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United States Patent (19) 11 Patent Number: 5,548,046 Sanchez 45) Date of Patent: Aug

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United States Patent (19) 11 Patent Number: 5,548,046 Sanchez 45) Date of Patent: Aug US005548046A United States Patent (19) 11 Patent Number: 5,548,046 Sanchez 45) Date of Patent: Aug. 20, 1996 54). STABILIZED DIALKYL OTHER PUBLICATIONS PEROXYDICARBONATE COMPOSITIONS AND THEIR USES J. Am. Chem. Soc., 1950, 72, 1254-1263. 75) Inventor: Jose Sanchez, Erie, N.Y. Primary Examiner-Josepho L. Schofer (73) Assignee: Elf Atochem North America, Inc., Assistant Examiner-Wu C. Cheng Philadelphia, Pa. Attorney, Agent, or Firm-Stanley A. Marcus; Royal E. Bright (21) Appl. No.: 197,031 22 Filed: Feb. 16, 1994 57 ABSTRACT Thermally stabilized initiator compositions comprising: (51 Int. Cl. ............................ C08F 4/34; CO8F 120/20, C08F 14/06; CO8F 112/08; CO8F 110/02 (a) at least one dialkyl peroxydicarbonate, and 52 U.S. Cl. ....................... 526/230.5; 526/236; 526/328; (b) a stabilizing effective amount of a compound of 526/344; 526/346; 526/352; 526/217 Structure I: 58) Field of Search ................................. 526/230.5, 236, H Z I 526/328,344, 346, 352 N / C-C 56 References Cited R? Y, U.S. PATENT DOCUMENTS wherein R, R and Z are as defined in the summary of 3,413,277 11/1968 Crano et al. ......................... 526/230.5 the invention section, processes for their preparation 3,821,273 6/1974 D'Angelo ............................. 526/230.5 and use are disclosed. 5,155,192 10/1992 MacLeay ................................ 526/228 FOREIGN PATENT DOCUMENTS 56-167711 12/1981 Japan. 10 Claims, No Drawings 5,548,046 1 2 STABILIZED DIALKYL significant levels of hydroperoxides such as t-butyl hydro PEROXYDICARBONATE COMPOSTIONS peroxide and cumene hydroperoxide since these impurities AND THEIR USES are free-radical chain-transfer agents and can become incor porated into the resin molecular chains as peroxy end BACKGROUND OF THE INVENTION 5 groups. Such labile end groups can adversely affect the thermal and color stability of the resin. In addition, the lower Field of the Invention molecular weight t-alkyl hydroperoxides such as t-butyl and t-amyl hydroperoxides are sufficiently volatile to cause This invention relates to compositions classified in the art problems during recycle of vinyl chloride and other mono of chemistry as dialkyl peroxydicarbonates, more specifi 10 S. cally to new and novel thermally-stabilized initiator com The thermally stabilized dialkyl peroxydicarbonate com positions comprising dialkyl peroxydicarbonates stabilized positions of the instant invention, which contain compounds by the addition thereto of a stabilizing effective amount of at having ethylenically unsaturated groups conjugated with least one stabilizing compound having an ethylenically nitriles or ethylenically unsaturated groups conjugated with unsaturated functional group conjugated with an acetylenic 15 acetylenic groups advance the peroxide art and the poly or nitrile functional group. The invention further relates to merization art since they do not cause the above resin the use of such novel compositions as initiators of polymer stability problems or monomer recycle problems. ization or cure of ethylenically unsaturated monomers, oli It is generally known to organic peroxide producers, see gomers and polymers. The invention still further relates to the Strain reference cited above, that lower molecular weight the stabilization of dialkyl peroxydicarbonates during their 20 dialky peroxydicarbonates (such as diisopropyl peroxydi manufacture by the inclusion of a stabilizing effective carbonate), which are in the liquid state during their pro amount of at least one stabilizing compound having ethyl duction by reaction of an alkyl chloroformate with an enic unsaturation conjugated with acetylenic or nitrile unsat aqueous solution of hydrogen peroxide and an inorganic uration in the mixture of reactants from which a dialkyl base such as sodium hydroxide or potassium hydroxide, can peroxydicarbonate is to be prepared prior to, at the com 25 be thermally stabilized and prevented from undergoing auto mencement of or during the preparative reaction. or self-accelerating decomposition during manufacture by bubbling oxygen gas or an oxygen containing gas, e.g., air, DESCRIPTION OF THE PRIOR ART through the reaction mixture. However, in such processes at Generally, dialkyl peroxydicarbonates which are in liquid least one settling of the reaction mixture into an upper form (molten or in solution) above ca. 10° C. are very organic phase (dialkyl peroxydicarbonate) and a lower aque hazardous owing to auto-accelerated decomposition attrib ous phase is required. During these separations, agitation uted to induced decomposition of the dialkyl peroxydicar necessarily is terminated and bubbling of oxygen gas or an bonate. Strain, et al. (J. Am. Chem. Soc., 1950, 72, oxygen containing gas is stopped in order to enable com 1254-1263) found that auto-accelerated decomposition of plete separation of phases. During this quiescent period the diisopropyl peroxydicarbonate (IPP) at room temperature 35 organic dialkyl peroxydicarbonate phase is deprived of could oxygen stabilizer and a hazardous self-accelerating decom position of the liquid dialkyl peroxydicarbonate phase can CH CH IPP OCC. N / HC-O-C-OO-C-O-CH This invention provides a novel manufacturing process of 40 enhanced safety for production of liquid dialkyl peroxydi CH CH carbonates. The process employs a small quantity of an be largely suppressed by incorporating small quantities of ethylenically unsaturated nitrile or acetylenic compound additives such as iodine (1%), phenol (1%), hydroquinone during processing for enhancing the thermal stability of the (1%), resorcinol (1%), pyrogallol (1%), tetralin (1%), ethyl liquid dialkyl peroxydicarbonate during manufacture, thus acetoacetate (1%), acetanilide (1%), trinitrobenzene (1%), 45 suppressing self-accelerating decomposition of the liquid 30% hydrogen peroxide (1%) and several other additives. peroxydicarbonate during manufacture and enhancing the However, when such stabilizing compositions are used to thermal stability of the liquid dialkyl peroxydicarbonate polymerize vinyl chloride monomer (VCM), there is poten during Subsequent storage and handling. tial for contamination of the resulting PVC resin by the The novel processes providing enhanced safety for the additives. This contamination is undesirable, both for the 50 manufacture, storage, handling and use of pure liquid dialkyl PVC resin as well as for the environment. Because the peroxydicarbonates can be of the batch type, continuous thermally stabilized dialkyl peroxydicarbonate composi type or semi-continuous type. tions of the instant invention contain only small quantities of It should be noted that the addition of the organic hydro freeradically polymerizable unsaturated nitriles or unsatur peroxide stabilizers for dialkyl peroxydicarbcnates known in ated acetylenic compounds (such as methacrylonitrile), the 55 the art, such as those provided by the aforementioned U.S. stabilizing additives are copolymerized with VCM at very Pat. No. 5,155,192, during the process for production of pure low levels (ca. 1-5 parts per million), and thus do not liquid dialkyl peroxydicarbonates would not be effective for contaminate the PVC resin or the effluent from the poly thermally stabilizing the dialkyl peroxydicarbonates during merization process. processing or subsequent to processing since the art organic U.S. Pat. No. 5,155,192 discloses stabilized peroxydicar 60 hydroperoxide stabilizers are reactive with alkyl chlorofor bonate compositions containing small amounts (0.03 to 3.0 mares, forming OO-t-alkyl O-alkyl monoperoxycarbonates: equivalent percent) of compounds containing hydroperoxy groups. Such compositions are claimed to reduce sensitivity O to auto-accelerative decompositions, increase safe storage t-Alkyl-OO-C-O-Alkyl temperatures and increase self-accelerating decomposition 65 temperatures (SADTs). However, polymer producers such which are not known stabilizers for dialkyl peroxydicarbon as PVC producers do not like to employ initiators containing ates. Furthermore, many of the organic hydroperoxides of 5,548,046 3 4 the art are likely to partition into the aqueous phases that are Particular mention is also made of compositions of the involved in dialkyl peroxydicarbonate manufacturing pro first composition aspect of the invention wherein the dialkyl cesses, and, thus, the thermal stabilizers would not be peroxydicarbonate is selected from compounds having the present in the organic dialkyl peroxydicarbonate phase Structure II: where thermal stabilization is needed. Therefore, the stabi 5 lizing compounds having an ethylenic unsaturated func I tional group conjugated with an acetylenic or nitrile func R4-O-C-OO-C-O-Rs tional group, especially the unsaturated nitriles or the wherein R and Rs are the same or different and are selected unsaturated acetylenic compounds of Structure I of this from the group consisting of substituted or unsubstituted invention are also superior to the stabilizers previously 10 alkyl of 2 to 22 carbons, substituted or unsubstituted known for thermally stabilizing dialkyl peroxydicarbonates cycloalkyl of 5 to 12 carbons, substituted or unsubstituted during production, bicycloalkyl of 7 to 9 carbons, and substituted or unsubsti tuted aralkyl of 7 to 12 carbons, with substituents for alky being one or more alkyl of 1 to 4 carbons, alkoxy of 1 to 6 DEFINITIONS 5 carbons or phenoxy, substituents for cycloalkyl being one or As used herein and in the appended claims the following more alkyl of 1 to 6 carbons, substituents for bicycloalkyl
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