US3390158A - Aromatic quaternary ammonium salts with disinfectant activity - Google Patents

Aromatic quaternary ammonium salts with disinfectant activity Download PDF

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Publication number
US3390158A
US3390158A US414833A US41483364A US3390158A US 3390158 A US3390158 A US 3390158A US 414833 A US414833 A US 414833A US 41483364 A US41483364 A US 41483364A US 3390158 A US3390158 A US 3390158A
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United States
Prior art keywords
chloride
ether
acetone
ammonium salts
quaternary ammonium
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Expired - Lifetime
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US414833A
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English (en)
Inventor
Janata Vladimir
Bydzovsky Viktor
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Spofa Vereinigte Pharma Werke
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Spofa Vereinigte Pharma Werke
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, 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
    • A01N37/44Biocides, 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 containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids

Definitions

  • the compounds of the invention are useful as disinfectants and can be made in solid crystalline form.
  • An example of the compounds of the invention is acarbethoxypentadecyl benzyldimethylammonium chloride.
  • the invention relates to new quaternary ammonium salts with disinfectant activity and to the method of preparing same.
  • Ri-CH-COOR2 wherein R is a straight or branched aliphatic chain with 1016 carbon atoms, R is a straight or branched alkyl with l-8 carbon atoms, cycloalkyl or aralkyl, R is an alkyl with 1-4 carbon atoms, and the substituents Y and Z, identical or different, stand for an atom of hydrogen, halogen, or a methoxy group, and X is a halogen atom, preferably chlorine.
  • the quaternary salts of the above quoted general Formula I represent altogether definable crystalline substances showing disinfectant effect enhanced by their surface activity. They are readily soluble in water, lower alcohols and glycols, capable of forming solutions of 30 percent or even higher concentrations, stable at normal tempera ture.
  • Crystalline and chemically homogenous substances of this kind are advantageous above all in that they can secure constant effectiveness of disinfectants prepared with them, that they can be used mostly in the form of aqueous solutions of various concentrations, and in that they offer the possibility of determining the disinfectant effect by external conditions, permitting the study of the mechanism of their effect, etc. From an economical standpoint also the shipment of crystalline substances appears more advantageous and easier than the expensive, uncomfortable, and sometimes diflicult to handle aqueous solutions.
  • the reaction can be carried out either without any medium, or in the medium of polar organic solvents, such as acetone, ether, ethly acetate, or dimet'hyl formamide, at a temperature within the range of normal temperature of 1525 up to C., and at atmospheric pressure, or with pressures up to 5 atm.
  • polar organic solvents such as acetone, ether, ethly acetate, or dimet'hyl formamide
  • the quaternary salt described in Example 5 can be prepared also by heating 12 g. butylester of a-dimethylaminopalmitic acid with 5 g. benzyl chloride to 90 C. for 6 hours. After cooling down the reaction mixture is allowed to stand for 12 hours at room temperature, in order to get crystallized the major part of the quaternary salt formed, thereupon it is stirred up with ether, and further processed to the final product in the way already described.
  • the mother liquor obtained in the crystallization of the crude quaternary salt is evaporated and the residue extracted with 15 ml. water and 7.5 ml. ether.
  • the aqueous extract is washed with ether, the ethereal extract in turn with water, and both evaporated. From the aqueous extracts further 1.5 g. of the crude quaternary salt is obtained, and from the ethereal extracts 2 g. of the unreacted starting cyclohexylester of tit-dimet-hylaminolauric acid recovered.
  • the quaternary salt described in Example 7 can be obtained also by heating 8 g. cyclohexylester of a-dimethylarninolauric acid with 3.2 g. benzyl chloride in 10 ml. acetone or dimethylformamide at 40 C. for 4 days.
  • the thus obtained crude quaternary salt is readily soluble in water, giving a clear solution, which forms a heavy sediment by shaking; the salt is soluble in alcohols, acetone and ether, while insoluble in petroleum ether; therefore it is purified by precipitation with petroleum ether from the ethereal solution, thus yielding an amorphous substance, which after some time crystallizes to form a light-yellow substance of fat-like consistence with a low M.P., the ot-carbethoxypentadecyl-/3.4-dimethoxybenzyl/ dimethylammonium chloride.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US414833A 1963-12-05 1964-11-30 Aromatic quaternary ammonium salts with disinfectant activity Expired - Lifetime US3390158A (en)

Applications Claiming Priority (1)

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CS673163 1963-12-05

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US3390158A true US3390158A (en) 1968-06-25

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US414833A Expired - Lifetime US3390158A (en) 1963-12-05 1964-11-30 Aromatic quaternary ammonium salts with disinfectant activity

Country Status (7)

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US (1) US3390158A (de)
AT (1) AT249662B (de)
BE (1) BE656646A (de)
CH (1) CH472375A (de)
DE (1) DE1518289A1 (de)
GB (1) GB1029228A (de)
NL (1) NL6414103A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110170164A1 (en) * 2010-01-08 2011-07-14 Ligang Wang Tunable thin-film filter

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4267344A (en) * 1972-09-22 1981-05-12 Proteinkemisk Institut. Tilknyttet Akademiet For De Tekniske Videnskaber N-Substituted N-carboxyanhydrides of α-amino acids and their application in the preparation of peptides
GB201605100D0 (en) 2016-03-24 2016-05-11 Nicoventures Holdings Ltd Vapour provision system
GB201605102D0 (en) 2016-03-24 2016-05-11 Nicoventures Holdings Ltd Mechanical connector for electronic vapour provision system
GB201605105D0 (en) 2016-03-24 2016-05-11 Nicoventures Holdings Ltd Vapour provision apparatus
GB201605101D0 (en) 2016-03-24 2016-05-11 Nicoventures Holdings Ltd Electronic vapour provision system
AU201617188S (en) 2016-07-15 2017-01-16 Nicoventures Holdings Ltd Cartomizer for a Vaping Device
CN109476408A (zh) 2016-07-22 2019-03-15 尼科创业控股有限公司 蒸汽供应装置外壳

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2459062A (en) * 1944-02-08 1949-01-11 American Cyanamid Co Quaternary ammonium compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2459062A (en) * 1944-02-08 1949-01-11 American Cyanamid Co Quaternary ammonium compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110170164A1 (en) * 2010-01-08 2011-07-14 Ligang Wang Tunable thin-film filter

Also Published As

Publication number Publication date
BE656646A (de) 1965-04-01
DE1518289A1 (de) 1969-05-22
CH472375A (de) 1969-05-15
AT249662B (de) 1966-10-25
GB1029228A (en) 1966-05-11
NL6414103A (de) 1965-06-07

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