A New Creaseproof Finish for Wool Using 2-Iminothiorane Hydrochloride and Its Reaction Mechanism

Abstract

For the purpose of developing wool fabrics with good wrinkle recovery, we have studied the reaction mechanism of a new wool processed with 2-iminothiorane hydro chloride (2-IT). With 2-IT, a number of new disulfide (-SS-) groups are introduced into wool fabrics. We investigate the reactivity of 2-IT and L-phenylalanine (Phe) as the model compound of wool by adsorption chromatography. Also, we analyze the bond structure of the product obtained from the reaction of 2-IT and Phe by ¹H-NMR and SIMS. As a result, we confirm that 2-IT reacts with the amino group of Phe, and the -SH group finally replaces the amino group. Furthermore, the sulfur (S) content and wrinkle recovery clearly increase with increasing content of 2-IT, as revealed by x-ray fluorometry. The result of increasing the number of -SS- groups in the wool fabrics is that wrinkle recovery and setting ability improve.

Get full access to this article

View all access options for this article.

References

Barr, T. , and Speakman, J.B. , The Production of Un-shrinkability by Cross-Linking Formation in Wool, Part I: Woven Fabrics, J. Soc. Dyers. Colour. 60, 335 (1944).

Carlsson, J. , Drevin, H. , and Axén, R. , Protein Thiolation and Reversible Protein-Protein Conjugation, Biochem. J. 173, 723 (1978).

Duncan, R.J.S. , Weston, P.D. , Wrigglesworth , R. , A. New Reagent Which May Be Used to Introduce Sulfhydril Groups into Proteins, and Its Use in the Preparation of Conjugates for Immunoassay, Anal. Biochem. 132, 68 ( 1983).

Hayes, R.L. , Leeder, J.D. , and Taylor, D.S. , The Wrinkling Behavior of Wool Fabrics—Conditions of Testing, Textile Res. J. 45, 712 (1975).

Hori, M. , Wool Shape Memory Woven Product, Sen'i Gakkaishi 50 (10), 559 (1994).

Katz, H.J. , Wrinkling Behavior of Wool Fabrics, Part I: A Multiple Pleat Test , Textile Res. J. 36, 874 (1966).

Kitano, M. , Wool Treatment by Natural Polymers, Sensyoku Kogyo 43, 180 (1995).

Kuzuhara, A. , and Kaimori, M. , A New Testing Method for Wrinkle Recovery of Wool Fabrics, Sen'i Kikai Gakkaishi 51, T252 (1998).

Kuzuhara, A. , and Hori, T. , The Wrinkle Behavior of Wool Fabrics with Introduced Thiol Groups and the Effects of Hg Ion Adsorption, Sen'i Gakkaishi 56 (2), 69 (2000).

10.

Kuzuhara, A. , and Hori, T. , Reducing Wrinkle Formation in Wool with 2-Iminothiorane Hydrochloride, Textile Res. J. 72, 285-289 (2002).

11.

Leeder, J.D. , Wrinkling Behavior of Wool Fabrics: Changes Induced by Chemical Modification, Textile Chem. Color. 3, 193 (1971).

12.

Leeder, J.D. , Improvement in Wrinkle Recovery of Wool Fabrics , Wool Sci. Rev. 53 ( 1977).

13.

Perham, N.R. , and Thomas, J.O. , Reaction of Tobacco Mosaic Virus with a Thiol-Containing Imidoester and a Possible Application to X-ray Diffraction Analysis, J. Molec. Biol. 62, 415 (1971).

14.

Schramm, H.J. , and Dülffer, T. , The Use of 2-Iminothiolane as a Protein Crosslinking Reagent, Hoppe-Seyler's Z. Physiol. Chem. 358, 137 (1977 ).

15.

Weston, P.D. , Devries, J.A. , and Wrigglesworth , R. , Conjugation of Enzymes to Immunoglobulins Using Dimaleimides, Biochem. Biophys. Acta 612, 40 ( 1980).

16.

White, F.H. , Jr., "Methods in Enzymology," vol. 25 ( C. H. W. Hirs. , and N. Timasheff , Eds.), Academic Press, 1972, p. 541.