Plasticizers benzoate esters

Benzisoxazolone couplers, 19 254 Benzisoxazolone dye releasers, 19 290 Benzoate esters, 10 513-513 aroma chemicals, 3 257 Benzoate plasticizers, 25 184 Benzoates... 

Plasticizers can also be used in polyurethane adhesives to lower viscosity, improve filler loadings, improve low-temperature performanee, and plastieize the polynrethane adhesive. Phthalate esters, benzoate esters, phosphates, and aromatie oils are common examples [48]. Plasticizers should be used sparingly, as adhesion will generally decrease as levels increase. 

Flexibilizers based on ethylene copolymer resin can be used to replace liquid plasticizers in flame retardant compounds. These flexibilizers substantially reduce smoke and help in retaining mechanical performance of PVC. " A new plasticizer was developed for flame retarded polyurethanes. " It is based on benzoate esters which are popular in PU application but a new plasticizer contains at least one (and up to four) bromine atoms in benzene ring. 

It is useful to note that individual polyurethane elastomer classes are truly compatible with only specific plasticizer classes. Polyether-based urethanes are compatible with phthalate ester plasticizers such as dioctyl-phthalate (DOP) and its analogues, whilst polyester-based urethanes are only compatible with benzoate ester-type plasticizers. 

In PVC compounds, they act as high solvators but, unlike benzoate esters of older technology, they are low in volatile organic compounds (VOCs). Compared with other plasticizers they are often more efficient (up to 20% more efficient than DINP, it is claimed) and it may be necessary to reformulate some plastisols. They are also claimed to have very desirable environmental, health, and safety profiles. 

Fast-fusing plasticizers enable the PVC material to be processed faster or at lower temperatures. Generally it is in the area of plasfisol applications where the uses of faster fusing plasticizers are preferred. Examples of fast-fiising plasticizers include butyl benzyl phthalate (BBP), citrates, the epoxidized fatty acid plasticizer methyl epoxy stearate, alkyl sulfonic acid esters of phenol, dibutyl phthalates and tere-phthalates, and dibenzoate esters and benzoate ester blends. It should be noted that the use of BBP in PVC has rapidly declined because of product restrictions, while the use of dibutyl phthalate (DBP) declined in North America and in Europe years ago because of its high volatility. 

Most of the benzoate ester plasticizers are sold in blends. One of the top performing dibenzoate... 

In addition to these major market segments, plasticizers are used in a variety of smaller segments. Adhesives and sealants generally use lower molecular weight phthalate esters, benzoate esters and diesters, and dibutyl terephthalate because of improved solvency and lower fusion temperatures. One major use of plasticized PVC is automotive underbody coatings these products are highly filled plastisols that are mostly commonly based upon GP plasticizers often with a fast fusing plasticizer added to improve processability however, plasticizer volatility can be a major concern. 

Polyvinyl acetate (PVAc) emulsion polymers are used for adhesives, sealants, and paints. PVAc homopolymer is too brittle for most end uses, so much of fte PVAc used in the paint industry is internally plasticized through the incorporation of comonomers into the polymer backbone. However, there are some uses of externally plasticized PVAc in adhesives. The most common plasticizers used with adhesives are a variety of benzoate esters, although dibutyl terephthalate is now being promoted for this application. 

Furthermore, the increased ability to process at higher temperatures reduced the need for strong-solvating plasticizers in the new composition tiles. Thus, GP plasticizers, such as DOP and DINP, are currently used at 50-100 percent of the plasticizer system. When they are not used as the sole plasticizer, the balance is a stronger-solvating plasticizer, such as BBP, DIHP, or a benzoate ester, which improves processability. 

Benzoate plasticizers have been recognized since the 1940s as useful plasticizers for PVC. It was not until the mid-1950s, however, that benzoates useful in vinyl compositions were specifically identified and commercialized. Benzoate esters can be produced by direct esterification, transesterifleation, via the acid chloride route, or Schotten-Bauman reaction. The current preferred method for most benzoate esters... 

Monobenzoates and dibenzoates dominate the types of benzoates commercially available. The largest producer of benzoate esters is Velsicol Chemical Corporation their trade name is Benzoflex . Listed below are the various types of benzoate plasticizers manufactured by Velsicol ... 

Benzoflex 352 1,4-cyclohexane dimethanol dibenzoate. This benzoate ester is a high-melting-point plasticizer that is compatible with PVC and is useful as a processing aid. 

Specialty plasticizers are used in vinyl compositions to provide perfonnance that is beyond that which can be obtained with a general purpose phthalate. These plasticizers can be used by themselves in specific compositions, but are often used in combination with other plasticizers to complement each other s peifoimance. Several major types of specialty plasticizers have been covered in this chapter benzoate esters, polyester polymeries and citrate esters. Each class has specific performance attributes ... 

Benzoate esters. As a class, these specialty plasticizers are known as high sol-vators for vinyl compositions. Within this class of plasticizers, the applications range from viscosity reducers for plastisols to bleed-resistant plastisols for screen ink. They arc considered as phthalate alternates for applications requiring phthalate-free compositions. 

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. 

Uses Preparation of sodium and butyl benzoates, benzoyl chloride, phenol, caprolactum, and esters for perfume and flavor industry plasticizers manufacture of alkyl resins preservative for food, fats, and fatty oils seasoning tobacco dentifrices standard in analytical chemistry antifungal agent synthetic resins and coatings pharmaceutical and cosmetic preparations plasticizer manufacturing (to modify resins such as polyvinyl chloride, polyvinyl acetate, phenol-formaldehyde). 

CA 44, 11173(1950XNonyl esters, especially the benzoate, chlorobenzoate formate as plasticizers for NC other cellulose derivs) 64)H.A.Aaronson, PATR 1786(1950) (Kinetics of soln of NC s in expl plasticizers) 65)BritCelanese, Ltd, BritP 654771(1951) CA 47, 605(1953XM°noethers of l,4-butaned ol, such as mono-Bu ether, as plasticizers for NC) 65a)L.Brissaud M.Leclercq, MP 33, 473 80... 

The long extensions of the -R groups are three-dimensionally arranged around the polymer back-bone chain, and the floppy chains prevent the formation of a lattice and therefore crystallization. Plasticization with materials ester-benzoates would further separate the molecules and provide more flexible hardened cement. 

Ethylcellulose is compatible with the following plasticizers dibutyl phthalate diethyl phthalate dibutyl sebacate triethyl citrate tributyl citrate acetylated monoglyceride acetyl tributyl citrate triacetin dimethyl phthalate benzyl benzoate butyl and glycol esters of fatty acids refined mineral oils oleic acid stearic acid ethyl alcohol stearyl alcohol castor oil corn oil and camphor. 

In addition numerous compounds were detected which may serve as potential anthropogenic markers with respect to their source specifity and environmental persistence. Plasticizers (alkylsulfonic acid aryl esters, tributyl and tricresyl phosphates), synthetic fragrances (galaxolide, tonalide, 4-oxoisophorone) and additives of personal care products (4-methoxycinnamic acid 2-ethylhexyl ester, benzyl benzoate, dibenzyl ether, benzophenone) occurred due to sewage treatment plant effluents and reflect therefore an anthropogenic contamination of the particulate riverine matter, even in marine systems. 

Beilstein Handbook Reference) AI3-02247 BRN 1912251 Dimethyl 1,3-benzenedi-carboxylate Dimethyl isophthalate Dimethyl m-phthalate Dimethylester kyseliny isoftalove EINECS 215-951-9 HSDB 6138 Isophthalic acid dimethyl ester Methyl 3-(carbomethoxy)benzoate Methyl isophthalate Morflex 1129 NSC 15313 Uniplex 270. Chemical intermediate in the synthesis of polyesters. Used as a plasticizer, modifies clarity and melting point of PET resins used in films, blow-molded bottles, and similar products. Needles mp = 67.5° bp = 282° d = 1.194 Xm = 280, 288 nm (MeOH) slightly soluble in H2O, Morfiex Unitex. 

Beilstein Handbook Reference) 1,3-Benzenediol, monobenzoate Benzoic acid, m-hydroxyphenyl ester BRN 1873897 Eastman Inhibitor RMB EINECS 205-241-7 3-Hydroxyphenyl benzoate NSC 4807 Resorcinol monobenzoate. Industrial grade UV absorber/stabilizer for cellulosic plastics and PVC formulations. White crystalline solid mp = 133-135" insoluble in H2O, CeHe, soluble in EtOH, MezCO LDso (rat orl) = 1600 mg/kg. Eastman Chem. Co Monomer -Polymer Dajac. 

The heat of polymerization of vinyl esters exhibits essentially no dependence on the length of the carboxylic acid. Generally the range of the heats of polymerization is between 20.5 and 21 kcal/mole. Steric strain is thought to reduce this value in the case of vinyl benzoate and the plasticizing effect of the side chains is believed to raise the value slightly in the case of vinyl 2-ethylhex-anoate [17,18],... 

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