An investigation was undertaken of the variation in the reaction extent of formaldehyde with wool at the various re action sites as a function of variation in the formaldehyde content and/or the conditions of treatment. It was found that primary amino groups, tyrosyl residues, and tryptophyl residues reacted extensively and contributed in different extents to the total formaldehyde uptake by the wool. Tyrosyl and tryptophyl residues reacted more extensively at low and high pH levels than at intermediate levels. Amino groups showed less variation in reaction extent with pH than did the other two types of residue. It was demonstrated that some of the amino groups reacted with formaldehyde to give products which were stable to rinsing in distilled water at room temperature but which were broken down by aqueous pyridine at 100°C.
Alexander, P. and Block, R.J., "A Laboratory Manual of Analytical Methods of Protein Chemistry," U. K. Pergamon Press, 1960, p. 92.
2.
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3.
Alexander, P. , Hudson, R.F., and Earland, C., "Wool: Its Chemistry and Physics," 2nd edition, London, Chapman and Hall, 1963, p. 79.
4.
Beyer, H. and Schenk, U., Determination of Dinitrophenyl Amino Acids in Structural Proteins by Chromatography on Nylon Powder Columns, J. Chrom.39, 482-496( 1969).
5.
Blass, J., Bizzini, B., and Raynaud, M., Études sur le Mécanisme de la Détoxification des Toxines par le formol , Bull. Chim. Soc. Fr., 39573965 (1967).
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Breslauer, J. and Pictet, A., Uber einige Kondensationsprodukte des Formaldehyds , Ber.40, 3784-3786 (1907 ).
7.
Brown, A.E., Hornstein, L.R., and Harris, M., The Chemical Modification of Wool Treatment with Formaldehyde Solutions , Textile Res. J.21, 222227 ( 1951).
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Burr, G.O. and Gortner, R.A., The Humin Formed by the Acid Hydrolysis of Proteins. VIII. The Condensation of Indole Derivatives with Aldehydes. J. A mer. Chem. Soc.46, 1224-1246 (1924).
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Cegarra, J. and Gacen, J., A Method of Determining the Amount of Tryptophan in Wool by Hydrolysis with Sulphuric Acid for Short Periods, J. Soc. Dyers Colorists84, 216-220 (1968).
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Ceriotti, G. and Spandrio, L., Colorimetric Determination of Tyrosine, Biochem. J.66, 607-610 (1957).
11.
Croston, C.B. , Stabilization of Zein Filaments, Ind. Eng. Chem.42, 484-486 (1950).
12.
Decroix, G. , Mazingue, G., and van Overbeke , M., Crosslinking of Wool with Aldehydes, Bull. Inst. Textile France, No. 84, 33-47 (1959).
13.
Fraenkel-Conrat, H., Brandon, B.A., and Olcott, H.S., Chemical Characterisation and Crystallization of Formaldehyde Derivatives of Gramicidin, Federation Proc.5, 134 (1946).
14.
Fraenkel-Conrat, H., Brandon, B.A., and Olcott, H.S., The Reaction of Formaldehyde with Proteins. IV. Participation of Indole Groups. Gramicidin , J. Biol. Chem.168, 99-118 (1947).
15.
Fraenkel-Conrat, H. and Olcott, H.S., The Reaction of Formaldehyde with Proteins. V. Cross-Linking Between Amino and Primary Amide or Guanidyl Groups, J. Amer. Chem. Soc.70, 2673-2684 (1948 ).
16.
Fraenkel-Conrat, H. and Olcott, H.S., Reaction of Formaldehyde with Proteins. VI. Cross-Linking of Amino Groups with Phenol, Imidazole or Indole Groups , J. Biol. Chem.174, 827-843 (1948).
17.
French, D. and Edsall, J.T., The Reaction of Formaldehyde with Amino Acids and Proteins, Adv. Protein Chem.2, 277-335 (1945).
18.
Gortner, R.A. and Holm, G.E., On the Origin of the Humin Formed by the Acid Hydrolysis of Proteins. III. Hydrolysis in the Presence of Aldehydes , J. Amer. Chem. Soc.39, 2477-2501 (1917 ).
19.
Gruen, L.C. and Nicholls, P.W., The Effect of Thiourea and Formaldehyde Treatment on the Chemical Analyses of Wool, Aust. J. Chem.22, 2137-2143 (1969).
20.
Holm, G.E. and Gortner, R.A., On the Origin of the Humin Formed by the Acid Hydrolysis of Proteins. IV. Hydrolysis in the Presence of Aldehydes, J. Amer. Chem. Soc.42, 632-640 (1920).
21.
Jacobs, W.A. and Craig, L.C., The Ergot Alkaloids. VIII. The Synthesis of 4-Carboline Carbonic Acids, J. Biol. Chem.113, 759-765, (1936).
22.
Lugg, J.W.H. , On the Use of Mercuric Salts and Nitrous Acid in the Colorimetric Determination of Tyrosine and Tryptophan Present in Solution , Biochem. J.31, 1422-1433 (1937 ).
23.
McPhee, J.R. , The Reaction of Formaldehyde with Wool and its Effect on Digestion by Insects, Textile Res. J.28, 303-314 (1958).
24.
Middlebrook, W.R., The Irreversible Combination of Formaldehyde with Proteins, Biochem. J.44, 17-23 (1949).
25.
Petersen, H. , Reaction Mechanisms , Structures, and Properties ofMethylol Compounds in Cross-Linking Cotton, Textile Res. J.38, 156-176 (1968).
26.
Reddie, R.N. and Nicholls, C.H., Absorption of Formaldehyde by Wool, Textile Res. J.41, 303-311 (1971).
27.
Siepman, E. and Zahn, H., Automatic Analysis of Watersoluble 2,4-dinitrophenyl-amino-acids by Chromatography on Nylon Powder, 3rd Intern. Wool Textile Res. Conf., Paris, Section 1, 303-310 (1965).
28.
Steinhardt, J., Fugitt, C.H., and Harris, M., The Effect of Formaldehyde on the Acidic and Basic Properties of Wool, J. Biol. Chem.165, 285-291 (1946).
29.
Swain, A.P. , Kokes, E.L., Hipp , N.J., Wood, J.L., and Jackson, R.W., Combination of Formaldehyde with Casein , Ind. and Eng. Chem.40, 465-469 (1948).
30.
Thomas, L.E. , A New Method for the Determination of Tyrosine and its use in Determining the Tyrosine Content of Edestin, Casein and Tobacco Mosaic Virus, Arch. Biochem.5, 175-181 (1944).
31.
Walker, J.F. , "Formaldehyde," 3rd ed., New York, Reinhold, 1967 p. 266.
32.
Walker, J.F. , ibid. p. 306.
33.
Walker, J.F. , ibid., p. 308.
34.
Zahn, H., Einbau von kunstlichen Querbrucken in Faserproteine, Das Leder19, 144-153 (1968).
