Bisphenol disodium salt

The first aromatic sulfone polymer produced commercially was introduced as Bakelite polysulfone but now is sold by Union Carbide under the trade name Udel. It is made by reaction of the disodium salt of bisphenol A (BPA) with 4,4 -dichIorodiphenyl sulfone in a mixed solvent of chlorobenzene and dimethyl sulfoxide (eq. 12). 

DMSO is an effective solvent for the polymerization as it affords good solubiUty for both the polymer and disodium bisphenol A [2444-90-8]. Typical polymerization temperatures for polysulfone are in the range 130—160°C. At temperatures below 130°C, the polymerization slows down considerably due to poor solubiUty of the disodium bisphenol A salt. 

Solvent for Displacement Reactions. As the most polar of the common aprotic solvents, DMSO is a favored solvent for displacement reactions because of its high dielectric constant and because anions are less solvated in it (87). Rates for these reactions are sometimes a thousand times faster in DMSO than in alcohols. Suitable nucleophiles include acetyUde ion, alkoxide ion, hydroxide ion, azide ion, carbanions, carboxylate ions, cyanide ion, hahde ions, mercaptide ions, phenoxide ions, nitrite ions, and thiocyanate ions (31). Rates of displacement by amides or amines are also greater in DMSO than in alcohol or aqueous solutions. Dimethyl sulfoxide is used as the reaction solvent in the manufacture of high performance, polyaryl ether polymers by reaction of bis(4,4 -chlorophenyl) sulfone with the disodium salts of dihydroxyphenols, eg, bisphenol A or 4,4 -sulfonylbisphenol (88). These and related reactions are made more economical by efficient recycling of DMSO (89). Nucleophilic displacement of activated aromatic nitro groups with aryloxy anion in DMSO is a versatile and useful reaction for the synthesis of aromatic ethers and polyethers (90). 

It is prepared from the polycondensation of the disodium salt of bisphenol A and 4,4-dichlorodiphenyl sulfone in a polar aprotic solvent such as dimethyl sulfoxide (26). 

Chemical Name 4,4 -(2-pyridinylmethylene)bisphenol bis(hydrogen sulfate) (ester) disodium salt... 

Epoxy adhesives are prepared in two steps. S -2 reaction of the disodium salt of bisphenol A with cpichlorohydrin forms a "prepolymer," which is then "cured" by treatment with a triaminc such as I-I2NCH2CH2NHCH2CH2NEI2-... 

Figure 4. Preparation of the bis-(4-nitrophenyl) ether of bisphenol A via reaction of bisphenol A disodium salt with 4-chloronitrobenzene. Bis salt = biS (4 dihexylaminopyridinium) decane dibromide. Mono salt = N-(2-ethylhexyl) 4-dihexylaminopyridinium mesylate.

Polyetherimides (PEI) are polyimides containing sufficient ether as well as other flexibi-lizing structural units to impart melt processability by conventional techniques, such as injection molding and extrusion. The commercially available PEI (trade name Ultem) is the polymer synthesized by nucleophilic aromatic substitution between 1,3-bis(4-nitrophthalimido) benzene and the disodium salt of bisphenol A (Eq. 2-209) [Clagett, 1986]. This is the same reaction as that used to synthesize polyethersulfones and polyetherketones (Eq. 2-206) except that nitrite ion is displaced instead of halide. Polymerization is carried out at 80-130°C in a polar solvent (NMP, DMAC). It is also possible to synthesize the same polymer by using the diamine-dianhydride reaction. Everything being equal (cost and availability of pure reactants), the nucleophilic substitution reaction is probably the preferred route due to the more moderate reaction conditions. 

Bisphenol-A is present as the disodium salt in the aqueous phase of the two-phase mixture. Phosgene enters the system and dissolves in the organic phase. It is believed that the reaction between phosgene and bisphenol-A occurs at the organic-aqueous interface to form the monochloroformate—Reaction 1—or bischloroformate—Reaction 2— ester of bisphenol-A. The chloroformate esters that form grow to oligomers by reaction with additional bisphenol-A or by self-condensation —Reactions 3 and 4, respectively. 

Bisphenol A disodium salt Bisphenol A sodium salt Diphenylolpropane disodium salt Disodium 4,4 -isopropylidenediphenolate EINECS 219-488-3 HSDB 5660 Phenol. 4,4 -(1-methylethylidene)bis-, disodium salt Phenol. 4,4 -isopropylidenedi-, dIsodium sail Sodium, (isopropylidenebis p-phenyleneoxy))di-. 

The synthesis of poly(ether imide)s by condensation of the disodium salt of bisphenol-A with bis(chlorophthalimide)s under microwave irradiation conditions has been described by Zhang et al. (Scheme 14.21) [50]. The polymerization reactions were performed under phase-transfer catalysis (PTC) conditions in o-dichlorobenzene solution. For this purpose a mixture of 16.12 mmol bis(chloro-phthalimide)s and 16.12 mmol disodium salt of bisphenol-A in 60 mL o-dichlorobenzene with 0.56 mmol hexaethylguanidinium bromide was irradiated in a domestic microwave oven for 25 min and the product was precipitated by addition of methanol. The polymerization reactions, in comparison with those under the action of conventional heating, proceeded rapidly (25 min compared with 4 h at 200 °C) and polymers with inherent viscosities in the range 0.55 to 0.90 dL g were obtained. 

Originally, polycarbonate was produced by interfacial (organic/aqueous) polycondensation of phosgene (COClj) with disodium salt of a bisphenol, such as 2,2-bis(4-hydroxyphenyl)propane (bisphenol A or BPA). Initially, the reaction produces an intermediate chloroformate R0C(0)C1 (Eq. (12.1)), which subsequently reacts with another phenoxide molecule, growing a polymer chain... 

Another (family of linear aromatic polymers is the polysulfones. They are tough, high-temperature-resistant engineering thermoplastics. Polysulfones may be synthesized by the nucleophihc substitution of alkali salts of biphenates with activated aromatic dihalides. A typical example is the preparation of bisphenol A polysulfone (21) from the reaction of disodium salt of bisphenol A with dichlorodiphenyl sulfone ... 

The polymerization reaction involves the initial preparation of the disodium salt of bisphenol A by the addition of aqueous NaOH to bisphenol A in dimethyl sulfoxide (DMSO). A solution of dichlorodiphenyl sulfone is added, and polymerization is carried out at 160°C. 

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