WO2008156327A2 - Lipide présentant un groupe fonctionnel et composition pour soins personnels comprenant le lipide - Google Patents
Lipide présentant un groupe fonctionnel et composition pour soins personnels comprenant le lipide Download PDFInfo
- Publication number
- WO2008156327A2 WO2008156327A2 PCT/KR2008/003510 KR2008003510W WO2008156327A2 WO 2008156327 A2 WO2008156327 A2 WO 2008156327A2 KR 2008003510 W KR2008003510 W KR 2008003510W WO 2008156327 A2 WO2008156327 A2 WO 2008156327A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lipid
- hair
- functional group
- group
- aαjording
- Prior art date
Links
- 150000002632 lipids Chemical class 0.000 title claims abstract description 80
- 125000000524 functional group Chemical group 0.000 title claims abstract description 66
- 239000000203 mixture Substances 0.000 title claims description 22
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 19
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims description 17
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- -1 18-methyleicosanoyl group Chemical group 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 claims description 5
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- JNFDQAYPZCYWLD-UHFFFAOYSA-N bis[2-(2-ethoxyethoxy)ethyl] cyclohexane-1,4-dicarboxylate Chemical compound CCOCCOCCOC(=O)C1CCC(C(=O)OCCOCCOCC)CC1 JNFDQAYPZCYWLD-UHFFFAOYSA-N 0.000 claims description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 4
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 150000003573 thiols Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 3
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 229940106189 ceramide Drugs 0.000 claims description 2
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- 229940051250 hexylene glycol Drugs 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 2
- OKXGHXHZNCJMSV-UHFFFAOYSA-N nitro phenyl carbonate Chemical compound [O-][N+](=O)OC(=O)OC1=CC=CC=C1 OKXGHXHZNCJMSV-UHFFFAOYSA-N 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 claims 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 235000021355 Stearic acid Nutrition 0.000 claims 1
- 235000019445 benzyl alcohol Nutrition 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 239000008117 stearic acid Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 36
- 230000003020 moisturizing effect Effects 0.000 abstract description 15
- 230000002209 hydrophobic effect Effects 0.000 abstract description 9
- 230000008439 repair process Effects 0.000 description 24
- 230000003750 conditioning effect Effects 0.000 description 23
- 230000003699 hair surface Effects 0.000 description 22
- 230000000052 comparative effect Effects 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 5
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
- 239000002953 phosphate buffered saline Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 239000001993 wax Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WSRCOZWDQPJAQT-UHFFFAOYSA-N 18-methylicosanoic acid Chemical compound CCC(C)CCCCCCCCCCCCCCCCC(O)=O WSRCOZWDQPJAQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 230000005661 hydrophobic surface Effects 0.000 description 2
- 230000003752 improving hair Effects 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 244000303965 Cyamopsis psoralioides Species 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 229940098234 c12-14 pareth-3 Drugs 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N cystine group Chemical group C([C@@H](C(=O)O)N)SSC[C@@H](C(=O)O)N LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000003681 hair reduction Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 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
- 235000011929 mousse Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001024 permanent hair color Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 229940095673 shampoo product Drugs 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001027 temporary hair color Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
- A61K8/466—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
- D06M13/148—Polyalcohols, e.g. glycerol or glucose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/94—Involves covalent bonding to the substrate
Definitions
- the present invention relates to a personal care product which provides hair or skin with cosmetic conditioning effects, for example soft, moisturizing, silky or resilient effect.
- the present invention relates to a reactive personal care product capable of providing skin or hair with semi-permanent conditioning effect.
- the present invention relates to a product capable of providing fiber or clothing with semi-permanent conditioning effect.
- a personal care product for skin or hair provides skin or hair with cosmetically beneficial conditioning effects, for example, soft, moisturizing, silky or resilient effect.
- the personal care product may have additional functions svch as cleansing or washing.
- To improve the conditioning effects of the personal care prodvct various methods have been steadily studied, however in most cases, even though some methods have excellent conditioning effect, the conditioning effects do not last long. This is because a material having conditioning effects is weakly bonded to hair surface, for example by a hydrogen bond, an electrostatic bond or Van der Waals bonding, which is easily broken due to reaction with water, and thus the material is liable to separate from the hair surface.
- Japanese Patent Laid-open Publication No. 2004-182731 discloses a cosmetic containing a conditioning compound having a functional group that covalently bonds the conditioning compound of hair or skin surface.
- hair is activated using a separate material svch as chitosan or polyvinylalcohol and the conditioning compound having the functional group is applied to the activated hair, and accordingly, this prior art needs a step for activating hair in advance and a step for washing hair, and because the temperature of hair activation is high, for example 6O 0 C, has disadvantages of a complicated usage and difficult treatment conditions.
- Korean Patent Laid-open Publication No. 10-2006-0035343 discloses a semipermanent hair coating composition, in which a polyethylene glycol derivative as a conditioning compound is covalently bonded to cystine or amine of hair to coat the hair surface with a polymer layer, so that the entire thickness of hair is increased and a positive property of polymer is transmitted to hair. Therefore, hair is provided with a moisturizing effect of polyethylene glycol and has the increased thickness and improved volume through covalent bonds, however this prior art makes hair surface hydrophilic, similarly to property of damaged hair, consequently hair contains moisture more than necessary under humid weather conditions as in summer, and hair does not keep in shape and becomes damp. Further, this prior art can not obtain conditioning effects for hair or skin or fiber, for example damage repair or prevention, or silky, shiny or coating effect. Disclosure of Invention Technical Problem
- An object of the present invention is to provide a material which can continuously provide beneficial properties that may be obtained by a hydrophobic surface, for example damage repair and prevention, or silky, shiny or coating effect for hair or skin or a fiber, and a product comprising the material.
- the present invention provides a lipid having a functional group that is covalently bonded to protein of hair or skin surface.
- a lipid portion of the lipid having a functional group is a branched-chain lipid that has 8 to 28 carbon atoms and is an iso-fatty add or its derivative, or an anteiso-fatty add or its derivative.
- the branched-chain lipid is a methyleicosanoyl group, and the functional group is hydroxy surinimidyl ester or maleimide.
- the present invention provides a personal care product or a product for treating fiber/clothing, which comprises the lipid having a functional group.
- the present invention provides a lipid having a functional group that is covalently bonded to protein of hair or skin surface, and a personal care product for skin or hair or a fiber treatment product that comprises the lipid as a conditioning component.
- the present invention provides properties of health natural hair, and the effect is maintained by the functional group introduced to the lipid, preferably a branched-chain lipid.
- the present invention recovers hair surface damaged by exposure of protein residue to a natural hydrophobic hair surface by induing a reaction between the lipid having a functional group that is covalently bonded to protein residue, preferably a branched- chain lipid and the damaged hair surface, and covalently bonding the lipid to hair with great strength.
- the lipid having a functional group according to the present invention is bonded to hair components sirh as protein to reduce friction of the hair surface, so that it makes hair feeling soft when combing, and in addition to the damage repair effect, the lipid having a functional group according to the present invention provides beneficial properties obtained from a hydrophobic surface, for example silky, resilient, shiny or coating effect.
- a lipid portion of the lipid having a functional group according to the present invention may be ceramide, cholesterol, a fatty add having a carbon chain of 6 to 22 carbon atoms, a fatty alcohol having a carbon chain of 6 to 22 carbon atoms, a natural oil extracted from almond, castor, avocado, corn or olive, a natural wax such as beeswax or ppba oil, fatty esters sirh as glycol stearate, oxyethylenated or oxypropylenated waxes, alcohol-based fatty adds, phospholipid or 18-methyleicosanoic add.
- the lipid portion of the lipid having a functional group according to the present invention is a branched-chain lipid.
- the branched-chain lipid has a low melting point due to its branched chain, and thus provides a soft feeling when combing. Further, the branched-chain lipid is strongly bonded to hair protein, and thus, does not easily adhere to hands and has the continuity of effect in different way of other oily substances that provide an excessive oily feeling and have the reduced effect with time.
- the hair may become damp and may not keep in shape according to external environmental conditions, however the branched-chain lipid according to the present invention is bonded to hair surface to form a moisturizing layer, and thus allows hair to maintain a preferable moisture content irrespective of external environmental conditions.
- a double-chain fatty add has a low melting point, but is vulnerable to oxidation, thereby resulting in weak stability of a raw material, however the branched-chain fatty add according to the present invention has a low melting point and is not subject to oxidation of a raw material, thereby resulting in excellent stability of a raw material and stable produdbility. And, the branched-chain fatty add is not bonded to hair surface with high density due to its branched chain, thereby resulting in low crystallization. Therefore, the branched-chain fatty add serves as a lubricant on hair surface, thereby improving hair feeling when combing.
- the branched-chain lipid has 8 to 28 carbon atoms of a carbon backbone, and is an iso-fatty add or its derivative, or an anteiso-fatty add or its derivative to provide hair or skin surface with benefidal properties, and most preferably the branched-chain lipid is 18-methyleicosanoyl group or its derivative to provide benefidal properties, in particular, benefidal conditioning effects.
- the lipid having a functional group preferably a branched-chain lipid having a functional group reacts with the damaged surface of hair, in which protein residue is exposed by damage of an outermost layer due to chemical hair treatment sirh as perm or dying and washing, so that the damaged hair surface is recovered to healthy natural hair semi-permanently.
- the lipid has a functional group capable of covalent bonding to protein residue of hair surface. That is, as disclosed in Korean Patent Laid-open Publication No. 10-2006-0035343, protein of hair or skin has a reactive residue such as thiol, hydroxyl, carboxyl or amine, and the protein residue forms a covalent bond to the functional group of the conditioning component.
- the functional group of the conditioning component may be carbonate, aldehyde, propionaldehyde, butylaldehyde, nitrophenyl carbonate, aziridine, isocyanate, thiocyanate, epoxide, tresylate, sucinimide, hydroxysucinimidyl ester, imidazole, oxycarbonylamidazole, imine, thiol, maleimide, vinylsulfone, ethyleneimine, thioether, acrylonitrile, acrylic add or methacrylic ester, disulfide, ketone or a functional group represented as RX (R is any one selected from the group consisting of alkyl, aryl, aralkyl, a cycle and a unsaturated cycle, and X is I, Br or Cl).
- RX is any one selected from the group consisting of alkyl, aryl, aralkyl, a cycle and a unsaturated cycle, and X is I, Br or
- the functional group capable of covalent bonding to protein residue of hair surface is suxinimide, hydroxysurinimidyl ester, maleimide, vinylsulfone, aldehyde, isocyanate or epoxide in aspect of easiness and stability of reaction, and more preferably, hydroxysudnimidyl ester, maleimide or a mixture thereof.
- the present invention is a branched-chain lipid having maleimide or hydroxysudnimidyl ester as a functional group.
- maleimide reacts with a thiol group of keratine, the reaction occurs properly in an aqueous solution of about pH 6 to 7 and normal temperature, and finishes within 10 to 60 minutes.
- the reaction oxurs properly in an aqueous solution of normal temperature and pH 7 to 11, preferably pH 9 in consideration of the damage degree of hair, and finishes within 10 to 60 minutes, and thus maleimide or hydroxysudnimidyl ester is preferable for application to a personal care product.
- Synthesis of a branched-chain lipid having an activated hydroxysudnimidyl ester group as a functional group may be obtained by reacting a branched-chain fatty add having a carboxyl group, N-hydroxysurinimide (NHS) and carbodiimide, for example l-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) as a catalyst.
- NHS N-hydroxysurinimide
- EDC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide
- DCC dicyclohexyl carbodiimide
- Synthesis of a branched-chain lipid having maleimide may be obtained by reacting a branched-chain fatty amine having an amine group, maleic anhydride and ammonia, in other words, a branched-chain lipid having a terminal replaced by maleimide is otained.
- R is methyl or ethyl
- n is an integer from 5 to 19.
- the compound of the Chemistry Figure 1 is an anteiso fatty add having N- hydroxysudnimide ester group as a functional group.
- the compound of the Chemistry Figure 2 is an anteiso fatty acid having a maleimide group as a functional group.
- the compound of the Chemistry Figure 3 is an iso fatty add having N- hydroxysudnimide ester group as a functional group.
- the compound of the Chemistry Figure 4 is an iso fatty add having a maleimide group as a functional group.
- the conditioning component of the present invention that is bonded to hair or skin is not removed from hair or skin when general washing using shampoo, a detergent or soap, but is adhered to hair or skin permanently.
- a reactive personal care product for hair may further comprise a fatty add sirh as a palmitic add or a stearic add, fatty alcohol, a cataionic surfactant sirh as long-chain alkyl quaternary ammonium chloride of straight chain and branched chain, a cationic polymer such as cationic cellulose, cationic guar or cationic polyvinylpyrrolidone, or silicon, so that a hair repair effect can be improved.
- a fatty add sirh as a palmitic add or a stearic add
- fatty alcohol e.g., a cataionic surfactant sirh as long-chain alkyl quaternary ammonium chloride of straight chain and branched chain
- a cationic polymer such as cationic cellulose, cationic guar or cationic polyvinylpyrrolidone, or silicon
- the reactive personal care product for hair according to the present invention may further comprise a solvent, a surfactant, a thickening agent, a stabilizer, an antiseptic, a stain, a pH controller, a sequestering agent, a pearlescent agent, an appearance enhancer, a pigment or powdery particles.
- the reactive personal care product according to the present invention comprises a branched-chain lipid component having a functional group and may be applied to all personal care products.
- the personal care product may include all cosmetic products for hair and human body including a pre-shampoo product, shampoo, rinse treatment, wax, spray, mousse, hair lotion, essence, hair cream, permanent hair dye, temporary hair dye, and a perm solution.
- the present invention is based on a remarkable fact that a personal care product according to the present invention has a non-aqueous formulation.
- the reactive personal care product according to the present invention comprises a branched-chain lipid having a functional group, and the functional group may lose its active property in a non-aqueous solution. Therefore, it is preferable that the functional group maintains its active property in a non-aqueous formulation, and for pH control, the personal care product is mixed with a buffer solution immediately before use, and for reaction, the personal care product is contacted with water during washing.
- the non-aqueous formulation may be a typical non-aqueous cosmetic formulation including sheet-type, powder-type, dose-type, oil, wax, ample or gel.
- the reactive personal care product according to the present invention uses, as a solvent, dibasic add esters sirh as dioctyl succinate, dioctyl adipate or diethyl sebacate, polyol, polyethylene glycol, propylene glycol, hexylene glycol, butanediol and their isomers, glycerol, benzyl alcohol, or ethoxydiglycol and its derivative.
- dibasic add esters sirh as dioctyl succinate, dioctyl adipate or diethyl sebacate
- polyol polyethylene glycol, propylene glycol, hexylene glycol, butanediol and their isomers
- glycerol glycerol
- benzyl alcohol benzyl alcohol
- ethoxydiglycol and its derivative ethoxydiglycol and its derivative.
- the materials of the above Chemistry Figures 1 to 4 are soluble in dibasic acid esters, ethoxydiglycol and their derivatives, and although the materials are liquidized, an active property of the functional group is maintained, and when hair is treated with the materials, an inherently hydrophobic property of hair is increased double.
- the reactive personal care product according to the present invention uses diethyl sebacate, ethoxydiglycol or bis-ethoxydiglycol cyclohexane 1,4 dicarboxylate as a solvent.
- a lipid having a functional group according to the present invention preferably a branched-chain lipid having a functional group and a product comprising the same repair a bound lipid of hair or skin surface semi-permanently, and specially, recover the damaged surface to a surface having a hydrophobic property, similarly to property of healthy hair before damage.
- the present invention forms a soft coating layer on hair surface, which serves as a lubricant, using a branched-chain lipid, and thus can improve hair feeling when combing.
- the functional group of the lipid is covalently bonded to protein residue of hair surface, thereby providing hair with continuous and good hair repair effect.
- compositions of the examples 1 to 17 shown in Table 1 were prepared svch that
- compositions of the comparative examples 2 to 11 shown in Table 2 were prepared such that 10 weight% of powdery or liquid material was dissolved in 90 weight% of 50 mM phosphate buffered saline of pH 7 at 70 0 C, and the comparative example 1 used only 50 mM phosphate buffered saline of pH 7.
- the hair tress was heated at 50 0 C for 40 minutes, the weight of the hair tress was measured after 38 minutes, and a first moisture content was calculated using the measured weight as an indicator of an absorbed moisture amount of hair surface.
- the hair tress was heated at 180 0 C for 30 minutes, the weight of the hair tress was measured after 68 minutes, and a second moisture content was calculated using the measured weight as an indicator of a bound moisture amount in hair.
- First and second moisture ratios (%) were calculated using values of A, B and C through Math Figures 1 and 2, and the results were shown in Table 3. [54] Math Figure 1
- Second moisture ratiouj ⁇ .. . . ——r xlOO v Second initial weight B '
- compositions of the examples 1 to 17 oould provide higher moisturizing effect than the compositions of the comparative examples 1 to 11. This is because the comparative examples without covalent bonds are liable to removal of a moisturizing layer made of a lipid only, but the examples with induced covalent bonds are inclined to maintain a moisturizing layer of strong bond. And, it was found that as the length of a lipid is more similar to 18-MEA, the moisturizing effect is higher.
- the hair tress was cut into pieces of lcm length, and a moisture content of 500mg of the cut hair tress was measured using a moisture analyzer of HR83-P model made by METLLER.
- the hair tress was heated at 50 0 C for 40 minutes, the weight of the hair tress was measured after 38 minutes, and a first moisture content was calculated using the measured weight as an indicator of an absorbed moisture amount of hair surface.
- the hair tress was heated at 180 0 C for 30 minutes, the weight of the hair tress was measured after 68 minutes, and a second moisture content was calculated using the measured weight as an indicator of a bound moisture amount in hair.
- First and second moisture ratios (%) after 7-time shampooing were calculated using values of A, B and C through Math Figures 1 and 2, and the results were shown in Table 4. [61] Table 4 [Table 4] [Table ]
- the compositions of the examples 1 to 17 could provide higher moisturizing effect than the compositions of the comparative examples 1 to 11. This is because the comparative examples without covalent bonds are liable to removal of a moisturizing layer made of only a lipid through 7 -time shampooing, but the examples with induced covalent bonds are inclined to maintain a moisturizing layer of strong bond. And, it was found that as the length of a lipid is more similar to 18-MEA, the moisturizing effect is higher in the same way of Table 3.
- the hair tress was treated with the compositions of the examples and comparative examples 5 times and shampooed 5 times, and a panel of 30 men and 30 women of twenties to forties evaluated a hair repair effect of the hair tress every shampooing.
- the hair repair effect was evaluated according to the following evaluation item and effect evaluation standard, and the results were shown in Table 6.
- Evaluation item easiness of combing and hair repair in a dry state according to the number of shampooing. [71] Effect evaluation standard: very bad (1-2), bad (3-4), normal (5-6), good (7-8), very good (9-10) [72] Table 6
- the examples 'd' and 'e' showed that diethyl sebacate and bis- ethoxydiglycol cyclohexane 1,4 dicarboxylate as preferable solvents according to the present specification provide better effect to hair than 1,3-BG and glycerine, and the examples T to V showed that N-hydroxysucinimidyl ester or maleimide provides larger hair repair effect than other functional groups.
- a fatty acid of straight chain or branched chain or a cationic lipid used in the comparative examples 'a' to 'e' has excellent hair repair at the initial use, but is liable to removal by reaction with water and a surfactant when shampooing, and thus as the number of shampooing increases, the hair repair effect is not maintained, but is remarkably reduced.
- a normal hair before damage has a contact angle of about 110° and exhibits a hydrophobic property, however hair damaged by dyeing or perm has a low contact angle of 60°or less and exhibits a hydrophilic property. Therefore, a contact angle of hair may be an indicator for determining hair repair effect.
- the comparative examples 'b', 'c' and 'e' without functional groups are liable to separate from hair surface than the examples 'a' to 'c' comprising a lipid having a functional group, and thus provide lower hair repair effect immediately after treatment and continuity of hair repair effect.
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Abstract
La présente invention concerne un lipide présentant un groupe fonctionnel et un produit pour soins personnels comprenant ledit lipide. Plus spécifiquement, le produit pour soins personnels selon la présente invention comprend un lipide présentant un groupe fonctionnel qui est lié de manière covalente à un résidu protéique de la peau ou des cheveux. Le lipide rend la partie endommagée des cheveux hydrophobe de manière semi-permanente, c.-à-d. qu'il forme une couche lipidique liée de manière covalente sur une couche extérieure des cheveux afin de faire retrouver à la partie endommagée des cheveux un état de cheveux sains avant endommagement. Par conséquent, la présente invention permet d'obtenir des cheveux présentant des effets brillants, hydratants, soyeux et doux.
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KR10-2007-0060456 | 2007-06-20 | ||
KR1020070060456A KR100932800B1 (ko) | 2007-06-20 | 2007-06-20 | 특정 관능기를 갖는 지질을 포함하는 반응성 퍼스널 케어조성물 |
KR10-2008-0015434 | 2008-02-20 | ||
KR20080015434A KR101490465B1 (ko) | 2008-02-20 | 2008-02-20 | 피부 또는 모발의 단백질과 결합하는 반응성 분기쇄의 지질화합물과 이를 포함하는 반응성 퍼스널 케어 제품 |
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WO2012004419A2 (fr) | 2010-07-09 | 2012-01-12 | Université De Bretagne Occidentale | Construction modulaire de lipophospholipides |
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WO2017029336A1 (fr) * | 2015-08-17 | 2017-02-23 | L'oreal | Procédé de traitement de fibres de kératine avec un polymère d'alcoxysilane portant un groupe nucléophile et un (thio)ester activé |
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WO2018059788A1 (fr) * | 2016-09-30 | 2018-04-05 | Henkel Ag & Co. Kgaa | Agents de traitement capillaire à effet conditionnant amélioré et résistants au lavage |
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