EP1286589A2 - Zusammensetzung und verfahren zur bioziden behandlung von oberflächen - Google Patents

Zusammensetzung und verfahren zur bioziden behandlung von oberflächen

Info

Publication number
EP1286589A2
EP1286589A2 EP01940669A EP01940669A EP1286589A2 EP 1286589 A2 EP1286589 A2 EP 1286589A2 EP 01940669 A EP01940669 A EP 01940669A EP 01940669 A EP01940669 A EP 01940669A EP 1286589 A2 EP1286589 A2 EP 1286589A2
Authority
EP
European Patent Office
Prior art keywords
weight
composition
water
composition according
biocidal
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.)
Withdrawn
Application number
EP01940669A
Other languages
English (en)
French (fr)
Inventor
Olivier Anthony
Mathieu Joanicot
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.)
Rhodia Chimie SAS
Original Assignee
Rhodia Chimie SAS
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 Rhodia Chimie SAS filed Critical Rhodia Chimie SAS
Publication of EP1286589A2 publication Critical patent/EP1286589A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, 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
    • A01N25/08Biocides, 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 solids as carriers or diluents
    • A01N25/10Macromolecular compounds
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, 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
    • A01N25/30Biocides, 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 characterised by the surfactants
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N33/00Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02Amines; Quaternary ammonium compounds
    • A01N33/12Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/411Aromatic amines, i.e. where the amino group is directly linked to the aromatic nucleus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/737Galactomannans, e.g. guar; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90Block copolymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426Polymers characterized by specific structures/properties characterized by the charge cationic
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/594Mixtures of polymers

Definitions

  • the subject of the present invention is a composition with a delayed or persistent biocidal effect and a process for the biocidal treatment of skin or keratin surfaces, as well as hard industrial, domestic or corporate surfaces.
  • the present invention also relates to a method of using said aqueous biocidal composition for the treatment and disinfection with lasting effect of skin surfaces, as well as hard industrial, domestic or community surfaces, by slow, gradual release of said biocide after application, by contact with the water of the treated surface.
  • Aqueous biocidal compositions for the treatment of hard surfaces generally have the disadvantage of rapidly losing their effectiveness after their application, in particular when the treated surfaces are then washed.
  • film-forming organic polymers in these compositions, in order to form, after application, a physical barrier making it possible to combat the too rapid release of the biocide.
  • An illustration of this technique (WO 97/06675 from Rhône-Poulenc Chemicals Ltd.) consists in associating with a biocide a terephthalic copolyester having in its polymer chain polyoxyethylene or polyoxyethyleneterephthalate units.
  • H has been proposed (WO 99/18784 by Rhodia Chimie) an aqueous system based on a biocide and a polyorganosil ⁇ xane with polyether functions, as well as its use for the disinfection with a lasting effect of hard surfaces by slow release. , progressive of said biocide after application, by contact with the water of the treated surface.
  • the Applicant has found an aqueous biocidal composition of superior performance. Indeed, this composition applied to the surface to be treated and after evaporation of the water has an effective biocidal action, even after several rinses with water of said treated surface.
  • a first subject of the invention consists of a composition with a delayed or persistent biocidal effect comprising: (a) water,
  • At least one water-soluble block copolymer comprising at least one anionic hydrophilic block and at least one nonionic hydrophilic block.
  • a second object of the invention consists of a method of biocidal treatment of skin surfaces, as well as industrial, domestic or community hard surfaces, with a view to imparting to said surfaces a residual biocidal effect even after several washes or rinses, by application on said surfaces an amount with an effective biocidal effect of an aqueous composition with a residual biocidal effect according to the invention, followed by evaporation of the water.
  • This evaporation of the water can take place at ambient temperature, which is the case in particular for detergent compositions for washing clothes by hand, for rinsing the clothes, for personal hygiene compositions and for cleaning and disinfection of hard industrial, domestic or community surfaces.
  • This evaporation can take place at a temperature above room temperature, which is the case for example for laundry treated and dried in a tumble dryer.
  • an effective amount of the biocide is released (released) each time the surface to be treated is rinsed with water.
  • the number of effective rinses can vary between a few units to several tens.
  • There are other methods for applying the composition. One of these methods consists in precipitating the constituents (b), (c) and (d) of the composition on the surface to be treated without evaporating the water, this water then being eliminated by simple flow.
  • Compound (b) can be a cationic surfactant with a biocidal effect.
  • This compound (b) can also be a polymer with a biocidal effect and, in this case, it is not necessary that this polymer also has surfactant properties.
  • Compound (b) can therefore be a chemical product formed from a surfactant part and from another part with a biocidal effect.
  • product (b) we can cite:
  • R represents a C8-C24 alkyl group
  • R and R which are similar or different, represent a C1-C4 alkyl or hydroxyalkyl group
  • X " is a solubilizing anion such as halide (for example chloride, bromide, iodide), sulphate or methyl sulphate;
  • V 2 'R and R similar or different, represent a C8-C24, y 4' alkyl group
  • R and R which are similar or different, represent a C1-C4 alkyl group
  • X ′′ is a solubilizing anion such as halide (for example chloride, bromide, iodide), sulfate or methyl sulfate; - the products of formula:
  • R represents a C8-C24 alkyl group
  • X " is a solubilizing anion such as halide (for example chloride, bromide, iodide), sulphate or methyl sulphate.
  • halide for example chloride, bromide, iodide
  • sulphate or methyl sulphate.
  • heterocyclic monoquaternary amines such as the chlorides of laurylpyridinium, of cetylpyridinium, of C12-C14 alkyl benzyl imidazolium, as well as the salts of fatty alkyl triphenyl phosphonium such as myristyl triphenyl phosphonium bromide.
  • cationic polymer biocides without notable surfactant properties such as those originating from the reaction: epichlorohydrin and dimethylamine or diethylamine 1,3-dichloro-2-propanol epichlorohydrin and imidazole and 1,3-dichloro-2-propanol dimethylamine and 1,3-bis (dimethylamino) -2-propanol of ethylene dichloride and 1,3-bis (dimethyl-amino) -2-propanol - bis (2-chloroethyl) ether and N, N'-bis (dimethylaminopropyl) urea or thiourea
  • a polymer biocide which is more particularly suitable is the product of the reaction of dimethylamine with epichlorohydrin and sold in particular under the name GLOKILL by the company RHODIA. This polymer has units of formula
  • n is an integer whose value gives the polymer a molecular weight by weight of between 1000 and 20,000, generally between 5,000 and 11,000.
  • Compound (c) is a film-forming polymer forming a transparent film after evaporation of the water contained in the composition deposited on the surface to be treated.
  • an anionic guar is obtained by reacting a natural guar with a base and then with a monochloroacetate in order to obtain a carboxymethyl guar.
  • anionic guar can be used in the context of the present invention are marketed under the tradenames GALAXY ® 707D by Aqualon and JAGUAR 800 JAGUAR ® and 8707 ® marketed by Hi-Tek.
  • Compound (d) is a water-soluble block copolymer comprising at least one anionic hydrophilic block and at least one nonionic hydrophilic block. These copolymers have a number-average molecular weight generally between 2,000 and 20,000, preferably between 4,000 and 10,000 g / mole.
  • the anionic blocks include for example polymethacrylic acid and its salts, polyacrylic acid and its salts, copolymers of methacrylic acid and its salts, copolymers of acrylic acid and its salts, heparin, polyphosphate, polyamino acids such as polyaspartic acid, polyglutamic acid, polymalic acid, polylactic acid.
  • the anionic blocks preferred in the context of the present invention are the blocks having in the polymer chain carboxylic groups.
  • Examples of monomers making it possible to prepare such blocks are acrylic acid, aspartic acid, citraconic acid, p-hydroxy cinnamic acid, trans-glutaconic acid, glutamic acid, itaconic acid , linoleic acid, methacrylic acid, maleic acid, oleic acid, maleic anhydride, mesaconic acid, 2-propene 1-sulfonic acid and vinylsulfonic acid.
  • Nonionic blocks include, for example, polyether glycols, in other words polyethylene oxides, propylene polyoxides, copolymers of ethylene oxide and propylene oxide, polysaccharides, polyacrylamides, polyacrylic esters, polymethacrylamide , polyvinyl alcohol, polyvinyl pyrrolidone, polyortho esters, polyamino acids, and polyglycerols.
  • polyether glycols in other words polyethylene oxides, propylene polyoxides, copolymers of ethylene oxide and propylene oxide, polysaccharides, polyacrylamides, polyacrylic esters, polymethacrylamide , polyvinyl alcohol, polyvinyl pyrrolidone, polyortho esters, polyamino acids, and polyglycerols.
  • anionic polymerization with the sequential addition of two monomers as for example described by Scmolka, J. Am. Oil Chem. Soc. 1977, 54, 110; or else Wilczek-
  • Another usable method consists in initiating the polymerization of a polymer block at each of the ends of another polymer block as for example described by Katayose and Kataoka, Proc . Intern. Symp. Control. Rel. Bioact. Materials, 1996, 23, 899.
  • this type of polymerization more particularly recommended are the block copolymers which can be obtained by any process of so-called living or controlled polymerization such as, for example:
  • ATRP - radical polymerization by atom transfer
  • composition according to the invention can also optionally comprise a nonionic surfactant (e).
  • nonionic surfactant e
  • compound (b) which can be used in the compositions according to the present invention, mention may also be made of: - polyoxyalkylenated (polyoxyethylenated, polyoxypropylenated, polyoxybutylenated) alkylphenols in which the alkyl substituent is C 6 -C 12 and containing from 5 to 25 oxyalkylene units; by way of example, mention may be made of the Triton X-45, X-114, X-100 or X-102 sold by Rohm & Haas Cy. ;
  • TERGITOL 15-S-9 TERGITOL 24-L-6 NMW sold by Union Carbide Corp.
  • NEODOL 45-9 NEODOL 23-65, NEODOL 45-7, NEODOL 45-4 marketed by Shell Chemical Cy.
  • RHODASURF IDO60 RHODASURF LA90, RHODASURF IT070 marketed by the company RHODIA.
  • amine oxides such as C10-8 dimethylamine alkyl oxides, C8-C22 alkoxy ethyl dihydroxy ethylamine oxides;
  • compositions according to the invention are in the form of a monophasic aqueous solution of all of its constituents, which is a desirable property and difficult to obtain for compositions of this type.
  • the Applicant is of the opinion that the compound (b) and the compound (a) combine in aggregates or micelles whose size is of the order of a few tens of nanometers.
  • the core of the aggregate would be formed of a coalescat of the anionic part (d) with the compound (b).
  • These aggregates have a sufficient size to remain trapped in the film-forming polymer network (c) after application of the solution and evaporation of the water.
  • the particulate structure of this coalescat ensures a slow and appropriate release of the biocide during rinsing.
  • the compositions according to the present invention comprise: (a) 100 parts by weight of water,
  • compositions according to the present invention comprise: (a) 100 parts by weight of water,
  • biocidal surfactant used depends on the desired application (personal hygiene, disinfection of various hard surfaces).
  • biocidal agent (b) The quantity of biocidal agent (b) to be used depends on the field of application for which the method of the invention is implemented.
  • the amount of biocide (b) used is generally of the order of 0.05 to 0.3% to comply with the legislation in force.
  • biocidal composition used to carry out the process of the invention may be of different type, depending on the field of application for which the process of the invention is implemented.
  • It may be a body hygiene composition for the hair or the skin, in particular in the form of shampoos, lotions, shower gels, for the hair or the body, liquid soaps for the face or the body. .
  • biocidal compositions for the treatment of hard surfaces can also comprise additives such as chelating agents such as aminocarboxylates (ethylenediaminetetraacetates, nitrilotriacetates, N, N-bis (carboxymethyl) glutamates, citrates), alcohols (ethanol, isopropanol, glycols ), detergency builders (phosphates, silicates), surfactants, colorants, perfumes or the like.
  • chelating agents such as aminocarboxylates (ethylenediaminetetraacetates, nitrilotriacetates, N, N-bis (carboxymethyl) glutamates, citrates), alcohols (ethanol, isopropanol, glycols ), detergency builders (phosphates, silicates), surfactants, colorants, perfumes or the like.
  • Hair and skin hygiene compositions may also contain surfactants, humectants, emollients, viscosifiers or gelling agents, sequestering agents, conditioning agents, colorants, perfumes or the like.
  • Said biocidal treatment process for the surfaces which are the subject of the invention can be used to carry out the treatment of keratinous or cutaneous body surfaces, of various hard surfaces, such as tiles, floors, walls, work surfaces, equipment. , furniture, instruments, ... in industry, the food industry, domestic areas (kitchens, bathrooms, sanitary ...) and communities.
  • hard surfaces which can be treated, mention may in particular be made of ceramic, porcelain, glass, polyvinyl chloride, formica or other hard organic polymer, stainless steel, aluminum, wood, etc.
  • the disinfection operation consists in applying or bringing into contact said aqueous biocidal composition, optionally diluted from 1 to 1000 times, preferably from 1 to 100 times, on or with the surface to be treated, then allowing the water to evaporate. .
  • Gram negative bacteria such as: Pseudomonas aeruginosa; Escherichia coli; Proteus mirabilis
  • Gram positive bacteria such as: Staphylococcus aureus; Streptococcus faecium .
  • other dangerous bacteria in the diet such as: Salmonella tvphimurium; Listeria monocvto ⁇ enes; Campylobacter jejuni; Yersinia enterocolitica
  • yeasts such as: Saccharomyces cerevisiae; Candida albicans.
  • fungi such as: Aspergillus niger; Fusarium solani; Pencillium chrvsoqenum
  • algae such as: Chlorella saccharophilia; Chlorella emersonii; Chlorella vul ⁇ aris; Chlamydomonas eugametos
  • the hydrolysis of the PAEt-b-PVAc copolymer described in Example 1 is carried out in the synthesis reactor of the diblock polymer used in Example 1, on an equivalent of 400 g of dry matter (i.e. 1045 g of latex at 38 , 25% dry extract).
  • the pH of the latex is adjusted to 8 with a 1N sodium hydroxide solution.
  • the reactor is heated to 60 ° C. and maintained under a stream of nitrogen. With vigorous stirring, 1115 g of 4N sodium hydroxide are added for 1 hour. The system is kept at this temperature for 11 hours.
  • the final dry extract is 16.25%.
  • a sample taken at the end of the reaction is analyzed by 1 H NMR. The analysis confirms the disappearance of the peaks characteristic of the acrylic esters and of the acetate group.
  • the di-block sodium polyacrylate / polyvinyl alcohol copolymer synthesized according to Example 2 is used.
  • the polyvinyl alcohol and sodium polyacrylate blocks respectively contain 184 polyvinyl alcohol monomers and 44 sodium acrylate monomers.
  • the copolymer is then purified in the following manner: a 5% by weight solution of the copolymer in water is precipitated dropwise in a large excess of acetone, then redissolved in water. We do it twice this cycle to obtain a very transparent pale yellow solution.
  • the pH is then adjusted to 10 by adding sodium hydroxide. The number-average molecular mass of this polymer is 20,200.
  • the biocide used is benzyl dodecyl dimethyl ammonium chloride.
  • the isotherm of fixation of benzyl dodecyl dimethyl ammonium chloride on the di-block copolymer sodium polyacrylate / polyvinyl alcohol was determined by potentiometry using an electrode specific to this cationic surfactant. The results obtained are collated in Table 1 below.
  • the electrode is as follows: Ag / AgCI
  • C tot is the concentration total of added surfactant, C, the concentration of free surfactant, not attached to the polym re, and the C s binding sites on the polymer concentration, that is to say the charge concentration.
  • C is determined using a calibration curve previously established in the absence of copolymer. As indicated in table 1, the appearance of a slight turbidity is observed for values of ⁇ close to 1, that is to say when the charges of the fixed surfactants compensate for the charges present on the acrylic acid block of the copolymer di-block.
  • Example 3 For comparison, the procedure of Example 3 is repeated exactly except that the di-block copolymer is replaced by an acid homopolymer acrylic comprising 111 acrylic acid units per polymer chain.
  • the pH was also adjusted to 10 with sodium hydroxide (Table 1).
  • the polymer concentration was adjusted so that the concentration of sodium acrylate units was equal to that used in the experiment carried out with the di-block, that is to say 0.03% by weight.
  • the concentration of critical aggregation (cac), that is to say the minimum concentration above which the fixation of the surfactant on the polymer, of benzyl dodecyl dimethyl ammonium chloride is observed is substantially the same as for the di-block copolymer: approximately 9 ⁇ 10 -4 % by weight.
  • the solution becomes slightly cloudy for a value of ⁇ close to 0.1 and macroscopic precipitation is observed for a value of ⁇ close to 0.8 , these two phenomena do not appear with the di-block.
  • Table 1 Isotherm for fixing benzyl dodecyl dimethyl ammonium chloride on the sodium polyacrylate / polyvinyl alcohol di-block copolymer (diblock copolymer) and on a sodium acrylate homopolymer (PAA).
  • the di-block copolymer and the biocidal cationic surfactant described in Example 3 are again used in a more concentrated formulation.
  • a solution of 1.5% by weight of cationic surfactant and 1% by weight of di-block copolymer is prepared.
  • This complex is completely redissolved by the addition of a total concentration of 5% by weight of nonionic surfactant (RHODASURF DA639, an isododecyl ether hexaoxyethylene glycol sold by the company Rhodia).
  • RHODASURF DA639 an isododecyl ether hexaoxyethylene glycol sold by the company Rhodia.
  • This redissolution shows the co-micellization of the cationic and neutral surfactants on the polymer.
  • the nonionic surfactant provides sufficient hydrophilicity to avoid phase separation.
  • aqueous anionic guar solution is then added (carboxymethyl guar, CMG, of molecular mass 2.3 million and degree of anionic substitution of 0.10).
  • carboxymethyl guar is 0.15%.
  • the addition of this polymer does not induce phase separation in the solution. A single-phase detergent solution is thus obtained.
  • the cationic and nonionic surfactants, as well as the block copolymer and the anionic guar are identical to those of Example 4.
  • the covered surface of the dried film is then sprayed with water using a spray bottle. Each spray projects 1 ml of water onto the surface. The liquid falling from the surface is collected in the beaker, and 2.5 ml is taken from the beaker after each spraying.
  • the benzyl dodecyl dimethyl ammonium chloride concentration is determined by measuring the UV absorbance of the solution sampled at 262.5 nm and by referring to a calibration curve carried out previously. We used for this measurement a Hitachi model U3410 spectrometer.
  • This concentration allows us to calculate the amount of benzyl dodecyl dimethyl ammonium chloride remaining on the tiles despite rinsing.
  • the results are collated in Table 2 below giving the percentage of benzyl dodecyl dimethyl ammonium chloride remaining on the surface of the tiling as a function of the number of rinses.
  • Formula A 1.5% by weight of benzyl dodecyl dimethyl ammonium chloride
  • Formula B 1.5% by weight of benzyl dodecyl dimethyl ammonium chloride
  • Formula C 1.5% by weight of benzyl dodecyl dimethyl ammonium chloride
  • GLOKILL PQ is added, which is a biocidal polymer of quaternary amine positively charged at all pH, product marketed by RHODIA.
  • the structure of the recurring units of this polymer biocide is as follows:
  • n is an integer whose value gives the polymer a molecular weight by weight of between 5,000 and 11,000.
  • the di-block copolymer described in Example 3 is again used and as a cationic agent with a biocidal effect, GLOKILL used in Example 6 above is added.
  • the composition also contains the neutral surfactant and is prepared in the following manner:
  • the nonionic surfactant described in Example 4 (RHODASURF DA639, an isododecyl ether hexaoxyethylene glycol) and GLOKILL are added in order to obtain a solution of 0.6% by weight in di-block , 0.156% by weight in GLOKILL and 5% in nonionic surfactant.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Toxicology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
EP01940669A 2000-06-08 2001-06-01 Zusammensetzung und verfahren zur bioziden behandlung von oberflächen Withdrawn EP1286589A2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US590117 1984-03-16
US59011700A 2000-06-08 2000-06-08
PCT/FR2001/001709 WO2001093810A2 (fr) 2000-06-08 2001-06-01 Composition et procede pour le traitement biocide des surfaces

Publications (1)

Publication Number Publication Date
EP1286589A2 true EP1286589A2 (de) 2003-03-05

Family

ID=24360940

Family Applications (1)

Application Number Title Priority Date Filing Date
EP01940669A Withdrawn EP1286589A2 (de) 2000-06-08 2001-06-01 Zusammensetzung und verfahren zur bioziden behandlung von oberflächen

Country Status (4)

Country Link
US (1) US20030147826A1 (de)
EP (1) EP1286589A2 (de)
AU (1) AU2001274181A1 (de)
WO (1) WO2001093810A2 (de)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030100465A1 (en) * 2000-12-14 2003-05-29 The Clorox Company, A Delaware Corporation Cleaning composition
US7799751B2 (en) * 2000-12-14 2010-09-21 The Clorox Company Cleaning composition
US20030114342A1 (en) * 2001-09-20 2003-06-19 Lonza Inc. Compositions comprising quaternary ammonium compounds and dendritic polymers with antimicrobial activity
DE60233691D1 (de) * 2001-12-12 2009-10-22 Rhodia Chimie Sa Kosmetische Zusammensetzung mit einem Blockcopolymer
DE60231742D1 (de) 2001-12-12 2009-05-07 Rhodia Chimie Sa Formulierung enthaltend eine anionische verbindung, ein polyionisches polymer und ein copolymer
FR2864895A1 (fr) * 2004-01-13 2005-07-15 Oreal Composition de revetement des fibres keratiniques comprenant un polymere sequence, un polymere cationique et un polymere anionique
FR2889531B1 (fr) * 2005-08-05 2008-12-19 Rhodia Chimie Sa Composion comprenantun extrait de guar et utilisation d'un extrait de guar comme agent de traitement et/ou de modification de surfaces
FR2889530B1 (fr) * 2005-08-05 2008-02-01 Rhodia Chimie Sa Produit issu d'un extrait proteinique de guar, procede de preparation et utilisations
DE102007002073A1 (de) * 2007-01-09 2008-07-10 Matthias Habenicht Mittel zur Pflege und antimikrobiellen Behandlung der Haut
US9474269B2 (en) 2010-03-29 2016-10-25 The Clorox Company Aqueous compositions comprising associative polyelectrolyte complexes (PEC)
US9309435B2 (en) 2010-03-29 2016-04-12 The Clorox Company Precursor polyelectrolyte complexes compositions comprising oxidants
US20110236582A1 (en) 2010-03-29 2011-09-29 Scheuing David R Polyelectrolyte Complexes
CA2835211C (en) 2011-05-10 2019-09-24 Next Science, Llc Antimicrobial solid and methods of making and using same
AU2015261645B2 (en) * 2011-05-10 2017-10-19 Next Science IP Holdings Pty Ltd Antimicrobial solid and methods of making and using same
AU2014343368B2 (en) 2013-10-31 2018-03-08 Specialty Operations France Hydrophilization polymers and methods for use
US8975220B1 (en) 2014-08-11 2015-03-10 The Clorox Company Hypohalite compositions comprising a cationic polymer
CN106279680A (zh) * 2016-08-12 2017-01-04 贯硕磉 季铵盐阳离子表面活性剂及其制备方法
US11116220B2 (en) 2017-12-22 2021-09-14 Ecolab Usa Inc. Antimicrobial compositions with enhanced efficacy

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2931753A (en) * 1953-11-18 1960-04-05 Erskine Organic ammonium salts of polysaccharide carboxylic acids
US5158766A (en) * 1989-04-13 1992-10-27 Ecolab, Inc. Storage stable aqueous soluble germicidal film forming composition
GB2304286B (en) * 1995-08-18 1999-09-29 Rhone Poulenc Chemicals Biocidal hard surface treatment
EP1094706A1 (de) * 1998-07-09 2001-05-02 Rhodia Chimie Verfahren zur biozide behandlung von oberflächen
US6262152B1 (en) * 1998-10-06 2001-07-17 E. I. Du Pont De Nemours And Company Particles dispersed w/polymer dispersant having liquid soluble and cross-linkable insoluble segments

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0193810A2 *

Also Published As

Publication number Publication date
US20030147826A1 (en) 2003-08-07
AU2001274181A1 (en) 2001-12-17
WO2001093810A3 (fr) 2002-03-21
WO2001093810A2 (fr) 2001-12-13

Similar Documents

Publication Publication Date Title
WO2001093810A2 (fr) Composition et procede pour le traitement biocide des surfaces
EP1558658B1 (de) Copolymer mit kontrollierter struktur mit einem amphoteren oder zwitterionischen teil
EP2215134B1 (de) Verminderung der biofilmbildung durch multifunktionelle copolymere
EP3545066B1 (de) Copolymer enthaltende reinigungsmittelzusammensetzungen
CN114423405B (zh) 包含去头皮屑剂的个人护理组合物
FR2797381A1 (fr) Utilisation d'un polymere hydrosoluble dans une composition biocide pour le traitement des surfaces dures
EP1456502B1 (de) Verwendung von gefüllten amphiphilen statistischen polymeren zum eindicken von riesenmizellen enthaltenden phasen und wässrige zusammensetzung davon
EP0494022B1 (de) Copolymere auf Basis von N-Alkylacrylamid, deren Herstellung und deren Verwendung als Verdickungsmittel in Shampoozusammensetzungen
EP1196523A1 (de) Ein wasserlösliches oder wasserdispergierbares polymer enthaltendes reinigungsmittel
WO2007068744A1 (fr) Copolymere comprenant des unites zwitterioniques et d'autres unites, composition comprenant le copolymere, et utilisation
FR2887450A1 (fr) Ingredient concentre pour le traitement et/ou la modification de surfaces, et son utilisation dans des compositions cosmetiques
FR3024736A1 (fr) Utilisation dans des compositions detergentes de polymeres obtenus par polymerisation en emulsion inverse basse concentration avec un faible taux de monomeres neutralises
EP3545011B1 (de) Copolymere und deren verwendung in reinigungsmittel-zusammensetzungen
EP1151068A1 (de) Verwendung von filmbildenden titandioxiddispersionen zur reinigung und desinfektion von oberflächen, filmbildenden titandioxiddispersionen
WO2017189589A1 (en) An antimicrobial composition, process for preparing the same and method of use thereof
EP1922331B1 (de) Guar extract zur behandlung von oberflächen
EP3545012A1 (de) Copolymere und deren verwendung in reinigungsmittel-zusammensetzungen
EP1667637A2 (de) Wässrige zusammensetzung mit einem polyionischen dendritischen polymer und einem ionischen tensid
DE102007058343A1 (de) Verminderung der Adhäsion von Schmutz, Staub und biologischem Material durch Polyesteramide
JP2003300820A (ja) アニオン性界面活性剤とカチオン性ポリマーと両親媒性分岐ブロックアクリルコポリマーとを含有する化粧品組成物及びそれを用いた毛髪処理方法
CN107847416B (zh) 分散的内酰胺
WO2020074826A1 (fr) Composition désinfectante a usage topique
EP4057985A1 (de) Reinigungsmittelzusammensetzung
EP3946637A1 (de) Kosmetische zusammensetzung für das haar
FR2859209A1 (fr) Copolymere a structure controlee presentant une partie amphotere ou zwitterionique

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20021209

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

AX Request for extension of the european patent

Extension state: AL LT LV MK RO SI

17Q First examination report despatched

Effective date: 20031211

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20040422