CN100528956C - Nano particle of enwrapping water-soluble active ingredient, and preparation method - Google Patents
Nano particle of enwrapping water-soluble active ingredient, and preparation method Download PDFInfo
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- CN100528956C CN100528956C CNB200710044082XA CN200710044082A CN100528956C CN 100528956 C CN100528956 C CN 100528956C CN B200710044082X A CNB200710044082X A CN B200710044082XA CN 200710044082 A CN200710044082 A CN 200710044082A CN 100528956 C CN100528956 C CN 100528956C
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Abstract
This invention discloses a method for preparing nanoparticles containing water-soluble active component. The cores are composed of water-soluble active component, and the shells are composed of polymer of alkyl alpha-cyanoacrylate monomer. The average diameter of the nanoparticles at 25 deg.C is 100-500 nm. The water-soluble active component is one or more of vitamin C, vitamin B, hyaluronic acid and hyaluronic acid derivatives. The alkyl alpha-cyanoacrylate monomer is ethyl alpha-cyanoacrylate monomer or butyl alpha-cyanoacrylate monomer. The carrier material has such advantages as high biocompatibility, and high safety in cosmetic field. The method has such advantages as simple operation and high stability. The obtained nanoparticles have such advantages as small and uniform sizes, high permeability to skin, high drug loading rate, and stable protection of sensitive active substances.
Description
Technical field
The present invention relates to the w/o type nanoparticle that is prepared from by interfacial polymerization method, more particularly relate to nanoparticle of a kind of enwrapping water-soluble active ingredient that can be used for makeup and preparation method thereof with infiltration and slow releasing function.
Background technology
The medicament slow release technology comes across the eighties, realizes that with the nano controlled release pharmaceutical carrier medicament slow release technology is highly effective mode.This technology is applied to cosmetic field; the active substance nanoparticle that obtains has that penetration power is strong, had good sustained release effect, good characteristic such as be difficult for running off, sensitive composition is protected; can effectively improve skin mesocuticle and hair follicle gland assimilated efficiency to nutritive substance; avoid activeconstituents to run off and lose, in functional cosmetics, be with a wide range of applications with makeup.Because the sebum film that the skin outside has one deck to be invisible to the naked eye, for the skin-protection product of external application, skin can absorb fat-soluble nutritive ingredient wherein substantially.And for water-soluble vitamins, comprise vitamins C and vitamin B group etc., it water-soluble and light and heat is had unstable influenced its absorption and effect, therefore in most of the cases, the water-soluble vitamins isoreactivity material that adds in the skin-protection product all passes through the modification processing, for example vitamins C uses its derivative, can keep stability on the one hand, also is beneficial to the absorption of skin on the other hand.But the effect of this analog derivative is poor before than modification, thereby has influenced the performance of the finished product.Research indicates, as avoids water-soluble active ingredient directly to contact with airborne oxygen, can effectively improve the stability of activeconstituents, infiltration and absorption that the application of nanometer transmission system simultaneously can effectively improve nutritive substance.
Summary of the invention
It is simple that technical problem to be solved by this invention provides a kind of preparation method, and nano particle diameter is less and size is even, and the carrying drug ratio height has the nanoparticle and preparation method thereof of the enwrapping water-soluble active ingredient of stable provide protection to the susceptibility active substance.
The technical solution used in the present invention: a kind of nanoparticle of enwrapping water-soluble active ingredient, its microballoon kernel is a water-soluble active ingredient, its shell is the polymkeric substance that a-alkyl cyanoacrylate monomer polymerization produces, the median size of nanoparticle is 100～500 nanometers in the time of 25 ℃, wherein said water-soluble active ingredient is selected from one or more the mixture in vitamins C, vitamins B, hyaluronic acid, the hyaluronate sodium, and the polymkeric substance that described a-alkyl cyanoacrylate monomer polymerization produces is a-Tisuacryl or a-cyanacrylate.
The nanometer particle process method of above-mentioned enwrapping water-soluble active ingredient comprises the following steps:
A. with two kinds of nonionogenic tensides of span80/tween80 with 3～6: 1 proportioning is dissolved in the oil phase normal hexane, stirs fully dissolving, and the concentration of span80/tween80 compound emulsifying agent in normal hexane is 4.8～12% (wt);
B. water-soluble active ingredient is dissolved in the water, drip acetum and regulate pH value to 1.0～5.0, under the sonic oscillation, the drips of solution of water-soluble active ingredient is added in the oil phase of step a, oil phase and water volume ratio are 20～50: 1, stir after 0.5～1.0 hour, made the w/o type microemulsion that contains water-soluble active ingredient, wherein said water-soluble active ingredient is selected from one or more the mixture in vitamins C, vitamins B, hyaluronic acid or the hyaluronate sodium;
C. stir with a-alkyl cyanoacrylate monomer dropping in above-mentioned microemulsion, the monomeric consumption of a-alkyl cyanoacrylate is 0.06%～0.18% (wt), reacted 6.0～15.0 hours, after reaction finishes, to the reaction system centrifugation, 4000～6000 rev/mins of centrifugal rotational speeds are removed supernatant liquid after centrifugal 5～15 minutes, the Off-white solid nano drug-carrying particle that obtains separating out is the polyalkylcyanoacrylanano nano particle of enwrapping water-soluble active ingredient.
Beneficial effect of the present invention: the polyalkylcyanoacrylanano nano particle of the enwrapping water-soluble active ingredient of the present invention's preparation, particle diameter is 100～500 nanometers in the time of 25 ℃, can control the size of nanoparticle microballoon by the consumption of control a-alkyl cyanoacrylate monomer consumption, oil phase and water volume ratio, pH value of solution value, compound emulsifying agent.In the certain limit, the monomer consumption increases, and microspherulite diameter increases; Water oil ratio increases, and microspherulite diameter increases; The pH value of solution value increases, and microspherulite diameter increases; The emulsifying agent consumption increases, and particle diameter reduces.α-cyanoacrylate class solid support material good biocompatibility that the present invention is used; it is safe to be used for cosmetic field; the preparation method is simple to operate; stability is high; the gained nano particle diameter is less and size is even; percutaneous permeability is good, and the carrying drug ratio height is obvious to the stable provide protection of susceptibility active substance.
Description of drawings
Fig. 1 is the electromicroscopic photograph of nanoparticle of the present invention after phospho-wolframic acid dyeing;
Fig. 2 contains the electromicroscopic photograph of ascorbic nanoparticle after phospho-wolframic acid dyeing.
Embodiment
Below by embodiment the present invention is described in further detail:
A kind of nanoparticle of enwrapping water-soluble active ingredient, its microballoon kernel is a water-soluble active ingredient, its shell is the polymkeric substance that a-alkyl cyanoacrylate monomer polymerization produces, the median size of nanoparticle is 100～500 nanometers in the time of 25 ℃, wherein said water-soluble active ingredient is selected from one or more the mixture in vitamins C, vitamins B, hyaluronic acid or the hyaluronate sodium, and the polymkeric substance that described a-alkyl cyanoacrylate monomer polymerization produces is a-Tisuacryl or a-cyanacrylate.
The nanometer particle process method of enwrapping water-soluble active ingredient, comprise the following steps: a. with two kinds of nonionogenic tensides of span80/tween80 with 3～6: 1 proportioning is dissolved in the oil phase normal hexane, stir fully dissolving, the concentration of span80/tween80 compound emulsifying agent in normal hexane is 4.8～12% (wt); B. water-soluble active ingredient is dissolved in the water, drip acetum and regulate pH value to 1.0～5.0, under the sonic oscillation, the drips of solution of water-soluble active ingredient is added in the oil phase of step a, oil phase and water volume ratio are 20～50: 1, stir after 0.5～1.0 hour, made the w/o type microemulsion that contains water-soluble active ingredient, wherein said water-soluble active ingredient is selected from one or more the mixture in vitamins C, vitamins B, hyaluronic acid or the hyaluronate sodium; C. stir with a-alkyl cyanoacrylate monomer dropping in above-mentioned microemulsion, the monomeric consumption of a-alkyl cyanoacrylate is 0.06%～0.18% (wt), reacted 6.0～15.0 hours, after reaction finishes, to the reaction system centrifugation, 4000～6000 rev/mins of centrifugal rotational speeds are removed supernatant liquid after centrifugal 5～15 minutes, the Off-white solid nano drug-carrying particle that obtains separating out is the polyalkylcyanoacrylanano nano particle of enwrapping water-soluble active ingredient.
Embodiment 1
Get in the 0.15g vitamins C dry powder adding 50mL water and dissolve, and regulate pH value to 2.0.3.0g span80 and 0.6g tween80 are dissolved in the 50mL normal hexane, under the sonic oscillation, the 1mL vitamins C aqueous solution is added drop-wise in the oil phase that is dissolved with emulsifying agent, stir and made the system stable homogeneous in 0.5 hour and keep comparatively transparent clarifying state, and, present even micro emulsion shape with a kind of blue light phenomenon.Under stirring a-Tisuacryl monomer 0.02g slowly is added drop-wise in the good system of emulsification, reaction is 15 hours under the room temperature.Reaction is carried out centrifugation with system after finishing, and the rotating speed when centrifugal is 5000 rev/mins, centrifugation time 10 minutes, remove supernatant liquid, obtained the Off-white solid nano drug-carrying particle of separating out, be the paracyanogen base ethyl propenoate nano drug-carrying particulate of enwrapping water-soluble active ingredient.As shown in Figure 1, prepared microspherulite diameter is 280nm at 25 ℃, and carrying drug ratio is 17.6%, and encapsulation rate is 11.87%.80 ℃ of ascorbic storage rates after following 24 hours are 90%, far above 38% of the vitamins C aqueous solution under the equal conditions.As illustrated in fig. 1 and 2, gained contained the vitamins C nanoparticle after phospho-wolframic acid dyeing, adopt the shape characteristic and the distribution situation thereof of high resolving power transmission electron microscope observing particle, can find by electromicroscopic photograph, prepared nanoparticle is spherical in shape, and median size is about 150nm, and particle has tangible shell-core structure, dark matter is a water-soluble vitamin c in the middle of the particle, is divided into fat-soluble wall materials/substances than superficial part on every side.
Embodiment 2
Get in the 0.15g vitamins C dry powder adding 50mL water and dissolve, and regulate pH value to 3.0.3.0g span80 and 0.6g tween80 are dissolved in the 50mL normal hexane, under the sonic oscillation, the 1mL vitamins C aqueous solution is added drop-wise in the oil phase that is dissolved with emulsifying agent, stir and made the system stable homogeneous in 0.5 hour and keep comparatively transparent clarifying state, and, present even micro emulsion shape with a kind of blue light phenomenon.Under stirring a-Tisuacryl monomer 0.15g slowly is added drop-wise in the good system of emulsification, reacted again under the room temperature 15 hours.Reaction is carried out centrifugation with system after finishing, and the rotating speed when centrifugal is 5000 rev/mins, centrifugation time 10 minutes, remove top clear liquid, obtained the Off-white solid nano drug-carrying particle of separating out, be the paracyanogen base ethyl propenoate nano drug-carrying particulate of enwrapping water-soluble active ingredient.Prepared microspherulite diameter is 380nm at 25 ℃, and carrying drug ratio is 12.1%, and encapsulation rate is 8.16%.
Embodiment 3
Get in the 0.15g vitamins C dry powder adding 50mL water and dissolve, and regulate pH value to 4.0.3.0g span80 and 0.6g tween80 are dissolved in the 50mL normal hexane, under the sonic oscillation, the 1mL vitamins C aqueous solution is added drop-wise in the oil phase that is dissolved with emulsifying agent, stir and made the system stable homogeneous in 0.5 hour and keep comparatively transparent clarifying state, and, present even micro emulsion shape with a kind of blue light phenomenon.Under stirring a-Tisuacryl monomer 0.02g slowly is added drop-wise in the good system of emulsification, reacted again under the room temperature 15 hours.Reaction is carried out centrifugation with system after finishing, and the rotating speed when centrifugal is 5000 rev/mins, centrifugation time 10 minutes, remove top clear liquid, obtained the Off-white solid nano drug-carrying particle of separating out, be the paracyanogen base ethyl propenoate nano drug-carrying particulate of enwrapping water-soluble active ingredient.Prepared microspherulite diameter is 450nm at 25 ℃, and carrying drug ratio is 10.3%, and encapsulation rate is 6.95%.
Embodiment 4
Get in the 0.3g vitamins C dry powder adding 50mL water and dissolve, and regulate pH value to 2.0.3.0gspan80 and 0.6g tween80 are dissolved in the 50mL normal hexane, under the sonic oscillation, the 1mL vitamins C aqueous solution is added drop-wise in the oil phase that is dissolved with emulsifying agent, stir and made the system stable homogeneous in 0.5 hour and keep comparatively transparent clarifying state, and, present even micro emulsion shape with a kind of blue light phenomenon.Under stirring a-Tisuacryl monomer 0.02g slowly is added drop-wise in the good system of emulsification, reacted again under the room temperature 15 hours.Reaction is carried out centrifugation with system after finishing, and the rotating speed when centrifugal is 5000 rev/mins, centrifugation time 10 minutes, remove top clear liquid, obtained the Off-white solid nano drug-carrying particle of separating out, be the paracyanogen base ethyl propenoate nano drug-carrying particulate of enwrapping water-soluble active ingredient.Prepared microspherulite diameter is 320nm at 25 ℃, and carrying drug ratio is 15.8%, and encapsulation rate is 10.65%.
Embodiment 5
Get in the 0.2g hyaluronate sodium adding 50mL water and dissolve, and regulate pH value to 2.0.3.0gspan80 and 0.6g tween80 are dissolved in the 50mL normal hexane, under the sonic oscillation, the 1mL water dispersion is added drop-wise in the oil phase that is dissolved with emulsifying agent, stirs system stable homogeneous and the comparatively transparent clarifying state of maintenance of making in 0.5 hour, and, present even micro emulsion shape with a kind of blue light phenomenon.Under stirring a-Tisuacryl monomer 0.02g slowly is added drop-wise in the good system of emulsification, reacted again under the room temperature 15 hours.Reaction is carried out centrifugation with system after finishing, and the rotating speed when centrifugal is 5000 rev/mins, centrifugation time 10 minutes, remove supernatant liquor, obtained the Off-white solid nano drug-carrying particle of separating out, be the paracyanogen base ethyl propenoate nano drug-carrying particulate of enwrapping water-soluble active ingredient.Prepared microspherulite diameter is 210nm at 25 ℃, and carrying drug ratio is 9.8%, and encapsulation rate is 42.0%.
Above said content only is the basic explanation of the present invention under conceiving, and according to any equivalent transformation that technical scheme of the present invention is done, all should belong to protection scope of the present invention.
Claims (2)
1. the nanoparticle of an enwrapping water-soluble active ingredient, its microballoon kernel is a water-soluble active ingredient, its shell is the polymkeric substance that a-alkyl cyanoacrylate monomer polymerization produces, the median size of nanoparticle is 100～500 nanometers in the time of 25 ℃, wherein said water-soluble active ingredient is selected from one or more the mixture in vitamins C, vitamins B, hyaluronic acid, the hyaluronate sodium, and the polymkeric substance that described a-alkyl cyanoacrylate monomer polymerization produces is a-Tisuacryl or a-cyanacrylate.
2. the nanometer particle process method of the described enwrapping water-soluble active ingredient of claim 1 comprises the following steps:
A. with two kinds of nonionogenic tensides of span80/tween80 with 3～6: 1 proportioning is dissolved in the oil phase normal hexane, stirs fully dissolving, and the concentration of span80/tween80 compound emulsifying agent in normal hexane is 4.8～12% (wt);
B. water-soluble active ingredient is dissolved in the water, drip acetum and regulate pH value to 1.0～5.0, under the sonic oscillation, the drips of solution of water-soluble active ingredient is added in the oil phase of step a, oil phase and water volume ratio are 20～50: 1, stir after 0.5～1.0 hour, made the w/o type microemulsion that contains water-soluble active ingredient, wherein said water-soluble active ingredient is selected from one or more the mixture in vitamins C, vitamins B, hyaluronic acid or the hyaluronate sodium;
C. stir with a-alkyl cyanoacrylate monomer dropping in above-mentioned microemulsion, the monomeric consumption of a-alkyl cyanoacrylate is 0.06%～0.18% (wt), reacted 6.0～15.0 hours, after reaction finishes, to the reaction system centrifugation, 4000～6000 rev/mins of centrifugal rotational speeds are removed supernatant liquid after centrifugal 5～15 minutes, the Off-white solid nano drug-carrying particle that obtains separating out is the polyalkylcyanoacrylanano nano particle of enwrapping water-soluble active ingredient.
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| Application Number | Priority Date | Filing Date | Title |
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| CNB200710044082XA CN100528956C (en) | 2007-07-20 | 2007-07-20 | Nano particle of enwrapping water-soluble active ingredient, and preparation method |
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| CNB200710044082XA CN100528956C (en) | 2007-07-20 | 2007-07-20 | Nano particle of enwrapping water-soluble active ingredient, and preparation method |
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| CN100528956C true CN100528956C (en) | 2009-08-19 |
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| CN104510631B (en) * | 2013-09-27 | 2017-03-29 | 华熙福瑞达生物医药有限公司 | A kind of oil dispersed hyaluronate sodium and its production and use |
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