Bisphenol A-derived resins

Epichlorohydrin and Bisphenol A-Derived Resins. The most widely used epoxy resins are diglycidyl ethers of bisphenol A [25068-38-6] (1) derived from bisphenol A [80-05-7] and epichlorohydrin [106-89-8],... 

Epichlorohydrin and Bisphenol A-Derived Resins. Liquid epoxy resins maybe synthesized by a two-step reaction of an excess of epichl orohydrin to bisphenol A in the presence of an alkaline catalyst. The reaction consists initially in the formation of the dichi orohydrin of bisphenol A and further reaction by dehydrohalogenation of the intermediate product with a stoichiometric quantity of alkaH. 

Epichlorohydrin and Bisphenol A-Derived Resins. The most widely used epoxy resins are diglycidyl ethers of bisphenol A... 

Triglycidylp-AminophenoI DerivedResins. Resins derived from triglycidyl -aminophenol [5026-74-7] originally developed by Union Carbide Corp. (7) are currendy marketed by CIBA-GEIGY. Synthesis is conducted by reaction of epichlorohydrin with the phenoHc and amino groups followed by dehydrohalogenation. The product is a viscous Hquid (1.5-5 Pa-s (15—50 P) at 25 C) which is considerably more reactive toward amines than standard bisphenol A-derived resins. The epoxy equivalent weight is 105—114. 

The bisphenol A-derived epoxy resins are most frequendy cured with anhydrides, aUphatic amines, or polyamides, depending on desired end properties. Some of the outstanding properties are superior electrical properties, chemical resistance, heat resistance, and adhesion. Conventional epoxy resins range from low viscosity Hquids to soHd resins. 

The cycloahphatic products are generally Hquids of lower viscosity than the standard glycidyl ether resins. The peroxidized resins contain no chlorine and low ash content and their ring-contained oxirane group (cyclohexene oxide type) reacts more readily with acidic curing agents than the bisphenol A-derived epoxy resins. 

Bisphenol A-derived epoxy resins, 10 356 Bisphenol A epoxy novolacs, 10 370 Bisphenol A manufacture, microporous catalysts and, 14 420 Bisphenol A moiety, 10 355-356 Bisphenol A polycarbonate (BPA-PC),... 

Standard bisphenol-A fumarate resins are derived from the propylene glycol or oxide diether of bisphenol-A and fumaric acid. The aromatic structure provided by the bisphenol-A provides several benefits. Thermal stability is improved, and the heat distortion point of the resin is mainly raised from the more rigid nature of the aromatic structure. The number of interior chain ester groups is reduced so the resistance to hydrolysis and saponification is increased. Bisphenol A fumarate polyesters have the best hydrolysis resistance of any commercial unsaturated polyester. 

Miscellaneous Applications. Ben2otrifluoride derivatives have been incorporated into polymers for different appHcations. 2,4-Dichloroben2otrifluoride or 2,3,5,6-tetrafluoroben2otrifluoride [651-80-9] have been condensed with bisphenol A [80-05-7] to give ben2otrifluoride aryl ether semipermeable gas membranes (336,337). 3,5-Diaminoben2otrifluoride [368-53-6] and aromatic dianhydrides form polyimide resins for high temperature composites (qv) and adhesives (qv), as well as in the electronics industry (338,339). 

The largest outlet for phenol worldwide is phenoHc resins (qv). However, the growth rate of bisphenol A is higher than that of the other significant derivatives and is projected to become the principal use of phenol in the future (see Epoxy resins Polycarbonates). Table 6 shows the portion of world phenol demand by use and the anticipated growth rate of the uses. 

Other minor raw materials are used for specific needs. Eumaric acid [110-17-8] the geometric isomer of maleic acid, is selected to maximize thermal or corrosion performance and is the sole acid esterified with bisphenol A diol derivatives to obtain optimum polymer performance. CycloaUphatics such as hydrogenated bisphenol A (HBPA) and cyclohexanedimethanol (CHDM) are used in selective formulations for electrical apphcations. TetrahydrophthaUc anhydride [85-43-8] (THPA) can be used to improve resiUence and impart useful air-drying properties to polyester resins intended for coating or lining apphcations. 

Methacrylate monomers are most effective with derivatives of bisphenol A epoxy dimethacrylates, in which the methacrylate—methacrylate cross-linking reaction proceeds at a much faster pace than with styrene monomer. This proves beneficial in some fabrication processes requiring faster cure, such as pultmsion and resin-transfer mol ding (RTM). 

Polynuclear Phenol—Glycidyl Ether-Derived Resins. This is one of the first commercially available polyfunctional products. Its polyfunctionahty permits upgrading of thermal stabiUty, chemical resistance, and electrical and mechanical properties of bisphenol A—epoxy systems. It is used in mol ding compounds and adhesives. 

Phenol was the 33rd highest-volume chemical. The 1994 U.S. production of phenol was approximately 4 billion pounds. The current world capacity is approximately 15 billion pounds. Many chemicals and polymers derive from phenol. Approximately 50% of production goes to phenolic resins. Phenol and acetone produce bis-phenol A, an important monomer for epoxy resins and polycarbonates. It is produced by condensing acetone and phenol in the presence of HCI, or by using a cation exchange resin. Figure 10-8 shows the Chiyoda Corp. bisphenol A process. 

Substituted phenols such as cresols, p-fcrf-butylphenol, / -phcnylphenol, resorcinol, and cardanol (derived from cashew nut shells) have also been used as precursors for phenolic resins. Alkylphenols with at least three carbons in the substituent lead to more hydrophobic phenolic resins that are compatible with many oils, natural resins, and rubbers.7 Such alkylphenolic resins are used as modifying and crosslinking agents for oil varnishes, as coatings and printing inks, and as antioxidants and stabilizers. Bisphenol-A (2,2-p-hydroxyphenylpropane),... 

Phenol is also used to manufacture several important monomers. Bisphenol A, a phenol derivative, is used to make very strong polycarbonate plastics and epoxy resins (the kind you buy in two tubes and mix to make glue). Ocher applications of epoxy resins include paints, fiberglass binder, and construction adhesives. 

Bisphenol A, a compound highly used in the production of epoxy resins and polycarbonate plastics, forms monochloro-, dichloro, trichloro-, and tetrachloro derivatives when chlorinated [127], Its reaction with ozone produces as major transformation products, catechol, orthoquinone, muconic acid derivatives of bisphenol A, benzoquinone, and 2-(4-hydroxyphenyl)-propan-2-ol [128],... 

All the materials in this study are commercially available and were used as received. The compositions of the mixtures are given in Table I. The components can be described as follows Resin is a proprietary blend of acrylated epoxy resins with an number average molecular weight (Mn) of "4800, based on acrylated diglycidyl bisphenol A, DGEBAcr is the diacrylate derivative of diglycidyl bisphenol A, IBOA is isobomyl acrylate, TMPTA is trimethyloltriacrylate and DMPA is 2,2-dimethoxy-2-phenyl acetophenone. 

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