Fyrol

Oligomeric 2-ChloroethylPhosphate. Akzo s Fyrol 99 [109640-81-5] is produced either by self-condensation of tris(2-chloroethyl) phosphate (82) or by insertion of phosphoms pentoxide into this phosphate (82) followed by ethoxylation. It is low in volatihty and useful in resin-impregnated air filters, in flexible urethane foam, rebonded foam, and stmctural foam. 

Organophosphorus Monomers. Many vinyl monomers containing phosphoms have been described in the Hterature (76), but few have gone beyond the laboratory. Bis(2-chloroethyl) vinylphosphonate [115-98-0] C H Cl O P, is a commercially available monomer (Akzo s Fyrol Bis-Beta) made from bis(2-chloroethyl) 2-chloroethylphosphonate. 

Several appHcations have been found for bis(2-chloroethyl) vinylphosphonate as a comonomer imparting flame retardancy for textiles and specialty wood and paper appHcations. Its copolymerization characteristics have been reviewed (76,109). This monomer can be hydrolyzed by concentrated hydrochloric acid to vinylphosphonic acid, polymers of which have photoHthographic plate coating utiHty (see Lithography). It is also an intermediate for the preparation of an oligomeric vinylphosphonate textile finish, Akzo s Fyrol 76 [41222-33-7] (110). 

The product contains 12.6% phosphoms and has an OH number in the 450 mg KOH/g range. Fyrol 6 is used to impart a permanent Class 11 E-84 flame spread rating to rigid foam for insulating walls and roofs. Particular advantages are low viscosity, stabiHty in polyol—catalyst mixtures, and outstanding humid aging resistance. Fyrol 6 is used in both spray foam, froth, pour-in-place, and slab stock. 

Oligomeric Vinylphosphonate. A water-soluble oligomer, Fyrol 76 [41222-33-7] is produced by reaction of bis(2-chloroethyl) vinylphosphonate and dimethyl methylphosphonate with elimination of all the chlorine as methyl chloride (127,128). This Hquid, containing 22.5% P, is curable by free-radical initiation, on cotton or other fabrics. Nitrogen components, such as A/-methylolacrylamide or methylolmelamines, are usually included in the finish, which can be durable to multiple launderings (129,130). 

Ra.dia.tlon. Use of radiation to affect fixation of some flame retardants is being investigated (110). Electron-beam fixation requires the selection of compounds that can be insolubilized inside or outside of the fiber with high yield in a short time. Polyunsaturated compounds, eg, Fyrol 76, have shown promise (see Radiation curing). 

THPOH-NH andFyrol76. The THPOH—NH finish and the Fyrol 76 finish also impart flame retardancy to certain polyester—cotton blends if the blends contain at least 65% cotton. 

Flame retardants (qv) are incorporated into the formulations in amounts necessary to satisfy existing requirements. Reactive-type diols, such as A/ A/-bis(2-hydroxyethyl)aminomethylphosphonate (Fyrol 6), are preferred, but nonreactive phosphates (Fyrol CEF, Fyrol PCF) are also used. Often, the necessary results are achieved using mineral fillers, such as alumina trihydrate or melamine. Melamine melts away from the flame and forms both a nonflammable gaseous environment and a molten barrier that helps to isolate the combustible polyurethane foam from the flame. Alumina trihydrate releases water of hydration to cool the flame, forming a noncombustible inorganic protective char at the flame front. Flame-resistant upholstery fabric or liners are also used (27). 

Fyrol 76 [41222-33-7] - [FLAME RETARD ANTS - PHOSPHORUS FLAME RETARDANTS] (Vol 10)... 

Flame relardanls are used in smolder-resistant upholstery fabric, combination flame retardant-durable press performance, flame-retardant treatments for wool, thermoplastic fibers (Tris. decabromodiphenyl oxide-polyacrylate finishes. Antihlu/e 19. nylon finishes), polyester-cotton fiber blends (THPOH-ummonju-Tris finish, decabromodiphenyl oxide-polyacrylate finish. THPC-amide-polytv illy I bromide) finish, THPOH-NHi and Fyrol 76. LRC-UX) finish, phusphonium salt-urea precondcn-satej. cotton-wool blends, and core-yam fabric,... 

The use of fire-retardant plasticizers, such as Fyrol PCF at levels of 5 to 10 parts, will reduce the hardness by 3 to 4 points while providing improved fire resistance. 

One embodiment of this general reaction led to a product which was commercially produced for several years by Stauffer as Fyrol 76 (9), a copolycondensation product of dimethyl methyl-phosphonate with bis(2-chloroethyl) vinylphosphonate. The features of Fyrol 76 were high phosphorus content (20%), water solubility, and ability to be polymerized by means of a radical initiator to a crosslinked polymer. A related polycondensation product was developed from tris(2-chloroethyl) phosphate and dimethyl methylphosphonate. By control of the reagents and procedure used for neutralization, these oligomeric products were produced with primary alcohol functional groups (7). 

Several commercial products have resulted from our phosphorus oligomer research. Fyrol 99, a 2-chloroethyl ethylene phosphate oligomer, has been successfully used as a flame retardant additive in rebonded urethane foam, in thermoset resins, in intumes-cent coatings, adhesives, paper air filters (13), and related uses. This product is less volatile and has a higher flame retardant efficacy than the parent compound tris(2-chloroethyl) phosphate. A related product was developed especially for use in flexible polyurethane foams. A vinylphosphonate/methylphospho-... 

The major commercial alternative to DOPO and its derivatives for reactively flame retarding epoxy resins, especially for electronic applications, is an oligo(l,3-phenylene methylphosphonate) (Structure 5.18) marketed by Supresta under the tradename Fyrol PMP. Fyrol PMP has a functionality higher than that of DOPO and can be used either as a hardener (curing agent) or be precondensed with an epoxy. 

At Bolton, we also have attempted to introduce volatile and possible vapor phase-active, phosphorus-based FR components in back-coating formulations.60 62 The selected FRs included tributyl phosphate (TBP), a monomeric cyclic phosphate Antiblaze CU (Rhodia Specialties) and the oligomeric phosphate-phosphonate Fyrol 51 (Akzo). When combined with an intumescent char-forming pentaerythritol (PER) derivative (NH1197, Chemtura) and applied as a back-coating on to cotton and polypropylene substrates, significant improvements in overall flame retardancy were observed. 

SYNS CELLUFLEX FYROL CEF NCI-C60128 NIAX FLAME RETARDANT 3 CF TRICHLORETHYL PHOSPHATE TRI-P-CHLOROETHYL PHOSPHATE TRI(2-CHLOROETHYL)PHOSPHATE TRIS(2-CHLOROETHYL)ESTER PHOSPHORIC ACID TRIS(p-CHLOROETHYL) PHOSPHATE TRIS(2-CHLOROETH-YL) PHOSPHATE... 

FLACAVON R FLAMMEX AP FYROL HB32 NCI-C03270 n PHOSPHORIC ACID, TRIS(2,3-DI-BROMOPROPYL) ESTER RCRA WASTE NUMBER U235... 

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