MICROBIOCIDAL AGENTS ON THE BASIS OF ALKYL- DIGUANIDINIUM SALTS

AGENTS MICROBICIDE A BASE DE SELS D'ALKYLDIGUANIDINIUM

English Abstract

Abstract of the Disclosure:

A microbiocidal agent consisting of 10 to 40 parts by
weight of the salt of an alkyl-diguanidine of the for-
mula I


Image

in which R is C8-C18 alkyl and m is an integer of from 2
to 6 and 10 to 40 parts by weight of a block polymer of the
formula

Image

in which a, b and c denote integers which ate chosen in such
a manner that the block polymer has a molecular weight in
the range of from 1,000 to 16,000 and the portion by
weight of the polyoxethylene chains in the total molecule is
in the range of from 10 to 90 %, the balance being water
and/or a short chain, water-suluble alochol.

Claims

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What is claimed is:

A microbiocidal agent consisting of 10 to 40 parts by
weight of the salt of an alkyl-diguanidinium of the for-
mula I



Image (I)

in which R is C8-C18 alkyl and m is an integer of from 2
to 6 and 10 to 40 parts by weight of a block polymer of the
formula
(II)
Image

in which a, b and c denote integers which are chosen in such
a manner that the block polymer has a molecular weight in
the range of from 1,000 to 16,000 and the proportion by
weight of the polyoxethylene chains in the total molecule is
in the range of from 10 to 90 %, the balance being water
and/or a short chain, water-soluble alcohol.

Description

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It is known that alkyl-diguanidinium salts have a
good bactericidal and fungicidal effect (DE-PS 1,249,457).
Owing to their partially unsatisfactory solubi~ity in
water and their poor compatibility, especially with hard
water or water containing sodium chloride, their possibi-
lities of application are, however, limited.
To improve the solubility and stability in water
containing sodium chloride or in hard water it has been
proposed to combine the aforesaid salts witn quaternary
ammonium compounds or phosphonium compounds or with long
chain alkyl diamine salts. It is, however, disadvanta-
geous that the said emulsifiers have a negative effect on
the microbiocidal activity of the alkyl-diguanidinium
salts.
It has now been found that combinations of the salts
of alkyl-diguanidines with polyoxethylene-polyoxpropylene
block polymers yield stable formulations with improved
microbiocidal effect.
It is, therefore, the object of the present inven-

tion to provide microbiocidal agents consisting of 10 to40, preferably 20 to 30, parts by weight of the salt of an
alkyl-diguanidine of the formula I
R H
H2N-cl-N-(cH2)m-N-c-NH2 (I)
NH NH
in which R is C&-C1~ alkyl and m is an integer of from
2 to ~ and 10 to 40 preferably 20 to 30, parts by weight
of a block polymer of the formula

HO-(CH2-ch2-) 2- ( Ch -c~;2 - ) b-(C~2-~;20)c-~
C 3


;27 ~
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in which a, b and c denote integers which are chosen in
such a manner that the block polymer has a molecular
weight in the range of from 1,000 to 16,000 and the
proportion by weight of the polyoxethylene chains in the
total molecule is in the range of from 10 to 90 %, the
balance being water and/or a short chain, water-soluble
a]cohol, preferably isopropanol.
The alkyl-diguanidines to be used according to the
invention can be prepared by known processes, for example
by reacting diamines of the formula
~ - NH - (CH2)m - NH2
in which R and m have the aforesaid meaning, with cyan-
amide or S-alkyl-isothiourea.
For salt formation mono- and polybasic inorganic or
organic acids can be used, for example sulfuric acid,
nitric acid, phosphoric acid, hydrochloric acid, formic
acid, acetic acid and, above all, high molecular weight
aliphatic carboxylic acids such as lauric acid, stearic
acid, oleic acid and the like, and mixtures of the said
; acids. Instead of uniform salts there can also be used
mixtures thereof, optionally in admixture with other
microbiocides.
The microbiocidal agents of the invention, which are
prepared by simply mixing the specified components, are
distinguished by a good solubility in water and are well
compatible with hard water and water containing sodium
chloride. Moreover, it is worth mentioning 'hat they have
an improved microbiocidal effect compared with the hither-




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to known formulations with quaternary ammoniur, compounds.
The following example illus,trates the-invention.
E X A M P L E
The following components are mixed:
25 parts of laurylpropylene-diaminoguanidinium mono-
lactate
25 parts of polyoxethylene-polyoxpropylene block po-
lymer having a total molecular weight of
8,000 and a molecular weight of the polyox-
ethylene proportion of 6,300
30 parts of isopropanol
20 parts of water.
The formulation obtained is stable under the condi-
tions of the rocking test. It can be further diluted wi~h
water in any desired proportion to give a limpid solution.
The microbiocidal effect in ~ /ml was tested by the
555-test of Fytopharmacie at Wageningen/Netherlands. In
this test the minimum concentration in ~/ml necessary to
reduce 107 germs per milliliter by 105 germs per
milliliter is ascertained, the time of contact being 5
minutes.
As comparative agent a commercial formulation consist-
ing of the following components
25 parts of laurylpropylene-diamine guanidinium lac-
tate
25 parts of soya trimethyl ammonium chloride
50 parts af sclvent and water
was used.




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Determination of the bactericidial and fungicidial effect


time of contact 5 minutes
minimum concentration for the reduction by 105 germs/ml
type of germ comparative product according to Example
of invention
Salm. Typh. 2500 ~/ml 250 ~/ml
Ps. aerug. about 3000 ~/ml 250 ~ /ml
Strept. Faec. 1500 ~/ml 500 ~ /ml
10 5taph. aureus. 2000 ~ /ml 500 ~ /ml
Cand. alb. 3000 ~ /ml 250 ~ /ml
The table reveals that the mixture according to the
invention has an improved microbiocidal effect as compared
to the commercial product.
15 In order to reduce the number of germs by 105 germs
per milliliter with a time of contact of 5 minutes a much
lower concentration of the formulation of the invention is
required.




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