# US 12,110,366 B2 · Semi-aromatic, semi-crystalline polyamide polymers and corresponding polymer compositions and articles

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 12,110,366 B2
- Document ID: US12110366B2
- Status: Granted
- Kind: B2
- Application number: 17/424,988
- Filed: 2020-01-21
- Published: 2022-04-28
- Granted: 2024-10-08
- Earliest claimed: 2019-01-22
- Assignees: Solvay Specialty Polymers USA, LLC
- Applicants: Solvay Specialty Polymers USA, LLC
- Inventors: Joel W. Flores; Stéphane Jeol
- Web page: https://patentgrep.com/patent/US12110366B2

## CPC

- C08G 69/265: {from at least two different diamines or at least two different dicarboxylic acids}
- C08K 3/32: Phosphorus-containing compounds
- C08K 2003/329: {Phosphorus containing acids}
- C08L 77/06: Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Described herein are polyamide polymers having improved glass transition temperatures (“Tg”) and relatively small values of Tm−Tg, where Tm is the melting temperature of the polyamide polymer. The polyamide polymers are semi-aromatic, semi-crystalline polyamide polymers that include recurring units formed the polycondensation of (1) a linear aliphatic diamine and a cycloaliphatic diamine with (2) an aromatic dicarboxylic acid. Due at least in part to the improved Tg, the polyamide polymers can be desirably incorporated into application settings including, but not limited to, mobile electronic devices, automotive, aerospace, building and construction, oil and gas, industrial, electrical and electronics, consumer goods, medical and healthcare. Furthermore, the polyamide polymers have relatively small values of Tm−Tg and, therefore, articles including the polyamide polymers can be more efficiently produced due to relatively small cycle times.

## Claims

### Claim 1

A polymer comprising recurring units RPA1, RPA2, RPA3, RPA4,
wherein
a) recurring unit RPA1 is represented by the following formula:
wherein
R1 and R2, at each location, is independently selected from the group consisting of a hydrogen, a halogen, an alkenyl, an alkynyl, on aryl, an ether, a thioether, a carboxylic acid, an ester, an amide, an imide, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, an alkali or alkaline earth metal phosphonate, an alkyl phosphonate, an amine, and a quaternary ammonium, and
R3 to R6 are independently selected from the group consisting of a hydrogen, a halogen, an alkyl, an alkenyl, an alkynyl, an aryl, an ether, a thioether, a carboxylic acid, an ester, an amide, an imide, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, an alkali or alkaline earth metal phosphonate, an alkyl phosphonate, an amine, and a quaternary ammonium;
b) Recurring unit RPA2 is represented by a formula selected from the following group of formulae:
Wherein R7 to R10, at each location, and R11 to R24 are independently selected from the group consisting of a hydrogen, a halogen, an alkyl, an alkenyl, an alkynyl, an aryl, an ether, a thioether, a carboxylic acid, an ester, an amide, an imide, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, an alkali or alkaline earth metal phosphonate, an alkyl phosphonate, an amine, and a quaternary ammonium; and n1 and n2 are independently selected integers from 1 to 10;
c) recurring unit RPA3 is distinct from recurring unit RPA1 and represented by Formula (1) or the following
formula:
d) recurring unit RPA4 is distinct from recurring unit RPA2 and is represented by a formula selected from Formulae (3) to (6).

### Claim 2 (depends on 1)

The polyamide polymer of claim 1, wherein recurring unit RPA1 is represented by Formula (1) and RPA2 is represented by Formula (3).

### Claim 3 (depends on 1)

The polyamide polymer of claim 1, wherein recurring unit RPA1 is represented by Formula (1) and RPA2 is represented by Formula (5).

### Claim 4 (depends on 1)

The polyamide polymer of claim 1, wherein R1, R2 and R7 to R10, at each location, is a hydrogen and R3 to R6 and R11 to R24 are all hydrogen.

### Claim 5 (depends on 1)

The polyamide polymer of claim 1, wherein the polyamide polymer is either PA 5,T/5,I/1,3-BAC,T/1,3-BAC,I or PA 5,T/5,I/1,4-BAC,T/1,4-BAC,I.

### Claim 6 (depends on 1)

The polyamide polymer of claim 1, wherein the polyamide polymer comprises, in total, at least 90 mol % of recurring units RPA1 to RPA4.

### Claim 7 (depends on 1)

The polyamide polymer of claim 1, wherein the polyamide polymer comprises a glass transition temperature (“Tg”) of at least 150º C.

### Claim 8 (depends on 1)

The polyamide polymer of claim 1, wherein the difference between the melting temperature (“Tm”) of the polyamide polymer and the Tg of the polyamide polymer (Tm−Tg) is no more than 170º C.

### Claim 9 (depends on 1)

A polyamide polymer composition comprising:
the polyamide polymer of claim 1 and
a reinforcing fiber
optionally, an additive selected from the group consisting of ultra-violet (“UV”) stabilizers, heat stabilizers, pigments, dyes, flame retardants, impact modifiers, processing aids, nucleating agents, mineral fillers, and any combination of one or more thereof; and
optionally, an additional polymer selected from the group consisting of a distinct polyamide polymer, a polyester polymer, a polyaryl ether sulfone polymer, a polyaryl ether ketone polymer, a polyarylene sulfide polymer, a polyaryl ether polymer, a liquid crystal polymers, and any combination of one or more thereof.

### Claim 10 (depends on 1)

An article comprising
the polyamide polymer claim 1
wherein the article is either
a mobile electronic device component or
an automotive component selected from the group consisting of connectors, tubings, housing, pans, switches, sockets, caps, rings, flanges, impellers, brackets, valves, covers, structural supports, washers and any combination of one or more thereof.

### Claim 11 (depends on 1)

A method for making the polyamide polymer of claim 1, the method comprising polycondensing (1) a linear aliphatic diamine and a cycloaliphatic diamine with (2) an aromatic dicarboxylic acid, wherein
the linear aliphatic diamine is represented by the following formula:
H2N—(R2R1C)5—NH2; (7)
the cycloaliphatic diamine is represented by a formula selected from the following group of formulae:
the aromatic dicarboxylic acid is represented by the following formula:
wherein R25 to R28 are independently selected from the group consisting of a hydrogen, a hydroxyl, a halogen, an alkyl, an alkenyl, an alkynyl, an aryl, an ether, a thioether, a carboxylic acid, an ester, an amide, an imide, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, an alkali or alkaline earth metal phosphonate, an alkyl phosphonate, an amine, and a quaternary ammonium.