Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
2000-03-07
2001-04-10
Barts, Samuel (Department: 1621)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S653000, C514S669000, C424S078080, C424S078370
Reexamination Certificate
active
06214885
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to the use of polymers containing &bgr;-hydroxyalkylvinylamine units, as obtainable by reacting polymers containing vinylamine units with epoxides, as biocides.
2. Description of Related Art
Polymers containing vinylamine units are prepared, as is known, by polymerizing acyclic N-vinylcarboxamides, preferably N-vinylformamide, and then hydrolyzing the polymers using acids or bases; cf. U.S. Pat. Nos. 4,421,602, 3,597,314, 4,578,515 and 4,255,548.
The preparation of modified polyvinylamines is also known from the literature. For example, the water-solubility of polyvinylamines is improved by grafting ethylene oxide or propylene oxide onto polyvinylamine; cf. Ikemura, Kobunshi Kagaku, 26 (288), 306-310 (1969).
U.S. Pat. No. 5,324,787 discloses modified polyvinylamines obtainable by reacting at least 0.1 mol % of the amine units of polyvinylamine with a glycidyl ether compound. The reaction produces hydrophobicized polyvinylamines which are used as retention agents in papermaking.
The reaction of polyalkylenepolyamines and monoepoxides or polyepoxides for preparing water-dispersible reactive resins which contain epoxide groups and are used in coating materials is known from U.S. Pat. Nos. 5,246,984 and 5,350,784.
Z. Chem. 27 (1987) 1 discloses specially functionalized polyvinyl alcohols, polyacrylates and polyethylenimines 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.
SU-A-1,071,630 discloses that copolymers of diallyldimethyl-ammonium 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 45 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. 4,005,193 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.
BRIEF DESCRIPTION OF THE INVENTION
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 of polymers containing &bgr;-hydroxyalkyl-vinylamine units, as obtainable by reacting polymers containing vinylamine units with epoxides of the formula
in which R is C
2
-C
28
alkyl, phenyl, C
1
-C
18
alkylphenyl or C
2
-C
18
alkenyl.
DETAILED DESCRIPTION OF THE INVENTION
The polymers to be used in accordance with the invention, and a process for preparing them, are described in the earlier application P 1 96 17983.1.
Polymers containing vinylamine units are known; cf., for example, U.S. Pat. No. 4,217,214, EP-A-0 071 050 and EP-A-0 216 387. These polymers are obtainable by copolymerizing open-chain N-vinylcarboxamides, alone or together with other monoethylenically unsaturated monomers, and then eliminating the formyl or alkylcarbonyl group from the copolymerized open-chain N-vinylcarboxamide units using acids, bases or enzymes, with the formation of vinylamine units.
The polymers containing vinylamine units are prepared starting, for example, from open-chain N-vinylcarboxamides of the formula
in which R
1
and R
2
can be identical or different and are hydrogen or C
1
-C
6
alkyl. Examples of suitable monomers are N-vinylformamide (R
1
=R
2
=H in formula I), N-vinyl-N-methylformamide, N-vinylacetamide, N-vinyl-N-methylacetamide, N-vinyl-N-ethylacetamide, N-vinyl-N-methylpropionamide and N-vinylpropionamide. To prepare the polymers, the abovementioned monomers can be polymerized either alone, in a mixture with one another, or together with other monoethylenically unsaturated monomers. It is preferred to start from polymers of N-vinylformamide.
Suitable monoethylenically unsaturated monomers are all compounds which can be copolymerized with the open-chain vinylcarboxamides. Examples thereof are vinyl esters of saturated carboxylic acids of 1 to 6 carbon atoms, such as vinyl formate, vinyl acetate, vinyl propionate and vinyl butyrate. Further suitable comonomers are ethylenically unsaturated C
3
-C
6
carboxylic acids, examples being acrylic acid, methacrylic acid, maleic acid, crotonic acid, itaconic acid and vinylacetic acid and also their alkali metal and alkaline earth metal salts, esters, amides and nitriles, examples being methyl acrylate, methyl methacrylate, ethyl acrylate and ethyl methacrylate. Further suitable carboxylic esters are derived from glycols or polyalkylene glycols, with only one OH group being esterified in each case; examples are hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxybutyl acrylate, hydroxypropyl methacrylate, hydroxybutyl methacrylate and also acrylic monoesters of polyalkylene glycols having a molecular mass of from 500 to 10,000. Further suitable comonomers are esters of ethylenically unsaturated carboxylic acids with amino alcohols, such as, for example, dimethylaminoethyl acrylate, dimethylaminoethyl methacrylate, diethylaminoethyl acrylate, diethylaminomethyl methacrylate, dimethylaminopropyl acrylate, dimethylaminopropyl methacrylate, diethylaminopropyl acrylate, dimethylaminobutyl acrylate and diethylaminobutyl acrylate. The basic acrylates can be used in the form of the free bases, the salts with mineral acids such as hydrochloric acid, sulfuric acid or nitric acid, the salts with organic acids such as formic acid, acetic acid, propionic acid or sulfonic acid, or in quaternized form. Examples of suitable quaternizing agents are dimethyl sulfate, diethyl sulfate, methyl chloride, ethyl chloride and benzyl chloride. Further suitable comonomers are amides of ethylenically unsaturated carboxylic acids, such as acrylamide, methacrylamide and also N-alkylmonoamides and -diamides of monoethylenically unsaturated carboxylic acids having alkyl radicals of 1 to 6 carbon atoms, examples being N-methylacrylamide, N,N-dimethylacrylamide, N-methylmethacrylamide, N-ethylacrylamide, N-propylacrylamide and tert-butylacrylamide, and also basic (meth)acrylamides, such as dimethylaminoethylacrylamide, dimethylaminoethylmethacrylamide, diethylaminoethylacrylamide, diethylaminoethylmethacrylamide, dimethylaminopropylacrylamide, diethylaminopropylacrylamide, dimethylaminopropylmethacrylamide and diethylaminopropylmethacrylamide, for example.
Further suitable comonomers are N-vinylpyrrolidone, N-vinylcaprolactam, acrylonitrile, methacrylonitrile, N-vinylimidazole and also substituted N-vinylimidazoles such as, for example, N-vinyl-2-methylimidazole, N-vinyl-4-methylimidazole, N-vinyl-5-methylimidazole, N-vinyl-2-ethylimidazole and N-vinylimidazolines such as vinylimidazoline, N-vinyl-2-methylimidazoline and N-vinyl-2-ethylimidazoline, for example. In addition to the free base form, N-vinylimidazoles and N-vinylimidazolines are also used neutralized with mineral acids or organic acids or in quaternized form, quaternization being performed preferably with dimethyl sulfate, diethyl sulfate, methyl chloride or benzyl chloride.
Further suitable comonomers are monomers containing sulfo groups, such as vinylsulfonic acid, allylsulfonic acid, methallylsulfonic acid, styrenesulfonic acid, the alkali metal or ammonium salts of these acids, or 3-sulfopropyl acrylate, for example.
The copolymers also include terpolymers and those polymers which in addition contain at least one further monomer in copolymerized form.
In order to prepare copolymers containing vinylamine units, it is preferred to start from homopolymers of N-vinylformamide or from copolymers containing in copolymerized fo
Decker Jurgen
Mahr Norbert
Negele Anton
Tropsch Jurgen
Zeller Dieter
Barts Samuel
BASF - Aktiengesellschaft
Davis Brian J.
Keil & Weinkauf
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