CA2588307A1 - Polyester based cobalt concentrates for oxygen scavenging compositions - Google Patents

Polyester based cobalt concentrates for oxygen scavenging compositions Download PDF

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Publication number
CA2588307A1
CA2588307A1 CA002588307A CA2588307A CA2588307A1 CA 2588307 A1 CA2588307 A1 CA 2588307A1 CA 002588307 A CA002588307 A CA 002588307A CA 2588307 A CA2588307 A CA 2588307A CA 2588307 A1 CA2588307 A1 CA 2588307A1
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CA
Canada
Prior art keywords
concentrate
mole
residues
polyester polymer
hydroxyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002588307A
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French (fr)
Other versions
CA2588307C (en
Inventor
Mark Edward Stewart
Emerson Eston Sharpe, Jr.
Benjamin Bradford Gamble
Steven Lee Stafford
Robert Noah Estep
James Carl Williams
Thomas Roger Clark
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Chemical Co
Original Assignee
Eastman Chemical Company
Mark Edward Stewart
Emerson Eston Sharpe, Jr.
Benjamin Bradford Gamble
Steven Lee Stafford
Robert Noah Estep
James Carl Williams
Thomas Roger Clark
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Application filed by Eastman Chemical Company, Mark Edward Stewart, Emerson Eston Sharpe, Jr., Benjamin Bradford Gamble, Steven Lee Stafford, Robert Noah Estep, James Carl Williams, Thomas Roger Clark filed Critical Eastman Chemical Company
Publication of CA2588307A1 publication Critical patent/CA2588307A1/en
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Publication of CA2588307C publication Critical patent/CA2588307C/en
Expired - Fee Related legal-status Critical Current
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Classifications

    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/04—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polycarbonamides, polyesteramides or polyimides
    • 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
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, 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
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/48—Polymers modified by chemical after-treatment
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • 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]
    • 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]
    • Y10T428/1379—Contains vapor or gas barrier, polymer derived from vinyl chloride or vinylidene chloride, or polymer containing a vinyl alcohol unit
    • Y10T428/1383—Vapor or gas barrier, polymer derived from vinyl chloride or vinylidene chloride, or polymer containing a vinyl alcohol unit is sandwiched between layers [continuous layer]

Abstract

A solid concentrate is provided having a combination of a transition metal present in an amount ranging from 1,000 to 40,000 ppm (weight by metal) and a polyester polymer present in an amount of at least 40 wt. % based on the weight of the concentrate. Concentrates made with highly modified polyester polymers are easy to compound with transition metals forming less brittle polymer upon melt extrusion. Bottle preforms and oxygen scavenging bottles can be made from these concentrates by combining solid polyester particles, solid polyamide particles, and solid these concentrate particles c into an melt processing zone, forming a melt, and forming an article directly from the melt. The b* color and the L* color and the haze levels of the preforms are improved over the preforms made with liquid carriers instead of solid concentrates. The particles are also advantageously simultaneously dried in a drying zone under conditions effective to at least partially remove moisture from the blend to thereby further improve the b* color and L* color.

Claims (59)

1. A solid concentrate obtained by melt compounding a transition metal compound in an amount ranging from 1000 ppm to 40,000 ppm (by metal) and a polyester polymer having an It.V. of at least 0.55 dL/g in an amount of at least 40 wt.%, each based on the weight of the concentrate.
2. The concentrate of claim 1, wherein the polyester polymer is present in an amount of at least 98 wt.%, based on the weight of all polymers in the concentrate.
3. The concentrate of claim2, wherein the concentrate is essentially free of polymers other than a polyester polymer.
4. The concentrate of claim 1, wherein the concentrate consists essentially of a polyester polymer and residues of cobalt compounds.
5. The concentrate of claim 2, wherein the transition metal comprises cobalt.
6. The concentrate of claim 5 wherein cobalt is present in the concentrate in an amount of at least 2000 ppm.
7. The concentrate of claim 6, wherein cobalt is present in the concentrate in an amount of at least 2000 ppm..
8. The concentrate of claim 7, wherein cobalt is present in the concentrate in an amount of at least 3000 ppm and up to 20,000 ppm.
9. The concentrate of claim 7, wherein cobalt is present in the concentrate in an amount ranging from 3,000 ppm to 10,000 ppm.
10. The concentrate of claim 5, wherein the source of cobalt comprises a cobalt carboxylate or cobalt neodecanoate.
11. The concentrate of claim 1, wherein the polyester polymer comprises polyethylene terephthalate, polytrimethylene terephthalate, polyethylene naphthalate, or poly(dimethyl cyclohexane terephthalate), optionally modified with up to 40 mole% of one or more modifier(s).
12. The concentrate of claim 1, wherein the polyester polymer comprises at least:
(i) a carboxylic acid component comprising at least 92.0 mole%
residues of terephthalic acid, or derivates of terephthalic acid, or mixtures thereof, and (ii) a hydroxyl component comprising at least 40 mole% residues of ethylene glycol, based on 100 mole percent of the carboxylic acid component residues and 100 mole percent hydroxyl component residues in the polyester polymer, respectively.
13. The concentrate of claim 1, wherein the hydroxyl component further comprises residues of a hydroxyl modifier in an amount of at least 20 mole% and up to 60 mole% based on 100 mole% of the:hydroxyl component residues..
14. The concentrate of claim 1, wherein the It.V. of the polyester polymer obtained in the melt phase polymerization process is at least 0.72 dL/g and the transition metal comprises cobalt.
15. The concentrate of claim 1, wherein the It.V. of the polyester polymer obtained in the melt phase polymerization process is at least 0.76 dL/g and the transition metal comprised cobalt.
16. The concentrate of claim 1, wherein the polyester polymer used to prepare the concentrate is not polymerized in the solid state and the transition metal comprises cobalt.
17. The concentrate of claim 1, wherein the metal comprises cobalt, and the cobalt is present in an amount ranging from 1500 ppm to 20000 ppm; the polyester polymer comprises:

(i) a carboxylic acid component comprising at least 92.0 mole%
residues of terephthalic acid, or derivates of terephthalic acid, or mixtures thereof, and (ii) a hydroxyl component comprising at least 40.0 mole%
residues of ethylene glycol, based on 100 mole percent of the carboxylic acid component residues and 100 mole percent hydroxyl component residues in the polyester polymer, respectively, and the concentrate is free of a polyamide polymer.
18. The concentrate of claim 13, wherein the transition metal comprises cobalt, and at least a portion of the cobalt is present in the concentrate in the +2 oxidation state.
19. The concentrate of claim 17, wherein the modifier comprises a, hydroxyl modifier, said hydroxyl modifier comprising butanediol, 1,4-cyclohexane dimethanol, 2,4- dihydroxy-1,1,3,3-tetramethyl-cyclobutane, trimethylene glycol, neopentyl glycol, or diethylene glycol or combinations thereof, wherein the cumulative amount of hydroxyl modifiers ranges from 25 mole% to 60 mole%, based on all moles of the hydroxyl component
20. A process for the manufacture of a preform comprising combining:
solid polyester particles comprising a polyester polymer, solid polyamide particles comprising polyamide polymers, and solid concentrate particles obtained by melt compounding a transition metal compound in an amount ranging from 1000 ppm to 40,000 ppm (by metal) and a polyester polymer having an It.V. of at least 0.55 dL/g in an amount of at least 40 wt.%, each based on the weight of the concentrate into a melt processing zone, forming a melt, and forming an article directly from the melt.
21. The process of claim 20, wherein the article comprises a bottle preform.
22. The process of claim 20, wherein the polyester polymer comprises:
(i) a carboxylic acid component comprising at least 92.0 mole%
residues of terephthalic acid, or derivates of terephthalic acid, or mixtures thereof, and (ii) a hydroxyl component comprising at least 40.0 mole%
residues of ethylene glycol, based on 100 mole percent of the carboxylic acid component residues and 100 mole percent hydroxyl component residues in the polyester polymer, respectively.
23. The process of claim 20, wherein the transition metal comprises cobalt present in an amount ranging from 1500 to 20,000 ppm based on the weight of the concentrate.
24. The process of claim 20, wherein the amount of polyester polymer present in the concentrate is at least 98 wt.%, based on the weight of the polymers in the concentrate.
25. The process of claim 20, wherein the concentrate is free of polymers other than the polyester polymer.
26. The process of claim 20, wherein the source of cobalt comprises a cobalt carboxylate or cobalt neodecanoate.
27. The process of claim 20, wherein the It.V. of the polyester polymers in both the polyester polymer particles and added to prepare the concentrate are at least 0.70 dL/g.
28. The process of claim 20, wherein the It.V. of the polyester polymers in the polyester polymer particles is at least 0.70 dL/g obtained in a melt phase polymerization process.
29. The process of claim 28, wherein said It.V. is at least 0.76 dL/g.
30. The process of claim 20, wherein the It.V. of the solid polyester polymer particles as the It.V. of the polyester polymers used to prepare the concentrate are each at least 0.70 dL/g obtained in a melt phase polymerization process.
31. The process of claim 20, wherein neither the solid polyester polymer particles nor the polyester polymers used to prepare the concentrate are solid state polymerized.
32. The process of claim 20, wherein at least a portion of the polyester polymer in the polyester polymer particles is different from at least a portion of the polyester polymers present in the concentrate.
33. The process of claim 20, wherein the article comprises a bottle preform having a composition comprising from 1 to 5 wt.% of an oxidizable polymer, 30 to 300 ppm cobalt, and polyester polymers present in an amount of at least 90 wt.%, each based on the weight of the preform.
34. The process of claim 20, wherein the oxidizable polymer comprises a polyamide polymer having repeating units with a benzylic hydrogen atom.
35. The process of claim 34, wherein the polyamide polymer is obtained from a reactant containing a xylylene moiety.
36. The process of claim 20, wherein the polyester polymer particles, the concentrate particles, and the polyamide polymer particles are combined into the melt processing zone as individual streams or as particle/particle dry blends.
37. The process of claim 20, wherein the polyester polymer contained in the concentrate comprises:

(i) a carboxylic acid component comprising at least 80.0 mole%
residues of terephthalic acid, or derivates of terephthalic acid, or mixtures thereof, and (ii) a hydroxyl component comprising at least 40.0 mole% residues of ethylene glycol and from 25 mole% to 60 mole% of a hydroxyl modifier compound, based on 100 mole percent of the carboxylic acid component residues and 100 mole percent hydroxyl component residues in the polyester polymer, respectively.
38. The process of claim 20, wherein the preform further comprises zinc.
39. The process of claim 20, wherein the concentrate contains a higher concentration of the metal than present in the article.
40. The process of claim 20, wherein the let down ratio of the metal concentration in the concentrate to the metal concentration in the article composition ranges from 30:1 to 100:1.
41. The concentrate of claim 20, wherein the polyester polymer contained in the concentrate is modified with a hydroxyl modifier in an amount of at least 30 mole% based on all moles of hydroxyl components.
42. A process for drying particles, comprising simultaneously drying in a drying zone a blend comprising solid polyester particles comprising polyester polymers, solid polyamide particles comprising polyamide polymers, and solid concentrate particles comprising a polyester polymer and a transition metal present in an amount ranging from 1000 ppm to 40,000 ppm, under conditions effective to at least partially remove moisture from the blend.
43. The process of claim 42, wherein the moisture level of the particle blend is 0.015 wt..% or less.
44. The process of claim 42, wherein the transition metal comprises cobalt in an amount ranging from 2000 to 20,000 ppm based on the weight of the concentrate.
45. The process of claim 44, wherein the (i) a polycarboxylic acid component comprises at least 85 mole%
residues of terephthalic acid, derivates of terephthalic acid, naphthalene-2,6-dicarboxylic acid, derivatives of naphthalene-2,6-dicarboxylic acid, or mixtures thereof, and (ii) a hydroxyl component comprising at least 85 mole% residues of C2 - C4 aliphatic saturated diols, based on 100 mole percent of the polycarboxylic acid residues and 100 mole percent hydroxyl residues in the polyester polymer.
46. A polyester polymer concentrate comprising a transition metal in an amount of at least 1000 ppm, and polyester polymers in an amount of least 40 wt.%, each based on the weight of the concentrate, wherein at least a portion of the polyester polymers comprise highly modified polyester polymers containing hydroxyl modifier residues in an amount ranging from 20 mole% to 60 mole%, based on the all the moles of hydroxyl compound residues present in the polyester polymer and/or polycarboxylic acid modifiers in an amount ranging from 20 mole% to 60 mole%, based on all the moles of polycarboxylic acid residues present in the polyester polymer.
47. The concentrate of claim 46, wherein the transition metal content ranges from 2,000 ppm to 20,000 ppm.
48. The concentrate of claim 46, wherein the amount of highly modified polyester polymers is at least 75 wt.% based on the total weight of all polyester polymers present in the concentrate.
49. The concentrate of claim 46, wherein said highly modified polyester polymers are obtained by copolymerizing polycarboxylic compounds with a hydroxyl compound and a hydroxyl modifier, such that the polymer contains hydroxyl modifier residues in an amount of at least 25 mole%, based on the moles of hydroxyl compound residues present in the polymer.
50. The concentrate of claim 49, wherein the amount of hydroxyl modifier residues ranges from 30 mole% to 60 mole%, based on all hydroxyl residues present in the polymer.
51. The concentrate of claim 49, wherein the transition metal is present in an amount ranging from 2000 to 20,000.
52. The concentrate of claim 51, wherein the transition metal comprises cobalt present in an amount ranging from 3000 to 20,000.
53. The concentrate of claim 46, wherein the transition metal is added into a melt phase process for making the polyester polymer.
54. The concentrate of claim 46, wherein the concentrate is obtained by melt compounding a polyester polymer with the transition metal.
55. The concentrate of claim 46, wherein the highly modified polyester polymer comprises:
(i) a polycarboxylic acid component comprising at least 92 mole%
residues of terephthalic acid or derivates of terephthalic acid or mixtures thereof, and (ii) a hydroxyl component comprising at least 40 mole% residues of ethylene glycol and at least 25 mole% and up to 60 mole% residues of a hydroxyl modifier based on 100 mole percent of the polycarboxylic acid residues and 100 mole percent hydroxyl residues in the polyester polymer
56. The concentrate of claim 46, wherein the It.V. of the highly modified polyester polymer is at least 0.72 dL/g obtained without solid state polymerization.
57. The concentrate of claim 56, wherein the It.V. of the highly modified polyester polymer is at least 0.80 dL/g.
58. The concentrate of claim 46, wherein the hydroxyl modifier residue comprises a residue of butanediol, 1,4-cyclohexane dimethanol, 2,4- dihydroxy-1,1,3,3-tetramethyl-cyclobutane, trimethylene glycol, neopentyl glycol, or diethylene glycol or combinations thereof.
59. The concentrate of claim 58, wherein the hydroxyl modifier residue comprises a residue of 1,4-cyclohexane dimethanol.
CA2588307A 2004-12-06 2005-12-02 Polyester based cobalt concentrates for oxygen scavenging compositions Expired - Fee Related CA2588307C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US63352404P 2004-12-06 2004-12-06
US60/633,524 2004-12-06
PCT/US2005/043609 WO2006062816A2 (en) 2004-12-06 2005-12-02 Polyester based cobalt concentrates for oxygen scavenging compositions
US11/292,441 2005-12-02
US11/292,441 US7288586B2 (en) 2004-12-06 2005-12-02 Polyester based cobalt concentrates for oxygen scavenging compositions

Publications (2)

Publication Number Publication Date
CA2588307A1 true CA2588307A1 (en) 2006-06-15
CA2588307C CA2588307C (en) 2010-10-12

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CA2588307A Expired - Fee Related CA2588307C (en) 2004-12-06 2005-12-02 Polyester based cobalt concentrates for oxygen scavenging compositions

Country Status (13)

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US (3) US7288586B2 (en)
EP (1) EP1824920B9 (en)
JP (1) JP2008523170A (en)
KR (1) KR20070085810A (en)
CN (1) CN101072820B (en)
AT (1) ATE443102T1 (en)
BR (1) BRPI0518849A2 (en)
CA (1) CA2588307C (en)
DE (1) DE602005016714D1 (en)
ES (1) ES2331145T3 (en)
MX (1) MX2007006662A (en)
PL (1) PL1824920T3 (en)
WO (1) WO2006062816A2 (en)

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