WO1997030057A1 - Aminoacides antibacteriens, leurs sels inorganiques et leur procede de preparation et d'utilisation - Google Patents
Aminoacides antibacteriens, leurs sels inorganiques et leur procede de preparation et d'utilisation Download PDFInfo
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- WO1997030057A1 WO1997030057A1 PCT/JP1997/000445 JP9700445W WO9730057A1 WO 1997030057 A1 WO1997030057 A1 WO 1997030057A1 JP 9700445 W JP9700445 W JP 9700445W WO 9730057 A1 WO9730057 A1 WO 9730057A1
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- Prior art keywords
- antibacterial
- amino acid
- long
- basic amino
- chain
- Prior art date
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- 150000001413 amino acids Chemical class 0.000 title claims abstract description 57
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 55
- 150000003839 salts Chemical class 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 229910021645 metal ion Inorganic materials 0.000 claims abstract description 9
- 239000004094 surface-active agent Substances 0.000 claims abstract description 7
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 150000002736 metal compounds Chemical class 0.000 claims abstract 2
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 18
- 239000007864 aqueous solution Substances 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000000845 anti-microbial effect Effects 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 239000004475 Arginine Substances 0.000 claims description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004472 Lysine Substances 0.000 claims description 4
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 239000012670 alkaline solution Substances 0.000 abstract description 2
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- 229910001961 silver nitrate Inorganic materials 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- VWYVABSAUVXYNS-QFIPXVFZSA-N (2s)-6-amino-2-(octadecanoylamino)hexanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCCCN VWYVABSAUVXYNS-QFIPXVFZSA-N 0.000 description 6
- -1 amino acid salt Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- OLDGKSQBWGEFNM-UHFFFAOYSA-N 6-amino-2-(hexadecanoylamino)hexanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NC(C(O)=O)CCCCN OLDGKSQBWGEFNM-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DENIQPHQUIGDJZ-IBGZPJMESA-N (2s)-5-(diaminomethylideneamino)-2-(hexadecanoylamino)pentanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCCNC(N)=N DENIQPHQUIGDJZ-IBGZPJMESA-N 0.000 description 2
- ANKFOZDLPDQNEO-UHFFFAOYSA-N 5-(diaminomethylideneamino)-2-(tetradecanoylamino)pentanoic acid Chemical compound CCCCCCCCCCCCCC(=O)NC(C(O)=O)CCCN=C(N)N ANKFOZDLPDQNEO-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
- RBWNDBNSJFCLBZ-UHFFFAOYSA-N 7-methyl-5,6,7,8-tetrahydro-3h-[1]benzothiolo[2,3-d]pyrimidine-4-thione Chemical compound N1=CNC(=S)C2=C1SC1=C2CCC(C)C1 RBWNDBNSJFCLBZ-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- DVHIYVOBSKWPJD-SFHVURJKSA-N N-myristoyl lysine Chemical compound CCCCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCCCN DVHIYVOBSKWPJD-SFHVURJKSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZSILVJLXKHGNPL-UHFFFAOYSA-L S(=S)(=O)([O-])[O-].[Ag+2] Chemical compound S(=S)(=O)([O-])[O-].[Ag+2] ZSILVJLXKHGNPL-UHFFFAOYSA-L 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- YRNNKGFMTBWUGL-UHFFFAOYSA-L copper(ii) perchlorate Chemical compound [Cu+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O YRNNKGFMTBWUGL-UHFFFAOYSA-L 0.000 description 1
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- YPNVIBVEFVRZPJ-UHFFFAOYSA-L silver sulfate Chemical compound [Ag+].[Ag+].[O-]S([O-])(=O)=O YPNVIBVEFVRZPJ-UHFFFAOYSA-L 0.000 description 1
- 229910000367 silver sulfate Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000005211 surface analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
Definitions
- Antimicrobial amino acid and inorganic salt thereof production method thereof and use thereof
- the present invention relates to an antibacterial amino acid and an inorganic salt thereof useful as a surfactant, a method for producing the same, and a use as a surfactant.
- N-long chain basic amino acids have been used widely as detergents, emulsifiers or dispersants because of their surface activity.
- the N-long-chain-basic-basic-amino acid used as a raw material for the amino acid salt is, for example, an alkali in a mixed solvent of water and a hydrophilic organic solution.
- N-long-chain acyl basic amino acids synthesized by reacting basic amino acids with long-chain fatty acid halides in the presence of 10 amino acids are separated from this synthesis reaction solution without using a crystallization step. No. 57-747092).
- the pH is adjusted from 40 ° C to the boiling point of the hydrophilic organic solvent.
- N-long-chain-basyl basic amino acid obtained by removing the solvent from the obtained organic layer can be used as it is. It has a high purity and can separate N-long-chain-basic-amino acids from the N-long-chain-basic-amino-acid synthesizing reaction solution. It can also be applied to the purification of N-acyl basic amino acids.
- an object of the present invention is to provide an N-long-chain acetyl basic amino acid having antibacterial activity and a method for producing the same.
- the present invention provides an antibacterial amino acid or an inorganic salt thereof, in which a compound of an antibacterial metal ion and / or an antibacterial metal is coordinated with an N-long-chain acetyl basic amino acid.
- the present invention also provides the antibacterial N-long-chain basic amino acid of the present invention, which comprises mixing and neutralizing a strongly alkaline aqueous solution of an N-long-chain basic amino acid with an antibacterial metal or a compound thereof.
- a method for producing an amino acid or an inorganic salt thereof is provided.
- the present invention provides a surfactant having an antibacterial activity, comprising the antibacterial N-long-chain acetyl basic amino acid of the present invention or an inorganic salt thereof.
- the present invention provides a surfactant having an antibacterial activity, produced by the method of the present invention. Since the antibacterial N-acyl basic amino acid of the present invention has both surface activity and excellent antibacterial activity, it can be used in cosmetics, chemicals, fibers, resins, etc., which require antibacterial properties, as detergents, emulsifiers, and dispersants. It can be applied as an agent or the like.
- the antimicrobial N- long-chain N- long chain Ashiru group Ashiru basic Amino acids of the present invention are not limited to, C n H 2n + 1 C0- ( n is an integer of 1 2-2 2) Those represented by are preferred.
- the alkyl group in the acyl group may be linear or branched, but is preferably linear.
- Specific examples of preferred long-chain acryl groups include myristoyl groups, palmitoyl groups, stearoyl groups, oleoyl groups, and the like.
- the term “basic amino acid” to which a long-chain acryl group binds means an amino acid that shows basicity in an aqueous solution, and preferred specific examples include lysine and arginine.
- the basic amino acid usually has a plurality of nitrogen atoms, but the long-chain acetyl group may be bonded to any of the nitrogen atoms. May be bonded to the nitrogen atom. However, it is preferable that one long-chain acryl group is bonded to the ⁇ -amino group.
- preferred ⁇ -long chain basic amino acids include ⁇ -sparoylysine and ⁇ -myristoyl Examples include, but are not limited to, lysine, N-sparyoylarginine, N-myristoylarginine, N-palmitoyllysine, N-palmitoylarginine and the like.
- the N-long chain sacyl basic amino acid may also be in the form of an inorganic salt.
- preferred examples of the metal constituting the inorganic salt include alkali metal such as sodium and potassium.
- an antibacterial metal ion or compound is coordinated to the N-basic basic amino acid or the inorganic salt thereof.
- Preferred examples of the antibacterial metal include, but are not limited to, silver, copper, and zinc, which are highly safe for the human body.
- the ion or compound of the antibacterial metal coordinate with the nitrogen atom in the basic amino acid.
- Basic amino acids usually have a plurality of nitrogen atoms, but an antibacterial metal ion or compound may be coordinated to any of the nitrogen atoms, or may be coordinated to a plurality of nitrogen atoms. . Further, a compound of an antibacterial metal such as chloride may be coordinated.
- the N-long chain acetyl basic amino acid or the inorganic salt thereof of the present invention can be produced by mixing a strong alkali aqueous solution or a strong acid aqueous solution of an N-long chain acryl basic amino acid with an antibacterial metal or a compound thereof. Can be. Mixing can be performed at room temperature.
- Preferred examples of the strong alkali used in this method include sodium hydroxide and potassium hydroxide, but are not limited thereto.
- Preferred examples of the strong acid include hydrochloric acid, but are not limited thereto.
- the concentration of the alkali in the strong alkali aqueous solution is not particularly limited, but is preferably about 1 to 20% by weight.
- the concentration of the strong acid in the strong acid aqueous solution is preferably about 1 to 20% by weight.
- the concentration of the N-long-chain acetyl basic amino acid in the strong aqueous solution or the strong acid aqueous solution is usually about 1 to 20% by weight, preferably 3 to 10% by weight.
- the antibacterial metal can be added as a simple metal when it is dissolved in a strong acid or strong alkaline solution to be used to generate metal ions, but it is preferable to use an ionic compound, particularly a water-soluble salt.
- an ionic compound particularly a water-soluble salt.
- a water-soluble salt Silver nitrate, silver sulfate, silver acetate, silver lactate, silver perchlorate, silver thiosulfate, etc., which produce copper ions, copper nitrate, copper sulfate, copper acetate, copper formate, copper perchlorate
- Examples of those that generate zinc ions include zinc nitrate, zinc sulfate, zinc acetate, zinc perchlorate, and the like.
- the same water-soluble metal salts can be used.
- the addition amount of the antibacterial metal or its compound is preferably about 0.01 to 3.0% by weight, more preferably 0.5 to 1.0% by weight, based on the N-long chain basic amino acid. About 0% is preferable.
- the antibacterial N-long-chain-basic-amino acid formed by the above method is present as a precipitate in the strong acid or strong aqueous solution.
- the precipitate is washed with distilled water or the like, filtered and taken out, and then dried, or the solution is neutralized and then filtered and dried, whereby a powdery antibacterial amino acid can be recovered.
- hydrochloric acid is preferably used in the case of basicity
- sodium hydroxide or sodium hydroxide is preferably used in the case of acidity.
- antibacterial N-long-chain-basic-basic amino acid and the inorganic salt thereof of the present invention have surface activity and antibacterial activity, they can be used for cosmetics, detergents, chemicals, fibers, resins, etc., which require antibacterial properties. It can be used as an activator.
- Antibacterial N-long chain basic amino acids and their inorganic salts can be applied by dissolving or kneading the powder or high-concentration solution into the composition, or kneading with fibers or resins. Alternatively, it can be applied by being included in a coating agent composition.
- N-myristoylarginine was dissolved in 100 ml of a 1% aqueous sodium hydroxide solution, and 0.2 g of silver lactate was added, followed by thorough stirring.
- N-palmitoyl lysine was dissolved in 10 OmI of a 15% aqueous potassium hydroxide solution, and 0.17 g of silver lactate was added thereto, followed by thorough stirring.
- N-sparoylysine was dissolved in 100 ml of a 10% aqueous sodium hydroxide solution, and 0.5 g of chloroauric acid was added, followed by thorough stirring.
- N-sparoylysine was dissolved in 10 OmI of a 10% aqueous potassium hydroxide solution, and 0.5 g of zinc nitrate was added, followed by thorough stirring.
- N-palmitoylarginine was dissolved in 100 ml of an aqueous solution of 10 ⁇ 1 ⁇ 2 hydrogen chloride, and 0.16 g of silver nitrate was added, followed by stirring well.
- FIG. 1 shows the result of powder X-ray diffraction of this sample. The upper part of FIG.
- the precipitates obtained in Examples 1 to 9 were washed, filtered, and dried to obtain powder samples. Antimicrobial tests were performed by the shake flask method with the concentration of these samples being 0.1 ppm. For comparison, a similar test was performed using N-sparoylysine, silver chloride and silver nitrate. Silver nitrate was also tested when the sample concentration was set to 0.05 ppm in addition to 0.1
- this test method involves adding a test sample to a culture solution containing Escherichia coli to the above-mentioned concentration, setting the density of Escherichia coli to 1.6 ⁇ 10 5 nom I, shaking culture at 25 ° C, The number of E. coli after 12 hours and after 12 hours is measured. The results are shown in Table 1 below.
- Example 2 1.6 x 10 s 10 10
- Example 3 1.6 x 10 5 10
- Example 4 1.6 x 10 P 10 ku 10
- Example 5 1.6 ⁇ 10 a ku 10 ku 10
- Example 6 1.6 ⁇ 10 10
- Example 7 1.6 1.610. 10
- Example 8 1.6 ⁇ 10. 10
- Example 9 1.6 ⁇ 10. C 10 c 10
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Abstract
Cette invention concerne des aminoacides de base N-(acyle à chaîne longue) et leurs sels inorganiques, qui présentent une activité de surface et une activité antibactérienne et qui comportent des composés de coordination constitués d'aminoacides de base N-(acyle à chaîne longue) et d'ions ou de composés métalliques antibactériens. On prépare ces aminoacides en mélangeant une solution aqueuse fortement alcaline contenant un aminoacide de base N-(acyle à chaîne longue) avec un composé métallique antibactérien. Ces composés sont utiles en tant que tensioactifs antibactériens.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8/53678 | 1996-02-19 | ||
| JP5367896 | 1996-02-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997030057A1 true WO1997030057A1 (fr) | 1997-08-21 |
Family
ID=12949489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1997/000445 WO1997030057A1 (fr) | 1996-02-19 | 1997-02-19 | Aminoacides antibacteriens, leurs sels inorganiques et leur procede de preparation et d'utilisation |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO1997030057A1 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6630172B2 (en) | 2001-01-22 | 2003-10-07 | Kareem I. Batarseh | Microbicidal composition containing potassium sodium tartrate |
| US6939566B2 (en) | 1999-04-20 | 2005-09-06 | Kareem I. Batarseh | Microbicidal formulations and methods to control microorganisms |
| WO2009069296A1 (fr) * | 2007-11-28 | 2009-06-04 | Kao Corporation | Agent d'élimination d'un biolfilm |
| JP2009149857A (ja) * | 2007-11-28 | 2009-07-09 | Kao Corp | バイオフィルム除去剤 |
| JP2015195826A (ja) * | 2014-03-31 | 2015-11-09 | 株式会社Ｎｂｃメッシュテック | 殺菌・抗ウイルス性部材 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH029852A (ja) * | 1988-06-28 | 1990-01-12 | Kenji Ichikawa | 抗菌作用性物質、それを含有する抗菌性樹脂成形物、抗菌性合成繊維、抗菌性を有する紙、抗菌性塗料および合成樹脂製抗菌性水槽 |
-
1997
- 1997-02-19 WO PCT/JP1997/000445 patent/WO1997030057A1/fr active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH029852A (ja) * | 1988-06-28 | 1990-01-12 | Kenji Ichikawa | 抗菌作用性物質、それを含有する抗菌性樹脂成形物、抗菌性合成繊維、抗菌性を有する紙、抗菌性塗料および合成樹脂製抗菌性水槽 |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6939566B2 (en) | 1999-04-20 | 2005-09-06 | Kareem I. Batarseh | Microbicidal formulations and methods to control microorganisms |
| US6630172B2 (en) | 2001-01-22 | 2003-10-07 | Kareem I. Batarseh | Microbicidal composition containing potassium sodium tartrate |
| WO2009069296A1 (fr) * | 2007-11-28 | 2009-06-04 | Kao Corporation | Agent d'élimination d'un biolfilm |
| JP2009149857A (ja) * | 2007-11-28 | 2009-07-09 | Kao Corp | バイオフィルム除去剤 |
| JP2010013655A (ja) * | 2007-11-28 | 2010-01-21 | Kao Corp | 医療機器の洗浄方法 |
| US8382912B2 (en) | 2007-11-28 | 2013-02-26 | Kao Corporation | Biofilm-removing agent |
| CN101878290B (zh) * | 2007-11-28 | 2013-11-13 | 花王株式会社 | 生物膜除去剂 |
| JP2015195826A (ja) * | 2014-03-31 | 2015-11-09 | 株式会社Ｎｂｃメッシュテック | 殺菌・抗ウイルス性部材 |
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