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United States Patent Office 2,610,164

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United States Patent Office 2,610,164 Patented Sept. 9, 1952 2,610,164 UNITED STATES PATENT OFFICE 2,610,164. COMPOSITIONS OF WINYL CHLORIDE RESINS AND AROMATIC ESTERS OF . suLFONATED ALKANES Earl W. Gluesenkamp, Centerville, and Joachim Dazzi, Dayton, Ohio, assignors to Monsanto Chemical Company, St. Louis, Mo., a corpora tion of Delaware NoDrawing. Application August 20, 1949, serial No. 111,562 Claims. (Cl. 260-30.8) This invention relates to vinyl chloride com Thus, the... useful. plasticizers2 for practicing this positions having unusual flexibility and high invention are the esters corresponding to the stability at elevated temperatures. More Specif following structural formula ically the invention relates to a novel group of plasticizers for vinyl chloride polymers which X. O , have unusual efficacy in developing desirable physical properties. X >-o-s-ch,-(CH)-ons6. The esters of sulfonated aliphatic hydrocar wherein X is a radical of the group consisting bons are known chemical compounds, some of of hydrogen, chlorine and methyl, and wherein which have been used as plasticizers. The esters, n is a whole number from eight to twelve. which are prepared from petroleum products The new esters may be prepared from 1-olefins are mixtures of very many different compounds. as derived from the Fischer-Tropsch reaction, They have wide variations in the length and or from the primary n-mercaptains. The 1-olefins configuration of the aliphatic chain and in the may be reacted with hydrogen sulfide or 6-mer place on the chain where the sulfonic acid group captoethanol. The mercaptain, its thial, or the is substituted. Many of the ester mixtures are alkyl mercaptoethanols are then oxidized, for too volatile for successful application as plasti example with nitric acid and thereby converted cizers, and others are incompatible and conse to the corresponding sulfonic acids. The sul quently of little value. Other ester mixtures fonic acids may be readily converted to the Sul will impart flexibility over a small temperature 20 fonyl halide. Which can be reacted. With phenol, range, but are of little utility at temperatures cresol, or a chlorine Substituted phenol. In ac below 0° C. cordance with these methods the esters will have The primary purpose of this invention is to all of their Sulfonic acid groups. Substituted on provide new effective compositions for plasti a terminal carbon atom of the hydrocarbon. cizing vinyl chloride polymers. A further pur 2 5 chain. pose of this invention is to provide vinyl chlo The new esters are valuable plasticizers for ride resins which are useful over wide ranges of polyvinyl chloride and copolymers of more than temperature. A still further purpose of the in 70 percent of vinyl chloride and up to 30 percent vention is to utilize abundantly available raw of other polymerizable monomers copolymerized materials of low cost and to prepare useful and 30 therewith, for example vinyl acetate and other inexpensive agents for modifying vinyl chloride vinyl esters of monocarboxylic acids, ethyl male resins. ate, ethyl fumarate and other alkyl esters of In copending application Serial No. 111,563 maleic and fumaric acids. filed August 20, 1949, by Earl W. Gluesenkamp The plasticizers are blended with the winyl and Joachim Dazzi, there are described and resin in the conventional manner, for example claimed esters of sulfonated hydrocarbons hav by mixing on a roll mill, a Banbury type mixer or ing at least 80 percent by weight of aromatic any other suitable mixing device. The plasti esters of sulfonated alkanes wherein the alkane cizers are used in proportions necessary to achieve has from 19 to 21 carbon atoms in its molecule. the desired plasticity. Although the quantity of such compositions are of unusual utility as 40 plasticizer Will depend upon the particular poly plasticizers for vinyl chloride resins. mer to be plasticized and upon its molecular It has now been found that the optimum length weight it is generally found that compositions of the aliphatic chain is materially different having from five to 50 percent of plasticizer will when the sulfonic acid substituent is in the in most cases be satisfactory for general utility. one position on the chain. When the Sulfonic 45 Such quantity of plasticizer will generally re acid group is substituted randomly at a Wide main as a permanent part of the vinyl resin and variety of positions along the chain the Optimum the modified vinyl resin So prepared will not carbon length is approximately twenty. How deteriorate or become embrittled by reason of ever, if the sulfonic acid group is Substituted in the loss of the plasticizer during use. a terminal position on a straight chain alkane 50 The value of the plasticizers are estimated by the optimum plasticizer properties are developed three tests (1) compatibility (2) volatility and with ten to fourteen carbon atoms in the aliphatic (3) Clash-Berg flex temperature. The com chain. The aromatic esters of alkane Sulfonic patibility is determined by visual inspection, acids having fewer than ten carbon atoms in clarity being a requisite in most applications for the hydrocarbon chain are too volatile for use vinyl chloride polymers. The Wolatility is esti as general purpose plasticizers. On the other mated by the test of heating at 105 C. for 24 hand, if the aliphatic hydrocarbon chain con hours and nea,Suring the percentage of the tains more than fourteen carbon atoms the plasticizers evaporated by loss of weight. The esters of mixtures thereof are frequently ifl Clash-Berg flex temperature is determined by compatible with the vinyl chloride polymers. 60 cooling the polymer Sample to about -50°C, 2,6i0,164 - 4 and observing the change in the modulus of polyvinyl chloride containing intimately dis rigidity as the sample warms up to room tem persed therein an ester of the following struc perature, the flex temperature being that at tural formula: which the modulus of rigidity is 135,000 pounds per Square inch. Of these tests the compatibility s X O is of primary importance while the others are K D-0--CH-CH-)-CH, only critical for certain applications. If the O polymer is to be Subjected to outside Weather conditions flex temperatures of -20 to -30° C. wherein X is a radical of the group consisting are desirable, otherwise 0° C. is satisfactory. If O of hydrogen, chlorine and methyl, and Wherein the polymer is to be subjected to elevated tem n is a whole number from eight to tWelve. peratures a volatility of five to ten percent is 3. A vinyl chloride resin, which comprises a advantageous, otherwise volatilities as high as copolymer of at least 70 percent by weight of 25 percent are often not objectionable. The vinyl chloride and up to 30 percent of an olefinic volatilities and flex temperature, of polymer 5 monomer copolymerizable therewith, said co plasticizer blends are difficult to predict and polymer having intimately dispersed therein a often havno apparent relationship to the physi compound having the structural formula: cal constants of the plasticizer. The new plasticizers are of general utility in X -- softening vinyl chloride polymers. They may be 20 R }-o-i-CH-CH-)-CH. used as the only plasticizing component in a O - compounded vinyl chloride polymer or they may be used in conjunction with other plasticizers. where X is a radical of the group consisting of Further details of the practice of this invention hydrogen, chlorine and methyl, and wherein n. are Set forth with respect to the following Spe 25 is a whole number from eight to twelve. cific examples. 4. A vinyl chloride resin, which comprises a Eacample 1 copolymer of at least 70 percent by weight of A phenyl ester of 1-dodecane Sulfonic acid vinyl chloride and up to 30 percent of a monomer was evaluated as a plasticizer by milling 40 parts of the group consisting of the vinyl esters of by weight of the ester with 60 parts of polyvinyl 30 carboxylic acid, the alkyl maleates and the alkyl chloride and one part of a standard commercially fumarates, having intimately dispersed therein available heat, stabilizer. The thoroughly milled a compound having the structural formula: sample was molded into appropriate test pieces X O and tested by means of the Clash-Berg flex tem . perature procedure and for volatility. The con & D-0- S-CH-(CH2)-CH3 positions were found to have a flex temperature O of -42.2° C. and a volatility of 4.0 percent. The phenyl esters of dodecane sulfonic acid wherein X is a radical of the group consisting of having the sulfonate group distributed at ran hydrogen, chlorine and methyl, and wherein 12 40 is a whole number from eight to twelve. dom throughout the dodecane chain Were pre 5. A vinyl chloride composition, which com pared by direct sulfochlorination of n-dodecane prises polyvinyl chloride having intimately dis and subsequent reaction. With phenol. Polyvinyl persed therein a phenyl ester of a primary nor chloride samples plasticized with this material mal alkane sulfonic acid wherein the alkane radi were found to have a volatility of 9.2 and a flex cal has from ten to fourteen carbon atoms, said temperature of -28 C. ester being from five to 50 percent of the weight Eacample 2 of the composition. For the purpose of demonstrating the critical 6. A vinyl chloride composition, which com nature of the number of carbon atoms in the prises polyvinyl chloride having intimately dis hydrocarbon chain, the cresyl ester of the sul persed therein a cresyl ester of a primary nor fonic acids of n-hexadecane having all of the mal alkane Sulfonic acid wherein the alkane radi sulfonate groups Substituted on terminal carbon cal has from ten to fourteen carbon atoms, said atoms, was prepared but was found to be incon ester being from five to 50 percent of the weight patible, at 40% concentrations.
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