Bisphenol A-glycidyl methacrylate

Numerous thermal analysis studies have been performed by other groups on resin composites, which are used for small anterior restorations that do not experience substantial stress and with caution for posterior teeth because of concern about wear [1-3]. The polymer matrix contains the oligomer bis-GMA (bisphenol A-glycidyl methacrylate) or urethane dimethacrylate, and triethylene glycol dimethacrylate is a diluent. Filler particles are silane-coated for chemical bonding with tire matrix. Free-radical polymerization is carried out by chemical... 

Figure 7 Methacrylates and acrylates widely used In medicine and dentistry (a) PMMA, (b) poly(acrylic acid), (c) pHEMA, (d) poly(2-phenylethyl methacrylate), and (e) 2,2-bls[4-(2-hydroxy-3-methacryloyolxypropoxy)phenyl]propane monomer (BIsGMA) (also called bisphenol A-glycidyl methacrylate).

Bisphenol A glycidyl methacrylate (bis-GMA) is an epoxy-methacrylate. Sensitization occurs in dentists. 

The earliest bone cement was based on poly(methyl methacrylate), introduced around 1960 (107). Now, after more than 40 years, acrylic cements are still the most frequently used method and material for the fixation of total joint prostheses. Important modifications include the replacement of poly (methyl methacrylate) with bisphenol-A-glycidyl methacrylate, bis-GM A, a densely cross-linking material with the structure ... 

Liu et al., 1998b,c) Polyethylene glycol and poly(butylene terephthalate) (PEG/PBT) block copolymer (Liu et al., 1997,1998a) Bisphenol A glycidyl methacrylate (BisGMA) (Santos et al., 2002) Polyethylene (Wang and Bonfield, 2001), high-density polyethylene (HDPE) (Sousa et al., 2003)... 

Some dental composite materials (Kingman et al., 2012) are based on bisphe-nol A-glycidyl methacrylate (bis-GMA) that may also contain other monomer modifiers such as bisphenol A dimethacrylate (bis-DMA) (Fung et al., 2000). BPA itself is not directly used in the composite. It is the bis-DMA and bis-GMA (the prepolymer used can have as much as 70% monomer) in the composite that can be converted into BPA and leached into the sahva of patients (within 1-3 h after dental sealant is applied) (Heisch et al., 2010). The levels reported in saliva are typically low the highest reported is 931 pgA. 

The addition—reaction product of bisphenol A [80-05-07] and glycidyl methacrylate [106-91-2] is a compromise between epoxy and methacrylate resins (245). This BSI—GMA resin polymerizes through a free-radical induced covalent bonding of methacrylate rather than the epoxide reaction of epoxy resins (246). Mineral fillers coated with a silane coupling agent, which bond the powdered inorganic fillers chemically to the resin matrix, are incorporated into BSI—GMA monomer diluted with other methacrylate monomers to make it less viscous (245). A second monomer commonly used to make composites is urethane dimethacrylate [69766-88-7]. 

Unsaturated polyesters having hydroxyl groups can be prepared by the reaction of glycols, maleic anhydride and dicarboxylic acids in more than the stoichiometric amount of glycols/carboxylic acids (13, 34). Edwards discussed the application of isophthalic unsaturated polyester urethane hybrids in conventional molding techniques (13). He also applied the hybrids to foamed products (21). Vinyl esters can be prepared by the reaction of bisphenol A with glycidyl methacrylate (21). 

Methacrylate esters have been prepared by the reaction of methacrylic acid with epoxies such as the diglycidyl ethers of bisphenol A (XXXVII) [37]. Methacrylate esters suitable for anaerobic adhesives have also been prepared by the reaction of glycidyl methacrylate (XXXVIII) with a hydroxyl-terminated polyester [38]. The reaction of isocyanatoethyl methacrylate (XXXIX) with polyols resulted in monomers that could be formulated into anaerobic adhesives and sealants [39]. 

SR 355. See Ditrimethylolpropane tetraacrylate SR 365, SR 376. See Zinc methacrylate SR 378. See Glycidyl acrylate SR 379. See Glycidyl methacrylate SR 395. See Isodecyl acrylate SR 416. See Zinc diacrylate SR 423. See Isobornyl methacrylate SR 439. See n-Hexyl acrylate SR 440. See Isooctyl acrylate SR 444. See Pentaerythrityl triacrylate SR 480. See PEG-10 bisphenol A dimethacrylate... 

Epoxy, bisphenol A Epoxy, bisphenol F Neopentyl glycol diglycidyl ether flooring compounds, industrial Methyl methacrylate flooring modifier Alkyl (C12-14) glycidyl ether floor-sweeping compounds Fuller s earth flotation... 

The addition-reaction product of bisphenol A and glycidyl methacrylate or an epoxy resin and methacrylic acid is bis-GMA 2,2- 7Z5 4-(2-hydroxy-3-methacryloxypropoxy)phenyl propane (Fig. 5). Bis-GMA can therefore be classified as a dimethacrylated epoxy, although it does not contain a reactive epoxy group. Bis-GMA is the most commonly used prepolymer in dental composite restorative materials. Several similar compounds have also appeared as substitutes for Bis-GMA or in addition to it in dental resins. Such dimethacrylates based on bisphenol A with various chain lengths are bis-MA 2,2- fs(4-(metha-cryloxy)phenyl)-propane, bis-EMA 2,2-i7is(4-(2-met-hacryloxyethoxy)phenyl)-propane and bis-PMA 2,2- s(4-(3-methacryloxypropoxy)phenyl)-propane. 

The first epoxy dimethacrylate, known as bis-GMA (2,2-bfs(4-(2-hydroxy-3-methacryloxypropoxy)phenyl)-propane) [CAS 1565-94-2] (Fig. 6), was developed by Bowen in 1956. bis-GMA is manufactured from DGEBA and methacryUc acid or bisphenol A and glycidyl methacrylate (Bowen 1962 Jolanki et al. 1995). Analyses have shown that epoxy di(methacrylate) products may contain DGEBA as an impurity (Kanerva et al. 1989 Henriks-Eckerman and Kanerva 1997). bis-GA (2,2-bfs[4-(2-hydroxy-3-acryloxypropoxy)phenyl]-... 

Because of excessive shrinkage (about 5%), a high coefficient of thermal expansion, and poor abrasion resistance, these materials were replaced by a series of composite materials based on a fundamental patent by Bowen.The polymer portion was a single, densely crosslinked network formed by polymerizing the reaction product of glycidyl methacrylate with bisphenol A. The monomer, known as bis-GMA, had the structure... 

There are very many new applications of polymers in the biomedical field. In Table 13.13, the reaction product of glycidyl methacrylate with bisphenol A, known widely as hw-GMA filled with fumed silicas forms the basis for... 

Reaction of glycidyl acrylate or methacrylate with bisphenol A (catalyzed by dimethyl-/ -toluidine) at 60°C [144]. 

The monomer BisGMA may be obtained by either the reaction of bisphenol A (BPA) and glycidyl methacrylate (GMA), or the reaction of the diglycidyl ether of bisphenol A (DGEBPA) and methacrylic acid (MA). The following reactions take place ... 

The "Bowen-monomer" Bis-GMA may be pictured as the reaction product of bisphenol-A and glycidyl methacrylate. The resultant molecule contains two hydroxyl groups. Recently, analogous monomers have been proposed which do not contain these hydroxyls. Dental restorations made with these monomers are said to be low in water uptake and water solubility. Candidate monomers would be those iit... 

There is a need to further enhance the durability of dental composite restorative and sealant materials. Dimethacrylates such as BIS-GMA (the diadduct of bisphenol A and glycidyl methacrylate) are now widely used to formulate the resin component of these materials. Some of the deficiencies of dental composites and sealants are traceable to impurities and inherent structural imperfections in the monomer systems. Structure-property studies are needed to explore ways of achieving minimal shrinkage on polymerization, reducing water sorption, promoting adhesion, generally optimizing the chemical,... 

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