US3708527A - Quaternary ammonium aryl carboxylic acid salts - Google Patents

Quaternary ammonium aryl carboxylic acid salts Download PDF

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Publication number
US3708527A
US3708527A US00010308A US3708527DA US3708527A US 3708527 A US3708527 A US 3708527A US 00010308 A US00010308 A US 00010308A US 3708527D A US3708527D A US 3708527DA US 3708527 A US3708527 A US 3708527A
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Prior art keywords
acid
formula
compounds
quaternary ammonium
residue
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US00010308A
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M Schellenbaum
M Duennenberger
F Casagrande
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Novartis AG
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Ciba Geigy AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/12—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • G—PHYSICS
    • G07—CHECKING-DEVICES
    • G07F—COIN-FREED OR LIKE APPARATUS
    • G07F7/00—Mechanisms actuated by objects other than coins to free or to actuate vending, hiring, coin or paper currency dispensing or refunding apparatus

Definitions

  • the subject of the invention are quaternary ammonium compounds of formula wherein A denotes an organic residue bonded to X by a carbon atom, X denotes a OO', SO or SO group, R denotes a higher molecular aliphatic residue, R denotes a monocyclic benzene residue, R and R each denote a short-chain divalent aliphatic residue and n denotes an integer-having a value of at most 2.
  • quaternary ammonium compounds of are of interest wherein A denotes an at most bicyclic aromatic residue, a monocyclic heterocyclic residue, a monocyclic cyloaliphatic residue, a monocyclic araliphatic residue or an aliphatic residue and R R R R X and n have the indicated significance.
  • Preferred quaternary ammonium compounds correspond to the formula (3) V liar-OH H: RrcHr-N lh] [GOX]] A,
  • A denotes an optionally substituted phenyl, diphenyl, furyl or thienyl residue bonded to X by a ring carbon atom, or an optionally substituted phenylalkyl, alkyl, alkenyl, phenylpolyglycol or thiodialkyl residue, and R R R 11,, X and n have the indicated significance.
  • the substituents of A, A A or A can for example be halogen atoms, alkyl residues or alkoxy residues.
  • Cycloaliphatic residues A preferably contain 3 to 5 ring members, Aliphatic residues A or A are appropriately built up from carbon chains which can also be interrupted by oxygen or sulphur atoms.
  • Y denotes a hydrogen atom, a halogen atom, an alkyl group with at most 4 carbon atoms, an alkoxy group with at most 2 carbon atoms, a hydroxyl group or a monocyclic benzene residue
  • Y and Y each denote a hydrogen atom, a halogen atom or an alkyl group with at most 4 carbon atoms
  • X, R R R and R have the indicated significance.
  • Y Y or Y represent halogen atoms, there are preferably chlorine atoms.
  • Possible alkyl groups for Y Y and Y are both straight-chain and branched residues, for example methyl, ethyl, n-propyl, isopropyl,n-butyl, and tert. butyl residues.
  • Y is preferably in the para-position to X.
  • quaternary ammonium compounds are derived from carboxylic acids and correspond to the formula wherein A, X, R R R R and n have the indicated significance.
  • Quaternary ammonium compounds of formula wherein r denotes an integer having a value of at most 3 and R R X, A and n have the indicated significance, are also of particular interest.
  • Quaternary ammonium compounds of formula wherein R denotes an alkyl residue containing 8 to 22, preferably 10 to 18, carbon atoms and R A, X and n have the indicated significance, are also particularly suitable.
  • the compounds of Formulae 1 to 17 are new and can I-Iere quaternary ammonium compounds of formula be manufactured according to methods which are in themwherein G denotes a methyl group or a hydrogen or selves known, by reaction of (a) a compound of formula chlorine atom and R Y Y Y and r have the in- (18) as e dicated significance should be highlighted.
  • Y denotes a hydrogen, chlorine or bro i atom ately reacted with one another in equivalent amounts, that or a hydroxyl, methyl, methoxy, butyl or phenyl residue, 15 y
  • Y denotes a hydrogen, chlorine or bro i atom ately reacted with one another in equivalent amounts, that or a hydroxyl, methyl, methoxy, butyl or phenyl residue, 15 y
  • 1 mol of a compound of Formula and R5 and G1 have the indicated i nifi n 18 is reacted with 1 mol of a compound of Formula 19,
  • the end products are as a rule colourless crystals.
  • the reaction medium as well as the cation Q and the anion Z of the starting products, must in each case be so chosen that either the salt [QZ] or the quaternary ammonium compound of Formula 1 separate out from the reaction mixture as an insoluble product and that either the quaternary ammonium compound or the salt [QZ] remains in solution.
  • the salt [QZ] precipitates and the compound of Formula 1 remains dissolved when working in an organic solvent as the reaction medium, and in the case of an aqueous reaction medium the compound of Formula 1 precipitates and the salt [QZ] remains in solution.
  • the component (a) in the form of an alkali metal salt is reacted with a halide of the component (b).
  • Possible halogen atoms are preferably chlorine or bromine atoms and alkali salts are above all sodium or potassium salts of the organic acids.
  • the compounds of Formulae 2 to 17 are manufactured by reacting (a) a compound of formula (20) o oat-X 4] or of formula or of formula 2 Y 3) 1 a Q9 o-X-- Y: or of formula or of formula wherein Q, A, A A A X, Y Y Y and n have the indicated significance, with (b) a compound of Formula 19 wherein R R R and R have the indicated significance and Z represents a halogen atom.
  • the monocyclic benzene residue of the starting compound of Formula 19 can be both substituted and unsubstituted.
  • Halogen atoms or alkyl residues with 1 to 4 carbon atoms as substituents are preferred.
  • R in Formulae 1 to 9, 19 or R in Formula 10 can thus for example represent a 4-chlorophenyl, 3,4-dichlorophenyl or 4-methylphenyl residue.
  • the compounds of Formulae 2 to 17 are accordingly manufactured by reaction of (a) a compound of Formula 18 or of Formulae 20 to 25 with (b) a compound of formula (26) (CH2CH10),H
  • R -CHzN R Z memo-Ln or of formula (27) CHZCHzOH Brent-Nita Z HzOHzOH or of formula (28) CH2GH2OH sCH2N- a Ze HzCHzOH or of formula or of formula wherein the residues R R R R G, G r and Z have the indicated significance.
  • both monobasic and dibasic acids can be used such as for example: acetic acid, chloracetic acid, trichloracetic acid, bromacetic acid, propionic acid, 2-chloropropionic acid, 3-chloropropionic acid, 2,2-dichloropropionic acid, 2,2-dimethylpropionic acid, butyric acid, isobutyric acid, valeric acid, isovaleric acid, caproic acid, heptylic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, acrylic acid, crotonic acid, vinylacetic acid, sorbic acid, undecylenic acid, oleic acid, linoleic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fum
  • a particularly surprising feature of the compounds of Formula 1 is the broad antibacterial range of action, which in some of these compounds extends both to gram-positive and also gram-negative bacteria.
  • the absence of odour and of colour of the compound of Formula 1 is of particular value as regards technical use aspects.
  • the present invention also comprises the use of the compounds of Formula 1 in combating pests quite generally.
  • the use of the antimicrobial compounds is possible on a very broad basis, especially for the protection of organic substrates against attack by destructive and pathogenic (also phytopathogenic) micro-organisms.
  • the antimicrobial agents mentioned are accordingly suitable both for use as preservatives and for use as disinfectants for technical products of all kinds, in plant protection, in agriculture, in veterinary medicine and in cosmetics.
  • non-textile technical products which can be preserved with the aid of the compounds of Formula 1, the following may be selected as examples: glues, adhesives, paints, textile aids or finishing agents, colour pastes and printing pastes and similar preparations based on organic and inorganic dyestuffs and pigments, including also those which contain casein or other organic compounds as admixtures.
  • Wall paints and ceiling paints for example those containing an albuminous colour binder, are also protected against attack by pests through an addition of the new compounds. The use for the protection of timber is also possible.
  • the compounds of Formula 1 can also be employed as preservatives in the cellulose and paper industry, inter alia for prevention of the known slime formation, caused by microorganisms, in equipment used for producing paper.
  • detergents and cleaning agents having an excellent antibacterial or anti-mycotic action are obtained by combining the compounds of Formula 1 with surfaceactive substances especially with detergent substances.
  • the compounds of Formula 1 can for example be incorporated into soaps or be combined with soap-free, detergent or otherwise surface-active substances, especially also non-ionic or cationic detergents, or can be combined together with mixtures of soaps and soap-free detergent substances, with their antimicrobial activity remaining fully preserved in these combinations.
  • aqueous preparations of such detergent and cleansing agents which contain compounds of Formula 1 it is for example possible to impart an antimicrobial finish to textile materials on washing, since the active substance can be substantively absorbed on the textile material.
  • Cleansing agents which contain the compounds of the above-mentioned formula can also be employed in industry and in households, as well as in the foodstuff trade, for example dairies, breweries and abattoirs.
  • the present compounds can also be used as a component of preparations which serve for the purpose of cleansing or disinfection.
  • the action of the compounds of Formula 1 can also be utilised in preservative and disinfectant finishes of plastics.
  • plasticisers it is advantageous to add the antimicrobial additive, dissolved or dispersed in the plasticiser, to the plastic. It is desirable to ensure as uniform as possible a distribution in the plastic.
  • the plastics with antimocrobial properties can be used for utensils of all kinds in which an activity against the most diverse germs, such as for example bacteria and fungi, is desired, as for example in doormats, bathroom curtains, lavatory seats, foot grids in swimming baths, wall coverings and the like.
  • Floor and furniture polishes with a disinfectant action are obtained by incorporation into appropriate wax and polishing compositions.
  • the compounds of Formula 1 can furthermore be used for the preservative and disinfectant finishing of fibres and textiles, it being possible to apply them to natural and synthetic fibres, where they develop a long-lasting action against harmful (including pathogenic) micro-organisms, for example fungi and bacteria.
  • the compounds can be added before, simultaneously with, or after a treatment of these textiles with other substances, for example dyestuffs or printing pastes, flameproofing agents, agents for softening the handle, and other finishes and the like.
  • Textiles treated in this way also show protection against the occurrence of perspiration odour, as is caused by microorganisms.
  • the antimicrobial active substances can be applied in the most diverse manner to the textile materials to be protected, for example by impregnation or spraying with solutions or suspensions which contain the abovementioned compounds as the active substance, or by successive impregnation r spraying with solutions of the starting compounds required for the manufacture of the active substances, with the active substance only being formed in situ on the material to be protected.
  • the active substance content can be between 1 and 30 g. of active substance per litre of treatment liquid.
  • textile materials of both synthetic or natural origin are adequately protected against fungal and bacterial attack by a content of 0.1 to 3% of active substance.
  • the active substances mentioned can be employed together with other textile auxiliaries such as finishing agents, creaseproof finishes and the like.
  • the use forms of the active substances according to the invention can correspond to the usual formulations of pesticides; for example, agents which contain the said active substances can optionally also contain additives such as solvents, dispersing agents, Wetting agents or adhesives and the like, as well as other pesticides.
  • the agents can however also contain a solid or liquid diluent or a solid or liquid carrier in addition to the active substance of Formula 1.
  • EXAMPLE 1 40 parts of benzyl-bis-(Z-hydroxyethyl)-dodecyl-ammonium chloride are dissolved in 70 parts of Water and added at 55 to 60 C. to a solution of 13.6 parts of ptoluic acid, 4 parts of sodium hydroxide and 50 parts of water. The mixture is stirred for a further hour at the same temperature and cooled to 10 C., whereupon the product of Formula 101 according to Table I precipitates in the form of colourless crystals. After recrystallising once from methanol-water, the product for analysis melts at 74 to 75 C.
  • EXAMPLE 2 A solution of 13.8 parts of salicylic acid in 50 parts by volume of methanol is mixed at 25 C., whilst stirring, firstly with 8.4 parts of sodium bicarbonate and then with 40.0 parts of benzyl-bis-(Z-hydroxyethyl)-dodecyl-ammonium chloride, after which the reaction mixture is boiled for minutes under refiux. The sodium chloride which has precipitated is filtered off and the filtrate evaporated in vacuo (12 mm. Hg).
  • the product of Formula 102 according to Table I is left as a viscous oil which crystallises on standing.
  • the yield is about 46 parts.
  • the product which has been purified by recrystallisation from ether or acetonitrile shows a melting point of 73 to 75 C.
  • EXAMPLE 3 A solution of 12.0 parts of 3-chlorobenzyl-di-(2-hydroxyethyl)-dodecyl-ammonium bromide in 25 parts of Water is added to 5.0 parts of diphenyl-4carboxylic acid and 1.4 parts of potassium hydroxide in 75 parts of water at C. over the course of 10 minutes. The reaction mixture is cooled to 5 C. and the product of Formula 130' according to Table II is filtered off, washed with water and dried. The yield is 14 parts; melting point to 108 C. The product which has been purified by recrystallisation from acetic acid ethyl ester melts at 110 to 111 C.
  • H 01 H 12 1 110-111 01 H H 12 1 ins-122.5 0 H H 01 12 1 122.5-123 9 H H CH3 12 1 s3-s5 o H H H s 1 118-119 H H H 12 2 on H H H 12 3 on H H H 18 1 118-11 0 H H H s 1 87-88 & H H H 12 2 on 0 H H H 12 3 on H H H 13 1 94.5-96
  • EXAMPLE 4 TABLEContinued Determination of the minimum inhibitory concentration Minimuminmbitow (MIC) against bacteria and fungi in the gradient plate Bacteriostasis Fungistasis 1 2 test Formula Staphylococcus Escherichia Aspergillus Trichophyton The compounds of Formula 1 1n the sultable formula- No. harm coli 'aigcr mentagrophytcs tions (for example as solutions in dimethylsulphoxide) of 3 1O 100 10 a certain concentration are mixed with warm brain heart 10 10 10 10 infusion agar (bacteria) and mycophil-agar (fungi) re- -2 i8 18 i8 spectively.
  • MIC Minimuminmbitow
  • the liquid mixtures are cast onto a solidified 4 10 1o 10 wedge-shaped base agar layer and are also allowed to 5 i3 38 $8 solidify. 2. 5 10 so 10
  • the test organisms are now applied in a line at right ,3 3?, 8 angles to the gradient by means of a Pasteur pipette. 2 i 10 g After an incubation of 24 hours at 37 C. (bacteria) or g 3 38 1 72 hours at C. (fungi) respectively, the length of 2 2.
  • g 5 g the germs which have grown on the inoculation smear are 6 60 20 10 measured and expressed in p.p.m. of active substance. 1 )0 198 fig 4.5 30 20 10 1 W.
  • Drying is carried out in a fully automatic drier at 80 C. for 90 minutes for cotton poplin and 60 minutes for cotton frott, respectively.
  • mm. diameter discs are placed on brain heart infusion agar plates which are inoculated beforehand with Staphylococcus aureus. The plates are thereafter incubated for 18 hours at 37 C.
  • the inhibition zone (HZ in mm.) arising around the discs, on the one hand, and the microscopically detectable growth (W in percent) under and on the fabric, on the other, are assessed.
  • the fabric finished by means of the combined treatment with laundry softening rinse agent and antimicrobial agent shows a good soft handle.
  • EXAMPLE 7 350 g. of 80% strength 3-(dimethylphosphono)-propionic acid methylolamide in 300 ml. of water, 80 g. of 60% strength pentamethylol-melamine-dimethyl-ether in 65 ml. of water and 20 g. of a 20% strength polyethylene emulsion in 40 ml. of water are mixed together.
  • the fabric finished by the combined treatment with fiameproofing agent and antimicrobial agent shows very good fiameproof behaviour.
  • the antimicrobial agent and the flameproofing agent do not mutually impair each others action.
  • R is alkyl containing 8 to 22 carbon atoms
  • r is l, 2 or 3,
  • Y is hydrogen or hydroXy
  • Y is hydrogen, chloro, bromo, and
  • Y is alkyl of l to 4 carbon atoms, chloro, phenyl,
  • R is alkyl containing 8 to 22 carbon atoms
  • Y Y and Y independently are hydrogen or alkyl with at most 4 carbon atoms.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US00010308A 1969-02-26 1970-02-10 Quaternary ammonium aryl carboxylic acid salts Expired - Lifetime US3708527A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH289769A CH509038A (de) 1969-02-26 1969-02-26 Verwendung von quaternären Ammoniumverbindungen zum antimikrobiellen Ausrüsten bzw. zum Schützen von Textilien gegen schädliche Mikroorganismen

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US3708527A true US3708527A (en) 1973-01-02

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US (1) US3708527A (enrdf_load_stackoverflow)
AT (1) AT298446B (enrdf_load_stackoverflow)
BE (1) BE746498A (enrdf_load_stackoverflow)
BR (1) BR7017046D0 (enrdf_load_stackoverflow)
CH (2) CH509038A (enrdf_load_stackoverflow)
CS (1) CS172323B2 (enrdf_load_stackoverflow)
DE (1) DE2007428A1 (enrdf_load_stackoverflow)
FR (1) FR2032745A5 (enrdf_load_stackoverflow)
GB (1) GB1292906A (enrdf_load_stackoverflow)
NL (1) NL7002679A (enrdf_load_stackoverflow)
SE (1) SE368701B (enrdf_load_stackoverflow)
SU (1) SU486504A3 (enrdf_load_stackoverflow)
ZA (1) ZA70912B (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4654175A (en) * 1982-05-12 1987-03-31 Xerox Corporation Organic sulfate and sulfonate compositions
US20040167195A1 (en) * 2002-01-07 2004-08-26 Rainer Muller Microbicidal agent and composition for cosmetic treatment containing it
US20050136015A1 (en) * 2003-12-17 2005-06-23 McKie Derrick B. Topical use of halosalicylic acid derivatives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK0906177T3 (da) * 1996-05-28 2002-07-08 Lonza Ag Trækonserveringsmidler

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4654175A (en) * 1982-05-12 1987-03-31 Xerox Corporation Organic sulfate and sulfonate compositions
US20040167195A1 (en) * 2002-01-07 2004-08-26 Rainer Muller Microbicidal agent and composition for cosmetic treatment containing it
US20050136015A1 (en) * 2003-12-17 2005-06-23 McKie Derrick B. Topical use of halosalicylic acid derivatives
WO2005058230A3 (en) * 2003-12-17 2006-02-02 Avon Prod Inc Topical use of halosalicylic acid derivatives

Also Published As

Publication number Publication date
BR7017046D0 (pt) 1973-02-08
SU486504A3 (ru) 1975-09-30
ZA70912B (en) 1971-04-28
GB1292906A (en) 1972-10-18
SE368701B (enrdf_load_stackoverflow) 1974-07-15
CH289769A4 (enrdf_load_stackoverflow) 1971-01-29
CH509038A (de) 1971-01-29
BE746498A (fr) 1970-08-25
NL7002679A (enrdf_load_stackoverflow) 1970-08-28
DE2007428A1 (de) 1970-09-17
FR2032745A5 (enrdf_load_stackoverflow) 1970-11-27
CS172323B2 (enrdf_load_stackoverflow) 1976-12-29
AT298446B (de) 1972-05-10

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