Drug – bio-affecting and body treating compositions – Solid synthetic organic polymer as designated organic active... – Polymer from ethylenic monomers only
Reexamination Certificate
2000-03-07
2002-10-01
Wilson, D. R. (Department: 1713)
Drug, bio-affecting and body treating compositions
Solid synthetic organic polymer as designated organic active...
Polymer from ethylenic monomers only
C523S122000, C525S328200, C525S328400, C525S384000, C525S386000, C526S304000
Reexamination Certificate
active
06458348
ABSTRACT:
The invention relates to the use of polymers comprising as essential structural elements units of the formula I and/or II
in which
R
1
is H, alkyl, cycloalkyl, aryl or aralkyl,
R
2
and R
3
independently of one another are defined as for R
1
or are selected from substituted alkyl, substituted cycloalkyl, substituted aryl or substituted aralkyl, the substituents being selected from OH, O-alkyl, O-aryl, SH, S-alkyl, S-aryl, NH
2
, NH-alkyl, NH-aryl, N(alkyl)
2
, in protonated form if desired,
N(alkyl)
3
+
Z
−
, where Z is the radical of an organic or inorganic acid, COOH, COO-alkyl, CONH
2
, CONH-alkyl, CON(alkyl)
2
, CN and SO
3
H; and
the indices x in each case independently of one another are an integer from 1 to 20,
and their corresponding acid addition salts as biocides.
Z. Chem. 27 (1987) 1 discloses specially functionalized polyvinyl alcohols, polyacrylates and polyethyleneimines for immobilizing antimicrobially active substances. In the course of the use of such systems, the active substances are released in a controlled manner. According to the information in the publication, however, the antimicrobial activity is based on the release of the biocidal active substances.
U.S. Pat. No. 1,071,630 discloses that copolymers of diallyldimethylammonium chloride and sodium acrylate have a bactericidal activity. EP-A 0 331 528 discloses copolymers of ethylene and dialkylaminoalkylacrylamides having biocidal activity.
Antimicrobially active polymers containing vinylphosphonium and vinylsulfonium groups were reported in J. Polym. Sci. part A: Polym. Chem., Vol. 31, 335, 1441, 1467 and 2873 and also in Arch. Pharm. (Weinheim) 321 (1988) 89. Biocidally active polymers containing vinylamine units are known from Makromol. Chemie.
U.S. Pat. No. 4,493,193 describes N-containing polymers as biocides. However, the nitrogen atoms are situated in the main chain of the polymer. Similar polymer structures are also described in U.S. Pat. No. 3,714,259.
It is an object of the present invention to provide novel biocidal compositions.
We have found that this object is achieved in accordance with the invention by the use as biocides of the polymers defined at the outset.
The polymers to be used in accordance with the invention are known from the earlier application P1 96/30977.8. Essential structural elements present in these polymers are hydroxy-substituted N-vinylcarboxamide units.
Unless specified otherwise, the specific description given below of the polymers to be used in accordance with the invention is subject to the following definitions.
Alkyl radicals embrace straight-chain or branched, saturated carbon chains of 1 to 20 carbon atoms. The following radicals may be mentioned by way of example: alkyl radicals having 1 to 12 carbon atoms, such as the C
1
-C
6
alkyl radicals methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, t-butyl, n-pentyl, sec-pentyl, isopentyl, n-hexyl, 1-, 2- and 3-methylpentyl; and longer-chain radicals, such as unbranched heptyl, octyl, nonyl, decyl, undecyl, lauryl and the singly or multiply branched analogs thereof; and also alkyl radicals having more than 12 carbon atoms, such as unbranched tridecyl, myristyl, pentadecyl, palmityl, heptadecyl, stearyl, nonadecyl and eicosyl and also the singly or multiply branched analogs thereof.
Cycloalkyl radicals embrace in particular C
3
-C
12
cycloalkyl radicals, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylethyl, cyclopentylpropyl, cyclopentylbutyl, cyclopentylpentyl, cyclopentylhexyl, and the like.
Examples of preferred aralkyl radicals are phenyl and naphthyl, especially phenyl.
Examples of aralkyl radicals are aryl-C
1
-C
10
-alkyl and especially aryl-C
1
-C
6
-alkyl radicals, the aryl and alkyl moieties being as defined above.
The sum of all percentages (mol %, % by weight) for describing a composition is in each case 100.
Preferred substituents of the radicals R
2
and R
3
are —OH, —O—C
1
-C
6
-alkyl, —O-phenyl, —SH, —S—C
1
-C
6
-alkyl, —S—-phenyl, —NH
2
, —NH—C
1
-C
6
-alkyl, —NH-phenyl, —N(C
1
-C
6
-alkyl)
2
, —N(C
1
-C
6
-alkyl)
3
+
Z
−
, —COOH, —COO—C
1
-C
6
-alkyl, —CONH
2
, —CONH—C
1
-C
6
-alkyl, —CON(C
1
-C
6
-alkyl)
2
, —CN and —SO
3
H.
Preferred counterions Z
−
are Cl
−
, Br
−
, H
2
PO
4
−
, SO
4
2−
, NO
3
−
, HCOO
−
, phenyl-SO
3
−
.
One preferred embodiment of the invention uses polymers comprising
a) from 0.1 to 100 mol % units of the above formulae I and/or II
b) from 0 to 99.9 mol % of vinylamine units of the formula III
in which R
1
is as defined above,
c) from 0 to 99.9 mol % of monoethylenically unsaturated monomer units other than a) and b), selected preferably from N-vinylcarboxamides such as N-vinyl-C
1
-C
6
-carboxamides, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylurea, N-vinylimidazoles, N-vinylimidazolines, vinyl alcohol, vinyl formate, vinyl acetate, vinylpropionate, vinyl butyrate, C
1
-C
6
vinyl ethers, monoethylenically unsaturated C
3
-C
8
carboxylic acids and dicarboxylic acids, and the esters, amides, anhydrides and nitriles thereof; and
d) from 0 to 5 mol % of at least diethylenically unsaturated monomer units, preferably methylenebisacrylamide, glycol diacrylate, glycerol triacrylate, glycol dimethacrylate, glycerol trimethacrylate, divinylbenzene, divinyldioxane, pentaerythritol triallyl ether, pentaallylsucrose, divinylurea and divinylethyleneurea.
Particular preference is given to the use of polymers comprising
a) from 1 to 100 mol %, in particular from about 5 to 100 mol %, of units of the formula I and/or II in which R
1
is H, R
2
and R
3
are selected independently of one another from H, C
1
-C
6
alkyl and phenyl, and x is an integer from 1 to 10,
b) from 0 to 99 mol %, in particular from about 0 to 95 mol %, of vinylamine units of the formula III, in which R
1
is H, and
c) from 0 to 99 mol %, in particular from about 0 to 95 mol %, of at least one other ethylenically unsaturated monomer selected from N-vinylformamide, N-vinylpyrrolidone, N-vinylcaprolactam, N-vinylurea, vinyl alcohol, vinyl formate, vinyl acetate, vinyl propionate, C
1
-C
6
vinyl ethers, acrylic acid, methacrylic acid and the esters, amides, anhydrides and nitriles thereof.
Special preference is given to the use of polymers comprising
a) from 1 to 100 mol %, in particular from about 5 to 95 mol %, of units of the formula I and/or II in which R
1
is H, one of the radicals R
2
and R
3
is H and the other radical is H or methyl, and x is an integer from 1 to 6, and
b) from 0 to 99 mol %, in particular from about 0 to 95 mol %, of vinylamine units, and
c) from 0 to 99 mol %, in particular from about 0 to 95 mol %, of N-vinylformamide units.
The polymers to be used in accordance with the invention and comprising as essential structural elements units of the formula IV and/or V
in which
R
1
is alkyl, cycloalkyl, aryl or aralkyl and the radicals R
5
independently of one another are selected from alkyl, cycloalkyl, aryl and aralkyl, substituted one or more times if desired by OH, O-alkyl, O-aryl, SH, S-alkyl, S-aryl, NH
2
, NH-alkyl, NH-aryl, N(alkyl)
2
, in protonated form if desired, N(alkyl)
3
+
Z
−
,
where Z is the radical of an organic or inorganic acid, COOH, COO-alkyl, CONH
2
, CONH-alkyl, CON(alkyl)
2
, CN or SO
3
H; or are a radical of the formula VI
in which R
2
, R
3
and x are as defined above and R
2
and R
3
can also independently of one another be OH,
and the corresponding acid addition salts of these polymers are preferably prepared by reacting a prepolymer containing vinylamine units of the formula III
in which R
1
is as defined above with a compound of the formula VII
in which
R
5
is as defined above and
R
6
is alkyl, aralkyl or aryl, or
R
5
and R
6
together are a group of the formula VI
in which R
2
, R
3
and x are as defined above, and converting the product, if desired, into the corresponding acid addition sal
Decker Jürgen
Mahr Norbert
Negele Anton
Tropsch Jürgen
Zeller Dieter
BASF - Aktiengesellschaft
Keil & Weinkauf
Wilson D. R.
LandOfFree
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