WO1995009605A1 - Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants - Google Patents

Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants

Info

Publication number
WO1995009605A1
WO1995009605A1 PCT/US1994/010911 US9410911W WO1995009605A1 WO 1995009605 A1 WO1995009605 A1 WO 1995009605A1 US 9410911 W US9410911 W US 9410911W WO 1995009605 A1 WO1995009605 A1 WO 1995009605A1
Authority
WO
Grant status
Application
Patent type
Prior art keywords
group
atoms
carbon
compound
alkyl
Prior art date
Application number
PCT/US1994/010911
Other languages
French (fr)
Inventor
Sureshchandra G. Desai
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

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/604Alkylpolyglycosides; Derivatives thereof, e.g. esters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q17/00Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/662Carbohydrates or derivatives
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/24Organic compounds containing halogen
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL AND VEGETABLE OILS, FATS, FATTY SUBSTANCES AND WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Abstract

An aqueous disinfectant cleaning composition incorporating an effective amount of a compound of the formula (I): R-O(-G)n, wherein R is an alkyl group having from about 8 to about 22 carbon atoms, G is a saccharide residue having 5 or 6 carbon atoms; and n is a number from 1 to 10 into an aqueous composition which contains a phenolic 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, and halo-substituted bis(hydroxyphenyl)alkanes, is provided. Also provided is a method of improving a disinfectant cleaning composition by incorporating an effective amount of an alkyl glycoside of formula (I) and a method of cleaning skin which employs such compositions.

Description

IMPROVING PHENOLIC DISINFECTANT CLEANING COMPOSITIONS WITH ALKYLPOLYGLUCOSIDE SURFACTANTS

BACKGROUND OF THE INVENTION

Field of the Invention

This invention relates to compositions useful as disinfectant cleaning compositions, to a method for improving a disinfectant cleaning composition, and to the use of disinfectant cleaning compositions.

Background Art

Alkyl glycosides have been disclosed as potentiating agents for antiseptic biguanidine compounds as set forth in U.S. Patent No. 4,748,158 (Bierman et al.). The Bierman patent also discloses that investigations into the microbiological activities of alkyl glycosides have shown that they exhibit no significant antimicrobial activity even at concentrations as high as 10,000 ppm. Further, the Bierman patent discloses that combinations of alkyl glycosides with quaternary ammonium compounds are similarly undistinguished in their antimicrobial effect. While quaternary ammonium compounds exhibit bactericidal activity, their use with an alkyl glycoside surfactant, as described, for example, in U.S. Pat. No. 3,547,828, produces no increased or unexpected bactericidal effect. U.S. 4,834,903 teaches compositions in which oxyalkylated long chain glycoside compositions are utilized in combination with one or more anionic, cationic or nonionic cosurfactant ingredients and/or with one or more detergent builder components. Phenolic compounds are a known class of disinfectants. See e.g.

"Disinfectants and Antiseptics", Encyclopedia of Chemical Technology, vol. 7, pp. 808-81 5 (Kirk-Othmer, eds., John Wiley & Sons, Inc. N.Y., N.Y., 3d ed. 1979). As this article states, 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. For example, 3,5- dimethyl-4-chlorophenol is discussed at pages 810 and 81 1 of that article and 2,4,4'-trichloro-2'-hydroxydiphenyl ether is discussed at page 81 2.

SUMMARY OF THE INVENTION It has been found that an aqueous disinfectant cleaning composition can be improved by incorporating an effective amount of a compound of the formula I: R-O(-G)n wherein R is an alkyl group having from about 8 to about 22 carbon atoms, G is a saccharide residue having 5 or 6 carbon atoms; and n is a number from 1 to 10, into an aqueous composition which contains a phenolic 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, and halo-substituted bis(hydroxyphenyl)alkanes. Thus, this invention relates to compositions comprising a mixture of compounds of formula I and a phenolic compound as set forth herein. This invention also relates to a process of improving an aqueous cleaning composition comprising adding an effective amount of the compound of formula I to an aqueous composition comprised of a phenolic compound as set forth herein. This invention also relates to a method of cleansing skin comprising contacting skin with an effective amount of the aqueous cleaning composition of this invention.

Preferred phenolic compounds have the formula II:

wherein:

R1 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms, an alkoxy group having from about 1 to about 7 carbon atoms, an aryl group having from about 6 to 10 carbon atoms, an aryloxy group having from about 6 to 10 carbon atoms, an aralkyl group having from about 6 to about 24 carbon atoms (e.g. a benzyl or C**.4 alkyl substituted benzyl group), an aralkoxy group having from about 6 to about 24 carbon atoms, an alkaryl group having from about 6 to about 24 carbon atoms and an alkaryloxy group having from about 6 to about 24 carbon atoms, each X is independently a halogen selected from the group consisting of chlorine and bromine,

M is a counter-ion selected from the group consisting of hydrogen, alkali metals, alkaline earth metais and ammonium, and a is 1 , 2 or 3, b is 1 , 2, or 3, and c is 1 or 2, provided the sum of a, b, and c may not exceed 6. In particularly preferred compositions, the phenolic compound has the formula III:

( FT ) ( X )

wherein:

R2 is selected from the same group as R\ more preferably from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms, each X is independently a halogen selected from the group consisting of chlorine and bromine, each M is a counter-ion selected from the group consisting of hydrogen, alkali metals, alkaline earth metals and ammonium,

Y is a linking group selected from the group consisting of oxygen and methylene, and each of a and d is independently 1 , 2, or 3, preferably a and d are both 1 , each of b and e is independently 1 , 2, or 3, f is 0 or 1 , and g is 0, 1 or 2, provided the sum of a, b, f, and g may not exceed 6 and the sum of d and e may not exceed 4. Detailed Description of the Invention

Compounds of the formula I are commercial surfactants and are available, for example, from Henkel Corporation, Ambler, PA., 1 9002 under the trademark names APG®, Plantaren™, or Glucopon™. Examples of such surfactants include but are not limited to:

1 . Glucopon™ 225 - an alkylpolyglycoside in which the alkyl group contains 8 to 10 carbon atoms.

2. APG® 325 - an alkyl polyglycoside in which the alkyl group contains 9 to 1 1 carbon atoms. 3. Glucopon™ 625 - an alkyl polyglycoside in which the alkyl groups contains 1 2 to 1 6 carbon atoms. 4. APG® 300 - an alkyl polyglycoside substantially the same as the 325 product above but having a different average degree of polymerization. 5. Glucopon™ 600 - an alkylpolyglycoside substantially the same as the

625 product above but having a different average degree of polymerization.

6. Plantaren® 2000 - a C8.16 alkyl polyglycoside.

7. Plantaren® 1 300 - a C12.16 alkyl polyglycoside. 8. Plantaren® 1200 - a C12_16 alkyl polyglycoside.

Other examples include alkyl polyglycoside surfactant compositions which are comprised of mixtures of compounds of formula IV wherein G represents a moiety derived from a reducing saccharide containing 5 or 6 carbon atoms; n is a number from 1 .0 to 3; and R is an alkyl radical having from 8 to 20 carbon atoms. The composition is characterized in that it has increased surfactant properties and an HLB in the range of about 10 to about 1 6 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. Such compositions can be prepared by separation of the monoglycoside from the original reaction mixture of alkyl monoglycoside and alkyl polyglycosides after removal of the alcohol. This separation may be carried out by molecular distillation and normally results in the removal of about 70-95% by weight of the alkyl monoglycosides. After removal of the alkyl monoglycosides, 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 copending application serial number 07/810,588, filed on 12/19/91 , the entire contents of which are incorporated herein by reference. The skilled artisan may find it beneficial to use a mixture of compounds of the formula I in order to obtain a maximum improvement of a disinfectant cleaning composition. The preferred compounds of formula I are Glucopon™ 425 surfactant and Glucopon™ 625 surfactant. An effective amount of a compound of formula I is any amount which will increase the efficacy of a compound of formula II. The effective amount will typically be in the range of the ratio of a compound of formula I to phenolic compound of from 30:1 to 1 :2, preferably from 20: 1 to 2: 1 , and more preferably from 1 5: 1 to 5: 1 .

The bactericidal compounds useful according to the invention are phenolic compounds. Representative examples of phenolic compounds, e.g. compounds within the scope of formula II, are disclosed in "Disinfectants and Antiseptics", Encyclopedia of Chemical Technology, vol. 7, pp. 808-81 5 (Kirk-Othmer, eds., John Wiley & Sons, Inc. N.Y., N.Y., 3d ed. 1 979), the disclosure of which is incorporated herein by reference. As stated above, the compounds useful in this invention are selected from the group consisting of halo-substituted monohydric phenol compounds, halo- substituted dihydric phenol compounds, halo-substituted trihydric phenol compounds, halo-substituted hydroxybenzoic acid compounds, and halo- substituted bis(hydroxyphenyl)alkane compounds.

By "halo-substituted" 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. The terms 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.

Examples of 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 C7 normal alkyl-substituted halo-phenols (e.g. 2-chloro-4-methyl-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- phenyDalkanes, preferably bis(hydroxy-halo-phenyl)methanes (e.g. 2,2'- methylenebis(4-chlorophenol) and 2,2'-methylenebis(3,4,6-trichlorophenol). The preferred compounds of formula II are 4-chloro-3,5-dimethyl-phenol and 2,4,4'-trichloro-2'-hydroxydiphenyl ether.

The amount of the phenolic compound typically in a disinfectant cleaning composition to be improved by incorporation of the compound of formula I will typically be from the weight ratio of a compound of formula I to phenolic compound of from 30: 1 to 1 :2, preferably 20:: 1 to 2: 1 , and more preferably 10:0 to 5: 1 . The disinfectant cleaning compositions to be improved by incorporation of compound of the formula I can also contain other compounds normally used in such compositions such as builders, brighteners, emollients, moisturizers, etc. The aqueous compositions of this invention are advantageously used in personal care products, e.g. they are applied to, or otherwise contact, human skin. In such products, the major component on a weight basis is water (typically at least 60% by weight). The composition may be in the form of a concentrate (i.e only a minor amount by weight of water), which is diluted with water to form the final product. A preferred use of the compositions of this invention is in a liquid hand soap.

One preferred embodiment of the present invention is a process wherein in the compound of formula I R is a C8.16 alkyl group, G is a glucose residue, and n is 1.6. Another preferred embodiment of the present invention is a process wherein in the compound of formula I R is a C12.16 alkyl group, G is a glucose residue, and n is 1.6. The following examples are meant to illustrate but not limit the invention.

EXAMPLE 1 A disinfectant cleaning composition having the formulation set forth below was prepared by mixing the ingredients together. This composition contained the dihydric phenol 2,4,4'-trichloro-2'-hydroxydiphenyl ether (a.k.a. triclosan) as the active bactericidal ingredient and is labelled Sample A, below.

Alkylpolyglucoside was used to prepare an antibacterial liquid hand soap concentrate as shown below.

COMPOUNDS Parts by weight

Sodium lauryl sulfate(Standapol WAQLC) 66.68 Alkylpolyglucoside (Glucopon-625) 15.68

Coconut Betaine (Velvetex BA-35) 1 1.76

Triclosan (Irgasan DP 300) 1.96

Propylene Glycol 0.98

Glycerine 0.98 Sodium Chloride 1 .96

100.8

From the above concentrate formulation, an antibacterial liquid hand soap was made as shown below.

PARTS

COMPONENTS BY

WEIGHT

Concentrate from above 25

Deionized Water 72.8

25% Sodilum Chloride Solution 2^2 100

The liquid hand soap composition (the concentrate diluted as shown above) was then tested side-by-side with a commercially available liquid hand soap, denoted as Sample B, below, (containing 0.19% of the active ingredient triclosan and presumably having a different formulation with respect to the other ingredients) for their ability to inhibit the growth of the test organisms Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, as follows. (It should be noted that the composition of Sample B was unknown with the exception of the percent of an active ingredient.) Test cultures of each organism were prepared by incubating at 35 °C in Tryptic Soy Broth for 24 hours. Stock dilutions of each test sample were prepared by making an initial 2% dilution (weight/volume) in sterile distilled water. This was then subjected to "doubling dilutions" in sterile distilled water, to yield 2%, 1 %, 0.5%, 0.25%, 0.125%, 0.063%, 0.031 % and 0.016%. These stock dilutions were respectively labelled 20000, 10000, 5000, 1250, 625, 313, and 156 parts per million (ppm). Test systems were then prepared for each organisms. These consisted of test tubes containing 9 ml of the same media as that used for culture preparation. Addition of 1 ml of the stock dilutions to these tubes yielded in-test concentrations of one-tenth the stock dilution concentrations, or 2000, 1000, 5000, 250, 125, 62.5,, 31.3, and 15.6 ppm. One ml of sterile distilled water was added to an additional 9 ml tube of media, to serve as a positive growth control (labelled "0 ppm").

Finally, one drop (from a sterile pipette) of the test cultures/ suspensions were added to the test systems, and incubated. At the conclusion of the incubation period, the tubes were observed for growth. The results of the tests are as set forth in Table 1 , below.

Table 1

Microbiological Recovery

Sample A Sample B

Sa1 Ec2 Pa3 Sa Ec Pa

0 + + + + + + + + + + + +

1 5.6 + *+ + + + + + + + +

31 .35 + + + + + + + + +

62.5 ± ± + + + + + + +

1 25 — ± + + — + + + +

250 — — + + - + + + +

500 — — + + - + + + +

1000 -- -- + + -- — + +

2000 — — + + - — + +

Sa is S. aureus

Ec is E. coli

Pa is P. aeruginosa

+ + is heavy growth

+ is growth

± is little growth

— is no growth

EXAMPLE 2

A disinfectant cleaning composition having the formulation set forth above was tested in a different protocol side-by-side with a second sample of the liquid hand soap of Sample B, and a sample of a second commercially available liquid hand soap denoted below as Sample C (containing 0.26% of the active ingredient triclosan and presumably having a different formulation with respect to the other ingredients) for their ability to inhibit the growth of the test organisms Staphylococcus aureus and Kleb. pneumoniae as follows. (It should be noted that the composition of Samples B and C was unknown with the exception of the percent of an active ingredient of each.) The method employed was a suspension/challenge - serial dilution/viable cell count. An inoculum was prepared by mixing 0.25 mis. of a 24 hour broth culture with 9.75 mis. of sterile distilled water. A baseline count was determined by performing a serial dilution/viable cell count on the inoculum/test formulation mixture. One ml of inoculum was added to 9 mis. of test formulation and mixed with a glass rod; followed by a viable cell count performed after 120 seconds of contact time. Serial dilutions and subsequent plate counts were performed in broth and agar, respectively, containing triclosan neutralizing ingredients (polysorbate 80 and lecithin, available as Lethee broth and agar from Difco) in order to differentiate between cidal and static antibacterial activity. The viable cell counts (vcc or colony forming units) for each test organism, after 120 seconds of contact time, were compared to a baseline count in order to calculate a reduction factor (RF). The RF is expressed in log and percent reductions.

TABLE 2

vcc/ml: RF:

Samples Organism

Baseline 120 Seconds Log/(%)

A Sa 3,900,000 12,250 2.51 /(99.68)

B Sa 3,900.00 5,800 2.83/(99.85)

C Sa 3,900,00 < 100 >4.59/(99.99)

A Kp 6,400.000 660,000 0 .99/(89.6)

B Kp 6,400.000 1 ,625,000 0.59/(74.6)

C Kp 6,400,00 1 ,800,000 0.55/(71.8) EXAMPLE 3

A disinfectant cleaning composition having the formulation set forth below was prepared by mixing the ingredients together. This composition contained the monohydric phenol 4-chloro-3,5-dimethyl- phenol (a.k.a. p-chloro-meta-xylenol) as the active bactericidal ingredient.

Alkylpolyglucoside was used to prepare an antibacterial liquid hand soap concentrate as shown below.

COMPOUNDS Parts by weight

Sodium lauryl sulfate(Standapol WAQLC) 66.68

Alkylpolyglucoside (Glucopon-625) 15.68

Coconut Betaine (Velvetex BA-35) 11.76

4-chloro-3,5-dimethyl-phenol 1.96

Propylene GlycoF 0.98

Glycerine 0.98

Sodium Chloride 1.96

100.8

From the above concentrate formulation, an antibacterial liquid hand soap was made as shown below.

COMPONENTS PARTS BY WEIGHT

Concentrate from above 25

Deionized water 72.8

25% Sodium Chloride Solution 2.2

100.0

Claims

What is claimed is:
1. A composition useful as a disinfectant cleaning composition comprising: an effective amount of a compound of the formula I: R-O(-G)n wherein R is an alkyl group having from about 8 to about 22 carbon atoms, G is a saccharide residue having 5 or 6 carbon atoms; and n is a number from 1 to 10, and an effective amount of a phenolic 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, and halo- substituted bis(hydroxyphenyl)alkanes.
2. A composition of claim 1 wherein said phenolic compound has the formula II:
wherein: R1 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms, an alkoxy group having from about 1 to about 7 carbon atoms, an aryl group having from about 6 to about 10 carbon atoms, an aryloxy group having from about 6 to about 10 carbon atoms, an aralkyi group having from about 6 to about 24 carbon atoms, an aralkoxy group having from about 6 to about 24 carbon atoms, an alkaryl group having from about 6 to about 24 carbon atoms and an alkaryloxy group having from about 6 to about 24 carbon atoms, each X is independently a halogen selected from the group consisting of chlorine and bromine,
M is a counter-ion selected from the group consisting of hydrogen, alkali metals, alkaline earth metals and ammonium, and a is 1 , 2 or 3, b is 1 , 2, or 3, and c is 1 or 2, provided the sum of a, b, and c may not exceed 6.
3. A composition of claim 1 wherein said phenolic compound has the formula III:
( R < ) ( X )
wherein:
R2 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms, an alkoxy group having from about 1 to about 7 carbon atoms, an aryl group having from about 6 to 10 carbon atoms, an aryloxy group having from about 6 to 10 carbon atoms, an aralkyi group having from about 6 to about 24 carbon atoms, an aralkoxy group having from about 6 to about 24 carbon atoms, an alkaryl group having from about 6 to about 24 carbon atoms and an alkaryloxy group having from about 6 to about 24 carbon atoms, each X is independently a halogen selected from the group consisting of chlorine and bromine, each M is a counter-ion selected from the group consisting of hydrogen, alkali metals, alkaline earth metals and ammonium, Y is a linking group selected from the group consisting of oxygen and methylene, and each of a and d is independently 1 , 2, or 3, preferably a and d are both 1 , each of b and e is independently 1 , 2, or 3, f is 0 or 1 , and g is 0, 1 or 2, provided the sum of a, b, f, and g may not exceed 6 and the sum of d and e may not exceed 4.
4. A composition of claim 3 wherein R2 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms
5. A composition of claim 3 wherein in said compound of formula I, R is an alkyl group having from 8 to 22 carbon atoms, G is a glucose residue and n is from 1 to 3.
6. A composition of claim 1 wherein said phenolic compound is selected from the group consisting of halo-substituted monohydric phenol compounds, halo-substituted dihydric phenol compounds, and halo-substituted trihydric phenol compounds.
7. A composition of claim 1 wherein said phenolic compound is 4-chloro-3,5-dimethyl-phenol.
8. A composition of claim 1 wherein said phenolic compound is 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
9. A composition of claim 1 wherein in said compound of formula I, R is an alkyl group having from 8 to 22 carbon atoms, G is a glucose residue and n is from 1 to 3.
10. A composition of claim 9 wherein said phenolic compound is 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
1 1 . A composition of claim 1 wherein in said compound of formula I R is a C8.16 alkyl group, G is a glucose residue, and n is 1.6.
12. A composition of claim 1 wherein in said compound of formula I R is a C12.16 alkyl group, G is a glucose residue, and n is 1.6.
13. A composition of claim 12 wherein said phenolic compound is 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
14. A composition of claim 13 wherein the weight ratio of said compound of formula I to said phenolic compound is from about 30: 1 to about 1 :2.
15. A composition of claim 1 wherein the weight ratio of said compound of formula I to said phenolic compound is from about 30: 1 to about 1 :2.
16. A composition of claim 1 further comprising a major amount by weight of water.
17. A composition of claim 1 further comprising a minor amount by weight of sodium chloride.
18. A process for improving an aqueous disinfectant cleaning formulation which comprises adding to said aqueous disinfectant cleaning formulation an effective amount of a compound of the formula I R-O(-G)n wherein R is an alkyl group having from about 8 to about 22 carbon atoms, G is a saccharide residue having 5 or 6 carbon atoms; and n is a number from 1 to 10; wherein said formulation is comprised of a phenolic 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, and halo-substituted bis(hydroxyphenyl)alkanes.
19. A process of claim 16 wherein said phenolic compound has the formula II:
wherein:
R1 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms, an alkoxy group having from about 1 to about 7 carbon atoms, an aryl group having from about 6 to 10 carbon atoms, an aryloxy group having from about 6 to 10 carbon atoms, an aralkyi group having from about 6 to about 24 carbon atoms (e.g. a benzyl or C,^ alkyl substituted benzyl group), an aralkoxy group having from about 6 to about 24 carbon atoms, an alkaryl group having from about 6 to about 24 carbon atoms and an alkaryloxy group having from about 6 to about
24 carbon atoms, each X is independently a halogen selected from the group consisting of chlorine and bromine, M is a counter-ion selected from the group consisting of hydrogen, alkali metals, alkaline earth metals and ammonium, and a is 1 , 2 or 3, b is 1 , 2, or 3, and c is 1 or 2, provided the sum of a, b, and c may not exceed 6.
20. A process of claim 16 wherein said phenolic compound has the formula III:
( R ) ( X )
wherein:
R2 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms, an alkoxy group having from about 1 to about 7 carbon atoms, an aryl group having from about 6 to 10 carbon atoms, an aryloxy group having from about 6 to 10 carbon atoms, an aralkyi group having from about 6 to about 24 carbon atoms, an aralkoxy group having from about 6 to about 24 carbon atoms, an alkaryl group having from about 6 to about 24 carbon atoms and an alkaryloxy group having from about 6 to about 24 carbon atoms, each X is independently a halogen selected from the group consisting of chlorine and bromine, each M is a counter-ion selected from the group consisting of hydrogen, alkali metals, alkaline earth metals and ammonium,
Y is a linking group selected from the group consisting of oxygen and methylene, and each of a and d is independently 1 , 2, or 3, preferably a and d are both 1 , each of b and e is independently 1 , 2, or 3, f is 0 or 1 , and g is 0, 1 or 2, provided the sum of a, b, f, and g may not exceed 6 and the sum of d and e may not exceed 4.
21 . A process of claim 18 wherein R2 is selected from the group consisting of an alkyl group having from about 1 to about 7 carbon atoms.
22. A process of claim 18 wherein in said compound of formula I, R is an alkyl group having from 8 to 22 carbon atoms, G is a glucose residue and n is from 1 to 3.
23. A process of claim 16 wherein said phenolic compound is selected from the group consisting of halo-substituted monohydric phenol compounds, halo-substituted dihydric phenol compounds, and halo-substituted trihydric phenol compounds.
24. A process of claim 16 wherein said phenolic compound is 4- chloro-3,5-dimethyl-phenol.
25. A process of claim 16 wherein said phenolic compound is 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
26. A process of claim 16 wherein in said compound of formula I, R is an alkyl group having from 8 to 22 carbon atoms, G is a glucose residue and n is from 1 to 3.
27. A process of claim 24 wherein said phenolic compound is 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
28. A process of claim 16 wherein in said compound of formula I R is a C8.16 alkyl group, G is a glucose residue, and n is 1.6.
29. A process of claim 16 wherein in said compound of formula I R is a C12. alkyl group, G is a glucose residue, and n is 1.6.
30. A process of claim 27 wherein said phenolic compound is 2,4,4'-trichloro-2'-hydroxydiphenyl ether.
31 . A process of claim 28 wherein the weight ratio of said compound of formula I to said phenolic compound is from about 30: 1 to about 1 :2.
32. A process of claim 16 wherein the weight ratio of said compound of formula I to said phenolic compound is from about 30:1 to about 1 :2.
33. A process of claim 16 wherein said aqueous disinfectant cleaning composition is comprised of a major amount by weight of water.
34. A process of claim 16 wherein said aqueous disinfectant cleaning composition is comprised of a minor amount by weight of sodium chloride.
35. A method of cleansing skin comprising contacting skin with an effective amount of an aqueous cleaning composition of claim 1.
PCT/US1994/010911 1993-10-06 1994-09-30 Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants WO1995009605A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US13273393 true 1993-10-06 1993-10-06
US08/132,733 1993-10-06

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19940929897 EP0739196A4 (en) 1993-10-06 1994-09-30 Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants

Publications (1)

Publication Number Publication Date
WO1995009605A1 true true WO1995009605A1 (en) 1995-04-13

Family

ID=22455351

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/010911 WO1995009605A1 (en) 1993-10-06 1994-09-30 Improving phenolic disinfectant cleaning compositions with alkylpolyglucoside surfactants

Country Status (2)

Country Link
EP (1) EP0739196A4 (en)
WO (1) WO1995009605A1 (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0776191A1 (en) * 1995-06-13 1997-06-04 Zahra Mansouri Methods of delivering materials into the skin, and compositions used therein
WO1998001110A1 (en) * 1996-07-10 1998-01-15 Calgon Vestal, Inc. Triclosan skin wash with enhanced efficacy
US6107261A (en) * 1999-06-23 2000-08-22 The Dial Corporation Compositions containing a high percent saturation concentration of antibacterial agent
WO2000078275A2 (en) * 1999-06-23 2000-12-28 The Dial Corporation Antibacterial compositions
DE19933404A1 (en) * 1999-07-21 2001-01-25 Henkel Kgaa Use of sugar surfactant(s) to adjust the viscosity of an aqueous surfactant-containing medium to give a thickened medium for disinfecting and/or cleaning sanitary surfaces
WO2001039728A2 (en) * 1999-12-01 2001-06-07 Henkel Ecolab Gmbh & Co. Ohg Hand washing lotion for a refillable foam-producing device
WO2002094330A1 (en) * 2000-11-28 2002-11-28 Kimberly-Clark Worldwide, Inc. Nonwovens modified with alkyl polyglycoside surfactants
FR2827763A1 (en) * 2001-07-24 2003-01-31 Cs Topical compositions containing alkylosides to prevent fixation of microorganism on corneocytes, for treatment of acne
US6531434B1 (en) 1997-05-20 2003-03-11 Novapharm Research (Australia) Pty. Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism
US6579516B1 (en) 1995-06-13 2003-06-17 Zahra Mansouri Methods of delivering materials into the skin, and compositions used therein
US6616922B2 (en) 2001-03-27 2003-09-09 The Dial Corporation Antibacterial compositions
US6861397B2 (en) 1999-06-23 2005-03-01 The Dial Corporation Compositions having enhanced deposition of a topically active compound on a surface
WO2006026732A1 (en) * 2004-08-30 2006-03-09 California Institute Of Technology Chemical system for improved oil recovery
EP2018856A3 (en) * 2007-07-23 2009-05-20 Antiseptica Chemisch-Pharmazeutische Produkte GmbH Multi-part medicinal product for wound cleansing and healing
EP2436754A1 (en) * 2011-09-30 2012-04-04 Basf Se Antimicrobial cleaning compound
WO2014146958A1 (en) * 2013-03-22 2014-09-25 Basf Se Mixtures of alkyl polyglycosides, their preparation, and uses
US8859481B2 (en) 2005-12-15 2014-10-14 Kimberly-Clark Worldwide, Inc. Wiper for use with disinfectants

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0086878A1 (en) * 1982-02-22 1983-08-31 Dexide, Inc. Mild antimicrobial detergent composition
US4440661A (en) * 1981-10-16 1984-04-03 Fuji Kasei Co., Ltd. Powdered cleaning composition
US5057311A (en) * 1988-04-12 1991-10-15 Kao Corporation Low-irritation detergent composition

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU84416A1 (en) * 1982-10-11 1984-05-10 Oreal gentle cleaning composition
DE3903348A1 (en) * 1989-02-04 1990-08-30 Henkel Kgaa Oral and dental care products with polysaccharide-enzymes

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440661A (en) * 1981-10-16 1984-04-03 Fuji Kasei Co., Ltd. Powdered cleaning composition
EP0086878A1 (en) * 1982-02-22 1983-08-31 Dexide, Inc. Mild antimicrobial detergent composition
US5057311A (en) * 1988-04-12 1991-10-15 Kao Corporation Low-irritation detergent composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0739196A4 *

Cited By (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6579516B1 (en) 1995-06-13 2003-06-17 Zahra Mansouri Methods of delivering materials into the skin, and compositions used therein
EP0776191A4 (en) * 1995-06-13 1999-01-20 Zahra Mansouri Methods of delivering materials into the skin, and compositions used therein
US7655250B2 (en) 1995-06-13 2010-02-02 Laboratory Skin Care, Inc. Topical formulations comprising ceramic hydroxyapatite particles
US7771753B2 (en) 1995-06-13 2010-08-10 Laboratory Skin Care, Inc. Topical formulations comprising ceramic hydroxyapatite particles
EP0776191A1 (en) * 1995-06-13 1997-06-04 Zahra Mansouri Methods of delivering materials into the skin, and compositions used therein
WO1998001110A1 (en) * 1996-07-10 1998-01-15 Calgon Vestal, Inc. Triclosan skin wash with enhanced efficacy
US5955408A (en) * 1996-07-10 1999-09-21 Steris Inc. Triclosan skin wash with enhanced efficacy
US6090772A (en) * 1996-07-10 2000-07-18 Steris Inc Triclosan skin wash with enhanced efficacy
US7163914B2 (en) 1997-05-20 2007-01-16 Novapharm Research (Australia) Pty. Ltd. Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism
US6531434B1 (en) 1997-05-20 2003-03-11 Novapharm Research (Australia) Pty. Alkylpolyglucosides containing disinfectant compositions active against pseudomonas microorganism
US6107261A (en) * 1999-06-23 2000-08-22 The Dial Corporation Compositions containing a high percent saturation concentration of antibacterial agent
WO2000078275A3 (en) * 1999-06-23 2001-09-27 Dial Corp Antibacterial compositions
WO2000078275A2 (en) * 1999-06-23 2000-12-28 The Dial Corporation Antibacterial compositions
US6451748B1 (en) 1999-06-23 2002-09-17 The Dial Corporation Compositions containing a high percent saturation concentration of antibacterial agent
US6861397B2 (en) 1999-06-23 2005-03-01 The Dial Corporation Compositions having enhanced deposition of a topically active compound on a surface
US6136771A (en) * 1999-06-23 2000-10-24 The Dial Corporation Compositions containing a high percent saturation concentration of antibacterial agent
US6204230B1 (en) 1999-06-23 2001-03-20 The Dial Corporation Antibacterial compositions containing a solvent, hydrotrope, and surfactant
DE19933404A1 (en) * 1999-07-21 2001-01-25 Henkel Kgaa Use of sugar surfactant(s) to adjust the viscosity of an aqueous surfactant-containing medium to give a thickened medium for disinfecting and/or cleaning sanitary surfaces
WO2001039728A3 (en) * 1999-12-01 2002-05-16 Henkel Ecolab Gmbh & Co Ohg Hand washing lotion for a refillable foam-producing device
WO2001039728A2 (en) * 1999-12-01 2001-06-07 Henkel Ecolab Gmbh & Co. Ohg Hand washing lotion for a refillable foam-producing device
GB2387329A (en) * 2000-11-28 2003-10-15 Kimberly Clark Co Nonwovens modified with alkyl polyglycoside surfactants
US6767508B1 (en) 2000-11-28 2004-07-27 Kimberly-Clark Worldwide, Inc. Nonwovens modified with alkyl polyglycoside surfactants
WO2002094330A1 (en) * 2000-11-28 2002-11-28 Kimberly-Clark Worldwide, Inc. Nonwovens modified with alkyl polyglycoside surfactants
KR100863085B1 (en) * 2000-11-28 2008-10-13 킴벌리-클라크 월드와이드, 인크. Nonwovens Modified with Alkyl Polyglycoside Surfactants
US6616922B2 (en) 2001-03-27 2003-09-09 The Dial Corporation Antibacterial compositions
EP1283033A1 (en) * 2001-07-24 2003-02-12 Cs Combination of alkylglycoside and pyridine carboxamide
FR2827763A1 (en) * 2001-07-24 2003-01-31 Cs Topical compositions containing alkylosides to prevent fixation of microorganism on corneocytes, for treatment of acne
WO2006026732A1 (en) * 2004-08-30 2006-03-09 California Institute Of Technology Chemical system for improved oil recovery
US8859481B2 (en) 2005-12-15 2014-10-14 Kimberly-Clark Worldwide, Inc. Wiper for use with disinfectants
EP2018856A3 (en) * 2007-07-23 2009-05-20 Antiseptica Chemisch-Pharmazeutische Produkte GmbH Multi-part medicinal product for wound cleansing and healing
CN103827281A (en) * 2011-09-30 2014-05-28 巴斯夫欧洲公司 Antimicrobial cleaning composition
WO2013045340A1 (en) * 2011-09-30 2013-04-04 Basf Se Antimicrobial cleaning composition
CN103827281B (en) * 2011-09-30 2017-04-26 巴斯夫欧洲公司 The antimicrobial cleaning composition
EP2436754A1 (en) * 2011-09-30 2012-04-04 Basf Se Antimicrobial cleaning compound
JP2014528019A (en) * 2011-09-30 2014-10-23 ビーエーエスエフ ソシエタス・ヨーロピアBasf Se Antimicrobial cleaning composition
CN105073968A (en) * 2013-03-22 2015-11-18 巴斯夫欧洲公司 Mixtures of alkyl polyglycosides, their preparation, and uses
WO2014146958A1 (en) * 2013-03-22 2014-09-25 Basf Se Mixtures of alkyl polyglycosides, their preparation, and uses
US9845446B2 (en) 2013-03-22 2017-12-19 Basf Se Mixtures, their preparation, and uses

Also Published As

Publication number Publication date Type
EP0739196A4 (en) 1997-06-11 application
EP0739196A1 (en) 1996-10-30 application

Similar Documents

Publication Publication Date Title
US4272395A (en) Germicidal compositions
US4748158A (en) Alkyl glycosides as potentiating agents in antiseptic, disinfecting and cleaning preparations to increase microbicidal activity
US6087320A (en) Viscosity-adjusted surfactant concentrate compositions
US5266690A (en) Preparation of alkylpolyglycosides
US5576284A (en) Disinfecting cleanser for hard surfaces
US5025069A (en) Mild alkyl glycoside-based detergent compositions, further comprising terpene and isothiazolone derivatives
US5798329A (en) Germicidal liquid laundry detergent compositions
US5229103A (en) Antiplaque mouthwash concentrate
US6262038B1 (en) Germicidal composition
US5403587A (en) Disinfectant and sanitizing compositions based on essential oils
US5154850A (en) Neutral liquid detergent composition
US6358906B1 (en) Concentrated liquid accumulations comprising a microbicidally active ingredient
US6046146A (en) Antibacterial liquid hand surface cleaning compositions comprising zinc salt
US4118332A (en) Synergistic antibacterial composition containing mixtures of certain halogenated diphenyl ethers and trichlorocarbanilides
US4477361A (en) Antifungal-antibacterial detergents containing cinnamic compounds
US5693318A (en) Stable salicylic acid and peroxide containing skin and hair cleanser composition
US6255270B1 (en) Cleaning and disinfecting compositions with electrolytic disinfecting booster
US6147039A (en) Antibacterial liquid hand cleaning compositions containing a hydroxy containing organic acid
US6204230B1 (en) Antibacterial compositions containing a solvent, hydrotrope, and surfactant
US6066674A (en) Germicidal-disinfectant detergent composition
US5734029A (en) Preparation of improved alkypolygloycoside surfactant mixtures
US3824190A (en) Phenolic synthetic detergent-disinfectant
US5728667A (en) Compositions containing organic compounds
US5266598A (en) Skin disinfectant compositions
US5449763A (en) Preparation of alkylpolyglycosides

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

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

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): KE MW SD SZ AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN ML MR NE SN TD TG

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
WWE Wipo information: entry into national phase

Ref document number: 1994929897

Country of ref document: EP

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase in:

Ref country code: CA

WWP Wipo information: published in national office

Ref document number: 1994929897

Country of ref document: EP

WWW Wipo information: withdrawn in national office

Ref document number: 1994929897

Country of ref document: EP