CH643589A5 - Cyclische amide enthaltende antibakterielle oberflaechenaktive mittel. - Google Patents
Cyclische amide enthaltende antibakterielle oberflaechenaktive mittel. Download PDFInfo
- Publication number
- CH643589A5 CH643589A5 CH881980A CH881980A CH643589A5 CH 643589 A5 CH643589 A5 CH 643589A5 CH 881980 A CH881980 A CH 881980A CH 881980 A CH881980 A CH 881980A CH 643589 A5 CH643589 A5 CH 643589A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- mol
- spectrum
- same
- cyclic amide
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 39
- 239000004094 surface-active agent Substances 0.000 title claims description 27
- -1 4- (2-hydroxyhexadecyl) aminoethyl-7-methyl-3,6-dihydro-2H-1,4-diazepine -5-one Chemical compound 0.000 claims description 91
- 150000001408 amides Chemical class 0.000 claims description 74
- 150000003950 cyclic amides Chemical class 0.000 claims description 23
- 150000007524 organic acids Chemical group 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004948 alkyl aryl alkyl group Chemical group 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- XGNTYYMJBAVALB-UHFFFAOYSA-N 4-[2-(dodecylamino)ethyl]-7-methyl-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCNCCN1CCN=C(C)CC1=O XGNTYYMJBAVALB-UHFFFAOYSA-N 0.000 claims description 2
- JYXYDLWBJAIUBM-UHFFFAOYSA-N 4-[2-[2-(dodecylamino)ethylamino]ethyl]-7-methyl-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCNCCNCCN1CCN=C(C)CC1=O JYXYDLWBJAIUBM-UHFFFAOYSA-N 0.000 claims description 2
- YGCIPINCUKCWDF-UHFFFAOYSA-N 6-methyl-4-[2-(tetradecylamino)ethyl]-2,3,6,7-tetrahydro-1,4-diazocin-5-one Chemical compound CCCCCCCCCCCCCCNCCN1CCN=CCC(C)C1=O YGCIPINCUKCWDF-UHFFFAOYSA-N 0.000 claims description 2
- VBHGJHCUFRHCCX-UHFFFAOYSA-N 4-[2-(2-hydroxyhexadecylamino)ethyl]-6-methyl-2,3,6,7-tetrahydro-1,4-diazocin-5-one Chemical compound CCCCCCCCCCCCCCC(O)CNCCN1CCN=CCC(C)C1=O VBHGJHCUFRHCCX-UHFFFAOYSA-N 0.000 claims 1
- ZNIXZCOKNYQVTF-UHFFFAOYSA-N 4-[2-(2-hydroxyhexadecylamino)ethyl]-6-methyl-3,6-dihydro-2h-1,4-diazepin-5-one Chemical group CCCCCCCCCCCCCCC(O)CNCCN1CCN=CC(C)C1=O ZNIXZCOKNYQVTF-UHFFFAOYSA-N 0.000 claims 1
- XHDVJMLRBCAHCO-UHFFFAOYSA-N 6-methyl-4-[2-(tetradecylamino)ethyl]-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCCCNCCN1CCN=CC(C)C1=O XHDVJMLRBCAHCO-UHFFFAOYSA-N 0.000 claims 1
- PORGQFKPWCSERF-UHFFFAOYSA-N n-[2-(5-methyl-7-oxo-3,6-dihydro-2h-1,4-diazepin-1-yl)ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCN1CCN=C(C)CC1=O PORGQFKPWCSERF-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 156
- 238000002329 infrared spectrum Methods 0.000 description 137
- 238000000921 elemental analysis Methods 0.000 description 133
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 81
- 150000001412 amines Chemical class 0.000 description 74
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 73
- TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 71
- 239000000047 product Substances 0.000 description 71
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- 230000015572 biosynthetic process Effects 0.000 description 63
- 150000001875 compounds Chemical class 0.000 description 40
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 34
- 150000003951 lactams Chemical class 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 25
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 19
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 229920000768 polyamine Polymers 0.000 description 13
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 12
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 10
- 229920001281 polyalkylene Polymers 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 239000012530 fluid Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 description 8
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 8
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 125000001183 hydrocarbyl group Chemical group 0.000 description 7
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 7
- KPFSGNRRZMYZPH-UHFFFAOYSA-M potassium;2-chloroacetate Chemical compound [K+].[O-]C(=O)CCl KPFSGNRRZMYZPH-UHFFFAOYSA-M 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 6
- 239000005639 Lauric acid Substances 0.000 description 6
- 238000005260 corrosion Methods 0.000 description 6
- 230000007797 corrosion Effects 0.000 description 6
- VVCYNVCCODBCOE-UHFFFAOYSA-N ethyl 2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C=O VVCYNVCCODBCOE-UHFFFAOYSA-N 0.000 description 6
- IZLFUDHPNDYYHS-UHFFFAOYSA-M potassium;2-bromoacetate Chemical compound [K+].[O-]C(=O)CBr IZLFUDHPNDYYHS-UHFFFAOYSA-M 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- QHQSHYOEXCBEKP-UHFFFAOYSA-N 1-[2-(2-aminoethylamino)ethylamino]hexadecan-2-ol Chemical compound CCCCCCCCCCCCCCC(O)CNCCNCCN QHQSHYOEXCBEKP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 235000021357 Behenic acid Nutrition 0.000 description 5
- 229910001369 Brass Inorganic materials 0.000 description 5
- 229910001018 Cast iron Inorganic materials 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 241000191967 Staphylococcus aureus Species 0.000 description 5
- 229910000831 Steel Inorganic materials 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229940116226 behenic acid Drugs 0.000 description 5
- 239000010951 brass Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- HWYJZXYVLPKDLM-UHFFFAOYSA-N methyl 2-methyl-3-oxopropanoate Chemical compound COC(=O)C(C)C=O HWYJZXYVLPKDLM-UHFFFAOYSA-N 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000010959 steel Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
- 239000005028 tinplate Substances 0.000 description 5
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- REIYHFWZISXFKU-UHFFFAOYSA-N Butyl acetoacetate Chemical compound CCCCOC(=O)CC(C)=O REIYHFWZISXFKU-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 4
- 239000012496 blank sample Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- TVXSKFHWYGYFIX-UHFFFAOYSA-N n'-[2-(tetradecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCNCCNCCN TVXSKFHWYGYFIX-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 241000605716 Desulfovibrio Species 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 238000010640 amide synthesis reaction Methods 0.000 description 3
- DOVJROOSBVOVCS-UHFFFAOYSA-N ethane-1,1,1,2,2-pentol Chemical compound OC(O)C(O)(O)O DOVJROOSBVOVCS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- XFKYUMYFILZJGG-UHFFFAOYSA-N methyl 2,2-dimethyl-3-oxopropanoate Chemical compound COC(=O)C(C)(C)C=O XFKYUMYFILZJGG-UHFFFAOYSA-N 0.000 description 3
- DVEKCXOJTLDBFE-UHFFFAOYSA-N n-dodecyl-n,n-dimethylglycinate Chemical compound CCCCCCCCCCCC[N+](C)(C)CC([O-])=O DVEKCXOJTLDBFE-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- SESSOVUNEZQNBV-UHFFFAOYSA-M sodium;2-bromoacetate Chemical compound [Na+].[O-]C(=O)CBr SESSOVUNEZQNBV-UHFFFAOYSA-M 0.000 description 3
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 2
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- VOKUMXABRRXHAR-UHFFFAOYSA-N 2-methyl-3-oxopropanoic acid Chemical class O=CC(C)C(O)=O VOKUMXABRRXHAR-UHFFFAOYSA-N 0.000 description 2
- USLIBZMIIDAESG-UHFFFAOYSA-N 4-dodecyl-7-methyl-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCN1CCN=C(C)CC1=O USLIBZMIIDAESG-UHFFFAOYSA-N 0.000 description 2
- UDKPLYKZVZCVOE-UHFFFAOYSA-N 7-methyl-4-(3-octoxypropyl)-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCOCCCN1CCN=C(C)CC1=O UDKPLYKZVZCVOE-UHFFFAOYSA-N 0.000 description 2
- 244000063299 Bacillus subtilis Species 0.000 description 2
- 235000014469 Bacillus subtilis Nutrition 0.000 description 2
- AXCQZCMANWYBSF-UHFFFAOYSA-N CCCCCCCCCCCCNC(C)NCCNCCCC1C(C)=NCCCNC1=O Chemical compound CCCCCCCCCCCCNC(C)NCCNCCCC1C(C)=NCCCNC1=O AXCQZCMANWYBSF-UHFFFAOYSA-N 0.000 description 2
- 241000605739 Desulfovibrio desulfuricans Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- KDPAWGWELVVRCH-UHFFFAOYSA-N bromoacetic acid Chemical compound OC(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- MEHIMRNYHHEUFC-UHFFFAOYSA-N methyl 2-methyl-4-oxobutanoate Chemical compound COC(=O)C(C)CC=O MEHIMRNYHHEUFC-UHFFFAOYSA-N 0.000 description 2
- DLZVZNAPRCRXEG-UHFFFAOYSA-N methyl 4-oxobutanoate Chemical compound COC(=O)CCC=O DLZVZNAPRCRXEG-UHFFFAOYSA-N 0.000 description 2
- JNOWMEDLDWPZGA-UHFFFAOYSA-N n'-(3-octoxypropyl)ethane-1,2-diamine Chemical compound CCCCCCCCOCCCNCCN JNOWMEDLDWPZGA-UHFFFAOYSA-N 0.000 description 2
- QCENGKPIBJNODL-UHFFFAOYSA-N n'-dodecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCN QCENGKPIBJNODL-UHFFFAOYSA-N 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- 229960003656 ricinoleic acid Drugs 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- OMKNAWLMVVVCLD-AATRIKPKSA-N (E)-oct-4-en-2-one Chemical compound CCC\C=C\CC(C)=O OMKNAWLMVVVCLD-AATRIKPKSA-N 0.000 description 1
- SURVUDPNZQGEJD-UHFFFAOYSA-N 1,4-diazepin-5-one Chemical compound O=C1C=CN=CC=N1 SURVUDPNZQGEJD-UHFFFAOYSA-N 0.000 description 1
- FPHKYQIDIXQGFS-UHFFFAOYSA-N 1-(1-aminopropan-2-ylamino)propan-2-ol Chemical compound CC(O)CNC(C)CN FPHKYQIDIXQGFS-UHFFFAOYSA-N 0.000 description 1
- ZYOIBBDPPTYGJR-UHFFFAOYSA-N 1-(6-methyl-8-oxo-2,3,4,7-tetrahydro-1h-1,5-diazocin-7-yl)propyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OC(CC)C1C(C)=NCCCNC1=O ZYOIBBDPPTYGJR-UHFFFAOYSA-N 0.000 description 1
- IQVUJBYYLBKJPY-UHFFFAOYSA-N 1-[2-(2-aminoethylamino)ethylamino]tetradecan-2-ol Chemical compound CCCCCCCCCCCCC(O)CNCCNCCN IQVUJBYYLBKJPY-UHFFFAOYSA-N 0.000 description 1
- OZYSEEDWQJGNSW-UHFFFAOYSA-N 1-[2-(octoxyamino)ethylamino]propan-2-ol Chemical compound CCCCCCCCONCCNCC(C)O OZYSEEDWQJGNSW-UHFFFAOYSA-N 0.000 description 1
- DBBZOURVEFUJEW-UHFFFAOYSA-N 1-n-dodecylpropane-1,2-diamine Chemical compound CCCCCCCCCCCCNCC(C)N DBBZOURVEFUJEW-UHFFFAOYSA-N 0.000 description 1
- UNBRWYDNGMTGDD-UHFFFAOYSA-N 16-methyl-N-[2-(5-methyl-7-oxo-3,6-dihydro-2H-1,4-diazepin-1-yl)ethyl]heptadecanamide Chemical compound C(CCCCCCCCCCCCCCC(C)C)(=O)NCCN1CCN=C(CC1=O)C UNBRWYDNGMTGDD-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- SUMZWDXUXLTFFX-UHFFFAOYSA-N 2,2-dimethyl-3-oxopropanoic acid Chemical compound O=CC(C)(C)C(O)=O SUMZWDXUXLTFFX-UHFFFAOYSA-N 0.000 description 1
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 1
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 description 1
- DEYKQSCMVQKCNU-UHFFFAOYSA-N 2-(6-methyl-7-oxo-3,6-dihydro-2h-1,4-diazepin-1-yl)ethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCN1CCN=CC(C)C1=O DEYKQSCMVQKCNU-UHFFFAOYSA-N 0.000 description 1
- OAAKYYCOMWZCTK-UHFFFAOYSA-N 2-ethyltetradecanamide Chemical compound CCCCCCCCCCCCC(CC)C(N)=O OAAKYYCOMWZCTK-UHFFFAOYSA-N 0.000 description 1
- RXJJIFUOUWVKTA-UHFFFAOYSA-N 2-methyl-4-oxobutanoic acid Chemical compound OC(=O)C(C)CC=O RXJJIFUOUWVKTA-UHFFFAOYSA-N 0.000 description 1
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 1
- KTLIZDDPOZZHCD-UHFFFAOYSA-N 3-(2-aminoethylamino)propan-1-ol Chemical compound NCCNCCCO KTLIZDDPOZZHCD-UHFFFAOYSA-N 0.000 description 1
- LJSUIIHXGIFTAO-UHFFFAOYSA-N 3-(3-aminopropylamino)propan-1-ol Chemical compound NCCCNCCCO LJSUIIHXGIFTAO-UHFFFAOYSA-N 0.000 description 1
- XKNRJOZQFHDNFT-UHFFFAOYSA-N 3-(7-methyl-8-oxo-2,3,6,7-tetrahydro-1,4-diazocin-1-yl)propyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCN1CCN=CCC(C)C1=O XKNRJOZQFHDNFT-UHFFFAOYSA-N 0.000 description 1
- QBUSZEPSFLRYAQ-UHFFFAOYSA-N 4-[2-(2-dodecoxyethylamino)ethyl]-7-methyl-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCOCCNCCN1CCN=C(C)CC1=O QBUSZEPSFLRYAQ-UHFFFAOYSA-N 0.000 description 1
- GSEZNBSCIMIKBL-UHFFFAOYSA-N 4-[2-(2-hydroxytetradecylamino)ethyl]-7-methyl-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCC(O)CNCCN1CCN=C(C)CC1=O GSEZNBSCIMIKBL-UHFFFAOYSA-N 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- ULNTZIDIVVUMNV-UHFFFAOYSA-N 7-methyl-4-[2-(tetradecylamino)ethyl]-3,6-dihydro-2h-1,4-diazepin-5-one Chemical compound CCCCCCCCCCCCCCNCCN1CCN=C(C)CC1=O ULNTZIDIVVUMNV-UHFFFAOYSA-N 0.000 description 1
- WYEVUSFYIBELBR-UHFFFAOYSA-N 7-methyl-7-[1-(tetradecylamino)ethyl]-1,2,3,4-tetrahydro-1,5-diazocin-8-one Chemical compound CCCCCCCCCCCCCCNC(C)C1(C)C=NCCCNC1=O WYEVUSFYIBELBR-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- HZMQEVKYXLHEAA-UHFFFAOYSA-N N-[2-(8-oxo-2,3,6,7-tetrahydro-1,4-diazocin-1-yl)ethyl]octanamide Chemical compound CCCCCCCC(=O)NCCN1CCN=CCCC1=O HZMQEVKYXLHEAA-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- XKGDWZQXVZSXAO-ADYSOMBNSA-N Ricinoleic Acid methyl ester Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OC XKGDWZQXVZSXAO-ADYSOMBNSA-N 0.000 description 1
- XKGDWZQXVZSXAO-SFHVURJKSA-N Ricinolsaeure-methylester Natural products CCCCCC[C@H](O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-SFHVURJKSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- SBXDIOUSGQVPAE-UHFFFAOYSA-N butyl 2,2-dimethyl-3-oxopropanoate Chemical compound CCCCOC(=O)C(C)(C)C=O SBXDIOUSGQVPAE-UHFFFAOYSA-N 0.000 description 1
- XYEAHHMVTWHTLR-UHFFFAOYSA-N butyl 2-methyl-4-oxobutanoate Chemical compound CCCCOC(=O)C(C)CC=O XYEAHHMVTWHTLR-UHFFFAOYSA-N 0.000 description 1
- HSPIFAMGAFNNTQ-UHFFFAOYSA-N butyl 4-oxobutanoate Chemical compound CCCCOC(=O)CCC=O HSPIFAMGAFNNTQ-UHFFFAOYSA-N 0.000 description 1
- BELZJFWUNQWBES-UHFFFAOYSA-N caldopentamine Chemical compound NCCCNCCCNCCCNCCCN BELZJFWUNQWBES-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 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
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- VIBDJEWPNNCFQO-UHFFFAOYSA-N ethane-1,1,2-triol Chemical compound OCC(O)O VIBDJEWPNNCFQO-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- UZVRCQLCLZZCOG-UHFFFAOYSA-N ethyl 2,2-dimethyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)(C)C=O UZVRCQLCLZZCOG-UHFFFAOYSA-N 0.000 description 1
- OPRPECIXNZNSTF-UHFFFAOYSA-N ethyl 2-methyl-4-oxobutanoate Chemical compound CCOC(=O)C(C)CC=O OPRPECIXNZNSTF-UHFFFAOYSA-N 0.000 description 1
- QFMPHCGACBODIJ-UHFFFAOYSA-N ethyl 4-oxobutanoate Chemical compound CCOC(=O)CCC=O QFMPHCGACBODIJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NALVEJDESUKJCS-UHFFFAOYSA-N n'-[2-(2-dodecoxyethylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCOCCNCCNCCN NALVEJDESUKJCS-UHFFFAOYSA-N 0.000 description 1
- RRHLGOOTLYHTEW-UHFFFAOYSA-N n'-[2-(dodecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCN RRHLGOOTLYHTEW-UHFFFAOYSA-N 0.000 description 1
- DWZJYSSNBXBMLS-UHFFFAOYSA-N n'-[2-[2-(dodecylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCNCCN DWZJYSSNBXBMLS-UHFFFAOYSA-N 0.000 description 1
- SLEYAGWXAGXUAS-UHFFFAOYSA-N n'-hexadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCNCCN SLEYAGWXAGXUAS-UHFFFAOYSA-N 0.000 description 1
- DDQBWEOPDZBVJW-UHFFFAOYSA-N n'-octadec-9-enylethane-1,2-diamine Chemical compound CCCCCCCCC=CCCCCCCCCNCCN DDQBWEOPDZBVJW-UHFFFAOYSA-N 0.000 description 1
- JVKAWJASTRPFQY-UHFFFAOYSA-N n-(2-aminoethyl)hydroxylamine Chemical compound NCCNO JVKAWJASTRPFQY-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- KJUFHTJXFMEKHZ-UHFFFAOYSA-N n-[2-(6-methyl-7-oxo-3,6-dihydro-2h-1,4-diazepin-1-yl)ethyl]dodecanamide Chemical compound CCCCCCCCCCCC(=O)NCCN1CCN=CC(C)C1=O KJUFHTJXFMEKHZ-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- VSFALEMGEHABMF-UHFFFAOYSA-N propan-2-yl 2,2-dimethyl-3-oxopropanoate Chemical compound CC(C)OC(=O)C(C)(C)C=O VSFALEMGEHABMF-UHFFFAOYSA-N 0.000 description 1
- RWMBBBSWXBGMEX-UHFFFAOYSA-N propan-2-yl 2-methyl-4-oxobutanoate Chemical compound CC(C)OC(=O)C(C)CC=O RWMBBBSWXBGMEX-UHFFFAOYSA-N 0.000 description 1
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- JLZOUIYSBSQWPN-UHFFFAOYSA-N propyl 4-oxobutanoate Chemical compound CCCOC(=O)CCC=O JLZOUIYSBSQWPN-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- XKGDWZQXVZSXAO-UHFFFAOYSA-N ricinoleic acid methyl ester Natural products CCCCCCC(O)CC=CCCCCCCCC(=O)OC XKGDWZQXVZSXAO-UHFFFAOYSA-N 0.000 description 1
- QPXCWKLWAQHVKP-UHFFFAOYSA-M sodium;[dimethyl(propyl)silyl]methanesulfonate Chemical compound [Na+].CCC[Si](C)(C)CS([O-])(=O)=O QPXCWKLWAQHVKP-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D245/00—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
- C07D245/02—Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/58—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/104—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/107—Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
- C10M2215/26—Amines
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/04—Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2217/046—Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials Engineering (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3825479A JPS55136268A (en) | 1979-03-30 | 1979-03-30 | Azalkenelactam having long chain hydrocarbon group, its betaine form, their preparation, and germicides and metal-corrosion inhibitor containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643589A5 true CH643589A5 (de) | 1984-06-15 |
Family
ID=12520168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH881980A CH643589A5 (de) | 1979-03-30 | 1980-03-28 | Cyclische amide enthaltende antibakterielle oberflaechenaktive mittel. |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4346087A (https=) |
| JP (1) | JPS55136268A (https=) |
| CH (1) | CH643589A5 (https=) |
| GB (1) | GB2065115B (https=) |
| WO (1) | WO1980002155A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9500810D0 (sv) | 1995-03-07 | 1995-03-07 | Perstorp Flooring Ab | Golvplatta |
| US7131242B2 (en) | 1995-03-07 | 2006-11-07 | Pergo (Europe) Ab | Flooring panel or wall panel and use thereof |
| US6441172B1 (en) * | 1996-11-07 | 2002-08-27 | Torrey Pines Institute For Molecular Studies | Diketodiazacyclic compounds, diazacyclic compounds and combinatorial libraries thereof |
| US7992358B2 (en) | 1998-02-04 | 2011-08-09 | Pergo AG | Guiding means at a joint |
| SE514645C2 (sv) | 1998-10-06 | 2001-03-26 | Perstorp Flooring Ab | Golvbeläggningsmaterial innefattande skivformiga golvelement avsedda att sammanfogas av separata sammanfogningsprofiler |
| SE518184C2 (sv) | 2000-03-31 | 2002-09-03 | Perstorp Flooring Ab | Golvbeläggningsmaterial innefattande skivformiga golvelement vilka sammanfogas med hjälp av sammankopplingsorgan |
| EP2124895A2 (en) * | 2006-12-22 | 2009-12-02 | Imuthes Limited | Lipids and their use as non-viral delivery vehicle |
| DE102010004717A1 (de) | 2010-01-15 | 2011-07-21 | Pergo (Europe) Ab | Set aus Paneelen umfassend Halteprofile mit einem separaten Clip sowie Verfahren zum Einbringen des Clips |
| CN104831904B (zh) | 2010-05-10 | 2017-05-24 | 佩尔戈(欧洲)股份公司 | 地板组件 |
| BR112013009966B1 (pt) | 2010-10-25 | 2019-04-09 | Stepan Company | Amina graxa, amidoamina graxa, derivado, formulação deglifosato, limpador de superfície áspera, formulação de detergente para vestuário sujo, produto de limpeza pessoalou sabonete, dispersante de parafina, espumante de poço de gás, inibidor de corrosão para uso em aplicações de campo petrolífero, tinta ou composição aditiva de revestimento,espumante, aditivo de espuma ou dispersante para uso em gesso, concreto ou aplicações de combate a incêndios |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH460441A (de) * | 1964-07-13 | 1968-07-31 | Agripat Sa | Fungizides Mittel und seine Verwendung |
-
1979
- 1979-03-30 JP JP3825479A patent/JPS55136268A/ja active Granted
-
1980
- 1980-03-28 CH CH881980A patent/CH643589A5/de not_active IP Right Cessation
- 1980-03-28 WO PCT/JP1980/000055 patent/WO1980002155A1/ja not_active Ceased
- 1980-03-28 US US06/224,520 patent/US4346087A/en not_active Expired - Lifetime
- 1980-03-28 GB GB8038038A patent/GB2065115B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6312067B2 (https=) | 1988-03-17 |
| WO1980002155A1 (fr) | 1980-10-16 |
| US4346087A (en) | 1982-08-24 |
| JPS55136268A (en) | 1980-10-23 |
| GB2065115B (en) | 1983-04-20 |
| GB2065115A (en) | 1981-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69032819T2 (de) | Mikrobizide Zusammensetzungen von Dimethylamin-Epichlorhydrin-Amin-Polymeren | |
| DE69204054T2 (de) | Diaminacetat enthaltende antimikrobenschmiermittelzusammensetzung. | |
| DE69308974T2 (de) | Überbasische,natürliche öle als additive für schmiermittel,kunststoffe,antriebmittel, tinten und schmierfette | |
| DE2902380C2 (de) | Verwendung von wäßrigen Lösungen von Alkanolaminsalzen von Polyoxyalkylenverbindungen als Schmiermittel | |
| DE1810852A1 (de) | Herstellung oelloeslicher Borderivate komplexer substituierter Alkylenpolyamine | |
| DE1570870B2 (de) | Aminacylierungsprodukte von kohlenwasserstoffsubstituierter Bernsteinsäure und deren Verwendung | |
| DE2233295A1 (de) | Verfahren zur herstellung von schmieradditiven | |
| DE2213152B2 (de) | Verwendung eines hydroxyalkyl- substituierten polyamins als ein die oxidationsstabilitaet sowie die reinigungs- und dispersionseigenschaften verbessernder bestandteil einer schmieroelmischung | |
| DE2745909A1 (de) | Kombination von schmieroelzusaetzen | |
| CH643589A5 (de) | Cyclische amide enthaltende antibakterielle oberflaechenaktive mittel. | |
| DE3225000C2 (https=) | ||
| DE69207406T2 (de) | Verfahren zur herstellung eines amid-produktgemisches, ein amid-produktgemisch und seine verwendung | |
| EP0249162A1 (de) | Verwendung von acylierten 3-Amino-1,2,4-triazolen als Korrosionsinhibitoren für Buntmetalle | |
| DE2648240C3 (de) | Verfahren zur Herstellung von SUylalkylaminhydrochloriden | |
| DE3022263C2 (de) | Verfahren zur Herstellung von Dispergier-Additiven für Schmiermittel | |
| DE2722819A1 (de) | Korrosionsinhibierendes kuehl- und metallbearbeitungsmittel | |
| DE69432153T2 (de) | Erhöhung der reibungsbeständigkeit von kraftübertragungsflüssigkeiten durch die verwendung von öllöslichen konkurierenden additiven | |
| DE69821084T2 (de) | Reduzierung der Oberflächenenergie mit hohen alkylierten Polyaminen | |
| DE69126560T2 (de) | Verfahren zur Herstellung von Esterderivaten, ihre Verwendung als Kraftstoff- und Schmierstoffadditive sowie danach hergestellte Esterverbindungen | |
| DE1745812A1 (de) | Schmieroel | |
| EP2828419B1 (de) | Wässrige oberflächenaktive und korrosionsschützende zubereitung sowie ölhaltiges, wassermischbares emulsionskonzentrat für die behandlung von metalloberflächen | |
| DE69132250T2 (de) | Antikorrosive Zusammensetzung | |
| DE10043040A1 (de) | Verwendung von N-Alkyl-beta-alanin-Derivaten zur Herstellung von reinigenden Korrosionsschutzmitteln | |
| EP0216280B1 (de) | Verwendung von Alkenylbernsteinsäurehalbamiden als Korrosionsschutzmittel | |
| EP0231524B1 (de) | Verwendung von Alkylbenzoylacrylsäuren als Korrosionsinhibitoren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |