EP4258868A1 - Lactamzusammensetzung und verwendung - Google Patents

Lactamzusammensetzung und verwendung

Info

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
Application number
EP21802747.2A
Other languages
English (en)
French (fr)
Inventor
Nicholas Joseph BROWNBILL
Joanne Clare O'keeffe
Neil James Parry
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 EP4258868A1 publication Critical patent/EP4258868A1/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
    • 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.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP21802747.2A 2020-12-09 2021-11-05 Lactamzusammensetzung und verwendung Pending EP4258868A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP20212740 2020-12-09
PCT/EP2021/080767 WO2022122265A1 (en) 2020-12-09 2021-11-05 Lactam composition and use

Publications (1)

Publication Number Publication Date
EP4258868A1 true EP4258868A1 (de) 2023-10-18

Family

ID=73789919

Family Applications (1)

Application Number Title Priority Date Filing Date
EP21802747.2A Pending EP4258868A1 (de) 2020-12-09 2021-11-05 Lactamzusammensetzung und verwendung

Country Status (3)

Country Link
EP (1) EP4258868A1 (de)
CN (1) CN116648138A (de)
WO (1) WO2022122265A1 (de)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009069006A2 (en) * 2007-11-30 2009-06-04 Foamix Ltd. Foam containing benzoyl peroxide
US9930888B2 (en) * 2013-02-01 2018-04-03 Conopco, Inc. Composition
BR112018002983B1 (pt) * 2015-08-20 2021-06-29 Unilever Ip Holdings B.V. Composição compreendendo uma lactama e um álcool
BR112021004540A2 (pt) * 2018-09-14 2021-06-08 Unilever Ip Holdings B.V. composição em mousse e uso de uma combinação de lactama com um álcool

Also Published As

Publication number Publication date
WO2022122265A1 (en) 2022-06-16
CN116648138A (zh) 2023-08-25

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