Patent GB-498328-A (GB)
Title: Aromatic polyether amines
IPC: C08K5/17
Filed: 1937-07-20
Abstract: Amino ethers are obtained by the action of primary or secondary aromatic amines on halogenated ethers of the formula ROAOAX or ROAOAOAX, in which R is an aryl radicle, preferably of the benzene or naphthalene series, A is an alkylene radicle containing at least two carbon atoms, and X is a halogen atom; the radicle R may contain substituents, e.g. an alkyl, aralkyl, cycloalkyl or nitro group.  The aromatic amines used are of the type HNYR1, in which R1 is an aryl radicle and Y is hydrogen or an alkyl or aryl group.  The reaction may be effected at 100-160 DEG  C. in the presence or absence of an inert organic diluent and/or an inorganic base.  In the examples, products are prepared from (1) b -phenoxy-chlorodiethyl ether and aniline; (2) b -p-tert.-octylphenoxy-b 1-chlorodiethyl ether and aniline; (3) b -p-cyclohexylphenoxy-b 1-chlorodiethyl ether and aniline; (4) b -(b -naphthyloxy)-b 1-chlorodiethyl ether and o-toluidine; (5) b -phenoxy-b 1-chlorodiethyl ether and a -naphthylamine; (6) b -p-tert.-butylphenoxy-b 1-chlorodiethyl ether and methylaniline; (7) b -(b 11-phenoxy) ethoxy-b 1-chlorodiethyl ether and aniline; (8) b -p-tert.-butylphenoxy-b 1-chloroisopropyl ether and aniline.  g -Aryloxy-g 1-chloropropyl ethers also are specified as starting materials.  The products may be added to lubricating-oils to retard oxidation.  Specifications 494,766; and 494,767, [Group IV], are referred to.  The Specification as open to inspection under Sect. 91 mentions xylidines, diphenylamine, dinaphthylamines and N-methylnaphthylamines as aromatic amines which may be used. This subject-matter does not appear in the Specification as accepted.ALSO:Amino ethers are obtained by the action of primary or secondary aromatic amines on halogenated ethers of the formula ROAOAX or ROAOAOAX, in which R is an aryl radicle, preferably of the benzene or naphthalene series, A is an alkylene radicle containing at least two carbon atoms, and X is a halogen atom; the radicle R may contain substituents, e.g. an alkyl, aralkyl, cycloalkyl or nitro group.  The aromatic amines used are of the type HNYR1, in which R1 is an aryl radicle and Y is hydrogen or an alkyl or aryl group.  The reaction may be effected at 100-160 DEG  C. in the presence or absence of an inert organic diluent and/or an inorganic base.  In the examples, products are prepared from (1) b -phenoxy-b 1-chlorodiethyl ether and aniline, (2) b -p-tert.-octylphenoxy-b 1-chlorodiethyl ether and aniline, (3) b -p-cyclohexylphenoxy-b 1-chlorodiethyl ether and aniline, (4) b -(b -naphthyloxy)-b 1-chlorodiethyl ether and o-toluidine, (5) b -phenoxy-b 1-chlorodiethyl ether and a -naphthylamine, (6) b -p-tert.-butylphenoxy-b 1-chlorodiethyl ether and methylaniline, (7) b -(b 11-phenoxy)ethoxy-b 1-chlorodiethyl ether and aniline, (8) b -p-tert.-butylphenoxy-b 1-chloroisopropyl ether and aniline.  g -Aryloxy-g 1-chloropropyl ethers are also specified as starting materials.  The products may be added to rubber and lubricating-oils, to retard oxidation. Specifications 494,766 and 494,767 are referred to.  The Specification as open to inspection under Sect. 91 mentions xylidines, diphenylamine, dinaphthylamines and N-methylnaphthylamines as aromatic amines which may be used. This subject-matter does not appear in the Specification as accepted.ALSO:Amino ethers are obtained by the action of primary or secondary aromatic amines on halogenated ethers of the formula ROAOAX or ROAOAOAX, in which R is an aryl radicle, preferably of the benzene or naphthalene series, A is an alkylene radicle containing at least two carbon atoms, and X is a halogen atom; the radicle R may contain substituents, e.g. an alkyl, aralkyl, cycloalkyl or nitro group.  The aromatic amines used are of the type HNYR1, in which R1 is an aryl radicle and Y is hydrogen or an alkyl or aryl group.  The products may be added to rubber to retard oxidation.  Specifications 494,766 and 494,767, [both in Group IV], are referred to.  The Specification as open to inspection under Sect. 91 mentions xylidines, diphenylamine, dinaphthylamines and N-methylnaphthylamines as aromatic amines which may be used. This subject-matter does not appear in the Specification as accepted.