CN114767564A - Preservative, preparation method thereof and cosmetic - Google Patents
Preservative, preparation method thereof and cosmetic Download PDFInfo
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- CN114767564A CN114767564A CN202210359200.0A CN202210359200A CN114767564A CN 114767564 A CN114767564 A CN 114767564A CN 202210359200 A CN202210359200 A CN 202210359200A CN 114767564 A CN114767564 A CN 114767564A
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- China
- Prior art keywords
- preservative
- acid
- anisic acid
- weak
- weak base
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- 239000003755 preservative agent Substances 0.000 title claims abstract description 84
- 230000002335 preservative effect Effects 0.000 title claims abstract description 82
- 239000002537 cosmetic Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title abstract description 15
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims abstract description 193
- WNGSUWLDMZFYNZ-UHFFFAOYSA-N Leonurine Chemical compound COC1=CC(C(=O)OCCCCN=C(N)N)=CC(OC)=C1O WNGSUWLDMZFYNZ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- ZSBXGIUJOOQZMP-UHFFFAOYSA-N Isomatrine Natural products C1CCC2CN3C(=O)CCCC3C3C2N1CCC3 ZSBXGIUJOOQZMP-UHFFFAOYSA-N 0.000 claims abstract description 23
- ZSBXGIUJOOQZMP-JLNYLFASSA-N Matrine Chemical compound C1CC[C@H]2CN3C(=O)CCC[C@@H]3[C@@H]3[C@H]2N1CCC3 ZSBXGIUJOOQZMP-JLNYLFASSA-N 0.000 claims abstract description 23
- 229930014456 matrine Natural products 0.000 claims abstract description 23
- 239000004475 Arginine Substances 0.000 claims abstract description 21
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000004472 Lysine Substances 0.000 claims abstract description 21
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 17
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims abstract description 9
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical class COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 claims description 24
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 17
- 229940071248 anisate Drugs 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000001291 vacuum drying Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 8
- 238000001953 recrystallisation Methods 0.000 claims description 8
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 239000012266 salt solution Substances 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000002421 anti-septic effect Effects 0.000 abstract description 9
- 230000006378 damage Effects 0.000 abstract description 9
- 241000894006 Bacteria Species 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
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- 230000001580 bacterial effect Effects 0.000 description 11
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- 239000000843 powder Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000523 sample Substances 0.000 description 8
- 238000005260 corrosion Methods 0.000 description 7
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 7
- 239000000341 volatile oil Substances 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
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- 238000012258 culturing Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
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- 241000228245 Aspergillus niger Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 150000003797 alkaloid derivatives Chemical class 0.000 description 3
- 239000000686 essence Substances 0.000 description 3
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- 230000000813 microbial effect Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 230000003405 preventing effect Effects 0.000 description 3
- VUWCWMOCWKCZTA-UHFFFAOYSA-N 1,2-thiazol-4-one Chemical class O=C1CSN=C1 VUWCWMOCWKCZTA-UHFFFAOYSA-N 0.000 description 2
- 241000228197 Aspergillus flavus Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 241000228153 Penicillium citrinum Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000223014 Syzygium aromaticum Species 0.000 description 2
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 2
- -1 aromatic alcohols Chemical class 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000125205 Anethum Species 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 208000012639 Balance disease Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000009024 Ceanothus sanguineus Nutrition 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 241000207923 Lamiaceae Species 0.000 description 1
- 241000218195 Lauraceae Species 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 240000002817 Leonurus sibiricus Species 0.000 description 1
- 235000002434 Leonurus sibiricus Nutrition 0.000 description 1
- 240000003553 Leptospermum scoparium Species 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 240000002262 Litsea cubeba Species 0.000 description 1
- 235000012854 Litsea cubeba Nutrition 0.000 description 1
- 235000015459 Lycium barbarum Nutrition 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 235000007265 Myrrhis odorata Nutrition 0.000 description 1
- 241000219926 Myrtaceae Species 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 240000004760 Pimpinella anisum Species 0.000 description 1
- 235000012550 Pimpinella anisum Nutrition 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241001093501 Rutaceae Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 241000246044 Sophora flavescens Species 0.000 description 1
- 241000234299 Zingiberaceae Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005536 corrosion prevention Methods 0.000 description 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 description 1
- 229960003964 deoxycholic acid Drugs 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000018343 nutrient deficiency Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000037307 sensitive skin Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
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- 208000006379 syphilis Diseases 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000001993 wax Substances 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- 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
- A61K8/34—Alcohols
- A61K8/345—Alcohols 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
-
- 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
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
Abstract
The application relates to a preservative, a preparation method thereof and a cosmetic, wherein the preservative comprises: (A) salts of anisic acid with a weak base selected from matrine, leonurine, lysine, arginine or combinations thereof; (B) and (b) a solvent, wherein the molar concentration of the component (A) is 0.02-0.1 mol/L. The preservative provided by the application is characterized in that the anisic acid is dissolved in the solvent in the form of a salt of the anisic acid and a weak base, so that the problem of low solubility of the anisic acid is solved, and the preservative effect of the anisic acid is enhanced. The antiseptic can be used as natural antiseptic in cosmetics without causing damage to human skin.
Description
Technical Field
The application belongs to the technical field of chemical material modification, and particularly relates to a preservative, a preparation method thereof and cosmetics.
Background
Preservatives are substances which have a continuous inhibitory effect on the growth of microorganisms. The sources of preservatives in general are of three general types: 1) aromatic alcohols, benzoic acid and derivatives thereof, aromatic ethers, isothiazolinones; 2) ethanol, essential oils, etc., such as litsea cubeba essential oil, lavender essential oil, clove essential oil, tea tree essential oil; wherein the clove essential oil inhibits gram-positive and gram-negative bacteria, mold, yeast; 3) the Chinese medicinal extract component also has antiseptic effect, and is commonly found in Compositae, Leguminosae, Liliaceae, Zingiberaceae, Rutaceae, Myrtaceae, Lauraceae, semen Cassiae alcohol, etc.
Preservatives are an essential class of ingredients in cosmetics. Cosmetic preservatives are used primarily to protect products from microbial contamination during manufacture or use. The traditional preservative can inhibit bacteria, has certain damage to human skin, and is easy to cause skin allergy and irritation reaction.
Disclosure of Invention
The application provides a preservative, a preparation method thereof and cosmetics, and aims to solve the problem that the traditional preservative damages the skin of a human body.
In one aspect, embodiments herein provide a preservative comprising: (A) salts of anisic acid with a weak base selected from matrine, leonurine, lysine, arginine or combinations thereof; (B) and the solvent is used, wherein the molar concentration of the component (A) in the component (B) is 0.02-0.1 mol/L.
Preferably, the component (a) is a salt of anisic acid with matrine and/or leonurine.
Preferably, the component (a) is a salt of anisic acid with lysine and/or arginine.
Preferably, the solvent comprises a polyol preservative.
Preferably, the polyol preservative comprises 1, 2-pentanediol.
In another aspect, embodiments of the present application also provide a method for preparing a preservative, comprising the steps of:
(1) mixing anisic acid and weak base in water for reaction to obtain solution of anisic acid weak base and weak base, wherein the weak base is selected from matrine, leonurine, basic amino acid or their combination;
(2) obtaining weak acid and weak base salt of anisic acid from the weak acid and weak base salt solution of anisic acid;
(3) and dissolving the weak acid base salt of anisic acid in a solvent at a molar concentration of 0.02-0.1 mol/L to obtain the preservative.
Preferably, the mixing and reacting anisic acid with weak base in water in the step (1) comprises the following steps: adding anisic acid and weak base into water, and stirring for 0.5-1 h.
Preferably, said obtaining of the weak acid and weak base anisate salt from said weak acid and weak base anisate salt solution in step (2) comprises: and carrying out reduced pressure distillation, recrystallization and drying treatment on the solution of the weak acid and weak base of the anisic acid to obtain the weak acid and weak base salt of the anisic acid.
Preferably, the drying treatment comprises vacuum drying treatment at 40-50 ℃ for 12-24 h.
In yet another aspect, embodiments of the present application also provide a cosmetic including the above-described preservative or the preservative prepared by the above-described method.
Anisic acid has a remarkable bacteriostatic effect on staphylococcus aureus, escherichia coli, bacillus subtilis, aspergillus niger, aspergillus flavus and penicillium citrinum, but anisic acid is difficult to dissolve in water. In the preservative provided by the application, the anisic acid is dissolved in the solvent in the form of a salt of the anisic acid and a weak base, so that the problem of low solubility of the anisic acid is solved, and the preservative effect of the anisic acid is enhanced. Wherein the weak base is selected from matrine, leonurine, basic amino acid or their combination. The antiseptic can be used as natural antiseptic in cosmetics without causing damage to human skin.
Detailed Description
In order to make the objects, technical solutions and advantageous technical effects of the present invention clearer, the present invention is further described in detail with reference to the following embodiments. It should be understood that the embodiments described in this specification are only for the purpose of explaining the present invention and are not intended to limit the present invention.
For the sake of brevity, only some numerical ranges are explicitly disclosed herein. However, any lower limit may be combined with any upper limit to form ranges not explicitly recited; and any lower limit may be combined with any other lower limit to form a range not explicitly recited, and similarly any upper limit may be combined with any other upper limit to form a range not explicitly recited. Also, although not explicitly recited, each point or individual numerical value between the endpoints of a range is encompassed within that range. Thus, each point or individual value can form a range not explicitly recited as its own lower or upper limit in combination with any other point or individual value or in combination with other lower or upper limits.
In the description herein, it is to be noted that, unless otherwise specified, "above" and "below" are inclusive, and "a plurality" of "one or more" means two or more.
Preservative agent
Embodiments of the first aspect of the present application provide a preservative comprising: (A) salts of anisic acid with a weak base selected from matrine, leonurine, lysine, arginine or combinations thereof; (B) and (B) a solvent, wherein the molar concentration of the component (A) in the component (B) is 0.02-0.1 mol/L.
Anisic acid is isolated from essential oil of the plant Anethum vulgare flower. Anisic acid is also called 4-methoxybenzoic acid, P-anisic acid, P-anisic acid, 4-anisic acid or P-anisic acid, can be used as antibacterial agent, pH regulator and essence perfume raw material, has no irritation to human skin, and has a safety risk of grade 1; under the acidic condition, the synthesis of the fungicin can be prevented, the traditional preservative is replaced, and the antibacterial effect is achieved; has lasting fragrance of fructus crataegi, can mask unpleasant odor, and can be used as essence and perfume; can adjust the pH of the system and is used as a pH regulator. p-anisic acid, an acid naturally present in anise, is frequently used as an odor inhibitor in cosmetics and has antifungal properties, and can replace conventional preservatives for preservation.
Anisic acid has significant bacteriostatic effect on staphylococcus aureus, escherichia coli, bacillus subtilis, aspergillus niger, aspergillus flavus and penicillium citrinum. However, the inventors found that anisic acid is hardly soluble in water and has a solubility in water of 0.3g/L at 20 ℃. However, 0.3g/L is not enough to meet the requirement of product preservation, and can not be directly used as a preservative.
Matrine and leonurine both belong to alkaloids that can use the cosmetic raw materials category. The matrine is prepared from dried root, plant, and fruit of Sophora flavescens ait of Leguminosae by extracting, and can be dissolved in water (with low solubility), chloroform, methanol, and ethanol. Matrine can form weak acid weak base salt with anisic acid. Leonurine is extracted from leaf of Leonurus sibiricus of Labiatae, has effects of promoting blood circulation, removing blood stasis, inducing diuresis, and relieving swelling, and is also an alkaloid with alkalescence, and is dissolved in cold water with hot water solubility of 1% -2%, and is dissolved in pentanol. Leonurine can also form weak acid weak base salts with anisic acid.
The basic amino acids include lysine and arginine, and have important medical value, and the lysine can be used for treating nutritional deficiency, hypoplasia and nitrogen balance disorder; the compound preparation (Minuofen) prepared from arginine and deoxycholic acid is an effective medicine for mainly treating syphilis, viral jaundice and other diseases.
The inventors have found that anisic acid can form a salt with a specific weak base (such as matrine, leonurine, lysine, arginine or a combination thereof), that such a salt of anisic acid with a weak base can be easily dispersed in a solvent at a desired concentration, and that when the molar concentration of the salt of anisic acid with a weak base in a solvent is 0.02 to 0.1mol/L, an excellent preservative effect can be provided. For example, the molar concentration of the salt of anisic acid with a weak base in the solvent is 0.02mol/L, 0.03mol/L, 0.04mol/L, 0.05mol/L, 0.06mol/L, 0.07mol/L, 0.08mol/L, 0.09mol/L, or 0.1 mol/L. The molar concentration of the salt of anisic acid with the weak base in the solvent may also be in any combination of the above values. Salts of anisic acid with weak bases solve the problem of solubility of anisic acid.
The requirement of the beauty industry on the preservative is safe, non-allergic, natural, degradable and environment-friendly; the antiseptic is used as natural antiseptic and applied in cosmetics without damage to skin.
In the examples of the present application, the component (a) is a salt of anisic acid with matrine and/or leonurine. For example, a mixture of a salt of anisic acid and matrine, a salt of anisic acid and leonurine, a salt of anisic acid and matrine, and a salt of anisic acid and leonurine is component (a).
In the examples of the present application, the component (a) is a salt of anisic acid with lysine and/or arginine. For example, a mixture of a salt of anisic acid with lysine as component (a), a salt of anisic acid with arginine as component (a), a salt of anisic acid with lysine as component (a), and a salt of anisic acid with arginine as component (a).
In embodiments of the present application, the solvent comprises a polyol preservative.
According to the cosmetic industry, the preservative can be divided into surface-internal preservative and surface-external preservative, wherein the surface-internal preservative comprises alcohols, parabens, isothiazolinones, formaldehyde releasers and organic acids; the external preservative comprises polyhydric alcohol, ketone, middle and long carbon chain polar amphiphilic substance and organic acid.
In embodiments herein, the polyol preservative includes 1, 2-pentanediol.
The 1, 2-pentanediol has broad-spectrum preservative activity, has good synergistic preservative effect with the anisic acid, can be used as a preservative auxiliary agent, reduces the dosage of the traditional preservative, strengthens the preservative effect of the product, reduces the irritation of the product caused by the use of the preservative, and is particularly suitable for sensitive and delicate skin.
Preparation of preservatives
Embodiments of the second aspect of the present application provide a method of preparing a preservative comprising the steps of:
(1) mixing anisic acid and weak base in water for reaction to obtain solution of weak base of anisic acid, wherein the weak base is selected from matrine, leonurine, lysine, arginine or their combination;
(2) obtaining weak acid and weak base salt of anisic acid from the weak acid and weak base salt solution of anisic acid;
(3) and dissolving the weak acid base salt of anisic acid in a solvent at a molar concentration of 0.02-0.1 mol/L to obtain the preservative.
In the embodiment of the present application, the mixing and reacting anisic acid with weak base in water in step (1) comprises: adding anisic acid and weak base into water, and stirring for 0.5-1 h.
In some embodiments, anisic acid is mixed with a weak base in water at a molar ratio of 1:1 and reacted with stirring to form a weak base solution of anisic acid. Wherein the stirring reaction time is 0.5-1h, such as 0.5h, 0.6h, 0.7h, 0.8h, 0.9h or 1.0 h. The stirring reaction time may be in any combination of the above values.
In the examples of the present application, said obtaining of the weak acid base anisate salt from said weak acid base anisate salt solution in step (2) comprises: and carrying out reduced pressure distillation, recrystallization and drying treatment on the solution of the weak acid and weak base of the anisic acid to obtain the weak acid and weak base salt of the anisic acid.
In the embodiment of the application, the drying treatment comprises vacuum drying treatment for 12-24 hours at 40-50 ℃.
In some embodiments, the drying treatment is vacuum drying at 50 ℃ for 24h to obtain the weak acid and weak base anisate salt.
In some embodiments, the solvent is a polyol preservative, such as 1, 2-pentanediol.
The method for preparing the preservative provided by the embodiment of the invention can be used for preparing the preservative, the process is simple, the prepared preservative is stable in system, and the preservative belongs to a preservative of a natural source and cannot cause damage to human skin when being used in cosmetics.
Cosmetic preparation
Embodiments of the third aspect of the invention provide a cosmetic product comprising a preservative as provided in embodiments of the first aspect of the invention or as prepared by a method as provided in embodiments of the second aspect of the invention.
According to the embodiment provided by the invention, the preservative contained in the cosmetic is a natural preservative, no chemical component exists in the cosmetic, no damage is caused to the skin of a human body, and the cosmetic is particularly suitable for people with sensitive skin.
In an embodiment of the present application, the cosmetic product is a lipstick.
Lipstick is a cosmetic mainly used on lips and capable of increasing the color of the lips or changing the color of the lips, and comprises pigments, fillers, waxes, oils, pearling agents, essences, preservatives and the like as main components. The lipstick is easily carried into the mouth or body by the user during use, and the safety of the preservatives in the lipstick is even more important.
According to the embodiment of the application, the preservative used in the lipstick is a natural source, and the preservative cannot cause damage to human skin and harm to body health when being used in the lipstick.
Examples
The present disclosure is more particularly described in the following examples that are intended as illustrative only, since various modifications and changes within the scope of the present disclosure will be apparent to those skilled in the art. Unless otherwise indicated, all parts, percentages, and ratios reported in the following examples are on a weight basis, and all reagents used in the examples are commercially available or synthesized according to conventional methods and can be used directly without further treatment, and the equipment used in the examples is commercially available.
Example 1
In this example, matrine was selected as the weak base, and the preparation method of the preservative includes the following steps:
adding matrine into water, adding anisic acid, and reacting under stirring to obtain weak acid and weak base anisate salt, wherein the molar ratio of the weak base anisate salt to the weak base anisate salt is 1:1, stirring for 0.5-1 h; carrying out reduced pressure distillation, recrystallization and drying treatment on the product after reaction; preferably carrying out vacuum drying treatment at the temperature of 40-50 ℃ for 12-24 h; obtaining solid powder of matrine anisate; the solid powder was taken 1.5% by mass and dissolved in 1, 2-pentanediol to give the natural preservative of example 1 (the molar concentration of matrine anisate was about 0.037 mol/L).
Example 2
In this example, leonurine was selected as the weak base, and the preparation method of the preservative includes the following steps:
adding leonurine into water, then adding anisic acid, and reacting under stirring to generate a product, namely the weak acid and weak base anisate salt, wherein the molar ratio of the leonurine to the anisic acid is 1:1, stirring for 0.5-1 h; carrying out reduced pressure distillation, recrystallization and drying treatment on the product after reaction; preferably carrying out vacuum drying treatment at the temperature of 40-50 ℃ for 12-24 h; obtaining leonurine anisate as solid powder; this solid powder was taken 1.5% by mass and dissolved in 1, 2-pentanediol to give the natural preservative of example 2 (the molar concentration of leonurine anisate was about 0.032 mol/L).
Example 3
Arginine was selected as the weak base in this example, and the preservative was prepared by the following steps:
adding arginine into water, adding anisic acid, and stirring to generate a product which is the weak acid and weak base salt of anisic acid, wherein the molar ratio of the weak acid and the weak base salt of anisic acid is 1:1, stirring for 0.5-1 h; carrying out reduced pressure distillation, recrystallization and drying treatment on the product after reaction; preferably performing vacuum drying treatment at 40-50 deg.C for 12-24 h; obtaining arginine anisate as a solid powder; the solid powder was taken and dissolved in 1.5% by mass in 1, 2-pentanediol to give the natural preservative of example 3 (arginine anisate at a molar concentration of about 0.045 mol/L).
Example 4
In the embodiment, lysine is selected as weak base, and the preparation method of the preservative comprises the following steps:
adding lysine into water, adding anisic acid, and stirring to generate a product which is the weak acid and weak base salt of anisic acid, wherein the molar ratio of the two is 1:1, stirring for 0.5-1h, preferably 40 min; carrying out reduced pressure distillation, recrystallization and drying treatment on the product after reaction; preferably vacuum drying at 40-50 deg.C for 12-24 hr, more preferably at 50 deg.C for 24 hr; obtaining solid powder lysine anisate; this solid powder was taken to be 1.5% by mass and dissolved in 1, 2-pentanediol to obtain the natural preservative of example 4 (the molar concentration of lysine anisate was about 0.049 mol/L).
Example 5
In this example, histidine was selected as the weak base, and the preservative was prepared by the following steps:
adding histidine into water, adding anisic acid, and stirring to obtain weak acid and weak base anisate salt as the product, wherein the molar ratio of the weak acid and the weak base anisate salt is 1:1, stirring for 0.5-1h, preferably 40 min; carrying out reduced pressure distillation, recrystallization and drying treatment on the product after reaction; preferably vacuum drying at 40-50 deg.C for 12-24h, more preferably at 50 deg.C for 24 h; obtaining histidine anisate as a solid powder; the solid powder was taken and 1.5% by mass was dissolved in 1, 2-pentanediol to give the natural preservative of example five (histidine anisate at a molar concentration of about 0.048 mol/L).
Comparative example
Comparative example 1
1.5% by mass of alcohol (95% content) was dissolved in 1, 2-pentanediol to obtain a mixture.
Comparative example 2
1.5 mass percent of deionized water was dissolved in 1, 2-pentanediol to obtain a mixture.
Performance test
First, Water solubility test
(ii) a sample having a solubility in 100g of water of less than 0.01g at 20 ℃ is defined as being poorly soluble or insoluble; solubility between 0.01g and 1g, defined as slightly soluble; solubility is defined as soluble between 1-10 g; solubility greater than 10g is defined as readily soluble; above 50g, it is defined as very soluble.
Preparing 7 cups of 100g of water, adding 0.01g of seven samples of examples 1-5 and comparative examples 1-2 respectively, and if dissolved, continuing to add to 1g of the samples; adding to 10g if dissolution continues; if dissolution continues, add to 50 g. The solubility of the seven samples in the aqueous solution was recorded separately, giving the results shown in the following table (table 1):
TABLE 1 Water solubility test results of examples and comparative examples
| Sample(s) | Solubility in water |
| Example 1 | Is easy to dissolve |
| Example 2 | Is easy to dissolve |
| Example 3 | Is easy to dissolve |
| Example 4 | Is easy to dissolve |
| Example 5 | Is easy to dissolve |
| Comparative example 1 | Is very soluble in water |
| Comparative example 2 | Is very soluble in water |
From the above experimental results, it was found that the modified anisic acid changed from being hardly soluble in water (the water-soluble solubility of anisic acid was 0.3g/L) to being easily soluble in water in the 1, 2-hexanediol solution. The modified anisic acid does indeed increase the solubility in aqueous solutions.
Second, corrosion resistance test
The preservative test uses examples and comparative examples as experimental samples, combines the preservative principle and effect of anisic acid, alkaloid/basic amino acid and 1, 2-pentanediol, selects bacteria (staphylococcus aureus, escherichia coli, pseudomonas aeruginosa), candida albicans and mold (aspergillus niger); preparing standard suspension, bacterial suspension and mould suspension; wherein the culture medium is beef extract peptone culture medium and agar culture medium.
1. Preparation of bacterial liquid for test
(1) Preparation of Standard suspensions
9.9mL of 1% sulfuric acid and 0.1mL of 1% barium chloride are mixed to prepare a suspension with the concentration of 3X 108cfu/mL, this suspension was diluted three more times.
(2) Preparation of bacterial suspensions
Before the experiment, the strain is inoculated on each culture medium slant and cultured at the constant temperature of 36 ℃ for 48 h. Washing the cultured active strains in a sterilized conical flask by using sterilized normal saline, fully oscillating and shaking up, and sucking bacterial liquid from the conical flask by using a pipettor for dilution until the turbidity is the same as that of the standard suspension; diluting the diluted bacterial liquid by three times to obtain the required 1 × 108cfu/mL of bacterial suspension, and the total number of bacteria is determined.
(3) Preparation of mould suspension
Washing the cultured active strains in a sterilized conical flask by using sterilized normal saline, and fully shaking up; the bacteria liquid is sucked from the conical flask by a pipette gun for ten-fold dilution in sequence, the total number of the molds in 5 middle lattices is required to be 190-210 by adopting a blood counting plate technology for each dilution, and the required 1X 10 of the bacteria suspension falling in the range is8cfu/mL of mold suspension, and determining the number of molds by taking the total number of the molds.
2. Inoculation of
Single-bacterium inoculation: each test strain was individually subjected to a challenge test. Inoculating once at the beginning of the test, and carrying out the whole test period28 days (28 day microbial challenge experiment with one addition); taking 30g of sample to be tested, correspondingly adding 0.3mL of sample with the concentration of 1X 107cfu/mL-1×108Uniformly stirring cfu/mL bacterial suspension and mould suspension with a clean sterile spoon, covering with a preservative film, culturing bacteria in an incubator at 32.5 +/-2.5 ℃, and culturing mould in an incubator at 22.5 +/-2.5 ℃.
Since the examples and comparative examples are water-soluble samples, 90mL of sterile physiological saline was added to 10g of the sample, and 1mL of the sample solution was diluted and added to 9mL of sterile physiological saline to sequentially dilute 10g of the sample solution-1、10-2、10-3、10-4、10-5、10-6、10-7Equal dilution; three samples with appropriate dilution are taken, 1mL of the samples are respectively sucked and added into a sterilized plate, and colony counting is carried out, and two parallel operations are carried out.
3. Culturing
Culturing the bacteria in an incubator at 32.5 +/-25 ℃;
the mold is cultured in an incubator at 22.5 +/-2.5 ℃.
4. Colony counting
And separating and calculating bacteria and molds in the sample on days 0, 7, 14, 21 and 28 respectively, and after the total number of the bacteria and the total number of the molds are calculated each time, putting the plate back to the incubator for the next observation.
Standard method for colony counting:
1) selecting a plate with the average bacterial colony number between 30 and 300 as a total bacterial colony number measuring range, and selecting a plate with the average bacterial colony number between 5 and 20 as a total mould colony number measuring range;
2) two dilutions are between 30-300, and the ratio is calculated; if the ratio is more than 2, calculating the total number of bacteria by using the smaller dilution; otherwise, reporting the average number;
3) all dilutions were greater than 300, calculated as the average colony with the highest dilution;
4) all dilutions were less than 30, calculated as the average colony with the lowest dilution;
5) all dilutions were outside of 30-300, one of which was greater than 300, and the adjacent plus one dilution was less than 30, calculated as the average colony count closest to 30 or 300;
6) if the plate contains colonies which are connected into a sheet shape or flower dot shape and spread and grow, the calculation is not suitable;
7) if the plate colonies are less than half of the plate and the colonies are uniform in the other half, the plate colonies can be counted and multiplied by 2 to report the number of colonies in the whole plate.
5. Evaluation criteria
The initial inoculum size of mold and bacteria of the CTFA (american cosmetic association) method was 10000CFU/g (ml) and 1000000CFU/g (ml) (CFU is colony unit), respectively, requiring a 90% reduction in mold, a 99.9% reduction in bacteria at day seven and a continuous reduction in bacteria count over 28 days.
TABLE 2 evaluation criteria for microbial preservation challenge experiments with one-time addition of bacteria for CTFA
Examples 1-5, comparative examples 1-2 were subjected to the corrosion challenge test described above, according to the CTFA test standard in the united states, to obtain the results of the following table (table 3):
TABLE 3 results of corrosion prevention experiments of examples and comparative examples
| Sample (I) | Results |
| Example 1 | Excellent anticorrosion effect |
| Example 2 | The anticorrosion effect is marginal |
| Example 3 | The anticorrosion effect is marginal |
| Example 4 | Has excellent anti-corrosion effect |
| Example 5 | Ineffective corrosion preventing effect |
| Comparative example 1 | Ineffective corrosion preventing effect |
| Comparative example 2 | Ineffective corrosion preventing effect |
The experimental result shows that the anisate/1, 2-pentanediol preservative has higher preservative efficacy than the leonurine anisic acid/1, 2-pentanediol for alkaloid; lysine anisic acid/1, 2-pentanediol is the most potent preservative efficacy for the basic amino acids, arginine anisic acid/1, 2-pentanediol is the second, and histidine anisic acid/1, 2-pentanediol is the lowest preservative efficacy; whereas comparative example 1.5% ethanol/1, 2-pentanediol and 1.5% deionized water/1, 2-pentanediol corrosion protection challenges failed; the experimental results show that the antiseptic efficacy of the matrine anisic acid/1, 2-pentanediol and the lysine anisic acid/1, 2-pentanediol is strongest, and the matrine has a certain inhibition effect on bacterial mold and has a synergistic antiseptic effect with the anisic acid and the 1, 2-pentanediol; for basic amino acids, the order of the degree of basicity is: arginine > lysine > histidine; arginine is too basic, so that the hydrogen bonding effect on anisic acid is too strong, the solubility of the aqueous solution is enhanced, and the preservative effect of the anisic acid is inhibited; histidine, however, is not very soluble in aqueous solutions and has a low concentration of active substances, although it does not inhibit the preservative efficacy of anisic acid too much because of its too weak hydrogen bonding.
While the present application has been described with reference to preferred embodiments, various modifications may be made and equivalents may be substituted for elements thereof without departing from the scope of the present application, and in particular, features shown in the various embodiments may be combined in any manner as long as there is no structural conflict. The present application is not intended to be limited to the particular embodiments disclosed herein but is to cover all embodiments that may fall within the scope of the appended claims.
Claims (10)
1. A preservative, characterized in that the preservative comprises:
(A) salts of anisic acid with a weak base selected from matrine, leonurine, lysine, arginine or combinations thereof;
(B) a solvent, a water-soluble organic solvent,
wherein the molar concentration of the component (A) in the component (B) is 0.02-0.1 mol/L.
2. Preservative according to claim 1, characterized in that said component (a) is a salt of anisic acid with matrine and/or leonurine.
3. Preservative according to claim 1, characterized in that component (A) is a salt of anisic acid with lysine and/or arginine.
4. The preservative of claim 1, wherein the solvent comprises a polyol preservative.
5. The preservative of claim 4, wherein the polyol preservative comprises 1, 2-pentanediol.
6. A method of preparing a preservative comprising the steps of:
(1) mixing anisic acid and weak base in water for reaction to obtain solution of weak base and weak acid of anisic acid,
wherein the weak base is selected from matrine, leonurine, lysine, arginine or their combination;
(2) obtaining weak acid and weak base salt of anisic acid from the weak acid and weak base salt solution of anisic acid;
(3) and dissolving the weak base salt of the anisic acid weak acid in a solvent at a molar concentration of 0.02-0.1 mol/L to prepare the preservative.
7. The method for preparing antiseptic agent according to claim 6, wherein the mixing and reacting anisic acid with weak base in water in step (1) comprises:
adding anisic acid and weak base into water, and stirring for 0.5-1 h.
8. The method of claim 6, wherein the step (2) of obtaining the weak acid base anisate salt from the weak acid base anisate solution comprises:
and carrying out reduced pressure distillation, recrystallization and drying treatment on the solution of the weak acid and weak base of the anisic acid to obtain the weak acid and weak base salt of the anisic acid.
9. The method for preparing the preservative according to claim 8, wherein the drying treatment comprises vacuum drying treatment at 40-50 ℃ for 12-24 hours.
10. A cosmetic comprising the preservative according to any one of claims 1 to 5 or the preservative produced by the method according to any one of claims 6 to 9.
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| US20200352840A1 (en) * | 2019-05-06 | 2020-11-12 | Spinart, LLC | Formulations and methods for preparing stable cosmetic compositions |
| KR20210026896A (en) * | 2019-09-02 | 2021-03-10 | 주식회사 코스나 | Method for Natural preservative composition containing Illicium Verum (Anise) Fruit/Seed Oil |
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| US20200352840A1 (en) * | 2019-05-06 | 2020-11-12 | Spinart, LLC | Formulations and methods for preparing stable cosmetic compositions |
| KR20210026896A (en) * | 2019-09-02 | 2021-03-10 | 주식회사 코스나 | Method for Natural preservative composition containing Illicium Verum (Anise) Fruit/Seed Oil |
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