724
H. Shao et al. / Journal of Fluorine Chemistry 125 (2004) 721–724
À122.60 (m, 6F), À122.90 (s, 2F), À123.52 (s, 2F), À126.41
s, 2F).
m/z: 576(15), 533(7), 475(13), 127(6), 121(18), 91(13),
58(100), 42(24), 41(19). Anal. Calc. for C H F INO Si:
(
2
2
31 17
5
C, 30.46; H, 3.60; N, 1.61. Found: C, 29.27; H, 3.24; N,
1.20%.
3
.3. Ester 4
A 500-ml flask was equipped with an automatic water
3.5. Surface modification of cotton fabrics with
compound 5
separator carrying an efficient reflux condenser at its upper
end. Then acid 3 (31.1 g, 63.1 mmol), 3-dimethylamino-1-
propanol (7.5 g, 75.1 mmol), p-toluenesulfonic acid (0.05 g,
The fabrics were padded with the 3% (w/w) compound 5
in MeOH and water (95/5, v/v), the impregnated specimens
were dried at 80 8C for 3 min and cured at 160 8C for 3 min.
0
.263 mmol) and toluene (200 ml) were added. The reaction
mixture was refluxed until no water was collected in the water
separator. The solvent was removed invacuo. The residuewas
dissolved in 100 ml ether, then washed three times with water
(
50 ml), brine, dried over anhydrous MgSO . After the
4
Acknowledgements
removal of solvent, the residue was purified by column
chromatography on silica gel (CH Cl :MeOH acetate ¼
We thank the Ministry of Education of China for financial
support.
2
2
1
0 : 1) to give compound 4 (20.8 g, 57% yield) as a pale
1
yellow oil. H NMR (300 MHz, CDCl ) d 1.85 (m, 2H), 2.26
3
(
s, 6H), 2.38 (t, J ¼ 7:2 Hz, 2H), 2.40–2.56 (m, 2H), 2.64 (t,
19
J ¼ 7:8 Hz, 2H), 4.20 (t, J ¼ 7:2 Hz, 2H). F NMR
References
(
(
282 MHz, CDCl ) d À80.81 (t, J ¼ 9:9 Hz, 3F), À114.79
3
m, 2F), À121.79 to À122.00 (m, 6F), À122.85 (s, 2F),
[
[
[
1] J.C. Tiller, C.J. Liao, K. Lewis, A.M. Klibanov, Proc. Natl. Acad.
Sci. USA 98 (2001) 5981–5985.
2] J.C. Tiller, S.B. Lee, K. Lewis, A.M. Klibanov, Biotechnol. Bioeng.
À123.59 (s, 2F), À126.21 (s, 2F). IR (thin film): 2955,
2
1
4
823, 2773, 1774, 1465, 1336, 1243, 1208, 1152, 1114,
043, 984, 705, 658, 529. MS m/z: 577(19), 558(5),
75(21), 457(2), 86(8), 84(8), 58(100). Anal. Calc. for
7
9 (2002) 465–471.
3] R.S. Nohr, G.J. Macdonald, J. Biomater. Sci. Polym. Ed. 5 (1994)
07–619.
6
C H F NO : C, 33.29; H, 2.79; N, 2.43. Found: C,
1
6
16 17
2
[4] K.K. Leonas, INDA J. Nonwovens Res. 5 (1993) 22–26.
[5] S. Lee, J.S. Cho, G. Cho, Textile Res. J. 69 (1999) 104–112.
3
2.89; H, 2.75; N, 2.60%.
[
6] V. Castelvetro, G. Francini, G. Ciardelli, M. Ceccato, Textile Res. J.
1 (2001) 399–406.
7
3
.4. Quaternary ammonium silane coupling agent 5
A mixture of ester 4 (9.04 g, 15.66 mmol), (3-iodopro-
pyl)trimethoxysilane (6.62 g, 22.8 mmol) and anhydrous
[
7] (a) H. Sawada, K. Yanagida, Y. Inaba, M. Sugiya, T. Kawase, T.
Tomita, Eur. Polym. J. 37 (2001) 1433–1439;
(
b) H. Sawada, Y. Murai, M. Kurachi, T. Kawase, T. Minami, J.
Kyokane, T. Tomita, J. Mater. Chem. 12 (2002) 188–194.
8] J.M. Vincent, A. Rabion, V.K. Yachandra, R.H. Fish, Angew. Chem.,
Int. Ed. Engl. 36 (21) (1997) 2346–2349.
[
[
CH CN (15 ml) was stirred at 50 8C for 24 h. The solvent
3
was removed in vacuo. The residue was washed with
anhydrous ether (5 Â 20 ml) to give quaternary ammonium
9] AATCC Technical Manual, American Association of Textile
Chemists and Colorists, Research Triangle Park, NC, 1989.
1
salt 5 (13.1 g, 96%) as a pale yellow viscous solid. H NMR
(
[
10] O. Yuke, Test Method of Antimicrobial Finished Fabrics, Anti-
microfinish, The Antimicrobial Finish Society of Japan Textiles Co.,
300 MHz, CDCl ) d 0.61 (t, J ¼ 7:8 Hz, 2H), 1.81–1.94 (m,
3
1
989, pp. 182–184.
4
3
2
3
H), 2.40–2.50 (m, 2H), 2.54–2.62 (m, 2H), 3.04 (s, 6H),
.66 (m, 2H), 3.30 (s, 9H), 3.36 (m, 2H), 3.62(t, J ¼ 5:7 Hz,
[
[
11] W.A. Zisman, in: Contact Angle, Wettability, and Adhesion, ACS
Washington, DC, 1964, p. 1.
1
9
H). F NMR (282 MHz, CDCl ) d À80.50 (t, J ¼ 9:9 Hz,
3
12] Annual Book of ASTM Standards, Test Method F 1670-98, The
American Society for Testing and Materials, West Conshohocken,
PA, 1998.
F), À114.04 (m, 2F), À120.87 to À121.05 (m, 6F),
À121.95 (s, 2F), À122.78 (s, 2F), À125.50 (s, 2F). MS