WO2023094383A1 - Composition de soin buccal comprenant un matériau composite bipolaire - Google Patents

Composition de soin buccal comprenant un matériau composite bipolaire Download PDF

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Publication number
WO2023094383A1
WO2023094383A1 PCT/EP2022/082819 EP2022082819W WO2023094383A1 WO 2023094383 A1 WO2023094383 A1 WO 2023094383A1 EP 2022082819 W EP2022082819 W EP 2022082819W WO 2023094383 A1 WO2023094383 A1 WO 2023094383A1
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WO
WIPO (PCT)
Prior art keywords
clay
chloride
composition
external surface
octahedral
Prior art date
Application number
PCT/EP2022/082819
Other languages
English (en)
Inventor
Sembian CHANDRASEKARAN
Alison Katharine Green
Madalasa Srivastava
Original Assignee
Unilever Ip Holdings B.V.
Unilever Global Ip Limited
Conopco, Inc., D/B/A Unilever
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 Ip Holdings B.V., Unilever Global Ip Limited, Conopco, Inc., D/B/A Unilever filed Critical Unilever Ip Holdings B.V.
Publication of WO2023094383A1 publication Critical patent/WO2023094383A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4425—Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6921—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere
    • A61K47/6923—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit the form being a particulate, a powder, an adsorbate, a bead or a sphere the form being an inorganic particle, e.g. ceramic particles, silica particles, ferrite or synsorb
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26—Aluminium; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/58—Metal complex; Coordination compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals

Definitions

  • the present invention is concerned with oral care compositions.
  • the benefit associated with oral care products are many including prevention and treatment of gingivitis, tooth whitening, breath freshness mitigation of tooth decay and mitigation of tooth sensitivity.
  • W014102032A1 discloses a composite bipolar material is highly effective at controlling re-growth of bacteria, as well as at providing immediate control on the bacterial count.
  • the present invention has found that certain oral care compositions can be effective in the for use in the reduction of transmission of SARS-CoV-2 (covid 19).
  • the present invention relates to a bipolar composite material comprising:
  • a clay whose precursor is an asymmetric 1 :1 or 2:1 : 1 clay particle comprising alternating tetrahedral and octahedral sheets terminating with a tetrahedral sheet at one external surface plane and an octahedral sheet at another;
  • antimicrobial quaternary ammonium compound attached to a coordinating cation on one of the external surface planes, in a composition for use in the reduction of transmission of SARS-CoV-2 (covid 19).
  • the invention also relates to the use of a bipolar composite material in the reduction of transmission of SARS-CoV-2 (covid 19) in which the bipolar material comprises:
  • a clay whose precursor is an asymmetric 1 :1 or 2:1 : 1 clay particle comprising alternating tetrahedral and octahedral sheets terminating with a tetrahedral sheet at one external surface plane and an octahedral sheet at another;
  • the invention further relates to the use of a polar composite material comprising:
  • a clay whose precursor is an asymmetric 1 :1 or 2:1 : 1 clay particle comprising alternating tetrahedral and octahedral sheets terminating with a tetrahedral sheet at one external surface plane and an octahedral sheet at another;
  • Water-insoluble refers to the solubility of a material in water at 25°C and atmospheric pressure being 0.1 % by weight or less.
  • transmission incudes infecting others with human coronavirus SARS-CoV-2 (covid 19) and becoming infected yourself with the virus.
  • median particle size (D50) of the polar composite material is 0.1 to 10 pm, more preferably 0.4 to 1 pm and most preferably 0.5 to 0.8 pm.
  • Particle size distribution (D50) is also known as the median diameter or the medium value of the particle size distribution, it is the value of the particle diameter at 50 percent in the cumulative distribution. For example, if D50 is 5.8 pm, then 50 % of the particles in the sample are larger than 5.8 pm and 50 percent smaller than 5.8 pm.
  • D50 is usually used to represent the particle size of group of particles. The D50 is the size in microns that splits the distribution with half above and half below this diameter.
  • the precursor of the clay is an asymmetric 1 :1 clay particle.
  • Preferred 1:1 clays include kaolinite and serpentine subgroups of minerals.
  • the species included within the kaolinite subgroup include but are not limited to kaolinite, dickite, halloysite and nacrite.
  • the species within the serpentine subgroup include but are not limited to chrysolite, lizardite, and amesite.
  • the precursor of the clay is an asymmetric 2:1 :1 clay particle.
  • Preferred 2:1 :1 clays include chlorite group of minerals.
  • the chlorite comprises tetrahedral- octahedral-tetrahedral sheets like 2:1 clays, with an extra weakly bound brucite like layer between tetrahedral layers.
  • the tetrahedral sheet preferably comprises coordinating tetrahedral cations of silicon.
  • the tetrahedral sheet may also include isomorphously substituted coordinating tetrahedral cations which are not silicon. Isomorphously substituted coordinating tetrahedral cations include, but are not limited to, cations of aluminum, iron or boron.
  • the octahedral sheet has coordinating octahedral cations of aluminum.
  • the octahedral sheet may also comprise isomorphously substituted coordinating octahedral cations which are not aluminium.
  • Isomorphously substituted coordinating octahedral cations include cations of magnesium and iron.
  • the antimicrobial agent is attached to the coordinating cations on the exterior side of one of the external surface planes. Accordingly, the cationic quaternary compound is attached to coordinating cations on the exterior side of the tetrahedral sheet.
  • the cationic quaternary compound is attached to the coordinating cations on the exterior side of the octahedral sheet.
  • Coordinating cations on the exterior side of each of the tetrahedral and the octahedral surface sheets are attached to the cationic quaternary compound, with the proviso that the cationic quaternary compound attached to the coordinating cations on the exterior side of the tetrahedral surface sheet is not identical to the molecule attached to the coordinating cations on the exterior side of the octahedral surface sheet.
  • the cationic quaternary compound is preferably attached to the coordinating cations on the external surface of the octahedral surface plane and is not preferably attached to coordination cations of non-exterior tetrahedral or octahedral plane or on the interior side of the surface sheets.
  • the ratio of the clay: quaternary ammonium compound is from 1 :0.001 to 1 : 1 , more preferably from 1 :0.001 and 1:0.1 parts by weight of the bipolar composite material.
  • the antibacterial quaternary ammonium compound is attached to coordinating cations on the external surface of the octahedral surface plane. It is preferred that oral care compositions of the invention comprise 0.1 to 10 wt% of the bipolar antimicrobial material of the total composition, more preferably 0.2 to 5 wt%, most preferably 0.5 to 3 wt%
  • the quaternary ammonium compound is one or more of cetylpyridinium chloride (CPC), cetyltrimethylammonium chloride (CTAC), cetyltrimethylammonium bromide (CTAB), benzalkonium chloride (BKC), benzethonium chloride, cetrimide, quatemium, tetrabutyl ammonium bromide, undecylenamido propyltrimonium methosulphate, methylbenzethonium chloride, cetethyldimonium bromide, cetromonium tosylate, cocotrimonium chloride, dodecylbenzyltrimonium chloride, lauryl isoquinolium bromide, laurylpyridinium chloride, dequalinium chloride or domiphen bromide.
  • CPC cetylpyridinium chloride
  • CTC cetyltrimethylammonium chloride
  • CTAB cetyltrimethylammonium bromide
  • precursor of the clay is a 1 : 1 clay particle. Further preferably the precursor of the clay is kaolinite. It is particularly preferred that the antimicrobial quaternary ammonium compound is cetyl pyridinium chloride (CPC). It is further particularly preferred that when the precursor of the clay is kaolinite, the antimicrobial quaternary ammonium compound is cetyl pyridinium chloride (CPC).
  • composition of the invention is preferably used to clean the surfaces of the oral cavity and is known as an oral care composition.
  • compositions of the invention are preferred, particularly preferred product forms for compositions of the invention are those which are suitable for brushing and/or rinsing the surfaces of the oral cavity.
  • the composition of the invention is most preferably in the form of a toothpaste.
  • teethpaste denotes an oral composition which is used to clean the surfaces of the oral cavity. Such a composition is not intentionally swallowed for purposes of systemic administration of therapeutic agents, but is applied to the oral cavity, used to treat the oral cavity and then expectorated. Typically such a composition is used in conjunction with a cleaning implement such as a toothbrush, usually by applying it to the bristles of the toothbrush and then brushing the accessible surfaces of the oral cavity.
  • the toothpaste is in the form of an extrudable semi-solid such as a cream, paste or gel (or mixture thereof).
  • a composition according to the invention (such as a dentifrice/toothpaste) will generally contain further ingredients to enhance performance and/or consumer acceptability.
  • compositions according to the invention preferably comprise particulate abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, calcium pyrophosphates, hydroxyapatites, trimetaphosphates, insoluble hexametaphosphates and so on, including agglomerated particulate abrasive materials, usually in amounts between 10 and 60% by weight of the oral care composition.
  • abrasive materials such as silicas, aluminas, calcium carbonates, dicalciumphosphates, calcium pyrophosphates, hydroxyapatites, trimetaphosphates, insoluble hexametaphosphates and so on, including agglomerated particulate abrasive materials, usually in amounts between 10 and 60% by weight of the oral care composition.
  • the composition comprises from 20 to 50 wt% and most preferably 45 to 55 wt% abrasive which may be silica based or calcium based.
  • Preferred toothpaste compositions have 25 to 60 wt% abrasive.
  • Preferred toothpaste compositions will have calcium containing abrasive.
  • a particularly preferred abrasive is fine ground natural chalk (FGNC). It is obtained from limestone or marble.
  • FGNC may also be modified chemically or physically by coating during or after milling by heat treatment. Typical coating materials include magnesium stearate and oleate.
  • the morphology of FGNC may also be modified during the milling process by using different milling techniques, for example, ball milling, airclassifier milling or spiral jet milling.
  • FGNC can be used as the sole calcium containing abrasive. However, FGNC can also be used with other calcium containing abrasives to balance the abrasion.
  • DCP dicalcium phosphate
  • PCC precipitated calcium carbonate
  • FGNC is 35 to 100 %, more preferably 75 to 100 % and especially from 95 to 100 % of the total abrasive.
  • the balance most preferably, is PCC.
  • abrasive silicas used are those with a low refractive index.
  • suitable low refractive index abrasive silicas e.g. having an R.l. of between 1.435 and 1.445
  • Tixosil 63 and 73 ex Rhone Poulenc Tixosil 63 and 73 ex Rhone Poulenc; Sident 10 ex Degussa; Zeodent 113 ex Zeofinn; Zeodent 124 ex Huber, Sorbosil AC 77 ex Crosfield Chemicals (having an R.l. of approximately 1.440).
  • the amount of these silicas in the composition generally ranges from 5-60% by weight, usually 5-20% by weight.
  • composition particularly if a toothpaste preferably comprises an inorganic or a natural or synthetic thickener or gelling agent in proportions of about 0.10 to about 15% by weight depending on the material chosen.
  • thickeners in the dentifrice compositions of the present invention form an extrudable, shape-retaining product which can be squeezed from a tube onto a toothbrush and will not fall between the bristles of the brush but rather, will substantially maintain its shape thereon.
  • Suitable thickeners or gelling agents useful in the practice of the present invention include inorganic thickening silicas such as amorphous silicas available from Huber Corporation under the trade designation Zeodent 165, Irish moss, iota-carrageenan, gum tragacanth, and polyvinylpyrrolidone.
  • inorganic thickening silicas such as amorphous silicas available from Huber Corporation under the trade designation Zeodent 165, Irish moss, iota-carrageenan, gum tragacanth, and polyvinylpyrrolidone.
  • compositions according to the invention preferably comprise a polymeric deposition aid.
  • the composition comprises acid anhydride polymers, particularly preferred are co-polymers of maleic anhydride with methyl vinylether, in which the anhydride moiety may be in a partially or fully hydrolysed or alcoholysed form.
  • Preferred copolymers include Gantrez(R) polymers such as: Gantrez S-95: molecular weight 216,000; free acid;
  • Gantrez S-96 molecular weight 700,000; free acid
  • Gantrez S-97 molecular weight 1 ,500,000; free acid
  • Gantrez MS-955 molecular weight 1,060,000; calcium/sodium salt.
  • Particularly preferred co-polymers of maleic acid and methyl vinylether have a molecular weight of 1 ,000,000 or greater and an especially preferred material is Gantrez S-97.
  • compositions according to the invention may comprise a tooth whitening agent.
  • the whitening agent preferably comprises a green and/or a blue pigment.
  • a pigment is generally understood to be a shade/material which is insoluble in the relevant medium, at the relevant temperature. This is in contrast to dyes which are soluble.
  • the "relevant medium” is human saliva, the liquid medium in which the composition is used, at the temperature of the oral cavity during brushing of the teeth, i.e. up to 37 Degrees C. As a reasonable approximation, the relevant medium may be considered to be water and the relevant temperature to be 25 Degrees C.
  • the blue pigment is Pigment Blue 15, more preferably Pigment Blue 15:1 , 15:2, 15:3, 15:4, 15:5 or 15:6, most preferably 15:1.
  • a preferred pigment is blue pigment is Phthalocyanine Blue Pigment, Cl No. 74160, blue covarine.
  • the preferred Green pigment is Phthalocyanine Green, preferably Phthalocyanine Green CI-74260.
  • the total level of pigment in the composition is from 0.01 wt% to 3 wt, more preferably from 0.02 to 2 wt%.
  • composition is a toothpaste it may be a dual phase paste, with the whitening pigments present in one phase.
  • Compositions according to the invention may comprise water-soluble or sparingly water-soluble sources of metal salts, preferred are zinc ions such as zinc chloride, zinc acetate, zinc gluconate, zinc sulphate, zinc fluoride, zinc citrate, zinc lactate, zinc oxide, zinc monoglycerolate, zinc tartrate, zinc pyrophosphate and zinc maleate; also preferred are stannous ions such as stannous fluoride and stannous chloride.
  • zinc ions such as zinc chloride, zinc acetate, zinc gluconate, zinc sulphate, zinc fluoride, zinc citrate, zinc lactate, zinc oxide, zinc monoglycerolate, zinc tartrate, zinc pyrophosphate and zinc maleate
  • stannous ions such as stannous fluoride and stannous chloride.
  • Compositions of the invention may comprise fluoride sources such as sodium fluoride, stannous fluoride, sodium monofluorophosphate, zinc ammonium fluoride, tin ammonium fluoride, calcium fluoride, cobalt ammonium fluoride and mixtures thereof.
  • fluoride sources such as sodium fluoride, stannous fluoride, sodium monofluorophosphate, zinc ammonium fluoride, tin ammonium fluoride, calcium fluoride, cobalt ammonium fluoride and mixtures thereof.
  • composition according the invention will comprise further ingredients which are common in the art, such as: antimicrobial agents, e.g. chlorhexidine, sanguinarine extract, metronidazole, quaternary ammonium compounds, such as cetylpyridinium chloride; bis-guanides, such as chlorhexidine digluconate, hexetidine, octenidine, alexidine; and halogenated bisphenolic compounds, such as 2,2' methylenebis-(4-chloro-6-bromophenol); anti-inflammatory agents such as ibuprofen, flurbiprofen, aspirin, indomethacin etc.; anti-caries agents such as sodium- and stannous fluoride, aminefluorides, sodium monofluorophosphate, sodium trimeta phosphate and casein; plaque buffers such as urea, calcium lactate, calcium glycerophosphate and strontium polyacrylates; vitamins such as Vitamins A, C and E; plant extracts; plant-
  • surfactants such as anionic, nonionic, cationic and zwitterionic or amphoteric surfactants
  • humectants such as glycerol, sorbitol, propyleneglycol, xylitol, lactitol etc.
  • oral care enzyme systems such as hydrogen peroxide producing enzyme systems (e.g.
  • bleaching agents such as peroxy compounds e.g. potassium peroxydiphosphate, effervescing systems such as sodium bicarbonate/c

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Inorganic Chemistry (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Ceramic Engineering (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un matériau composite bipolaire comprenant : (i) une argile dont le précurseur est une particule d'argile 1 : 1 ou 2 : 1 : 1 asymétrique, comprenant des feuilles tétraédriques et octaédriques alternées se terminant par une feuille tétraédrique au niveau d'un plan de surface externe et une feuille octaédrique au niveau d'un autre ; et, (ii) un composé d'ammonium quaternaire antimicrobien fixé à un cation de coordination sur l'un desdits plans de surface externe, dans une composition destinée à être utilisée pour réduire la transmission du SARS-CoV-2 (Covid-19).
PCT/EP2022/082819 2021-11-26 2022-11-22 Composition de soin buccal comprenant un matériau composite bipolaire WO2023094383A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP21210760 2021-11-26
EP21210760.1 2021-11-26

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Publication Number Publication Date
WO2023094383A1 true WO2023094383A1 (fr) 2023-06-01

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117138610A (zh) * 2023-10-27 2023-12-01 成都理工大学 一种抑制碳酸盐岩中粘土溶解的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005046738A2 (fr) * 2003-11-07 2005-05-26 Viratox, L.L.C. Activites virocides du chlorure de cetylpyridinium
WO2007093808A2 (fr) * 2006-02-16 2007-08-23 Queen Mary & Westfield College Substances virucides
WO2014102032A1 (fr) 2012-12-27 2014-07-03 Unilever N.V. Composition de soin buccal comportant un adduit d'argile et un agent antibactérien

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005046738A2 (fr) * 2003-11-07 2005-05-26 Viratox, L.L.C. Activites virocides du chlorure de cetylpyridinium
WO2007093808A2 (fr) * 2006-02-16 2007-08-23 Queen Mary & Westfield College Substances virucides
WO2014102032A1 (fr) 2012-12-27 2014-07-03 Unilever N.V. Composition de soin buccal comportant un adduit d'argile et un agent antibactérien

Non-Patent Citations (1)

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Title
CIEJKA JUSTYNA ET AL: "Biopolymeric nano/microspheres for selective and reversible adsorption of coronaviruses", MATERIALS SCIENCE AND ENGINEERING C, ELSEVIER SCIENCE S.A, CH, vol. 76, 6 March 2017 (2017-03-06), pages 735 - 742, XP029995402, ISSN: 0928-4931, DOI: 10.1016/J.MSEC.2017.03.047 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117138610A (zh) * 2023-10-27 2023-12-01 成都理工大学 一种抑制碳酸盐岩中粘土溶解的方法
CN117138610B (zh) * 2023-10-27 2024-01-09 成都理工大学 一种抑制碳酸盐岩中粘土溶解的方法

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