EP1042265A2 - O-derivate halogenierter diphenyletherverbindungen - Google Patents

O-derivate halogenierter diphenyletherverbindungen

Info

Publication number
EP1042265A2
EP1042265A2 EP98965241A EP98965241A EP1042265A2 EP 1042265 A2 EP1042265 A2 EP 1042265A2 EP 98965241 A EP98965241 A EP 98965241A EP 98965241 A EP98965241 A EP 98965241A EP 1042265 A2 EP1042265 A2 EP 1042265A2
Authority
EP
European Patent Office
Prior art keywords
formula
compound
radical
compounds
sulfo
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Withdrawn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
EP98965241A
Other languages
English (en)
French (fr)
Inventor
Werner Hölzl
Dietmar Hüglin
Thomas Maier
Jianwen Mao
Dietmar Ochs
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 Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
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 Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Priority to EP98965241A priority Critical patent/EP1042265A2/de
Publication of EP1042265A2 publication Critical patent/EP1042265A2/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • 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
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/02—Monocyclic aromatic halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds

Definitions

  • the present invention relates to O-derivatives of halogenated diphenyl ether compounds, to a process for the preparation of these compounds, to their use as antimicrobial active substance.
  • halogenated diphenyl ether compounds have an excellent antimicrobial activity. These compounds are therefore widely used, for example as active substances for the antimicrobial finishing of medical items and household articles, as detergent additive and in the hygiene sector, for example in soaps or dental hygiene products.
  • Polymeric materials can be antimicrobially finished by incorporating halogenated diphenyl ether compounds, the active substances being, as a result of their excellent migration properties, constantly conveyed to the surface of the corresponding material ("slow release"). For certain industrial applications, this effect is undesired since the long-term effect of antimicrobially finished materials such as textiles, paper, plastics, cellulose sponges etc. is reduced at the same time.
  • the object of the present invention is thus to provide diphenyl ether compounds which have antimicrobial activity and which, at the same time, are stable to migration.
  • the present invention thus provides O-derivatives of halogenated diphenyl ether compounds of the formula
  • R, and R 2 independently of one another are F, CI or Br; is a radical of the formula (1 a) -(CH 2 ) — CH - 0-R 4 ; (1 b)
  • R 3 is C C 22 alkyl; C.-C ⁇ alkoxy; phenyl; phenyl-C.-C ⁇ lkyl; — (CH 2 ) p - A + R 5 R 6 R 7 ;
  • R 5 , R 6 , R 7 and R 8 independently of one another are hydrogen; C 1 -C 4 all yl; sulfo- C ⁇ C ⁇ Ikyl; or R 5 and R 6 together with A form a cyclic radical unsubstituted or substituted by sulfo groups; or R 7 and R 8 together with N form a cyclic radical unsubstituted or substituted by sulfo groups;
  • A is N or P
  • Z is fluorine, chlorine, the radical of the formula (1 g)
  • Z 2 is fluorine, chlorine, d-Caaalkoxy, C C 22 alkylthio or CrC 22 -monoalkylamino or
  • C C-aadialkylamino each of which is unsubstituted or substituted by OH, NH 2 or sulfo; C 6 -C 12 aryloxy, C 6 -C 12 arylthio or C 6 -C ⁇ 2 monoarylamino or C 6 -C 12 diarylamino, each of which is unsubstituted or substituted by OH, NH 2 or sulfo; m is from 1 to 3; n is 1 or 2; and p p 2 , p 3> p 4 and p 5 independently of one another are 1-4.
  • C.-C ⁇ alkyl and C ⁇ C ⁇ alkoxy are straight-chain or branched alkyl radicals, for example methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, amyl, isoamyl or tert-amyl, hexyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl or eicosyl, and methoxy, ethoxy, propoxy, butyloxy, pentyloxy, amyloxy, isoamyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy
  • Phenyl-C 1 -C 4 all ⁇ yl is, for example, phenylethyl, phenylpropyl, phenylbutyl or, preferably, benzyl.
  • the derivatives according to the invention are ester, ether or glucoside derivatives of halogenated diphenyl compounds.
  • Preferred ester derivatives are those of the formula
  • R 1t R 2 , R 3 , m and n are as defined in formula (1).
  • R 3 is C.,-C 12 alkyl; or phenyl; and, in particular, to those compounds of the formula (2) in which
  • R, and R 2 are chlorine
  • R 3 is C.-C ⁇ alkyl; m is 1 or 2; and n is 1;
  • Illustrative ester derivatives of halogenated diphenyl compounds according to the invention are those of the formula
  • R 3 is C ⁇ C ⁇ alkyl or phenyl.
  • ester derivatives according to the invention are those of the formulae: o ⁇ n 8
  • R v R 2 , m and n are as defined in formula (1); and R 8 , R 9 and R 10 independently of one another are hydrogen; or C.-C 4 alkyl.
  • Preferred ether derivatives according to the invention are those of the formula
  • R R 2 , R 4 , X, m, n, p, and p 2 are as defined in formula (1 )
  • R 4 is C 1 -C22alkyl. or of the formula
  • ether derivatives according to the invention are those of the formulae (12) v-0 — ,
  • V is a radical of the formula (1 h), preferably (1 i) or (1 k); R 8 , R 9 and R 10 are hydrogen; or C ⁇ C ⁇ Ikyl; and Z, is -O-V; and Z 2 is CI; or N(CH 2 CH 2 OH) 2 .
  • Preferred glucoside derivatives according to the invention are those of the formula
  • V is a radical of the formula (1 h), or, preferably, (1 i) or (1 k).
  • halogenated diphenyl ether derivatives according to the invention which have a phosphate, sulfate or glucoside group are hydrophilic compounds, which are readily obtainable synthetically in high yields.
  • Y is a radical of the formula (1b);
  • R 3 is -(CH 2 ) p4 -N + R 5 R6R 7 ; are obtained in good yields by reacting the chloroacetate of the compound of the formula
  • Sulfobetaines i.e. compounds of the formula (1), in which
  • Y is a radical of the formula (1 b); R 3 is -(CH 2 ) p4 -A-N + R 5 R 6 R 7 ;
  • R 5 is sulfoalkyl; or R 5 and R 6 with A form a cyclic radical, are obtained by reacting corresponding N-dialkyl- or -monoalkylbetaine esters of the compound of the formula (15) with aqueous MSO 3 solution and a suitable catalyst system.
  • Y is a radical of the formula (1f);
  • chlorophosphate the compound of the formula • anc * corresponding amine.
  • the glucoside derivatives are obtainable by reacting the phenolic OH group of the compound of the formula (15) with peracetylated glucose and subsequently hydrolyzing the ester protective groups.
  • the hydrophilic derivatives are colourless, high-melting compounds having good solubility in water.
  • Hydrophobic halogenated diphenyl ether derivatives for example compounds of the formulae (3a), (3b), (10a), (10b) and (11a) and (11b) are obtainable in a single-stage reaction by esterifying or etherifying the phenolic OH group of the compound of the formula (15). Solubility and melting point of the acylated derivatives can be varied within a wide range by the choice of reactant.
  • the diphenyl ether derivatives according to the invention are thermally stable and antimicrobially effective compounds of low volatility and having a severely reduced tendency to migrate. They are therefore preferably suitable for the antimicrobial finishing of polymeric compounds, for example in plastics, rubbers, paints, surface coatings, (textile) fibres which are exposed to a microbially contaminated environment.
  • polymers and other substrates which can be antimicrobially finished in this way are:
  • polyurethanes derived from polyethers, polyesters and polybutadienes having terminal hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates on the other, and precursors thereof, - polyamides and copolyamides derived from diamines and dicarboxylic acids and/or from aminocarboxylic acids or the corresponding lactams,
  • polyureas polyimides, polyamide-imides. poiyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles,
  • - natural polymers such as cellulose, natural rubber, gelatine, and derivatives thereof modified chemically in a polymer-homologous manner, such as cellulose acetates, cellulose propionates cellulose butyrates, or the cellulose ethers, such as methylcellulose; and also rosins and derivatives.
  • the invention thus also provides a composition
  • a composition comprising
  • the invention also relates to a process for the antimicrobial finishing of an organic material, which comprises adding at least one compound of the formula (1 ) thereto, and to the use of the compound of the formula (1) for the antimicrobial finishing of polymeric materials.
  • the amount of antimicrobial active substance to be used depends on the organic material to be antimicrobially finished and on the intended use of the material finished in this way.
  • the composition according to the invention generally comprises, per 100 parts by weight of component (A), from 0.01 to 15 parts by weight, in particular from 0.05 to 10 parts by weight, and especially from 0.1 to 5 parts by weight of the antimicrobial active substance (component (B)).
  • the antimicrobial active substance (component (B)) can also be a mixture of two or more compounds of the formula (1).
  • the compositions according to the invention can, in addition to the compounds according to the invention, also comprise other additives, for example antioxidants or light protection agents.
  • Incorporation into the organic polymers can take place by adding the halogenated diphenyl ether compound according to the invention and, if desired, other additives by the methods customary in the art. Incorporation can expediently take place before or during shaping, for example by mixing the pulverulent components or by adding the antimicrobial active substance to the melt or solution of the polymer, or by applying the dissolved or dispersed compounds to the polymer, if desired with subsequent evaporation of the solvent.
  • Another method of incorporating the mixtures according to the invention into polymers involves adding the former before or during polymerization of the corresponding monomers or before crosslinking.
  • the mixtures according to the invention can also be added to the organic polymers to be finished in the form of a masterbatch which comprises these compounds, for example, in a concentration of from 2.5 to 25% by weight.
  • the resulting antimicrobially finished polymer compositions can be converted into shaped articles, for example fibres, films, tapes, sheets, multi-wall sheets, containers, tubes and other profiles, by conventional methods, for example by hot pressing, spinning, extrusion or injection moulding.
  • the diphenyl ether derivatives of the formula (1 ) are also suitable for the antimicrobial finishing of undyed and dyed or printed fibre materials made, for example, of silk, wool, polyamide or polyurethane, and in particular of cellulosic fibre materials of all types.
  • Such fibre materials are the natural cellulose fibres, such as cotton, linen, jute and hemp, and also pulp and regenerated cellulose. Preference is given to textile fibre materials made of cotton.
  • the diphenyl ether derivatives according to the invention are also suitable for the antimicrobial finishing of hydroxyl-group-containing fibres which are present in mixed fabrics, for example, of mixtures of cotton with polyester fibres or polyamide fibres.
  • one or more compounds of the formula (1) are advantageously applied to the textile fibre material in an amount of from 0.01 to 5% by weight, preferably 0.1-3% by weight, and in particular from 0.25 to 2% by weight, based on the weight of the fibre material, in a process analogous to dyeing.
  • the diphenyl ether derivatives according to the invention can be applied to the fibre material and fixed to the fibre in different ways, in particular in the form of aqueous dispersions or printing pastes.
  • the textile fibre materials finished using the compounds of the formula (1 ) according to the invention have an excellent and long-lasting antimicrobial protection.
  • the diphenyl ether derivatives according to the invention are also useful for the disinfection of the skin, mucous membrane and hair, preferably for the disinfection of hands and wounds.
  • these compounds are suitable as an antimicrobial active substance in personal care products as shampoos, bath- and shower additives, hair-care products, liquid and bar soaps, lotions and cremes, deodorants, other aqueous or alcoholic solutions, for example cleaning solutions for the skin, moist cleaning sheets, oils and powders.
  • a further subject of the present invention is therefore a personal care composition
  • a personal care composition comprising at least one compound of the formula (1) and cosmetically tolerable carriers or auxiliaries.
  • the personal care composition according to the present invention comprises 0.01 to 15, preferably 0.5 to 10 % b.w. of the diphenyl ether derivative of formula (1) and cosmetically tolerable carriers or auxiliaries.
  • the personal care composition according to the invention can be formulated as a water-in-oil or oil-in-water emulsion, as an oil-in-alcohol lotion, as a vesicular dispersion of an ionic or non-ionic amphiphilic lipid, as a gel, solid stick or as an aerosol formulation.
  • the cosmetically compatible auxiliary preferably contains 5 to 50% of an oil phase, 5 to 20% of an emulsifier and 30 to 90% of water.
  • the oil phase can in this case contain any oil suitable for cosmetic formulations, e.g.
  • hydrocarbon oils one or more hydrocarbon oils, a wax, a natural oil, a silicone oil, a fatty acid ester or a fatty alcohol.
  • Preferred mono- or polyols are ethanol, isopropanol, propylene glycol, hexylene glycol, glycerol and sorbitol.
  • diphenyl ether derivatives according to the invention are useful as household cleaners for the cleaning and disinfection of hard surfaces.
  • Example 8 Determination of the antimicrobial activity of the compound of the formula
  • Test bacteria Staphylococcus aureus ATCC 9144 Escherichia coli NCTC 8196
  • wells having a diameter of 1 cm are cut out using a cork borer (a maximum of 4 wells per plate).
  • 100 ⁇ i of the compound of the formula (102) are poured into each well, and the plates are incubated at 37°C (E. coli and S. aureus for 24 hours). Dilutions of the compound of the formula (102) are prepared in 96% analytical grade ethanol.
  • Example 9 Determination of the antimicrobial activity of the compound of the formula (103) An agar well test corresponding to method CG 126 is carried out with the following modifications:
  • Test bacteria Staphylococcus aureus ATCC 9144 Escherichia coli NCTC 8196
  • Example 10 Determination of the minimum inhibitory concentration (MIC) of the compound of the formula (101):
  • test substances are dissolved in methyl Cellosolve, and a dilution series of the compound of the formula (101) in agar are prepared.
  • the cells are floated out using NaCI solution and adjusted to a density of about 10 6 CFU/ml (live bacterial count).
  • each bacterial suspension 1 ⁇ l of each bacterial suspension is dropped onto the agar plates containing the test substance, and the plates are then incubated at 37°C for 2 days.
  • the bacterial suspensions are applied to agar plates without test substances.
  • the bacterial suspensions are applied to agar plates containing methyl Cellosolve, but without test substance. After the plates have been incubated, the growth of the bacteria on the test-substance-containing plates is compared with that on the control plates.
  • the minimum inhibitory concentration (MIC) is given as the lowest concentration which shows clear inhibition compared with the control.
  • the MIC values are given in the table below.
  • composition (100% active ingredients) % w/w A Compound of formula (102) 1% B Sodium Laureth-2 Sulfate 10.0%
  • (C) is added by stirring to 50% of the calculated amount of the formulation.
  • the suspension is heated up to about 60°C and stirred until (C) is dissolved completely.
  • composition (100% active ingredients) % w/w
  • (C) is added by stirring to 50% of the calculated amount of the formulation.
  • the suspension is heated up to about 60°C and stirred until (C) is dissolved completely.
  • composition (100% active inqredients) % w/w
  • composition (100% active inqredients) % w/w
  • composition (100% active inqredients) % w/w
  • Solution (2) is added to (1) and stirred at maximum speed. Then slowly cool down under continuos stirring. G is added at ⁇ 40°C.
  • composition (100% active ingredients) % w/w
  • Solution (2) is added to (1 ) and stirred at maximum speed. Then slowly cool down under continuos stirring. (G) is added at ⁇ 40°C.
  • Example 17 Preparation of a liguid laundry detergent
  • composition (100% active ingredients) % w/w
  • composition (100% active inqredients) % w/w
  • composition (100% active ingredients) % w/w
  • Non-ionic surfactants 2.9%
  • Example 20 Preparation of a laundry detergent powder
  • composition (100% active ingredients) % w/w
  • Non-ionic surfactants 2.9%
  • composition (100% active ingredients) % w/w
  • Example 22 10 grams of the compound of formula (102) is added into 45 grams of low density polyethylene (Escorene LL6301 XR, from Exxon) and 45 grams of low density polyethylene (Escorene LL6301 RQ, from Exxon). The mixture is tumble mixed for 10 minutes followed by addition into a 29mm twin-extruder to produce a master batch. The extrusion temperature is set at 180°C.
  • Example 23 10 gram of the resulting master batch (contains 10% of compound of formula 102) in Example 22 is added into 90 grams of low density polyethylene pellets (Escorene LL6301 XR, from Exxon) and well mixed. The mixture is then charged into an injection moulding machine to produce low density polyethylene plates (10 x 20 cm, thickness 2mm). The resulting low density polyethylene plates contain 1% of compound of formula (102). The plates are then cut into discs of 2 cm in diameter and tested for antimicrobial efficacy in agar diffusion test by using the same procedures as described in Example 8.
  • low density polyethylene pellets Escorene LL6301 XR, from Exxon

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP98965241A 1997-12-12 1998-12-09 O-derivate halogenierter diphenyletherverbindungen Withdrawn EP1042265A2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP98965241A EP1042265A2 (de) 1997-12-12 1998-12-09 O-derivate halogenierter diphenyletherverbindungen

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP97810977 1997-12-12
EP97810977 1997-12-12
EP98965241A EP1042265A2 (de) 1997-12-12 1998-12-09 O-derivate halogenierter diphenyletherverbindungen
PCT/EP1998/007997 WO1999031036A2 (en) 1997-12-12 1998-12-09 O-derivatives of halogenated diphenyl ether compounds

Publications (1)

Publication Number Publication Date
EP1042265A2 true EP1042265A2 (de) 2000-10-11

Family

ID=8230519

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98965241A Withdrawn EP1042265A2 (de) 1997-12-12 1998-12-09 O-derivate halogenierter diphenyletherverbindungen

Country Status (3)

Country Link
EP (1) EP1042265A2 (de)
AU (1) AU2052599A (de)
WO (1) WO1999031036A2 (de)

Cited By (1)

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Publication number Priority date Publication date Assignee Title
WO2001089518A1 (en) * 2000-05-23 2001-11-29 Ian Gillam Method of determining a dosage of anti-oxidant for an individual

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US6683056B2 (en) * 2000-03-30 2004-01-27 Bristol-Myers Squibb Company O-aryl glucoside SGLT2 inhibitors and method
FR2839448A1 (fr) * 2002-05-07 2003-11-14 Oreal Utilisation d'esters de triclosan, de piroctone et de tropolone dans une composition a liberation controlee
EP1845087A1 (de) 2006-04-14 2007-10-17 Mutabilis SA Hydroxyphenylerivate und deren biologische Anwendungen
CN101484390A (zh) * 2006-07-05 2009-07-15 西巴控股公司 二卤代-羟基二苯醚作为抗微生物剂在水处理中的用途
US8629210B2 (en) 2008-10-10 2014-01-14 Ndsu Research Foundation Zwitterionic/amphiphilic pentablock copolymers and coatings therefrom
DK2473480T3 (en) 2009-09-01 2016-09-05 Fab Pharma Sas Novel antibacterial hydroxyphenylforbindelse
US20110171279A1 (en) * 2009-11-02 2011-07-14 Ndsu Research Foundation Polyethylenimine biocides
EP2386589A1 (de) 2010-04-23 2011-11-16 Centre National de la Recherche Scientifique (C.N.R.S) Neue antimikrobielle Zusammensetzung, Verwendung damit und Herstellung davon
CN103857440B (zh) 2011-06-22 2018-09-25 维奥姆生物科学有限公司 基于缀合物的抗真菌和抗细菌前药
CN106349718B (zh) * 2016-10-25 2019-04-12 齐鲁工业大学 一种抗菌性胶原的制备方法
CN115536543B (zh) * 2022-11-10 2023-11-03 贵州大学 一种含异丙醇胺结构的三氯生类化合物及其制备方法和应用

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US3629477A (en) * 1966-08-08 1971-12-21 Geigy Chem Corp Halogenated diphenyether-containing compositions and control of pests therewith
CA2185056A1 (en) * 1995-09-08 1997-03-09 You Ling Fan Biostatic coatings and processes

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001089518A1 (en) * 2000-05-23 2001-11-29 Ian Gillam Method of determining a dosage of anti-oxidant for an individual

Also Published As

Publication number Publication date
WO1999031036A3 (en) 1999-11-04
AU2052599A (en) 1999-07-05
WO1999031036A2 (en) 1999-06-24

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