Cyclobutanediol Polyester Composition for Slower Crystallization

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Solution Overview

Problem

Current polyester compositions based on terephthalic acid and 1,4-cyclohexanedimethanol crystallize rapidly, making it difficult to form amorphous articles, and existing modifications to slow crystallization, such as adding ethylene glycol, result in undesirable properties like higher ductile-to-brittle transition temperatures and lower glass transition temperatures.

Innovation Solution

A polyester composition comprising 70-100 mole % terephthalic acid residues, 10-30 mole % aromatic dicarboxylic acid residues, and 10-30 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues, with 70-90 mole % 1,4-cyclohexanedimethanol, achieving a balance of high impact strength, moderate glass transition temperature, and long crystallization half-times while maintaining processability on standard equipment.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Loss of time

If sufficient ethylene glycol is included to provide long crystallization half-times, then amorphous products can be formed, but glass transition temperature decreases and ductile-to-brittle transition temperature increases

Engineering Contradiction:
Improvecrystallization half-timeVSAvoidglass transition temperature
Core Design Contradiction:
Loss of timeVSTemperature

Solution Approach 1:

The patent changes the chemical composition parameters by introducing 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues (10-30 mole %) as a alternative modifying agent instead of ethylene glycol. This compositional parameter change achieves long crystallization half-times while maintaining higher glass transition temperatures (95-115°C) and lower ductile-to-brittle transition temperatures, resolving the trade-off between crystallization rate control and thermal properties

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent creates a composite polyester composition containing multiple components: terephthalic acid residues (70-100 mole %), aromatic dicarboxylic acid residues (0-30 mole %), and a glycol component comprising 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues (10-30 mole %) and 1,4-cyclohexanedimethanol residues (70-90 mole %). This composite structure combines the benefits of slowed crystallization with maintained thermal properties

Inventive Principle:
Principle #40Composite materials

2Loss of time

If 2,2,4,4-tetramethyl-1,3-cyclobutanediol is used to slow crystallization, then crystallization half-time increases, but inherent viscosity and melt viscosity become too high for standard equipment

Engineering Contradiction:
Improvecrystallization half-timeVSAvoidprocessability
Core Design Contradiction:
Loss of timeVSEase of manufacture

Solution Approach 1:

The patent optimizes the concentration parameter of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues to 10-30 mole %, which is sufficient to achieve long crystallization half-times (greater than 5 minutes at 170°C) while keeping inherent viscosity in the range of 0.50 to less than 0.75 dL/g. This parameter optimization ensures the polyester can be processed on standard industry equipment without requiring specialized high-viscosity processing equipment

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces aromatic dicarboxylic acid residues (0-30 mole %) as a additional modifying component that locally adjusts the polymer structure to further reduce melt viscosity and improve processability while maintaining the crystallization modification effects of the cyclobutanediol component

Inventive Principle:
Principle #3Local quality

3Strength

If PCT crystallizes rapidly, then high strength and stiffness are achieved, but it is very difficult to form amorphous articles by extrusion or injection molding

Engineering Contradiction:
Improvecrystallization rateVSAvoidformability of amorphous articles
Core Design Contradiction:
StrengthVSEase of manufacture

Solution Approach 1:

The patent uses 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues and aromatic dicarboxylic acid residues as intermediary components that intervene in the crystallization process of PCT. These intermediaries slow down the crystallization rate by disrupting the regular packing of polymer chains, allowing sufficient time for amorphous article formation through extrusion or injection molding while still achieving eventual crystallization for strength

Inventive Principle:
Principle #24Intermediary (Mediator)

Data Source

PatentEP1891137B1Polyester compositions containing cyclobutanediol having a certain combination of inherent viscosity and moderate glass transition temperature and articles made therefrom
Publication Date: 2011.03.16 EASTMAN CHEM CO
  • EP1891137B1 patent drawingFigure 1
  • EP1891137B1 patent drawingFigure 2
  • EP1891137B1 patent drawingFigure 3

AI summary

Described are polyesters comprising (a) a dicarboxylic acid component comprising terephthalic acid residues; optionally, aromatic dicarboxylic acid residues or aliphatic dicarboxylic acid residues; 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and 1,4-cyclohexanedimethanol residues. The polyesters may be manufactured into articles such as fibers, films, bottles or sheets.