Surface modification of nylon 6,6 using a carbene insertion approach

Chemical modification of materials by reaction with diaryl diazomethanes

“…7 The method relies upon the generation of carbenes by thermolytic or photolytic methods and their irreversible attachment by insertion into available surface chemical groups; a similar approach has recently been reported by Hayes. [8][9][10] Significantly, this approach permits the possibility of a post-polymerisation step for control of surface properties, but without changing the bulk characteristics of the underlying substrate, and since the applicable substrates may be both organic and inorganic polymers and materials, it is potentially very wide in scope. We have not as yet examined in detail the nature of the surface modification, and report here a study of several substrate types, which have been modified by the introduction of carboxylate, amine and alkyl substituents, using combustion analysis, attenuated total reflection (ATR) IR, reflectance UV and X-ray photoelectron spectroscopy (XPS), giving some direct information concerning the chemical and physical nature of the modified substrates.…”

Three‐Membered Heterocycles. Structure and Reactivity

“…In their study of the underlying chemistry of these processes, Hayes and coworkers photolyzed the fluorenone-modified diazirine 782 in the presence of acetic acid, n-butylamine, and N-butylbutanamide as models of the functional group environment encountered in a medium of nylon 6,6 (and, incidentally, proteins in vivo). In all cases, they observed extremely efficient (>95%) insertion reactions, leading to the products 783, 784, and 785, deriving from OÀH insertion, amine NÀH insertion, and amide NÀH insertion, respectively [761] (Scheme 2.112). …”

Enzymatic biofinishes for synthetic textiles

“…Furthermore, these groups have been used to increase hydrogen binding and to facilitate chemical bonds between substrates and adhesives. Several works have been published about the introduction of specifi c reactive groups at the surface of polyamide supports in order to reach higher levels of functionalization (Buche ń ska, 1996 ; Marcin č in, 2002 ; Tobiesen and Michielsen, 2002 ;de Gooijer et al ., 2004 ;Saïhi et al ., 2005 ;Blencowe et al ., 2006 ;Jia et al ., 2006 ;Herrera-Alonso et al ., 2006 ;Makhlouf et al ., 2007 ). Recently the covalent attachment of bioactive compounds to functionalize polymer surfaces, including relevant techniques in polymer surface modifi cation such as wet chemical, organosilanization, ionized gas treatments and UV radiation, have been described (Shearer et al ., 2000 ;Goddard and Hotchkiss, 2007 ).…”