Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1995-04-26
1997-10-07
Schofer, Joseph L.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
5262305, 5262196, C08F 434, C08F 438, C08F 404
Patent
active
056749589
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for (co)polymerizing vinyl monomers in the presence of a radical polymerization initiator.
Various t-alkylperoxy alkanoate compounds have been described as radical polymerization initiators in the (co)polymerization of vinyl monomers.
U.S. Pat. Nos. 3,726,847 and 3,624,123 disclose a long list of t-alkylperoxy esters and their precursors, viz. hydroperoxides. The long list of hydroperoxides includes 3-methyl-3-hydroperoxy pentyne-1, which may also be used as a saturated hydroperoxide. These patent publications suggest that t-alkylperoxy esters can be used in the polymerization of vinyl monomers. Among others, t-butylperoxy pivalate (TBPP), t-butylperoxy neodecanoate (TX23), and .alpha.-cumylperoxy neodecanoate (CND) are exemplified. However, 3-methylpentyl-3-peroxy alkanoates are neither exemplified nor preferred.
Dutch patent application 69 15160 discloses the use of t-hexylperoxy alkanoate for the polymerization and/or curing of vinyl monomers. No specifics are given on the structure of this t-hexyl compound. However, from U.S. Pat. Nos. 4,057,567 and 4,063,013 it can be concluded that t-hexylperoxy alkanoate is 2-methylpentyl-2-peroxy alkanoate. These patent publications also disclose the use of 2-methylpentyl-2-peroxyalkanoates in the polymerization of vinyl monomers. Exemplified is 2-methylpentyl-2-peroxy neodecanoate (THPND).
There are several drawbacks to using the disclosed radical polymerization initiators in the (co)polymerization of vinyl monomers. The polymerization activity of TBPP is insufficient and the polymer conversion is relatively low, though the properties of the obtained polymer are satisfactory. It has also been found that the use of THPND results in a low polymer conversion. In addition, CND imparts a peculiar, offensive smell to the polymer due to the presence of decomposition products.
Furthermore, the synthetic resin industry demands reduction of the polymerization time. Although it was attempted to attain this requirement by increasing the amount of initiator, this method appeared to be impracticable, the resulting polymers being coloured.
An object of the present invention is to provide a polymerization process having high polymerization velocity, a short polymerization time, and an increase in conversion. Another object of the present invention is to provide a polymerization process for producing a colourless polymer having no offensive smell.
Therefore, the present invention relates to a process for (co)polymerizing vinyl monomers in the presence of a radical polymerization initiator, characterized in that said radical polymerization initiator is a 3-methylpentyl-3-peroxy alkanoate of the formula (I) ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 represent alkyl groups each having at most 9 carbon atoms with the proviso that the total number of carbon atoms of R.sub.1, R.sub.2 and R.sub.3 is at most 11, said 3-methylpentyl-3-peroxy alkanoate being employed in an amount of 0.002 to 2.0 parts by weight, based on 100 parts by weight of monomers present, said process being carried out at a temperature above 20.degree. C.
The use of 3-methylpentyl-3-peroxy alkanoates in the present invention surprisingly and unexpectedly results in a higher polymerization velocity, a shortened polymerization time, and an increase in conversion as compared with the results obtained by using other radical polymerization inititators. It has also been found that the obtained polymer has excellent thermal stability and is not affected by odour or colouration. Thus the industrial value of the radical polymerization initiator of the present invention is remarkably high.
Examples of the 3-methylpentyl-3-peroxy alkanoate of the formula (I) to be used in the present invention include 3-methylpentyl-3-peroxy pivalate (3MPPP), 3-methylpentyl-3-peroxy neohexanoate, 3-methylpentyl-3-peroxy neoheptanoate, 3-methylpentyl-3-peroxy neooctanoate, 3-methylpentyl-3-peroxy neononanoate, 3-methylpentyl-3-peroxy neodecanoate (3MPPND) and 3-methylpentyl-3-peroxy neotridecanoate.
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Yurzhenko, T.I., et al., Zh. Org. Khim. 3 (9), 1705-6 (1967) Abstract only.
Fukumura Takumi
Meijer John
Cheng Wu C.
Kayaku Akzo Corporation
Mancini Ralph J.
Morris Louis A.
Schofer Joseph L.
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