GB1022744A - New phenolic antimicrobial compositions - Google Patents

New phenolic antimicrobial compositions

Info

Publication number
GB1022744A
GB1022744A GB732964A GB732964A GB1022744A GB 1022744 A GB1022744 A GB 1022744A GB 732964 A GB732964 A GB 732964A GB 732964 A GB732964 A GB 732964A GB 1022744 A GB1022744 A GB 1022744A
Authority
GB
United Kingdom
Prior art keywords
methoxy
ether
hydrolysed
dichloro
hydrogen
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.)
Expired
Application number
GB732964A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB1022744A publication Critical patent/GB1022744A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
    • 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
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/13—Phenols; Phenolates
    • C08K5/136—Phenols containing halogens
    • 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

Abstract

Halogen substituted o-hydroxy diphenyl ethers, (o-phenoxy phenols) of the general formula <FORM:1022744/C2/1> wherein X, Y and Z may each be Cl or Br, and one of Y and Z may be hydrogen, are prepared by two different processes: (A) the corresponding o-aminodiphenyl ether is converted to a diazonium salt, which is then hydrolysed; (B) the corresponding o-methoxy compound is demethylated. In accordance with A, an example is given wherein 2-amino-4,41-dichlorodiphenyl ether is first reached with nitrosyl sulphuric acid in C.H2SO4, and then hydrolysed with water in the presence of o-dichlorobenzene, to 2-hydroxy-4,41-dichlorodiphenyl ether. Other analogous ethers are prepared in like manner. Procedure (B) is exemplified by reaction of 4-chloro-2-methoxy phenol with 3,4-dichloro-1-nitrobenzene to give 2 - methoxy - 4,21 - dichloro - 41 - nitro - diphenyl ether, which is catalytically reduced, (H2 and Ni) to the corresponding 2-methoxy-4,21-dichloro-4-amino diphenyl ether. This is then diazotized and reacted with either freshly made cuprous chloride in c.HCl to replace the amino group with halogen, giving 2-methoxy-4,21,41-trichlorodiphenyl ether, or with copper powder in boiling ethanol, to replace the amino group with hydrogen giving 2-methoxy-4,21-dichlorodiphenyl ether. The methoxy group is then hydrolysed off by reaction with aluminium chloride in boiling benzene, or heating with aqueous or acetic hydrobromic acid to give the corresponding o-phenoxy phenol. Other ethers are prepared in like manner. The compounds are used for internal and external antimicrobial compositions (see Divisions A5).ALSO:Antimicrobial compositions, for internal and external use, comprise at least one halogenated o-hydroxydiphenyl ether, of general formula: <FORM:1022744/A5-A6/1> wherein X, Y, and Z are each Cl or Br, and one only of Y and Z may be hydrogen, together with an appropriate carrier, and, optionally other known antimicrobial agents. Forms stated for the compositions are ointments, powders, tinctures, gargles, and mouthwashes (or tablets therefor) for external use, and tablets or dragees for internal use, for disinfecting the urinal and p intestinal tract, conventional excipients being used in all cases. Other active ingredients named are sulphur, for use in powders, and zinc stearate for ointments.
GB732964A 1963-02-22 1964-02-21 New phenolic antimicrobial compositions Expired GB1022744A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH225063A CH406127A (en) 1963-02-22 1963-02-22 Process for the antimicrobial finishing of textiles

Publications (1)

Publication Number Publication Date
GB1022744A true GB1022744A (en) 1966-03-16

Family

ID=4229370

Family Applications (3)

Application Number Title Priority Date Filing Date
GB739964A Expired GB1024022A (en) 1963-02-22 1964-02-21 Process and materials for protection of organic materials against micro-organism contamination
GB732864A Expired GB1038185A (en) 1963-02-22 1964-02-21 New diphenyl ethers and processes for their production, and pharmaceutical compositions containing them
GB732964A Expired GB1022744A (en) 1963-02-22 1964-02-21 New phenolic antimicrobial compositions

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB739964A Expired GB1024022A (en) 1963-02-22 1964-02-21 Process and materials for protection of organic materials against micro-organism contamination
GB732864A Expired GB1038185A (en) 1963-02-22 1964-02-21 New diphenyl ethers and processes for their production, and pharmaceutical compositions containing them

Country Status (15)

Country Link
AT (5) AT277471B (en)
AU (1) AU278661B2 (en)
BE (2) BE644153A (en)
BR (2) BR6457019D0 (en)
CH (4) CH431780A (en)
DE (2) DE1216882B (en)
DK (3) DK109518C (en)
ES (4) ES296709A1 (en)
FI (1) FI41831B (en)
FR (3) FR1385825A (en)
GB (3) GB1024022A (en)
IT (1) IT1149232B (en)
MY (2) MY6900160A (en)
NL (2) NL123731C (en)
SE (3) SE301324B (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3764696A (en) * 1967-08-01 1973-10-09 Ciba Geigy Corp Combatting bacteria with diphenyl thiocarbonates
EP0455475A2 (en) * 1990-05-03 1991-11-06 Reckitt And Colman Products Limited Use of triclosan in the treatment of diseases of the gastrointestinal tract
US5447923A (en) * 1993-09-20 1995-09-05 The Proctor & Gamble Company Methods and compositions of diphenyl ether phosphate esters for the treatment of gastrointestinal disorders
EP0908553A2 (en) * 1997-10-13 1999-04-14 Ciba SC Holding AG Process for the treatment of textile materials with an antimicrobial agent

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4118332A (en) * 1965-10-22 1978-10-03 Colgate-Palmolive Company Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides
US4057648A (en) 1970-05-16 1977-11-08 Ciba-Geigy Corporation Compositions for the control of microorganisms
BE750969A (en) 1970-05-26 1970-11-03 Geigy Ag J R COMPOSITION TO FIGHT MICRO-ORGANISMS,
US4284828A (en) * 1978-11-21 1981-08-18 Ciba-Geigy Corporation Process for the manufacture of 4,5-dichloro-2-(4-chlorophenoxy)phenol
DE3060975D1 (en) * 1979-11-16 1982-11-25 Ciba Geigy Ag Soap bar with an antimicrobial activity and process for the reduction of its discoloration
DE3004610A1 (en) * 1980-02-08 1981-08-13 Hoechst Ag, 6000 Frankfurt METHOD FOR PRODUCING 4-PHENOXYPHENOLS
US4490562A (en) * 1982-02-11 1984-12-25 Ciba-Geigy Corporation Process for the preparation of a very pure commercial form of 4,2',4'-trichloro-2-hydroxydiphenyl ether
GB8313634D0 (en) * 1982-06-18 1983-06-22 Ici Plc Halogenophenyl glyceride esters
CA1199273A (en) * 1982-07-15 1986-01-14 Ctibor Schindlery Anti-inflammatory composition
JPS611615A (en) * 1984-06-12 1986-01-07 Yougo Takaoka External drug for athlete's foot
FR2765469B1 (en) * 1997-07-07 1999-09-24 Elysees Balzac Financiere MATERIAL BASED ON REGENERATED CELLULOSE HAVING SUSTAINABLE RESISTANCE TO MICROORGANISMS AND PREPARATION THEREOF
US5968207A (en) * 1998-02-20 1999-10-19 Milliken & Company Esterified triclosan derivatives as improved textile antimicrobial agents
US6258455B1 (en) * 1999-03-29 2001-07-10 Sweports Limited Antimicrobial ultra-microfiber cloth
US7987539B2 (en) * 2004-03-23 2011-08-02 BASF SE Ludwigshafen Fungicidal detergent compositions

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE569726C (en) * 1930-05-09 1933-02-07 Ig Farbenindustrie Ag Process for the preparation of bis (halo-oxyaryl) oxides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3764696A (en) * 1967-08-01 1973-10-09 Ciba Geigy Corp Combatting bacteria with diphenyl thiocarbonates
EP0455475A2 (en) * 1990-05-03 1991-11-06 Reckitt And Colman Products Limited Use of triclosan in the treatment of diseases of the gastrointestinal tract
EP0455475A3 (en) * 1990-05-03 1992-02-26 Reckitt And Colman Products Limited Use of triclosan in the treatment of diseases of the gastrointestinal tract
US5286492A (en) * 1990-05-03 1994-02-15 Reckitt & Colman Products Limited Method of treatment of Heliobacter pylori infections with triclosan
US5447923A (en) * 1993-09-20 1995-09-05 The Proctor & Gamble Company Methods and compositions of diphenyl ether phosphate esters for the treatment of gastrointestinal disorders
EP0908553A2 (en) * 1997-10-13 1999-04-14 Ciba SC Holding AG Process for the treatment of textile materials with an antimicrobial agent
EP0908553A3 (en) * 1997-10-13 2001-03-07 Ciba SC Holding AG Process for the treatment of textile materials with an antimicrobial agent

Also Published As

Publication number Publication date
CH1509564A4 (en) 1967-10-14
MY6900159A (en) 1969-12-31
BR6457019D0 (en) 1973-08-28
MY6900160A (en) 1969-12-31
ES296707A1 (en) 1964-07-16
ES296708A1 (en) 1964-07-16
ES296709A1 (en) 1964-07-01
CH406127A (en) 1966-08-15
IT1149232B (en) 1986-12-03
AU278661B2 (en) 1967-10-24
DE1216882B (en) 1966-05-18
NL123731C (en) 1968-02-15
AT246725B (en) 1966-05-10
BE644153A (en) 1964-08-21
DK109518C (en) 1968-05-06
AT245555B (en) 1966-03-10
CH450348A (en) 1968-04-30
AT262512B (en) 1968-06-10
DK108923C (en) 1968-02-26
CH196564A4 (en) 1967-10-14
ES296710A1 (en) 1964-07-16
DE1492346A1 (en) 1971-11-11
FI41831B (en) 1969-12-01
AT277471B (en) 1969-12-29
AU4119464A (en) 1965-08-26
SE301324B (en) 1968-06-04
CH450347A (en) 1968-04-30
GB1038185A (en) 1966-08-10
AT245554B (en) 1966-03-10
NL6401661A (en) 1964-08-24
DE1793664A1 (en) 1972-04-13
GB1024022A (en) 1966-03-30
CH431780A (en) 1967-03-15
SE309781B (en) 1969-04-08
FR3486M (en) 1965-09-17
DK109146C (en) 1968-03-25
SE309780B (en) 1969-04-08
BE644154A (en) 1964-08-21
DE1793664B2 (en) 1975-08-28
CH225063A4 (en) 1965-09-30
BR6457018D0 (en) 1973-07-19
FR1385825A (en) 1965-01-15
FR1386731A (en) 1965-01-22
NL6401664A (en) 1964-08-24

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