EP4258876A1 - Lactamzusammensetzung und verwendung - Google Patents

Lactamzusammensetzung und verwendung

Info

Publication number
EP4258876A1
EP4258876A1 EP21802746.4A EP21802746A EP4258876A1 EP 4258876 A1 EP4258876 A1 EP 4258876A1 EP 21802746 A EP21802746 A EP 21802746A EP 4258876 A1 EP4258876 A1 EP 4258876A1
Authority
EP
European Patent Office
Prior art keywords
lactam
hydrogen
film
polymers
polyvinylalcohol
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
Application number
EP21802746.4A
Other languages
English (en)
French (fr)
Inventor
Nicholas BROWNBILL
Joanne Clare O'keeffe
Neil James Parry
Craig Warren Jones
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever Global IP Ltd
Unilever IP Holdings BV
Original Assignee
Unilever Global IP Ltd
Unilever IP Holdings BV
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Unilever Global IP Ltd, Unilever IP Holdings BV filed Critical Unilever Global IP Ltd
Publication of EP4258876A1 publication Critical patent/EP4258876A1/de
Pending legal-status Critical Current

Links

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
    • 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
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • 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 displays improved inhibition of bacterial species.
  • 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:-
  • a film-forming polymer from 0.1 to 80 wt.%, preferably from 0.25 to 40 wt.%, more preferably from 0.5 to 35 wt.% of a film-forming polymer; wherein the film-forming polymer is selected from polysaccharides, quaternised polysaccharide derivatives, polyvinylpyrrolidone (PVP) and co-polymers thereof, and, polyvinylalcohol (PVA) and co-polymers of polyvinylalcohol, and/or mixtures thereof; and, wherein the lactam is of formula (I) or (II):
  • R1 and R2 are each independently selected from hydrogen, halogen, alkyl, cycloalkyl, alkoxy, oxoalkyl, alkenyl, heterocyclyl, heteroaryl, aryl and aralalkyl;
  • R4 and R5 are independently selected from hydrogen, aryl, heterocyclyl, heteroaryl, and arylalkyl;
  • Re is selected from hydrogen and methyl
  • R1, R4 and R5 are H;
  • R3 is H, or (CH2) n N + (CH3)3, where n is an integer from 1 to 16, preferably 2 to 8;
  • R2 is a phenyl group, or a monosubstituted phenyl group; preferably R2 is selected from phenyl, 4-fluorophenyl, 2- fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4-methylphenyl.
  • the lactam is a lactam selected from:
  • lactam is selected from:
  • lactam is: -chlorophenyl)-5-methylene-pyrrol-2-one
  • the lactam is delivered from an aqueous based composition, preferably comprising from 0.1 to 99 wt.%, preferably from 0.5 to 98 wt.%, more preferably from 1 to 98 wt.% water.
  • the solvent is preferably 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 selected from the group: 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.
  • Preferred natural polymers are polysaccharides, for example xanthan and hydroxypropyl methylcellulose (HPMC), and quaternised polysaccharide derivative polymers, for example Celquat.
  • Preferred synthetic polymers include polyvinylpyrrolidone (PVP) and co-polymers thereof, polyvinylalcohol (PVA) and co-polymers of polyvinylalcohol.
  • More preferred film-forming polymers are polysaccharides, quaternised polysaccharide derivates, polyvinylpyrrolidone (PVP) and co-polymers thereof, and, polyvinylalcohol (PVA) and co-polymers of polyvinylalcohol.
  • Most preferred film-forming polymers are quaternised polysaccharide derivates, polyvinylpyrrolidone (PVP) and co-polymers thereof, and, polyvinylalcohol (PVA) and copolymers of polyvinylalcohol.
  • 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 invention relates in a second aspect to a non-therapeutic 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 of a combination of a lactam and a film forming polymer to improve inhibition of bacterial species, wherein the film-forming polymer is selected from polysaccharides, quaternised polysaccharide derivatives, polyvinylpyrrolidone (PVP) and co-polymers thereof, and, polyvinylalcohol (PVA) and co-polymers of polyvinylalcohol, and/or mixtures thereof; and, wherein the lactam is of formula (I) or (II): wherein:
  • R1 and R2 are each independently selected from hydrogen, halogen, alkyl, cycloalkyl, alkoxy, oxoalkyl, alkenyl, heterocyclyl, heteroaryl, aryl and aralalkyl;
  • R4 and R5 are independently selected from hydrogen, aryl, heterocyclyl, heteroaryl, and arylalkyl;
  • Re is selected from hydrogen and methyl
  • the lactam is selected from: Detailed Description of the Invention
  • indefinite article “a” or “an” and its corresponding definite article “the” as used herein means at least one, or one or more, unless specified otherwise.
  • a lactam is a cyclic amide.
  • Preferred lactams are y-lactams which have 5 ring atoms.
  • the lactam is of formula (I) or (II): wherein:
  • Ri and R2 are each independently selected from hydrogen, halogen, alkyl, cycloalkyl, alkoxy, oxoalkyl, alkenyl, heterocyclyl, heteroaryl, aryl and aralalkyl; and
  • R4 and R5 are independently selected from hydrogen, aryl, heterocyclyl, heteroaryl, and arylalkyl;
  • Re is selected from hydrogen and methyl
  • R4 and R5 are hydrogen. It will be appreciated that, where appropriate groups may be optionally substituted. Optional substituents may include halogens, Ci-4alkyl, Ci.4haloalkyl (for example, CF3) and Ci.4alkoxy.
  • Alkyls may, for example, be Ci. ⁇ alkyls, such as Ci-ealkyls.
  • Aryls may, for example, be Ce- aryls, for example, phenyls.
  • At least one of R1 and R2 is selected from heterocyclyl, heteroaryl, aryl and arylalkyl.
  • R1 is hydrogen.
  • R3 is hydrogen, or (CH2) n N + (R a )3, where n is an integer from 1 to 16, preferably 2 to 8, and where each R a is independently H or C1.4 alkyl, more preferably R a is CH3;
  • R4 is hydrogen.
  • R5 is hydrogen.
  • Re is hydrogen.
  • R? is hydrogen.
  • R2 is aryl or aralalkyl. More preferably, R2 is a phenyl group or a substituted phenyl group, for example, a monosubstituted phenyl group. Substitution may be ortho, meta, or para.
  • R2 may be selected from phenyl, 4-fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4-methylphenyl.
  • R1, R4 and R5 are H;
  • R3 is H, or (CH2) n N + (CH3)3, where n is an integer from 1 to 16, preferably 2 to 8;
  • R2 is a phenyl group, or a mono-substituted phenyl group; preferably R2 is selected from phenyl, 4- fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4- methylphenyl.
  • the lactam is of formula (I), R1, R4 and R5 are H; R3 is H, or (CH2) n N + (CH3)3, where n is an integer from 1 to 16, preferably 2 to 8; and R2 is a phenyl group, or a mono-substituted phenyl group; preferably R2 is selected from phenyl, 4- fluorophenyl, 2-fluorophenyl, 4-chlorophenyl, 3-chlorophenyl, 4-bromophenyl and 4- methylphenyl.
  • the lactam is cationic in nature, it can be used as such, or suitably with a counterion (e.g. iodide)
  • a counterion e.g. iodide
  • the lactam is a lactam selected from:
  • lactam is selected from:
  • lactam is: -chlorophenyl)-5-methylene-pyrrol-2-one.
  • the lactam is cationic in nature
  • the cation can be used or with a suitable counterion (e.g. iodide).
  • 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 99 wt.%, preferably from 0.5 to 98 wt.%, more preferably from 1 to 98 wt.% water.
  • 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.
  • preferred levels of water include from 60 to 98 wt.%, preferably from 70 to 98 wt.%, more preferably from 80 to 98 wt.%, even more preferably from 85 to 98 wt.% or even from 90 to 98 wt.%.
  • the composition comprises a solvent, said solvent preferably selected from the group: alcohol; levulinate derivatives; lactate derivatives; and, solvents with a dielectric constant of 15 of higher.
  • alcohol solvents examples include glycols, for example propylene glycols, and polyethylene glycols; methanol, ethanol, propanol, butanol, isopropanol, benzyl alcohol, lanolin alcohols, and fatty alcohols.
  • examples of other solvent include ethyl acetate, oleic acid, and isopropyl myristate.
  • 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 (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 selected from the group: 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 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 a film-forming polymer.
  • a film-forming polymer is a substance capable of forming a film upon application to a solid surface.
  • the materials most commonly used as film-forming materials include reactive (irreversible) oligomers such as alkyd, phenol-formaldehyde, epoxy, and polyester resins, as well as non- reactive (reversible) polymers of relatively low molecular weight, among them chlorinated polyvinyl chloride resins, polyacrylates, and cellulose nitrates.
  • reactive (irreversible) oligomers such as alkyd, phenol-formaldehyde, epoxy, and polyester resins
  • non- reactive (reversible) polymers of relatively low molecular weight among them chlorinated polyvinyl chloride resins, polyacrylates, and cellulose nitrates.
  • Natural film-forming materials include particularly vegetable oils and rosin derivatives.
  • Film-forming materials are most often used in the form of solutions and dispersions in organic solvents; they can also be aqueous solutions or dispersions and are applied by various methods known to those skilled in the art.
  • Nonreactive film-forming materials form films as a result of evaporation of the solvent; film formation by reactive materials is accompanied by chemical transformations.
  • the general properties of film-forming materials may include (1) good wetting of the surface to be protected; (2) firm binding of any particles in the film; (3) rapid drying in a thin layer (from a few minutes to 24 hrs at 15°-200°C), with formation of strong moisture- and gasresistant films that can withstand prolonged action of the external medium; and (4) good adhesion to the surface being protected. In many cases, these properties are obtained by combining two or more film-forming materials, as well as by the introduction of plasticizers.
  • a range of useful film forming polymers includes:
  • HPMC Hydroxy(propylmethyl) cellulose
  • Ethylcellulose which are commercially available under the tradenames of EthocelTM including the grades 100, 200, 300
  • Poly(vinyl pyrolidine (PVP) which are commercially available under the tradenames of Kolidon® 30; Kolidon® 64; PVP K-30
  • P A Poly(vinyl alcohol) which are commercially available under the tradenames of SelvolTM 205; 503; 805; 823; 840; MowiolTM 18-88; 5-88
  • Methacrylic acid co-polymers which are commercially available under the tradenames of Eudragit® L-30; D-55; E; RS 100, RL 100, NE, RS 30D, S 100
  • Poly(ethylene oxides) which are commercially available under the tradenames PolyoxTM WSR N10; N 750
  • Preferred molecular weight ranges of the film-forming polymers are from 3,000-800,000 Daltons.
  • Preferred film forming polymers are PVA, vinyl alcohol/vinyl acetate copolymers, PVP, polysaccharides, and mixtures of any of the foregoing.
  • the film forming polymer may be further modified with various reagents commonly employed in the art such as plasticizers, surfactants, antifoamers, defoamers, biocides, and the like.
  • plasticizers include glycerol, polyethylene glycol, trimethylolpropane, polyglycerols, alkane diols such as diethylene glycol, triethylene glycol, tetra(ethyleneglycol) and 1 ,3- butanediol; alkanolamines such as triethanolamine; alkanolamine acetates such as triethanolamine acetate; and alkanolacetamides such as ethanol acetamide.
  • the plasticizers may be used in amounts conventionally employed in the film forming art to provide sufficient plasticization, for example, about 20-40% on weight of film forming polymer.
  • Particularly preferred film-forming polymers include natural film-forming polymers and synthetic film-forming polymers.
  • Preferred natural polymers are polysaccharides, for example xanthan and hydroxypropyl methylcellulose (HPMC), and quaternised polysaccharide derivative polymers, for example Celquat.
  • Preferred synthetic polymers include polyvinylpyrrolidone (PVP) and co-polymers thereof, polyvinylalcohol (PVA) and copolymers of polyvinylalcohol.
  • the film-forming polymers are polysaccharides, quaternised polysaccharide derivates, polyvinylpyrrolidone (PVP) and co-polymers thereof, and, polyvinylalcohol (PVA) and copolymers of polyvinylalcohol.
  • Most preferred film-forming polymers are selected from: quaternised polysaccharide derivatives, polyvinylpyrrolidone (PVP) and co-polymers thereof, and, polyvinylalcohol (PVA) and co-polymers of polyvinylalcohol, and/or mixtures thereof; and,
  • the level of the film-forming polymer is from 0.1 to 80 wt.%, preferably from 0.25 to 40 wt.%, more preferably from 0.5 to 35 wt.%. Further preferable weight ranges of the film-forming polymer include 0.5 to 20 wt.%, 0.5 to 15 wt.% or even 0.5 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 keep 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.
  • Solvents used butyl lactate (BL) or ethyl levulinate glycerol ketal (LGK)
  • This example shows the effect of the combination of the film-forming polymer with the lactam.
  • the lactam 488 was solubilised using a solvent, either butyl lactate (BL) or ethyl levulinate glycerol ketal (LGK) to form a 5 mg/ml solution.
  • BL butyl lactate
  • LGK ethyl levulinate glycerol ketal
  • This material was added into an aqueous base formulation containing 2 wt.% nonionic surfactant, and 4 wt.% citric acid.
  • the total amount of lactam in the composition was 0.01 wt.%.
  • the amount of solvent was 2 wt.%; the amount of film-forming polymer (when present) was 0.5 wt.% and the remaining amount up to 100 wt.% was water.
  • the above base formulation included polymer, but no lactam.
  • the inhibition activity of the solubilised lactam was tested against various microorganisms (P. aeruginosa and P. mirabilis). Comparators of the base formulation with the film-forming polymer and chosen solvent were also tested for inhibition. These comparators were found to not inhibit bacterial re-growth. Samples were dried down neat in wells of a microplate, then a bacterial suspension added for 1 hr. Unattached cells were removed, and media added. Remaining cells then grew overnight. The inhibition effect was determined by the frequency of samples (from 18 replicates) where no further growth was detected.
  • lactam and film-forming polymer as made above were tested, these gave a statistically significant improvement for the combination of the lactam with the film- forming polymer over either the polymer alone or the lactam alone, or the additive effects of polymer alone + lactam alone.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP21802746.4A 2020-12-09 2021-11-05 Lactamzusammensetzung und verwendung Pending EP4258876A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20212786 2020-12-09
PCT/EP2021/080764 WO2022122263A1 (en) 2020-12-09 2021-11-05 Lactam composition and use

Publications (1)

Publication Number Publication Date
EP4258876A1 true EP4258876A1 (de) 2023-10-18

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EP (1) EP4258876A1 (de)
CN (1) CN116583180A (de)
WO (1) WO2022122263A1 (de)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR112021004549A2 (pt) * 2018-09-14 2021-06-08 Unilever Ip Holdings B.V. tecido modificado e uso de uma lactama
US20210321611A1 (en) * 2018-09-14 2021-10-21 Conopco, Inc., D/B/A Unilever Wipe
EP3880758A1 (de) * 2018-11-08 2021-09-22 Unilever Global Ip Limited Verfahren zur behandlung einer oberfläche
EP3963017A2 (de) * 2019-05-01 2022-03-09 Novochem Green Additives B.V. Eutektische zusammensetzung

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WO2022122263A1 (en) 2022-06-16

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