Abstract:
Diesters of succinic, glutaric, adipic, and phthalic acid with hexyloxyethoxyethanol or butoxyethoxyethoxyethanol are disclosed. They are useful as plasticizers with extended temperature ranges in elastomers.

Description:
BACKGROUND OF THE INVENTION 
     The use of plasticizers to extend and soften rubber is an old and well-known technique. Many plasticizers have been used for improving the processing or lowering the cost of rubber compounds. Specialty rubbers, such as neoprene, nitriles, chlorinated and chlorosulfonated polyethylene, polyacrylates, polyurethanes, and polyepichlorohydrins, present a special problem when a suitable plasticizer is desired. A specialty rubber, which is normally more costly, is most often selected because of a desire for better high temperature performance, better solvent and/or oil resistance, and/or better ageing characteristics or physical properties. Incorporation of polar functions into the molecular structure of the rubber is responsible for the enhancement of the desired characteristics. While the presence of these polar functions tends to improve the hydrocarbon solvent resistance and/or the high temperature performance of a particular rubber, it also introduces undesirable effects on the low temperature properties by raising the glass transition temperature, and rendering the polymer brittle. To counteract this and improve the low temperature performance a plasticizer may be compounded with the rubber. As the plasticizer is an extractable and relatively volatile component of the mixture, its addition reduces the solvent resistance and high temperature performance of the rubber, but to obtain reasonable low temperature performance it has been necessary to compromise high temperature performance and solvent resistance. 
     Because of a growing need for high performance materials in mechanical applications evidenced by higher engine operating temperature for automobiles and machinery as well as use of fuels with increased solvent power, and the extension of areas of use into both the Arctic and Tropics, there has been a continual search for plasticizers which will broaden the working range of specialty rubbers. 
     Some of the parameters which have been suggested for use in matching a plasticizer and a rubber include, the solubility parameter, the hydrogen bonding effect, free volume of solvents, and the glass transition temperature. A number of statistical and thermodynamic theories have been proposed to account for the effects of a plasticizer in a rubber formulation. While these are useful in selecting particular categories of compounds as likely candidates, no compound can be predicted as particularly useful until it has been treated in actual formulations. 
     Among the variables of potential plasticizers it is known that polarity, aromaticity, and molecular weight are of importance. This is particularly true of polarity in the case of the specialty rubbers, which contain polar functions and require that a plasticizer have polarity so as to match the solubility parameter and hydrogen bonding effects. Among the more common polar groups used in plasticizers are halogens, nitriles, ethers, esters, and urethanes. Aromaticity is a factor as high aromaticity favors compatibility, in general lowers volatility but normally gives poorer low temperature properties. Molecular weight, of course, affects volatility but high molecular weight compounds in general show lowered compatibility and tend sometimes to bleed out of a particular system at elevated temperatures. 
     Although many varied plasticizers have been and are used in formulations with the specialty rubbers, desirable low temperature properties, resistance to extraction by solvents, and low volatility are not possessed, to the maximum desired extent, by any. 
     Di-(butoxyethoxyethanol)adipate is known as a plasticizer, and a polyether plasticizer derived from butoxyethoxyethoxyethanol and thiodiglycol is disclosed in U.S. Pat. No. 3,163,620. The present compounds are polyether esters of selected dibasic acis and they provide significantly better use properties. 
     SUMMARY OF THE INVENTION 
     The invention provides a composition of matter having the formula ##STR1## wherein R is --(CH 2 ) 3  --, --(CH 2 ) 4  --, ##STR2## a mixture of --(CH 2 ) 3  -- and --(CH 2 ) 4  --, or a mixture of --(CH 2 ) 2  --, (CH 2 ) 3  --, and --(CH 2 ) 4  --; and n and m are 3, or n is 2 and m is 5. 
     The tangible embodiments of the principal composition aspect possess the inherent physical characteristics of being liquids, substantially volatile only at elevated temperatures, and reduced pressure, and being substantially insoluble in water. 
     The tangible embodiments of the principal composition aspect of the invention posses the inherent applied use characteristics of being plasticizers for elastomeric goods over an extended temperature range, as established by examination of actual elastomeric formulations by standard tests. 
     A preferred aspect of this composition aspect of the invention resides in the concept of a composition of matter of Formula I wherein R is --(CH 2 ) 3  --. A particularly preferred aspect of this preferred aspect of the invention is the compound di-(butoxyethoxyethoxyethanol)-glutarate. Another preferred aspect of this composition aspect of the invention resides in the concept of a composition of matter of Formula I wherein R is --(CH 2 ) 4  --. Another preferred aspect of this composition aspect of the invention resides in the concept of a composition of matter of Formula I wherein R is ##STR3## Another preferred aspect of this composition aspect of the invention resides in the concept of a composition of matter of Formula I wherein R is a mixture of --(CH 2 ) 3  --, and --(CH 2   4  --; or --(CH 2 ) 2  --, --(CH 2 ) 3  -- and --(CH 2 ) 4  --. 
     The invention further provides the concept of an elastomeric composition having solvent resistance, high temperature stability and extended low temperature properties which comprises: 
     a. an effective amount of a composition of matter of Formula I; and 
     b. a specialty rubber. 
     The tangible embodiments of the second composition aspect of the invention possess the inherent applied use characteristic of being elastomers suitable for use where exposed to extreme ranges of high and low temperature conditions such as, in hose, gaskets and other elastomeric articles for &#34;under the hood&#34; use in automobiles where the temperatures may range from about -30° F to about 300° F or more. 
     The invention further provides in a process aspect, the concept of an improved process for the preparation of an elastomeric composition, containing a plasticizer, having solvent resistance, high temperature stability and extended low temperature properties which comprises: compounding a specialty rubber with a composition of matter of Formula I as the plasticizer. 
     DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     The compositions of Formula I may be prepared by standard techniques well known to those in the art. Butoxyethoxyethoxyethanol, or hexyloxyethoxyethanol are reacted with the desired dibasic acid or with a suitable derivative such as an acid anhydride, acid halide, or an ester. The reaction is normally run at an elevated temperature either neat or in an inert solvent optionally in the presence of a catalyst. The product may be recovered by conventional methods. Typically, dimethyl glutarate and butoxyethoxyethoxyethanol are heated at reflux in the presence of a catalytic amount of dibutyl tin oxide for a short period of time and then the methanol and water formed during the reaction are gradually removed by distillation, conveniently while gradually reducing the pressure in the reaction vessel. Treatment with calcium oxide, decolorizing charcoal, distillation of excess starting butoxyethoxyethoxyethanol under vacuum and clarification by filtration is a convenient method of obtaining di-(butoxyethoxyethoxyethanol)glutarate of purity sufficient for use. 
     One skilled in the art of organic chemistry could of course, if desired, substitute the other alternative starting materials for the dimethyl glutarate and butoxyethoxyethoxyethanol illustrated and obtain the alternative embodiments of the compositions of matter of Formula I contemplated as part of the invention. It will similarly be obvious that instead of a starting material based on a single acid, that either mixed acids or a mixture of esters derived from mixed acids may be substituted in the reaction and that the product will then be a mixture of esters derived from a single alkoxy alkanol and the mixed acid starting material. 
     The starting materials for the practice of the invention are all commercially available. Hexyloxyethoxyethanol and butoxyethoxyethoxyethanol are marketed by Union Carbide Corp. under the tradenames Hexyl Carbitol and Butoxytriglycol respectively. Adipic, glutaric, and phthalic acids, and various alkanoic esters and anhydrides thereof are all staples of commerce. Mixture of dimethyl succinate, dimethyl glutarate and dimethyl adipate are marketed by the DuPont Co. 
     In using the compositions of Formula I they made be used in compounding elastomer formulations in conventional ways. If desired other conventional additives may be included in the formulations. The compounding may be with any specialty rubber which is desired for a particular application. 
     As used herein and in the appended claims the term specialty rubber means one of the elastomers normally selected by those skilled in the art when ability to resist high and low temperature while being substantially oil and solvent resistant are desired. Illustrative of these but without limitation thereto are such rubbers as, for example, neoprene, nitrile, Hypalon, polyacrylates, polyurethanes, polyepichlorohydrin, and polysulfides. 
    
    
     The following examples further illustrate the best mode contemplated by the inventors for the practice of their invention. 
     EXAMPLE 1 
     Di-(hexyloxyethoxyethanol)adipate 
     A mixture of adipic acid (526.1 g; 3.60 moles) and hexyloxyethoxyethanol (1712.5 g; 9.00 moles) was heated in a 5 liter three necked flask, equipped with a mechanical stirrer, a thermometer, an inlet for dry nitrogen gas, and a 12&#34; Vigreux column with split-drop head. After 1.25 hours, the pot temperature was 167° C, and the mixture was boiling. Reaction was continued under total reflux for 32 minutes, the temperature falling to 146° C, after which distillate was collected for 4.7 hours, while the temperature rose to 263° C. The mixture was cooled and allowed to stand overnight, after which it was again heated for 3.1 hours. The final temperature was 272° C, and the total volume of distillate was 136 ml., including 128 ml. of an aqueous layer. The residue was stripped by heating to a final pot temperature of 212° C at 0.4 mm. pressure. The yield of the title product n D   25  1.4499, was 1645.3 g, (93.1%). 
     Analysis: 
     Acid No. 7.3 
     Hydroxyl No. (Corr.) 10 
     Water (%) 0.14 
     EXAMPLE 2 
     Di-(butyloxyethoxyethoxyethanol)-Glutarate 
     In an apparatus similar to that used for Example 1, were placed 640.7 g, (4.00 moles) of dimethyl glutarate, 2063 g, (10.00 moles) of butoxyethoxyethoxyethanol, and 2.84 g of dibutyltin oxide (0.05 wt. % tin metal, based on total reactant). The mixture was heated over an hour to 144° C, at which temperature it was boiling, then held under total reflux for 15 minutes, the temperature falling to 136° C. Heating under atmospheric pressure was continued for 2.5 hours; the temperature rose to 229° C, and 264 ml. of distillate (mostly methanol) was collected. Heating was continued under a partial vacuum for an additional 1.5 hours; the temperature rose to 249° C, while the pressure was reduced gradually to 189 mm. Distillate collected during this interval amounted to 60 ml. The mixture was cooled, calcium oxide (3.6 g) and activated carbon (Darco G-60; 40.7 g) were added, and the residue was freed of BTG by stripping in two stages, to a final pot temperature of 233° C at 0.9 mm. pressure. The mixture was cooled, a filter aid (Celite 545; 22 g) was added and it was filtered. The yield of title product n D   25  1.4506, was 1817.5 g (89.3%). The purity of this product by gas chromatography was 88.5%. 
     Analysis: 
     Acid No. 0.15 
     Hydroxyl No. (Corr) 3.8 
     Water (%) 0.29 
     EXAMPLE 3 
     Di-(hexyloxyethoxyethanol)-Phthalate 
     In a 3 liter three necked flask, equipped with a nitrogen inlet, a thermometer, a stirrer, and a Dean-Stark trap, connected to a reflux condenser, were placed 296.2 g (2.00 moles) of phthalic anhydride, 837.1 g (4.40 moles) of hexyloxyethoxyethanol, 8.4 g (0.044 moles) of toluenesulfonic acid monohydrate, and 260 ml. of toluene. This mixture was heated under reflux (pot temperature 145°-150° C) for 21.6 hours. About 38 ml. of water was collected in the trap, and the acid number of the residue was 3.7. To the cooled mixture was added 16.7 g of anhydrous Na 2  CO 3  ; it was then heated at reflux for about 17 minutes, cooled to 60° C, and diluted with 350 ml. of water. After the aqueous phase had been removed, the organic solution was washed with five 500 ml. portions of deionized water. (Ethanol was used when necessary to aid in breaking an emulsion). Toluene was removed by heating to 152°  C at 30 mm. pressure, and stripping was completed by heating to 218° C at 0.35 mm. The yield of title product was 945.6 g (92.6%). 
     Analysis: 
     Acid No. 0.07 
     Hydroxyl No. (Corr.) 2.9 
     Water (%) 0.09 
     If desired, this product may be stabilized by the addition of an antioxidant. 
     EXAMPLE 4 
     Di-(butoxyethoxyethoxyethanol)-Phthalate 
     In a 2 liter flask, equipped as described in Example 1, were placed 296.2 g (2.00 moles) of phthalic anhydride, 907.5 g (4.40 moles) of butoxyethoxyethoxyethanol and 1.05 g of stannous oxalate (0.05 wt. % Sn, based on total reactants). The mixture was heated over 43 minutes to the boiling point (222° C), heated under reflux at 222°-214° C for 5 minutes, heated under atmospheric pressure at 213°-230° C for 3.1 hours with removal of distillate, and distilled at pot temperature 206°-230° C for 1.6 hours while the pressure was gradually reduced to about 145 mm. At this point, 39.5 ml. of distillate had been removed, and the acid number was 4.2. Heating was continued for 5 hours at 212°-227° C and 130-131 mm. pressure; 20 ml. of distillate was collected, and the acid number fell to 0.30.  The crude product was stripped to 199° C at 3.2 mm. pressure and cooled; after 21.7 g of Celite 545 had been added, it was filtered. The yield of title product was 1031.1 g (95.0%). 
     Analysis: 
     Acid No. 0.33 
     Hydroxyl No. (Corr.) 9.3 
     Water (%) 0.03 
     If desired, this product may be stabilized by the addition of an antioxidant. 
     EXAMPLE 5 
     Di-(hexyloxyethoxyethanol)-Adipate 
     In an apparatus similar to that used for Example 1, were placed 1903 g (10.00 moles) of hexyloxyethoxyethanol, 585 g (4.00 moles) of adipic acid, and 0.37 g of concentrated sulfuric acid. The mixture was heated over 1.1 hours to 141° C, at which point it was boiling, and then was held under reflux for 0.6 hours, the temperature falling to 128° C. Heating with removal of distillate (water) was continued for 5.9 hours to a pot temperature of 249° C; at this time the acid number was 9.2. Further heating for 5.3 hours at 222°-270° C reduced the acid number to 4.9. After 2.0 g of Ca(OH) 2  had been added, the mixture was stripped by heating to a pot temperature of 292° C at 1.2 mm. pressure. 
     The residue was cooled and filtered in the presence of a filter aid (Celite 535; 40 g). Analytical data refer to a sample decolorized by treatment with activated carbon, (Darco G-60). They yield of title product was 1724.3 g (87.8%), n D   24  1.4449. 
     Analysis 
     Acid No.: 3.1 
     Hydroxyl No. (Corr.) 6.0 
     Water (%) 0.08 
     EXAMPLE 6 
     Mixed Dibutoxyethoxyethoxyethanol Esters of Succinic, Adipic, and Glutaric Acids 
     Butoxyethoxyethoxyethanol (1897 g, 9.20 moles), a mixture of dimethyl succinate (24 wt. %), dimethyl glutarate (49 wt. %) and dimethyl adipate (27 wt. %) (643 g, 4.02 moles) and conc. sulfuric acid (0.2 ml) were heated, in an apparatus similar to that described for Example 1, over a period of 1.2 hours to a temperature of 167° C and held under reflux for 0.55 hours. During this period the pot temperature fell to 145° C. Distillate was then removed over a period of 5.75 hours, the temperature rising to 245° C. After cooling and adding Ca(OH) 2  (2.0 g), stripping was effected by heating to 255° C at 2.1 mm pressure. The residue was cooled, decolorized by heating for 2 hours at 90° in the presence of 40 g of Celite 535, 22 g of Super Cel and 20 g of Darco G-60 and filtering. 
      Analysis 
     Acid No.: 0.13 
     Hydroxyl No. (Corr.) 1.3 
     Water (%) 0.14 
     EXAMPLE 7 
     Di-(Hexyloxyethoxyethanol)-Glutarate 
     Following a procedure analogous to that described in Example 6 there is obtained from hexyloxyethoxyethanol, and dimethyl glutarate in the presence of a catalytic amount of sulfuric acid an 85.5% yield of the title product. 
     Analysis 
     Acid No.: 0.07 
     Hydroxyl No. (Corr.) 3.8 
     Water (%) 0.19 
     EXAMPLE 8 
     Di-(Butoxyethoxyethoxyethanol)-Glutarate 
     Following a procedure analogous to that described in Example 6 there is obtained from butoxyethoxyethoxyethanol, and dimethyl glutarate, in the presence of a catalytic amount of sulfuric acid, the title product. 
     Analysis 
     Acid No.: 0.37 
     Hydroxyl No. (Corr.) 3.5 
     Water (%) 0.10 
     EXAMPLE 9 
     Di-(Hexyloxyethoxyethanol)-Glutarate 
     Following a procedure analogous to that described in Example 2, there is obtained from hexyloxyethoxyethanol and dimethyl glutarate, in the presence of a catalytic amount of dibutyl tin oxide a 77% yield of the title product. 
     Analysis 
     Acid No.: 0.38 
     Hydroxyl No. (Corr.) 0.4 
     Water (%) 0.19 
     EXAMPLE 10 
     Mixed Dihexyloxyethoxyethanol Ester of Succinic, Glutaric and Adipic Acids 
     Following a procedure analogous to that described in Example 2, there is obtained from hexyloxyethoxyethanol, and a mixture of the dimethyl esters of succinic acid (0-3 wt. %), glutaric acid (62-68 wt. %), and adipic acid (31-37 wt. %), in the presence of a catalytic amount of dibutyl tin oxide, 89.5% of the title product. 
     Analysis 
     Acid No.: 0.11 
     Hydroxyl No. (Corr.) 2.4 
     Water (%) 0.12 
     EXAMPLE 11 
     Mixed Di-butoxyethoxyethoxyethanol Esters of Dialkanoic Acids 
     Following a procedure analogous to that described in Example 2, there is obtained from butoxyethoxyethoxyethanol, and the dimethyl esters of succinic acid (0-3 wt. %), glutaric acid (62-68 wt. %), and adipic acid (31-37 wt. %), in the presence of a catalytic amount of dibutyl tin oxide, there is obtained 92% of the title product. 
     Analysis 
     Acid No.: 0.35 
     Hydroxyl No. (Corr.) 6.5 
     Water (%) 0.23 
     EXAMPLE 12 
     Di-(Butoxyethoxyethoxyethanol)-Phthalate 
     Following a procedure analogous to that described for Example 3, there is obtained from butoxyethoxyethoxyethanol, and phthalic anhydride, in the presence of a catalytic amount of para toluene sulfonic acid monohydrate, on 86% yield of the title product. 
     Analysis 
     Acid No.: 0.05 
     Hydroxyl No. (Corr.) 2.7 
     Water (%) 0.09 
     EXAMPLE 13 
     Elastomer formulations were compounded in the formulations shown. Test properties found after cure and after ageing are shown in the tables following: 
     
         ______________________________________Formulations                Parts______________________________________1.  Neoprene WRT (duPont)       100    Semi-Reinforcing Furnace (SRF)#3,    Carbon Black                60    Zinc Oxide                  5    Extra Light Calcined Magnesia                           4    Stearic Acid                0.5    2-Mercaptoimidazoline       0.5    Plasticizer                 302.  Hycar 1051*                 100    SRF#3 Carbon Black          60    Zinc Oxide                  5    Sulfur                      1.75    Benzothiozyldisulfide       1.5    Symmetric Diphenylguanidine 0.25    Plasticizer                 303.  Polyacrylate Rubber (ethyl acrylate,    allylglycidyl ether; 95-5-0.1)                           100    Fast Extrusion Furnace Carbon Black                           60    Zinc Dimethyldithiocarbamate                           2    Phenyl- -naphthylamine      1.5    Stearic Acid                1    Plasticizer                 304.  Hydrin 200 (epichlorohydrin copolymer with    ethylene oxide) (B. F. Goodrich)                           100    Fast Extrusion Furnace Carbon Black                           30    Red Lead                    5    2-Mercaptoimidazoline       1.5    TE-75 (Internal Lubricant) (Tech. Proc.    Inc., Patterson, N.J.)      1.5    Nickeldithiodibutylcarbamate                           1    Plasticizer                 305.  Toluene diisocyanate-polylactone polyol                           100    rubber based on caprolactone, M.W.    polyactone polyol=1250) or Toluene di-    isocyanate-ethylene propylene polyadipate    rubber (M.W. polyadipate=2700)    Super Abrasion Furnance Carbon Black                           60    Benzothiazyldisulfide       4    Mercaptobenzoylthiazole     2    Sulfur                      1.5    Partial complex of ZnCl.sub.2 with    benzothiazyldisulfide (duPont)                           1    TE-75                       1    Cadmium Stearate            0.5    Plasticizer                 30______________________________________ *HYCAR 1051 (B. F. Goodrich) is a high-nitrile rubber (nominal acrylonitrile content about 41%). 
    
     
                                           TABLE I__________________________________________________________________________Evaluation of Plasticizers Compounded -    30 phr in Neoprene WRT    Control (No Plasticizer)                        Butoxyethoxyethanol Formal    70 hrs. H. Aging    70 hrs. H. Aging    Orig.               Orig.Physical Prop.    Prop.         212° F              225° F                   250° F                        Prop. 212° F                                   225° F                                        250° F__________________________________________________________________________Tensile, psi    3000 2900 2830 1460 1660  2050 2160 1970Elong. % 200  190  200  90   290   300  280  120100% Mod.    1150 1400 1350 --   350   420  500  1570200% Mod.    2870 --   --   --   d 900 1070 1300 --Shore A  82   82   82   88   60    65   70   88Wt. % Loss.sup.(1)    --   0    0    0.13 --    6    9    14% Plast. Loss.sup.(2)    --   --   --   --   --    39%  61%  95%G.sub.10,000    -39° F         -28° F              -28° F                   -23° F                         -71° F                              -63° F                                   -55° F                                        -25° FCompatibility    --                  OK    Di-(Hexyloxyethoxyethanol)-Adipate                        Di:(Butoxyethoxyethoxyethanol)-Glutarate__________________________________________________________________________Tensile, psi    2100 1990 1750 1290 2060  1950 1830 1370Elong., %    280  270  250  90   280   250  250  90100% Mod.    460  450  450  --   420   450  470  --200% Mod.    1360 1350 1260 --   1250  1450 1375 --Shore A  63   65   66   83   60    63   68   87Wt. % Loss    --   1    1    6    --    2    2    7% Plast. Loss    --   8%   8%   28%  --    11%  15%  4 % ?G.sub.10,000    -63° F         -61° F              -59° F                   -34° F                        -59° F                              -58° F                                   -49° F                                        --%?Compatibility    OK                  OK__________________________________________________________________________ .sup.(1) Based on total wt. of cured compound. .sup.(2) Based on plasticizer present in formulation. 
    
     
                                           TABLE II__________________________________________________________________________Evaluation of Plasticizers Compounded at 30 phr in Hycar 1051                                          Di-(Hexyloxyethoxyethanol)-                                          1          Control (No Plasticizer)                          Butoxyethoxyethanol Formal                                          Adipate              70 hrs. H. Aging                              70 hrs. H. Aging                                          70 hrs. H. AgingPhysical       Orig.              212 225 250 Orig.                              212 225 250 Orig.                                              212 225 250Prop.          Prop.              ° F                  ° F                      ° F                          Prop.                              ° F                                  ° F                                      ° F                                          Prop.                                              ° F                                                  ° F                                                      °__________________________________________________________________________                                                      FTensile, psi   2810              3000                  2710                      2570                          2160                              2375                                  2610                                      2700                                          2180                                              2170                                                  2060                                                      2120Elong., %      270 220 190 170 470 340 300 230 500 330 260 225100% Mod.      850 1125                  1250                      1530                          350 510 780 1070                                          270 450 570 770200% Mod.      2250              2750                  --  --  850 1350                                  1750                                      2400                                          645 1200                                                  1550                                                      2000300% Mod.      --  --  --  --  1410                              2150                                  2610                                      --  1200                                              1950                                                  --  --Shore A        79  81  82  83  59  68  80  83  58  63  66  72Wt. % Loss.sup.(1)          --  .54 .23 .88 --  10  13.5                                      15  --  1.2 1.2 NA% Plast. Loss.sup.(2)          --  --  --  --  --  61% 74% 95% --  8%  8%  9%G.sub.10,000   +9° F              +13° F                  +12° F                      +15° F                          -44° F                              -6° F                                  +3° F                                      +14° F                                          -46° F                                              -41° F                                                  -33° FCompatibility  --              OK              OK                                          Di-(Butoxyethoxyethoxyethan                                          ol)-Di-(Butoxxyethoxyethoxyetthanol)-Glutarate     Mixed Esters (From Example                                          6)__________________________________________________________________________Tensile, psi   2075              1960                  2190                      2000                1975                                              2140                                                  1990                                                      1800Elong., %      490 310 300 200                 470 340 270 200100% Mod.      290 450 540 825                 275 390 510 740200% Mod.      700 1170                  1450                      1970                680 1060                                                  1375                                                      1800300% Mod.      1260              1880                  --  --                  1250                                              1850                                                  --  --Shore A        58  63  65  69                  58  63  67  70Wt. % Loss     --  1.3 1.5 NA                  --  1.5 1.5 NA% Plast. Loss  --  9%  10% 15%                 --  10% 10% 15%G.sub.10,000   -49° F              -45° F                  -45° F                      -37° F       -49° F                                              -44° F                                                  -44°                                                      -35° FCompatibility  OK                              OK__________________________________________________________________________ .sup.(1) Based on total wt. of cured compound. .sup.(2) Based on plasticizer present in cured formulation. 
    
     
                                           TABLE III__________________________________________________________________________Evaluation of Plasticizers Compounded at 30 phr in Hydrin 200        Control (No Plasticizer)                            Butoxyethoxyethanol Formal              70 Hrs. H. Aging   70 Hrs. H. AgingPhysical     Orig.             212  225  250  Orig.                                 212  225 250Prop.        Prop.             ° F                  ° F                       ° F                            Prop.                                 ° F                                      ° F                                          ° F__________________________________________________________________________Tensile, psi 1895 2125 2350 2050 1200 1200 1475                                          1860Elong., %    380  330  350  300  505  380  420 440100% Mod.    475  500  500  480  210  220  250 310200% Mod.    1045 1230 1210 1200 440  510  560 625300% Mod.    1625 1975 2010 --   720  925  1000                                          1125Shore A      66   68   67   67   47   52   57  62Wt. % Loss.sup.(1)        --   NA   0.27 0.35 --   8    12.5                                          17.5% Plast. Loss.sup.(2)        --   --   --   --   --   44%  69% 97%G.sub.10,000 Not available       Not availableCompatibility        --                  OK        Di-(Hexyloxyethoxyethanol)-                            Di(Butoxyethoxyethoxyethanol)-        Adipate             Glutarate__________________________________________________________________________Tensile, psi 1040 1373 1270 1295 1060 1425 1370 1310Elong., %    410  510  460  500  440  480  470  460100% Mod.    175  200  195  170  195  225  200  195200% Mod.    390  425  420  390  445  500  470  440300% Mod.    652  725  745  670  725  840  825  780Shore A      48   50   50   49   46   49   50   51Wt. % Loss   --   2    2.3  2.6  --   2.3  3.4  4% Plast. Loss        --   10%  12%  13%  --   13%  18%  21%G.sub.10,000      Not available       Not availableCompatibility        OK                  OK__________________________________________________________________________        Di-(Butoxyethoxyethoxyethanol) mixed        ester (from Example 6)             70 Hrs. H. AgingPhysical     Orig.             212  225  250Prop.        Prop.               F  ° F                       ° F__________________________________________________________________________Tensile, psi 1175 1245 1240 1100Elong., %    430  420  405  390100% Mod.    180  205  200  200200% Mod.    425  500  470  450300% Mod.    725  875  860  810Shore A      48   49   49   51Wt. % Loss   --   2.6  3.6  4% Plast. Loss        --   15%  19%  21%G.sub.10,000 Not availableCompatibility        OK__________________________________________________________________________ .sup.(1) Based on total wt. of cured compound. .sup.(2) Based on plasticizer present in cured formulation. 
    
     
                                           TABLE IV__________________________________________________________________________Heat Aging Evaluation, 70 hrs/300° F in Hydrin 200                                             Di-(Butoxyethoxyethoxy-                  Di-(Hexyloxyethoxyethanol                                Di-(Butoxyethoxyethoxy-                                             ethanol)-mixed ester                                             from     Control            Adipate                  ethanol)-Glutarate                                Example 6     Orig. Prop.            Oven Aged                  Orig. Prop.                         Oven Aged                                Orig. Prop.                                       Oven Aged                                             Orig.                                                    Oven__________________________________________________________________________                                                    AgedTensile, psi     1895   1610  1040   786    1060   890   1175   830Elong., % 380    270   410    400    440    405   430    390100% Mod. 475    450   175    145    195    150   180    141200% Mod. 1045   1100  390    300    445    328   425    315300% Mod. 1625   --    625    545    725    600   725    580Shore A   66     63    48     45     46     43    48     45Wt. % Loss       2.5   --     7      --     7     --     6% Plast. Loss     --     --    --     27.5%  --     27%   --     22%G.sub.10,000                  Not available__________________________________________________________________________ 
    
     
                                           TABLE V__________________________________________________________________________Evaluation of Plasticizers Compounded at 30 phr in Polyacrylate RubberControl                    Di-(Butoxyethoxyethanol)                                        Di-(Hexyloxyethoxyethanol)-(No Plasticizer)          Adipate           AdipateF-671-49WP    70 Hrs. H. Aging 70 Hrs. H. Aging  70 Hrs. H. AgingPhysical  Orig.         212 225 250 Orig.                          212 225 250  Orig.                                            212 225 250Prop.     Prop.         ° F             ° F                 ° F                     Prop.                          ° F                              ° F                                  ° F                                       Prop.                                            ° F                                                ° F                                                    °__________________________________________________________________________                                                    FTensile, psi     1850         1700             1690                 1750                     1150 1150                              1190                                  1170 1150 1150                                                1090                                                    1125Elong., % 240 240 250 250 380  360 380 360  430  410 440 420100% Mod. 720 575 520 530 250  230 220 250  230  220 220 200200% Mod. 1700         1475             1475                 1525                     645  650 650 670  600  580 590 575300% Mod. --  --  --  --  975  1000                              1010                                  1040 925  930 910 950Shore A   73  73  72  72  53   53  52  55   52   51  52  52Tempering,Wt. % Loss     .38%         --  --  --  3.5% --  --  --   2%   --  --  --% Plast. Loss     --  --  --  --  20%  --  --  --   9%   --  --  --Wt. % Loss     --              --   4   4.4 5    --   2.7 N.A.                                                    2.3% Plast. Loss     --              --   2.4%                              26% 28.5%                                       --   15% N.A.                                                    12% G.sub.10,000     Not available   Not available     Not available     Di-(Butoxyethoxyethoxy-                     Di-(Butoxyethoxyethoxyethanol)-     ethanol)-Glutarate                     mixed ester from Example 6__________________________________________________________________________Tensile, psi     1150         1150             1150                 1150                     1150 1200                              1200                                  1150Elong., % 390 390 390 390 370  390 420 370100% Mod. 210 200 190 200 210  225 180 210200% Mod. 600 600 560 590 575  645 560 600300% Mod. 960 950 940 970 925  1010                              950 1000Shore A   53  53  48  52  50   49  50  50Tempering,Wt. % Loss     2%  --  --  --  2%   --  --  --% Plast. Loss     10% --  --  --  10.5%                          --  --  --Wt. % Loss     --  2.5 3   2.6 --   2.5 3   3% Plast. Loss     --  14% 15  14% --   13% 15  16% G.sub.10,000     Not available   Not available__________________________________________________________________________ 
    
     
                                           TABLE VI__________________________________________________________________________Evaluation of Plasticizers Compounded at 30 phr in Toluenediisocyanate-ethylenepropylene Polyadipate Rubber     Control          Di-(Butoxyethoxyethanol)-                                       Di(Hexyloxyethoxyethanol)-     (No Plasticizer) Adipate          AdipateF-671-38-WP    70 hrs. H. Aging 70 hrs. H. Aging 70 hrs. H. AgingPhysical  Orig.          212 225 250 Orig.                           212 225 250 Orig.                                            212 225 250Prop.     Prop.          ° F              ° F                  ° F                      Prop.                           ° F                               ° F                                   ° F                                       Prop.                                            ° F                                                ° F                                                    °__________________________________________________________________________                                                    FTensile, psi     4175 4200              4690                  4000                      2360 2500                               2190                                   1800                                       2850 3060                                                2850                                                    1930Elong., % 300  190 190 170 360  240 190 170 360  280 240 190100% Mod. 1650 2250              2730                  2650                      510  875 1000                                   980 650  900200% Mod. 3500 --  --  --  1200 2100                               --  --  1575 2220                                                --  --300% Mod. 4160 --  --  --  2000 --  --  --  2450 --  --  --Shore A   93   95  97  96  73   85  84  85  75   84  85  84Wt. % Loss(1)     --   1.5 2   2   --   3   3.6 5   --   1.5 2   2.4% Plast. Loss(2)     --   --  --  --  --   18% 20% 27% --   9%  13% 14% G.sub.10,000     -4° F              Not available                      -49° F                               Not available                                       -48° F                                            Not availableCampatibility     --   --  --  --  OK   --  --  --  OK   --  --  --__________________________________________________________________________     Di-(Butoxyethoxyethox-                     Di-(Butoxyethoxyethoxyethanol)     yethanol Glutarate                     mixed ester from Example 6__________________________________________________________________________Tensile, psi     2600 2595              2350                  1700                      2770 2710                               2590                                   1910Elong., % 340  230 190 160 350  250 205 180100% Mod. 600  910 1000                  950 650  900 1050                                   1000200% Mod. 1500 2250              --  --  1510 2210                               2480                                   --300% Mod. 2360 --  --  --  2410 --  --  --Shore A   73   84  84  84  77   84  84  84Wt. % Loss     --   1.8 2.3 3   --   1.5 2   3% Plast. Loss     --   10% 13% 16% --   9%  13% 15% G.sub.10,000     -48° F          Not available                      -47° F                           Not availableCompatibility     OK               OK__________________________________________________________________________ (1)Based on total wt. of cured compound. (2)Based on plasticizer present in cured formulation. 
    
     EXAMPLE 14 
     Elastomers are compounded according to the following formulations. The properties after cure and after heat ageing are shown in the following tables: 
     
         __________________________________________________________________________Formulations:1. Neoprene WRT  a.    Standard Recipe            Parts    Neoprene WRT               100    SFR #3 Carbon Black        60    Zinc Oxide                 5    Extra Light Calcined Magnesia                          4    Stearic Acid               0.5    2-Mercaptoimidazoline      0.5    Plasticizer                30  b.    High Temperature Formulation    Neoprene WRT               100    SRF #3 Carbon Black        58    Zinc Oxide                 10    Extra Light Calcined Magnesia                          4    Stearic Acid               0.5    2-Mercaptoimidazoline      0.75    p(p-toluenesulfonamido)-diphenylamine                          1    Octylated Diphenylamine    4    Plasticizer                302. Hycar 1051Hycar 1051                     100SRF #3 Carbon Black            f 60Zinc Oxide                     5Sulfur                         1.75Benzothiazyldisulfide          1.5Sym-Diphenylguanidine          0.25Plasticizer                    303. Toluene diisocyanate-polylactone polyl rubber (M. W.                          100  polyactone polyol = 1250) or  Toluene diisocyanated-ethylenepropylene adipate rubber                          100  (M. W. polyadipated-2700)Super Abrasion Furnace         60Carbon BlackBenzothiazyldisulfide          4Mercaptobenzoylthiazole        2Sulfur                         1.5Partial complex of ZnCl.sub.2 with                          1benzothiazyldisulfide (duPont)TE-75                          1Cadmium Stearate               0.5Plasticizer                    30__________________________________________________________________________ 
    
     
                                           TABLE VII__________________________________________________________________________Evaluation of Plasticizers in Neoprene WRT-High Temperature Recipe    Butoxyethoxyethanol                Di-(Butoxyethoxyethanol)-                                Di-(Hexyloxyethoxy-    Formal      Glutarate       ethanol)-Glutarate    70 hrs. H. Aging                70 hrs. H. Aging                                70 hrs. H. AgingPhysical Orig. 250   Orig.   250     Orig. 250Properties    Prop. ° F                Prop.   ° F                                Prop. ° F__________________________________________________________________________Tensile, psi    1590  1890  1900    1950    2025  2030Elong., %    240   160   260     240     330   290100% Mod.    500   1320  500     690     325   510200% Mod.    1300  --    1380    1610    875   1230Shore A  66    92    66      76      58    59Wt. % Loss    ×          14.4  × 4       ×                                      3.7% Plast. Loss    ×          100%  ×  28%    ×                                       18%Low Temp.    -68° F          -26° F                -61° F                        -51° F                                66° F                                      -52° F% Perm. Set    1     1     0       1       1     2__________________________________________________________________________ 
    
     
                                           TABLE VIII__________________________________________________________________________Evaluation of Plasticizers in Neoprene WRT-Standard Recipe  Butoxyethoxyethanol Formal                  Di-(Butoxyethoxyethanol)-Glutarate                                      Di-Hexyloxyethoxyethanol)-Gluta                                      ratePhysical  Orig.      70 Hrs. H. Aging                  Orig.                       70 Hrs. H. Aging                                      Orig.                                           70 Hrs. H. AgingProperties  Prop.      212° F          225° F              250° F                  Prop.                       212° F                            225° F                                 250° F                                      Prop.                                           212° F                                                225° F                                                     250°__________________________________________________________________________                                                     FTensile, psi  1940      1960          2120              1940                  1950 1910 1670 1200 2010 1840 1670 1330Elong., %  295 250 260 55  280  270  230  40   310  320  300  100100% Mod.  370 510 680 --  380  450  540  --   350  350  370  --200% Mod.  995 1420          1650              --  1100 1175 1430 --   950  940  990  --Shore A   59  71  77 93  58   65   67   92    58  60   60   82Wt. % Loss  --   9   11 14.5                  --   2.7  3.5   7   --   1.5  1.8   6% Plast. Loss  --  60% 72% 97% --   18%  23%  48%  --   10%  12%  38%G.sub.10,000(LTT)  -68° F      -56° F          NA  -18° F                  -65° F                       -61° F                            -52° F                                 -20°F                                      -67° F                                           -63°F                                                -58°                                                     -°__________________________________________________________________________                                                     F 
    
     
                                           TABLE IX__________________________________________________________________________Evaluation of New Plasticizers in Hycar 1051  Butoxyethoxyethanol Formal                  Di-(Butoxyethoxyethanol)-Glutarate                                      Di-(Hexyloxyethoxyethanol)-Glut                                      aratePhysical  Orig.      70 Hrs. H. Aging                  Orig.                       70 Hrs. H. Aging                                      Orig.                                           70 Hrs. H. AgingProperties  Prop.      212° F          225° F              250° F                  Prop.                       212° F                            225° F                                 250° F                                      Prop.                                           212° F                                                225° F                                                     250°__________________________________________________________________________                                                     FTensile, psi  2175      2600          2720              2800                  2325 2250 2390 2210 2280 2360 2370 2400Elong., %  470 350 305  210                  470  330  305  240  480  370  310  280100% Mod.  390 560 800 1300                  390  490  600  690  380  500  595  675200% Mod.  890 1400          1800              2600                  890  1225 1470 1790 975  1250 1540 1810Shore A   62  72  77  87  62  68   69   73   62   65   66   70Wt. % Loss  --  8.6  13  15 --   2    2    3.5  --   1.1  1.4  2% Plast. Loss  --  57% 84% 100%                  --   13%  13%  23%  --   7%   9%G.sub.10,000(LTT)  -41° F      -19° F          0° F              +15° F                  38° F                       NA   -27° F                                 -26° F                                      -37° F                                           30°                                                -30°                                                     -23°__________________________________________________________________________                                                     F 
    
     
                                           TABLE X__________________________________________________________________________Evaluation of Plasticizers in Hycar 1051 at 300 PHR  Di-(Butoxyethoxyethanol)-                  Di-(Butoxyethoxyethoxyethanol)-                                      Di-(Butoxyethoxyethoxyethanol)-                                      .  Glutorate       Glutarate-Ex.-2     Glutarate-Ex. 8Physical  Orig.      70 Hrs. H. Aging                  Orig.                       70 Hrs. H. Aging                                      Orig.                                           70 Hrs. H. AgingProperties  Prop.      212° F          225° F              250° F                  Prop.                       212° F                            225° F                                 250° F                                      Prop.                                           212° F                                                225° F                                                     250°__________________________________________________________________________                                                     FTensile, psi  2300      2400          2130              2400                  2300 2400 2130 2400 2300 2300 2210 2350Elong., %  480 325 280 230 480  325  280  230  505  330  290  230100% Mod.  370 510 620 810 370  510  620  810  350  560  580  775200% Mod.  875 1440          1680              2070                  875  1440 1680 2070 830  1410 1390 1920Shore A   60  67  68  70  60  67   68   74    58  68    66Wt. % Loss  --   2  2.5 3.5 --   2    2.5  3.5  --   1.7   2   3% Plast. Loss  --  13%  17%              23% --   13%  17%  23%  --   11%  14%  21%G.sub.10,000(LTT)  -32° F      -29° F          24° F              -22° F                  -32° F                       -29° F                            -24°F                                 -22° F                                      -33° F                                           -29°                                                -27°                                                     -23°__________________________________________________________________________                                                     F 
    
     
                                           TABLE XI__________________________________________________________________________Evaluation of Plasticizer in Neoprene WRT* at 300 PHR                      Di-(Butoxyethoxyethoxy-                                      Di-(Butoxyethoxyethoxy-  Di-(Butoxyethoxyethanol)=Glutarate                      ethanol)-Glutarate-Ex. 2                                      ethanol)-Glutarate-Ex. 8Physical  Orig.       70 Hrs. H. Aging                      Orig.                          70 Hrs. H. Aging                                      Orig.                                           70 Hrs. H. AgingProperties  Prop.       212° F            225° F                 250° F                      Prop.                          212° F                              225° F                                  250° F                                      Prop.                                           212° F                                                225° F                                                     250°__________________________________________________________________________                                                     FTensile, psi  1950 1910 1670 1200 1810                          1590                              1570                                  900 2060 1770 1810 1040Elong., %  280  270  230  40   265 250 220 45  285  270  280  55100% Mod.  380  450  540  --   360 400 500 --  350  380  440  --200% Mod.  1100 1175 1430 --   1080                          1100                              1390                                  --  1100 1100 1310 --Shore A   58  65   67   92    57  61  63 87  58   62   63   88Wt. % Loss  --   2.7  3.5   7   --  2.2 3.1  7  --   2    3     6% Plast. Loss  --   18%  23%  48%  --  15% 21% 46% --   13%  22%  42%G.sub.10,000(LTT)  -65° F       -61° F            -52° F                 -20° F                      -64° F                          -54° F                              -47° F                                  -22° F                                      -62° F                                           -56°                                                -46°                                                     -25°__________________________________________________________________________                                                     F *Standard Recipe 
    
     
                                           TABLE XII__________________________________________________________________________Plasticizers in Herclor H at 20 PHR                                     Di-(Butoxy- (High M.W.               Di-(Butoxy-     Di-(Hexy-                                     ethoxy-                                           Di-(Hexy-                                                 Polyester       di-(Butoxy-               ethoxyethanol)-                       Di-(Butoxy-                               loxyethoxy-                                     ethoxy-                                           loxyethoxy-                                                 Plasticizer)Plasticizers       ethoxyethanol)-               Adipate ethoxyethanol)-                               ethanol)-                                     ethanol)-                                           ethanol)-                                                 paraplex G-25Orig. Properties   None       Adipate Stripped                       Glutarate                               Adipate                                     Phthalate                                           Phthalate                                                 (Rohm &amp;__________________________________________________________________________                                                 Haas)Tensile, psi   2300       1770    1770    1860    1800  2050  1950  2200Elong., %    240        360    330     310     350   320   310   400100% Mod.   1070        460    560     550     490   550   560   500200% Mod.   2100       1070    1220    1280    1110  1300  1300  1150Shore A  81  65      72      70      71    69    70    69G-10,000   -6° F       -36° F               -39° F                       -38° F                               -34° F                                     -24° F                                           -26° F                                                 -23° F% Perm. Set   1%  3%      1%      1%      2%    3%    3%    3%Compatibility   --  OK      OK      OK      OK    OK    OK    OKSamples Heat Aged 70 Hrs. 250° FTensile, psi   2650       1980    1850    2020    2000  2180  2080  2230Elong., %    180       300     280     270     305   280   280   310100% Mod.   1640       590     660     650     610   680   660   600200% Mod.   --  1340    1420    1510    1350  1600  1530  1410Shore A  91  76      78      79      76    74    75    77Wt. % Loss    0.6       3.3     2.3     2.7      2     1     1    0.8% Plast. Loss   --  24%     16%     19%     13%   4%    4%     2.7%G-10,000   --  -29° F               -34° F                       -34° F                               31° F                                     -23° F                                           -25° F                                                 -19° FSamples Heat Aged 70 Hrs. 300° FTensile, psi   23500       1925    1850    2000    1820  2050  1890  2225Elong., %    140       250     220      210    250   240   240   260100% Mod.    1750       820     900     1050    710   750   775   830200% Mod.   --  1620    1700    1940    1510  1730  1620  1800Shore A   93        83      86      87      83    81    81    83Wt. % Loss   0.8 5.7      5      7.3      3    1.4   1.7   1.2% Plast. Loss   --  45%     37%     59%     20%   6%    8%    4%G-10,000   -4° F       -24° F               -27° F                       -21° F                               -33° F                                     -29° F                                           -28° F                                                 -21°__________________________________________________________________________                                                 F 
    
     
                                           TABLE XIII__________________________________________________________________________Plasticizers in Herclor H at 20 phr.Cured 60&#39;/320° F                                Polyester (Polymeric                                                  (Polymeric       Di-(Butoxyethoxyethoxy-                    (High M.W. Polyester                                Plasticizer                                          Plasticizer)                                                  Plasticizer)Plasticizers       ethanol)-Mixed Esters                    Plasticizer) Paraplex                                Paraplex G-50                                          (Union Camp)                                                  (Union Camp)Orig. Properties   None       from Example 11                    G-25 (Rohm &amp; Haas)                                (Rohm &amp; Haas)                                          Uniflex 300                                                  Uniflex__________________________________________________________________________                                                  300Tensile, psi   2300       1900         2200        2090      2100    2100Elong., %    240       320          400         380       360     380100% Mod.   1070       590          500         530       590     510200% Mod.   2100       1290         1150        1220      1300    1200Shore A  81  69           69          71        70      70G-10,000   -6% -35° F                    -23° F                                -17° F                                          -180° F                                                  -18° F% Perm. Set    1% 2%           3%          5%        5%      5%Compatibility   --  OK           OK          OK        OK      OKSamples Heat Aged at 250° F for 70 Hrs.Tensile, psi   2650       1990         2230         2150     2150    2200Elong., %   180 250          310         310       290     305100% Mod.   1640       740          600         680       610     690200% Mod.   --  1610         1410        1410      1500    1500Shore A  91  78           77          79        79      78Wt. % Loss   0.6 2.1          0.8         1.1       0.95    0.81% Plast. Loss   --  14%          2.7%        5%        4%      3%Samples Heat Aged at 300° F for 70 Hrs.Tensile, psi   2350       1810         2225        1900      1950    2000Elong., %    140       210          260         250       250     270100% Mod.   1750       900          830         750       710     780200% Mod.   --  1700         1800        1550      1630    1600Shore A  93  80           83          79        80      80Wt. % Loss   0.8 2.8          1.2         1.6       1.4     1.1% Plast. Loss   --  18%          4%          8%        6%      4%G-10,000   -4° F       -29° F                    -21° F                                15° F                                          18° F                                                  -17°__________________________________________________________________________                                                  F 
    
     EXAMPLE 15 
     Elastomers were compounded in the formulations shown. The test data on curing and after heat ageing is shown in the following tables. 
     
         ______________________________________FORMULATIONS               Parts______________________________________1.  Hypalon 40 (chlorosulphonated polyethylene                          100    Rubber-duPont)    Magnesium Oxide            4    A/C Polyethylene 617A      2    Benzothiazyldisulfide      0.5    Dipentamethylene-thiuram tetrasulfide                          2    SRF Carbon Black           55    Plasticizer                20 or 302.  Herclor H (polyepichlorohydrin rubber)                          100    (Hercules)    Zinc Stearate              1    2-Mercaptoimidazoline      1.5    Red Lead                   5    Nickel dithiodibutylcarbamate                          1    SRF -3 Carbon Black        50    Plasticizer                203.  Hydrin 100 (polyepichlorohydrin rubber)                          100    (B. F. Goodrich)    Zinc Stearate              1    2-Mercaptoimidazoline      1.5    Red Lead                   5    Nickel dithiodibutylcarbamate                          1    SRF -3 Carbon Black        50    Plasticizer                20 or 30______________________________________ 
    
     
                                           TABLE XIV__________________________________________________________________________Plasticizers in Hypalon 40 at 20 PHRCured 30&#39;/307° F               Di-(Butoxy-     Di-(Hexy-                                      Di-(Butoxy-       Di-(Butoxy-               ethoxyethanol)-                       Di-(Butoxy-                               loxyethoxy-                                      ethoxyethoxy-                                             Di-(Hexyloxy-Plasticizers       ethoxyethanol)-               Adipate ethoxyethanol)-                               ethanol)-                                      ethanol)-                                             ethoxyethanol)-                                                     Dioctyl-Orig. Properties   None       Adipate Stripped                       Glutarate                               Adipate                                      Phthalate                                             Phthalate                                                     Sebacate__________________________________________________________________________Tensile, psi   3900       2900    3090    2700    3120   3180   2810    2800Elong., %    210       250     280     240     290    300    260     250100% Mod.   1450       700     700     780     670    610    690     890200% Mod.   3750       2100    2100    2140    2090   2000   2100    2200Shore A  83  70      69      70      73     71     73      77G-10,000   +9° F       -31° F               -34° F                       -33° F                               -33° F                                      -22° F                                             -23° F                                                     -34° F% Perm. Set   1%  1%      2%      0       1%     1%     1%      1%Samples Heat Aged 70 hrs. 250° FTensile, psi   3400       3150    3200    3000    3270   3130   3220    3060Elong., %   180  210     240     220    250    250    250      230100% Mod.   2000       1160    1040    1070    880    840    860     1000200% Mod.   --  2875    2710    2750    2550   2520   2560    2675Shore A  85  77      75      77      74     73     73      73Wt. % Loss   0.65       2.6     1.2       2     0.8    1.2    1.2     1.8% Plast. Loss   --  18%     6%      15%     2%     6%     6%      11%G-10,000   +3° F       -29° F               -34° F                       -32° F                               -29° F                                      -22° F                                             -22° F                                                     -32° FTensile, psi   2475       2700    2480    3010    2660   2525   2520    2510Elong., %    90 110     120     140     140    130    120     105100% Mod.   --  2500    2180    2400    2080   2275   2250    2200200% Mod.   --  --      --      --      --     --     --      --Shore A  88  92      88      89      90     90     90      90Wt. % Loss   1.8 8.3     6.8     8.5      6     5.5    5.6     8.3% Plast. Loss   --  61%     47%     63%     39%    36%    37%     61%G-10,000   +2° F       -5° F               -9° F                       -3° F                               -14° F                                      -12° F                                             -14° F                                                     -10°__________________________________________________________________________                                                     F 
    
     
                                           TABLE XV__________________________________________________________________________Evaluation of Plasticizers in Hypalon 40 at 30 phr.                Di-(Butoxyethoxy-                              Di-(Butoxyethoxy-                                            Di-(Hexyloxyethoxyethanol    Control (No Plasticizer)                ethanol)-Glutarate                              ethanol)-Adipate                                            Mixed Esters-Example 10    Orig.        70 Hrs. Aging                Orig.                     70 Hrs. Aging                              Orig.                                   70 Hrs. Aging                                            Orig.                                                 70 Hrs. AgingPhysical Prop.    Prop.        250° F            300° F                Prop.                     250° F                          300° F                              Prop.                                   250° F                                        300° F                                            Prop.                                                 250°                                                      300°__________________________________________________________________________                                                      FTensile, psi    3900        3400            2475                2690 2800     2820 3000     2790 2580Elong., %    210 180 90  260  230      290  250      280  220100% Mod.    1450        2000    640  800      600  900      690  710200% Mod.    3750        1920 2330     1840 2500     1900 2200Shore A  83  85  88  65   72       65   71       65   69Wt. % Loss    X   0.65            1.8 X    2.2      X    3.3      X    1.6% Plast. Loss    X   X   X   X    11       X    18       X    7Perm. Set    1   1   1   NA   1        NA   1        NA   1Low Temp (PNT)    +9° F        +3° F            +2° F                -46° F                     -45° F                              -41° F                                   &#34;37° F                                            -34° F                                                 -34°__________________________________________________________________________                                                 E     Di-(Butoxyethoxyethoxy-     ethanol)mixed esters     from Example 11                   Dioctyl Sebacate                                  Dioctyl PhthalateTensile, psi            2650 2800 2075 2900 3150 2800Elong., %               270  230  120  300  240  90100% Mod.               600  750  1800 600  850  --200% Mod. Bleeding at R.T.                   1750 2250 --   1700 2450 --Shore A   After Molding 63   66   85   62   73   96Wt. % Loss              X    1.5  11.2 X    4    17% Plast. Loss           X    6    62   X    21   99Perm. Set               1    1    0Low Temp. (PNT)         -49° F                        -42° F                             -27° F                                  -36° F                                       -19° F                                            -6° F__________________________________________________________________________ 
    
     
                                           TABLE XVI__________________________________________________________________________Evaluation of Plasticizers in Hydrin 100 at 30 phr.                   Di-(Butoxyethoxy-                                  Di-(Butoxyethoxy-    Control (No Plasticizer)                   ethanol)-Glutarate                                  ethanol)-Adipate    Orig.         70 Hrs. H. Aging                   Orig.                        70 Hrs. H. Aging                                  Orig.                                       70 Hrs. H. AgingPhysical Prop.    Prop.         250° F              300° F                   Prop.                        250° F                             300° F                                  Prop.                                       250° F                                            300° F__________________________________________________________________________Tensile, psi    2400 2600 2110 1085 1290 1310 960  1200 1010Elong., %    360  290  230  430  350  305  410  370  300100% Mod.    490  600  800  190  250  390  200  210  320200% Mod.    1220 1700 1900 470  610  810  440  520  690Shore A  65   71   76   42   50   65   46   52   59Wt. % Loss    X    1    1.3  X    3.6  12.1 X    4.3  7.3% Plast. Loss    X    X    X    X    16   62   X    20   35Perm. Set    NA   1    2    NA   2    3    NA   2    3G-10,000 (LTT)    -8° F         -7°  F              -7° F                   -53° -F                        -44° F                             -28° F                                  -49° F                                       -42°                                            -37°__________________________________________________________________________                                            F    Di-(Hexyloxyethoxyethanol)-                   Di-(Butethoxyethoxyethanol)-    Mixed Esters Example 10                   mixed esters-Ex. 11Tensile, psi    1060 1200 1000 1080 1190 900Elong., %    410  340  280  340  290  220100% Mod.    210  250  300  260  300  370200% Mod.    490  600  700  620  710  800Shore A  44   52   60   47   56   60Wt. % Loss    X    3    5.5  X    2.8  3.6% Plast. Loss    X    12   25   X    11   14Perm. Set    NA   2    1    NA   1    1G-10,000 (LTT)    -50° F         -47° F              -39° F                   -48° F                        -44° F                             -42° F__________________________________________________________________________ 
    
     EXAMPLE 16 
     Elastomers are compounded of the formulations shown. Test data of the compounds on curing and after ageing are shown in the following tables. 
     
         ______________________________________FORMULATIONS                 Parts______________________________________1.  Herclor H                    100    Zinc Stearate                1    2-Mercaptoimidazoline        1.5    Red Lead                     5    Nickel dithiodibutylcarbamate                            1    SRF #3 Carbon Black          50    Plasticizer                  20    Cured 60 min. at 320° F2.  Herclor C (epichlorohydrin copolymer with ethylene                            100    oxide) (Hercules)    Zinc Stearate                1    2-Mercaptoimidazoline        1.5    Red Lead                     5    Nickel dithiodibutylcarbamate                            1    SRF #3 Carbon Black          50    Plasticizer                  20    Cured 45 min. at 340° F3.  Hydrin 100                   100    Zinc Stearate                1    2-Mercaptoimidazoline        1.5    Red Lead                     5    Nickel dithiodibutylcarbamate                            1    SRF #Carbon Black            50    Plasticizer                  20    Cured 45 min. at 310° F                            204.  Hydrin 200                   100    Zinc Stearate                1    2-Mercaptoimidazoline        1.5    Red Lead                     5    Nickel dithiodibutylcarbamate                            1    SRF #3 Carbon Black          50    Plasticizer                  20    Cured 45 min. at 310° F5.  Hypalon 40                   100    Magnesium Oxide              4    A/C Polyethylene 617A        2    Benzothiazldisulfide         0.5    Dipentamethylene-thiuram tetrasulfide                            2    SRF Carbon Black             55    Plasticizer                  20    Cured 30 min. at 307° F______________________________________ 
    
     
                                           TABLE XVII__________________________________________________________________________Plasticizers in Herclor H                                    B.T.P.Plasticizers   Di-(Butoxyethoxy-                          Paraplex  (Stabilized with UniflexOrig. Properties     None ethanol)-Adipate                     DOP  G-25 B.T.P.                                    antioxidant)                                             B.T. DBE-2                                                     330__________________________________________________________________________Tensile, psi     2300 1750     2000   2100 2000 1920   1800     2100Elong., % 240  340      350    380  340  320    310      380100% Mod. 1070 450      475    500  500  515    475      510200% Mod. 2100 1125     1175   1200 1250 1250   1150     1200Shore A   81   66       67     68   68   68     66       70G-10,000  -6° F          -38° F                   -29°                          -21° F                               -26° F                                    -26° F                                           -36° F                                                    -18° F% Perm. Set     1%   3        5      3    3    2      3        5Compatibility     --   OK       OK     OK   OK   OK     OK       OKSamples Heat Aged 70 Hrs. 250° FTensile, psi     2650 1910     2190   2220 2130 2160   2040     2200Elong., % 180  260      300    300  280  290    290      305100% Mod. 1640 610      600    650  625  640    660      690200% Mod. --   1420     1480   1520 1550 1560   1500     1500Shore A   91   77       74     75   73   74     75       78Wt. % Loss     0.6  2.6      3.8    0.8  0.9  1.2    2.8      0.8% Plast. Loss     --   23%      34%    7%   8%   11%    25%      7%G-10,000  NA   NA       NA     NA   NA   NA     NA       NASamples Heat Aged 70 Hrs. 300°FTensile, psi     2350 1920     2250   2175 1650 2100   1940     2000Elong., % 140  230      205    250  200  260    240      270100% Mod. 1750 800      1240   800  750  750    775      780200% Mod. --   1750     2175   1755 --   1650   1680     1600Shore A   93   83       87     82   78   20     81       80Wt. % Loss     0.8  6        12     1.0  1.5  1.8    3.3      1.1% Plast. Loss     --   55%      100%   9%   13%  16%    30%      10%G-10,000  -4° F          -22° F                   -7° F                          -18° F                               -23° F                                    -22° F                                           -29° F                                                    -17°__________________________________________________________________________                                                    F DOP = Dioctyl Phthalate B.T.P. = Di-(Butoxyethoxyethoxyethanol)-Phthalate B.T.DBE-2 = Di-Butoxyethoxyethoxyethanol)-Mixed Esters-Example 11 
    
     
                                           TABLE XVIII__________________________________________________________________________Plasticizers in Herclor C                               B.T.P.Plasticizers   Di-(Butoxyethoxy-    (Stabilized withOrig. Properties     None ethanol)-Adipate                     DOP  B.T.P.                               antioxidant)                                         B.T.DBE-2__________________________________________________________________________Tensile, psi     2325 1750     1900   1950 1920    1750Elong., % 270  380      360    380  380     350100% Mod. 800  450      425    500  450     450200% Mod. 1850 1050     1050   1150 1100    1050Shore A   77   67       65     65   68      65G-10,000  -41° F          -59° F                   -52° F                          -52° F                               -51° F                                       -57° F% Perm. Set     1    5        3      3    3       2Compatibility     --   OK       OK     OK   OK      OKSamples Heat Aged 70 Hrs. 250° FTensile, psi     2460 1900     2020   2080 1950    1810Elong. %  220  310      300    310  300     280100% Mod. 590  550      570    550  550     520200% Mod. 2250 1300     1300   1350 1290    1230Shore A   82   73       74     70   72      74Wt. % Loss     0.9  2.7      5.5    1.5  1.8     3.5% Plast. Loss     --   25%      49%    14%  16%     31%G-10,000  NA   NA       NA     NA   NA      NATensile, psi     2180 1650     1940   1690 1550    1725Elong., % 190  270      220    270  250     260100% Mod. 1050 600      920    550  575     600200% Mod. --   1250     1775   1250 1275    1275Shore A   95   78       87     74   76      77Wt. % Loss     1.3  5.6      12.0   2.0  2.6     4.3% Plast. Loss     --   50%      100%   18%  24%     38%G-10,000  -39°F          -49° F                   -39° F                          -51° F                               -48° F                                       -52° F__________________________________________________________________________ DOP = Dioctyl Phthalate B.T.P. = Di-(Butoxyethoxyethanol)-Phthalate B.T.DBE-2 = Di-(Butoxyethoxyethanol)-Mixed Esters-Example 11 
    
     
                                           TABLE XIX__________________________________________________________________________Plasticizers in Hydrin 100                               B.T.P.Plasticizers   Di-(Butoxyethoxy-    (Stabilized withOrig. Properties     None ethanol-Adipate                     DOP  B.T.P.                               antioxidant                                         B.T.DBE-2__________________________________________________________________________Tensile, psi     2420 1750       1945 1960 1950      1830Elong., %  960  390        390  360  360       350100% Mod.  990  450        470  500  520       510200% Mod. 2020 1000       1100 1140 1175      1180Shore A    85   66         69   70   69        70G-10,000  -5° F          -34° F                     -27° F                          -24° F                               -26° F                                         -33° F% Perm. Set     2%    7%         8%   3%   6%        8%Compatibility     --   OK         OK   OK   OK        OKSamples Heat Aged 70 Hrs. 250° FTensile, psi     2640 1980       2040 2130 2100      1990Elong., %  205  290        280  260  260       270100% Mod. 1350  680        700  710  720       710200% Mod. 2580 1490       1520 1680 1700      1595Shore A    87   77         81   75   75        76Wt. % Loss     0.9  2.8        5.7  1.0  1.3       2.6% Plast. Loss     --   25%        51%  69%  11%       23%G-10,00        NA         NA   NA   NA        NATensile, psi     2460 1850       2150 1975 1925      1880Elong., %  160  250        230  230  240       220100% Mod. 1825  750       1050  825  850       875200% Mod. --   1525       1900 1725 1700      1725Shore A    92   75         88   72   83        83Wt. % Loss     1.2  4.6        10.6 1.5  1.9       3.5% Plast. Loss     --   41%        95%  13%  16%       32%G-10,000  -5° F          -29° F                     -8° F                          -24° F                               -23° F                                         -28° F__________________________________________________________________________ DOP = Dicotyl Phthalate B.T.P. = Di-(Butoxyethoxyethoxyethanol)-Phthalate B.T.BDE-2 = Di-(Butoxyethoxyethoxyethanol)-Mixed Esters Example 11 
    
     
                                           TABLE XX__________________________________________________________________________Plasticizers in Hydrin 200                                    B.T.P.Plasticizers   Di-(Butoxyethoxy-                          Paraplex  (Stabilized withOrig. Properties     None ethanol-Adipate                     DOP  G-25 B.T.P.                                    antioxidant)                                              B.T.DBE-2__________________________________________________________________________Tensile, psi     2150 1670       1870 1960 1870 1850      1750Elong., %  260  430        430  480  420  430       420100% Mod.  940  400        450  410  460  440       410200% Mod. 1790  880        960  950 1010 1000       910Shore A    82   65         63   65   66   66        66G-10,000  -41° F          -64° F                     -57° F                          -49° F                               -55° F                                    -55° F                                              -61° F% Perm. Set      3%  3%           5%         5%   5%   3%   2%Compatibility     OK   OK         OK   OK   0K   OK        OKSamples Heat Aged 70 Hrs. 250° FTensile, psi     2650 2000       2200 2090 2100  2175     2150Elong., %  230  360        340  340  320  310       340100% Mod. 1200  500        575  480  550  580       550200% Mod. 2375 1110       1290 1175 1250 1325      1275Shore A    85   70         72   69   72   73        73Wt. % Loss     1.0  3.1        4.6  1.4  1.5  1.7       3.1% Plast. Loss     --   28%         42% 13%  13%  15%       28%G-10,000  NA   NA         NA   NA   NA   NA        NATensile, psi     2245 1800       2050 1970 1850 1800      1700Elong., %  200  290        240  300  280  290       280100% Mod. 1200  560        850  570  550  550       550200% Mod. --   1280       1720 1375 1225 1225      1250Shore A    88   77         84   73   74   76        77Wt. % Loss     1.1  6.4        13.0 1.7  2.0  2.5       4.4% Plast. Loss     --   54%        100% 15%  18%  22%       39%G-10,000  -41° F          -52° F                     -41° F                          -49° F                               -52° F                                    -52°  F                                              -53° F__________________________________________________________________________ DOP = Dicotyl Phthalate B.T.P. = Butoxyethoxyethoxyethanol)-Phthalate B.T.DBE-2 = Butoxyethoxyethoxyethanol)-Mixed Esters-Example 11 
    
     
                                           TABLE XXI__________________________________________________________________________Plasticizers in Hypalon 40                           B.T.P.Plasticizers       Di-(Butoxyethoxy-   (Stabilized withOrig. Properties   None       ethanol)-Adipate                 DOS  B.T.P                           antioxidant)                                   B.T.BDE-2                                           330  H.C.P.                                                     H.C.A.__________________________________________________________________________Tensile, psi   3900       2720      2845                      2875 2810 3120Elong., %    210        240       270                       200  260  290100% Mod.   1450       `775       750                      1025  690  670200% Mod.   3750       2260      2110 BLEED-                           BLEEDING.sup.1                                   BLEEDING.sup.2                                           2850 2100 2090Shore A  83  72        71  ING                   75   73   73G-10,000   +9° F       -35° F                 -39° F             -7° F                                                -23° F                                                     -33° F% Perm. Set   1%   1%        2%                       0     1%   1%Compatibility   --  OK        OK                        OK   OK   OKSamples Heat Aged 70 Hrs. 250° FTensile, psi   3400       3025      2980                           3220 3270Elong., %    180        200       220                       250  250100% Mod.   2000       1200      1050                       860  880200% Mod.   --  --        2725                      BLEED-                                                2560 2550Shore A  85  79        75                       ING.sup.3                                                 73   74Wt. % Loss    0.65       2.2       1.5                       1.2  1.3% Plast. Loss   --  20%       13%                       11%  12%G-10,000   +3° F       NA        NA                        NA   NASamples Heat Aged 70 Hrs. 300° FTensile, psi   2475       2850      2410                      2440 2520 2660Elong., %    90  105       110                       105  120  140100% Mod.   --  2750      2270                      2050 2250 2080200% Mod.   --  --        --                        --   --   --Shore A  88  93        92                        91   90   90Wt. % Loss   1.8 8.7       7.1                       2.4  5.6     6% Plast. Loss   --  79%       65%                       22%  52%  54%G-10,000   +2° F       -9° F                 -26° F             -6° F                                                -14° F                                                     -14°__________________________________________________________________________                                                     F .sup.1 This sample, with antioxidant, bleeds more than identical plasticizer, which has no stabilizer. .sup.2 The Di-(Butoxyethoxyethoxyethanol)-Mixed Esters-Example 2 ester bleeds more than the butoxy triglycol phthalate. .sup.3 After 70 hrs. 250° F this sample looked similar to the original R.T. Di-(Butoxyethoxyethoxyethanol)-phthalate (with hydroquinone sample. .sup.4 Although bleeding, 70 hrs. at 300° F only showed a 27% plasticizer loss. DOS = Dioctyl Sebacate B.T.P. = Di-(Butoxyethoxyethoxyethanol)-Phthalate B.T.DBE-2 = Di-(Butoxyethoxyethoxyethanol)-Mixed Esters-Example 11 H.C.P. = Di-(Hexyloxyethoxyethanol)Phthalate H.C.A = Di-(Hexyloxyethoxyethanol)-Adipate 
    
     EXAMPLE 17 
     Elastomer formulations were compounded in the proportions shown. The results obtained after cure and on heat ageing and exposure to various solvents are shown in the following tables. 
     
         ______________________________________FORMULATIONS              Parts______________________________________1.   Hydrin 100               100Red Lead                 52-Mercaptoimidazoline    1.5TE-75                    1.5Nickel dithiodibutylcarbamate                         1SRF #3 Carbon Black      50Plasticizer              20Cured 45 min. at 310° F2.   Hydrin 200               100Red Lead                 52-Mercaptoimidazoline    1.5TE-75                    1.5Nickel dithiodibutylcarbamate                         1SRF #3 Carbon Black      50Plasticizer              20Cured 45 min. at 310° F______________________________________ 
    
     
                                           TABLE XXII__________________________________________________________________________Plasticizers in Hydrin 100               Di(Butoxyethoxy-                          Di-(Butoxyethoxyethoxy-     Di-(Butoxyethoxy-               ethoxyethanol)-                          ethanol)-mixedplasticizer     ethanol)-Adipate               Phthalate  Esters-Example 11__________________________________________________________________________Orig. PropertiesTensile, psi     1660      1860       1750Elongation %     330       330        300100% Mod. 500       520        500200% Mod. 1080      1200       1110Duro A    69        69         68Tear Die &#34;C&#34;     160       165        150L.T.T. (G10,000° F)     -39       -27        -34Compatibility     OK        OK         OKHeat Ageing Properties-70 Hrs./300° FTensile, psi     1960      1695       1510% Change  +21       -9         -13Elongation %     200       200        190% Change  -39       -39        -36100% Mod. 1150      900        810200% Mod. 1960      1695       --Duro A    87        80         80Pts. Change     +18       +11        +12L.T.T. (G10,000° F)     -19       -23        -28Plasticizer Loss %     4         2          2Heat Ageing Properties-7 days at 300° FTensile, psi     1260      1130       1110% Change  -24       -31        -36Elongation %     185       190        210% Change  -46       -42        -30100% Mod. 810       600        510200% Mod. --        --         1070Duro A    87        80         80Pts. Change     +18       +11        +12L.T.T. (G10,000° F)     -9        -22        -27Plasticizer Loss %     14        7          6Immersion Tests-Ref. Fuel A24 Hrs. at R.T.Tensile, psi     1630      1840       1710% Change  -2        -1         -2Elongation %     290       300        270% Change  -13       -10        -11Duro A    68        67         67Pts. Change     -1        -2         -1Volume Swell %     0         0          0Ref. Fuel B24 Hrs. at R.T.Tensile, psi     1500      1640       1560% Change  -10       -12        -11Elongation %     260       250        240% Change  -22 -23   -20Duro A    64        63         64Pts. Change     -5        -6         -4Volume Swell %     +9        +10        +9ASTM Oil #370 Hrs. at 300° FTensile, psi     1610      1760       1640% Change  -3        -5         -6Elongation %     270       270        240% Change  - 17      -19        -20Duro A    63        61         61Pts. Change     -6        -8         -7Volume Swell %     +5        +7         +6__________________________________________________________________________ 
    
     
                                           TABLE XXIII__________________________________________________________________________Plasticizers in Hydrin 200               Di-(Butoxyethoxy-                          Di-(Butoxyethoxyethoxy-     Di-(Butoxyethoxy-               ethoxyethanol)-                          ethanol)-Mixed Esters-Plasticizer     ethanol)-Adipate               Phthalate  Example 11__________________________________________________________________________Orig. PropertiesTensile, psi     1650      1760       1710Elongation %     400       370        380100% Mod. 400       420        410200% Mod. 910       1020       970Duro A    66        67         64Tear Die &#34;C&#34;     195       200        190L.T.T. (G10,000° F)     -60       -52        -58Compatibility     OK        OK         OKHeat Ageing Properties-70 Hrs. at 300° FTensile, psi     1800      1560       1610% Change  +9        -11        -6Elongation %     230       230        250% Change  -42       -45        -34100% Mod. 740       600        575200% Mod. 600       1350       1270Duro A    83        74         75Pts. Change     +17       +7         +11L.T.T. (G10,000° F)     -50       -49        -58Plasticizer Loss %     3         3          3Heat Ageing Properties-7 days at 300° FALL SAMPLES BRITTLEImmersion Tests-Ref. Fuel A24 Hrs. at R. T.Tensile, psi     1680      1720       1760% Change  +2        +4         +3Elongation %     390       350        360% Change  -2        -4         -5Duro A    67        69         65Pts. Change     +1        +2         +1Volume Swell %     +5        +6         +5Ref. Fuel B24 Hrs. at R.T.Tensile, psi     1570      1640       1610% Change  -5        -7         -6Elongation %     360       330        350% Change  -9        -10        -9Duro A    61        60         58Pts. Change     -5        -7         -6Volume Swell %     +17       +20        +18ASTM Oil #370 Hrs. at 300° FTensile, psi     1700      1850       1780% Change  +3        +5         +4Elongation %     340       300        320% Change  -15       -18        -17Duro A    60        59         57Pts. Change     -6        -8         -7Volume Swell %     +9        +11        +10__________________________________________________________________________ 
    
     EXAMPLE 18 
     Elastomer formulations were compounded in the proportions shown. The results obtained after cure and on heat ageing are shown in the following tables. 
     
         ______________________________________Formulations            A-1    A-2    A-3______________________________________Hycar 1052 (Nitrile Rubber)                   100    100    100(B. F. Goodrich)SRF #3 Carbon Black     60     60     60Zinc Oxide              5      5      5Stearic Acid            1.5    1.5    1.5Sulfur                  1.75   1.75   1.75Benzothiazyldisulfide   1.5    1.5    1.5Sym-Diphenylguanidine   0.25   0.25   0.25Di-(Butoxyethoxyethanol)-Adipate                   20     --     --Di-(Butoxyethoxyethoxyethanol)-Adipate                   --     20     --Di-(Butoxyethoxyethoxyethanol)-Mixed Esters                   --     --     20(Example 11)Cure: 30 minutes at 310° F                   B-1    B-2    B-3______________________________________Hypalon 40              100    100    100Litharge                20     20     20Magnesium Oxide         10     10     10SRF Carbon Black        55     55     55Nickel Dithiodibutylcarbamate                   3      3      3Benzothiazyldisulfide   0.5    0.5    0.5Dipentamethylenethiuramtetrasulfide                   2      2      2Di-(Butoxyethoxyethanol)-Adipate                   20     --     --Di-(Butoxyethoxyethoxyethanol)-Adipate                   --     20     --Di-(Butoxyethoxyethoxyethanol)-Mixed Esters                   --     --     20(Example 11)Cure: 30 minutes at 310° F                   C-1    C-2    C-3______________________________________Toluene diisocyanate-ethylene propylene-                   100    100    100polyadipate rubber (M.W. polyester=2700)SRF Carbon Black        30     30     30Benzothiazyldisulfide   4      4      4Mercaptobenzothiazol    2      2      2Partial Complex of ZnCl.sub.2 with Benzothioxyl-                   1      1      1disulfide (Caytur #4-duPont)Cadmium Stearate        0.5    0.5    0.5Sulfur                  1.5    1.5    1.5Di-(Butoxyethoxyethanol)-Adipate                   20     --     --Di-(Butoxyethoxyethoxyethanol)-Adipate                   --     20     --Di-(Butoxyethoxyethoxyethanol)-Mixed Esters-                   --     --     20(Example 11)Cure: 45 minutes 287° F                   D-1    D-2    D-3______________________________________Toluene diisocyanate-polylactone polyol                   100    100    100rubber based on caprolactone (M.W.polyactone polyol=1250)SAF Carbon Black        30     30     30Benzothiazyldisulfide   4      4      4Mercaptobenzothiazol    2      2      2Caytur #4               1      1      1Cadmium Stearate        0.5    0.5    0.5Sulfur                  1.5    1.5    1.5Di-(Butoxyethoxyethanol)-Adipate                   20     --     --Di-(Butoxyethoxyethoxyethanol)-Adipate                   --     20     --Di-(Butoxyethoxyethoxyethanol)-Mixed Esters                   --     --     20(Example 11)Cure: 45 minutes at 287° F______________________________________ 
    
     
                       TABLE XXIV______________________________________Plasticizers in Hycar 1052Formulations            A-1    A-2    A-3______________________________________Original PropertiesTensile, psi            2320   2680   2380Elongation, %           550    605    510100% Mod.               275    280    275200% Mod.               660    700    720Duro A                  60     62     61L.T.T. (G10,000)° F                   -43    -29    -37L.T. Brittleness D-746  -59    -38    -48Compatibility           OK     OK     OKHeat Ageing Properties-70 Hrs./212° FTensile, psi            2550   2610   2510% Change                +10    3      +5Elongation, %           370    390    360% change                32     35     29100% Mod.               470    450    470200% Mod.               1220   1200   1270Duro A                  71     70     71Pts. Change             +11    +8     +10L.T.T.(G10,000)° F                   -28    -26    -32L.T. Brittleness D-746  -42    -38    -42% Plasticizer Loss      4      1      1Heat Ageing Properties-70 Hrs./225° FTensile, psi            2870   2660   2570% Change                +23    1      +8Elongation, %           300    305    290% Change                45     49     43100% Mod.               860    700    625200% Mod.               2040   1700   1740Duro A                  81     74     73Pts. Change             +21    +12    +12L.T.T. (G10,000)°  F                   -7     -24    -33L.T. Brittleness D-746  -27    -37    -45% Plasticizer Loss      8      2      2Heat Ageing Properties-70 Hrs./250° FTensile, psi            2580   2240   2300% change                +11    18     3Elongation, %           170    205    190% Change                69     66     62100% Mod.               1520   900    960200% Mod.               --     2100   --Duro A                  87     76     78Pts. Change             +27    +14    +17L.T.T. (G10,000)° F                   -3     -24    -29L.T. Brittleness D-746  -20    -33    -38% Plasticizer Loss      10     3      3______________________________________ 
    
     
                       TABLE XXV______________________________________Plasticizers in Hypalon 40Formulations            B-1    B-2    B-3______________________________________Original PropertiesTensile, psi            2850   2910   2890Elongation, %           260    210    230100% Mod.               575    1000   900200% Mod.               1990   2750   2500Duro A                  71     77     77L.T.T.(G10,00)° F                   -34    -23    -31L.T. Brittleness D-746  -47    -34    -44Compatibility           OK     OK     OKHeat Ageing Properties-70 Hrs./300° FTensile, psi            2150   2820   2350% Change                25     3      18Elongation, %           160    200    160% Change                38     5      31100% Mod.               1300   1390   1380Duro A                  84     83     84Pts. Change             +13    +6     +7L.T.T. (G10,000)° F                   -19    -24    -27L.T. Brittleness D-746  -37    -36    -46% Plasticizer Loss      5      3      3______________________________________ 
    
     
                       TABLE XXVI______________________________________Plasticizers in Polyester Urethane RubberFormulations            C-1    C-2    C-3______________________________________Original PropertiesTensile, psi            3000   3740   3610Elongation, %           430    480    500100% Mod.               400    410    410200% Mod.               950    1000   1000Duro A                  65     67     65L.T.T. (G10,000)° F                   -39    -28    -36L.T. Brittleness D-746  -47    -33    -44Compatibility           OK     OK     OKHeat Ageing Properties-70 Hrs./212° FTensile, psi            3320   3825   3600% Change                +1     +2     -1Elongation, %           390    410    410% Change                9      15     18100% Mod.               450    550    520200% Mod.               1250   1420   1350Duro A                  69     72     70Pts. Change             +4     +5     +5L.T.T. (G10,000)° F                   -30    -23    -28L.T. Brittleness D-746  -41    -35    -38% Plasticizer Loss      3      1      1Heat Ageing Properties-70 Hrs./225°°F -Tensile,                   2850   3640   3110% Change                5      3      13Elongation, %           330    390    360% Change                23     18     28100% Mod.               510    540    550200% MOd.               1370   1475   1450Duro A                  70     70     69Pts. Change             +5     +3     +4L.T.T. (G10,000)° F                   -30    -22    -28L.T. Brittleness D-746  -37    -29    -38% Plasticizer Loss      4      2      2Heat Ageing Properties-70 Hrs./250° FTensile, psi            1880   1750   1850% Change                37     53     31Elongation, %           270    270    280% Change                36     43     44100% Mod.               510    450    460200% Mod.               1340   1200   1200Duro A                  69     68     67Pts. Change             +4     +1     +2L.T.T. (G10,000)° F                   -27    -25    -25L.T.T. Brittleness D-746                   -33    -33    -32% Plasticizer Loss      5      3      3______________________________________ 
    
     
                       TABLE XXVII______________________________________Plasticizers in Polylactonepolyol Urethane RubberFormulations            D-1    D-2    D-3______________________________________Original PropertiesTensile, psi            2740   3850   3100Elongation, %           420    480    425100% Mod.               375    420    400200% Mod.               950    1050   950Duro A                  64     69     66L.T.T. (G10,000)° F                   -44    -31    -40L.T. Brittleness D-746  -57    -55    -58Compatibility           OK     OK     OKHeat Ageing Properties-70 Hrs./212° FTensile, psi            2650   3490   2830% Change                3      9      9Elongation, %           285    300    280% Change                32     37     34100% Mod.               610    660    650200% Mod.               1550   1810   1640Duro A                  73     75     74Pts. Change             +9     +6     +8L.T.T. (G10,000)° F                   -39    -24    -36L.T. Brittleness D-746  -58    -47    -53% Plasticizer Loss      3      1      1Heat Ageing Properties-70 Hrs./225° FTensile, psi            2450   3060   2740% Change                11     21     11Elongation, %           240    270    275100% Mod.               690    700    700200% Mod.               1790   1980   1900Duro A                  74     75     74Pts. Change             +10    +6     +8L.T.T. (G10,000)°  F                   -37    -28    -36L.T. Brittleness D-746  -52    -40    -52% Plasticizer Loss      4      2      2Heat Ageing Properties-70 Hrs./250° FTensile, psi            2200   2900   2100% Change                19     24     32Elongation, %           240    285    240% Change                42     40     41100% Mod.               660    610    590200% Mod.               1610   1675   1590Duro A                  71     72     70Pts. Change             +7     +3     +4L.T.T. (G10,000)° F                   -38    -29    -36L.T. Brittleness D-746  -51    -49    -52% Plasticizer Loss      5      3      3______________________________________ 
    
     EXAMPLE 19 
     Elastomer formulations were compounded in the proportions shown. The results obtained after cure and on heat ageing are shown in the following tables. 
     
         ______________________________________Formulations            A-1    A-2    A-3______________________________________Hycar 4041 (B. F. Goodrich)                   100    100    100Stearic Acid            2      2      2Fast Extrusion Furnace Carbon Black                   60     60     60Acrawax C (Glyco Chem. Co.)                   1      1      1Hexamethylene diamine carbamate                   1      1      1Di-(Butoxyethoxyethanol)-Adipate                   20     --     --Di-(Butoxyethoxyethoxyethanol)-Adipate                   --     20     --Di-(Butoxyethoxyethoxyethanol)-Mixed Esters                   --     --     20 (Example 11)Cure: 30 minutes at 300° F, - Tempered at 24 hours at 300°                   B-1    B-2    B-3______________________________________Ethyl Acrylate-Allyl glycidyl ether-                   100    100    100allyl methacrylate (95-5-0.1) RubberStearic Acid            1      1      1Fast Extrusion Furnace Carbon Black                   60     60     60Polymerized 1,2-dihydro-2,2,4-trimethyl-                   1.5    1.5    1.5quinoline (Flectol H Monsanto)Hexamethylene diamine carbamate                   1      1      1Di-(Butoxyethoxyethanol)-Adipate                   20     --     --Di-(Butoxyethoxyethoxyethanol)-Adipate                   --     20     --Di-(Butoxyethoxyethoxyethanol)-Mixed Esters                   --     --     20 (Example 11)Cure: 30 minutes at 300° F, Tempered at 24 hours at 300° F______________________________________ 
    
     
                       TABLE XXVIII______________________________________Plasticizers in Hycar 4041Formulation             A-1    A-2    A-3______________________________________Original PropertiesTensile, psi            1140   1250   1210Elongation, %           290    270    260100% Mod.               350    400    420200% Mod.               820    950    960Duro A                  72     65     69L.T.T. (G10,000)° F                   -24    -28    -34L.T. Brittleness, D-746 -30    -27    -38Compatibility           OK     OK     OKHeat Ageing Properties-70 Hrs./300° FTensile, psi            1480   1170   1240% Change                +30    6      3Elongation, %           240    270    270% Change                17     0      +4100% Mod.               550    380    450200% Mod.               1310   860    1000Duro A                  80     69     72Pts. Change             +8     +4     +3L.T.T. T. (G10,000)° F                   -13    -26    -32L.T. Brittleness D-746  -14    -23    -33Plasticizer Loss %      4      2      2Heat Ageing Properties-70 Hrs./350° FTensile, psi            1175   1210   1250% Change                +3     3      +3Elongation, %           200    240    215% Change                31     11     17100% Mod.               780    530    590200% Mod.               1175   1080   1160Duro A                  91     82     80Pts. Change             +19    +17    +11L.T.T. (G10,000)° F                   +7     -6     -15L.T. Brittleness D-746  +1     -12    -17Plasticizer Loss %      8      6      4______________________________________ 
    
     
                       TABLE XXIX______________________________________Plasticizers in Acrylate RubberFormulation             B-1    B-2    B-3______________________________________Original PropertiesTensile, psi            1570   1490   1530Elongation, %           270    190    210100% Mod.               510    690    600200% Mod.               1250   1520   1480Duro A                  66     65     60L.T.T. (G10,000)° F                   -28    -26    -32L.T. Brittleness D-746  -33    -31    -36Compatibility           OK     OK     OKHeat Ageing Properties-70 Hrs./300° FTensile, psi            1400   1275   1450% Change                11     14     5Elongation %            210    180    205% Change                22     5      2100% Mod.               550    600    475200% Mod.               1270   1480   1400Duro A                  79     69     64Pts. Change             +13    +4     +4L.T.T. (G10,000)° F                   -6     -23    -27L.T. Brittleness D-746  -22    -27    -32Plasticizer Loss %      5      2      2Heat Ageing Properties-70 Hrs./350° FTensile, psi            1500   1490   1420% Change                4      0      7Elongation, %           220    210    220% Change                18     +10    +5100% Mod.               740    520    490200% Mod.               1350   1400   1210Duro A                  85     69     72Pts. Change             +19    +4     + 12L.T.T. (G10,000)° F                   +4     -17    -19L.T. Brittleness D-746  +3     -18    -23Plasticizer Loss %      5      3      3______________________________________ 
    
     EXAMPLE 20 
     Elastomer formulations were compounded in the proportions shown. The results obtained after cure and on heat ageing are shown in the following table. 
     
         ______________________________________Formulation          1      2      3    4______________________________________CPE-CM0136 (Chlorinated Poly-                100    100    100  100 ethylene Rubber Dow Chemical)White Lead           10     10     10   10Drapex 6.8 (Epoxidized Soybean Oil-                10     10     10   10Argus Chemical)SRF Carbon Black     60     60     60   60Triallyl Isocyanurate                2      2      2    2Dicumyl Peroxide     7.5    7.5    7.5  7.5Butoxyethoxyethanol Formal                --     20     --   --Di-(Butoxyethoxyethanol)-Adipate                --     --     20   --Di-(Butoxyethoxyethoxyethanol)-MixedEsters-(Example 11)  --     --     --   20Cure: 30 minutes at 320° F______________________________________ 
    
     
                       TABLE XXX______________________________________Plasticizers in Chlorinated Polyethylene RubberFormulationOrig. Properties     1      2      3    4______________________________________Tensile, psi         3460   1640   2200 1800Elongation, %        190    550    400  480100% Mod.            2000   260    350  300200% Mod.            3540   600    100  740Duro A               85     69     70   69L.T.T. (G10,000)° F                -1     -42    -34  -35L.T. Brittleness D-746                -6     -47    -39  -40Compatibility        --     OK     OK   OKHeat Ageing Properties-70 hrs. at 212° FTensile, psi         3350   1970   2225 1950% Change             -31    +20    +1   +8Elongation, %        160    490    380  490% Change             -15    -10    -5   -2100% Mod.            2100   550    470  340200% Mod.            --     1150   1200 860Duro A               87     83     75   73Pts. Change          +2     +14    +5   +4L.T.T. (G10,000)° F                +3     -9     -28  -30L.T. Brittleness D-746                +8     -14    -33  `35Plasticizer Loss %   --     8      2    1Heat Ageing Properties-70 hrs. at 300°FTensile, psi         1230   1160   1330 1330% Change             -64    -29    -39  -26Elongation, %        70     90     90   200% Change             -63    -83    -77  -58100% Mod.            --     1275   1380 720200% Mod.            --     --     --   1330Duro A               93     93     90   83Pts. Change          +8     +24    +20  +14L.T.T. (G10,000)° F                +15    +15    +6   -14L.T. Brittleness D-746                +20    +20    +11  -19Plasticizer Loss %   --     10     9    7______________________________________