Methods Of Producing Amine-Terminated Caprolactone Polymers And Uses Of The Produced Polymers

1 - 22 . (canceled)

23 . A method for the preparation of an amine-terminated caprolactone polymer having at least two terminal ends with a primary amine located thereon, comprising the steps of:

a) using a polycarboxylic acid as an initiator in the ring opening polymerisation of epsilon-caprolactone to produce a polycaprolactone polymer having at least two terminal ends with a carboxylic acid located thereon; and then

b) reacting the product of step a) with a polyamine at a temperature above 50° C. to produce an amine-terminated polycaprolactone polymer.

24 . The method of claim 23 , wherein the reaction of step b) is carried out at temperature below 80° C.

25 . The method of claim 23 , wherein the polyamine used in step b) is a diamine.

26 . The method of claim 24 , wherein the polyamine used in step b) is a diamine.

27 . The method of claim 23 , wherein the polycarboxylic acid used in step a) is a dicarboxylic acid.

28 . The method of claim 24 , wherein the polycarboxylic acid used in step a) is a dicarboxylic acid.

29 . The method of claim 23 , wherein the polyamine used in step b) is selected from the group consisting of: Hexamethylenediamine (HMDA); ethylenediamine; N,N′-dimethylethyenediamine; piperazine and piperazine derivatives such as 2-methylpiperazine, 2,5-dimethylpiperazine, 2,3-dimethylpiperazine, 1,4-bis(3-aminopropyl)piperazine and N-aminoethylpiperazine; isophoronediamine; polyoxypropylenediamine; bis(4-amino-3-methyldicyclohexyl)methane; diaminodicyclohexylmethane; bis(aminomethyl)cyclohexane; m-xylylenediamine; alpha-(m-aminophenyl)ethylamine; alpha-(p-aminophenyl)ethylamine; metaphenylenediamine; diaminodiphenylmethane; diaminodiphenylsulfone; norbomenediamine; and also including conventional aliphatic, alicyclic, and aromatic amines.

30 . The method of claim 24 , wherein the polyamine used in step b) is selected from the group consisting of: Hexamethylenediamine (HMDA); ethylenediamine; N,N′-dimethylethyenediamine; piperazine and piperazine derivatives such as 2-methylpiperazine, 2,5-dimethylpiperazine, 2,3-dimethylpiperazine, 1,4-bis(3-aminopropyl)piperazine and N-aminoethylpiperazine; isophoronediamine; polyoxypropylenediamine; bis(4-amino-3-methyldicyclohexyl)methane; diaminodicyclohexylmethane; bis(aminomethyl)cyclohexane; m-xylylenediamine; alpha-(m-aminophenyl)ethylamine; alpha-(p-aminophenyl)ethylamine; metaphenylenediamine; diaminodiphenylmethane; diaminodiphenylsulfone; norbomenediamine; and also including conventional aliphatic, alicyclic, and aromatic amines.

31 . The method of claim 23 , wherein the polycarboxylic acid used in step a) is selected from the group consisting of: adipic acid; succinic acid; dodecanedioic acid; and citric acid.

32 . The method of claim 24 , wherein the polycarboxylic acid used in step a) is selected from the group consisting of: adipic acid; succinic acid; dodecanedioic acid; and citric acid.

33 . The method claim 23 , wherein step a) further involves an acid catalyst.

34 . The method claim 24 , wherein step a) further involves an acid catalyst.

35 . The method of claim 33 , wherein the acid catalyst is an organic acid such as p-Tolunesulphonic acid.

36 . The method of claim 33 , wherein the role of acid catalyst is provided by the polycarboxylic acid initiator.

37 . The method of claim 23 , wherein the ratio of monomer/initiator/catalyst used in step a) is 4269:731:5.

38 . The method of claim 24 , wherein the ratio of monomer/initiator/catalyst used in step a) is 4269:731:5.

39 . The method of claim 23 , wherein the ratio of monomer/initiator/catalyst used in step a) is 4126:373:5.

40 . The method of claim 24 , wherein the ratio of monomer/initiator/catalyst used in step a) is 4126:373:5.

41 . A method of using an amine-terminated caprolactone polymer produced by the method of claim 23 as a epoxy resin curative.

42 . A method of using an amine-terminated caprolactone polymer produced by the method of claim 24 as a epoxy resin curative.

43 . A method of using an amine-terminated caprolactone polymer produced by method of claim 23 in the production of polyurea.

44 . A method of using an amine-terminated caprolactone polymer produced by method of claim 24 in the production of polyurea.

45 . The method of claim 43 , wherein the caprolactone polymer is reacted with isocyanate to produce a polyurea polymer.

46 . An amine-terminated caprolactone polymer having the general formula:

H 2 N—(CH 2 ) 6 —NH—CO—(CH 2 ) 5 O—[C(═O)—(CH 2 ) 5 —O] n —C(═O)—R 1 —C(═O)—[O—(CH 2 ) 5 —C(═O)] m —O—(CH 2 ) 5 CO—NH—(CH 2 ) 6 —NH 2

Wherein R 1 ═(CH 2 ) p R 2 ;

R 2 ═CH 2 or CH—(CH 2 ) q —C(═O)—[O—(CH 2 ) 5 —C(═O)] s —NH—(CH 2 ) 6 —NH 2

m is a whole number between 0 and 500;

n is a whole number between 0 and 500;

wherein m+n is >/=3;

s is a whole number between 0 and 500;

p is a whole number between 0 and 100; and

q is a whole number between 0 and 100.

47 . the caprolactone polymer of claim 46 , wherein p is 3.

48 . The caprolactone polymer of claim 46 , wherein n is </=20.

49 . The caprolactone polymer of claim 47 , wherein n is </=20.

50 . The caprolactone polymer of claim 46 , wherein m is </=20.

51 . The caprolactone polymer of claim 47 , wherein m is </=20.

52 . The caprolactone polymer of claim 46 , wherein m+n is </=20.

53 . The caprolactone polymer of claim 47 , wherein m+n is </=20.

54 . A method of using an amine-terminated caprolactone polymer according to claim 46 as an epoxy resin curative.

55 . A method of using an amine-terminated caprolactone polymer according to claim 47 as an epoxy resin curative.

56 . A method of using an amine-terminated caprolactone polymer according to claim 46 in the production of polyureas.

57 . A method of using an amine-terminated caprolactone polymer according to claim 47 in the production of polyureas.

58 . The method of claim 56 , wherein the caprolactone polymer is reacted with isocyanate to produce a polyurea polymer.