EP2470156A2 - Utilisation de 1,3-diols comme biocides - Google Patents

Utilisation de 1,3-diols comme biocides

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Publication number
EP2470156A2
EP2470156A2 EP10742169A EP10742169A EP2470156A2 EP 2470156 A2 EP2470156 A2 EP 2470156A2 EP 10742169 A EP10742169 A EP 10742169A EP 10742169 A EP10742169 A EP 10742169A EP 2470156 A2 EP2470156 A2 EP 2470156A2
Authority
EP
European Patent Office
Prior art keywords
biozid
diol
diols
propane
use according
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Withdrawn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
EP10742169A
Other languages
German (de)
English (en)
Inventor
Darijo Mijolovic
Volker Wendel
Anja Suckert
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP10742169A priority Critical patent/EP2470156A2/fr
Publication of EP2470156A2 publication Critical patent/EP2470156A2/fr
Withdrawn legal-status Critical Current

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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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • 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
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/345—Alcohols containing more than one hydroxy group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61P31/02—Local antiseptics
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2048—Dihydric alcohols branched
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2041—Dihydric alcohols
    • C11D3/2051—Dihydric alcohols cyclic; polycyclic
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87—Application Devices; Containers; Packaging
    • A61K2800/874—Roll-on
    • 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
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the use of 1,3-diols as biocides relates to a use of a diol as a biocidal active ingredient, which is characterized in that the diol is one of the formula I. in which R 1 and R 2 independently of one another are an organic radical each having at least one C atom or R 1 and R 2 together form a ring system of at least 4 C atoms, which may optionally be substituted (in the following summary short 1, 3-diol called).
  • Biocidal agents kill microorganisms such as bacteria, fungi, yeasts, algae or viruses or at least prevent their reproduction and / or growth.
  • substrates there is the desire or often the need for biocidal equipment. It is e.g. substrates for medical applications, applications in the sanitary or hygiene sector, in the food sector, in particular in food packaging, or substrates for a variety of industrial applications, in particular filters, e.g. for air conditioners.
  • Biocides are also used as preservatives. Of particular importance here is the use as a preservative for liquid preparations, which are used for medical, hygienic, cosmetic or dermatological purposes.
  • Biocidal effects were found with different chemical compounds. In connection with alcohols, it is known that 1, 2-alkanediols have a good biocidal activity, as also by Gerhard Schmaus, Antje Pfeiffer, Sabine Lange and Aurelie Trunet in Cosmetics & Toiletries, VoI 123, No 10, October 2008, page 53 bis 64 will be described. For the manifold uses of biocidal active ingredients, alternative solutions are constantly being sought.
  • Object of the present invention were therefore biocidal agents that have a good biocidal activity against as many microorganisms, are easy to handle and can be used in many ways.
  • the diol used according to the invention is a diol of the formula I.
  • Diols of the formula I are also referred to below as 1, 3-diol or 1, 3-diols.
  • R 1 and R 2 independently of one another represent an organic radical having in each case at least one carbon atom (alternative 1), moreover, R 1 and R 2 may together form a ring system of at least 4 carbon atoms, which may optionally be substituted (2 Alternative).
  • R 1 and R 2 independently of one another are a hydrocarbon radical having 1 to 12 C atoms. These may be aliphatic, cycloaliphatic or aromatic hydrocarbon radicals. Suitable aliphatic hydrocarbon radicals are, in particular, alkyl groups; the cycloaliphatic hydrocarbon radical is e.g. the cyclohexyl group and, as the aromatic hydrocarbon radical, in particular the phenyl group.
  • R1 and R2 independently of one another being a C1 to C12-alkyl group, particularly preferably a C1-C10-alkyl group.
  • the two alkyl groups can be independently linear or branched.
  • the sum of the C atoms in R1 and R2 is preferably not more than 16, in particular not more than 12.
  • R1 and R2 together form a cycloaliphatic ring system.
  • the ring system may be replaced by other organic groups, e.g. Alkyl groups substituted. Particularly preferred is an unsubstituted cycloaliphatic ring system.
  • the cycloaliphatic ring system may optionally also contain one or two double bonds.
  • the ring system preferably consists of at most 12 C atoms (sum of all C atoms in R1 and R2, including the C atom to which R1 and R2 are bonded).
  • DMCP 1, 1-Dimethylolcyclopentane
  • DMCD 1, 1-dimethylolcyclododecane
  • PPPD and MBPPD are e.g. also described in PCT / EP 2009/057133 (PF 60933); By a preferred method of preparation described therein mixtures of PPPD and MPPPD are obtained which can be used in the context of this invention.
  • mixtures of the above diols are also suitable for the use according to the invention.
  • the above 1,3-diols can also be used in combination with other biocides (see Table 1).
  • the compounds described in this invention show significant anti-microbial activity, e.g. against Gram-positive and Gram-negative bacteria, against yeasts and molds. They are therefore suitable for the disinfection of a wide variety of surfaces and objects, for the deodorization of surfaces and objects and various body regions as well as for the general antimicrobial treatment of skin and mucous membranes, technical materials.
  • the 1, 3-diols are suitable for the biocidal finishing of moldings.
  • the 1, 3-diols can be applied as such or in the form of a liquid preparation on the moldings.
  • Suitable liquid preparations are solutions or emulsions of the 1,3-diols in a solvent.
  • Suitable solvents are water or organic solvents, for. As alcohols and ethers.
  • the liquid preparations may contain further biocides or other additives, as also described by R. Gumbleter, H. Müller in Taschenbuch der Kunststoffadditive, 3rd edition, 1990, ISBN 3-446-15627-5. Further biocides are in particular in chap. 15 "Biostabilizers", 823 et seq.
  • Biocide-finished molded articles can be obtained by coating, impregnating or otherwise treating the desired shaped articles with the 1,3-diol or its solution or emulsion.
  • the treatment with the solution or emulsion can be carried out at room temperature, after drying, the shaped body is equipped according to biocidal.
  • the amount of 1,3-diol may be e.g. 0.001 to 1000 mg, more preferably 0.1 to 10 mg of 1, 3-diol per square meter surface area of the molding to be equipped with the biocide.
  • molded body is understood to mean here any objects which, in contrast to liquids or gases, are present in a defined form.
  • textiles made of natural or synthetic materials These materials may be colored or undyed or printed and e.g. made of silk, wool, polyamides, polyurethanes or cellulose fibers of any kind. Such fibers are e.g. Cotton, linen, jute or hemp.
  • non-woven materials such as e.g. Diapers, sanitary napkins or garments for medical, hygiene or household uses can be antimicrobially equipped with diols for the purposes of the invention.
  • the antimicrobial substances of this invention may also be used for the treatment, especially the antimicrobial finish, or the preservation of plastic moldings, e.g. As films or containers made of plastic, other plastic packaging, paper, cardboard, molded metal or molded body of combinations of different materials. Examples include floor coatings, plastic coatings, plastic containers and packaging materials, kitchen and bath utensils, plastic articles in medical applications such as nutritional material, syringes, catheters or dog shoes, for sanitary and sanitary applications, food packaging or industrial use , z. B. filters in air conditioners.
  • the moldings equipped with the 1, 3-diol are, in particular, moldings for medical applications, for sanitary and hygienic applications. for packaging or storage of foodstuffs or for industrial purposes, eg. B. filters in air conditioners.
  • the 1, 3-diols are also suitable as preservatives in liquid preparations, in gaseous preparations, sprays, foams or gels.
  • the antimicrobial substances of this invention may also be used for the treatment, especially the antimicrobial finish, or the preservation of industrial formulations, e.g. Paints, varnishes or coatings.
  • the antimicrobial formulation is a coating, it may be in the form of a liquid, solution or suspension, paste, gel or oil or in solid form, e.g. as a powder, which is subsequently cured by irradiation with UV light, heat or other methods.
  • paper used for sanitary purposes may be equipped with the antimicrobial properties of this invention.
  • the antimicrobial substances of this invention may also be used in washing or cleaning formulations, e.g. Liquid or powder detergents or softeners.
  • the substances of this invention can be used.
  • the diols of this invention may also be used for the antimicrobial treatment of wood or leather or for the preservation of leather or for the antimicrobial finishing of leather.
  • the substances described here can also be used to protect cosmetic preparations, pharmaceutical products or household products from microfinance.
  • the antimicrobials of this invention may also be used in crop protection to protect plants on fields or forests, plant parts or seeds from disease or spoilage.
  • Corresponding compositions consist of at least one of the diols of this invention. The composition can be applied to seedlings, seeds or the soil.
  • the invention includes personal care compositions containing one or more of the diols described, either alone or in combination with nonionic surfactants and / or anionic surfactants and / or cationic surfactants and / or amphoteric surfactants.
  • the diols are used at an effective concentration that preserves the composition and / or results in an antimicrobial effect on the applied surface.
  • a wide range of cosmetic preparations contain antimicrobial agents. In particular, e.g. the following preparations are suitable:
  • Skin care products e.g. Skin washing and cleaning products in the nature of soap bars, liquid soap, soap-free products,
  • - Bath products e.g. liquid shower / bath products (bubble baths, milk,
  • Skin care products such as Emulsions, multi-emulsions or oils
  • Cosmetic products e.g. Face make-up in the form of a day cream or powder cream, face powder, rouge or cream make-up
  • eye care products such as, for example, Shadow, mascara, eyeliners, lip care products, such as Lipsticks, lip gloss
  • nail care products such as Nail polish, nail polish remover, nail hardener
  • Foot care products such as Foot baths, foot powders, foot creams, foot balm, special deodorants and antiperspirants
  • Light protective preparations e.g. Suntan lotion, lotions, creams or oils, self-tanner or after-sun products
  • Anti-insect agents e.g. Oils, lotions, sprays or sticks
  • Deodorants e.g. Sprays, deodorant aerosols, pump sprays, deodorant gels, sticks or roll-ons, and also anhydrous deodorant aerosols or sticks - antiperspirants, e.g. Antiperspirant sticks, creams, roll-ons also anhydrous antiperspirant sticks or aerosols
  • Products for cleaning and care products such as Peels and masks Hair removal products in chemical form, e.g. powdery or liquid preparations, creams or pastes or gels or aerosol foams; shaving products, e.g. Rasurseife, foaming shaving cream, non-foaming shaving cream, foams or gels, Preshave products for dry shaving, aftershaves or aftershave delusions
  • Perfume products such as Perfume oils or perfume creams
  • Cosmetic hair care products e.g. Shampoos or conditioners
  • hair care products such as hair care products.
  • Hair lotions
  • Styling creams styling gels, pomades, hair conditioners, hair treatments, products for the production and care of curls, hair straightening products, mousse, hair sprays, hair colors, hair tints
  • Anti-dandruff products in the form of shampoos, conditioners, hair lotions, styling creams or gels or hair conditioners in the form of shampoos, conditioners, hair lotions, styling creams or gels or hair conditioners
  • Corresponding cosmetic preparations can occur in a large waistband width, e.g.
  • liquid preparations such as W / O, O / W, O / W / O, W / O / W or PIT emulsions all types of microemulsions
  • the cosmetic or pharmaceutical preparations may e.g. as cream, gel, lotion, alcoholic or aqueous / alcoholic solution, wax / fat product, stick, powder or ointment.
  • Water-containing and oil-containing emulsions eg W / O, O / W, O / W / O and W / O / W emulsions or microemulsions or PIT emulsions
  • These formulations contain, for example, from 0.01 to 30% w / w, preferably from 0.1 to 15% w / w and particularly preferably from 0.5 to 10% w / w of an antimicrobial active ingredient They contain at least one oil component of from 0 to 30% w / w, especially from 1 to 30% w / w and more preferably from 4 to 20% w / w based on the total weight of the formulation
  • These formulations also contain at least one emulsifier from 10 to 90% w / w, especially from 30 to 90% w / w, of water from 0 to 88.9% w / w especially from 1 to 50% w / w and from other cosmetically acceptable additives.
  • the personal care products mentioned here contain diols in a physiologically acceptable medium.
  • the formulation is non-toxic, non-irritating and suitable for contact with surfaces of the human body. Such surfaces include, for example, hair, skin, mucous membranes, teeth. Whether the composition is physiologically acceptable can be determined by tests of the art. Household products and technical products
  • Household products describes a composition used in the typical environment of humans. These products are generally non-toxic.
  • the Household Product category may contain at least one other ingredient in addition to surfactants or alcohols, which may be both soluble and insoluble, such as other antimicrobials, enzymes, bleaches, whiteners, colorants, fabric softeners , Color transfer inhibitors, complexing agents, aerosol propellants and they may also contain surfactants or other alcohols.
  • the preparations of the category "household products” can be in very different forms, such as in an aqueous, non-aqueous or oily phase and they can also contain emulsifiers, as well as gelling or thickening agents. These preparations can be used as liquid, paste, gel, pieces, Tablets, sprays, foams, powders or granules.
  • the diols described herein may be present either alone or in combination with one or more other antimicrobial agents and / or biocides and may be added to e.g. Preservation of cosmetic or pharmaceutical products, for the preservation of personal care products, such. Toiletries, oral care products, for preserving household products, e.g. All-purpose cleaners, detergents or softeners and other products with a corresponding proportion of water, which must be protected by preservation by the microbial spoilage.
  • an "antimicrobial agent” is a substance capable of producing an antimicrobial effect
  • the present invention encompasses antimicrobial agents having bacteriostatic, bacteriocidal, virucidal, virostatic, fungistatic or fungicidal activity.
  • the substances of the present invention may also be used together with biogenic active ingredients.
  • biogenic active ingredients e.g. Tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, essential oils, plant extracts and vitamins.
  • pyrithiones especially zinc complexes (ZPT); Octopirox®; Climbazol®, selenium sulfide, dimethyldimethylol, hydantoin (Glydant®) Methylchloroisothiazolinone / methylisothiazolinone (Kathon CG®), sodium sulfites, sodium bisulfite, imidazolidinyl urea (Germall 15®, diazolidinyl urea (Germaill II®), benzyl alcohol, 2-bromo-2-nitropropane-1,3-diol (Bronopol®); formalin (formaldehyde); iodopropenyl butylcarbamate (polyphase P100®); Chloroacetamide; Methane amines; Methyldibromonitrile glutaronitri
  • 2,4,4'-trichloro-2'-hydroxy-diphenyl ether (Triclosan® or TCS); 2,2'-dihydroxy-5,5'-dibromo-diphenyl ether; Phenolic substances; Phenol; 2-methyl-phenol; 3-methylphenol; 4-methyl-phenol; 4-ethyl-phenol; 2,4-dimethyl-phenol; 2,5-dimethyl phenol; 3,4-dimethyl-phenol; 2,6-dimethyl-phenol; 4-n-propyl-phenol; 4-n-butyl phenol; 4-n-amyl-phenol; 4-tert-amyl-phenol; 4-n-hexyl-phenol; 4-n-heptyl-phenol; Mono and polyalkyl and aromatic halophenols; p-chlorophenol; Methyl p-chlorophenol; Ethyl p-chlorophenol; n-propyl p-chlorophenol; n-butyl p-chlorophenol
  • mixtures of the above antimicrobial preservatives are also suitable.
  • the invention also includes compositions comprising other "natural antimicrobial agents.” These may be proteins, corresponding peptides alone or with each other, natural essential oils or their derivatives, and some natural oils having antibacterial activity include oils of anise, lime, orange, rosemary, thyme, lavender, tea tree, lemon, wheat, lemongrass, cedar, cinnamon, eucalyptus, peppermint, basil, fennel, menthol, ocmea origanum, hydastis carradensis, berberidaceae daceae, ratanhiae and turmeric lon
  • mixtures of the above antimicrobial preservatives are also suitable.To achieve the broadest possible spectrum of action, better formulatability or better handling for the manufacturers of household products or personal care products, mixtures of different antimicrobial agents are available, which are used as preservatives or as antimicrobial agents Akti Substance that give the final product special anti
  • the concentration of the individual biocidal substances in the BIOZID combinations are between 1% and 99%, in particular between 10% and 90%.
  • the application concentration of these BIOZID combinations in household and personal care products is typically in the range of 0.05% to 5% and in particular in the range of 0.05% to 2%.
  • Other biocide combinations include:
  • the weight ratio of biocides for combinations of two biocides is 1: 1 or 1: 2 or 1: 3 or 1: 4 or 1: 5 or 1: 6 or 1: 7 or 1: 8 or 1: 9 or 1: 10 or 2: 1 or 3: 1 or 4: 1 or 5: 1 or 6: 1 or 7: 1 or 8: 1 or 9: 1 or 10: 1. In some cases, the ratio may even be between 1:10 and 1: 100 or 10: 1 and 100: 1.
  • BIOZIDE may be (as shown in Table 1) BIOZID 1, or BIOZIDE 2, or BIOZID 3, or BIOZIDE 4, or BIOZIDE 5, or BIOZIDE 6, or BIOZIDE 7, or BIOZIDE 8, or BIOZIDE 9, or BIOZID 10, or BIOZID 1 1, or BIOZID 12, or BIOZID 13, or BIOZID 14, or BIOZID 15, or BIOZID 16, or BIOZID 17, or BIOZID 18, or BIOZID 19, or BIOZID 20, or BIOZID 21, or BIOZIDE 22, or biocide 23, or biocide 24, or biocide 25, or biocide 26, or biocide 27, or biocide 28, or biocide 29, or biocide 30, or biocide 31, or biocide 32, or biocide 33, or biocide 34, or BIOZID 35, or BIOZID 36, or BIOZID 37, or BIOZID 38, or BIOZID 39, or BIOZID 40, or BIOZID 41, or BIOZID 42, or BIOZID 43, or BIOZID 44, or BIOZID 45, or
  • the liquid preparations generally contain at least one solvent and at least one further chemical compound, be it an organic compound, eg also a polymer, or an inorganic compound.
  • such formulations contain a variety of other different compounds that are desired or required for the particular application of the formulation.
  • the solvents used are water or organic solvents or mixtures of water and organic solvents, eg. As alcohols, into consideration; in the latter case it may be homogeneous mixtures or emulsions of water in organic solvents or vice versa (water in oil or oil in water emulsions).
  • the other constituents of the preparation are dissolved, emulsified or dispersed.
  • the diols may also be formulated in personal care or household products containing one or more preservative enhancers such as ethylhexylglycerol, propylene glycol, butylene glycol, PEG 40-hydrogenated castor oil, 1,2-propanediol, 1,3-propanediol, 1,2 Pentanediol, 1, 2-hexanediol, 1, 2-octanediol, 1, 2-decanediol, 4-methyl-4-phenyl-2-pentanol.
  • preservative enhancers such as ethylhexylglycerol, propylene glycol, butylene glycol, PEG 40-hydrogenated castor oil, 1,2-propanediol, 1,3-propanediol, 1,2 Pentanediol, 1, 2-hexanediol, 1, 2-octanediol, 1, 2-decaned
  • the liquid preparations may be e.g. be polymer dispersions or polymer solutions which optionally contain other additives, e.g. Pigments, dyes, stabilizers, thickeners, leveling agents, emulsifiers and co-emulsifiers, surfactants, oils, other preservatives, perfume oils, cosmetic care and
  • additives e.g. Pigments, dyes, stabilizers, thickeners, leveling agents, emulsifiers and co-emulsifiers, surfactants, oils, other preservatives, perfume oils, cosmetic care and
  • Active substances such as AHA acids, fruit acids, ceramides, phytantriol, collagen, vitamins and provitamins, for example vitamins A, E and C, retinol, bisabolol, panthenol, natural and synthetic light stabilizers, natural substances, opacifiers, solubilizers, repellents, bleaches, colorants, tinting agents , Browning agents (eg dihydroxyacetone), micropigments such as titanium oxide or zinc oxide, superfatting agents, pearlescent waxes, solubilizers, complexing agents, fats, waxes, silicone compounds, hydrotropes, dyes, pH regulators, reflectors, proteins and protein hydrolyzates, salts, gelling agents, other bodying agents, silicones , Moisturizers, moisturizers, UV sunscreens, antioxidants, defoamers, antistatics, emollients, plasticisers, peroxides, etc.
  • vitamins and provitamins for example vitamins A, E and C, retin
  • the preparations may also contain antibacterial metal salts.
  • This group includes a metal salt of Groups 3b-7b, 8 and 3a-5a. Particularly useful are the salts of aluminum, zirconium, zinc, gold, silver and copper.
  • the preparation may also contain complexing agents, e.g. EDTA, EDETA, chitosan derivatives or NTA.
  • complexing agents e.g. EDTA, EDETA, chitosan derivatives or NTA.
  • Such complexing agents can produce additional effects or synergistic effects together with the diols described herein.
  • Diols may also be incorporated into hair care formulations or may be dandruff-active applications. This is especially true for combinations with other antimicrobials, e.g. Zinc pyrithione, octopirox, climbazole, sulfur, imidazole derivatives, salicylic derivatives or proteins or peptides, such as e.g. in (WO 2009 080306 A1).
  • the diols can also be used as deodorant agents for personal care and household applications, such as forearm deodorant, forearm transpirant / deodorant, room fresher aerosols.
  • the invention includes personal care and household deodorants combined with one or more of the following: triclosan, triclocarban, organic acids such as benzoic acid, sorbic acid, silver compounds such as Tinosan SDC or the diols described herein.
  • the invention also includes personal care compositions which include a deodorant and one or more antiperspirant actives, such as Aluminum chlorohydrate, zirconium chlorohydrate and other salts of aluminum, zinc or zirconium, alcohol, complexing agents or antioxidants.
  • Esterase inhibitors may also be added to the preparations mentioned, as further deodorant.
  • Such inhibitors are especially trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and especially triethyl citrate (Hydagen CAT, Henkel). They inhibit enzyme activity and thereby reduce the formation of body odors.
  • sterol sulfates or phosphates such as lanosterol, cholesterol, dicarboxylic acids and their esters, can also be used as esterase inhibitors.
  • such ingredients may enhance or qualitatively alter the antimicrobial activity of the diols described herein.
  • the diols can be used alone or in mixtures for the treatment of acne. It can e.g. Combinations of the diols described herein with other substances such as phenoxyethanol, phenoxypropanol, benzalkonium chloride, cetrimonium bromide, benzethonium chloride or salicylic acid can be used. If the mixture is applied to a skin area affected by acne, the mixture will have an anti-acne effect. A wide variety of anionic surfactants may be useful in presentations of this invention.
  • Non-limiting examples of anionic surfactants can be selected from the group of alkyl and alkyl ether sulfates or from the group consisting of sulfonated monoglycerides, sulfonated olefins, alkylaryl sulfonates, primary or secondary alkanesulfonates, alkyl sulfosuccinates, acyl taurates, acyl isethionates, alkyl glyceryl ether sulfonates, sulfonated methyl esters, sulfonated fatty acids, alkyl phosphates, acyl glutamates, acyl sacosinates, alkyl sulfoacetates, acylated peptides, alkyl ether carboxylates, acyl lactylates, anionic fluorinated surfactants, and mixtures thereof.
  • Anionic surfactants can be used effectively for some illustrations of this invention.
  • the present invention includes personal care and household applications consisting of one or more nonionic surfactants.
  • Some nonionic surfactants are condensation products of ethylene oxide with very different components that have reactive hydrogen atoms and long hydrophobic chains (C12-C20).
  • Such products contain long hydrophilic polyoxyethylene subunits, such as condensation products of poly (ethylene oxide) with fatty acids, fatty alcohols, fatty amides, polyhydric alcohols and polypropylene oxide.
  • Polyoxamers include, for example, block copolymers of polyoxyethylenes and polyoxypropylene having an average molecular weight of 3,000 to 5,000 and a preferred average molecular weight of 3,500 to 4,000.
  • ionic surfactants are, for example, alkyl polyglut cosides, alcanolamides, ethers of fatty acids with ethylene oxide or propylene oxide, aminosides, eg cocamidopropylamine oxide.
  • the invention also includes personal care and household product formulations containing one or more amphoteric surfactants.
  • amphoteric surfactants are: secondary or tertiary aliphatic amine derivatives in which the aliphatic chain, linear or branched, has at least 8 to 22 C atoms and an anionic group such as carboxylates, sulfonates, sulfates, phosphates or phosphonates, acyl / Dialkylethylenediamines, acylamphoacetates, disodium acylamphodipropionates, sodium acylamphohydroxypropylsulfonates, disodium acylamphoacetates, sodium acylamphopropionates in which the acyl group represents either an alkyl or an alkenyl group, N-alkylamino acids or imino acids, such as aminopropylalkylglutamide, alkylaminopropionic acid, sodium alkyliminopropionate
  • amphoteric surfactants include C 10 -C 20 alkylamidoCi-C4 alkylene betaines and / or coco fatty acid amide propyl betaine.
  • the invention includes personal care and household product formulations consisting of a combination of anionic, nonionic and amphoteric surfactants.
  • the diols may also be formulated together with "mildness-enhancing" agents in personal care or household products. cationic and nonionic polymers, co-surfactants, moisturizing substances or mixtures thereof.
  • stabilizers are also incorporated in most cases in order to lead to improved stress and storage stability.
  • it is preferred to use stabilizers containing hydroxyl groups e.g. 12-hydroxystearic acid, 9,10-dihydroxystearic acid, tri-9,10-dihydroxystearin and tri-12-hydroxystearin (hydrogenated castor oil consists for the most part of tri-12-hydroxystearin).
  • the stabilizers that are added to the antimicrobial preparations consist of polymeric thickeners.
  • a thickener is a substance that can increase the viscosity of a liquid preparation.
  • Thickeners can be divided into two groups: those that have the best effect in water-based formulations and those that have the best effect in oil-based formulations. Thickeners can also be divided according to their origin, for example synthetic polymers, natural polymers and their derivatives, mineral polymers or according to their ionic character (anionic, cationic, nonionic or amphoteric thickeners).
  • dispersed amorphous silica e.g. evaporated silica, precipitated silica and mixtures thereof.
  • the term "dispersed amorphous silica” refers to finely divided, non-crystalline silica having an average particle size of silica agglomerates of less than 100 microns.
  • amorphous silica is used as the stabilizer, it is added in the range of 0.1 to 10%, preferably in the range of 0.25-8%, and more preferably in the range of 0.5-5%.
  • Another class of stabilizers used in the antimicrobial formulations of the present invention are the dispersed smectide clay from the group of bentonites and hectorites and mixtures thereof. Bentonite is a colloidal aluminum sulphate-containing clay. Hectorite is a clay consisting of sodium, magnesium, lithium, silicon, oxygen, hydrogen and fluorine. When disperse clay-containing soils are used in detergents, they are usually incorporated in the formulation from 0.1 to 10%, preferably from 0.25 to 8%, and more preferably from 0.5 to 5%.
  • passivation agents for stabilization, e.g. Hectorite, bentonite, montmorollonite, nontronite, saponite, sauconite, beidellite, allevardite, illite, halloysite, attapulgite, sepiolite and talc. These substances are often used in Deoelectricn, aerosols or sticks to keep contained antiperspirants in solution.
  • stabilizers such as fatty acids or fatty alcohols, may also be used in some of the formulations mentioned herein.
  • ingredients may be included to the diols in antimicrobial preparations.
  • These ingredients may be classified into the following functional classes: abrasives, anti-acne agents, anticaking agents, antioxidants, binders, biological additives, bulking agents, chelating agents, chemical additives, dyes, cosmetic astringents, cosmetic biocides, denaturants, emulsifiers, emollients , Film-forming agents, perfumes, humectants, opaque pigments, preservatives, propellants, reducing agents, skin bleaching substances, skin-repellent agents, skin protection agents, anti-wrinkle agents, adjuvants, solvents, foam boosters, hydrotropic agents, solubilizers, dispersants, gelling agents, sun protection agents, UV light filters , Viscosity enhancers or reducers, antibiofilm agents, antiplaque agents, antigin agents givitis agents, antiperiodontitis agents, flavorings, sweeteners, fluorinators,
  • the water as a solvent, either as the sole solvent or in admixture with other solvents.
  • the liquid preparations may be low-viscosity to high-viscosity preparations.
  • aqueous preparations containing organic compounds are often a good breeding ground for microorganisms and should be preserved by the addition of biocides.
  • the liquid preparations generally contain at least one solvent and at least one further chemical compound, be it an organic compound, e.g. also a polymer, or an inorganic compound.
  • such formulations contain a variety of other different compounds that are desired or required for the particular application of the formulation.
  • the solvents used are water or organic solvents or mixtures of water and organic solvents, eg. As alcohols, into consideration; in the latter case it may be homogeneous mixtures or emulsions of water in organic solvents or vice versa (water in oil or oil in water emulsions).
  • the other constituents of the preparation are dissolved, emulsified or dispersed.
  • the liquid preparations may be e.g. be polymer dispersions or polymer solutions which optionally contain other additives, e.g. Pigments, dyes, stabilizers, thickeners, leveling agents, emulsifiers and co-emulsifiers, surfactants, oils, other preservatives, perfume oils, cosmetic care and
  • additives e.g. Pigments, dyes, stabilizers, thickeners, leveling agents, emulsifiers and co-emulsifiers, surfactants, oils, other preservatives, perfume oils, cosmetic care and
  • Active substances such as AHA acids, fruit acids, ceramides, phytantriol, collagen, vitamins and provitamins, for example vitamin A, E and C, retinol, bisabolol, panthenol, natural and synthetic light stabilizers, natural substances, opacifiers, solubilizers, repellents, bleaching agents, colorants, tinting agents , Browning agents (eg dihydroxyacetone), micropigments such as titanium oxide or zinc oxide, superfatting agents, pearlescent waxes, solubilizers, complexing agents, fats, waxes, silicone compounds, hydrotropes, dyes, pH regulators, reflectors, proteins and protein hydrolyzates, salts, gelling agents, other bodying agents, silicones , Moisturizers, moisturizers, UV sunscreens, antioxidants, defoamers, antistatics, emollients, plasticisers, peroxides, etc.
  • vitamins and provitamins for example vitamin A, E and C, retin
  • the water as a solvent, either as the sole solvent or in admixture with other solvents.
  • the liquid preparations may be low-viscosity to high-viscosity preparations.
  • High-viscosity preparations are in particular also ointments, creams or gels.
  • Gaseous preparations are in particular sprays, z. B. as an aerosol or pump spray.
  • preparations solids-stabilized formulations, stick formulations, PIT formulations, in the form of creams, foams, sprays (pump spray or aerosol), gels, gel sprays, lotions, oils, oil gels or mousses.
  • liquid preparations including high viscosity preparations such as ointments or creams
  • gaseous preparations may be e.g. to be those for medical, hygienic, cosmetic or dermatological purposes, are also detergents or cleaning agents.
  • the content of the 1,3-diols in the preparations should preferably be at least 0.001, particularly preferably at least 0.01 and very particularly preferably at least 0.05 part by weight of 1,3-diol per 100 parts by weight of the preparation. For the intended effect, it is generally meaningless to use more than 2 parts by weight or more than 1 part by weight of 1,3-diol per 100 parts by weight of the preparation.
  • 1, 3-diols as biocide, be it in the above preparations or for the biocidal finishing of moldings, a single, defined 1, 3-diol or a mixture of 1, 3-diols can be used.
  • 1, 3 diols can always be used in combination with other biocides and thus support the action of other biocides.
  • the 1, 3-diols as biocides have excellent activity against microorganisms, such as viruses, yeasts, fungi, algae and especially against bacteria, are gram-negative or gram-positive bacteria. They are therefore suitable for biocidal finishing of moldings and for the preservation of liquid preparations, sprays, foams or gels in order to protect them against infestation and growth of various microorganisms.
  • the invention encompasses the use of diols of the formula (1) for antimicrobial treatment, for antimicrobial finishing, for deodorising and disinfecting the skin, mucous membranes, tooth surfaces, nail surfaces and hair.
  • the invention encompasses the use of diols of the formula (1) as antishock agents in hair care products.
  • the invention encompasses the use of diols of formula (1) as an antimicrobial active substance for the treatment of skin infections and mucous membrane infections and nails.
  • the invention includes the use of diols of formula (1) for the treatment of skin and mucous membrane injuries.
  • the invention encompasses the use of diols of the formula (1) as active substance of medical materials.
  • the invention encompasses the use of diols of formula (1) for the preservation, stabilization, antimicrobial treatment, disinfection and deodorizing of inanimate surfaces and materials.
  • the invention includes the use of diols of formula (1) for the antimicrobial treatment of textiles.
  • the invention encompasses the use of diols of formula (1) for the preservation of household products, cosmetic products and pharmaceutical products and pharmaceutical products.
  • the invention encompasses the use of diols of the formula (1) in washing and cleaning formulations.
  • the invention encompasses the use of diols of formula (1) for the antibacterial finishing and preservation of plastic products, paper products, nonwoven materials, wood and leather.
  • the invention includes the use of diols of formula (1) for antimicrobial finishing and preservation of engineering products.
  • the invention encompasses the use of diols of the formula (1) as a biocide in industrial processes.
  • the invention includes personal care products which comprise a) 0.01 to 15% w / w with respect to the total weight of the formulation containing the substance defined in claim 1 of formula (1) b) cosmetically compatible ingredients.
  • the invention includes oral care products which include
  • the invention includes pharmaceutical products which include
  • the invention includes the use of diols of formula (1) for inhibiting biofilms and / or destroying biofilms and / or for inhibiting or killing microorganisms capable of forming biofilms.
  • the 1, 3-diols were tested as biocides and, for comparison, propylene glycol (which was used as solvent), 1, 2-pentanediol (high biocidal effect known) and 2,4-pentanediol (low biocidal effect).
  • a 40 weight percent solution of a diol in propylene glycol at 60 0 C was prepared in each case.
  • This solution was diluted with a double starch soybean solution (double strengh Tryptone Soy Broth) as a nutrient medium in a volume ratio of 1: 1.
  • solutions were prepared with the following concentrations: 400,000ppm (40%), 200,000ppm (20%), 100,000ppm (10%), 50,000ppm (5%), 25,000ppm (2.5%), 12,500ppm (1.25%), 6,250ppm (0.625%), 3,125ppm (0.3125%)
  • microorganisms were used to test the biocidal activity against different bacteria and fungi:
  • the positive control was a solution of 5 ml soya solution, which was admixed with 0.1 ml of the respective microorganism.
  • the test solutions consisted of 5 ml of the above-described soya solutions of diols of respective concentration, which were mixed with 0.1 ml of the respective microorganism.
  • the samples and controls were incubated in the case of bacteria at 30 0 C for 48 hours in fungi for 5 days at 25 ° C.
  • the MIC (Minimum Inhibitory Concentration) value was determined in each case. This value indicates the minimum concentration at which the growth of the microorganisms visibly hindered compared to the corresponding sample without the addition of the diol. The lower the MIC value, the greater the biocidal effect.
  • test was considered positive if the test solution was comparable to the positive control by visual assessment. For example, this was recognizable by the appearance of turbidity or visible growth of the microorganism. A test was considered negative if the test solution had the same appearance as the negative control.
  • the MIC value is a range between the next higher concentration of a positive test and the same and / or lower concentration of a first negative test.
  • the last line of the tables below shows a value "Maximum", which indicates the highest measured MIC value of the series of microorganisms tested.
  • the bactericidal activity of the substances of this invention was carried out in a suspension test according to the European standard EN 1040 and compared with the activities of common market products. Only minor modifications were made.
  • the substances of formula (1) were dissolved in water or ethanol to give a 1% stock solution.
  • test mixtures were selected such that 1000 ppm of active substance were contained in an aqueous solution. The same procedure was used for the comparative samples.
  • test batches with the following bacterial strains were inoculated such that the specified bacterial densities were present in the test batches.
  • the fungicidal activity was determined according to the European standard EN 1275 and compared with the activities of common market products, with only minor modifications.
  • the substances of formula (1) were dissolved in water or ethanol to give a 1% stock solution.
  • test mixtures were selected such that 1000 ppm of active substance were contained in an aqueous solution.
  • active concentration of 1% was chosen in the test. The same procedure was used for the comparative samples.
  • test batches with the following yeast and mold fungi strains were inoculated in such a way that the stated bacterial densities were present in the test batches.
  • A. niger ATCC 16404 1 - 2.5 x 10 5 cfu / ml The assay mixtures were incubated at room temperature (22 ° C +/- 2 ° C). After defined contact times, 1 ml aliquots were taken to determine the surviving germ count. To inactivate the microbicidal activity of the diols, the aliquots were diluted in 1:10 dilution steps in a solution of Sabouraud medium with 10% Tween, 3% lecithin, 0.1% histidine and 0.5% sodium thiosulfate and the 10 " 2 10" 3 and 10 "4 dilution used for determining the survivor seed deposited. for this purpose, appropriate aliquots were plated on Sabouraudmedium with neutralizers and incubated for 2 d at 30 0 C.
  • the determined survivor counts were each related to a water (water control) approach by determining the logarithmic reduction in survivor counts relative to the water control
  • KBT preservation challenge tests
  • the method is used to determine sufficient preservation in the case of finished products such as cosmetics and household products as well as technical raw materials (dyes, liquid soaps, shampoos, emulsions, creams, etc.).
  • the products are stored, possibly opened several times, refilled, etc. This can lead to contamination by microorganisms.
  • microorganisms In the preservation stress test, this is simulated by artificial contamination with microorganisms. These can either be inoculated as a mixed population or individually in independent approaches. The inoculated product samples are incubated under defined conditions and samples taken at defined times to determine the germ load. With sufficient preservation, the number of microorganisms should either decrease or remain constant depending on the species, e.g. in the Ph. Eur. 6.0 requirements.
  • Example Formulation 1 Stundard Emulsion O / W
  • dilution medium phosphate buffer, 0.07 molar pH 7.4 (+/- 0.2), with 1% Tween 80 + 0.3% soybean lecithin
  • the inoculated product samples are then incubated for a total of 28d at 20-25 ° C. Aliquots were taken after 2d, 7d, 14d and after 28d and diluted in dilution medium (phosphate buffer, 0.07 molar pH 7.4 (+/- 0.2), with 1% Tween 80 + 0.3% soya lecithin). In the dilution steps 10 " 1 to 10" 4 the surviving germ counts were determined. As a reference point for the determination of the reduction of the number of bacteria, the respective immediate value of the sample was used. The results were given as logarithmic reductions. The following strains were used for the tests:

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Abstract

Utilisation d'un diol comme agent biocide, caractérisée en ce que le diol est un diol représenté formule (I), dans laquelle R1 et R2 représentent chacun séparément un résidu organique comprenant chacun au moins un atome C, ou R1 et R2 forment ensemble une structure cyclique constituée d'au moins 4 atomes C, éventuellement substituée (désigné ci-après par la forme abrégée "1,3 Diol").
EP10742169A 2009-08-26 2010-08-16 Utilisation de 1,3-diols comme biocides Withdrawn EP2470156A2 (fr)

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WO2011023582A3 (fr) 2012-01-26
JP2013503123A (ja) 2013-01-31
WO2011023582A2 (fr) 2011-03-03
KR20120058571A (ko) 2012-06-07
BR112012004153A2 (pt) 2016-03-22
CN102481242A (zh) 2012-05-30
US20120152149A1 (en) 2012-06-21

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