Polyamide copolymer and method of making the same
A method of making a polyamide copolymer includes subjecting a reaction mixture to conditions sufficient to form the polyamide copolymer, the reaction mixture including adduct A and adduct B. Adduct A is a 1:1 adduct of a diamine having the structure H2N-R1-NH2, or a salt thereof and an aliphatic diacid having the structure HO—C(O)—R2-C(O)—OH, or a salt thereof. Adduct B is a 1:1 adduct of the diamine having the structure H2N-R1-NH2, or a salt thereof, and an aromatic diacid having the structure HO—C(O)—R3-C(O)—OH, or a salt thereof. At each occurrence, R1 and R2 can be independently a substituted or unsubstituted (C1-C20)alkylene. At each occurrence, R3 can be independently a substituted or unsubstituted (C6-C20)arylene. The molar ratio of adduct A to adduct B in the reaction mixture can be about 61:39 to about 90:10.
1. A method of making a polyamide copolymer, the method comprising:
subjecting a reaction mixture to conditions sufficient to form the polyamide copolymer, the reaction mixture comprising adduct A and adduct B, wherein
adduct A is a 1:1 adduct of a diamine having the structure H 2 N—R 1 —NH 2 , or a salt thereof, and an aliphatic diacid having the structure HO—C(O)—R 2 —C(O)—OH, or a salt thereof,
adduct B is a 1:1 adduct of the diamine having the structure H 2 N—R 1 —NH 2 , or a salt thereof, and an aromatic diacid having the structure HO—C(O)—R 3 —C(O)—OH, or a salt thereof,
at each occurrence, R 1 is independently a substituted or unsubstituted (C 1 -C 20 )alkylene,
at each occurrence, R 2 is independently a substituted or unsubstituted (C 1 -C 20 )alkylene,
at each occurrence, R 3 is independently a substituted or unsubstituted (C 6 -C 20 )arylene,
the molar ratio of adduct A to adduct B in the reaction mixture is about 61:39 to about 90:10,
the polyamide copolymer comprises repeating units having the structure:
and the repeating units are in block or random configuration in the copolymer, wherein the subjecting of the reaction mixture to conditions sufficient to form the polyamide copolymer is performed in a reactor; and
removing a majority of the polyamide copolymer from the reactor while leaving a minor amount of the polyamide copolymer on inner surfaces of the reactor and subsequently performing the subjecting of a reaction mixture to conditions sufficient to form the polyamide copolymer in the reactor again.
2. The method of claim 1 , wherein the molar ratio of adduct A to adduct B in the reaction mixture is about 61:39 to about 85:15.
3. The method of claim 2 , wherein the melting point of all of the polyamide copolymer formed during the method is less than or equal to about 300° C.
4. The method of claim 3 , wherein the melting point of the polyamide copolymer is about 200° C. to about 300° C.
5. The method of claim 4 , wherein R 1 is hexylene and the diamine is hexamethylenediamine.
6. The method of claim 5 , wherein R 2 is butylene and the aliphatic diacid is adipic acid.
7. The method of claim 6 , wherein R 3 is phenyl and the aromatic diacid is terephthalic acid.
8. The method of claim 7 , wherein the polyamide copolymer comprises repeating units having the structure:
wherein repeating units are in block or random configuration in the copolymer.
9. The method of claim 8 , wherein the polyamide copolymer has the structure:
or a salt thereof, wherein repeating units are in block or random configuration in the copolymer.
10. The method of claim 1 , wherein during the subsequent performance of the subjecting of a reaction mixture to conditions sufficient to form the polyamide copolymer in the reactor again, no polyamide copolymer remains unmelted, unhydrolyzed, undispersed, or a combination thereof, in the reactor.
11. The method of claim 1 , wherein the subjecting of the reaction mixture to conditions sufficient to form the polyamide copolymer comprises removing water from the reaction mixture.
12. The method of claim 1 , wherein the subjecting of the reaction mixture to conditions sufficient to form the polyamide copolymer comprises subjecting the reaction mixture to a temperature of about 200° C. to about 300° C.
13. A method of making a polyamide copolymer, the method comprising:
subjecting a reaction mixture to conditions sufficient to form the polyamide copolymer, the reaction mixture comprising adduct A and adduct B, wherein
adduct A is a 1:1 adduct of a diamine having the structure H 2 N—R 1 —NH 2 , or a salt thereof, and an aliphatic diacid having the structure HO—C(O)—R 2 —C(O)—OH, or a salt thereof,
adduct B is a 1:1 adduct of the diamine having the structure H 2 N—R 1 —NH 2 , or a salt thereof, and an aromatic diacid having the structure HO—C(O)—R 3 —C(O)—OH, or a salt thereof,
R 1 is hexylene and the diamine is hexamethylenediamine,
R 2 is butylene and the aliphatic diacid is adipic acid,
R 3 is phenyl and the aromatic diacid is terephthalic acid,
the molar ratio of adduct A to adduct B in the reaction mixture is about 65:35 to about 75:25,
the polyamide copolymer comprises repeating units having the structure:
the repeating units are in block or random configuration in the copolymer, and
the melting point of all of the polyamide copolymer formed during the method is less than or equal to about 300° C., wherein the subjecting of the reaction mixture to conditions sufficient to form the polyamide copolymer is performed in a reactor; and
removing a majority of the polyamide copolymer from the reactor while leaving a minor amount of the polyamide copolymer on inner surfaces of the reactor and subsequently performing the subjecting of a reaction mixture to conditions sufficient to form the polyamide copolymer in the reactor again.
14. A polyamide copolymer produced from the subsequent performance of the subjecting of a reaction mixture to conditions sufficient to form the polyamide of claim 1 , the polyamide copolymer comprising repeating units having the structure:
wherein
the molar ratio of repeating unit A to repeating unit B is about 61:39 to about 90:10, and
the melting point of the polyamide copolymer is less than or equal to about 300° C.