O NH2 C NH2 H2N N N N NH2 XXVII XXVIII NH2 in .NET

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Polymerization of urea and formadehyde yields various methylolureas such as XXIX and a mixture of higher oligomers as was the case for the phenolic prepolymers. The relative
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amounts of the various components is dependent on reaction conditions. The crosslinking reaction involves methylene (XXX), methylene ether (XXXI), and cyclic (XXXII) bridges between urea units [Ebdon and Heaton, 1977; Tomita and Ono, 1979]. As in the
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HOCH2 NH CO NH2 XXIXa (HOCH2)2N CO N(CH2OH)2 XXIXb
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CH2 NH CO N CH2 NH CO NH CH2 O CH2 NH CO NH CH2 N CO NH CH2 XXXI CH2 NH CO N H2C N CO NH CH2 N XXXII N CO NH CH2 CH2
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phenol-formaldehyde system, there is considerable evidence that the assumption of equal reactivity of functional groups is invalid for both urea and formaldehyde [Kumar and Katiyar, 1990; Tomita and Hirose, 1977]. The formation and curing of prepolymers from formaldehyde and melamine (2,4,6-triamino-s-triazine) follows in a similar manner. The United States production of amino plastics was more than 3 billion pounds in 2001. The urea formadehyde polymers account for slightly more than 85% of the total. The amino plastics are similar in properties to the phenolics but are clearer and colorless. They are also harder but have somewhat lower impact strength and resistance to heat and moisture. The melamine resins are better than the ureas in hardness and resistance to heat and moisture. The melamine and urea resins are rated for continuous use at temperatures of 130 150 C and 100 C, respectively. The general applications of the amino and phenolic plastics are the same but there are uses where the amino plastics are superior. The melamine resins nd an important niche due to their combination of clarity and lack of color compared to the phenolics and their superior hardness and heat and moisture resistance compared to
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urea resins. Molding and laminating techniques are used to produce colored dinnerware and dinnerware with decorative patterns. A combination of phenolic and melamine plastics are used to produce decorative laminated plastic sheets for tabletop and counters. The combination gives a superior product a phenolic backing imparts superior mechanical properties while a top melamine layer imparts outstanding clarity and hardness. Amino resins are used to impart crease resistance and wash-and-wear properties to cellulosic fabrics. A garment with its appropriate creases and containing the low-molecular-weight amino resin is heated to achieve curing. Curing involves reaction of the amino resin with hydroxyl groups of the cellulosic fabric, and this sets the garment into its shape. Amino resins also nd extensive as automotive paints; the cheaper ureas are used as primers while the melamines are used as topcoats.
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Epoxy resins or plastics are typically formed by the reaction of epichlorohydrin and bisphenol A [Dewprashad and Eisenbraun, 1994; McAdams and Gannon, 1988] (Eq. 2-177).
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O (n + 2)CH2CHCH2Cl + (n + 1)HO C(CH3)2 OH (n + 2)HCl +
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The reaction actually involves the sodium salt of bisphenol A since polymerization is carried out in the presence of an equivalent of sodium hydroxide. Reaction temperatures are in the range 50 95 C. Side reactions (hydrolysis of epichlorohydrin, reaction of epichlorohydrin with hydroxyl groups of polymer or impurities) as well as the stoichiometric ratio need to be controlled to produce a prepolymer with two epoxide end groups. Either liquid or solid prepolymers are produced by control of molecular weight; typical values of n are less than 1 for liquid prepolymers and in the range 2 30 for solid prepolymers. Epichlorohydrin is reacted with a variety of hydroxy, carboxy, and amino compounds to form monomers with two or more epoxide groups, and these monomers are then used in the reaction with bisphenol A [Lohse, 1987]. Examples are the diglycidyl derivative of cyclohexane-1,2-dicarboxylic acid, the triglycidyl derivatives of p-aminophenol and cyanuric acid, and the polyglycidyl derivative of phenolic prepolymers. Epoxidized diole ns are also employed (Sec. 9-8). A variety of coreactants are used to cure epoxy resins, either through the epoxide or hydroxyl groups [Mezzenga et al., 2000; Mijovic and Wijaya, 1994; Trappe et al., 1991]. Polyamines are the most common curing agent with reaction involving ring-opening addition of amine (Eq. 2-178). Both primary and secondary amines are used; primary amines are more reactive than secondary amines [Glover et al., 1988; Zvetkov, 2002]. Since each nitrogen hydrogen bond is reactive in the curing reaction, primary and secondary amine groups are biand monofunctional, respectively. A variety of amines are used as crosslinking agents, including diethylene triamine f 5 , triethylene tetramine f 6 , 4,40 -diaminodiphenylmethane f 4 , and polyaminoamides (e.g., the diamide formed from diethylene triamine
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