Phenolic resins phenol derivatives

Some other phenol derivatives are somewhat local in appHcation. Eor example, aniline is produced from phenol at only two plants, one in Japan and one in the United States. Likewise, phenol is used in the production of nylon, via caprolactam (qv) or adipic acid (qv) by only one United States producer and one European producer. These markets, like the phenoHc resin and polycarbonate markets, are quite cycHcal. Thus, the entire phenol market tends to be cycHcal and closely tied to the housing and automotive markets. 

Prices of phenolic resins vary substantially depending on the appHcation. In 1995, the price of general-purpose and semisoHds was 1.50— 1.80/kg, whereas epoxy-hardener grades can exceed 2.20/kg. Because raw materials of phenoHc resins are derived from cmde oil and natural gas, the prices of phenohc resins depend on the prices of these resources. 

Alkylated phenol derivatives are used as raw materials for the production of resins, novolaks (alcohol-soluble resins of the phenol—formaldehyde type), herbicides, insecticides, antioxidants, and other chemicals. The synthesis of 2,6-xylenol [576-26-1] h.a.s become commercially important since PPO resin, poly(2,6-dimethyl phenylene oxide), an engineering thermoplastic, was developed (114,115). The demand for (9-cresol and 2,6-xylenol (2,6-dimethylphenol) increased further in the 1980s along with the growing use of epoxy cresol novolak (ECN) in the electronics industries and poly(phenylene ether) resin in the automobile industries. The ECN is derived from o-cresol, and poly(phenylene ether) resin is derived from 2,6-xylenol. 

Carbon, hydrogen and possibly oxygen Resin and derivatives Natural drying oils Cellulose derivatives Alkyd resins Epoxy resins (uncured) Phenol-formaldehyde resins Polystyrene Acrylic resins Natural and synthetic rubbers Carbon monoxide Aldehydes (particularly formaldehyde, acrolein and unsaturated aldehydes) Carboxylic acids Phenols Unsaturated hydrocarbons Monomers, e.g. from polystyrene and acrylic resins... 

Group of plastics whose resins are derived from the condensation of phenols (e.g., phenol and cresol, with aldehydes). 

Cured phenol-formaldehydes are resistant to attack by most chemicals. Organic solvents and water have no effect on them, though they will swell in boiling phenols. Simple resins are readily attacked by sodium hydroxide solutions, but resins based on phenol derivatives, such as cresol, tend to be less affected by such solutions. Simple phenol-formaldehyde polymers are resistant to most acids, though formic and nitric acids will tend to attack them. Again, cresol-based polymers have resistance to such attack. 

Cardanol, a main component obtained by thermal treatment of cashew nut shell liquid (CNSL), is a phenol derivative having mainly the meta substituent of a C15 unsaturated hydrocarbon chain with one to three double bonds as the major. Since CNSL is nearly one-third of the total nut weight, a great amount of CNSL is obtained as byproducts from mechanical processes for the edible use of the cashew kernel. Only a small part of cardanol obtained in the production of cashew kernel is used in industrial fields, though it has various potential industrial utilizations such as resins, friction-lining materials, and surface coatings. Therefore, development of new applications for cardanol is very attractive. 

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. 

Baekeland recognized that the trifunctional phenol would produce network polymers and therefore used difunctional ortho- or para-substituted phenols to produce linear paint resins. Linear thermoplastic products are formed by alkaline or acid condensation of formaldehyde with phenol derivatives such as /r-cresol (structure 4.81). 

Title Novel Sulfur-containing Phenolic Resin, Process for Preparing the Same, Phenol Derivatives Having Thioether Structure or Disulfide Structure, Process for Preparing the Same and Epoxy Resin Composition Adhesive... 

Phenolic derivatives were prepared and then converted into thioether analogs using ethanedithol followed by oxidation of this intermediate to the disulfide. Phenolic resins were prepared by electrophilic substitution of allyl phenol derivatives with formaldehyde and then flee radically copolymerizing with ethanedithol. Epoxidation was performed using epichlarohydrine. 

Under comparable reaction conditions the much more reactive formaldehyde and phenol do not only give the para- but also the ortho-substituted phenol derivative. This reaction ultimately leads to the three-dimensional network of formaldehyde/phenol condensation resins such as Bakelite and to related, well-defined receptor molecules known as cahxarenes. 

Benzoic Acid. Benzoic acid can be produced by the LPO of toluene using a catalyst such as cobalt or manganese. Domestic production of benzoic acid was about 130 million lb in 2000. Of this amount, about one half went to make phenol or phenolic derivatives. Other uses are in the synthesis of caprolactam and terephthalic acid, and as food additive, and as a plasticizer and resin intermediate. 

Other phenol derivatives that are used to form the backbone of an epoxy resin include bisphenol E, bisphenol F, resorcinol, brominated bisphenols, and more highly functionalized molecules such as tetrakisphenylolethane. Alcohols, amines, and carboxylic acids may be combined with epichlorohydrin to give a range of diglycidyl ether based epoxy resins. Non-aromatic, commercially available epoxides are produced by peracid epoxidation of alkenes and dienes, such as vinyl cyclohexene and esters of cyclohexane carboxylic acids [23]. The chemical formulas for two common uncured polymers are shown below ... 

Three novel model compounds, bis(2-hydroxy-4,6-dimethylphenyl)methane (46), (2-hydroxy-4,6-dimethylphenyl-4 -hydroxy-2, 6 -dimethylphenyl)methane (47) and bis(4-hydroxy-2,6-dimethylphenyl)methane (48), were synthesized from 3,5-dunethylphenol. These were used to show that a resole-type resin formed from 3,5-dimethylphenol had a highly condensed, predominately linear structure, linked by ortho-ortho and ortho-para methylene bridges. This is quite unlike the behaviour of phenol-derived resole resins. 

Products of coupling reactions between phenolic derivatives and formaldehyde have been used to produce resins 1 that have been used widely as bulk chemicals Current address Unilever Research Development Port Sunlight, Bebington, CH63 3JW. UK. 

The benzylic ester resin 20 derived from Merrifield resin was described in the 1970s by Leznoff and coworkers for the selective synthesis of monotrityl ethers of symmetrical aliphatic diols, phenols and porphyrins [66-68]. More recently, the... 

Km Kem . [Kenrich Petrochemicals] Cun l phenol derivs. modifier for epoxy, fu and phenolic resins epoxy cure acoeleratm chemical hiteiii -ate. 

Phenoxyl radicals (Ph-0 ) are known not to iiutiate radical polymerization in most cases (2) and may be RTCP catalysts if they can activate Polymer-I. Based on this idea, we attempted to use phenol derivatives as catalysts, thus extending the element of the catalyst to O (Figure 1). Notably, the phenols include common antioxidants for foods and resins and natural compounds such as vitamins (Figure 1). Their commonness (hence cheapness) and environmental safety may be highly attractive for practical applications. In this paper, we will present the results of the styrene and methyl methacrylate (MMA) polymerizations, along with a mechanistic study. 

Brominated flame retardants (BFRs) are a structurally diverse group of compounds including aromatics, cyclic aliphatics, phenolic derivatives, ahphatics, and phthahc anhydride derivatives (Figure 31.3). The most common BFRs are tetrabromobisphenol A (TBBPA), polybrominated diphenyl ethers (PBDE), hexabromocyclododecane (HBCD), and polybrominated biphenyls (PBB). The primary use of TBBPA is as reactive additive in epoxy resin circuit boards, while decabromodiphenyloxide (DBDO) is primarily used in high impact polystyrene for electronic enclosures. PBDEs are typically used as the additive type of flame retardant in high impact polystyrene, acrylonitrile butadiene styrene, flexible polyurethane foam, textile coatings, wire and cable insulation and electrical connectors. 

Other epoxy resins are also being manufactured, but their commercial j utilization is not so far advanced as those based on bisphenol A and i epichlorohydrin. For instance, resorcinol and a mixture of diphenol-poly-(hydroxyphenyl)-pentadecanes, obtained by the addition reaction of phenol with an unsaturated phenol derived from cashew-nut oil (see structure below) can be reacted with epichlorohydrin to produce epoxy resins. ... 

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