Poly sulfonamides

Thiazetidine 1,1-dioxides or 3-sultams can be polymerized to high-molecular-weight polysulfonamides.l,2-Thiazetidin-3-one 1,1-dioxides react with aliphatic diamines to give polyamide-poly sulfonamide polymers. Fluorinated 3-keto and 3-imino derivatives were investigated as surface-active agents, and Ai-malonyl derivatives of l,2-thiazetidin-3-one 1,1-dioxide are said to be yellow couplers for color photography. ... 

Poly sulfonamide type (from disulfochloride +diamine)... 

Exploratory studies with a variety of phthalimides, containing trimethylsilyl-terminated poly-sulfonamide, poly-ether and poly-thioether chains, showed that these substances undergo modestly to highly efficient photocyclization reactions to produce the corresponding macrocyclic products. Examples of these processes are shown in Scheme 5.10 through Scheme 5.15 [25,26]. 

Fractionation by Zone Melting VII-333 Poly(sulfonamides) VII41 6... 

POLY(SULFIDES), POLY(SULFONES), POLY(SULFONAMIDES) Poly( 1 -(n-alkylthio)-1 -propynes)... 

Resinous products ha e been obtained by reaction of a wide riety of di-and polyamides and su If amides Anth formaldehyde. Poly sulfonamides alsogiA-e resins on heating with formaldehyde and acids". 

A variety of waxy hydrophobic hydrocarbon-based soHd phases are used including fatty acid amides and sulfonamides, hydrocarbon waxes such as montan wax [8002-53-7], and soHd fatty acids and esters. The amides are particularly important commercially. One example is the use of ethylenediamine distearamide [110-30-5] as a component of latex paint and paper pulp blackHquor defoamer (11). Hydrocarbon-based polymers are also used as the soHd components of antifoaming compositions (5) examples include polyethylene [9002-88-4], poly(vinyl chloride) [9002-86-2], and polymeric ion-exchange resins. 

Superheated water at 100°-240 °C, with its obvious benefits of low cost and low toxicity, was proposed as a solvent for reversed-phase chromatography.59 Hydrophobic compounds such as parabens, sulfonamides, and barbiturates were separated rapidly on poly(styrene-divinyl benzene) and graphitic phases. Elution of simple aromatic compounds with acetonitrile-water heated at 30°-130 °C was studied on coupled colums of zirconia coated with polybutadiene and carbon.60 The retention order on the polybutadiene phase is essentially uncorrelated to that on the carbon phase, so adjusting the temperature of one of the columns allows the resolution of critical pairs of... 

A different pH-triggered deshielding concept with hydrophilic polymers is based on reversing noncovalent electrostatic bonds [78, 195, 197]. For example, a pH-responsive sulfonamide/PEl system was developed for tumor-specific pDNA delivery [195]. At pH 7.4, the pH-sensitive diblock copolymer, poly(methacryloyl sulfadimethoxine) (PSD)-hZocA -PEG (PSD-b-PEG), binds to DNA/PEI polyplexes and shields against cell interaction. At pH 6.6 (such as in a hypoxic extracellular tumor environment or in endosomes), PSD-b-PEG becomes uncharged due to sulfonamide protonation and detaches from the nanoparticles, permitting PEI to interact with cells. In this fashion PSD-b-PEG is able to discern the small difference in pH between normal and tumor tissues. 

Cho et al. have recently described the synthesis of a sulfonimide containing monomer and the resulting poly (ary lene ether sulfone) copolymers. In this procedure 3,3 -disulfonate-4,4 —dichlorodiphenyl sulfone was refluxed in thionyl chloride, isolated, and then reacted with trifluoromethanesulfonamide in the presence of triethylamine to form the sulfonamide analogue monomer as shown in Figure 44. This... 

Kawahara et al. 95 fabricated an aromatic poly(amide imide sulfonamide) reverse osmosis membrane 36 from N-4 -chlorosulfonylphthalimide and p-phenylenediamine. 

The introduction of azobenzene units into the side chains of poly(L-lysine) has been achieved be means of various procedures and different azo reagents. The polymers described initially contained azobenzene units linked to the lysine side chains by means of an amide moiety 29-311 (Scheme 4, Structure V). More recently, Fissi et al. 321 have described azo-modified poly(L-lysine) in which the azobenzene units are linked to the Lys side chains by means of a sulfonamide function (Scheme 4, Structure VI). The two families of azo-modified poly(L-lysine) have been found to exhibit completely different conformational and photoresponsive behavior. 

Poly(L-lysine) containing azobenzene units linked to the side chains by means of a sulfonamide function (Scheme 4, Structure VI), was obtained by treating poly(L-lysine) with p-phenylazobenzenesulfonyl chloride. The poly(a-amino acid) was modified quantitatively conversion to the azo-lysine units of VI was effectively 100%. The azo-modified polypeptide was soluble in HFP, in which it exhibited an intense photochromism attributed to the trans-cis photoisomerization of the azobenzene units. Like other sulfonated azobenzene compounds, 33 azosulfonyl-modified polymers of L-lysine were found to be very stable in their tis form, and no thermal decay was observed at room temperature over periods of times as long as several weeks. Interconversion between the two forms at room temperature could only be effected by irradiation at appropriate wavelengths. This behavior allowed the authors to purify the trans and cis forms of the model compound NE-azobenzenesulfonyl-L-lysine (VII) by chromatography, and to measure the absorption spectra of the two pure photoisomers. 

Allylation of aldimines and sulfonimines with indium powder in poly(propylene) glycol (MW 1000), a benign and recyclable reaction medium, results in the formation of the corresponding homoallylic amines and sulfonamides in high yields (Equation (62)).265... 

An attempt to formulate a poly(4-hydroxy styrene)-based resist was less than completely successful because the difference in the rates of dissolution were too small to be used to give high contrast images. Other small molecules were added to the NDS/novolac resist and these were also found to have a profound effect upon the performance of the resist, particularly the development properties. When it was necessary to obtain higher dissolution rates, several triazoles and sulfonamides were found to improve the rate of development in the exposed areas without causing unacceptable thickness losses in the unexposed areas. Dyes incorporated to minimize problems of reflection and scattered light were also found to alter the dissolution behavior of the resist coating. 

A soluble poly(ethylene glycol)-supported derivative of the 2-(trimethylsilyl)e-thylsulfonyl protective group (PEG-supported SES) has been utilized to anchor (S)-allylglycine methyl ester (105). After N-aUcylation of the resulting sulfonamide with various unsaturated bromides, RCM with Grubbs catalysts has been performed, leading to cyclic a-amino esters of various ring sizes (108) (Scheme 24) [223]. 

A more recent example by Balzani and Vbgtle provided an additional chro-mophore for cascade energy transfer [115]. Poly(aryl ether) dendrons with naphthyl groups at the periphery were attached to the sulfonamides of the second generation dansyl terminated dendrimers to create a super dendrimer 86 consisting of three different types of chromophores 32 naphthyls, 24 alkoxybenzenes, and 8 dansyls (Scheme 44). When eosin is extracted into... 

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