WO2017124162A1 - Processo de produção de agente regulador de temperatura nanoencapsulado (artn) via polimerização interfacial - Google Patents
Processo de produção de agente regulador de temperatura nanoencapsulado (artn) via polimerização interfacial Download PDFInfo
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- WO2017124162A1 WO2017124162A1 PCT/BR2016/050009 BR2016050009W WO2017124162A1 WO 2017124162 A1 WO2017124162 A1 WO 2017124162A1 BR 2016050009 W BR2016050009 W BR 2016050009W WO 2017124162 A1 WO2017124162 A1 WO 2017124162A1
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- WIPO (PCT)
- Prior art keywords
- artn
- regulating agent
- temperature regulating
- rpm
- nanoencapsulated
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- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 claims abstract description 4
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- 239000007787 solid Substances 0.000 description 26
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 18
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 7
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- 238000004313 potentiometry Methods 0.000 description 7
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- 229950006451 sorbitan laurate Drugs 0.000 description 7
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 7
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- 229920000428 triblock copolymer Polymers 0.000 description 7
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 6
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- PFNQVRZLDWYSCW-UHFFFAOYSA-N (fluoren-9-ylideneamino) n-naphthalen-1-ylcarbamate Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1=NOC(=O)NC1=CC=CC2=CC=CC=C12 PFNQVRZLDWYSCW-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
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- 239000002775 capsule Substances 0.000 description 1
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 description 1
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- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
- C09K5/06—Materials undergoing a change of physical state when used the change of state being from liquid to solid or vice versa
- C09K5/063—Materials absorbing or liberating heat during crystallisation; Heat storage materials
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/53—Core-shell polymer
Definitions
- the invention pertains to the materials sector for the production of heat or cold by chemical reactions other than combustion, the thermal effect being accompanied by a change from liquid to solid physical state or vice versa containing organic active ingredients. and inorganic compounds that promote temperature regulation using two associated physical principles in the same nanocapsule nanostructure, namely: phase change by melting / solidification of an organic material and reflection of infrared radiation present in white light which affects the surface containing the nanostructured temperature regulating agent.
- the process relates to the interfacial polymerization of cyanoacrylate-type monomer at the interface between the mixture of organic material and colloidal oxide nanoparticles with the aqueous medium as an emulsion. Because it is an interfacial polymerization, the formed nanostructure is characterized by the shell-core type, being the polymeric shell and the core containing the mixture of the materials that regulate the temperature.
- This temperature regulating agent can be applied in the generation of products related to the fields of cosmetics, pharmaceuticals, medical equipment, prosthetics, textiles, paints, coatings, composites, packaging, construction, electrical or electronic equipment, automotive. and paper.
- the search for a better quality of life for humans is a goal that permeates almost all activities in industry and commerce.
- this search for more favorable living conditions there is the comfort provided by buildings, clothing, vehicles and many other products that promote protection and reduce stress and fatigue in the daily activities of men.
- the search for better conditions in thermal comfort stands out, represented by methods or products that minimize temperature variations of environments, objects, clothing or even applied to the skin itself.
- Thermal comfort is strongly related to temperature, humidity, air velocity and solar incidence, as well as the influence of rainfall, vegetation, soil permeability, surface or groundwater and topography.
- Temperature regulators based on the melt / solidification process can be of the organic or inorganic type, and for organic materials, waxes and paraffins are highlighted and Inorganic salts include some eutectic salts or mixtures of salts and water.
- Inorganic salts include some eutectic salts or mixtures of salts and water.
- these temperature regulating materials need to be encapsulated so that during the melting process they do not diffuse into the substrate they are applying or permeate into the skin for cosmetic products and thus maintain. its main characteristic is that it absorbs and releases heat cyclically and with the same thermal efficiency as enthalpy of fusion and solidification.
- the present process of producing nanoencapsulated temperature regulating agent (artn) via interfacial polymerization reveals a process of obtaining ARTN by the interfacial polymerization of cyanoacrylate monomer at the interface between organic material mixture and nanoparticles. of colloidal oxide with the aqueous medium as an emulsion. Because it is an interfacial polymerization, the formed nanostructure is characterized by the shell-core type, being the polymeric shell and the core containing the mixture of the materials that regulate the temperature.
- the synthesis of the ARTN comprises six consecutive processing steps for the generation of nanoencapsulates, being step a) solubilization of the organic material and dispersion of colloidal oxide nanoparticles in a solvent, called the organic phase; step b) pre-emulsifying the organic phase in a solution of water and emulsifiers; step c) diffusion of this preemulsion into an aqueous phase containing emulsifiers; step d) distillation of solvents; and finally, step e) polymerization of the monomer and peeling of the nanocapsules, optionally having a step f) of drying the product.
- step b) pre-emulsifying the organic phase in a solution of water and emulsifiers step c) diffusion of this preemulsion into an aqueous phase containing emulsifiers
- step d) distill
- the generated ARTN may be in the form of a colloidal dispersion in aqueous medium or in nanoparticle form if the aqueous dispersion of the NRNAs is subjected to the optional drying step as spray-drying, fluid bed drying, filtration, lyophilization, centrifugation, among others. Due to its versatility and different forms of presentation, the ARTN obtained by this process allows the obtaining of different types of products for application in the cosmetics, pharmaceutical, medical equipment, prostheses, textiles, paints, coats, composites industries. , packaging, construction, electrical or electronic equipment, automotive and paper.
- Figure 1 shows an illustrative schematic of the mechanism of action obtained for the nanocapsulated temperature regulating agent, showing the polymeric shell (1) and the PCM core with UV radiation filter (2).
- Figure 2 shows a photograph of a plate containing the product obtained after exposure to the temperature of ⁇ ° C in an air circulation oven (Example 1).
- Figure 3 shows a photomicrograph of the obtained nanoencapsulated product (Example 1).
- Figure 4 shows the DSC curve for 3 consecutive heating and cooling cycles with respective enthalpy values of the obtained nanoencapsulated product (Example 1)
- Figure 5 shows a photograph of a plate containing the product obtained after exposure to the temperature of ⁇ ° C in an air circulation oven (Example 2).
- Figure 6 shows a photomicrograph of the nanocapsulated product obtained (Example 2).
- Figure 7 shows consecutive dynamic turbidimetry (stability) scans of the obtained nanocapsulated product (Example 2).
- Figure 8 shows a photograph of a plate containing the product obtained after reaction exposed at 40 ° C in an air circulation oven (Example 3).
- Figure 9 shows a photomicrograph of the nanoencapsulated product obtained (Example 3).
- Figure 10 shows a photograph of a plate containing the product obtained after reaction exposed at 40 ° C in an air circulation oven (Example 4).
- Figure 11 shows a photomicrograph of the nanocapsulated product obtained (Example 4).
- Figure 12 shows a photograph of a plate containing the product obtained after reaction exposed at 40 ° C in an air circulation oven (Example 5)
- Figure 13 shows a photomicrograph of the nanocapsulated product obtained (Example 5).
- Figure 14 shows consecutive dynamic turbidimetry (stability) scans of the nanocapsulated product (Example 5)
- Figure 15 shows a photograph of a plate containing the product after reaction exposed to a temperature of 40 ° C in an air circulation oven (Example 6).
- Figure 16 shows a photomicrograph of the nanocapsulated product (Example 6).
- Figure 17 shows consecutive dynamic turbidimetry scans of the nanocapsulated product (Example 6)
- Figure 18 shows a photograph of a plate containing the product obtained after reaction exposed at 40 ° C in an air circulation oven (Example 7).
- Figure 19 shows a photomicrograph of the nanoencapsulated product obtained (Example 7).
- Figure 20 shows the DSC curve showing 20 consecutive heating and cooling cycles of the obtained nanocapsulated product (Example 7)
- Figure 21 shows the transmittance spectrum of the ARTN samples obtained in Example 2 compared to conventional PCM (Example 8).
- the present process of producing nanoencapsulated temperature regulating agent (artn) via interfacial polymerization is an approach for the production of thermal regulation systems without the use of electricity, that is, using fusion / solidification mechanisms. heat exchange material and also the use of materials that promote reflection of infrared radiation, responsible for heating or cooling objects, surfaces or bodies.
- ARTN The production of ARTN is comprised of the execution of six consecutive processing steps that allow the generation of the nano-encapsulated of interest, being:
- step d distillation of solvents
- Step e polymerization and formation of the nanocapsulated shell.
- step f product drying.
- the preparation of the organic phase - FO, step a), is carried out by mechanical (preferred) or magnetic stirring of the inputs and generates a dispersion which simultaneously contains the solvent, a nonionic emulsifier, the organic material, a colloid. protector, colloidal oxide nanoparticles and the shell-forming monomer, therefore, appearing as a colloidal suspension. It should be noted that inclusion of colloidal oxide nanoparticles is optional.
- the solvent used should have partial solubility in water with values up to 20% by mass and boiling point lower than that of water, and may be from the family of acetates, preferably ethyl acetate.
- the organic material responsible for the melt / solidification heat absorption or release process can be wax, butter, paraffin, salt or soluble polymer or blends of these materials having a melting / solidification point in the range of 10 to 120 °, preferably between 29 ° C. at 32 ⁇ .
- the colloidal oxide to be used should have an average particle size of less than 200 nm, preferably less than 50 nm.
- the colloidal oxide may be based on titanium or zinc, preferably zinc.
- the monomer to be used in peel formation and NRNA generation should be cyanoacrylate, preferably butylcyanoacrylate type.
- the nonionic emulsifier and protective colloid may be poly (ethylene oxide) derivatives.
- the mass ratio of organic material / colloidal oxide nanoparticle / monomer may range from 47: 35: 16 to 92: 0.01: 7.99, preferably 73: 15: 12.
- the content of active material (organic material) present in the organic phase it may range from 12 to 35%, preferably 28% by mass.
- Step b) which makes up the preparation of the ARTN, consists of pre-emulsifying the organic phase - FO into an aqueous phase containing emulsifiers (FA-1).
- Emulsifiers may be anionic, cationic, nonionic or amphiphilic, preferably anionic, with anionic sulfated organic compounds.
- Preemulsification is carried out by preferably preferably mechanical stirring of the organic phase in the aqueous phase (FA1) in the emulsifier / water ratio from 0.1: 9.9 to 1: 1, preferably 1: 9 by mass. at a speed of 100 to 30,000 rpm, preferably 7,000 rpm, for the time required to complete emulsification at a temperature ranging from 10 to 80 ⁇ , preferably at room temperature, the ratio being between the organic and aqueous phases from 8 to 0.2 mass, preferably 2.5.
- FA1 aqueous phase
- Step c) is performed by diluting the generated pre-emulsion (FA-1) in the previous phase, enabling the diffusion of solvents in water.
- This dilution is performed with the addition of water under stirring which may range from 100 to 30,000 rpm, preferably at a speed of 7,000 rpm, for the time required until complete dilution.
- the dilution ratio of the preemulsion with water may be from 10 to 0.5, preferably 2.0 by mass.
- the dispersion is kept under stirring from 10 to 7,000 rpm, preferably 250 rpm, at a temperature ranging from 25 to 90 ° C, preferably 50 ° C, for a period of time for solvent removal and ranging from 1 to 4 hours, preferably 1 hour.
- the nanocapsulated polymerization and peeling step e) is carried out wherein the dispersion remains under agitation at 10 to 7,000 rpm, preferably 250 rpm, at a temperature ranging from 25 to 90 °, preferably 50 ° C. ⁇ for a period of time system stabilization which may range from 1 to 4 hours, preferably 2 hours.
- a drying step f) may be carried out if the aqueous dispersion of the NRNAs is subjected to any drying process such as spray-drying, fluid bed drying, filtration, lyophilization. , centrifugation, among others.
- the product generated in this invention has the following characteristics: average particle size ranging from 70 to 1500 nm preferably 250 nm, pH range from 3.0 to 8.0 preferably 4.2; solids content 5.0 to 50.0%, preferably 34%, spherical morphology and, when dry, it is powdery, partially agglomerated or in the form of dispersed particles and easily redispersed in aqueous medium.
- average particle size ranging from 70 to 1500 nm preferably 250 nm, pH range from 3.0 to 8.0 preferably 4.2
- EXAMPLE 1 Production of Nanoencapsulated Temperature Regulating Agent containing 80% / 13% / 7% by weight ratio of organic material / monomer / colloidal oxide
- aqueous phases were prepared for preemulsification and dilution of the preemulsion formed.
- the aqueous phase used for pre-emulsification (FA-1) was prepared with 17 g of distilled water, 1.5 g of sodium lauryl ether sulfate (LESS) and 1.5 g of ethyl acetate; and the second aqueous phase to be used for diluting the preemulsion (FA-2) was only 50 g distilled water.
- the system was stirred at 200 rpm at 50 ° C for 5 minutes.
- the preemulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and at room temperature for approximately 10 minutes, then adding FA-2 and the material. It was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask. The solvent distillation procedure was performed under the following conditions: temperature 50 ⁇ , stirring 280 rpm and negative pressure 380 mmHg for 1 hour. After distillation, the formulation was kept in reactor for a further 2 hours.
- the obtained nanoencapsulated product was subjected to particle size characterization by dynamic light scattering technique, pH by potentiometry, morphology by scanning electron microscopy technique, total solids content by thermogravimetry technique and thermal analysis by technique. differential scanning calorimetry (DSC).
- Table 1 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was on the order of 33.3% by mass, the average particle size of 171.6 nm and pH 8.0.
- Figure 2 shows a photograph of a plate containing the product after reaction exposed to the temperature of 4 ° C in an air circulation oven. As can be seen, the appearance of the sample is "dry", that is, without the presence of molten organic material, which melts at 32 ° C, indicating that it has been nanocapsulated by the interfacial polymerization process.
- Figure 3 shows a photomicrograph of the nanocapsules and, as can be seen, the particle size was in nanometer order.
- Figure 4 shows the DSC curve for the nanoencapsulated sample, showing consecutive heating and cooling cycles and showing that the enthalpy of melting of the material does not change. significant evidence proving that nanocapsules show a cyclic effect of energy absorption.
- EXAMPLE 2 Production of Nanoencapsulated Temperature Regulating Agent containing 73% / 12% / 15% mass ratio of organic material / monomer / colloidal oxide
- aqueous phases were prepared for preemulsification and dilution of the preemulsion formed.
- the aqueous phase used for preemulsification (FA-1) was prepared with 17 g of distilled water, 1.5 g of sodium lauryl ether sulfate (LESS) and 1.5 g of ethyl acetate; and the second aqueous phase to be used for diluting the preemulsion (FA-2) was only 50 g distilled water.
- the system was stirred at 200 rpm at 50 ⁇ for 5 minutes.
- the preemulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and at room temperature for approximately 10 minutes, then adding FA-2 and the material. It was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask.
- the solvent distillation procedure was carried out under the following conditions: temperature 50 ° C, stirring 28 rpm and negative pressure 440 mmHg for 40 minutes. After distillation, the formulation was kept in reactor for a further 2 hours.
- the obtained nanoencapsulated product was subjected to particle size characterization by the dynamic light scattering technique, pH by potentiometry, scanning electron microscopy morphology, colloidal physical stability by the dynamic scanning turbidimetry technique and the total solids content by thermogravimetry technique.
- Table 2 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was of the order of 33.8% by mass and the average particle size of 253.8 nm and pH 8.2.
- Figure 5 shows a photograph of a plate containing the product after reaction exposed at 40 ⁇ ° C and in an air circulation oven. As can be seen, the appearance of the sample is "dry", that is, without the presence of molten organic material which melts at 32 ° C, indicating that it has been nano encapsulated by the interfacial polymerization process.
- Figure 6 shows a photomicrograph of the nanoencapsulated product and, as can be seen, the particle size was in the nanometer order.
- Figure 7 shows a dynamic turbidimetry image of the sample, analyzed for a period of 24 consecutive hours after sample preparation, scanning the entire height of the sample holder every 1 hour. As can be observed, a behavior of colloidal physical stability over time is evidenced, with no difference in the backlight scattering of the sample for the evaluated times.
- EXAMPLE 3 Production of Nanoencapsulated Temperature Regulating Agent containing 57% / 19% / 24% by weight ratio of organic material / monomer / colloidal oxide
- 12 g of ethyl acetate, 1.7 g of sorbitan laurate (80 moles of ethylene oxide), 2 g of poly (ethylene oxide) triblock copolymer were added.
- aqueous phase used for preemulsification was prepared with 17 g of distilled water, 1.5 g of sodium lauryl ether sulfate (LESS) and 1.5 g of ethyl acetate; and the second aqueous phase to be used for diluting the preemulsion (FA-2) was only 50 g distilled water.
- the system was stirred at 200 rpm at 50 ⁇ for 5 minutes.
- the preemulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and room temperature, approximately 10 minutes, then adding FA-2 and the material. It was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask.
- the solvent distillation procedure was performed under the following conditions: temperature 50 ° C, stirring 28 rpm and negative pressure 440 mmHg for 40 minutes. After distillation, the formulation remained in reactor for a further 2 hours and 20 minutes.
- the obtained nanoencapsulated product was subjected to particle size characterization by dynamic light scattering technique, pH by potentiometry, morphology by scanning electron microscopy technique, and total solids content by thermogravimetry technique.
- Table 3 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was about 33.8% by mass and the average particle size 281.0 nm and pH 8.3.
- Figure 8 shows a photograph of a plate containing the product after reaction exposed to a temperature of 40 ° C in an air circulation oven. As can be seen, the appearance of the sample is "dry", that is, without the presence of molten organic material which melts at 32 ° C, indicating that it has been nano encapsulated by the interfacial polymerization process.
- Figure 9 shows a photomicrograph of the nanocapsules and, as can be seen, the particle size was in the nanometer order.
- EXAMPLE 4 Production of Nanoencapsulated Temperature Regulating Agent containing 80% / 9% / 11% w / w ratio of organic material / monomer / colloidal oxide
- aqueous phases were prepared for preemulsification and dilution of the preemulsion formed.
- the aqueous phase used for preemulsification (FA-1) was prepared with 17 g of distilled water, 1.5 g of sodium lauryl ether sulfate (LESS) and 1.5 g of ethyl acetate; and the second The aqueous phase to be used for diluting the preemulsion (FA-2) was only 50 g of distilled water.
- the system was stirred at 200 rpm at 50 ° C for 5 minutes.
- the preemulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and room temperature, approximately 10 minutes, then adding FA-2 and The material was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask.
- the solvent distillation procedure was performed under the following conditions: temperature 50 ° C, stirring 28 rpm and negative pressure 440 mmHg for 40 minutes. After distillation the formulation was kept in reactor for a further 2 hours and 20 minutes.
- the obtained nanoencapsulated product was subjected to particle size characterization by dynamic light scattering technique, pH by potentiometry, morphology by scanning electron microscopy technique, and total solids content by thermogravimetry technique.
- Table 4 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was on the order of 36.4 mass% and the average particle size 244.3 nm and pH 8.3.
- Figure 10 shows a photograph of a plate containing the product after reaction exposed at 40 ° C in an air circulation oven. As can be seen the appearance of the sample is "dry", ie without the presence of molten organic material which melts at 32 ° C indicating that it has been encapsulated by the interfacial polymerization process.
- Figure 11 shows a photomicrograph of the nanocapsules and, as can be seen, the particle size was in nanometer order.
- aqueous phases were prepared for preemulsification and dilution of the preemulsion formed.
- the aqueous phase used for preemulsification (FA-1) was prepared with 17 g of distilled water, 1.5 g of sodium lauryl ether sulfate (LESS) and 1.5 g of ethyl acetate; and the second aqueous phase to be used for diluting the preemulsion (FA-2) was only 50 g distilled water.
- the system was stirred at 200 rpm at 50 ⁇ for 5 minutes.
- the pre-emulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and room temperature, approximately 10 minutes, then adding FA-2 and The material was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask.
- the solvent distillation procedure was performed under the following conditions: temperature 50 ° C, stirring 2880 rpm and negative pressure 380 mmHg for 1 hour. After distillation, the formulation remained in reactor for a further 2 hours.
- the obtained nanoencapsulated product was subjected to particle size characterization by the dynamic light scattering technique, pH by potentiometry, morphology by the scanning electron microscopy technique, colloidal physical stability by the dynamic scanning turbidimetry technique and the total solids content by thermogravimetry technique.
- Table 5 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was on the order of 29.36 mass%, the average particle size 226.8 nm and pH 8.3.
- Figure 12 shows a photograph of a plate containing the product after reaction exposed to a temperature of 40 ° C in an air circulation oven. As can be seen, the appearance of the sample is "dry", that is, without the presence of molten organic material, which melts at 32 ° C, proving that it was nanoen encapsulated by the interfacial polymerization process.
- Figure 13 shows a photomicrograph of the nanocapsules and, as can be seen, the particle size was in the nanometric order.
- Figure 14 shows a dynamic turbidimetry image of the sample, analyzed for a period of 17 consecutive hours after preparation, performing full-length sweeps every 1 hour. As can be observed, a behavior of colloidal physical stability over time is evidenced, with no difference in the backlight scattering of the sample for the evaluated times.
- EXAMPLE 6 Production of Nanoencapsulated Temperature Regulating Agent containing 48% / 36% / 16% by weight ratio of organic material / monomer / colloidal oxide
- 10 g of ethyl acetate, 1.7 g of sorbitan laurate (80 moles of ethylene oxide), 2 g of poly (ethylene oxide) triblock copolymer were added.
- the preemulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and room temperature, approximately 10 minutes, then adding FA-2 and the material. It was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask.
- the solvent distillation procedure was performed under the following conditions: temperature 50 ° C, stirring 28 rpm and negative pressure 380 mmHg for 1 hour. After distillation the formulation was kept in reactor for a further 2 hours.
- the obtained nanoencapsulated product was subjected to particle size characterization by dynamic light scattering technique, pH by potentiometry, scanning electron microscopy morphology, colloidal physical stability by dynamic scanning turbidimetry technique and the content of total solids by thermogravimetry technique.
- Table 6 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was of the order of 31.21% by mass, the average particle size of 266.0 nm and pH of 8.21.
- Figure 15 shows a photograph of a plate containing the product after reaction exposed to a temperature of 40 ° C and in an air circulation oven. As can be seen, the appearance of the sample is "dry", that is, without the presence of molten organic material, which melts at 32 ° C, proving that it was nanoen encapsulated by the interfacial polymerization process.
- Figure 16 shows a photomicrograph of the nanocapsules and, as can be seen, the particle size was in nanometer order.
- Figure 17 shows a dynamic turbidimetry image of the sample, analyzed for a period of 24 consecutive hours after sample preparation, scanning the entire height of the sample holder every 1 hour. As can be observed, a behavior of colloidal physical stability over time is evidenced, with no difference in light backscattering of the sample for the evaluated times.
- EXAMPLE 7 Production of Nanoencapsulated Temperature Regulating Agent containing 48% / 36% / 16% by weight ratio of organic material / monomer / colloidal oxide
- aqueous phases were prepared for preemulsification and dilution of the preemulsion formed.
- the aqueous phase used for preemulsification (FA-1) was prepared with 17 g of distilled water, 1.5 g of sodium laureth sulfate (LESS) and 1.5 g of ethyl acetate; and the second aqueous phase to be used for diluting the preemulsion (FA-2) was only 50 g of distilled water.
- the system was stirred at 200 rpm at 50 ° C for 5 minutes.
- the preemulsion was prepared by slowly adding the organic phase - FO to FA-1 under mechanical stirring of 7,000 rpm and room temperature, approximately 10 minutes, then adding FA-2 and the material. It was transferred to the jacketed glass reactor and equipped with a distillation condenser, thermostated bath, mechanical stirring, vacuum pump and distillate collection flask.
- the solvent distillation procedure was carried out under the following conditions: temperature 50 ° C, stirring 280 rpm and negative pressure 380 mmHg for 1 hour. After distillation the formulation was kept in reactor for a further 2 hours.
- the obtained nanoencapsulated product was subjected to particle size characterization by the dynamic light scattering technique, pH by potentiometry, scanning electron microscopy morphology, colloidal physical stability by the dynamic scanning turbidimetry technique and the content. total solids by thermogravimetry technique.
- Table 7 presents the results of average particle size, pH, total solids content. As can be seen, the solids content was on the order of 31.89 mass%, the average particle size 226.6 nm and pH 7.9.
- Figure 18 shows a photograph of a plate containing the product after reaction exposed to a temperature of 40 ° C and in an air circulation oven. As can be seen, the appearance of the sample is "dry", that is, without the presence of molten organic material, which melts at 32 ° C, indicating that it has been nanocapsulated by the interfacial polymerization process.
- Figure 19 shows a photomicrograph of the nanocapsules and, as can be seen, the particle size was in the nanometric order.
- Figure 20 shows the DSC curve for the nanocapsulated sample showing 20 consecutive heating and cooling cycles, showing that the melting enthalpy of the material does not change significantly, and the nanocapsules show a cyclic effect of energy absorption.
- EXAMPLE 8 Evaluation of the efficiency of the obtained ARTN in blocking infrared radiation.
- Figure 21 shows an overlap of the infrared spectra obtained in transmittance mode through the films of the evaluated materials.
- the ARTN blocked almost all of infrared radiation, while conventional PCM blocked only 50% of the radiation. This result demonstrates the production of an ARTN capable of blocking infrared radiation and consequently modifying the heating profile of any surface to which it is applied.
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Abstract
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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EP16718598.2A EP3406690A1 (en) | 2016-01-22 | 2016-01-22 | Process for producing nanoencapsulated temperature regulating agent (ntra) by inferfacial polymerization |
US16/072,098 US20190031937A1 (en) | 2016-01-22 | 2016-01-22 | A PROCESS FOR PRODUCING NANOENCAPSULATED TEMPERATURE REGULATING AGENT (ntra) VIA INFERFACIAL POLYMERIZATION |
AU2016387182A AU2016387182A1 (en) | 2016-01-22 | 2016-01-22 | Process for producing nanoencapsulated temperature regulating agent (NTRA) by inferfacial polymerization |
PCT/BR2016/050009 WO2017124162A1 (pt) | 2016-01-22 | 2016-01-22 | Processo de produção de agente regulador de temperatura nanoencapsulado (artn) via polimerização interfacial |
CL2018001981A CL2018001981A1 (es) | 2016-01-22 | 2018-07-20 | Proceso para producir un agente regulador de temperatura nanoencapsulado (ntra) vía polimerización interfacial. |
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PCT/BR2016/050009 WO2017124162A1 (pt) | 2016-01-22 | 2016-01-22 | Processo de produção de agente regulador de temperatura nanoencapsulado (artn) via polimerização interfacial |
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US (1) | US20190031937A1 (pt) |
EP (1) | EP3406690A1 (pt) |
AU (1) | AU2016387182A1 (pt) |
CL (1) | CL2018001981A1 (pt) |
WO (1) | WO2017124162A1 (pt) |
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GB1235706A (en) * | 1967-06-23 | 1971-06-16 | Pelikan Werke Wagner Guenther | Process for the production of microcapsules |
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US20070224899A1 (en) | 2004-04-29 | 2007-09-27 | Dungworth Howard R | Particulate Compositions and Their Manufacture |
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KR20130067128A (ko) | 2011-12-13 | 2013-06-21 | 현대자동차주식회사 | 열제어 소재용 상변화 물질과 전도성 필러의 복합입자와 그 제조방법 |
US20130177616A1 (en) * | 2010-03-19 | 2013-07-11 | Instituto De Pesquisas Tecnologicas Do Estado De Sao Paulo S.A.-Ipt | Nanostructured sun protection agent and process |
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Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2009126441A1 (en) * | 2008-04-10 | 2009-10-15 | Board Of Regents, The University Of Texas System | Compositions and methods for thermo-sensitive nanoparticles and magnetic nanoparticles |
-
2016
- 2016-01-22 EP EP16718598.2A patent/EP3406690A1/en not_active Withdrawn
- 2016-01-22 US US16/072,098 patent/US20190031937A1/en not_active Abandoned
- 2016-01-22 WO PCT/BR2016/050009 patent/WO2017124162A1/pt active Application Filing
- 2016-01-22 AU AU2016387182A patent/AU2016387182A1/en not_active Abandoned
-
2018
- 2018-07-20 CL CL2018001981A patent/CL2018001981A1/es unknown
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GB1235706A (en) * | 1967-06-23 | 1971-06-16 | Pelikan Werke Wagner Guenther | Process for the production of microcapsules |
US20070224899A1 (en) | 2004-04-29 | 2007-09-27 | Dungworth Howard R | Particulate Compositions and Their Manufacture |
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US20130216834A1 (en) | 2010-09-13 | 2013-08-22 | Sakai Chemical Industry Co., Ltd, | Zinc oxide particles and cosmetic |
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CL2018001981A1 (es) | 2019-08-09 |
EP3406690A1 (en) | 2018-11-28 |
US20190031937A1 (en) | 2019-01-31 |
AU2016387182A1 (en) | 2018-09-06 |
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