buta-1,3-diene;furan-2,5-dione

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same apparatus and method as used in comparative Example 1 were employed for the reaction of 2,500 milliliters acetone, 294 grams maleic anhydride, 162 grams butadiene, 4.9 grams azo-bis-isobutylnitrile and 18.0 grams n-dodecylmercaptan. There was obtained 278 grams butadiene-maleic acid anhydride copolymer. The viscosity of this polymer was 0.21. Its sulfur content was 0.33 percent. Terminal dodecylthio radicals as calculated from the sulfur content were 2.2 percent of the polymer, well corresponding to an NMR value of 2.3. 15.5 grams polymer was charged to a separable flask of the type used in comparative Example 1, followed by the addition of 155 grams water and 10.7 grams potassium hydroxide. The whole was stirred at room temperature for 4 hours. The solution thereby obtained was added with 130 milliliters of 1 mol/liter magnesium sulfate and stirred vigorously. It was then heated for 2 hours with use of a hot bath of 100° C. but with no stirring, whereupon the solution was separated into a rubber-like solid phase and a liquid phase, respectively. The liquid layer was removed, and thereafter the flask was cooled, whereby the rubbery solid became progressively liquefied. After a lapse of one hour, there was obtained a viscous transparent liquid. This will be hereafter referred to as E-1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: of the same butadiene-maleic anhydride copolymer as in Example 11, 40g. of cyclohexylamine and 500 ml. of water were fed in a separable 1 liter flask equipped with a stirrer and a reflux condenser. A reaction was carried out for 1 hour at 100° C. under a nitrogen gas atmosphere to give a transparent, viscous, aqueous butadiene-maleic acid copolymer cyclohexylamine salt solution. To this aqueous solution was added over a period of 10 minutes a separately prepared aqueous solution of 56g. of magnesium acetate tetrahydrate in 100 ml. of water. After completion of the addition, heating was applied up to near 100° C. while a violent stirring was applied to the interior pf the flask, resulting in that there were deposited many solids in the form of small lumps. The solids were separated from the liquid phase by means of hot filtration and collected in a flask. Cooling of the flask in an ice-water bath resulted in that after 5 minutes the solids therein were completely converted into an aqueous solution. To the aqueous solution thus obtained there were repeatedly applied such heating and cooling operations. At every repetition the aqueous solution on heating was converted into a rubber-like matter and on cooling reverted to its original liquid phase. equipped with a stirrer and a reflux condenser

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same apparatus and method as used in comparative Example 1 were employed for the reaction of 2,500 milliliters acetone, 294 grams maleic anhydride, 162 grams butadiene, 4.9 grams azo-bis-isobutylnitrile and 18.0 grams n-dodecylmercaptan. There was obtained 278 grams butadiene-maleic acid anhydride copolymer. The viscosity of this polymer was 0.21. Its sulfur content was 0.33 percent. Terminal dodecylthio radicals as calculated from the sulfur content were 2.2 percent of the polymer, well corresponding to an NMR value of 2.3. 15.5 grams polymer was charged to a separable flask of the type used in comparative Example 1, followed by the addition of 155 grams water and 10.7 grams potassium hydroxide. The whole was stirred at room temperature for 4 hours. The solution thereby obtained was added with 130 milliliters of 1 mol/liter magnesium sulfate and stirred vigorously. It was then heated for 2 hours with use of a hot bath of 100° C. but with no stirring, whereupon the solution was separated into a rubber-like solid phase and a liquid phase, respectively. The liquid layer was removed, and thereafter the flask was cooled, whereby the rubbery solid became progressively liquefied. After a lapse of one hour, there was obtained a viscous transparent liquid. This will be hereafter referred to as E-1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the invention, an example of the process used for obtaining the butadiene/maleic acid anhydride mixture for the reaction of step (1) comprises the oxidation of n-butene to give butadiene. According to the invention it is possible for this oxidation to be followed by addition of maleic acid anhydride (MA) to the crude butadiene in order to obtain a butadiene/maleic acid anhydride mixture for the reaction of step (1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the invention, an example of the process used for obtaining the butadiene/maleic acid anhydride mixture for the reaction of step (1) comprises the oxidation of n-butene to give butadiene. According to the invention it is possible for this oxidation to be followed by addition of maleic acid anhydride (MA) to the crude butadiene in order to obtain a butadiene/maleic acid anhydride mixture for the reaction of step (1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: According to the invention, an example of the process used for obtaining the butadiene/maleic acid anhydride mixture for the reaction of step (1) comprises the oxidation of n-butene to give butadiene. According to the invention it is possible for this oxidation to be followed by addition of maleic acid anhydride (MA) to the crude butadiene in order to obtain a butadiene/maleic acid anhydride mixture for the reaction of step (1).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: of the same butadiene-maleic anhydride copolymer as in Example 11, 40g. of cyclohexylamine and 500 ml. of water were fed in a separable 1 liter flask equipped with a stirrer and a reflux condenser. A reaction was carried out for 1 hour at 100° C. under a nitrogen gas atmosphere to give a transparent, viscous, aqueous butadiene-maleic acid copolymer cyclohexylamine salt solution. To this aqueous solution was added over a period of 10 minutes a separately prepared aqueous solution of 56g. of magnesium acetate tetrahydrate in 100 ml. of water. After completion of the addition, heating was applied up to near 100° C. while a violent stirring was applied to the interior pf the flask, resulting in that there were deposited many solids in the form of small lumps. The solids were separated from the liquid phase by means of hot filtration and collected in a flask. Cooling of the flask in an ice-water bath resulted in that after 5 minutes the solids therein were completely converted into an aqueous solution. To the aqueous solution thus obtained there were repeatedly applied such heating and cooling operations. At every repetition the aqueous solution on heating was converted into a rubber-like matter and on cooling reverted to its original liquid phase. equipped with a stirrer and a reflux condenser

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The same apparatus and method as used in comparative Example 1 were employed for the reaction of 2,500 milliliters acetone, 294 grams maleic anhydride, 162 grams butadiene, 4.9 grams azo-bis-isobutylnitrile and 18.0 grams n-dodecylmercaptan. There was obtained 278 grams butadiene-maleic acid anhydride copolymer. The viscosity of this polymer was 0.21. Its sulfur content was 0.33 percent. Terminal dodecylthio radicals as calculated from the sulfur content were 2.2 percent of the polymer, well corresponding to an NMR value of 2.3. 15.5 grams polymer was charged to a separable flask of the type used in comparative Example 1, followed by the addition of 155 grams water and 10.7 grams potassium hydroxide. The whole was stirred at room temperature for 4 hours. The solution thereby obtained was added with 130 milliliters of 1 mol/liter magnesium sulfate and stirred vigorously. It was then heated for 2 hours with use of a hot bath of 100° C. but with no stirring, whereupon the solution was separated into a rubber-like solid phase and a liquid phase, respectively. The liquid layer was removed, and thereafter the flask was cooled, whereby the rubbery solid became progressively liquefied. After a lapse of one hour, there was obtained a viscous transparent liquid. This will be hereafter referred to as E-1.