CN104054704A - Hydroxypropyl-beta-cyclodextrin supermolecular inclusion complex of methylparaben, preparation method of inclusion complex and use method of inclusion complex - Google Patents
Hydroxypropyl-beta-cyclodextrin supermolecular inclusion complex of methylparaben, preparation method of inclusion complex and use method of inclusion complex Download PDFInfo
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- CN104054704A CN104054704A CN201410116251.6A CN201410116251A CN104054704A CN 104054704 A CN104054704 A CN 104054704A CN 201410116251 A CN201410116251 A CN 201410116251A CN 104054704 A CN104054704 A CN 104054704A
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- methyl hydroxybenzoate
- methylparaben
- inclusion compound
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Abstract
The invention discloses a supermolecular inclusion (conjunction) complex of mildew-proof and antimicrobial medicaments, namely methylparaben and hydroxypropyl-beta-cyclodextrin, a preparation method of the inclusion complex and a use method of the inclusion complex. The supermolecular inclusion complex comprises the methylparaben and the hydroxypropyl-beta-cyclodextrin according to a weight ratio which is less than or equal to 1 to 10. The hydroxypropyl-beta-cyclodextrin supermolecular inclusion complex of the methylparaben solves the problems that the methylparaben is difficult to dissolve in water and is difficultly applied in an aqueous solution; the problems that an organic solvent is required to be added when being used in the aqueous solution and the methylparaben is affected by operation processes such as an adding method are solved; the problems that the methylparaben is easy to separate out and loses effect easily in the operation process under a low-temperature condition are solved; the phenomena that the methylparaben is easy to degrade and the methylparaben easily loses the antimicrobial effect due to the possible mixing problem are avoided. Therefore, the methylparaben is extremely high in water solubility, and the water solubility is converted from being indissolvable into being dissolvable; the problems of difficulties in application and operation of the methylparaben in the aqueous solution are solved, and the methylparaben can be applied under a high-concentration condition.
Description
Technical field
The present invention relates to a kind of antimildew and antibacterial field, relate in particular to a kind of HP-β-CD super molecule inclusion compound, preparation method and using method of methyl hydroxybenzoate.
Background technology
Methyl hydroxybenzoate claims again hydroxyl styrax methyl esters, 4-HBA methyl esters, this product is white, needle-shaped crystals or colourless crystallization, soluble in ethanol, ether, acetone and other organic solvent, atomic molten in water, boiling point 270-280 DEG C, it is the preservative of the wide spectrum of generally acknowledging in the world, efficient, low toxicity, the states such as the U.S., Europe, Japan, Canada, Korea S, Russia all allow the application of methyl hydroxybenzoate in fields such as food, cosmetics, medicine and feeds, and in the GB2760 of China, also regulation methyl hydroxybenzoate sodium salt can be used as food preservative.
Methyl hydroxybenzoate is owing to having phenolic hydroxyl structure, so antibacterium performance is all stronger than benzoic acid, sorbic acid, its mechanism of action is: the cell membrane of destroy microorganisms, makes intracellular protein denaturation, and can suppress the activity of respiratory enzyme system with the electronics transmission enzyme system of microbial cell.The bacteriostatic activity of methyl hydroxybenzoate is mainly that molecular state works, and its esterification of intramolecular hydroxyl, and no longer ionization, so it all has good fungistatic effect in the scope of PH3～8.But atomic molten in this product water, carry out when anticorrosion utilizing the organic solvents such as ethanol to carry out hydrotropy to improve its water solvability for aqueous solution, and organic solvent is difficult for removing from the aqueous solution, and with the volatilization of organic solvent or the reduction of temperature, methyl hydroxybenzoate is separated out gradually and is lost antisepsis from solution, affect use and the antibacterial bacteriostatic usefulness of methyl hydroxybenzoate in aqueous solution, affected the convenience, the safety that use with operation.
Therefore, need to adopt and not only kept the effect of methyl hydroxybenzoate wide spectrum, efficient, low toxicity antiseptic and inhibiting bacteria function but also the measure of raising methyl hydroxybenzoate solvability, stability in water that can be larger, in the situation that improving methyl hydroxybenzoate ease of use, stability, and further widen compatibility and the range of application of methyl hydroxybenzoate, meet the demand of product.
Summary of the invention
In view of this, the object of the present invention is to provide a kind of HP-β-CD super molecule inclusion compound, preparation method and using method of methyl hydroxybenzoate, can keep the effect of methyl hydroxybenzoate wide spectrum, efficient, low toxicity antiseptic and inhibiting bacteria function, raising methyl hydroxybenzoate that again can be larger solvability and stability in water, thereby use methyl hydroxybenzoate that can be convenient, further widens the range of application of methyl hydroxybenzoate.
The HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate of the present invention, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD≤1:10;
Further, comprise following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:20;
Further, comprise following raw material by weight: HP-β-CD: methyl hydroxybenzoate=1:15;
Further, comprise following raw material by weight: HP-β-CD: methyl hydroxybenzoate=1:30;
Further, described HP-β-CD is one or both in 2-HP-BETA-CD, 3-HP-β-CD.
The present invention also discloses a kind of preparation method of HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate, by weight by water: add the methyl hydroxybenzoate of setting weight ratio after HP-β-CD is water-soluble with HP-β-CD >=1 and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
Further, in preparation method, comprise by weight: HP-β-CD: water=0.5, dissolve HP-β-CD in water temperature in higher than 60 DEG C of situations;
Further, first HP-β-CD is dissolved in to 80 DEG C of water, then adds methyl hydroxybenzoate, under insulation, be constantly stirred to methyl hydroxybenzoate and dissolve completely, after the dry or freeze drying of spraying and get final product.
The present invention also discloses a kind of using method of HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate, in food and solution-type oral drug preparation, uses according to methyl hydroxybenzoate concentration 0.03%～0.05% metering therein; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.1%～0.2% metering use.
Beneficial effect of the present invention: the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate, has overcome indissoluble in methyl hydroxybenzoate water, the problem that is difficult to apply in aqueous solution; Overcome and needed the problem of adding organic solvent and being added the operating process such as method to affect for aqueous solution process; Overcome in operating process and low temperature condition under easily separate out the problem of inefficacy; Overcome the easy degraded of methyl hydroxybenzoate and contingent compatibility problems and lost antibacterial and bacteriostasis; Methyl hydroxybenzoate has obtained good water-soluble, and in water, solvability becomes Yi Rong from indissoluble, has solved in methyl hydroxybenzoate aqueous solution and has been difficult to apply and operational issue, and can in higher concentration situation, apply; Obtain good ease for use, can directly add water in aqueous solution or together with other components directly to dissolve use; Obtained good stability, due to the protection of HP-β-CD overcome with solution in the contingent chemical compatibility of other component and degraded lost efficacy; Supermolecule inclusion (knot) thing of methyl hydroxybenzoate and HP-β-CD keep the effect of its antibacterial bacteriostatic and scope constant.HP-β-CD has great solvability in water, this inclusion in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%; Methyl hydroxybenzoate wraps in HP-β-CD circulus with non-covalent bond active force, make it obtain solvability and chemical stability in great water, and keep the antibacterial and bacteriostasis of its wide spectrum, efficient, low toxicity, can be applied in aqueous solution with larger concentration range, expand the compatibility with other material, increase and simplified application method, as dissolve rear use, directly mix use etc. with dry material.This product can be used for the antimildew and antibacterial of food, cosmetics, medicine, feed and construction material etc., extends operating period, the shelf-life of material.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of methyl hydroxybenzoate and HP-β-CD super molecule inclusion compound;
Fig. 2 is HP-β-CD infrared spectrogram;
Fig. 3 is methyl hydroxybenzoate infrared spectrogram.
Embodiment
The HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate of the present invention, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD≤1:10.
Be preferably, comprise following raw material by weight: HP-β-CD: methyl hydroxybenzoate=1:20.
Be preferably, comprise following raw material by weight: HP-β-CD: methyl hydroxybenzoate=1:15.
Be preferably, comprise following raw material by weight: HP-β-CD: methyl hydroxybenzoate=1:30.
In the present embodiment, described HP-β-CD is one or both in 2-HP-BETA-CD, 3-HP-β-CD.
The present invention also discloses a kind of preparation method of HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate, by weight by HP-β-CD with HP-β-CD: after water≤1 is water-soluble, add the methyl hydroxybenzoate of setting weight ratio and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
In the present embodiment, after water temperature is dissolved HP-β-CD in higher than 60 DEG C of situations, add methyl hydroxybenzoate, then under heating or insulation, be constantly stirred to methyl hydroxybenzoate and dissolve completely;
In the present embodiment, by weight by HP-β-CD with HP-β-CD: water=0.5 is dissolved in 80 DEG C of water.
The present invention also discloses a kind of using method of HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate, in food and solution-type oral drug preparation, uses according to methyl hydroxybenzoate concentration 0.03%～0.05% metering therein; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.1%～0.2% metering use.
By specifically having implemented, the present invention is further elaborated below.
Embodiment mono-
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, comprises following raw material by weight: HP-β-CD: methyl hydroxybenzoate=1:20.
In the present embodiment, HP-β-CD is 2-HP-BETA-CD, adopt the hydroxypropyl derivatives (3-HP-β-CD) of close other beta-schardinger dextrin-of physico chemical property to replace 2-HP-BETA-CD, for the performance of product and have no significant effect.
The preparation method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, by weight by HP-β-CD taking HP-β-CD: water=0.5 is dissolved in the methyl hydroxybenzoate that temperature adds setting weight ratio after the water of 80 DEG C, then under heating or insulation, being constantly stirred to methyl hydroxybenzoate dissolves completely, adjust its concentration and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
The using method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment is used according to methyl hydroxybenzoate concentration 0.04% metering therein in food and solution-type oral drug preparation; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.15% metering use.
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate that the present embodiment makes, this inclusion in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%.
Embodiment bis-
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:10.
In the present embodiment, HP-β-CD is 3-HP-β-CD, adopt the hydroxypropyl derivatives (2-HP-BETA-CD) of close other beta-schardinger dextrin-of physico chemical property to replace 3-HP-β-CD, for the performance of product and have no significant effect.
The preparation method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, by weight by HP-β-CD taking HP-β-CD: water=0.3 is dissolved in the methyl hydroxybenzoate that temperature adds setting weight ratio after the water of 70 DEG C, then under heating or insulation, being constantly stirred to methyl hydroxybenzoate dissolves completely, adjust its concentration and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
The using method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment is used according to methyl hydroxybenzoate concentration 0.03% metering therein in food and solution-type oral drug preparation; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.1% metering use.
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate that the present embodiment makes, this inclusion compound in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%.
Embodiment tri-
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:30.
In the present embodiment, HP-β-CD is 3-HP-β-CD, adopt the hydroxypropyl derivatives (2-HP-BETA-CD) of close other beta-schardinger dextrin-of physico chemical property to replace 3-HP-β-CD, for the performance of product and have no significant effect.
The preparation method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, by weight by HP-β-CD with HP-β-CD: water=1, be dissolved in temperature and be the methyl hydroxybenzoate that adds setting weight ratio after the water of 65 DEG C, then under heating or insulation, being constantly stirred to methyl hydroxybenzoate dissolves completely, adjust its concentration and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
The using method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment is used according to methyl hydroxybenzoate concentration 0.05% metering therein in food and solution-type oral drug preparation; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.2% metering use.
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate that the present embodiment makes, this inclusion in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%.
Embodiment tetra-
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:25.
In the present embodiment, HP-β-CD is 2-HP-BETA-CD, adopt the hydroxypropyl derivatives (3-HP-β-CD) of close other beta-schardinger dextrin-of physico chemical property to replace 2-HP-BETA-CD, for the performance of product and have no significant effect.
The preparation method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, by weight by HP-β-CD taking HP-β-CD: water=0.2 is dissolved in the methyl hydroxybenzoate that temperature adds setting weight ratio after the water of 90 DEG C, then under heating or insulation, being constantly stirred to methyl hydroxybenzoate dissolves completely, adjust its concentration and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
The using method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment is used according to methyl hydroxybenzoate concentration 0.035% metering therein in food and solution-type oral drug preparation; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.15% metering use.
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate that the present embodiment makes, this inclusion in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%.
Embodiment five
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:28.
In the present embodiment, HP-β-CD is 2-HP-BETA-CD, adopt the hydroxypropyl derivatives (3-HP-β-CD) of close other beta-schardinger dextrin-of physico chemical property to replace 2-HP-BETA-CD, for the performance of product and have no significant effect.
The preparation method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, by weight by HP-β-CD with HP-β-CD: water=0.1, be dissolved in temperature and be the methyl hydroxybenzoate that adds setting weight ratio after the water of 65 DEG C, then under heating or insulation, being constantly stirred to methyl hydroxybenzoate dissolves completely, adjust its concentration and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
The using method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment is used according to methyl hydroxybenzoate concentration 0.035% metering therein in food and solution-type oral drug preparation; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.15% metering use.
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate that the present embodiment makes, this inclusion in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%.
Embodiment six
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, comprises following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:15.
In the present embodiment, HP-β-CD is 2-HP-BETA-CD, adopt the hydroxypropyl derivatives (3-HP-β-CD) of close other beta-schardinger dextrin-of physico chemical property to replace 2-HP-BETA-CD, for the performance of product and have no significant effect.
The preparation method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment, by weight by HP-β-CD with HP-β-CD: water=0.25, be dissolved in temperature and be the methyl hydroxybenzoate that adds setting weight ratio after the water of 75 DEG C, then under heating or insulation, being constantly stirred to methyl hydroxybenzoate dissolves completely, adjust its concentration and spray dry or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.
The using method of the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate of the present embodiment is used according to methyl hydroxybenzoate concentration 0.035% metering therein in food and solution-type oral drug preparation; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.2% metering use.
The HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate that the present embodiment makes, this inclusion in solvability in the water of methyl hydroxybenzoate by 0.25%(20 DEG C) following being increased to more than 7.5%.
As seen from the above-described embodiment, and for above technique effect, the proportioning of embodiment mono-and technological parameter, result of use is best, is obviously better than other embodiment, is the best.
Finally explanation is, above embodiment is only unrestricted in order to technical scheme of the present invention to be described, although the present invention is had been described in detail with reference to preferred embodiment, those of ordinary skill in the art is to be understood that, can modify or be equal to replacement technical scheme of the present invention, and not departing from aim and the scope of technical solution of the present invention, it all should be encompassed in the middle of claim scope of the present invention.
Claims (7)
1. a HP-β-CD super molecule inclusion compound for methyl hydroxybenzoate, is characterized in that: comprise following raw material by weight: methyl hydroxybenzoate: HP-β-CD≤1:10.
2. the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate according to claim 1, is characterized in that: comprise following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:20.
3. the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate according to claim 1, is characterized in that: comprise following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:15.
4. the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate according to claim 1, is characterized in that: comprise following raw material by weight: methyl hydroxybenzoate: HP-β-CD=1:30.
5. according to the HP-β-CD super molecule inclusion compound of the methyl hydroxybenzoate described in the arbitrary claim of claim 1～4, it is characterized in that: described HP-β-CD is one or both in 2-HP-BETA-CD, 3-HP-β-CD.
6. the preparation method of the HP-β-CD super molecule inclusion compound of a methyl hydroxybenzoate claimed in claim 1, it is characterized in that: HP-β-CD by weight: water≤1, after HP-β-CD is water-soluble, add the methyl hydroxybenzoate of setting weight ratio, after dissolving, spray and be dried or freeze drying, obtain the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate.5. the preparation method of the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate according to claim 4, it is characterized in that: after water temperature is dissolved HP-β-CD during higher than 60 DEG C, add methyl hydroxybenzoate, then under heating or insulation, be constantly stirred to methyl hydroxybenzoate and dissolve completely.6. the preparation method of the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate according to claim 5, it is characterized in that: HP-β-CD by weight: water=0.5, first HP-β-CD is dissolved in to 80 DEG C of water, add again methyl hydroxybenzoate, under insulation, be constantly stirred to methyl hydroxybenzoate and dissolve completely, after the dry or freeze drying of spraying and get final product.
7. a using method for the HP-β-CD super molecule inclusion compound of methyl hydroxybenzoate claimed in claim 1, is characterized in that: in food and solution-type oral drug preparation, use according to methyl hydroxybenzoate concentration 0.03%～0.05% metering therein; In cosmetics, emulsifiable paste semisolid preparation, feed, construction material according to methyl hydroxybenzoate wherein concentration 0.1%～0.2% metering use.
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Application publication date: 20140924 |