Polyamine resins

Another significant end-use for polyamines is in preparation of paper wet-strength resins. These are polyamide, modified formaldehyde, and polyamine resins used to improve the physical strength of tissue, toweling, and packaging paper products. The cationic formaldehyde resins include both urea—formaldehyde and melamine—formaldehyde types (248,249). Cationic functionaHty is imparted by incorporation of DETA, TETA, and/or TEPA in... 

Several resins have been used frequently in reactant sequestration. Ami-nomethylpolystyrene 1 and the more highly functionalized polyamine resins 2 and 3 have been reported to sequester excesses of solution-phase electrophiles, including isocyanates, isothiocyanates, sulfonyl chlorides, acid chlorides, anhydrides, aldehydes, and imines. Cross-site reactivity is not an issue with the more densely functionalized sequestering resins so their use in an automated laboratory environment offers a significant resin and volume economy compared to less densely functionalized resins. 

A single, functionalized resin can be designed to capture more than one reactant. For instance, resin 3 has been used to sequester excess alde-hydes/ketones and thioacetic acids.28 Specifically, the polyamine resin 3 did this by forming the resin-bound thiazolidinones 11 and salts from the excess reagents, leaving the desired thiazolidinones in solution. 

Several new phases applied to maltosaccharide analysis that seem to be promising have been described in the literature, for instance, a silica-phase covered with polymeric polyamine resin, and an entirely polymeric resin containing an amide function (35). In any case, partition chromatography is restricted mainly to the utilization of polar-bonded phases, as already described. Nevertheless, there have been a certain number of applications of reversed-phase chromatography that permit relatively simple separations to be achieved. Octadecyl-bonded silica phases are the most widely used, although few applications involve carbohydrate analysis. Their interest lies rather in the analysis of derivated sugars, where the selectivity increases (36). 

Phenylpentan-l-ol (46). A solution of benzaldehyde (0.5 mmol) in THF (2 ml) was treated at 78° with a solution of n-buthyllithium (0.36 ml, 1.6 M solution in hexanes, 0.57 mmol). The resulting reaction mixture was allowed to slowly reach RT and stirred for 2.5 h. Then carboxylic acid resin (5, 0.80 g, 8 mmol, 10.0 mequiv./g) was added and the suspension was stirred for 4 h. The resin was filtered and rinsed with THF a few times until complete washing of the product. Upon evaporation of the filtrate, lithium-free product was obtained, which was then dissolved in DCM followed by the addition of polyamine resin (0.50 g, 1.49 mmol). This suspension was stirred at room temperature for 5 h. The reaction mixture was then filtered and the resin rinsed with DCM until complete washing of the product. Upon evaporation of the solvent, pure (benzaldehyde-free) 1-phenylpentan-l-ol was obtained. 

Bolto, B. A. The role of polyamine resins in thermally regenerable ion exchange, in Polymeric amines and ammonium salts, (ed.) Goethals, E. J., p. 365, New York, Pergamon Press 1980... 

Stanax 1166 Standard Chemical Products polyamine resin... 

ON THE PICKUP OF HYDROCHLORIC AND SULFURIC ACIDS ON A POLYAMINE RESIN... 

The number of nitrogens in the chain can vary from two on up. In many cases the nitrogen-carbon bond is an integral part of the polymer network. There are more than two carbons between nitrogens in some cases, and the carbons may carry other substitutions. The actual ionogenic functionality is a mixture of primary, secondary and tertiary amines. Polyamine resins made by condensing phenol, formaldehyde and polyamine were among the first commercial resins. Other methods of manufacture include the reaction of a polyamine with a chloromethylated styrene-divinyl-benzene copolymer, and condensation of epichlorhydrin with ammonia or polyamines. 

In water treatment these resins are used to remove mineral acids from solution, usually as the second step in demineralization. The most important property to the engineer is their operating capacity. How much mineral acid can the resin remove under a given set of conditions The operating capacity of a polyamine resin has been found to be a function of a number of operating conditions. The operating capacity ... 

These explanations are based on conditions inside the resin. Changing conditions outside the resin should have only minor effects over fairly wide ranges. The change from hydrochloric to sulfuric acid does not seem to fit this pattern. This difference in behaviour between hydrochloric acid and sulfuric acid is due to the step-wise ionization of the sulfuric acid molecule. Both equilibrium and kinetic components are involved. These can be seen in data taken on a recently introduced polyamine resin, Duolite ES-340. This resin is made by an inverse suspension condensation of a polyamine and epichlorhydrin. 

Not all polyamine resins show these characteristics to the same degree. Duolite ES-340 has a relatively high basicity and good column performance. The basicity of some polyamine resins is low enough that their operating capacity to sulfuric acid is condition dependent. The polyamine resins based on chloromethylated styrene-... 

Water molecules are so small and cellulose and so hydrophilic that this solution usually affords only temporary protection. Formaldehyde, glyoxal, polyethylen-imine, and, more recently, derivatized starch (50) and derivatized cationic polyacrylamide resins (51) have been used to provide temporary wet strength. The first two materials must be applied to the formed paper, but the other materials are substantive to the fiber and may be used as wet-end additives. Carboxymethylcellulose-calcium chloride and locust-bean gum-borax are examples of two-component systems applied separately to paper that were used to a limited extent before the advent of the amino resins. Today three major types of wet-strength resins are used in papermaking polyamide-polyamine resins cross-linked with epichlorohydrin (52) are used in neutral to alkaline papers cationic polyacrylamide resins cross-linked with glyoxal are used for acid to neutral papers and melamine-formaldehyde resins are used for acid papers. 

---