CN117586143A - Polyether amide, preparation method thereof and application thereof in hair injury repair - Google Patents
Polyether amide, preparation method thereof and application thereof in hair injury repair Download PDFInfo
- Publication number
- CN117586143A CN117586143A CN202410070607.0A CN202410070607A CN117586143A CN 117586143 A CN117586143 A CN 117586143A CN 202410070607 A CN202410070607 A CN 202410070607A CN 117586143 A CN117586143 A CN 117586143A
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- CN
- China
- Prior art keywords
- hair
- salt
- stereoisomer
- polyether amide
- repairing
- 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.)
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- 229920002614 Polyether block amide Polymers 0.000 title claims abstract description 70
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 230000008439 repair process Effects 0.000 title claims abstract description 28
- 230000006378 damage Effects 0.000 title abstract description 16
- 208000027418 Wounds and injury Diseases 0.000 title abstract description 5
- 208000014674 injury Diseases 0.000 title abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 23
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 15
- 229920000570 polyether Polymers 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 46
- 239000002453 shampoo Substances 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 159000000000 sodium salts Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 23
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 238000005342 ion exchange Methods 0.000 abstract description 4
- 230000002045 lasting effect Effects 0.000 abstract description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 74
- 230000000052 comparative effect Effects 0.000 description 38
- 238000003756 stirring Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- 239000002994 raw material Substances 0.000 description 19
- 238000004949 mass spectrometry Methods 0.000 description 18
- 239000007787 solid Substances 0.000 description 15
- -1 but not limited to Chemical class 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 9
- 239000011976 maleic acid Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 7
- 229910001948 sodium oxide Inorganic materials 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 238000011010 flushing procedure Methods 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 230000003472 neutralizing effect Effects 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000007844 bleaching agent Substances 0.000 description 4
- 230000003766 combability Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920002545 silicone oil Polymers 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 2
- BQJLEQAXRYBKPQ-UHFFFAOYSA-N 2-amino-2-methylpropane-1,1-diol Chemical compound CC(C)(N)C(O)O BQJLEQAXRYBKPQ-UHFFFAOYSA-N 0.000 description 2
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 2
- 239000004475 Arginine Substances 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 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 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002385 Sodium hyaluronate Polymers 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000004985 diamines Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 230000003700 hair damage Effects 0.000 description 2
- 230000003699 hair surface Effects 0.000 description 2
- 239000013003 healing agent Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 150000007529 inorganic bases Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 229940044591 methyl glucose dioleate Drugs 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052913 potassium silicate Inorganic materials 0.000 description 2
- 235000019353 potassium silicate Nutrition 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 2
- 229940010747 sodium hyaluronate Drugs 0.000 description 2
- 235000019795 sodium metasilicate Nutrition 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000002888 zwitterionic surfactant Substances 0.000 description 2
- BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical group NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- FECNOIODIVNEKI-UHFFFAOYSA-N 2-[(2-aminobenzoyl)amino]benzoic acid Chemical class NC1=CC=CC=C1C(=O)NC1=CC=CC=C1C(O)=O FECNOIODIVNEKI-UHFFFAOYSA-N 0.000 description 1
- MQFYRUGXOJAUQK-UHFFFAOYSA-N 2-[2-[2-(2-octadecanoyloxyethoxy)ethoxy]ethoxy]ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCOCCOCCOC(=O)CCCCCCCCCCCCCCCCC MQFYRUGXOJAUQK-UHFFFAOYSA-N 0.000 description 1
- TWMBOHVOMWFMJI-UHFFFAOYSA-N 2-hydroxyethyl phosphono hydrogen phosphate Chemical compound OCCOP(O)(=O)OP(O)(O)=O TWMBOHVOMWFMJI-UHFFFAOYSA-N 0.000 description 1
- CLAHOZSYMRNIPY-UHFFFAOYSA-N 2-hydroxyethylurea Chemical compound NC(=O)NCCO CLAHOZSYMRNIPY-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- 229940099451 3-iodo-2-propynylbutylcarbamate Drugs 0.000 description 1
- WYVVKGNFXHOCQV-UHFFFAOYSA-N 3-iodoprop-2-yn-1-yl butylcarbamate Chemical compound CCCCNC(=O)OCC#CI WYVVKGNFXHOCQV-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
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- RTIXKCRFFJGDFG-UHFFFAOYSA-N Chrysin Natural products C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 RTIXKCRFFJGDFG-UHFFFAOYSA-N 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
- 239000011703 D-panthenol Substances 0.000 description 1
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 1
- 235000004866 D-panthenol Nutrition 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
- FPVVYTCTZKCSOJ-UHFFFAOYSA-N Ethylene glycol distearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCCCCCCCC FPVVYTCTZKCSOJ-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
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- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- 241000772415 Neovison vison Species 0.000 description 1
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- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- JUIUXBHZFNHITF-IEOSBIPESA-N [(2r)-2,5,7,8-tetramethyl-2-[(4r,8r)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-yl] dihydrogen phosphate Chemical compound OP(=O)(O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C JUIUXBHZFNHITF-IEOSBIPESA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- ZZTCCAPMZLDHFM-UHFFFAOYSA-N ammonium thioglycolate Chemical compound [NH4+].[O-]C(=O)CS ZZTCCAPMZLDHFM-UHFFFAOYSA-N 0.000 description 1
- 229940075861 ammonium thioglycolate Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- YSJGOMATDFSEED-UHFFFAOYSA-M behentrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C YSJGOMATDFSEED-UHFFFAOYSA-M 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- 229940082500 cetostearyl alcohol Drugs 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000012650 click reaction Methods 0.000 description 1
- MRUAUOIMASANKQ-UHFFFAOYSA-N cocamidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](C)(C)CC([O-])=O MRUAUOIMASANKQ-UHFFFAOYSA-N 0.000 description 1
- 229940073507 cocamidopropyl betaine Drugs 0.000 description 1
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- 230000003750 conditioning effect Effects 0.000 description 1
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- 229960003949 dexpanthenol Drugs 0.000 description 1
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
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- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229940100608 glycol distearate Drugs 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940031575 hydroxyethyl urea Drugs 0.000 description 1
- 230000003752 improving hair Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- AIHDCSAXVMAMJH-GFBKWZILSA-N levan Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)OC[C@@H]1[C@@H](O)[C@H](O)[C@](CO)(CO[C@@H]2[C@H]([C@H](O)[C@@](O)(CO)O2)O)O1 AIHDCSAXVMAMJH-GFBKWZILSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical group NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- URFCJEUYXNAHFI-ZDUSSCGKSA-N pinocembrin Chemical compound C1([C@@H]2CC(=O)C3=C(O)C=C(C=C3O2)O)=CC=CC=C1 URFCJEUYXNAHFI-ZDUSSCGKSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940045885 sodium lauroyl sarcosinate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940048109 sodium methyl cocoyl taurate Drugs 0.000 description 1
- 229940045920 sodium pyrrolidone carboxylate Drugs 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- HYRLWUFWDYFEES-UHFFFAOYSA-M sodium;2-oxopyrrolidine-1-carboxylate Chemical compound [Na+].[O-]C(=O)N1CCCC1=O HYRLWUFWDYFEES-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to polyether amide, a preparation method thereof and application thereof in hair injury repair. The polyether amide has a structure shown in a formula (1), wherein A is a residue of polyether amine after removing amino, and p is more than or equal to 2. The invention provides a poly (ethylene)The etheramide or the stereoisomer or the salt thereof can be used as a repairing agent for repairing damaged hair, can enhance the glossiness, strength and flexibility of the hair, can effectively repair hair scales, and has good lasting repairing and nourishing effects on the damaged hair. In addition, the amide group formed by covalent bonding of the amino group in the polyetheramine and the maleic anhydride through reaction is very stable, the phenomenon of ion exchange can not occur in water and in the repairing process, the structural stability is good, and the repairing agent has better repairing effect than the repairing agent bonded by ionic bonds when being used for repairing damaged hair.
Description
Technical Field
The invention belongs to the technical field of daily chemical products, and particularly relates to polyether amide, a preparation method thereof and application thereof in hair injury repair.
Background
The hair is a fiber material which takes keratin as a main component and contains lipid, moisture, melanin and the like, and a plurality of chemical bonds such as peptide bonds, disulfide bonds, ionic bonds and the like and non-bonding acting forces such as Van der Waals force exist in the hair, and the factors directly determine a series of performances of the hair. Hair may be damaged in various ways, such as exposure to sunlight for a long period of time, exposure to ultraviolet radiation and heat, causing the hair to become dry and frizzy; excessive cleaning, the heat of the blower and forced hair combing cause the hair to become fragile; frequent permanent waving and dyeing causes damage to the hair.
The hair dyeing process is a process of blocking pigment deposits between hair fibers by breaking disulfide bonds of hair, allowing colored substances formed by polymerization of dye intermediates to deposit on the hair surface, and reconnecting disulfide bonds by oxidation. Because the reaction is carried out in a disordered environment and the reaction time is limited, a large amount of deposited pigment is not fixed by proper and enough disulfide bonds, so that the firmness of dyeing is not effectively ensured for a long time. Usually, after hair dyeing for several months and daily hair washing and other processes, the color of hair is lost in a large amount, frequent re-dyeing and scalding are needed, and great trouble is brought to consumers. Repeated dyeing and ironing can cause that disulfide bonds of hair are damaged in a larger range and cannot be recovered, hair is also more fragile and rough, and the problems of hair friability, dryness, even broken hair and the like are brought to consumers.
Patent CN105431128A discloses a method for repairing hair, the method comprising: a formulation comprising an effective amount of a binding agent covalently bonded to free sulfhydryl groups is applied to hair to repair the hair. The binding agent is formed by bonding a connector and a reactive part in an ionic mode, wherein the connector is an amino substituted alkoxy with 1 to 10 carbon atoms, and the reactive part reacts with a free sulfhydryl group to form a C-S covalent bond, so that hair restoration is realized.
Disclosure of Invention
Based on this, it is an object of the present invention to provide a new restoration agent for restoring damaged hair and a restoration method.
In order to achieve the above object, the present invention includes the following technical solutions.
In a first aspect, the present invention provides a polyether amide having a structure represented by formula (1):
；
(1)
Wherein A is the residue of polyetheramine after removing amino group, and p is more than or equal to 2.
In a second aspect, the invention provides a preparation method of the polyether amide, which comprises the following steps: polyether amine and maleic anhydride react to obtain the product. Wherein the structure of the polyetheramine corresponds to the polyetheramine moiety in the polyetheramide.
In a third aspect, the present invention provides the use of said polyetheramide or a stereoisomer or a salt thereof as an active ingredient in the preparation of a restorative agent for restoration of damaged hair.
In a fourth aspect, the present invention provides a restoration agent for restoring damaged hair, the active ingredient of which comprises the polyether amide or a stereoisomer or a salt thereof according to the present invention.
In a fifth aspect, the present invention provides a method for preparing a restoration agent for restoring damaged hair, comprising the steps of: polyether amine reacts with maleic anhydride, the pH value of the obtained reaction mixture or reaction product is regulated, and water is added for dilution to the specified concentration, thus obtaining the catalyst.
In a sixth aspect, the present invention provides the use of said polyetheramide or a stereoisomer or a salt thereof, or of said restorative agent of the invention as an active ingredient in the preparation of a restorative product for restoration of damaged hair.
In a seventh aspect, the present invention provides a shampoo or conditioner for repairing damaged hair, the active ingredient of which comprises the polyether amide or stereoisomer or salt thereof according to the present invention, or the active ingredient of which comprises the repairing agent according to the present invention.
In an eighth aspect, the present invention provides a method of repairing damaged hair, comprising the steps of: the repairing agent or the shampoo or the conditioner disclosed by the invention is coated on the surface of damaged hair to repair the damaged hair.
The polyether amide or the stereoisomer or the salt thereof with the structure shown in the formula (1) provided by the invention has the advantages that the double bond of the maleic amide group part and free sulfhydryl in damaged hair can perform click reaction, and broken disulfide bonds in the damaged hair can be bridged to form a multi-bridged stable structure, so that the effect of repairing the damaged hair can be achieved, the glossiness, the strength and the flexibility of the hair can be enhanced, the hair scales can be effectively repaired, and the hair repairing agent has good lasting repairing and nourishing effects on the damaged hair. In addition, the amide group formed by covalent bonding of the amino group in the polyetheramine and the maleic anhydride through reaction is very stable, the phenomenon of ion exchange can not occur in water and in the repairing process, the structural stability is good, and the repairing agent has better repairing effect than the repairing agent bonded by ionic bonds when being used for repairing damaged hair.
Drawings
Fig. 1 is a scanning electron microscope contrast chart of hair damaged by hydrogen peroxide after treatment with hair conditioner sample No. 4 (example 6), no. 2 (comparative example 5) and blank treatment, respectively.
Detailed Description
The present invention will be described more fully hereinafter in order to facilitate an understanding of the present invention. This invention may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
The experimental procedures, which do not address the specific conditions in the examples below, are generally carried out under conventional conditions or under conditions recommended by the manufacturer. The various chemicals commonly used in the examples are commercially available.
Unless otherwise defined, all technical and scientific terms used herein and belonging to the same
The meaning is generally understood by those skilled in the art. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
Furthermore, as used herein, the term "or" is an inclusive "or" symbol and is equivalent to the term "and/or" unless the context clearly dictates otherwise. The term "based on" is not exclusive and allows for being based on other factors not described, unless the context clearly dictates otherwise. Furthermore, throughout the specification, the meaning of "a", "an", and "the" include plural referents. The meaning of "in" is included "in" and "on".
In the compounds of the present invention, when any variable (e.g., R, etc.) occurs more than once in any component, the definition of each occurrence is independent of the definition of each other occurrence. For example, the number of the cells to be processed,there are n+1R in this structure, and these n+1R may be the same or different. In the present invention, "in chemical group or chemical structure">"represents a bond attachment location.
In one embodiment of the present invention, there is provided a polyether amide having a structure represented by formula (1):
；
(1)
Wherein A is the residue of polyetheramine after removing amino group, and p is more than or equal to 2.
Of the compounds represented by the formula (1),the direction of the single bond is not fixed, and the single bond may form a cis structure or a trans structure. That is, the maleimide group will be partially converted to fumaramide groups in aqueous solution, that is, the carbon-carbon double bond linked substituent may exist as a cis-trans isomer in aqueous solution, and thus, the polyether amide may be in cis-configuration, or trans-configuration, or a mixture of cis-trans isomers thereof.
Polyether amide with a structure shown in formula (1) or stereoisomer or salt thereof, wherein double bonds of a maleimido part of the polyether amide can bridge broken disulfide bonds in damaged hair, so that the effect of repairing the damaged hair can be achieved, glossiness, strength and flexibility of the hair can be enhanced, hair scales can be effectively repaired, and the polyether amide has good repairing and nourishing effects on the damaged hair. In addition, the amide group formed by covalent bonding of the amino group in the polyetheramine and the maleic anhydride through reaction is very stable, the phenomenon of ion exchange can not occur in water and in the repairing process, the structural stability is good, and the repairing agent has better repairing effect than the repairing agent bonded by ionic bonds when being used for repairing damaged hair.
In some embodiments, p is selected from: 2. 3, 4.
In some embodiments, a is selected from:
、
wherein each R is independently selected from: hydrogen, methyl, ethyl;
R 1 selected from: hydrogen, methyl, ethyl, propyl,；
n=1-150, n1=1-10, n2=1-10, n3=1-10, n4=1-10, each m is independently 1 or 2.
When A isIn the case of this polyether amide, the multi-arm structure of the "three-arm" or "four-arm" is more effective in repairing damaged hair than the "two-arm" structure.
In some of these embodiments, n=1 to 50, preferably 1 to 40, preferably 1 to 30, preferably 1 to 25, preferably 1 to 18.
In some of these embodiments, n1=1-5, n2=1-5, n3=1-5, n4=1-5.
In some of these embodiments, n1+n2+n3=5-6, n4=1-2.
In some of these embodiments, R 1 Selected from: hydrogen, methyl, ethyl, propyl,Wherein R is selected from: hydrogen, methyl, ethyl; n4=1-2, m is 1 or 2.
In some embodiments, the polyether amide has a structural formula as shown in formula (2):
；
(2)
Wherein each m is independently 1 or 2, n=1-18, preferably 1, 2, 3, 4 or 5.
In some of these embodiments, the polyether amide has a structural formula as shown in formula (3):
；
(3)
Wherein each m is independently 1 or 2, x1=0-20, x2=0-20, x3=0-20, and x1, x2, and x3 are not simultaneously 0; each R is independently selected from: hydrogen, methyl, ethyl.
In some of these embodiments, x1=0-8, x2=0-20, x3=0-8 in formula (3), and x1, x2, and x3 are not simultaneously 0.
In some of these embodiments, x1+x3=0.2-6, x2=0-15 in formula (3).
In some embodiments, each R in formula (3) is independently selected from: methyl, ethyl.
In some embodiments, the polyether amide has a structural formula as shown in formula (4):
；
(4)
Wherein each R is independently selected from: hydrogen, methyl, ethyl;
R 1 selected from: hydrogen, methyl, ethyl, propyl;
n1=1-10，n2=1-10，n3=1-10。
in some of these embodiments, n1+n2+n3=5-6 in formula (4).
In some embodiments, each R in formula (4) is independently selected from: hydrogen, methyl; r is R 1 Selected from: hydrogen, methyl, ethyl.
In some of these embodiments, the polyetheramide is selected from:
，，
wherein i1+i2+i3=5-6,
，
wherein x2=9.0, x1+x3=2.6; or x1=1-2, x2=x3=0; or x2=0, x1+x3=5.1; or x2=2.0, x1+x3=0.2; or x2=12.5, x1+x3=5.0.
In some of these embodiments, the polyether amide salt is a sodium salt, potassium salt, ammonium salt.
In another embodiment of the present invention, there is also provided a method for preparing the polyether amide, comprising the steps of: polyether amine and maleic anhydride react to obtain the product. Wherein the structure of the polyetheramine corresponds to the polyetheramine moiety in the polyetheramide.
Wherein the reaction molar ratio of the polyetheramine and the maleic anhydride is dependent on the number of amino groups in the polyetheramine. For example, when the polyetheramine is diamine, the theoretical molar ratio of polyetheramine to maleic anhydride is 1:2, and the person skilled in the art can properly adjust the molar ratio according to the actual situation, so as to make the polyetheramine react completely.
Among them, the solvent for the reaction is selected from commonly used carboxylic acids, alcohols, ketones, ethers, water, etc., preferably acetic acid or water. The amount of the solvent to be used is preferably 1 to 5 times the mass sum of the polyether amine and maleic anhydride, and is not particularly limited.
When acetic acid is used as a solvent, maleic anhydride is dissolved in acetic acid under stirring, ice water bath is cooled to 15-20 ℃, polyether amine is dripped at 15-20 ℃, then the reaction is carried out for 2-6 hours at normal temperature, solid is collected by filtration, and is washed twice by methyl tertiary butyl ether, and polyether amide is obtained by drying.
When water is selected as a solvent, polyether amine is dissolved in water under stirring, then maleic anhydride is added in batches, and the reaction is carried out for 1 to 10 hours at normal temperature, thus obtaining polyether amide.
In some of these embodiments, the polyetheramine is selected from: EDR-148, ED-600, T-403, CAD-230, MA-240, EDR-176, HK-511, ED-900.
In another embodiment of the present invention, there is also provided the use of said polyetheramide or a stereoisomer or a salt thereof as an active ingredient in the preparation of a restorative agent for restoration of damaged hair.
In another embodiment of the present invention, there is also provided a restoration agent for restoring damaged hair, the active ingredient of which comprises the polyether amide or a stereoisomer thereof or a salt thereof according to the present invention. The repairing agent is applied to damaged hair, can enhance the glossiness and strength of the hair, improve the smoothness of comb and has good repairing effect on damaged hair.
In some of these embodiments, the polyether amide or stereoisomer or salt thereof is added to the repair agent in an amount of from 0.2mmol/g to 5mmol/g, preferably from 0.5mmol/g to 3mmol/g, and from 0.8mmol/g to 2mmol/g, based on the molar concentration of amide groups.
In some embodiments, the agent for repairing damaged hair further comprises an alkaline neutralizing agent.
Specifically, the alkaline neutralizer is selected from inorganic bases including, but not limited to, any one or a combination of at least two of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium metasilicate and potassium metasilicate, and/or organic bases including, but not limited to, any one or a combination of at least two of ethanolamine, arginine, lysine, sodium citrate, N-ethylethanolamine, triethanolamine, diethylaminoethanol, and 2-amino-2-methylpropanediol. These basic neutralizing agents may react with the polyetheramide in the healing agent to form the corresponding salts.
In some of these embodiments, the pH of the restorative agent for repairing damaged hair is 3-9, preferably 4-8, more preferably 4.5-7, still more preferably 5-6.
In another embodiment of the present invention, there is also provided a method for preparing a restoration agent for restoring damaged hair, comprising the steps of: polyether amine reacts with maleic anhydride, the pH value of the obtained reaction mixture or reaction product is regulated, and water is added for dilution to the specified concentration, thus obtaining the catalyst.
In some of these embodiments, the pH of the resulting reaction mixture or reaction product is adjusted with an alkaline neutralizing agent. Specifically, the alkaline neutralizer is selected from inorganic bases including, but not limited to, any one or a combination of at least two of sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide, sodium metasilicate and potassium metasilicate, and/or organic bases including, but not limited to, any one or a combination of at least two of ethanolamine, arginine, lysine, sodium citrate, N-ethylethanolamine, triethanolamine, diethylaminoethanol, and 2-amino-2-methylpropanediol. These basic neutralizing agents can react with polyetheramides in the healing agent to form the corresponding salts.
Wherein the reaction molar ratio of the polyetheramine and the maleic anhydride is dependent on the number of amino groups in the polyetheramine. For example, when the polyetheramine is diamine, the theoretical molar ratio of polyetheramine to maleic anhydride is 1:2, and the person skilled in the art can properly adjust the molar ratio according to the actual situation, so as to make the polyetheramine react completely.
Among them, the solvent for the reaction is selected from commonly used carboxylic acids, alcohols, ketones, ethers, water, etc., preferably acetic acid or water. The amount of the solvent to be used is preferably 1 to 5 times the mass sum of the polyether amine and maleic anhydride, and is not particularly limited.
When acetic acid is used as a solvent, maleic anhydride is dissolved in acetic acid under stirring, ice water bath is cooled to 15-20 ℃, polyether amine is dripped at 15-20 ℃, then normal temperature reaction is carried out for 2-6 hours, solid is collected through filtration and washed twice with methyl tertiary butyl ether, polyether amide products are obtained after drying, the products are dispersed in water, pH is regulated to 3-9 (preferably 4-8, more preferably 4.5-7, still more preferably 5-6) by using an alkaline neutralizer, and the products are diluted to a specified concentration by using water, thus obtaining the repairing agent.
When water is selected as a solvent, polyether amine is dissolved in water under stirring, then maleic anhydride is added in batches and reacts for 1-10 hours at normal temperature to obtain a dispersion liquid containing solid (polyether amide), the pH of the dispersion liquid is adjusted to 3-9 (preferably 4-8, more preferably 4.5-7, still more preferably 5-6) by an alkaline neutralizing agent to obtain a clear solution, and the clear solution is diluted to a specified concentration by water to obtain the repairing agent.
In another embodiment of the invention, there is also provided the use of the polyether amide of the invention or a stereoisomer or a salt thereof, or the restorative of the invention as an active ingredient in the preparation of a repair product for repairing damaged hair. The repair products of the present invention include, but are not limited to, aqueous, cream, emulsion, oily, solid or semi-solid products having shampoo and/or hair care benefits, including, but not limited to, shampoos and conditioners.
In another embodiment of the present invention, there is also provided a shampoo or conditioner for repairing damaged hair, the active ingredient of which comprises the polyether amide or a stereoisomer or a salt thereof according to the present invention, or the active ingredient of which comprises the repairing agent according to the present invention.
In some embodiments, the restoration agent is added to the restoration product, such as a shampoo or conditioner, in an amount of 0.1wt% to 50wt%, preferably 0.5wt% to 25wt%, more preferably 1.0wt% to 20wt%, even more preferably 1.0wt% to 10wt%, even more preferably 5.0wt% to 10wt%, and even more preferably 7.0wt% to 9.0wt%.
The repair product, such as shampoo or conditioner, may further comprise any one or at least two of moisturizer, anionic surfactant, zwitterionic surfactant, nonionic surfactant, chelating agent, ester forming agent, preservative, thickener, conditioner and perfume.
Specifically, the humectant is at least one selected from propylene glycol, glycerol, butanediol, dipropylene glycol, sorbitol, polyethylene glycol, D-panthenol, sodium hyaluronate, sodium pyrrolidone carboxylate, lactic acid, sodium lactate, and betaine.
Specifically, the anionic surfactant is selected from any one or at least two of sodium laureth sulfate, sodium laurylsulfate, sodium lauroyl sarcosinate, cocoyl glutamic acid TEA salt and sodium methyl cocoyl taurate.
Specifically, the zwitterionic surfactant is selected from any one or at least two of cocamidopropyl betaine, cocamidopropyl hydroxysulfobetaine and sodium cocoyl amphoacetate.
Specifically, the nonionic surfactant is selected from any one or at least two of Tween 20, tween 28, cocamide DEA, cocamide MEA, alkyl glycoside and cocamide methyl MEA.
Specifically, the chelating agent is selected from any one or at least two of hydroxyethyldiphosphate, EDTA-2Na and EDTA-4 Na.
Specifically, the ester forming agent comprises any one or at least two of glycol distearate, PEG-120 methyl glucose dioleate, PEG-150 distearate, PEG-7 glycerol cocoate, PPG-3 octyl ether, polydimethylsiloxane and mink oil.
Specifically, the preservative includes, but is not limited to, any one or at least two selected from the group consisting of pinocembrin, DMDMH, parabens, phenoxyethanol, sodium benzoate, potassium sorbate, iodopropynyl butylcarbamate.
Specifically, the thickener is selected from any one or at least two of sodium chloride, cetostearyl alcohol, 250HHR (hydroxyethyl cellulose), cocoamide MEA, PEG-120 methyl glucose dioleate, polyacrylic copolymer and polyacrylate copolymer.
Specifically, conditioning agents include, but are not limited to, any one or at least two of squalane, hydroxyethyl urea, cationic guar gum, polyquaternary ammonium salts, behenyl trimethyl ammonium chloride, polydimethylsiloxane, bis-aminopropyl polydimethylsiloxane, ceramide, jojoba oil, levan, sodium hyaluronate, sodium tocopheryl phosphate.
Specifically, the flavoring agent is essence or natural aromatic essential oil.
In another embodiment of the present invention, there is also provided a method for repairing damaged hair, comprising the steps of: the shampoo or the hair conditioner disclosed by the invention is smeared on the surface of damaged hair for restoration.
The dosage of the shampoo or the conditioner applied to the surface of the damaged hair can be determined according to the damage degree of the hair, and generally, 0.1-1g of the shampoo or the conditioner can be used for each gram of hair; the application time of the restoration agent, shampoo or conditioner applied to the damaged hair surface can be determined according to the damaged degree of hair, and can be generally 1-30min.
The present invention will be described in further detail with reference to specific examples.
Example 1
The preparation method of the repairing agent of the embodiment is as follows:
EDR-148 (44.4 g,0.3 mol) (molecular weight 148, from Yu Hengsi man) was dissolved in 150g of water with stirring, then maleic anhydride (58.8 g,0.6 mol) was added, and reacted at ordinary temperature for 1.5 hours with stirring to obtain a dispersion containing solids, the pH of the dispersion was adjusted to 6 with 40% sodium hydroxide solution to obtain a clear solution, and diluted with water to 300g to obtain sample CG1 having a mass molar concentration of active groups of 2mmol/g.
The clear solution was taken for mass spectrometry and the product LC-MS main peak ESI (+): 345.23.
mass spectrometry analysis is carried out on raw material amine EDR-148, and main peak ESI (+) of raw material LC-Ms is carried out: 149.23.
the molecular weight difference 196 between the product and the starting material, from which it is known that the polyether amide contained in sample CG1 is mainly a diacylated product, having the following structural formula:
example 2
The preparation method of the repairing agent of the embodiment is as follows:
58.8g of maleic anhydride (0.6 mol) were dissolved in 200g of acetic acid with stirring, cooled to 15-20℃in an ice-water bath, EDR-148 (44.4 g,0.3 mol) (molecular weight 148, from Yu Hengsi Man) was added dropwise at 15-20℃and then reacted at room temperature for 4 hours, the solid was collected by filtration and washed twice with methyl tert-butyl ether, and dried to give about 100g of a product. The product (68.8 g,0.2 mol) was dispersed in 100ml of water, pH was adjusted to 6 with 40% sodium hydroxide solution, and diluted with water to 200g to give sample CG2 having a molar concentration of active groups of 2mmol/g.
Solid body 1 H-NMR（400MHz，DMSO-d6）δ 14.86（bs，2H），9.15（s，2H），6.46-6.25（dd，4H），3.58（s，4H），3.53-3.50（t，4H），3.38-3.34（m，4H）。
The obtained solid was taken for mass spectrometry, and the product LC-MS main peak ESI (+): 345.23.
mass spectrometry analysis is carried out on raw material amine EDR-148, and main peak ESI (+) of raw material LC-Ms is carried out: 149.23.
the molecular weight difference 196 between the product and the starting material, from which it is known that the polyether amide contained in sample CG2 is mainly a diacylated product, having the following structural formula:
example 3
The preparation method of the repairing agent of the embodiment is as follows:
ED-600 (120 g,0.2 mol) (molecular weight 600, available from Yu Hengsi M) was dissolved in 200g of water with stirring, then maleic anhydride (39.2 g,0.4 mol) was added, and reacted at ordinary temperature with stirring for 2 hours to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 5 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 400g to obtain sample CG3 having a molar concentration of active groups of 1mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 681.25, 739.38, 783.32, 841.33, 885.28, 943.33, 988.32.
Taking raw material amine ED-600 for mass spectrometry, and carrying out main peak ESI (+) (LC-Ms) of the raw material: 485.25, 543.38, 587.32, 645.33, 689.28, 747.33, 792.32.
The molecular weight difference 196 between the product and the starting material, from which it is known that the polyether amide contained in sample CG3 is mainly a diacylated product, having the following structural formula:
Wherein x2=9.0, x1+x3=2.6.
Example 4
The preparation method of the repairing agent of the embodiment is as follows:
t-403 (87.9 g,0.2 mol) (molecular weight 440, from Yu Hengsi M) was dissolved in 100g of water with stirring, then maleic anhydride (58.8 g,0.6 mol) was added, and the mixture was reacted at ordinary temperature with stirring for 3 hours to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 5 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 300g to obtain sample CG4 having a mass molar concentration of active groups of 2mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 716.28, 774.30, 832.35, 890.42, 948.30, 1006.39, 1064.50.
Taking raw material amine T-403 for mass spectrometry, and carrying out main peak ESI (+)'s of raw material LC-Ms: 422.28, 480.30, 538.35, 596.42, 654.30, 712.39, 770.50.
The molecular weight difference 294 between the product and the starting material, from which it is seen that the polyether amide contained in sample CG4 is mainly a triacylated product, having the following structural formula:
wherein i1+i2+i3=5-6.
Example 5
The preparation method of the repairing agent of the embodiment is as follows:
CAD-230 (69 g,0.3 mol) (molecular weight 230, available from Chemie, yangzhou) was dissolved in 150g of water with stirring, then 58.8g of maleic anhydride (58.8 g,0.6 mol) was added thereto, and reacted at ordinary temperature with stirring for 2 hours to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 6 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 300g to obtain sample CG5 having a mass molar concentration of active groups of 2mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 387.19, 445.15, 503.20, 561.19, 619.54, 677.30, 735.34.
Taking raw material amine CAD-230 for mass spectrometry analysis, and taking a main peak ESI (+) of the raw material LC-Ms: 191.19, 249.15, 307.20, 365.19, 423.54, 481.30, 539.34.
The molecular weight difference 196 between the product and the starting material, from which it is seen that the polyether amide contained in sample CG5 is mainly a diacylated product, having the following structural formula:
wherein x1=1-2, x2=x3=0.
Example 6
The preparation method of the repairing agent of the embodiment is as follows:
MA-240 (129 g,0.3 mol) (molecular weight 430, available from Yu Jining Hua Kai resin) was dissolved in 220g of water with stirring, then maleic anhydride (58.8 g,0.6 mol) was added, and reacted at ordinary temperature with stirring for 4 hours to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 6 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 600g to obtain sample CG6 having a mass molar concentration of active groups of 1mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 503.19, 561.26, 619.36, 677.38, 735.37, 793.36, 851.37, 909.38, 967.27, 1025.32.
Mass spectrometry analysis is carried out on raw material amine MA-240, and main peak ESI (+) of raw material LC-Ms is carried out: 307.19, 365.26, 423.36, 481.38, 539.37, 597.36, 655.37, 713.38, 771.27, 829.32.
The molecular weight difference 196 between the product and the starting material, from which it is seen that the polyether amide contained in sample CG6 is mainly a diacylated product, having the following structural formula:
wherein x1+x3=5.1, x2=0.
Example 7
The preparation method of the repairing agent of the embodiment is as follows:
EDR-176 (52.8 g,0.3 mol) (molecular weight 176, from Yu Hengsi man) was dissolved in 150g of water with stirring, then maleic anhydride (58.8 g,0.6 mol) was added, and reacted at ordinary temperature with stirring for 3 hours to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 6 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 300g, to obtain sample CG7 having a mass molar concentration of active groups of 2mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 373.12.
mass spectrometry analysis is carried out on raw material amine EDR-176, and main peak ESI (+) of raw material LC-Ms is carried out: 177.13.
the molecular weight difference 196 between the product and the starting material, from which it is seen that the polyether amide contained in sample CG7 is predominantly a diacylated product having the following structural formula:
Example 8
The preparation method of the repairing agent of the embodiment is as follows:
HK-511 (66 g,0.3 mol) (molecular weight 220, available from Yu Hengsi man) was dissolved in 150g of water with stirring, then maleic anhydride (58.8 g,0.6 mol) was added thereto, and reacted at ordinary temperature with stirring for 4 hours to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 6 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 300g to obtain sample CG8 having a mass molar concentration of active groups of 2mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 416.18, 479.20, 532.19.
Mass spectrometry analysis is carried out on the raw material amine HK-511, and the main peak ESI (+) of the raw material LC-Ms is carried out: 220.18, 278.20, 336.19.
The molecular weight difference 196 between the product and the starting material, from which it is seen that the polyether amide contained in sample CG8 is predominantly a diacylated product having the following structural formula:
wherein x2=2.0, x1+x3=0.2.
Example 9
The preparation method of the repairing agent of the embodiment is as follows:
ED-900 (90 g,0.1 mol) (molecular weight 900, available from Yu Hengsi M) was dissolved in 100g of water with stirring, then maleic anhydride (19.6 g,0.2 mol) was added, and reacted at ordinary temperature for 2.5 hours with stirring to obtain a solid-containing dispersion, the pH of the reaction solution was adjusted to 6 with a 40% sodium oxide solution to obtain a clear solution, and diluted with water to 250g, to obtain sample CG9 having a mass molar concentration of active groups of 0.8mmol/g.
The clear solution was taken for mass spectrometry and the product LC-Ms main peak ESI (+): 725.23, 769.27, 813.28, 857.26, 901.30, 945.26, 989.25, 1033.27, 1134.36, 1178.35.
Taking raw material amine ED-900 for mass spectrometry, and carrying out main peak ESI (+)'s of raw material LC-Ms: 529.23, 573.27, 617.28, 661.26, 705.30, 749.26, 793.25, 837.27, 938.36, 982.35.
The molecular weight difference 196 between the product and the starting material, from which it is seen that the polyether amide contained in sample CG9 is predominantly a diacylated product having the following structural formula:
/>
wherein x2=12.5, x1+x3=5.0.
Comparative example 1
The preparation method of the repairing agent of the comparative example is as follows:
EDR-148 (44.4 g,0.3 mol) (molecular weight 148, from Yu Hengsi Man) was dissolved in 186g of water with stirring, then maleic acid (69.6 g,0.6 mol) was added, and reacted at room temperature with stirring for 1.5 hours to prepare a sample A1 having a molar concentration of active groups of 2 mmol/g by mass and the structural formula was as follows:
comparative example 2
The preparation method of the repairing agent of the comparative example is as follows:
ED-600 (120 g,0.2 mol) (molecular weight 600, available from Yu Hengsi man) was dissolved in 233.6g of water with stirring, then (46.4 g,0.4 mol) maleic acid was added, and reacted at room temperature with stirring for 2 hours to obtain sample A2, the molar concentration of active groups of which was 1mmol/g, and the structural formula was as follows:
Wherein x2=9.0, x1+x3=2.6.
Comparative example 3
The preparation method of the repairing agent of the comparative example is as follows:
t-403 (87.9 g,0.2 mol) (molecular weight 440, available from Yu Hengsi man) was dissolved in 142.5g of water with stirring, then maleic acid (69.6 g,0.6 mol) was added, and reacted at room temperature with stirring for 3 hours to prepare sample A3, active group mass molar concentration 2mmol/g, structural formula as follows:
wherein i1+i2+i3=5-6.
Comparative example 4
The preparation method of the repairing agent of the comparative example is as follows:
CAD-230 (69 g,0.3 mol) (molecular weight 230, available from Yangzhou morning) was dissolved in 161.5g of water with stirring, then maleic acid (69.6 g,0.6 mol) was added and reacted for 2 hours at room temperature with stirring to give sample A4 having a molar concentration of active groups of 2mmol/g by mass and the formula:
wherein x1=1-2, x2=x3=0.
Comparative example 5
The preparation method of the repairing agent of the comparative example is as follows:
MA-240 (129 g,0.3 mol) (molecular weight 430, from Yu Jining Hua Kai resin) was dissolved in 401.4 water with stirring, then maleic acid (69.6 g,0.6 mol) was added and reacted at room temperature with stirring for 4 hours to prepare sample A5 having a molar concentration of active groups of 1mmol/g by mass and the structural formula as follows:
wherein x2=0, x1+x3=5.1.
Comparative example 6
The preparation method of the repairing agent of the comparative example is as follows:
EDR-176 (52.8 g,0.3 mol) (molecular weight 176, available from Yu Hengsi man) was dissolved in 177.6g of water with stirring, then maleic acid (69.6 g,0.6 mol) was added, and reacted at room temperature with stirring for 3 hours to prepare sample A6 having a molar concentration of active groups of 2mmol/g by mass and the structural formula as follows:
。
comparative example 7
The preparation method of the repairing agent of the comparative example is as follows:
HK-511 (66 g,0.3 mol) (molecular weight 220, from Yu Hengsi man) was dissolved in 164.4g of water with stirring, and then maleic acid (69.6 g,0.6 mol) was added thereto, and reacted at ordinary temperature with stirring for 4 hours to prepare a sample A7 having a molar concentration of active groups of 2mmol/g by mass and the structural formula as follows:
wherein x2=2.0, x1+x3=0.2.
Comparative example 8
The preparation method of the repairing agent of the comparative example is as follows:
ED-900 (90 g,0.1mol (molecular weight 900, from Yu Hengsi M.) was dissolved in 136.8g of water with stirring, then maleic acid (23.2 g,0.2 mol) was added, and reacted at room temperature with stirring for 2.5 hours to give sample A8 having a molar concentration of active groups of 0.8 mmol/g, which had the following structural formula:
wherein x2=12.5, x1+x3=5.0.
The following effect tests were conducted on the restorative samples prepared in examples 1 to 9 and comparative examples 1 to 8 described above.
1. Marcel damage repair test
Pretreatment of hair bundles: an untreated in-vitro healthy hair bundle is selected, the hair bundle is divided into two halves, and is cleaned by 10 percent of K12 aqueous solution, and is dried at normal temperature for standby.
Hair bundle damage treatment: selecting L' OREAL elastic multi-position hair waving liquid/Bo cold waving liquid, treating hair bundles, fixing hair with a same number of hair curlers, washing with tap water until the hair bundles are wet, wiping excessive moisture with a towel, uniformly coating the hair curler (A agent and ammonium thioglycolate), placing the hair curler in a sealed bag for 20min (checking the curl after 15min, prolonging the time if the curl is insufficient), thoroughly washing the hair curler with clear water, wiping excessive moisture, uniformly coating a setting agent (B agent and sodium bromate) on hair curlers, standing for 10min, washing with clear water for 3min, naturally airing, and testing after 24 h.
Test article preparation: the amino acid shampoo without silicone oil is used as a matrix, each repairing agent sample and pure water (blank) are respectively added, the addition amount is 7.9%, and the mixture is mixed to obtain a test product (pH value is 6), and the formula is shown in table 1.
Repair of damaged hair tresses: the method comprises the steps of fixing the scalded hair bundles, flushing and soaking the hair bundles with clear water, uniformly smearing the hair bundles on the surface of the hair bundles according to the dosage of 0.2g of test product per gram of hair bundles (in each performance test, 3 groups of hair bundles are treated (half of the hair bundles are taken) per test sample, two samples are tested simultaneously by each group of hair bundles (under the influence of the hair bundles, different hair bundles possibly have obvious differences), and in order to ensure the accuracy of test results, only two samples are tested simultaneously by each group of hair bundles, namely the examples and the corresponding comparative examples, or the examples and the blanks are respectively compared pairwise), standing for 1min after gentle rubbing for 2min, flushing the hair bundles with clear water for 3min, and airing at normal temperature for standby.
TABLE 1 formula of shampoo for test (test article) (unit: g, total mass 100 g)
Test of combing Property
The test principle is as follows: the combing performance of the hair was judged by the rapid movement of the hair tresses (the repaired, permed hair tresses described above) from the root to the tip of the hair on a combing test instrument, recording the displacement, time, force (or load), and determining the average force (combing force) or energy absorption J (combing work) from the test. The greater the force and work, the worse the comb properties, and vice versa.
The testing method comprises the following steps: and fixing the hair bundle at a test position, and performing a comb property circulation test after setting test parameters. More than 15 times of test are required, the cycle times are guaranteed to be 12 times of effective times, after the variance treatment is carried out according to the test result, 3 data with relatively large fluctuation are removed, 12 effective data are reserved, each sample takes the average value of the effective data of three groups of hair bundles (the average value of combing force and the average value of energy absorption J, namely combing work) as the combing performance of the test data, and the test result is shown in table 2.
TABLE 2 results of the test for the combability of the damaged strands of scalded hair
Note that: 1. the smaller the combing force and combing work, the more flexible the hair bundle and the better the combing property;
2. The improvement rate is the change rate between the test results of the examples and the corresponding comparative examples or blanks, taking the absolute value.
From the results in table 2, it can be seen that the restoration effect of the restoration agent samples of the examples on damaged hair was significantly better than the corresponding comparative examples or blank.
(II) glossiness test
The test principle is as follows: a gloss meter is an instrument for measuring specular reflection from a surface, as determined by projecting a light beam at a fixed intensity and angle onto the surface of an object and measuring the amount of reflected light at equal but opposite angles. Gloss of hairIs an important sign reflecting the hair care status, and the better the hair care status is indicated by the more lustrous hair, and the serious hair damage is indicated by the opposite.
The testing method comprises the following steps: and (3) starting up and correcting the glossiness meter, and after the correction is successful, performing multi-angle test on the test background to ensure that the test data of the background plate are not different, and performing hair-tie test. The treatment hair bundles are combed smoothly, spread on a background plate, the instrument is attached to the hair bundles, each group of hair bundles are circularly tested for 15 times, the circulation times ensure the effective times for 12 times, and the glossiness of the hair bundles is tested by the test instrumentAs evaluation dimensions, 3 groups of averages were taken for each test sample as this test data, and the test results are shown in table 3./ >
TABLE 3 results of the test for the gloss of the damaged strands of hair
Note that: 1. gloss levelThe larger the indicating the better the luster of the hair strand;
2. the improvement rate is the change rate between the test results of the examples and the corresponding comparative examples or blanks, taking the absolute value.
As can be seen from Table 3, the restoration agent samples of examples 3, 4, and 6 have significantly better effect on improving the gloss of damaged hair than the corresponding comparative examples or blank, and all of the examples have gloss as compared with the corresponding comparative examplesAre all improved.
(III) testing of obdurability
The test principle is as follows: and stretching the hairline at a constant speed through an instrument until the hairline breaks, and calculating the tensile strength and the breaking work according to the curve for evaluating the strength and the toughness of the hair.
The testing method comprises the following steps: the hair bundle (the hair bundle subjected to the hair perming damage treatment and the repair) is subjected to sample feeding (test sample) cleaning, and then is subjected to test after being dried at normal temperature. The hair is fixed by the hair bundle fixer, the hair is not stretched too tightly or too loose as far as possible, after the fixing is completed, the test is started, three groups of 15 hair are tested for each sample, preferably 12 data (the hair with the same cross section or no significant difference selected by two comparison samples is used as a test sample) are selected for each group, the average value of the test results of 3 groups of hair bundles is taken as effective data, and the test results are shown in table 4.
TABLE 4 results of the measurement of the strength and toughness of the damaged hair strands
；
Note that: 1. the larger the tensile strength and the breaking work are, the better the hair bundle strength is;
2. when the p value is less than or equal to 0.05, the example has obvious difference with the corresponding comparative example or blank;
3. the improvement rate is the change rate between the test results of the examples and the corresponding comparative examples or blanks, taking the absolute value.
As can be seen from Table 4, all examples have improved tensile strength and anti-breakage effect compared with the corresponding comparative examples or blanks, indicating that the inventive restorative samples are used for damaged hair, and can improve the tensile strength and anti-breakage effect of damaged hair.
The results show that compared with a sample of the repairing agent prepared by combining polyetheramine and maleic acid through ionic bonds, the covalently bonded polyether amide repairing agent prepared by the invention has better repairing effect on hair damaged by perming, and can more effectively improve the comb property, glossiness and toughness of the damaged hair.
2. Hydrogen peroxide damage repair test
Hair bundle damage treatment: the SYOSS bleach is selected to treat the hair strands. According to the requirement of the using mode of the product, the product is used for drying hair. Uniformly coating the uniformly mixed hair bleach on an isolated real hair bundle, timing for 45min after uniformly coating, scraping the hair bleach by a comb, directly coating the mixed hair bleach on the hair again, waiting for 45min again, and washing with water.
Hair bundle sample feeding treatment: selecting the repairing agent samples prepared in the above examples 3, 6, 2 and 5, preparing a 0# 4 hair conditioner sample (pH value is 5.5) according to the formula of Table 5, cleaning the freshly rinsed hair bundles with blank shampoo (0.25 g shampoo/g hair) in Table 1, rinsing with running water for 2min, rinsing the hair bundles cleanly, uniformly applying each hair conditioner sample to the hair bundles according to the amount of 0.3g/g hair, timing after uniformly applying, standing for 10min, rinsing with running water for 2min, removing excessive moisture of the hair bundles, and naturally airing at normal temperature to perform the test. Wherein each test hair bundle is divided into two parts for pairwise comparison; each conditioner sample was tested in parallel for 3 groups of hair tresses.
TABLE 5 formula of test conditioner (unit: g, total mass 100 g)
Firstly, testing comb property, glossiness and toughness
The hair tresses treated with the 6 hair conditioner samples (blank, 0# were tested according to the combability, glossiness, and toughness test principles and methods described above in the hair perming damage repair test, wherein in each performance test, 3 hair tresses were treated in parallel per hair conditioner sample, and the average of the 3 hair tresses test results was taken, and the test results are shown in tables 6-8.
TABLE 6 results of damaged Hydrogen peroxide tress comb test
TABLE 7 results of Hydrogen peroxide damaged tress gloss test
TABLE 8 results of the strength and toughness test of damaged hydrogen peroxide hair bundles
As can be seen from table 5, the sample of the 0# conditioner contained silicone oil (polydimethylsiloxane, bis-aminopropyl polydimethylsiloxane), which was a light, smooth, breathable grease, and formed a protective film on the surface of the hair, wrapping the hair, and allowing the hair to be smooth, soft, and shinier. Therefore, the hair conditioner added with the silicone oil is smoother and glossy.
Analysis of tables 6-8 shows that, in gloss restoration, the 3# and 4# conditioner samples are better than the 0# conditioner sample, and significantly better than the 1# and #2 conditioner samples and the blank, respectively. In the combing property test and the toughness test, the 3# and 4# hair conditioner samples have obvious advantages compared with the 0# and 1# hair conditioner samples and the 2# hair conditioner samples and blanks. The 3# and 4# hair conditioner samples can obviously improve the combing smoothness and strength of damaged hair, and simultaneously have a certain improvement effect on the glossiness of the damaged hair.
(II) scanning analysis by electron microscope
The hair scales of each hair bundle sample after 4# (example 6), 2# (comparative example 5) and blank treatment are analyzed by a scanning electron microscope (the hair bundles for scanning electron microscope analysis are homologous, namely, are derived from the same in-vitro hair), so that the repairing effect of the sample on the hair can be judged. When damaged, the hair scales are damaged, which is manifested by tilting and falling off, and when the hair scales are repaired, the hair scales are attached to the hair, and the result is shown in fig. 1.
By comparison, the degree of closure of hair scales of hair treated by the No. 4 hair conditioner is more compact than that of hair scales of hair treated by the No. 2 hair conditioner and hair scales treated by a blank treatment, the edges of the hair scales are excessively smooth, and the effect of repairing damaged hair is better, namely, the hair conditioner sample prepared by taking the repairing agent sample prepared in the example 6 as a raw material can effectively smooth the hair scales, so that damaged hair is smooth and glossy.
3. Persistent repair effect test
Hair bundle damage treatment: the same treatment as described above for the hair tresses in the permanent wave damage repair test.
Hair bundle sample feeding treatment: the blank shampoo of table 1 was used as a matrix, and a G1 sample (example 1), a G3 sample (example 3), a G6 sample (example 6), an A1 sample (comparative example 1), an A2 sample (comparative example 2), and an A5 sample (comparative example 5) were added to the shampoo matrix to prepare A5 # -7# shampoo sample and A5 # '-7#' shampoo sample (pH 6). The method comprises the steps of (1) fixing the scalded hair bundles, flushing and soaking the hair bundles with clear water, uniformly coating 5# 7# and 5#' -7# shampoo samples on the hair bundle surface according to the dosage of 0.2g per gram of hair bundles (in each performance test, 3 groups of hair bundles are treated by each shampoo sample, half of the same group of hair bundles are treated by the 5# and 5# shampoo samples, half of the same group of hair bundles are treated by the 6# and 6# shampoo samples, half of the same group of hair bundles are treated by the 7# and 7# shampoo samples), lightly kneading the hair bundles for 2min, standing for 1min, flushing the hair bundles with clear water for 3min, and naturally airing the hair bundles at room temperature; this step was then repeated 10 times with 10% aqueous K12 (0.25 g/g hair) and the hair tresses were tested for comb, gloss and toughness after 0, 1, 3, 5, 10 washes, respectively.
Blank silicone oil free conditioner in table 5 was used as matrix: the hair conditioner matrix was added with the G1 sample (example 1), the G3 sample (example 3), the G6 sample (example 6), the A1 sample (comparative example 1), the A2 sample (comparative example 2), and the A5 sample (comparative example 5) to prepare 8# -10#, 8# '-10#' hair conditioner samples (pH 7). The method comprises the steps of cleaning the hair bundles which are finished through the blank shampoo (0.25 g/g hair) in table 1, flushing the hair bundles with flowing water for 2min after 2min, uniformly coating 0.3g of hair conditioner samples on the surface of the hair bundles according to each gram of hair bundles after the hair bundles are flushed, wherein in each performance test, each hair conditioner sample is used for treating 3 groups of hair bundles, 8# and 8# of hair conditioner samples are used for respectively treating half of the same groups of hair bundles, 9# and 9# of hair conditioner samples are used for respectively treating half of the same groups of hair bundles, 10# and 10# of hair conditioner samples are used for respectively treating half of the same groups of hair bundles, timing after the hair bundles are uniformly coated, flushing the hair bundles with flowing water for 2min after the hair bundles are left for 10min, removing redundant moisture of the hair bundles, and naturally airing the hair bundles at room temperature for standby. The hair tresses were then rinsed 10 times (without conditioner) with 10% aqueous K12 (0.25 g/g hair) in the same manner and tested for comb, gloss and toughness after 0, 1, 3, 5, 10 rinses, respectively.
Comb property, gloss, toughness test: comb properties, glossiness and toughness of hair bundles after the treatment of the above 6 shampoo samples and 6 conditioner samples and washing for 0 times, 1 time, 3 times, 5 times, 10 times were tested according to the comb properties, glossiness and toughness test principle and method in the hair waving damage test (part of hair bundles after washing for 0 times, 1 time, 3 times, 5 times, 10 times were used for toughness test) and test results are shown in tables 9 to 14.
TABLE 9 permanent comb property test results after repair of hair perming damaged shampoo sample
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TABLE 10 permanent combability test results after repair of a perm damaged conditioner sample
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As can be seen from tables 9 and 10, the restorative samples prepared in examples 1, 3 and 6 are significantly better in improving hair combability than the restorative samples prepared in comparative examples 1, 2 and 5, respectively, regardless of whether they are shampoo bases or conditioner bases; and with the increase of the cleaning times, the improvement rate of the repairing agent sample of the embodiment of the invention on the smoothness of the hair is obviously better than that of the corresponding comparative sample.
TABLE 11 permanent gloss test results after repair of a hair perming damaged shampoo sample
TABLE 12 permanent gloss test results after repair of perm damaged conditioner samples
It can be seen from tables 11 and 12 that the effect of the restorative samples of the examples of the present invention on improving the permanent gloss of damaged hair was even better than the corresponding comparative examples at different wash times, regardless of whether the shampoo or conditioner base was used.
TABLE 13 permanent strength and toughness test results after repair of hair-perming damaged shampoo sample
TABLE 14 permanent strength and toughness test results after repair of perm damaged conditioner samples
It can be seen from tables 13 and 14 that the repair effect of the repair agent samples of the examples of the present invention on the permanent toughness of damaged hair is still better than the corresponding comparative examples, regardless of the number of washes of the shampoo base or the conditioner base.
In conclusion, the polyether amine and the maleic anhydride react to form the polyether amide, and the maleic anhydride and the amine group of the polyether amine are covalently bonded to form the polyether amide, so that the polyether amide can be used as a repairing agent for hair damage, and ion exchange can not occur in repairing application, and the structure is stable. Therefore, after the hair injury repairing agent is applied to injured hair, the damaged hair can be effectively repaired, the comb property, the glossiness and the strength of the damaged hair are improved, the damaged hair has lasting repairing effect, and the comprehensive effect is obviously better than that of the repairing agent bonded by ions.
The above examples illustrate only a few embodiments of the invention, which are described in detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.
Claims (21)
1. A polyether amide having a structure represented by formula (1) or a stereoisomer thereof or a salt thereof:
；
(1)
Wherein A is the residue of polyetheramine after removing amino group, and p is more than or equal to 2.
2. Polyether amide or a stereoisomer or salt thereof according to claim 1, wherein p is selected from: 2. 3, 4.
3. Polyether amide or a stereoisomer or a salt thereof according to claim 1, wherein a is selected from:
、
；
wherein each R is independently selected from: hydrogen, methyl, ethyl;
R 1 selected from: hydrogen, methyl, ethyl, propyl,；
n=1-150, n1=1-10, n2=1-10, n3=1-10, n4=1-10, each m is independently 1 or 2.
4. The polyether amide or a stereoisomer or a salt thereof of claim 1, wherein the polyether amide has a structural formula as shown in formula (2), formula (3) or formula (4):
；
(2)
；
(3)
；
(4)
Wherein each m is independently 1 or 2;
n=1-18；
x1=0-20, x2=0-20, x3=0-20, and x1, x2, and x3 are not 0 at the same time;
each R is independently selected from: hydrogen, methyl, ethyl;
R 1 selected from: hydrogen, methyl, ethyl, propyl;
n1=1-10，n2=1-10，n3=1-10。
5. the polyether amide or a stereoisomer or a salt thereof of claim 4, wherein the polyether amide has a structural formula represented by formula (3):
；
(3)
Wherein x1=0-8, x2=0-20, x3=0-8, and x1, x2, and x3 are not 0 at the same time; each R in formula (3) is independently selected from: methyl, ethyl.
6. The polyetheramide or stereoisomer or salt thereof of claim 5, wherein x1+x3=0.2-6 and x2=0-15.
7. The polyether amide or a stereoisomer or a salt thereof of claim 4, wherein the polyether amide has a structural formula of formula (4):
；
(4)
Wherein n1+n2+n3=5-6; each R in formula (4) is independently selected from: hydrogen, methyl; r is R 1 Selected from: hydrogen, methyl, ethyl.
8. The polyetheramide or stereoisomer or salt thereof of claim 1, wherein the polyetheramide is selected from the group consisting of:
，，Wherein i1+i2+i3=5 to 6,
，
wherein x2=9.0, x1+x3=2.6; or x1=1-2, x2=x3=0; or x2=0, x1+x3=5.1; or x2=2.0, x1+x3=0.2; or x2=12.5, x1+x3=5.0.
9. The polyetheramide or stereoisomer or salt thereof according to any of claims 1-8, wherein the salt is a sodium salt, potassium salt, ammonium salt.
10. A process for the preparation of polyetheramides according to any one of claims 1 to 9, comprising the steps of: polyether amine and maleic anhydride react to obtain the product.
11. The method of preparing polyetheramide of claim 10, wherein the polyetheramine is selected from the group consisting of: EDR-148, ED-600, T-403, CAD-230, MA-240, EDR-176, HK-511, ED-900.
12. Use of a polyetheramide according to any one of claims 1 to 9 or a stereoisomer or a salt thereof as an active ingredient in the preparation of a restorative agent for restoration of damaged hair.
13. A restoration agent for restoring damaged hair, characterized in that its active ingredient comprises the polyether amide as defined in any one of claims 1 to 9 or a stereoisomer or a salt thereof.
14. A restoration agent for restoration of damaged hair according to claim 13, wherein the polyether amide or a stereoisomer or a salt thereof is added to the restoration agent in an amount of 0.2mmol/g-5mmol/g in terms of the molar concentration of amide groups.
15. A restoration agent for restoration of damaged hair as recited in claim 13, further comprising an alkaline neutralizer.
16. A restoration agent for restoration of damaged hair as claimed in any one of claims 13-15, characterized in that the pH of said restoration agent is 3-9.
17. A method of preparing a restoration agent for restoration of damaged hair as claimed in any one of claims 13-16, characterized by comprising the steps of:
polyether amine reacts with maleic anhydride, the pH value of the obtained reaction mixture or reaction product is regulated, and water is added for dilution to the specified concentration, thus obtaining the catalyst.
18. Use of a polyether amide according to any one of claims 1 to 9 or a stereoisomer or a salt thereof, or a restoration agent according to any one of claims 13 to 16 as an active ingredient in the preparation of a restoration product for restoring damaged hair.
19. A shampoo or conditioner for repairing damaged hair, characterized in that its active ingredient comprises the polyether amide according to any one of claims 1 to 9 or a stereoisomer or a salt thereof, or its active ingredient comprises the repairing agent according to any one of claims 13 to 16.
20. The shampoo or conditioner for repairing damaged hair according to claim 19 wherein the repair agent is added to the shampoo or conditioner in an amount of 0.1wt% to 50wt%.
21. A method of repairing damaged hair comprising the steps of: a shampoo or conditioner according to any one of claims 19 to 20 applied to the surface of damaged hair for repair.
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| US4304889A (en) * | 1980-07-11 | 1981-12-08 | Texaco Inc. | Solvent resistant epoxy coatings |
| US4518749A (en) * | 1983-11-07 | 1985-05-21 | Texaco Inc. | Epoxy resin curatives |
| US4859374A (en) * | 1987-03-07 | 1989-08-22 | Bayer Aktiengesellschaft | Sulfosuccinamido acids of polyoxypropylenediamines and their use as emulsifiers |
| DE19607641A1 (en) * | 1996-02-29 | 1997-09-04 | Basf Ag | Water-soluble condensation products for use in paper production |
| US6297325B1 (en) * | 2000-02-25 | 2001-10-02 | The Goodyear Tire & Rubber Company | Rubber composition comprised of cis-1,4-polyisoprene and polymeric di-maleamic acid and articles, including tires, having at least one component comprised thereof |
| CN107075067A (en) * | 2014-09-25 | 2017-08-18 | 巴斯夫欧洲公司 | Polyetheramine based on 1,3 glycol |
| WO2023148138A1 (en) * | 2022-02-02 | 2023-08-10 | Clariant International Ltd | Compounds for use as hair repair agents or fabric repair agents |
-
2024
- 2024-01-18 CN CN202410070607.0A patent/CN117586143A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304889A (en) * | 1980-07-11 | 1981-12-08 | Texaco Inc. | Solvent resistant epoxy coatings |
| US4518749A (en) * | 1983-11-07 | 1985-05-21 | Texaco Inc. | Epoxy resin curatives |
| US4859374A (en) * | 1987-03-07 | 1989-08-22 | Bayer Aktiengesellschaft | Sulfosuccinamido acids of polyoxypropylenediamines and their use as emulsifiers |
| DE19607641A1 (en) * | 1996-02-29 | 1997-09-04 | Basf Ag | Water-soluble condensation products for use in paper production |
| US6297325B1 (en) * | 2000-02-25 | 2001-10-02 | The Goodyear Tire & Rubber Company | Rubber composition comprised of cis-1,4-polyisoprene and polymeric di-maleamic acid and articles, including tires, having at least one component comprised thereof |
| CN107075067A (en) * | 2014-09-25 | 2017-08-18 | 巴斯夫欧洲公司 | Polyetheramine based on 1,3 glycol |
| WO2023148138A1 (en) * | 2022-02-02 | 2023-08-10 | Clariant International Ltd | Compounds for use as hair repair agents or fabric repair agents |
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