CN114569496A - Macromolecular thickener and preparation method and application thereof - Google Patents
Macromolecular thickener and preparation method and application thereof Download PDFInfo
- Publication number
- CN114569496A CN114569496A CN202210268670.6A CN202210268670A CN114569496A CN 114569496 A CN114569496 A CN 114569496A CN 202210268670 A CN202210268670 A CN 202210268670A CN 114569496 A CN114569496 A CN 114569496A
- Authority
- CN
- China
- Prior art keywords
- oil
- reaction kettle
- thickener
- component
- glyceryl
- 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.)
- Granted
Links
- 239000002562 thickening agent Substances 0.000 title claims abstract description 62
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 230000002378 acidificating effect Effects 0.000 claims abstract description 24
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 238000003756 stirring Methods 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000008367 deionised water Substances 0.000 claims description 18
- 229910021641 deionized water Inorganic materials 0.000 claims description 18
- 239000003431 cross linking reagent Substances 0.000 claims description 17
- 239000003921 oil Substances 0.000 claims description 16
- -1 polyoxyethylene Polymers 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000002537 cosmetic Substances 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 12
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 10
- 239000002480 mineral oil Substances 0.000 claims description 10
- 235000010446 mineral oil Nutrition 0.000 claims description 10
- 229940051841 polyoxyethylene ether Drugs 0.000 claims description 10
- 229920000056 polyoxyethylene ether Polymers 0.000 claims description 10
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229920002545 silicone oil Polymers 0.000 claims description 9
- XHZPRMZZQOIPDS-UHFFFAOYSA-N 2-Methyl-2-[(1-oxo-2-propenyl)amino]-1-propanesulfonic acid Chemical group OS(=O)(=O)CC(C)(C)NC(=O)C=C XHZPRMZZQOIPDS-UHFFFAOYSA-N 0.000 claims description 8
- BANXPJUEBPWEOT-UHFFFAOYSA-N 2-methyl-Pentadecane Chemical compound CCCCCCCCCCCCCC(C)C BANXPJUEBPWEOT-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 8
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 7
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims description 7
- 239000001593 sorbitan monooleate Substances 0.000 claims description 7
- 229940035049 sorbitan monooleate Drugs 0.000 claims description 7
- 235000011069 sorbitan monooleate Nutrition 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004519 grease Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 claims description 6
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 5
- 229940075507 glyceryl monostearate Drugs 0.000 claims description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 5
- 239000001587 sorbitan monostearate Substances 0.000 claims description 5
- 229940035048 sorbitan monostearate Drugs 0.000 claims description 5
- 235000011076 sorbitan monostearate Nutrition 0.000 claims description 5
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 claims description 4
- 229940043268 2,2,4,4,6,8,8-heptamethylnonane Drugs 0.000 claims description 4
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 claims description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 4
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 claims description 4
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 claims description 4
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 4
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005456 glyceride group Chemical group 0.000 claims description 4
- KUVMKLCGXIYSNH-UHFFFAOYSA-N isopentadecane Natural products CCCCCCCCCCCCC(C)C KUVMKLCGXIYSNH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 229940127557 pharmaceutical product Drugs 0.000 claims description 4
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 4
- 229960005078 sorbitan sesquioleate Drugs 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 claims description 3
- 229940055577 oleyl alcohol Drugs 0.000 claims description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 3
- 229940031709 peg-30-dipolyhydroxystearate Drugs 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 229940100515 sorbitan Drugs 0.000 claims description 3
- 229940032094 squalane Drugs 0.000 claims description 3
- 229940099259 vaseline Drugs 0.000 claims description 3
- DRAWQKGUORNASA-UHFFFAOYSA-N (2-hydroxy-3-octadec-9-enoyloxypropyl) octadec-9-enoate Chemical compound CCCCCCCCC=CCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCC=CCCCCCCCC DRAWQKGUORNASA-UHFFFAOYSA-N 0.000 claims description 2
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 2
- CMPDPBDUZTUXAD-UHFFFAOYSA-N [3-hydroxy-2-(16-methylheptadecanoyloxy)propyl] 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC(C)C CMPDPBDUZTUXAD-UHFFFAOYSA-N 0.000 claims description 2
- 150000005215 alkyl ethers Chemical class 0.000 claims description 2
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 claims description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 229940074045 glyceryl distearate Drugs 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 2
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical group 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- OKJMLYFJRFYBPS-UHFFFAOYSA-J tetraazanium;cerium(4+);tetrasulfate Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OKJMLYFJRFYBPS-UHFFFAOYSA-J 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 claims 1
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims 1
- 229940117972 triolein Drugs 0.000 claims 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract description 20
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 abstract description 16
- 229920000642 polymer Polymers 0.000 abstract description 13
- 230000008719 thickening Effects 0.000 abstract description 11
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 abstract description 10
- 239000002994 raw material Substances 0.000 abstract description 8
- 230000001804 emulsifying effect Effects 0.000 abstract description 6
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract description 5
- 229960004889 salicylic acid Drugs 0.000 abstract description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 150000007942 carboxylates Chemical group 0.000 abstract description 2
- 235000014655 lactic acid Nutrition 0.000 abstract description 2
- 239000004310 lactic acid Substances 0.000 abstract description 2
- 238000003860 storage Methods 0.000 abstract description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical group NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 9
- 125000004386 diacrylate group Chemical group 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
- CMVNWVONJDMTSH-UHFFFAOYSA-N 7-bromo-2-methyl-1h-quinazolin-4-one Chemical compound C1=CC(Br)=CC2=NC(C)=NC(O)=C21 CMVNWVONJDMTSH-UHFFFAOYSA-N 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- 239000004641 Diallyl-phthalate Substances 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229940008099 dimethicone Drugs 0.000 description 2
- KHAYCTOSKLIHEP-UHFFFAOYSA-N docosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCCCOC(=O)C=C KHAYCTOSKLIHEP-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006322 acrylamide copolymer Polymers 0.000 description 1
- 229940086737 allyl sucrose Drugs 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001536 azelaic acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 229940074052 glyceryl isostearate Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- NGYRYRBDIPYKTL-UHFFFAOYSA-N icosyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCCCOC(=O)C=C NGYRYRBDIPYKTL-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229940060184 oil ingredients Drugs 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229940116406 poloxamer 184 Drugs 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
- 229940044476 poloxamer 407 Drugs 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 150000003870 salicylic acids Chemical class 0.000 description 1
- 229940083037 simethicone Drugs 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
-
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/23—Sulfur; Selenium; Tellurium; Compounds 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
- A61K8/31—Hydrocarbons
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- A61K8/41—Amines
-
- 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
- A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
-
- 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
- A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/86—Polyethers
-
- 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
- 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
- A61K2800/10—General cosmetic use
-
- 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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses a macromolecular thickener, a preparation method and application thereof, and belongs to the technical field of thickening. The macromolecular thickener is mainly prepared by synthesizing a monomer containing a taurate group and a monomer containing a carboxylate group. The polymer thickener has strong thickening capability in an acidic environment with the pH value of 2-4, can well thicken acidic nonionic raw materials such as glycolic acid, lactic acid, salicylic acid, azelaic acid and the like, and remarkably improves the storage stability of an acidic formula system; enabling the formula containing 20 wt% of azelaic acid to be stored for a long time at normal temperature of 25-30 ℃ and low temperature of 3-10 ℃ without separating out azelaic acid crystals; and the formula containing 2-5 wt% of salicylic acid is not easy to change color, and the good stability is kept for a long time. The macromolecular thickener also has certain emulsifying capacity, and can obtain a more stable emulsifying system by being compounded with the nonionic small molecular emulsifier.
Description
Technical Field
The invention belongs to the technical field of thickening, and particularly relates to a high-molecular thickening agent, and a preparation method and application thereof.
Background
In the cosmetic and pharmaceutical industries, the macromolecular thickening agent is generally used in cream, essence and other dosage forms and plays roles of thickening, suspending and the like. The synthetic polymer thickener includes two categories of oil solubility and water solubility, and if not specifically stated, the invention is exclusively directed to a water-soluble polymer thickener (hereinafter referred to as a polymer thickener).
Among the polymeric thickeners used in cosmetics and pharmaceuticals, carbomers are most commonly used. Also, Simugel series polymers from Seppic (e.g., Simugel EG), as well as acrylamide copolymers Sepigel 305, xanthan gum, locust bean gum, and less commonly poloxamer 407, poloxamer 184, etc.
In recent years, with the introduction of relevant regulations and further improvement of requirements of consumers on the efficacy of cosmetics and medical skin products, the market capacity of acidic system cosmetics and medical skin products is increasing, and the search amount of fruit acids, salicylic acids and azelaic acids on each large network platform is increasing. However, the addition of acidic substances to conventional polymeric thickeners results in system collapse (a sharp drop in consistency or poor cold-heat stability); or the addition amount is too large, for example, poloxamer needs to be added by more than 10 wt%, so that the odor is very big, the skin feel is not good, and the cost is very high; for example, a formula with 20 wt% of azelaic acid is added, and a large amount of azelaic acid crystals are separated out after the mixture is stored for a certain time at normal temperature or low temperature; the formula with 2-5 wt% of salicylic acid is added, so that the problems of color change or poor stability and the like exist.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention has the first aim of providing a macromolecular thickening agent and a preparation method thereof; the macromolecular thickener is mainly synthesized by monomers containing taurate groups and carboxylate groups, and has strong thickening capability in an acidic environment (pH is 2-4). The second purpose of the invention is to provide the application of the macromolecular thickening agent in acidic cosmetics or medicines and other products, wherein the macromolecular thickening agent can play a good thickening role in the products and can obviously improve the stability of the products.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a macromolecular thickener is prepared from the following components:
the component A is at least one of vinyl long-chain alkyl ether, acrylic long-chain alkyl ester and methacrylic long-chain alkyl ester with the total carbon atom number of 10-30; the component B is acryloyl dimethyl taurine; the component C is at least one of acrylic acid and methacrylic acid.
Preferably, the organic base is at least one of triisopropanolamine, triethanolamine, tetrahydroxypropylethylenediamine and aminomethylpropanol.
Preferably, the crosslinking agent is a polyol or an organic compound containing at least two unsaturated double bonds.
Preferably, the cross-linking agent is at least one of 1, 3-propanediol, glycerol, 1, 3-butanediol, diallyl phthalate, N-methylolacrylamide, N' -methylenebisacrylamide, polyethylene glycol (200) diacrylate, polyethylene glycol (400) diacrylate, polyethylene glycol (600) diacrylate, polyethylene glycol (1000) diacrylate, polyethylene glycol (200) dimethacrylate, polyethylene glycol (400) dimethacrylate, polyethylene glycol (600) dimethacrylate, polyethylene glycol (1000) dimethacrylate, PEG-15 trimethylpropyl ether triacrylate, allyl sucrose ether.
Preferably, the initiator is at least one of cerium ammonium sulfate, ammonium persulfate, sodium persulfate, potassium persulfate, azobisisobutyronitrile, azobisisobutylamidine hydrochloride, dibenzoyl peroxide and tert-butyl hydroperoxide.
Preferably, the grease is isohexadecane, synthetic squalane, 10#White mineral oil, 15#White mineral oil, 26#White mineral oil, 36#At least one of white mineral oil, vaseline, 50cs dimethyl silicone oil, 100cs dimethyl silicone oil and 350cs dimethyl silicone oil.
Preferably, the water-in-oil emulsifier is at least one of glyceryl monostearate, glyceryl monooleate, glyceryl dioleate trimer, glyceryl diisostearate trimer, glyceryl distearate trimer, glyceryl isostearate monoglyceride isostearate, decaglyceryl decaoleate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan sesquiisostearate, oleyl alcohol polyoxyethylene (2) ether, PEG-30 dipolyhydroxystearate, polyethylene/polypropylene glycol-10/1 dimethicone, and PEG-10 dimethicone.
Preferably, the oil-in-water emulsifier is at least one of stearyl alcohol polyoxyethylene ether (40), oleyl alcohol polyoxyethylene ether (20), polyoxyethylene ether (20) sorbitan monostearate, polyoxyethylene ether (20) sorbitan monooleate, polyoxyethylene ether (20) methyl glucoside sesquioleate, polyoxyethylene ether (7) coco glyceride, polyglycerol-10 monolaurate, polyglycerol-10 dilaurate, polyglycerol-10 monooleate, polyglycerol-10 dioleate and polyglycerol-3 decanoate.
The invention also provides a preparation method of the macromolecular thickener, which comprises the following steps:
(1) under the condition of stirring, sequentially adding deionized water, organic base and the component B into a reaction kettle, and uniformly mixing, wherein the temperature of the reaction kettle is controlled within 80 ℃ (including 80 ℃);
(2) controlling the temperature of the reaction kettle to be within 80 ℃, adding the grease, the water-in-oil emulsifier and the component A into the reaction kettle under the stirring condition, and dissolving and uniformly mixing;
(3) slowly adding the cross-linking agent into the reaction kettle under the stirring condition, uniformly stirring after the addition is finished, controlling the temperature to be 20-80 ℃, and introducing nitrogen for protection;
(4) adding an initiator into the reaction kettle, uniformly stirring, and controlling the temperature to be 20-110 ℃;
(5) and (4) after the reaction in the step (4) is finished, adding the oil-in-water emulsifier into the reaction kettle, and uniformly stirring to obtain the macromolecular thickener.
Preferably, the stirring speed in the preparation method is 30-800 rpm.
Preferably, when the polymeric thickener formulation contains component C, said component C is added after component B is added in step (1).
Preferably, when the cross-linking agent is water-soluble, the cross-linking agent is firstly prepared into a solution by deionized water and then added into a reaction kettle; when the cross-linking agent is oil-soluble, it is added directly to the oil phase.
The invention also provides the application of the macromolecular thickening agent in preparing acidic system products; preferably, the acidic system product is an acidic cosmetic or pharmaceutical product.
An acidic system product comprising the polymeric thickener; preferably, the acidic system product is an acidic cosmetic or pharmaceutical product.
Compared with the prior art, the invention has the beneficial effects that:
1. the macromolecular chain of the macromolecular thickener contains lipophilic groups and hydrophilic groups, has certain emulsifying capacity, and can obtain a more stable emulsifying system by being compounded with the nonionic micromolecular emulsifier;
2. the macromolecular thickener is a micro-crosslinking structure, anionic charged groups on the side chains of the macromolecular thickener can generate mutual repulsion after meeting water and swell in water, intermolecular acting forces such as hydrogen bonds, Van der Waals force and the like exist between each group of a macromolecular chain segment and water molecules, and the acting forces can prevent or delay coalescence among liquid drops, thereby playing a good role in suspension stabilization;
3. the macromolecular thickener is dispersed in water, so that the pH of a dispersion liquid is 2.0-5.0, the dispersion liquid is weakly acidic, the dispersion liquid has strong thickening capability in an acidic environment (the pH is 2-4), acidic nonionic raw materials such as glycolic acid, lactic acid, salicylic acid, azelaic acid and the like can be thickened well, and the storage stability of an acidic formula system is improved remarkably; enabling the formula containing 20 wt% of azelaic acid to be stored for a long time at normal temperature (25-30 ℃) and low temperature (3-10 ℃) without separating out azelaic acid crystals; and the formula containing 2-5 wt% of salicylic acid is not easy to change color, and better stability is kept for a long time;
4. the macromolecular thickening agent does not contain the forbidden components in the standards of cosmetics and medicines, and is safe and nontoxic.
Detailed Description
The technical solutions of the present invention will be further described with reference to the following embodiments, and it should be apparent that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without making any creative effort based on the embodiments in the present invention, belong to the protection scope of the present invention. The starting materials used in the examples of the present invention were commercially available and were used in parallel experiments.
Example 1
The raw materials in table 1 were used to prepare the polymeric thickeners.
TABLE 1 proportion of the components of the polymeric thickener (total amount: 100kg)
| Serial number | Name of raw materials | wt％ |
| 01 | Acryloyl dimethyl taurine (component B) | 35.0 |
| 02 | 10#Cosmetic grade white mineral oil (grease) | 11.0 |
| 03 | Glyceryl monostearate (Water-in-oil type emulsifier) | 2.0 |
| 04 | Glyceryl monooleate (Water-in-oil type emulsifier) | 2.5 |
| 05 | Behenyl acrylate (component A) | 1.5 |
| 06 | 350cs dimethyl silicone oil (grease) | 2.0 |
| 07 | PEG-20 sorbitan monooleate (oil-in-water emulsifier) | 3.0 |
| 08 | Triethanolamine (organic base) | 25.0 |
| 09 | Sodium persulfate (initiator) | 0.15 |
| 10 | Polyethylene glycol (1000) diacrylate (crosslinker) | 0.12 |
| 11 | Deionized water | To 100 of |
The preparation process comprises the following steps:
(1) starting the reaction kettle, continuously stirring (the stirring speed is 30-800 rpm), sequentially adding a proper amount of deionized water, triethanolamine and acryloyl dimethyl taurine into the reaction kettle, and uniformly mixing, wherein the temperature is controlled within 65 ℃;
(2) preparing polyethylene glycol (1000) diacrylate into a cross-linking agent solution by using deionized water;
(3) adding 10 into a reaction kettle#Uniformly stirring, dissolving and mixing cosmetic grade white mineral oil, 350cs dimethyl silicone oil, glyceryl monostearate, glyceryl monooleate and behenyl acrylate, and controlling the temperature to be 65 ℃;
(4) slowly adding the cross-linking agent solution obtained in the step (2) into the reaction kettle under the stirring state, uniformly stirring after 30min of feeding, controlling the temperature at 70 ℃, and introducing nitrogen for 30min of protection;
(5) adding sodium persulfate into the reaction kettle, and uniformly stirring, wherein the temperature is controlled within 100 ℃;
(6) and after the reaction is finished, adding PEG-20 sorbitan monooleate, and uniformly stirring to obtain the macromolecular thickening agent.
The polymeric thickener prepared in example 1 was dissolved in deionized water at an addition amount of 5 wt% to prepare a dispersion, and the dispersion was examined to have a pH of 4.0 and a viscosity of 1500mpa.s at 25 ℃.
And (3) testing thickening performance: an aqueous solution of 5% by mass glycolic acid (viscosity at 25 ℃ C. of <10mPa.s, pH 1.86) was prepared. The polymer thickener prepared in example 1 was added to the glycolic acid aqueous solution in an amount of 5 wt%, stirred and mixed uniformly, and the system viscosity was measured. The detection result shows that the pH value of the system is 2.29, and the viscosity at 25 ℃ is 800 mPa.s.
Example 2
The raw materials in table 2 were used to prepare the polymeric thickeners.
TABLE 2 proportion of the components of the polymer thickener (total amount: 100kg)
The preparation process comprises the following steps:
(1) starting the reaction kettle, continuously stirring (the stirring speed is 30-800 rpm), sequentially adding deionized water, triethanolamine, acryloyl dimethyl taurine and acrylic acid into the reaction kettle, and uniformly mixing, wherein the temperature is controlled within 75 ℃;
(2) adding 26# white oil, vaseline, PEG-30 dipolyhydroxystearate, glycerol monooleate and lauryl methacrylate into a reaction kettle, stirring, dissolving and uniformly mixing, and controlling the temperature at 75 ℃;
(3) slowly adding diallyl phthalate into the reaction kettle under the stirring state, uniformly stirring after 30min of feeding, controlling the temperature at 75 ℃, and introducing nitrogen for protection for 30 min;
(4) adding potassium persulfate into the reaction kettle, uniformly stirring, and controlling the temperature to be 80 ℃;
(5) and after the reaction is finished, adding polyglycerol-10 laurate, and uniformly stirring to obtain the macromolecular thickening agent.
The polymeric thickener prepared in example 2 was dissolved in deionized water at an addition level of 4 wt% to prepare a dispersion, and the dispersion was examined to have a pH of 4.5 and a viscosity of 35000mpa.s at 25 ℃.
And (3) testing thickening performance: an aqueous solution of 5% by mass glycolic acid (viscosity <10mpa.s at 25 ℃ and pH 1.86) was prepared. The polymer thickener prepared in example 2 was added to the glycolic acid aqueous solution in an amount of 5 wt%, stirred and mixed uniformly, and the system viscosity was measured. The measurement results showed that the pH of the system was 2.55 and the viscosity at 25 ℃ was 4500 mPa.s.
Example 3
The polymeric thickeners were prepared using the raw materials in table 3.
TABLE 3 proportion of the components of the polymer thickener (total amount 100kg)
The preparation process comprises the following steps:
(1) starting the reaction kettle, continuously stirring (the stirring speed is 30-800 rpm), sequentially adding a proper amount of deionized water, triethanolamine, acryloyl dimethyl taurine and acrylic acid into the reaction kettle, and uniformly mixing, wherein the temperature is controlled within 80 ℃;
(2) preparing PEG-15 trimethyl propyl ether triacrylate into a cross-linking agent solution by using deionized water;
(3) adding synthesized squalane, sorbitan monostearate, sorbitan sesquiisostearate and eicosyl acrylate into a reaction kettle, stirring, dissolving and uniformly mixing, and controlling the temperature to be 80 ℃;
(4) slowly adding the cross-linking agent solution obtained in the step (2) into the reaction kettle under the stirring state, uniformly stirring after 30min of feeding, controlling the temperature at 80 ℃, and introducing nitrogen for 30min of protection;
(5) adding azodiisobutyl amidine hydrochloride into a reaction kettle, uniformly stirring, and controlling the temperature at 95 ℃;
(6) and after the reaction is finished, adding PEG-20 sorbitan monooleate, and uniformly stirring to obtain the macromolecular thickening agent for the acidic system.
The polymer thickener prepared in example 3 was dissolved in deionized water in an amount of 3 wt% to prepare a dispersion, and it was found that the dispersion had a pH of 4.25 and a viscosity of 55200mpa.s at 25 ℃.
And (3) testing thickening performance: an aqueous solution of 5% by mass glycolic acid (viscosity <10mpa.s at 25 ℃ and pH 1.86) was prepared. The polymer thickener prepared in example 3 was added to the glycolic acid aqueous solution in an amount of 5 wt%, stirred and mixed uniformly, and the system viscosity was measured. The measurement results showed that the pH of the system was 2.41 and the viscosity at 25 ℃ was 5200 mPa.s.
And (3) testing the emulsifying property: the polymer thickener prepared in example 3 is added into No. 26 white oil (the other component is deionized water) with the addition of 3 wt%, the mixture is stirred and mixed evenly and is placed for 24 hours at low temperature (5 ℃) and high temperature (45 ℃) respectively, and after seven cycles, the paste is still in a stable state and does not become thin and produce oil. The polymer thickener is compounded with the nonionic micromolecule emulsifier, so that a more stable emulsifying system can be obtained.
Example 4
The polymeric thickeners were prepared using the raw materials in table 4.
TABLE 4 proportion of the components of the polymer thickener (total amount: 100kg)
| Serial number | Name of raw materials | wt％ |
| 01 | Acryloyl dimethyl taurine (component B) | 34.5 |
| 02 | Isohexadecane (oil) | 14.0 |
| 03 | Sorbitan sesquioleate (water-in-oil type emulsifier) | 3.2 |
| 04 | PEG-10 polydimethylsiloxane (Water-in-oil emulsifier) | 2.0 |
| 05 | Behenyl methacrylate (component A) | 3.5 |
| 06 | 100cs dimethyl silicone oil (grease) | 2.0 |
| 07 | PEG-7 Cocoanoic acid glyceride (oil-in-water emulsifier) | 8.0 |
| 08 | Triisopropanolamine (organic base) | 25.0 |
| 09 | Ammonium persulfate (initiator) | 0.10 |
| 10 | N, N' -methylenebisacrylamide (crosslinker) | 0.11 |
| 11 | Acrylic acid (component C) | 2.2 |
| 12 | Deionized water | To 100 of |
The preparation process comprises the following steps:
(1) starting the reaction kettle, continuously stirring (the stirring speed is 30-800 rpm), sequentially adding a proper amount of deionized water, triisopropanolamine, acryloyl dimethyl taurine and acrylic acid into the reaction kettle, and uniformly mixing, wherein the temperature is controlled within 80 ℃;
(2) preparing N, N' -methylene bisacrylamide into a cross-linking agent solution by using deionized water;
(3) adding isohexadecane, 100cs simethicone, sorbitan sesquioleate, PEG-10 polydimethylsiloxane and behenyl methacrylate into a reaction kettle, stirring, dissolving and mixing uniformly, and controlling the temperature at 80 ℃;
(4) slowly adding the cross-linking agent solution obtained in the step (2) into the reaction kettle under the stirring state, uniformly stirring after 30min of feeding, controlling the temperature at 80 ℃, and introducing nitrogen for 30min of protection;
(5) adding an ammonium persulfate aqueous solution into a reaction kettle, uniformly stirring, and controlling the temperature to be 85 ℃;
(6) after the reaction is finished, adding PEG-7 coconutate glyceride, and uniformly stirring to obtain the macromolecular thickening agent.
The polymeric thickener prepared in example 4 was dissolved in deionized water at an addition level of 3 wt% to make a dispersion, which was tested to have a pH of 3.50 and a viscosity of 2635mpa.s at 25 ℃.
And (3) testing thickening performance: an aqueous solution of 5% by mass glycolic acid (viscosity <10mpa.s at 25 ℃ and pH 1.86) was prepared. The polymer thickener prepared in example 4 was added to the glycolic acid aqueous solution in an amount of 5 wt%, stirred and mixed uniformly, and the system viscosity was measured. The detection result shows that the pH value of the system is 2.43, and the viscosity at 25 ℃ is 8400 mPa.s.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. The macromolecular thickener is characterized by being prepared from the following components:
the component A is at least one of vinyl long-chain alkyl ether, acrylic long-chain alkyl ester and methacrylic long-chain alkyl ester with the total carbon atom number of 10-30; the component B is acryloyl dimethyl taurine; the component C is at least one of acrylic acid and methacrylic acid.
2. The polymeric thickener of claim 1, wherein said organic base is at least one of triisopropanolamine, triethanolamine, tetrahydroxypropylethylenediamine, and aminomethylpropanol.
3. The polymeric thickener of claim 1, wherein said cross-linking agent is a polyol or an organic compound containing at least two unsaturated double bonds.
4. The polymeric thickener of claim 1, wherein said initiator is at least one of cerium ammonium sulfate, ammonium persulfate, sodium persulfate, potassium persulfate, azobisisobutyronitrile, azobisisobutylamidine hydrochloride, dibenzoyl peroxide, tert-butyl hydroperoxide.
5. The polymeric thickener of claim 1, wherein said oil is isohexadecane, synthetic squalane, 10#White mineral oil, 15#White mineral oil, 26#White mineral oil, 36#At least one of white mineral oil, vaseline, 50cs dimethyl silicone oil, 100cs dimethyl silicone oil and 350cs dimethyl silicone oil.
6. The polymeric thickener according to claim 1, wherein the water-in-oil emulsifier is at least one of glyceryl monostearate, glyceryl monooleate, glyceryl dioleate, glyceryl trioleate, glyceryl diisostearate, glyceryl distearate, glyceryl monostearate, glyceryl decaglyceryl decaoleate, sorbitan monostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan sesquiisostearate, oleyl alcohol polyoxyethylene (2) ether, PEG-30 dipolyhydroxystearate, polyethylene/polypropylene glycol-10/1 dimethylsiloxane, and PEG-10 polydimethylsiloxane.
7. The polymeric thickener of claim 1, wherein the oil-in-water emulsifier is at least one of polyoxyethylene stearyl ether (40), polyoxyethylene oleyl ether (20), polyoxyethylene ether (20) sorbitan monostearate, polyoxyethylene ether (20) sorbitan monooleate, polyoxyethylene ether (20) methyl glucoside sesquioleate, polyoxyethylene ether (7) coco glyceride, polyglycerol-10 monolaurate, polyglycerol-10 dilaurate, polyglycerol-10 monooleate, polyglycerol-10 dioleate, and polyglycerol-3 decanoate.
8. The method for producing a polymeric thickener according to any of claims 1 to 7, comprising the steps of:
(1) under the condition of stirring, sequentially adding deionized water, organic base and the component B into a reaction kettle, uniformly mixing, and controlling the temperature of the reaction kettle within 80 ℃;
(2) controlling the temperature of the reaction kettle to be within 80 ℃, adding the grease, the water-in-oil emulsifier and the component A into the reaction kettle under the stirring condition, and dissolving and uniformly mixing;
(3) slowly adding the cross-linking agent into the reaction kettle under the stirring condition, uniformly stirring after the addition is finished, controlling the temperature to be 20-80 ℃, and introducing nitrogen for protection;
(4) adding an initiator into the reaction kettle, uniformly stirring, and controlling the temperature to be 20-110 ℃;
(5) after the reaction in the step (4) is finished, adding an oil-in-water emulsifier into the reaction kettle and uniformly stirring to obtain the macromolecular thickener;
preferably, when the formulation of the polymeric thickener contains component C, said component C is added after component B is added in step (1);
preferably, when the cross-linking agent is water-soluble, the cross-linking agent is firstly prepared into a solution by deionized water and then added into a reaction kettle; when the cross-linking agent is oil-soluble, it is added directly to the oil phase.
9. The use of a polymeric thickener according to any of claims 1 to 7 in the preparation of an acidic system product; preferably, the acidic system product is an acidic cosmetic or pharmaceutical product.
10. An acidic system product comprising the polymeric thickener according to any one of claims 1 to 7; preferably, the acidic system product is an acidic cosmetic or pharmaceutical product.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111487871.7A CN114224784A (en) | 2021-12-06 | 2021-12-06 | Macromolecular thickener and preparation method and application thereof |
| CN2021114878717 | 2021-12-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114569496A true CN114569496A (en) | 2022-06-03 |
| CN114569496B CN114569496B (en) | 2024-02-27 |
Family
ID=80753794
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111487871.7A Withdrawn CN114224784A (en) | 2021-12-06 | 2021-12-06 | Macromolecular thickener and preparation method and application thereof |
| CN202210268670.6A Active CN114569496B (en) | 2021-12-06 | 2022-03-18 | Polymer thickener and preparation method and application thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111487871.7A Withdrawn CN114224784A (en) | 2021-12-06 | 2021-12-06 | Macromolecular thickener and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (2) | CN114224784A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116606562B (en) * | 2023-04-27 | 2024-03-12 | 英德市城泰化工有限公司 | Preparation method of high-dispersivity paste benzoyl peroxide for sheet metal ash |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1908026A (en) * | 2006-08-17 | 2007-02-07 | 广州市天赐高新材料科技有限公司 | Acrylamide crosslinking copolymer emulsion and preparation method thereof |
| CN103976893A (en) * | 2014-05-09 | 2014-08-13 | 广州百孚润化工有限公司 | Novel macromolecule emulsifier for cosmetics and preparation method thereof |
-
2021
- 2021-12-06 CN CN202111487871.7A patent/CN114224784A/en not_active Withdrawn
-
2022
- 2022-03-18 CN CN202210268670.6A patent/CN114569496B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1908026A (en) * | 2006-08-17 | 2007-02-07 | 广州市天赐高新材料科技有限公司 | Acrylamide crosslinking copolymer emulsion and preparation method thereof |
| CN103976893A (en) * | 2014-05-09 | 2014-08-13 | 广州百孚润化工有限公司 | Novel macromolecule emulsifier for cosmetics and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 宋天文: "丙烯酸系耐盐型增稠剂的合成及性能研究", 国家科技图书文献中心 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114224784A (en) | 2022-03-25 |
| CN114569496B (en) | 2024-02-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1116733B1 (en) | Water-soluble or water-swellable crosslinked copolymers | |
| US6355752B1 (en) | Neutralized crosslinked polymers of acrylamidoalkylsulfonic acids and N-vinylamides | |
| US5990233A (en) | Rheology modifiers for use in aqueous compositions | |
| JPH11180824A (en) | Stable w/o/w emulsion and cosmetic and/or its use as composition for dermatology | |
| CN114569496A (en) | Macromolecular thickener and preparation method and application thereof | |
| JP3180814B2 (en) | Use of a copolymer comprising a carboxylic acid and a long-chain compound having an isolated CC multiple bond as a thickener or dispersant | |
| US6664356B1 (en) | Leach resistant oil based carrier for cosmetically and pharmaceutically active agents | |
| CN103976893B (en) | A kind of macromolecule emulsifier used for cosmetic and preparation method thereof | |
| US20060275240A1 (en) | Synthetic thickeners for cosmetics | |
| US9138703B2 (en) | Composition made of polyalkoxylated derivatives of trimethylolpropane and fatty alcohols, method for preparing said composition, and use thereof as a reverser in self-reversible reverse latexes | |
| US6566473B1 (en) | Process for making a vinyl amide polymer composition for skin and hair compositions | |
| DE4141693A1 (en) | METHOD FOR PRODUCING A WATER-SOLUBLE POLYMER SUSPENSION | |
| US9333162B2 (en) | Thickening polymer reducing the stickiness of glycerine-based cosmetic formulas | |
| US20070258927A1 (en) | Inverse Emulsions as Thickeners for Cosmetics | |
| CN117586447A (en) | Fast wetting type ion-resistant carbomer and preparation method and application thereof | |
| DE102008008179A1 (en) | Process for the preparation of polymers by ion exchange | |
| CN114195943A (en) | Carbomer thickening agent capable of being quickly wetted and dispersed and preparation method thereof | |
| KR101249687B1 (en) | Crosslinked copolymer based on monomer containing phosphorylcholine-like group, inverse emulsion, and cosmetic composition | |
| EP1464659A1 (en) | Process for preparing stable polymer concentrates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |