Tetrabromophthalic anhydride

TetrabromophthalicAnhydride. Tetrabromophthalic anhydride [632-79-1] (TBPA) is widely used as a reactive flame retardant in unsaturated polyesters as weU as the precursor to a number of other fine retardants. Polyesters prepared from this compound have relatively poor photochemical stabiUty and tend to discolor upon exposure to light. This tendency to discolor can be reduced, but not eliminated, by the use of uv stabilizers. 

Diester/Ether Diol of Tetrabromophthalic Anhydride. This material [77098-07-8] is prepared from TBPA in a two-step reaction. First TBPA reacts with diethylene glycol to produce an acid ester. The acid ester and propylene oxide then react to give a diester. The final product, a triol having two primary and one secondary hydroxyl group, is used exclusively as a flame retardant for rigid polyurethane foam (53,54). 

Various additives show considerable extraction resistance, such as impact modifiers (polyacrylates and polyblends PVC/EVA, PVC/ABS, etc.), highpolymeric processing aids (PMMA-based), elastomers as high-MW plasticisers, reactive flame retardants (e.g. tetrabromobisphenol-A, tetrabromophthalic anhydride, tetrabromophthalate diol, dibromostyrene). Direct measurement of additives by UV and IR spectroscopy of moulded films is particularly useful in analysing for additives that are difficult to extract, although in such cases the calibration of standards may present a problem and interferences from other additives are possible. 

The pyrolysis of a number of compounds at temperatures around 600— 800° and at pressures of the order of 10 2 mm. has been shown to give rise to benzyne. These compounds include for example indanetrione 29>, and phthalic anhydride 30 38>. The dimerisation of benzyne to yield biphenylene has been used preparatively 31 33>, an(j the pyrolysis of tetrafluorophthalic anhydride 34>, and tetrachlorophthalic anhydride 3i-33) gave the corresponding octahalobiphenylenes. In the case of the pyrolysis of tetrachlorophthalic anhydride some hexachlorobenzene is also formed, while the pyrolysis of tetrabromophthalic anhydride results in the formation of hexabromobenzene but no octabromobiphenylene. The disproportionation of tetrabromobenzyne to form carbon and bromine is a function of the high temperature involved and, as we shall see later, both tetrabromo- and tetraiodo-benzyne behave normally in solution. 

The first fire retardant polyester containing a reactive fire retardant monomer was introduced by the Hooker Electrochemical Corporation in the early 1950 s containing chlorendic acid as the reactive monomer (6). This pioneering development rapidly led to the introduction of variety of reactive halogen and phosphorus containing monomers, such as tetrabromophthalic anhydride, chlorostyrene and tetrabromobisphenol A, which found application in a wide variety of condensation polymer systems. 

Dies, in bar soap manufacture, 22 752 Diester/ether diol of tetrabromophthalic anhydride, 11 478 Diester production, 10 489 Die swell, 20 172 Diet, 2 823... 

Tetrabromophthalic anhydride physical properties of, 4 357t Tetrabromophthalic anhydride/diol physical properties of, 4 357t Tetrabutylammonium bromide (TBAB), 2 550t, 76 557-558, 566 Tetrabutylphosphonium hydroxide, 22 573 Tetrabutyltin, toxicity of, 24 831 Tetrabutylurea, 2 550t Tetracalcium aluminate,... 

The resistance of polymers to flame may be increased by the addition of halogenated compounds and antimony oxide. Organic phosphate additives inhibit the glow of the char formed in burning polymers. Polymers with chlorine pendant groups, such as PVC, and those with halogen-substituted phenyl groups, such as polyesters produced from tetrabromophthalic anhydride, are more flame-resistant than hydrocarbon polymers. 

Halogenated intermediates, dibromoneopentyl glycol [3296-90-0] (DBNPG), and alkoxylated derivatives of tetrabromobisphenol A are used extensively in flame-retardant applications. Similar properties can be derived from halogenated dibasic acids, chlorendic anhydride [115-27-5] (CAN), and tetrabromophthalic anhydride [632-79-1] (TBPA). Processes can be used to produce brominated products by the in situ bromination of polymers derived from tetrahydrophthalic anhydride. 

Flame-Retardant Resins. Flame-retardant resins are formulated to conform to fire safety specifications developed for construction as well as marine and electrical applications. Resins produced from halogenated intermediates (Table 5) are usually processed at lower temperatures (180°C) to prevent excessive discoloration. Dibromoneopentyl glycol [3296-90-0] (DBNPG) also requires glass-lined equipment due to its corrosive nature. Tetrabromophthalic anhydride (TBPA) and chlorendic anhydride (8) are formulated with ethylene glycols to maximize flame-retardant properties reaction cycle times are about 12 h. Resins are also produced commercially by the in situ bromination of polyester resins derived from tetrahydrophthalic anhydride... 

Tetrachlorophthalic anhydride gave a relatively low yield of products derived from tetrachlorobenzyne. The pyrolysis tube was badly carbonized evidently extensive decomposition of the anhydride, the aryne, or the chlorinated products had occurred. Tetrabromophthalic anhydride gave a still lower yield of products. These are not listed in the table because none of them retained all four bromine atoms and could be definitely ascribed to reactions of tetrabromobenzyne, although tri-bromo- and dibromonaphthalene were present in appreciable amounts. Tetraphenylphthalic anhydride also gave low yields of products of the reaction of tetraphenylbenzyne with pyridine. This was not because of the stability of the anhydride and its reluctance to form the aryne, but rather because the aryne preferred to stabilize itself intramolecularly. The behavior of tetraphenylphthalic anhydride is discussed in another Section. 

Another flame-retardant treatment for wool based on exhanstion of an anionic species is the use of tetrabromophthalic anhydride, TBPA (Fig. 8.16), which hydrolyses to the carboxylic form during application. Use of TBPA at 10 % on weight of fabric under acid conditions provides effective flame retardancy that is dnrable to dry cleaning and mild laundering conditions (cold water washing at nentral pH). But TBPA is suspected to generate polybrominated dioxins under burning conditions. 

The bromine linked to a double bond or linked to an aromatic nucleus are much more stable structures (not easily decomposed to HBr as dibromo neopentylglycol, a saturated aliphatic bromine compound). Thus, a very successful bromine containing diol, produced industrially [4, 24], is based on tetrabromophthalic anhydride. Tetrabromophthalic anhydride is reacted first with diethylene glycol and the resulting half ester is reacted with propylene oxide (PO) (reaction 18.5) [3]. 

FG 400 FG 4000 FireMaster PHT 4 Great Lakes PHT4 HSDB 5438 NSC 4874 PHT 4 Phthalio acid, tetrabromo-, anhydride Phthalic anhydride, tetrabromo- Saytex RB 49 Tetrabromo-phthalio acid anhydride Tetrabromophthalic anhydride ... 

Tetrabromophthalic anhydride. Flame retardant in production of unsaturated polyester resins and rigid PU polyols co-hardener for epoxy resins cost efficient additive for latex emulsions derivatives used as flame retardants in diverse applications (wire coating, and wool, etc.). Crystals mp = 279-281 insoluble in H2O. Ethyl Corp. Great Lakes Firm Chem. 

Analytes CB, chlorobenzenes DDE, l,l-dichloro-2,3-bis(4-chlorophenyl)ethane DDT, l,l-dichloro-2,3-bis(4-chlorophenyl)ethylene DBF, decabromobiphenyls HBCD, Hexabromo-cyclododecane HpBB, heptabromobiphenyl PBB, polybrominated biphenyl PBCCH, pentabromochlorocyclohexane PBDE, polybrominated diphenyl ether PBT, Polybutylene terephthalate PCB, Polychlorinated biphenyl PBDD, polybrominated dibenzo-/ -dioxins PBDF, polybrominated dibenzofuranes PCN, polychlorinated naphthalenes PCP, polychlorinated phenols PBB, polybrominated biphenyl PeBDE, pentabromodiphenyl ether PET, Polyethylene terephthalate PXDDs, polyhalogenated dibenzo-p-dioxins PXDFs, polyhalogenated dibenzofurans TBBPA, tetrabromobisphenol A TBPA, tetrabromophthalic anhydride TCBPA, tetrachlorobisphenol A TDBPP, tris(2,3-dibromopropyl)phosphate. 

Phthalide (241) has been used as an additive used to prepare polyesters with low molten viscosity <91JAP(K)03200859>. Phthalic anhydride (242), prepared by the oxidation of o-xylene, is of major importance to the chemical industry with 1992 production over 400000 tonnes <93CEN38>. It is used as a monomer in the preparation of alkyd resins (a polyester with glycerol and other polyols) and thermosetting polymers (with maleic anhydride and polyols). Another important application is in the production of dioctyl phthalate (243), which is used as a plasticizer for PVC (1991 production, 123000 tonnes). Over 400 references pertaining to the use of phthalic anhydride in polymer compositions have appeared since 1982. Tetrabromophthalic anhydride (244) has been used to prepare flame-retardant bisphthalimides as polymer additives <90JAP(K)02145568>. 

Bromine compounds with exclusively aromatic-bound bromine are produced in large quantities. Occupying the first place is tetrabromobios-phenol-A, which is employed as a reactive flame retardant in polycarbonates and epoxy resins. Similarly, tetrabromophthalic anhydride has been used in the production of flame-retarded unsaturated polyester resins. 

See 2-Bromo-2-nitropropane-1,3-diol 1-Bromopropane. Seen-Propyl bromide Bromphthal. See Tetrabromophthalic anhydride Bronopol. See2-Bromo-2-nitropropane-1,3-diol Bronze. See Bronze powder... 

TBPA. See Tetrabromophthalic anhydride TBPAE. See Tribromophenylallyl ether... 

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