Condensation polymer phenol-formaldehyde

A polymer satisfying either or both of the above definitions is classified as a condensation polymer. Phenol-formaldehyde, for example, satisfies the first definition but not the second. Some condensation polymers along with their repeating units and condensation reactions by which they can be synthesized are shown in Table 1.2. Some high-performance polymers prepared by polycondensation are listed in Table 1.3. 

To overcome such problems, an alternative definition has been introduced. According to this definition, polymers whose main chains consist entirely of C-C bonds are classified as addition polymers, whereas those in which heteratoms (O, N, S, Si) are present in the polymer backbone are considered to be condensation polymers. A polymer which satisfies both the original definition (of Carothers) and the alternative definition or either of them, is classified as a condensation polymer. Phenol-formaldehyde condensation polymers, for example, satisfy the first definition but not the second. 

In far too many instances trade-name polymer nomenclature conveys very little meaning regarding the structure of a polymer. Many condensation polymers, in fact, seem not to have names. Thus the polymer obtained by the step polymerization of formaldehyde and phenol is variously referred to a phenol-formaldehyde polymer, phenol-formaldehyde resin, phenolic, phenolic resin, and phenoplast. Polymers of formaldehyde or other aldehydes with urea or melamine are generally referred to as amino resins or aminoplasts without any more specific names. It is often extremely difficult to determine which aldehyde and which amino monomers have been used to synthesize a particular polymer being referred to as an amino resin. More specific nomenclature, if it can be called that, is afforded by indicating the two reactants as in names such as urea-formaldehyde resin or melamine-formaldehyde resin. 

A condensation polymer is one in which the repeating unit lacks certain atoms which were present in the monomer(s) from which the polymer was formed or to which it can be degraded by chemical means. Condensation polymers are formed from bi- or polyfunctional monomers by reactions which involve elimination of some smaller molecule. Polyesters (e.g., 1-5) and polyamides like 1-6 are examples of such thermoplastic polymers. Phenol-formaldehyde resins (Fig. 5-1) are thermosetting condensation polymers. All these polymers are directly synthesized by condensation reactions. Other condensation polymers like cellulose (1-11) or starches can be hydrolyzed to glucose units. Their chemical structure indicates that their repealing units consist of linked glucose entities which lack the elements of water. They are also considered to be condensation polymers although they have not been synthesized yet in the laboratory. 

X HE SCIENCE AND TECHNOLOGY of polymers have had a profound influence on the quality of life in the 20th century. Indeed, the utility of polymeric materials was widely appreciated long before scientists understood the molecular basis of this class of materials. Early telephone handsets, for example, were made from a condensation polymer of formaldehyde and phenol, but it was many years later before the macromolecular concept of a polymer molecule was proposed, much less accepted. 

Phenol is mainly derived from benzene, but can also be obtained from propylene. It serves as the basis for several important monomers, in addition to its direct use as a reactive monomer via condensation with formaldehyde. This first man-made polymer, phenol-formaldehyde, appeared in 1901 and bears the trademark Bakelite , after its inventor Bakeland. By reacting phenol with acetone, bis-phenol A is obtained. This serves as the basis for the manufacture of epoxy and polycarbonate. 

Platinum-group metals (qv) form complexes with chelating polymers with various 8-mercaptoquinoline [491-33-8] derivatives (83) (see Chelating agents). Hydroxy-substituted quinolines have been incorporated in phenol—formaldehyde resins (84). Stannic chloride catalyzes the condensation of bis(chloromethyl)benzene with quinoline (85). 

Most processors of fiber-reinforced composites choose a phenol formaldehyde (phenoHc) resin because these resins are inherently fire retardant, are highly heat resistant, and are very low in cost. When exposed to flames they give off very Htde smoke and that smoke is of low immediate toxicity. PhenoHc resins (qv) are often not chosen, however, because the resole types have limited shelf stabiHty, both resole and novolac types release volatiles during their condensation cure, formaldehyde [50-00-0] emissions are possible during both handling and cure, and the polymers formed are brittle compared with other thermosetting resins. 

Though less prevalent than addition polymerization, condensation polymerization produces important polymers such as polyesters, polyamides (nylons), polycarbonates, polyurethanes, and phenol-formaldehyde resins (Chapter 12). 

Acid catalysts, such as metal oxides and sulfonic acids, generally catalyze condensation polymerizations. However, some condensation polymers form under alkaline conditions. For example, the reaction of formaldehyde with phenol under alkaline conditions produces methy-lolphenols, which further condense to a thermosetting polymer. 

Phenol-formaldehyde resins are the oldest thermosetting polymers. They are produced by a condensation reaction between phenol and formaldehyde. Although many attempts were made to use the product and control the conditions for the acid-catalyzed reaction described by Bayer in 1872, there was no commercial production of the resin until the exhaustive work by Baekeland was published in 1909. In this paper, he describes the product as far superior to amber for pipe stem and similar articles, less flexible but more durable than celluloid, odorless, and fire-resistant. ° The reaction between phenol and formaldehyde is either base or acid catalyzed, and the polymers are termed resols (for the base catalyzed) and novalacs (for the acid catalyzed). 

One of the earliest, and still one of the most important, polymers is the material known as Bakelite, which is a condensation polymer of phenol, C6H5OH, and formaldehyde, H2C=0. Formaldehyde will react with phenol to produce the following compounds when the ratio is 1 1 ... 

Condensation polymers commercial, 20 392-393t phenol-formaldehyde, 70 409 Condensation polymerization, of silicone fluids, 22 573... 

Some other example of condensation polymers are Dacron (a polymer of ethylene glycol), polyester (a polymer of p-terephthalic acid), Bakelite (a polymer of phenol and formaldehyde). 

The workhorse of the VLSI industry today is a composite novolac-diazonaphthoquinone photoresist that evolved from similar materials developed for the manufacture of photoplates used in the printing industry in the early 1900 s (23). The novolac matrix resin is a condensation polymer of a substituted phenol and formaldehyde that is rendered insoluble in aqueous base through addition of 10-20 wt% of a diazonaphthoquinone photoactive dissolution inhibitor (PAC). Upon irradiation, the PAC undergoes a Wolff rearrangement followed by hydrolysis to afford a base-soluble indene carboxylic acid. This reaction renders the exposed regions of the composite films soluble in aqueous base, and allows image formation. A schematic representation of the chemistry of this solution inhibition resist is shown in Figure 6. 

Phenol - formaldehyde polymers are the oldest synthetic polymers. These are obtained by the condensation reaction of phenol with formaldehyde in the presence of either an acid or a base catalyst. The reaction starts with the initial formation of o-and/or p-hydroxymethylphenol derivatives, which further react with phenol to form compounds having rings joined to each other through -CH2 groups. The initial product could be a linear product - Novolac used in paints. 

While condensation polymers account for only a modest fraction of all synthetic polymers, most natural polymers are of the condensation type. The first all-synthetic polymer, Bakelite, was produced by the stepwise polycondensation of phenol and formaldehyde. 

Baekeland found that a relatively stable resole prepolymer could be obtained by the controlled condensation of phenol and formaldehyde under alkaline conditions. These linear polymers of phenol-formaldehyde (PF) may be converted to infusible cross-linked polymers called resites by heating or by the addition of mineral acids. As shown in structure 4.80, the initial products obtained when formaldehyde is condensed with phenol are hydroxybenzyl alcohols. The linear resole polymer is called an A-stage resin, and the cross-linked resite is called a C-stage resin. 

Highly cross-linked condensation materials form the basis for a number of important adhesives and bulk materials, especially phenolic and amino plastics. Most of these products have formaldehyde as one of their starting reactants. These materials are thermosets that decompose prior to melting, and are therefore more difficult to recycle than most condensation polymers that are thermoplastics and do melt prior to decomposition. 

Bakelite Polymer produced by condensation of phenol and formaldehyde first by Leo Baekeland, bifnnctional Molecule with two active functional groups, bisphenol A 2,2 -bis(4-hydroxphenol)propane. 

Bayer, A. 1878. Phenol-formaldehyde condensates. Ber. Bunsenges. Phys. Chem., 5 280, 1094. Brunelle, D.J. and Korn, M. 2005. Advances in Polycarbonates. Oxford University Press, New York. Carothers, W.H. 1929. An introduction to the general theory of condensation polymers. J. Amer. Chem. Soc., 51 2548. 

Little rhyme or reason is associated with many of the common names of polymers. Some names are derived from the place of origin of the material, such as Hevea brasilliensis literally rubber from Brazil —for natural rubber. Other polymers are named after their discoverer, as is Bakelite, the three-dimensional polymer produced by condensation of phenol and formaldehyde, which was commercialized by Leo Baekeland in 1905. 

BakeUte Polymer produced by the condensation of phenol and formaldehyde, cellulose Naturally occurring carbohydrate polymer, elastomer Rubber. 

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