Stabilization of compounds containing iodine having polymers comprising nitrogen

Patent metadata

Field	Value
Publication number	US-9326502-B2
Application number	US-201214354035-A
Country	US
Kind code	B2
Filing date	Nov 15, 2012
Priority date	Nov 16, 2011
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

The invention relates to the production of nitrogen containing polymers from aziridines, to the use of these nitrogen containing polymers for stabilizing iodine containing compounds, to compositions comprising at least the nitrogen containing polymers and also iodine containing compounds, and to the use of these compositions as biocides and/or for controlling microorganisms.

First claim

What is claimed is:

1. A method for stabilizing iodine containing compounds, the method comprising contacting iodine containing compounds with nitrogen containing polymers obtained by reaction of aziridines in the presence of water, wherein 5% or less of the nitrogen in the nitrogen containing polymers is aziridine nitrogen.

2. The method according to claim 1 , wherein the iodine containing compounds are at least one of iodoalkynyl compounds and compounds in which one or more iodine atoms are bonded to one of sp 2 -hybridized carbon atoms of olefinic double bonds or sp 3 -hybridized carbon atoms.

3. The method according to claim 2 , wherein the iodine containing compounds have biocidal activity and are selected from a group that includes N—(C 1 -C 12 )-alkyl-iodotetrazoles, N—(C 6 -C 15 )-aryl-iodotetrazoles, N—(C 6 -C 15 )-arylalkyl-iodotetrazoles, diiodomethyl p-tolyl sulphone, diiodomethyl p-chlorophenyl sulphone, 3-bromo-2,3-diiodo-2-propenyl alcohol, 2,3,3-triiodoallyl alcohol, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone (CAS RN: 120955-77-3), iodofenphos, 3-iodo-2-propynyl 2,4,5-trichlorophenyl ether, 3-iodo-2-propynyl 4-chlorophenyl formal (IPCF), N-iodopropargyloxycarbonyl-alanine, N-iodopropargyloxycarbonyl-alanine ethyl ester, 3-(3-iodopropargyl)benzoxazol-2-one, 3-(3-iodopropargyl)-6-chlorobenzoxazol-2-one, 3-iodo-2-propynyl alcohol, 4-chlorophenyl 3-iodopropargyl formal, 3-iodo-2-propynyl propylcarbamate, 3-iodo-2-propynyl butylcarbamate (IPBC), 3-iodo-2-propynyl m-chlorophenylcarbamate, 3-iodo-2-propynyl phenylcarbamate, di-(3-iodo-2-propynyl)hexyl dicarbamate, 3-iodo-2-propynyloxyethanol ethylcarbamate, 3-iodo-2-propynyloxyethanol phenylcarbamate, 3-iodo-2-propynyl thioxothioethylcarbamate, 3-iodo-2-propynyl-carbamic ester (IPC), 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate and 3-iodo-2-propynyl cyclohexylcarbamate.

4. The method according to claim 1 wherein the nitrogen containing polymers have a weight-average molecular weight of more than 1000 g/mol.

5. The method according to claim 1 wherein the nitrogen containing polymers have a nitrogen content of 1% to 20% by weight.

6. The method according to claim 1 wherein the nitrogen containing polymers are polymers possessing at least one beta-aminoamine function.

7. The method according to claim 1 , wherein the nitrogen containing polymers have a weight-average molecular weight of 3000 to 60,000 g/mol, a nitrogen content of 5% to 12% by weight, and two or more beta-aminoamine functions.

8. The method according to claim 1 , wherein the aziridines are aziridine compounds of the formula (I)

where
R 1 is hydrogen, alkyl or cycloalkyl, each of which is unsubstituted or substituted and/or mono- or polyethylenically unsaturated, or in each case substituted or unsubstituted fullerenyl, aryl, alkoxy, alkoxycarbonyl, arylcarbonyl or alkanoyl,
R 2 , R 3 , R 4 and R 5 independently of one another are the compounds as defined by R 1 , halogen, hydroxyl, carboxyl, alkylsulphonyl, arylsulphonyl, nitrile, or isonitrile, or R 2 and R 4 , or R 3 and R 5 , together with the carbon atoms to which they are attached, form a 5- to 10-membered carbocyclic ring which is unsubstituted or substituted and/or mono- or polyethylenically unsaturated.

9. Biocidal compositions comprising:
a) at least one iodine containing compound having biocidal action; and
b) at least one nitrogen containing polymer obtained by reaction of aziridines in the presence of water, wherein 5% or less of the nitrogen in the nitrogen containing polymers is aziridine nitrogen.

10. The biocidal composition according to claim 9 , wherein the nitrogen containing polymers have a weight-average molecular weight of more than 1000 g/mol, a nitrogen content of 1% to 20% by weight, and at least one beta-aminoamine function.

11. The biocidal composition according to claim 9 , further comprising acid.

12. The biocidal composition according to claim 9 , further comprising active ingredients selected from a group that includes antimicrobially active compounds, fungicides, bactericides, herbicides and insecticides.

13. A binder formulation comprising:
a) at least one binder,
b) at least one iodine containing compound with biocidal action, and
c) at least one nitrogen containing polymer obtained by reaction of aziridines in the presence of water, wherein 5% or less of the nitrogen in the nitrogen containing polymers is aziridine nitrogen.

14. The binder formulation according to claim 13 , wherein the nitrogen containing polymers have a weight-average molecular weight of more than 1000 g/mol, a nitrogen content of 1% to 20% by weight, and at least one beta-aminoamine function.

15. The binder formulation according to claim 13 , further comprising at least one transition metal dryer.

16. A method for protecting industrial materials against destruction or infestation by microorganisms, the method comprising contacting the industrial materials with the biocidal compositions according to claim 9 .

17. The method according to claim 8 , wherein:
the iodine containing compounds have biocidal activity and are selected from a group that includes N—(C 1 -C 12 )-alkyl-iodotetrazoles, N—(C 6 -C 15 )-aryl-iodotetrazoles, N—(C 6 -C 15 )-arylalkyl-iodotetrazoles, diiodomethyl p-tolyl sulphone, diiodomethyl p-chlorophenyl sulphone, 3-bromo-2,3-diiodo-2-propenyl alcohol, 2,3,3-triiodoallyl alcohol, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone (CAS RN: 120955-77-3), iodofenphos, 3-iodo-2-propynyl 2,4,5-trichlorophenyl ether, 3-iodo-2-propynyl 4-chlorophenyl formal (IPCF), N-iodopropargyloxycarbonyl-alanine, N-iodopropargyloxycarbonyl-alanine ethyl ester, 3-(3-iodopropargyl)benzoxazol-2-one, 3-(3-iodopropargyl)-6-chlorobenzoxazol-2-one, 3-iodo-2-propynyl alcohol, 4-chlorophenyl 3-iodopropargyl formal, 3-iodo-2-propynyl propylcarbamate, 3-iodo-2-propynyl butylcarbamate (IPBC), 3-iodo-2-propynyl m-chlorophenylcarbamate, 3-iodo-2-propynyl phenylcarbamate, di-(3-iodo-2-propynyl)hexyl dicarbamate, 3-iodo-2-propynyloxyethanol ethylcarbamate, 3-iodo-2-propynyloxyethanol phenylcarbamate, 3-iodo-2-propynyl thioxothioethylcarbamate, 3-iodo-2-propynyl-carbamic ester (IPC), 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate, and 3-iodo-2-propynyl cyclohexylcarbamate;
the nitrogen containing polymers have a weight-average molecular weight of more than 1000 g/mol, a nitrogen content of 1% to 20% by weight, and at least one, beta-aminoamine function; and
the nitrogen containing polymers contain no detectable amounts of aziridine rings.

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Boettcher Andreas
• Uhr Hermann
• Spetmann Peter
• Jaetsch Thomas
• Fuehr Joerg

Classifications

• A61P31/10

  Antimycotics · CPC title

• A61P31/04

  Antibacterial agents · CPC title

• C08G73/0213

  Preparatory process · CPC title

• C08G73/0206

  Polyalkylene(poly)amines · CPC title

• A01N25/22 Primary

  containing ingredients stabilising the active ingredients · CPC title