2095-06-9

A method efficiently and safely manufactures, on an industrial scale, a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group. (1) an amine compound or a solution thereof, (2) epichlorohydrin or a solution thereof, and (3) an acidic compound or a solution thereof are continuously supplied to a flow reactor and reacted at a reaction temperature of 40 to 130° C. and a liquid space velocity of 0.2 to 10 h?1 so that a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group is manufactured. The obtained compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group is dehydrochlorinated by reaction with an alkali so that a polyfunctional glycidylamine type epoxy compound is manufactured.

In this study, two series of epoxy-based azo polymers with high chromophore density were synthesized and self-structured surface pattern formation on the polymer films was studied by laser light irradiation under different conditions. To synthesize the azo polymers, two epoxy-based precursor polymers (PEP-AN and PEP-35AN) were prepared by step polymerizations of N,N-di(epoxypropyl)aniline and N,N-di(epoxypropyl)-3,5-dimethylaniline with aniline and 3,5-dimethylaniline, respectively. The azo polymers were obtained through postpolymerization azo-coupling reactions between the precursor polymers and diazonium salts of 4-chloroaniline, 4-aminobenzonitrile, 4-nitroaniline, and 2-methyl-4-nitroaniline. The epoxy-based precursor polymers and azo polymers were characterized by using 1H NMR, FT-IR, UV-vis, and DSC analyses. The self-structured surface pattern formation on films of the two series of azo polymers was studied by irradiating the polymer films with a normal-incident laser beam at two different wavelengths (488 and 532 nm). The results show that the photoinduced surface pattern formation is closely related with the structure of azo chormophores, excitation wavelength, and light polarization condition. The efficient excitation wavelength is closely related with the absorption band position, which is mainly determined by the electron-withdrawing groups on the azo chromophores. The methyl substituents on the azo chromophores can enhance the photoinduced surface pattern formation ability in some cases. For comparison, the surface-relief-grating (SRG) formation was studied by irradiating the polymer films with interfering laser light. The SRG formation rate is also dependent on the azo chromophore structure and wavelength of the incident laser light. The self-structured surface pattern formation needs a higher energy input and shows stricter wavelength requirement compared with those of the SRG formation. These observations could lead to the deeper understanding of the mechanism of the self-structured surface pattern formation and development of materials with better performance.

New chemical modifiers for gelatin, glycidylamines, are synthesized.Acid-base properties of glycidylamines and the kinetics of reactions of oxirane compounds with nucleophilic reagents, among them aqueous solution of gelatin, are studied.

An amide group-containing epoxy resin obtained by reacting an epoxy resin with an amide group-containing diisocyanate obtained by reacting a diisocyanate with a dicarboxylic acid gives a uniform cured article showing high adhesiveness and is usable as an adhesive, a coating composition, and the like.

α,ω-polymethacrylate dicarboxylic acids of the general formula STR1 wherein R1 is an optionally halogenated alkyl group with 1 to 22 carbon atoms, wherein the R1 group can assume different meanings in the polymer molecule, R2 is the group of a known chain transfer agent, which has a terminal --COOH croup and a has a value not less than 4. The invention furthermore relates to the synthesis of these compounds and their use as sole or partial components for the synthesis or modification of polyepoxides, polyesters, polyamides, alkyd resins or polyurethanes.