Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1992-05-15
1998-01-13
Schofer, Joseph L.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
526319, 526328, 526335, 526341, 526346, 526348, C08F 436, C08F11804, C08F12018, C08F13602, C08F12044, C08F11206
Patent
active
057081042
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel allyl peroxide chain transfer agents, methods of radically polymerizing monomers in the presence of said peroxides to thereby control the molecular weights of the resulting polymers and to polymers and shaped objects containing polymers produced by the instant polymerization methods.
The general cgncept of employing a molecular weight regulating agent, also known as a chain transfer agent, as an additive during polymerization reactions has been known for a long time. A number of different chain transfer agents having an olefinic group therein, have been employed for this purpose.
Perhaps one of the earlier disclosures of such a polymerization modifying material can be found in U.S. Pat. No. 3,248,374 published on 24 Jun. 1966, wherein the use of an olefin of the formula I as a polymerization modifier is disclosed. ##STR1## wherein R is hydrogen, halogen or a saturated aliphatic radical and X is halogen, cyanide, phenyl, carboxyl, carbonate, phenyloxy, --CONH.sub.2, --CONH-alkyl or --CON-dialkyl. The presence of these olefinic materials during the polymerization of vinylidene chloride with other olefinic materials rendered the resultant polymer more water soluble.
U.S. Pat. No. 3,726,832 published on 10 Apr. 1973, discloses the use of a cyclic ether or a vinyl ether as a moiecular weight regulator for the polymerization of dienes.
U.S. Pat. No. 4,176,219 published on 27 Nov. 1979, discloses the use of allyl halides, benzyl halides or a tertiary aliphatic halide compound as molecular weight regulators fort the production of 1,2-polybutadiene.
U.S. Pat. No. 4,405,742, published on 20 Sep. 1983, discloses the use as a regulator, of unsaturated ethers, thioethers, amines, and acrylates and thioacrylates of acrylamides for the purpose of polymerizing chloroprene toproduce an improved polychloroprene product.
Finally, PCT patent application WO 88/04304 published on 16 Jun. 1988 discloses the use of compounds of the formula (II) for the purpose of controlling the molecular weight and end group functionality of polymers. ##STR2## wherein R.sub.1 is hydrogen or a group capable of activating the vinylic carbon towards free radical addition; Y is OR.sub.2 or CH.sub.2 X(R.sub.2).sub.n, where R.sub.2 is an optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, or optionally substituted saturated or unsaturated carbocyclic or heterocyclic ring; X is an element other than carbon selected from Groups IV, V, VI or VII of the Periodic Table or a group consisting of an element selected from Groups IV, V or VI to which is attached one or more oxygen atoms: and n is a number from 0 to 3 such that the valency of X is satisfied and, when n is greater than 1, the groups represented by R.sub.2 may be identical or different.
When this broad formula is literally interpreted and Y is selected to be CH.sub.2 XR.sub.2 and X is selected to be an element from Group VI to which is attached one or more oxygen atoms and that element from Group VI is oxygen, one obtains, as one of a multitude of possibilites, an unsaturated peroxide. However, the application text itself makes no reference to the possibility that compounds of the formula II can, in fact, be peroxides and no examples employing peroxides of the formula II are included in the text of the application. Further, oxygen is not included in the more specific list of suitable elements for X and peroxides are not included in the list of suitable oxygen containing groups represented by X. Finally, on page 5 it is disclosed that when compounds of the formula II wherein Y is CH.sub.2 XR.sub.2 are employed as chain transfer agents, a polymer or oligomer is produced which contains a polymerizable olefinic group at one end thereof. This last statement clearly excludes peroxides from, being considered by one of ordinary skill in the art because, as will be later discussed herein, the use of such an unsaturated peroxide would not produce the required polymerizable olefinic group at one end of the polymer or oligomer. According
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Maillard Bernard Jean
Meijer John
Vertommen Luc Louis Theophile
Cheng Wu C.
E.I. duPont de Nemours & Co.
Schofer Joseph L.
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