CA2576919A1 - Spheroidal polyester polymer particles - Google Patents

Spheroidal polyester polymer particles Download PDF

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Publication number
CA2576919A1
CA2576919A1 CA002576919A CA2576919A CA2576919A1 CA 2576919 A1 CA2576919 A1 CA 2576919A1 CA 002576919 A CA002576919 A CA 002576919A CA 2576919 A CA2576919 A CA 2576919A CA 2576919 A1 CA2576919 A1 CA 2576919A1
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CA
Canada
Prior art keywords
spheroids
residues
bulk
mole
polyester polymer
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Granted
Application number
CA002576919A
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French (fr)
Other versions
CA2576919C (en
Inventor
Stephen Weinhold
Frederick Leslie Colhoun
Michael Paul Ekart
Benjamin Bradford Gamble
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Grupo Petrotemex SA de CV
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Individual
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Publication of CA2576919A1 publication Critical patent/CA2576919A1/en
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Classifications

    • 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
    • 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
    • C08G63/88—Post-polymerisation treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B13/00—Conditioning or physical treatment of the material to be shaped
    • B29B13/06—Conditioning or physical treatment of the material to be shaped by drying
    • B29B13/065—Conditioning or physical treatment of the material to be shaped by drying of powder or pellets
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B7/00—Mixing; Kneading
    • B29B7/002—Methods
    • B29B7/007—Methods for continuous mixing
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B7/00—Mixing; Kneading
    • B29B7/30—Mixing; Kneading continuous, with mechanical mixing or kneading devices
    • B29B7/58—Component parts, details or accessories; Auxiliary operations
    • B29B7/72—Measuring, controlling or regulating
    • B29B7/726—Measuring properties of mixture, e.g. temperature or density
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B9/00—Making granules
    • B29B9/12—Making granules characterised by structure or composition
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B9/00—Making granules
    • B29B9/16—Auxiliary treatment of granules
    • 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
    • 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
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26—DRYING
    • F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B17/00—Machines or apparatus for drying materials in loose, plastic, or fluidised form, e.g. granules, staple fibres, with progressive movement
    • F26B17/12—Machines or apparatus for drying materials in loose, plastic, or fluidised form, e.g. granules, staple fibres, with progressive movement with movement performed solely by gravity, i.e. the material moving through a substantially vertical drying enclosure, e.g. shaft
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B9/00—Making granules
    • B29B9/16—Auxiliary treatment of granules
    • B29B2009/165—Crystallizing granules
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F26—DRYING
    • F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
    • F26B2200/00—Drying processes and machines for solid materials characterised by the specific requirements of the drying good
    • F26B2200/08—Granular materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1334—Nonself-supporting tubular film or bag [e.g., pouch, envelope, packet, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]
    • Y10T428/1355—Elemental metal containing [e.g., substrate, foil, film, coating, etc.]

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mechanical Engineering (AREA)
  • General Engineering & Computer Science (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
  • Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)

Abstract

Spheroidal polyester polymer particles, as well as preforms and stretch blow molded bottles made from the spheroidal particles, are provided which have: A) an lt.V. of at least 0.72 dL/g, and either B) at least two melting peaks (on a DSC first heating scan), wherein one of said at least two melting peaks is a low peak melting point having a peak temperature within a range of 140 ~C to 220 ~C and having a melting endotherm area of at least the absolute value of 1 J/g, or C) a low degree of crystallinity within a range of at least 20% and a maximum degree of crystallinity Tcmax defined by the equation: Tcmax = 50% -CA - OH where CA is the total mole % of all carboxylic acid residues other than terephthalic acid residues, based on 100 mole % of carboxylic acid residues in the polyester polymer, and OH is the total mole % of hydroxyl functional compound residues other than ethylene glycol residues, based on 100 mole % of the hydroxyl functional compounds residues; or both B) and C); and optionally but: preferably D) 10 ppm or less of residual acetaldehyde.

Claims (44)

1 A bulk comprising polyester polymer spheroids having:
A) an average lt.V. of at least 0.72 dL/g, and either B) melting points characterized by:
a. at least two melting peaks, wherein one of said at least two melting peaks when measured on a first DSC scan is a low peak melting point having a peak temperature within a range of 140°C to 220 °C
and having a melting endotherm area of at least the absolute value of I J/g, or b. having one or more melting points which, when measured on a DSC first heating scan, has a heating curve departing from a baseline in the endothermic direction at a temperature of less than or equal to 200°C, or C) a low degree of crystallinity within a range of at least 20% and a maximum degree of crystallinity T cmax defined by the equation:

T cmax = 50% - CA - OH
where CA is the total mole % of all carboxylic acid residues other than terephthalic acid residues, based on 100 mole% of carboxylic acid residues in the polyester polymer, and OH is the total mole % of hydroxyl functional compound residues other than ethylene glycol residues, based on 100 mole%
of the hydroxyl functional compounds residues; or both B) and C).
2. The bulk of claim 1, wherein the bulk comprises at least 75% virgin polyester polymer.
3. The bulk of claim 2, wherein the bulk has a residual acetaldehyde level of ppm or less.
4. The bulk of claim 1, wherein the spheroids have an angle of repose of less than 34.00 measured by a gate test with an actual pellet temperature of 165°C after hours.
5. The bulk of claim 4, wherein the angle of repose is less than 32°.
6. The bulk of claim 5, wherein the angle of repose is less 31° or less.
7. The bulk of claim 1, wherein the spheroids have a roundness distribution, and the mode of the distribution is less than 1.4.
8. The bulk of claim 5, wherein the mode of the roundness distribution is 1.2 or less.
9. The bulk of claim 1, wherein the spheroids are characterized by both B) and C).
10. The bulk of claim 1, wherein the polyester polymer spheroids comprise:
(a) a carboxylic acid component comprising at least 80 mole% of the residues of terephthalic acid or derivatives of terephthalic acid, or mixtures thereof, and (b) a hydroxyl component comprising at least 80 mole% of the residues of ethylene glycol, based on 100 mole percent of carboxylic acid component residues and 100 mole percent of hydroxyl component residues in the polyester polymer.
11. The bulk of claim 10, wherein the polyester polymer spheroids comprise:
(a) a carboxylic acid component comprising at least 90 mole% of the residues of terephthalic acid and/or derivatives of terephthalic acid, and (b) a hydroxyl component comprising at least 90 mole% of the residues of ethylene glycol, based on 100 mole percent of the carboxylic acid component residues and 100 mole percent of the hydroxyl component residues in the polyester polymer.
12. The bulk of claim 1, wherein the spheroids have a low peak melting point within a range of 160°C to 210°C, a degree of crystallinity ranging from 25% to 45%, the number average weight of the spheroids is at least 1.0 grams per 100 particles and does not exceed 100 grams per 100 particles, and the residual acetaldehyde content is 7 ppm or less.
13. The bulk of claim 12, wherein the spheroids have an It.V. ranging from 0.75 dL/g up to about 1.1 dL/g, and contain 2 ppm or less of residual acetaldehyde.
14. The bulk of claim 1, wherein the spheroids have a low peak melting point shoulder.
15. The bulk of claim 1, wherein the It.V. of the spheroids ranges from 0.78 dL/g to 1.1 dL/g.
16. The bulk of claim 1, wherein the It.V. of the spheroids ranges from 0.81 dL/g to 1.2 dL/g.
17. The bulk of claim 1, wherein the spheroids are contained in a shipping container, and the spheroids are not solid state polymerized.
18. The bulk of claim 1, wherein the spheroids are obtained by underwater cutting the polyester polymer.
19. The bulk of claim 1, wherein the spheroids have a degree of crystallinity obtained by thermal crystallization of the spheroids in a liquid medium comprising water at a temperature above the T g of the polyester polymer.
20. A method for drying and melt processing polyester polymer spheroids comprising:
A) drying polyester polymer spheroids in a drying zone to produce dried spheroids;
B) introducing the dried spheroids into a melting processing zone;
C) melting the polyester polymer spheroids in the melt processing zone, and D) forming an article from the molten polymer;
wherein the polyester polymer spheroids introduced into the drying zone are not solid state polymerized.
21. The method of claim 20, wherein the residual acetaldehyde level of the spheroids introduced into the drying zone is 10 ppm or less.
22. The method of claim 20, wherein the spheroids have degree of crystallinity ranging from 25% to 45%.
23. The method of claim 20, wherein the spheroids have one or more melting point characterized by:

a. at least two melting peaks, wherein one of said at least two melting peaks when measured on a DSC first heating scan is a low peak melting point having a peak temperature within a range of 140°C to 220 °C and having a melting endotherm area of at least the absolute value of 1 J/g, or b. having one or more melting points which, when measured on a DSC first heating scan, has a heating curve departing from a baseline in the endothermic direction at a temperature of less than or equal to 200°C.
24. The method of claim 20, wherein the spheroids introduced into the drying zone have:
A) an average lt.V. of at least 0.72 dL/g, and either B) melting points characterized by:
(i) at least two melting peaks, wherein one of said at least two melting peaks when measured on a DSC first heating scan is a low peak melting point having a peak temperature within a range of 140°C to 220 °C and having a melting endotherm area of at least the absolute value of I J/g, or (ii) having one or more melting points which, when measured on a DSC first heating scan, has a heating curve departing from a baseline in the endothermic direction at a temperature of less than or equal to 200°C, or C) a low degree of crystallinity within a range of at least 20% and a maximum degree of crystallinity T cmax defined by the equation:

T cmax = 50% - CA - OH
where CA is the total mole % of all carboxylic acid residues other than terephthalic acid residues, based on 100 mole% of carboxylic acid residues in the polyester polymer, and OH is the total mole % of hydroxyl functional compound residues other than ethylene glycol residues, based on 100 mole%
of the hydroxyl functional compounds residues; and D) a residual acetaldehyde level of 10 ppm or less.
25. The method of claim 20, wherein the spheroids introduced into the drying zone comprise at least 75% virgin polyester polymer.
26. The method of claim 20, wherein the spheroids introduced into the drying zone comprise have an angle of repose of less than 34.00 measured by a gate test with an actual pellet temperature of 165°C after 5 hours.
27. The method of claim 26, wherein the angle of repose is less than 32°.
28. The method of claim 20, wherein the spheroids introduced into the drying zone have a roundness distribution, and the mode of the distribution is less than 1.4.
29. The method of claim 20, wherein the mode is 1.2 or less.
30. The method of claim 20, wherein the spheroids introduced into the drying zone comprise:
(a) a carboxylic acid component comprising at least 80 mole% of the residues of terephthalic acid or derivatives of terephthalic acid, or mixtures thereof, and (b) a hydroxyl component comprising at least 80 mole% of the residues of ethylene glycol, based on 100 mole percent of carboxylic acid component residues and 100 mole percent of hydroxyl component residues in the polyester polymer.
31. The method of claim 20, wherein the spheroids introduced into the drying zone comprise:
(a) a carboxylic acid component comprising at least 90 mole% of the residues of terephthalic acid and/or derivatives of terephthalic acid, and (b) a hydroxyl component comprising at least 90 mole% of the residues of ethylene glycol, based on 100 mole percent of the carboxylic acid component residues and 100 mole percent of the hydroxyl component residues in the polyester polymer.
32. The method of claim 20, wherein the spheroids introduced into the drying zone have a low peak melting point within a range of 160°C to 210°C, a degree of crystallinity ranging from 25% to 45%, the number average weight of the spheroids is at least 1.0 grams per 100 particles and does not exceed 100 grams per 100 particles, and the residual acetaldehyde content is 7 ppm or less.
33. The method of claim 20, wherein the spheroids introduced into the drying zone have an lt.V. within the range of 0.78 dL/g to 1.1 dL/g.
34. The method of claim 20, wherein the spheroids introduced into the drying zone are obtained by underwater cutting the polyester polymer.
35. The method of claim 20, wherein the spheroids have a degree of crystallinity obtained by thermal crystallization of the spheroids in a liquid medium comprising water at a temperature above the T g of the polyester polymer.
36. A preform obtained by the method of claim 20.
37. A stretch blow molded bottle obtained by the method of claim 20.
38. A perform obtained by the method of claim 24.
39. A stretch blow molded bottle obtained by the method of claim 24.
40. A perform obtained from the bulk of claim 1.
41. A stretch blow molded bottle obtained from the bulk of claim 1.
42. The method of claim 20, wherein the article is a sheet.
43. The method of claim 24, wherein the article is a sheet.
44. A sheet obtained from the bulk of claim 1.
CA2576919A 2004-09-02 2005-08-29 Spheroidal polyester polymer particles Active CA2576919C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US60672704P 2004-09-02 2004-09-02
US60/606,727 2004-09-02
US61895104P 2004-10-15 2004-10-15
US60/618,951 2004-10-15
US11/018,357 2004-12-21
US11/018,357 US20060047102A1 (en) 2004-09-02 2004-12-21 Spheroidal polyester polymer particles
PCT/US2005/030535 WO2006028749A2 (en) 2004-09-02 2005-08-29 Spheroidal polyester polymer particles

Publications (2)

Publication Number Publication Date
CA2576919A1 true CA2576919A1 (en) 2006-03-16
CA2576919C CA2576919C (en) 2012-03-20

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CA2576919A Active CA2576919C (en) 2004-09-02 2005-08-29 Spheroidal polyester polymer particles

Country Status (15)

Country Link
US (2) US20060047102A1 (en)
EP (2) EP2289969B1 (en)
JP (6) JP2008511732A (en)
KR (2) KR101198712B1 (en)
CN (3) CN101023114B (en)
AR (2) AR050854A1 (en)
BR (1) BRPI0514775B1 (en)
CA (1) CA2576919C (en)
ES (1) ES2460740T3 (en)
MX (1) MX2007002405A (en)
MY (1) MY150897A (en)
PL (1) PL1784439T3 (en)
PT (1) PT1784439E (en)
TW (1) TWI313276B (en)
WO (1) WO2006028749A2 (en)

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