Tetrakis hydroxymethyl phosphonium salts

Phosphonium, tetrakis(hydroxymethyl)-, sulfate (2 1) (salt) 

Phosphonium, tetrakis(hydroxymethyl)-, chloride 

Tetrakis(hydroxymethyl)phosphonium salts are used to produce crease-resistant and flame-retardant finishes on textile fabrics, including children s nightwear. No data on occupational exposure levels were available (lARC, 1990). 

Tetrakis(hydroxymethyl)phosphonium sulfate was tested for carcinogenicity by oral administration in one strain of mice and one strain of rats. No dose-related increase in the incidence of any tumour was observed, but in males receiving the low dose there was an increased incidence of malignant lymphomas in mice and of mononuclear-cell leukaemia in rats. 

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Tetrakis(hydroxymethyl)phosphonium Salts. The reaction of formaldehyde (qv) and phosphine in aqueous hydrochloric or sulfuric acid yields tetrakis-(hydroxymethyl)phosphonium chloride [124-62-1/, Albright Wilson s Retardol C, or the sulfate [55566-30-8] (Retardol S), (C4H 2C4P)2SO [55566-30-8]. 

LRC-100Finish. The use of LRC-100 flame retardant for 50/50 polyester cotton blends has been reported (144). It is a condensation product of tetrakis(hydroxymethyl)-phosphonium salt (THP salt) and A/A7,A7 -trimethylphosphoramide [6326-72-3] (TMPA). The precondensate is prepared by heating the THP salt and TMPA in a 2.3-to-l.0-mole ratio for one hour at 60—65°C. It is appUed in conjunction with urea and trimethylolmelamine in a pad-dry-cure oxidation wash procedure. Phosphoms contents of 3.5—4.0% are needed to enable blends to pass the FF 3-71 Test. 

Textile Flame Retardants. The first known commercial appHcation for phosphine derivatives was as a durable textile flame retardant for cotton and cotton—polyester blends. The compounds are tetrakis(hydroxymethyl)phosphonium salts (10) which are prepared by the acid-cataly2ed addition of phosphine to formaldehyde. The reaction proceeds ia two stages. Initially, the iatermediate tris(hydroxymethyl)phosphine [2767-80-8] is formed. 

Offshore oil production is one area in which environmental pollution has been highlighted as an issue, particularly in the use of biocides in production waters. Tetrakis-hydroxymethyl phosphonium salts exhibit acceptable environmental profiles [1120], and they are regarded as the preferred products for bacterial control within the oil production industry. 

Tetrakis (dimethylthiocarbamato) tellurium(IV), 24 428 Tetrakis(hydroxymethyl)phosphonium salts, 11 498 hydroxide, 19 67... 

World Health Organisation (WHO) (2000) Flame retardants Tris(2-butoxyethyl)phosphate, tris(2-ethylhexyl) phosphate and tetrakis(hydroxymethyl)phosphonium salts. Environmental Health Criteria 218, WHO, Geneva... 

Tetrakis(hydroxymethyl)phosphonium salts Tetramethyllead see Lead and lead compounds)... 

During formation of the addition compounds 12 and 16, no free formaldehyde accumulates. We assume that the liberated formaldehyde immediately reacts with tris-hydroxymethyl-phosphine, forming the quaternary tetrakis-hydroxymethyl-phosphonium salt 13. The addition compounds 12 and 16 are relatively unstable, but can be purified for analysis. Intermediates 12 and 16 can also be employed in the synthesis of symmetrical or unsymmetrical phosphamethin-cyanines. For example, Klapproth synthesized 18 in 60% yield by condensing 16 with 77. 

No epidemiological relevant to the carcinogenicity of tetrakis(hydroxymethyl)-phosphonium salts were available. 

There is inadequate evidence in experimental animals for the carcinogenicity of tetrakis(hydroxymethyl)phosphonium salts. 

Tetrakis(hydroxymethyl)phosphonium salts are not classifiable as to their carcinogenicity to humans (Group 3). 

WHO/ICPS. Environmental Health Criteria 218 Flameretardants tris[2 butoxyethyl] phosphate, tris[2 ethylhexyljphosphate and tetrakis [hydroxymethyl] phosphonium salts. World Health Organization, Geneva, 2000. 

Spiro(5,5)phosphonia-undecane chloride (12) was produced in low yield by the reaction of dimethylurea with the little exploited, readily available, tetrakis(hydroxymethyl)-phosphonium salts <81PS(10)147>. Tetrathiodibenzo quasiphosphonium salts (24 R = Dop X = PFe") have been produced by the reaction of silylated dithiocatechol (123) with PF5 <73CC144>. Spiro(5,5)phosphazenes (20) may be made directly from trichlorophosphine and diaminophosphazene, H2NPR2=PR2NH2,... 

Meanwhile there is a fourth candidate, used for many decades in certain flame-resistant cotton apparel fabrics. This is tetrakis hydroxymethyl phosphonium salts (THPS), with trade names such as Proban. 

Flame-Retardant Finishes on Cellulosic Substrates. The flame retarding of cotton and viscose-rayon fabrics has been the object of a large worldwide effort on phosphorus-containing finishes (217-219). The commercial cotton finishes are based on tetrakis(hydroxymethyl)phosphonium salts, usually the chloride or sulfate (220). These salts are prepared by reaction of formaldehyde with phosphine in the presence of an acid. 

The tetrakis(hydroxymethyl)phosphonium salts are applied to cellulosic fabric, most commonly as a urea precondensate (Albright Wilson s, now Rhodia s Proban), and cured with ammonia vapor (221-223). The finish, after oxidation by air or hydrogen peroxide, has phosphine oxide structures in a cross-linked amino resin network, probably also lightly linked to the cellulose. This finish is durable to multiple launderings and is used for industrial cotton garments (224). 

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