WO1980002155A1 - Agent tensioactif antibacterien contenant de l'azaalkelelactame - Google Patents

Agent tensioactif antibacterien contenant de l'azaalkelelactame Download PDF

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WO1980002155A1
WO1980002155A1 PCT/JP1980/000055 JP8000055W WO8002155A1 WO 1980002155 A1 WO1980002155 A1 WO 1980002155A1 JP 8000055 W JP8000055 W JP 8000055W WO 8002155 A1 WO8002155 A1 WO 8002155A1
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mol
value
methyl
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water
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French (fr)
Japanese (ja)
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M Shinano
H Hamanaka
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Toho Chemical Industry Co Ltd
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Toho Chemical Industry Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/62Biocides, 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D245/00Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms
    • C07D245/02Heterocyclic compounds containing rings of more than seven members having two nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16Amines or polyamines
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/58Heterocyclic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/104Polyethers, i.e. containing di- or higher polyoxyalkylene groups of alkylene oxides containing two carbon atoms only
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/10Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/103Polyethers, i.e. containing di- or higher polyoxyalkylene groups
    • C10M2209/107Polyethers, i.e. containing di- or higher polyoxyalkylene groups of two or more specified different alkylene oxides covered by groups C10M2209/104 - C10M2209/106
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24Organic 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
    • C10M2215/26Amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/04Macromolecular compounds from nitrogen-containing monomers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/046Polyamines, i.e. macromoleculars obtained by condensation of more than eleven amine monomers
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10NINDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00Specified use or application for which the lubricating composition is intended
    • C10N2040/08Hydraulic fluids, e.g. brake-fluids

Definitions

  • the present invention relates to a novel antibacterial surfactant containing a novel cyclic amide. More specifically, the antibacterial surfactant of the present invention has a seven-membered ring containing a hydrophobic group consisting of 8 to 22 carbon bond chains and a basic nitrogen as shown below. Has a hydrophilic group consisting of an 8-membered lactam group in the same molecule.
  • (CH 2 ) n including compounds that can be covalently bonded to an organic acid at a basic nitrogen moiety or have a structure to which an organic acid or an inorganic acid is added.
  • the antibacterial surfactant compound of the present invention is ethylenediamine or 1-, 3-propylenediamine per mole of ethylenediamine. It is necessary to add 3 moles or hydrogenate after adding acrylonitrile.
  • the reaction mole ratio per reaction is 1 mole of acrylonitrile and 2 moles of hydrogen per mole of starting amine.
  • the terminal monoalkylated product of polyalkylenepolyamine obtained by performing both reactions (however, the hydrocarbon group may be an alkyl group, an alkyl group, or an alkyl group).
  • Alkoxy, Alkoxy Alkyl, Alkoxy Alkyl, Alkoxy Alkyl, and Alkoxy Alkoxy Includes hydroxyalkyl groups.
  • No acylated compounds (however, the hydrocarbon group may be an alkynole group, an alkenyl group, a hydroxy group, or a hydroxy group.
  • R is an alkyl group having a total carbon number of 8 to 22, an alkyl group, an alkyl group, an alkyl group, an alkyl group, an alkyl group, A hydroxy phenol group, a hydroxyl group and a benzo-substituted acyl group
  • A is a hydrogen atom or a hydroxy group 0 W ⁇ 1, u 0 X + ⁇ ⁇ 3 ⁇ 4 0 ⁇ 3, 1 ⁇ a + b + 1 or and also least for a of c 4 der Ru in the compound that will be I table, and the number 4 or more carbon atoms (Oriremi I Lev 0 o: ⁇ 3 ⁇ 4 scan 'Les
  • the alcohol in the lower alcohol reacts with the ester acetate, or is ethylamine or 1,3-F. Mouth pyramid "I-mol is attached to ethylene rim 1-
  • reaction mol ratio is 1 mol of raw material amine). (1 mol of acrylonitrile and 2 mol of hydrogen), or by carrying out both of the above two reactions.
  • Acetonitrile ester of alkylene porphyrin containing at least one of alkylene polyamines and phenols having a carbon number of 4 or less. After reacting with an ester of pionic acid, the phenol group has 7 to 21 carbon atoms, an alkenyl group, a hydroxy-substituted alkyl group or a carbonyl group. A carboxylic acid having a hydroxy-substituted alkenyl group is reacted, or ethylenediamine or 1,3-phenylene.
  • Mono-hydroxyl teriyaki or monohydric terrestrial of propylene range ° mouth pillow-animal and alcohol with 4 or less carbon atoms Acetate acetate or holmyl propyl ester.
  • an alkyl group having 7 to 21 carbon atoms an alkenyl group, a ⁇ -pixy substituted alkyl group or It is also possible to react a carboxylic acid having a hydroxy-substituted alkenyl group ⁇ , followed by a monochloro or monob mouth.
  • General formula which can react the obtained carboxylic acid or a salt thereof.
  • R is a phenol group having a total of 8 to 22 carbon atoms, an alkyl group, an alkyl group, an alkyl group, an alkyl group, Hydroxyl group, acyl group and hydroxy-substituted acyl group, H ,, R "and" '"are hydrogen atom or methyl group,
  • A is a hydrogen atom or a hydroxyl, ⁇ W 1, 0 X + z 3, 0 ⁇ ⁇ ⁇ 30 ⁇ +
  • An atom can be covalently bonded to an organic acid as necessary, or can have a structure to which an organic acid or an inorganic acid is added.
  • polyalkylene polyamine which is a raw material of the amines used, is polyethylene glycol and polyethylene glycol.
  • Rui-Daniru examples include Mono-no-Chiru-Ichi, Mono-No-Ni-Ri-Dani, Mono-Doshi-Ri-Dai, Mono-no-De-Shirai-Dani, Mono-Do-De-Sil Compounds, monolithic delicatessens, mononotes, denominations, monopentanes, delicatessens, monohedrals Monosil (9-octadecenyl), mono-ecosil stilt, monodokosyl stilt, mono (2-hide) Lokeshi) Dodeciri Dani, Mono (2-Hydroxi) Hexa de Siriu Dani, Mono (2-Hydroxii) Tetra de Siriu Dani , Mono (2-hin (
  • 2-fosolemilf is used as the honolemil propionate ester.
  • ⁇ pin on-acid 3 one ho Honoré mil off 0 necked Pio phosphate, 2 - ho Honoré Mi Honoré one 2 - main Chi le flop port arsenide.
  • Each eye Chi Norre of mouth heat ° on-acid, E Ji Norre, flop opening non-zero Norre, butyrate Norre et scan te Norre cited et al.
  • ⁇ l Canolevonic acid includes octylic acid, rauric acid, myristinic acid, and phenol. Noremic acid, stearic acid, oleic acid, linoleic acid, 12-hydroxy styrene acid, ricinolenoic acid, etc.
  • Monochlorogendicarboxylic acid is, for example, monochloroacetic acid, monofluoromonic acid, and mononuclear acid.
  • Arsenide 0 O phosphate etc. can be mentioned et be [pi.
  • antimicrobial surface-active compounds put that port real key record emissions E 0 Li Ryo ⁇ down New ⁇ Le key Le Po Li for the preparation of the present invention
  • Ryoru key record emission port 1 Ryo Mi emissions New - A le co ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇
  • OMPI Clean porphyrin, monohydro quinone, porcelain porcelain, porcelain porcelain, and carbon Monoamide and acetoacetate ester produced by acid are also available.
  • the reaction with the pionic acid ester is dehydrated and deaerated at reduced pressure or atmospheric pressure at 50-250 ° C, preferably 10-180 ° C.
  • the procedure proceeds by performing the N-alkyl-alkaline lactam of the present invention.
  • a catalyst and a solvent are not particularly required.
  • the flow of an inert gas such as nitrogen gas or carbon dioxide gas is effective since the completion of the reaction is accelerated.
  • the reaction between N-alkylazaalkane lactam and monoha-genated carbohydrate or acid is water or alcohol or dioxan.
  • Adiamine and acetate acetate stells are also available.
  • the reaction between the reaction product of carboxylic acid ester and carboxylic acid is performed under reduced pressure in the same manner as in the known amidation reaction and esterification reaction. Dehydration proceeds at 50 to 250 ° C, or preferably at 120 to '200 ° C, under normal pressure, but also in this case, it is a catalyst.
  • a reaction solvent is not particularly required, and the inflow of an inert gas such as nitrogen gas or carbon dioxide gas makes the reaction easier to complete.
  • FIG. 1 shows the 4-dodecyl 7-methyl-13, ⁇ —dihydro—2H—1,4—dazepine-5 produced according to Example 1.
  • Fig. 3 ® and Fig. 4 ® ® are 4-dodecyl-
  • FIG. 1 is a 1 H-NMR spectrum diagram of -1- acetate.
  • Fig. 5 is a mass vector diagram of 4-dodecyl-7-methyl-3, 6-diphenyl-2 H-1, 4-diazene-5- Oh
  • N-alkyl lactone an organic antioxidant containing the cyclic amide of the present invention, and its organic oxide are aerobic bacteria and anaerobic. It produces antimicrobial activity in small amounts, whether bacteria, Gram-positive or Gram-negative, so it acts not only as a fungicide and pesticide for humans, animals and the environment, but also as a bacterium. It can also act as an inhibitor of corrosive metal corrosion, and itself forms a coating on a variety of metals to suppress corrosion. Best Mode for Carrying Out the Invention Used as a Disinfectant Mixed with Various Diluents According to the Purpose
  • N-dodecylethylamine 2 was attached to a square flask equipped with a stirrer, a thermometer, a gas flow tube, and a water sample tube connecting the reflux condenser. 2 8.1 ⁇ (1 mol) and acetate acetate 1 30.1 ⁇ (1 mol) were charged, and nitrogen was added.
  • Example 2 In the same apparatus as in Example 1, one dodecinole, ethylene triamine 27.1 (1 mol) and methyl acetate acetate 10.1 ⁇ (1 mol) were added. ), And distill 18 water and 52 methanol at 140 to 150 ° C, and then give 4-red-decinole amino in a pale red liquid. Ethanol—7-methyl-3, ⁇ —dihydro—2H-1,4—dazepine-5-one was obtained.
  • TRACH P low 1,5-diacin-2-on 39 9 0.29-(1 mol) was added dropwise, and acetic acidification was carried out from 70 to 80-1-(9- 1 4-Mesinol — 1 — Hazardous 5-Azo, 2 octanes — 4 — Gen — 2 — On — 51 Were synthesized.
  • Example 2 The same apparatus as in Example 1 was equipped with a polyethylene rim-
  • Example 10 (MNR spectrum N-CH 2 C00-proton 2.03 ppm, DSS standard, 50 MHz)
  • Example 10 The same equipment as in Example 1, but with a polyethylene rim
  • Example 1 2'-N-hydroxyethyl ethylamine 104.2 (1 mol) and acetate ethyl acetate were added to the same apparatus as in Example 1. 13 0.19- (1 mol) was charged, and 18 water and 40 ⁇ ethanol were distilled off at 150 to 100 ° C. Next, the solution is subjected to esterification at 200 to 210 ° C by adding 20.0.3 (1 mol) of Lauric acid to distill 8 ⁇ water. 4-Raw mouth yloxyethyl-7-methyl'-3, ⁇ -dihydro-2H-1 and 4-Hazepin-5-one.
  • Example 2 The same apparatus as in Example 1 was prepared by adding ⁇ -hydroxylethylene dimethylamine “I04.29- (1 mol) and acetoacetate acetate 130.1 ⁇ (1 mol) ), And 150 to 100. In C, 18 water and 46 ⁇ ethanol were distilled off. ) At 200 to 215 ° C to distill the water of 189-, and give the 4-year-old 7-Methyl — 3, ⁇ — Dihydro-2H-1, 4-Zypin-5-on.
  • N-alkyl obtained in a solution obtained by dissolving 94.5 (1 mol) of acetic acid (monoxide) in 4.50 water was obtained.
  • Alkyl lactam 380.8 (1 mol) was added dropwise and mixed at 00 to 70 ° C, and then hydroxy hydrium 40.0 ( 1 mol) was added, and the reaction was carried out at the same temperature to synthesize vinegar oxide.
  • the mixture was mixed at 00 ° C, and further, 40.0-(1 mol) of hydroxy thinium was added to carry out a reaction to synthesize vinegar oxide. ⁇
  • a mounting device similar to that in Example 11 of the present embodiment is provided with an N-octyl-enoxy resin. Mouth Pyrenean Kissif. Mouth hi. Nore Ethylene> Amine 408.5 (1 mol) and methyl acetate acetate
  • N-alkyl alcohol was dissolved in a solution obtained by dissolving sodium monochloroacetate 10.5- (1 mol) in water of 1000. Endurance Lactum 4 9 5.8 9- (1 mol) is dropped, and then 0 to 70. The reaction was carried out with C to obtain an acetate.
  • Example 21 1 The same apparatus as in Example 1 was replaced with ⁇ -hydroxypropyl-1 and ⁇ -7 °. 13.2 ⁇ (1 mol) and methyl acetate acetate (10.1 ⁇ ) (1 mol) were charged, and at 140 to 150 ° C, 18 ⁇ water and 3 Distilled out 2 ⁇ methanol. Next, ricinoleic acid (298.5 ⁇ '(1 mol)) was added to ⁇ to 220-225. The esterification was carried out in C, and 18 water was distilled out to synthesize N-alkylazaalkane lactam.
  • Example 25 5 Use the same method as in Example 12.], N-hydroxy: 7 ° port pill-1, 3-off. Mouth pandiamin 152.2 ⁇ (1 mol), methyl acetate acetate 10.1 ⁇ (1 mol) and benenoic acid 340.5 ⁇ (1 mol) as raw materials Then, first, 1- ⁇ , Noir, Kissif. Mouth pill-4-Methyl-3, 6, 7,
  • Example 2 The same apparatus as in Example 1 was prepared by adding N- (2-hydroxy) tetradecyl dimethyltriamine 3 1 5.59 (1 mol) and acetoacetic acid Charge butyric 158.1 ⁇ (1 mol), add 150 ⁇ water and 74 ⁇ butanol under reduced pressure of 50 dishes Hg at 150 ° C Distilled, 4-(2-hydroxytetradecyl) aminoethyl-7-methyl ⁇ ⁇ dihydro 2 ⁇ 4-diazepi
  • the same device as in the first embodiment is provided with an N-octoxy (2-hydroxy) buffer. Mouth pill ethylenediamine 2 18.5 ⁇ (1 mol) and acetate acetate 130.19 (1 mol) were charged, and 150 to 100 ° C. to distill 1 8 ⁇ of water and 4 0 ⁇ of error data Roh Lumpur in, 4 - O click preparative key sheet (2 - arsenate de port key sheet) profile arsenide 0 Honoré - 7 - main Chi Honoré - 3 , ⁇ -dihydro — 2 ⁇ -1, 4-azezepine-5-on.
  • N-nonyl phenol was added to the same device as in the first embodiment.
  • Tetrahydro-1,5-diacin-2-one 3 82.5 ⁇ (1 mol) is added dropwise, and after mixing at 50 to 00 ° C Then, a solution prepared by dissolving 50.19 (1 mol) of potassium hydroxide in 200 ⁇ of water was added thereto, and the reaction was carried out at the same temperature. The reaction was carried out at 1-doxoxy (2-hydroxy). ) Pouch pill-4-Methyl-1-Hazard-5-Hazard Cycle-4-Pen-2-On-5-F. I got a mouth pionate.
  • Example 3 ⁇ N-dodecyl 7 ° Prepare the propylene triamine (299.5 ⁇ (1mol)) and acetate acetate 150.1 ⁇ (1mol) at 150 ⁇ 100 ° C. Distill out 18 ⁇ water and 46 ⁇ ethanol to give 1-dodecylamino propyl-4-methyl-5, ⁇ ,,
  • Example 3 7 The same device as in Example 1 was used, except that a ⁇ -year-old decyl sulfide was used. Charged with ethyl acetate 15 0.19- (1 mol), distilled 18 water and 4 ethanol at 150 to 1 ⁇ . ⁇ ° G, and 1-year-old Tadecylaminopropyl — 4 — Methyl —
  • Tetrahydro-1, 5-diazane ⁇ Sin-2-one 4 47.79 (1 mol) was added dropwise and mixed at 70-80 ° C. 1-octadecyl Aminoff is reacted at the same temperature by charging a stream 4 0.09 (1 mol). Mouth-4-Methyl-1-Hazard-5-Radio cycle-4-En-2-On-5-F. I got a mouth pionart.
  • Example 40 Apparatus similar to that of Example 1 ⁇ , ⁇ -Tetradecyldiethylentriamin 29.9.59 (1 mol) and 2-holmilf. Methyl ropionate 1 1 0.1 ⁇ (1 mol) was charged,
  • N- (2-hydroxy) dodecylethyleneamine 244.4 (1 mol) and 2 holmilf were used. Mouth pionic acid. Lo hee. Charged with 144.29- (1 mol), 1850 water and ⁇ 0 ⁇ isof at 150-155 ° C. Distilled out of the pillar alcohol, 4-
  • Example 4 5 In the same manner as in Example 1, N— (2-hydroxy) dodecyl propylene range amine 25 6.5 9 ( 1 mol) and 2-holmilf. Methyl pionic acid 1 1 6.19 (1 mol) was charged, and 18 ⁇ water and 32 ⁇ methanol were distilled off at 130 to 135 ° C. 1 One (2-Hydroxy) Dodecyl ⁇ Methinole- ⁇ ⁇ 7 8-Tetraso '
  • Example 2 The same apparatus as in Example 1 was prepared by adding ethylene triamine 0 5. ⁇ (1 mol) and 2-formyl 7 ° -opening methyl pionate 1 1 0.19 (1 ), 130 to 1 55
  • Example 52 The same device as in Example 1 was used,
  • Example 5 The same apparatus as in Example 1, but with Amine 295.59 (one mole) and 3—holmylpropane methyl 1 10.1 ⁇ (one mole) were charged, and 125 to 130. In G, 18 ⁇ of water and 32 ⁇ of methanol were distilled off, and 4 -tetradecinole was removed.
  • Example 2 The same equipment as in Example 1 includes ⁇ - (9-year-old cinnabarium) ethylene-min (30.1 0.1 f1 mol) and 3-holmylprophy. Provide 18.5 8.2 ⁇ (1 mol) At 150 ° C, distill 18 ⁇ water and 74 ⁇ datanol under reduced pressure of 50 miHg to obtain 4-(9-year-old female)- 2, 3, 0, 7-Tetrahydrido 1, 4-Jacin-5-on.
  • Dia-cin-5-one 370.0 (1 mol) was added dropwise and mixed at 65-75 ° G. ⁇ (1 mol) is injected and the reaction is carried out at the same temperature, and 4-(9-year-old decane)-4--1- ⁇ ⁇ 8--1-5-ON-1-I got an acetate.
  • An apparatus similar to that of the first embodiment is provided with a ⁇ -monotetradecylamine reagent. 15.5 g (1 And 2 — Holminor 2-methyl olefins. Fill the mouth cavity with 158.2 (1 mol), and at 150-155 ° C, 18 ⁇ water and ⁇ 0 ⁇ isof. Distillation of the pill alcohol is carried out, and 1-tetradecylaminoethyl-, 3-dimethylamino-6, 7, 8—trihydro-1 5 — r
  • Trich mouth-1,5-diacin-5 -one ⁇ 93.69 (1mol) is added dropwise and mixed at 70 ⁇ 80 ° C, then potassium hydroxide 5 ⁇ 1 ⁇ (1 mol) is charged and the reaction is carried out at the same temperature, and the reaction is carried out at 1-tetradecyl amine.
  • Elemental analysis value C 1 3 ⁇ 4 H 34 O 2 2 Calculated value ⁇ c 69.05 H 11.05 9.02 Experimental value c 09.00 H 1.04 9.05 Amin value 180.7 (Theoretical value 180.7) IR spectrum 1010C7 / T 1 ), 1055cm " 1
  • N-tetradecyl dimethyltriamine 29 99.5 S- (1 mol) and 3-formyl-2-methyl 7 ° Mouth Methyl 130.19 (1 mol) was charged, and 18 ⁇ water and 52 ⁇ methanol were distilled off at 145-150 ° C to obtain 4-tetradecyl.
  • N-alkyl was obtained in a solution of sodium monoacetate 10.5 ⁇ (1mol) in 100 ⁇ water.
  • Lucent lactam 5 0 9.8 ⁇ (1
  • Tables 1, 2, and 3 show the results of antibacterial tests of ⁇ -alkyl-substituted azaalkane lactams and their organic oxides in judgments 1 to 70. Indicated.
  • the test method is based on the Japanese Society of Chemotherapy standard method,
  • Desulfovibrils Desulfolicans (Desulfovi3 ⁇ 4rio desulfur cans) IO3699 (sulfate-reducing bacteria), pseudomonas alginosa

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PCT/JP1980/000055 1979-03-30 1980-03-28 Agent tensioactif antibacterien contenant de l'azaalkelelactame Ceased WO1980002155A1 (fr)

Priority Applications (1)

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DE19803041419 DE3041419A1 (de) 1979-03-30 1980-03-28 Antibacterial surfactant containing azaalkenelactam

Applications Claiming Priority (2)

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
JP79/38254 1979-03-30

Publications (1)

Publication Number Publication Date
WO1980002155A1 true WO1980002155A1 (fr) 1980-10-16

Family

ID=12520168

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1980/000055 Ceased WO1980002155A1 (fr) 1979-03-30 1980-03-28 Agent tensioactif antibacterien contenant de l'azaalkelelactame

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=)

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Also Published As

Publication number Publication date
JPS6312067B2 (https=) 1988-03-17
US4346087A (en) 1982-08-24
CH643589A5 (de) 1984-06-15
JPS55136268A (en) 1980-10-23
GB2065115B (en) 1983-04-20
GB2065115A (en) 1981-06-24

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