Phillips Petroleum Company

James T Edmonds, Jr

Robert W Campbell

Lacey E Scoggins

Fred T Sherk

Jon F Geibel

Rex L Bobsein

Dale O Tieszen

Harold Wayne Hill, Jr

Jim J Straw

Willie W Crouch

A two-step process to make a poly(arylene sulfide sulfone) polymer exhibiting improved high temperature properties is described. In the first step a prepolymer characterized as dihalo-terminated polyethersulfone oligomers is prepared by reacting an aromatic diphenol with an excess of a dihalo aromatic sulfone. In the second step the excess dihalo aromatic sulfone and the oligomers are copolymerized in the presence of a sulfur source to form a poly(arylene sulfide sulfone) polymer. An alkali metal carboxylate is present in the second step. The polymers exhibit improved softening temperature and glass transition temperature and are useful in high temperature applications.

Poly(arylene sulfide sulfone) polymer containing ether groups

A method for producing a polymer in which lithium hydroxide, optionally also employing either lithium chloride or lithium acetate, is contacted with N-methyl-pyrrolidone in the presence of lithium halide to produce a reaction product mixture containing lithium N-methyl-4-aminobutyrate with this reaction mixture then being contacted with hydrogen sulfide and polyhalo aromatic compound in the presence of additional N-methyl-pyrrolidone under conditions to form a polymer. Lithium halide produced as a by-product is substantially recovered from the reaction mixture, converted to lithium hydroxide and can be recycled to the process.

Production of arylene sulfide polymer beads

A method for producing arylene sulfide polymer in which a reaction mixture containing at least one polyhalo-substituted aromatic compound, at least one organic amide, at least one alkali metal carboxylate, H.sub.2 S and water in an amount up to 5 weight percent of the total of the reaction mixture components is contacted at polymerization conditions for a time sufficient to produce polymer. In a preferred embodiment, at least one alkali metal carboxylate is present in the reaction mixture.

Arylene sulfide polymer preparation

Arylene sulfide polymers containing ash-forming impurities or materials are purified by contacting an aqueous mixture of such polymer with molecular oxygen under conditions sufficient to reduce the ash-forming impurities and concurrently at least partially cure the polymer.

Arylene sulfide polymer purification

A method for producing arylene sulfide polymer in which an anhydrous reaction mixture containing at least one polyhalo-substituted aromatic compound, at least one organic amide, at least one alkali metal hydroxide, and H.sub.2 S is maintained at polymerization conditions for a time sufficient to produce polymer. In a preferred embodiment the reaction mixture contains at least one alkali metal salt derived from a monocarboxylic acid or carbonic acid.

Arylene sulfide polymers containing ash-forming impurities or materials are purified by contacting an aqueous mixture of such polymer with molecular oxygen and a chemical treating agent under conditions sufficient to reduce the ash-forming impurities and concurrently at least partially cure the polymer. In another embodiment, at least partially cured arylene sulfide polymers are treated with a chemical treating agent in the absence of molecular oxygen to stabilize the melt flow of the resin.

Alkali metal aminoalkanoate is prepared by contacting in the presence of an alkali metal carboxylate a reaction mixture in which there is at least one alkali metal hydroxide, at least one lactam, and water. Arylene sulfide polymer is prepared by contacting at polymerization conditions a reaction mixture that contains at least one alkali metal aminoalkanoate prepared as described above; at least one polyhalo-substituted aromatic compound; at least one organic amide as solvent and H.sub.2 S. In an embodiment of the polymerization the organic amide used as solvent can be the same as the lactam from which the alkali metal aminoalkanoate was produced.

Preparation of alkali metal aminoalkanoates

Arylene sulfide polymer prepared from aminoalkanoate

Branched arylene sulfide polymers of low melt flow are produced by employing (1) a p-dihalobenzene, (2) a polyhalo aromatic compound having more than two halogen substituents per molecule, (3) an alkali metal sulfide, (4) an N-alkyl lactam, and (5) controlled amounts of water in the presence or absence of a sodium carboxylate. The resulting polymers without prior curing can be fabricated into shaped products having desirable properties.

Branched arylene sulfide polymer production

A method is provided for producing a p-phenylene sulfide polymer by contacting at least one p-dihalobenzene, at least one alkali metal sulfide, at least one alkali metal carboxylate, at least one organic amide and at least one alkali metal hydroxide to form a composition at polymerization conditions. The use of an alkali metal hydroxide in addition to the other compounds used in the reaction mixture results in p-phenylene sulfide polymers of higher molecular weight than produced without the alkali metal hydroxide, as evidenced by lower melt flow of the polymer than produced by the compared methods.

Production of p-phenylene sulfide polymers

A method is provided in the production of an arylene sulfide polymer by employing a p-dihalobenzene, optionally together with a minor amount of a polyhalo aromatic compound having more than two halogen substituents per molecule; an alkali metal sulfide; an alkali metal carboxylate; a base selected from alkali metal hydroxides and alkali metal carbonates; and an organic amide using a profile of selected temperature ranges within the range of polymerization reaction temperature for the process which results in a polymer of lower melt flow than that of the polymer produced when one polymerization temperature is used throughout the polymerization stage.

Temperature programming in the production of arylene sulfide polymers

Arylene sulfide polymers containing ash-forming impurities or materials are purified by heating such polymers with an organic amide and an alkali metal salt selected from carboxylates, carbonates, and selected lithium halides under conditions sufficient to reduce the ash-forming impurities without extensive polymer degradation.

A method is provided for producing arylene sulfide polymers employing a p-dihalobenzene, an alkali metal sulfide, lithium acetate, an N-alkyl-2-pyrrolidone, and optionally a polyhalo aromatic compound having more than two halogen substituents per molecule, preferably with the addition of a base selected from alkali metal hydroxides and alkali metal carbonates at polymerization conditions. A first composition comprising N-alkyl-2-pyrrolidone, lithium acetate and water is prepared and subjected to dehydration conditions after which a composition containing at least 50 weight percent water, an alkali metal sulfide and preferably containing a base is added to the first dehydrated composition and a second dehydration performed. A composition resulting from the second dehydration is then contacted with a p-dihalobenzene, and optionally a polyhalo aromatic compound having more than two halogen substituents per molecule, at polymerization conditions to form arylene sulfide polymers of higher molecular weight than produced without the two-step dehydration. The two-step dehydration also results in less foaming and flooding of the distillation column as compared with the process using a single dehydration.

Production of arylene sulfide polymers

Block copolymers and the processes of preparing them are disclosed wherein alpha-olefins and/or mixtures of alpha-olefins are alternately polymerized in the presence of a catalyst comprising a titanium halide and an aluminum alkyl compound.

Preparation of block copolymers

A method by which arylene sulfide polymers are produced by admixing p-dihalobenzene, optionally together with a polyhalo aromatic compound having more than two halogen substituents per molecule, an alkali metal sulfide, an alkali metal carboxylate or a lithium halide, an alkali metal hydroxide, and N-methyl-2-pyrrolidone at polymerization conditions with the addition of carbon dioxide either during the polymerization or upon completion of the polymerization but prior to removal of N-methyl-2-pyrrolidone by distillation at elevated temperatures thereby producing a polymer, after washing, of lower melt flow than is obtained without the addition of carbon dioxide. In an embodiment of the invention the use of carbon dioxide makes unnecessary the use of vacuum distillation in recovering N-methyl-2-pyrrolidone from the reaction effluent and also makes possible improved recovery of N-methyl-2-pyrrolidone.

Growing community of inventors

Bartlesville, OK, United States of America

James T Edmonds, Jr