CH512430A - Verfahren zur Herstellung von quaternären Ammoniumhalogeniden und deren Verwendung - Google Patents
Verfahren zur Herstellung von quaternären Ammoniumhalogeniden und deren VerwendungInfo
- Publication number
- CH512430A CH512430A CH1721866A CH1721866A CH512430A CH 512430 A CH512430 A CH 512430A CH 1721866 A CH1721866 A CH 1721866A CH 1721866 A CH1721866 A CH 1721866A CH 512430 A CH512430 A CH 512430A
- Authority
- CH
- Switzerland
- Prior art keywords
- alkyl group
- quaternary ammonium
- formula
- chloride
- halogen
- Prior art date
Links
- -1 Quaternary ammonium halides Chemical class 0.000 title claims abstract description 28
- 230000000845 anti-microbial effect Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 17
- 230000002070 germicidal effect Effects 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000003512 tertiary amines Chemical class 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 210000003296 saliva Anatomy 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229960000228 cetalkonium chloride Drugs 0.000 claims description 2
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 claims description 2
- 229960001927 cetylpyridinium chloride Drugs 0.000 claims description 2
- VUFOSBDICLTFMS-UHFFFAOYSA-M ethyl-hexadecyl-dimethylazanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)CC VUFOSBDICLTFMS-UHFFFAOYSA-M 0.000 claims description 2
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 claims 1
- 239000002324 mouth wash Substances 0.000 abstract description 15
- 235000013305 food Nutrition 0.000 abstract description 5
- 239000000243 solution Substances 0.000 abstract description 5
- 239000004599 antimicrobial Substances 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 238000004140 cleaning Methods 0.000 abstract description 3
- 229910052740 iodine Inorganic materials 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 18
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 15
- 229940051866 mouthwash Drugs 0.000 description 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 239000000203 mixture Substances 0.000 description 9
- 229920001817 Agar Polymers 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- VNHUKFSXXYAFRU-UHFFFAOYSA-M benzyl-(2-hydroxydodecyl)-(2-hydroxyethyl)-methylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCC(O)C[N+](C)(CCO)CC1=CC=CC=C1 VNHUKFSXXYAFRU-UHFFFAOYSA-M 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000002421 anti-septic effect Effects 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000000844 anti-bacterial effect Effects 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 238000011081 inoculation Methods 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 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 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YLRBJYMANQKEAW-UHFFFAOYSA-N 1-bromo-4-(bromomethyl)benzene Chemical compound BrCC1=CC=C(Br)C=C1 YLRBJYMANQKEAW-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 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
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 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
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 2
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-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
- GXOYTMXAKFMIRK-UHFFFAOYSA-N 2-heptyloxirane Chemical compound CCCCCCCC1CO1 GXOYTMXAKFMIRK-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
- YJFSKTXFJSLNKF-UHFFFAOYSA-N 3-hexadecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCC1=CC=C[NH+]=C1 YJFSKTXFJSLNKF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VTGWDXBAGACBTG-UHFFFAOYSA-N CN(CCCCCCCCCCCCO)CCO Chemical compound CN(CCCCCCCCCCCCO)CCO VTGWDXBAGACBTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- CHQDMQJDPLMSTI-UHFFFAOYSA-M benzyl-(2-hydroxyethyl)-(2-hydroxytetradecyl)-methylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC(O)C[N+](C)(CCO)CC1=CC=CC=C1 CHQDMQJDPLMSTI-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- QDYLMAYUEZBUFO-UHFFFAOYSA-N cetalkonium chloride Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 QDYLMAYUEZBUFO-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000010630 cinnamon oil Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 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 1
- 230000000249 desinfective effect Effects 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
- 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 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine 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
- 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
- 239000000463 material Substances 0.000 description 1
- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 235000011837 pasties 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
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 125000004079 stearyl 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])[H] 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000000606 toothpaste Substances 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Birds (AREA)
- Epidemiology (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)
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 |
|---|---|
| CH512430A true CH512430A (de) | 1971-09-15 |
Family
ID=24034079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1721866A CH512430A (de) | 1965-12-02 | 1966-12-02 | Verfahren zur Herstellung von quaternären Ammoniumhalogeniden und deren Verwendung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3369046A (en]) |
| AT (1) | AT277967B (en]) |
| BE (1) | BE690625A (en]) |
| BR (1) | BR6685042D0 (en]) |
| CH (1) | CH512430A (en]) |
| DE (1) | DE1274281B (en]) |
| DK (1) | DK124399B (en]) |
| ES (1) | ES334038A1 (en]) |
| FI (1) | FI43368B (en]) |
| FR (1) | FR1504196A (en]) |
| GB (1) | GB1156027A (en]) |
| LU (1) | LU52502A1 (en]) |
| NL (1) | NL6616961A (en]) |
| NO (1) | NO116914B (en]) |
| SE (1) | SE348459B (en]) |
Families Citing this family (8)
| 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 |
| JPS5238008B2 (en]) * | 1971-10-29 | 1977-09-27 | ||
| US3928618A (en) * | 1972-04-10 | 1975-12-23 | Colgate Palmolive Co | Oral compositions |
| DE2305911C2 (de) * | 1973-02-07 | 1986-05-22 | Water Research Centre, Marlow, Buckinghamshire | Verwendung einer wäßrigen Masse als Schmiermittel für Rohr-Steckverbindungen |
| 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 |
| ATE11010T1 (de) * | 1979-10-02 | 1985-01-15 | Gaba International Ag | Orale kompositionen mit stabilisierten zinnsalzen. |
| DE3345781A1 (de) * | 1983-12-17 | 1985-06-27 | Henkel KGaA, 4000 Düsseldorf | Mund- und zahnpflegemittel |
| US6797178B2 (en) * | 2000-03-24 | 2004-09-28 | Ada Technologies, Inc. | Method for removing mercury and mercuric compounds from dental effluents |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| CH301409A (de) * | 1951-07-30 | 1954-09-15 | Friedrich Steinfels Ag Seifenf | Verfahren zur Herstellung einer quaternären Ammoniumverbindung. |
| US2759975A (en) * | 1952-05-28 | 1956-08-21 | Gen Aniline & Film Corp | Mixed alkyl-benzyl-alkylol quaternary ammonium salts |
-
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 BR BR185042/66A patent/BR6685042D0/pt unknown
- 1966-12-01 FR FR85822A patent/FR1504196A/fr not_active Expired
- 1966-12-01 FI FI3185/66A patent/FI43368B/fi active
- 1966-12-01 ES ES0334038A patent/ES334038A1/es not_active Expired
- 1966-12-01 NO NO165831A patent/NO116914B/no unknown
- 1966-12-01 GB GB53767/66A patent/GB1156027A/en not_active Expired
- 1966-12-01 AT AT1111866A patent/AT277967B/de not_active IP Right Cessation
- 1966-12-01 NL NL6616961A patent/NL6616961A/xx unknown
- 1966-12-01 DK DK624366AA patent/DK124399B/da unknown
- 1966-12-02 LU LU52502D patent/LU52502A1/xx unknown
- 1966-12-02 CH CH1721866A patent/CH512430A/de not_active IP Right Cessation
- 1966-12-02 BE BE690625D patent/BE690625A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK124399B (da) | 1972-10-16 |
| FR1504196A (fr) | 1967-12-01 |
| ES334038A1 (es) | 1967-12-16 |
| LU52502A1 (en]) | 1967-06-02 |
| AT277967B (de) | 1970-01-12 |
| NL6616961A (en]) | 1967-06-05 |
| US3369046A (en) | 1968-02-13 |
| GB1156027A (en) | 1969-06-25 |
| BR6685042D0 (pt) | 1973-12-18 |
| NO116914B (en]) | 1969-06-09 |
| FI43368B (en]) | 1970-11-30 |
| SE348459B (en]) | 1972-09-04 |
| DE1274281B (de) | 1968-08-01 |
| BE690625A (en]) | 1967-06-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1492331A1 (de) | Sporentoetende Mischung | |
| DE1593552A1 (de) | Verfahren zur Herstellung von neuen Salicylamid-Verbindungen | |
| DE2606519B2 (de) | Desinfizierende Zusammensetzung | |
| DE2711087C2 (en]) | ||
| CH512430A (de) | Verfahren zur Herstellung von quaternären Ammoniumhalogeniden und deren Verwendung | |
| DE2223766A1 (de) | Bis-biguanidsalze,Verfahren zu deren Herstellung und deren Verwendung | |
| DE2338031A1 (de) | Antimikrobielle komposition | |
| DE2947649A1 (de) | Insektizide mittel | |
| DE2530243C2 (de) | Verwendung von N-substituierten Aminoalkanolen als antimikrobielle Wirkstoffe | |
| DE3414933C2 (de) | Quaternäre Ammoniumverbindung und Desinfektionslösung, die eine quaternäre Ammoniumverbindung in wäßriger Lösung enthält | |
| DE68918785T2 (de) | Reiningungsmittel für die örtliche Desinfektion. | |
| EP0262587A2 (de) | Salicylsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE4241491C2 (de) | Verwendung von Bisbiguanidverbindungen | |
| DE3334555A1 (de) | Antimikrobielles gemisch | |
| DE1287259B (de) | Verwendung von Nitroalkoholen als Potenzierungsmittel in antimikrobiellen Mitteln | |
| DE2415981A1 (de) | Desinfektionszubereitung | |
| DE2833135A1 (de) | Verwendung von substituierten oligocarbamidinen als mikrobistatika sowie diese enthaltende antimikrobielle mittel | |
| DE2723118C3 (de) | Flüssige mikrobizide Mittel | |
| DE2536975C2 (en]) | ||
| DE2462073C2 (de) | Konservierungs- und Desinfektionsmittel | |
| DE1617135B2 (de) | Saure Reinigungsmittel mit antimikrobieller Wirksamkeit | |
| DE2008683C3 (de) | Desinfektionsmittel | |
| DE1668195C3 (de) | Brom-nitroalkyl-N-phenylcarbamate und diese enthaltende antimikrobiellen Mittel | |
| DE694005C (de) | Desinfektionsmittel | |
| DE1001854C2 (de) | Fungicide Mittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |