Stabilization of compounds comprising iodine

Patent metadata

Field	Value
Publication number	US-9585384-B2
Application number	US-201414551123-A
Country	US
Kind code	B2
Filing date	Nov 24, 2014
Priority date	Apr 1, 2009
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

Use of aziridines for stabilizing iodine-containing compounds, especially biocides.

First claim

What is claimed is:

1. A binder formulation comprising:
at least one alkyd resin binder,
at least one iodine containing compound, and
at least one aziridine compound of the formula (I)

where
R 1 is hydrogen, alkyl or cycloalkyl, each of which are 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 have the same definition as R 1 and additionally independently are halogen, hydroxyl, carboxyl, alkylsulphonyl, arylsulphonyl, nitrile, isonitrile, and/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.

2. The binder formulation according to claim 1 , further comprising at least one transition metal dryer.

3. The binder formulation according w claim 1 , further comprising at least one polar organic solvent.

4. The binder formulation according to claim 1 , comprising
1% to 80% by weight of the alkyd resin binder(s),
0% w 50% by weight of colour pigments,
0.01% to 5% by weight of the iodine-containing compound,
0.001% to 5% by weight of the aziridine compound,
2% to 97% by weight of solvent(s), and
0.001% to 3% by weight of a transition metal dryer.

5. Industrial materials comprising the binder formulation according to claim 1 .

6. The binder formulation according to claim 1 , wherein the iodine-containing compound is selected from the group consisting of 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), iodofenfos, 3-iodo-2-propynyl 2,4,5-trichlorophenyl ether, 3-iodo-2-propynyl 4-chlorophenyl formal (IPCF), N-iodopropargyloxycarbonylalanine, N-iodopropargyloxycarbonylalanine 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-do-2-propynyl phenylcarbamate, di(3-iodo-2-propynyl) hexyldicarbamate, 3-iodo-2-propynyloxyethanol ethylcarbamate, 3-iodo-2-propynyloxyethanol phenylcarbamate, 3-iodo-2-propynyl thioxothioethylcarbamate, 3-iodo-2-propynyl carbamate (IPC), 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate and 3-iodo-2-propynyl cyclohexylcarbamate.

7. The binder formulation according to claim 1 , wherein the iodine-containing compound is selected from the group consisting of 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) hexyldicarbamate, 3-iodo-2-propynyloxyethanol ethylcarbamate, 3-iodo-2-propynyloxyethanol phenylcarbamate, 3-Iodo-2-propynyl thioxothioethylcarbamate, 3-iodo-2-propynyl carbamate (IPC), 3-bromo-23-diiodo-2-propenyl ethylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate and 3-iodo-2-propynyl cyclohexylcarbamate.

8. The binder formulation according to claim 1 , wherein the iodine-containing compound is selected from the group consisting of N-alkyl-iodotetrazoles, N-aryl-iodotetrazoles, and N-aralkyl-iodotetrazoles.

9. A binder formulation comprising:
at least one alkyd resin binder,
at least one iodine containing compound, and
at least one aziridine compound of the formula (II)

where
the carbocyclic ring is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, hydroxyl, oxo, carboxyl, alkylsulphonyl, arylsulphonyl, nitrile, isonitrile, alkyl or cycloalkyl, each of which is unsubstituted or substituted and/or mono- or polyethylenically unsaturated, or substituted or unsubstituted fullerenyl, aryl, alkoxy, alkoxycarbonyl or alkanoyl, and
n is a number from 0 to 6.

10. The binder formulation according to claim 9 , further comprising at least one transition metal dryer.

11. The binder formulation according w claim 9 , further comprising at least one polar organic solvent.

12. The binder formulation according to claim 9 , comprising
1% to 80% by weight of the alkyd resin binder(s),
0% w 50% by weight of colour pigments,
0.01% to 5% by weight of the iodine-containing compound,
0.001% to 5% by weight of the aziridine compound,
2% to 97% by weight of solvent(s), and
0.001% to 3% by weight of a transition metal dryer.

13. Industrial materials comprising the binder formulation according to claim 9 .

14. The binder formulation according to claim 9 , wherein the iodine-containing compound is selected from the group consisting of 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), iodofenfos, 3-iodo-2-propynyl 2,4,5-trichlorophenyl ether, 3-iodo-2-propynyl 4-chlorophenyl formal (IPCF), N-iodopropargyloxycarbonylalanine, N-iodopropargyloxycarbonylalanine 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) hexyldicarbamate, 3-iodo-2-propynyloxyethanol ethylcarbamate, 3-iodo-2-propynyloxyethanol phenylcarbamate, 3-iodo-2-propynyl thioxothioethylcarbamate, 3-iodo-2-propynyl carbamate (IPC), 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate and 3-iodo-2-propynyl cyclohexylcarbamate.

15. The binder formulation according to claim 9 , wherein the iodine-containing compound is selected from the group consisting of 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) hexyldicarbamate, 3-iodo-2-propynyloxyethanol ethylcarbamate, 3-iodo-2-propynyloxyethanol phenylcarbamate, 3-iodo-2-propynyl thioxothioethylcarbamate, 3-iodo-2-propynyl carbamate (IPC), 3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 3-iodo-2-propynyl n-hexylcarbamate and 3-iodo-2-propynyl cyclohexylcarbamate.

16. The binder formulation according to claim 9 , wherein the iodine-containing compound is selected from the group consisting of N-alkyl-iodotetrazoles, N-aryl-iodotetrazoles, and N-aralkyl-iodotetrazoles.

Assignees

• Lanxess Deutschland Gmbh

Inventors

• Bottcher Andreas
• Koop Bernd
• Spetmann Peter

Classifications

• A01N43/44

  three- or four-membered rings · CPC title

• C09D5/14

  Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence) · CPC title

• A01N25/22 Primary

  containing ingredients stabilising the active ingredients · CPC title

• C08K5/205

  Compounds containing [IMAGE cpc-sch-C08K-1010.gif] groups, e.g. carbamates · CPC title

• C08L67/06

  Unsaturated polyesters · CPC title