Copolyamide Composition for Tunable Tg and Melt Processability

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Solution Overview

Problem

Existing polyamides derived from 1,4-aminomethylcyclohexanecarboxylic acid (1,4-AMCC) have high melting temperatures, making them unsuitable for melt processing due to decomposition, and copolymerization with caprolactam results in isomorphic structures that limit tunability of glass transition temperature (Tg) and melt processability.

Innovation Solution

Development of polyamides comprising recurring units X, Y, and Z, with specific mole percentages and substituents, allowing for amorphous or semi-crystalline structures with improved Tg and Tm, avoiding isomorphism and enabling melt processability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Adaptability or versatility

If polyamides are derived from 1,4-aminomethylcyclohexanecarboxylic acid (1,4-AMCC), then the glass transition temperature (Tg) tunability is improved, but the melting temperature becomes extremely high making melt processing impossible

Engineering Contradiction:
ImproveTg tunabilityVSAvoidmelting temperature
Core Design Contradiction:
Adaptability or versatilityVSTemperature

Solution Approach 1:

The patent applies parameter changes by systematically varying the composition ratios of different recurring units (X, Y, and Z) in the copolymer. By adjusting the mole percentages of 1,4-AMCC-derived units, caprolactam units, and other comonomer units, the invention achieves continuous tuning of both Tg and Tm parameters, enabling melt processability while maintaining desired thermal properties.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates composite copolymer structures combining multiple recurring units with different functions. The copolymer comprises 1,4-AMCC-derived units for Tg control, caprolactam units for flexibility and processability, and additional comonomer units to adjust crystallinity and melting behavior, achieving a balanced material with both high Tg tunability and acceptable Tm for processing.

Inventive Principle:
Principle #40Composite materials

2Ease of manufacture

If copolymerization with caprolactam is performed, then melt processability is improved, but isomorphic structures are formed limiting further Tg tunability

Engineering Contradiction:
Improvemelt processabilityVSAvoidTg tunability
Core Design Contradiction:
Ease of manufactureVSAdaptability or versatility

Solution Approach 1:

The patent segments the copolymer into distinct recurring units with specific functions: Unit X (from 1,4-AMCC) provides high Tg contribution, Unit Y (from caprolactam) provides flexibility and processability, and Unit Z (from other comonomers) provides additional tuning capability. This segmentation allows independent optimization of each unit's contribution to avoid isomorphic limitations.

Inventive Principle:
Principle #1Segmentation

Solution Approach 2:

The patent applies local quality by assigning specific functional roles to different segments of the copolymer chain. The 1,4-AMCC-derived units locally contribute to high Tg, caprolactam units locally provide chain flexibility for processability, and other comonomer units locally adjust crystallinity and melting points, achieving overall material properties that transcend simple isomorphic copolymer behavior.

Inventive Principle:
Principle #3Local quality

Data Source

PatentUS12473401B2Polyamides and corresponding polymer compositions and articles
Publication Date: 2025.11.18 SYENSQO SPECIALTY POLYMERS USA LLC
  • US12473401B2 patent drawing
  • US12473401B2 patent drawing
  • US12473401B2 patent drawing

AI summary

The present invention relates to a polyamide (PA) comprising recurring units X, Y, and Z and is represented by the following formula (1): wherein—nx, ny and nz are respectively the mole percent (mol. %) of each recurring units X, Y and Z; —10 mol %≤nx≤90 mol %; —0 mol %≤ny≤90 mol %; —0 mol %≤nz≤90 mol %; —nx+ny+nz≤100 mol. %; and—at least one of ny and nz is greater than 0 mol. %, and wherein—R1 is selected from the group consisting of a hydrogen, an alkyl, or an aryl—R′i, at each location, is independently selected from the group consisting of an alkyl, an aryl, an alkali or alkaline earth metal sulfonate, an alkyl sulfonate, and a quaternary ammonium; —i is an integer from 0 to 10; —R2 is selected from the group consisting of a bond, a C1-C15 alkyl and a C6-C30 aryl, optionally comprising one or more heteroatoms (e.g. O, N or S) and optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy (—OH), sulfo (—SO3M), C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 acyl, formyl, cyano, C6-C15 aryloxy and C6-C15 aryl; —R3 is selected from the group consisting of a C1-C20 alkyl, a phenyl, an indanyl, and a napthyl, optionally comprising one or more heteroatoms (e.g. O, N or S) and optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy (—OH), sulfo (—SO3M), C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 acyl, formyl, cyano, C6-C15 aryloxy and C6-C15 aryl; and—R4 is selected from the group consisting of a linear or branched C6-C14 alkyl, optionally comprising one or more heteroatoms (e.g. O, N or S) and optionally substituted with one or more substituents selected from the group consisting of a halogen, hydroxy (—OH), sulfo (—SO3M), C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 acyl, formyl, cyano, and C6-C15 aryloxy and C6-C15 aryl; and—M in each of R2 to R4 is independently selected from the group consisting of H, Na, K, Li, Ag, Zn, Mg and Ca; with the provisios that—if recurring unit Y is formed from the condensation of p-xylylene diamine and a C12 dicarboxylic acid then: —30 mol %≤nx≤90 mol %; —0 mol %≤ny≤70 mol %; and—0 mol %≤nz≤70 mol %; —nx+ny+nz≤100 mol. %; and—If recurring unit Y is formed from the condensation of terephthalic acid with a diamine, R2 is selected from the group consisting of a bond, a C1-C9 alkyl, a C11-C15 alkyl, and a C6-C30 aryl, optionally comprising one or more heteroatoms (e.g. O, N or S) and optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy (—OH), sulfo (—SO3M), C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 acyl, formyl, cyano, C6-C15 aryloxy and C6-C15 aryl.