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TETRAKIS(HYROXYETHY) PHOSPHONIUM SALTS 1. Chemical and Physical Data 1.1 Synonyms Tetrakis(hydroxyethyl) phosphonium sulfate Chem. Abstr. Services Reg. No.: 55566-30-8 Chem. Abstr. Name: Phosphonium, tetrakis(hydroxyethyl)-, sulfate (2:1) (salt) IUPAC Systematic Name: Bis(tetrakis(hydroxymethyl) phosphonium) sulfate (salt) Synonym: Octakis(hydroxyethyl) phosphonium sulfate; 1RPS Tetrakis(hydroxyethyl) phosphonium chloride Chem. Abstr. Services Reg. No.: 124-64-1 Chem. Abstr. Name: Phosphonium, tetrakis(hydroxymethyl)-, chloride IUP AC Systematic Name: Tetrakis(hydroxyethyl) phosphonium chloride Synonym: Tetrahydroxyethylphosphonium chloride; 1RPC Tetrakis(hydroxymethyl) phosphonium acetate/phosphate Chem. Abstr. Services Reg. No.: 55818-96-7 Chem. Abstr. Name: Phosphonium, tetrakis(hydroxyethyl)-, acetate (salt), mixure with tetrakis(hydroxymethyl) phosphonium phosphate (3:1) (salt) IUPAC Systematic Name: Tetrakis(hydroxyethyl) phosphonium acetate (salt), mix- ture with tris(tetrakis(hydroxymethyl) phosphonium) phosphate (salt) See Table 1 for CAS numbers and names of other tetrakis(hydroxymethyl) phosphonium salts. -95- lAC MONOGRAHS VOLUME 48 96 Table 1. Chemical Abstracts Servces Registry numbers of tetrakis(hydroxyethyl) phosphonium salts Salt CAS No. Acetate 758037-2 Acetate-phosphate (1:1) 62588-94-7 Bromide 6-Carboxycellulos salt Cellulose carboxyethyl ether salt Formate 59409-2 73082-49-2 73083-23-5 25151-36- H ydroxybutanedioate 39734-92-4 2- H ydroxyropionate 396878-7 692412-0 Iodide 1-Naphthalenesulfonate 2-Naphthalenesulfonate 79481-21-3 79481-22-4 53211-22-6 52221-67-7 22031-17-0 15652-65-0 Oxalate (1:1) Oxalate (2:1) Phosphate Tetraphenylborate-tetraacetate paa-Toluenesulfonate 75019-908 1.2 Structural and molecular formulae and molecular weights Tetrakis(hydroxyethyl) phosphonium sulfate ~ p+/ /~ CH20H CH20H 504 -2 CH20H CH20H CaH24012P 2S 2 MoL. wt: 40.28 Tetrakis(hydroxyethyl) phosphonium chloride ~ p+ CI/ CH20H / CH20H CH20H C4H12CI04P ~ CH,OH MoL. wt: 190.56 TETRAS(HYDROXYMETHYL) PHOSPHONIUM SALTS 97 Tetrakis(hydroxyethyl) phosphonium acetate/phosphate ~/ /~ CHzOH p+ C~ /CH,OH CHzOH CZH30Z - CHzOH CHzOH /~ P04 -3 p+ CHzOH CHzOH 3 C4H1204P . C2H302/(C4HI204P)3 . P04 MoL. wt: 214.16/560.30 1.3 Chemical and physical properties of the pure substance Tetrakis(hydroxyethyl) phosphonium sulfate (a) Description: Ciystalline solid (Weil, 1980) (b) Solubility: Soluble in water (Weil, 1980) Tetrakis(hydroxyethyl) phosphonium chloride (a) Description: Ciystalline solid (Weil, 1980) (b) Melting-point: 154°C (Grasseli & Ritchey, 1975) (c) Spectroscopy data: lnfrared (prism (13510); grating (47569PD, ultraviolet and nu- clear magnetic resonance (proton (1166)) spectral data have been reported (Sadtler Research Laboratories, 1980; National Toxicology Program, 1987). (d) Solubility: Soluble in water (Weil, 1980) Tetrakis(hydroxyethyl) phosphonium acetate/phosphate No data were available to the Workig Group. 1.4 Technical products and impurities Tetrakis(hydroxyethyl) phosphonium sulfate Trade names: Pyoset TKO; Retardol S Tetrakis(hydroxyethyl) phosphonium chloride Trade names: Proban CC; Pyoset TKC; Retardol C Tetrakis(hydroxyethyl) phosphonium acetate/phosphate Trade names: Pyoset Flame Retardant TK; Pyoset TK Tetrakis(hydroxyethyl) phosphonium chloride (IPC) and tetrakis(hydroxyethyl) phosphonium sulfate (lPS) are marketed in concentrated aqueous solutions at approximately 80 and 75 wt%, respectively (Albright & Wilson Americas, lnc., 1988a,b). Commercil THPC has been reported to contain free formaldehyde (see lARC, 1982; 3.8% at the pH at which THPS is available, pH 0.4; Ulsamer et aL., 1980). Tetrakis(hydroxymethyl) phospho- IAC MONOGRAHS VOLUME 48 98 nium acetate/phosphate (IPA/P) was available in the USA as a clear, nearly colourless solution with a pH of approxiately 5, containing 10% active phosphorus (Hooper et aL., 1976a). 2. Production, Use, Occurrence and Analysis 2.1 Production and use (a) Production Tetraki(hydroxyethyl) phosphonium salts have been produced for commercial use since the 1950s. The first, llPC, was introduced in 1953. The salts are produced by the reaction of formaldehyde with phosphine in the appropriate aqueous acid (Weil, 1980; Hawley, 1981). Two US companies supply THPS and THPC. Combined annual use of each compound in the USA is 90-4500 tonnes (National Toxicology Program, 1987). (b) Use Tetrakis(hydroxyethyl) phosphonium salts are used to produce crease-resistant flame-retardant finishes on cotton textiles and cellulosic fabrics (Hooper, 1973; Hooper et aL., 1976a,b). llPC, THPS and THPA/P can be cured on the fabric with amine compounds (e.g., ammonia, urea, melamine-formaldehyde resins) to form durable, cross-linked es (Weil, 1980). Recently, THPS has largely replaced THPC in commercial use (Duffy, 1983); THPA/P has never been a major commercial product. Many co-reactants have been used to form flame-retardant finishes with these compounds. One of the most popular processes has been the tetrakis(hydroxyethyl) phosphonium hydroxen cured on the fabric by reaction with ammonia gas (Weil, 1980). ln 1974, over 14 milion metres of cotton flannel for children's nightwear were estimated to have been treated with tetrakis(hydroxyethyl) phosphonium salts in the USA flame-retardant resin finish ide-ammonIa finish, in which llPS is converted to a free organic base and th (Hooper et aL., 19700). (c) Regulatory status and guidelines No regulatoiy standard or guideline has been established for tetrakis(hydroxymethyl) phosphonium salts. 2.2 Occurrence (a) Naturaloccurrence These compounds are not known to ocur as natural products. (b) Occupational exsure Approxiately 100 workers were potentially expsed to THPC in the USA in 1972-74 (National lnstitute for Occupational Safety and Health, 1977). TETRS(HYDROXYMETHYL) PHOSPHONIUM SALTS 99 No data on levels of expsure were available to the Workig Group. 2.3 Analysis A number of analytical methods have been used to identIf and characterie THPC-based fIame-retardant polymers on fabric. These include potassium iodate-thiosulfate titration (Frank, 1977), thermogravietric and differential thermal analysis, differential scnning calorietry, scnning and transmission electron microscopy, electron spin reso- nance and energy disersive X-ray analysis (Frank et al., 1982). No data were available to the Workig Group on methods for the analysis of tetrakis(hydroxyethyl) phosphonium salts in the workplace or in the envionment. 3. Biological Data Relevant to the Evaluation of Carcinogenic Risk to Humans 3.1 Carcinogenicity studies in animais Tetrakis(hydroxyethyl) phosphonium sulfate Oral administration Mouse: Groups of 50 male and 50 female B6C3F, miee, seven weeks of age, received 0, 5 or 10 mg/kg bw llPS dissolved in distiled water (72:28 vol % ) by gavage on five days a week for 104 weeks; aIl survvors were kiled at 112 weeks of age. No difference in survival or mean boy weight was observed between control and treated mice. The incidence of malignant lymphomas in males showed a negative trend: control, 2/50; low-dose, 9/50; high-dose, 0/50 (National Toxicology Program, 1987). Rat: Groups of 49 or 50 male and female Fischer 344/N rats, six weeks of age, received 0, 5 or 10 mg/kg bw llPS in distiled water (72:28 vol % ) by gavage on five days a week for 104 weeks. AIl survvors were kiled at 112 weeks of age. Survval of treated males was reduced as compared to controls; mean boy weights of treated animaIs were comparable to those of controls. The incidence of mononuclear-cell leukaemIa in males showed a negative trend: control, 30/50; low-dose, 36/50; high-dose, 20/50 (National Toxicology Program, 1987). Tetrakis(hydroxyethyl) phosphonium chloride (a) Oral administration Mouse: Groups of 50 male and 50 female B6C3F, mice, eight weeks of age, received 0, 7.5 or 15 (males) and 0, 15 or 30 (females) mglkg bw llPC dissolved in deionized water (75:25 vol%) by gavage on five days a week for 103 weeks; all survvors were kiled at 112-113 weeks of age. No difference in survval or in mean boy weight was observed between control and treated mice. There was no significant increase in the incidence of any tumour in any organ in treated mice of either sex (National Toxicology Program, 1987). !AC MONOGRAHS VOLUME 48 100 Rat: Groups of 50 male and 50 female Fischer 344/N rats, seven weeks of age, received 0, 3.5 or 7.5 mg/kg bw THPC in deiònized water (75:25 vol % ) by gavage on five days a week for 103 weeks; aU survvors were kiled at 111 weeks of age. Survval of high-dose females after week 70 was lower than that of controls; mean bo weights of treated animaIs were comparable to those of controls. The incidence of mononuclear-cell leukaemia in males showed a negative trend: control, 19/50; low-dose, 25/50; high-dose, 16/50 (National Toxicology Program, 1987). (b) Skin application Mouse: Groups of 20 female lCR/Ha Swiss mice, six to eight weeks of age, received ski applications of 2 mg/mouse llPC in dimethyl sulfoxide (DMSO) to examine the initiating (1), promoting (II) and complete carcinogenie (III) potential in ski carcinogenesis. Two groups of 20 miee (l) received a single application of 1rPC in DMSO followed byapplications of 2.5 J.g/animal phorbl myrstyl acetate (JA) in acetone or acetone alone three times a week for 57 weeks. No ski tumour ocurred in either group. Three groups of 20 12-dimethylbenz(a)anthracene in acetone foUowed by applications of either 2 mg/animal 1rPC in DMSO, 2.5 J.g/animal TPA in acemiee (Il) received a single application of 20 J.g 7, tone (psitive control) or DMSO alone three times a week for 57 weeks. The numbers of miee with squamous-cell papilomas and carcinomas of the ski were 3/20 (three with a carci- noma fp :; 0.05)), 19/20 (nine with a carcinoma) and 0/20, respectively. A further group of miee (Ill) received applications of 2 mg/animal THPC in DMSO alone three times a week for 57 weeks; one squamous-ceU carcinoma of the ski developed, whereas no ski tumour was observed in an untreated group (Lewengart & Van Duuren, 1977). A group of 60 female ICR/Ha Swiss miee, six to eight weeks of age, received ski applise THPC in acetone three times a week for 71 weeks. Control groups of 249 and 29 miee (effective numbers necropsied) received no treatment and treatment with 0.1 ml acetone, respectively. The numbers of miee with papilary tumours of the lung were cations of 2 mg/mou 90/249 (36%), 7/29 (24%) and 17/59 (29% ) in the two control and the THPC-treated groups, respectively; the numbers with papilomas of the forestomach were 6/249 (2% ) and 1/59 (2%) in the untreated control and the treated groups, respectively (Van Duuren et al., 1978). Tetrakis(hydroxyethyl) phosphonium acetate/phosphate Skin applicaton Mouse: ln a two-stage carcinogenicity study, groups of 20 female lCR/Ha Swis mice, 12-dimethylbenz(a)anthra- six to eight weeks of age, received a single application of 20 J.g 7, cene in acetone foUowed by applications of 7 mg/animal Pyoset TK (fPAI), 2.5 J.g/ani- mal TPA (psitive control) or acetone three times a week for 57 weeks. The numbers of mice with squamous-cell papilomas and carciomas of the ski in the THPA/-, TPA- and acetone-treated groups were 7/20 (two with a carcinoma fp = 0.00)), 19/20 (nine with a cacinoma) and 0/20, respectively. When THPA/ was given alone, no ski tumour was observed (Lewengart & Van Duuren, 1977). TETRAS(HYDROXYMETHYL) PHOSPHONIUM SALTS 101 3.2 Other relevant data (a) Exprimental systems (i) Absorption, distribution, exretion and metabolism No data were available to the Workig Group. (ü) Toxic effects Tetrakis(hydroxyethyl) phosphonium sulfate Administration by gavage of 2-50 mg/kg bw per day THPS in saline to male ICR Swiss miee for 14 days resulted in deaths in the group given 50 mg/kg bw after the fifth day. Application of 125-100 mg/kg bw per day THPS to chemicaIly depilated back ski of male ICR Swis miee daily for up to 14 days resulted in reduced boy weight, paralysis and supedicial necrosis of the treated area at doses of 700 mg/kg and above (Connor et al., 1980). ln gavage studies, Fischer 344/N rats and B6C3F1 miee received single doses of 20- 160 mg/kg bw 11fPS; aIl rats at the highest dose and aIl miee receivig 400 mg/kg bw or more died. AlI rats and 8/10 miee that received doses of 100 mglkg bw per day for 14 days died. Of animaIs dosed for 90 days on five days per week, male rats died after doses of 60 mg/kg bw per day and mice of each sex after 40 mg/kg bw per day or higher. ln the last studies, hepatoce vacuolar degeneration, whieh appeared to be related to treatment, was seen at doses of 10 mg/kg per day and above in rats and at 20 mg/kg per day and above in mice (National Toxicology Program, 1987). ln two-year studies (see also section 3.1), non-neoplastie lesions attributed to administration of THPS in rats included cystie degeneration of the liver in males and hepatoce cyoplasmie vacuoliztion in animaIs of each sex. No significant non-neoplastic lesion attributable to the treatment was se en in miee (National Toxicology Program, 1987). Tetrakis(hydroxyethyl) phosphonium chloride The oral LD50 for THPC was reported to be 282 mg/kg bw in male rats (Ulsamer et al., 1980). The compound was irtating to rats and rabbits following dermal application, and daily dermal exposures to a 30% solution were fatal to rats nine days after the first dose (Aoyama, 1975). ln gavage studies, aIl Fischer 344/N rats and B6C3F1 mice that received single doses of 150 mg/kg bw and 300 mg/kg bw THPC, respectively, died. ln 14-day studies, deaths were observed in rats that received 75 mg/kg bw and in mice that received 300 mg/kg bw. Deaths also ocurred in 9O-day studies in rats that received 15 mg/kg bw and in mice that received 135 mg/kg bw per day on five days a week. ln the last studies, clinical signs of neurotoxicity and hepatocellular necrosis and vacuoliztion were seen in rats and mice (National Toxicology Program, 1987). ln two-year studies (see also section 3.1), non-neoplastic 1esions in miee and rats treated with THPC included hepatoce cyoplasmic vacuoliztion in animaIs of each sex, cystic degeneration of the liver in male rats, haematopoiesis of the spleen in female rats and follcular-cell hyperplasia of the thyroid in female miee (National Toxicology Program, 1987). llPC reacts in vitro with the 2-amino group of guanosine to form a stable product (Lewengart & Van Duuren, 1976). IAC MONOGRAHS VOLUME 48 102 (ii) Effects on reproduction an prenatal toxicity No data were available to the Workig Group. (iv) Genetic an related effects (see Appendix 1) Tetrakis(hydroxyethyl) phosphonium sulfate llPS was not mutagenie to several strains of Salmonella typhimurium in the presence or absence of an exogenous metabolic system from Aroclor 1254-induced rat liver (Connor et al., 1980; MacGregor et al., 1980). Negative results in S. typmmurium strains TA1535, TA1537, TA1538, TA98 and TA100 were also obtained in mutagenicity assays pedormed on 2O-J.i samples of urie from male ICR Swiss mice treated with 1HPS by gavage (2 mglkg bw or 50 mg/kg bw for 14 days, 50 mg/kg bw for five days) or by dermal application (125-100 mg/kg bw, 13-16 days) or by feeding several doses of a cotton fabric treated with THPS and mixed in the diet over 14 days. These assays were conducted in the absence of exogenous metabolic activation and in the presence or absence of ß-glucuronidase (Connor et al., 1980). llPS caused mutation at the TK locus in L5178Y mouse lymphoma cells in culture at 5 J.g/ml in the absence of an exogenous metabolic system (National Toxicology Program, 1987). This compound did not induce micronuclei in bone marrow of male ICR SwIss mice treated dermally. A two-fold increase in the incidence of chromatid breaks was seen, however, in bone marrow of miee treated orally with 10 mg/kg bw THPS, and a six-fold increase in en in miee treated dermally with 1 g/kg (Connor et al., 1980). Tetrakis(hydroxyethyl) phosphonium chloride THC was not mutagenic to several strains of S. typhimurium in the presence or absence of an exogenous metabolie system from Aroclor 1254-induced rat liver (MacGregor et aL., 1980; National Toxicology Program, 1987) or Syran hamster liver (National Toxicology polyploidy was se Program, 1987). The compound caused mutation at the TK locus in L5178Y mouse lymphoma cells at 5 J.g/ml in the absence of an exogenous metabolie system (National Toxicology Program, 1987). llPC induced sister chromatid exchange in the Chinese hamster CHO cell line in the presence and absence of an exogenous metabolic activation system from Aroclor 1254-induced rat liver at doses of 20 and 15 J.g/ml (National Toxicology Program, 1987) and 40 and 50 J.g/ml (Lovedayet al., 1989), respectively. It induced chromosomal aberrations in the CHO cell line, in the presence and absence of an exogenous metabolic system from Aroclor 1254-induced rat liver at 50 and 30 J.g/ml, respectively (National Toxicology Program, 1987). ln the absence of an exogenous metabolic system, it induced chromosomal aberrations in CHO cells at 30-50 J.g/ml (Lovedayet al., 1989), in Chinese hamster lung cells at 30 J.g/ml (lshidate, 1983) and in the Chinese hamster DON cellline at 19 J.g/ml (Sasaki et al., 1980). DMSO extracts of fabrics that had been treated with either THPS or 1HPC induced ouabain resistance in the Chinese hamster V79 cellline, in the presence and absence of an exogenous metabolic system from Aroclor 1254-induced rat liver, and cell transformation in mouse BALB/c 3T3 cells (Ehrlich et al., 1980). TETRAS(HYDROXYMETHYL) PHOSPHONIUM SALTS 103 (b) Human No data were available to the Workig Group. 3.3 Case reports and epidemiological studies of carcinogenicity to humans No data were available to the Workig Group. 4. Summary of Data Reported and Evaluation 4.1 Exposure data Tetrakis(hydroxyethyl) phosphonium salts are used to produce crease-resistant and es on textile fabrics, including children's nightwear. No data on occupational exposure levels were available. flame-retardant finish 4.2 Experimental carcinogenicity data Tetrakis(hydroxyethyl) phosphonium sulfate was tested for carcinogenicity by oral administration in one strain of miee and in one strain of rats. No dose-related increase in the incidence of any tumour was observed, but in males receivig the low dose there was an in- creased incidence of malignant lymphomas in mice and of mononuclear-cell leukaemia in rats. Tetrakis(hydroxyethyl) phosphonium chloride was tested for carcinogenicity by oral administration in one strain of mice and in one strain of rats. No dose-related increase in the incidence of any tumour was observed; however, in male rats receivig the low dose there was an increased incidence of mononuclear-cellieukaemia. Tetrakis(hydroxymethyl) phosphonium chloride did not show significant promoting activity in a two-stage ski carcinoge- nicity test in mice. A mIxed acetate/phosphate salt of tetraki(hydroxyethyl) phosphonium base showed weak promoting activity in a two-stage ski carcinogenicity study. 4.3 Human carcinogenicity data No data were available to the Workig Group. 4.4 Other relevant data ln single studies, tetrakis(hydroxyethyl) phosphonium sulfate did not induce micronuclei but caused a marginal increase in the frequency of chromosomal aberrations in mouse bone marrow in vivo and induced mutation in mouse cells in vitro. It was not mutagenic to bacteria either in the presence or absence of an exogenous metabolic system. ~ ~ Summary table of genetic and related effects of tetrakis(hydroxyethyl) phosphonium chloride Nonmammalian systems Prokaryotes Plants Lower ~ Mammalian systems s: Inseets Animal cells D G o z o ln vivo ln vitro eukarotes D R G A D G C R G C A D - G S +1 + M C A T 1 D G S Humans Animais Human cells M C A T 1 D G S M C DL A D S Ci M C A + A aneuploidy; C, ehrom05mal aberrtions; D, DNA damage; DL, dominant lethal mutation; G, gene mutation; l, inhibition of intercellular communication; M, micronuclei; R, mitotic recmbination and gene conversion; S, sister ehromatid exhange; 1; cell transformation ln completing the tables, the following symbols indicaJe the consnsus of the Worldng Group with regard to the reults for eah end considere to be negative + 1 considered to be poitive, but only one valid study wa avalable to the Working Group + considered to be poitive for the speifie endpoint and level of biological complexity ~ :: en ~ o E point: s: tT ~ '" t: ~ cr ~~ Summary table of genetic and relatedeffects of tetrakis(hydroxyethyl) phosphonium sulfate Insts Plants Lower Prokaryotes o ~ Mammalian systems Nonmammalian systems ln vitro eukarotes G D R G A D G C R G C A D G S M C A T 1 D G S M C A +1 - T 1 D G ~ Humans Animais Human cells Animal cells D ~ ln vivo S M C _1 +1 DL A D S s: M C A ~ ~ ,c "" A aneuploidy; C, chromosmal aberrtions; D, DNA damage; DL, dominant lethal mutation; G, gene mutation; L inhibition of intercellular communication; M, micronuclei; R, mitotic recmbination and gene conversion; S, sister chromatid exchange; 1; cell transfonnation ln completing the tables, th fo/lowing symbo indu:aie the consnsus of the Worling Group with rear to the rets for ea end considered to be negative + 1 considere to be poitive, but only one valid study wa avalable to the Working Group. considered to be negative, but only one valid study wa avalable to the Working Group point: :: ocr "" :: o ~ a: cr ~ cr ..o Ul lAC MONOGRAHS VOLUME 48 106 Tetraki(hydroxyethyl) phosphonium chloride induced sister chromatid exchange and chromosomal aberrations in Chinese hamster cells in vitro and, in a single study, mutation in mouse cells in vitro. It was not mutagenie to bacteri either in the presence or absence of an exogenous metabolic system. 4.5 Evaluation 1 There is inadequate evidence for the carciogenicity of tetraki(hydroxyethyl) phosphonium salts in experiental animaIs. No data were available from studies in humans on the carcinogenicity of tetrakis- (hydroxyethyl) phosphonium salts. Overall evaluation Tetraki(hydroxyethyl) phosphonium salts are not classifiable as to their carcinogenicity to human (Group 3). 5. References Albright & Wilson America, Ine. (1988a) Materi Safety Data Sheet: Retardol C, Richmond, VA Albright & Wilsn America, Ine. (1988b) Materi Sa/ety Data Sheet: Retardol S, Richmond, VA Aoyama, M. (1975) Effect of anti-flame treating agents on the skIn. Nagoya med. J., 20, 11-19 Connor, IH., Meyne, J. & Legator, M.S. (1980) The mutagenic evaluation of tetrak(hydroxyethyl)phosphonium sulfate using a combined testing approach. 1 environ. Pathol. Toxicol., 4, 145-158 Duff, J.J. (1983) Source control: modification of a flame retardant chemicaI. PlantlOper. Progr., 2, 241-243 Ehrlich, K., Hulett, A. & Tumham, l (1980) Mammalian cell culture mutagenicity and cacinogenicity testing of dimethyl sulfoxide extract of flame retardant-treated cotton fabrics.l Toxicol. environ. Heath, 6, 259-271 Frank, A. W. (1977) The iodometric determination of P(III) in flame retardants for cotton. 4. Reaction of THPC with iodate. 1 Tex. Re., 47, 601 Frank A. w., Daigle, D.J. & Vail, S.L (1982) Chemistry of hydroxyethyl phosphoru compounds. III. Phosphines, phosphine oxides, and phosphonium hydroxides. 1 Tex. Re., 52, 738-750 Grasll, J.G. & Ritchey, W.M., ed (1975) CRC A/laso/Spetra Data and PhysicaJ Constants forOrganic Compounds, Vol. 4, Cleveland, OH, CRC Pres, p. 120 Hawley, G.G. (1981) Condensed ChemicaJ Dictionar, lOth ed., New York, Van Nostrand Reinhold, p. 100 1For desption of the italiciz terms and criteria for making the evaluation, se Preamble, pp. 25-29. TETRAS(HYDROXYMETHYL) PHOSPHONIUM SALTS 107 Hooper, G. (1973) Phosphine-basd fire retardants for cellulosic textiles. ln: LeBlanc, R.B., ed., Proceedings of the First Symposium on Texile Flammability, East Greenwich, RI, LeBlanc Research COIp., pp. 50- (Chem. Abstr., 84, 32438z) Hooper, G., Nakajima, WN. & Herbes, WE (1976a) The use of various phosphonium salts for flame retardancy by the ammonia cure technique. ln: Bhatnagar, Y.M., ed., Fire Retardants, Proceedings of 1975 International Symposium on Flammabilityand Fire Retardants, May 22-23,1975, Montrea, Canada, Westprt, CT, Technomic Publishing Co., pp. 98-114 Hooper, G., Nakajima, WN. & Herbes, WE (1976b) The use of varous phosphonium salts for flame retardancy by the ammonia cure technique. 1 coated Fabr., 6, 105-120 (Chem. Abstr., 86, 91593k) the Carinogenic Risk ofChemicals to Human, Vol. 29, Some Industrial Chemicals and Dyestuff, Lyon, pp. 345-389 Ishidate, M., ed. (1983) Chromosomal Aberration Test ln Vitro, Tokyo, Realize, Inc., p. 539 lAC (1982)IARC Monographon the Evaluation of Lowengart, C & Van Duuren, B.L (1976) The reaction of guanosine with tetrakis(hydroxyethyl)phosphonium chloride. Tetraedron LeU., 39,3473-3476 Lowengar, G. & Van Duuren, B.L (1977) Evaluation of chemical flame retardants for carcinogenic potentiaL.l Toxicol. environ. Health, 2,539-546 Loveday, K.S., Lugo, M.H., Resnick, M.A, Anderson, B.E. & Zeiger, E. (1989) Chromosome aberration and sis ter chromatid exchange tests in Chinese hamster ovar cells in vitro. II. Results with 20 chemicals. Environ. mol. Mutagenesis, 13, 6094 MacGregor, J.1, Diamond, M.J., Mazzeno, LW, Jr & Friedman, M. (1980) Mutagenicity tests of fab- ric-finishing agents in Salmonella typhimurium: fiber-reactive wool dyes and cotton f1ame retardants. Environ. Mutagenesis, 2,405-418 National Institute for Ocpational Safety and Health (1977) National Occupational Hazard SU/vey (NOHS), Cincinnati, OH National Toxicology Program (1987) Toxicology and Carinogenesis Studies of Tetrakis(hydroxymethyl) Phosphonium Sulfate (THPS) ¡CAS No. 55566-30-8) and Tetrakis(hydroxymethyl) Phosphonium Chloride (THPC) ¡CAS No. 124-64-1) in F344/N Rats and B6C3F1 Mice (Gavage Studies) (Technical Report No. 296; NIH Publ. No. 87-2552), Research Tnangle Park, NC Sadtler Research Laboratones (1980) Standard Spectra Collection, 1980 Cumulative Index, Philadelphia, PA Sasaki, M., Sugimura, K., Yoshida, M.A & Abe, S. (1980) Cytogenetic effects of 60 chemicals on cultured human and Chinese hamster cells. Senshokutai, 20, 574-584 Ulsamer, AG., Osterberg, R.E. & McLaughlin, J., Jr (1980) Flame-retardant chemicals ¡n textiles. Clin. Toxicol., 17, 101-131 Van Duuren, B.L, Lowengart, G., Seidman, 1., Smith, AC. & Melchionne, S. (1978) Mouse skin carcinogenicity tests of the flame retardants tris(2,3-dibromopropyl)phosphate, tetrakis(hydroxyethyl)phosphonium chloride, and polyvnyl bromide. Cancer Re., 38, 3236-3240 Weil, E.D. (1980) Flame retardants (phosphorous compounds). ln: Mark, H.E, Othmer, D.E, Overberger, CG., Seaborg, G.T & Graysn, M., eds, Kirl-Othmer Encyclopedia ofChemical Technolo- gy, 3rd ed., VoL. 10, New York, John Wiley & Sons, pp. 411-412