NO129382B - - Google Patents
Download PDFInfo
- Publication number
- NO129382B NO129382B NO13971A NO13971A NO129382B NO 129382 B NO129382 B NO 129382B NO 13971 A NO13971 A NO 13971A NO 13971 A NO13971 A NO 13971A NO 129382 B NO129382 B NO 129382B
- Authority
- NO
- Norway
- Prior art keywords
- mol
- compounds
- propylenediamine
- formula
- effect
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004659 sterilization and disinfection Methods 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 9
- FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 230000000721 bacterilogical effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000000199 molecular distillation Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DBBZOURVEFUJEW-UHFFFAOYSA-N 1-n-dodecylpropane-1,2-diamine Chemical compound CCCCCCCCCCCCNCC(C)N DBBZOURVEFUJEW-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- YBUMEUMBIWOBBF-UHFFFAOYSA-N n'-[2-(octylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCNCCNCCN YBUMEUMBIWOBBF-UHFFFAOYSA-N 0.000 description 3
- KPZNJYFFUWANHA-UHFFFAOYSA-N n'-octylpropane-1,3-diamine Chemical compound CCCCCCCCNCCCN KPZNJYFFUWANHA-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FYWYVUPOHVJFEL-UHFFFAOYSA-N 1-n-decylpropane-1,2-diamine Chemical compound CCCCCCCCCCNCC(C)N FYWYVUPOHVJFEL-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 230000000622 irritating effect Effects 0.000 description 2
- RRHLGOOTLYHTEW-UHFFFAOYSA-N n'-[2-(dodecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCNCCNCCN RRHLGOOTLYHTEW-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YVLLFYIFMKAGCT-KHPPLWFESA-N 1-n-[(z)-octadec-9-enyl]propane-1,2-diamine Chemical compound CCCCCCCC\C=C/CCCCCCCCNCC(C)N YVLLFYIFMKAGCT-KHPPLWFESA-N 0.000 description 1
- ZZEKLJMQENPGEU-UHFFFAOYSA-N 1-n-octadecylpropane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCC(C)N ZZEKLJMQENPGEU-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- -1 alkyl radical Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 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
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000014103 egg white Nutrition 0.000 description 1
- 210000000969 egg white Anatomy 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 235000010944 ethyl methyl cellulose Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920003087 methylethyl cellulose Polymers 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 231100000286 mucous membrane, eye irritation or corrosion testing Toxicity 0.000 description 1
- UZWLVTABZVASMA-UHFFFAOYSA-N n'-[2-(decylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCNCCNCCN UZWLVTABZVASMA-UHFFFAOYSA-N 0.000 description 1
- MVCXBMAXWHWFSV-UHFFFAOYSA-N n'-[2-(hexadecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCNCCNCCN MVCXBMAXWHWFSV-UHFFFAOYSA-N 0.000 description 1
- ZHOMXZBLEQJUIK-UHFFFAOYSA-N n'-[2-(octadec-1-enylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCC=CNCCNCCN ZHOMXZBLEQJUIK-UHFFFAOYSA-N 0.000 description 1
- DBNYMXPUYZOHQN-UHFFFAOYSA-N n'-[2-(octadecylamino)ethyl]ethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCNCCN DBNYMXPUYZOHQN-UHFFFAOYSA-N 0.000 description 1
- SSSZZOVUXFLWCQ-UHFFFAOYSA-N n'-tetradecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCCCNCCCN SSSZZOVUXFLWCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Detergent Compositions (AREA)
Description
Den utpregede' desinfeksjons- og sanitære rensevirkning av forbindelser med den generelle formel I kunne ikke forutsees og er derfor overraskende. Således er f.eks. de nedenfor oppførte forbindelser med formel III bakteriologisk praktisk talt virknings- The pronounced disinfection and sanitary cleaning effect of compounds of the general formula I could not be foreseen and is therefore surprising. Thus, e.g. the compounds of formula III listed below are bacteriologically practically effective
løse, enskjønt de. kjemisk er oppbygget tilsvarende som forbindel- resolve, although they chemically is structured similarly to
sene med formel I. tendon with formula I.
I analogi til en alifatisk aminrekke, hvor f.eks. In analogy to an aliphatic amine series, where e.g.
i in
forbindelsen oktylamin og N-oktyl-propylendiamm i samme grad viser svak bakteriologisk virkning og forbindelser som dodecylamin og N-dodecyl-propylendiamin viser sammenligningsmessig god bakteriolo- the compound octylamine and N-octyl-propylenediamine to the same degree show a weak bacteriological effect and compounds such as dodecylamine and N-dodecyl-propylenediamine show comparatively good bacteriological
gisk virkning, hadde man nemlig for forbindelsene med formel I og III enten måttet vente den samme bakteriologiske virkning eller gic effect, namely for the compounds of formulas I and III one would either have had to expect the same bacteriological effect or
uvirksomhet. idleness.
Overraskende er det videre at forbindelsene I ifølge It is also surprising that the compounds I according to
oppfinnelsen, sammenlignet med overflateaktive aminer eller kvaternære ammoniumforbindelser, utøver en betraktelig lavere irritasjonsvirkning på hud og slimhud, mens ved andre baktericider vanligvis er en spesielt god baktericidi koplet med spesielt sterk irritasjonsvirkning. the invention, compared to surface-active amines or quaternary ammonium compounds, exerts a considerably lower irritating effect on the skin and mucous membranes, while with other bactericides a particularly good bactericide is usually coupled with a particularly strong irritating effect.
En spesiell fordel ved forbindelsene I ifølge opp- A particular advantage of the compounds I according to op-
finnelsen er endelig å se deri at de utfolder deres fortrinnlige baktericide egenskaper allerede ved sure pH-verdier, f.eks. ved pH 4,' mens f.eks. kvaternære ammoniumforbindelser eller ampholyt- the invention is finally to be seen in that they unfold their excellent bactericidal properties already at acidic pH values, e.g. at pH 4,' while e.g. quaternary ammonium compounds or ampholyte
såper først er fullt virksomme ved pH-verdier over 7. Dessuten er forbindelsene I ifølge oppfinnelsen langt mindre følsomme overfor eggehvite og anioniske detergenter enn f.eks. kvaternære ammonium- soaps are first fully effective at pH values above 7. Moreover, the compounds I according to the invention are far less sensitive to egg whites and anionic detergents than e.g. quaternary ammonium
forbindelser. Dermed egner forbindelsene ifølge oppfinnelsen seg helt spesielt for anvendelse f.eks. i drikkevareindustrien, i meierier, i fiske- og kjøttforarbeidende bedrifter. connections. Thus, the compounds according to the invention are particularly suitable for use e.g. in the beverage industry, in dairies, in fish and meat processing companies.
Fremstillingen av forbindelsene ifølge oppfinnelsen The preparation of the compounds according to the invention
foregår fortrinnsvis ved omsetning av 2,6-diklorpyridin med 1 til 4 mol av et amin med den generelle formel II takes place preferably by reacting 2,6-dichloropyridine with 1 to 4 mol of an amine of the general formula II
idet n, m og R har den ovenfor angitte betydning, ved temperaturer fra 100 til 180°C i nærvær av en syreakseptor. Anvendelsen av oppløsningsmidler som etylglykol, dioksan, propylenglykol, er mulig ved reaksjonen, men for det meste ikke nødvendig. where n, m and R have the above meaning, at temperatures from 100 to 180°C in the presence of an acid acceptor. The use of solvents such as ethyl glycol, dioxane, propylene glycol is possible in the reaction, but mostly not necessary.
Som aminer ifølge formel II kommer det på tale: N-oktyl-propylendiamin, N-decyl-propylendiamin, N-dodecyl-propylendiamin, N-tetradecylpropylendiamin, N-heksade.cy 1-propylendiamin, N-oktadecylpropylendiamin, N-oktadeceny1-propylendiamin, N-oktyl-dietylentriamin, N-decyldietylentriamin, N-dodecyl-dietylentriamin, N-tetradecyl-dietylentriaminj N-heksadecyl-dietylentriamin, N-oktadecyldietylentriamin og N-oktadecenyl-dietylentriamin. Spesielt økonomiske er blandinger av ovennevnte aminer, f.eks. N-kokos-alkylpropylendiamin eller -dietylentriamin, hvis alkylrest altså stammer fra en kokosfettsyre eller slike aminer hvis alkylrest avleder,seg fra produkter fra oksosyntesen. Amines according to formula II include: N-octyl-propylenediamine, N-decyl-propylenediamine, N-dodecyl-propylenediamine, N-tetradecylpropylenediamine, N-hexade.cy1-propylenediamine, N-octadecylpropylenediamine, N-octadeceny1-propylenediamine , N-octyldiethylenetriamine, N-decyldiethylenetriamine, N-dodecyldiethylenetriamine, N-tetradecyldiethylenetriaminej N-hexadecyldiethylenetriamine, N-octadecyldiethylenetriamine and N-octadecenyldiethylenetriamine. Particularly economical are mixtures of the above-mentioned amines, e.g. N-coco-alkylpropylenediamine or -diethylenetriamine, whose alkyl residue therefore originates from a coconut fatty acid or such amines whose alkyl residue derives from products of oxosynthesis.
Som syreakseptorer egner det seg f.eks. natriumhydroksyd, kaliumhydroksyd, kalsiumhydroksyd, natriumkarbonat, kaliumkarbonat og natriumbikarbonat resp. de i overskudd tilstedeværende aminer ifølge formel II. As acid acceptors, e.g. sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate and sodium bicarbonate resp. the amines according to formula II present in excess.
Forbindelsene ifølge "oppfinnelsen med formel I anvendes fortrinnsvis i form av deres salter, f.eks. som acetater, laktater, tartrater, glukonater, citrater, hydroklorider, fosfater og nitrater. Disse salter er vannoppløselige eller vanndispergerbare. Dessuten oppløser de seg i oppløsningsmidler som metanol, etanol, metyl-glykol, etylglykol, etylenglykol, propylenglykol (1,2), glycerin og iseddik. The compounds according to the invention with formula I are preferably used in the form of their salts, for example as acetates, lactates, tartrates, gluconates, citrates, hydrochlorides, phosphates and nitrates. These salts are water-soluble or water-dispersible. Furthermore, they dissolve in solvents which methanol, ethanol, methyl glycol, ethyl glycol, ethylene glycol, propylene glycol (1,2), glycerin and glacial acetic acid.
Desinfeksjons- og sanitære rensetilberedninger med et virksomt innhold av forbindelsene ifølge oppfinnelsen med formel I kan i tillegg inneholde ikke ionogene tensider, som etoksylerings-produktene av laurylalkohol, isotridecylalkohol, nonylfenol, isooktyl-fenol og fettsyreglycerider, samt blandingspolymerisatene av etylen-oksyd og propylenoksyd. Disse tilberedninger kan være av flytende, fast eller pastøs konsistens og inneholde ekstra fortykningsmidler, som metyl-, hydroksyetyl- og karboksymetylcellulose, polyakrylsyre og deres derivater, polyvinylalkohol, samt polyvinylpyrrolidon, indifferente fyllstoffer, som høydispers kiselsyre, aluminiumoksyd, sinksulfid, titandioksyd, samt urinstoff, rørsukker og cellulose og endelig også fargestoffer og luktestoffer. Disinfection and sanitary cleaning preparations with an active content of the compounds according to the invention with formula I may also contain non-ionic surfactants, such as the ethoxylation products of lauryl alcohol, isotridecyl alcohol, nonylphenol, isooctylphenol and fatty acid glycerides, as well as the mixed polymers of ethylene oxide and propylene oxide. These preparations can be of a liquid, solid or pasty consistency and contain additional thickeners, such as methyl, hydroxyethyl and carboxymethyl cellulose, polyacrylic acid and their derivatives, polyvinyl alcohol, as well as polyvinyl pyrrolidone, indifferent fillers, such as highly dispersed silicic acid, aluminum oxide, zinc sulphide, titanium dioxide, and urea , cane sugar and cellulose and finally also dyes and fragrances.
I de følgende eksempler omtales fremstillingen av forbindelsene ifølge oppfinnelaen og deres tilberedninger nærmere. Eksempel 1. In the following examples, the preparation of the compounds according to the invention and their preparations are discussed in more detail. Example 1.
Fremstilling av Manufacture of
I en 1 liters firehalset kolbe med røreverk, tilbake-løpskjøler og termometer innføres 2 mol N-oktyl-propylendiamin (373 g). 1 mol 2,6-diklorpyridin (148 g), 1,5 mol NaOH og 5 ml vann. Kolbeinnholdet oppvarmes deretter under omrøring i 3 timer ved 130 til l40°C. Deretter dekanteres den organiske flytende fase varmt fra uorganiske bunnlegemer og i vakuum avdestilleres ikke omsatt N-propylendiamin. Destillasjonsresiduet som inneholder reak-sjonsproduktet ifølge oppfinnelsen i rå form, underkastes nå en såkalt molekylardestillasjon. Derved fåes 235 g renprodukt som går over ved en varmebadtemperatur fra 120 til 125°C og 0,1 mm Hg. Elementæranalyse. 100 g 2 mol of N-octyl-propylenediamine (373 g) are introduced into a 1 liter four-necked flask with a stirrer, reflux condenser and thermometer. 1 mol of 2,6-dichloropyridine (148 g), 1.5 mol of NaOH and 5 ml of water. The contents of the flask are then heated with stirring for 3 hours at 130 to 140°C. The organic liquid phase is then decanted hot from inorganic sediments and unreacted N-propylenediamine is distilled off in a vacuum. The distillation residue, which contains the reaction product according to the invention in crude form, is now subjected to a so-called molecular distillation. Thereby, 235 g of pure product is obtained which converts at a heat bath temperature of 120 to 125°C and 0.1 mm Hg. Elementary analysis. 100 g
200 ml eddiksyre, 100 ml n-propanol, 20 g Na-acetat og 580 ml H20 homogeniseres under omrøring og oppvarmning ved ca. 40°C, idet det fremkommer en klar, gul oppløsning som er vannfortynnbar etter ønske. 200 ml of acetic acid, 100 ml of n-propanol, 20 g of Na-acetate and 580 ml of H20 are homogenised while stirring and heating at approx. 40°C, as a clear, yellow solution appears which can be diluted with water as desired.
Eksempel 2. Example 2.
Fremstilling av Manufacture of
1 mol 2,6-diklorpyridin (148 g), 3 mol N-oktyl-dietylentriamin (646 g), 1,5 mol NaOH (60 g) og 10 ml H20 innføres i en firehalset kolbe med røreverk, tilbakeløpskjøler og termometer. Blandingen oppvarmes deretter i 3 timer ved 130°C. Deretter dekanteres den organiske fase varmt fra fast uorganisk residuum og ikke omsatt N-oktyl-dietylentriamin avdestilleres best mulig i vakuum. Destillasjonsresiduet som i det vesentlige inneholder reaksjons-produktet ifølge oppfinnelsen av den ovennevnte formel, renses nå ved hjelp av en såkalt molekylardestillasjonsapparatur. Ved varmebadtemperaturer fra 120 til 140°C og trykk fra 0,1 til 0,5 mm Hg går det over 240 g analyserent produkt. 1 mol of 2,6-dichloropyridine (148 g), 3 mol of N-octyl-diethylenetriamine (646 g), 1.5 mol of NaOH (60 g) and 10 ml of H 2 O are introduced into a four-necked flask with a stirrer, reflux condenser and thermometer. The mixture is then heated for 3 hours at 130°C. The organic phase is then decanted hot from the solid inorganic residue and unreacted N-octyl-diethylenetriamine is best distilled off in a vacuum. The distillation residue, which essentially contains the reaction product according to the invention of the above-mentioned formula, is now purified using a so-called molecular distillation apparatus. At heat bath temperatures from 120 to 140°C and pressure from 0.1 to 0.5 mm Hg, more than 240 g of analytically pure product passes through.
Elementæranalyse. Elementary analysis.
Eksempel 3-Fremstilling av 1 mol 2,6-diklorpyridin (148 g), 1,2 mol N-lauryl-propylendiamin, 1,1 mol NaOH (60 g) og 5 ml^HgO innføres i en firehalset kolbe med røreverk, tilbakeløpskjøler og termometer. Etter ifølge eksempel 1 analog reaksjon og opparbeidelse fåes ved molekylardestillasjon 230 g av det analyserene produkt ifølge oppfinnelsen av ovennevnte formel, som går over ved varmebadtemperaturer fra 140 til 160°C og trykk fra 5 . 10~<2> til $ . IO-1 mm Hg. Elementæranalyse. Example 3-Preparation of 1 mol of 2,6-dichloropyridine (148 g), 1.2 mol of N-lauryl-propylenediamine, 1.1 mol of NaOH (60 g) and 5 ml of HgO are introduced into a four-necked flask with stirrer, reflux condenser and thermometer. After an analogous reaction and work-up according to example 1, 230 g of the analyzed product according to the invention of the above-mentioned formula is obtained by molecular distillation, which converts at heat bath temperatures from 140 to 160°C and pressure from 5 . 10~<2> to $ . 10-1 mm Hg. Elementary analysis.
Eksempel 4. Example 4.
Fremstilling av Manufacture of
1 mol 2,6-diklorpyridin (148 g), 2 mol N-lauryldietylen-triamin (543 g), 1,5 mol NaOH og 5 ml H20 omBettes analogt eksempel 1 med den forskjell at reakajonstemperaturen utgjør l40°C og reak-sjonstiden 5 timer. Ved molekylardestillasjon fåes ved varmebadtemperaturer fra 140 til 160°C og trykk fra 5 • 10~2 til IO"<1> mm Hg 245 g av de analyserene produkter ifølge oppfinnelsen med ovennevnte formel. 1 mol of 2,6-dichloropyridine (148 g), 2 mol of N-lauryldiethylenetriamine (543 g), 1.5 mol of NaOH and 5 ml of H20 about Bette's analogous example 1 with the difference that the reaction temperature is 140°C and the reaction time 5 hours. By molecular distillation, at heat bath temperatures from 140 to 160°C and pressure from 5 • 10~2 to 10"<1> mm Hg, 245 g of the analyzed products according to the invention with the above formula are obtained.
Elementæranalyse. Elementary analysis.
10 g av ovennevnte produkt, 20 ml konsentrert eddiksyre, 2 g natriumacetat, 20 ml «tanol og 48 ml vann oppvarmes under omrøring ved ca. 50°C, idet det oppstår en klar oppløsning som er blandbar med vann etter ønske. 10 g of the above product, 20 ml of concentrated acetic acid, 2 g of sodium acetate, 20 ml of ethanol and 48 ml of water are heated with stirring at approx. 50°C, as a clear solution is formed which is miscible with water as desired.
Eksempel 5. Example 5.
Fremstilling av Manufacture of
1 mol 2,6-diklorpyridin, 2 mol N-decyl-propylendiamin, 1,5 mol NaOH og 5 ml U^ O omsettes og opparbeides analogt eksempel 1. Man får ved molekylardestillasjon 250 g renprodukt, som går over ved varmebadtemperaturer fra 130 til 140 C og trykk fra 5 • 10" til IO'<1> mm Hg. 1 mol of 2,6-dichloropyridine, 2 mol of N-decyl-propylenediamine, 1.5 mol of NaOH and 5 ml of U^O are reacted and worked up analogously to example 1. By molecular distillation, 250 g of pure product is obtained, which converts at heat bath temperatures from 130 to 140 C and pressure from 5 • 10" to IO'<1> mm Hg.
Elementæranalyse. Elementary analysis.
Eksempel 6. Example 6.
Fremstilling av Manufacture of
1 mol 2,6-diklorpyridin, 2 mol N-oleyl-propylendiamin, 1,5 mol NaOH og 5 ml HgO omsettes og opparbeides analogt eksempel 4. Man får ved molekylardestillasjon som foregår ved varmebadtemperaturer fra 160 til 200°C og trykk fra 5 . IO<-2> til IO<-1>1 mol of 2,6-dichloropyridine, 2 mol of N-oleyl-propylenediamine, 1.5 mol of NaOH and 5 ml of HgO are reacted and worked up analogously to example 4. It is obtained by molecular distillation which takes place at heat bath temperatures from 160 to 200°C and pressure from 5 . IO<-2> to IO<-1>
mm Hg, 260 g rent produkt. mm Hg, 260 g pure product.
Elementæranalyse. Elementary analysis.
Eksempel 7. Example 7.
Fremstilling av Manufacture of
Herved er R et alkylradikal som stammer fra en kokosfettsyre og danner en blanding av 8 til 18 C-atomer holdige karbon-kjeder av følgende vektprosentmessige sammensetning: Here, R is an alkyl radical which originates from a coconut fatty acid and forms a mixture of 8 to 18 carbon atoms containing carbon chains of the following weight percentage composition:
Cg: 0,55K Cg: 0.55K
C10: 2, k% C10: 2.k%
C12: 60, 5% C12: 60.5%
Cl4: 29,0$ Cl4: 29.0$
Cl6: 5,3* ;Cl8: 2, 3% 1 mol 2,6-diklorpyridin, 1,5 mol N-kokospropylendiamin, 1,5 mol NaOH og 5 ml HgO omsettes og opparbeides analogt eksempel 4. ;Av de nedenforstående bakteriologiske tabeller fremgår den fortrinnlige baktericide virkning av forbindelsen ifølge oppfinnelsen. ;Bestemmelsen av den bakteriologiske virkning foregikk ifølge retningslinjene fra Deutschen Gesellschaft fiir Hygiene und Mikrobiologie. ;1. Prøvestoff: ;;(ifølge eksempel 4) ;pH: 5 (0,1% virksom stoff holdig vandig oppløsning). ;2. Prøvestoff ;(ifølge eksempel 7) ;pH: 4,5 ( 0, 1% virksom stoffholdig vandig oppløsning). ;3. Prøvestoff: ;(ifølge eksempel 1) ;pH: 5 ( 0, 1% virksom stoffholdig vandig oppløsning). ;4. Baktericid virkning av forbindelsen ifølge oppfinnelsen: ;(ifølge eksempel 7) .;pH: 4 (1* virksom stoffholdig stamoppløsning) Cl6: 5.3*; Cl8: 2.3% 1 mol of 2,6-dichloropyridine, 1.5 mol of N-cocopropylenediamine, 1.5 mol of NaOH and 5 ml of HgO are reacted and worked up analogously to example 4. ;Of the following bacteriological tables show the advantageous bactericidal effect of the compound according to the invention. The determination of the bacteriological effect took place according to the guidelines of the Deutsche Gesellschaft fiir Hygiene und Mikrobiologie. ;1. Test substance: ;;(according to example 4) ;pH: 5 (0.1% active substance containing aqueous solution). ;2. Test substance (according to example 7) pH: 4.5 (0.1% active substance-containing aqueous solution). ; 3. Test substance: ;(according to example 1) ;pH: 5 (0.1% active substance-containing aqueous solution). ; 4. Bactericidal effect of the compound according to the invention: (according to example 7) .;pH: 4 (1* stock solution containing active substance)
a) i nærvær av 20% serum a) in the presence of 20% serum
b) i nærvær av 0, 1% bløt såpe. b) in the presence of 0.1% soft soap.
Av det følgende fremgår den bakteriologiske virkning av en til teknikkens stand hørende kvaternær ammoniumforbindelse i nærvær av serum resp. bløt såpe. The following shows the bacteriological effect of a prior art quaternary ammonium compound in the presence of serum or soft soap.
5. Sammenligning. 5. Comparison.
Bakteriologisk virkning av en handelsvanlig kvaternær ammoniumforbindelse med 40 vektprosent alkylgrupper med 12, 50 vektprosent alkylgrupper med 14 og 10 vektprosent alkylgrupper med 16 karbonatomer (N-alkyl-benzyl-dimetylammoniumklorid). Bacteriological effect of a commercially available quaternary ammonium compound with 40% by weight alkyl groups with 12, 50% by weight alkyl groups with 14 and 10% by weight alkyl groups with 16 carbon atoms (N-alkyl-benzyl-dimethylammonium chloride).
a) i nærvær av 20% serum a) in the presence of 20% serum
b) i nærvær av 0,1$ bløt såpe. b) in the presence of 0.1$ soft soap.
Ved sammenligning av den bakteriologiske virkning av forbindelsen ifølge oppfinnelsen med den til teknikkens stand hørende kvaternære ammoniumforbindelse kan det uten videre sees overlegenheten av førstnevnte og dermed dens fremskritt. When comparing the bacteriological action of the compound according to the invention with the prior art quaternary ammonium compound, the superiority of the former and thus its progress can be seen without further ado.
6. Øyeirritasjonsprøve på kaniner ifølge Draize. 6. Eye irritation test on rabbits according to Draize.
(J.H. Draize og E.A. Kelley, Drug and Cosmetic Ind., 71 (1952), 36-37 og 118-120). (J.H. Draize and E.A. Kelley, Drug and Cosmetic Ind., 71 (1952), 36-37 and 118-120).
Prøvestoff: Sample material:
pH: 4,5 ( 0, 5% virksom stoffholdig vandig oppløsning). pH: 4.5 (0.5% active substance-containing aqueous solution).
Irritasjonsvirkning av forbindelsene ifølge oppfinnelsen er å betegne som liten til måtelig på grunn av den fullstendige reversibilitet av innvirkningsymptomene inntil 7. dag. Irritation effect of the compounds according to the invention is to be described as small to moderate due to the complete reversibility of the impact symptoms up to the 7th day.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19702007100 DE2007100A1 (en) | 1970-02-17 | 1970-02-17 | Biocidal pyridine compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
NO129382B true NO129382B (en) | 1974-04-08 |
Family
ID=5762461
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO13971A NO129382B (en) | 1970-02-17 | 1971-01-14 |
Country Status (10)
Country | Link |
---|---|
AT (1) | AT303039B (en) |
BE (1) | BE760979A (en) |
CH (1) | CH539635A (en) |
DE (1) | DE2007100A1 (en) |
ES (1) | ES387795A1 (en) |
FR (1) | FR2078639A5 (en) |
GB (1) | GB1298054A (en) |
NL (1) | NL7101802A (en) |
NO (1) | NO129382B (en) |
SE (1) | SE383256B (en) |
-
1970
- 1970-02-17 DE DE19702007100 patent/DE2007100A1/en active Granted
- 1970-12-17 CH CH1869070A patent/CH539635A/en not_active IP Right Cessation
- 1970-12-29 BE BE760979A patent/BE760979A/en unknown
-
1971
- 1971-01-14 NO NO13971A patent/NO129382B/no unknown
- 1971-01-21 ES ES387795A patent/ES387795A1/en not_active Expired
- 1971-02-11 NL NL7101802A patent/NL7101802A/xx unknown
- 1971-02-16 FR FR7105153A patent/FR2078639A5/fr not_active Expired
- 1971-02-16 SE SE195271A patent/SE383256B/en unknown
- 1971-02-17 AT AT136871A patent/AT303039B/en not_active IP Right Cessation
- 1971-04-19 GB GB2074071A patent/GB1298054A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
AT303039B (en) | 1972-11-10 |
GB1298054A (en) | 1972-11-29 |
SE383256B (en) | 1976-03-08 |
FR2078639A5 (en) | 1971-11-05 |
CH539635A (en) | 1973-07-31 |
BE760979A (en) | 1971-05-27 |
ES387795A1 (en) | 1973-05-16 |
NL7101802A (en) | 1971-08-19 |
DE2007100A1 (en) | 1971-09-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0607198B1 (en) | Preparation of improved alkylpolyglycoside surfactant mixtures | |
JP2588570B2 (en) | Skin conditioning / cleansing composition containing propoxylated glycerol derivative | |
CA2119638A1 (en) | Preparation of alkylpolyglycosides | |
EP0091237B1 (en) | Detergent composition | |
EP0609391A1 (en) | Novel alkylpolyosides, compositions containing same, process for their preparation and applications as surface agents | |
JPS6094904A (en) | Cosmetic | |
US4481187A (en) | Clear liquid skin cosmetic compositions | |
NO311253B1 (en) | Amine hydrofluorides and their use as oral hygiene preparations | |
JPH02164891A (en) | Substituted glucoside | |
NO129382B (en) | ||
JP2004532319A (en) | Method for producing surfactant mixture | |
US11123277B2 (en) | Oral composition | |
US11071704B2 (en) | Oral composition | |
JP6260111B2 (en) | Anti-wrinkle composition and cosmetic | |
JP4467306B2 (en) | Alkyl and / or alkylene oligoglycoside betaine ester quarts | |
WO1996005281A1 (en) | Detergent composition | |
JPH09227479A (en) | New amideestercarboxylic acid or its salt, their production, and cleaning agent composition containing the same | |
JP3150781B2 (en) | External preparation for skin | |
JPH0970528A (en) | Surfactant | |
NO132674B (en) | ||
JP3164673B2 (en) | Novel sugar aminosulfonic acid compound, process for producing the same, and surfactant composition containing the same | |
JP4011247B2 (en) | Cosmetics | |
RU1536673C (en) | Insulation composition for treating granules and sheets in rubber mixtures | |
WO2024111142A1 (en) | Ascorbic acid derivative or salt thereof, and cosmetic thereof | |
JP3590531B2 (en) | External preparation for skin |