Patents Assigned to Laboratorios Miret, S.A.
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Patent number: 10130830Abstract: Preservative systems on the basis of cationic surfactants are known i n the art, a typical example of such cationic surfactants is the ethyl ester of the lauramide of arginine monohydrochloride (LAE) (2). Besides the chloride form the corresponding bromide and sulphate salts are known. It was found that other salts of the cationic surfactants display excellent properties, such as the salts of lactic acid, glutamic acid and acetic acid. It was further found that the combination of the cationic surfactants with at least one salt of an organic or inorganic acid displayed an excellent preservative action. A further preservative system with favourable properties was the combination of the cationic surfactants with at least one ester compound, amide or enzyme inhibitor. Also the combination of the cationic surfactant with a further cationic molecule such as ethyl arginate, glucosamine or chitosan led to an effective preservative system.Type: GrantFiled: August 1, 2005Date of Patent: November 20, 2018Assignee: Laboratorios Miret, S.A.Inventors: Jordi Miret Carceller, Sergi Figueras Roca, Roger Segret Pons
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Patent number: 8933122Abstract: Cationic surfactants derived from the condensation of fatty acids and esterified dibasic amino acids, such as from lauric acid and arginine, in particular the ethyl ester of the lauramide of the arginine monohydrochloride (LAE), may be used for the treatment of objects which are infected with spores. The spores may originate from bacteria or fungi.Type: GrantFiled: June 30, 2009Date of Patent: January 13, 2015Assignee: Laboratorios Miret, S.A.Inventors: Xavier Rocabayera Bonvila, Sergi Figueras Roca, Roger Segret Pons, Eva Piera Eroles
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Patent number: 8388986Abstract: The invention relates to a new use of cationic surfactants derived from the condensation of fatty acids and esterified dibasic amino acids, according to the following formula: where: X? is Br?, Cl?, or HSO4?. R1: is linear alkyl chain from a saturated fatty acid, or hydroxyacid from 8 to 14 atoms of carbon bonded to the ?-amino acid group through amidic bond. R2: is a lineal or branched alkyl chain from 1 to 18 carbon atoms or aromatic, and R3: is: and n can be from 0 to 4. This class of compounds turned out to be highly suitable for use as preservatives in cosmetic or dermatological preparations. A particularly suitable compound is the ethyl ester of the lauramide of arginine hydrochloride (LAE).Type: GrantFiled: August 9, 2001Date of Patent: March 5, 2013Assignee: Laboratorios Miret S.A.Inventors: Joan Baptista Urgell Beltran, Joan Seguer Bonaventrua
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Publication number: 20110275714Abstract: This invention relates to a use of a composition for protecting against mites and ticks containing cationic surfactants such as ethyl-N?-lauroyl-L-arginate HCl (LAE). It has been found that cationic surfactants such as ethyl-N?-lauroyl-L-arginate HCl (LAE) and its salts are effective acaricidal agents.Type: ApplicationFiled: January 12, 2010Publication date: November 10, 2011Applicant: LABORATORIOS MIRET, S. A.Inventors: Xavier Rocabayera Bonvila, Sergi Figueras Roca
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Publication number: 20110144203Abstract: Cationic surfactants derived from the condensation of fatty acids and esterified dibasic amino acids, such as from lauric acid and arginine, in particular the ethyl ester of the lauramide of the arginine monohydrochloride (LAE), may be used for the treatment of objects which are infected with spores. The spores may originate from bacteria or fungi.Type: ApplicationFiled: June 30, 2009Publication date: June 16, 2011Applicant: LABORATORIOS MIRET, S.A.Inventors: Xavier Rocabayera Bonvila, Sergi Figueras Roca, Roger Segret Pons, Eva Piera Eroles
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Patent number: 7862842Abstract: A novel use of cationic preservatives and preparations according to this novel use. A cationic preservative derived from lauric acid and arginine, in particular, the ethyl ester of the lauramide of the arginine monohydrochloride, hereafter named LAE, can be used for the protection against the growth of microorganisms. LAE and related compounds are particularly suitable to be used in the preservation of all perishable food products. The composition optionally comprises auxiliary components and excipients.Type: GrantFiled: July 31, 2008Date of Patent: January 4, 2011Assignee: Laboratorios Miret, S.A.Inventors: Joan Baptista Urgell Beltran, Joan Seguer Bonaventura
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Publication number: 20100305055Abstract: A solid composition comprising a cationic surfactant, such as the ethyl ester of the lauramide of the arginine mono-hydrochloride (LAE) and a polyene fungicide such as natamycin is provided. The solid composition is the basis for providing solutions of natamycin of increased concentration. The solid composition may be used for providing a dispersion of natamycin in a suitable liquid, such as tap water or an organic solvent. The dispersion may be further diluted with water. This leads to a solution of natamycin in water. The combination of the cationic surfactant and the polyene fungicide displays a biological effect which is stronger than the effect of each of the two components alone.Type: ApplicationFiled: October 5, 2007Publication date: December 2, 2010Applicant: Laboratorios Miret, S.A.Inventors: Xavier Rocabayera Bonvila, Sergi Figueras Roca, Roger Segret Pons, Eva Piera Eroles
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Patent number: 7758851Abstract: The invention relates to preservative systems which are particularly suitable in cosmetic and dermatological preparations. The preservative system which comprises a cationic surfactant, derived from the condensation of fatty acids and esterified dibasic amino acids, having the formula (I) where: X? is Br?, Cl?, or HSO4 R1: is a straight alkyl chain from an acid or saturated fatty hydroxy acid from 8 to 14 atoms of carbon bonded to the ?-amino acid group through amidic bond. R2: is a straight or branched alkyl chain from 1 to 18 carbon atoms or aromatic. R3: is: (II) where n can be from 0 to 4, is combined with at least one other ionic or non-ionic preservative agent, whereby the combination displays a synergetic activity. A preservative system, wherein the cationic surfactant preservative derived from the condensation of fatty acids and esterified dibasic amino acid is LAE is particularly preferred.Type: GrantFiled: August 9, 2001Date of Patent: July 20, 2010Assignee: Laboratorios Miret, S.A.Inventors: Joan Baptista Urgell Beltran, Joan Seguer Bonaventrua
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Publication number: 20100092420Abstract: Preservative systems on the basis of cationic surfactants are known i n the art, a typical example of such cationic surfactants is the ethyl ester of the lauramide of arginine monohydrochloride (LAE) (2). Besides the chloride form the corresponding bromide and sulphate salts are known. It was found that other salts of the cationic surfactants display excellent properties, such as the salts of lactic acid, glutamic acid and acetic acid. It was further found that the combination of the cationic surfactants with at least one salt of an organic or inorganic acid displayed an excellent preservative action. A further preservative system with favourable properties was the combination of the cationic surfactants with at least one ester compound, amide or enzyme inhibitor. Also the combination of the cationic surfactant with a further cationic molecule such as ethyl arginate, glucosamine or chitosan led to an effective preservative system.Type: ApplicationFiled: August 1, 2005Publication date: April 15, 2010Applicant: LABORATORIOS MIRET, S.A.Inventors: Jordi Miret Carceller, Sergi Figueras Roca, Roger Segret Pons
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Patent number: 7662417Abstract: This invention relates to compositions comprising cationic preservatives and anionic hydrocolloids, to methods of preparing them and their application in food microbiological protection. Due to their composition, food products are susceptible to act as a culture medium for microorganisms, and this constitutes a possible risk to human health. Thus, food products require good protection against microbiological contamination. The present invention relates to the interaction between cationic preservatives derived from the condensation of fatty acids and esterified dibasic amino acids and anionic hydrocolloids, such as pectins, xanthan gums, carrageenans, acacia gums or agars. The most preferred cationic preservative is the ethyl ester of the lauramide of arginine monohydrochloride (LAE). As a result of this interaction, some anionic hydrocolloids are able to absorb LAE and precipitate together by the enhancement of their lipophilic properties.Type: GrantFiled: May 8, 2002Date of Patent: February 16, 2010Assignee: Laboratorios Miret, S.A.Inventors: Joan Seguer Bonaventura, Xavier Rocabayera Bonvila, Mariano A. Martinez Rubio
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Publication number: 20100028325Abstract: Use of cationic surfactants, derived from the condensation of fatty acids and esterified dibasic amino acids, of the formula (1): occasionally leads to a bitter taste, when the compound is present in a large concentration. The bitter taste can be masked by combination with a second component selected from the list consisting of sucralose, neohespiridin (NHDC), ?-cyclodextrin, mono ammonium glycyrrhizinate (MAG), banana, mentholyptus, sodium dodecyl sulphate (SDS), anetol, menthol, thaumatin, adenosine monophosphate (AMP), aloten, arginine, sodium acetate, arilic acids (ferulic acid, caffeic acid), sclareolide, maltol, anane, phosphatidic acid, eucalyptol, lactisole, lysozyme, lactoglobulin, timol, borneol, acetol, phosphothreonine, phosphotyrosine, phosphoserine, Masking flavour 501521T, Masking flavour 501522, saccharine, aspartame, MK22 N&A FL for masking #25682, MM24 Prosweet N&A FL Enhancer, neodiosmin, xylitol, stevia and Natural and Functional Flavour (NAF®).Type: ApplicationFiled: February 7, 2007Publication date: February 4, 2010Applicant: LABORATORIOS MIRET, S.A.Inventors: Xavier Rocabayera Bonvila, Sergi Figueras Roca, Roger Segret Pons, Eva Piera Eroles
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Publication number: 20090326022Abstract: The invention relates to a concentrated solution of TCMTB for the preparation of an emulsion of TCMTB. The concentrated solution comprises (i) 2-(thiocyanomethylthio)-benzothiazole, (ii) an ester of a C6-C20 fatty acid derived from vegetable oil or a blend of such esters of C6-C20 fatty acids, (iii) a surfactant or blend of surfactants, (iv) optionally a further biocide, and (v) optionally a hydrocarbon solvent. The concentrated solution can be diluted with water and the diluted preparation can be used for the preservation of leather during the tanning process. The biocidal compositions according to the invention can be also applied to protect wood, paper, paperboard, cellulose pulp and cellulose products, preventing the growth of fungi on their surfaces or preventing the formation of slimes on materials, equipment and structures used in industrial processes.Type: ApplicationFiled: August 2, 2006Publication date: December 31, 2009Applicant: LABORATORIOS MIRET, S.A.Inventors: Amaro Izquierdo Ramis, Joan Seguer Bonaventura, Albert Beltran Gimeno
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Patent number: 7407679Abstract: A novel use of cationic preservatives and preparations according to this novel use. A cationic preservative derived from lauric acid and arginine, in particular, the ethyl ester of the lauramide of the arginine monohydrochloride, hereafter named LAE, can be used for the protection against the growth of microorganisms. LAE and related compounds are particularly suitable to be used in the preservation of all perishable food products. The composition optionally comprises auxiliary components and excipients.Type: GrantFiled: October 25, 2001Date of Patent: August 5, 2008Assignee: Laboratorios Miret, S.A.Inventors: Joan Baptista Urgell Beltran, Joan Seguer Bonaventura
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Patent number: 7399616Abstract: The invention relates to a process for preparing a Na-acyl-L-arginine ester, derived from fatty acids and esterified dibasic amino acids, according to the following formula (I), where: X— is Br—, Cl—, or HSO4— R1: is linear alkyl chain from an saturated fatty acid, or hydroxy-acid from 8 to 14 atoms of carbon bonded to the ?-amino acid group through amidic bond. R2: is a linear or branched alkyl chain from 1 to 18 carbon atoms or aromatic. R3: is formula (II), where n can be from 0 to 4, from the appropriate organic acid and alcohol. The process is catalyzed by a hydrolase, more in particular a protease, the protease papain from <i> Carica papaya being highly suitable </i>. In order for the esterification reaction to run as wanted, the process is performed in a low-water-content organic medium. When the highly suitable papain from Carica papaya is used, a water activity of between 0.03 and 0.5 is selected.Type: GrantFiled: February 1, 2002Date of Patent: July 15, 2008Assignee: Laboratorios Miret, S.A.Inventors: Joan Seguer Bonaventura, Xavier Rocabayera Bonvila
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Patent number: 7196117Abstract: Antimicrobial system which comprises a cationic surfactant, derived from the condensation of fatty acids and esterified dibasic amino acids, according to the following formula (I), where: X is Br, Cl or HSO4R1: is linear alkyl chain from an saturated fatty acid, or hydroxyacid from 8 to 14 atoms of carbon bonded to the ?-amino acid group through amidic bond. R2 is a linear or branched alkyl chain from 1 to 18 carbon atoms or aromatic. R3: is Formula (II), where n can be from 0 to 4, and at least one antimicrobial agent characterised for its enhanced activity.Type: GrantFiled: November 25, 2001Date of Patent: March 27, 2007Assignee: Laboratorios Miret, S.A.Inventors: Joan Baptista Urgell Beltran, Joan Seguer Bonaventura
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Patent number: 7087769Abstract: The invention concerns the preparation of cationic surfactants derived from the condensation of an acid, preferably a fatty acid or a hydroxy acid with a number of carbon atoms of 8–14 with esterified amino acids, preferably basic-type amino acids, more preferably (L)-arginine. The method comprises a first step in which the esterifiction of the amino acid with an alcohol is performed and a second step for the condensation with a chloride of an acid, preferably an acyl chloride of a fatty acid or a hydroxy acid, whereby the second step is performed in an aqueous environment with a pH value between (6 and 7), preferably between (6, 7) and (6, 9).Type: GrantFiled: June 3, 2000Date of Patent: August 8, 2006Assignee: Laboratorios Miret, S.A.Inventors: Alex Contijoch Manent, legal representative, Monica Contijoch Manent, legal representative, Maria Contijoch Manent, legal representative, Javier Rodriguez Martinez, Joan Seguer Bonaventura, Agustin Contijoch Mestres, deceased
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Patent number: 5780658Abstract: The process of the invention is directed to the synthesis of cationic type surfactant compounds consisting of natural basic-character amino acids, and any of their homologs, suitably modified for the purpose of obtaining products having specific applications as antimicrobial (biocidal) agents. The process comprises a first step of esterification of an amino acid, and a second step of the condensation of a fatty acid chloride with an esterified amino acid derivative. Nontoxic reaction media and catalysts are used, and a final product free from impurities is obtained. The cost of the process of the invention is reduced from prior art processes due to the use of cheaper starting materials and simpler equipment.Type: GrantFiled: September 10, 1996Date of Patent: July 14, 1998Assignee: Laboratorios Miret, S.A.Inventors: Marta Rosa Infante Martinez-Pardo, Augustin Contijoch Mestres, Pilar Erra Serrabasa