Polyamine and method for producing thereof

Abstract

A method for producing a polyamine is described that provides excellent safety, a lot of flexibility regarding a variety of its productions, and that can produce a polyamine of high-molecular weight easily and inexpensively. The polyamine includes a combination of units of formula (1) or (2): —(NH—(CH 2 ) m —NH—(CH 2 ) n )—  (1) (in the formula (1), independently in every unit, “m” indicates an integral number of 0 or more and “n” indicates an integral number of 3 or more.) —(NH—Y—NH—Z)—  (2) (in the formula (2), independently in every unit, “Y” and “Z” are the same as or different from each other, and they indicate substituted or unsubstituted groups including unsaturated aliphatic, cyclic aliphatic or aromatic hydrocarbon radicals that can include hetero atoms.).

1 . A polyamine comprising a combination of units of formula (1) or (2):
   —(NH—(CH 2 ) m —NH—(CH 2 ) n )—  (1)
   (in the formula (1), independently in every unit, “m” indicates an integral number of 0 or more and “n” indicates an integral number of 3 or more.)
   —(NH—Y—NH—Z)—  (2)
 
   (in the formula (2), independently in every unit, “Y” and “Z” are the same as or different from each other, and they indicate substituted or unsubstituted groups comprising unsaturated aliphatic, cyclic aliphatic or aromatic hydrocarbon radicals that can include hetero atoms.)   
     
     
         2 . The polyamine according to  claim 1 , wherein m and/or n of the formula (1) are the same as each other among the combined units. 
     
     
         3 . The polyamine as defined by  claim 1 , wherein the and/or Z of the formula (2) are the same as each other among combined units. 
     
     
         4 . The polyamine as defined by  claim 1 , wherein the polyamine comprises a polymer with a molecular weight of 1,000 or more as it is measured by a mass spectrum. 
     
     
         5 . A polyamine obtained by a reductive polycondensation polymerization of diamine and dinitrile, wherein the diamine is at least one member selected from the group consisting of a substituted diamine, an unsubstituted diamine, an aliphatic diamine, an aromatic diamine and an aliphatic-aromatic combined diamine. 
     
     
         6 . The polyamine according to  claim 5 , wherein
 the aliphatic diamine is at least one member selected from the group consisting of ethylenediamine, 1,2-propylenediamine, 1,3-propylenediamine, 1,2-butylenediamine, 1,3-butylenediamine, 1,4-butylenediamine, 2,3-butylenediamine, 1,2-cyclohexanediamine, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, hydrazine, pentamethylenediamine, hexamethylenediamine, heptamethylenediamine, octamethylenediamine, nonamethylenediamine, decamethylenediamine, undecamethylenediamine, dodecamethylenediamine, piperazine, diaminopiperazine, imidazolidine, diethylenetriamine, triethylenetetramine, 3-oxa-1,5-diaminopentane, 1,3-diamino-2-propanol, 2-acetoxy-1,3-propanediamine, lysine, 2,4-diaminobutanoic acid and 2,3-diaminosuccinic acid,   the aromatic diamine is at least one member selected from the group consisting of 1,2-phenylenediamine, 1,3-phenylenediamine, 1,4-phenylenediamine, tolylenediamine, naphthalenediamine, N,N-diphenylethylenediamine, 3,3′-methylenedianiline, 4,4′-methylenedianiline, 1,1′-binaphthyl-2,2′-diamine, diaminoferrocene, 2,2′-diaminobiphenyl, 2,3′-diaminobiphenyl, 2,4′-diaminobiphenyl, 3,3′-diaminobiphenyl, 3,4′-diaminobiphenyl, benzidine, 2,7-diamino-9H-fluorene, 2,3-diaminopyridine, 2,4-diaminopyridine, 2,5-diaminopyridine, 2,6-diaminopyridine, 3,4-diaminopyridine, 3,5-diaminopyridine, 2,3-diaminophenol, 2,4-diaminophenol, 2,5-diaminophenol, 2,6-diaminophenol, 3,4-diaminophenol, 3,5-diaminophenol, 2,4-diaminopyrimidine, 2,5-diaminopyrimidine, 4,5-diaminopyrimidine, 4,6-diaminopyrimidine, 2,3-diaminobenzotrifluoride, 2,4-diaminobenzotrifluoride, 2,5-diaminobenzotrifluoride, 2,6-diaminobenzotrifluoride, 3,4-diaminobenzotrifluoride, 3,5-diaminobenzotrifluoride, 2,3-diaminobenzoic acid, 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid, 2,6-diaminobenzoic acid, 3,4-diaminobenzoic acid, 3,5-diaminobenzoic acid, 2,3-diaminobenzamide, 2,4-diaminobenzamide, 2,5-diaminobenzamide, 2,6-diaminobenzamide, 3,4-diaminobenzamide and 3,5-diaminobenzamide,   the aliphatic-aromatic combined diamine is at least one member selected from the group consisting of o-xylenediamine, m-xylenediamine, p-xylenediamine and methylaminoaniline, and   the substituted group is at least one member selected from the group consisting of an alkyl group, a carboxyl group, an ester group, an alkoxy group, a hydroxyl group, a tertiary amine, an aromatic hydrocarbon group and a perfluoro alkyl group.   
     
     
         7 . The polyamine as defined by  claim 5 , wherein the dinitrile is at least one selected member from the group consisting of an aliphatic dinitrile, an aromatic dinitrile and an aliphatic-aromatic combined dinitrile. 
     
     
         8 . The polyamine according to  claim 7 , wherein
 the aliphatic dinitrile is at least one member selected from the group consisting of malononitrile, succinonitrile, trimethylenedinitrile, adiponitrile, 2-methylglutaronitirile, pimelonitrile, suberonitrile, decanedinitrile, undecanedinitrile, dodecanedinitrile, 3-oxaglutaronitrile, 1,2-cyclopentanedinitirle, 1,3-cyclopentanedinitirle, 1,2-cyclohexanedinitrile, 1,3-cyclohexanedinitrile, 1,4-cyclohexanedinitrile, 2,4-dicyano-3-methylglutaramide, 4-azaheptanedinitirle and N-alkyl-4-azaheptanedinitrile,   the aromatic dinitrile is at least one member selected from the group consisting of phthalonitrile, isophthalonitrile, terephthalonitrile, toluylenediamine, naphthalenedinitirle, 2,4-dicyanoimidazole, 2,5-dicyanoimidazole, 4,5-dicyanoimidazole, 2,3-dicyanopyridine, 2,4-dicyanopyridine, 2,5-dicyanopyridine, 3,4-dicyanopyridine, 3,5-dicyanopyridine and tetrafluorophthalonitile,   the aliphatic-aromatic combined dinitrile is at least one member selected from the group consisting of 1,2-phenylenediacetonitrile, 1,3-phenylenediacetonitrile, 1,4-phenylenediacetonitrile, 1,2-cyanomethylbenzonitrile, 1,3-cyanomethylbenzonitrile, 1,4-cyanomethylbenzonitrile, 3-(2-cyanophenoxy)propionitrile, 3-(3-cyanophenoxy)propionitrile, 3-(4-cyanophenoxy)propionitrile, 1,2-di(2-cyanoethoxy)benzene, 1,3-di(2-cyanoethoxy)benzene and 1,4-di(2-cyanoethoxy)benzene, and   the substituted group is at least one member selected from the group consisting of an alkyl group, a carboxyl group, an ester group, an alkoxy group, a hydroxyl group, a tertiary amine, an aromatic hydrocarbon group and a perfluoro alkyl group.   
     
     
         9 .- 25 . (canceled)