The side reactions of the polymerization of tetrakis(hydroxymethyl)phosphonium hydroxide-ammonia (THPOH-NH 3) for flame-retardant treatment of cotton textiles yield water-soluble products. This report attempts to answer some of the questions which relate to the kinetics and thermodynamics of these side reactions and to characterize some of the products. Hexamethylenetetramine was established by adsorption chromatography and by internal reflection infrared spectroscopy as a competing side-reaction product. Also, aminomethanol and hexahydro-1,3-5-triazine are strongly suggested as associated intermediate compounds.
Beninate, J.V. , Boylston, E.K., Drake, G.L., Jr., and Reeves , W.A., Application of a New Phosphonium Flame Retardant, Amer. Dyest. Rep.57, P981-P985 (1968).
3.
Beninate, J.V. , Boylston, E.K., Drake, G.L., Jr., and Reeves , W.A., Conventional Pad-Dry-Cure Process for Durable-Flame and Wrinkle Resistance with Tetrakis-(hydroxymethyl)Phosphonium Hydroxide (THPOH), Textile Res. J. 38, 267-272 (1968).
4.
Beninate; J.V. , Perkins, R.M., Drake, G.L., Jr., and Reeves , W.A., An Economical Durable Flame-Retardant Finish for Cotton, Textile Res. J. 39, 368-374 (1969).
5.
Beninate, J.V. , Boylston, E.K., Drake, G.L., Jr., and Reeves , W.A., (to Sec. of Agr.). Imparting Flame Resistance to Fibrous Textiles from an Alkaline Medium, U. S. Patent 3,607,356 (Sept. 21, 1971).
6.
Bichowsky, F.R. and Rossini, F.D., "The Thermochemistry of the Chemical Substances ," New York, Reinhold, 1936, p. 207.
Daniels, F., "Outlines of Physical Chemistry," 3rd Ed., New York, Wiley, 1948, p. 157.
9.
Drake, G.L., Jr., Beninate, J.V., Cooper, A.S., Jr., Walker, A.N., and Reeves, W.A., "A Chemical Drying and Curing Technique for Imparting Flame Resistance to Cotton," Symp. Int. Rech. Text. Cotonnière, 1st, Paris, 1969, Inst. Text. de France, Boulogne-sur-Seine, 721-733 (1969).
10.
Ellzey, S.E. , Jr., Connick, W.J., Jr., Boudreaux , G.J., and Klapper, H., A Nuclear Magnetic Resonance Study of the Formaldehyde-Induced Exchange of Methylol Groups in Tetrakis(hydroxymethyl)phosphonium Chloride and Tris-(hydroxymethyl)phosphine , J. Org. Chem.37, 3453-3457 (1972 ).
11.
Guthrie, J.D. , Drake, G.L., Jr., and Reeves , W.A., Application of the THPC Flame-Retardant Process to Cotton Fabrics, Amer. Dyest. Rep.44, P328-P332 (1955).
12.
Inoue, M. and Kawai, M.Urea Resins. VII. pH Change of Urea-Formaldehyde Solution by Alkaline Catalyst , Nagoya-shi Kôgyô Kenkyûsho Kenkyu Hôkoku17, 6-12 (1957).
13.
Morris, N.M. , McCall, E.R., and Tripp, V.W., Identifying Finishes by Infrared Spectroscopy: Fluorochemicals and Flame Retardants, Textile Chem. Color4, 283-286 (1972).
14.
Moore, S. and Stein, W.H., A Modified Ninhydrin Reagent for the Photometric Determination of Amino Acids and Related Compounds, J. Biol. Chem.211, 907-913 (1954).
15.
Partridge, S.M. and Westall, R.G., Filter-paper Partition Chromatography of Sugars, Biochem. J.42, 238-248 (1948).
16.
Perkins, R.M. , Beninate, J.V., Mazzeno, L.W., Jr., Reeves, W.A., and Hoffman, M.J., The THPOH-NH3 Process— Current Pilot-Plant Application to Cotton Fabric, Colourage20, 29-32 ( 1973).
17.
Perkins, R.M. , Calamari, T.A., Moore, H.B., Schreiber, S.P., and Cooper, A.S., Jr., Ammonia Reactor for Continuous Production of Fire Retardant Cottons, Amer. Dyest. Rep.63, 30, 32, 34, 36-38, 52-53 (1974).
18.
Reeves, W.A. , Drake, G.L., Jr., Beninate , J.V., and Perkins, R.M., A Comparison of Four Flame Retardants, Textile Chem. Color.1, 365-369 (1969).
19.
Reeves, W.A. , Perkins, R.M., Piccolo, B., and Drake, G.L., Jr., Some Chemical and Physical Factors Influencing Flame Retardancy, Textile Res. J.40, 223-231 (1970).
20.
Reeves, W.A. , Daigle, D.J., Donaldson, D.J., and Drake, G.L., Jr., Methylol Phosphorus Polymers Used for Flame Retardants, Textile Chem. Color.2, 283-285 (1970).
21.
Reeves, W.A. and Perkins, R.M., Chemistry of THPC in Flame Retardants for Cotton, Colourage Annual, 1971, 1-7.
22.
Zinzadze, C. , Colorimetric Methods for the Determination of Phosphorus, Ind. Eng. Chem., Anal. Ed.7, 227-230 (1935).
