JP2009503191A - ペンダントポリ(アルキレンオキシ)置換基を備えたポリマー及びパーソナルケア用途におけるそれらの使用 - Google Patents
ペンダントポリ(アルキレンオキシ)置換基を備えたポリマー及びパーソナルケア用途におけるそれらの使用 Download PDFInfo
- Publication number
- JP2009503191A JP2009503191A JP2008524071A JP2008524071A JP2009503191A JP 2009503191 A JP2009503191 A JP 2009503191A JP 2008524071 A JP2008524071 A JP 2008524071A JP 2008524071 A JP2008524071 A JP 2008524071A JP 2009503191 A JP2009503191 A JP 2009503191A
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- Prior art keywords
- polymer
- independently
- alkyleneoxy
- formula
- personal care
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims abstract description 89
- 125000001424 substituent group Chemical group 0.000 title claims abstract description 28
- 125000005529 alkyleneoxy group Chemical group 0.000 title claims abstract description 26
- 239000000178 monomer Substances 0.000 claims abstract description 54
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 210000004209 hair Anatomy 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229920001519 homopolymer Polymers 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000001747 exhibiting effect Effects 0.000 abstract description 2
- 238000011282 treatment Methods 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003999 initiator Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical class CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 230000003741 hair volume Effects 0.000 description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- -1 N, N-dimethylaminoethyl methacrylate methyl chloride Benzyl dimethyl ammonium ethyl acrylate chloride Chemical compound 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000010191 image analysis Methods 0.000 description 4
- 239000012991 xanthate Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
- 239000003518 caustics Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000001542 size-exclusion chromatography Methods 0.000 description 3
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000012669 compression test Methods 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- DOMLXBPXLNDFAB-UHFFFAOYSA-N ethoxyethane;methyl prop-2-enoate Chemical compound CCOCC.COC(=O)C=C DOMLXBPXLNDFAB-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 229920000847 nonoxynol Polymers 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- DXMQZKIEVHKNTN-UHFFFAOYSA-N 2-[carbamimidoyl(ethyl)amino]acetic acid Chemical compound CCN(C(N)=N)CC(O)=O DXMQZKIEVHKNTN-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- MXRGSJAOLKBZLU-UHFFFAOYSA-N 3-ethenylazepan-2-one Chemical compound C=CC1CCCCNC1=O MXRGSJAOLKBZLU-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 229930003270 Vitamin B Natural products 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- BXUULZJBSDRIOL-UHFFFAOYSA-N benzyl(dimethyl)azanium;ethyl 2-methylprop-2-enoate;chloride Chemical compound [Cl-].CCOC(=O)C(C)=C.C[NH+](C)CC1=CC=CC=C1 BXUULZJBSDRIOL-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- WQHCGPGATAYRLN-UHFFFAOYSA-N chloromethane;2-(dimethylamino)ethyl prop-2-enoate Chemical compound ClC.CN(C)CCOC(=O)C=C WQHCGPGATAYRLN-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229920013750 conditioning polymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- ZAKOWWREFLAJOT-UHFFFAOYSA-N d-alpha-Tocopheryl acetate Natural products CC(=O)OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
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- 238000013467 fragmentation Methods 0.000 description 1
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- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- ZCTXEAQXZGPWFG-UHFFFAOYSA-N imidurea Chemical compound O=C1NC(=O)N(CO)C1NC(=O)NCNC(=O)NC1C(=O)NC(=O)N1CO ZCTXEAQXZGPWFG-UHFFFAOYSA-N 0.000 description 1
- 230000003752 improving hair Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
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- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- MMNOTXXCQAFCLV-UHFFFAOYSA-N n,n-dimethylmethanamine;2-methyl-n-propylprop-2-enamide;hydrochloride Chemical compound [Cl-].C[NH+](C)C.CCCNC(=O)C(C)=C MMNOTXXCQAFCLV-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CLQAIPMPVHYANA-UHFFFAOYSA-N n-propylprop-2-enamide;trimethylazanium;chloride Chemical compound [Cl-].C[NH+](C)C.CCCNC(=O)C=C CLQAIPMPVHYANA-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
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- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000001543 one-way ANOVA Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 239000002304 perfume Substances 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
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- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
-
- 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
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Abstract
各R1は独立して、H、メチル又はエチルであり、各R2は独立して、H又は(C1〜C6)アルキルであり、各nは独立して、約5から約500の整数である)によるペンダントポリ(アルキレンオキシ)置換基を含むモノマー単位を、該ポリマーのモノマー単位の総数を基準として50%より多く含み、且つモル当たり約1,000から約1,000,000グラムの重量平均分子量を示すポリマーは、パーソナルケア用途において有用である。
Description
本発明は、ポリマーに、一層特にはペンダントポリ(アルキレンオキシ)置換基を備えた或るポリマー及びパーソナルケア用途におけるかかるポリマーの使用に関する。
もっぱら頭髪を洗浄するためにもくろまれた製品は、毛髪を絡み合ったそして扱いにくいままにし得る。櫛すき摩擦を低減することにより並びにしなやかで滑らかな触感及び艶のある外観を毛髪に与えることにより毛髪状態を改善するためのコンディショニングポリマー及び有益剤が知られている。しかしながら、多くの場合において、かかるポリマー及び有益剤はまた、毛髪上におけるポリマーコンディショナーの付着に因る毛髪容積の減少及び髪の毛間の摩擦の減少に因る毛髪の腰への悪影響のようないくつかの望ましくない効果を生じ得る。
第1側面において、本発明は、ポリマーであって、モノマー単位当たり少なくとも1個の式(I)
〔ここで、
各R1は独立して、H、メチル又はエチルであり、
各R2は独立して、H又は(C1〜C6)アルキルであり、
各nは独立して、約5から約500の整数である〕
によるペンダントポリ(アルキレンオキシ)置換基を含むモノマー単位を、該ポリマーのモノマー単位の総数を基準として50パーセントより多く含み、且つモル当たり約1,000から約1,000,000グラムの重量平均分子量を示すポリマーに向けられる。
ポリ(アルキレンオキシ)置換基に関して本明細書において用いられる場合の用語「ペンダント」は、ポリマー鎖に結合されている側基としてかかる基が存在することを意味する。
によるモノマーに由来し、そしてかかるモノマー単位の各々は式(III)
によるものであり、しかしてここで
各R3は独立して、H又は(C1〜C4)アルキルであり、
R1、R2及びnは各々、上記のとおり定義される。
(a)約90%から100%未満一層典型的には約95%から100%未満更に一層典型的には約99%から100%未満の第1モノマー単位、しかもそれらの各々は
(i)モノマー単位当たり少なくとも1個の式(I)(ここで、R1、R2及びnは各々上記に記載されたとおりである)によるペンダントポリ(アルキレンオキシ)置換基を含み、及び/又は
(ii)構造(III)(ここで、R1、R2、R3及びnは各々上記に記載されたとおりである)によるものであり、
並びに
(b)0%より多いから約10%一層典型的には0%より多いから約5%更に一層典型的には0%から多いから約1%の、式(I)によるポリ(アルキレンオキシ)置換基を含まない第2モノマー単位
を含む。
実施例1のポリ(ノナエチレングリコールメチルエーテルアクリレート(「p(nEGA)」)ホモポリマーをMADIXにより作り、そして30,000g/molの理論分子量を有していた。開始剤(水中25.1%溶液として添加された0.1826gの過硫酸アンモニウム及び2gのすすぎ水)及び制御移動剤(0.833gのキサンテート,Robinson Bros.のロジキサン(Rhodixan)A1)の存在下で(5のキサンテート対開始剤のモル比でもって)、4.4:1の水対エタノール(重量による)の混合物中で、20重量%のノナエチレングリコールメチルエーテルアクリレートモノマー(120g)を70℃にて17時間にわたって重合することにより、該p(nEGA)ポリマーを合成した。モノマーを反応の始めに反応器に装填し、そしてキサンテート添加を行った5分以内に開始剤を一度に添加した。苛性加水分解されたポリマーは、各々サイズ排除クロマトグラフィー及びポリ(アクリル酸)標準との溶離画分の屈折率の比較により決定された場合、8,600g/molのMn及び11,800g/molのMwを示した。加水分解されたポリマーについて測定された分子量を逆算して、元の(加水分解されていない)p(nEGA)ポリマーについて約50,000g/molのMn及び約74,000g/molのMwが得られ、そして加水分解されていないポリマーについての多分散性指数は約1.5であると算出された。
デルタ(容積)=容積(処置された)−容積(処置されていない) (A)
ここで、「容積(処置されていない)」はポリマーでの処置前に測定された容積を意味し、そして「容積(処置された)」はポリマーでの処置後に測定された容積を意味する。所与処置条件について、デルタ(容積)平均をデルタ(容積)値の算術平均として算出した。各場合において、報告された「下限」及び「上限」は、所与処置条件について決定されたデルタ(容積)値についての95%信頼区間のそれぞれ「下限」及び「上限」である。
デルタ(仕事量)=仕事量(処置された)−仕事量(処置されていない) (C)
ここで、「仕事量(処置された)」はポリマーでの処置後に測定された仕事量に相当し、そして「仕事量(処置されていない)」はポリマーでの処置前に測定された仕事量に相当する。ANOVAを用いて、データを統計的に解析した。各平均を囲む区間は、95%の信頼水準(すなわち、平均区間が重なる場合は、対応する処置間に95%の信頼度において有意差がない)におけるフィッシャーの最小有意差(LSD)手法に基づいた。
実施例2のp(nEGA)ホモポリマーを慣用のフリーラジカル重合により作った。水中の30重量%NEGAモノマー(200g)を、開始剤(水中1%溶液として添加された0.0734gの過硫酸ナトリウム)の存在下で、0.07%の開始剤対モノマーのモル比でもって75℃にて9時間にわたって重合することにより、p(nEGA)を合成した。開始剤は80分にわたって5回に分けて添加され、一方モノマーの10%は90分にわたって供給された。初期p(nEGA)ホモポリマーの苛性加水分解後に残留アクリル酸を測定することにより、モノマー転化率を評価した。実験最終濃度は、29.62%であると測定された。ポリマー(苛性加水分解に付されていない)の分子量を、サイズ排除クロマトグラフィーによるポリマーの溶液の分画及び溶離画分によって散乱された光の強度の測定により決定した。ポリマーは、240,000g/molのMn、430,000g/molのMw及び約1.8の多分散性指数を示した。
Claims (15)
- ポリマーが、モノマー単位当たり少なくとも1個の式(I)によるペンダントポリ(アルキレンオキシ)置換基を含むモノマー単位を、該ポリマーのモノマー単位の総数を基準として約80パーセントに等しいか又はより多く含む、請求項1に記載のポリマー。
- ポリマーがホモポリマーである、請求項1に記載のポリマー。
- ポリマーが、該ポリマーのモノマー単位の総数を基準として、
(a)約90%から100%未満の第1モノマー単位(複数)、しかもそれらの第1のモノマー単位の各々はモノマー単位当たり少なくとも1個の式(I)によるペンダントポリ(アルキレンオキシ)置換基を含み、及び
(b)0%より多いから約10%の、式(I)によるポリ(アルキレンオキシ)置換基を含まない第2モノマー単位
を含む、請求項1に記載のポリマー。 - ポリマーが、モル当たり約2,500から約900,000グラムの重量平均分子量を示す、請求項1に記載のポリマー。
- ポリマーが、モル当たり約2,500から約750,000グラムの数平均分子量を示す、請求項1に記載のポリマー。
- ポリマーのモノマー単位の各々が、少なくとも1個の式(I)(ここで、各R1及び各R2は独立してH又はCH3であり、そして各nは独立して約5から約100の整数である)によるペンダントポリ(アルキレンオキシ)置換基を含む、請求項1に記載のポリマー。
- 各R1、各R2及び各R3が独立してH又はCH3であり、そして各nが独立して約5から約100の整数である、請求項9に記載のポリマー。
- パーソナルケア用組成物であって、請求項1に記載のポリマー及び化粧品上受容可能な担体を含むパーソナルケア用組成物。
- 化粧品上受容可能な担体が、水、有機溶媒、2種又はそれ以上の水混和性有機溶媒の混合物及び水と1種又はそれ以上の水混和性有機溶媒との混合物から選択される、請求項12に記載のパーソナルケア用組成物。
- パーソナルケア用組成物が、整髪用組成物であって、パーソナルケア用組成物の100重量部を基準として、約0.1から約10pbwのポリマーと、約90から約99.9pbwの、水を含む担体とを含む整髪用組成物である、請求項12に記載のパーソナルケア用組成物。
- パーソナルケア用組成物が洗浄用組成物であり、担体が水を含み、そしてパーソナルケア用組成物が更に1種又はそれ以上の界面活性剤を含む、請求項12に記載のパーソナルケア用組成物。
- 頭髪又は皮膚を処置する方法であって、頭髪又は皮膚を請求項1に記載のポリマーと接触させることを含む方法。
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| JP2003231609A (ja) * | 2001-12-05 | 2003-08-19 | Pola Chem Ind Inc | 皮膚外用剤及びそれに用いられるコポリマー |
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| JPH01131106A (ja) * | 1988-05-23 | 1989-05-24 | Nippon Oil & Fats Co Ltd | 化粧料基剤 |
| JPH0818950B2 (ja) * | 1992-05-01 | 1996-02-28 | 花王株式会社 | 化粧料 |
| JPH07206627A (ja) † | 1994-01-21 | 1995-08-08 | Nippon Oil & Fats Co Ltd | 化粧料 |
| US6375932B1 (en) * | 1996-09-10 | 2002-04-23 | Mitsubishi Chemical Corporation | Hair cosmetic composition containing amine-oxide polymer |
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| EP0922446A1 (en) * | 1997-12-03 | 1999-06-16 | Applied Research Systems Ars Holding N.V. | Solution-phase site-specific preparation of GRF-PEG conjugates |
| DE50015912D1 (de) * | 1999-07-15 | 2010-06-10 | Clariant Produkte Deutschland | Wasserlösliche Polymere und ihre Verwendung in kosmetischen und pharmazeutischen Mitteln |
| JP4822629B2 (ja) * | 2001-08-10 | 2011-11-24 | 大阪有機化学工業株式会社 | 毛髪用樹脂組成物およびそれからなる毛髪用化粧料 |
| US6906128B2 (en) * | 2001-12-12 | 2005-06-14 | Rhodia Chimie | Method for depositing a polymer onto a surface by applying a composition onto said surface |
| US6933340B2 (en) * | 2001-12-12 | 2005-08-23 | Rhodia Chimie | Formulation comprising an ionic compound, a polyionic polymer, and a block copolymer |
| EP1854843B1 (en) * | 2001-12-12 | 2009-09-09 | Rhodia Chimie | Cosmetic composition comprising a block copolymer |
| JP2004203761A (ja) * | 2002-12-24 | 2004-07-22 | Osaka Organic Chem Ind Ltd | 毛髪用樹脂組成物 |
| US20050152855A1 (en) * | 2003-09-19 | 2005-07-14 | Damian Hajduk | Materials for enhanced delivery of hydrophilic active agents in personal care formulations |
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2006
- 2006-07-26 KR KR1020077030670A patent/KR101353365B1/ko not_active Expired - Fee Related
- 2006-07-26 EP EP06788450.2A patent/EP1907067B2/en not_active Not-in-force
- 2006-07-26 WO PCT/US2006/028870 patent/WO2007016105A2/en not_active Ceased
- 2006-07-26 US US11/493,420 patent/US20070027301A1/en not_active Abandoned
- 2006-07-26 BR BRPI0614185A patent/BRPI0614185B1/pt not_active IP Right Cessation
- 2006-07-26 CN CN200680027433XA patent/CN101232921B/zh not_active Expired - Fee Related
- 2006-07-26 JP JP2008524071A patent/JP2009503191A/ja active Pending
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2012
- 2012-11-22 JP JP2012256569A patent/JP5770707B2/ja not_active Expired - Fee Related
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2015
- 2015-03-20 JP JP2015057375A patent/JP2015155420A/ja active Pending
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| JPH01213221A (ja) * | 1988-02-23 | 1989-08-28 | Goou Kagaku Kogyo Kk | 頭髪着色料固着用樹脂組成物及びそれを用いた頭髪着色剤 |
| JP2000226419A (ja) * | 1998-11-30 | 2000-08-15 | Pola Chem Ind Inc | 表面改質用の共重合体 |
| JP2001316435A (ja) * | 2000-05-09 | 2001-11-13 | Pola Chem Ind Inc | コポリマー及びそれを含有してなる化粧料 |
| JP2001316422A (ja) * | 2000-05-09 | 2001-11-13 | Pola Chem Ind Inc | コポリマー及びそれを含有してなる化粧料 |
| JP2002226521A (ja) * | 2001-02-02 | 2002-08-14 | Otsuka Chem Co Ltd | 紫外線吸収性共重合体 |
| JP2003231609A (ja) * | 2001-12-05 | 2003-08-19 | Pola Chem Ind Inc | 皮膚外用剤及びそれに用いられるコポリマー |
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| JP2012031087A (ja) * | 2010-07-30 | 2012-02-16 | Fancl Corp | 高分子乳化剤および乳化組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101232921B (zh) | 2012-04-04 |
| EP1907067A4 (en) | 2010-03-17 |
| KR20080027797A (ko) | 2008-03-28 |
| JP5770707B2 (ja) | 2015-08-26 |
| WO2007016105A3 (en) | 2007-06-14 |
| EP1907067B2 (en) | 2017-06-28 |
| BRPI0614185A2 (pt) | 2011-03-15 |
| JP2013079245A (ja) | 2013-05-02 |
| JP2015155420A (ja) | 2015-08-27 |
| EP1907067A2 (en) | 2008-04-09 |
| EP1907067B1 (en) | 2013-09-04 |
| BRPI0614185B1 (pt) | 2015-10-27 |
| US20070027301A1 (en) | 2007-02-01 |
| KR101353365B1 (ko) | 2014-01-20 |
| WO2007016105A2 (en) | 2007-02-08 |
| CN101232921A (zh) | 2008-07-30 |
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