CN114515249A - Preparation method of antibacterial powder with different colors under illumination - Google Patents

Preparation method of antibacterial powder with different colors under illumination Download PDF

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Publication number
CN114515249A
CN114515249A CN202111634316.2A CN202111634316A CN114515249A CN 114515249 A CN114515249 A CN 114515249A CN 202111634316 A CN202111634316 A CN 202111634316A CN 114515249 A CN114515249 A CN 114515249A
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coupling agent
silane coupling
titanium dioxide
nano titanium
different colors
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Inventor
张千
张川
张建平
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HEBEI MILSON TITANIUM DIOXIDE CO Ltd
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HEBEI MILSON TITANIUM DIOXIDE CO Ltd
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Priority to CN202111634316.2A priority Critical patent/CN114515249A/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/29—Titanium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/022—Powders; Compacted Powders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • 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
    • 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
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • 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
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/438—Thermochromatic; Photochromic; Phototropic
    • 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
    • A61K2800/84—Products or compounds obtained by lyophilisation, freeze-drying
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Cosmetics (AREA)

Abstract

The invention relates to the technical field of cosmetics, and provides a preparation method of antibacterial powder with different colors under illumination. Through the technical scheme, the problems of poor skin-friendly property, insufficient antibacterial property and false white under illumination of the powder in the prior art are solved.

Description

Preparation method of antibacterial powder with different colors under illumination
Technical Field
The invention relates to the technical field of cosmetics, in particular to a preparation method of antibacterial powder with different colors under illumination.
Background
Titanium dioxide of the formula TiO2White powder, nontoxic and tasteless, insoluble in water and organic acid, stable in chemical property, basically free from reaction with other substances at room temperature, commonly called titanium dioxide. In nature, titanium dioxide exists in three crystal forms, namely anatase type, rutile type and brookite type.
Nano TiO 22Besides the advantages of common nano material, it also has photocatalytic activity and UV absorptionThe antibacterial and bactericidal coating has the advantages of stable performance, stable chemical performance, transparency, low price, easy obtainment, good biocompatibility and the like, and is widely applied to the fields of environmental protection, medical treatment, energy, papermaking, coating, ceramics, plastics, cosmetics and the like. Because the nanometer titanium dioxide has small particle size and can block ultraviolet rays, the nanometer titanium dioxide is widely applied to the field of cosmetics, for example, titanium dioxide is added into foundation liquid, loose powder and pressed powder, and the effects of inhibiting bacteria, modifying skin color and blocking ultraviolet rays can be achieved at the same time. However, the nano titanium dioxide matrix applied to the base makeup product has the problems of poor skin-friendly property, easy makeup removal and the like, and when the ultraviolet rays are strong in summer, the nano titanium dioxide matrix may reflect light and be white, so that the use feeling of a user is influenced.
Disclosure of Invention
The invention provides a preparation method of antibacterial powder with different colors under illumination, which solves the problems in the related art.
The technical scheme of the invention is as follows:
the preparation method of antibacterial powder with different colors under illumination is characterized by taking dicarboxy azobenzene modified hyaluronic acid and silane coupling agent modified nano titanium dioxide as raw materials and carrying out amidation reaction to prepare the antibacterial powder.
As a further technical scheme, the preparation method of the antibacterial powder with different colors under illumination comprises the following steps:
s1, dissolving dicarboxylazobenzene modified hyaluronic acid, dicyclohexylcarbodiimide and silane coupling agent modified nano titanium dioxide in a buffer solution;
s2, adding the silane coupling agent to modify the nano titanium dioxide again for reaction;
and S3, carrying out post-treatment to obtain the antibacterial powder.
As a further technical scheme, the mass-to-volume ratio of the dicarboxylazobenzene modified hyaluronic acid, the dicyclohexylcarbodiimide and the silane coupling agent modified nano titanium dioxide in the step S1 is as follows: (220- & ltSUB & gt 250mg) & lt (1-2ml) & lt (120- & gt 150 mg).
As a further technical scheme, the ratio of the silane coupling agent modified nano titanium dioxide in the step S2 to the silane coupling agent modified nano titanium dioxide in the step S1 is 1 (1.2-1.5).
As a further technical scheme, in the step S1, the buffer solution is PBS buffer solution with pH 6.4.
As a further technical scheme, the post-treatment is specifically centrifugation treatment, dialysis and freeze drying.
As a further technical scheme, the conditions of the centrifugal treatment are 15000rpm/min and 4 ℃.
As a further technical proposal, the dialysis is carried out in water/acetone solution for three days, and the molecular weight of the dialysis membrane is 6000-8000 MW.
As a further technical scheme, the preparation method of the dicarboxy azobenzene modified hyaluronic acid comprises the following steps: dissolving hyaluronic acid, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide in a buffer solution, adding an acetone solution of dicarboxy azobenzene, and reacting to obtain the dicarboxy azobenzene modified hyaluronic acid.
Preferably, the preparation method of the dicarboxylazobenzene modified hyaluronic acid comprises the following steps: hyaluronic acid, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide are dissolved in PBS buffer solution with the pH value of 7.4, acetone solution of dicarboxylazobenzene is dripped into the PBS buffer solution to react for 48 hours, and the mixture is frozen and dried after centrifugal dialysis.
As a further technical scheme, the preparation method of the silane coupling agent modified nano titanium dioxide comprises the following steps: mixing KH-550 silane coupling agent, water and ethanol, adjusting pH, heating, adding nano titanium dioxide, dispersing, stirring, washing, centrifuging and drying to obtain silane coupling agent modified nano titanium dioxide.
Preferably, the preparation method of the silane coupling agent modified nano titanium dioxide comprises the following steps: mixing KH-550 silane coupling agent, water and ethanol, adjusting pH to 4, heating to 60 ℃, adding nano titanium dioxide, performing ultrasonic dispersion, keeping the temperature at 60 ℃, stirring for 1h, washing, centrifuging and drying to obtain the silane coupling agent modified nano titanium dioxide.
The synthetic route of the invention is as follows:
Figure BDA0003441316840000021
Figure BDA0003441316840000031
the invention has the beneficial effects that:
1. in the invention, dicarboxylazobenzene (Azo) is used for modifying hyaluronic acid (Azo-HA), carboxyl and functional hydroxyl are two most common modification sites of HA, and the modified hyaluronic acid can react with epoxy compounds, alcohols, acids and acid anhydrides to generate HA esterified derivatives. The physical and chemical properties and biological properties of HA are changed to a certain extent by esterifying and modifying the HA with dicarboxy azobenzene, thereby expanding the application field of HA. The HA carboxyl activity is high and is usually the recognition point of an HA receptor or hyaluronidase, so that the HA carboxyl can be modified, not only can be subjected to esterification reaction, but also can be subjected to amidation reaction with various amine substances to obtain an HA amidated derivative, and the HA amidated derivative can be subjected to amidation reaction with the amino-introduced silane coupling agent modified titanium dioxide to truly attach light sensation, moisture retention and skin affinity to the nano titanium dioxide powder.
2. The antibacterial powder can be prepared into makeup and foundation, has skin nourishing and moisturizing effects and excellent sunscreen effect, has good skin feel and skin adhesion without adding a skin feel regulator, and also has good antibacterial effect. The antibacterial powder can adjust different colors according to illumination, and avoid the occurrence of whitening and brightening.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any inventive step, are intended to be within the scope of the present invention.
Example 1
S1, modifying the nano titanium dioxide by using KH-550 (coupling agent):
taking 1mL of KH-550, 10mL of deionized water and 90mL of absolute ethyl alcohol, adjusting the pH value to 4 by using hydrochloric acid and sodium hydroxide solution, controlling the temperature to be 60 ℃, and stirring for 1h to obtain a mixed solution; weighing 1.0g of nano TiO2Adding into the mixed solution of deionized water and anhydrous ethanol, ultrasonic dispersing for 5min, and adding into the mixed solution; stirring at 60 deg.C for 1h, cleaning with mixed solution of deionized water and anhydrous ethanol, centrifuging, dispersing in mixed solution again, and repeating for 5 times; drying at 100 deg.C for 6 hr, grinding, and marking the obtained powder as m-TiO2。
S2, modifying hyaluronic acid by dicarboxy azobenzene:
HA (190mg) and 2mL of 1-ethyl- (3-dimethylaminopropyl) carbodiimide (EDC) and 1mL of N-hydroxysuccinimide (NHS) were dissolved in 200mL of PBS buffer (pH 7.4) and stirred well for 2h to achieve a molar ratio of glucuronic acid residues in HA of 1:1: 1. Then, 100mL of an Azo (140mg) acetone solution was added dropwise, and after stirring at room temperature for 48 hours, the resulting mixture was centrifuged at 15000rpm at 4 ℃ in a centrifuge. Dialyzing in mixed solution of water/acetone (v1/v2 ═ 3:1) for 3 days, wherein the molecular weight of the dialysis membrane is 6000-.
S3, synthesizing antibacterial powder with different color effects:
240mg of Azo-HA, 2ml of dicyclohexylcarbodiimide (DDC) and 130mg of m-TiO were taken2The two solutions were dissolved together in 200mL of PBS buffer solution with pH 6.4 and stirred at room temperature for 2h until the solution became homogeneous. 100mg of m-TiO was added to the solution2And stirred at room temperature for 12 h. The reaction mixture was centrifuged at 15000rpm at 4 ℃ in a centrifuge until the solution was not clear. Dialyzing in mixed solution of water/acetone (v1/v2 ═ 3:1) for 3 days, wherein the molecular weight of the dialysis membrane is 6000-.
Example 2
S1, S2 are the same as in example 1, and S3 is prepared according to the following steps:
220mg of Azo-HA and 1ml of twoCyclohexylcarbodiimide (DDC) and 120mg of m-TiO2The two solutions were dissolved together in 200mL of PBS buffer solution with pH 6.4 and stirred at room temperature for 2h until the solution became homogeneous. 100mg of m-TiO was added to the solution2And stirred at room temperature for 12 h. The reaction mixture was centrifuged at 15000rpm at 4 ℃ in a centrifuge until the solution was not clear. Dialyzing in mixed solution of water/acetone (v1/v2 ═ 3:1) for 3 days, wherein the molecular weight of the dialysis membrane is 6000-.
Example 3
S1, S2 are the same as in example 1, and S3 is prepared according to the following steps:
250mg of Azo-HA, 2ml of dicyclohexylcarbodiimide (DDC) and 150mg of m-TiO were taken2The two solutions were dissolved together in 200mL of PBS buffer solution with pH 6.4 and stirred at room temperature for 2h until the solution became homogeneous. 100mg of m-TiO was added to the solution2And stirred at room temperature for 12 h. The reaction mixture was centrifuged at 15000rpm at 4 ℃ in a centrifuge until the solution was not clear. Dialyzing in mixed solution of water/acetone (v1/v2 ═ 3:1) for 3 days, wherein the molecular weight of the dialysis membrane is 6000-.
The present invention is not limited to the above preferred embodiments, and any modifications, equivalent substitutions, improvements, etc. within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims (10)

1. The preparation method of the antibacterial powder with different colors under illumination is characterized in that dicarboxylazobenzene modified hyaluronic acid and silane coupling agent modified nano titanium dioxide are used as raw materials and are prepared through amidation reaction.
2. The method for preparing antibacterial powder with different colors under illumination according to claim 1, characterized by comprising the following steps:
s1, dissolving dicarboxylazobenzene modified hyaluronic acid, dicyclohexylcarbodiimide and silane coupling agent modified nano titanium dioxide in a buffer solution;
s2, adding the silane coupling agent to modify the nano titanium dioxide again for reaction;
and S3, carrying out post-treatment to obtain the antibacterial powder.
3. The method for preparing antibacterial powder with different colors under illumination according to claim 2, wherein the mass-to-volume ratio of the dicarboxylazobenzene modified hyaluronic acid, the dicyclohexylcarbodiimide and the silane coupling agent modified nano titanium dioxide in the step S1 is as follows: (220- & ltSUB & gt 250mg) & lt (1-2ml) & lt (120- & gt 150 mg).
4. The method of claim 3, wherein the ratio of the silane coupling agent modified nano-titania in step S2 to the silane coupling agent modified nano-titania in S1 is 1 (1.2-1.5).
5. The method according to claim 3, wherein the buffer solution in step S1 is PBS buffer solution with pH 6.4.
6. The method of claim 2, wherein the post-treatment comprises centrifugation, dialysis, and freeze-drying.
7. The method of claim 6, wherein the centrifugation is performed at 15000rpm/min and 4 ℃.
8. The method as claimed in claim 6, wherein the dialysis is performed in water/acetone solution for three days, and the molecular weight of the dialysis membrane is 6000-8000 MW.
9. The method for preparing antimicrobial powder with different colors under illumination according to claim 1, wherein the method for preparing dicarboxylazobenzene modified hyaluronic acid comprises the following steps: dissolving hyaluronic acid, 1-ethyl- (3-dimethylaminopropyl) carbodiimide and N-hydroxysuccinimide in a buffer solution, adding an acetone solution of dicarboxylazobenzene, and reacting to obtain dicarboxylazobenzene modified hyaluronic acid.
10. The method for preparing antibacterial powder with different colors under illumination according to claim 1, wherein the method for preparing the silane coupling agent modified nano titanium dioxide comprises the following steps: mixing KH-550 silane coupling agent, water and ethanol, adjusting pH, heating, adding nano titanium dioxide, dispersing, stirring, washing, centrifuging and drying to obtain silane coupling agent modified nano titanium dioxide.
CN202111634316.2A 2021-12-29 2021-12-29 Preparation method of antibacterial powder with different colors under illumination Pending CN114515249A (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103110535A (en) * 2013-02-05 2013-05-22 华东理工大学 Sunscreening granule with TiO2-HA core-shell structure as well as preparation method and application thereof
CN108619527A (en) * 2018-05-22 2018-10-09 大连理工大学 Antitumor drug resistant mesoporous TiO 2 Nano medication composition of one kind and preparation method thereof
CN110894302A (en) * 2019-11-19 2020-03-20 福建医科大学孟超肝胆医院(福州市传染病医院) Antibacterial hydrogel based on imine bond and acylhydrazone bond and preparation method thereof
CN113583262A (en) * 2021-06-24 2021-11-02 四川大学 Near-infrared response hyaluronic acid hydrogel for articular cartilage repair and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103110535A (en) * 2013-02-05 2013-05-22 华东理工大学 Sunscreening granule with TiO2-HA core-shell structure as well as preparation method and application thereof
CN108619527A (en) * 2018-05-22 2018-10-09 大连理工大学 Antitumor drug resistant mesoporous TiO 2 Nano medication composition of one kind and preparation method thereof
CN110894302A (en) * 2019-11-19 2020-03-20 福建医科大学孟超肝胆医院(福州市传染病医院) Antibacterial hydrogel based on imine bond and acylhydrazone bond and preparation method thereof
CN113583262A (en) * 2021-06-24 2021-11-02 四川大学 Near-infrared response hyaluronic acid hydrogel for articular cartilage repair and preparation method thereof

Non-Patent Citations (2)

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Title
RAHUL DEV MUKHOPADHYAY: "《Light driven mesoscale assembly of a coordination polymeric gelator into flowers and stars with distinct properties》", 《CHEMICAL SCIENCE》, no. 11, pages 110 *
艾玲: "《氨基多糖光敏改性研究》", 《中国优秀硕士学位论文全文数据库工程科技I辑》, no. 08, pages 9 *

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