Sulfonic acid containing fluorocarbon vinyl ethers
Claim OF THE DISCLOSURE Vinyl ethers of the formula CF =CFOCF CFXSO Me, wherein X is F or CF and Me is alkali metal, are made by contacting and reacting an alkali metal alkoxide with a compound of the formula in an inert organic solvent. The vinyl ether reaction products can be copolymerized with fluorocarbon monomers, e.g., tetrafluoroethylene, to form ionically conductive material for use as fuel cell membranes. This invention relates to a process for preparing certain sulfonyl-containing fluorocarbon vinyl ethers.
It has now been discovered that certain sulfonyl-containing fluorocarbon vinyl ethers can be obtained by contacting and reacting an alkali metal alkoxide with a cyclic sulfonic of the formula wherein X is F or 0P in an inert organic liquid which is a solvent for the sulfonic. The resultant vinyl ether salts have the formula CF =CFOCF CFXSO Me, wherein X has the above-indicated meaning and me is the alkali metal of the alkoxide.
Preparation of sulfonic acid containing fluorocarbon vinyl ethers
The vinyl ether salts can be converted to the corresponding sulfonyl chloride (SOCl) by reaction with P01 and in turn to the corresponding sulfonyl fluoride (-SO F) by reaction of the sulfonyl chloride with NaF.
The vinyl ether salts can be converted to the corresponding sulfonic acid (-SO H) by reaction with a strong inorganic acid such as H SO .The conversion reactions, i.e., salt to halide, acid, or other derivative, can be practiced on polymer containing repeat units derived from the vinyl ether. Copolymers containing the sulfonic acid form of the vinyl monomer prepared herein can be used as ionically conductive membranes in such applications as fuel cells and batteries as disclosed in U.S. patent application Ser.
The process of the present invention is conducted merely by adding the alkoxide and cyclic sulfone to the inert organic solvent in about equimolar quantities conveniently at ambient temperatures, but higher or lower temperatures such as from -20 to 200 C. can be used. The reaction can also be conducted at atmospheric pressure, although higher or lower pressures can be used.
The solvent should also be anhydrous. Examples of suitable solvents include benzene and substituted benzene such as chlorobenzene, nitrobenzene, ethers such as diethyl ether and diphenyl ether, and cyclic ethers such as Tetrahydrofuran. Sufficient solvent is used to dissolve the amount of sulfone reactant that is present.
Sulfonic acid and fluorocarbon vinyl ethers
The alkoxide reactant can be represented by the formula ROMe where in me any alkali metal, preferably Na or K, is and R is any hydrocarbon group which does not interfere with the reaction.
The alkoxide reactant need not be soluble in the particular solvent used. Examples of suitable alkoxides include sodium methoxide, potassium methoxide, cesium methoxide, lithium methoxide, rubidium methoxide, sodium ethoxide, potassium butoxide, and sodium phen oxide.
Hydroxybenzophenone containing sulfonic acid groups
sulfonic acids having sulfone groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring.
Acrylamido-sulfonic acid polymers and their use
The present disclosure is directed to polymers and copolymers of acrylamido-sulfonic acid compounds and their use basically as dispersants for particles contained in aqueous systems. Exemplary of the sulfonic acid compound is 2-acrylamido-2-methylpropane sulfonic acid, or water-soluble salt thereof; and representative of the co-monomers which the acid is copolymerized with can be mentioned, acrylic acid and derivatives thereof, acrylamide and derivatives thereof, vinyl pyrrolidone, etc. The polymers and copolymers are specifically useful in dispersing water-insoluble compounds of iron, calcium, magnesium and aluminum and such commonly occurring particles of slit and clay.
Organic sulfonic acid oligomers
Organic disulfonic acids are produced by heating a sulfonate monomer at a temperature ABOVE 110* C. in the substantial absence of water. Olefin sulfonation product mixtures, hydroxyalkane sulfonic acids, alkane sultones, alkene sulfonic acids and mixtures thereof are oligomerized under these conditions.
Sulfonic acid group-containing polyvinyl alcohol, solid polymer electrolyte, composite polymer membrane, method for producing the same and electrode, Sulfonic acid group-containing polyvinyl alcohol having crosslinked structures, which is obtained by heat treating a mixed solution of polyvinyl alcohol, a sulfonating agent and a crosslinking agent, a composite polymer membrane excellent in proton conductivity and methanol barrier property, which is obtained by applying the mixed solution to a water-absorptive or hydrophilic polymer membrane, followed by sulfonation and crosslinking, and an electrode for a fuel cell excellent in catalytic activity, which comprises sulfonic acid group-containing polyvinyl alcohol having crosslinked structures and fine catalyst particles carried on porous particles.