US3369046A - 2-hydroxy-alkyl-benzyl quaternary ammonium compounds - Google Patents
2-hydroxy-alkyl-benzyl quaternary ammonium compounds Download PDFInfo
- Publication number
- US3369046A US3369046A US511247A US51124765A US3369046A US 3369046 A US3369046 A US 3369046A US 511247 A US511247 A US 511247A US 51124765 A US51124765 A US 51124765A US 3369046 A US3369046 A US 3369046A
- Authority
- US
- United States
- Prior art keywords
- quaternary ammonium
- hydroxyethyl
- ammonium compounds
- methyl
- chloride
- 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 - Lifetime
Links
- -1 AMMONIUM HALIDE Chemical class 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 27
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- 230000002421 anti-septic effect Effects 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000002324 mouth wash Substances 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000001805 chlorine compounds Chemical group 0.000 description 8
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 7
- 229940051866 mouthwash Drugs 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 210000003296 saliva Anatomy 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 230000003385 bacteriostatic effect Effects 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- 229910052736 halogen Chemical group 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
- 229940073608 benzyl chloride Drugs 0.000 description 3
- 150000001649 bromium compounds Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000002070 germicidal effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- BVYUYDBWQMSOKM-UHFFFAOYSA-N (4-bromophenyl)methanamine;hydron;chloride Chemical compound Cl.NCC1=CC=C(Br)C=C1 BVYUYDBWQMSOKM-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- LXVAZSIZYQIZCR-UHFFFAOYSA-N 2-nonyloxirane Chemical compound CCCCCCCCCC1CO1 LXVAZSIZYQIZCR-UHFFFAOYSA-N 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- QMIBIXKZPBEGTE-UHFFFAOYSA-N 2-tridecyloxirane Chemical compound CCCCCCCCCCCCCC1CO1 QMIBIXKZPBEGTE-UHFFFAOYSA-N 0.000 description 1
- ZKAPVLMBPUYKKP-UHFFFAOYSA-N 2-undecyloxirane Chemical compound CCCCCCCCCCCC1CO1 ZKAPVLMBPUYKKP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 description 1
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012956 testing procedure Methods 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
Definitions
- This invention relates to quaternary ammonium compounds and, more particularly, to 2-hydroxyalkyl quaternary ammonium compounds having a pronounced antiseptic character.
- antiseptic is used in its broad sense and is intended to include all bacteriological activity, including bacteriostatic and bactericidal activity.
- Quaternary ammonium compounds are Widely employed as germicidal agents due to their recognized microbial activity. They have been found to exhibit both bacteriostatic and bactericidal properties, as well as significant surface active properties. In view of these characteristics quaternary ammonium compounds have gained wide acceptance as effective agents for the sterilization of surgical and dental instruments, eating utensils, and food processing machinery and equipment.
- Quaternary ammonium compounds have been found to be particularly suited for such personal use in that they are eifective when used in solutions of moderate strength and also exhibit a prolonged bacteriostatic activity.
- Quaternary ammonium compounds may be characterized as nitrogen compounds in which four carbon atoms are directly linked to the nitrogen atom through covalent bonds and in which an anion is linked to the nitrogen atom through an electrovalent bond.
- Compounds which are illustrative of the general class of quaternary ammonium compounds include the alkenyldimethylethylammonium halides, alkenyltrimethylammonium halides, alkyldimethylbenzylamrnonium halides, alkyltrimethylammonium halides, dialkyldimethylammonium halides, and the like.
- R and R are the same or different groups such 3,369,046 Patented Feb. 13, 1968 ice as C to C alkyl groups, for example, methyl, ethyl, npropyl, isopropyl and the like, or a C to C alkanol group, such as ethanol, n-propanol, isopropanol and the like;
- R is an alkyl radical having from 6 to 18 carbon atoms, preferably from 6 to 16 carbon atoms, e.g., hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl and hexadecyl, heptadecyl, and nonadecyl;
- X is hydrogen or a halogen, such as chlorine, iodine or bromine; and Y is a halogen
- Illustrative quaternary ammonium compounds include N-propyl-N- Z-hydroxyethyl) -N- (2hydroxyoctyl -N- benzyl ammonium chloride,
- the preferred quaternary ammonium compounds are N-rnethyl-N- Z-hydroxyethyl) -N- 2-hydroxydodecyl) N-benzyl ammonium chloride and N-methyl-N- Z-hydroxyethyl) -N- 2-hydroxydodecyl) N-(p-bromobenzyl) ammonium bromide.
- novel 2-hydroxyalkyl quaternary ammonium compounds are prepared by condensing an appropriate 1,2- epoxyalkane with an equimolar amount of a suitable secondary amine to provide a tertiary amine characterized by the presence of a 2-hydroxy group on the longest alkyl radical attached to the nitrogen atom.
- the corre sponding quaternary ammonium compound is then prepared by condensing the thus prepared tertiary amine with an equimolar amount of a suitable arylalkyl halide compound, such as a benzyl halide or a p-halobenzyl halide.
- Illustrative 1,2-epoxyalkanes which can be used for the preparation of tertiary amines suitable for use in preparing the novel Z-hydroxyalkyl quaternary ammonium compounds include 1,2-epoxyoctane, l,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2epoxytridecane, 1,2-epoxytetradecane, 1,2- epoxypentadecane, 1,2-epoxyhexadecane, and the like as well as mixtures of these compounds, e.g., mixture of epoxyalkanes containing both even and odd numbers of carbon atoms in the alkyl chain.
- Illustrative secondary amine reactants include dimethylamine, diethylamine, methylethylamine, diethanolamine, dipropanolamine, methylmonoethanolamine and the like.
- Organic halides suitable for condensation with the tertiary amines referred to above include arylalkyl halides, such as benzyl chloride, benzyl bromide, benzyl iodide; halobenzyl halides, such as p-bromobenzyl bromide, pchlorobenzyl chloride and the like.
- bacteriologically active amounts represents that amount of the particular compound which will kill or inhibit the growth of microorganisms.
- factors such as possible contact time, the nature of the micro-organisms and the conditions under which the antiseptic composition is to be used determine what constitutes a bacteriologically active amount.
- Example 1Cndensati0n of LZ-epcrxyalkanes with merhyl-monoethanolamine N methyl N (2 hydroxyethyl) 2 hydroxyalkylamines were produced by heating a reaction mixture comprising 0.5 mole of a 1,2-epoxyalkane and 0.5 mole of methyl-monoethanolamine dissolved in about 75 milliliters of ethyl alcohol on a steam bath until a homogeneous solution was obtained. The temperature was then increased and the ethyl alcohol distilled oh; the final traces of ethyl alcohol were removed at reduced pressure.
- Table I presents data on a series of N-methyl-N-(2- hydroxyethyl)-2-hydroxyalkylamines prepared as described above.
- the alkyl groups shown in the first column of Table I represent R of Formula 1, above.
- Example 3 N methyl N (2 hydroxyethyl) (2-hydroxyalkyl)- N-benzyl ammonium chlorides were prepared by refluxing equimolar quantities (0.05 mole) of a tertiary amine prepared as described in Example 1, with benzyl chloride in 30 grams of ethanol. The reaction mixture was refluxed at 50 C. for 24 hours, after which it was cooled to room temperature and stored at room temperature for 10 days. At the end of this period, the ethanol was removed and the reaction product was stored over concentrated sulfuric acid at a pressure of 200 millimeters of mercury until the product crystallized.
- Example 5 N,N-bis(2-hydroxyethyl) N (2 hydroxyalkyl) N- benzyl ammonium chlorides were prepared by refluxing together equimolar amounts (0.1 mole) of an N-(Z-hydroxyalkyl) diethanolamine prepared as described in Example 2 and benzyl chloride in 75 milliliters of npropyl alcohol for a period of 6 hours. The n-propyl alcohol was then removed by evaporation. The last traces of n-propyl alcohol were removed by heating the reaction product to 54 C. at a pressure of 30 millimeters of mercury. The resulting product was then dried over concentrated sulfuric acid at a pressure of 0.5 millimeters of mercury.
- Quaternary ammonium compounds of the type described herein have been tested for germicidal activity and have been found to possess a significant degree of such activity.
- the minimum effective concentration for representative quaternary ammonium compounds was determined by means of a gradient plate tech nique in which agar plates having a gradual proportional increase in the concentration of antiseptic compound along the gradient axis were employed. Such plates are poured with two layers of nutrient, the bottom layer consisting of plain nutrient which is allowed to harden while the plate is slanted so that a wedge-shaped layer is formed. A second nutrient layer containing the antiseptic material is then poured while the plate is fiat. Downward diffusion of the antiseptic establishes a uniform linear concentration gradient during incubation. The plates are inoculated by streaking a bacterial culture suspension across the surface of the nutrient. The plates are incubated at 37 C. overnight and the extent of bacterial growth is measured.
- the Compound agamstinitial inoculum density is calculated from quadruplicate onguclear wli loop samples taken from a control tube incubated as above which is prepared by admixing 1 milliliter of 0.1 percent gy i-( r y hy i; -lay y- 44 84 peptone water and 1 milliliter of a 10* dilution of the iii g i ffii gi gfigt itfihfiigagg r--- pooled saliva.
- the average colony count in the control ggg gzg g- -tr y ammonium 1 66 multiplied by the dilution factor represents the initial fi idl(ifini-bfiifig iji i liififi dgi inoculum density of the test mixture. Since the test mixdodecyll-N'bemyl ammonium chloride tures containing mouthwash employ undiluted saliva, any 15 count showing the same number of colonies as the con- A group of quaternary ammonium compounds containtrol represents 99.9% kill of the initial inoculum. The ing a 2-hydroxy substituent in the longest alkyl chain was time required to effect a 99.9% kill is recorded.
- aureus Saliva Bacteriostatic activity was determined by an Agar Dilution Cup test (ADC) in which a standard Petri Dish NirInEethyl-N-(2-hylroxgeglyb- Z-hydroxydo ecy was filled w1th 40 milliliters of thioglycollate agar seeded 25 bemyl ammonium chloride M2 1p 4 3 at 1 percent with a culture of S. aureus. After hardening, 0. 05 3.5 2.7 M a cylnidrical plug is cut from the agar forming a cup into which is pipetted a 10 percent agar dilution of mouthbenzyl ammonium chloride.
- ADC Agar Dilution Cup test
- aureus is poured on a base of 40 milliliters of sterile N-methyl-N-(Z-hydroxyethyl)-N-(2 hydroxydodecyl)- thioglycollate agar in a Petri dish.
- Calf skin discs are then N-benzyl ammonium chloride in a mouthwash formulahydrated in distilled water, agitated in themouthwash sotion was compared to commercially available quaternary lution and thoroughly rinsed in water for 15 minutes.
- ammonium compounds at various concentration levels by Excess water is removed from the disc which is then the testing procedures described above. The results, placed on the surface of the prepared seed agar plate.
- Bactericidal activity was determined by a Bactericidal Contact Time test (BCT) in which whole saliva from a group of donors is pooled and then 1 milliliter of pooled
- BCT Bactericidal Contact Time test
- a quaternary ammonium halide having at least one 2-hydroxyalkyl substituent characterized by the formula wherein R and R are selected from the group consisting of alkyl groups having from 1 to 3 carbon atoms and hydroxyalkyl groups having from 2 to 3 carbon atoms; R; is an alkyl radical having from 6 to 18 carbon atoms; X is selected from the group consisting of hydrogen and halogen; and Y is a halogen.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Closures For Containers (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US511247A US3369046A (en) | 1965-12-02 | 1965-12-02 | 2-hydroxy-alkyl-benzyl quaternary ammonium compounds |
| SE16392/66A SE348459B (enrdf_load_stackoverflow) | 1965-12-02 | 1966-11-30 | |
| DEU13316A DE1274281B (de) | 1965-12-02 | 1966-11-30 | Keimtoetendes Mittel |
| NO165831A NO116914B (enrdf_load_stackoverflow) | 1965-12-02 | 1966-12-01 | |
| AT1111866A AT277967B (de) | 1965-12-02 | 1966-12-01 | Verfahren zur Herstellung von neuen quaternären Ammoniumverbindungen |
| ES0334038A ES334038A1 (es) | 1965-12-02 | 1966-12-01 | Procedimiento para preparar un haluro de amonio cuaternario. |
| DK624366AA DK124399B (da) | 1965-12-02 | 1966-12-01 | Kvaternært ammoniumhalogenid med desinficerende virkning. |
| FI3185/66A FI43368B (enrdf_load_stackoverflow) | 1965-12-02 | 1966-12-01 | |
| GB53767/66A GB1156027A (en) | 1965-12-02 | 1966-12-01 | Quaternary Ammonium Compounds |
| NL6616961A NL6616961A (enrdf_load_stackoverflow) | 1965-12-02 | 1966-12-01 | |
| BR185042/66A BR6685042D0 (pt) | 1965-12-02 | 1966-12-01 | Compostos de amonio quaternario |
| FR85822A FR1504196A (fr) | 1965-12-02 | 1966-12-01 | Composés d'ammonium quaternaires |
| BE690625D BE690625A (enrdf_load_stackoverflow) | 1965-12-02 | 1966-12-02 | |
| LU52502D LU52502A1 (enrdf_load_stackoverflow) | 1965-12-02 | 1966-12-02 | |
| CH1721866A CH512430A (de) | 1965-12-02 | 1966-12-02 | Verfahren zur Herstellung von quaternären Ammoniumhalogeniden und deren Verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US511247A US3369046A (en) | 1965-12-02 | 1965-12-02 | 2-hydroxy-alkyl-benzyl quaternary ammonium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3369046A true US3369046A (en) | 1968-02-13 |
Family
ID=24034079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US511247A Expired - Lifetime US3369046A (en) | 1965-12-02 | 1965-12-02 | 2-hydroxy-alkyl-benzyl quaternary ammonium compounds |
Country Status (15)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4852712A (enrdf_load_stackoverflow) * | 1971-10-29 | 1973-07-24 | ||
| US3928618A (en) * | 1972-04-10 | 1975-12-23 | Colgate Palmolive Co | Oral compositions |
| US3956479A (en) * | 1966-09-13 | 1976-05-11 | Colgate-Palmolive Company | Pharmaceutical composition containing novel quaternary ammonium compounds |
| US4042368A (en) * | 1975-06-27 | 1977-08-16 | Epic Chemical Inc. | Additive for quaternary amine bactericides and algicides, compositions containing same and method of manufacture |
| US4820507A (en) * | 1983-12-17 | 1989-04-11 | Henkel Kommanditgesellschaft Auf Aktien | Oral and dental hygiene preparations |
| US20050034651A1 (en) * | 2000-03-24 | 2005-02-17 | Ada Technologies, Inc. | Apparatus and method for removing mercury and mercuric compounds from dental effluents |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2305911C2 (de) * | 1973-02-07 | 1986-05-22 | Water Research Centre, Marlow, Buckinghamshire | Verwendung einer wäßrigen Masse als Schmiermittel für Rohr-Steckverbindungen |
| EP0026539B2 (de) * | 1979-10-02 | 1989-10-18 | Gaba International AG | Orale Kompositionen mit stabilisierten Zinnsalzen |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2759975A (en) * | 1952-05-28 | 1956-08-21 | Gen Aniline & Film Corp | Mixed alkyl-benzyl-alkylol quaternary ammonium salts |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH301409A (de) * | 1951-07-30 | 1954-09-15 | Friedrich Steinfels Ag Seifenf | Verfahren zur Herstellung einer quaternären Ammoniumverbindung. |
| CH303514A (de) * | 1951-07-30 | 1954-11-30 | Friedrich Steinfels Ag Seifenf | Verfahren zur Herstellung einer quaternären Ammoniumverbindung. |
| CH303510A (de) * | 1951-07-30 | 1954-11-30 | Friedrich Steinfels Ag Seifenf | Verfahren zur Herstellung einer quaternären Ammoniumverbindung. |
-
1965
- 1965-12-02 US US511247A patent/US3369046A/en not_active Expired - Lifetime
-
1966
- 1966-11-30 DE DEU13316A patent/DE1274281B/de active Pending
- 1966-11-30 SE SE16392/66A patent/SE348459B/xx unknown
- 1966-12-01 NL NL6616961A patent/NL6616961A/xx unknown
- 1966-12-01 GB GB53767/66A patent/GB1156027A/en not_active Expired
- 1966-12-01 FR FR85822A patent/FR1504196A/fr not_active Expired
- 1966-12-01 FI FI3185/66A patent/FI43368B/fi active
- 1966-12-01 AT AT1111866A patent/AT277967B/de not_active IP Right Cessation
- 1966-12-01 DK DK624366AA patent/DK124399B/da unknown
- 1966-12-01 NO NO165831A patent/NO116914B/no unknown
- 1966-12-01 BR BR185042/66A patent/BR6685042D0/pt unknown
- 1966-12-01 ES ES0334038A patent/ES334038A1/es not_active Expired
- 1966-12-02 CH CH1721866A patent/CH512430A/de not_active IP Right Cessation
- 1966-12-02 LU LU52502D patent/LU52502A1/xx unknown
- 1966-12-02 BE BE690625D patent/BE690625A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2759975A (en) * | 1952-05-28 | 1956-08-21 | Gen Aniline & Film Corp | Mixed alkyl-benzyl-alkylol quaternary ammonium salts |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3956479A (en) * | 1966-09-13 | 1976-05-11 | Colgate-Palmolive Company | Pharmaceutical composition containing novel quaternary ammonium compounds |
| JPS4852712A (enrdf_load_stackoverflow) * | 1971-10-29 | 1973-07-24 | ||
| US3928618A (en) * | 1972-04-10 | 1975-12-23 | Colgate Palmolive Co | Oral compositions |
| US4042368A (en) * | 1975-06-27 | 1977-08-16 | Epic Chemical Inc. | Additive for quaternary amine bactericides and algicides, compositions containing same and method of manufacture |
| US4820507A (en) * | 1983-12-17 | 1989-04-11 | Henkel Kommanditgesellschaft Auf Aktien | Oral and dental hygiene preparations |
| US20050034651A1 (en) * | 2000-03-24 | 2005-02-17 | Ada Technologies, Inc. | Apparatus and method for removing mercury and mercuric compounds from dental effluents |
Also Published As
| Publication number | Publication date |
|---|---|
| DK124399B (da) | 1972-10-16 |
| DE1274281B (de) | 1968-08-01 |
| SE348459B (enrdf_load_stackoverflow) | 1972-09-04 |
| NL6616961A (enrdf_load_stackoverflow) | 1967-06-05 |
| NO116914B (enrdf_load_stackoverflow) | 1969-06-09 |
| FI43368B (enrdf_load_stackoverflow) | 1970-11-30 |
| BR6685042D0 (pt) | 1973-12-18 |
| BE690625A (enrdf_load_stackoverflow) | 1967-06-02 |
| CH512430A (de) | 1971-09-15 |
| GB1156027A (en) | 1969-06-25 |
| AT277967B (de) | 1970-01-12 |
| LU52502A1 (enrdf_load_stackoverflow) | 1967-06-02 |
| FR1504196A (fr) | 1967-12-01 |
| ES334038A1 (es) | 1967-12-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3282775A (en) | Sporicidal compositions comprising a saturated dialdehyde and a cationic surfactant | |
| US3296145A (en) | Quaternary ammonium-tertiary amine oxide compositions | |
| US4587266A (en) | Antimicrobial compositions | |
| ES2200369T3 (es) | Composiciones limpiadoras y desinfectantes acidas espesadas. | |
| US2271378A (en) | Pest control | |
| US2246524A (en) | Germicide | |
| US3484523A (en) | Quaternary ammonium-tertiary amine oxide compositions | |
| US4865844A (en) | Method of treating tinea pedis and related dermatophytic infections | |
| US5215976A (en) | Phospholipids useful as spermicidal agents | |
| PL193943B1 (pl) | Kompozycja przeciwbakteryjna zawierająca alkohol i triklosan oraz emulsja przeciwbakteryjna | |
| JPS61140508A (ja) | 消毒製剤および殺菌洗浄製剤の賦活剤としてのアルキルグリコシドの用途 | |
| US3369046A (en) | 2-hydroxy-alkyl-benzyl quaternary ammonium compounds | |
| GB2300565A (en) | Antimicrobial agent containing quaternary ammonium salt | |
| RU96115269A (ru) | Антимикробная композиция с низкой токсичностью, содержащая четвертичный аммоний | |
| US3888947A (en) | Bis-biguanides | |
| KR970002875B1 (ko) | 저 함량의 자유 포름알데히드 메틸올히단토인의 제조방법 및 그 조성물 | |
| Ridenour et al. | Some factors affecting the properties of quaternary ammonium compounds as sanitizers | |
| US3198828A (en) | Compounds of citric acid | |
| US3888978A (en) | Certain phosphorus acid esters as disinfectants | |
| US4091113A (en) | Randomly terminated capped polymers | |
| US3303201A (en) | Halogenated anilides of thiophene carboxylic acids | |
| US3493615A (en) | Surfactant anti-microbial compounds | |
| US2918402A (en) | Bactericidal-fungicidal compositions | |
| JPS6024762B2 (ja) | 静菌及び殺菌剤組成物 | |
| JP3167724B2 (ja) | 沃素化合物を含む殺菌組成物 |