Cyclobutanediol Polyester Bottles for Heat-Resistant Barrier Performance

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Solution Overview

Problem

Current plastic materials for containers, such as PET and polycarbonate, face challenges with high-heat applications due to poor barrier properties and processing difficulties, particularly in maintaining properties like impact strength, glass transition temperature, and chemical resistance while being processable on standard equipment.

Innovation Solution

A polyester composition comprising terephthalic acid, 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and 1,4-cyclohexanedimethanol, with specific mole percentages and inherent viscosities, which offers high impact strength, hydrolytic stability, chemical resistance, and thermoformability, while maintaining heat resistance and processability on standard industry equipment.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Reliability

If PET is used for container production, then good barrier properties are achieved, but the material becomes difficult to use at elevated temperatures such as pasteurization or retort applications

Engineering Contradiction:
Improvebarrier propertiesVSAvoidheat resistance
Core Design Contradiction:
ReliabilityVSTemperature

Solution Approach 1:

The patent uses a copolyester composition combining three different monomers (terephthalic acid or dimethyl terephthalate, 1,4-cyclohexanedimethanol, and 2,2,4,4-tetramethyl-1,3-cyclobutanediol) to create a material that integrates the heat resistance of polycarbonate with the barrier properties of polyester, resolving the contradiction between barrier performance and temperature tolerance

Inventive Principle:
Principle #40Composite materials

2Temperature

If polycarbonate or acrylic polymers are used for high-heat applications, then heat resistance is improved, but the barrier properties become poor

Engineering Contradiction:
Improveheat resistanceVSAvoidbarrier properties
Core Design Contradiction:
TemperatureVSReliability

Solution Approach 1:

The copolyester composition integrates functional groups from different monomers to simultaneously achieve the heat resistance characteristic of polycarbonate and the barrier properties characteristic of traditional polyester, eliminating the need to choose between these conflicting properties

Inventive Principle:
Principle #40Composite materials

3Stability of the object's composition

If PCT is used to produce amorphous articles, then rapid crystallization is achieved, but it becomes very difficult to form amorphous articles by known methods

Engineering Contradiction:
Improvecrystallization rateVSAvoidformability of amorphous articles
Core Design Contradiction:
Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent introduces a third monomer (2,2,4,4-tetramethyl-1,3-cyclobutanediol) with specific local molecular structure characteristics that interfere with crystallization ordering, creating local structural irregularities that prevent crystal formation while maintaining overall material stability

Inventive Principle:
Principle #3Local quality

Solution Approach 2:

The patent modifies the crystallization behavior by changing the chemical composition parameters of the polyester, specifically incorporating cyclic diols with bulky side groups that increase free volume and reduce chain packing efficiency, thereby slowing crystallization rate to enable amorphous article formation

Inventive Principle:
Principle #35Parameter changes

4Duration of action of stationary object

If ethylene glycol or isophthalic acid is added to PCT to slow crystallization, then crystallization half-time is increased, but glass transition temperature and impact strength deteriorate

Engineering Contradiction:
Improvecrystallization half-timeVSAvoidimpact strength
Core Design Contradiction:
Duration of action of stationary objectVSStrength

Solution Approach 1:

The patent changes the chemical parameters by selecting specific cyclic diol monomers with rigid cyclic structures and bulky substituents that slow crystallization through steric hindrance rather than through chain flexibility modification, thereby avoiding the degradation of mechanical properties that occurs with linear glycol additives

Inventive Principle:
Principle #35Parameter changes

5Temperature

If bisphenol A polycarbonate is used as an alternative, then heat resistance and impact strength are improved, but melt viscosity becomes relatively high leading to poor melt processability

Engineering Contradiction:
Improveheat resistanceVSAvoidmelt processability
Core Design Contradiction:
TemperatureVSEase of manufacture

Solution Approach 1:

The patent modifies the molecular weight and chain architecture parameters of the polyester by using a triad of specific monomers that create a balance between chain rigidity (for heat resistance) and chain mobility (for processability), achieving polycarbonate-like heat resistance with superior melt flow characteristics

Inventive Principle:
Principle #35Parameter changes

6Strength

If polymers containing 2,2,4,4-tetramethyl-1,3-cyclobutanediol are used, then inherent viscosity and Tg are increased, but equipment becomes insufficient to manufacture or post-polymerize these materials

Engineering Contradiction:
Improveinherent viscosityVSAvoidprocessability on standard equipment
Core Design Contradiction:
StrengthVSEase of manufacture

Solution Approach 1:

The patent optimizes the molar ratio parameters of the three monomers in the copolyester, limiting the concentration of the high-viscosity-contributing cyclobutanediol monomer to a specific range that provides sufficient heat resistance and structural stability while maintaining melt viscosity within the processing capability of standard industrial equipment

Inventive Principle:
Principle #35Parameter changes

Data Source

PatentEP1907439B1Containers comprising polyester compositions which comprise cyclobutanediol
Publication Date: 2010.07.28 EASTMAN CHEM CO
  • EP1907439B1 patent drawingFigure 1
  • EP1907439B1 patent drawingFigure 2
  • EP1907439B1 patent drawingFigure 3

AI summary

Described are bottle(s) comprising polyesters comprising (a) a dicarboxylicacidcomponent comprising terephthalic acid residues; optionally, aromatic dicarboxylic acid or aliphatic dicarboxylic acid residues; 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues; and 1,4-cyclohexanedimethanol residues.