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United States Patent Office Patented Sept 3,692,599 United States Patent Office Patented Sept. 19, 1972 2 tend to undergo decomposition at temperatures in the 3,692,599 PROCESS OF FORMINGHGH-ENERGY range of 10° to 60° C. and even the decomposition prod PROPELLANT BNDERS ucts, such as isopropyl alcohol, formed from the diiso John B. Gardiner, Mountainside, and Herschel T. White, propyl peroxydicarbonate promote violent decomposition Montclair, N.J., assignors to Esso Research and Engi of the ester. Thus, it can be seen that it is important in neering Company using a peroxydicarbonate in admixture with other sub No Drawing. Fied Feb. 28, 1963, Ser. No. 262,296 stances that the other substances should not cause ex Int, C. C06d 5/06 plosive decomposition. U.S. C. 49-9 4. Claims The high-energy polyether acrylates containing NF2 This invention relates to a method of forming stronger 0 groups to be used in forming the cured binders are vis high-energy binders, particularly polyacrylate binders con cous liquid polymers having molecular weights in the taining NF2 oxidizing groups, by using esters of peroxy range of about 500 to about 5,000. The starting materials carbonic acid as initiators in curing acrylates of NF for these polymers are polyethers having a suitable high containing polymers. content of NF groups attached to carbon atoms and As described in U.S. application Ser. No. 224,885, 5 OH functionality. Some of the NF2-containing polyethers filed Sept. 11, 1962 by John B. Gardiner and Anthony may be made by expoxidizing an NF-containing olefin J. Passannate, high-energy oxidizer binders obtained from and polymerizing the resulting NF-containing epoxide. NF-containing polyether acrylates have shown promise The preferred NF-containing polyethers have been made in chemical and physical characteristics for use in solid by reacting NFA with unsaturated polyethers, e.g. react rocket propellants. Such binders are employed in propor 20 ing NF with polypentadiene monoxide which is ob tions of about 5 to 30 wt. percent of the propellant to tained by polymerizing pentadiene monoxide. hold together other components which are dispersed in The OH functionality of the polyether may be con the binders, such as liquid oxidizers, solid oxidizers, and trolled by using modifiers such as glycidol, ethylene glycol, fuels, e.g. powdered metals of the class comprising B, Al, water or trimethylol propane. Be, Li and Mg, and compounds of such metals, such as 25 The NF-containing polyethers are acrylated, prefer their hydrides. ably when an excess of acrylating agent, such as acryloyl The liquid oxidizers that are most suitable for making chloride, acrylic anhydride, acrylic acid, and others which the high-energy propellants are mainly organic com may have substituents and which may react with OH pounds which contain NF2 substituents, as in tetrakis groups attached to the polyethers, which may be termed (NF2) butane and tetrakis (NF) tetrahydrofuran. The 30 NF-polyether alcohols. The terms acrylates, poly liquids are absorbed in the NF2-containing binders and acrylates and acrylating agent are intended to include behave in the manner of plasticizers while they impart the alpha-substituted methyl and homologous modifica a desired high-energy value to the propellant. tions. In the development of the NF-containing polymers and While a variety of steps may be used in arriving at curing of these polymers with high loading of liquid NF the final high-energy binder compositions, the present in containing oxidizers, a number of defects have been found vention is concerned with the curing of the viscous to arise, such as low tensile strength and low elongation liquid acrylate polymers that are to be loaded with ox at high strain rates, when curing is carried out with a idizers and fuels before the curing or casting. The initial conventional acrylate curing catalyst, such as dichloro 40 materials, insofar as the present invention is concerned, benzoyl peroxide. The physical defects of the cured are the NF-polyether acrylates such as are obtained by binders made with conventional curing catalysts are reacting the NF2-polyether alcohols with an acrylating phenomena which are difficult to understand, but may agent. A brief description will be given of the acrylated be partly attributed to inadequate polymerization at NF-polyether alcohols, how they are formed, and then ordinary temperature conditions. It is difficult to use high how they are cured to the desired binder compositions. curing temperatures, e.g. above 50° C., and avoid de PREPARATION OF NF-POLYETHER composition of the heat-sensitive components. ALCOHOLS It has now been found, in accordance with the present invention, that the high-energy NF-containing poly In a preferred preparation of an NF2-polyether alco acrylates can be cured more effectively with unexpected hol for alkylation, 1,4-pentadiene monoxide having the improvements in physical properties by using esters of 50 formula: peroxycarbonic acids as initiators at Suitable low curing O temperatures. / N Esters of peroxycarbonic acids are described in an CH2=CH-CH-CH-CH2 article by F. Strain et al. in the “Journal of American Chemical Society," vol. 72, 1254 (1950). The preferred is polymerized with an epoxide polymerization catalyst, esters are the dialkyl peroxydicarbonates represented by such as PF, using 0.01 to 10 wt. percent of the catalyst the formula: admixed with the epoxide monomer and carrying out the polymerization at 20° to 25 C. for a period of 0.5 to 72 RO COO COR 60 hours until a viscous liquid polymer having a molecular wherein R represents alkyl groups having 2 to 4 carbon weight in the range of about 500 to 5,000 is obtained. atoms, as in diethyl peroxydicarbonate and diisopropyl The OH functionlity of the polyether is controlled by peroxydicarbonate. The suitable peroxydicarbonates are addition of relatively small proportions of modifiers, such to be employed as the binder curing initiators in propor as preferably trimethylol propane. The resulting unsatu tions of about 0.1 to 4 wt. percent, based on the poly 65 rated polyether alcohol reacts with N2F smoothly using mer which is to be cured. an excess of NF-chloroform or other halogen-substituted It is important to note that the peroxycarbonates, in alkane solvent at 80 to 100° C. The resulting NFA adduct general, are unstable compounds which decompose and of the unsaturated polyether alcohol then contains NF2 may decompose explosively at normal temperatures, groups attached to carbon atoms which were linked to especially depending upon the kinds of other substances gether by double bonds. The adduct made from the polyn present. For example, esters of peroxydicarbonic acid erized 1,4-pentadiene monoxide may be termed poly(4,5- 3,692,599 3 4 bis(difluoramino) pentene-1 oxide) and has a recurring polyether acrylates using initiators such as dichlorobenzoyl unit formula represented as follows: peroxide and azoisobutyronitrile, a number of studies have shown that there are variations of tensile strength and -CE-C-O- elongation with temperature and rate of strain which made improvement of the physical characteristics desirable. The HNF need for the improvement in physical characteristics of (HNF, the cured binder has, in some instances, shown up only In this polyether, the recurring unit is present in a number after the curing of the binder is carried out in the presence n times, for example, 4 to 50. The number of OH groups of other components, such as the solid oxygen-oxidizers. attached to the polymer chain depends on the method of O It is with respect to the improved curing of the NF2-poly modifying the polyether as it is formed with a modifying ether acrylates in propellant formulations with liquid agent and, generally, it has an average of 1.5 to 2.5 or 3 NF-containing oxidizers, solid oxygen oxidizers, and pow OH groups per molecule, but this number may be higher. dered metal fuels that the peroxycarbonate initiators Other NF-polyether alcohols which have been made showed up particularly well, especially with the curing 15 of the formulations being carried out at temperatures in similarly by forming NF2 adducts of the polymerized un the range of 20 to 50° C., and preferably at about 25 saturated epoxides are polydivinylethylene oxide-NF ad to 45° C. Some of the improvements showed up without duct having the recurring unit composition the loading of the polymer by the other components. CH(NF2).O. As an example, diethyl peroxydicarbonate was made as poly(3-methylene oxetane)-NF, adduct having the re 20 follows: curring unit composition ICH6(NF2)2O), polybutadiene 2.2 g of NaOH is dissolved in 25 mi. of water with oxide-NFA adduct having the recurring unit composition stirring. The mixture is cooled to 10° C. and 3.4 ml. of ICHs (NF2)2O). In general, the NF-containing polyether 30% hydrogen peroxide added. This solution of NaO alcohols are indicated by the composition: is slowly added to 4.75 ml. of ethyl chloroformate at be 25 tween 6 to 10° C. The mass is kept at 10° C. for 30 (-CHy (NF ) O-I r minutes. The product is kept as solid or in solution in a wherein x is 4 to 6, y is 6 to 8, 2 is 2 to 4, and n is 4 to -25 C. freezer. Analysis shows 60% pure peroxide. 50. Experiments were made to determine whether the di ethyl peroxydicarbonate could be used in comparison to ACRYLATION OF NF-POLYETHER ALCOHOLS 30 other initiators for polymerizing polypentadiene mon To form the pre-cured acrylates, the NFpolyether oxide-NF4 adduct acrylate at room temperature and it alcohols are reacted with acrylating agents, preferably in an was found that the diethyl peroxydicarbonate executed excess of stoichiometric proportions, in the presence of a polymerization of the acrylate in 1 hour at room temper solvent such as acetonitrile and a catalyst in a dry system.
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