DE2013375A1 - Antibacterial sulphuric acid salts - Google Patents
Antibacterial sulphuric acid saltsInfo
- Publication number
- DE2013375A1 DE2013375A1 DE19702013375 DE2013375A DE2013375A1 DE 2013375 A1 DE2013375 A1 DE 2013375A1 DE 19702013375 DE19702013375 DE 19702013375 DE 2013375 A DE2013375 A DE 2013375A DE 2013375 A1 DE2013375 A1 DE 2013375A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfinic acid
- sodium salt
- formula
- aqueous
- salts
- 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.)
- Pending
Links
- 230000000844 anti-bacterial effect Effects 0.000 title abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title 1
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229920000768 polyamine Polymers 0.000 claims abstract description 3
- -1 alkyl radicals Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 150000001412 amines Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 244000060011 Cocos nucifera Species 0.000 claims description 8
- 235000013162 Cocos nucifera Nutrition 0.000 claims description 8
- QRYAGUUNWIVCFG-UHFFFAOYSA-N [3-(dodecylamino)propylamino]methanesulfinic acid Chemical compound C(CCCCCCCCCCC)NCCCNCS(=O)O QRYAGUUNWIVCFG-UHFFFAOYSA-N 0.000 claims description 7
- 230000002353 algacidal effect Effects 0.000 claims description 6
- 230000000249 desinfective effect Effects 0.000 claims description 6
- 238000004140 cleaning Methods 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 150000003455 sulfinic acids Chemical class 0.000 claims description 4
- DXFZOZQSEKEDKT-UHFFFAOYSA-N (dodecylamino)methanesulfinic acid Chemical compound C(CCCCCCCCCCC)NCS(=O)O DXFZOZQSEKEDKT-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- GDNCXORZAMVMIW-UHFFFAOYSA-N dodecane Chemical compound [CH2]CCCCCCCCCCC GDNCXORZAMVMIW-UHFFFAOYSA-N 0.000 claims description 2
- XNEFVTBPCXGIRX-UHFFFAOYSA-N methanesulfinic acid Chemical class CS(O)=O XNEFVTBPCXGIRX-UHFFFAOYSA-N 0.000 claims description 2
- NDUSMKIINIYGHT-UHFFFAOYSA-N propylaminomethanesulfinic acid Chemical class C(CC)NCS(=O)O NDUSMKIINIYGHT-UHFFFAOYSA-N 0.000 claims description 2
- RLLGYHYJGZHKNF-UHFFFAOYSA-N (octadecylamino)methanesulfinic acid Chemical compound C(CCCCCCCCCCCCCCCCC)NCS(=O)O RLLGYHYJGZHKNF-UHFFFAOYSA-N 0.000 claims 1
- AJRPMXMNHNPNDD-UHFFFAOYSA-N [2-(dodecylamino)ethylamino]methanesulfinic acid Chemical compound C(CCCCCCCCCCC)NCCNCS(=O)O AJRPMXMNHNPNDD-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 239000000645 desinfectant Substances 0.000 abstract description 10
- 239000003619 algicide Substances 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000003899 bactericide agent Substances 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000012459 cleaning agent Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000004659 sterilization and disinfection Methods 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 3
- 241000737241 Cocos Species 0.000 description 3
- 241000195493 Cryptophyta Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 235000010419 agar Nutrition 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 3
- FGHHGPKVHYOUGV-UHFFFAOYSA-N 1-hydroxybutane-1-sulfinic acid Chemical compound CCCC(O)S(O)=O FGHHGPKVHYOUGV-UHFFFAOYSA-N 0.000 description 2
- LZCZEOOJQGXTAF-UHFFFAOYSA-N 1-hydroxypropane-1-sulfinic acid Chemical compound CCC(O)S(O)=O LZCZEOOJQGXTAF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000196169 Ankistrodesmus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- SAJLIOLJORWJIO-UHFFFAOYSA-N hydroxymethanesulfinic acid;sodium Chemical compound [Na].OCS(O)=O SAJLIOLJORWJIO-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NZTZKCVOQYVLDO-UHFFFAOYSA-N n'-[2-(didodecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCN(CCNCCN)CCCCCCCCCCCC NZTZKCVOQYVLDO-UHFFFAOYSA-N 0.000 description 2
- QCENGKPIBJNODL-UHFFFAOYSA-N n'-dodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCN QCENGKPIBJNODL-UHFFFAOYSA-N 0.000 description 2
- XMMDVXFQGOEOKH-UHFFFAOYSA-N n'-dodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCN XMMDVXFQGOEOKH-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 2
- LPMBTLLQQJBUOO-KTKRTIGZSA-N (z)-n,n-bis(2-hydroxyethyl)octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(CCO)CCO LPMBTLLQQJBUOO-KTKRTIGZSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- MNPWBESCUAMGHN-UHFFFAOYSA-N 1-hydroxyethanesulfinic acid Chemical class CC(O)S(O)=O MNPWBESCUAMGHN-UHFFFAOYSA-N 0.000 description 1
- UPFFQWNDECRHRY-UHFFFAOYSA-N 2-[2-(dodecylamino)ethylamino]acetic acid Chemical compound CCCCCCCCCCCCNCCNCC(O)=O UPFFQWNDECRHRY-UHFFFAOYSA-N 0.000 description 1
- JXJMYPUDIPBWSB-UHFFFAOYSA-N 2-bromoethanesulfinic acid Chemical compound OS(=O)CCBr JXJMYPUDIPBWSB-UHFFFAOYSA-N 0.000 description 1
- RRSCOUPNURHZBJ-UHFFFAOYSA-N 2-chloroethanesulfinic acid Chemical compound OS(=O)CCCl RRSCOUPNURHZBJ-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- KKIQAPWHIAUJSX-UHFFFAOYSA-N 3-bromopropane-1-sulfinic acid Chemical compound OS(=O)CCCBr KKIQAPWHIAUJSX-UHFFFAOYSA-N 0.000 description 1
- FLYMXAFCDJLWNS-UHFFFAOYSA-N 4-bromobutane-1-sulfinic acid Chemical compound OS(=O)CCCCBr FLYMXAFCDJLWNS-UHFFFAOYSA-N 0.000 description 1
- LIFHMKCDDVTICL-UHFFFAOYSA-N 6-(chloromethyl)phenanthridine Chemical compound C1=CC=C2C(CCl)=NC3=CC=CC=C3C2=C1 LIFHMKCDDVTICL-UHFFFAOYSA-N 0.000 description 1
- IAPQLUKIZKXZCM-UHFFFAOYSA-N 6-bromohexane-1-sulfinic acid Chemical compound OS(=O)CCCCCCBr IAPQLUKIZKXZCM-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001480043 Arthrodermataceae Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- DODSXGMGBLYCCV-UHFFFAOYSA-N C(CCCCCCCCCCC)NCCC(N)(S(=O)O)CCNCCCCCCCCCCCC Chemical class C(CCCCCCCCCCC)NCCC(N)(S(=O)O)CCNCCCCCCCCCCCC DODSXGMGBLYCCV-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000195585 Chlamydomonas Species 0.000 description 1
- 241000195649 Chlorella <Chlorellales> Species 0.000 description 1
- 244000249214 Chlorella pyrenoidosa Species 0.000 description 1
- 235000007091 Chlorella pyrenoidosa Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241001478778 Cladophora Species 0.000 description 1
- 241001465364 Cosmarium Species 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
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical class OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000199920 Ectocarpus Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000195620 Euglena Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 241000250507 Gigaspora candida Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000228404 Histoplasma capsulatum Species 0.000 description 1
- 241000502321 Navicula Species 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000192656 Nostoc Species 0.000 description 1
- 241000192497 Oscillatoria Species 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000195663 Scenedesmus Species 0.000 description 1
- 244000249201 Scenedesmus obliquus Species 0.000 description 1
- 235000007122 Scenedesmus obliquus Nutrition 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 241000196294 Spirogyra Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241001148696 Stichococcus Species 0.000 description 1
- 241001504046 Stichococcus bacillaris Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 241000192707 Synechococcus Species 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 241000200212 Vaucheria Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000037304 dermatophytes Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PQTSAJIDHPKODS-UHFFFAOYSA-N n'-[2-[2-(octadecylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCNCCNCCN PQTSAJIDHPKODS-UHFFFAOYSA-N 0.000 description 1
- FNDBKEJKVBORFC-UHFFFAOYSA-N n'-[3-(dodecylamino)propyl]propane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCNCCCN FNDBKEJKVBORFC-UHFFFAOYSA-N 0.000 description 1
- DXYUWQFEDOQSQY-UHFFFAOYSA-N n'-octadecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCCN DXYUWQFEDOQSQY-UHFFFAOYSA-N 0.000 description 1
- KPZNJYFFUWANHA-UHFFFAOYSA-N n'-octylpropane-1,3-diamine Chemical compound CCCCCCCCNCCCN KPZNJYFFUWANHA-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052572 stoneware Inorganic materials 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/50—Treatment of water, waste water, or sewage by addition or application of a germicide or by oligodynamic treatment
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Hydrology & Water Resources (AREA)
- Environmental & Geological Engineering (AREA)
- Water Supply & Treatment (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Alkylaminoalkyl-sulfinsaure Salze Die Erfindung betrifft neue alkylaminoalkyl-sulfinsaure Salze der allgemeinen Formel I 1 R-CnH2n-SO2M worin R eine sekundäre oder tertiä,re, I von einem geradkettigen oder verzweigten gesättigten aliphatischen Amin oder Polyamin abgeleitete, insgesamt 1 - 4 N-Atome und 8-- 40 C-Atome enthaltende Aminogruppe, die an mindestens einem N-Atom durch eine Alkylgruppe mit 8 - 18 C-Atomen substituiert ist, n eine ganze Zahl von i - 6 einschließ-. Alkylaminoalkyl-sulfinic acid salts The invention relates to new alkylaminoalkyl-sulfinic acid Salts of the general formula I 1 R-CnH2n-SO2M where R is a secondary or tertiary, I from a straight-chain or branched saturated aliphatic amine or polyamine derived amino group containing a total of 1 - 4 N atoms and 8--40 C atoms, substituted on at least one nitrogen atom by an alkyl group with 8-18 carbon atoms is, n including an integer from i - 6.
lich und M ein Aequivalent eines Metalls oder gegebenenfalls substituiertes Ammonium bedeuten. Lich and M is an equivalent of a metal or an optionally substituted one Mean ammonium.
Es wurde gefunden, daß dicse Verbindungen eine starke keimtötende Wirkung auf grampositive und gramnegative Bakterien sowie gute oberflächenaktive Eigenschaften besitzen und.daher als Desinfektions- und Reinigungsmittel verwendet werden können. So wurdenbeispielsweise verschiedene Bakterienstämme (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus) mit einer 0,005 C60,igen wässerigen Lösung des Natriumsalzes der 3-Dodecylaminopropylamino-methylsulfinsäure bei 220 innerhalb 1 Minute abgetötet, während unter den gleichen Bedingungen die mit einer 0,005 %igen wässerigen Lösung des Natriumsalzes der konstitutionell ähnlichen Dodecylaminoäthyl-aminoessigsäure (Handelspräparat) erzielten Abtötungszeiten 30 bzw. 2 bzw. 10 Minuten betrugen.These compounds have been found to be potent germicidal Effect on gram-positive and gram-negative bacteria as well as good surface-active Have properties and are therefore used as a disinfectant and cleaning agent can be. For example, different bacterial strains (Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus) with a 0.005 C60, igen water Solution of the sodium salt of 3-dodecylaminopropylamino-methylsulfinic acid at 220 killed within 1 minute, while under the same conditions those with a 0.005% aqueous solution of the sodium salt of the constitutionally similar dodecylaminoethylaminoacetic acid (Commercial preparation) achieved kill times were 30, 2 and 10 minutes.
Gegenüber den bakterizid wirksamen "Invertseifen" (langkettigen quartären Ammoniumverbindungen) zeichnen sich die neuen Verbindungen der Formel I durch stärkere Reinigungskraft sowie durch Verträglichkeit mit anionischen Seifen und mit Eiweiß aus.Compared to the bactericidal "invert soaps" (long-chain quaternary Ammonium compounds), the new compounds of the formula I are more powerful Cleaning power as well as compatibility with anionic soaps and with protein the end.
Ferner zeigen die Verbindungen der Formel I fungizide Wirkungen (gegen Dermatophyten, z.B. Trichophyton mentagrophytes,Hefe-, z.B. Candida albicans oder Histoplasma capsulatumZund Schimmelpilze, z .B. Aspergillus niger) sowie algizide Wirkungen (z,B gegen Organismen der Gattungen Anacystis,Ankistrodesmus, Bangia, Chara, Chlamydomonas, Chlorella, Cladophora, Cosmarium, Ectocarpus, Euglena, Navicula, Nostoc, Oscillatoria, Scenedesmus, Spirogyra, Stichococcus, Vaucheria); sie können daher auch als fungizide und/oder algizide Mittel verwendet werden. Insbesondere zeigte das genannte Natriumsalz der S-Dodecylamtno-propylaminomethylsulfinsäure gute Wirkungen gegen Ankistrodesmus braunii, Chlorella pyrenoidosa, Scenedesmus obliquus und Stichococcus bacillaris, Dabei lag die bakterizide Wirksamkeit in der gleichen Größenordnung wie die algizide Wirksamkeit; die Verbindungen sind daher besonders vorteilhaft als Schwimmbecken-Algizide verwendbar, da es nicht notwendig ist, gleichzeitig weitere Desinfektionsmittel (wie Chlorkalk) zuzusetzen.Furthermore, the compounds of the formula I show fungicidal effects (against Dermatophytes, e.g. Trichophyton mentagrophytes, yeast, e.g. Candida albicans or Histoplasma capsulatum and molds, e.g. Aspergillus niger) and algicides Effects (e.g. against organisms of the genera Anacystis, Ankistrodesmus, Bangia, Chara, Chlamydomonas, Chlorella, Cladophora, Cosmarium, Ectocarpus, Euglena, Navicula, Nostoc, Oscillatoria, Scenedesmus, Spirogyra, Stichococcus, Vaucheria); you can therefore can also be used as fungicidal and / or algicidal agents. In particular showed the mentioned sodium salt of S-dodecylamino-propylaminomethylsulfinic acid good effects against Ankistrodesmus braunii, Chlorella pyrenoidosa, Scenedesmus obliquus and Stichococcus bacillaris, the bactericidal effectiveness was in the same order of magnitude as the algicidal effectiveness; the connections are therefore Can be used particularly advantageously as a swimming pool algaecide, since it is not necessary is to add further disinfectants (such as chlorinated lime) at the same time.
Die algizide Wirkung kann nach folgenden Methoden ermittelt werden: a) Agar-PlattenTest: Man pipettiert 1 ml der Wirkstoff-Lösung auf ein steriles Filter und legt dieses auf eine Petrischale, die noch warmen Nähr-Agar (Zusammensetzung: 1 g Ca(NO3)2, 0,25 g MgSO4 # 7H2O, 0,25 g KKiP04, 0,25 g KNO3, 0,02 g FeS04, 30 g Agar, 3000 ml Wasser) enthält. Nach dem Erkalten setzt man einen Tropfen einer Suspension der betreffenden Algenart auf, hält 7 Tage bei Kunstlicht und wertet dann aus. In Kontrollversuchen entstehen an den Tropfstellen intensiv grdne Flecken.The algicidal effect can be determined using the following methods: a) Agar plate test: 1 ml of the active ingredient solution is pipetted onto a sterile filter and places it on a Petri dish, which is still warm nutrient agar (composition: 1 g Ca (NO3) 2, 0.25 g MgSO4 # 7H2O, 0.25 g KKiP04, 0.25 g KNO3, 0.02 g FeS04, 30 g agar, 3000 ml water). After cooling down, add a drop a suspension of the algae concerned, lasts 7 days in artificial light and evaluates then off. In control tests, intensely green stains appear at the drip points.
b) Schüttel-Test.b) shake test.
20 ml einer sterilisierten Nährlösung (Zusammensetzung wie bei a), aber ohne Agar-Zusatz) werden mit 0,2 ml Wirkstoff-Lösung und dann mit einer Aufschwemmung von ca. 106 Zellen der betreffenden Algenart in 1 ml Wasser versetzt. Man schdttelt anschließend 7 Tage bei 220 und Tageslicht unter Luftzutritt auf einem Schütteltisch mit 80 Bewegungen pro Minute und bestimmt danach die Zahl der Algenzellen durch Auszählen. 20 ml of a sterilized nutrient solution (composition as in a), but without the addition of agar) with 0.2 ml of active ingredient solution and then with a suspension of approx. 106 cells of the algae concerned are added to 1 ml of water. One shakes then 7 days at 220 and daylight with access to air on a shaking table with 80 movements per minute and then determines the number of algae cells Counting out.
Gegenstand der Erfindung sind somit alkylaminoalkyl-sulfinsaure Salze der Formel I sowie insbesondere solche der nachstehenden bevorzugten allgemeinen Formeln Ia bis Ip (worin R, n und M die bei Formel I angegebene Bedeutung haben und worin innerhalb desselben Moleküls mehrfach vorkommende Reste bzw. Indices R1, R2, m und p gleich oder voneinander verschieden sein können): Ia R1-(NR2-CmH2m)p-NR2-CnH2n-SO2M worin Rl Alkyl mit 8 - 18 C-Atomen, R2 H; Alkyl mit 1 - 18 C-Atomen oder R1-(NR2-CmH2m)p, n eine ganze Zahl von 2 - 6 einschließlich und p eine ganze Zahl von 0 - 3 einschließlich bedeuten; Ib R1-(NH-CmH2m)p-NR3-CnH2n-SO2M worin R3 H oder R1-(NH-CmH2m)p bedeutet und R1, m und p die bei Formel Ia angegebene Bedeutung haben.The invention thus relates to alkylaminoalkyl-sulfinic acid salts of the formula I and, in particular, those of the general ones preferred below Formulas Ia to Ip (in which R, n and M have the meanings given for formula I. and in which within the same molecule residues or indices R1 occurring several times, R2, m and p can be the same or different from one another): Ia R1- (NR2-CmH2m) p-NR2-CnH2n-SO2M wherein R1 is alkyl having 8-18 carbon atoms, R2 is H; Alkyl with 1 - 18 carbon atoms or R1- (NR2-CmH2m) p, n is an integer from 2 to 6 inclusive and p is an integer from 0 to 3 inclusive mean; Ib R1- (NH-CmH2m) p -NR3-CnH2n-SO2M where R3 is H or R1- (NH-CmH2m) p and R1, m and p have the meaning given for formula Ia.
Ic R1-(NH-CmH2m)p-NH-CnH2n-SO2M Id R1-NH-(CH2)m-NH-CnH2n-SO2M Ie R1-NH-CnH2n-SO2M If R1-(NR2-CmH2m)p-NR2-CH2-SO2M Ig R1-(NH-CmH2m)p-NR3-CH2-SO2M Ih R1-(NH-CmH2m)p-NH-CH2-SO2M Ii R1-NH-(CH2)m-NH-CH2-SO2M Ij R1-NH-CH2-SO2M Ik R1-(NR2-CmH2m)p-NR2-CH2Na Il R1-(NH-CmH2m)p-NR3-CH2-SO2Na Im R1-(NH-CmH2m)p-NH-CH2-SO2Na In R1-NH-(CH2)m-NH-CH2-SO2Na Io R1-NH-CH2-SO2Na Ip R*-NH-(CH2)3-NH-CH2-SO2Na worin den Dodecylrest oder ein Gemisch (nachstehend als "Cocos" bezeichnet) der Alkylreste von 8 - 18 C-Atomen, wie sie in den Aminen des natürlichen handelsüblichen Cocosfettamins vorliegen, bedeutet.Ic R1- (NH-CmH2m) p-NH-CnH2n-SO2M Id R1-NH- (CH2) m-NH-CnH2n-SO2M Ie R1-NH-CnH2n-SO2M If R1- (NR2-CmH2m) p-NR2-CH2-SO2M Ig R1- (NH-CmH2m) p-NR3-CH2-SO2M Ih R1- (NH-CmH2m) p-NH-CH2-SO2M Ii R1-NH- (CH2) m-NH-CH2-SO2M Ij R1-NH-CH2-SO2M Ik R1- (NR2-CmH2m) p-NR2-CH2Na Il R1- (NH-CmH2m) p-NR3-CH2- SO2Na Im R1- (NH-CmH2m) p-NH-CH2-SO2Na In R1-NH- (CH2) m-NH-CH2-SO2Na Io R1-NH-CH2-SO2Na Ip R * -NH- (CH2) 3-NH-CH2-SO2Na wherein the dodecyl radical or a mixture (hereinafter referred to as "Cocos") the alkyl radicals of 8-18 carbon atoms, such as them present in the amines of the natural commercial coconut fatty amine, means.
Unter den erfindungsgemäßen Salzen der Formeln I sowie Ia bis Ij sind die Alkalimetallsalze, insbesondere die Natriumsalze bevorzugt. Der Rest M kann aber auch ein Aequivalent eines anderen Metalles, z. B. K, Ca, Ba, Cu, Zn, Cd, Pb, Sn oder gegebenenfalls substituiertes Ammonium, z. 13. Pyridinium oder Mono-, Di- pzw. Triäthanolammonium, bedeuten.Among the salts according to the invention of the formulas I and Ia to Ij are the alkali metal salts, especially the sodium salts, are preferred. The rest M can but also an equivalent of another metal, e.g. B. K, Ca, Ba, Cu, Zn, Cd, Pb, Sn or optionally substituted ammonium, e.g. 13. Pyridinium or mono-, di- pzw. Triethanolammonium.
Gegenstand der Erfind-ung ist ferner ein Verfahren zur Herstellung von alkylaminoalkyl-sulfinsauren Salzen der Formel I, dadurch gekennzeichnet, daß man ein Amin der Formel II - II II mit einem sulfinsauren Salz der Formel III X-CnH2n-SO2M worin X eine gegebenenfalls funktionell abgewandelte 011-Gruppe, C1, Br oder J bedeutet, in wässerigem Medium zur Reaktion bringt.The invention also relates to a method of production of alkylaminoalkyl-sulfinic acid salts of the formula I, characterized in that an amine of the formula II - II II with a sulfinic acid salt of the formula III X-CnH2n-SO2M wherein X is an optionally functionally modified 011 group, C1, Br or J, reacts in an aqueous medium.
Als Amine der Formel II können unter anderen beispielsweise Octylamin, Dodecylamin, Palmitylamin (Hexadecylamin), Stearylamin (Octadecylamin), Dodecylaminoäthylamin, Dodecylaminopropylamin, Dodecylamino-polyäthylenamino-äthylamine, Dodecylamino-polypropylenamino-propylamine, Didodecyldiäthylentriamin (C12H25NHCH2CH2NHCH2CH2NHC12H25), das natürliche Cocosfettamingemisch ("Cocosamin"; ein Gemisch primärer Amine der allgemeinen Formel "Cocos"-NH2, worin der "Cocos"-Rest etwa 50 % C12H25 enthält) oder 3-"Cocosamino"-propylamin eingesetzt werden.As amines of the formula II, for example, octylamine, Dodecylamine, palmitylamine (hexadecylamine), stearylamine (octadecylamine), dodecylaminoethylamine, Dodecylaminopropylamine, Dodecylamino-polyethyleneamino-ethylamine, Dodecylamino-polypropylenamino-propylamine, Didodecyl diethylenetriamine (C12H25NHCH2CH2NHCH2CH2NHC12H25), the natural coconut fatty amine mixture ("Cocosamine"; a mixture of primary amines of the general formula "Cocos" -NH2, in which the "Cocos" residue contains about 50% C12H25) or 3- "Cocosamino" propylamine is used will.
Als sulfin-saure Salze der'Formel III kommen hauptsächlich die Salze, insbesondere das Natriumsalz, der llydroxymethansulfinsäure in Frage, ferner die Salze, insbesondere die Natriumsalze, beispielsweise der i-Hydroxyäthansulfinsäure, 2-Chloräthansulfinsäure, 1-Hydroxypropansulfinsäure, 1-Hydroxybutansulfindsäure.The sulfinic acid salts of Formula III are mainly the salts in particular the sodium salt, llydroxymethanesulfinic acid in question, also the Salts, especially the sodium salts, for example i-hydroxyethanesulfinic acid, 2-chloroethanesulfinic acid, 1-hydroxypropanesulfinic acid, 1-hydroxybutanesulfinic acid.
Zur herstellung der erfindungsgemäßen Verbindungen werden vorzugsweise äquimolare Mengen der beiden Komponenten in wässeriger Lösung bei einem pll-'irert zwischen 7 und 9 mehrere Stunden bei 40 - 800 gerührt. Aus der Reaktionslösung können die erfindungsgemäßen Verbindungen durch Eindampfen gewonnen werden. In dieser Weise werden sie als farblose viskos-ölige Substanzen erhalten, die durch Elementaranalyse1 sowie durch ihre Infrarot- und kernmagnetischen Resonanzspektren charakterisiert werden können.For the preparation of the compounds according to the invention, preference is given to Equimolar amounts of the two components in aqueous solution with a pll-'irert between 7 and 9 for several hours at 40-800. From the reaction solution can the compounds according to the invention can be obtained by evaporation. That way they are obtained as colorless viscous-oily substances, which by elemental analysis1 as well as characterized by their infrared and nuclear magnetic resonance spectra can be.
Nach den IR-Spektren enthalten die Endprodukte keine primären Aminogruppen. Außerdem kann man mit Oxydationsmitteln das Vorhandensein der Sulfinsäure-Gruppen nachweisen.According to the IR spectra, the end products do not contain any primary amino groups. In addition, one can detect the presence of sulfinic acid groups with oxidizing agents prove.
Die Reaktionslösungen können auch als solche, gegebenenfalls nach Verdünnen, z. 13. mit irassor und/oder mit vorzugsweise 5 - 20 Volumenprozent eines Alkohols mit 1 - 4 C-Atomen wie Methanol, Aethanol, n-Propanol, Isopropanol, n-Butanol oder Isobutanol, als Desinfektions- und Reinigungsmittel verwendet werden.The reaction solutions can also be used as such, if appropriate after Thinning, e.g. 13. with irassor and / or with preferably 5 - 20 percent by volume of one Alcohol with 1 - 4 carbon atoms such as methanol, ethanol, n-propanol, isopropanol, n-butanol or isobutanol, can be used as a disinfectant and cleaning agent.
Die erfindungsgemäßen Suflinsäuresalze weisen nach mehreren Monaten noch die volle baktericide Wirkung auf. Die entsprechenden Sulfonsäuresalze, die als mögliche Oxadationsprodukte der Sulfinsäuresalze in Frage kämen, sind um Zehnerpotenzen inaktiver.The sulfonic acid salts according to the invention show after several months the full bactericidal effect. The corresponding sulfonic acid salts that as possible oxadation products of the sulfinic acid salts are in the order of powers of ten more inactive.
Gegenstand der Erfindung sind ferner Desinfektions- und Reinigungsmittel, die nindestens eine Verbindung der Formel I enthalten. Diese Llittel werden, vorzugsweise in flüssiger Form, überall dort eingesetzt, wo neben einer gründlichen Desinfektion auch ihre ohnehin wertvolle Eigenschaft als Reinigungsmittel besonders gefordert ist.The invention also relates to disinfectants and cleaning agents, which contain at least one compound of the formula I. These means are, preferably in liquid form, used wherever in addition to thorough disinfection its already valuable property as a cleaning agent is also particularly in demand is.
Allgemein eignen sie sich zum Desinfizieren der menschlichen Haut sowie zur Desinfektion von Oberflächen, insbesondere z. B.In general, they are suitable for disinfecting human skin as well as for the disinfection of surfaces, especially z. B.
von Glas, Porzellan, Steinzeug, Holz, Metall, Kunststoffen.of glass, porcelain, stoneware, wood, metal, plastics.
Beispielsweise sind sie zur Desinfektion der Hände, zur Desinfektion von medizinischen Geräten (z.B. chirurgischen Instrumenten) oder zur Desinfektion von sanitären Anlagen gut geeignet.For example, they are used to disinfect the hands, for disinfection of medical devices (e.g. surgical instruments) or for disinfection well suited for sanitary facilities.
Weiterhin können sie bei der Verarbeitung, der Abpackung und dem Transport von Nahrungsmitteln verwendet werden, z. 13. zur des infoktion von Rohrleitungen in Lebensmittelbetrieben, von Milchkannen oder -flaschen.They can also be used during processing, packaging and transport used by food, e.g. 13. for the information of pipelines in food factories, from milk cans or bottles.
Als Desinfektions- und Reinigungsmittel werden insbesondere wässerige oder wässerig-alkoholische Konzentrate verwendet, die 0,1 bis 20 % der erfindungsgemäßen Verbindungen, besonders deren Alkalimetallsalze, enthalten und die nach Bedarf bis zu einem Gehalt von 0,00o IS herunter verdünnt werden. Aber auch höhere Verdünnungen sind noch bakterizid wirksam. Die Lösungen werden, falls erforderlich, durch Zugabe von Säuren, Laugen oder Puffersubstanzen im allgemeinen auf einen pH-Wert zwischen 7 und 12, vorzugsweise 8 und 9, eingestellt.In particular, water-based disinfectants and cleaning agents are used or aqueous-alcoholic concentrates used which contain 0.1 to 20% of the inventive Compounds, especially their alkali metal salts, contain and as required up to be diluted down to a content of 0.00% IS. But also higher dilutions are still bactericidal. The solutions are, if necessary, by adding of acids, alkalis or buffer substances in general to a pH value between 7 and 12, preferably 8 and 9, are set.
Die erfindungsgemäßen Desinfektions- und Reinigungsmittel können auch weitere Wirkstoffe enthalten. Beispielsweise, kann man den flüssigen Mitteln bei Bedarf anionische Seifen, z. B. Fettalkoholsulfate, Fettalkoholsulfonate, zusetzen. Die Wirkstoffe der Formel I können auch in feste Seifen eingearbeitet werden. The disinfectants and cleaning agents according to the invention can also contain other active ingredients. For example, one can use liquid funds if necessary, anionic soaps, e.g. B. fatty alcohol sulfates, fatty alcohol sulfonates, add. The active ingredients of the formula I can also be incorporated into solid soaps.
Die Mittel können beispielsweise ferner Zusätze an Verdickungsstoffen, (z.B. Celluloseäther wie Methylcellulose oder Carboxymethyleellulose, Traganth, Alginate, Agar-Agar, Gummi arabicum), Emulgatoren (z.B. Kondensationsprodukte aus Aethylenoxid und Rizinusöl, Sulfosuccinate wie Dioctylnatrium-sulfosuccinat, Sorbitan-fettsäureester oder Polyoxyäthylensorbitan-fettsäureester), Feuchthaltemitteln(z.B. Glycerin, Sorbit), Chelatbildnern(z.B. The agents can, for example, also contain additives to thickeners, (e.g. cellulose ethers such as methyl cellulose or carboxymethyl cellulose, tragacanth, Alginates, agar-agar, gum arabic), emulsifiers (e.g. condensation products from Ethylene oxide and castor oil, sulfosuccinates such as dioctyl sodium sulfosuccinate, sorbitan fatty acid esters or polyoxyethylene sorbitan fatty acid ester), humectants (e.g. glycerine, sorbitol), Chelating agents (e.g.
Salze der Aethylendiamintetraessigsäure), Enthärtungsmitteln (z*B. Polyphosphate), Farbstoffen, Parfüms enthalton. Salts of ethylenediaminetetraacetic acid), softening agents (e.g. Polyphosphates), coloring agents, perfumes containing.
Beispiel 1 92,6 g Dodeoylamin werden in 1 Liter Wasser mit 59 g hydroxymethansulfinsaurem Natrium 4 Stunden bei 60° gerührt. Das Wasser wird abdestillicrt, der Rückstand in Chloroform aufgenommen, mit Natriumsulfat getrocknet und nach Filtrat ion zur Trockne eingodampft. Man erhält 100 g farbloses Produkt der Zusammensetzung C13H28NNaO2S (Natriumsalz der Dodecylaminomethyl-sulfinsäure). Example 1 92.6 g of dodeoylamine are dissolved in 1 liter of water with 59 g of hydroxymethanesulfinic acid Sodium stirred for 4 hours at 60 °. The water is distilled off, the residue taken up in chloroform, dried with sodium sulfate and after Filtrat ion for Evaporated to dryness. 100 g of colorless product with the composition C13H28NNaO2S are obtained (Sodium salt of dodecylaminomethyl sulfinic acid).
Elementaranalyse: S 11,5 % (berechnet 11,2 %). Elemental analysis: S 11.5% (calculated 11.2%).
Analog crhält man mit Octylamin, Nonylamin, Decylamin, Undecylamin, Tridecylamin, Tetradecylamin, Pentadecylamin, Hexadecylamin, Heptadecylamin bzw. Octadecylamin die Natriumsalze der Octylaminomethyl-sulfinsäure Nonylaminomethyl-sulfinsäure Decylaminomethyl-sulfinsäure Undecylaminomethyl-sulfinsäure Tridecylaminomethyl-sulfinsäure Tetradecylaminomethyl-sulfinsäure Pentadecylaminomethyl-sulfinsäure Hexadecylaminomethyl-sulfinsäure Heptadecylaminomethyl-sulfinsäure Octadecylaminomethyl-sulfinsäure. The same applies to octylamine, nonylamine, decylamine, undecylamine, Tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine or Octadecylamine the sodium salts of octylaminomethyl sulfinic acid, nonylaminomethyl sulfinic acid Decylaminomethyl-sulfinic acid Undecylaminomethyl-sulfinic acid Tridecylaminomethyl-sulfinic acid Tetradecylaminomethyl sulfinic acid Pentadecylaminomethyl sulfinic acid Hexadecylaminomethyl-sulfinic acid Heptadecylaminomethyl-sulfinic acid Octadecylaminomethyl-sulfinic acid.
Analog erhält man mit dem natürlichen Cocosfettamingemisch ("Cocosamin") ein Gemisch der Natriumsalze der "Cocosamino"-methyl-sulfinsäuren.Similarly, with the natural coconut fatty amine mixture ("coconut amine") a mixture of the sodium salts of the "coconut amino" methyl sulfinic acids.
Beispiel 2 a) 12 g 3-Dodecylamino-propylamin werden in 250 ml Wasser mit 5,9 g hydroxymethansulfinsaurem Natrium 4 Stunden bei 600 gerührt. Nach Abdestillation des Wassers Wird in Chloroform gelöst, mit Natriumsulfat getrocknet und nach Filtration zur Trockne eingedampft. Man erhält 12 g farblose, ölige Substanz der Zusammensetzung zu Sr C161135N2Na02S (Natriumsalz der 3-Dodecylamino-propylaminomethylsulfinsäure). Sulfinsäure-Gehalt: 16,2 % SO2 (berechnet: 16,55 %). Kernresonanzspektrum: Signal für 2 Protonen bei # = 3,7 ppm.Example 2 a) 12 g of 3-dodecylaminopropylamine are dissolved in 250 ml of water stirred with 5.9 g of sodium hydroxymethanesulfinate for 4 hours at 600. After distillation of the water is dissolved in chloroform, dried with sodium sulfate and after filtration evaporated to dryness. 12 g of a colorless, oily substance of the composition are obtained to Sr C161135N2Na02S (sodium salt of 3-dodecylamino-propylaminomethylsulfinic acid). Sulphinic acid content: 16.2% SO2 (calculated: 16.55%). Nuclear magnetic resonance spectrum: signal for 2 protons at # = 3.7 ppm.
Analog erhält man mit 2-Dodecylamino-äthylamin, 3-Octylaminopropylamin, 3-Octadecyiamino-propylamin, 2-(2-Dodecylaminopropylamin)-äthylamin, 3-(3-Dodecylamino-propylamino)-propylamin, 2-[2-(2-Dodecylamino-äthylamino)-äthylaminl]-äthylamin bzw. 2-[2-(2-Octadecylamino-äthylamino)-äthylamino]-äthylamin die Natriumsalze der 2-Dodecylamino-äthylaminomethyl-sulfinsäure 3-Octylamino-propylaminomethyl-sulfinsäure 3-Octadecylamino-propylaminomethyl-sulfinsäure 2- (2-Dodooylamino-propylamino 5 3-(3-Dodecylamino-propylamino)-propylaminomethyl-sulfinsäure 2-[2-(2-Dodecylamino-äthylamino)-äthylamino]-äthylaminomethyl sulfinsäure 2-[2-(2-Octadecylamino-äthylamino)-äthylamino]-äthylaminomethylsulfinsäure b) 10 g des nach a) erhaltenen Natriumsalzes der 3-Dodecylaminopropylaminomethyl-sulfinsaure werden in 100 ml 40 %igem wässerigem Isopropanol gelöst. Man gibt die Lösung über eine Säule aus 7 g eines stark sauren Kationenaustauschers (z.B. Analogously with 2-dodecylamino-ethylamine, 3-octylaminopropylamine, 3-octadecylamino-propylamine, 2- (2-dodecylaminopropylamine) -ethylamine, 3- (3-dodecylamino-propylamino) -propylamine, 2- [2- (2-dodecylamino-ethylamino) -ethylamine] -ethylamine or 2- [2- (2-octadecylamino-ethylamino) -ethylamino] -ethylamine the sodium salts of 2-dodecylamino-ethylaminomethyl-sulfinic acid 3-octylamino-propylaminomethyl-sulfinic acid 3-Octadecylamino-propylaminomethyl-sulfinic acid 2- (2-Dodooylamino-propylamino 5 3- (3-Dodecylamino-propylamino) -propylaminomethyl-sulfinic acid 2- [2- (2-Dodecylamino-ethylamino) -ethylamino] -ethylaminomethyl sulfinic acid 2- [2- (2-octadecylamino-ethylamino) -ethylamino] -ethylaminomethylsulfinic acid b) 10 g of the sodium salt of 3-dodecylaminopropylaminomethylsulfinic acid obtained according to a) are dissolved in 100 ml of 40% aqueous isopropanol. The solution is handed over a column of 7 g of a strongly acidic cation exchanger (e.g.
E.Mcrok Ionenaustauscher I), läßt das Eluat in eine Lösung der berechneten Menge Pyridin in 20 ml 40 %igem Isopropanol einfließen und erhalt nach dem Eindampfen 10 g Pyridiniumsalz der 3-Dodecylamino-propylaminomethyl-sulfinsäure. E.Mcrok ion exchanger I), leaves the eluate in a solution of the calculated Pour the amount of pyridine into 20 ml of 40% isopropanol and obtain after evaporation 10 g pyridinium salt of 3-dodecylamino-propylaminomethyl-sulfinic acid.
Analog erhält man unter Verwendung berechneter Mengen anderer Basen wie Ammoniak, Piperidin, Triäthanolamin oder Kaliumhydroxid die entsprechenden Salze, z. B. das AI:1moniumsalz, Piperidiniumsalz, Triäthanolammoniumsalz, Kaliumsalz der 3-Dodecylamino-propylaminomethyl-sulfinsäure Beispiel 3 10,25 g t?Cocostrimethylendiamin1t (Duomeen # C) werden in 100 ml Wasser mit 5 g hydroxymethansulfinsaurem#Natrium 4 Stunden bei 50 gerührt. Man dampft die Reaktionslösung (A) ein, löst in Chloroform, trocknet über Na2S04, filtriert und dampft ein, wobei man eine farblose ölige Substanz (Gemisch der Natriumsalze der 3-"Cocosamino"-propylaminomethyl-sulfinsäuren) mit einem Sulfinsäure-Gehalt von 15,5 % SOa erhält. Kernresonanzspektrum: Signal für 2 Protonen bei # = 3,7 ppm. Analogously, using calculated amounts of other bases, one obtains such as ammonia, piperidine, triethanolamine or potassium hydroxide the corresponding salts, z. B. the AI: 1monium salt, piperidinium salt, triethanolammonium salt, potassium salt of 3-dodecylamino-propylaminomethyl-sulfinic acid Example 3 10.25 g t-cocostrimethylenediamine 1 t (Duomeen # C) are dissolved in 100 ml of water with 5 g of sodium hydroxymethanesulfinic acid Stirred at 50 for 4 hours. The reaction solution (A) is evaporated, dissolved in chloroform, dried over Na2S04, filtered and evaporated, leaving a colorless oily substance (Mixture of the sodium salts of 3- "Cocosamino" -propylaminomethyl-sulfinic acids) with a sulfinic acid content of 15.5% SOa. Nuclear magnetic resonance spectrum: signal for 2 protons at # = 3.7 ppm.
Analog erhält man mit den Natriumsalzen der 1-Hydroxyäthan-1-sulfinsäure, 1-Hydroxypropan-1-sulfinsäure, 1-Hydroxybutan-1-sulfinsäure, 1-Hydroxypentan-1-sulfinsäure, 1-Hydroxyhexan-1-sulfinsäure, 2-Hydroxy- bzw. 2-Chlor- bzw. 2-Brom-äthan-1-sulfinsAure, 3-iIydroxy- bzw. 3-Chlor- bzw. 3-Brom-propan-1-sulfinsäure, 4-Hydroxy- bzw. 4-Chlor- bzw. 4-Brombutan-1-sulfinsäure, 5-Hydroxy-bzw. 5-Chlor- bzw. 5-Brom-Pentan-1-sulfinsäure, 6-Hydroxy- bzw.Analogously, with the sodium salts of 1-hydroxyethane-1-sulfinic acid, 1-hydroxypropane-1-sulfinic acid, 1-hydroxybutane-1-sulfinic acid, 1-hydroxypentane-1-sulfinic acid, 1-hydroxyhexane-1-sulfinic acid, 2-hydroxy- or 2-chloro- or 2-bromo-ethane-1-sulfinic acid, 3-hydroxy or 3-chloro or 3-bromopropane-1-sulfinic acid, 4-hydroxy or 4-chloro or 4-bromobutane-1-sulfinic acid, 5-hydroxy or. 5-chloro- or 5-bromo-pentane-1-sulfinic acid, 6-hydroxy resp.
6-Chlor- bzw. 6-Brom-hexan-1-sulfinsäure die Gemische der Natriumsalze von 1-(3-"Cocosamino"-propylamino)-äthan-1-sulfinsäure 1-(3-"Cocosamino"-propylamino)-propan-1-sulfinsäure 1-(3-"Cocosamino"-propylamino)-butan-1-sulfinsäure 1-(3-"Cocosamino"-propylamino)-pentan-1-sulfinsäure 1-(3-"Cocosamino"-propylamino)-hexan-1-sulfinsäure 2-(3-"Cocosamino"-propylamino)-äthan-1-sulfinsäure 3-(3-"Cocosamino"-propylamino)-propan-1-sulfinsäure 4-(3-"Cocosamino"-propylamino)-butan-1-sulfinsäure 5-(3-"Cocosamino"-propylamino)-pentan-1-sulfinsäure 6-(3-"Cocosamino"-propylamino)-hexan-1-sulfinsäure Beispiel 4 20,4 g 2-(2-Dodecylamino-äthylamino)-äthylamin (Dodecyldiäthylentriamin) werden in 250 ml Wasser mit 8,8 g hydroxymethansulfinsaurem Natrium 4 Stunden bei 600 gerührt. Nach Abdestillation des Wassers wird in Chloroform gelöst, mit Natriumsulfat getrocknet und nach Filtration zur Trockne eingedampft. Man erhält 23 g farblose, ölige Substanz der Zusammensetzung C17H38N3NaO2S (Natriumsalz der 2-(2-Dodecylamino-äthylamino)-äthylaminomethylsulfinsäure). Elementaranalyse: N lt 11,1 d (berechnet: 11,3 5 S: 8,5 % (berechnet: 8,6 %) Beispiel 5 21,95 g Bis-(2-dodecylaminoäthyl)-amin (Didodecyldiäthylentriamin) werden in 300 nl Wasser mit 5,9 g hydroxymethansulfinsaurem Natrium 4 Stunden bei 600 gerührt. Das Wasser wird abdestilliert, der rückstand in Chloroform aufgenommen, mit Natriumsulfat getrocknet und zur Trockene eingedanpft. Man erhält 24 g farblose, ölige Substanz der Zusaimensetzung C29H62N3NaO2S (Gemisch der-Natriumsalze der Bis-(2-dodecylaminoäthyl)-aminomethylsulfinsäure und der N-Dodecyl-N-[2-(2-dodecylamino-äthylamino)-äthyl]-aminomethylsulfinsäure). Elementaranalyse: N 7,9 g0 (berechnet: 7,8 %); S 5,6 Cjo' berechnet: 5,9 %).6-chloro- or 6-bromo-hexane-1-sulfinic acid, the mixtures of the sodium salts from 1- (3- "Cocosamino" -propylamino) -ethane-1-sulfinic acid 1- (3- "Cocosamino" -propylamino) -propane-1-sulfinic acid 1- (3- "Cocosamino" -propylamino) -butane-1-sulfinic acid 1- (3- "Cocosamino" -propylamino) -pentane-1-sulfinic acid 1- (3- "Cocosamino" -propylamino) -hexane-1-sulfinic acid 2- (3- "Cocosamino" -propylamino) -ethane-1-sulfinic acid 3- (3- "Cocosamino" -propylamino) -propane-1-sulfinic acid 4- (3- "Cocosamino" -propylamino) -butane-1-sulfinic acid 5- (3- "Cocosamino" -propylamino) -pentane-1-sulfinic acid 6- (3- "Cocosamino" -propylamino) -hexane-1-sulfinic acid Example 4 20.4 g of 2- (2-dodecylamino-ethylamino) -ethylamine (dodecyl diethylenetriamine) are in 250 ml of water with 8.8 g of sodium hydroxymethanesulfinate for 4 hours 600 stirred. After the water has been distilled off, it is dissolved in chloroform with sodium sulfate dried and, after filtration, evaporated to dryness. 23 g of colorless, oily substance with the composition C17H38N3NaO2S (sodium salt of 2- (2-dodecylamino-ethylamino) -ethylaminomethylsulfinic acid). Elemental analysis: N lt 11.1 d (calculated: 11.3 5 S: 8.5% (calculated: 8.6%) Example 5 21.95 g of bis (2-dodecylaminoethyl) amine (didodecyl diethylenetriamine) are in 300 nl water with 5.9 g of sodium hydroxymethanesulfinate was stirred at 600 for 4 hours. The water is distilled off, the residue is taken up in chloroform with sodium sulfate dried and evaporated to dryness. 24 g of a colorless, oily substance are obtained the composition C29H62N3NaO2S (mixture of the sodium salts of bis (2-dodecylaminoethyl) aminomethylsulfinic acid and N-dodecyl-N- [2- (2-dodecylamino-ethylamino) -ethyl] -aminomethylsulfinic acid). Elemental analysis: N 7.9 g0 (calculated: 7.8%); S 5.6 Cjo 'calculated: 5.9%).
Verwendungsbeispiele: Beispiel A Die nach Beispiel 3 erhaltene Reaktionslösung (A) wird mit 10 ml Isopropanol versetzt und kann so direkt als DesinSektions- und Reinigungskonzentrat verwendet worden; der Gehalt an Natriumsalzen der 3-"Cocosamino"-propylaminomethyl-sulfinsäuren betrugt ca. 12 e/o, Nach Bedarf kann dieses Konzentrat verdünnt werden.Examples of use: Example A The reaction solution obtained according to Example 3 (A) is mixed with 10 ml of isopropanol and can be used directly as a disinfection and Cleaning concentrate has been used; the content of sodium salts of 3- "cocosamino" -propylaminomethyl-sulfinic acids was approx. 12 e / o, this concentrate can be diluted if necessary.
Beispiel B Eine Lösung von 20 Gewichtsteilen Natriumsalzen der 3-"Cocosamino"-propylaminomethyl-sulfinsäuren wird in einem Gemisch aus 20 Gewichtsteilen Isopropanol und 60 Gewiehtsteilen Wasser gelöst. Diese Lösung kann nach Bedarf verdünnt und dann in üblicher Weise, z. 3.Example B A solution of 20 parts by weight of sodium salts of 3-"cocosamino" propylaminomethylsulfinic acids is in a mixture of 20 parts by weight of isopropanol and 60 parts by weight of water solved. This solution can be diluted as required and then in the usual way, for. 3.
auch durch Versprühen, als Desinfektions- und Reinigungsmittel verwendet werden.also used by spraying, as a disinfectant and cleaning agent will.
Die nachstehenden Formulierungen werden durch Mischung der angegebenen Bestandteile erhalten (die Zahlen sind Gewichtsteile): Beispiel C: Desinfizierendes Allzweck-Reinigungsmittel (Konzentrat) Natriumsalz der Dodecylaminomethyl-sulfinsäure 10 Natrium-laurylsulfat a Oelsäurediäthanolamid 1 Acthylondiamintetraessigsaure-Natriumsalz 0,3 Isopropanol 20 Wasser G3,7 Beispiel D: Desinfizierendes Handwaschmittel Natriumsalz der 3-Dodecylamino-propylaminomethylsulfinsäure 0,5 Natrium-N-lauroyl-methyltaurid 10 Natrium-N-lauroyl-sarcosinat 10 Glycerin 2 Wasser 77,5 Beispiel E: Desinfizierendes Spülmittel (Konzentrat) Natriumsalze der 3-"Cocosamino"-propylaminomethylsulfinsäuren 10 Dodecylbenzolsulfonat (Triäthanolaminsalz) 2,5 Nonylphenol-polyglykoläther 1 Aethanol 10 Wasser 76,5 Beispiel F: Desinfizierendes Waschmittel (I(onzentrat) Natriumsalz der 2-(2-Dodecylamino-äthylamino)-äthylamino methyl-sulfinsäure 15 Fettalkohol-polyglykoläther 5 Triäthanolaminlaurylsulfat 10 Cocosfettsäurediäthanolamid 2 Isopropanol 15 Wasser 53The following formulations are made by mixing the specified Ingredients received (the numbers are parts by weight): Example C: Disinfectant All-purpose cleaning agent (concentrate) sodium salt of dodecylaminomethyl sulfinic acid 10 sodium lauryl sulfate a oleic acid diethanolamide 1 acylondiamine tetraacetic acid sodium salt 0.3 isopropanol 20 water G3.7 Example D: Disinfecting hand detergent Sodium salt of 3-dodecylamino-propylaminomethylsulfinic acid 0.5 Sodium-N-lauroyl-methyltauride 10 Sodium N-lauroyl sarcosinate 10 Glycerin 2 Water 77.5 Example E: Disinfectant Dishwashing detergent (concentrate) sodium salts of 3- "Cocosamino" -propylaminomethylsulfinic acids 10 Dodecylbenzenesulfonate (triethanolamine salt) 2.5 Nonylphenol polyglycol ether 1 Ethanol 10 Water 76.5 Example F: Disinfecting detergent (I (concentrate) sodium salt the 2- (2-dodecylamino-ethylamino) -ethylamino methyl sulfinic acid 15 fatty alcohol polyglycol ether 5 triethanolamine lauryl sulfate 10 coconut fatty acid diethanolamide 2 isopropanol 15 water 53
Claims (19)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702013375 DE2013375A1 (en) | 1970-03-20 | 1970-03-20 | Antibacterial sulphuric acid salts |
| GB24152/70A GB1261874A (en) | 1969-07-12 | 1970-05-19 | Alkylaminoalkylsulphonic acid salts |
| NL7007528A NL7007528A (en) | 1969-07-12 | 1970-05-25 | |
| IT26493/70A IT961362B (en) | 1969-07-12 | 1970-06-24 | ALKYLAMINOALKYLSULFINE SALTS |
| FR7025154A FR2054266A5 (en) | 1969-07-12 | 1970-07-07 | |
| BE753313D BE753313A (en) | 1969-07-12 | 1970-07-10 | ALCOYLAMINO-ALCOYL-SULFINIC ACID SALTS |
| JP45060342A JPS4829209B1 (en) | 1969-07-12 | 1970-07-11 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702013375 DE2013375A1 (en) | 1970-03-20 | 1970-03-20 | Antibacterial sulphuric acid salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2013375A1 true DE2013375A1 (en) | 1971-10-14 |
Family
ID=5765731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702013375 Pending DE2013375A1 (en) | 1969-07-12 | 1970-03-20 | Antibacterial sulphuric acid salts |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2013375A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1166780A3 (en) * | 2000-07-01 | 2002-07-24 | Beiersdorf AG | Use of physiologically acceptable sulfinic acid as antioxidant or radical scavenger in cosmetic or dermatologic preparations |
-
1970
- 1970-03-20 DE DE19702013375 patent/DE2013375A1/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1166780A3 (en) * | 2000-07-01 | 2002-07-24 | Beiersdorf AG | Use of physiologically acceptable sulfinic acid as antioxidant or radical scavenger in cosmetic or dermatologic preparations |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69129227T2 (en) | N, N'-DIHALOGENIMIDAZOLIDIN-4-ONE | |
| DE2164723C3 (en) | Antimicrobial agent and its use to fight bacteria, fungi and algae | |
| DE2510525C3 (en) | 2-alkyl imidazolium quaternary salts | |
| DE2309747A1 (en) | COMPOUNDS AND METHODS FOR TREATMENT OF WATER | |
| CH619112A5 (en) | ||
| DE19842116A1 (en) | Use of derivatives of methylenebisoxazolidine and compositions obtained thereby | |
| EP1189507A1 (en) | Disinfectants | |
| DE69329506T2 (en) | Quaternary ammonium ion polymers containing sulfur and their use as microbicides | |
| DE2248880A1 (en) | BIS- (2-PYRIDYL-1-OXIDE) -DISULPHIDE ADDUCTS WITH EARTH ALKALI METAL SALT, METHOD FOR THEIR PRODUCTION AND COSMETIC PREPARATIONS CONTAINING THESE ADDUCTS | |
| DE2808943A1 (en) | NEW GUANIDINIUM SALTS, THE PROCEDURE FOR THEIR PRODUCTION AND MICROBICIDAL PREPARATIONS CONTAINING THESE COMPOUNDS | |
| DE2635389C2 (en) | Preservatives and disinfectants | |
| DE2013375A1 (en) | Antibacterial sulphuric acid salts | |
| DE2244778C3 (en) | 1 -n-dodecylaminomethyl-2-aminocyclopentane, its production and use as a microbicidal active ingredient | |
| DE3307733C2 (en) | ||
| US3770817A (en) | Alkylaminoalkylsulfinic acid salts | |
| DE2504548A1 (en) | 2,3-DICYAN-5,6-DIHYDRO-P-DITHIINE, IN PARTICULAR WITH A FUNGICIDAL EFFECT | |
| DE1907149A1 (en) | Biocidal amino acid derivatives | |
| EP0081679A2 (en) | Substituted benzylimidazolium salts and microbicides containing them | |
| AT351316B (en) | FUNGICIDALS AND BACTERICIDAL AGENTS | |
| DE2738041A1 (en) | ANTIMICROBAL INGREDIENTS AND METHOD FOR THEIR PRODUCTION | |
| DE2247370C3 (en) | 1,3,3-Trimethyl-1-noctylaminomethyl-5-n-octylamino-cyclohexane, process for their preparation and their use as a microbicidal active ingredient | |
| DE1951156B1 (en) | Biocide preparation | |
| DE1642501C (en) | New biocidal compounds | |
| DE2244884C3 (en) | 1 -n-Octylaminomethyl ^ -n-octylamino-cyclopentane, a process for its production and its use as a microbicidal active ingredient | |
| DD234782A1 (en) | BIOZIDE MEDIUM |