2,970,145 United States Patent Office Patented Jan. 31, 1961 1. 2 Typical of the groups that R3 may represent include methyl, ethyl, propyl, butyl, pentyl, hexyl, octyl, nonyl, 2,970,145 decyl, dodecyl, pentadecyl, octadecyl; allyl, methallyl, butenyl, pentenyl, hexenyl, octenyl, decenyl, dodecenyl, AMINOACETAMIDOXIMIC QUATERNARY 6 tetradecenyl, octadecenyl, propynyl, butynyl, pentynyl, AMMONUM COMPOUNDS hexynyl, octynyl, decynyl, dodecynyl, octadecynyl; meth Peter. L. de Benneville, Philadelphia, Pa., assignor to oxyethyl, methoxybutyl, methoxypentyl, methoxyoctyl, Rohm & Haas Company, Philadelphia, Pa., a corpo methoxyldecyl, methoxydodecyl, methoxyoctadecyl, eth ration of Delaware oxyethyl, ethoxypropyl, ethoxyhexyl, ethoxynonyl, eth 10 oxydecyl, ethoxytetradecyl, ethoxyoctadecyl, propoxy No Drawing. Filed Dec. 23, 1957, Ser. No. 704,332 ethyl, propoxypropyl, propoxyhepty, propoxydecyl, pro 6 Claims. (Cl. 260-247.5) poxytetradecyl, propoxyheptadecyl, butoxyethyl, butoxy butyl, butoxyoctyl, butoxyundecyl, butoxyhexadecyl, pen toxyethyl, pentoxypentyl, pentoxyhexyl, pentoxypenta This invention deals with aminoacetamidoximic qua 15 decyl, hexoxyethyl, hexoxybutyl, hexoxyhexyl, hexoxy ternary ammonium compounds as new compositions of dodecyl, hexoxytetradecyl, heptoxyethyl, heptoxyheptyl, matter. It further concerns a method for the prepara heptoxydodecyl, octoxyethyl, octoxypropyl, octoxybutyl, tion of these compounds. octoxyoctyl, octoxydecyl, nonoxyethyl, nonoxypentyl, The compounds of the present invention may be rep nonoxynonyl, nonoxydecyl, decoxyethyl, decoxypropyl, resented by the formula 20 decoxypentyl, decoxydecyl, undecoxyethyl, undecoxyhep tyl, dodecoxyethyl, dodecoxypentyl, dodecoxyoctyl, tridec oxytheyl, tridecoxyheptyl, tetradecoxyethyl, tetradecoxy butyl, pentadecoxyethyl, pentadecoxypentyl, hexadecoxy ethyl, heptadecoxyethyl, octadecoxyethyl, vinoxyethyl, in which R and R2 may be alkyl groups of no more than 25 vinoxybutyl, vinoxyoctyl, vinoxydecyl, vinoxydodecyl, two carbon atoms, that is methyl or ethyl. Also R1 and vinoxyoctadecyl, alloxyethyl, alloxypropyl, alloxynonyl, R* may be considered collectively to represent a divalent alloxytetradecyl, butenoxyethyl, butenoxypentyl, bu Saturated chain that forms with the amino nitrogen atom, tenoxyheptyl, butenoxyundecyl, butenoxytetradecyl, pen a heteromonocyclicamine group such as a pyrrolidine, tenoxyethyl, pentenoxypentyl, pentenoxydodecyl, pen piperidine, thiamorpholine, or morpholine ring, or their 30 tenoxytridecyl, hexenoxyethyl, hexenoxyhexyl, hex C-alkylated derivatives. The symbol R3 may represent " enoxynonyl, hexenoxytetradecyl, nonenoxyethyl, non an alkyl group of one to eighteen carbon atoms, an al enoxypentyl, nonenoxyhexyl, nonenoxynonyl, decen kenyl group of three to eighteen carbon atoms, an al oxyethyl, decenoxyoctyl, undecenoxyethyl, undecen kynyl group of three to eighten carbon atoms, an al oxyoctvl, dodecenoxyethyl, dodecenoxypentyl, tridecen koxyalkyl or alkenoxyalkyl group of three to twenty car 35 oxyethyl, tridecenoxyheptyl, tetradecenoxyethyl, tetradec bon atoms in which the alkoxy group or alkenoxy group enoxybutyl, pentadecenoxyethyl, pentadecenoxypentyl, is no closer than the beta position with respect to the hexadecenoxyethyl, heptadecenoxyethyl, octadecenoxy amino nitrogen atom, a hydroxyalkyl group of two to ethyl; hydroxyethyl, hydroxypropyl, hydroxybutyl, hy eighteen carbon atoms in which the hydroxy group is no droxypentyl, hydroxyoctyl, hydroxydecyl, hydroxydo closer than the beta position with respect to the amino decyl, hydroxyoctadecyl; benzyl, butylbenzyl, octylben nitrogen atom, an alkoxyarylalkyl, aryloxyalkyl, or al zyl, dodecylbenzyl, dimethylbenzyl, methylbutylbenzyl, kylaryloxyalkyl group of no more than twenty-one car dihexylbenzyl, phenylethyl, butylphenylethyl, phenylbu -bon atoms, an arylalkyl group of seven to twenty-one tyl, phenyldodecyl, naphthylethyl, naphthylbutyl, naph carbon atoms, alkylarylalkyl group of eight to twenty thyloctyl, phenylbutenyl, phenyloctenyl, phenyldecenyl, one carbon atoms, or arylalkenyl group of eight to 45 phenyldodecenyl, octylphenylbutenyl; chlorobenzyl, di twenty-one carbon atoms, arylalkyl groups having halo chlorobenzyl, bromobenzyl, cyanobenzyl, nitrobenzyl; gen or nitro Substituents, a carbamoylalkyl group of two methoxybenzyl, butylmethoxybenzyl, butoxybenzyl, oc -to eighteen carbon atoms, an alkoxycarbonylalkyl or toxybenzyl, phenoxyethyl, octylphenoxyethyl, octylphen acyloxyalkyl group of three to twenty carbon atoms, and oxybutyl; methoxycarbonylmethyl, methoxycarbonylbul an alkylcarbonylalkyl group of three to twenty carbon 50 tyl, methoxycarbonyldecyl, methoxycarbonyloctadecyl, atoms or arylcarbonylalkyl group of eight to twenty ethoxycarbonylmethyl, ethoxycarbonyloctyl, ethoxycar carbon atoms. yldecvi, ethoxycarbonylundecyl, propoxycarbonylmethyl, The symbol R3 may exhibit all of the possible con propoxycarbonylpropyl, propoxycarbonyloctyl, butoxy figurations and structures. Substituents in the group R3 carbonylpentyl, butoxycarbonyldodecyl, pentoxycarbon may occupy any of the possible structural locations. 55 ylbutyl, pentoxycarbonvltetradecyl, hexoxycarbonylnon The symbol m represents an integer of one to two, yl, hexoxycarbonyldodecyl, heptoxycarbonvlethyl, hep preferably one. toxycarbonyltridecyl, octoxvicarbonylmethyl, octoxycar The symbol X represents an anion. In this respect, bonvoctyl, octoxvicarbonvlhexadecyl, nonoxvicarbonyl there may be used chloride, bromide, iodide, sulfate, methyl, decoxycarbonylmethyl, decoxycarbonylbutyl, dec methosulfate, phosphate, acetate, lactate, hydroxide, tar 60 oxycarbonylhexyl, undecoxycarbonylbutyl, dodecoxy trate, thiocyanate, nitrate, pentachlorophenate, and the carbonylmethyl, dodecoxycarbonylnonyl, tridecoxycar like. The halogens having an atomic weight of about bonylmethyl, tetra decoxycarbonvlmethyl, hexadecoxycar 35.5 to 127 are preferred. Anions other than the halo bonvleth v1. octadecoxvicarbonylmethyl, octadecoxycar gens or the hydroxide may be supplied directly or by bonylpentyl, acetoxymethyl, propionoxybutyl, butyroxy metathesis with the halide or hydroxide form of the 65 pentyl, valeroxyethyl, pelargonyloxypropyl, undecylenyl present quaternary ammonium compounds. An anion oxyoctyl, stearoyloxyhexyl, methoxycarbonylbenzyl, eth exchange resin may also be used to supply the desired oxycarbonylbenzyl, octoxycarbonylbenzyl, butoxycarbon ion. It will be apparent to one skilled in the art that ylethylphenylethyl, butoxycarbonylphenylbutyl, octoxy the identity of the cationic portion of the present com carbonylphenyinonyl; carbamoylmethyl, carbamoylethyl, pounds is the critical consideration and that the anionic carbamoylpropyl, carbamoylbutyl, carbamoyloctyl, car -portion is relatively unimportant. v bamoyldodecyl, carbamoylheptadecyl, methylcarbonyl -- 2,970,145 . - 3 4. methyl, methylcarbonylethyl, methylcarbonylbutyl, meth apparent to one skilled in the art, the longer reaction ylcarbonyloctyl, methylcarbonyldecyl, methylcarbonyldo times generally favor higher yields, up to a point. Also, decyl, methylcarbonyloctadecyl, ethylcarbonylmethyl, Some reactants combine more speedily than others. In ethylcarbonylethyl, ethylcarbonylbutyl, ethylcarbonylhep order to assure completeness of reaction and concomitant tyl, ethylcarbonylnonyl, ethylcarbonyltetradecyl, ethyl 5 Substantially quantitative results, if desired, there may carbonyloctadecyl, propylcarbonylmethyl, propylcarbon be determined the amount of ionizable anion, particu ylpropyl, propylcarbonylphentyl, propylcarbonylundecyl, larly when halide is involved. When the theoretical propylcarbonylheptadecyl, butylcarbonylmethyl, butyl amount of anion is present, the reaction is complete. carbonylbutyl, butylcarbonylhexyl, butylcarbonyltridecyl, The reactants of this invention combine in substan butylcarbonyloctadecyl, pentylcarbonylmethyl, pentyl 10 tially equimolecular amounts to form the quaternary am carbonylpentyl, pentylcarbonyldodecyl, hexylcarbonyl monium products of this invention in substantially quan methyl, hexylcarbonylhexyl, hexylcarbonyldecyl, hexy titative amounts. Either reactant may be employed in carbonylpentadecyl, heptylcarbonylmethyl, heptylcarbon excess, if desired. It is preferable to employ an excess ylheptyl, heptylcarbonylhexadecyl, octylcarbonylmethyl, of RX if one reactant is desired in excess. octylcarbonyloctyl, octylcarbonylpentadecyl, nonylcar At the conclusion of the reaction, any solvent used bonylmethyl, nonylcarbonylpentyl, nonylcarbonylnonyl, may be removed by stripping, preferably under reduced nonylcarbonyltetradecyl, decylcarbonylmethyl, decylcar pressure. It is possible, and frequently advantageous, in bonyltridecyl, undecylcarbonylmethyl, undecylcarbonyl the preparation of some of the instant compounds to first decyl, dodecylcarbonylmethyl, dodecylcarbonylundecyl, prepare the halide form, such as chloride, in a manner tridecylcarbonylmethyl, tetradecylcarbonylethyl, penta 20 already set forth, and then prepare any other desired decyclicarbonylpropyl, hexadecylcarbonylhepty, hepta form within the present definition by metathesis or ion ex decylcarbonylbutyl, octadecylcarbonylethyl, phenylcar change methods. For instance, any of the present com bonylmethyl, phenylcarbonylethyl, phenylcarbonylpropyl, pounds in halide form may be converted to the hydroxide phenylcarbonylbutyl, phenylcarbonyloctyl, phenylcarbon form through the use of silver oxide, or the like, and then yldecyl, phenylcarbonyldodecyl, phenylcarbonyltetrade 25 converted to any desired anion form by acidifying with cyl, phenylcarbonylheptadecyl, napthylcarbonylmethyl, an acid of choice such as sulfuric, phosphoric, acetic, and naphthylcarbonylethyl, naphthylcarbonylpenty, naph others within the range and spirit of this invention. As thylcarbonyloctyl, naphthylcarbonyldodecyl, naphthyl an alternative, an anion-exchange resin may be em carbonyltridecyl, butylphenylcarbonyloctyl, ethylnaph ployed. Any of the present compounds, in halide or hy thylcarbonylhexyl, and octylphenylcarbonylpenty1. 30 droxide form, may be converted to any desired anion The compounds of this invention are produced by form through the use of an anion-exchange resin in the bringing together in a reacting temperature and thereby desired anion form. For instance, there may be used an effecting quaternization a compound having the formula insoluble, cross-linked, styrene-divinylbenzene copoly RSX, with a compound having the formula meric quaternary ammonium salt in its sulfate, phosphate, 35 or the like, form to convert a present compound in halide R 2 NOH or hydroxide form to a desired form, such as sulfate, phosphate, and the like. It is also possible to make the present quaternary am in which the symbols have the significance previously monium compounds by quaternary ammonium com referred to. The aminoalkanamidoxime reactants are 40 pounds by quaternizing the corresponding aminoacetoni prepared according to the method disclosed in United trile with the reactant R3X under the condition described States application Serial Number 704,331, filed Decem previously and then reacting that quaternary ammonium ber 23, 1957. compound with hydroxylamine. If the hydroxylamine is Typical representations of the R3X reactants, illus used in one of its common salt forms, common bases, trated in chloride form, include octyl chloride, butenyl 45 such as sodium carbonate, sodium hydroxide, potassium chloride, hexynyl chloride, ethoxydecyl chloride, vinoxy carbonate and the like are used to free the hydroxylamine ethyl chloride, hydroxyethyl chloride, benzyl chloride, for reaction. The reaction with hydroxylamine is con phenylbutenyl chloride, butylphenylethyl chloride, meth veniently carried out in aqueous or aqueous lower al oxybenzyl chloride, dodecoxybenzyl chloride, methoxy kanolic solution at temperatures ranging from 0 to butylbenzyl chloride, octylphenoxyethyl chloride, cyano 50 80° C. benzyl chloride, bromobenzyl chloride, nitrobenzyl chlo The present compounds are produced in yields that ride, methyl chloroacetate, chlorobutyl acetate, benzyl constantly approach quantitativeness. They are crystal chloropropionate, octyl chloromethylbenzoate, chloro line compounds or viscous oils and waxes, that are butanamide, chloro methyl methyl ketone, and chloro readily handled by well-known techniques. The present decyl phenyl ketone. Typical representations of the sub 55 compounds are effective bactericides particularly when stituted aminoacetamidoximes include diethylaminoacet applied against Micrococcus pyogenes var. aureus and amidoxime, morpholinopropionamidoxime, dimethyl Salmonella typhosa as determined by standard phenol aminoacetamidoxime, pyrrolidinoacetamidoxime, piperi coefficient tests. The bactericidal effect is highest in those dinoacetamidoxime and morpholinoacetamidoxime. compounds where the group R3 contains from 8 to 21 The quaternary ammonium compounds of this inven 60 carbon atoms and these groups are preferred. The in tion are prepared by bringing together the selected re stant compounds are useful fungicides in dilutions down actants at a reacting temperature in the range of about to one-half ounce in 100 gallons of formulation and low 20 C. to the reflux temperature of the reactant mixture, er, particularly when applied against Stemphylium sar preferably not above about 200° C. The preferred range cinaeforme and Monilina fructicola and evaluated by is about 25 to 100° C. The use of an inert volatile sol 65 standard methods. vent is advantageous and in this respect, there may be The compounds of this invention, in particular wherein employed methanol, ethanol, isopropanol, tert-butanol, the R3 group contains from 8 to 21 carbon atoms, are diethyl ether, acetonitrile, formamide, dioxane, dimethyl valuable as detergent-Sanitizers and may be employed in formamide, nitromethane, ethylene glycol, toluene, and meat plants to Sanitize cutting table, grinders, and the like, the like. 70 in fruit processing operations, for instance, to wash and Reaction times of about two to twenty-four hours and Sanitize lemons, oranges, and grapefruit, and in dairy more are generally employed depending largely on the farms to sanitize dairy equipment and utensils. reaction temperature, use and identity of a solvent, and A Suitable detergent-sanitizer formulation for use in "the particular reactants employed. The time of reaction meat plants includes, by weight, 5% of a compound of is not critical but merely influences the yield. As will be 75 this invention, 2.5 to 5.0% of octylphenoxypolyethoxy 2,970,145 ethanol, 20 to 40% soda ash, 20 to 40% sodium meta tially soluble in water. This syrup corersponds in an silicate, and the remainder sodium tripolyphosphate. One alysis to N - methyltridecylbenzyl - N,N-dimethylam ounce of this formulation is used per gallon of water. moniumacetamidoxime chloride. For sanitizing citrus fruit, there is preferably used one In the same way, dodecylbenzyl chloride is reacted part of a present compound in 5000 parts of water. For with a molecular equivalent of piperidinoacetamidoxime use in dairy farms, there may be used 10% of a quater to give nary ammonium compound of this invention, 10% of oc NOH tylphenoxypolyethoxyethanol, 7% of trisodium phos C.H.C.H.CHNCHC phate, and 73% of water. One ounce of this solu M. N. tion is used per four gallons of water. The in 10 CH, CH, eNH2 Cl stant compounds in aqueous solution in amounts of &H, ÖH, about 0.5 to one ounce to one hundred pounds of dry N / fabric, are excellent as a final diaper rinse to prevent CEI diaper rash. These compounds are also excellent premise In the same way, octylbenzyl chloride is reacted with sanitizers where they may be employed in concentrations 5 a molecular equivalent of pyrrolidinoacetamidoxime to of about 0.1 to 2.0% in aqueous cleaning solutions. give N - octylbenzylpyrrolidiniumacetamidoxime chloride The compounds of this invention, as well as the method and morpholinopropionamidoxime is reacted with octo for preparing them, may be more fully understood from decenyl bromide to produce N-octadecenyl-N-octylam the following examples, which are offered by way of il monium propionamidoxime bromide. lustration and not by way of limitation. Parts by weight 20 Example 4 are used throughout. . . . To an aqueous solution of 44 parts of N-cyanomethyl Example I N-benzyl-N,N-dimethyl ammonium chloride in 8 parts of A mixture is made of 117 parts of dimethylaminoacet water is added 80 parts of ethanol and then 17.5 parts amidoxime, 202 parts of 5,5,7,7-tetramethyl-2-octenyl 25 of hydroxylamine hydrochloride dissolved in 50 parts of chloride (dodecenyl chloride), and 300 parts of isopro water. To the mixture is added slowly a solution of 13.3 pyl alcohol. The mixture is stirred at room tempera parts of sodium carbonate in 50 parts of water. The ture for twenty-four hours. The isopropyl alcohol is re mixture is stirred for two to three hours. It is evaporat moved by stripping under vacuum to yield a gummy solid ed to dryness in vacuo. The solid is extracted with 300 which is suspended in acetone, filtered and dried. There 30 parts of dry ethyl acetate and filtered. The residue is is recovered a colorless solid melting at 168-170° C. dissolved in 150 parts of methanol, filtered to remove This product corresponds in analysis to N-5,5,7,7-tetra salt, and placed in a refrigerator. The colorless product methyl - 2 - octenyl - N,N-dimethylammoniumacetam is filtered. A sample dried in vacuo at 60° C. melts at idoxime chloride. 176-178 C. It corresponds in analysis to N-benzyl-N, When 331 parts of 9-octadecenyl bromide is substi 35 N-dimethylammoniumacetamidoxime chloride, of the tuted for the 5,5,7,7-tetramethyl-2-octenyl chloride in formula the above preparation, there is obtained a viscous oil, - “... NOH characterized as N-9-octadecenyl-N,N-dimethylammoni ^ -- - 2 umacetamidoxime bromide. CHN(CH-CH.C. C Example 2 40. The product is outstanding in inhibiting the growth of A mixture is made of 32 parts of morpholinoacetamid .Stemphylium sarcinaeforme and Monilinia fructicola. oxime, 50 parts of n-dodecyl bromide, and 60 parts of In a similar manner, from N-cyanomethyl-N-allyl-N, isopropyl alcohol. The mixture is heated for twelve N-dimethylammonium chloride, hydroxylamine hydro hours at 60° C. and stripped under vacuum to yield a tan 45 chloride, and sodium carbonate in substantially equiva solid which corresponds to N-n-dodecylmorpholinium lent amounts, there is obtained allyldimethylammonium acetamidoxime bromide, acetamidoxime chloride as a colorless crystalline solid. CHCH2 NOH N+ 2 Example 5 O N. : : - / NCHC " . Br 50 A mixture is made of 11.7 parts of N,N-dimethyl CHCH YH, aminoacetamidoxime, 12.7 parts of benzyl chloride, and 12H25 20 parts of isopropyl alcohol. It is heated at 50° C. for eight hours and allowed to stand sixteen hours. The iso In the same way, n-dodecyl bromide is reacted with a propyl alcohol is removed by distillation in vacuo to molecular equivalent of dimethylaminoacetamidoxime to 55 give a quantitative yield of the product of Example 4. give When 17 parts of p-nitrobenzyl chloride is substituted - " NOH 4- 2 for the benzyl chloride in above procedure there is ob (CH)-NCHC B tained a yellow solid corresponding in composition to 2Fis NH2 p-nitrobenzyldimethylammoniumacetamidoxime chloride. and with diethylaminoacetamidoxime to give N-n-dodec 60. When 24 parts of octylphenoxyethyl bromide is substi yl-N,N-dmimethylammonium acetamidoxime bromide. tuted for the benzyl chloride, there is obtained an alco In the same way, from 234 parts of dimethylamino holic solution of the quaternary ammonium salt having acetamidoxime, 650 parts of octadecyl bromide, and 640 the formula: parts of isopropyl alcohol, there is obtained a soft solid: NOH which corresponds in analysis to N-octadecyl-N,N-di 65 methylammoniurnacetamidoxime bromide. It is substan chic Hochschisch).ch.c? tially water-soluble. NHe Example 3 It is extremely bactericidal towards Micrococcus pyogenes Wa. diets. A mixture is made of 60 parts of methyltridecylbenzyl 70 When 19.5 parts of 2,4-dichlorobenzyl chloride is sub chloride which is predominantly the 2-methyl-5-tridecyl stituted for the benzyl chloride in the above procedure isomer, 23 parts of dimethylaminoacetamidoxime and there is obtained on evaporation a colorless solid corre 64 parts of isopropyl alcohol. It is heated at 75° C. sponding in composition to 2,4-dichlorobenzyldimethyl (under reflux ) for six hours. The isopropyl alcohol is ammoniumacetamidoxime chloride. removed in vacuo to give a tan syrup which is substan- 75 When 16.7 parts of phenylbutenyl chloride is substi 2,970,145 7 8 tuted for the benzyl chloride in the above procedure, I claim: . . . there is obtained an alcohol solution of the compound: 1. As a composition of matter the compound having NOH the formula w a - R NoH CHCH-CH=CHCHN(CH-CH.C. Cl N(CH).cf. X N / N This solution strikingly inhibits the growth of Stemphyl R2 R3 NE ium saicinaeforme. When 12 parts of propargyl bromide is substituted for in which R1 and R2 considered singularly are alkyl groups the benzyl chloride in the above procedure, there is ob O of 1 to 2 carbon atoms and considered collectively repre tained propargyldimethylammoniumacetamidoxime bro sent a divalent saturated chain that forms with the amino mide. nitrogen atom a 5 to 6 membered heteromonocyclic When 12.5 parts of ethylene bromohydrin is substituted amine selected from the group consisting of pyrrolidinyl, for the benzyl chloride in the above procedure, there is piperidino, morpholino, and thiomorpholino, R3 is a 15 member of the class consisting of alkyl of 1 to 18 carbon obtained a thick oil which corresponds in composition atoms, alkenyl of 3 to 18 carbon atoms, alkynyl of 3 to to the structure 18 carbon atoms, alkenoxyalkyl of 3 to 20 carbon atoms NO w a in which the alkenoxy group is located on the alkyl group (CH3)N(CH2CH2OH) CHC Br in a position of remoteness of at least beta with respect 20 to the amino nitrogen atom, alkoxyalkyl of 3 to 20 car NH bon atoms in which the alkoxy group is located on the When 19 parts of octyloxyethyl chloride is substituted alkyl group in a position of remoteness of at least beta for benzyl chloride in the above example, there is ob with respect to the amino nitrogen atom, hydroxyalkyl tained a water-soluble oil which has the structure: of 2 to 18 carbon atoms in which the hydroxy group is NOH 25 located on the alkyl group in a position of remoteness of -- 2. at least beta with respect to the amino nitrogen atom, CHOCH2CHN(CH3)2CH2C. r alkoxyarylalkyl having up to 21 carbon atoms, aryloxy YH, alkyl having up to 21 carbon atoms, alkylaryloxyalkyl When 14 parts of methyl iodide is substituted for benzyl having up to 21 carbon atoms, arylalkyl of 7 to 21 carbon chloride in the above example, there is obtained a color 30 atoms, alkylarylalkyl of 8 to 21 carbon atoms, arylalkenyl less crystalline solid which is water-soluble and corre of 8 to 21 carbon atoms, carbamoylalkyl of 2 to 18 car sponds in composition to trimethylammoniumacetamidox bon atoms, alkoxycarbonylalkyl of 3 to 20 carbon atoms, ime iodide. acyloxyalkyl of 3 to 20 carbon atoms, alkylcarbonylalkyl When 31 parts of 4-dodecyloxybenzyl chloride is sub of 3 to 20 carbon atoms and arylcarbonylalkyl of 8 to 20 stituted for benzyl chloride in the above example, there 35 carbon atoms, in which all of the aryl groups in R are is obtained a viscous oil which is water-soluble and has members from the class consisting of phenyl and naph effective bactericidal and surface active properties. It thyl, m is an integer of 1 to 2 and X is an anion selected corresponds in structure to N-4-dodecoxybenzyl-N,N-di from the group consisting of chloride, bromide, iodide, methylammoniumacetamidoxime chloride. sulfate, methosulfate, phosphate, acetate, lactate, hydrox When 20 parts of phenoxyethyl bromide is substituted 40 ide, tartrate, thiocyanate, nitrate, and pentachlorophenate. for benzyl chloride in the above examples there is ob 2. As a composition of matter N-5,5,7,7-tetramethyl tained a crystalline solid which corresponds in structure 2-octenyl-N,N-dimethyl - ammoniumacetamidoxime chlo to phenoxyethyldimethylammoniumacetamidoxime bro ride. mide. 3. A composition of matter having the formula When 13 parts of bromoacetamide is substituted for 45 benzylchloride in the above example, there is obtained CECH NOE - N - carbamoylmethyl-N,N-dimethylammoniumacetam / Yat ea o NCIC . Br idioxime bromide. / N N When 16 parts of phenacyl chloride ar substituted for CHCH dodecyl NH, benzyl chloride in the above example, there is obtained phenacyldimethylammoniumacetamidoxime chloride, of 50 4. A composition of matter having the formula the structure: NO NOE a -- 2 s 2 C.H.CooHN(CH)-CH.C. Cle 55 NH emist.dodecyl NI r Chloromethyl heptadecyl ketone can be used in the same 5. As a composition of matter N-methyltridecylbenzyl way to provide N-heptadecylcarbonylmethyl-N,N-di N,N-dimethyl-ammoniumacetamidoxime chloride. methyammonium acetamidoxime chloride. 6. As a composition of matter N-benzyl-N,N-dimethyl When 17 parts of ethyl bromoacetate is substituted for 60 benzyl chloride in the above example, there is obtained ammoniumacetamidoxime chloride. N - ethoxycarbonylmethyi - N,N- dimethylammonium acetamidoxime bromide. References Cited in the file of this patent When 39 parts of 2-bromoethyl stearate is substituted . UNITED STATES PATENTS for the benzyl chloride in the above example, there is obtained a waxy solid which corresponds in composition 65 2,676,968 Burtner ------Apr. 27, 1954. to: 2,851,457 Zimmermann ------Sept. 9, 1958 NOE d 2 CH35 COO CHCHN (CH3)3CIIC Br N