Octylphenols

Many different types of foaming agents are used, but nonionic surfactants are the most common, eg, ethoxylated fatty alcohols, fatty acid alkanolamides, fatty amine oxides, nonylphenol ethoxylates, and octylphenol ethoxylates, to name a few (see Alkylphenols). Anionic surfactants can be used, but with caution, due to potential complexing with cationic polymers commonly used in mousses. 

Typically, soHd stabilizers utilize natural saturated fatty acid ligands with chain lengths of Cg—C g. Ziac stearate [557-05-1/, ziac neodecanoate [27253-29-8] calcium stearate [1592-23-0] barium stearate [6865-35-6] and cadmium laurate [2605-44-9] are some examples. To complete the package, the soHd products also contain other soHd additives such as polyols, antioxidants, and lubricants. Liquid stabilizers can make use of metal soaps of oleic acid, tall oil acids, 2-ethyl-hexanoic acid, octylphenol, and nonylphenol. Barium bis(nonylphenate) [41157-58-8] ziac 2-ethyIhexanoate [136-53-8], cadmium 2-ethyIhexanoate [2420-98-6], and overbased barium tallate [68855-79-8] are normally used ia the Hquid formulations along with solubilizers such as plasticizers, phosphites, and/or epoxidized oils. The majority of the Hquid barium—cadmium formulations rely on barium nonylphenate as the source of that metal. There are even some mixed metal stabilizers suppHed as pastes. The U.S. FDA approved calcium—zinc stabilizers are good examples because they contain a mixture of calcium stearate and ziac stearate suspended ia epoxidized soya oil. Table 4 shows examples of typical mixed metal stabilizers. 

For monosubstituted alkylphenols, the position of the alkyl radical relative to the hydroxyl function is designated either with a numerical locant or ortho, meta, or para. The alkyl side chain typically retains a trivial name. Thus 4-(l,l,3,3-tetramethylbutyl)phenol, 4-/ f2 octylphenol, and para-tert-octy Tph.eno (PTOP) all refer to stmcture (1). 

Another important apphcation for 4-/ f2 -octylphenol is ia the production of phenoHc resias. Novolak resias based oa 4-/ f2 -octylpheaol are widely used ia the tire iadustry as tackifiers. The tackiaess of these resias biads the many parts of an automobile tire prior to final vulcanization. A specialty use for novolak resias based oa 4-/ f2 -octylpheaol is the productioa of a ziacated resia, which is formulated as a dispersioa ia water and coated onto paper ia combination with eacapsulated leuco dyes to yield carbonless copy paper (see Microencapsulation). Pressure from writing bursts the encapsulated leuco dye, which is converted from its colorless form to its colored form by the ncated resin (53). Novolak resias based oa 4-/ f2 -octylpheaol are also used ia the productioa of specialty printing inks. 

Other apphcatioas for 4-/ f2 -octylpheaol iaclude chaia termination of polycarboaates (54). The properties of low molecular weight polycarboaates used ia injection-molding apphcatioas to form compact disks are enhanced when the polymer is termiaated usiag 4-/ f2 -octylphenoL... 

Another use of 4-/ f2 octylphenol is ia the productioa of uv stabilizers. 4-/ f2 -Octylpheaol reacts with sulfur dichloride to yield the thio-hisphenol derivative, which thea reacts with nickel acetate to form 2,2 -thiobis(4-/ f2 octylphenolate)-A/-butylamiQe nickel [14516-71 -3]. This type of stabilizer is widely used in the production of outdoor carpeting based on polypropylene fibers. Nickel compounds give a green discoloration which limits their apphcatioas. A second class of uv stabilizers based on the benzotriazole stmcture. 2-(2 -hydroxy-5 -/ f2 octylphenyl)benzotriazole [3147-75-9] is produced from 4-/ i -octylphenol (55). 

Di- and Triisobutylcncs. Diisobutylene [18923-87-0] and tnisobutylenes are prepared by heating the sulfuric acid extract of isobutylene from a separation process to about 90°C. A 90% yield containing 80% dimers and 20% trimers results. Use centers on the dimer, CgH, a mixture of 2,4,4-trimethylpentene-1 and -2. Most of the dimer-trimer mixture is added to the gasoline pool as an octane improver. The balance is used for alkylation of phenols to yield octylphenol, which in turn is ethoxylated or condensed with formaldehyde. The water-soluble ethoxylated phenols are used as surface-active agents in textiles, paints, caulks, and sealants (see Alkylphenols). 

The octylphenol condensate is used as an additive to lubricating oils and surface-active agents. Other uses of dimer are amination to octylamine and octyldiphenylamine, used in mbber processing hydroformylation to nonyl alcohol for phthalate production and carboxylation via Koch synthesis to yield acids in formulating paint driers (see Drying). 

Technical-grade chloroform generally contains one or more stabilizers, which vary according to specification requirements. The most common is 50 ppm 2-methyl-2-butene [513-35-9]. Other stabilizers are industrial methylated spirit (0.2%), absolute alcohol (0.6—1%), thymol, /-butylphenol, or -octylphenol (0.0005—0.01%). A representative technical quaUty chloroform contains the following amounts of the indicated substances (maximum) ... 

Non-ionic surfactants used in detergents, paints, herbicides, pesticides and plastics. Breakdown products, such as nonylphenol and octylphenol, are found in sewage and industrial efffuents Products of combustion of many materials Widely used as plasticisers for PVC. Common environmental pollutants... 

A few synthetic substituted phenols are also used in the manufacture of oil-soluble resins. They include p-tert-butylphenol, / -tert-amylphenol, p-tert-octylphenol, /7-phenylphenol and dihydroxyphenylpropane (bis-phenol A). 

Table 17 shows the CMCs of sodium alcohol propoxysulfates at 20°C determined from surface tension measurements by the maximum bubble pressure [127] and Table 18 shows the critical micelle concentrations of sodium pro-poxylated octylphenol and propoxylated nonylphenol sulfates. Surface tension... 

Bangsgaard, K., Madsen, S.S., and Korsgaard, B. (2006). Effect of waterhome exposnre to 4-tert-octylphenol and 17(beta)-estradiol on smoltification and downstream migration in Atlantic salmon, Salmo salar. Aquatic Toxicology 80, 23-32. 

Analogous reactions may be presumed to have taken place in the transformation of a ieri-octylphenol... 

Tanghe T, W Dhooge, W Verstraete (2000) Formation of the metabolic intermediate 2,4,5-trimethyl-2-pentanol during incubation of a Sphingomonas sp. strain with the xeno-estrogenic octylphenol. Biodegradation 11 11-19. 

Ball HA, M Reinhard, PL McCarty (1989) Biotransformation of halogenatednonhalogenated octylphenol polyethoxylate residues under aerobic and anaerobic conditions. Environ Sci Technol 23 951-961. 

Gilsonite is active as a fluid loss additive because the permeability of cement is reduced. Latex additives also act as fluid loss additives. They also act as bonding aids, gas migration preventers, and matrix intensifiers. They improve the elasticity of the cement and the resistance to corrosive fluids [921]. A styrene-butadiene latex in combination with nonionic and anionic surfactants shows less fluid loss. The styrene-butadiene latex is added in an amount up to 30% by weight of the dry cement. The ratio of styrene to butadiene in the latex is typically 2 1. In addition, a nonionic surfactant (octylphenol ethoxylate and polyethylene oxide) or an anionic surfactant, a copolymer of maleic anhydride, and 2-hydroxypropyl acrylate [719] can be added in amounts up to 2%. 

Figure 6.3 Conparlson of the separation of the octylphenol poly(ethylene glycol) ether, Triton X-16S on a packed column, left, and an open tubular column, right, using UV detection. For the packed column separation al0cmx2mmI.D. column packed with Nucleosil C g, d. 3 micrometers, temperature > 170 C, and mobile phase carbon dioxide (2 ml/min] and methanol (0.15 nl/rnin). pressure programmed from 130 to 375 bar in 12 min were used. For the open tubular column separation a 10 m x 50 micrometers I.O., SB-Biphenyl-30, temperature = 175°C, mobile phase carbon dioxide (0.175 ml/min) and 2-propanol (0.0265 ml/min) pressure programmed, 125 bar for 5 min, then ramped from 125 to 380 bar over 19.5 min, and held at 380 bar for 15 min. were used. (Reproduced with permission from ref. 57. Copyright Preston Publications, Inc.) ...

Free-radical scavenger n-Butylamine nickel-2,2 -thio-bis-(4-t-octylphenolate) P, Ni, S... 

FIGURE 18.2 Capillary gel electrophoresis separation of an octylphenol ethoxylate sulfate (with an ethylene oxide chain length from 1 to 8). Run conditions pH 8.3 (100 mM tris-borate, 7 M urea) 50 pm x 75 cm J W polyacrylamide gel capillary (PAGE-5, 5%T, and 5%C) run at 20 kV with a 5kV injection for 5 s UV detection at 260nm. 

Surfactants are separated according to adsorption or partitioning differences with a polar stationary phase in NPLC. This retention of the polar surfactant moiety allows for the separation of the ethylene oxide distribution. Of all the NPLC packings that have been utilized to separate nonionic surfactants, the aminopropyl-bonded stationary phases have been shown to give the best resolution (Jandera et al., 1990). The separation of the octylphenol ethoxylate oligomers on an amino silica column is shown in Fig. 18.4. Similar to the capabilities of CE for ionic surfactants, the ethylene oxide distribution can be quantitatively determined by NPLC if identity and response factors for each oligomer are known. 

Similar results were previously seen with a similar column and a gradient (Ibrahim and Wheals, 1996). Although PEG was not analyzed in this work, nonylphenol ethoxylates eluted after octylphenol ethoxylates, suggesting an alkyl contribution to retention. Since AE s have both a hydrophobic and a hydrophilic section, the alkyl portion may be interacting with the hydrophobic siloxane functionality and the EO portion may be interacting with the hydrophilic silanol functionality of the silica. 

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