Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Compositions to be polymerized by wave energy wherein said...
Patent
1995-02-23
1996-09-24
Chapman, Mark
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Compositions to be polymerized by wave energy wherein said...
522904, 528196, 525370, 525371, 524800, 524841, C08F 246
Patent
active
055591620
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to polymeric peroxycarbonates, a process for making the polymeric peroxycarbonates and initiator compositions comprising these polymeric peroxycarbonates. The polymeric peroxycarbonates of the present invention provide significant advantages in the polymerization of vinyl monomers.
Several types of polymeric peroxides are known in the prior art. For example, in Chemical Abstracts, Vol. 60, 5293d and 10892e (1964) one finds diacyl-type polymeric peroxides obtained by reaction of a chloride of an aliphatic dibasic acid and sodium peroxide. Ester-type polymeric peroxides are known, for example, from European Patent applications 0 384 660 and 0 364 169.
Further, from Zh. Org. Khim., Vol. 13, No. 9, page 1,842 (1977) it is known that the reaction of an aliphatic or aromatic dibasic acid chloride with 2,5-dimethylhexane-2,5-dihydroperoxide results in the production of the corresponding polymeric peroxy ester. A similar preparation process is also disclosed in U.S. Pat. No. 3,117,166.
Also known are a wide variety of polymers which contain several peroxide groups therein. Examples of acyl peroxide-containing polymers can be found in U.S. Pat. No. 4,304,882. Peroxycarbonate group-containing polymers can be found in Japanese patent application J5 8023-807 and U.S. Pat. No. 3,879,353. However, none of these publications discloses the peroxycarbonate polymers of the present invention.
None of the foregoing polymeric peroxides offer a combination of low-temperature initiation, storage stability and high molecular weight polymer products which is satisfactory for a wide range of applications. Accordingly, the present invention is directed to a specific peroxycarbonate polymer which exhibits a unique combination of properties which makes it particularly suitable for polymerization of vinyl monomers.
The present invention relates to a polymeric peroxycarbonate which comprises at least two structural units represented by the formula I: ##STR1## wherein R is selected from C.sub.1 -C.sub.6 alkylene, alkyne, alkadiyne, 1,3-phenylene, 1,4-phenylene, cis- or trans-alkene, and alkadiene; R.sub.1 and R.sub.2 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.6 -C.sub.10 aryl and R.sub.1 and R.sub.2 may combine to form a C.sub.3 -C.sub.12 alkyl ring; and R.sub.3 is selected from (A)-(F): ##STR2## wherein R.sub.4 and R.sub.5 are independently selected from C.sub.1 -C.sub.6 alkyl, C.sub.6 -C.sub.10 aryl and R.sub.4 and R.sub.5 may combine to form a C.sub.3 -C.sub.12 alkyl ring; R.sub.6 is selected from methylene, 1,4-phenylene, ##STR3## wherein R.sub.7 is selected from hydrogen and methyl; ##STR4## wherein R.sub.8 is selected from nothing, methyl, ethyl and ethoxy; ##STR5## wherein R.sub.8 is as defined above; ##STR6## wherein R.sub.9 is nothing or methyl; ##STR7## wherein R.sub.9 is as defined above; ##STR8## wherein R.sub.10 is selected from C.sub.3 -C.sub.12 alkyl; 2-butenediyl-1,4; 2,4-hexadienediyl; 2-butynediyl-1,4; 2,4-hexadiynediyl-1,6; 3-hexynediyl-1,4; 3-methylpentadiyl-1,5; and --O--R.sub.3 --O-- can be represented by ##STR9## wherein p+q+r+s can be a value from 1 up to a value giving a maximum molecular weight of 10,000 grams/mole.
The present invention also relates to initiator compositions comprising one or more of the above-identified polymeric peroxycarbonates and a process for making these polymeric peroxycarbonates.
The closest peroxymonocarbonates to the structural unit of the formula I above are disclosed in European Patent application 0 266 966 and in U.S. Pat. Nos. 4,119,657 and 2,374,789. Further, bisperoxycarbonates are known from U.S. Pat. No. 3,652,631.
The polymeric peroxycarbonates of the present invention may take on one of two distinct forms. In one case, these materials are linear polymers having distinctive end groups which terminate the molecules. In a second embodiment, the repeating structural units are bound to themselves on both ends leading to a continuous molecule having no distinct beginning or end groups. Both of these types of molecules are encompass
REFERENCES:
patent: 2374789 (1945-05-01), Strain
patent: 3117166 (1964-01-01), Harrison
patent: 3652631 (1972-03-01), Stevens et al.
patent: 3879353 (1975-04-01), Crawford
patent: 3935243 (1976-01-01), Priddy
patent: 4119657 (1978-10-01), Komai et al.
patent: 4304882 (1981-12-01), D'Angelo et al.
English Translation Equivalent (which consists of pp. 1707-1711) for Zhurnal Organicheskoi Khimii, vol. 13, No. 9, pp. 1842-1846 (1977).
Chemical Abstracts, Physical Organic Chemistry, vol. 60, 5293d and 10892e (1964).
Alferink Petrus J. T.
Meijer John
Akzo Nobel NV
Chapman Mark
Mancini Ralph J.
Morris Louis A.
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