Surface-active preparations

Details Surface-active preparations Surface-active preparations

2001-06-19

2003-09-16

Pryor, Alton N. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ether doai

Reexamination Certificate

active

06620854

ABSTRACT:

The present invention relates to surface-active preparations, to the use thereof in disinfecting and cleaning human skin and hands and hard objects, and to the use thereof in washing and cleaning formulations for textile fibre materials.
Hydroxydiphenyl ethers are used as microbicidal active ingredients in household cleaning agents. Such formulations generally have high contents of synthetic detergents or soaps, which greatly reduce the bactericidal action of hydroxydiphenyl ether in the formulations, that is to say the bactericidal activity is unsatisfactory, but the formulations are known to have a very good long-term (persistent) microbiostatic activity on the treated surfaces (inanimate surfaces, such as textiles, plastics, carpets, tiles, etc.).
Surprisingly it has been found that, as a result of the addition of hydrotropic agents and/or alcohols, household cleaning formulations exhibit very strong bactericidal activity despite high contents of synthetic detergents or soaps.
The present invention accordingly relates to a surface-active preparation containing
(a) from 0.01 to 2% by weight of an antimicrobial active ingredient from the class of diphenyl ethers,
(b) from 0.1 to 30% by weight of a hydrotropic agent,
(c) from 6.0 to 50% by weight of one or more synthetic detergents or soaps or a combination of such substances,
(d) from 0 to 70% by weight of a monohydric or dihydric alcohol, and
(e) tap water or deionised water ad 100%.
Soap compositions are to be understood as aqueous soap solutions. These may be in the form of soap solutions or so-called syndet solutions (=synthetic detergents).
The antimicrobial action of the preparation according to the invention extends to Gram-positive and Gram-negative bacteria as well as to yeasts, dermatophytes, etc.
As component (a) there come into consideration especially hydroxydiphenyl ethers of the general formula
wherein
Y is chlorine or bromine,
X is C
1
-C
20
alkyl, hydroxy-substituted C
1
-C
20
alkyl, C
5
-C
7
cycloalkyl, hydroxy, formyl, acetonyl, C
1
-C
6
alkylcarbonyl, C
2
-C
20
alkenyl, carboxy, carboxy-C
1
-C
3
alkyl or carboxyallyl;
Z is hydrogen, hydroxy, C
1
-C
20
alkyl, C
5
-C
7
cycloalkyl, C
1
-C
6
alkylcarbonyl, C
1
-C
20
alkoxy, phenyl or phenyl-C
1
-C
3
alkyl;
m is 1 or 2;
n is 0 or 1;
o is from 0 to 3;
p is 0 or 1;
q is from 0 to 3; and
r is 1 or 2.
Of special interest are compounds of formula (1) wherein
Y is chlorine or bromine,
m is 1,
n is 0 or 1,
o is 0,
p is 0 or 1,
r is 1 or 2, and
q is 0.
Of very special interest are compounds of formula (1) wherein
Y is chlorine,
m is 1,
n is 0,
o is 0,
p is 0 or 1,
q is 0,
r is 1 or 2 and
p is 0.
Especially preferred are the compounds of formulae
Also of interest are halogen-free diphenyl ethers of formula (1), for example compounds of formula (1) wherein
p and r are 0.
Especially preferred compounds accordingly correspond to formula
wherein
R
1
and R
2
are each independently of the other hydrogen, C
1
-C
20
alkyl, C
5
-C
7
cycloalkyl, C
1
-C
6
alkylcarbonyl, C
1
-C
20
alkoxy, phenyl or phenyl-C
1
-C
3
alkyl;
R
3
is hydrogen, C
1
-C
20
alkyl or C
1
-C
20
alkoxy;
R
4
is hydrogen, C
1
-C
20
alkyl, hydroxy-substituted C
1
-C
20
alkyl, C
5
-C
7
cycloalkyl, hydroxy, formyl, acetonyl, C
1
-C
6
alkylcarbonyl, C
2
-C
20
alkenyl, carboxy, carboxy-C
1
-C
3
alkyl, C
1
-C
3
-alkylcarbonyl, C
1
-C
3
alkyl or carboxyallyl.
Very especially preferred compounds correspond to formulae
The following compounds come into consideration as component (b):
sulfonates of terpenoids or of mono- or di-nuclear aromatic compounds, e.g. sulfonates of camphor, toluene, xylene, cumene or of naphthol;
saturated or unsaturated C
3
-C
12
-di- or -poly-carboxylic acids, e.g. malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic and sebacic acid, undecane- and dodecane-dioic acid, fumaric, maleic, tartaric and malic acid and also citric and aconitic acid;
aminocarboxylic acids, such as ethylenediaminetetraacetic acid, hydroxyethylethylene-diaminetetraacetic acid and nitrilotriacetic acid;
cycloaliphatic carboxylic acids, such as camphoric acid;
aromatic carboxylic acids, such as benzoic, phenylacetic, phenoxyacetic and cinnamic acid, 2-, 3- and 4-hydroxybenzoic acid, anilinic acid, o-, m- and p-chlorophenylacetic acid and o-, m- and p-chlorophenoxyacetic acid;
isethionic acid;
tannic acid;
acid amides of formula (9)
wherein
R
1
is hydrogen or C
1
-C
12
alkyl and
R
2
and R
3
are each independently of the other hydrogen, C
1
-C
12
alkyl, C
2
-C
12
alkenyl, hydroxy-C
1
-C
12
-alkenyl, hydroxy-C
2
-C
12
alkyl, or a polyglycol ether chain having from 1 to 30—CH
2
—CH
2
—O— or —CHY
1
—CHY
2
—O— groupings, wherein one of the radicals Y
1
and Y
2
is hydrogen and the other is methyl, such as N-methylacetamide;
urea derivatives of formula (10)
wherein
R
1
, R
2
, R
3
and R
4
are each independently of the others hydrogen, C
1
-C
8
alkyl, C
2
-C
8
-alkenyl, C
1
-C
8
hydroxyalkyl or C
2
-C
8
hydroxyalkenyl.
All the organic acids mentioned under (b) can also be in the form of their water-soluble salts, such as the alkali metal salts, especially the sodium or potassium salts or the amine (NR
1
R
2
R
3
) salts, wherein
R
1
, R
2
and R
3
are each independently of the others hydrogen, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
1
-C
8
hydroxyalkyl, C
5
-C
8
cycloalkyl or polyalkenyleneoxy-C
1
-C
18
alkyl or
R
1
, R
2
and R
3
together with the nitrogen atom to which they are bonded form unsubstituted or C
1
-C
4
alkyl-substituted morpholino.
Component (b) may be a single compound or may consist of a plurality of different compounds.
Special preference is given to a combination of cumene sulfonate and citric acid monohydrate.
As component (c) there come into consideration anionic, nonionic, cationic and zwitterionic and amphoteric synthetic detergents.
Anionic detergents are
sulfates, such as, for example, fatty alcohol sulfates, the alkyl chain of which has from 8 to 18 carbon atoms, such as, for example, sulfated lauryl alcohol;
fatty alcohol ether sulfates, such as, for example, the acid esters or salts thereof of a polyadduct of from 2 to 30 mol of ethylene oxide and 1 mol of a C
8
-C
22
fatty alcohol; the alkali metal, ammonium or amine salts of C
8
-C
20
fatty acids, referred to as soaps, such as, for example, coconut fatty acid;
alkylamide sulfates;
alkylamine sulfates, such as monoethanolamine lauryl sulfate;
alkylamide ether sulfates;
alkylryl polyether sulfates;
monoglyceride sulfates;
alkanesulfonates, the alkyl chain of which contains from 8 to 20 carbon atoms, e.g. dodecyl sulfonate;
alkylamide sulfonates;
alkylaryl sulfonates;
&agr;-olefin sulfonates;
sulfosuccinic acid derivatives, such as alkyl sulfosuccinates, alkyl ether sulfosuccinates or alkylsulfosuccinamide derivatives;
N-[alkylamidoalkyl]amino acids of formula (12)
wherein
X is hydrogen, C
1
-C
4
alkyl or —COO—M
+
,
Y is hydrogen or C
1
-C
4
alkyl,
Z is —(CH
2
)
1−1
—
m
1
is from 1 to 5,
n
1
is an integer from 6 to 18, and
M is an alkali metal cation or amine cation,
alkyl and alkylaryl ether carboxylates of formula (13) CH
3
—X—Y—A, wherein
X is a radical of formula —(CH
2
)
5-19
—O—,
R is hydrogen or C
1
-C
4
alkyl,
Y is —(CHCHO)
1-50
—,
A is (CH
2
)
m2−1
—COO
−
M
+
or
m
2
is from 1 to 6 and
M is an alkali metal cation or amine cation.
Also used as anionic surfactants are fatty acid methyl taurides, alkyl isothionates, fatty acid polypeptide condensation products and fatty alcohol phosphoric acid esters. The alkyl radicals occurring in those compounds preferably have from 8 to 24 carbon atoms.
The anionic surfactants are generally in the form of their water-soluble salts, such as the alkali metal, ammonium or amine salts. Examples of such salts include lithium, sodium, potassium, ammonium, triethylamine, ethanolamine, diethanolamine and triethanolamine salts. The sodium, potassium or ammonium (NR
1
R
2
R
3
) salts, especially, are used, with R
1
, R
2
and R
3
each independently of the others being hydrogen, C
1
-C
4
alkyl or C
1
-C
4
hydroxy-alkyl.
Especially preferred anio

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