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Publication numberUS3093591 A
Publication typeGrant
Publication dateJun 11, 1963
Filing dateMay 3, 1957
Priority dateMay 3, 1957
Also published asDE1130956B
Publication numberUS 3093591 A, US 3093591A, US-A-3093591, US3093591 A, US3093591A
InventorsRoyce G Freese
Original AssigneeGen Mills Inc
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Compositions containing nu-alkyl-betaamino propionates and germicidal quaternary ammonium compounds
US 3093591 A
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Description  (OCR text may contain errors)

l l l l i l 3,093,591 COMPGSIIIONS CONTAINING N-ALKYL-BETA- AMINO PROPIONATES AND GERMICIDAL QUATERNARY ()NllUM CUMPOUNDS 3,093,591 Patented June 11, 1963 The salt-forming :group of the amphoteric anionic-form surface active agent, i.e., the monoand di-propionate adducts will generally be their alkali metal salts, preferably sodium or potassium, due to their case of prepara- "ice Royce G. Freese, Minneapolis, Mimn, assignor to General 5 tion and the economics of the situation. However, for Mills, Inc. a corporation of Delaware certain specialty applications it may be preferable to use N0 Drawlhg- Filed y 1957, 656,773 an organic salt. in these instances the salts of triethanol 3 Claims- 252-106) amine have been found to be useful. In any case it will This invention relates to new and useful compositions beltappreglated the g g acuvlty of these containing an amphoteric anionic-form detergent and a sa to epresanceo era c S cationic quaternary compound. and RHNCH2CH2COO- Heretofore, it has been the practiceto mix quaternary N(OH CH (:O0) compounds wlth elther non-ionic or catlonlc surface active agents due to the fact that they were incompatible with It also noted f thls type of Surface active agent only anionic acting detergents. The usual result accompanying 15 foam? a exhlbits known desirable detergent chafh mixing f a quatgrnary compound and an anionic acterlstlcs when it is present in its anionic form. acting detergent is the formation of an insoluble pre- It will also be appreciated that the unique combination i i of an amphoteric anionic-form detergent and cationic qua- It has now been discovered that various germicidally telnary cPmpounds taught this invention y be active quaternary compounds f a Compatible and mlxed with other substances commonly utilized in the stable mixture with amphoteric anionic-form detergents applications to which it is to be p y Obviously, of th general Structural fo l RHNCHZCHZCOOX it will generally be employed in the form of a water soluand RN(CH2CH2COOX)Z whgre R is an aliphatic hydr0 tion. Other common ingredients which may be admixed carbon radical containing 8 to 22 carbon atoms, and X is with the compositions of this invention are hen-ionic a 1t f i radical, h r i ft f d to as the 25 surface active agents, humectants such as glycol, lower d dj ro ion t dd of the various f tt alcohols, preferably ethyl alcohol, and phosphates. In amines RNH the preparation of the various solutions contemplated by It is therefore, the primary object of this invention to this invention, the amphotefie anionic-form detergent disclose compositions that contain quaternary compounds either monodi'adduct must be Present 011 a weight and amphoteric anionic-form surface active agents which basis at least in the ratio of 1 t0 1 t0 the amount of form a compatible and stable mixture and which retain quaternary compound in OTdel to Obtain Water solutions and enhance their useful properties in various applications. containing at least 10% solids y Weight Concentrated For instance, the germicidal activity of the quaternary solutions of this p may he mefchahdised as shamPees compgunds are i i d as are h urf activity andother liquid detergent compositions and the stability characteristics of the amphotelic anionic-form detergent. and compatihihty 0f the ingredients are retained at the T ese compositions are especially useful in shampoos, lower concentrations employed in the actual utilization sanitizers, textile treating agents, clothes softening comof the compositions Depending on application positions, liquid dishwashing compositions, and the like. which the compositions are to be employed, the ratio of Various quaternary compounds may be employed in ingredients may vary from the above ratio which is the the practice of this invention. They may be represented 40 lower limit for p o of compatibility- For instance, structurally by the following formula R R R R NY Where as much as 15 parts f the amphoteric anionic-form R R R and R are hydrocarbyl radicals and Y is an detergent y be p y in admixture with 1 p f inorganic anion such as chloride, sulfate, bromide, and the germicidal quaternary Compoundsrelated radicals. A commercially important class of qua- This invention y be illustrated further y reference ternary compounds is where R and R are lower alkyl 1ihe following examples in which all p a radicals containing 1 to 4 carbon atoms, R is an aralkyl Pressed as Parts y weight and all Percentages are radical, and R is an aliphatic hydrocarbon group con- Pressed as Pefeeht y Weight, unless specified Otherwisetaining 8 to 22 carbon atoms. One readily available and I effective member of this class is lauryl dirnethyl benzyl EXAMPLE I ammonium chloride. Another useful class of quaternary Test solutions were prepared of lauryl dimethyl benzyl compounds are those in which R and R are lower alkyl ammonium chloride and coco beta-aminopropionate (the radicals containing 1 to 4 carbon atoms, and R and R compound derived from the mixed amines of coconut oil are aliphatic hydrocarbon radicals from fatty acids conacids). These test solutions were combined in various taining 8 to 22 carbon atoms. An efiective member of proportions as indicated in the following table and were this is dicoco dimethyl ammonium chloride, where coco tested at different levels for their germicidal properties on represents the fact that these aliphatic hydrocarbon radi- Each and S.aureus. The results are indicated in the cals were derived from the fatty acids of coconut oil. following table.

Test solution, percent Active conein ppm. E. coli S. aureus Lauryl 0n basis dimetl'lyl Coco beta of On basis 30sec. 2min. 30 sec. 2min. benzyl aminodetergent 0t expos. expoS. expos. expos. ammonium propionate and santicizcr chloride santicizer 100 0 200 200 0 0 0 0 100 100 l 0 0 0 25 200 150 0 0 0 0 75 1 0 0 0 50 50 200 100 0 0 o 0 100 50 1 0 0 0 25 75 200 50 3 0 s 0 100 25 40 0 *TNTC 0 0 100 200 0 1,200 26 TNTC 'IN'IC 100 0 TNT 1,000 TNTC TNTC *TNTC-Too numerous to count.

3 Solutions bufiered at pH .8 with 0.1 M K HPO Twenty-four hour broth cultures of organisms used.

These data illustrate that the germicidal eifectiveness of the quaternary amomnium compound is unimpaired by the presence of the coco beta-aminopropionate.

EXAMPLE H A solution of 1.0% lauryl dimethyl benzyl ammonium chloride plus 6.0% coco-beta-aminopropionate was prepared. 'Ilhe solution was perfectly clear, no precipitation occurred after an extended period. This solution was next divided into two portions and diluted to typical use concentrations in the shampoo trade.

Solution I:

1.0% coco beta-aminopropionate 0.1667 lauryl dimethyl benzyl amomnium chloride Solution p 0.5% coco beta-aminopropionate I 0.083% lauryl dimethyl benzyl ammonium chloride Comparable solutions containing only coco aminopropiona-te were also prepared.

Solution III: 1.0% coco beta-aminopropionate Solution IV: 0.5 coco beta-aminopropionate Solutions I and III were compared for foaming proper-ties in the standard Ross-Miles test at original pH.

Solution IV.

The combination material at 1.0% concentration (Solution \I) yields a foam height equivalent to that of a lauryl alcohol sulfate which holds a dominant position in the shampoo trade. I

The comparison of Solutions II and IV shows that the foaming of coco beta-aminopropionate is essentially unchanged by addition of the cationic genmicide.

EXAMPLE IIII To a one liter solution containing gms. of stearyl dimethyl benzyl ammonium chloride was added 60 gms. of coc'o beta-aminopropionate. The addition of coco betaaminopropionate did not cause any further clouding of the solution nor was any evidence of precipitation visible.

EXAMPLE IV A typical dishwashing test was used to determine if the addition of the cationic germicide, lauryl dimethyl benzyl amomnium chloride, would effect the d-ishwashing properties of coco beta-aminopropionate.

Test Conditions (1) Soil-plates for soil by depositing thereon 5 gms. of non-emulsified shortening and the shortening allowed to age 1 hour on the plate.

(2) End point-point at which half of the washing surface of the aqueous liquid was no longer covered by foam.

(3) Temperature-415 F.

(4) Water hardness-75 ppm.

(5 Volume of washing solution-5 liters.

(6) Suds on the surface of the washing solution were created by pouring a stream of water into the dishpan containing the dissolved detergent.

Test accuracy is =i=2% plates.

It will be apparent from the above that the quaternary ammonium compound does not adversely afiect the detergent properties of the bea-aminopropionate. It is thus possible to have a liquid dishwashing product with germicidal activity.

EXAMPLE V *In order to study the compatibility and stability of various monoand di-propionate adducts of various amines and various quaternary compounds, the following solutions were prepared: (a) 2 parts dicoco dimethyl ammonium chloride and 8 parts of the sodium salt of the monoapropionate adduct of coco amine 'were dissolved and shown to be compatible with 90 parts of water, (b) 5 parts of the dihydrogenated tallow dimethyl ammonium chloride (-tallow designates that the fatty acid source was tallow) and 15 parts of the sodium salt of the monopropionate adduct of coco amine were dissolved and shown to be compatible with parts of water, (c) 1 part mono tallow trimethyl ammonium chloride and 1 part of the sodium salt of the mono-propionate adduct of coco amine were dissolved and shown to [be compatible with 18 parts of water, (d) 2 parts dicoco dimethyl ammonium chloride and 30 parts of the triethanolamine salt of the mono-propionate adduct of coco amine were dissolved and shown to be compatible wtih 68 parts of water, (e) 1 part mono-tallow trimethyl ammonium chloride and 3 0 parts of the triethanolamine salt of the monopropionate adduct of coco amine were dissolved and shown to be compatible with 18 parts of water, (1) 5 parts of the dihydrogenated tallow dimethyl ammonium chloride and 15 parts of the di-sodium salt of the di-propionate adduct of lauryl amine were dissolved and shown to be compatible with 80 parts of water, and (g) 1 part monotallow trimethyl ammonium chloride and 15 parts of the di-sodium salt of the di-pnopionate adduct of lauryl amine were dissolved and shown to be compatible with 18 parts of water.

EXAMPLE VI Table I shows various liquid detergent sanitizer compositions which may he prepared using the teachings of this invention.

Table I Comp'osi- Quater- Diad- Non- 'IKPP Water Ethatlou nary 1 duct 1 Ionic 3 1101 A 10 15 10 65 B 10 15 5 10 73 2 C 9. 1 11. 7 5. 1 9. 1 64 2 from the spirit and scope thereof, and therefore only such limitations should be imposed are are indicated in the appended claims.

The present application is a continuation-in-part of application Serial No. 483,170 filed January 20, 1955, now abandoned.

Now, therefore, I claim:

1. A compatible and stable composition which comprises an amphoteric anionic-form surface active agent selected from the group consisting of RHNCH CH COOX and RN (CH CH COOX) Where R is an aliphatic hydrocarbon radical containing 8 to 22 carbon atoms and X is a salt forming group, and a cationic germicidal quaternary compound in which said surface active agent is present at least in equal parts by weight to the amount of the quaternary compound employed.

2. A sanitizer composition comprising an ar'nph'oteric anionic-form detergent of the formula where R is an aliphatic hydrocarbon radical containing 8 to 22 carbon atoms, the cationic germicidal quaternary lauryl dimethyl benzyl ammonium chloride, and tetrapotassium pyrophosphate in which said amphoteric anionic-form detergent is present at least in equal parts by weight to the amount of lauryl dimeth-yl benzyl ammonium chloride.

3. A shampoo composition which comprises a concentrated aqueous solution of an amphoteric anionic-form 6 detergent selected from the group consisting of RHNCH CH COOX and RN(OH CH C0OX) where R is an aliphatic hydrocarbon radical containing 8 to 22 canbon atoms and X is a salt forming group and a quaternary compound of the structural formula R R R R NY Where R and R are lower alkyl radicals containing 1 to 4 carbon atoms, R is an aliphatic hydrocarbon radical containing 8 to 22 carbon atoms and derived from a fatty acid, R is selected from the group consisting of benzyl and aliphatic hydrocarbon radicals containing 8 to 22 carbon atoms and derived from a fatty acid and Y is a halogen radical, in which said amphoteric anionic-form detergent is present at least in equal parts by Weight to the amount of the quaternary compound employed.

References Cited in the file of this patent UNITED STATES PATENTS 2,468,012 Isbell Apr. 19, 1949 2,491,992 Malkemus Dec. 20, 1949 2,528,379 Mannheimer Oct. 31, 1950 2,577,773 Lambert Dec. 11, 1951 2,619,467 Isbell Nov. 25, 1952 2,820,042 Rainey et a1 Jan. 14, 1958 OTHER REFERENCES Quaternary Ammonium Germicides, Lawrence Academic Press, New York 0) page 198.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2468012 *Aug 6, 1945Apr 19, 1949Gen Mills IncBeta amino propionates
US2491992 *Dec 29, 1945Dec 20, 1949Colgate Palmolive Peet CoDetergent composition
US2528379 *Oct 7, 1948Oct 31, 1950John J Mccabe JrCycloimidine derivatives and methods for preparing them
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US2820042 *Mar 7, 1955Jan 14, 1958Schenley Ind Inc2-(dialkylaminoalkylthio) benzoxazoles and processes for their production
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3223711 *Mar 20, 1962Dec 14, 1965Hollichem CorpCyclic imide addition products
US3349033 *Aug 26, 1964Oct 24, 1967Millmaster Onyx CorpStable microbiologically active laundry softener
US3589715 *Oct 7, 1968Jun 29, 1971Joseph W MarkConvertible foldable exercise cot
US3622378 *Aug 9, 1968Nov 23, 1971Du PontFibers with anionic-cationic finish
US3904533 *Sep 14, 1970Sep 9, 1975Lever Brothers LtdFabric conditioners
US4013576 *Nov 21, 1973Mar 22, 1977Wesley-Jessen Inc.Contact lens treating composition
US4053423 *Jan 30, 1975Oct 11, 1977Basf Wyandotte CorporationCompositions for souring and softening laundered textile materials, method of preparing the same, and stock solutions prepared therefrom
US4089786 *May 26, 1977May 16, 1978Basf Wyandotte CorporationAmmonium silicofluoride, potassium silicofluoride
US4178256 *May 26, 1977Dec 11, 1979Basf Wyandotte CorporationCompositions for souring and softening laundered textile materials, method of preparing the same, and stock solutions prepared therefrom
US4258063 *Jun 23, 1978Mar 24, 1981Henkel CorporationAmphoteric surfactant, fatty alcohol
US4374853 *Mar 31, 1981Feb 22, 1983Workman Lester JMethod for controlling ectoparasites
US4544494 *Apr 12, 1984Oct 1, 1985Fmc CorporationHomogeneous laundry detergent slurries containing amphoteric surface-active agents
US4743395 *Sep 12, 1986May 10, 1988The Drackett CompanyThickened acid cleaner compositions containing quaternary ammonium germicides and having improved thermal stability
US5486315 *May 20, 1994Jan 23, 1996Lonza Inc.Low foam branched alkyldimethylamine oxides
US5679633 *Oct 17, 1995Oct 21, 1997Lonza Inc.Low foam branched alkyldimethylamine oxides
US6017561 *Apr 4, 1997Jan 25, 2000The Clorox CompanyA quaternary ammonium compound, an anionic polymer having an acid number greater than 10 wherein the anionic polymer is partially or completely neutralized by the ammonium compound to form a polymer complex, a dispersing agent
US6080387 *Jul 15, 1998Jun 27, 2000The Clorox CompanyAerosol antimicrobial compositions
US6270754Jul 1, 1999Aug 7, 2001The Clorox CompanyAntimicrobial cleaning composition
US6482392Jun 23, 2000Nov 19, 2002The Clorox CompanyAerosol antimicrobial compositions
WO1995032270A1 *May 22, 1995Nov 30, 1995Lonza AgLow foam branched alkyldimethylamine oxides
Classifications
U.S. Classification510/123, 510/384, 514/643, 510/480, 516/15, 510/237, 510/391, 510/504, 516/DIG.700, 510/490
International ClassificationA01N37/44, C11D1/88, C11D1/00, C11D1/62, C11D1/10, C11D3/48
Cooperative ClassificationA61K8/416, C11D1/10, A61Q5/02, C11D1/88, C11D3/48, C11D1/62, A61Q17/005, Y10S516/07, A61K8/44
European ClassificationC11D1/88, C11D3/48, C11D1/10, C11D1/62, A61Q17/00F, A61K8/44, A61K8/41L