Plasticizers phthalate

Phtlialaldehydic acid Phthalated gelatin Phthalate esters Phthalate plasticizers Phthalates... 

Emissions During Plasticizer Production and Distribution. Phthalate plasticizers are produced by esterification of phthaUc anhydride in closed systems hence losses to atmosphere are minimal. Inquiries of all the principal plasticizer producers indicate a maximum total emission in Western Europe of 220 t/yr, 90% of which is to the water compartment. This level is expected to decrease in the future due to increa sing plant water treatment. 

The growth of demand for benzoic acid is expected to increase at a rate of between 1 and 2% per year (17). Glycol dibenzoate plasticizers have been growing at close to 10% annually for the past several years, in part due to environmental concerns with regard to phthalate plasticizers (qv). The growth of the diet soft drink market has increased the demand for sodium and potassium benzoates (17). 

Preplastici d. A plasticizer can be iacorporated iato the mbber duriag the manufacturiag process. By adding a phthalate plasticizer to the mbber latex prior to coagulation and drying, the NBR producer can prepare a mbber that is particularly well suited to low hardness appHcations such as roUs (21). 

Plasticizers. Plasticizers are materials that soften and flexibilize inherently rigid, and even britde polymers. Organic esters are widely used as plasticizers in polymers (97,98). These esters include the benzoats, phthalates, terephthalates, and trimeUitates, and aUphatic dibasic acid esters. Eor example, triethylene glycol bis(2-ethylbutyrate) [95-08-9] is a plasticizer for poly(vinyl butyral) [63148-65-2] which is used in laminated safety glass (see Vinyl POLYMERS, poly(vinyl acetals)). Di(2-ethyUiexyl)phthalate [117-81-7] (DOP) is a preeminent plasticizer. Variation of acid and/or alcohol component(s) modifies the efficacy of the resultant ester as a plasticizer. In phthalate plasticizers, molecular sizes of the alcohol moiety can be varied from methyl to tridecyl to control permanence, compatibiUty, and efficiency branched (eg, 2-ethylhexyl, isodecyl) for rapid absorption and fusion linear (C6—Cll) for low temperature flexibiUty and low volatility and aromatic (benzyl) for solvating. Terephthalates are recognized for their migration resistance, and trimeUitates for their low volatility in plasticizer appHcations. 

Plasticizers can be classified according to their chemical nature. The most important classes of plasticizers used in rubber adhesives are phthalates, polymeric plasticizers, and esters. The group phthalate plasticizers constitutes the biggest and most widely used plasticizers. The linear alkyl phthalates impart improved low-temperature performance and have reduced volatility. Most of the polymeric plasticizers are saturated polyesters obtained by reaction of a diol with a dicarboxylic acid. The most common diols are propanediol, 1,3- and 1,4-butanediol, and 1,6-hexanediol. Adipic, phthalic and sebacic acids are common carboxylic acids used in the manufacture of polymeric plasticizers. Some poly-hydroxybutyrates are used in rubber adhesive formulations. Both the molecular weight and the chemical nature determine the performance of the polymeric plasticizers. Increasing the molecular weight reduces the volatility of the plasticizer but reduces the plasticizing efficiency and low-temperature properties. Typical esters used as plasticizers are n-butyl acetate and cellulose acetobutyrate. 

A better combination of fiber and polymer is achieved by an impregnation of [44] the reinforcing fabrics with polymer matrixes compatible with the polymer. Polymer solutions [40,45] or dispersions [46] of ]ow viscosity are used for this purpose. For a number of interesting polymers, the lack of solvents limits the use of the method of impregnation [44]. When cellulose fibers are impregnated with a bytyl benzyl phthalate plasticized polyvinylchloride (PVC) dispersion, excellent partitions can be achieved in polystyrene (PS). This significantly lowers the viscosity of the compound and the plasticator and results in cosolvent action for both PS and PVC [46]. 

Ethyl-1-hexanol, used in the synthesis of di(2-ethylhexyl) phthalate plasticizer, is made commercially from bulanal. Show the likely synthesis route. 

Jobling, S., Reynolds, T., and White, R. et al. (1995). A variety of environmentally persistent chemicals, including some phthalate plasticizers, are weakly estrogenic. Environmental Health Perspectives 103, 582-587. 

Hydroformylation is an important industrial process carried out using rhodium phosphine or cobalt carbonyl catalysts. The major industrial process using the rhodium catalyst is hydroformylation of propene with synthesis gas (potentially obtainable from a renewable resource, see Chapter 6). The product, butyraldehyde, is formed as a mixture of n- and iso- isomers the n-isomer is the most desired product, being used for conversion to butanol via hydrogenation) and 2-ethylhexanol via aldol condensation and hydrogenation). Butanol is a valuable solvent in many surface coating formulations whilst 2-ethylhexanol is widely used in the production of phthalate plasticizers. 

To illustrate the LCA method [1] and its relevance for risk-based management of additives, an example is elaborated for a phthalate plasticizer, di (2-ethylhexyl) phthalate (DEHP), as used in the application in cushion vinyl floor covering. 

Si element ATR-FTIR spectroscopy was used to analyze this residue, and its spectrum, along with the closest library matches, are shown in Figure 41. The absorbance of this residue is low as a consequence of the thin layer present on the plate. This makes matching the sample spectrum with a reference spectrum somewhat difficult. The closest matches extracted from the library interrogated are to ester-based plasticizer materials, which is consistent with a phthalate-plasticized PVC. A more specific identification could have been made with further testing such as subjecting the residue to GC-MS analysis, but the information suggested by the ATR-FTIR analysis was, in this case sufficient. 

Addition of a dioctyl phthalate plasticizer (DOP) increases flammability and incompatability of PVC with flame retardants. 

Vicki Barwick obtained a first degree in Chemistry from the University of Nottingham. She then joined the Laboratory of the Government Chemist (which became LGC in 1996) as an analyst in the Consumer Safety Group. Vicki was involved with a number of projects to assess the safety of consumer products, including developing test methods for the identification of colourants in cosmetics and the quantitation of phthalate plasticizers in child-care items. 

Mathur SP. 1974b. Respirometric evidence of the utilization of di-octyl and di-2-ethylhexyl phthalate plasticizers. J Environ Quality 3 207-209. 

A lot of concern also focuses on additives from packaging materials ending up in food (e.g., phthalate plasticizers, which are accused of many serious, chronic health effects). 

Shea, K.M. (2003). Pediatric exposure and potential toxicity of phthalate plasticizers, American Academy of Pediatrics, Technical Report, Pediatrics, 111, 6, 1467-1474. 

Material Substitution Replacement of the entire backing with a different material, e.g. a different plastic polymer that does not require phthalate plasticizers removes the need for these chemicals. Other hazards associated with PVC are also then avoided, with potential economic benefits in the medium to long-term. An innovative use of this approach is demonstrated in Annex I (6). 

PVC can also contain phthalates, plasticizers that make materials flexible. Phthalates have been linked to cancer, kidney damage, and problems with the reproductive system. 

Scholz, N., Diefenbach, R., Rademacher, I., and Linnemann, D. Biodegradration of DEHP, DBF. and DINP poorly water soluble and widely used phthalate plasticizers. Bull. Environ. Contain. Toxicol., 58(4) 527-534, 1997. 

Presented in Figures la and 2a are reconstructed partial total ion current chromatograms obtained by the CGC/MS/DA run on the May, 1985 samples. Figures lb and 2b show mass spectra taken at a certain specified time and peak number. Figure lb shows the mass spectrum of phthalate plasticizer in the soil... 

An investigation of residues of di(2-ethylhexyl) phthalate in retail whole milk samples from 14 Danish dairies about six months after the use of di(2-ethylhexyl) phthalate-plasticized milk tubing was banned in Denmark in August 1989 revealed a mean concentration lower than 50 ig/L (Petersen, 1991). 

Di(2-ethylhexyl) phthalate was found in both the packaging and in a number of contacted foods sampled in a 1985-89 survey as part of the Canadian Health Protection Branch Total Diet Program. Low levels (65 lg/kg [L] average in beverages and 29 ig/kg average in foods) associated with the use of di(2-ethylhexyl) phthalate-plasticized cap or lid seals were found in a variety of glass-packaged foods. It was... 

Stem, I.J., Miripol, J.E., Izzo, R.S. Lueck, J.D. (1977) Physicochemical aspects of the extraction in blood and the disposition in rats of di-(2-ethylhexyl)phthalate plasticizer. 

Various chemicals, such as the fibrate (e.g., clofibrate, bezafibrate, and ciprofibrate) and other lipid-lowering drugs (e.g., Wy-14643) and phthalate plasticizers (e.g., diethylhexyl phthalate), bind to and activate PPARa and are also hepa to carcinogenic in rodents. However, different compounds bind with different affinities, from strong (e.g., Wy-14643) to weak (e.g., phthalates). Thus, it is believed that peroxisomal proliferators act via the receptor (PPARa) to cause some of the effects seen. 

Phthalate esters of these linear alcohols were prepared by standard esterification techniques, and no problems were encountered in producing light-colored esters comparable to commercial phthalate plasticizers. For convenience, the plasticizers tested and the controls were given the code names listed in Table I. 

Since there were no commercially available phthalate plasticizers comparable to the linear heptyl and nonvl derivatives, they were bracketed between the even numbered oxo phthalates for comparison. Table IV shows that DL7P was the most efficient of all the plasticizers tested and is superior to DHP and DIOP in low temperature flexibility. It is considerably less volatile than DHP and only slightly... 

Figure 13. Tensile strength/temperature curves for phthalate plasticizers of different molecular weight...

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