Dinitriles, diamines, and polyamides
AssigneePhillips Petroleum Company
InventorsCharles A. Drake, Stanley D. Turk
Life of this patent
Estimating the term…
Abstract
Unsaturated dinitriles are reacted with an aromatic compound such as benzene in the presence of a Lewis acid such as aluminum chloride to yield novel aralkylenedinitriles, such as 5-methyl-5-phenylnonanedinitrile and isomers thereof. The aralkylenedinitriles can be reduced to novel aralkylenediamines or novel cycloalkylalkylenediamines. Polymerization of the aralkylenediamines or cycloalkylalkylenediamines with polycarboxylic acids provides novel polyamides of tough, clear, colorless character.
Claims21
As compositions of matter, aralkylenediamines represented by:
- ##STR5## wherein each R' is an alkylene or alkylidene radical of at least one carbon atom, R" is an alkyl radical of at least one carbon atom, and Ar is a divalent phenylene or naphthylene radical wherein Q represents hydrogen or other substituent on said Ar, and wherein said --Ar--Q contains 6 to 22 carbon atoms,
- and wherein Q is selected from the group consisting of --H, --X, --R"', --N(R"').sub.2, --NH.sub.2 'HX, --OR"', --SH, --OH, and --SR"', wherein X is a halogen and is fluorine, chlorine, bromine, or iodine, and R"' is an alkyl radical of 1 to 6 carbon atoms.
As compositions of matter, aralkylenediamines as defined by claim 16 prepared by hydrogenating one or more aralkylenedinitriles represented by the formula:
- ##STR6## under hydrogenation conditions including the presence of hydrogen and ammonia sufficient to effectuate reduction of the --C.tbd.N groups substantially without reduction of double bonds in said aralkylenedinitriles.
As compositions of matter, cycloalkylalkylenediamines represented by:
- ##STR7## wherein each R' is a linear or branched alkylene or alkylidene radical of at least one carbon atom with one valence attached to the aminomethyl group as indicated by the formulae;
- R" is a linear or branched alkyl radical of at least one carbon atom;
- Cy represents a cyclohexylene or perhydronaphthylene radical and wherein Q represents hydrogen, --X, --R"', --N(R"').sub.2, --NH.sub.2.HX, --OR"', --SH, --OH, or --SR"', wherein X is fluorine, chlorine, bromine, or iodine, and wherein R"' is an alkyl radical of 1 to 6 carbon atoms.
As compositions of matter, cycloalkylalkylenediamines represented by one or more of the formulae:
- ##STR8## prepared by the process which comprises hydrogentating one or more aralkylenediamines represented by the formulae:
- ##STR9## under hydrogenation conditions including the presence of hydrogen, and catalyst, effective to hydrogenate said Ar to said Cy,
- wherein each R' is a linear or branched alkylene or alkylidene radical of at least one carbon atom with one valence attached to the aminomethyl group as indicated by the formulae;
- R" is a linear or branched alkyl radical of at least one carbon atom;
- said Ar represents a phenylene or naphthylene radical wherein Q represents hydrogen, --X, --R"', --N(R"').sub.2, --NH.sub.2.Hx, --OR"', --SH, --OH, or --SR"', wherein X is fluorine, chlorine, bromine, or iodine, and R"' is an alkyl radical of up to 6 carbon atoms, and wherein Cy represents a fully hydrogenated Ar.
Dependencies are inferred from the claim text.