Composition for the immediate termination of a free-radical polymerization and uses thereof
The invention relates to a composition for the immediate termination of a free-radical polymerization, the use thereof for the stabilization of free-radically polymerizable monomers against free-radical polymerization and a method for the immediate termination of free-radical polymerizations.
1. A composition comprising:
(i) at least one compound of formula (I):
R 1 OOC-A-CONR 2 R 3 (I)
wherein A is a C 2 -C 5 alkylene, R 1 , R 2 and R 3 , identical or different, are a C 1 -C 6 alkyl, and
(ii) at least one free-radical polymerization inhibitor.
2. The composition according to claim 1 wherein the at least one free-radical polymerization inhibitor is selected from the group consisting of phenothiazine derivative, para-methoxyphenol and TEMPO derivative.
3. The composition according to claim 1 wherein the at least one compound of formula (I) is methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate.
4. The composition according to claim 1 wherein the amount of the at least one compound of formula (I) is of at least 30% by weight based on the total weight of the composition.
5. The composition according to claim 2 wherein the phenothiazine derivative is a compound of general formula (II):
wherein R 4 and R 5 are each, identical or different, selected from the group consisting of H, and C 1 -C 12 -alkyl.
6. The composition according to claim 1 comprising at least 5% by weight of the at least one free-radical polymerization inhibitor based on the total weight of the composition.
7. The composition according to claim 2 comprising between 2.5 and 12.5% by weight of the para-methoxyphenol based on the total weight of the composition.
8. The composition according to claim 1 further comprising a glycol ether solvent.
9. The composition according to claim 1 comprising at least one further inhibitor selected from the group consisting of hydroquinone, catechol, 2,6-di-tert-butyl-4-methylphenol (BHT), tert-butylhydroquinone (TBHQ), 4-tert-butylcatechol (TBC), tocopherol derivatives, vitamin E, para-benzoquinone, derivatives of phenylene diamines, aromatic nitro or nitroso derivatives, manganese complexes, and copper complexes having an oxidation state of 2.
10. A method for immediately terminating free-radical polymerization, comprising: adding the composition according to claim 1 to a composition comprising at least one free-radically polymerizable monomer.
11. The method according to claim 10 wherein the free-radically polymerizable monomer comprises acrylonitrile, acrolein, methacrolein, acrylic acid, methacrylic acid, acrylic esters and/or methacrylic esters.
12. A method of stabilizing a free-radically polymerizable monomer, comprising: adding the composition of claim 1 to a composition comprising at least one free-radically polymerizable monomer.
13. The method according to claim 12 , wherein the free-radically polymerizable monomer comprises acrylonitrile, acrolein, methacrolein, acrylic acid, methacrylic acid, acrylic esters, and/or methacrylic esters.
14. The composition according to claim 4 wherein the amount of the at least one compound of formula (I) is of at least 50% by weight based on the total weight of the composition.
15. The composition according to claim 6 comprising the at least one free-radical polymerization inhibitor is present at at least 20% by weight of based on the total weight of the composition.
16. The composition according to claim 8 wherein the glycol ether solvent is diethylene glycol monomethylether (DEGME), or diethylene glycol monobutylether (DEGBE).
17. The composition according to claim 9 , wherein the at least one further inhibitor is manganese acetate, copper dibutyl dithiocarbamate or copper acetate.