Quaternary ammonium compounds

• US 4,874,784 A
• Filed: 02/17/1989
• Issued: 10/17/1989
• Est. Priority Date: 10/01/1985
• Status: Expired due to Fees

• Current Assignee: Albemarle Corporation
• Original Assignee: Ethyl Corporation (Newmarket Corporation)
• Inventors: Smith, Kim R., Sauer, Joe D., Borland, James E.
• Primary Examiner(s): ROBINSON, ALLEN JAY
• Application Number:
  US07/312,125
• Time in Patent Office: 242 Days
• Field of Search: 514/517
• US Class Current: 514/517
• CPC Class Codes: A01N 33/12 Quaternary ammonium compounds
• CPC Class Codes: A01N 37/12 containing the group , wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
• CPC Class Codes: A01N 37/44 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
• CPC Class Codes: A01N 41/02 containing a sulfur-to-oxygen double bond
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: C07C 211/63 having quaternised nitrogen atoms bound to acyclic carbon atoms
• CPC Class Codes: C07C 215/90 with quaternised amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 217/08 the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 217/16 the six-membered aromatic ring or condensed ring system containing that ring not being further substituted
• CPC Class Codes: C07C 219/06 having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 229/12 to carbon atoms of acyclic carbon skeletons
• CPC Class Codes: C07C 255/24 containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
• CPC Class Codes: C07C 305/06 Hydrogenosulfates
• CPC Class Codes: C07C 317/28 with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 321/14 of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 323/25 the carbon skeleton being acyclic and saturated

Abstract

Quarternary ammonium compounds have the formula R¹ R² R³ N⁺ (CH₂)_m Y X^- wherein R¹ is an alkyl containing 8-20 carbon atoms, R² is an alkyl containing 8-20 carbon atoms or methyl or ethyl, R³ is methyl or ethyl, m is an integer from 1-6, X is an anion and Y is a group having the structure --Z, --OH, --OR⁴, --OC(O)R⁵, --CN, --O--S(O)(O)--OQ, --C(O)OR⁶, --C═CH, --SR⁷, --S(O)(O)R⁸, --S(O)R⁹, --NR¹⁰ R¹¹ and --CH═CH₂ wherein R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹ are alkyls containing 1-12 carbon atoms or are phenyl and Z is halogen and Q is hydrogen or a cation having been found to be very effective bactericides.

Claims

1. A method of inhibiting the growth of bacteria, said method comprising contacting said bacteria with a bactericidal amount of a quaternary ammonium compound having the formula:

##STR9## wherein R¹ is an alkyl containing 8-10 carbon atoms, R² is an alkyl containing 8-20 carbon atoms, methyl or ethyl, R³ is methyl or ethyl, m is an integer from 1 to 6, X is an anion and Y is ##STR10##

2. The method of claim 1 wherein said quaternary ammonium compound is dioctyl methyl 2-hydrosulfatoethyl ammonium bromide.

3. The method of claim 1 wherein said quaternary ammonium compound is nonyl dimethyl (sodium 4-sulfatobutyl) ammonium chloride.

4. The method of claim 1 wherein said quaternary ammonium compound is octadecyl diethyl 2-hydrosulfatoethyl ammonium fluoride.

5. The method of claim 1 wherein said quaternary ammonium compound is dodecyl dimethyl 2-sulfatoethyl ammonium chloride.

6. The method of claim 1 wherein said quaternary ammonium compound is octyl dimethyl 2-hydrosulfatoethyl ammonium chloride.

7. The method of claim 1 wherein said quaternary ammonium compound is decyl dimethyl 2-hydrosulfatoethyl ammonium bromide.

8. The method of claim 1 wherein said quaternary ammonium compound is dodecyl dimethyl 2-hydrosulfatoethyl ammonium bromide.

9. The method of claim 1 wherein said quaternary ammonium compound is tetradecyl dimethyl 2-hydrosulfatoethyl ammonium chloride.