Biphenyl diquaternary ammonium compounds

Details Biphenyl diquaternary ammonium compounds Biphenyl diquaternary ammonium compounds

2001-09-19

2004-05-04

Boyer, Charles (Department: 1751)

Cleaning compositions for solid surfaces, auxiliary compositions

Cleaning compositions or processes of preparing

Specific organic component

C510S119000, C510S123000, C510S130000, C510S131000, C510S382000, C510S384000, C510S391000

Reexamination Certificate

active

06730655

ABSTRACT:

The present invention relates to new diquaternary ammonium compounds, to a process for the preparation thereof, to the use thereof as antimicrobial agents against gram-positive and gram-negative bacteria, yeasts, fungi and algae, to the use thereof as disinfectants and preservatives, and to the use thereof in the preparation of formulations for technical use, cosmetic use and use in hygiene.
The diquaternary ammonium compounds according to the invention correspond to formula:
wherein
R
1
is C
5
-C
16
alkyl, phenyl or phenyl-C
1
-C
10
alkyl,
R
4
is C
4
-C
16
alkyl, phenyl or phenyl-C
1
-C
10
alkyl,
R
2
, R
3
, R
5
and R
6
are each independently of the others C
1
-C
4
alkyl, and
A is a monovalent anion,
with the proviso that when R
1
and R
4
are benzyl and R
2
, R
3
, R
5
and R
6
are identical and are methyl or n-propyl, A is not Br
−
or I
−
.
C
4
-C
16
Alkyl radicals are unbranched or branched alkyl radicals, for example n-butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, decyl, dodecyl or hexadecyl.
C
5
-C
16
Alkyl radicals are unbranched or branched alkyl radicals, for example pentyl, hexyl, octyl, decyl, dodecyl or hexadecyl.
Phenyl-C
1
-C
10
alkyl is, for example, benzyl, phenethyl, phenylpropyl, phenylisopropyl, phenylbutyl, phenyl-sec-butyl, phenyl-tert-butyl or phenyldecyl.
C
1
-C
4
Alkyl radicals are unbranched or branched alkyl radicals, for example methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl or tert-butyl.
A is a monovalent anion, for example a halide anion, such as F
−
, Cl
−
, Br
−
or I
−
, or an inorganic or organic group, for example hydrogen carbonate, nitrate, hydrogen sulfate, chlorate, dihydrogen phosphate, formate, acetate, or p-toluene hydrogen sulfate. Preferred as halide anion is Cl
−
.
The identities of substituents R
1
, R
2
, R
3
, R
4
, R
5
and R
6
may each be independent of the others and have the meanings given. Preference is given to diquaternary ammonium compounds in which R
4
and R
1
, R
5
and R
2
, and R
6
and R
3
are identical, in accordance with formula (1′):
Of interest are compounds of formula (1′) wherein R
1
is C
5
-C
16
alkyl, preferably unbranched C
5
-C
16
alkyl, and especially C
6
-, C
8
-, C
12
- or C
16
-alkyl.
Also of interest are compounds of formula (1′) wherein R
2
and R
3
are each independently of the other unbranched C
1
-C
4
alkyl, especially a CH
3
group.
Of special interest are the mentioned compounds of formula (1′) wherein A is a halide anion, especially Cl
−
, preferably according to the following formulae:
The process according to the invention for the preparation of diquaternary ammonium compounds of formulae (1) and (1′) comprises a quaternisation reaction of a biphenyl compound of formula:
wherein X is halogen, such as fluorine, chlorine, bromine or iodine, or a monovalent, inorganic or organic, anion-forming leaving group, for example —CO
3
H, —NO
3
, —SO
4
H, —ClO
3
, —PO
4
H
2
, —COOH, —COOCH
3
or —SO
3
(C
6
H
4
)CH
3
,
with an amino compound of formula
wherein
R
1
, R
2
and R
3
are each independently of the others as defined hereinbefore, and with a further amino compound of formula
wherein
R
4
, R
5
and R
6
are each independently of the others as defined hereinbefore.
In the general process for the preparation of the diquaternary ammonium compound of formula (1), the reaction of the biphenyl compound (6) is carried out with two different amino compounds (7) and (8), which can result in a mixture of up to three different products which, if desired, can be separated, for example by chromatographic methods.
In the process for the preparation of the diquaternary ammonium compound of formula (1′), the reaction of the biphenyl compound (6), for example with an amino compound of formula (7), is carried out preferably in a polar solvent, with heating, there being possible as solvent, for example, water, an alcohol, for example MeOH, EtOH or isopropanol, a ketone, for example acetone, or DMF, DMSO, or a mixture of two or more such solvents. The amino compound (7) is preferably used in stoichiometric ratio or in stoichiometric excess relative to the biphenyl compound (6). Especially suitable amino compounds of formula (7) are those in which R
1
is unbranched C
5
-C
16
alkyl and R
2
and R
3
are each a CH
3
group. For example, N,N′-dimethylhexylamine is introduced into water and heated to approximately from 60 to 90° C. The biphenyl compound of formula (6), wherein X is preferably halogen and is especially —Cl, for example bis(chloromethyl)biphenyl, in a suitable solvent, for example isopropanol, is metered in in the course of approximately from 40 to 80 minutes. After stirring for a relatively long period (for example approximately 2 hours), the isopropanol is distilled off at approximately from 80 to 110° C., water simultaneously being added dropwise to the mixture. After concentration, the residue is brought to dryness in vacuo, yielding the diquaternary ammonium compound which, in the example mentioned, corresponds to formula (2). Further details relating to the preparation process according to the invention are given in the corresponding Examples.
The biphenyl compounds of formula (6) used in the preparation process are known or can be prepared in a manner known per se; for example they can be prepared according to the Blanc chloromethylation reaction from biphenyl, formaldehyde, and HCI in the presence of ZnCl
2
(e.g. DE-A-1 793 482).
The present invention relates also to the use, as antimicrobial agents, disinfectants and preservatives, of diquaternary ammonium compounds of formula:
wherein
R
1
and R
4
are each independently of the other C
4
-C
16
alkyl, phenyl or phenyl-C
1
-C
10
alkyl,
R
2
, R
3
, R
5
and R
6
are each independently of the others C
1
-C
4
alkyl, and
A is a monovalent anion.
The diquaternary ammonium compounds exhibit pronounced antimicrobial action, especially against gram-positive and gram-negative bacteria, against bacteria of the skin flora, against yeasts and moulds, and also against algae. They are accordingly suitable as antimicrobial agents, as disinfectants and as preservatives.
They are suitable especially for disinfection, deodorisation, and for general and antimicrobial treatment of the skin, mucosa and hair, more especially for the disinfection of hands, wounds and the throat. It has furthermore been demonstrated that, even at low concentrations, the antimicrobial activity is still assured.
They are also suitable for use in solid or liquid formulations, such as personal care preparations, shampoos, bath additives, haircare preparations, cosmetic and medicinal soaps, lotions, creams, deodorants, or cleansing solutions, for cleaning or rinsing solutions, for example for oral use in the household sector and in the hygiene sector, for example hospitals, retirement homes or doctors' surgeries, and for use in cleaning and disinfecting preparations for surfaces in the household sector, in industry and in the hygiene sector.
They are furthermore suitable for imparting antimicrobial properties to technical plant, such as cooling systems, paper treatment machines and swimming pools, and for antimicrobial water treatment for the purpose of reducing the growth of bacteria, fungi and algae and for controlling slime. In addition, they are suitable for the preservation of materials, for example filter materials for air and water filters, textile fibre materials, for example cellulose fibres, cotton, silk, wool, polyamide fibres, plastics, for example dressing materials, catheters and syringes, and for the preservation of paper, wood, leather, paints and surface coatings. They are furthermore suitable for the preservation of foodstuffs or drinks, for example beer.
Some of the mentioned applications for the preparation of formulations are listed hereinbelow:
A disinfectant preparation for the hands has, for example, the following composition:
0.01 to 5% by weight of a compound of formula (1)
60% by weight isopropanol
0.1% by weight perfume oil, and
water ad 100

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