• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Rosin microspheres and their derivatives as a system for incorporating active elements. The present invention relates to rosin microspheres, their method of obtaining them and their use as a system for incorporating active elements into materials and solutions. Therefore, the present invention is encompassed in compositions of natural resins and excipient-containing matrix-like microspheres or microcapsules for incorporation into other media. (Machine-translation by Google Translate, not legally binding)
    公开号:ES2764623A1
    申请号:ES202030422
    申请日:2020-05-11
    公开日:2020-06-03
    发明作者:Martínez Juan López；Vargas Cristina Paola Pavón；Madrigal María Dolores Samper；Carrasco Miguel Fernando Aldas；Bou Santiago Ferrándiz；La Rosa Ramírez Harrison De；Azor José Miguel Ferri；García Daniel García；Gimeno Rafael Antonio Balart；Enguidanos Juan Alberola；Arrieta Marina Patricia；Gimeno Octavio Angel Fenollar
    申请人:Universidad Politecnica de Valencia；
    IPC主号:
    专利说明:

    [0002] Rosin microspheres and its derivatives as a system for incorporating active elements
    [0004] The present invention relates to rosin microspheres, their process for obtaining them and their use as a system for incorporating active elements into materials and solutions. Therefore, the present invention is encompassed in compositions of natural resins and excipient-containing matrix-like microspheres or microcapsules for incorporation into other media.
    [0006] BACKGROUND OF THE INVENTION
    [0007] Currently, the plastics industry is constantly investigating alternatives that allow the life time after the final disposal of the material to be reduced. One of these alternatives is the use of natural sources, such as cellulose or polysaccharides, for the production of bio or green materials [PA Wilbon, F. Chu, and C. Tang, “Progress in renewable polymers from natural terpenes, terpenoids, and rosin, ” Macromol. Rapid Commun., Vol. 34, no. 1, pp. 8-37, 2013],
    [0009] Rosin is the solid residue of pine resin, which is obtained by heating the resin to evaporate the volatile or turpentine fraction. It is an acidic, semi-transparent material with a yellowish coloration, soluble in organic solvents, thermoplastic, rigid at room temperature, but melts when heated [S. Kumar and SK Gupta, "Rosin: a naturally derived excipient in drug delivery systems.," Polim. Med., Vol. 43, no. 1, pp. 45-8, 2013.]. The rosin is composed, in 90% by a mixture of diterpenoid resin acids of the abietic, pimárico and isopimárico type, and in 10% by neutral compounds [AJD Silvestre and A. Gandini, “Rosin: major sources, properties and applications,” in Monomers, Polymers and Composites from Renewable resources, 2008, pp. 67-88 and S. Prati, G. Sciutto, R. Mazzeo, C. Torri, and D. Fabbri, “Application of ATR-far-infrared spectroscopy to the analysis of natural resins,” Anal. Bioanal. Chem., Vol. 399, no. 9, pp. 3081-3091, 2011], Given the natural origin of rosin, it is biodegradable and biocompatible, so it is generally studied, together with its derivatives, in the pharmaceutical industry, for coatings and for microencapsulation and controlled release of substances [GR Mitchell , V. Mahendra, and D. Sousa, "Biopolymers Based on Rosin," Curr. Res. Biopolym., Vol. 2018, no. 01, p. 6, 2018 and W. II Baek, R. Nirmala, NAM Barakat, MH El-Newehy, SS Al-Deyab, and HY Kim, "Electrospun cross linked rosin fibers," Appl. Surf. Sci., Vol. 258, no. 4, pp. 1385-1389, Dec. 2011.].
    [0011] Electrospray is a novel technique that allows obtaining structures that have structural and functional advantages due to their size, however, they have not been explored in depth [J. Anu Bhushani and C. Anandharamakrishnan, “Electrospinning and electrospraying techniques: Potential food based applications,” Trends Foo / * 76d Sci. Technol., Vol. 38, no. 1, pp. 21-33, 2014.]. The electrospraying technique has the advantage of not leaving chemical by-products on the final material, unlike the chemical techniques that are used to prepare microspheres [A. Jaworek, "Micro- and nanoparticle production by electrospraying," Powder Technol., Vol.
    [0012] 176, no. 1, pp. 18-35, Jul. 2007],
    [0014] However, rosin microspheres have never been stabilized by electrospray technique.
    [0016] DESCRIPTION OF THE INVENTION
    [0018] The present invention relates to rosin microspheres, their method of obtaining by means of an electrospray process.
    [0020] In a first aspect, the present invention refers to microspheres characterized in that
    [0021] • each microsphere is composed of rosin; and
    [0022] • each microsphere is between 3pm and 8pm.
    [0024] In a preferred embodiment of the invention the microspheres are characterized in that they have a surface density of spheres of between 1.50-10.3 spheres / pm2 and 0.4041 spheres / pm2.
    [0026] The advantages of the microsphere is that it is biodegradable and biocompatible, and also due to its dimensions they present other allotropic advantages with respect to the macroscopic material. This size is small enough to allow the microspheres to be incorporated as an emulsion in aqueous or alcoholic solvents, but large enough to incorporate nanoparticles and active elements.
    [0027] In a preferred embodiment, the microsphere of the present invention further comprises within it a compound selected from biocide, antioxidant, healing, functionalized nanoclay and any combination of the above.
    [0029] In a more preferred embodiment, the biocides are selected from triclosan, silver nanoparticles, antibiotic, fungicide, antiseptic and disinfectant and insecticides. In an even more preferred embodiment the antibiotic is selected from among natural compounds such as carnasol, carvacrol, garlicin or synthetics such as amoxicillin and any combination of the above. In another even more preferred embodiment the fungicide is an antimiotic, such as rosemary oil or allicin and cinnamladehyde. In a still more preferred embodiment the antiseptic and disinfectant is selected from iodine-povidone, eugenol, thymol and chlorhexidine gluconate.
    [0031] In another more preferred embodiment the antioxidants are selected from phenols, polyphenols, carotenoids and lignin.
    [0033] In another more preferred embodiment, the healing agent is selected from Aloina, Aloeemodina, Emodin or retinol.
    [0035] In another more preferred embodiment the functionalized nanoclay is hallosite nanoclays or nanotubes. These active compounds allow the incorporation of the active components to be facilitated and also allow the subsequent controlled migration of the active principles incorporated into the selected medium. In this way, the microspheres can house different active compounds that, once incorporated into the microsphere, can be used vehicularly to deposit on structural materials such as wood, metal or plastic, and even for their natural character on living tissues. The active components are introduced in a controlled way, by quantified incorporation into the solvent used in the formation of the microspheres.
    [0037] A third aspect of the invention is a process for obtaining the microspheres described above, characterized in that it comprises the following steps: a) adding rosin of miera to
    [0038] i. a solution comprising chloroform to a concentration 45% by weight with respect to the miera rosin; or
    [0039] ¡I. a solution comprising dichloromethane to a concentration of 60% by weight with respect to the miera rosin; and shake for at least 24 h;
    [0040] b) feeding the solution obtained in (a) into a syringe pump and connecting said pump to a needle with an internal diameter of between 0.3 mm and 0.5 mm; c) apply a potential difference, by applying a high power source, connecting a positive pole to the needle in section (b) and the negative pole to a collecting plate, and located at a distance of between 10 cm and 20 cm from the needle, where the plate is also placed with its collection area facing the tip of the needle and along a longitudinal axis that crosses the entire needle;
    [0041] d) applying a flow to the syringe pump; and
    [0042] optionally incorporate in the solution of step (a) compound selected from among biocides, antioxidants, functionalized nanoclays and any combination of the above in a concentration of between 10% and 30% by weight with respect to the miera rosin.
    [0044] In a preferred embodiment of the method the potential difference of step c) is between 5 kV and 25 kV. In a more preferred embodiment the potential difference from step c) is between 10 kV and 15 kV. The narrowest size dispersions are obtained in this voltage range and a greater number of spheres appear per area, because it is high enough to generate an acceptable number of particles, but it is not excessively powerful for the particle size and its dispersion grows in excess.
    [0046] In a preferred embodiment of the method, the flow applied in step (d) is between 0.3 pL / min and 15 pL / min. In a more preferred embodiment the applied flow is between 0.5 pL / min and 5 pL / min. In this flow range, the narrowest dispersions are obtained and a greater number of spheres appear per area, it is the optimal range because a lower flow value would affect a smaller production of microspheres and a higher value would generate larger sizes and higher dispersion.
    [0048] In another preferred embodiment the solvent of step (a) is dichloromethane, the difference The potential of stage (c) is between 10 and 15 kV and the flow of stage (d) is between 0.5 pL / min and 1 pL / min. These conditions allow obtaining fairly stable densities and dispersions with an acceptable variability, which is important for production in large quantities.
    [0050] In another preferred embodiment the solvent from step (a) is chloroform, the potential difference from step (c) is between 10 and 15 kV and the flux from step (d) is between 0.5 pL / min and 1 pL / min. Such conditions allow fairly stable densities and dispersions.
    [0052] Another aspect of the invention is the use of the microspheres described above comprising biocides as antibiotics, fungicides, antiseptics and disinfectants, and / or insecticides on medical and / or surgical or structural materials.
    [0054] Medical and / or surgical materials are selected from among nonwovens (known as mats which are laminar tissues formed by chaotically woven fibers) of biocompatible, biodegradable and / or bioabsorbable polymer matrix such as poly (ecaprolactone), poly (3-hydroxybutyrate), poly (4-hydroxybutyrate), poly (lactic acid) or polysaccharides such as starch or chitosan. The purpose of these nonwovens is the treatment of wounds and protection against infections. One of the drawbacks that nonwovens present is that due to their porous and / or fibrous morphology they are prone to the adhesion of microorganisms, which can generate infections. The use of rosin spheres loaded with biocidal agents can help to overcome the inconvenience of adhesion of microorganisms.
    [0056] Structural materials are selected from wood, metal, plastic, and any combination thereof.
    [0058] Another aspect of the present invention is the use of the microspheres comprising healing agents as tissue healing.
    [0060] Throughout the description and claims, the word "comprises" and its variants are not intended to exclude other technical characteristics, additives, components or steps. For those skilled in the art, other objects, advantages and characteristics of the invention will emerge in part from the description and in part from the practice of the invention. The The following examples and figures are provided by way of illustration, and are not intended to be limiting of the present invention.
    [0062] BRIEF DESCRIPTION OF THE FIGURES
    [0064] Fig. 1. Morphology of the rosin microparticles and particle size distribution, using dichloromethane as solvent, from experiment a.
    [0066] Fig. 2. Morphology of the rosin microparticles and particle size distribution, using dichloromethane as solvent, from experiment b.
    [0068] Fig. 3. Morphology of the rosin microparticles and particle size distribution, using dichloromethane as solvent, from experiment c.
    [0070] Fig. 4. Morphology of the rosin microparticles and particle size distribution, using dichloromethane as solvent, from experiment d.
    [0072] Fig. 5. Morphology of the rosin microparticles and particle size distribution, using dichloromethane as solvent, from experiment e.
    [0074] Fig. 6. Rosin microparticle morphology and particle size distribution, using dichloromethane as solvent, from experiment f
    [0076] Fig. 7. Rosin microparticle morphology and particle size distribution, using dichloromethane as solvent, from experiment g.
    [0078] Fig. 8. Rosin microparticle morphology and particle size distribution, using chloroform as solvent, from experiment a '.
    [0080] Fig. 9. Rosin microparticle morphology and particle size distribution, using chloroform as solvent, from experiment b '.
    [0082] Fig. 10 Rosin microparticle morphology and particle size distribution, using chloroform as solvent, from experiment c '.
    [0083] Fig. 11. Rosin microparticle morphology and particle size distribution, using chloroform as solvent, from experiment d '.
    [0085] Fig. 12. Morphology of rosin microparticles and particle size distribution, using chloroform as solvent, from experiment e '.
    [0087] EXAMPLES
    [0089] Next, the invention will be illustrated by means of tests carried out by the inventors, which shows the effectiveness of the product of the invention.
    [0091] Example 1
    [0092] Solutions are prepared with Miera Rosin (GR) provided by Luresa Resinas S.L (Segovia, Spain), this resin has a softening point of 76 ° C, acid number of 167 and a color value of 4+ on the Gardner scale. Chloroform supplied by Panreac (Barcelona, Spain) with density> 1.48 g / cm3 at 20 ° C and purity of 99.8% is used as solvents. A concentration of 45% is used and the prepared solution is kept under constant stirring for 24 h at room temperature. The solution is fed to a syringe pump (SringePump, New York, United States) and this is connected to a metal needle with an internal diameter of 0.4 mm. To collect the spheres, a rectangular metal collecting plate is used on which a sheet of aluminum foil is placed. A high power source (Genvolt, Shropshire, UK) is used to supply the potential difference, which is connected to the positive pole attached to the metal needle and the negative pole to the collecting plate. It works with a needle-collector distance of 15 cm.
    [0094] Example 2
    [0095] Solutions are prepared with Miera Rosin (GR) provided by Luresa Resinas SL (Segovia, Spain), this resin has a softening point of 76 ° C, acid number of 167 and a color value of 4+ on the Gardner scale. Dichloromethane provided by Sigma-Aldrich Quimica SA (Madrid, Spain) with a density of 1,325 g / cm3 and purity of 99.8% with a concentration of 60% is used as the solvent and the prepared solution is kept under constant stirring for 24 h at room temperature . The solution was fed to a syringe pump (SringePump, New York, United States) and this is connected to a metallic needle with an internal diameter of 0.4 mm. To collect the spheres, a rectangular metal collecting plate was used on which a sheet of aluminum foil was placed. A high power source (Genvolt, Shropshire, UK) is used to supply the potential difference, which is connected to the positive pole attached to the metal needle and the negative pole to the collecting plate. It works with a needle-collector distance of 15 cm.
    [0097] Example 3
    [0098] The following electrospray experiments are performed, following the conditions used that are listed in Table 1 on Examples 1 and 2 as described.
    [0100] Table 1. Flow and potential conditions used for the different experiments carried out in the production of rosin microspheres.
    [0105] The spheres deposited on the aluminum foil were morphologically analyzed by scanning electron microscopy (SEM) in a Phenon SEM kit from FEI (Eindhiven, The Netherlands) with a potential of 5 kV.
    [0107] Example 4
    [0108] Characterization of the rosin microspheres obtained in dichloromethane as solvent.
    [0109] Figures 1 to 7 show the images obtained by scanning electron microscopy (SEM) and the particle size distribution of the rosin microspheres prepared by electrospray using dichloromethane as the solvent. In these images you can see the morphological differences obtained with different flows and work potentials.
    [0111] For the flow of 0.5 pL / min a density of spheres of 8.73x10'3 spheres / pm2 was found (Figure 1), 4.31x10'3 spheres / pm2 (Figure 2) and at 4.95x10'3 spheres / pm2 (Figure 3) with potentials of 10 kV, 15 kV and 20 kV respectively. With a flow of 1 pL / min the dispersion is 7.42x10'3 spheres / pm2 (Figure 4) with a potential of 10 kV and 0.0348 spheres / pm2 with a potential of 15 kV (Figure 5). And finally with a flow of 5 pL / min the dispersion for 10 kV is 9.17x10'3 spheres / pm2 (Figure 6) while when using 15 kV its value is 7.28x10'3 spheres / pm2 (Figure 7). All these values are collected in Table 2.
    [0113] Therefore, this range of fluxes and voltages allows fairly stable densities and dispersions to be obtained with acceptable variability, which is important for high volume production.
    [0115] Regarding the particle size, it is found that for a flow of 0.5 pL / min and a potential of 10 kV, the spheres have an average diameter of 6 pm (Figure 1) with low size dispersion, for a potential of 15 kV the size mean diameter is 8 pm (Figure 2), and with a potential of 20 kV 4pm spheres are produced (Figure 3) with a high dispersion in terms of particle size. While when working with a flow of 1 pL / min and 10 kV the average size is 5pm (Figure 4) and there is a low dispersion of the particle size, and at 15 kV the dispersion increases and the average diameter is 4 pm (Figure 5). Finally, for a flow of 5 pL / min, we have that with 10 kV an average diameter size of 7 pm is obtained (Figure 6) with low size dispersion, and with 15 kV an average size of 7 is also obtained pm (Figure 7) with greater dispersion. All these values are collected in Table 2.
    [0117] The trend continues that softer working conditions (lower flow and voltage) allow us smaller sizes with less dispersion, but it affects reducing the number of particles obtained.
    [0118] Table 2. Results of the density and diameter values of the rosin microspheres obtained in dichloromethane as solvent.
    [0120]
    [0123] Example 5
    [0124] Characterization of the rosin microspheres obtained in chloroform as solvent.
    [0126] Figure 2 shows the SEM images of the rosin microspheres prepared by electrospray using chloroform as the solvent. For a potential of 10 kV it can be seen that the density of spheres has a value of 0.0252 spheres / pm2 with a flow of 0.5 pL / min (Figure 8), 0.4041 spheres / pm2 at 1 pL / min (Figure 9), a value 0.0101 spheres / pm2 at 5 pL / min (Figure 10), and finally 1.50x10'3 spheres / pm2 with 10 pL / min (Figure 11), For the potential of 15 kV the density of spheres has been determined at a value 0.0107 spheres / pm2 (Figure 12). All these values are collected in Table 3. Therefore, this range of flows and voltages allows obtaining fairly stable densities and dispersions, although at the upper limit the dispersion begins to increase.
    [0128] Regarding the size of the particle diameter, it has been obtained that for a flow of 0.5 pL / min and a potential of 10 kV, there is an average size of 4 pm (Figure 8). For a flow of 1 pL / min and a potential of 10 kV, we have an average size of 3 pm (Figure 9). When using a flow of 5 pL / min and a potential of 10 kV, the size obtained is 5 pm (Figure 10), and with a potential of 15 kV, the average diameter size is 5 pm (Figure 11), in all these cases the particle diameter size dispersion is neither too high nor too low. And finally for a flow of 10 pL / min and a 10 kV potential, a diameter of 6 pm is obtained (Figure 12) and a high dispersion of sizes. All these values are collected in Table 3.
    [0130] Therefore, this range of flows and voltages allows obtaining fairly stable densities and dispersions.
    [0132] Table 3. Results of the density and diameter values of the rosin microspheres obtained in chloroform as solvent.
    [0134]
    [0137] Example 6
    [0138] The incorporation of a biocidal agent in the rosin microspheres can be carried out using the mixing method, which is the simplest process and allows the encapsulation of substances in a single step, unlike other methods such as surface modification or the coaxial process. . The method consists of mixing the biocide with the rosin solution prior to the electrospray process. To ensure sustained and prolonged release behavior of the substance, it is recommended to work with substances that have favorable physical interactions with the matrix. Biocidal compounds such as, for example: thymol, carvacrol, eugenol or cinnamladehyde can be used. The biocidal agent will be used in a composition of 10 to 30% by weight to ensure its encapsulation at the time of electrospray.
    [0140] Example 7
    [0141] Description of the use of rosin microspheres
    [0143] The microspheres of Example 6 can be added by immersion, casting or impregnation to biocompatible, biodegradable and / or bioabsorbable polymer matrix non mats such as poly (£ -caprolactone), poly (3-hydroxybutyrate), poly (4-hydroxybutyrate) ), poly (lactic acid) or polysaccharides such as starch or chitosan. The purpose of these nonwovens is the treatment of wounds and protection against infections. One of the drawbacks that nonwovens present is that due to their porous and / or fibrous morphology they are prone to the adhesion of microorganisms, which can generate infections. The use of rosin spheres loaded with biocidal agents can help to overcome the inconvenience of adhesion of microorganisms. Furthermore, as rosin is a natural and biocompatible agent, problems related to the use of nanoparticles in the body will be avoided.
    权利要求:
    Claims (16)
    [1]
    1. Some microspheres characterized by
    • each microsphere is made of miera rosin; and
    • each microsphere is between 3pm and 8pm.
    [2]
    2. Microspheres according to claim 1, characterized in that they have a surface density of spheres of between 1.50-10.3 spheres / pm2 and 0.4041 spheres / pm2.
    [3]
    3. Microspheres according to any of claims 1 or 2, characterized in that it further comprises inside a compound selected from among biocide, antioxidant, healing, functionalized nanoclay and any combination of the above.
    [4]
    4. Microspheres according to claim 3, characterized in that the biocides are selected from triclosan, silver nanoparticles, antibiotics, fungicides, antiseptics and disinfectants and insecticides.
    [5]
    5. Microspheres according to claim 4, where the antibiotic is selected from natural compounds such as carnasol, garlicin or synthetics such as amoxicillin.
    [6]
    6. Microspheres according to claim 4, where the fungicide is an antimiotic, such as rosemary oil or allicin and cinnamladehyde.
    [7]
    7. Microspheres according to claim 4, where the antiseptic and disinfectant is selected from iodo-povidone, eugenol, thymol and chlorhexidine gluconate.
    [8]
    8. Microspheres according to claim 3, characterized in that the antioxidants are selected from phenols, polyphenols, carotenoids and lignin.
    [9]
    9. Microspheres according to claim 3, characterized in that the healing agent is selected from Aloina, Aloe-emodin, Emodin or retinol.
    [10]
    10. Microspheres according to claim 3, characterized in that the functionalized nanoclay is hallosite nanoclays or nanotubes.
    [11]
    11. Procedure for obtaining the microspheres according to any of the Claims 1 to 5 characterized in that it comprises the following steps a) adding miera rosin to
    i. a solution comprising chloroform to a concentration of 45% by weight with respect to the miera rosin; or i. a solution comprising dichloromethane to a concentration of 60% by weight with respect to the miera rosin; and shake for at least 24 h;
    b) feeding the solution obtained in (a) into a syringe pump and connecting said pump to a needle with an internal diameter of between 0.3 mm and 0.5 mm; c) apply a potential difference, by applying a high power source, connecting a positive pole to the needle in section (b) and the negative pole to a collecting plate, and located at a distance of between 10 cm and 20 cm from the needle, where the plate is also placed with its collection area facing the tip of the needle and along a longitudinal axis that crosses the entire needle;
    d) applying a flow to the syringe pump; and
    optionally incorporate in the solution of step (a) compound selected from among biocides, antioxidants, functionalized nanoclays and any combination of the above in a concentration of between 10% and 30% by weight with respect to the miera rosin.
    [12]
    12. Obtaining procedure according to claim 11, where the potential difference of step c) is between 5 kV and 25 kV.
    [13]
    13. Preparation method according to claim 12, where the potential difference is between 10 kV and 15 kV.
    [14]
    14. Preparation process according to any of claims 11 to 13, wherein the flow applied in step (d) is between 0.3 pL / min and 15 pL / min.
    [15]
    15. Preparation method according to claim 14, where the applied flow is between 0.5 pL / min and 5 pL / min.
    [16]
    16. Use of the microspheres according to claims 4 to 7, which comprise biocides as antibiotics, fungicides, antiseptics and disinfectants, and / or insecticides on medical and / or surgical or structural materials.
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    同族专利:
    公开号 | 公开日
    ES2764623B2|2020-11-10|
    WO2021229126A1|2021-11-18|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    EP0455598A1|1990-05-04|1991-11-06|Warner-Lambert Company|Microencapsulated flavoring agents and methods for preparing same|
    JP2019098598A|2017-11-30|2019-06-24|株式会社Ｓｃｒｅｅｎホールディングス|Pretreatment agent composition, recording method, recording medium, and method for producing recording medium|
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    ES202030422A|ES2764623B2|2020-05-11|2020-05-11|ROSIN MICROSPHERES AND ITS DERIVATIVES AS A SYSTEM FOR INCORPORATION OF ACTIVE ELEMENTS|ES202030422A| ES2764623B2|2020-05-11|2020-05-11|ROSIN MICROSPHERES AND ITS DERIVATIVES AS A SYSTEM FOR INCORPORATION OF ACTIVE ELEMENTS|
    PCT/ES2021/070330| WO2021229126A1|2020-05-11|2021-05-11|Rosin microspheres and derivatives thereof as a system for incorporating active elements|
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