Caprolactam properties

Uses. The principal use of adiponitrile is for hydrogenation to hexamethylene diamine leading to nylon-6,6. However, as a result of BASE s new adiponitrile-to-caprolactam process, a significant fraction of ADN produced may find its way into nylon-6 production. Adipoquanamine, which is prepared by the reaction of adiponitrile with dicyandiamide [461-58-5] (cyanoguanidine), may have uses in melamine—urea amino resins (qv) (see "Benzonitrile, Uses"). Its typical Hquid nitrile properties suggest its use as an extractant for aromatic hydrocarbons. 

Nylon-6 [25038-54-4] was first made in 1899 by heating 6-aminohexanoic acid (143), but its commercially feasible synthesis from caprolactam was discovered by Paul Schlack at 1. G. Farbenindustrie in 1938. Like nylon-6,6, it is a tough, white translucent, semicrystalline sofld, but melts at a lower temperature (T = 230° C. The physical properties and primary producers of nylon-6 are Hsted in Tables 9 and 10, respectively. 

Caprolactam, mol wt 113.16, is a white, hygroscopic, crystalline soHd at ambient temperature, with a characteristic odor. It is very soluble in water and in most common organic solvents and is sparingly soluble in high molecular weight aUphatic hydrocarbons. Molten caprolactam is a powerful solvent for polar and nonpolar organic chemicals. Selected physical properties and solubiUties of caprolactam are Hsted in Tables 1 and 2, respectively. 

A further approach is used by Bayer with their polyesteramide BAK resins. A film grade, with mechanical and thermal properties similar to those of polyethylene is marketed as BAK 1095. Based on caprolactam, adipic acid and butane diol it may be considered as a nylon 6-co-polyester. An injection moulding grade, BAK 2195, with a higher melting point and faster crystallisation is referred to as a nylon 66-co-polyester and thus presumably based on hexamethylene diamine, adipic acid and butane diol. 

Weaker polar monomers like, vinylacetate, N-vinyl pyrrolidone, fV-vinyl caprolactam or MiV-dimethyl acrylamide may be used at levels as high as 30-40% of the total monomers. Combinations of polar monomers [65-67] can also be used to formulate acrylic PSAs with a good balance of properties. 

Epoxidized novolacs, 411 Epoxy -phenol networks, 411-416 properties of, 413-416 Epoxy-phenolic reaction kinetics of, 413 mechanism of, 411-412 Epoxy structures, 414 e-Caprolactam, 174... 

Dissolution/reprecipitation processes were evaluated for the recycling of poly-epsilon-caprolactam (PA6) and polyhexamethyleneadipamide (PA66). The process involved solution of the polyamide in an appropriate solvent, precipitation by the addition of a non-solvent, and recovery of the polymer by washing and drying. Dimethylsulphoxide was used as the solvent for PA6, and formic acid for PA66, and methylethylketone was used as the non-solvent for both polymers. The recycled polymers were evaluated by determination of molecular weight, crystallinity and grain size. Excellent recoveries were achieved, with no deterioration in the polymer properties. 33 refs. 

AlliedSignal s Infinity, Forever Renewable Nylon, prepared by recycling of polyamide-6, is briefly described. The polyamide is treated by depolymerisation, purification of the caprolactam monomer and repolymerisation. The new resin is said to exhibit the same properties as those of virgin polyamide-6. ALLIEDSIGNAL... 

Warshel, Levitt, and Lifson derived a partially optimised consistent force field for amides and lactams (25). It is composed of an alkane part and an amide-part. The former was taken over from analogous earlier calculations for saturated hydrocarbons (17). The potential constants of the amide-part were optimised with the help of a large number of experimental frequencies (taken from TV-methylform amide, acetamide, iV-methylacetamide, and several deuterated species) as well as experimental geometry data for 7V-methylacet-amide. The resulting force field was used for the calculation of vibrational and conformational properties of 2-pyrrolidone, 2-piperidone and e-caprolactam. 

A number of polymers have been made using ROP. Nylon-6, similar to structure and properties to nylon-6,6, is made from the ring opening of the lactam caprolactam. PEO is made from the ring opening of ethylene oxide and is made more stable by capping the ends preventing ready depolymerization. 

Anionic ring opening polymerization of lactams to generate polyamides has been studied quite extensively by Sebenda [8-10], Sekiguchi [11], and Wichterle [12-13], among others, in academia, and by Gabbert and Hedrick [14] and by us [23-25] in industry. By far, caprolactam is the most studied lactam and the nylon 6 prepared by this route compares favorably in properties with that prepared by conventional hydrolytic polymerization. 

Reduced and partially reduced azepines are more common. Perhydroazepine (hexamethylenimine) was first prepared in 1905 and chemically it behaves as a typical secondary amine (B-67MI51600). Its 2-oxo derivative (caprolactam) is a bulk chemical and is of great industrial importance as an intermediate in the manufacture of nylon. Many oxo and dioxo derivatives of azepines and benzazepines have been prepared, often with difficulty, in a mainly fruitless search for aromatic properties in these azatropone and benz-azatropone systems (see Section 5.16.3.1.2). 

Rogovin, Z. A., and U. Zhun-Zhui Structure and properties of cellulose and its esters. LXXXV. Synthesis of new derivatives of cellulose and other polysaccharides. IV. Synthesis of graft copolymers of carboxymethyl cellulose and caprolactam. Vysokomolekulyarnye Soedineniya 1, 1630 (1959). 

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