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Publication numberUS2388614 A
Publication typeGrant
Publication dateNov 6, 1945
Filing dateMay 5, 1942
Priority dateMay 5, 1942
Publication numberUS 2388614 A, US 2388614A, US-A-2388614, US2388614 A, US2388614A
InventorsEmory Kirby James, Frank Lontz John
Original AssigneeDu Pont
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Disinfectant compositions
US 2388614 A
Abstract  available in
Images(6)
Previous page
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Claims  available in
Description  (OCR text may contain errors)

Patented Nov. 6, 1945 DISINFWI'ANT COMPOSITIONS James Emory Kirby and John Frank Lontl, wumington, DeL, minors to E. I. du Pont do Nomonrs a; Company, Wilmington, Del., a corporation of Delaware No Drawing. Application May 5, 1942,

a cam. (,01. 167-22) This invention relates to bactericidal compositions and more particularly to bactericidal detergent compositions.

Attempts have'been made to combine in one composition both a bactericide and a detergent. Thus antiseptics such as coal tar, phenolic and cresolic preparations, mercuric salts, e. g., as the chloride and iodide, arsenic and silver compounds, and essential oils such as resin oil, terpenes, almond oil, oil of thyme, etc. have been employed with soaps, i. e., with alkali salts of long chain fatty acids. In the case of phenolic or cresolic antiseptics, soaps do not enhance but even interfere with the antiseptic action." Mercurial soaps while highly antiseptic and particularly useful in skin diseases are limited in their utility because of their toxic character and, as with other heavy metal soaps, because of their precipitating action on proteins.- The essential oils likewise have certain shortcomings, particularly low germicidal power. In general, the known antiseptic or ger-.- micidal detergent combinations fail primarily because of the interfering action of the soap. and the resulting combination is only slightly, if at all, superior to the soap itself for hygienic and remedial purposes. Antiseptic and bactericidal compositions containing water-soluble addition salts of basic nitrogen compounds having, attached to nitrogen, long chain hydrocarbon radicals, are seriously reduced in bactericidal efliciency by the presence of a fatty acid soap or a synthetic detergent of the long chain alcohol sulfate or long chain alkanesuifonate type.

This invention has as an object improved antiseptic compositions. A further object is the provision of effective antiseptic detergent compositions. Other objects will appear hereinafter.

These objects are accomplished by the followin invention which comprises antiseptic or bactericidal compositions containing a betaine having on an annular atom of the betaine (in its cyclic form) an alkyl group of at least eight carbon atoms, and a water-soluble bactericidal basic nitrogen compound which, in aqueous solution, furnishes an organic cation having mobility, i. e;, movement within the solution, independent of all the anions in said solution and is selected from the class consisting of monomeric water-soluble addition salts of basic nitrogen compounds having attached to nitrogen a monovalent aliphatic hydrocarbon radical of at least eight carbon atoms and water-soluble salts of linear polymeric nitrogen compounds having, in the multiply recurring linear polymeric unit and as an integral part valent organic radical preferably hydrocarbon and preferably aliphatic of at least 4 chain atoms, the terminal atoms of which are carbon.

The salts of the basicnitrogen compounds defined above are considerably reduced in activity in the presence of fatty acid soaps, of long chain alkanesulfonate, or of long chain alcohol sulfates, but in the presence of long chain betaines, the bactericidal efficiency is, in some cases increased and in others the efliciency is undiminished. In some cases the bactericidal efficiency is lessened but to a far less degree than is the case with soap or the sulfates or sulfonates.

The more detailedpractice of the invention is illustrated by the following examples, wherein parts given are by weight. There are of course many forms of the invention other than these specific embodiments.

, (11. indicating the number of polymeric units in the chain), prepared from N,N,N',N-tetramethylhexamethylenediamine and hexamethyiene dibromide according to Ritter, U. S. Patent 2,261,002 was tested against Staphylococcus aureus by the F. D. A. method at 3'1 C. in the presence of l.'% C-hexadecylbetaine. A similar titer was determined for I without the betaine for purposes of control. The results obtained are given in the following table, in which the conventional signs and are used to designate growth and kill, respectively, in the given cultures.

Tssrr: I

Control Dilution of I I 1:5,000 1:10,000 l:20,000 l:30,000

Cultures at 15 mins With betaine tsine 1'=1oo 1% 1:100 Cultures at 6 mins.

Cultures at 15 mins C-hexadecylbetaine in these tests has caused I no deleterious or inactivating effect upon the of the chain, a nitrogen atom attached to a bibactericidal potency of polyhexamethylenedimethylammonium bromide- In fact, the germicidal activity of the latter was slightly more rapid in the presence of the betaine, which as indicated below, has no germicidal activity of its own in a di1utionof-1:200.

Polyhexamethylenedimeth'ylammonium broq mide is reduced in efficiency by the presence of soap as shown by the following:

One volume of 1% solution of polyhexamethylenedlmethylammonium bromide was mixed with 9 volumes of 20% soft soap in distilled water. This preparation was titrated in water dilutions against Staphylococcus aureus at 37 C. A control was run at the same time with polyhexamethylenedimethlylammonium bromide without soap. The results are indicated in the following table, in which the conventional signs and are used to designate growth and kill, respectively, in the given cultures. A check titer on the organism with phenol is also given.

TABLI II Control (mama soap) Dilution olI 1:5,000 1:10,000 1:20 000 Cultures at 6 mins Cultures at 10 mins... Cultures at 15 mins Cultures at 10 mins Cultures at 15 mins From the above table it is apparent that the soap even in a concentration as low as 0.9 of 1% seriously reduces the germicidal potency of thepolymeric compound.

Thus, it is apparent that germicidal agents of the above type having high degree of activity can be rendered almost useless when used in the presence of soap. Such combinations could not therefore be used effectively where it is desired to combine a cleansing action with disinfection or sterilization.

The betaines are very powerful detergents and in addition they are not as sensitive to hard waters as the soaps. However, like the soaps they are not in themselves strong germicidal agents as is apparent from the following bactericidal titer against Staphylococcus aureus determined by the F. D. A. method at 37 C. for C-hexadecyl betaine which has the structure:

TABLE III Dilution oi -hexadecylbetaine 1: Cultures at mins Cultures at 15 mins Phenol Dilution Cultures at 5 mins Cultures at mins Cultures at 16 mins Even a dilution of the C-hexadecylbetaine as low as 1:200 failed to kill any of the organisms.

EXAMPLEH Polydecamethylenedimethylammonium chloride (11), a homolog of compound I prepared from N,N,N',N'-tetramethyldecamethylenediamine and decamethylene dibromide according to Ritter U. S. Patent 2,261,002 and. having the formula TABLI IV Killing Dilution m 6 mine. 10 mins. 15 mins.

Control (II alone) 1:10, 000 1:20, 000 1:30, 000 Wltlil soap 1:200 1:200 1:200

With 1 o C-oetylbetaine-. l 1150,000. 1:76, 000 1:100,000

The above results indicate decisively the interfering effect of soap, reducing, for example, the germicidal potency by 90% in the case of the cultures at 10 minutes. C-hexadecylbetaine, on the other hand, shows a definite synergistic effect by increasing the potency about 3 times in the 5 case of the cultures at 10 minutes.

EXAMPLEIII Decamethylene bis(dimethyldecylammonium bromide) (HI), having theformula CH: CH: CH: CH:

Br Br (III) on. our;

(312E: CH2

The results are as follows:

TABLI: V

Killing dilution in 15mins. 10mins. .15 ins. in

Control (IIIalone) 1:75,000 1:100,000 1:100,000 IIIwith1%N-dodecylbetaine. moaoco 1=1oo,0oo 1=1o0,0oo

In this combination the kill appears to be somewhat more rapid in the 5-minute cultures.

The bactericides used in Examples I and 11 above exemplify one type of linear polymeric salts, the linear polymeric quaternary ammonium o salts. Example 111 exemplifies another type, the

monomeric polyquaternary ammonium salts, useful in this invention.

The linear'polymeric quaternary ammonium salts exemplified in Examples I and II are disu-closed more fully and claimedper se'in 'Ritter U. 8. Patent 2,281,002. and as bactericides in Searle U. 8. Patent 2,271,378, the disclosures oi. which patents are hereby incorporated.

Another type of bactericidal basic nitrogen compound salts, the linear polymeric amidine salts is disclosed and claimed as such in copending application, Serial No. 350,108, now U. 8. 2,310,789, filed August 2, 1940, by Hunt and Kirby,

and as pest control agents in copending application, Serial No. 405,555, now U. 8. 2,310,799, filed August 5, 1941, by J. F. Lontz is illustratively employed with a long chain betaine in Examples IV, V and VI below.

EXAMPLE IV Polydecamethylenesebacamidine dlhydrochloride (IV), has a linear structure as follows:

n being the number or units in the polymeric chain. The titers 01" this compound alone and in the presence of soap, C-hexadecylbetaine and N-dodecylbetaine according to the F. D. A. method at 37 C. against Staphylococcus aureus are as follows:

'I'Aan: VI

Killing dilution in- 5 mins. mins. mins.

Control (IV alone) 1:20, 000 1:30, 000 1:30,000 IVwith 1% soap 1:1,000 1:1,000 1:1,000 IV with 1% C-hoxadeeylbe e 1 30,000 1:30,000 1:75,000 IV with 1% N-dodecylbetaine. 1: ,000

With soap, the germicidal titer of IV is reduced to $5 to A, while with the detergent N-dodecylbetaine the titer in 15 minutes is unaflected. In

the presence of C-hexadecylbetaine the titer in 15 minutes is more than doubled, indicating a definite synergistic effect since the detergent was used at a concentration beyond-the range of its own germicidal activity.

EXAIMPLEV A series of titers similar to those in Example IV were conducted with a homolog of compound IV, namely polydodecamethylenesebacamidine dihydrochloride (V), the linear structure of which i represented as follows:

Nanci NHHCI 11; being the number of units in the polymeric While soap has caused a reduction in germicidal activity to 3% or less, the bactericide is more than ten times more effective in the presence 01' the soap and is unaflected by the presence of N- The condensed format the betaines in the presdodecylbetaine.

EXAMPLE VI A series of titers similar to those in Example V were conducted.- with dodecamethyleneadipamidine dihydrochloride (VI) whose linear structure is represented as follows:

As in the previous examples, soap reduces the germicidal activity to 0.2% or Mm oi the activity without soap, while the betaine, though slightly decreasing the activity on shorter periods, makes no serious reductions on longer exposures.

In these germicidal-detergent combinations, the non-interfering property of these long-chain betaines is not shared by other types of detergents such as the salts of long-chain alcohol sulfates and the alkanesulfonic acids prepared from hydrocarbons, sulfur dioxide, and chlorine according to the U. S. Patent 2,046,090. These two types of detergents behave like soaps in seriously reducing the germicidal titer.

In so far as the effect of the germicidal agent on the betane detergent is concerned, standard detergent tests indicate that the detergent properties of the latter are improved slightly by the former in hard water. In soft water the betaine does not show any serious loss in detergency.

In addition to the Staphylococcus organism used in the above examples of the standard F. D. A. test, the germicidal compositions of this invention are also highly active against. otherorganisms such as B. coli, B. typhosus, Streptococcus; Pneumococcus, E. 0011', S. para-dysenteriae, S. dysenteriae, N..catarrhalis, M. albz'cans, Trichophytcn, and others.

In the compositions of this invention, there are two essential components-a bactericidal salt oi a long chain basic nitrogen compound and a long chain betaine, i. e., a betaine or internal salt having an alkyl substituent of eight to eighteen carbon atoms or an annular atom of the betaine in its cyclic form, the extracyclic valences of the basic hetero atom (nitrogen or sulfur) of the betaine being satisfied by alkyl radicals.

A particularly preferred class. of betaines is that of the aminoacetic acid betaines of the formule. (condensed or inner salt form) wherein R RF, and R are alkyl radicals, R is hydrogen or alkyl and at least one of the R radicals is an alkyl radical of eight to eighteen carbon atoms.

ence of water is in equilibrium with the open structure as illustrated by the following:

Ra 3' B H- The preparation of thesecompounds and speciflc examples thereof useful in the presentinvention are described in the U. 8. Patent 2,129,264. Any such betaine may be employed in the compositions oi the present invention, including N,N,N-dimethyloctylbetaine, N,N,N-diethyldecyl- V betaine, N,N,N-dimethyldodecylbetaine, N,N,N- dimethyloctadecylbetaine, N .N ,N -trimethyl-C- decylbetaine, N,N,N-triethyl-C-decylbetaine, and N,N,N-trimethyl-C-hexadecylbetaine.

Another class of betaines, that 0! the suite betaines or taurobetaines (Richter, vol. 1 (1913) page wherein R and R. are alkyl, RF is hydrogen or alkyl, at least one of R l t and B being alkyl of eight to eighteen carbon atoms. Any such thetine may be employed including S,S-me thyldecylthetine, S,S-methyldodecylthetine, S,S-ethy lhexadecylthetine, S,S-butyloctadecylthetine, S,S-dimethyl-C-decylthetine, and S,S-diethyl-C-hexadecylthetine.

The second essential component of thecompositions of this invention is a bactericidal watersoluble salt or a basic nitrogen compound which in aqueous solution iurnishes an organic cation having mobility, i. e., movement within the solution, independentoi all the anions in said solution and which is selected from the class consisting or addition salts of monomeric basic nitrogen compounds having attached to the basic nitr gen, a'monovalent aliphatic hydrocarbon radical of at least eight carbon atoms, and water soluble salts of linear polymeric basic nitrogen compounds which have, in the multiply recurring p lymeric unit and as an integral part of the linear chain, a nitrogen atom attached through aliphatic carbon to a bivalent organic, preferably hydrocarbon and preferably aliphatic, radical or at least four chain atoms, the terminal atoms or which are carbon.

Addition salts are the salts formed by add n an acid to a trivalent basic nitrogen, e. g., salts formed by the reaction oi a primary, secondary or tertiaryamine with .anacid.

The addition salts of monomeric basic nitrogen compounds containing, attached to the nitrogen, a monovalent aliphatic radical or at least eight carbon atoms include salts of amines, amidines, guanidines and isothioureas having a long chain alkyl radical on the basic nitrogen. Any of these may be employed including dodecylamine hydrochloride, N,N-dimethyldodecylamine hydrobromide, N-dodecylethylenediamine hydrobromide. dimethylbenzyldodecylammonium chloride, decamethylene bis(dimethyldecylammonium bromide) and the related compounds or U. 8. Patents 2,113,806 and 2,108,765, lauramidine hydrochloride, decylguanidine hydrochloride, and N -dodecyl-B-methylisothiourea hydrobromide.

The preferred types of compounds are those oi poly-functional nature including the linear polymeric and the double or his types since these show the highest bactericidal titers in the presence of the betaines.

The linear polymeric basic nitrogen salts include linear polymeric quaternary ammonium salts in which the multiply recurring linear polymeric umt comprises at least seven chain atoms,

two of which are quaternary ammonium atoms,

separated by organic radicals attached to the quaternary ammonium atoms through carbon, one of the valences on each quaternary ammonium nitrogen being satisfied by the anion of an acid and the remaining valences of the quaternary ammoniul'nnitrogen being satisfied by organic radicals attached to the quaternary ammonium nitrogen through carbon not more than one of the carbons attached to-the quaternary ammonium nitrogen 85 being in turn joined to another carbon by a multiple bond. These linear polymeric quaternary ammonium salts are disclosed in Searle U. S. Patent 2,271,378, the compounds of which are generally useful in the compositions of the present inven- 40 tion and include polydecamethylenedimethylammonium bromide, polyhexamethylenedimethylammonium bromide, polyhexamethylenedimethylammonium chloride, polyhexamethylenedimethylammonium iodide, po ydecamethylenedimethylammonium chloride, the polyquaternary ammonium salt from N,N,N' ,N'-tetramethylhexamethylenediamine and decamethylene dibromide, the polymeric quaternary ammonium salt from N,N,N,N' tetramethylhexamethylenediamine and p-xylylene dibromide, polymeric quaternary ammonium salt from N,N,N',N'-tetramethyldecamethylenediamine and hexamethylenedibromide, the polymeric quaternary ammonium salt from N,N,N',N'-tetramethyldecamethylenediamine and p-xylylenedibromide, the polymeric quaternary ammonium salt from 4,4-tetramethylenediaminodiphenylmethane and hexamethylene dibromide, the polymeric quaternary ammonium salt from 4,4'-tetramethyldiaminodiphenylmethane and decamethylene dibromide, and the polymeric quaternary ammonium salt from 4,4-tetramethyldiaminodiphenyl methane and p-xylylene dibromide.

Another class of linear polymeric basic nitrogen compounds generally useful in the compositions of the present invention is that of linear polymeric amidine salts having recurring amidine salt groups connected to divalent organic radicals of at least four chain atoms having their free valences stemming from carbon and free from groups reactive with amidine salt groups. The amidine groups have the formula R being hydrogen or an alkyl group of from one to four carbon atoms. These generally useful compounds are disclosed in greater detail in Lontz Serial No. 405,555, now U. 8. 2,310,799, filed August 5, 1941, and include polydecamethylenesebacamidine dih'ydrochloride, polymeric hexamethyleneadipodiamidine dihydrochloride, polymeric decamethyleneadipodiamidine dihydrochloride, polymeric decamethylenesebacodiami-.

dine dihydrochloride, polymeric hexamethylenesebacodiamidine dihydrochloride, polymeric hexamethylenedodecanodiamidine dihydrochloride, polymeric tetramethyleneadipodiamldlne dihydrochloride, and polymeric decamethylene-pphenylenediacetamidine dihydrochloride.

Still another class of linear polymeric basic nitrogen compounds of general usefulness in the compositions of the present invention are the linear polymeric guanidine salts wherein the intralinear guanidlne groups are connected by bivalent hydrocarbon or ether interrupted hydrocarbon radicals, of at least four chain atoms, the remaining valences of the nitrogens being satisfied by hydrogen or alkyl radicals of from one to seven carbon atoms and the acid of the salt has an ionization constant of at least 1X These generally useful compounds are disclosed by Ernsberger and Lontz in their application Serial No. 424,822, now U. S. 2,336,605, filed December 29, 1941, and include, polydecamethyleneguanidine hydrobromide, polymeric hexamethyleneguanidine hydrobromide, polymeric decamethyleneguanidine meric dodecamethyleneguanidine hydrobromide, and polymeric octadecamethyleneguanidine hydrobromide,

A' further class of these linear polymeric nitrogen bactericides is that of linear polymeric iso thioureas wherein the intralinear isothiourea salt groups where R and R. are hydrogen or alkyl groups of from one to six carbon atoms and X is the anion of an acid of dissociation constant of at least 1x10 and separated by bivalent organic radicals such as hydrocarbon or ether interrupted hydrocarbon radicals of at least four chain atoms whose free valences stem from only singly bonded carbons, These generally useful compounds are disclosed in Hunt application Serial No. 437.091, now U. S. 2,347,827, filed March 31, 1942, and include polymeric S,S'-hexamethylene-N,N'- hexamethylene diisothiourea hydrobromide, S,S'-hexamethy1e ne-N.N'-hexamethylene diisothiourea hydrobromide. S.S'-hexamethylene- N,N-decameth vlene dlisothiourea hydrobromide, S,S'-decamethylene-N,N-decamethylene dilsothiourea hydrobromide. S,S-he xamethylene- N,N'-p-xylylene diisothiourea hydrobromide, S,S'-decamethylene-N.N'-p-xylylene diisothiourea hydrobromide, S,S'-p-xylyiene-N,N-hexa methylene diisothiourea hydrobromide, and S ,S'- decamethylene-N,N'-hexamethylene diisothiourea hydrobromide,

In general, the combinations described in this invention are useful for all disinfecting and sterilizing processes or applications. and they are i even more efficacious than the mere use of a detergent or germicide in view of their added cleansing and penetrating power. There are many instances in which mere rinsing with a germicide solution is insumcient because of the lack of a thorough contact and penetration. In addition, the present combinations can be used as preservatives for which purpose only very small amounts are required in view of their high germicidal activity. These applications include the disinfection of seeds, drinking and eating utensils, milk and beverage glassware, bottles, cans, and other containers, wearing apparel, laundering equipment, floors and walls, the sterilization of surgical instruments, bandages,

masks, sutures, etc. and employment as antihydrobromide, polyseptic ingredients for soaps, cosmetics, mouth washes, tooth pastes, shaving cream, and such cosmetics as face powder, lipstick, rouge, etc.

The above description and examples are intended to be illustrative only. Any modification of or variation therefrom which conforms to the spirit of the invention is intended to be included.

What is claimed is: v

1. A bactericidal composition comprising a betainehaving, on an annular atom of the betaine ring, an alkyl group of atleast eight carbon atoms and a bactericidal, water-soluble, organic,

basic nitrogen-containing salt which, in aqueous solution furnishes an organic cation having mobility independent of all the anions of said solution and is selected from the class consisting of addition salts of monomeric basic nitrogen compounds having attached to the nitrogen a monovalent aliphatic hydrocarbon radical of at least eight carbon atoms and salts of linear polymeric compounds having multiply recurring intralinear basic nitrogen groups connected through bivalent organic radicals of at least four chain atoms, the terminal atoms of which are carbon atoms.

2. A bactericidal composition comprising a betaine having, on an annular atom thereof, an alkyl radical of at least eight carbon atoms and a water-soluble salt of a linear polymeric basic nitrogen compound having multiply recurring intralinear basic nitrogen groups connected through bivalent hydrocarbon radicals of at least six carbon atoms.

3. A bactericidal composition comprising a betaine having, on an annular atom thereof, an alkvl radical of at least eight carbon atoms and a water-soluble linear polymeric quaternary ammonium salt wherein the quaternary ammonium salt groups are separated by bivalent hydrocarbon radicals of at least six carbon atoms.

4. A bactericidal composition comprising a betaine having, on an annular atom thereof, an alkyl radical of at least eight carbon atoms and a water-solvable linear polymeric amidine salt whereinthe amidine salt groups are separated by bivalent hydrocarbon radicals of at least six carbon atoms.

5. A bactericidal composition comprising a betaine having, on an annular atom thereof, an alkyl radical of at least eight carbon atoms and a water-soluble salt of a linear polymeric basic nitrogen compound having multiply recurring intralinear basic nitrogen groups connected through bivalent aliphatic hydrocarbon radicals alkyl radical of at least eiaht carbon atoms and a water-soluble linear polymeric amidine salt wherein the amidine salt groups are separated by bivalent aliphatic hydrocarbon radicals of at least six carbon atoms.

8. A bactericidal composition comprising a betaine having. on an annular atom them! an alkyl radical or at least eight carbon atoms and decamethylene-bmdimemyldecylammonium bromide). r

9. A bactericidal composition comprising N- dodecylbetaine and decamethylene-bia(dimethyl- I decylammonium bromide).

JAMES mom: may. JOHN mam: mom.

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Classifications
U.S. Classification514/556, 510/382, 510/504, 424/49, 424/64, 510/384, 424/63, 510/490, 510/391, 528/397
International ClassificationA61K8/72, A61Q11/00, A61K8/84, C11D3/48
Cooperative ClassificationC11D3/48, A61K8/84, A61Q11/00
European ClassificationC11D3/48, A61Q11/00, A61K8/84