CN117551125A - Azelaic acid organic silicon supermolecule ionic salt and preparation method thereof - Google Patents
Azelaic acid organic silicon supermolecule ionic salt and preparation method thereof Download PDFInfo
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- CN117551125A CN117551125A CN202311543931.1A CN202311543931A CN117551125A CN 117551125 A CN117551125 A CN 117551125A CN 202311543931 A CN202311543931 A CN 202311543931A CN 117551125 A CN117551125 A CN 117551125A
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- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 title claims abstract description 180
- 150000003839 salts Chemical class 0.000 title claims abstract description 39
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 10
- 239000010703 silicon Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title abstract description 17
- -1 ion salt Chemical class 0.000 claims abstract description 41
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims abstract description 36
- 210000004209 hair Anatomy 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims description 18
- 230000000844 anti-bacterial effect Effects 0.000 claims description 11
- 239000002537 cosmetic Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 10
- 238000002604 ultrasonography Methods 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- 229940095673 shampoo product Drugs 0.000 claims description 4
- 230000003752 improving hair Effects 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000009210 therapy by ultrasound Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 26
- 239000007788 liquid Substances 0.000 abstract description 22
- 230000000694 effects Effects 0.000 abstract description 10
- 239000001257 hydrogen Substances 0.000 description 29
- 229910052739 hydrogen Inorganic materials 0.000 description 29
- 238000012360 testing method Methods 0.000 description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 20
- 239000000126 substance Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 12
- 239000000523 sample Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000002453 shampoo Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- 229960002504 capsaicin Drugs 0.000 description 7
- 235000017663 capsaicin Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 241000208422 Rhododendron Species 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 208000002874 Acne Vulgaris Diseases 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 206010000496 acne Diseases 0.000 description 4
- 238000007865 diluting Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009960 carding Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000005496 eutectics Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003676 hair preparation Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 210000003491 skin Anatomy 0.000 description 3
- 230000007928 solubilization Effects 0.000 description 3
- 238000005063 solubilization Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000006285 cell suspension Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
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- 230000009878 intermolecular interaction Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- PHIQHXFUZVPYII-ZCFIWIBFSA-N (R)-carnitine Chemical compound C[N+](C)(C)C[C@H](O)CC([O-])=O PHIQHXFUZVPYII-ZCFIWIBFSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 229920000832 Cutin Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 238000000861 blow drying Methods 0.000 description 1
- 229960004203 carnitine Drugs 0.000 description 1
- 229940059958 centella asiatica extract Drugs 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 231100000640 hair analysis Toxicity 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- 229960003493 octyltriethoxysilane Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 230000004783 oxidative metabolism Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036548 skin texture Effects 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/695—Silicon compounds
-
- 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
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/02—Local antiseptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/18—Azelaic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
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- Birds (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses azelaic acid organic silicon supermolecule ion salt and a preparation method thereof, belonging to the technical field of supermolecules. According to the invention, azelaic acid and gamma-aminopropyl triethoxy silane are adopted to form liquid ionic salt through the supermolecular effect, so that the water solubility of azelaic acid is effectively improved, the mutual solubility of azelaic acid ionic salt with high content (46 wt%) and water with any ratio can be realized, the practicability of azelaic acid in a product formula is greatly facilitated, and the effective concentration of azelaic acid is ensured. The gamma-aminopropyl triethoxy silane in the supermolecular ion salt of the invention synergistically improves the flexibility of the azelaic acid, and expands the application of the azelaic acid in hair products.
Description
Technical Field
The invention relates to azelaic acid organic silicon supermolecule ion salt and a preparation method thereof, belonging to the technical field of supermolecules.
Background
Azelaic acid is naturally present in cereal substances such as rye, barley and wheat, and has effects of anti-inflammatory, acne removing, whitening and mark removing. Azelaic acid can lighten skin color, and obviously improve uniformity of skin texture and lighten spots of the face. Azelaic acid is a weak acid, and has effects of dissolving cutin, controlling excessive keratinization of hair follicle, and also can partially dissolve acne, and reducing acne generation. Azelaic acid has good antibacterial effect on two common bacteria causing infection on skin surface, namely acne bacillus and staphylococcus epidermidis, and can inhibit cell oxidative metabolism, remove free radicals and inhibit inflammation.
However, azelaic acid has low solubility in water, common solvents and solubilizing agents, limiting its use. The addition amount of azelaic acid in cosmetics on the market at present is usually up to 15-20%, most of azelaic acid can only form paste under the use amount, transparent uniform stable liquid substances can not be formed at all, the recommended use amount of azelaic acid is difficult to achieve by common solubilizers or methods, and the solubility of azelaic acid in water and oil solvents is not ideal. Thus, researchers need to find more ways to increase the solubility of azelaic acid in order to better utilize the various functions of azelaic acid. Meanwhile, there are few reports on azelaic acid for hair cosmetics to improve softness.
In order to improve the water solubility of azelaic acid, patent CN 113248364a discloses a method for increasing the water solubility of azelaic acid by compounding an alkaline substance (such as theophylline, choline, carnitine, etc.) with azelaic acid to form a salt, but the preparation process needs a large amount of organic solvents and the flow is complex; patent CN 112624918A discloses a eutectic crystal of azelaic acid and organic base and a preparation method thereof, wherein solid eutectic crystal is prepared in an organic solvent under inert gas, and then a series of operations such as membrane filtration, recrystallization, organic solvent removal and the like are required to obtain a target eutectic crystal, which is not environment-friendly and complex in process, and specific solubilization values of azelaic acid are not explicitly pointed out in the patent; patent CN 110669226a discloses a process for the preparation of a polyethylene glycol/propylene glycol/azelaic acid supermolecule system, which comprises dissolving azelaic acid first with propylene glycol and polyethylene glycol as solvents, then adding the dissolved system hot to a large amount of water, propylene glycol and polyethylene glycol being solvents and solubilisers commonly used in cosmetic formulations, which essentially are the thermal solubilizations of azelaic acid under conventional alcohol and polyethylene glycol solubilisation, so that the solubility of azelaic acid can only be improved up to 3.33 times, i.e. about 8g/L; CN 110272353B discloses a capsaicin-azelaic acid ionic salt with whitening and antioxidation functions, the ionic salt preparation needs to dissolve azelaic acid in a solvent in advance and then react with capsaicin, and meanwhile, the ionic salt is solid, so that the target ionic salt can be obtained after the preparation is finished, and the whole process takes 75 hours. More importantly, it does not indicate whether azelaic acid is effective for solubilization.
Disclosure of Invention
[ technical problem ]
The solubility of azelaic acid is not obviously improved by the current method;
the conventional gamma-aminopropyl triethoxysilane is directly added into cosmetics and does not need to be combined with other substances;
there are few reports on the use of azelaic acid in hair cosmetics to improve softness and smoothness.
Technical scheme
In order to solve the problems, the invention selects specific gamma-aminopropyl triethoxy silane and specific azelaic acid to prepare the supermolecule ion salt, and aims at improving the water solubility of azelaic acid and simultaneously synergistically enhancing the softening efficacy of azelaic acid so as to expand the application of azelaic acid in hair cosmetics.
Gamma-aminopropyl triethoxysilane is a common organosilicon compound. In cosmetics, it can play a variety of functional roles. Firstly, gamma-aminopropyl triethoxysilane can be used as a thickener and an emulsifier, which can improve the texture and stability of cosmetics, increase the viscosity and viscosity thereof, and make the cosmetics easier to use and apply; in addition, it can form an emulsion between the oil and water, helping to mix the immiscible components and providing better dispersion. Secondly, the gamma-aminopropyl triethoxysilane also has the functions of moisturizing and moisturizing, can form a layer of film on the surface of the skin, reduces the evaporation of moisture and provides long-acting moisturizing effect. Meanwhile, because of the existence of an organosilicon structure, the gamma-aminopropyl triethoxysilane can be used in shampoo products to enhance the softness of hair.
The first object of the present invention is to provide an azelaic acid organosilicon supramolecular ionic salt having the structural formula i or ii:
in one embodiment, azelaic acid and gamma-aminopropyl triethoxysilane form liquid ionic salts through supermolecular action, and the ionic salts can be mixed with water in any proportion, so that the water solubility of azelaic acid can be effectively improved.
In one embodiment, the supramolecular ionic salt does not affect the bacteriostatic properties of azelaic acid and can synergistically impart a compliant efficacy thereto.
A second object of the present invention is to provide a process for preparing an azelaic acid organosilicon supramolecular ionic salt comprising the steps of:
according to the mole ratio of 1:1 or 1:2 mixing azelaic acid and gamma-aminopropyl triethoxysilane, stirring and heating or constant temperature ultrasonic treatment to obtain the azelaic acid organosilicon supermolecule ion salt.
In one embodiment, the atmosphere of stirring heating or constant temperature ultrasound is nitrogen or natural air.
In one embodiment, the temperature of the agitation heating or constant temperature ultrasound is 20 to 80 ℃.
In one embodiment, the stirring heating or constant temperature ultrasound is carried out for a period of 5 to 40 minutes.
In one embodiment, the rotational speed of the agitation heating is 200-1000 rpm and the power of the constant temperature ultrasound is 200-800W.
A third object of the present invention is the use of the ionic salts of organosilicon supramolecules of azelaic acid according to the invention in the cosmetic or pharmaceutical field.
The fourth object of the invention is to provide a hair care shampoo product with antibacterial and softening properties, which contains the azelaic acid organic silicon supermolecule ion salt.
In one embodiment, the organosilicon supramolecular ionic salt of azelaic acid is present in an amount of 0.1 to 30wt%.
In one embodiment, the hair care shampoo product comprises a hair care essence, shampoo, hair mask, and the like.
A fifth object of the present invention is a method for improving hair softness by employing the organosilicon supramolecular ion salt of azelaic acid of the present invention.
[ advantageous effects ]
(1) According to the invention, azelaic acid and gamma-aminopropyl triethoxy silane are adopted to form liquid ionic salt through the supermolecular effect, so that the water solubility of azelaic acid is effectively improved, the mutual solubility of azelaic acid ionic salt with high content (46 wt%) and water with any ratio can be realized, the practicability of azelaic acid in a product formula is greatly facilitated, and the effective concentration of azelaic acid is ensured.
(2) The gamma-aminopropyl triethoxy silane in the supermolecular ionic salt of the invention synergistically improves the flexibility of azelaic acid, and expands the application of azelaic acid in flexible hair products.
(3) From the perspective of environmental protection, the method for preparing the supermolecule ionic salt is environment-friendly, avoids the use and emission of toxic and harmful substances, and has the advantages of short reaction time, simple operation and easy large-scale production.
(4) The preparation process of the supermolecular ionic salt is very simple, green and safe, low in energy consumption and short in time consumption, and the obtained supermolecular ionic salt can be directly used as a raw material to be directly applied to the field of cosmetics or pharmacy without complicated post-treatment processes such as purification, separation and the like, so that the supermolecular ionic salt is suitable for industrial popularization.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of formula I in example 1.
FIG. 2 is a nuclear magnetic resonance spectrum of formula II in example 2.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for better illustration of the invention, and should not be construed as limiting the invention.
The testing method comprises the following steps:
1. nuclear magnetic data testing:
machine specification: AVANCE III HD 400MHz;
and (3) machine manufacturers: swiss bruke company;
experimental parameters: magnet: 9.4 Tesla, and the magnetic field drift is less than or equal to 8Hz/h; the probe width is 5mm, the sampling frequency is 400MHz, and the test temperature is 25 ℃.
2. Antibacterial performance test:
the antibacterial test comprises the preparation of a culture medium and the preparation of an experimental bacterial liquid, and the preparation of the culture mediumReferring to the evaluation of antibacterial protection of cosmetics in cosmetics microbiology, the preparation of the experimental bacterial liquid comprises the following steps: respectively inoculating standard strain, amplifying on culture medium, culturing at 36deg.C for 24 hr, respectively adding into eluent with corresponding concentration, eluting, and making into gel with colorimetric turbidity method with viable bacteria content of about 10 per 1mL 8 Cell suspensions of standard bacteria, and the number of bacteria per 1mL of cell suspension of standard bacteria was determined separately using a microbial limit check method. After culturing to the appropriate colony, a 28d microbiological challenge test of the disposable bacteria is performed. The samples were divided into two groups, and 30g of the test group solution and 30g of the control group solution were added, respectively. 1 part of test bacterial liquid (0.5 mL) is added into each detection sample, and the samples are fully mixed and uniformly stirred, sampled every 7, 14 and 28 days, and the bacterial content of the samples is measured and evaluated again. The conditions for the sample to pass the antimicrobial challenge test were: the log value of the bacterial number of 14d is reduced by not less than 2.0, and the bacterial number of 14-28 d is not increased; otherwise, it is considered as not passing.
3. Hair combing test:
taking a hair sample Slightly Damaged Chinese hair (slightly damaged hair tresses of Chinese) and carrying out pretreatment: washing with 1% K12 (sodium dodecyl sulfate) solution in 37 deg.C constant temperature water bath for 30min, washing with 4.8L/min tap water at 37 deg.C for 1min, printing with chipless paper towel to dry water, and hanging in constant temperature and humidity environment for 12-24 hr for natural air drying; the dry combing work is measured as the base value before sample receiving.
Then, the supermolecular ion salt obtained in this example was added to the same commercial shampoo (control group) and 0.5% by mass, respectively, to obtain a new shampoo (test group) machine-rinse.
And (3) washing for 15 times in a total continuous machine, wherein the middle process does not carry out blow-drying treatment, the hair bundle drying and carding work of the 1 st, 5 th, 10 th and 15 th times is respectively measured, and the change rate of the test index before and after each hair bundle sample is calculated according to the formula (1):
k= (after F use/before F use-1). Times.100% (1)
If the carding power change rate K of the hair piece before and after sample receiving is less than 0, the test sample has the effect of improving the hair carding property; if the change rate K of combing power before and after sample receiving is more than 0, namely the combing power is increased, the test sample does not have the effect of improving the combing property of the hair.
4. High-low temperature cycle:
freezing at-5 ℃, taking out and dissolving at 40 ℃ to obtain a circulation, and observing whether a uniform transparent and stable solution can be formed.
Example 1
An azelaic acid organic silicon supermolecule ion salt, which has the following structure:
the preparation method of azelaic acid organic silicon supermolecule ion salt comprises the following steps:
0.01mol of azelaic acid and 0.02mol of gamma-aminopropyl triethoxysilane are weighed and put into a reaction vessel, and stirred for 40min under the natural air atmosphere at 25 ℃ and 500rpm, thus obtaining uniform transparent and stable liquid supermolecule ionic salt.
The synthetic route is as follows:
the content of azelaic acid in the obtained supermolecule ion salt is 30wt%, the supermolecule ion salt is diluted by adding water for 1 time, 5 times, 10 times, 20 times and 50 times, and the obtained supermolecule ion salt and each diluted system are respectively placed for 3 months in natural light at room temperature, placed for 3 months in a baking oven at 45 ℃, and circulated for 15 times at high and low temperature (-5-40 ℃) without insoluble substances and color change.
The nuclear magnetic resonance hydrogen spectrum of the supermolecule ion salt is shown in figure 1;
the nuclear magnetic hydrogen spectrum data of the supermolecular ion salt is as follows:
1 H NMR(400MHz,DMSO)δ5.64(s,6H),3.79-3.69(m,6H),3.47-3.41(m,6H),2.70-2.52(m,4H),2.08-1.98(m,6H),1.53-1.41(m,6H),1.33-1.18(m,6H),1.15(t,J＝7.0Hz,9H),1.06(t,J＝7.0Hz,9H),0.68-0.44(m,4H).
as can be seen from fig. 1: azelaic acid in chemistryA distinct carboxyl proton peak was present at a shift of 11.93 ppm; meanwhile, in the nuclear magnetic hydrogen spectrum of the gamma-aminopropyl triethoxy silane, the peak position of the amino hydrogen which is active hydrogen is about 1.47ppm of chemical shift, and the total hydrogen number is 2. Compared with azelaic acid and gamma-aminopropyl triethoxysilane, the disappearance of carboxyl proton hydrogen signal of the supermolecular ion salt at 11.93ppm of hydrogen spectrum chemical shift, and the appearance of a new single broad peak at 5.64ppm of chemical shift with the total hydrogen number of 6 are 6 protonated amino (+NH) groups in the supermolecular ion salt 3 ) The hydrogen peaks. This is a very obvious indication that the carboxyl protons of azelaic acid undergo an amino transfer to gamma-aminopropyl triethoxysilane, effecting an intermolecular interaction. In addition, the number of hydrogen (62H) in the nuclear magnetic hydrogen spectrum of the supermolecular ion salt completely accords with the structure of the formula I, and besides the proton migration, other hydrogen has partial chemical shift phenomenon compared with azelaic acid and gamma-aminopropyl triethoxysilane monomer, which all indicate that the chemical environment in the obtained supermolecular ion salt is changed relative to two independent monomer molecules, namely azelaic acid serving as a hydrogen bond donor and gamma-aminopropyl triethoxysilane serving as a hydrogen bond acceptor form the supermolecular ion salt through intermolecular proton transfer.
Adding triple distilled water into the supermolecule ionic salt obtained in the example 1 to prepare a sample with azelaic acid concentration of 0.5mol/L as an experimental group; 0.05mol of azelaic acid and 0.05mol of sodium hydroxide are weighed, added into 100mL of triple distilled water, heated and dissolved, the pH of the solution is adjusted to 7.0 by 1mol/L of hydrochloric acid after the dissolution, and the solution after filtration and sterilization is used as a blank control for antibacterial property test and is recorded as a control group 1; a1 mol/L aqueous gamma-aminopropyl triethoxysilane triple distilled solution was prepared and used as a control group 2 for antibacterial property test.
The test results are shown in Table 1, and can be seen from Table 1: the number index of Escherichia coli, pseudomonas aeruginosa and Staphylococcus aureus was reduced by more than 2.0 at 14d for both experimental group and control group 1, and the number index was reduced relatively little at 14d for control group 2; the number of bacteria did not increase for all components 14-28 d, and all three passed the antimicrobial challenge test. The addition of the sample of the supramolecular ionic salt system of this example also enhances the sterilizing effect on escherichia coli and staphylococcus aureus at 7d, compared to azelaic acid and gamma-aminopropyl triethoxysilane monomers, indicating that the supramolecular ionic salt formed by azelaic acid and gamma-aminopropyl triethoxysilane has better antibacterial properties than the single molecule of azelaic acid and gamma-aminopropyl triethoxysilane itself, namely: the combination of the two has a synergistic effect on antibacterial properties.
TABLE 1
Note that: control group 2 data was presented after the slash.
TABLE 2
The results of the hair combing test are shown in Table 2, and can be seen from Table 2: after the hair bundle treated by the shampoo (test group) added with 0.5% of the supermolecular ion salt obtained in the embodiment is used for a plurality of times, compared with the hair bundle before the treatment, the average value of combing work of the hair bundle after the treatment is as follows: 0.293J, average K value of-62.045%, average value of combing work of hair bundles treated by common commercial shampoo of a control group of 0.306J, average K value of-55.95%, and larger average value reduction of the K value of an experimental group, which indicates that the overall improved hair combing performance of the experimental group is more excellent; and the K value of the experimental group after 15 times of samples is-46.89%, and the K value of the control group is only-30.45%, which shows that the experimental group is more excellent in improving the long-term stability of the hair comb property. Experiments show that the supermolecular ion salt obtained in the embodiment can effectively reduce hair combing work and improve hair combing performance.
Example 2
An azelaic acid organic silicon supermolecule ion salt, which has the following structure:
the preparation method comprises the following steps:
weighing 0.01mol of azelaic acid and 0.01mol of gamma-aminopropyl triethoxysilane, and placing the mixture into a reaction vessel; the reaction atmosphere is nitrogen, and ultrasonic treatment is carried out for 5min at 80 ℃ to obtain uniform transparent and stable liquid supermolecule ionic salt.
The synthetic route is as follows:
the content of azelaic acid in the obtained supermolecule ion salt is 46wt%, and the supermolecule ion salt and the diluted system are respectively placed in natural light at room temperature for 3 months, in an oven at 45 ℃ for 3 months, and in high and low temperature (-5-40 ℃) for 15 times without insoluble substances and color change after being diluted by 1 time, 5 times, 10 times, 20 times and 50 times of water.
The nuclear magnetic resonance hydrogen spectrum of azelaic acid, gamma-aminopropyl triethoxysilane and supermolecule ion salt is shown in figure 2:
the nuclear magnetic hydrogen spectrum data of the supermolecular ion salt is as follows:
1 H NMR(400MHz,CDCl 3 )δ4.51(s,4H),3.98-3.58(m,6H),2.94-2.77(m,2H),2.29-2.15(m,4H),1.90-1.67(m,2H),1.64-1.49(m,4H),1.44-1.30(m,4H),1.26-1.19(m,9H),0.9-0.79(m,2H),0.73-0.53(m,2H).
as can be seen from fig. 2: azelaic acid has a distinct peak of carboxyl protons at chemical shift 11.93 ppm; meanwhile, in the nuclear magnetic hydrogen spectrum of the gamma-aminopropyl triethoxy silane, the peak position of the amino hydrogen which is active hydrogen is about 1.47ppm of chemical shift, and the total hydrogen number is 2. The disappearance of the carboxyl proton hydrogen signal of the supramolecular ion salt at 11.93ppm of chemical shift in hydrogen spectrum compared with azelaic acid and gamma-aminopropyl triethoxysilane, and the appearance of a new peak at 4.51ppm of chemical shift with total hydrogen number of 4 are 3 protonated amino (+NH) groups in the supramolecular ion salt 3 ) The hydrogen peaks and the remaining 1 carboxyl active H also peaks at this position. This is a very obvious indication that the carboxyl protons of azelaic acid undergo an amino transfer to gamma-aminopropyl triethoxysilane, effecting an intermolecular interaction. At the same time, the remaining one carboxyl proton and protonThe peaks of the amino groups are positioned at the same position, which shows that in the supermolecular ionic salt, hydroxyl, amino protons and carboxyl protons are in a dynamic exchange state in the deuteration reagent, and further shows that azelaic acid and gamma-aminopropyl triethoxysilane form the supermolecular ionic salt through the supermolecular effect. In addition, the number of hydrogens (39H) in the nuclear magnetic hydrogen spectrum of the supramolecular ion salt corresponds to the structure of formula II, except for the above proton transfer (+NH) 3 ) In addition, other hydrogen has partial chemical displacement shift phenomenon compared with azelaic acid and gamma-aminopropyl triethoxy silane monomer, which indicates that the chemical environment in the obtained supermolecule ionic salt is changed relative to that of two independent monomer molecules, namely azelaic acid is taken as hydrogen bond donor and gamma-aminopropyl triethoxy silane is taken as hydrogen bond acceptor to form supermolecule ionic salt through intermolecular proton transfer.
To further illustrate the stability of the supramolecular ionic salts of the present invention in hair formulations, the supramolecular ionic salts of the present examples were formulated into hair care concentrates according to the following formulation in table 3:
table 3 formula table of hair care essence
Note that: centella asiatica extract was purchased from Gui Linniu tai biotechnology limited.
The preparation method of the hair care essence comprises the following steps:
adding raw materials No. 1-5, no. 7 and No. 8 into a main cup, dissolving uniformly, and heating to 75 ℃;
adding the raw materials No. 6 and No. 11 into a main cup, and uniformly stirring;
adding the No. 9 raw material into the main cup, and homogenizing uniformly;
cooling to 45deg.C, adding the materials of No. 10 and No. 12, and stirring to obtain hair care essence.
The hair care essence is subjected to stability test by GB/T26367-2010 standard, and the stability is qualified.
Comparative example 1
The gamma-aminopropyl triethoxysilane of example 1 was adjusted to be dimethiconol (viscosity 10000 cst), otherwise identical to example 1.
The result shows that: a stable liquid system cannot be formed, and the obtained system is a solid-liquid mixture; diluting the obtained solid-liquid mixture with water for 1 time, 5 times, 10 times, 20 times and 50 times, and making the mixture insoluble.
Comparative example 2
The gamma-aminopropyl triethoxysilane of example 1 was adjusted to serine, otherwise the same as in example 1.
The result shows that: a stable liquid system cannot be formed, and the obtained system is a solid-liquid mixture; diluting the obtained solid-liquid mixture with water for 1 time, 5 times, 10 times, 20 times and 50 times, and making the mixture insoluble.
Comparative example 3
The gamma-aminopropyl triethoxysilane of example 1 was adjusted to triethoxyoctyl silane, and the other was the same as in example 1.
The result shows that: a stable liquid system cannot be formed, and the obtained system is a solid-liquid mixture; diluting the obtained solid-liquid mixture with water for 1 time, 5 times, 10 times, 20 times and 50 times, and making the mixture insoluble.
Comparative example 4
The gamma-aminopropyl triethoxysilane of example 1 was adjusted to aminopropyl polydimethylsiloxane, otherwise identical to example 1.
The result shows that: a stable liquid system cannot be formed, and the obtained system is a solid-liquid mixture; diluting the obtained solid-liquid mixture with water for 1 time, 5 times, 10 times, 20 times and 50 times, and making the mixture insoluble.
Comparative example 5
The gamma-aminopropyl triethoxysilane of example 1 was adjusted to capsaicin, otherwise the same as in example 1.
The result shows that: a stable liquid system cannot be formed, and the obtained system is solid powder; the obtained solid powder is diluted by 1 time, 5 times, 10 times, 20 times and 50 times by adding water, and is insoluble, and has solid insoluble substances.
Comparative example 6
An azalea acid capsaicin ionic salt prepared by the following method:
adding capsaicin into an aqueous solution dissolved with azalea acid (0.5 mol/L) in a nitrogen atmosphere at a temperature of 40 ℃ under a warm water bath condition, and carrying out a neutralization reaction to obtain the azalea acid capsaicin ion salt; the molar ratio of the azalea acid to the capsaicin is 1:2; the neutralization reaction time is 12 hours; separating and purifying the obtained mixed solution through recrystallization, and carrying out suction filtration and drying treatment on the recrystallized product to obtain finished products of the azalea acid capsaicin ion salt; the drying temperature is 50 ℃ and the drying time is 48 hours. The scheme is long in time consumption, and needs to use an organic solvent to recrystallize the ionic salt and needs a large amount of post-treatment operations such as purification and the like. The obtained ionic salt is diluted by 1 time, 5 times, 10 times, 20 times and 50 times by water, and is insoluble, and a large amount of solid insoluble matters are formed.
The results of the hair combing test of the comparative examples are shown in table 4:
TABLE 4 Table 4
As can be seen from table 4: after the hair tress treated by the shampoo (test group) added with 0.5% of the product obtained in the comparative example is used for a plurality of times, the average value of combing work of the hair tress after treatment is as follows: 0.3225J, wherein the average K value is-53.73%, the average value of the combing work of the hair bundles after the treatment of common commercial shampoo in a control group is 0.306J, the average value of the K value is-55.95%, the average value of the K value in an experimental group is reduced to be similar to or even slightly lower than that in the control group, and the degree of reduction of the K value after 15 times of samples is similar, so that whether the product of the comparative example is added has little influence on the combing effect of the shampoo or not is indicated, namely, the product obtained in the comparative example does not have obvious effect of improving the combing property of the hair.
While the invention has been described with reference to the preferred embodiments, it is not limited thereto, and various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. An azelaic acid organosilicon supermolecule ion salt, which is characterized in that the structural formula is shown as the following formula I or formula II:
2. a process for preparing the organosilicon supramolecular ionic salt of azelaic acid according to claim 1, characterized in that it comprises the following steps:
according to the mole ratio of 1:1 or 1:2 mixing azelaic acid and gamma-aminopropyl triethoxysilane, stirring and heating or constant temperature ultrasonic treatment to obtain the azelaic acid organosilicon supermolecule ion salt.
3. The method according to claim 2, wherein the atmosphere of stirring heating or constant temperature ultrasound is nitrogen or natural air.
4. The method according to claim 2, wherein the temperature of stirring heating or constant temperature ultrasound is 20 to 80 o C。
5. The method according to claim 2, wherein the stirring heating or constant temperature ultrasound is carried out for a period of 5 to 40 minutes.
6. The method according to claim 2, wherein the stirring and heating speed is 200-1000 rpm and the constant temperature ultrasonic power is 200-800W.
7. Use of the organosilicon supramolecular ion salt of azelaic acid according to claim 1 in the cosmetic or pharmaceutical field.
8. A hair care shampoo product with antibacterial and softening properties, which comprises the azelaic acid organic silicon supermolecule ion salt as claimed in claim 1.
9. The hair care shampoo product with antibacterial and softening properties according to claim 8, wherein the amount of azelaic acid organic silicon supermolecule ion salt is 0.1-30wt%.
10. A method for improving hair softness, characterized in that the azelaic acid organosilicon supramolecular ionic salt according to claim 1 is used.
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