BR112016010479B1 - GRAPHENE-BASED POLYMER COMPOUNDS FOR THE PRODUCTION OF CONDOMS WITH HIGH THERMAL TRANSFER, IMPROVED SENSITIVITY AND DRUG ADMINISTRATION CAPACITY - Google Patents
GRAPHENE-BASED POLYMER COMPOUNDS FOR THE PRODUCTION OF CONDOMS WITH HIGH THERMAL TRANSFER, IMPROVED SENSITIVITY AND DRUG ADMINISTRATION CAPACITY Download PDFInfo
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- BR112016010479B1 BR112016010479B1 BR112016010479-0A BR112016010479A BR112016010479B1 BR 112016010479 B1 BR112016010479 B1 BR 112016010479B1 BR 112016010479 A BR112016010479 A BR 112016010479A BR 112016010479 B1 BR112016010479 B1 BR 112016010479B1
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Abstract
compósitos poliméricos à base de grafeno para produção de preservativos com alta transferência térmica, sensibilidade aperfeiçoada e capacidade de administração de fármacos. a presente invenção refere-se a um preservativo com maior resistência mecânica, transferência térmica e propriedades de carregamento de fármaco compostos de grafeno e nanocompósitos poliméricos à base de seus derivados é proporcionado. o grafeno e seus derivados carregados com ou sem ingredientes farmacêuticos são dispersos uniformemente em polímeros de formação de preservativos (cmps) usando métodos de dispersão, subsequentemente os preservativos são produzidos por métodos de moldagem por imersão. o grafeno e seus derivados são carregados com ingredientes farmacêuticos ativos para liberação durante a relação sexual para prevenção de doenças sexualmente transmissíveis (dsts), gravidez indesejada e para aumentar o prazer sexual.graphene-based polymeric composites for the production of condoms with high thermal transfer, improved sensitivity and drug delivery capacity. The present invention relates to a preservative with greater mechanical resistance, thermal transfer and drug loading properties composed of graphene and polymeric nanocomposites based on its derivatives. Graphene and its derivatives loaded with or without pharmaceutical ingredients are uniformly dispersed in preservative forming polymers (CMPs) using dispersion methods, subsequently condoms are produced by dip molding methods. Graphene and its derivatives are loaded with active pharmaceutical ingredients for release during sexual intercourse to prevent sexually transmitted diseases (STDs), unwanted pregnancies and to increase sexual pleasure.
Description
[001] A presente invenção refere-se, em geral, a preservativos, mais especificamente, a preservativos compostos de grafeno e seus nanocompósitos poliméricos incorporados derivados.[001] The present invention relates, in general, to condoms, more specifically, to condoms composed of graphene and its derivative embedded polymeric nanocomposites.
[002] Os preservativos são dispositivos de proteção usados tanto para contracepção quanto para prevenção de doenças sexualmente transmissíveis (DSTs) durante a relação sexual. Nos últimos anos, a incidência de DSTs tem aumentado, sendo esta uma razão para a ampla utilização dos preservativos. Os preservativos geralmente são feitos de borracha natural, borracha sintética, poliuretano,poliéster, etc. Os compósitos poliméricos têm sido utilizados para produzir diversos produtos úteis, inclusive preservativos, uma vez que os compósitos poliméricos apresentam propriedades físicas, químicas e mecânicas melhores que as do polímero hospedeiro. Diversos materiais estão sendo incorporados aos polímeros para a produção de compósitos poliméricos. Recentemente, o grafeno tem chamado bastante atenção por suas incríveis propriedades.[002] Condoms are protective devices used both for contraception and for the prevention of sexually transmitted diseases (STDs) during sexual intercourse. In recent years, the incidence of STDs has increased, which is one reason for the widespread use of condoms. Condoms are usually made from natural rubber, synthetic rubber, polyurethane, polyester, etc. Polymeric composites have been used to produce a variety of useful products, including preservatives, as polymer composites have better physical, chemical, and mechanical properties than the host polymer. Several materials are being incorporated into polymers to produce polymer composites. Recently, graphene has attracted a lot of attention for its amazing properties.
[003] O grafeno é uma forma cristalina de carbono e sua estrutura constitui uma única folha de átomos de carbono ligados uns aos outros por uma ligação sp2 disposta em uma rede cristalina hexagonal em forma de “favo de mel”. O grafeno é a unidade básica estrutural para alguns dos alótropos de carbono, tal como grafita, nanotubos de carbono e fulerenos. O grafeno é um material fino e transparente que apresenta excelente resistência mecânica, condutividade elétrica, propriedade de transferência térmica e ampla área de superfície. Além disso, descobriu- se que o Óxido de Grafeno (GO), graças à sua estrutura planar e estrutura n-conjugada e à possibilidade de funcionalização adicional, possui excelente capacidade de imobilizar uma grande variedade de substâncias, inclusive metais, fármacos, biomoléculas e moléculas fluorescentes.[003] Graphene is a crystalline form of carbon and its structure constitutes a single sheet of carbon atoms linked to each other by an sp2 bond arranged in a hexagonal crystal lattice in the form of a "honeycomb". Graphene is the basic structural unit for some of the carbon allotropes, such as graphite, carbon nanotubes and fullerenes. Graphene is a thin, transparent material that exhibits excellent mechanical strength, electrical conductivity, heat transfer property, and large surface area. Furthermore, it was found that Graphene Oxide (GO), thanks to its planar structure and n-conjugated structure and the possibility of additional functionalization, has an excellent ability to immobilize a wide variety of substances, including metals, drugs, biomolecules and fluorescent molecules.
[004] Os compósitos poliméricos à base de grafeno são conhecidos na técnica anterior. Por exemplo, os pedidos de patente indiano No 1893/DELNP/2009, 2612/KOLNP/2012,3845/CHENP/2012 e a publicação PCT No 2013/127712 discutem nanocompósitos poliméricos / de resina / de borracha reforçada com grafeno. Zahn et al. (J. Mater. Chem., 2012, 22, 10464) produziram compósitos de borracha natural/grafeno vulcanizado com uma rede segregada condutora apresentando boa condutividade elétrica, permeabilidade ao vapor d’água e alta resistência mecânica por automontagem em látex e prensagem a quente estática. No entanto, não se constata o uso do grafeno na produção de preservativos.[004] Graphene-based polymeric composites are known in the prior art. For example, Indian Patent Applications No. 1893/DELNP/2009, 2612/KOLNP/2012,3845/CHENP/2012 and PCT Publication No. 2013/127712 discuss polymeric / resin / graphene reinforced rubber nanocomposites. Zahn et al. (J. Mater. Chem., 2012, 22, 10464) produced natural rubber/vulcanized graphene composites with a conductive segregated network showing good electrical conductivity, permeability to water vapor and high mechanical strength by self-assembly in latex and hot pressing static. However, there is no evidence of the use of graphene in the production of condoms.
[005] A publicação PCT No 2012/099853 revela uma composição elastomérica para produção de artigos elastoméricos, como preservativos, luvas etc., e o artigo elastomérico inclui pelo menos um revestimento. Aditivos de alta condutividade térmica, tais como particulados de metal, grafenos, tubos de nanocarbono etc. também podem ser usados como revestimentos. Entretanto, ela não revela um compósito polimérico incorporado com grafeno para produção de preservativos.[005] PCT publication No. 2012/099853 discloses an elastomeric composition for producing elastomeric articles such as condoms, gloves etc., and the elastomeric article includes at least one coating. High thermal conductivity additives such as metal particulates, graphenes, nanocarbon tubes etc. can also be used as coatings. However, it does not reveal a polymer composite incorporated with graphene to produce condoms.
[006] Muitas patentes e pedidos existentes revelam preservativos contendo alótropos de carbono, tal como grafita, fulerenos e nanotubos de carbono. Por exemplo, o pedido de patente US No 2005/0152891 refere-se a nanotubos de carbono entranhados em polímero, em que os nanotubos contêm óxido nítrico ou um gás para distribuir óxido nítrico ao local de tratamento que está em risco de formação de coágulos, tal como na área de um stent implantado. O documento russo 2128484 revela um preservativo compreendendo fulerenos como cargas.[006] Many existing patents and applications disclose preservatives containing carbon allotropes such as graphite, fullerenes and carbon nanotubes. For example, US patent application No. 2005/0152891 relates to polymer-entrapped carbon nanotubes, where the nanotubes contain nitric oxide or a gas to deliver nitric oxide to the treatment site that is at risk of clot formation, such as in the area of an implanted stent. Russian document 2128484 discloses a condom comprising fullerenes as fillers.
[007] O pedido de patente americano No 2013/0150943 refere-se a um dispositivo implantável biodegradável compreendendo polímero biodegradável. A resistência e tenacidade do material polimérico são aprimoradas pela incorporação de aditivos, tais como nanotubos de carbono, ao material polimérico.[007] The American patent application No. 2013/0150943 refers to a biodegradable implantable device comprising biodegradable polymer. The strength and toughness of the polymeric material are improved by incorporating additives, such as carbon nanotubes, into the polymeric material.
[008] O documento alemão 3705293 revela um dispositivo contraceptivo que é constituído de borracha ou material similar. O dispositivo também contém material condutor elétrico, tal como carbono, grafita, para superar as características isolantes do material de borracha.[008] German document 3705293 discloses a contraceptive device that is made of rubber or similar material. The device also contains electrically conductive material, such as carbon, graphite, to overcome the insulating characteristics of the rubber material.
[009] O documento chinês 202154785 revela um preservativo em série com formato de pênis feito de um novo material elástico adesivo que contém nanotubos de carbono conectados aleatoriamente.[009] Chinese document 202154785 discloses a penis-shaped serial condom made of a new elastic adhesive material that contains randomly connected carbon nanotubes.
[010] O pedido de patente americano No 2001/0053813 descreve uma composição de borracha compreendendo partículas de borracha reticuladas, sílica e grafita. A composição de borracha pode ser convertida em uma borracha vulcanizada contendo excelente resistência à tração e resistência ao desgaste para produzir um material sanitário, tal como uma borracha contraceptiva.[010] American patent application No. 2001/0053813 describes a rubber composition comprising crosslinked rubber particles, silica and graphite. The rubber composition can be converted to a vulcanized rubber having excellent tensile strength and wear resistance to produce a sanitary material such as contraceptive rubber.
[011] A publicação PCT No 1995/021637 refere-se a um preservativo com propriedades antivirais feito de borracha látex revestida com fulereno de Langmuir-Blodgett.[011] PCT Publication No. 1995/021637 refers to a condom with antiviral properties made of Langmuir-Blodgett fullerene coated latex rubber.
[012] A patente americana No 6355350 revela filmes carbonáceos biocompatíveis e um método para fabricação de tais filmes em implantes médicos. O revestimento de filme carbonáceo pode ser aplicado a dispositivos intra-uterinos contraceptivos.[012] US patent No. 6355350 discloses biocompatible carbonaceous films and a method for manufacturing such films in medical implants. Carbonaceous film coating can be applied to contraceptive intrauterine devices.
[013] O documento de Taiwan 296519 refere-se a um método para produção de nanopreservativos higiênicos de maior satisfação sexual pela mistura de uma quantidade apropriada de nanopós de carbono elementar, metal, óxido metal, cerâmicas, mineral em diâmetro de partícula (menos de 1000 nm) com material de borracha.[013] Taiwan document 296519 refers to a method for producing more sexually satisfying hygienic nanocondoms by mixing an appropriate amount of elemental carbon, metal, metal oxide, ceramic, mineral nanopowders in particle diameter (less than 1000 nm) with rubber material.
[014] Embora esses documentos da técnica anterior discutam preservativos feitos de polímero incorporado com alótropos de carbono, como grafita, nanotubos de carbono e fulerenos com propriedades de condução térmica e/ou mecânica aperfeiçoadas, nenhum deles revela o uso de grafeno e seus derivados, que possuem qualidades superiores aos demais alótropos de carbono, em Polímeros de Formação de Preservativos (CMPs).[014] Although these prior art documents discuss preservatives made from polymer incorporated with carbon allotropes such as graphite, carbon nanotubes and fullerenes with improved thermal and/or mechanical conduction properties, none of them disclose the use of graphene and its derivatives, which have superior qualities to other carbon allotropes, in Condom Formation Polymers (CMPs).
[015] Por conseguinte, existe a necessidade de preservativos de próxima geração (um dispositivo preventivo de múltipla utilidade) feitos de compósitos poliméricos à base de grafeno com propriedades superiores de condução mecânica, térmica, e de carregamento de fármaco.[015] Therefore, there is a need for next-generation condoms (a multiple-use preventive device) made from graphene-based polymeric composites with superior mechanical, thermal, and drug-carrying properties.
[016] A presente invenção provê um preservativo composto de nanocompósitos poliméricos à base de grafeno. O grafeno e seus derivados são incorporados em polímeros de formação de preservativos (CMPs), tal como borracha natural, borracha sintética, poliuretano, poliéster, etc. para produzir preservativos mais finos com espessura menor do que 0,04 mm com propriedades superiores de condução mecânica e térmica e de carregamento de fármaco.[016] The present invention provides a condom composed of polymeric nanocomposites based on graphene. Graphene and its derivatives are incorporated into preservative-forming polymers (CMPs) such as natural rubber, synthetic rubber, polyurethane, polyester, etc. to produce thinner condoms less than 0.04mm thick with superior mechanical and thermal conduction and drug loading properties.
[017] O método de incorporação de grafeno e seus derivados carregados com ou sem ingredientes ativos farmacêuticos em Polímeros de Formação de Preservativos (CMPs) inclui (a) o método de dispersão não-covalente (b) o método de dispersão covalente. O método de dispersão não- covalente inclui alta força cisalhante / polimerização in situ e o método de dispersão covalente inclui enxerto de polímero ou oligômero / funcionalização do grafeno e seus derivados.[017] The method of incorporating graphene and its derivatives loaded with or without active pharmaceutical ingredients into Condom-Forming Polymers (CMPs) includes (a) the non-covalent dispersion method (b) the covalent dispersion method. The non-covalent dispersion method includes high shear strength / in situ polymerization and the covalent dispersion method includes polymer or oligomer grafting / functionalization of graphene and its derivatives.
[018] Na modalidade preferida da invenção, os ingredientes farmaceuticamente ativos, que incluem fármaco antiretroviral / espermicida / vasodilatadores / aromas, são carregados em grafeno e seus derivados para liberação durante a relação sexual para evitar doenças sexualmente transmissíveis (DSTs), gravidez indesejada e aumentar o prazer sexual.[018] In the preferred embodiment of the invention, the pharmaceutically active ingredients, which include antiretroviral drug / spermicide / vasodilators / aromas, are loaded in graphene and its derivatives for release during sexual intercourse to prevent sexually transmitted diseases (STDs), unwanted pregnancy and increase sexual pleasure.
[019] O objetivo da presente invenção será descrito agora em mais detalhes com referência ao desenho anexo, no qual:[019] The purpose of the present invention will now be described in more detail with reference to the attached drawing, in which:
[020] A Fig. 1 é um diagrama esquemático ilustrando grafeno carregado com ingredientes farmaceuticamente ativos e seus derivados, o qual é disperso uniformemente em polímeros de formação de preservativos (CMPs).[020] Fig. 1 is a schematic diagram illustrating graphene loaded with pharmaceutically active ingredients and their derivatives, which is uniformly dispersed in preservative-forming polymers (CMPs).
[021] A presente invenção refere-se a um preservativo, como mostra a Fig. 1, composto de grafeno carregado com ingredientes farmaceuticamente ativos e seus nanocompósitos poliméricos à base de seus derivados.[021] The present invention relates to a preservative, as shown in Fig. 1, composed of graphene loaded with pharmaceutically active ingredients and its polymeric nanocomposites based on their derivatives.
[022] De acordo com a presente invenção, o grafeno e seus derivados são incorporados em polímeros de formação de preservativos, tal como borracha natural, borracha sintética, poliuretano, poliéster, etc. para produzir preservativos mais finos com espessura menor do que 0,04 mm com propriedades superiores de condução mecânica e térmica e de carregamento de fármaco. Os derivados de grafeno incluem óxido de Grafeno (GO), amônia GO e grafeno funcionalizado (GO e seus derivados).[022] According to the present invention, graphene and its derivatives are incorporated into preservative-forming polymers, such as natural rubber, synthetic rubber, polyurethane, polyester, etc. to produce thinner condoms less than 0.04mm thick with superior mechanical and thermal conduction and drug loading properties. Graphene derivatives include graphene oxide (GO), GO ammonia and functionalized graphene (GO and its derivatives).
[023] O método de incorporação de grafeno e seus derivados carregados, com ou sem ingredientes farmaceuticamente ativos em Polímeros de Formação de Preservativos (CMPs), inclui (a) o método de dispersão não- covalente e (b) o método de dispersão covalente.[023] The method of incorporating graphene and its charged derivatives, with or without pharmaceutically active ingredients in Condom-Forming Polymers (CMPs), includes (a) the non-covalent dispersion method and (b) the covalent dispersion method .
[024] O método de dispersão não-covalente da presente invenção utiliza qualquer um dos seguintes dois métodos para dispersar grafeno e seus derivados em Polímero de Formação de Preservativos (CMP). O método inclui (1) alta força cisalhante (2) polimerização in situ.[024] The non-covalent dispersion method of the present invention uses any of the following two methods to disperse graphene and its derivatives in Condom-Forming Polymer (CMP). The method includes (1) high shear strength (2) in situ polymerization.
[025] As modalidades da invenção serão descritas a título de exemplo.[025] The embodiments of the invention will be described by way of example.
[026] Em uma modalidade da presente invenção, método de dispersão não-covalente usando alta força cisalhante: O grafeno ou derivados de Grafeno, tal como óxido de grafeno (GO) ou amônia de GO ou GO funcionalizado é disperso uniformemente nos Polímeros de Formação de Preservativos (CMPs) usando dispositivos de alto cisalhamento, tal como ultrassom e homogeneizador de alta pressão. Após a dispersão uniforme em polímeros de formação de preservativos (CMPs), GO e seus derivados ser reduzida usando agentes redutores, tal como monoidrato de hidrazina ou boroidreto de sódio ou agentes redutores ecologicamente redutores, tal como triptofano, ácido ascórbico etc., usando os mesmos dispositivos de alto cisalhamento.[026] In one embodiment of the present invention, non-covalent dispersion method using high shear strength: Graphene or Graphene derivatives such as graphene oxide (GO) or functionalized GO or GO ammonia is uniformly dispersed in the Formation Polymers Condoms (CMPs) using high-shear devices such as ultrasound and high-pressure homogenizer. After uniform dispersion in preservative-forming polymers (CMPs), GO and its derivatives are reduced using reducing agents such as hydrazine monohydrate or sodium borohydride or reducing ecologically reducing agents such as tryptophan, ascorbic acid etc., using them same high-shear devices.
[027] Dois métodos de processamento diferentes foram usados para incorporar GO reduzido e grafeno em CMP e são apresentados a seguir.[027] Two different processing methods were used to incorporate reduced GO and graphene into CMP and are presented below.
[028] Processo para incorporar rGO reduzido: o presente processo proporciona um novo produto e um novo método para a fabricação de preservativos masculinos incorporados com óxido de grafeno reduzido (rGO) a partir de látex de borracha natural.[028] Process to incorporate reduced rGO: the present process provides a new product and a new method for the manufacture of male condoms incorporated with reduced graphene oxide (rGO) from natural rubber latex.
[029] O pó de grafita comercialmente disponível é misturado com ácido sulfúrico a 98% (1:17,5%) em um béquer de 500 mL por aproximadamente 2 a 5 horas. Adiciona-se permanganato de potássio gradualmente (razão de 1:3 com relação à grafita) à solução acima (tempo de intervalo utilizado de 10 a 40 min). A temperatura deve estar sempre abaixo de 10 a 20oC. A mistura é então agitada à 30 - 40 oC por 4 a 5 horas. A solução resultante é então diluída pela adição de 80 a 100 mL de água sob agitação vigorosa e uma suspensão marrom escura é obtida. A suspensão foi então tratada pela adição de solução de peróxido de hidrogênio a 30% (5 a 10 mL) e 100 a 200 mL de água destilada. A suspensão de óxido de grafita resultante foi lavada por centrifugação repetida com HC1 a 5% seguido de água destilada até que o pH da solução se torne neutro (velocidade de centrifugação 5000 - 10000 rpm por 5 a 20 mins). A nanoestrutura de GO é então obtida pela adição de 100 a 200 mL de água ao precipitado resultante e então sonicada em banho (5 a 10 mins) para obter uma suspensão uniforme de GO.[029] Commercially available graphite powder is mixed with 98% sulfuric acid (1:17.5%) in a 500 mL beaker for approximately 2 to 5 hours. Potassium permanganate is added gradually (1:3 ratio with graphite) to the above solution (time interval used from 10 to 40 min). The temperature must always be below 10 to 20oC. The mixture is then stirred at 30 - 40 °C for 4 to 5 hours. The resulting solution is then diluted by adding 80 to 100 ml of water under vigorous stirring and a dark brown suspension is obtained. The suspension was then treated by adding 30% hydrogen peroxide solution (5 to 10 mL) and 100 to 200 mL of distilled water. The resulting graphite oxide suspension was washed by repeated centrifugation with 5% HCl followed by distilled water until the pH of the solution became neutral (centrifugation speed 5000 - 10000 rpm for 5 to 20 mins). The GO nanostructure is then obtained by adding 100 to 200 mL of water to the resulting precipitate and then bath sonicated (5 to 10 mins) to obtain a uniform suspension of GO.
[030] A suspensão de GO é então misturada com látex composto para preparar os preservativos de látex de Borracha Natural incorporada com rGO com teor de rGO variável (0,1 a 20 phr). A suspensão de GO é misturada com látex composto e toda a mistura é sonicada em sonda (amplitude de 30 a 90%) para obter uma dispersão uniforme de GO em látex de borracha natural tempo de sonicação variando de 1 a 10 mins). À esta mistura, adiciona-se um dos seguintes agentes redutores, tal como hidrato de hidrazina / triptofano / ácido ascórbico / uréia / tiouréia-amônia / enzimas etc. para obter o látex de borracha natural incorporada com rGO. Os preservativos de látex de borracha natural incorporada com rGO são então preparados por moldagem por imersão em moldes de vidro (velocidade da máquina ajustada para obter espessura adequada). O número de imersões também pode ser variado dependendo da espessura necessária. As amostras imersas são então vulcanizadas à 60-100 °C em uma estufa de ar quente e então retiradas dos moldes de vidro usando pó de sílica para obter os preservativos de látex de borracha natural incorporados com rGO.[030] The GO suspension is then mixed with composite latex to prepare the Natural Rubber latex condoms incorporated with rGO with variable rGO content (0.1 to 20 phr). The GO suspension is mixed with composite latex and the entire mixture is probe sonicated (range 30 to 90%) to obtain a uniform dispersion of GO in natural rubber latex sonication time ranging from 1 to 10 mins). To this mixture, add one of the following reducing agents such as hydrazine hydrate / tryptophan / ascorbic acid / urea / thiourea-ammonia / enzymes etc. to obtain natural rubber latex incorporated with rGO. Natural rubber latex condoms incorporated with rGO are then prepared by dip molding in glass molds (machine speed adjusted to obtain proper thickness). The number of dips can also be varied depending on the required thickness. The dipped samples are then vulcanized at 60-100 °C in a hot air oven and then removed from the glass molds using silica powder to obtain the natural rubber latex preservatives incorporated with rGO.
[031] Os preservativos de látex de borracha natural incorporados com rGO apresentaram um aumento de 50 a 100% nas propriedades mecânicas ao aumentar o teor de rGO de 0,1 phr para 20 phr. A condutividade térmica das amostras também foi aumentada em 50 a 100%.[031] Natural rubber latex condoms incorporated with rGO showed a 50 to 100% increase in mechanical properties by increasing the rGO content from 0.1 phr to 20 phr. The thermal conductivity of the samples was also increased by 50 to 100%.
[032] Processo para incorporar grafeno: O presente método oferece um novo produto e um novo processo para a fabricação de preservativos masculinos incorporados com grafeno a partir de látex de borracha natural.[032] Process for Embedding Graphene: The present method offers a new product and process for manufacturing graphene embedded male condoms from natural rubber latex.
[033] A presente investigação se concentra na esfoliação de grafita em grafeno usando moagem em moinho de esferas planetário na presença de melamina ou outros agentes de esfoliação adequados (Ester Vazquez et al. ACS Nano, 2014, 8 (1), pp 563-571). A grafita comercialmente disponível é misturada com derivados de melamina/curcuminóides/tetraidrocurcuminóies/triazina (com a razão variando de 1:0.5 a 1:10 de grafita e agente esfoliante) em um moinho de esferas planetário com velocidade (100 a 250 rpm) e tempo (1 a 3 horas) de moagem variáveis. A amostra moída a seco é então dispersa em água ou DMF para obter algumas camadas de grafeno. O grafeno esfoliado é então caracterizado por meio de XRD, espectroscopia de Raman, análise TEM e AFM. A dispersão pode ser adicionalmente estabilizada por meio do processo de sonicação da sonda.[033] The present investigation focuses on the exfoliation of graphite on graphene using grinding in a planetary ball mill in the presence of melamine or other suitable exfoliating agents (Ester Vazquez et al. ACS Nano, 2014, 8 (1), pp 563- 571). Commercially available graphite is mixed with melamine/curcuminoids/tetrahydrocurcuminoies/triazine derivatives (ranging from 1:0.5 to 1:10 graphite and exfoliating agent) in a planetary ball mill with speed (100 to 250 rpm) and variable grinding time (1 to 3 hours). The dry milled sample is then dispersed in water or DMF to obtain some layers of graphene. The exfoliated graphene is then characterized using XRD, Raman spectroscopy, TEM and AFM analysis. The dispersion can be further stabilized through the probe sonication process.
[034] A dispersão de grafeno é então misturada com látex composto para preparar os preservativos de látex de borracha natural incorporada com grafeno com teor de grafeno variável (0,1 a 20 phr). A dispersão de grafeno após a sonicação em sonda é misturada com látex composto e toda a mistura é sonicada em sonda novamente para obter uma dispersão uniforme de grafeno em látex de borracha natural (tempo de sonicação variando de 1 a 10 mins). Os preservativos de látex de borracha natural incorporada com grafeno são então preparados por moldagem por imersão em moldes de vidro (a velocidade da máquina é ajustada para obter a espessura adequada). O número de imersões também pode ser variado dependendo da espessura necessária. As amostras imersas são então vulcanizadas à 60-100 °C em uma estufa de ar quente e então retiradas dos moldes de vidro usando pó de sílica para obter os preservativos de látex de borracha natural incorporados com grafeno.[034] The graphene dispersion is then blended with composite latex to prepare the graphene-incorporated natural rubber latex condoms with varying graphene content (0.1 to 20 phr). The graphene dispersion after probe sonication is mixed with composite latex and the entire mixture is probe sonicated again to obtain a uniform dispersion of graphene in natural rubber latex (sonication time ranging from 1 to 10 mins). The graphene-incorporated natural rubber latex condoms are then prepared by dip molding in glass molds (machine speed is adjusted to obtain the proper thickness). The number of dips can also be varied depending on the required thickness. The dipped samples are then vulcanized at 60-100 °C in a hot air oven and then removed from the glass molds using silica powder to obtain the natural rubber latex preservatives incorporated with graphene.
[035] Os preservativos de látex de borracha natural incorporados com grafeno apresentaram um aumento de 50 a 100% nas propriedades mecânicas ao aumentar o teor de grafeno de 0,1 phr para 20 phr. A condutividade térmica das amostras também foi aumentada em 50 a 100%.[035] Graphene-incorporated natural rubber latex condoms showed a 50 to 100% increase in mechanical properties by increasing the graphene content from 0.1 phr to 20 phr. The thermal conductivity of the samples was also increased by 50 to 100%.
[036] Em outra modalidade da presente invenção, método de dispersão não-covalente usando polimerização in situ: o GO ou seus derivados é dissolvido nos monômeros,particularmente isopreno, de modo a preparar a emulsão. Adicionalmente, a emulsão é polimerizada. Durante a formação do produto, o Óxido de Grafeno (GO) é reduzido usando agentes redutores, tal como monoidrato de hidrazina ou boroidreto de sódio ou agentes redutores ecologicamente corretos, tal como triptofano, ácido ascórbico etc.[036] In another embodiment of the present invention, non-covalent dispersion method using in situ polymerization: the GO or its derivatives is dissolved in the monomers, particularly isoprene, in order to prepare the emulsion. Additionally, the emulsion is polymerized. During product formation, Graphene Oxide (GO) is reduced using reducing agents such as hydrazine monohydrate or sodium borohydride or environmentally friendly reducing agents such as tryptophan, ascorbic acid etc.
[037] O teor total de sólidos da mistura de reação a 10- 40% misturando-se 7,5-30% em peso de isopreno, óxido de grafeno 0,5-2% e vinil carbazol 2-8% em água. Então, o agente tensoativo (SDS-7% da reação total) e o estabilizador (hexadecano-5% da solução monomérica) são misturados no sistema usando agitação magnética até que um sistema homogêneo seja obtido. Então, a solução de reação foi expurgada por 10 minutos por gás N2 para assegurar a remoção completa do ar da mistura de reação.[037] The total solids content of the 10-40% reaction mixture by mixing 7.5-30% by weight of isoprene, 0.5-2% graphene oxide and 2-8% vinyl carbazole in water. Then, the surface-active agent (SDS-7% of the total reaction) and the stabilizer (hexadecane-5% of the monomeric solution) are mixed in the system using magnetic stirring until a homogeneous system is obtained. Then, the reaction solution was purged for 10 minutes by N2 gas to ensure complete removal of air from the reaction mixture.
[038] A miniemulsão foi então preparada por sonicação em sonda contínua por 2 minutos. Após a sonicação, a reação é iniciada pelo uso do iniciador (persulfato de potássio/peróxido de benzoíla - 0-2% do peso monomérico). Após a adição do iniciador, toda a mistura de reação foi mantida à temperatura ambiente sob atmosfera de N2 por 4 a 5 horas. O andamento da reação foi monitorado usando estudos cinéticos. A mistura acima é então misturada com látex composto, e então o óxido de grafeno é reduzido pela adição de agentes redutores adequados, como ácido ascórbico/hidrato de hidrazina/dióxido de tiouréia/NH3/uréia para preparar os preservativos de látex de borracha natural incorporada com rGO com teor de rGO variável (0,1 a 20 phr). A dispersão de rGO após a sonicação é misturada com látex composto e toda a mistura é sonicada novamente para obter uma dispersão uniforme de rGO no látex de borracha natural (tempo de sonicação variando de 1 a 10 mins). Os preservativos de látex de borracha natural incorporada com rGO são então preparados por moldagem por imersão sobre moldes de vidro (a velocidade da máquina é ajustada para obter a espessura apropriada). O número de imersões também pode ser variado dependendo da espessura necessária. As amostras imersas são então vulcanizadas à 60-100 °C em uma estufa de ar quente e então retiradas dos moldes de vidro usando pó de sílica para obter os preservativos de látex de borracha natural incorporados com rGO.[038] The miniemulsion was then prepared by continuous probe sonication for 2 minutes. After sonication, the reaction is initiated by using the initiator (potassium persulfate/benzoyl peroxide - 0-2% monomeric weight). After addition of the initiator, the entire reaction mixture was kept at room temperature under a N2 atmosphere for 4 to 5 hours. The progress of the reaction was monitored using kinetic studies. The above mixture is then mixed with composite latex, and then graphene oxide is reduced by adding suitable reducing agents such as ascorbic acid/hydrazine hydrate/thiourea dioxide/NH3/urea to prepare the incorporated natural rubber latex preservatives with rGO with variable rGO content (0.1 to 20 phr). The rGO dispersion after sonication is mixed with composite latex and the entire mixture is sonicated again to obtain a uniform dispersion of rGO in the natural rubber latex (sonication time ranging from 1 to 10 mins). The natural rubber latex condoms incorporated with rGO are then prepared by dip molding onto glass molds (machine speed is adjusted to obtain the proper thickness). The number of dips can also be varied depending on the required thickness. The dipped samples are then vulcanized at 60-100 °C in a hot air oven and then removed from the glass molds using silica powder to obtain the natural rubber latex preservatives incorporated with rGO.
[039] Os preservativos de látex de borracha natural incorporados com rGO apresentaram um aumento de 20 a 50% nas propriedades mecânicas ao aumentar o teor de rGO de 0,1 phr para 20 phr. A condutividade térmica das amostras também foi aumentada em 20 a 50%.[039] Natural rubber latex condoms incorporated with rGO showed a 20 to 50% increase in mechanical properties by increasing the rGO content from 0.1 phr to 20 phr. The thermal conductivity of the samples was also increased by 20 to 50%.
[040] O método de dispersão covalente da presente invenção utiliza qualquer um dos seguintes dois métodos para dispersar o grafeno e seus derivados em Polímeros de Formação de Preservativos (CMP). O método inclui (1) Enxerto de polímero ou oligômero (2) Funcionalização do GO ou seus derivados.[040] The covalent dispersion method of the present invention uses any of the following two methods to disperse graphene and its derivatives in Condom-Forming Polymers (CMP). The method includes (1) Polymer or oligomer graft (2) Functionalization of GO or its derivatives.
[041] Em uma modalidade adicional da presente invenção, método de dispersão covalente por enxerto de Polímero ou Oligômero: Os Polímeros de Formação de Preservativos (CMPs) ou seus oligômeros são enxertados em GO e seus derivados, seja pela abordagem “grafting to” (enxertia indireta) ou “grafting from” (enxertia direta no substrato). A abordagem de enxertia indireta envolve realizar a polimerização radical controlada dos iniciadores que são ligados de forma covalente por esterificação/amidação com os ácidos carboxílicos/alcoóis/aminas presentes em toda a superfície plaquetária do GO. A abordagem de enxertia indireta inclui primeiramente produzir CMPs funcionalizados com terminal alcino/amina e enxertar com GO funcionalizado com azida por cicloadição entre azida e alcino catalisada por Cu1/acoplamento de carbodiimida.[041] In an additional embodiment of the present invention, method of covalent dispersion by grafting Polymer or Oligomer: Condom Formation Polymers (CMPs) or their oligomers are grafted onto GO and its derivatives, either by the "grafting to" approach ( indirect grafting) or “grafting from” (direct grafting on the substrate). The indirect grafting approach involves performing controlled radical polymerization of initiators that are covalently linked by esterification/amidation with the carboxylic acids/alcohols/amines present on the entire platelet surface of the GO. The indirect grafting approach includes first producing alkyne/amine-terminal functionalized CMPs and grafting with azide-functionalized GO by Cu1/carbodiimide coupling catalyzed cycloaddition between azide and alkyne.
[042] Etapa 1: O iniciador de polimerização radicalar por transferência de átomos (ATRP), 2-bromoisobutirato de propargila (PgBiB), foi sintetizado de acordo com o protocolo disponível na literatura (1. N. V. Tsarevsky, B. S. Sumerlin, K. Matyjaszewski, Macromolecules 2005, 38, 3558. 2. L. Ragupathy, D. G. Millar, N, Tirelli, F. Cellesi, Macromolecular Bioscience 2014.) O iniciador ATRP produzido (1 a 3 mmol) é misturado com o monômero isopreno (30 a 50 mmol) em um tubo reator paralelo. A mistura é primeiramente desgaseificada por purga por nitrogênio por 30 min. Em seguida, adiciona-se THF (grau HPLC, 5 a 10 mL) à mistura de reação, agitando-a por alguns minutos. O catalisador de cobre (Cu(I)Cl; 1-1.5/0.5-1/0.1-0.5 mmol) e o ligante bipiridina (2-2.5/1-1.5/0.5-1 mmol) são então rapidamente adicionados à mistura de reação. A mistura de reação é então agitada magneticamente por 4 h à aproximadamente 40 a 60oC. A polimerização pode ser terminada por diluição com THF aerado. A mistura de reação se tornará de marrom para azul esverdeado, indicando a oxidação pelo ar de Cu (I) para Cu (II). O catalisador de cobre pode ser removido por passagem em coluna de gel de sílica. O solvente pode ser removido sob pressão reduzida para obter o oligômero ou polímero.[042] Step 1: The atom transfer radical polymerization initiator (ATRP), propargyl 2-bromoisobutyrate (PgBiB), was synthesized according to the protocol available in the literature (1. NV Tsarevsky, BS Sumerlin, K. Matyjaszewski) , Macromolecules 2005, 38, 3558. 2. L. Ragupathy, DG Millar, N, Tirelli, F. Cellesi, Macromolecular Bioscience 2014.) The produced ATRP initiator (1 to 3 mmol) is mixed with the monomer isoprene (30 to 50 mmol) in a parallel reactor tube. The mixture is first degassed by nitrogen purging for 30 min. Then, THF (HPLC grade, 5 to 10 mL) is added to the reaction mixture, stirring it for a few minutes. Copper catalyst (Cu(I)Cl; 1-1.5/0.5-1/0.1-0.5 mmol) and bipyridine linker (2-2.5/1-1.5/0.5-1 mmol) are then quickly added to the reaction mixture . The reaction mixture is then magnetically stirred for 4 h at approximately 40 to 60oC. Polymerization can be terminated by dilution with aerated THF. The reaction mixture will turn brown to greenish blue, indicating air oxidation of Cu(I) to Cu(II). Copper catalyst can be removed by passing through a silica gel column. Solvent can be removed under reduced pressure to obtain the oligomer or polymer.
[043] Etapa 2: O óxido de grafeno é reagido com 11-azido- 3,6,9-trioxaundecan-1-amina (1:1 - 1:5) em água/meio DMF usando o mecanismo de acoplamento EDC. 100 mL de dispersão de óxido de grafeno (1 mg/mL) em DMF ou água por sonicação em sonicador de banho por 1,5 h. Após cada 15 minutos, a água no sonicador de banho é substituída para reduzir o calor produzido. A dispersão GO mencionada acima é colocada em um frasco de fundo redondo, e então 30 a 50 mmol de N- hidróxi succinimida (NHS) são adicionados seguido da adição de 30 a 50 mmol de 1-etil-3-(3- dimetilaminopropil)carbodiimida (EDC) sob atmosfera de N2 e condição extremamente fria. A esta mistura de reação, adiciona-se 0,3 a 0,5 M de NaHCO3 [0,3M] para neutralizar o cloridrato. A reação é mantida em agitação sob condição extremamente fria por 2 a 4 horas. Após duas horas, a esta mistura de reação, adicionam-se 15 a 20 mmol de 11-azido - 3,6,9-trioxaundecan-1-amina e a mistura de reação é mantida em agitação à temperatura ambiente por 24 h.[043] Step 2: Graphene oxide is reacted with 11-azido-3,6,9-trioxaundecan-1-amine (1:1 - 1:5) in water/DMF medium using the EDC coupling mechanism. 100 mL of graphene oxide dispersion (1 mg/mL) in DMF or water by bath sonicator sonication for 1.5 h. After every 15 minutes, the water in the bath sonicator is replaced to reduce the heat produced. The GO dispersion mentioned above is placed in a round bottom flask, and then 30 to 50 mmol of N-hydroxy succinimide (NHS) is added followed by the addition of 30 to 50 mmol of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDC) under N2 atmosphere and extremely cold condition. To this reaction mixture, 0.3 to 0.5 M of NaHCO3 [0.3M] is added to neutralize the hydrochloride. The reaction is kept under stirring under extremely cold condition for 2 to 4 hours. After two hours, to this reaction mixture, 15 to 20 mmol of 11-azido-3,6,9-trioxaundecan-1-amine are added and the reaction mixture is kept under stirring at room temperature for 24 h.
[044] Etapa 3: Os produtos obtidos a partir da etapa 1 e da etapa 2 são acoplados usando a reação de cicloadição de Huisgen do tipo “click” entre alcino e azida. 1:1 a 1:5 % em peso dos produtos da etapa 1 e 2, respectivamente, foram coletados em DMF ou água. A mistura de reação foi expurgada com argônio por 5 min. Em seguida, o ligante hexametil- trietileno tetraamina e o catalisador CuBr (1 equiv. relativo a -C=CH) foram adicionados à mistura de reação e agitados à temperatura ambiente por 24 h. Subsequentemente, a mistura de reação foi centrifugada com excesso de água para obter o produto final.[044] Step 3: The products obtained from step 1 and step 2 are coupled using the Huisgen cycloaddition reaction of the "click" type between alkyne and azide. 1:1 to 1:5% by weight of the products from step 1 and 2, respectively, were collected in DMF or water. The reaction mixture was purged with argon for 5 min. Then, the hexamethyl-triethylene tetraamine linker and the CuBr catalyst (1 equiv. relative to -C=CH) were added to the reaction mixture and stirred at room temperature for 24 h. Subsequently, the reaction mixture was centrifuged with excess water to obtain the final product.
[045] Etapa 1: O iniciador GO-ATRP foi produzido adotando-se a literatura relatada. 15 a 20 mmol de ácido 2- bromoisobutírico são dissolvidos em 50 mL de DMF. Então, 30 a 50 mmol de N-hidróxi succinimida (NHS) são adicionados seguido da adição de 30 a 50 mmol de 1-etil-3-(3- dimetilaminopropil)carbodiimida (EDC) sob atmosfera de N2 e condição extremamente fria. A esta mistura de reação, adiciona-se 0.3 a 0.5 M de NaHCO3 para neutralizar a mistura de reação. Em seguida, 10 a 100 mL de dispersão de óxido de grafeno (1 mg/mL) são preparados em DMF ou água por sonicação em sonicador de banho por 1.5 h. A dispersão de GO mencionada acima é adicionada a esta mistura de reação e mantida sob agitação à temperatura ambiente por 24 h. Em seguida, a mistura de reação foi centrifugada com excesso de água para obter o produto final.[045] Step 1: The GO-ATRP initiator was produced adopting the reported literature. 15 to 20 mmol of 2-bromoisobutyric acid are dissolved in 50 ml of DMF. Then, 30 to 50 mmol of N-hydroxy succinimide (NHS) are added followed by the addition of 30 to 50 mmol of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) under N2 atmosphere and extremely cold condition. To this reaction mixture, 0.3 to 0.5 M NaHCO3 is added to neutralize the reaction mixture. Then, 10 to 100 mL of graphene oxide dispersion (1 mg/mL) is prepared in DMF or water by sonication in a bath sonicator for 1.5 h. The dispersion of GO mentioned above is added to this reaction mixture and kept under stirring at room temperature for 24 h. Then, the reaction mixture was centrifuged with excess water to obtain the final product.
[046] Etapa 2: o produto obtido anteriormente é então sujeito à reação ATRP com isopreno em THF usando o protocolo fornecido acima (abordagem de enxertia direta, etapa 1).[046] Step 2: The product obtained above is then subjected to the ATRP reaction with isoprene in THF using the protocol given above (direct grafting approach, step 1).
[047] Os produtos obtidos a partir da abordagem de enxertia direta e enxertia indireta são então adicionados ao látex de borracha natural composto com teor variável (0,3 a 5 phr) para obter o produto de preservativo final. As propriedades mecânicas e a condutividade térmica são testadas com base na variação no teor de phr do grafeno ou de seus derivados.[047] The products obtained from the direct grafting and indirect grafting approach are then added to composite natural rubber latex with varying content (0.3 to 5 phr) to obtain the final preservative product. Mechanical properties and thermal conductivity are tested based on the variation in the phr content of graphene or its derivatives.
[048] Os produtos obtidos a partir da abordagem de enxertia direta e enxertia indireta apresentam um percentual de aumento de 20 a 50% nas propriedades mecânicas ao aumentar o teor de rGO de 0,1 phr para 20 phr. A condutividade térmica das amostras também foi aumentada em 30 a 60%.[048] The products obtained from the direct grafting and indirect grafting approach show a percentage increase of 20 to 50% in mechanical properties when increasing the rGO content from 0.1 phr to 20 phr. The thermal conductivity of the samples was also increased by 30 to 60%.
[049] Em uma modalidade adicional da presente invenção, método de dispersão covalente por Funcionalização do GO ou seus derivados: Funcionalização do GO e seus derivados com anidrido acrílico/cloreto de acriloíla seguido pela mistura e reticulação com Polímeros de Formação de Preservativos (CMPs) durante o processo de fabricação de preservativos.[049] In an additional embodiment of the present invention, covalent dispersion method by Functionalization of GO or its derivatives: Functionalization of GO and its derivatives with acrylic anhydride/acryloyl chloride followed by mixing and crosslinking with Condom Formation Polymers (CMPs) during the condom manufacturing process.
[050] 100 mL de GO em DMF (1 mg/mL) e tietilamina (1:2 % em peso) foram colocados em um frasco de fundo redondo e agitados a temperatura extremamente fria. Então, 5 a 20% em peso de cloreto de aciloíla foram adicionados à mistura de reação lentamente e agitados à temperatura ambiente por 24 h. Então, esta mistura foi centrifugada com quantidade de água em excesso para obter o produto final, que é novamente reduzido usando os mesmos agentes redutores mencionados acima. Diferentes quantidades de rGO acrilado (0,3 a 10 phr) foram adicionadas ao látex para produzir os preservativos.[050] 100 ml of GO in DMF (1 mg/ml) and thiethylamine (1:2 % by weight) were placed in a round bottom flask and stirred at extremely cold temperature. Then, 5 to 20% by weight of acyloyl chloride was added to the reaction mixture slowly and stirred at room temperature for 24 h. Then, this mixture was centrifuged with excess amount of water to obtain the final product, which is again reduced using the same reducing agents mentioned above. Different amounts of acrylated rGO (0.3 to 10 phr) were added to the latex to produce the condoms.
[051] Os preservativos obtidos a partir da acrilação de GO e seguidos pela incorporação em látex apresentam um aumento de 20 a 50 % nas propriedades mecânicas ao aumentar o teor de rGO de 0,1 phr para 20 phr. A condutividade térmica das amostras também foi aumentada em 30 a 60%.[051] Condoms obtained from GO acrylation and followed by incorporation in latex show a 20 to 50% increase in mechanical properties by increasing the rGO content from 0.1 phr to 20 phr. The thermal conductivity of the samples was also increased by 30 to 60%.
[052] Na modalidade preferida da invenção, incorporação dos ingredientes farmacêuticos em preservativos: ingredientes farmacêuticos que incluem fármacos antiretrovirais / espermicidas / vasodilatadores / aromas são carregados em grafeno e seus derivados para liberação durante a relação sexual para evitar doenças sexualmente transmissíveis (DSTs), gravidez indesejada e aumentar o prazer sexual.[052] In the preferred embodiment of the invention, incorporation of pharmaceutical ingredients in condoms: pharmaceutical ingredients that include antiretroviral drugs / spermicides / vasodilators / aromas are loaded in graphene and its derivatives for release during sexual intercourse to prevent sexually transmitted diseases (STDs), unwanted pregnancy and increase sexual pleasure.
[053] De acordo com a presente invenção, os fármacos antiretrovirais (isto é) Dapivirina ou Tenofovir ou Curcumina e o espermicida Nonoxinol-9 são carregados em grafeno, GO e GOs funcionalizados pela dissolução de fármacos antiretrovirais e espermicida em DMSO/DMA/DMF com grafeno, GO ou GOs funcionalizados em solução de água. Os fármacos precipitados em excesso, descarregados, são removidos por centrifugação. Como alternativa, os fármacos antiretrovirais e o espermicida são carregados em grafeno, GO e GOs funcionalizados por sonicação ao pH > 6 por 0,5 h seguido de agitação durante a noite à temperatura ambiente. Todas as amostras são ajustadas ao pH < 6 com cloridrato 1 M e então ultracentrifugadas a 14.000 rpm por 1 h. Finalmente, o grafeno carregado com fármaco, GO e seus derivados são dispersos uniformemente nos polímeros de formação de preservativos usando qualquer um dos métodos de dispersão mencionados acima. O nanomaterial disperse uniformemente também forma uma rede durante as condições de processamento otimizadas.[053] According to the present invention, antiretroviral drugs (ie) Dapivirine or Tenofovir or Curcumin and the spermicide Nonoxynol-9 are loaded in graphene, GO and GOs functionalized by dissolving antiretroviral drugs and spermicide in DMSO/DMA/DMF with graphene, GO or GOs functionalized in water solution. Excess precipitated, discharged drugs are removed by centrifugation. Alternatively, the antiretroviral drugs and spermicide are loaded onto graphene, GO, and functionalized GOs by sonication at pH > 6 for 0.5 h followed by stirring overnight at room temperature. All samples are adjusted to pH < 6 with 1 M hydrochloride and then ultracentrifuged at 14,000 rpm for 1 h. Finally, the drug-loaded graphene, GO and its derivatives are evenly dispersed in the preservative-forming polymers using any of the dispersion methods mentioned above. The evenly dispersed nanomaterial also forms a network during the optimized processing conditions.
[054] Pequenos pedaços (2cm x 2cm) dos preservativos carregados com fármaco supracitados foram colocados em um líquido vaginal artificial (10 mL) em um agitador à 37 oC. Uma pequena quantidade de amostra foi retirada após 2, 5, 10, 30 e 60 minutos) para análise HPLC para calcular a quantidade de fármaco liberado.[054] Small pieces (2cm x 2cm) of the aforementioned drug-loaded condoms were placed in an artificial vaginal fluid (10 mL) on a shaker at 37 oC. A small amount of sample was taken after 2, 5, 10, 30 and 60 minutes) for HPLC analysis to calculate the amount of drug released.
[055] Embora a presente invenção tenha sido ilustrada e descrita particularmente com referência a modalidades preferidas da mesma, será entendido pelos versados na técnica que várias alterações na forma e nos detalhes podem ser feitas na mesma sem divergir do âmbito da presente invenção conforme revelado pelas reivindicações a seguir.[055] Although the present invention has been illustrated and described particularly with reference to preferred embodiments thereof, it will be understood by those skilled in the art that various changes in form and detail can be made thereto without departing from the scope of the present invention as disclosed by following claims.
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CN105764491A (en) | 2013-12-09 | 2016-07-13 | 度瑞公司 | Pharmaceutically active agent complexes, polymer complexes, and compositions and methods involving the same |
WO2017075460A1 (en) | 2015-10-29 | 2017-05-04 | Arizona Board Of Regents On Behalf Of Arizona State University | Skin-like condoms having active ingredients to enhance a male erection and a female arousal |
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