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Cosmetic Composition Containing Polyorganosiloxane-Containing Epsilon-Polylysine Polymer, and Polyhydric Alcohol, and Production Thereof

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Europäisches Patentamt *EP001604647A1* (19) European Patent Office Office européen des brevets (11) EP 1 604 647 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.7: A61K 7/48, A61K 7/06, 14.12.2005 Bulletin 2005/50 A61K 7/02, C08G 81/00, C08G 77/452, C08G 77/455, (21) Application number: 05010234.2 C08L 83/10 (22) Date of filing: 11.05.2005 (84) Designated Contracting States: (72) Inventors: AT BE BG CH CY CZ DE DK EE ES FI FR GB GR • Kawasaki, Yuji HU IE IS IT LI LT LU MC NL PL PT RO SE SI SK TR Ibi-gun Gifu 501-0521 (JP) Designated Extension States: • Hori, Michimasa AL BA HR LV MK YU Gifu-shi Gifu 500-8286 (JP) • Yamamoto, Yuichi (30) Priority: 12.05.2004 JP 2004141778 5-1 Goikaigan Ichiharashi Chiba 290-8551 (JP) • Hiraki, Jun (71) Applicants: Tokyo 104-8555 (JP) • Ichimaru Pharcos Co., Ltd. Motosu-shi, Gifu 501-0475 (JP) (74) Representative: HOFFMANN EITLE • Chisso Corporation Patent- und Rechtsanwälte Osaka-shi, Osaka-fu 530-0005 (JP) Arabellastrasse 4 81925 München (DE) (54) Cosmetic composition containing polyorganosiloxane-containing epsilon-polylysine polymer, and polyhydric alcohol, and production thereof (57) It has been desired to develop a highly preserv- by reducing the amount of antibacterial preservative ative and antibacterial cosmetic composition that can agent to be used. easily be applied to both emulsion and non-emulsion There is provided a cosmetic composition compris- type cosmetics. It has also been desired to develop a ing one or a combination of two or more of polyorganosi- method of improving a preservative and/or antibacterial loxane-containing epsilon-polylysine compounds ob- effect(s) of a cosmetic composition comprising polyor- tained by reacting epsilon-polylysine with polyorganosi- ganosiloxane-containing epsilon-polylysine and there- loxane or a physiologically acceptable salt thereof, and polyhydric alcohol. EP 1 604 647 A1 Printed by Jouve, 75001 PARIS (FR) EP 1 604 647 A1 Description [Technical Field] 5 [0001] The present invention relates to a cosmetic composition comprising a polyorganosiloxane-containing epsilon- polylysine compound or a physiologically acceptable salt thereof and polyhydric alcohol, and a method of producing such a compound. [Background Art] 10 [0002] More and more people are sensitive to chemical substances contained in cosmetics these days. To that end, a safe antibacterial preservative agent that exhibits enough antibacterial preservative effects has been desired in the cosmetic industries. It has also been desired to reduce the content of any antibacterial preservative agents used. [0003] Epsilon-polylysine, which is a kind of antimicrobial agent to be contained in cosmetics in order to preserve 15 the product itself or to provide antimicrobial/antibacterial effects, is safe to the skin and is stable with time after com- pounded in cosmetics. In addition, it exhibits good preservative and sterilization effects and is reported to be very useful as a preservative/sterilization agent for cosmetics [e.g., Japanese Patent Publication No. 05-6460 (Patent Reference 1)]. Epsilon-polylysine is an amino acid homopolymer with a significantly low volatility, so that the intended preservative/ sterilization effects are less likely to be lost due to evaporation of epsilon-polylysine. 20 [0004] In addition, epsilon-polylysine is highly soluble to common cosmetic bases, i.e., water or some alcoholic sol- vents because of its good water solubility, as well as has a high affinity for emulsion-type cosmetics, in particular, for silicone such as polyorganosiloxane that is a base widely used for emulsion-type cosmetics. Thus, epsilon-polylysine can hardly form a uniform mixture with polyorganosiloxane. This means the necessity of, for example, a surfactant to be added. 25 [Patent Reference 1] Japanese Patent Publication No. 05-64608 [Patent Reference 2] Japanese Patent No. 1245361 [Problems to be solved by the Invention] 30 [0005] Under the aforementioned circumstances, it has been desired to develop a highly preservative and antibac- terial cosmetic composition that can easily be applied to both emulsion and non-emulsion type cosmetics. It has also been desired to develop a method of improving a preservative and/or antibacterial effect(s) of a cosmetic composition comprising polyorganosiloxane-containing epsilon-polylysine and thereby reducing the amount of antibacterial pre- 35 servative agent to be used. Summary of the Invention [0006] A first aspect of the present invention is a cosmetic composition comprising one or a combination of two or 40 more of polyorganosiloxane-containing epsilon-polylysine compounds or a physiologically acceptable salt thereof, and polyhydric alcohol. Furthermore, a first aspect of the present invention is a cosmetic composition comprising one or a combination of two or more of polyorganosiloxane-containing epsilon-polylysine compounds represented by the general formula (1): 45 50 [in the general formula (1), V represents a random copolymer in which a first repeating unit represented by the general formula (5) : 55 2 EP 1 604 647 A1 5 10 is randomly polymerized with a second repeating unit represented by the general formula (6): 15 20 25 an alternating copolymer in which the first repeating unit alternates with the second repeating unit, or a block copolymer 30 in which a block consisting only of the first repeating units is connected to another block consisting only of the second repeating units, the number of repeats a of the first repeating unit being an integer of 0 to 50, the number of repeats b of the second repeating unit being an integer of 0 to 50, a + b being equal to an integer of 1 to 50, A1 represents a group represented by the general formula (2): 35 -X-Y-Z (2) {in the general formula (2), X represents 40 45 50 55 3 EP 1 604 647 A1 5 10 15 20 25 30 35 40 (wherein, R1 represents a linear or branched alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms or an arylene group having 6 to 10 carbon atoms), Y represents a linear or branched alkylene group having 1 to 1000 carbon atoms, of which any mutually non-adjacent methylene groups may be substituted with 45 -O-(ether), and Z represents a polyorganosiloxane group represented by the general formula (3) or (4): 50 55 4 EP 1 604 647 A1 5 10 (in the general formulae (3) and (4), R2 and R3 are each independently a linear or branched alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 10 carbon atoms, c is an integer of 1 to 1000, d is an integer of 1 to 1000, and e is an integer of 0 to 1000)}, and A2 and A3 are each independently an amino group or a group represented by. 15 the aforementioned general formula (2), A2 and A3 are not both amino group when a is equal to 0] or a physiologically acceptable salt thereof, and polyhydric alcohol. It is preferable that the number of repeats a of said first repeating unit be an integer of 0 to 20, the number of repeats b of the second repeating unit be an integer of 20 to 40, a + b be 10 to 40. It is further preferable that a + b be 30 to 40. 20 It is particularly preferable that X in the general formula (2) be 25 Furthermore, Z in the general formula (2), it is preferable that R2 and R3 be each independently an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and more preferably, be an alkyl group 30 having 1 to 5 carbon atoms or a phenyl group. Of these, the most preferable ones are a methyl group and a n-butyl group. [0007] In the cosmetic compositions according to the first aspect, it is preferable that polyorganosiloxane-containing epsilon-polylysine compounds or a physiologically acceptable salt thereof, in which the number of repeats b of the second repeating unit is 5 or greater, the second repeating unit being represented by the general formula (6): 35 40 45 In the cosmetic compositions according to the first aspect, it is preferable that the number of repeats a of the first repeating unit and the number of repeats b of the second.repeating unit satisfy the inequality 0.1 %b/(a + b) % 0.98, 50 the first repeating unit being represented by the general formula (5): 55 5 EP 1 604 647 A1 5 10 the second repeating unit being represented by the general formula (6): 15 20 25 the first and second repeating units forming the polyorganosiloxane-containing epsilon-polylysine compound. 30 [0008] In the cosmetic compositions according to the first aspect, it is preferable that X in the group represented by the general formula (2): -X-Y-Z (2) 35 forming the polyorganosiloxane-containing epsilon-polylysine compound is a group represented by: 40 45 50 55 In the cosmetic compositions according to the first aspect, it is preferable that X in the group represented by the general formula (2): 6 EP 1 604 647 A1 -X-Y-Z (2) forming the polyorganosiloxane-containing epsilon-polylysine compound is a group represented by: 5 10 or 15 20 (X in the general formula (2), R1 represents a linear or branched alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms or an arylene group having 6 to 10 carbon atoms). In the cosmetic compositions according to the first aspect, it is preferable that X in the group represented by the general formula (2): 25 -X-Y-Z (2) forming the polyorganosiloxane-containing epsilon-polylysine compound is a group represented by: 30 35 40 45 or 50 (X in the general formula (2), R1 represents a linear or branched alkylene group having 1 to 5 carbon atoms, an alkenylene group having 2 to 5 carbon atoms or an arylene group having 6 to 10 carbon atoms).
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  • Glycosylation of Caffeic Acid and Structural Analogues Catalyzed by Novel Glucansucrases from Leuconostoc and Weissella Species

    Glycosylation of Caffeic Acid and Structural Analogues Catalyzed by Novel Glucansucrases from Leuconostoc and Weissella Species

    Biocatalysis and Agricultural Biotechnology 19 (2019) 101114 Contents lists available at ScienceDirect Biocatalysis and Agricultural Biotechnology journal homepage: www.elsevier.com/locate/bab Glycosylation of caffeic acid and structural analogues catalyzed by novel T glucansucrases from Leuconostoc and Weissella species ∗ Johannes Nolte, Alexander Kempa, Arne Schlockermann, Matthias Hochgürtel, Ulrich Schörken Faculty of Applied Natural Sciences, TH Köln-Campus Leverkusen, Chempark Leverkusen E39, Kaiser-Wilhelm-Allee, 51368, Leverkusen, Germany ARTICLE INFO ABSTRACT Keywords: Twelve Leuconostoc and seven Weissella strains with extracellular glucansucrase activity were obtained from an Caffeic acid analysis of 41 lactic acid bacteria. Culture supernatants of all glucansucrase positive strains catalyzed the gly- Glucansucrase cosylation of caffeic acid with sucrose as donor substrate. Eighteen enzymes produced one major peak, which Leuconostoc was identified as caffeic acid-4′-O-α-D-monoglucoside by LC-MS and NMR spectroscopy. Only W. beninensis DSM Weissella 22752 formed significant amounts of the corresponding 3´-O-α-D-monoglucoside. The Weissella strain and five Acceptor reaction Leuconostoc strains with high glycosylation activity were selected for further studies. All glucansucrases cata- Transglycosylation lyzed the glycosylation of the catechol protocatechuic acid, a side-chain truncated analogue of caffeic acid. The Leuconostoc enzymes displayed a preference for the 4′-O-α-D isomer, while the DSM 22752 glucansucrase also produced the protocatechuic acid-3′-O-α-D-monoglucoside. Lower activities with non-catecholic caffeic acid derivatives and no activity with mono-methylated caffeic acid were observed with all glucansucrases. Time- course analyses confirmed that glucansucrase from L. citreum DSM 5577 was the most efficient biocatalyst for catechol glucosylation with yields of up to 74% caffeic acid glucosides after 24 h.
  • Frankland, and of Kolbe, 1849-1850. the Former Claimed To

    Frankland, and of Kolbe, 1849-1850. the Former Claimed To

    1170 EMIL FISCHER. Frankland, and of Kolbe, 1849-1850. The former claimed to have isolated the radicals-methyl, ethyl, etc.-by the action of zinc upon the corresponding iodides, while Kolbe obtained the same radicals by the hydrolysis of the sodium salts of acetic, propionic and such acids. In vain did Gerhard and Laurent insist that the molecular formulas of all these so-called free radicals must be doubled, in accordance with Avogadro’s hypothesis. The existence of free radicals was generally accepted as late as 1865, fifty years after Gay Lussac’s introduction of this idea into chemistry. Even Kekul6 for a time considered Frankland’s “methyl” as distinct from ethane. But in 1864 Schorlemmer showed by experimental evidence that Frankland’s and Kolbe’s methyl and ethyl were nothing else than ethane and butane. From that time on, the question relative to the existence of free radicals was never seriously raised until the discovery of triphenylmethyl. How parallel these two periods in the history of chemistry are! Now, as then, a methyl was prepared by the abstraction of halogen from the corresponding alkyl-halide. Now, as then, it was found that the molec- ular weight of the product must be doubled. But now, unlike as in the period of fifty years ago, it was possible to show, by physical and chemicaI evidence, that the product which results from the coupling of the radicals is at best unstable. It was possible to show that it does not retain its individuality, but tends to break down again and is in equilibrium with the truly free radicals.