+

WO1997000609A1 - Procede pour augmenter l'efficacite d'un agent deodorant - Google Patents

Procede pour augmenter l'efficacite d'un agent deodorant Download PDF

Info

Publication number
WO1997000609A1
WO1997000609A1 PCT/US1996/009244 US9609244W WO9700609A1 WO 1997000609 A1 WO1997000609 A1 WO 1997000609A1 US 9609244 W US9609244 W US 9609244W WO 9700609 A1 WO9700609 A1 WO 9700609A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
halo
substituted
composition
odor
Prior art date
Application number
PCT/US1996/009244
Other languages
English (en)
Inventor
Bruce W. Gesslein
Christine Demaio
Virginia L. Lazarowitz
Original Assignee
Henkel Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel Corporation filed Critical Henkel Corporation
Priority to BR9608342A priority Critical patent/BR9608342A/pt
Priority to AU62574/96A priority patent/AU6257496A/en
Publication of WO1997000609A1 publication Critical patent/WO1997000609A1/fr
Priority to MXPA/A/1997/010386A priority patent/MXPA97010386A/xx

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/12—Bis-chlorophenols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/83—Mixtures of non-ionic with anionic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers

Definitions

  • This invention relates to compositions and methods which reduce the unpleasant odor of cleaning compositions containing disinfectants.
  • the invention further relates to odor masking compositions for disinfectant cleaning compositions, to a method of increasing the efficacy of an odor masking or odor repressing agent, and to the use of odor-masked disinfectant compositions in disinfectant cleaning compositions.
  • Cleaning compositions such as personal cleansing preparations, hand and machine dishwashing detergents, hard surface cleaners, and liquid and solid laundry detergents which contain disinfectants such as bactericides or bacteriostats are becoming more widespread.
  • Phenol derivatives are a common class of disinfectants used in cleaning compositions. See e.g. "Disinfectants and Antiseptics", Encyclopedia of Chemical Technology, vol. 7, pp. 808-815 (Kirk-Othmer, eds., John Wiley & Sons, Inc. N.Y., N.Y., 3d ed. 1979).
  • phenol itself is of mostly historical interest or as a research tool in microbiology.
  • the disinfectant art progressed to homologues of phenol, halogenated phenols, halogenated homologues, dihydric and trihydric phenols, hydroxybenzoic acids, bis(hydroxyphenyl)alkanes, and hydroxyquinolines.
  • 3,5-dimethyl-4-chlorophenol is discussed at pages 810 and 811 of that article and 2,4,4'-trichloro-2'-hydroxydiphenyl ether is discussed at page 812.
  • odor masking or odor repressing agents are incorporated into cleaning compositions. Besides masking the odor of the disinfectants, such compounds can also mask the odor of perfumes used to enhance the aesthetic value of the cleaning compositions. In addition, the amounts of odor masking or odor repressing agents necessary to mask the odor of the disinfectants increases the cost of the cleaning products.
  • This invention relates to compositions and methods which reduce the unpleasant odor of cleaning compositions containing disinfectants.
  • One aspect of the present invention is a method for reducing the unpleasant odor of disinfectant cleaning compositions by increasing the efficacy of an odor masking or odor repressing agent in an aqueous cleaning composition containing a disinfectant such as a bactericide.
  • compositions according to the invention contain a nonionic sugar surfactant such as an alkyl glucose ester, an aldobionamide, a gluconamide, a glyceramide, a glyceroglycolipid and polyhydroxy fatty acid amide surfactant, an alkyl polyglycoside or any combination of such surfactants and a compound having anti-bacterial activity selected from the group consisting of halo-substituted monohydric phenol compounds, halo-substituted dihydric phenol compounds, halo-substituted trihydric phenol compounds, halo-substituted hydroxybenzoic acids, halo- substituted bis(hydroxyphenyl)alkanes and quaternary ammonium bromides selected from the group consisting of lauryl dimethylbenzyl ammonium bromide, alkyl trimethyl ammonium bromide, alkyl isoquinolinium bromide and an odor- masking agent selected from the group consisting
  • the present invention also relates to highly concentrated cleaning compositions containing elevated levels of disinfectants such as a bactericide as disclosed herein.
  • Such compositions can be made by combining a nonionic sugar surfactant such as alkyl glucose ester, aldobionamide, gluconamide, glyceramide, glyceroglycolipid and a polyhydroxy fatty acid amide surfactant, and an alkyl polyglycoside and either or both of: (a) an anionic surfactant such as an alkyl ether sulfate, (b) a mixture of at least two different alkyl polyglycosides wherein each alkyl polyglycoside has a different average carbon chain length in the alkyl moiety.
  • the incorporation of (a) and/or (b) above produces a composition which is more stable at high solids levels and permits the preparation of highly concentrated compositions according to the invention having relatively large amounts of disinfectant.
  • This invention also relates to a process for increasing the efficacy of an odor masking or odor repressing agent which comprises adding an effective amount of a nonionic sugar surfactant or a combination of an anionic surfactant and a sugar surfactant to a composition comprised of an anti-bacterial compound as set forth herein and an odor masking or odor repressing agent as set forth herein.
  • This invention also relates to a process for making an anti-bacterial cleaning composition which comprises adding a composition containing an effective amount of a nonionic sugar surfactant, an anti-bacterial compound as set forth herein and an odor masking or odor repressing agent as set forth herein to an aqueous composition containing one or more additional nonionic surfactants, anionic surfactants, amphoteric surfactants, and combinations thereof surfactants in addition to other compounds such as builders, hydrotropes, humectants, etc.
  • a process for making an anti-bacterial cleaning composition which comprises adding a composition containing an effective amount of a nonionic sugar surfactant, an anti-bacterial compound as set forth herein and an odor masking or odor repressing agent as set forth herein to an aqueous composition containing one or more additional nonionic surfactants, anionic surfactants, amphoteric surfactants, and combinations thereof surfactants in addition to other compounds such as builders, hydrotropes, humectant
  • nonionic sugar surfactant refers to surfactants that are based on saccharide moieties.
  • Representative examples of such nonionic sugar surfactants include, but are not limited thereto, alkyl glucose ester, aldobionamide, gluconamide, glyceramide, glyceroglycolipid and polyhydroxy fatty acid amide surfactants, and alkyl polyglycosides each of which is described more fully hereinbelow.
  • alkyl glucose ester sugar surfactants are generally disclosed in U.S. patent Nos. 5,109,127 and 5,190,747 the entire contents of both of which are incorporated herein by reference. These surfactants have the general formula I:
  • R represents a fatty acid residue of 6 to 20 carbon atoms, preferably 6 to 12 carbon atoms and R 1 represents an alkyl group having 2 to 6 carbon atoms.
  • alkyl glucose esters are 1 -ethyl-6- caprylglucoside, 1-ethyl-6-laurylglucoside, 1-butyl-6-caprylglucoside, 1 -ethyl-6- palmitylglucoside and 1-ethyl-6-oleylglucoside.
  • the aldobionamide sugar surfactants are generally disclosed in U.S.
  • An Aldobionamide is generally defined as the amide of an aldobionic acid or aldobionolactone and an aldobionic acid in turn is defined as a sugar substance (e.g. any cyclic sugar) in which the aldehyde group has been replaced by a carboxylic acid which upon drying is capable of cyclizing to form an aldonolactone.
  • the aldobionamides can be based on compounds comprising two saccharide units, e.g.
  • lactobionamides maltobionamides, cellobionamides, melibionamides, orgentiobionamides, or they can be based on compounds comprising more than two saccharide units provided that the polysaccharide has a terminal sugar unit with an aldehyde group available.
  • the preferred aldobionamides of the present invention are lactobionamides of the formula II
  • R 1 and R 2 are the same or different and are selected from hydrogen and an aliphatic hydrocarbon radical containing up to about 36 carbon atoms (e.g. alkyl groups and alkenyl groups which groups may also include a heteroatom such as N, O, S, present, for instance, as an amide, carboxy, ether and/or saccharide moiety) except that R 1 and R 2 cannot simultaneously be hydrogen.
  • an aliphatic hydrocarbon radical containing up to about 36 carbon atoms (e.g. alkyl groups and alkenyl groups which groups may also include a heteroatom such as N, O, S, present, for instance, as an amide, carboxy, ether and/or saccharide moiety) except that R 1 and R 2 cannot simultaneously be hydrogen.
  • the aliphatic hydrocarbon radical preferably contains up to 24 carbon atoms, most preferably from 8 to 18 carbon atoms.
  • lactobionamides are N-propyl lactobionamide, N-pentyl lactobionamide, N-decyl lactobionamide, N-hexadecyl lactobionamide, N-oleyl lactobionamide, N- dodecyl-N-methyl lactobionamide, and N-dodecyloxypropyl lactobionamide.
  • gluconamide sugar surfactants are generally disclosed in U.S. Patent 5,352,386 the entire contents ofwhich is inco ⁇ orated herein by reference. These have the general formula III: HOCH 2 -(CHOH) m -C(O)-NHR
  • R is a straight or branched, saturated or unsaturated aliphatic hydrocarbon having 4 to about 24 carbon atoms, preferably 8 to 24 carbon atoms, which R group can also contain a heteroatom selected from the group consisting of oxygen, nitrogen and sulfur.
  • Representative examples of such are N-octylerythronamide, N-decylerythronamide, N- dodecylerythronamide, N-tetradecylerythronamide, N-decylxylonamide and N- dodecylxylonamide.
  • glyceramide sugar surfactants are generally disclosed in U.S. Patent 5,352,387, the entire contents of which are incorporated herein by reference.
  • R is a C 8 to C 24 straight or branched chained, saturated or unsaturated aliphatic hydrocarbon in which the R group may also be substituted by a heteroatom selected from oxygen, nitrogen and sulfur.
  • Representative examples of such surfactants are N-octylglyceramide, N-decylglyceramide and N- hexadecylglyceramide.
  • the glyceroglycolipid sugar surfactants are generally disclosed in U.S.
  • the glyceroglycolipids can be of the formula IV:
  • a 1 is a saccharide, preferably having one or more saccharide units, more preferably a mono or disaccharide and most preferably a monosaccharide such as glucose or galactose;
  • R and R ⁇ are the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having from 1 to about 24, preferably from about 6 to about 18 carbon atoms;
  • B is OH or a NR 2 R 3 group, wherein R 2 and R 3 may be the same or different and are hydrogen, a branched or unbranched hydrocarbon radical having 1 to 24, preferably from 6 to 18 carbon atoms, and NRR ! and B are positionally interchangeable.
  • surfactants are 3-(butylamino)-2-hydroxypropyl- ⁇ -D- galactopyranoside, 3-(octylamino)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-
  • glyceroglycolipid surfactants are disclosed in published European Patent Application No. 550,280 which is incorporated herein by reference. These surfactants are of the formula:
  • a 1 is from 1 to 4 saccharide units and more preferably represents a mono or disaccharide, and most preferably a monosaccharide, for example, glucose or galactose;
  • R and R are the same or different and are hydrogen, or a branched or unbranched, saturated or unsaturated, hydrocarbon radical having from 1 to 24 carbon atoms, preferably from 6 to 18 carbon atoms.
  • surfactants are 3-(butyloxy)-2-hydroxypropyl- ⁇ -D- galactopyranoside, 3-(eicosyloxy)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3- (decyloxy)-2-hydroxypropyl- ⁇ -D-galactopyranoside, 3-(butyloxy)-2-hydroxypropyl- ⁇ -D-glucopyranoside, 3-(octyloxy)-2-hydroxypropyl- ⁇ -D-mannopyranoside, 3- (tetradecyloxy)-2-hydroxypropyl- ⁇ -D-lactoside, 3-(octadecyloxy)-2-hydroxypropyl- ⁇ -D-maltoside, 3-(octyloxy)-2-hydroxypropyl- ⁇ -D-galactotrioside, and 3- (dodecyloxy)-2-hydroxypropyl- ⁇ -D-cellotrioside.
  • the polyhydroxy fatty acid amide sugar surfactants are generally disclosed in U.S. Patent Nos. 5,174,927, 5,223,179 and 5,332,528 the entire disclosure of each ofwhich is incorporated herein by reference.
  • the polyhydroxy fatty acid amide surfactant component of the present invention comprises compounds of the structural formula V: R 2 C(O)N(R 1 )Z
  • R 1 is H, C C 4 hydrocarbyl, 2-hydroxy ethyl, 2-hydroxy propyl or a mixture thereof, preferably C r C 4 alkyl, more preferably C, or C 2 alkyl, most preferably C, alkyl (i.e., methyl); and R 2 is a C 5 -C 31 hydrocarbyl, preferably straight chain C 7 -C 19 alkyl or alkenyl, more preferably straight chain C 9 -C 17 alkyl or alkenyl, most preferably straight chain C ⁇ C 17 alkyl or alkenyl, or mixture thereof; and Z is a polyhydroxyhydrocarbyl having a linear hydrocarbyl chain with at least 3 hydroxyls directly connected to the chain, or an alkoxylated derivative (preferably ethoxylated or propoxylated) thereof. Z preferably will be derived from a reducing sugar in a reductive amination reaction; more preferably Z is a glycityl.
  • Suitable reducing sugars include glucose, fructose, maltose, lactose, galactose, mannose, and xylose.
  • high dextrose corn syrup, high fructose corn syrup, and high maltose corn syrup can be utilized as well as the individual sugars listed above. These corn syrups may yield a mix of sugar components for Z. It should be understood that it is by no means intended to exclude other suitable raw materials.
  • Z preferably will be selected from the group consisting of -C H 2 -(C H O H ) n-C H 2 O H , -C H (C H 2 O H )-(C H O H ) n . 1 -C H 2 O H ,
  • n is an integer from 3 to 5, inclusive, and R' is H or a cyclic or aliphatic monosaccharide, and alkoxylated derivatives thereof. Most preferred are glycityls wherein n is 4, particularly
  • R 1 can be, for example, N-methyl, N-ethyl, N-propyl, N-isopropyl, N-butyl, N-2-hydroxy ethyl, or N-2-hydroxy propyl.
  • R 2 C(O)N ⁇ can be, for example, cocamide, stearamide, oleamide, lauramide, myristamide, capricamide, palmitamide, tallowamide, etc.
  • Z can be 1-deoxyglucityl, 2-deoxyfructityl, 1-deoxymaltityl, 1-deoxylactityl, 1-deoxygalactityl, 1-deoxymannityl, 1-deoxymaltotriotityl, etc.
  • cosurfactants are N-methyl-N-1-deoxyglucityl cocoamide and N-methyl-N-1 -deoxyglucityl tallowamide.
  • Other suitable polyhydroxy fatty acid amide surfactants are those of the formula VI:
  • R is a C 7 -C 21 hydrocarbyl species, i.e. coconut, tallow, palm fatty alkyl and oleyl
  • R 1 is a C, to C 6 hydrocarbyl or substituted hydrocarbyl species, i.e. N-alkyl-N-(1 ,2-propanediol) and N-hydroxyalkyl-N-1 ,2-propane diol fatty acid amides.
  • cosurfactants are the tallow amide of 3-[2-(hydroxyethyl)amino]-1 ,2-propanediol (HEAPD), the palmitate amide of 3- methylamino-1 ,2-propanediol (MAPD) and the lauramide of MAPD.
  • alkyl polyglycoside surfactants are compounds of the formula Vll
  • R 1 O(R 2 O) b (Z) a VI I wherein R is a monovalent organic radical having from about 6 to about 30 carbon atoms; R 2 is divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6.
  • Preferred alkyl polyglycosides which can be used in the compositions according to the invention have the formula Vll wherein Z is a glucose residue and b is zero.
  • alkyl polyglycosides are commercially available, for example, as APG®, GLUCOPON®, or PLANTAREN®, surfactants from Henkel Corporation,
  • Examples of such surfactants include but are not limited to: 1. GLUCOPON® 225 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 10 carbon atoms and having an average degree of polymerization of 1.7. 2. GLUCOPON® 425 Surfactant - an alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.55.
  • GLUCOPON® 625 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
  • APG® 325 Surfactant - an alkyl polyglycoside in which the alkyl group contains 9 to 11 carbon atoms and having an average degree of polymerization of 1.6.
  • GLUCOPON® 600 Surfactant - an alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.4.
  • PLANTAREN® 2000 Surfactant - a C 8 . 16 alkyl polyglycoside in which the alkyl group contains 8 to 16 carbon atoms and having an average degree of polymerization of 1.4.
  • PLANTAREN® 1300 Surfactant - a C 12 . 16 alkyl polyglycoside in which the alkyl group contains 12 to 16 carbon atoms and having an average degree of polymerization of 1.6.
  • alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula Vll wherein Z represents a moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; a is a number having a value from 1 to about 6; b is zero; and R. is an alkyl radical having from 8 to 20 carbon atoms.
  • compositions are characterized in that they have increased surfactant properties and an HLB in the range of about 10 to about 16 and a non-Flory distribution of glycosides, which is comprised of a mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having varying degrees of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with the polyglycoside having a degree of polymerization of 3, predominate in relation to the amount of monoglycoside, said composition having an average degree of polymerization of about 1.8 to about 3.
  • compositions also known as peaked alkyl polyglycosides
  • the relative distribution of the various components, mono- and poly-glycosides, in the resulting product changes and the concentration in the product of the polyglycosides relative to the monoglycoside increases as well as the concentration of individual polyglycosides to the total, i.e. DP2 and DP3 fractions in relation to the sum of all DP fractions.
  • Such compositions are disclosed in U.S. patent 5,266,690, the entire contents ofwhich are incorporated herein by reference.
  • alkyl polyglycosides which can be used in the compositions according to the invention are those in which the alkyl moiety contains from 6 to 18 carbon atoms in which and the average carbon chain length of the composition is from about 9 to about 14 comprising a mixture of two or more of at least binary components of alkyl polyglycosides, wherein each binary component is present in the mixture in relation to its average carbon chain length in an amount effective to provide the surfactant composition with the average carbon chain length of about 9 to about 14 and wherein at least one, or both binary components, comprise a Flory distribution of polyglycosides derived from an acid-catalyzed reaction of an alcohol containing 6-20 carbon atoms and a suitable saccharide from which excess alcohol has been separated.
  • Preferred nonionic sugar surfactants are alkyl polyglycosides as set forth above.
  • the mixtures of alkyl polyglycosides which are useful for making highly concentrated cleaning compositions containing elevated levels of disinfectants such as a bactericide are combinations of alkyl polyglycosides wherein each of the alkyl moieties contains from 8 to 16 carbon atoms on the average.
  • a mixture containing an alkyl polyglycoside having an average carbon chain length of 8 carbons in the alkyl moiety and an alkyl polyglycoside having an average carbon chain length of 16 carbons in the alkyl moiety can be used to make highly concentrated cleaning compositions containing elevated levels of disinfectants such as a bactericide.
  • the preferred mixture of alkyl polyglycosides contains a C 10 and a C 12 alkyl polyglycoside.
  • the relative amount of each alkyl polyglycoside will depend upon a number of variables such as the nature of the alkyl polyglycosides, the type of antibacterial compound, the presence of other surfactants and the nature of the odor-masking agent.
  • the relative amount of each alkyl polyglycoside by weight can range from 30/70 to about 70/30 with the preferred being from 40/60 to about 60/40.
  • An effective amount of sugar surfactant according to the invention is any amount sufficient to decrease the amount of odor masking or odor repressing agent relative to the amount of odor masking or odor repressing agent that would be required without the use of a sugar surfactant. This amount can be readily determined by one of ordinary skill in the art and will typically vary from a sugar surfactant /odor masking agent weight ratio of from about 2/1 to about 45/1.
  • the preferred sugar surfactant is alkyl polyglycoside.
  • anti-bacterial agent as used herein includes compounds which are bacteriocidal and bactenostatic.
  • compositions and processes according to the invention are particularly effective when the anti-bacterial compound is a halo-substituted monohydric phenol, a halo-substituted dihydric phenol, a halo-substituted trihydric phenol compound, halo-substituted hydroxybenzoic acid, and a halo- substituted bis(hydroxyphenyl)alkane.
  • halo-substituted it is meant that the compound has one or more halogen atoms, preferably chlorine or bromine, covalently bonded to the phenolic ring.
  • the compounds may also have other substituents, e.g. alkyl groups, aralkyl groups, alkaryl groups, alkoxy groups, aryloxy groups, alkaryloxy groups, and aralkoxy groups.
  • dihydric phenol and trihydric phenol are meant to include both compounds wherein the hydroxyl groups of the compound are all on one phenyl group (e.g. a resorcinol derivative) and compounds wherein two or more hydroxyl groups are distributed among two or more phenyl groups in the compound (e.g. a hydroxyphenyl phenol derivative).
  • the compounds can be in the free hydroxyl form or a salt thereof, e.g. sodium, calcium, or ammonium.
  • Suitable phenolic compounds include but are not limited to halo-phenols, preferably ortho- or para-substituted (e.g. o-chlorophenol, p- chlorophenol, o-bromophenol, and p-bromophenol), alkyl-halo-phenols, for preferably C-, to C 7 normal alkyl-substituted halo-phenols (e.g.
  • 2-chloro-4-methyI- phenol 4-chloro-2-methyl-phenol, 2-bromo-4-methyl-phenol, 4-bromo-2-methyl- phenol, 2-chloro-4-(n-heptyl)-phenol 4-chloro-3,5-dimethyl-phenol, and 4-chloro- 3,5-di(n-heptyl)-phenol
  • aralkyl-halo-phenols preferably benzyl-halo-phenols (e.g. p-chloro-o-benzyl-phenol), aryl-halo-phenols, preferably phenyl-halo- phenols (e.g.
  • p-chloro-o-phenyl-phenol dihydric phenols, preferably hydroxy- halo-phenyloxy-halo-phenols (e.g. 2,4,4'-trichloro-2'-hydroxydiphenyl ether) and bis(hydroxy-halo-phenyl)alkanes, preferably bis(hydroxy-halo-phenyl)methanes
  • the process according to the invention is also particularly effective when the anti-bacterial compound is one or more quaternary ammonium bromide compounds selected from the group consisting of lauryl dimethylbenzyl ammonium bromide, commercially available as, for example, AMOMYL® BR 1244 a trademark product of Seppic; alkyl trimethyl ammonium bromide, commercially available as, for example, EMPIGEN® CHB 40, a trademark product of Albright & Wilson; alkyl isoquinolinium bromide, commercially available as, for example, CATINAL® CB 50, a trademark product of Toho Chemical.
  • lauryl dimethylbenzyl ammonium bromide commercially available as, for example, AMOMYL® BR 1244 a trademark product of Seppic
  • alkyl trimethyl ammonium bromide commercially available as, for example, EMPIGEN® CHB 40, a trademark product of Albright & Wilson
  • alkyl isoquinolinium bromide commercially available as,
  • the amount of anti-bacterial compound which can be used in cleaning compositions is any disinfecting amount or anti-bacterially effective amount and will depend upon the concentration or the use dilution. The amount will typically vary from 0.1% to 5% by weight.
  • anionic surfactants that can be used in combination with the sugar surfactants to produce disinfectant cleaning compositions which are more stable at elevated total solids levels are selected from the group consisting of alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkyl ether sulfonates, and sulfosuccinates.
  • the preferred type of anionic surfactant is an alkyl ether sulfate.
  • the amount of such anionic surfactant is any amount which will produce a stable composition that will not separate or become otherwise unstable upon prolonged standing.
  • the amount of anionic surfactant can be readily determined by one of ordinary skill in the art and will typically vary from an anionic surfactant/antibacterial compound weight from about 8/1 to about 17/1 with the preferred amount being from about 1/1 to about 3/1.
  • the process according to the invention can be employed for any type of odor masking or odor repressing agent such as those described in an article entitled "Odor Modification” in Encyclopedia of Chemical Technology, vol. 16, pp. 303-304 (Kirk-Othmer, eds., John Wiley & Sons, Inc. N.Y., N.Y., 3d ed.
  • odor masking or odor repressing agents include Mask #39741 and Fragrance 49627, which are combinations of aromatic aldehydes, esters, alcohols, and oxygenated monoterpenes such as ionones, available from
  • One preferred embodiment of the present invention is a composition containing an effective amount of an alkyl polyglycoside surfactant of the formula Vll R 1 O(R 2 O) b (Z) a Vl l wherein R, is a monovalent organic radical having from about 6 to about 30 carbon atoms; R 2 is divalent alkylene radical having from 2 to 4 carbon atoms; Z is a saccharide residue having 5 or 6 carbon atoms; b is a number having a value from 0 to about 12; a is a number having a value from 1 to about 6 is added to a composition comprised of an effective amount of 4-chloro-3,5- dimethyl-phenol (p-chloro-meta-xylenol) and an effective amount of Mask
  • a preferred alkyl polyglycoside is one in which the alkyl group contains
  • the following disinfectant cleaning composition was a clear fluid product:
  • PCMX 4-chloro-3,5-dimethyl-phenol
  • a clear, flowable, readily dilutable concentrate contained the following ingredients:
  • the first three ingredients were heated together with mixing to 70°C.
  • the PCMX was then slowly mixed in while heating at 75-80°C.
  • the mixture was cooled to room temperature and the Fragrance 49627 was added.
  • the pH was adjusted to 7.0 with a 50% citric acid solution.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Molecular Biology (AREA)
  • Toxicology (AREA)
  • Detergent Compositions (AREA)

Abstract

L'efficacité d'un agent qui supprime ou qui refoule les odeurs, dans un composé de nettoyage aqueux contenant un désinfectant tel qu'un bactéricide peut être améliorée par l'incorporation d'un tensio-actif de sucre non-ionique dans un composé aqueux qui contient un composé ayant une activité anti-bactérienne et un agent supprimant les odeurs.
PCT/US1996/009244 1995-06-21 1996-06-17 Procede pour augmenter l'efficacite d'un agent deodorant WO1997000609A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BR9608342A BR9608342A (pt) 1995-06-21 1996-06-17 Composição de limpeza desinfetante e processos para aumentar e eficácia de um agente de conter odor ou mascarar odor e preparar uma composição de limpeza desinfetante
AU62574/96A AU6257496A (en) 1995-06-21 1996-06-17 Method for increasing the efficacy of an odor masking agent
MXPA/A/1997/010386A MXPA97010386A (en) 1995-06-21 1997-12-18 Method to increase the effectiveness of an overcover agent

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US38095P 1995-06-21 1995-06-21
US60/000,380 1995-06-21
US66058996A 1996-06-11 1996-06-11
US08/660,589 1996-06-11

Publications (1)

Publication Number Publication Date
WO1997000609A1 true WO1997000609A1 (fr) 1997-01-09

Family

ID=26667549

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1996/009244 WO1997000609A1 (fr) 1995-06-21 1996-06-17 Procede pour augmenter l'efficacite d'un agent deodorant

Country Status (5)

Country Link
AR (1) AR002548A1 (fr)
AU (1) AU6257496A (fr)
BR (1) BR9608342A (fr)
CA (1) CA2225016A1 (fr)
WO (1) WO1997000609A1 (fr)

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998050519A1 (fr) * 1997-05-09 1998-11-12 Colgate-Palmolive Company Composition liquides de nettoyage
WO1999008517A1 (fr) * 1997-08-18 1999-02-25 Cognis Deutschland Gmbh Microemulsions
EP0916720A1 (fr) * 1997-11-17 1999-05-19 The Procter & Gamble Company Compositions liquides antibactériennes pour la vaisselle
DE19804042A1 (de) * 1998-02-03 1999-09-09 Widulle Geruchsbinder für aldehydhaltige Desinfektionsmittel
US6319958B1 (en) 1998-06-22 2001-11-20 Wisconsin Alumni Research Foundation Method of sensitizing microbial cells to antimicrobial compound
US6335004B1 (en) 2000-05-31 2002-01-01 Ecolab Inc. Odorless phenolic compositions
KR100423644B1 (ko) * 2000-07-18 2004-03-22 주식회사 만도 브레이크시스템용 솔레노이드밸브
WO2004035720A1 (fr) 2002-10-16 2004-04-29 Henkel Kommanditgesellschaft Auf Aktien Produit de nettoyage abrasif transparent, notamment produit de nettoyage de vaisselle a la main
EP1564283A2 (fr) 2000-01-27 2005-08-17 Henkel Kommanditgesellschaft auf Aktien combinaison de tensio-actifs
US7186675B2 (en) 2000-09-13 2007-03-06 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Quick drying washing and cleaning agent, comprising an anionic/cationic/amphoteric surfactant mixture
WO2008074070A1 (fr) * 2006-12-18 2008-06-26 Pestat Pty Ltd Composition pour la lutte contre les organismes nuisibles
US7393820B2 (en) 2002-10-16 2008-07-01 Henkel Kommanditgesellschaft Auf Aktien Transparent abrasive cleaning product, especially manual dishwashing liquid
WO2009125222A3 (fr) * 2008-04-11 2010-12-16 The Queen's University Of Belfast Système antimicrobien
US7998918B2 (en) 2006-12-05 2011-08-16 Henkel Ag & Co. Kgaa Cleaning compositions for hard surfaces comprising a silyl polyalkoxylate
US7998919B2 (en) 2006-12-05 2011-08-16 Henkel Ag & Co. Kgaa Compositions for treating hard surfaces comprising silyl polyalkoxylates
EP1082149B2 (fr) † 1998-05-29 2011-12-14 Kimberly-Clark Worldwide, Inc. Meilleure absorption des odeurs par des polymeres naturels et de synthese
DE102013001859A1 (de) 2013-02-01 2014-08-07 Henkel Ag & Co. Kgaa Neue Tenside mit niedriger CMC sowie Tensidsysteme und Waschmittel enthaltend diese
DE102016225902A1 (de) 2016-12-21 2018-06-21 Henkel Ag & Co. Kgaa Reinigungsmittel mit abrasiven vulkanischem Glas
EP3441447A1 (fr) 2017-08-09 2019-02-13 Henkel AG & Co. KGaA Éther de cellulose non ionique en tant que renforçateur d'élimination de salissures lors du nettoyage de surfaces dures
EP4105307A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Composition de nettoyage diluable visqueuse stable
EP4105304A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Concentré diluable auto-épaississant pour applications de nettoyage de surfaces dures et de lavage de vaisselle
EP4105306A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Composition détergente diluable super concentrée pour le lavage manuel de la vaisselle
EP4186969A1 (fr) 2021-11-26 2023-05-31 Henkel AG & Co. KGaA Poudre diluable super-concentrée pour laver la vaisselle
EP4379028A1 (fr) 2022-11-30 2024-06-05 Henkel AG & Co. KGaA Systeme de builder pour l'élimination des taches de protéines

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547828A (en) * 1968-09-03 1970-12-15 Rohm & Haas Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols
USH269H (en) * 1985-03-11 1987-05-05 A. E. Staley Manufacturing Company Disinfectant and/or sanitizing cleaner compositions
US4880558A (en) * 1987-06-19 1989-11-14 Henkel Kommanditgesellschaft Auf Aktien Liquid cleaning preparation for hard surfaces
US5025069A (en) * 1988-12-19 1991-06-18 Kao Corporation Mild alkyl glycoside-based detergent compositions, further comprising terpene and isothiazolone derivatives
US5330674A (en) * 1992-09-09 1994-07-19 Henkel Corporation Method for increasing the efficiency of a disinfectant cleaning composition using alkyl polyglycosides
US5370816A (en) * 1990-09-13 1994-12-06 Huels Aktiengesellschaft Detergent composition containing a mixture of alkyl polyglycosides
US5403505A (en) * 1990-03-12 1995-04-04 Henkel Kommanditgesellschaft Auf Aktien Cleaning and disinfecting agent containing an N-substituted propylene glutamic acid or derivative thereof, and an antimicrobially active compound

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3547828A (en) * 1968-09-03 1970-12-15 Rohm & Haas Alkyl oligosaccharides and their mixtures with alkyl glucosides and alkanols
USH269H (en) * 1985-03-11 1987-05-05 A. E. Staley Manufacturing Company Disinfectant and/or sanitizing cleaner compositions
US4880558A (en) * 1987-06-19 1989-11-14 Henkel Kommanditgesellschaft Auf Aktien Liquid cleaning preparation for hard surfaces
US5025069A (en) * 1988-12-19 1991-06-18 Kao Corporation Mild alkyl glycoside-based detergent compositions, further comprising terpene and isothiazolone derivatives
US5403505A (en) * 1990-03-12 1995-04-04 Henkel Kommanditgesellschaft Auf Aktien Cleaning and disinfecting agent containing an N-substituted propylene glutamic acid or derivative thereof, and an antimicrobially active compound
US5370816A (en) * 1990-09-13 1994-12-06 Huels Aktiengesellschaft Detergent composition containing a mixture of alkyl polyglycosides
US5330674A (en) * 1992-09-09 1994-07-19 Henkel Corporation Method for increasing the efficiency of a disinfectant cleaning composition using alkyl polyglycosides

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998050519A1 (fr) * 1997-05-09 1998-11-12 Colgate-Palmolive Company Composition liquides de nettoyage
WO1999008517A1 (fr) * 1997-08-18 1999-02-25 Cognis Deutschland Gmbh Microemulsions
US6255253B1 (en) 1997-08-18 2001-07-03 Cognis Deutschland Gmbh Microemulsions
EP0916720A1 (fr) * 1997-11-17 1999-05-19 The Procter & Gamble Company Compositions liquides antibactériennes pour la vaisselle
WO1999025800A1 (fr) * 1997-11-17 1999-05-27 The Procter & Gamble Company Compositions detergentes antibacteriennes, liquides, pour la vaisselle
DE19804042A1 (de) * 1998-02-03 1999-09-09 Widulle Geruchsbinder für aldehydhaltige Desinfektionsmittel
EP1082149B2 (fr) † 1998-05-29 2011-12-14 Kimberly-Clark Worldwide, Inc. Meilleure absorption des odeurs par des polymeres naturels et de synthese
US6319958B1 (en) 1998-06-22 2001-11-20 Wisconsin Alumni Research Foundation Method of sensitizing microbial cells to antimicrobial compound
EP1564283A2 (fr) 2000-01-27 2005-08-17 Henkel Kommanditgesellschaft auf Aktien combinaison de tensio-actifs
US6335004B1 (en) 2000-05-31 2002-01-01 Ecolab Inc. Odorless phenolic compositions
KR100423644B1 (ko) * 2000-07-18 2004-03-22 주식회사 만도 브레이크시스템용 솔레노이드밸브
US7186675B2 (en) 2000-09-13 2007-03-06 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Quick drying washing and cleaning agent, comprising an anionic/cationic/amphoteric surfactant mixture
WO2004035720A1 (fr) 2002-10-16 2004-04-29 Henkel Kommanditgesellschaft Auf Aktien Produit de nettoyage abrasif transparent, notamment produit de nettoyage de vaisselle a la main
US7393820B2 (en) 2002-10-16 2008-07-01 Henkel Kommanditgesellschaft Auf Aktien Transparent abrasive cleaning product, especially manual dishwashing liquid
US7998918B2 (en) 2006-12-05 2011-08-16 Henkel Ag & Co. Kgaa Cleaning compositions for hard surfaces comprising a silyl polyalkoxylate
US7998919B2 (en) 2006-12-05 2011-08-16 Henkel Ag & Co. Kgaa Compositions for treating hard surfaces comprising silyl polyalkoxylates
AU2007335245B2 (en) * 2006-12-18 2009-03-12 Pestat Pty Ltd Composition for pest control
WO2008074070A1 (fr) * 2006-12-18 2008-06-26 Pestat Pty Ltd Composition pour la lutte contre les organismes nuisibles
US8962694B2 (en) 2006-12-18 2015-02-24 Pestat Pty Ltd. Composition for pest control
WO2009125222A3 (fr) * 2008-04-11 2010-12-16 The Queen's University Of Belfast Système antimicrobien
DE102013001859A1 (de) 2013-02-01 2014-08-07 Henkel Ag & Co. Kgaa Neue Tenside mit niedriger CMC sowie Tensidsysteme und Waschmittel enthaltend diese
EP4112708A1 (fr) 2016-12-21 2023-01-04 Henkel AG & Co. KGaA Détergent comportant du verre volcanique abrasif
DE102016225902A1 (de) 2016-12-21 2018-06-21 Henkel Ag & Co. Kgaa Reinigungsmittel mit abrasiven vulkanischem Glas
WO2018114100A1 (fr) 2016-12-21 2018-06-28 Henkel Ag & Co. Kgaa Produit de nettoyage comprenant du verre volcanique abrasif
EP3441447A1 (fr) 2017-08-09 2019-02-13 Henkel AG & Co. KGaA Éther de cellulose non ionique en tant que renforçateur d'élimination de salissures lors du nettoyage de surfaces dures
EP4105304A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Concentré diluable auto-épaississant pour applications de nettoyage de surfaces dures et de lavage de vaisselle
EP4105306A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Composition détergente diluable super concentrée pour le lavage manuel de la vaisselle
EP4105305A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Composition de nettoyage diluable visqueuse stable
EP4105307A1 (fr) 2021-06-15 2022-12-21 Henkel AG & Co. KGaA Composition de nettoyage diluable visqueuse stable
EP4186969A1 (fr) 2021-11-26 2023-05-31 Henkel AG & Co. KGaA Poudre diluable super-concentrée pour laver la vaisselle
WO2023094115A1 (fr) 2021-11-26 2023-06-01 Henkel Ag & Co. Kgaa Poudre diluable super-concentrée pour application de lavage de vaisselle
EP4379028A1 (fr) 2022-11-30 2024-06-05 Henkel AG & Co. KGaA Systeme de builder pour l'élimination des taches de protéines

Also Published As

Publication number Publication date
CA2225016A1 (fr) 1997-01-09
BR9608342A (pt) 1999-01-05
MX9710386A (es) 1998-03-29
AR002548A1 (es) 1998-03-25
AU6257496A (en) 1997-01-22

Similar Documents

Publication Publication Date Title
WO1997000609A1 (fr) Procede pour augmenter l'efficacite d'un agent deodorant
US5962399A (en) Preparation of alkylpolyglycosides and cleaning compositions comprising same
US5266690A (en) Preparation of alkylpolyglycosides
AU768691B2 (en) Low residue aqueous hard surface cleaning compositions particularly adapted for cleaning glass and glossy hard surfaces
US6046146A (en) Antibacterial liquid hand surface cleaning compositions comprising zinc salt
DE4337032C1 (de) Verwendung von Detergensgemischen zur Herstellung von Toilettensteinen
CN108471742A (zh) 提供抗微生物益处的处理组合物
CZ351997A3 (cs) Nenáročné čistící prostředky
US5529721A (en) Liquid pearlizing composition
WO1993025650A1 (fr) Compositions de concentres de tensioactifs a viscosite controlee
US6777003B1 (en) Iodine complex of alkyl polyglycosides
US5500155A (en) Detergent mixtures of fatty acid isethionate salts and fatty alcohols
US5910476A (en) Abrasive-containing soap bars
RU2073700C1 (ru) Жидкая моющая композиция для мытья посуды
EP0739196A1 (fr) Composition phenolique de nottyage desinfectant ameliorees avec des agents tensioactifs a base d'alkylpolyglucosides
JPH08502310A (ja) 水性洗剤混合物
US6046147A (en) Process for making skin cleansing combination soap bars and cleansing liquids
JPH08502540A (ja) 低温安定性を改良したアニオン界面活性剤水溶液の製造方法
WO1997042281A1 (fr) Tensioactifs de glucidiques combines avec des composants polyquaternium specifiques
US6083893A (en) Shaped semi-solid or solid dishwashing detergent
JP2001526301A (ja) 抗細菌作用を有する食器洗剤
EP1075502B1 (fr) Produit pour laver la vaisselle a action antibacterienne
WO1996029977A1 (fr) Compositions basees sur l'apg et au moins un tensioactif a base de sucre non ionique additionnel
GB2362320A (en) Liquid bactericidal cleaning composition based on alkyl polyglycoside surfactant, surface active quaternary ammonium salt, halogen-free arylphenol & Dichlosan
JP2003096498A (ja) 硬表面用液体洗浄剤組成物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BB BG BR BY CA CH CN CZ DE DK EE ES FI GB GE HU IL IS JP KE KG KP KR KZ LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK TJ TM TR TT UA UG UZ VN AM AZ BY KG KZ MD RU TJ TM

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE LS MW SD SZ UG AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
ENP Entry into the national phase

Ref document number: 2225016

Country of ref document: CA

Ref country code: CA

Ref document number: 2225016

Kind code of ref document: A

Format of ref document f/p: F

WWE Wipo information: entry into national phase

Ref document number: PA/a/1997/010386

Country of ref document: MX

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载