Glycidyl compounds

The PGCBA resin is composed of various components, but the important one is the Tetra glycidyl compound of bisphenol A (abbreviated TGCBA)... 

J. Luston u. F. Vass, Makromol. Chem., Macromol. Symp. 27, 231-237 (1989) . .Functional Derivatives of Sterically Hindered Amines. 1. Glycidyl Compounds". 

Seiler, J.P (1984) The mutagenicity of mono- and difunctional aromatic glycidyl compounds. Mutat. Res., 135. 159-167... 

Exo and endo oxiranes of bicyclo[2.2.1]heptane can be well differentiated on the basis of their spectra.The effect of the molecular asymmetry on the chemical shift of the carbon in 0- and A -glycidyl compounds has been investigated. In the study of stereoisomeric epoxyspirocyclohexane derivatives, the effects of the equatorial and axial oxiranes have been observed on the carbon atoms of the cyclohexane ring. ... 

Fig. 5. Preparation of aryl glycidyl compounds by a peroxygen route...

The epoxidation of an appropriate O-allyl group gives the appropriate glycidyl compounds without the detrimental by-products of the epichlorhydrin route. However this transformation is not an easy one and whilst it works well for mono-allyl compounds, polyallyl substrates offer more problems. 

Fig. 1. Fragments of the network formed by the reaction of glycidyl compounds with amines, anhydrides, segments with carboxylic end groups, and Lewis acids.

It was hard to even guess that the glycidylic compounds discovered by the Swiss chemist P. Kastan in the 1930s would become so significant in 20 years. Many industrial branches would become potential fields of application of these products. Glass fiber-reinforced plastics, a wide variety of adhesives, and numerous elec-troinsulating materials the aeronautics and aerospace industries, electronics, and... 

The general procedure to prepare glycidyl compounds is from alcohols, phenols, or acids and epichlorohydrin. The reaction with bisphenol A, leading to diepoxide 5, is depicted in Scheme 2. 

Ahyl alcohol undergoes reactions typical of saturated, aUphatic alcohols. Ahyl compounds derived from ahyl alcohol and used industriahy, are widely manufactured by these reactions. For example, reactions of ahyl alcohol with acid anhydrides, esters, and acid chlorides yield ahyl esters, such as diahyl phthalates and ahyl methacrylate reaction with chloroformate yields carbonates, such as diethylene glycol bis(ahyl carbonate) addition of ahyl alcohol to epoxy groups yields products used to produce ahyl glycidyl ether (33,34). 

Specialty Epoxy Resins. In addition to bisphenol, other polyols such as aUphatic glycols and novolaks are used to produce specialty resins. Epoxy resins may also include compounds based on aUphatic, cycloaUphatic, aromatic, and heterocycHc backbones. Glycidylation of active hydrogen-containing stmctures with epichlorohydrin and epoxidation of olefins with peracetic acid remain the important commercial procedures for introducing the oxirane group into various precursors of epoxy resins. 

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. 

Vulcanisation can be effected by diamines, polyamines and lead compounds such as lead oxides and basic lead phosphite. The homopolymer vulcanisate is similar to butyl rubber in such characteristics as low air permeability, low resilience, excellent ozone resistance, good heat resistance and good weathering resistance. In addition the polyepichlorohydrins have good flame resistance. The copolymers have more resilience and lower brittle points but air impermeability and oil resistance are not so good. The inclusion of allyl glycidyl ether in the polymerisation recipe produces a sulphur-curable elastomer primarily of interest because of its better resistance to sour gas than conventional epichlorhydrin rubbers. 

Glycidyl ether resins are formed by reaction of epichlorohydrin with polyhydroxy compounds. In addition to the dominant use of bis-phenol A several other polyhydroxy compounds have been used. In particular there has been... 

Although the first and still most important epoxide resins are of the glycidyl ether type, other epoxide resins have been commercially marketed in recent years. These materials are generally prepared by epoxidising unsaturated compounds using hydrogen peroxide or peracetic acid. 

Compared with the experimental values for which was noted a high level of measurement error, a level of agreement was found that is not worse than the disparities found for a lot of compounds, which were the subject of independent measurement. Note in particular the good estimates obtained with two compounds that have relatively complex structures, such as styrene oxide and glycidyl acrylate. Nevertheless, there are two estimates that seem sufficiently different from the experimental values to require explanation. 

An inhibitor during drilling and servicing of oil and gas wells is a condensate of aminopyrazine and an epoxide compound, such as the glycidyl ether of a mixture of Cn to C14 alkanols [604]. 

Another example of interest with regard to the reaction mechanism is the analysis of epoxy groups. Durbetaki60 titrated a-epoxy compounds with HBr (cf., p. 260) in glacial acetic acid with crystal violet as indicator, but the method was slow for glycidyl esters, CH2—CHCH2OOCR. As it concerns a two-step... 

The syntheses of these three compounds share a common route as described by Brickner et al. [53] and Barbachyn et al. [54]. Namely, the coupling reaction of 3,4-difluoronitrobenzene (82) with piperazine, morpholine, or thiomorpholine to yield the corresponding 4-substituted 3-fluoro-nitrobenzene (83), which upon reduction gives rise to the aniline derivative (84). Carbobenzoxy protection of the active nitrogen of 84 using benzyloxy-carbonyl chloride (CbzCl) results in the formation of carbamates 85a and 85b. Treatment of 85a,b with n-BuLi and (i -glycidyl butyrate yields a 5-(R)-... 

The absence of an IR absorption peak around 913 cm1 (10.95 pm) for both 5 and 7 indicates that the glycidyl ether rings are mostly converted into resins through cross-linking.11 Heavily fluorinated compounds, 5 and 7, have very strong IR absorption in the region of 1300-1100 cm1. 

Figure 14.6 Simplified structure for random ethylene-acrylic ester-glycidyl methacrylate terpolymers which are effective rubber tougheners for PET compounds. The ethylene-acrylic ester segments provide elastomeric properties while the glycidyl methacrylate functionalities enable reactive grafting to the PET matrix via the hydroxyl and carboxyl chain ends of the latter...

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