Initiator mixture, composition, the use thereof, polyol polymer preparation method, and polyol polymer obtained by the method
View Patent ↗The present invention relates to an initiator mixture, a composition, use thereof, a process of preparing polymer polyol, and a polymer polyol obtained by the process. The initiator mixture comprises: a first peroxide of formula (I) R 1 —O—O—R 2 , wherein R 1 and R 2 are independent an alkyl group or an alkanoyl group comprising 1 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 4 to 20 carbon atoms; and a second peroxide of formula (II) R 3 —O—O—R 4 —O—O—R 5 , wherein R 3 and R 5 are independently an alkyl group comprising 1 to 30 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 5 to 10 carbon atoms, and R 4 is a cycloalkylene group comprising 3 to 30 carbon atoms, preferably 4 to 20 carbon atoms, and more preferably 5 to 10 carbon atoms.
1. An initiator mixture comprising a first peroxide of formula (I) and a second peroxide of formula (II):
R 1 —O—O—R 2 , (I)
wherein R 1 and R 2 are independently an alkyl group or an alkanoyl group comprising 1 to 30 carbon atoms, and
R 3 —O—O—R 4 —O—O—R 5 , (II)
wherein R 3 and R 5 are independently an alkyl group comprising 1 to 30 carbon atoms, and R 4 is a cycloalkylene group comprising 3 to 30 carbon atoms,
wherein the initiator mixture comprises 70 to 90 wt % of the first peroxide of formula (I) and 10 to 30 wt % of the second peroxide of formula (II), based on the total weight of the initiator mixture.
2. The initiator mixture according to claim 1 , wherein at least one of R 1 and R 2 is an alkanoyl group.
3. The initiator mixture according to claim 1 , wherein at least one of R 1 and R 2 is a t-amyl group.
4. The initiator mixture according to claim 1 , wherein at least one of R 1 is an alkanoyl group and R 2 is a t-amyl group.
5. The initiator mixture according to claim 1 , wherein R 1 is selected from the group consisting of formacyl, acetyl, propionyl, butyryl, valeryl, pivaloyl, caproyl, enanthyl, capryloyl, 2-ethylcaproyl, nonanoyl, decanoyl, undecanoyl, dodecanoyl, tridecanoyl, tetradecanoyl, hexadecanoyl, octadecanoyl, and eicosanoyl,
wherein R 2 , R 3 and R 5 are independently a tert-alkyl group comprising 4 to 30 carbon atoms, and
wherein R 4 is a 1,1-cycloalkylene group.
6. The initiator mixture according to claim 1 , wherein the first peroxide of formula (I) comprises t-amyl peroxy-2-ethylhexanoate, tertio-amyl peroxypivalate, tertio-butyl peroxy-2-ethylhexanoate, or tertio-amyl peroxyneodecanoate, and/or the second peroxide of formula (II) comprises 1,1-di(t-amylperoxy)-cyclohexane, 1,1-di(tertio-butylperoxy)-3,3,5-trimethylcyclohexane, or 1,1-di(tertio-butylperoxy)-cyclohexane.
7. An initiator mixture comprising a first peroxide of formula (I), a second peroxide of formula (II), and a third peroxide of formula (III):
R 1 —O—O—R 2 , (I)
wherein R 1 and R 2 are independently an alkyl group or an alkanoyl group comprising 1 to 30 carbon atoms, and
R 3 —O—O—R 4 —O—O—R 5 , (II)
wherein R 3 and R 5 are independently an alkyl group comprising 1 to 30 carbon atoms, and R 4 is a cycloalkylene group comprising 3 to 30 carbon atoms,
R 6 —O—O—C(═O)—O—R 7 , (III)
wherein R 6 and R 7 are independently an alkyl group comprising 1 to 30 carbon atoms.
8. The initiator mixture according to claim 7 , wherein R 6 is a tert-alkyl group comprising 4 to 30 carbon atoms, and wherein R 7 is selected from the group consisting of methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, cetyl, octadecyl, and eicosyl.
9. The initiator mixture according to claim 7 , wherein the third peroxide of formula (III) comprises OO-t-amyl-O-(2-ethylhexyl)-monoperoxycarbonate or OO-t-butyl-O-(2-ethylhexyl)-monoperoxycarbonate.
10. The initiator mixture according to claim 7 , wherein the initiator mixture comprises 50 to 90 wt % of the first peroxide of formula (I), 10 to 50 wt % of the second peroxide of formula (II), and greater than 0 and equal to or less than 30 wt % of the third peroxide of formula (III), based on the total weight of the initiator mixture.
11. A composition comprising the initiator mixture of claim 1 and a thiol-based chain transfer agent.
12. The composition of claim 11 , wherein the thiol-based chain transfer agent comprises a chain transfer agent of formula (IV):
SH—R 8 —C(═O)—O—R 9 , (IV)
wherein R 8 is an alkylene group comprising 1 to 30 carbon atoms and R 9 is an alkyl group comprising 1 to 30 carbon atoms.
13. The composition according to claim 12 , wherein R 8 is selected from the group consisting of methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, and decylene, and wherein R 9 is selected from the group consisting of methyl, ethyl, propyl, butyl, amyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, cetyl, octadecyl, and eicosyl.
14. The composition according to claim 12 , wherein the chain transfer agent of formula (IV) is 2-ethylhexyl thioglycolate.
15. The composition according to claim 11 , wherein the composition comprises 30 to 70 wt % of the initiator mixture and 30 to 70 wt % of the thiol-based chain transfer agent, based on the total weight of the composition.
16. A process of preparing a polymer polyol comprising polymerizing a reaction mixture comprising a polyol, an ethylenically unsaturated monomer, and optionally a macromonomer, in the presence of the initiator mixture of claim 1 .
17. The process according to claim 16 , wherein the amount of the initiator mixture is 0.1 to 0.8 wt % based on the weight of the reaction mixture.