IP Library Granted Patent US 11,396,580
Granted Patent B2
US 11,396,580 · App. 16/612,334 · Granted Jul 26, 2022

Polyamide terpolymers for manufacture of transparent articles

Inventors: Haoyu Liu (Parsippany, NJ); John V. Facinelli (Morris Plains, NJ)
Assignee: AdvanSix Resins & Chemicals LLC.
C08G69/26C08G69/14C08L77/02C08L77/06
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Quick Facts
Patent No.
US 11,396,580
App. No.
16/612,334
Granted
Jul 26, 2022
Kind
B2
Abstract

Amorphous polyamide terpolymers with a high level of transparency, transition glass temperature, flexibility, and chemical resistance. In one embodiment, the polyamide terpolymers are polymerized from caprolactam, at least one diamine, and at least one diacid.

Claims (24)

1. A polymeric base composition for use in manufacturing a finished article via melt processing, the polymeric base composition comprising:

at least one polyamide polymer polymerized from monomers including caprolactam, at least one diamine, and at least two diacids, the polymer having a glass transition temperature of at least 140° C., as measured by Differential Scanning calorimetry (DSC) according to ASTM D3418, a dry as molded (DAM) flexural modulus of at least 2000 MPa as determined by ASTM D790-15, and a transmittance value of at least 85% as measured by one of a hazemeter and a spectrophotometer according to ASTM D1003.

2. The polymeric base composition of claim 1 , wherein the at least one diamine includes at least one diamine selected from the group consisting of 4,4′-methylenebis(2-methylcyclohexylamine (MACM), 4,4′-methylenebis(cyclohexylamine) (PACM), isophorone diamine, and 2,2-bis(4-aminocyclohexyl)propane, and combinations of the foregoing.

3. The polymeric base composition of claim 2 , wherein the at least one diamine is MACM.

4. The polymeric base composition of claim 1 , wherein the at least one diacid includes at least one diacid selected from the group of consisting of dodecanedioic acid (C12 diacid), 1,4-cyclohexanedicarboxylic acid (1,4-CHDA), octadecanedioic acid (C18 diacid), and 1,3-cyclohexanedicarboxylic acid, and combinations of the foregoing.

5. The polymeric base composition of claim 4 , wherein the at least two diacids are C 12 diacid and 1,4-CHDA.

6. The polymeric base composition of claim 1 , wherein the at least one diamine and the at least one diacid form at least one diacid/diamine monomer of formula [—NHR 1 HC(O)R 2 C(O)—], wherein R 1 is one or more substituted or non-substituted non-aromatic cycloalkyl groups and R 2 is C 2 -C 18 alkyl, including hexyl, octyl, or decyl; or cycloalkyl, including cyclopropyl or cyclohexyl.

7. The polymeric base composition of claim 6 , wherein the at least one diacid/diamine monomer is formed of dodecanedioic acid (C 12 diacid) and 4, 4′-methylenebis(2-methylcyclohexylamine) (MACM), and has a formula of:

wherein y is between 5 and 30.

8. The polymeric base composition of claim 6 , wherein the at least one diacid/diamine monomer is formed of 1,4-cyclohexanedicarboxylic acid (1,4-CHDA) and 4, 4′-methylenebis(2-methylcyclohexylamine) (MACM), and has a formula of:

9. The polymeric base composition of claim 6 , wherein at least two diacid/diamine monomers are formed.

10. The polymeric base composition of claim 9 , wherein the two diacid/diamine monomers have a formula of:

wherein y is between 5 and 30, formed of dodecanedioic acid (C 12 diacid) and 4, 4′-methylenebis(2-methylcyclohexylamine) (MACM) and a formula of:

formed of 1,4-cyclohexanedicarboxylic acid (1,4-CHDA) and 4, 4′-methylenebis(2-methylcyclohexylamine) (MACM).

11. The polymeric base composition of claim 1 , wherein the polyamide polymer has a transparency, measured by one of a hazemeter and a spectrophotometer according to ASTM D1003, of at least 85%.

12. The polymeric base composition of claim 1 , wherein the polyamide polymer includes between 30 mol. % and 70 mol. % monomers based on caprolactam and between 30 mol. % and 70 mol. % monomers based on the at least one diacid and the at least one diamine.

13. The polymeric base composition of claim 1 , wherein the polyamide polymer includes less than 5 mol. % of aromatic groups, based on the total moles of the monomer components of the polymer.

14. An article of manufacture comprising:

a finished article formed from at least one polyamide polymer polymerized from monomers including caprolactam, at least one diamine, and at least two diacids; and

wherein the article has a glass transition temperature, measured by Differential Scanning calorimetry (DSC) according to ASTM D 3418, equal to or greater than 140° C. a dry as molded (DAM) flexural modulus of at least 2000 MPa as determined by ASTM D790-15, a transmittance value of at least 85% as measured by one of a hazemeter and a spectrophotometer according to ASTM D1003, and the polyamide polymer includes less than 5 mol. % of aromatic groups, based on the total moles of the monomer components of the polymer.

15. The article of manufacture of claim 14 , wherein the article has a water absorption at equilibrium, according to ASTM D570, of less than 3.5%.

16. The article of manufacture of claim 14 , wherein the finished article has a burst pressure, measured according to ASTM D790, between 1200 MPa and 2500 MPa.

17. The article of manufacture of claim 14 , wherein the polyamide polymer includes between 30 mol. % and 70 mol. % monomers based on caprolactam and between 30 mol. % and 70 mol. % monomers based on the at least one diacid and the at least one diamine.

18. The article of manufacture of claim 14 , wherein the finished article is selected from the group consisting of an optical lens, a safety/face shield, a water/fuel filter housing, and a medical component.

Assignments (2)
SECURITY INTEREST Recorded Oct 27, 2021
From: ADVANSIX INC.; ADVANSIX RESINS & CHEMICALS LLC
To: TRUIST BANK, AS ADMINISTRATIVE AGENT
Reel/Frame 057940/0794 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 13, 2021
From: LIU, HAOYU; FACINELLI, JOHN V.
To: ADVANSIX RESINS & CHEMICALS LLC.
Reel/Frame 055900/0465 →
Continuity (1)
Related Publication 20200255594A1 · Aug 13, 2020
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