US20120184668A1 - Clear Ternary Blends of Polycarbonate with an Aliphatic Polyester and an Aromatic-Aliphatic Polyester - Google Patents

Clear Ternary Blends of Polycarbonate with an Aliphatic Polyester and an Aromatic-Aliphatic Polyester Download PDF

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Publication number
US20120184668A1
US20120184668A1 US13/097,722 US201113097722A US2012184668A1 US 20120184668 A1 US20120184668 A1 US 20120184668A1 US 201113097722 A US201113097722 A US 201113097722A US 2012184668 A1 US2012184668 A1 US 2012184668A1
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mole
dicarboxylic acid
residues
component
cyclohexanedimethanol
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Gary Michael Stack
Wesley Raymond Hale
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Eastman Chemical Co
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Eastman Chemical Co
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Publication of US20120184668A1 publication Critical patent/US20120184668A1/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
    • A01N59/16—Heavy metals; Compounds thereof
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
    • C08G63/16—Dicarboxylic acids and dihydroxy compounds
    • C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
    • C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
    • C08K3/015—Biocides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/10—Metal compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C08K2003/0806—Silver
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2286—Oxides; Hydroxides of metals of silver
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C08K2003/321—Phosphates
    • C08K2003/328—Phosphates of heavy metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14—Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • C08L2666/18—Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/54—Inorganic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds

Definitions

  • the present disclosure generally relates to clear polymer blends comprising two high molecular weight polyesters and a bisphenol A polycarbonate.
  • the polymer blends of the present disclosure comprise: a) an aromatic-aliphatic polyester made from terephthalic acid, 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and either 1,4-cyclohexanedimethanol or ethylene glycol; b) an aliphatic polyester made from 1,4 cyclohexane dicarboxylic acid and 1,4 cyclohexanedimethanol (PCCD); and c) a polycarbonate of 4,4′-isopropylidenediphenol (bisphenol A).
  • compositions of the present disclosure have a certain combination of two or more properties of clarity, heat resistance, high glass transition temperatures, chemical resistance, toughness, miscibility and/or good flowability, while retaining processability, which allow them to be easily formed into items, for example, molded articles, films, and fibers.
  • plastics, films, and fibers can be produced with a variety of plastic materials by a variety of processes, such as extrusion blow molding, stretch blow molding, etc.
  • plastic materials may comprise mixtures of structurally different polymers or copolymers in multicomponent blends, which may have certain properties superior to those of the individual polymers.
  • desired properties include improved heat resistance, chemical resistance, and melt processability. Clarity is also a desired characteristic for various plastic materials, yet few blends comprising two or more polymers are clear.
  • One common copolyester used to produce films, sheeting, and molded articles is made from terephthalic acid, 1,4-cyclohexanedimethanol, and ethylene glycol. While these copolyesters are useful in many end-use applications, they exhibit deficiencies in properties such as glass transition temperature and impact strength when sufficient modifying ethylene glycol is included in the formulation in order to provide for long crystallization half-times.
  • bisphenol A polycarbonate The polycarbonate of 4,4′-isopropylidenediphenol (bisphenol A polycarbonate) has been used as an alternative for polyesters known in the art and is a well known engineering molding plastic.
  • Bisphenol A polycarbonate is a clear, high-performance plastic having good physical properties such as dimensional stability, high heat resistance, and good impact strength.
  • bisphenol-A polycarbonate has many potentially desirable physical properties, its relatively high melt viscosity leads to poor melt processability and the material exhibits poor chemical resistance.
  • Bisphenol-A polycarbonate is also difficult to thermoform.
  • the present disclosure relates to a ternary blend of PCCD, a bisphenol-A polycarbonate, and an aromatic-aliphatic polyester comprising 2,2,4,4-tetramethyl-1,3-cyclobutanediol and either 1,4-cyclohexanedimethanol or ethylene glycol, wherein the aromatic-aliphatic polyester and polycarbonate form a hazy blend, which is made clear by the addition of PCCD.
  • These polymer blends have a unique combination of two or more of the following properties: clarity, toughness, high glass transition temperatures, heat resistance, chemical resistance, miscibility and/or good flowability, while retaining processability on the standard equipment used in the industry.
  • the present disclosure relates to clear polymer blends comprising an aromatic-aliphatic polyester, an aliphatic polyester, and a bisphenol A polycarbonate.
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  • all embodiments of the invention can contain 20 to 80 weight % of the aliphatic-aromatic polyester and 20 to 80 weight % of the polycarbonate; or 20 to 60 weight % of the aliphatic-aromatic polyester and 40 to 80 weight % of the polycarbonate; or 30 to 60 weight % of the aliphatic-aromatic polyester and 40 to 70 weight % of the polycarbonate; or 40 to 60 weight % of the aliphatic-aromatic polyester and 40 to 80 weight % of the polycarbonate; or 40 to 50 weight % of the aliphatic-aromatic polyester and 50 to 60 weight % of the polycarbonate.
  • the polymer blends useful in the present disclosure have a unique combination of two or more physical properties such as clarity, toughness, high glass transition temperatures, heat resistance, chemical resistance, miscibility and/or good flowability, while retaining good processability thereby easily permitting them to be formed into articles.
  • the term “polyester” is intended to include “copolyesters” and is understood to mean a synthetic polymer prepared by the reaction of one or more difunctional carboxylic acids and/or multifunctional carboxylic acids with one or more difunctional hydroxyl compounds and/or multifunctional hydroxyl compounds.
  • the difunctional carboxylic acid can be a dicarboxylic acid and the difunctional hydroxyl compound can be a dihydric alcohol such as, for example, a glycol.
  • diacid or “dicarboxylic acid” includes multifunctional acids, such as branching agents.
  • glycol as used in this application includes, but is not limited to, diols, glycols, and/or multifunctional hydroxyl compounds.
  • the difunctional carboxylic acid may be a hydroxy carboxylic acid such as, for example, p-hydroxybenzoic acid
  • the difunctional hydroxyl compound may be an aromatic nucleus bearing 2 hydroxyl substituents such as, for example, hydroquinone.
  • an aromatic-aliphatic polyester refers to a polyester in which the carboxylic acid residues are derived from aromatic carboxylic acid and the glycol residues are derived from aliphatic alcohols.
  • An aliphatic polyester refers to a polyester in which both the carboxylic acid residues and the glycol residues are derived from aliphatic carboxylic acids and aliphatic alcohols respectively.
  • the term “residue”, as used herein, means any organic structure incorporated into a polymer through a polycondensation and/or an esterification reaction from the corresponding monomer.
  • the term “repeating unit”, as used herein, means an organic structure having a dicarboxylic acid residue and a diol residue bonded through a carbonyloxy group.
  • the dicarboxylic acid residues may be derived from a dicarboxylic acid monomer or its associated acid halides, esters, salts, anhydrides, or mixtures thereof.
  • dicarboxylic acid is intended to include dicarboxylic acids and any derivative of a dicarboxylic acid, including its associated isomers, acid halides, esters, half-esters, salts, half-salts, anhydrides, mixed anhydrides, or mixtures thereof, useful in a reaction process with a diol to make polyester.
  • polycarbonate is intended to include “copolycarbonates” and is understood to mean the condensation product of a carbonate source and a diol source.
  • terephthalic acid is intended to include terephthalic acid itself and residues thereof as well as any derivative of terephthalic acid, including its associated isomers, acid halides, esters, half-esters, salts, half-salts, anhydrides, mixed anhydrides, or mixtures thereof or residues thereof useful in a reaction process with a diol to make polyester.
  • terephthalic acid may be used as starting material for the aromatic-aliphatic polyester.
  • isophthalic acid may be used as starting material.
  • mixtures of terephthalic acid and isophthalic acid may be used as starting material and/or as an intermediate material.
  • the polyesters used in the present disclosure typically can be prepared from dicarboxylic acids and diols which react in substantially equal proportions and are incorporated into the polyester polymer component and polymer blends as their corresponding residues.
  • the polyesters of the present disclosure therefore, can contain substantially equal molar proportions of acid residues (100 mole %) and diol (and/or multifunctional hydroxyl compounds) residues (100 mole %) such that the total moles of repeating units is equal to 100 mole %.
  • the mole percentages provided in the present disclosure therefore, may be based on the total moles of acid residues, the total moles of diol residues, or the total moles of repeating units.
  • a polyester containing 30 mole % isophthalic acid means the polyester contains 30 mole % isophthalic acid residues out of a total of 100 mole % acid residues. Thus, there are 30 moles of isophthalic acid residues among every 100 moles of acid residues.
  • a polyester containing 30 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol means the polyester contains 30 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues out of a total of 100 mole % diol residues. Thus, there are 30 moles of 2,2,4,4-tetramethyl-1,3-cyclobutanediol residues among every 100 moles of diol residues.
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include, but are not limited to, at least one of the following combinations of ranges: 1 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 99 mole % 1,4-cyclohexanedimethanol; 1 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 99 mole % 1,4-cyclohexanedimethanol; 1 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 99 mole % 1,4-cyclohexanedimethanol; 1 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 99 mole % 1,4-cyclohexanedimethanol; 1 to 80 mole
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 5 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 95 mole % 1,4-cyclohexanedimethanol; 5 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 95 mole % 1,4-cyclohexanedimethanol; 5 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 95 mole % 1,4-cyclohexanedimethanol; 5 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 95 mole % 1,4-cyclohexanedimethanol; 5 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 10 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 90 mole % 1,4-cyclohexanedimethanol; 10 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 90 mole % 1,4-cyclohexanedimethanol; 10 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 90 mole % 1,4-cyclohexanedimethanol; 10 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 90 mole % 1,4-cyclohexanedimethanol; 10 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 15 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 85 mole % 1,4-cyclohexanedimethanol; 15 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 85 mole % 1,4-cyclohexanedimethanol; 15 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 85 mole % 1,4-cyclohexanedimethanol; 15 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 85 mole % 1,4-cyclohexanedimethanol; 15 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 20 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 80 mole % 1,4-cyclohexanedimethanol; 20 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 80 mole % 1,4-cyclohexanedimethanol; 20 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 80 mole % 1,4-cyclohexanedimethanol; 20 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 80 mole % 1,4-cyclohexanedimethanol; 20 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 25 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 75 mole % 1,4-cyclohexanedimethanol; 25 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 75 mole % 1,4-cyclohexanedimethanol; 25 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 75 mole % 1,4-cyclohexanedimethanol; 25 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 75 mole % 1,4-cyclohexanedimethanol; 25 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 30 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 70 mole % 1,4-cyclohexanedimethanol; 30 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 70 mole % 1,4-cyclohexanedimethanol; 30 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 70 mole % 1,4-cyclohexanedimethanol; 30 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 70 mole % 1,4-cyclohexanedimethanol; 30 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 35 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 65 mole % 1,4-cyclohexanedimethanol; 35 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 65 mole % 1,4-cyclohexanedimethanol; 35 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 65 mole % 1,4-cyclohexanedimethanol; 35 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 65 mole % 1,4-cyclohexanedimethanol; 35 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 40 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 60 mole % 1,4-cyclohexanedimethanol; 40 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 60 mole % 1,4-cyclohexanedimethanol; 40 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 60 mole % 1,4-cyclohexanedimethanol; 40 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 60 mole % 1,4-cyclohexanedimethanol; 40 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 45 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 55 mole % 1,4-cyclohexanedimethanol; 45 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 55 mole % 1,4-cyclohexanedimethanol; 45 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 55 mole % 1,4-cyclohexanedimethanol; 45 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 55 mole % 1,4-cyclohexanedimethanol; 45 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 50 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 50 mole % 1,4-cyclohexanedimethanol; 50 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 50 mole % 1,4-cyclohexanedimethanol; 50 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 50 mole % 1,4-cyclohexanedimethanol; 50 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 50 mole % 1,4-cyclohexanedimethanol; 50 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 55 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 45 mole % 1,4-cyclohexanedimethanol; 55 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 45 mole % 1,4-cyclohexanedimethanol; 55 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 45 mole % 1,4-cyclohexanedimethanol; 55 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 45 mole % 1,4-cyclohexanedimethanol; 55 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 60 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 40 mole % 1,4-cyclohexanedimethanol; 60 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 40 mole % 1,4-cyclohexanedimethanol; 60 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 40 mole % 1,4-cyclohexanedimethanol; 60 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 40 mole % 1,4-cyclohexanedimethanol; 60 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 65 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 35 mole % 1,4-cyclohexanedimethanol; 65 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 35 mole % 1,4-cyclohexanedimethanol; 65 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 35 mole % 1,4-cyclohexanedimethanol; 65 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 35 mole % 1,4-cyclohexanedimethanol; 65 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 70 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 30 mole % 1,4-cyclohexanedimethanol; 70 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 30 mole % 1,4-cyclohexanedimethanol; 70 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 30 mole % 1,4-cyclohexanedimethanol; 70 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 30 mole % 1,4-cyclohexanedimethanol; 70 to 80 mole %
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 75 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 25 mole % 1,4-cyclohexanedimethanol; 75 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 25 mole % 1,4-cyclohexanedimethanol; 75 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 25 mole % 1,4-cyclohexanedimethanol; 75 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 25 mole % 1,4-cyclohexanedimethanol; and 75 to 80 mole
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 80 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 20 mole % 1,4-cyclohexanedimethanol; 80 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 20 mole % 1,4-cyclohexanedimethanol; 80 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 20 mole % 1,4-cyclohexanedimethanol; and 80 to 85 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 15 to 20 mole % 1,4-cyclohexanedimethanol.
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following combinations of ranges: 85 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 15 mole % 1,4-cyclohexanedimethanol; 85 to 95 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 5 to 15 mole % 1,4-cyclohexanedimethanol; 85 to 90 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 10 to 15 mole % 1,4-cyclohexanedimethanol; 90 to 100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 0 to 10 mole % 1,4-cyclohexanedimethanol; 90 to 95 mole % 2,2,4,4-t
  • ethylene glycol may be used in place of, or in a mixture with, 1,4-cyclohexanedimethanol in the glycol component of the aromatic-aliphatic polyester.
  • the glycol component for the aromatic-aliphatic polyesters of the polymer blends disclosed herein include but are not limited to at least one of the following ranges: 1 to 99 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1 to 99 mole % ethylene glycol; 5 to 99 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1 to 95 mole % ethylene glycol; 10 to 99 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1 to 90 mole % ethylene glycol; 15 to 99 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and 1 to 85 mo
  • the molar ratio of cis/trans 2,2,4,4-tetramethyl-1,3-cyclobutanediol can vary from 1 to 0 and from 0 to 1, which includes the pure form of each isomer and mixtures thereof.
  • the molar percentages for cis and/or trans 2,2,4,4,-tetramethyl-1,3-cyclobutanediol are greater than 40 mole % cis and less than 60 mole % trans; or greater than 50 mole % cis and less than 50 mole % trans; or 30 to 70 mole % cis and 70 to 30% trans; or 40 to 60 mole % cis and 60 to 40 mole % trans; or 50 to 70 mole % trans and 50 to 30% cis or 50 to 70 mole % cis and 50 to 30% trans; or greater than 70 mole cis and less than 30 mole % trans; wherein the total sum of the mole percentages for cis- and trans-2,2,4,4-tetramethyl-1,3-cyclobutanediol is equal to 100 mole %.
  • the molar ratio of cis/trans 1,4-cyclohexandimethanol can vary from 1 to 0 and from 0 to 1, which includes the pure form of each isomer and mixtures thereof.
  • the molar percentages for cis and/or trans 1,4-cyclohexandimethanol are less than 50 mole % cis and greater than 50 mole % trans; or 25 to 75 mole % cis and 75 to 25% trans; or 40 to 60 mole % cis and 60 to 40 mole % trans; wherein the total sum of the mole percentages for cis- and trans-1,4-cyclohexandimethanol is equal to 100 mole %.
  • the glycol component of the aromatic-aliphatic polyester polyesters useful in the present disclosure can contain up to 10 mole % of one or more modifying glycols which are not 2,2,4,4-tetramethyl-1,3-cyclobutanediol or 1,4-cyclohexanedimethanol.
  • the polyesters useful in the present disclosure can contain up to 5 mole % one or more modifying glycols.
  • the polyesters useful in the present disclosure can contain up to 3 mole % of one or more modifying glycols.
  • the polyesters useful in the present disclosure can contain 0 mole % modifying glycols.
  • Certain embodiments can contain 0.01 or more mole %, such as 0.1 or more mole %, 1 or more mole %, or 5 or more mole % of one or more modifying glycols.
  • the amount of one or more modifying glycols can range from any of these preceding endpoint values including, for example, from 0.01 to 10 mole %, from 0.01 to 5 mole %, and from 0.1 to 3 mole %.
  • Modifying glycols useful in the aromatic-aliphatic polyesters of the polymer blends of the present disclosure refer to diols other than 2,2,4,4,-tetramethyl-1,3-cyclobutanediol and 1,4-cyclohexanedimethanol and may contain 2 to 16 carbon atoms.
  • suitable modifying glycols include, but are not limited to, ethylene glycol, 1,2-propanediol, 1,3-propanediol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, p-xylene glycol, or mixtures thereof.
  • the aromatic-aliphatic polyesters of the polymer blends useful in the present disclosure may be modified with polyethylene glycols or polytetramethylene glycols.
  • terephthalic acid or an ester thereof, or a mixture of terephthalic acid and an ester thereof makes up most or all of the dicarboxylic acid component used to form the aromatic-aliphatic polyesters useful in the present disclosure.
  • terephthalic acid residues can make up a portion or all of the dicarboxylic acid component used to form the present polyester at a concentration of at least 70 mole %, such as at least 80 mole %, at least 90 mole %, at least 95 mole %, at least 99 mole %, or 100 mole %.
  • dicarboxylic acid esters include, but are not limited to, the dimethyl, dipropyl, diisopropyl, dibutyl, and diphenyl esters.
  • the dicarboxylic acid component of the aromatic-aliphatic polyester useful in the present disclosure can comprise up to 25 mole %, up to 20 mole %, up to 15 mole %, up to 10 mole %, up to 5 mole %, or up to 1 mole % of one or more modifying aromatic dicarboxylic acids. Yet another embodiment may contain 0 mole % modifying aromatic dicarboxylic acids.
  • the amount of one or more modifying aromatic dicarboxylic acids can range from any of these preceding endpoint values including, for example, from 0.01 to 25 mole %, 0.01 to 20 mole %, from 0.01 to 15 mole %, from 0.01 to 10 mole %, from 0.01 to 5 mole % and from 0.01 to 1 mole.
  • modifying aromatic dicarboxylic acids that may be used in the present disclosure include but are not limited to those having up to 20 carbon atoms, and which can be linear, para-oriented, or symmetrical.
  • modifying aromatic dicarboxylic acids which may be used in the present disclosure include, but are not limited to, 4,4′-biphenyldicarboxylic acid, 1,5-, 2,6-, 2,7-naphthalenedicarboxylic acid, 4,4′-oxydibenzoic acid, trans-4,4′-stilbenedicarboxylic acid, and esters thereof.
  • the carboxylic acid component of the aromatic-aliphatic polyesters useful in the present disclosure can be further modified with up to 20 mole %, such as up to 15 mole %, or up to 10 mole %, or up to 5 mole %, or up to 1 mole % of one or more aliphatic dicarboxylic acids containing 6-12 carbon atoms, such as, for example, succinic, glutaric, adipic, sebacic, suberic, azelaic, decanedicarboxylic, and dodecanedicarboxylic acids.
  • up to 20 mole % such as up to 15 mole %, or up to 10 mole %, or up to 5 mole %, or up to 1 mole % of one or more aliphatic dicarboxylic acids containing 6-12 carbon atoms, such as, for example, succinic, glutaric, adipic, sebacic, suberic, azelaic, decanedicarboxy
  • Certain embodiments can also comprise 0.01 or more mole %, such as 0.1 or more mole %, 1 or more mole %, 5 or more mole %, or 10 or more mole % of one or more modifying aliphatic dicarboxylic acids. Yet another embodiment may contain 0 mole % modifying aliphatic dicarboxylic acids. Thus, if present, it is contemplated that the amount of one or more modifying aliphatic dicarboxylic acids can range from any of these preceding endpoint values including, for example, from 0.01 to 10 mole % and from 0.1 to 10 mole %. The total mole % of the dicarboxylic acid component is 100 mole %.
  • the glycol component of the aliphatic polyesters useful in the present disclosure can contain up to 10 mole % of one or more modifying glycols which are not 1,4-cyclohexanedimethanol.
  • the aliphatic polyesters useful in the present disclosure can contain up to 5 mole % one or more modifying glycols.
  • the polyesters useful in the present disclosure can contain up to 3 mole % of one or more modifying glycols.
  • the polyesters useful in the present disclosure can contain 0 mole % modifying glycols.
  • Certain embodiments can contain 0.01 or more mole %, such as 0.1 or more mole %, 1 or more mole %, or 5 or more mole % of one or more modifying glycols.
  • the amount of one or more modifying glycols can range from any of these preceding endpoint values including, for example, from 0.01 to 10 mole %, from 0.01 to 5 mole %, and from 0.1 to 3 mole %.
  • Modifying glycols useful in the aliphatic polyesters of the polymer blends of the present disclosure refer to diols other than 1,4-cyclohexanedimethanol and may contain 2 to 16 carbon atoms.
  • suitable modifying glycols include, but are not limited to, ethylene glycol, 1,2-propanediol, 1,3-propanediol, neopentyl glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, or mixtures thereof.
  • the aliphatic polyesters of the polymer blends useful in the present disclosure may be modified with polyethylene glycols or polytetramethylene glycols.
  • the molar ratio of cis/trans 1,4-cyclohexane dicarboxylic acid can vary from 1 to 0 and from 0 to 1, which includes the pure form of each isomer and mixtures thereof.
  • the molar percentages for cis and/or trans 1,4-cyclohexane dicarboxylic acid are less than 50 mole % cis and greater than 50 mole % trans; or less than 25 mole % cis and greater than 75 mole % trans; or 5 to 95 mole % cis and 95 to 5% trans; or 5 to 75 mole % cis and 95 to 25% trans; or 5 to 50 mole % cis and 95 to 50 mole % trans; or 5 to 25 mole % cis and 95 to 75% trans; wherein the total sum of the mole percentages for cis- and trans-1,4-cyclohexane dicarboxylic acid is equal to 100 mole %
  • the molar ratio of cis/trans 1,4-cyclohexanedimethanol can vary from 1 to 0 and from 0 to 1, which includes the pure form of each isomer and mixtures thereof.
  • the molar percentages for cis and/or trans 1,4-cyclohexanedimethanol are less than 50 mole % cis and greater than 50 mole % trans; or less than 35 mole % cis and greater than 65 mole % trans; or 10 to 95 mole % cis and 90 to 5% trans; or 10 to 75 mole % cis and 90 to 25% trans; or 10 to 50 mole % cis and 90 to 50 mole % trans; or 25 to 75 mole % cis and 75 to 25% trans; or 25 to 50 mole % cis and 75 to 50 mole % trans; wherein the total sum of the mole percentages for cis- and trans-1,4-cyclohexane
  • 1,4-cyclohexane dicarboxylic acid or an ester thereof, or a mixture of 1,4-cyclohexane dicarboxylic acid and an ester thereof makes up most or all of the dicarboxylic acid component used to form the aliphatic polyesters useful in the present disclosure.
  • 1,4-cyclohexane dicarboxylic acid residues can make up a portion or all of the dicarboxylic acid component used to form the aliphatic polyester at a concentration of at least 75 mole %, such as at least 80 mole %, at least 85 mole %, at least 90 mole %, at least 95 mole %, at least 99 mole %, or 100 mole %.
  • dicarboxylic acid esters include, but are not limited to, the dimethyl, dipropyl, diisopropyl, dibutyl, and diphenyl esters.
  • the dicarboxylic acid component of the aliphatic polyester useful in the present disclosure can comprise up to 25 mole %, up to 20 mole %, up to 15 mole %, up to 10 mole %, up to 5 mole %, or up to 1 mole % of one or more modifying aliphatic dicarboxylic acids containing 6-12 carbon atoms, such as, for example, succinic, glutaric, adipic, sebacic, suberic, azelaic, decanedicarboxylic, and dodecanedicarboxylic acids.
  • modifying aliphatic dicarboxylic acids containing 6-12 carbon atoms such as, for example, succinic, glutaric, adipic, sebacic, suberic, azelaic, decanedicarboxylic, and dodecanedicarboxylic acids.
  • Certain embodiments can also comprise 0.01 or more mole %, such as 0.1 or more mole %, 1 or more mole %, 5 or more mole %, or 10 or more mole % of one or more modifying aliphatic dicarboxylic acids. Yet another embodiment may contain 0 mole % modifying aliphatic dicarboxylic acids. Thus, if present, it is contemplated that the amount of one or more modifying aliphatic dicarboxylic acids can range from any of these preceding endpoint values including, for example, from 0.01 to 10 mole % and from 0.1 to 10 mole %. The total mole % of the dicarboxylic acid component is 100 mole %.
  • the aromatic-aliphatic polyesters and aliphatic polyesters may exhibit at least one of the following inherent viscosities as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.: 0.10 to 1.20 dL/g; 0.10 to 1.10 dL/g; 0.10 to 1.00 dL/g; 0.10 to 0.90 dL/g; 0.10 to 0.80 dL/g; 0.10 to 0.70 dL/g; 0.10 to 0.60 dL/g; 0.10 to 0.50 dL/g; 0.10 to 0.40 dL/g; 0.10 to 0.30 dL/g; 0.10 to 0.20 dL/g; 0.20 to 1.20 dL/g; 0.20 to 1.10 dL/g; 0.20 to 1.00 dL/g; 0.20 to 0.90 dL/g; 0.20
  • the glass transition temperature (Tg) of the polyester blends or the polyesters useful in the invention may be determined, for example, by using a Perkin Elmer differential scanning calorimeter (DSC) instrument at a scan rate of 20° C./min.
  • the Tg of the polyesters can be at least one of the following ranges: 80 to 130° C.; 80 to 125° C.; 80 to 120° C.; 80 to 115° C.; 80 to 110° C.; 80 to 105° C.; 80 to 100° C.; 80 to 95° C.; 80 to 90° C.; 80 to 85° C.; 85 to 130° C.; 85 to 125° C.; 85 to 120° C.; 85 to 115° C.; 85 to 110° C.; 85 to 105° C.; 85 to 100° C.; 85 to 95° C.; 85 to 90° C.; 90 to 130° C.; 90 to 125° C.; 90 to 120° C.; 90 to 115° C.;
  • Thermal stabilizers for polyesters are compounds that stabilize polyesters during polyester manufacture and/or post polymerization. These thermal stabilizers can be present in either of the aromatic-aliphatic polyesters or in the aliphatic polyesters useful in the present disclosure and include, but are not limited to, phosphorous compounds, such as, for example, phosphoric acid, phosphorous acid, phosphonic acid, phosphinic acid, phosphonous acid, and various esters and salts thereof.
  • the esters can be alkyl, branched alkyl, substituted alkyl, difunctional alkyl, alkyl ethers, aryl, and substituted aryl.
  • the number of ester groups present in the particular phosphorous compound can vary from zero up to the maximum allowable based on the number of hydroxyl groups present on the thermal stabilizer used.
  • thermal stabilizer is intended to include the reaction product(s) thereof.
  • reaction product as used in connection with the thermal stabilizers of the present disclosure refers to any product of a polycondensation or esterification reaction between the thermal stabilizer and any of the monomers used in making the polyester as well as the product of a polycondensation or esterification reaction between the catalyst and any other type of additive.
  • the thermal stabilizer(s) can be an organic compound such as, for example, a phosphorus acid ester containing halogenated or non-halogenated organic substituents.
  • the thermal stabilizer can comprise a wide range of phosphorus compounds well-known in the art such as, for example, phosphines, phosphites, phosphinites, phosphonites, phosphinates, phosphonates, phosphine oxides, and phosphates.
  • thermal stabilizers include tributyl phosphate, triethyl phosphate, tri-butoxyethyl phosphate, t-butylphenyl diphenyl phosphate, 2-ethylhexyl diphenyl phosphate, ethyl dimethyl phosphate, isodecyl diphenyl phosphate, trilauryl phosphate, triphenyl phosphate, tricresyl phosphate, trixylenyl phosphate, t-butylphenyl diphenylphosphate, resorcinol bis(diphenyl phosphate), tribenzyl phosphate, phenyl ethyl phosphate, trimethyl thionophosphate, phenyl ethyl thionophosphate, dimethyl methylphosphonate, diethyl methylphosphonate, diethyl pentylphosphonate, dilauryl methylphosphonate, diphenyl
  • thermal stabilizers can be any of the previously described phosphorus-based acids wherein one or more of the hydrogen atoms of the acid compound (bonded to either oxygen or phosphorus atoms) are replaced with alkyl, branched alkyl, substituted alkyl, alkyl ethers, substituted alkyl ethers, alkyl-aryl, alkyl-substituted aryl, aryl, substituted aryl, and mixtures thereof.
  • thermal stabilizers include but are not limited to, the above described compounds wherein at least one of the hydrogen atoms bonded to an oxygen atom of the compound is replaced with a metallic ion or an ammonium ion.
  • the esters can contain alkyl, branched alkyl, substituted alkyl, alkyl ethers, aryl, and/or substituted aryl groups.
  • the esters can also have at least one alkyl group and at least one aryl group.
  • the number of ester groups present in the particular phosphorus compound can vary from zero up to the maximum allowable based on the number of hydroxyl groups present on the phosphorus compound used.
  • an alkyl phosphate ester can include one or more of the mono-, di-, and tri alkyl phosphate esters; an aryl phosphate ester includes one or more of the mono-, di-, and tri aryl phosphate esters; and an alkyl phosphate ester and/or an aryl phosphate ester also include, but are not limited to, mixed alkyl aryl phosphate esters having at least one alkyl and one aryl group.
  • the thermal stabilizers include but are not limited to alkyl, aryl or mixed alkyl aryl esters or partial esters of phosphoric acid, phosphorus acid, phosphinic acid, phosphonic acid, or phosphonous acid.
  • the alkyl or aryl groups can contain one or more substituents.
  • the phosphorus compounds comprise at least one thermal stabilizer chosen from at least one of substituted or unsubstituted alkyl phosphate esters, substituted or unsubstituted aryl phosphate esters, substituted or unsubstituted mixed alkyl aryl phosphate esters, diphosphites, salts of phosphoric acid, phosphine oxides, and mixed aryl alkyl phosphites, reaction products thereof, and mixtures thereof.
  • the phosphate esters include esters in which the phosphoric acid is fully esterified or only partially esterified.
  • the thermal stabilizers can include at least one phosphate ester.
  • the phosphorus compounds useful in the present disclosure comprise at least one thermal stabilizer chosen from at least one of substituted or unsubstituted alkyl phosphate esters, substituted or unsubstituted aryl phosphate esters, mixed substituted or unsubstituted alkyl aryl phosphate esters, reaction products thereof, and mixtures thereof.
  • the phosphate esters include esters in which the phosphoric acid is fully esterified or only partially esterified.
  • the thermal stabilizers useful in the present disclosure can include at least one phosphate ester.
  • the phosphate esters useful in the present disclosure can include but are not limited to alkyl phosphate esters, aryl phosphate esters, mixed alkyl aryl phosphate esters, and/or mixtures thereof.
  • the phosphate esters useful in the present disclosure are those where the groups on the phosphate ester include are alkyl, alkoxy-alkyl, phenyl, or substituted phenyl groups. These phosphate esters are generally referred to herein as alkyl and/or aryl phosphate esters. Certain preferred embodiments include trialkyl phosphates, triaryl phosphates, alkyl diaryl phosphates, dialkyl aryl phosphates, and mixtures of such phosphates, wherein the alkyl groups are preferably those containing from 2 to 12 carbon atoms, and the aryl groups are preferably phenyl.
  • alkyl and branched alkyl groups are preferably those containing from 1-12 carbon atoms, including, but not limited to, ethyl, propyl, isopropyl, butyl, hexyl, cyclohexyl, 2-ethylhexyl, octyl, decyl and dodecyl.
  • Substituted alkyl groups include, but are not limited to, those containing at least one of carboxylic acid groups and esters thereof, hydroxyl groups, amino groups, keto groups, and the like.
  • alkyl-aryl and substituted alkyl-aryl groups are those wherein the alkyl portion contains from 1-12 carbon atoms, and the aryl group is phenyl or substituted phenyl wherein groups such as alkyl, branched alkyl, aryl, hydroxyl, and the like are substituted for hydrogen at any carbon position on the phenyl ring.
  • Preferred aryl groups include phenyl or substituted phenyl wherein groups such as alkyl, branched alkyl, aryl, hydroxyl and the like are substituted for hydrogen at any position on the phenyl ring.
  • the phosphate esters useful as thermal stabilizers in the present disclosure include but are not limited to dibutylphenyl phosphate, triphenyl phosphate, tricresyl phosphate, tributyl phosphate, tri-2-ethylhexyl phosphate, trioctyl phosphate, and/or mixtures thereof, including particularly mixtures of tributyl phosphate and tricresyl phosphate, and mixtures of isocetyl diphenyl phosphate and 2-ethylhexyl diphenyl phosphate.
  • the phosphate esters useful as thermal stabilizers in the present disclosure include but are not limited to, at least one of the following: trialkyl phosphates, triaryl phosphates, alkyl diaryl phosphates, and mixed alkyl aryl phosphates.
  • the phosphate esters useful as thermal stabilizers in the present disclosure include but are not limited to, at least one of the following: triaryl phosphates, alkyl diaryl phosphates, and mixed alkyl aryl phosphates.
  • the phosphate esters useful as thermal stabilizers in the present disclosure include but are not limited to, at least one of the following: triaryl phosphates and mixed alkyl aryl phosphates.
  • At least one thermal stabilizer useful in the present disclosure comprises, but is not limited to, triaryl phosphates, such as, for example, triphenyl phosphate.
  • at least one thermal stabilizer comprises, but is not limited to Merpol A.
  • at least one thermal stabilizer useful in the present disclosure comprises, but is not limited to, at least one of triphenyl phosphate and Merpol A.
  • Merpol A is a phosphate ester commercially available from Stepan Chemical Co and/or E.I. duPont de Nemours & Co. The CAS Registry number for Merpol A is believed to be CAS Registry #37208-27-8.
  • the polyester compositions and/or processes of the present disclosure may comprise 2-ethylhexyl diphenyl phosphate.
  • the polyester compositions and/or processes of the present disclosure may comprise 2-ethylhexyl diphenyl phosphate.
  • the phosphorus compounds useful in the present disclosure comprise, but are not limited to, at least one diphosphite.
  • the phosphorus compounds useful in the present disclosure comprise, but are not limited to, at least one diphosphite which contains a 2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane structure, such as, for example, Weston 619 (GE Specialty Chemicals, CAS#3806-34-6) and/or Doverphos S-9228 (Dover Chemicals, CAS#154862-43-8).
  • the phosphorus compounds useful in the present disclosure comprise at least one phosphine oxide, such as, for example, triphenylphosphine oxide.
  • the phosphorus compounds useful in the present disclosure comprise at least one mixed alkyl aryl phosphites, such as, for example, bis(2,4-dicumylphenyl)pentaerythritol diphosphite also known as Doverphos S-9228 (Dover Chemicals, CAS#154862-43-8).
  • mixed alkyl aryl phosphites such as, for example, bis(2,4-dicumylphenyl)pentaerythritol diphosphite also known as Doverphos S-9228 (Dover Chemicals, CAS#154862-43-8).
  • any of processes described herein for making the polyester compositions and/or polyesters comprise at least one of the phosphorus compounds described herein.
  • any of processes described herein for making any of the polyester compositions and/or polyesters can comprise at least one diphosphite.
  • any of the processes described herein for making any of the polyester compositions and/or polyesters can comprise, at least one diphosphite which contains a 2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane structure, such as, for example, Weston 619 (GE Specialty Chemicals, CAS#3806-34-6) and/or Doverphos S-9228 (Dover Chemicals, CAS#154862-43-8).
  • any of the processes described herein for making any of the polyester compositions and/or polyesters can comprise at least one phosphine oxide, such as, for example, triphenylphosphine oxide.
  • any of the processes described herein for making any of the polyester compositions and/or polyesters can comprise at least one mixed alkyl aryl phosphites, such as, for example, bis(2,4-dicumylphenyl)pentaerythritol diphosphite also known as Doverphos S-9228 (Dover Chemicals, CAS#154862-43-8).
  • mixed alkyl aryl phosphites such as, for example, bis(2,4-dicumylphenyl)pentaerythritol diphosphite also known as Doverphos S-9228 (Dover Chemicals, CAS#154862-43-8).
  • phosphorus When phosphorus is added to the polyesters and/or polyester compositions and/or process of making the polyesters of the present disclosure, it is added in the form of a phosphorus compound as described herein, for example, at least one phosphate ester, at least one diphosphite, at least one salt of phosphoric acid.
  • the amount of phosphorus compound(s), (for example, at least one diphosphite), is added to the polyesters of the present disclosure and/or polyester compositions of the present disclosure and/or processes of the present disclosure can be measured in the form of phosphorus atoms present in the final polyester, for example, by weight measured in ppm.
  • Amounts of thermal stabilizer added during polymerization or post manufacturing can include but are not limited to: 1 to 5000 ppm; 1 to 1000 ppm, 1 to 900 ppm, 1 to 800 ppm, 1 to 700 ppm. 1 to 600 ppm, 1 to 500 ppm, 1 to 400 ppm, 1 to 350 ppm, 1 to 300 ppm, 1 to 250 ppm, 1 to 200 ppm, 1 to 150 ppm, 1 to 100 ppm; 10 to 5000 ppm; 10 to 1000 ppm, 10 to 900 ppm, 10 to 800 ppm, 10 to 700 ppm.
  • amounts of the phosphorus compound (for example, diphosphite, phosphate ester, etc.) of the present disclosure added during polymerization are chosen from the following: 1 to 5000 ppm; 1 to 1000 ppm, 1 to 900 ppm, 1 to 800 ppm, 1 to 700 ppm. 1 to 600 ppm, 1 to 500 ppm, 1 to 400 ppm, 1 to 350 ppm, 1 to 300 ppm, 1 to 250 ppm, 1 to 200 ppm, 1 to 150 ppm, 1 to 100 ppm; 1 to 60 ppm; 2 to 5000 ppm; 2 to 1000 ppm, 2 to 900 ppm, 2 to 800 ppm, 2 to 700 ppm.
  • the polyesters of the aromatic-aliphatic polyesters or the aliphatic polyesters of the present disclosure can also comprise at least one chain extender.
  • Suitable chain extenders include, but are not limited to, multifunctional (including, but not limited to, bifunctional) isocyanates, multifunctional epoxides, including for example, epoxylated novolacs, and phenoxy resins.
  • chain extenders may be added at the end of the polymerization process or after the polymerization process. If added after the polymerization process, chain extenders can be incorporated by compounding or by addition during conversion processes such as injection molding or extrusion.
  • the amount of chain extender used can vary depending on the specific monomer composition used and the physical properties desired but is generally about 0.1 percent by weight to about 10 percent by weight, preferably about 0.1 to about 5 percent by weight, based on the total weight of the polyester.
  • certain aromatic-aliphatic polyesters and/or aliphatic polyesters useful in this present disclosure are visually clear.
  • the term “visually clear” is defined herein as an appreciable absence of cloudiness, haziness, and/or muddiness, when inspected visually.
  • the polyesters are blended with polycarbonate, including bisphenol A polycarbonates, the blends can be visually clear in one aspect of the present disclosure.
  • the aromatic-aliphatic polyesters and/or aliphatic polyesters useful in the present disclosure may have a yellowness index (ASTM D-1925) of less than 50, such as less than 20.
  • Polycarbonates useful in the present disclosure include the polycarbonate of 4,4′-isopropylidenediphenol (bisphenol A).
  • the polycarbonate portion of the blend is prepared in the melt, in solution, or by interfacial polymerization techniques well known in the art. Such known techniques include reacting a dihydroxyaromatic compound with a carbonate precursor such as phosgene, a haloformate or a carbonate ester, a molecular weight regulator, an acid acceptor and a catalyst.
  • a carbonate precursor such as phosgene, a haloformate or a carbonate ester
  • a molecular weight regulator such as phosgene, a haloformate or a carbonate ester
  • an acid acceptor and a catalyst such as phosgene, a haloformate or a carbonate ester
  • polycarbonates useful in the present disclosure can be made by reacting bisphenol A with phosgene, dibutyl carbonate, dipheny
  • the polycarbonate useful in the blends of the present disclosure does not contain dihydroxydiphenyl cycloalkanes. In another embodiment, the polycarbonate useful in the blends of the present disclosure does not contain dihydroxydiphenyl cycloalkanes such as those used in U.S. Pat. No. 6,043,322.
  • suitable carbonate precursors include, but are not limited to, carbonyl bromide, carbonyl chloride, or mixtures thereof; diphenyl carbonate; a di(halophenyl)carbonate, e.g., di(trichlorophenyl)carbonate, di(tribromophenyl)carbonate, and the like; di(alkylphenyl)carbonate, e.g., di(tolyl)carbonate; di(naphthyl)carbonate; di(chloronaphthyl)carbonate, or mixtures thereof; and bis-haloformates of dihydric phenols.
  • suitable molecular weight regulators include, but are not limited to, phenol, cyclohexanol, methanol, alkylated phenols, such as octylphenol, para-tertiary-butyl-phenol, and the like.
  • the molecular weight regulator is phenol or an alkylated phenol.
  • the acid acceptor may be either an organic or an inorganic acid acceptor.
  • a suitable organic acid acceptor can be a tertiary amine and includes, but is not limited to, such materials as pyridine, triethylamine, dimethylaniline, tributylamine, and the like.
  • the inorganic acid acceptor can be either a hydroxide, a carbonate, a bicarbonate, or a phosphate of an alkali or alkaline earth metal.
  • the catalysts that can be used include, but are not limited to, those that typically aid the polymerization of the monomer with phosgene.
  • Suitable catalysts include, but are not limited to, tertiary amines such as triethylamine, tripropylamine, N,N-dimethylaniline, quaternary ammonium compounds such as, for example, tetraethylammonium bromide, cetyl triethyl ammonium bromide, tetra-n-heptylammonium iodide, tetra-n-propyl ammonium bromide, tetramethyl ammonium chloride, tetra-methyl ammonium hydroxide, tetra-n-butyl ammonium iodide, benzyltrimethyl ammonium chloride and quaternary phosphonium compounds such as, for example, n-butyltriphenyl phosphonium bromide and methyltriphen
  • the polycarbonates useful in the polymer blends disclosed herein may exhibit at least one of the following inherent viscosities as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.: 0.20 to 1.0 dL/g; 0.20 to 0.75 dL/g; 0.30 dL/g to 1.0 dL/g; 0.30 to 0.75 dL/g; 0.50 to 1.0 gL/g; 0.50 to 0.75 dL/g; greater than 0.30 dL/g; greater than 0.40 dL/g; or greater than 0.50 dL/g.
  • the polyesters and/or the polycarbonates useful in the compositions of the present disclosure can comprise from 0 to 10 mole percent, for example, from 0.01 to 5 mole percent, from 0.01 to 1 mole percent, from 0.05 to 5 mole percent, from 0.05 to 1 mole percent, or from 0.1 to 0.7 mole percent, based the total mole percentages of either the diol or diacid residues; respectively, of one or more residues of a branching monomer, also referred to herein as a branching agent, having 3 or more carboxyl substituents, hydroxyl substituents, or a combination thereof.
  • the branching monomer or agent may be added prior to and/or during and/or after the polymerization of the polyester.
  • the polyester(s) useful in the present disclosure can thus be linear or branched.
  • the polycarbonate can also be linear or branched.
  • the branching monomer or agent may be added prior to and/or during and/or after the polymerization of the polycarbonate
  • branching monomers include, but are not limited to, multifunctional acids or multifunctional alcohols such as trimellitic acid, trimellitic anhydride, pyromellitic dianhydride, trimethylolpropane, glycerol, pentaerythritol, citric acid, tartaric acid, 3-hydroxyglutaric acid and the like.
  • the branching monomer residues can comprise 0.1 to 0.7 mole percent of one or more residues chosen from at least one of the following: trimellitic anhydride, pyromellitic dianhydride, glycerol, sorbitol, 1,2,6-hexanetriol, pentaerythritol, trimethylolethane, and/or trimesic acid.
  • the branching monomer may be added to the polyester reaction mixture or blended with the polyester in the form of a concentrate as described, for example, in U.S. Pat. Nos. 5,654,347 and 5,696,176, whose disclosure regarding branching monomers is incorporated herein by reference.
  • polyesters and/or the polycarbonates of the polymer blends useful in the present disclosure may also contain from 0.01 to 25% by weight of the overall polymer blend composition common additives such as colorants and/or dyes (if color is desired in the final blend), mold release agents, flame retardants, plasticizers, nucleating agents, stabilizers, including but not limited to, UV stabilizers, thermal stabilizers and/or reaction products thereof, fillers, and impact modifiers.
  • common additives such as colorants and/or dyes (if color is desired in the final blend), mold release agents, flame retardants, plasticizers, nucleating agents, stabilizers, including but not limited to, UV stabilizers, thermal stabilizers and/or reaction products thereof, fillers, and impact modifiers.
  • Examples of typical commercially available impact modifiers well known in the art and useful in this present disclosure include, but are not limited to, ethylene/propylene terpolymers; functionalized polyolefins, such as those containing methyl acrylate and/or glycidyl methacrylate; styrene-based block copolymeric impact modifiers, and various acrylic core/shell type impact modifiers. Residues of such additives are also contemplated as part of the polymer blend.
  • the polymer blend compositions of the present disclosure can be made by conventional mixing methods known in the art, such as melt blending or solution blending. Suitable methods include, but are not limited to, the steps of mixing the aliphatic-aromatic polyester, the aliphatic polyester, and the polycarbonate in powder or granular form in an extruder, extruding the mixture into strands, chopping the strands into pellets, and molding the pellets into the desired article(s). See U.S. Pat. No. 3,772,405 for methods of producing polyesters, the disclosure regarding such methods is hereby incorporated herein by reference.
  • suitable molecular weight regulators include, but are not limited to, phenol, cyclohexanol, methanol, alkylated phenols, such as octylphenol, para-tertiary-butyl-phenol, and the like.
  • the molecular weight regulator is phenol or an alkylated phenol.
  • the reinforcing materials may include, but are not limited to, carbon filaments, silicates, mica, clay, talc, titanium dioxide, Wollastonite, glass flakes, glass beads and fibers, and polymeric fibers and combinations thereof.
  • the reinforcing materials are glass, such as, fibrous glass filaments, mixtures of glass and talc, glass and mica, and glass and polymeric fibers.
  • the inherent viscosity of the polyesters was determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.
  • the glass transition temperature (T g ) was determined using a Perkin Elmer DSC instrument at a scan rate of 20° C./min.
  • the composition of the neat resins was determined by proton nuclear magnetic resonance (NMR) spectroscopy. All NMR spectra were recorded on a JEOL Eclipse Plus 600 MHz nuclear magnetic resonance spectrometer using either chloroform-trifluoroacetic acid (70-30 volume/volume) for polymers or, for oligomeric samples, 60/40 (wt/wt) phenol/tetrachloroethane with deuterated chloroform added for lock. Peak assignments for 2,2,4,4-tetramethyl-1,3-cyclobutanediol resonances were made by comparison to model mono- and dibenzoate esters of 2,2,4,4-tetramethyl-1,3-cyclobutanediol. These model compounds closely approximate the resonance positions found in the polymers and oligomers. The miscibility of the compositions herein was determined by the clarity of molded bars.
  • the heat deflection temperature was determined at 264 psi according to ASTM D648. Flexural modulus and flexural strength were determined according to ASTM D790. Tensile properties were determined according to ASTM D638.
  • the polycarbonate used in all of the examples was MakrolonTM 2608 (Bayer Material Science, Inc.) with a measured inherent viscosity of 0.522 dL/g.
  • polymer blends were prepared in a 19 mm Leistritz twin screw extruder.
  • the polyesters and polycarbonate were premixed by tumble blending and fed into the extruder.
  • the extruded strand was pelletized, and the pellets were injection molded into parts on a Toyo 90 injection molding machine.
  • the extruder was run at 350 rpms at a feed rate to give a machine torque between 80-100%.
  • the aliphatic-aromatic polyester was made from terephthalic acid, 46.6 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol (54.1 mole % cis isomer), and 53.7 mole % of cyclohexanedimethanol.
  • the inherent viscosity was measured to be 0.59 dL/g.
  • the aliphatic polyester was made from 1,4-cyclohexanedimethanol and 1,4-cyclohexane dicarboxylic acid and had a measured inherent viscosity of 1.08 dL/g.
  • the aliphatic-aromatic polyester was dried at 90° C., the aliphatic polyester was dried at 70° C., and the polycarbonate was dried at 120° C. Processing temperatures used were in the range of 270-290° C.
  • the compositions and properties of the blends are shown in Table 1.
  • Samples C, D, and E demonstrate how clear blends may be obtained by the addition of greater than 3% PCCD polyester.
  • Samples A and B illustrate hazy blends as comparative examples outside the scope of the present disclosure.
  • the aliphatic-aromatic polyester was made from terephthalic acid, 95.7 mole % of 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and 4.3 mole % of ethylene glycol.
  • the inherent viscosity of the aliphatic-aromatic polyester was 0.457 dL/g.
  • the aliphatic polyester was made from 1,4-cyclohexanedimethanol (30.4 mole % cis isomer) and 1,4-cyclohexane dicarboxylic acid (7.2 mole % cis isomer), and had a measured inherent viscosity of 1.08 dL/g.
  • the aliphatic-aromatic polyester was dried at 120° C.
  • the aliphatic polyester was dried at 70° C.
  • the polycarbonate was dried at 120° C. Processing temperatures used were in the range of 290-310° C.
  • the compositions and properties of the blends are shown in Table 2.
  • Samples B and C demonstrate how clear blends may be obtained by the addition of greater than 3% PCCD polyester.
  • the hazy blend of sample A serves as a comparative example.

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US20120184687A1 (en) 2012-07-19
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US20120184641A1 (en) 2012-07-19

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