、本発明はこれらに限定されるものではない。
まず最初に、本発明の共重合体の製造において用いた各モノマーの構造を以下に示す。
Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
First, the structure of each monomer used in the production of the copolymer of the present invention is shown below.
モノマーA1:
モノマーA2:
モノマーB1:
モノマーC1:
モノマーC2:
つづいて、本発明に用いる共重合体の合成方法について説明する。
共重合体1−1
攪拌機、温度計、還流冷却機を備えたガラス製フラスコ中に、上記一般式(11)で示されるメタクリル酸メチル(モノマーA1)35質量部、上記一般式(13)で示されるメタクリル酸ポリオキシエチレンエーテル(モノマーB1)5質量部、上記一般式(14)で示されるメタクリロキシプロピルポリジメチルシロキサン(モノマーC1)60質量部、イソプロパノール120質量部、及びジメチル−2,2’−アゾビス(2−メチルプロピオネート)4質量部を入れ、窒素気流下で加熱し、80℃で10時間重合反応を行なった。次いで、減圧下、揮発性成分を留去して共重合体1−1を得た。
Next, a method for synthesizing the copolymer used in the present invention will be described.
Copolymer 1-1
In a glass flask equipped with a stirrer, a thermometer, and a reflux condenser, 35 parts by mass of methyl methacrylate (monomer A1) represented by the above general formula (11) and polyoxymethacrylate represented by the above general formula (13) 5 parts by mass of ethylene ether (monomer B1), 60 parts by mass of methacryloxypropyl polydimethylsiloxane (monomer C1) represented by the general formula (14), 120 parts by mass of isopropanol, and dimethyl-2,2′-azobis (2- 4 parts by mass of methyl propionate) was added, heated under a nitrogen stream, and polymerized at 80 ° C. for 10 hours. Subsequently, the volatile component was distilled off under reduced pressure to obtain a copolymer 1-1.
本発明者らは、以上に示した合成方法に準じて各種共重合体を調製し、以下の評価を行った。
共重合体の配合
本発明者らは、まず最初に、上記製造例に準じて各種共重合体を調製し、当該共重合体を被膜形成成分として配合した口紅と、従来の被膜形成成分を配合した口紅との比較を行った。各試験例に用いた共重合体のモノマー組成及び口紅の配合組成と評価結果とを下記表1に併せて示す。なお、評価基準は以下の通りである。
The present inventors prepared various copolymers according to the synthesis method shown above, and performed the following evaluations.
Blending of copolymer The inventors first prepared various copolymers according to the above production example, blended a lipstick blended with the copolymer as a film-forming component, and a conventional film-forming component. A comparison was made with the lipstick. The monomer composition of the copolymer used in each test example, the blending composition of lipstick, and the evaluation results are shown in Table 1 below. The evaluation criteria are as follows.
(1)化粧持ち
各試験例の口紅の化粧持ちの有無について、専門パネラー10名により実使用試験を実施した。評価基準は以下の通りである
◎:パネラー8名以上が、化粧持ちが良好であると認めた。
○:パネラー6名以上8名未満が、化粧持ちが良好であると認めた。
△:パネラー3名以上6名未満が、化粧持ちが良好であると認めた。
×:パネラー3名未満が、化粧持ちが良好であると認めた。
(1) Makeup The actual use test was conducted by 10 expert panelists on the presence or absence of lipstick makeup in each test example. Evaluation criteria are as follows: A: Eight or more panelists recognized that makeup was good.
○: 6 or more panelists and less than 8 panelists admitted that they had good makeup.
Δ: 3 or more panelists and less than 6 panelists recognized that makeup was good.
X: Less than 3 panelists recognized that makeup was good.
(2)被膜感
各試験例の口紅の被膜感の有無について、専門パネラー10名により実使用試験を実施した。評価基準は以下の通りである
◎:パネラー8名以上が、被膜感が無いと認めた。
○:パネラー6名以上8名未満が、被膜感が無いと認めた。
△:パネラー3名以上6名未満が、被膜感が無いと認めた。
×:パネラー3名未満が、被膜感が無いと認めた。
(2) Feeling of the coating With regard to the presence or absence of the coating feeling of the lipstick in each test example, an actual use test was conducted by 10 professional panelists. Evaluation criteria are as follows: A: Eight or more panelists recognized that there was no film feeling.
○: 6 or more panelists and less than 8 panelists recognized that there was no film feeling.
Δ: 3 or more and less than 6 panelists recognized that there was no film feeling.
X: Less than 3 panelists recognized that there was no film feeling.
(3)つや
各試験例の口紅のつやの有無について、専門パネラー10名により実使用試験を実施した。評価基準は以下の通りである
◎:パネラー8名以上が、つやが良好であると認めた。
○:パネラー6名以上8名未満が、つやが良好であると認めた。
△:パネラー3名以上6名未満が、つやが良好であると認めた。
×:パネラー3名未満が、つやが良好であると認めた。
(3) Luster With regard to the presence or absence of lipstick in each test example, an actual use test was conducted by 10 professional panelists. The evaluation criteria are as follows: A: Eight or more panelists recognized that the gloss was good.
○: 6 or more panelists and less than 8 panelists recognized that gloss was good.
Δ: 3 or more panelists and less than 6 panelists recognized that gloss was good.
X: Less than 3 panelists recognized that gloss was good.
(4)処方中での溶解性
各試験例の口紅について共重合体の処方中での溶解性を評価した。評価基準は以下の通りである。
◎:溶解性が良かった。
×:溶解性が悪く製剤化できなかった。
(4) Solubility in formulation The solubility in the formulation of the copolymer was evaluated for the lipstick of each test example. The evaluation criteria are as follows.
A: The solubility was good.
X: Solubility was poor and could not be formulated.
上記表1より、前記共重合体1−1を被膜形成成分として配合した試験例1−1の口紅は、極めて優れた化粧持ちの効果を示すとともに、被膜感が著しく改善されているものであることが明らかとなった。
これに対して、モノマーAのみからなる共重合体1−2を配合した試験例1−2、モノマーA及びBからなる共重合体1−3を配合した試験例1−3の場合は、処方中での溶解性が悪いため、製剤化することができなかった。また、モノマーA及びCからなる共重合体1−4を配合した試験例1−4の場合では、***上に被膜感を生じてしまった。また、一般的な被膜形成成分として知られるトリメチルシロキシケイ酸を被膜形成成分として配合した試験例1−5では、化粧持ち、被膜感、つやのいずれも劣っているものであり、非水系ポリマーエマルションを配合した試験例1−6では、化粧持ち、被膜感、つやともに改善されてはいるものの、十分なものであるとは言い難い。
From Table 1 above, the lipstick of Test Example 1-1 in which the copolymer 1-1 was blended as a film-forming component showed an extremely excellent effect of makeup retention and the film feeling was remarkably improved. It became clear.
On the other hand, in the case of Test Example 1-2 in which the copolymer 1-2 consisting only of the monomer A is blended, and Test Example 1-3 in which the copolymer 1-3 consisting of the monomer A and B is blended, Due to poor solubility in it, it could not be formulated. In addition, in the case of Test Example 1-4 in which the copolymer 1-4 composed of monomers A and C was blended, a film feeling was produced on the lips. Further, in Test Example 1-5 in which trimethylsiloxysilicic acid, which is known as a general film-forming component, is blended as a film-forming component, all of the makeup durability, the film feeling, and the gloss are inferior. In the blended Test Example 1-6, although the makeup durability, the coating feeling, and the gloss are improved, it is difficult to say that it is sufficient.
共重合体のモノマー組成
つづいて、本発明者らは、共重合体の好適なモノマー組成について検討するため、上記製造例に準じてモノマー(A)の含有量を変化させた各種共重合体を調製し、それぞれの共重合体を配合した口紅についての評価を行なった。各試験例の口紅の配合組成と評価結果とを表2に併せて示す。なお、評価基準は前記試験と同様である。
Following the monomer composition of the copolymer, the present inventors found that a copolymer To investigate the preferred monomer composition of the various copolymers obtained by changing the content of the monomer (A) according to the above Production Example The lipsticks prepared and blended with the respective copolymers were evaluated. Table 2 shows the composition and evaluation results of the lipstick of each test example. The evaluation criteria are the same as in the above test.
上記表2より、モノマー(A)を全く含有していない共重合体1−5を用いた試験例1−7では、化粧持ちの点で著しく劣っている。一方で、共重合体中のモノマー(A)の割合が増えていくに従って、化粧持ちの点が改善されていく傾向にあることがわかるが、モノマー(A)の割合が20質量%未満である共重合体1−6,7を用いた試験例1−8,9においては、化粧持ちの点で十分なものであるものとは言い難い。これに対して、共重合体中のモノマー(A)の割合が20質量%以上である共重合体1−8〜11を用いた試験例1−10〜13では、化粧持ち、被膜感ともに極めて優れているものであることがわかった。
このことから、本発明にかかる***用組成物においては、共重合体中のモノマー(A)の割合が20質量%以上である必要があるものと考えられる。
From Table 2 above, Test Example 1-7 using the copolymer 1-5 containing no monomer (A) is significantly inferior in terms of longevity. On the other hand, as the proportion of the monomer (A) in the copolymer increases, it can be seen that the makeup holding point tends to be improved, but the proportion of the monomer (A) is less than 20% by mass. In Test Examples 1-8 and 9 using the copolymers 1-6 and 7, it is difficult to say that they are sufficient in terms of long lasting makeup. On the other hand, in Test Examples 1-10 to 13 using the copolymers 1-8 to 11 in which the proportion of the monomer (A) in the copolymer is 20% by mass or more, both the makeup durability and the film feeling are extremely high. It turned out to be excellent.
From this, in the composition for lips according to the present invention, it is considered that the proportion of the monomer (A) in the copolymer needs to be 20% by mass or more.
***用組成物中の共重合体濃度
つづいて、本発明者らは、***用組成物中へ配合する共重合体の好適な配合濃度について検討するため、共重合体の配合量を各種変化させた口紅を調製し、その評価を行なった。各試験例の口紅の配合組成と評価結果とを表3に併せて示す。なお、評価基準は前記試験と同様である。
Following copolymer concentration of lip compositions, the present inventors to consider the preferred formulation concentration of the copolymer to be blended into the lip compositions, the amount of the copolymer is varied is A lipstick was prepared and evaluated. Table 3 shows the composition of the lipstick and the evaluation results of each test example. The evaluation criteria are the same as in the above test.
上記表3より、共重合体1−1を1質量%程度配合した試験例1−15では、化粧持ち、被膜感、つやの改善効果が見られる。一方で、共重合体1−1を30質量%程度配合した試験例1−19では、被膜感の点で劣る傾向にある。このことから、本発明にかかる***用組成物においては、共重合体を1〜25質量%配合することが好適であるものと考えられる。 From Table 3 above, in Test Example 1-15 in which about 1% by mass of the copolymer 1-1 was blended, the effects of improving makeup, feeling of coating, and gloss can be seen. On the other hand, Test Example 1-19 containing about 30% by mass of copolymer 1-1 tends to be inferior in terms of film feeling. From this, it is thought that it is suitable to mix | blend 1-25 mass% of copolymers in the composition for lips concerning this invention.
以下に本発明のその他の実施例を挙げるが、本発明はこれらに限定されるものではない。
共重合体2−1
攪拌機、温度計、還流冷却機を備えたガラス製フラスコ中に、上記一般式(11)で示されるメタクリル酸メチル(モノマーA1)35質量部、上記一般式(13)で示されるメタクリル酸ポリオキシエチレンエーテル(モノマーB1)15質量部、上記一般式(14)で示されるメタクリロキシプロピルポリジメチルシロキサン(モノマーC1)50質量部、イソプロパノール120質量部、及びジメチル−2,2’−アゾビス(2−メチルプロピオネート)4質量部を入れ、窒素気流下で加熱し、80℃で10時間重合反応を行なった。次いで、減圧下、揮発性成分を留去して共重合体2−1を得た。
Other examples of the present invention will be given below, but the present invention is not limited thereto.
Copolymer 2-1
In a glass flask equipped with a stirrer, a thermometer, and a reflux condenser, 35 parts by mass of methyl methacrylate (monomer A1) represented by the above general formula (11) and polyoxymethacrylate represented by the above general formula (13) 15 parts by mass of ethylene ether (monomer B1), 50 parts by mass of methacryloxypropyl polydimethylsiloxane (monomer C1) represented by the general formula (14), 120 parts by mass of isopropanol, and dimethyl-2,2′-azobis (2- 4 parts by mass of methyl propionate) was added, heated under a nitrogen stream, and polymerized at 80 ° C. for 10 hours. Subsequently, the volatile component was distilled off under reduced pressure to obtain a copolymer 2-1.
共重合体2−2
攪拌機、温度計、還流冷却機を備えたガラス製フラスコ中に、上記一般式(11)で示されるメタクリル酸メチル(モノマーA1)35質量部、上記一般式(12)で示されるアクリル酸2−エチルヘキシル15質量部(モノマーA2)、上記一般式(13)で示されるメタクリル酸ポリオキシエチレンエーテル(モノマーB1)5質量部、上記一般式(15)で示されるメタクリロキシプロピルポリジメチルシロキサン(モノマーC2)45質量部、イソプロパノール120質量部、及びジメチル−2,2’−アゾビス(2−メチルプロピオネート)4質量部を入れ、窒素気流下で加熱し、80℃で10時間重合反応を行なった。次いで、減圧下、揮発性成分を留去して共重合体2−2を得た。
Copolymer 2-2
In a glass flask equipped with a stirrer, a thermometer and a reflux condenser, 35 parts by mass of methyl methacrylate (monomer A1) represented by the above general formula (11) and 2-acrylic acid represented by the above general formula (12) 15 parts by mass of ethylhexyl (monomer A2), 5 parts by mass of polyoxyethylene ether of methacrylic acid (monomer B1) represented by the above general formula (13), methacryloxypropyl polydimethylsiloxane represented by the above general formula (15) (monomer C2 ) 45 parts by mass, 120 parts by mass of isopropanol, and 4 parts by mass of dimethyl-2,2′-azobis (2-methylpropionate) were heated under a nitrogen stream, and a polymerization reaction was carried out at 80 ° C. for 10 hours. . Subsequently, the volatile component was distilled off under reduced pressure to obtain a copolymer 2-2.
実施例2−1
口紅 質量%
マイクロクリスタリンワックス 1.0
パラフィン 11.0
キャンデリラロウ 3.0
デカメチルシクロペンタシロキサン(一般式(5)中,y=5)残 部
ジメチルポリシロキサン(一般式(4)中,x=2) 20.0
アルキル変性シリコーン 10.0
(一般式(6)中,R9=C8H17)
共重合体2−1 10.0
ポリオキシエチレン変性シリコーン 3.0
メチルフェニルポリシロキサン 5.0
フッ素変性メチルフェニルシリコーン 10.0
(一般式(8)中,R11=Ph,R12=CH3,R13=C8F17,b=2、q=2、r=2、s=3)
アルコキシ変性シリコーン 2.0
(一般式(9)中,R14=C18H37,t=5、u=3)
パラメトキシケイ皮酸2−エチルヘキシル 1.0
シリカ(アエロジルR972:デグサ社製) 1.0
顔料 5.0
香料 適 量
(製法) 全成分を95℃にて混合溶解した後、容器に流し込み、冷却固化することにより口紅を得た。
上記実施例2−1の口紅は、化粧もちに優れ、被膜感が無く、さらにつやにも優れているものであった。
Example 2-1
Lipstick mass%
Microcrystalline wax 1.0
Paraffin 11.0
Candelilla Row 3.0
Decamethylcyclopentasiloxane (in general formula (5), y = 5) balance dimethylpolysiloxane (in general formula (4), x = 2) 20.0
Alkyl-modified silicone 10.0
(In the general formula (6), R 9 = C 8 H 17 )
Copolymer 2-1 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified methylphenyl silicone 10.0
(In general formula (8), R 11 = Ph, R 12 = CH 3 , R 13 = C 8 F 17 , b = 2, q = 2, r = 2, s = 3)
Alkoxy modified silicone 2.0
(In the general formula (9), R 14 = C 18 H 37 , t = 5, u = 3)
2-Ethylhexyl paramethoxycinnamate 1.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume appropriate amount
(Production Method) All components were mixed and dissolved at 95 ° C., then poured into a container and cooled and solidified to obtain a lipstick.
The lipstick of Example 2-1 was excellent in makeup, had no film feeling, and was excellent in gloss.
実施例2−2
口紅 質量%
マイクロクリスタリンワックス 0.5
キャンデリラロウ 1.0
合成ワックス(FNP−0090:日本精蝋社製) 8.0
デカメチルシクロペンタシロキサン 残 部
ジメチルポリシロキサン(一般式(4)中,x=2) 20.0
アルキル変性シリコーン 10.0
(一般式(6)中,R9=C8H17)
共重合体1−1 10.0
ポリオキシエチレン変性シリコーン 3.0
メチルフェニルポリシロキサン 5.0
フッ素変性メチルフェニルシリコーン 10.0
(一般式(8)中,R11=Ph,R12=CH3,R13=C8F17,b=2、q=2、r=2、s=3)
アルコキシ変性シリコーン 2.0
(一般式(9)中,R14=C18H37,t=5、u=3)
パラメトキシケイ皮酸2−エチルヘキシル 1.0
シリカ(アエロジルR972:デグサ社製) 1.0
顔料 5.0
香料 適 量
(製法) 全成分を95℃にて混合溶解した後、容器に流し込み、冷却固化することにより口紅を得た。
上記実施例2−2の口紅は、化粧もちに優れ、被膜感が無く、さらにつやにも優れているものであった。
Example 2-2
Lipstick mass%
Microcrystalline wax 0.5
Candelilla Row 1.0
Synthetic wax (FNP-0090: Nippon Seiwa Co., Ltd.) 8.0
Decamethylcyclopentasiloxane remainder dimethylpolysiloxane (in formula (4), x = 2) 20.0
Alkyl-modified silicone 10.0
(In the general formula (6), R 9 = C 8 H 17 )
Copolymer 1-1 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified methylphenyl silicone 10.0
(In general formula (8), R 11 = Ph, R 12 = CH 3 , R 13 = C 8 F 17 , b = 2, q = 2, r = 2, s = 3)
Alkoxy modified silicone 2.0
(In the general formula (9), R 14 = C 18 H 37 , t = 5, u = 3)
2-Ethylhexyl paramethoxycinnamate 1.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume appropriate amount
(Production Method) All components were mixed and dissolved at 95 ° C., then poured into a container and cooled and solidified to obtain a lipstick.
The lipstick of Example 2-2 was excellent in makeup, had no coating feeling, and was excellent in gloss.
実施例2−3
口紅 質量%
マイクロクリスタリンワックス 2.0
パラフィン 1.0
ポリエチレンワックス(平均分子量500) 10.0
カルナバロウ 1.0
デカメチルシクロペンタシロキサン 残 部
ジメチルポリシロキサン(一般式(4)中,x=2) 30.0
共重合体2−1 10.0
ポリオキシエチレン変性シリコーン 3.0
メチルフェニルポリシロキサン 5.0
フッ素変性ジメチルシリコーン 5.0
(一般式(7)中,R10=C8F17,a=11、o=11、p=75)
アルコキシ変性シリコーン 2.0
(一般式(9)中,R14=C18H37,t=5、u=3)
アルキル変性シリコーン 3.0
(一般式(10)中,R15=C18H37,v=5、w=3)
トリ(水添ロジン・イソステアリン酸)グリセリル 5.0
シリカ(アエロジルR972:デグサ社製) 1.0
顔料 5.0
香料 適 量
(製法) 全成分を95℃にて混合溶解した後、容器に流し込み、冷却固化することにより口紅を得た。
上記実施例2−3の口紅は、化粧もちに優れ、被膜感が無く、さらにつやにも優れているものであった。
Example 2-3
Lipstick mass%
Microcrystalline wax 2.0
Paraffin 1.0
Polyethylene wax (average molecular weight 500) 10.0
Carnavalou 1.0
Decamethylcyclopentasiloxane remainder dimethylpolysiloxane (in formula (4), x = 2) 30.0
Copolymer 2-1 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified dimethyl silicone 5.0
(In the general formula (7), R 10 = C 8 F 17 , a = 11, o = 11, p = 75)
Alkoxy modified silicone 2.0
(In the general formula (9), R 14 = C 18 H 37 , t = 5, u = 3)
Alkyl modified silicone 3.0
(In the general formula (10), R 15 = C 18 H 37 , v = 5, w = 3)
Tri (hydrogenated rosin / isostearic acid) glyceryl 5.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume appropriate amount
(Production Method) All components were mixed and dissolved at 95 ° C., then poured into a container and cooled and solidified to obtain a lipstick.
The lipstick of Example 2-3 was excellent in makeup, had no coating feeling, and was excellent in gloss.
実施例2−4
乳化口紅 質量%
マイクロクリスタリンワックス 1.0
パラフィン 12.0
キャンデリラロウ 2.0
デカメチルシクロペンタシロキサン 残 部
共重合体2−2 10.0
ポリオキシエチレン変性シリコーン 3.0
メチルフェニルポリシロキサン 5.0
トリ(水添ロジン・イソステアリン酸)グリセリル 5.0
シリカ(アエロジルR972:デグサ社製) 1.0
顔料 5.0
香料 適 量
ラポナイト 0.4
グリセリン 0.5
水 0.1
(製法) 水相パーツ(ラポナイト、グリセリン、水)以外の成分を95℃にて混合溶解し、撹拌しながら水相パーツを添加して乳化した後、容器に流し込み、冷却固化することにより乳化口紅を得た。
上記実施例2−4の口紅は、化粧もちに優れ、被膜感が無く、さらにつやにも優れているものであった。
Example 2-4
Emulsified lipstick mass%
Microcrystalline wax 1.0
Paraffin 12.0
Candelilla Row 2.0
Decamethylcyclopentasiloxane Remainder Copolymer 2-2 10.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Tri (hydrogenated rosin / isostearic acid) glyceryl 5.0
Silica (Aerosil R972: manufactured by Degussa) 1.0
Pigment 5.0
Perfume proper amount Laponite 0.4
Glycerin 0.5
Water 0.1
(Manufacturing method) Components other than aqueous phase parts (laponite, glycerin, water) are mixed and dissolved at 95 ° C, and after adding and emulsifying the aqueous phase parts with stirring, the mixture is poured into a container and cooled and solidified to emulsify lipstick. Got.
The lipstick of Example 2-4 was excellent in makeup, had no coating feeling, and was excellent in gloss.
実施例2−4
液状口紅 質量%
マイクロクリスタリンワックス 0.2
パラフィン 2.0
デカメチルシクロペンタシロキサン 残 部
共重合体2−2 15.0
ポリオキシエチレン変性シリコーン 3.0
メチルフェニルポリシロキサン 5.0
フッ素変性メチルフェニルシリコーン 20.0
(一般式(8)中,R11=Ph,R12=CH3,
R13=C8F17,b=3、q=6、r=20、s=100)
シリカ(アエロジルR972:デグサ社製) 2.0
顔料 5.0
香料 適 量
ラポナイト 0.4
グリセリン 0.5
水 0.1
(製法) 水相パーツ(ラポナイト、グリセリン、水)以外の成分を95℃にて混合溶解し、撹拌しながら水相パーツを添加して乳化した後、容器に流し込み、冷却固化することにより乳化口紅を得た。
上記実施例2−5の口紅は、化粧もちに優れ、被膜感が無く、さらにつやにも優れているものであった。
Example 2-4
Liquid lipstick mass%
Microcrystalline wax 0.2
Paraffin 2.0
Decamethylcyclopentasiloxane Residual copolymer 2-2 15.0
Polyoxyethylene-modified silicone 3.0
Methylphenylpolysiloxane 5.0
Fluorine-modified methylphenyl silicone 20.0
(In the general formula (8), R 11 = Ph, R 12 = CH 3 ,
R 13 = C 8 F 17 , b = 3, q = 6, r = 20, s = 100)
Silica (Aerosil R972: Degussa) 2.0
Pigment 5.0
Perfume proper amount Laponite 0.4
Glycerin 0.5
Water 0.1
(Manufacturing method) Components other than aqueous phase parts (laponite, glycerin, water) are mixed and dissolved at 95 ° C, and after adding and emulsifying the aqueous phase parts with stirring, the mixture is poured into a container and cooled and solidified to emulsify lipstick. Got.
The lipstick of Example 2-5 was excellent in makeup, had no coating feeling, and was excellent in gloss.
Claims (4)
The lip composition according to any one of claims 1 to 3, further comprising water and / or a humectant.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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JP2004170207A JP4219855B2 (en) | 2004-06-08 | 2004-06-08 | Lip composition |
US11/147,744 US20050271611A1 (en) | 2004-06-08 | 2005-06-08 | Cosmetic |
EP05105007A EP1604632B1 (en) | 2004-06-08 | 2005-06-08 | Cosmetic comprising a specific terpolymer |
DE602005001295T DE602005001295T2 (en) | 2004-06-08 | 2005-06-08 | Cosmetic composition containing a specific terpolymer |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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JP2004170207A JP4219855B2 (en) | 2004-06-08 | 2004-06-08 | Lip composition |
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JP4219855B2 true JP4219855B2 (en) | 2009-02-04 |
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JP6420052B2 (en) * | 2014-03-14 | 2018-11-07 | 株式会社コーセー | Oily solid cosmetic |
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