EP4258868A1 - Composition de lactame et utilisation - Google Patents
Composition de lactame et utilisationInfo
- Publication number
- EP4258868A1 EP4258868A1 EP21802747.2A EP21802747A EP4258868A1 EP 4258868 A1 EP4258868 A1 EP 4258868A1 EP 21802747 A EP21802747 A EP 21802747A EP 4258868 A1 EP4258868 A1 EP 4258868A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lactam
- composition
- lactate
- solvent
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 79
- 150000003951 lactams Chemical class 0.000 title claims abstract description 67
- 239000002904 solvent Substances 0.000 claims abstract description 45
- 230000001580 bacterial effect Effects 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 30
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims description 22
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 22
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 12
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 12
- 229940116333 ethyl lactate Drugs 0.000 claims description 11
- 150000004730 levulinic acid derivatives Chemical class 0.000 claims description 11
- 150000003903 lactic acid esters Chemical class 0.000 claims description 10
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 230000003139 buffering effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- HHCPGPHTKXVNHA-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-methylidenepyrrol-2-one Chemical compound C1=CC(Cl)=CC=C1C1=CC(=O)NC1=C HHCPGPHTKXVNHA-UHFFFAOYSA-N 0.000 description 5
- YSZWLEFVAJQHJS-UHFFFAOYSA-N 5-methylidene-4-(4-methylphenyl)pyrrol-2-one Chemical compound C1=CC(C)=CC=C1C1=CC(=O)NC1=C YSZWLEFVAJQHJS-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- PZQOWENOZPCUSJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-hydroxy-5-methyl-1H-pyrrol-2-one Chemical compound CC1(O)NC(=O)C=C1C1=CC=C(Cl)C=C1 PZQOWENOZPCUSJ-UHFFFAOYSA-N 0.000 description 3
- CPAOXJPVYYJEAF-UHFFFAOYSA-N 5-hydroxy-5-methyl-4-(4-methylphenyl)-1H-pyrrol-2-one Chemical compound CC1=CC=C(C=C1)C1=CC(=O)NC1(C)O CPAOXJPVYYJEAF-UHFFFAOYSA-N 0.000 description 3
- JTBGHWGTJYXHMI-UHFFFAOYSA-N 5-hydroxy-5-methyl-4-(4-methylphenyl)furan-2-one Chemical compound CC1=CC=C(C=C1)C1=CC(=O)OC1(C)O JTBGHWGTJYXHMI-UHFFFAOYSA-N 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- OVLMWAKWSBFBBQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-hydroxy-5-methylfuran-2-one Chemical compound CC1(O)OC(=O)C=C1C1=CC=C(Cl)C=C1 OVLMWAKWSBFBBQ-UHFFFAOYSA-N 0.000 description 2
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- MOOYVEVEDVVKGD-UHFFFAOYSA-N oxaldehydic acid;hydrate Chemical compound O.OC(=O)C=O MOOYVEVEDVVKGD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- WEJRYKSUUFKMBC-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C(Cl)C=C1 WEJRYKSUUFKMBC-UHFFFAOYSA-N 0.000 description 1
- NOXKUHSBIXPZBJ-UHFFFAOYSA-N 1-(4-methylphenyl)propan-2-one Chemical compound CC(=O)CC1=CC=C(C)C=C1 NOXKUHSBIXPZBJ-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- KVZLHPXEUGJPAH-UHFFFAOYSA-N 2-oxidanylpropanoic acid Chemical class CC(O)C(O)=O.CC(O)C(O)=O KVZLHPXEUGJPAH-UHFFFAOYSA-N 0.000 description 1
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical class CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940058352 levulinate Drugs 0.000 description 1
- 229940040102 levulinic acid Drugs 0.000 description 1
- 239000002029 lignocellulosic biomass Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
Definitions
- the invention relates to an improvement in the field of hygiene, in particular to a composition comprising a lactam which displays improved solubility and stability of the lactam.
- Hygiene in particular inhibition of bacterial species, is important to consumers.
- Lactams are known as inhibitors of bacterial species. They may be applied to surfaces to inhibit bacterial species.
- the invention relates in a first aspect to a composition
- a composition comprising:-
- composition has a pH of from 4 to 6.50, preferably pH 4 to 6.25, more preferably 4.50 to 6.00; wherein the lactam is selected from:
- the pH is from 4 to 5.40, more preferably from 4.50 to 5.40.
- lactam is selected from:
- lactam is:
- the lactam is delivered from an aqueous based composition, preferably comprising from 0.1 to 98 wt.%, preferably from 0.5 to 80 wt.%, more preferably from 1 to 75 wt.% water.
- the solvent is selected from the group: alcohol; levulinate derivatives; lactate derivatives; and solvents with a dielectric constant of 15 of higher, preferably the solvent is selected from the group: alcohol, levulinate derivatives; and lactate derivatives; more preferably the solvent is selected from the group: levulinate derivatives and lactate derivatives.
- solvents are: of alcohols, preferably a C1-C4 alcohol, more preferably ethanol; of lactate derivatives, preferably ethyl lactate and/or butyl lactate; of levulinate derivatives, preferably 2-methyltetrahydrofuran, ethyl levulinate, and/or ethyl levulinate glycerol ketal (LGK); and of solvents with a dielectric constant of 15 of higher, preferably dimethyl sulfoxide (DMSO).
- alcohols preferably a C1-C4 alcohol, more preferably ethanol
- lactate derivatives preferably ethyl lactate and/or butyl lactate
- levulinate derivatives preferably 2-methyltetrahydrofuran, ethyl levulinate, and/or ethyl levulinate glycerol ketal (LGK)
- LGK ethyl levulinate glycerol ketal
- the solvent is selected from the group: ethanol; ethyl lactate, butyl lactate; 2- methyltetrahydrofuran, ethyl levulinate, and ethyl levulinate glycerol ketal (LGK), or mixtures thereof.
- the solvent is selected from the group: levulinate derivatives; and lactate derivatives.
- the solvent is selected from the group: ethyl lactate, butyl lactate; 2- methyltetrahydrofuran, ethyl levulinate, and ethyl levulinate glycerol ketal (LGK), or mixtures thereof.
- the solvent is present at a level of from 0.5 to 95 wt.%, preferably from 0.5 to 90 wt.%, more preferably from 0.5 to 80 wt.%.
- the solvent may be present at a lowest level of from 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.% or even 5 wt.%.
- the solvent may be present at a highest level of from 95 wt.%, 90 wt.%, 85 wt.%, 80 wt.%, 70 wt.%, 60 wt.%, 50 wt.%, 40 wt.%, 30 wt.%, 25 wt.%, 20 wt.% or even 10 wt.%. Any higher level of solvent is meant to be combinable with any lower level of solvent.
- the composition comprises one or more surfactants.
- the surfactant may be present at a level of from 0.25 to 25 wt.%, preferably from 0.25 to 20 wt.%, more preferably from 0.25 to 15 wt.%, even more preferably from 0.25 to 10 wt.%, or even 0.5 to 10 wt.% or even 0.5 to 5 wt.%.
- the surfactant may be present at a level of from 0.25 to 25 wt.%, preferably from 0.25 to 20 wt.%, more preferably from 0.25 to 15 wt.%, even more preferably from 0.25 to 10 wt.%, or even 0.5 to 10 wt.% or even 0.5 to 5 wt.%.
- the surfactant is preferably selected from anionic, nonionic, cationic and/or amphoteric surfactants.
- Preferred surfactants are nonionic surfactants.
- the composition preferably comprises a buffer.
- the invention relates in a second aspect to a method of treatment of a surface, to improve resistance of said surface to bacterial fouling, by treatment with a composition according to the first aspect of the invention.
- the surface to be treated is selected from plastic, metal, wood, polymer, paper, textile, and/or wipes.
- the lactam is selected from:
- the invention further relates in a third aspect to the use in a lactam composition, of a combination of a solvent and application of pH at from 4 to 6.5, preferably 4 to 6.25, more preferably 4.50 to 6.00 to said composition, to improve the solubility and stability of said lactam in the composition.
- the lactam is selected from:
- Figure 1 is a photograph showing the solubility of the lactam 488 at pH 5, pH 7 and pH 8
- Figure 2 demonstrates the pH effect on the solubility and stability of the lactam 488. Lactam initial solubility (Left hand axis and circular data points) and stability (right hand axis and square data points) vs buffer pH, with lactam delivered in ethanol, to a total of 2% solvent and 100 ppm lactam in solution
- a lactam is a cyclic amide.
- the lactam is a lactam selected from:
- lactam is selected from: Most preferably the lactam is:
- the lactam is cationic in nature
- the cation can be used or with a suitable counterion (e.g. iodide).
- the lactam is present at a level of from 0.0001 to 2.5 wt.%, preferably from 0.0001 to 1 wt.%.
- the lactam may be suitably present at levels of 0.001 to 1 wt.%, or even 0.01 to 1 wt.%, or even 0.01 to 0.5 wt.%.
- the lactam is delivered from an aqueous based composition, preferably comprising from 0.1 to 98 wt.%, preferably from 0.5 to 80 wt.%, more preferably from 1 to 75 wt.% water.
- the composition may comprise any amount of water ranging from lower amounts of 0.1 , 0.5, 1, 1.5, 2 or even 5 wt.% water up to 30, 40, 50, 60, 70, 75, 80, 85, 90, 95, 96, 97, 98, or even 99 wt.% water.
- the composition comprises a solvent.
- Preferred solvents are selected from the group: alcohol; levulinate derivatives; lactate derivatives; and, solvents with a dielectric constant of 15 of higher.
- Preferred examples of solvents are: of alcohols, preferably a C1-C4 alcohol, more preferably ethanol; of lactate derivatives, preferably ethyl lactate and/or butyl lactate; of levulinate derivatives, preferably 2-methyltetrahydrofuran, ethyl levulinate, and/or ethyl levulinate glycerol ketal (LGK); and of solvents with a dielectric constant of 15 of higher, preferably dimethyl sulfoxide (DMSO).
- DMSO dimethyl sulfoxide
- the solvent is selected from the group: ethanol; ethyl lactate, butyl lactate; 2- methyltetrahydrofuran (2Me-THF), ethyl levulinate, and ethyl levulinate glycerol ketal (LGK), or mixtures thereof.
- the solvent is selected from the group: levulinate derivatives; and lactate derivatives.
- the solvent is selected from the group: ethyl lactate, butyl lactate; 2- methyltetrahydrofuran, ethyl levulinate, and ethyl levulinate glycerol ketal (LGK), or mixtures thereof.
- 2Me-THF, ethyl levulinate and LGK can be classed as levulinic acid derivatives (or levulinate derivatives).
- Levulinic acid may be derived from lignocellulosic biomass (i.e. corn husks, sugar cane waste etc), and can be converted in to 2Me-THF in a cyclisation reaction, ethyl levulinate in one step esterification, and LGK in 2 steps (esterification and ketal synthesis).
- Ethyl lactate and butyl lactate are lactic acid (lactate) derivatives. Lactic acid is a byproduct of fermentation which is then reacted with ethanol or butanol to generate ethyl and butyl lactate.
- the solvent is present at a level of from 0.5 to 95 wt.%, preferably from 0.5 to 90 wt.%, more preferably from 0.5 to 80 wt.%.
- the solvent may be present at a lowest level of from 0.5 wt.%, 0.75 wt.%, 1 wt.%, 1.5 wt.%, 2 wt.%, 2.5 wt.% or even 5 wt.%.
- the solvent may be present at a highest level of from 95 wt.%, 90 wt.%, 85 wt.%, 80 wt.%, 70 wt.%, 60 wt.%, 50 wt.%, 40 wt.%, 30 wt.%, 25 wt.%, 20 wt.% or even 10 wt.%. Any higher level of solvent is meant to be combinable with any lower level of solvent.
- the solvent may be present at a level of from 1 to 80 wt.%, preferably from 1 to 50 wt.%, more preferably from 1 to 40 wt.%.
- the solvent level may also be from 1 to 30 wt.%, 1 to 20 wt.%, or even 1 to 15 wt.% or 1 to 10 wt.%.
- the composition comprises one or more surfactants.
- the surfactant may be present at a level of from 0.25 to 25 wt.%, preferably from 0.25 to 20 wt.%, more preferably from 0.25 to 15 wt.%, even more preferably from 0.25 to 10 wt.%, or even 0.5 to 10 wt.% or even 0.5 to 5 wt.%.
- the surfactant is preferably selected from anionic, nonionic, cationic and/or amphoteric surfactants.
- Preferred surfactants are nonionic surfactants.
- the composition may preferably comprise a buffer to assist in maintaining any resulting composition within a specified pH range.
- Buffering systems may be any usual buffering system known in the art. These may for example include citrate, acetate, phosphate, and or carbonate buffers, or mixtures thereof.
- composition may comprise further ingredients such as surfactants, chelating agents, thickeners, pH modifiers, and perfumes.
- 1-(4-Chlorophenyl)propan-2-one (40.00 g, 34.75 mL, 237.2 mmol), glyoxylic acid monohydrate (32.75 g, 355.8 mmol) and phosphoric acid (69.74 g, 711.7 mmol) were combined at room temperature before heating to 85 °C overnight. After cooling to room temperature, the mixture was poured into a mixture of water (500 mL) and ethyl acetate (500 mL). The layers were separated and the aqueous phase extracted with ethyl acetate (500 mL).
- aqueous layer was extracted with dichloromethane (100 mL), and the combined organic layers washed with a 1 :1 mixture of water and saturated aqueous sodium hydrogen carbonate solution (100 mL), dried (MgSC and filtered. Silica was added to the filtrate and the mixture stirred for 10 minutes before filtering through a plug of silica, washing through with dichloromethane followed by a 3:1 mixture of dichloromethane:diethyl ether. Fractions containing the desired product were combined and concentrated under reduced pressure.
- lactam used was lactam 488.
- This example shows the effect of the pH on the solubility of the lactam in an aqueous based composition with a solvent included.
- a targeted 10,000 ppm stock of lactam 488 in EtOH was prepared and left on the bottle rollers for 24 hrs, before filtration through a syringe filter to yield a saturated solution (likely around 8000 ppm in EtOH).
- This stock solution was mixed in a 1 :2 ratio with 0.1 M acetate buffer at pH 5.2, or with 0.1M phosphate buffer at pH 7 or 8, agitated in vial and observed visually for any precipitate formed, indicating insolubility.
- Figure 1 glass picture
- the lactam was mostly solubilised to an acceptable level at 5, while at pH 7 and 8, the solubility was greatly reduced.
- Example 3 This example demonstrates the lack of stability of the lactam composition at pH below pH 4 and above pH 6.5.
- Lactam 488 was dissolved to maximum concentration ( ⁇ 10 mg/mL) in d6-DMSO, and mixed in a 2:1 ratio with a range of pH buffers (pH 7.4 0.2M phosphate buffer, pH 6 0.1 M citrate buffer, pH 5.2 0.1M acetate buffer, 4, 2) and water. These samples were then filtered and studied by water suppression 1 H NMR a weekly time points for 4 weeks. Relative %lactam remaining was quantified using the integration of the buffer peak compared to the lactam resonance at 5.22 ppm.
- the lactam is only initially solubilised and displays long term stability (4 weeks) for compositions where the pH is from 4 to 6.5. Above this pH, the composition does not solubilise well enough and is also not stable, and below pH 4, the composition is not stable.
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Abstract
L'invention concerne une composition comprenant : (a) de 0,0001 à 5 % en poids d'un lactame ; et (b) de 1 à 80 % en poids d'un solvant ; la composition ayant un pH de 4 à 6,50 ; le lactame étant choisi parmi les formules. L'invention concerne également un procédé de traitement d'une surface pour améliorer la résistance de ladite surface à l'encrassement bactérien ; et également l'utilisation, dans une composition de lactame, d'une combinaison d'un solvant et d'une application de pH allant de 4 à 6,50 à ladite composition pour améliorer la solubilité et la stabilité dudit lactame dans la composition.
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EP20212740 | 2020-12-09 | ||
PCT/EP2021/080767 WO2022122265A1 (fr) | 2020-12-09 | 2021-11-05 | Composition de lactame et utilisation |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2009069006A2 (fr) * | 2007-11-30 | 2009-06-04 | Foamix Ltd. | Peroxyde de benzoyle contenant de la mousse |
CN105050393B (zh) * | 2013-02-01 | 2018-07-03 | 荷兰联合利华有限公司 | 包含内酰胺和助水溶剂的抗微生物组合物 |
EP3337451B1 (fr) * | 2015-08-20 | 2018-12-26 | Unilever PLC | Solubilité de lactame améliorée |
WO2020053108A1 (fr) * | 2018-09-14 | 2020-03-19 | Unilever Plc | Composition de mousse |
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