CA2487437A1 - Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials - Google Patents

Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials Download PDF

Info

Publication number
CA2487437A1
CA2487437A1 CA 2487437 CA2487437A CA2487437A1 CA 2487437 A1 CA2487437 A1 CA 2487437A1 CA 2487437 CA2487437 CA 2487437 CA 2487437 A CA2487437 A CA 2487437A CA 2487437 A1 CA2487437 A1 CA 2487437A1
Authority
CA
Canada
Prior art keywords
cyclodextrin
weight
chip
polyester
parts
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
CA 2487437
Other languages
French (fr)
Other versions
CA2487437C (en
Inventor
Willard E. Wood
Neil J. Beaverson
Philip A. Lawonn
Xiaoyan Huang
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.)
Verdant Technologies LLC
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2487437A1 publication Critical patent/CA2487437A1/en
Application granted granted Critical
Publication of CA2487437C publication Critical patent/CA2487437C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/203—Solid polymers with solid and/or liquid additives
    • 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
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/22—Compounding polymers with additives, e.g. colouring using masterbatch techniques
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • C08L5/16—Cyclodextrin; Derivatives thereof
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
    • C09D105/16—Cyclodextrin; Derivatives thereof
    • 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
    • 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]
    • Y10T428/1397—Single layer [continuous layer]
    • 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
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • 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
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, 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
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • 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
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2998—Coated including synthetic resin or polymer
    • 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
    • Y10T428/31—Surface property or characteristic of web, sheet or block
    • 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, 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
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • Y10T428/31797—Next to addition polymer from unsaturated monomers

Abstract

Volatile organic compound or other materials are produced in the thermoplastic manufacture of thermoplastic polyester beverage containers. Such materials can be eluted into beverages such as carbonated beverages, sparkling or still water from the polyester. Such thermoplastic polyester resins can be manufactured with a material that can prevent the formation of, or react with, and absorb volatile by-products during the formation of thermoplastic preforms or containers from the thermoplastic pellet or chip. Further, as the preform is blown into a polyester container, the active materials of the invention prevent the generation of additional undesirable volatile materials. Lastly, the scavenger material can act as a barrier that prevents transport of materials from the exterior of the container into the container contents.

Claims (8)

1. A polyester chip comprising a coating formed substantially on the exterior of the chip comprising a substituted cyclodextrin compound, the chip comprising about 100 parts by weight to 1400 parts by weight of the substituted cyclodextrin compound per each one million parts of polyester resin, the cyclodextrin having a degree of substitution of about 0.3 to 1.8; wherein the substituted cyclodextrin is substantially free of a compound in the central pore of the cyclodextrin ring and the cyclodextrin is present in an effective amount to complex catalyst residue.
2. The chip of claim 1 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.
3. The chip of claim 1 wherein the polyester comprises at least 60 % by weight polyethylene naphthalate units and up to 40 % by weight other polymers.
4. The chip of claim 1 wherein the polyester comprises a copolymer of polyethylene terephthalate/isophthalate and the cyclodextrin is a non-reducing carbohydrate.
5. The chip of claim 1 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group at the -6 position of the glucose moiety in the cyclodextrin
6. The chip of claim 5 wherein the cyclodextrin compound comprises a 6-O-Methyl ether.
7. The chip of claim S wherein the cyclodextrin compound comprises a 6-O Acetyl ester.
8. The chip of claim 1 wherein the substituted cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 and is present in an amount of WE CLAIM:

1. A polyester chip comprising a coating formed substantially on the exterior of the chip comprising a substituted cyclodextrin compound, the chip comprising about 100 parts by weight to 1400 parts by weight of the substituted cyclodextrin compound per each one million parts of polyester resin, the cyclodextrin having a degree of substitution of about 0.3 to 1.8; wherein the substituted cyclodextrin is substantially free of a compound in the central pore of the cyclodextrin ring and the cyclodextrin is present in an effective amount to complex catalyst residue.

2. The chip of claim 1 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.

3. The chip of claim 1 wherein the polyester comprises at least 60 % by weight polyethylene naphthalate units and up to 40 % by weight other polymers.

4. The chip of claim 1 wherein the polyester comprises a copolymer of polyethylene terephthalate/isophthalate and the cyclodextrin is a non-reducing carbohydrate.

5. The chip of claim 1 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group at the -6 position of the glucose moiety in the cyclodextrin 6. The chip of claim 5 wherein the cyclodextrin compound comprises a 6-O-Methyl ether.

7. The chip of claim S wherein the cyclodextrin compound comprises a 6-O Acetyl ester.

8. The chip of claim 1 wherein the substituted cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 and is present in an amount of parts by weight to about 900 parts by weight of the cyclodextrin compound per each one million parts of polyester resin.

17. A thermoplastic polyester beverage container comprising a thermoplastic polyester and a substituted cyclodextrin compound, the container comprising about 100 parts by weight to 1400 parts by weight of the substituted cyclodextrin compound per each one million parts of polyester resin, the substituted cyclodextrin having a degree of substitution of about 0.5 to 1.8; wherein the cyclodextrin is substantially free of any compound in the central pore of the cyclodextrin ring and the cyclodextrin is present in an effective amount to complex catalyst residue.

18. The container of claim 17 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.

19. The container of claim 17 wherein the polyester comprises at least 60 % by weight polyethylene naphthalate units and up to 40 % by weight other polymers.

20. The chip of claim 17 wherein the polyester comprises a copolymer of polyethylene terephthalate/isophthalate and the cyclodextrin is a non-reducing carbohydrate.

21. The container of claim 17 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group on the -6 position of the glucose moiety in the cyclodextrin 22. The container of claim 21 wherein the cyclodextrin compound comprises a 6-O-Methyl.

23. The container of claim 21 wherein the cyclodextrin compound comprises a 6-O Acetyl ester.

24. The container of claim 17 wherein the cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 in an amount of about parts by weight to about 900 parts by weight of the cyclodextrin compound per each one million parts of polyester resin.

25. A method of malting a shaped polyester member comprising the steps of:
(a) forming a coating of a cyclodextrin material on the surface of a polyester pellet or chip in an amount of about 100 parts by weight to 1400 parts by weight of a substituted cyclodextrin per each one million parts of polyester to form a coated chip, the substituted cyclodextrin having a degree of substitution of about 0.3 to 1.8; wherein the substituted cyclodextrin is substantially free of any compound in the central pore of the cyclodextrin ring and the cyclodextrin is present in an effective amount to complex catalyst residue; and (b) melt extruding the coated chip in an extruder to form a polymer melt into a shaped polymer.

26. The method of claim 25 wherein the shaped polymer member comprises a parison, preform or container.

27. The method of claim 25 wherein the shaped polymer member comprises a polymer preform and further comprises the steps of inflating the polymer preform at an appropriate temperature and pressure to form a thermoplastic beverage container.

28. The method of claim 25 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.

29. The method of claim 25 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.

30. The chip of claim 25 wherein the polyester comprises at least 60 %
by weight polyethylene naphthalate units and up to 40 % by weight other polymers.

31. The chip of claim 25 wherein the polyester comprises a copolymer of polyethylene terephthalate/isophthalate and the cyclodextrin is a non-reducing carbohydrate.

32. The chip of claim 25 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group on the -6 position of the glucose moiety in the cyclodextrin 33. The chip of claim 32 wherein the cyclodextrin compound comprises a 6-O-Methyl ether.

34. The chip of claim 32 wherein the cyclodextrin compound comprises a 6-O Acetyl ester.

35. The chip of claim 25 wherein the cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 in an amount of about 350 parts by weight to about 900 parts by weight of the cyclodextrin compound per each one million parts of polyester resin.

36. A method of malting a polyester chip comprising the steps of:
(a) forming an aqueous solution of a substituted cyclodextrin compound, the solution comprising about 1.0 to 50 weight percent of the substituted cyclodextrin compound;
(b) contacting the aqueous solution with an activated carbon absorbent, an ion exchange resin, a reverse osmosis membrane or a nanofiltration membrane to reduce the concentration of impurities in the aqueous solution to form a purified aqueous solution;
(c) contacting a polyester chip with the purified aqueous solution to form a coating of a cyclodextrin material on the surface of a polyester chip in an amount of about 100 parts by weight to 1400 parts by weight of the cyclodextrin compound, per each one million parts by weight of the polymer chip to form a coated chip; and, (d) drying the coated chip.

37. The method of claim 36 wherein the coating is formed from a solution comprising about 3.0 to 40 wt.-% cyclodextrin in an aqueous medium.

38. The method of claim 36 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.

39. The method of claim 36 wherein the polyester comprises at least 60 % by weight polyethylene naphthalate units and up to 40 % by weight other polymers.

40. The chip of claim 36 wherein the polyester comprises a copolymer of polyethylene terephthalate/isophthalate and the cyclodextrin is a non-reducing carbohydrate.

41. The method of claim 36 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group on the -6 position of the glucose moiety in the cyclodextrin 42. The method of claim 41 wherein the cyclodextrin compound comprises a 6-O-Methyl ether.

43. The method of claim 41 wherein the cyclodextrin compound comprises a 6-O Acetyl ester.

44. The method of claim 41 wherein the cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 in an amount of about parts by weight to about 900 parts by weight of the cyclodextrin compound per each one million parts of polyester resin.

45. A method of malting a polyester beverage container comprising the steps of:
(a) forming an aqueous solution of a substituted cyclodextrin compound, the solution comprising about 1.0 to 50 weight percent of the substituted second action compound;
(b) contacting the aqueous solution with an activated carbon absorbent, an ion exchange resin or a reverse osmosis membrane, to reduce the concentration of impurities in the aqueous solution to form a purified aqueous solution;
(c) contacting a polyester chip with the purified aqueous solution to form a coating of a cyclodextrin material on the surface of the polyester chip in an amount of about 100 parts by weight to 1400 parts by weight of the cyclodextrin compound, per each one million parts by weight of the polymer chip to form a coated chip;
(d) drying the chip to form a coated chip; and (e) melt extruding the coated chip in an extruder to form a shaped beverage container.

46. The method of claim 45 wherein the shaped polymer comprises a polyester container having a volume of about 250mL to 5 Liters.

47. The method of claim 45 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.

48. The method of claim 45 wherein the polyester comprises at least 60 % by weight polyethylene naphthalate units and up to 40 % by weight other polymers.

49. The chip of claim 45 wherein the polyester comprises a copolymer of polyethylene terephthalate/isophthalate and the cyclodextrin is a non-reducing carbohydrate.

50. The method of claim 47 wherein a preform is melt formed prior to forming a shaped container.

51. The method of claim 45 wherein the polyester comprises see claim 2.

52. The method of claim 45 wherein the polyester comprises see claim 3, 3a.

53. The method of claim 45 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group on the -6 position of the glucose moiety in the cyclodextrin.

54. The method of claim 53 wherein the cyclodextrin compound comprises a 6-O-Methyl ether.

55. The method of claim 53 wherein the cyclodextrin compound comprises a 6-O Acetyl ester.

56. The method of claim 45 wherein the cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 in an amount of about parts by weight to about 900 parts by weight of the cyclodextrin compound per each one million parts of polyester resin.

57. A method of malting a polyester chip comprising the steps of:
(a) passing a stream comprising a molten polyester through a process device comprising an exit orifice;
(b) forming an liquid comprising a substituted cyclodextrin compound;
(b) introducing the liquid comprising the substituted cyclodextrin into the stream of molten polyester proximate to a mixing means in the process device to form a treated stream; and (d) passing the treated stream through the orifice forming the polyester chip.

58. The method of claim 57 wherein the liquid comprising about 1.0 to 50 weight percent of the substituted cyclodextrin compound 59. The method of claim 57 wherein the liquid comprises molten polyethylene terephthalate and the mixing means is proximate to the orifice.
60. The method of claim 57 wherein mixing means is next adjacent to the orifice.
61. The method of claim 57 wherein the liquid comprises an oil.
62. The method of claim 57 wherein the polyester comprises at least 60 % by weight polyethylene terephthalate units and up to 40 % by weight other polymers.
63. The method of claim 57 wherein the polyester comprises at least 60 % by weight polyethylene naphthalate units and up to 40 % by weight other polymers.
64. The method of claim 57 wherein the cyclodextrin compound has a substituent substantially on at least one -OH group on the -6 position of the glucose moiety in the cyclodextrin 65. The method of claim 57 wherein the cyclodextrin compound comprises a 6-O-Methyl ether.
66. The method of claim 57 wherein the cyclodextrin compound comprises a 6-O Acetyl ester.
67. The method of claim 57 wherein the cyclodextrin compound comprises a degree of substitution of about 0.5 to 1.2 in an amount of about parts by weight to about 900 parts by weight of the cyclodextrin compound per each one million parts of polyester resin.

68. The method of claim 59 wherein the liquid is formed by introducing a powdered cyclodextrin compound into a molten polyester stream in an extruder device.
69. The method of claim 57 wherein the chip is subjected to SSP
processing after chip formation.
CA 2487437 2002-06-05 2002-12-09 Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials Expired - Fee Related CA2487437C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US10/163,817 2002-06-05
US10/163,817 US6709746B2 (en) 2002-06-05 2002-06-05 Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials
PCT/US2002/039346 WO2003104308A1 (en) 2002-06-05 2002-12-09 Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials

Publications (2)

Publication Number Publication Date
CA2487437A1 true CA2487437A1 (en) 2003-12-18
CA2487437C CA2487437C (en) 2010-11-02

Family

ID=29731998

Family Applications (1)

Application Number Title Priority Date Filing Date
CA 2487437 Expired - Fee Related CA2487437C (en) 2002-06-05 2002-12-09 Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials

Country Status (13)

Country Link
US (4) US6709746B2 (en)
EP (1) EP1513887B8 (en)
JP (2) JP4264062B2 (en)
KR (1) KR100943925B1 (en)
CN (1) CN100569836C (en)
AT (1) ATE409718T1 (en)
AU (1) AU2002362111A1 (en)
CA (1) CA2487437C (en)
DE (1) DE60229171D1 (en)
ES (1) ES2310619T3 (en)
HK (1) HK1077314A1 (en)
MX (1) MXPA04012017A (en)
WO (1) WO2003104308A1 (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6709746B2 (en) * 2002-06-05 2004-03-23 Arteva North America S.á.r.l. Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials
US7166671B2 (en) * 2002-12-10 2007-01-23 Cellresin Technologies, Llc Grafted cyclodextrin
US7385004B2 (en) * 2002-12-10 2008-06-10 Cellresin Technologies, Llc Enhanced lubrication in polyolefin closure with polyolefin grafted cyclodextrin
US8129450B2 (en) 2002-12-10 2012-03-06 Cellresin Technologies, Llc Articles having a polymer grafted cyclodextrin
US20040146674A1 (en) * 2003-01-29 2004-07-29 Howell Earl Edmondson Acetaldehyde scavenging by addition of active scavengers to bottle closures
US20050049391A1 (en) * 2003-08-28 2005-03-03 Mark Rule Polyester composition and articles with reduced acetaldehyde content and method using vinyl esterification catalyst
ATE480592T1 (en) 2004-05-24 2010-09-15 Cellresin Tech Llc AMPHOTERE GRAFTED BARRIER MATERIALS
MX2007006005A (en) * 2004-11-22 2007-06-08 Invista Tech Sarl Process for crystallizing and solid state polymerizing polymers and the coated polymer.
JPWO2006115211A1 (en) * 2005-04-25 2008-12-18 株式会社カネカ Cyclodextrin-containing polyester polymer and process for producing the same
JP5260050B2 (en) * 2005-05-27 2013-08-14 麒麟麦酒株式会社 Gas barrier plastic container manufacturing apparatus and method for manufacturing the container
US8557950B2 (en) 2005-06-16 2013-10-15 Grupo Petrotemex, S.A. De C.V. High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates
US20060287471A1 (en) * 2005-06-16 2006-12-21 Schreiber Benjamin R Accelerated acetaldehyde testing of polymers
US8148389B2 (en) * 2005-11-28 2012-04-03 Senju Pharmaceutical Co., Ltd. Pharmaceutical comprising PPAR agonist
US8110518B2 (en) * 2006-04-28 2012-02-07 Fina Technology, Inc. Fluorinated transition metal catalysts and formation thereof
US20080075785A1 (en) * 2006-09-22 2008-03-27 San-Laung Chow Controlled release hydrogel formulation
US7771896B2 (en) * 2006-12-22 2010-08-10 Asml Netherlands B.V. Patterning device, method of providing a patterning device, photolithographic apparatus and device manufacturing method
EP2115045B1 (en) * 2007-02-20 2016-10-26 Cellresin Technologies, LLC Combination of substituted cyclodextrin compound and activated carbon
WO2009032199A1 (en) * 2007-08-31 2009-03-12 The Board Of Trustees Operating Beta-cyclodextrins as nucleating agents for poly(lactic acid)
US7635773B2 (en) 2008-04-28 2009-12-22 Cydex Pharmaceuticals, Inc. Sulfoalkyl ether cyclodextrin compositions
US8152902B2 (en) * 2009-09-30 2012-04-10 Cellresin Technologies, Llc Packaging material such as film, fiber, woven and nonwoven fabric with adsorbancy
CA2692211C (en) * 2009-12-14 2011-09-13 Cellresin Technologies, Llc Maturation or ripening inhibitor release from polymer, fiber, film, sheet or packaging
SI2690951T1 (en) 2011-03-27 2016-02-29 Cellresin Technologies, Llc Cyclodextrin compositions, articles, and methods
US10182567B2 (en) 2011-03-27 2019-01-22 Cellresin Technologies, Llc Cyclodextrin compositions, articles, and methods
DK3702374T3 (en) 2012-02-15 2022-06-27 Cydex Pharmaceuticals Inc PROCEDURE FOR MAKING CYCLODEXTRIN DERIVATIVES
US9320288B2 (en) 2012-11-30 2016-04-26 Cellresin Technologies, Llc Controlled release compositions and methods of using
US9421793B2 (en) 2014-06-26 2016-08-23 Cellresin Technologies, Llc Electrostatic printing of cyclodextrin compositions
US11618244B2 (en) 2017-10-26 2023-04-04 Advansix Resins & Chemicals Llc Multilayer package structure for ozone scavenging

Family Cites Families (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3740258A (en) 1968-01-10 1973-06-19 Dow Chemical Co Resinous enclosure members rendered impermeable by sulfonation
US3733309A (en) 1970-11-30 1973-05-15 Du Pont Biaxially oriented poly(ethylene terephthalate)bottle
US4127633A (en) 1976-04-21 1978-11-28 Imperial Chemical Industries Limited Process for fabricating biaxially oriented container of polyethylene terephthalate coated with a copolymer of vinylidene chloride
FR2389478B1 (en) 1977-05-04 1980-11-28 Rhone Poulenc Ind
US4108324A (en) 1977-05-23 1978-08-22 The Continental Group, Inc. Ribbed bottom structure for plastic container
US4223128A (en) 1978-05-16 1980-09-16 Celanese Corporation Process for preparing polyethylene terephthalate useful for beverage containers
SE423981B (en) 1979-06-11 1982-06-21 Plm Ab PROCEDURE AND DEVICE FOR THE ESTABLISHMENT OF ORIENTED MATERIAL PARTS IN THE PREPARATION OF TERMOPLASTIC MATERIAL
FR2466385A1 (en) 1979-10-01 1981-04-10 Plisson Jean Lionel MOTORCYCLE FRAME WITH STEERING COLUMN REINFORCEMENT
US4334627A (en) 1979-11-27 1982-06-15 The Continental Group, Inc. Blow molded plastic bottle
US4370368A (en) 1980-05-07 1983-01-25 Toyo Seikan Kaisha, Ltd. Plastic bottles and process for preparation thereof
US4381277A (en) 1980-05-29 1983-04-26 Plm Ab Method for producing containers
ATE9988T1 (en) * 1980-07-22 1984-11-15 Imperial Chemical Industries Plc ADDITION PRODUCTS OF ALDEHYDE AND THEIR USE IN A PROCESS TO SEPARATE ALDEHYDE.
US4318489A (en) 1980-07-31 1982-03-09 Pepsico, Inc. Plastic bottle
US4473515A (en) 1980-09-02 1984-09-25 Ryder Leonard B Injection blow molding method
JPS5749620A (en) 1980-09-11 1982-03-23 Teijin Ltd Improvement of polyester
US4342398A (en) 1980-10-16 1982-08-03 Owens-Illinois, Inc. Self-supporting plastic container for liquids
US4393106A (en) 1980-10-31 1983-07-12 Toyo Seikan Kaisha Ltd. Laminated plastic container and process for preparation thereof
US4368825A (en) 1980-11-28 1983-01-18 Standard Oil Company (Indiana) Self-standing bottle structure
DE3261884D1 (en) * 1981-03-20 1985-02-28 Akzo Nv Coloured polyethylene terephthalate moulding compound, a process for the preparation thereof and a container made therefrom
US4374814A (en) * 1981-04-28 1983-02-22 Pure Air, Inc. Method for removal of gaseous formaldehyde from the atmosphere
US4391971A (en) 1981-12-28 1983-07-05 The Goodyear Tire & Rubber Company Color improvement and acetaldehyde reduction in high molecular weight polyesters
US4463121A (en) 1982-08-18 1984-07-31 The Goodyear Tire & Rubber Company Thermoforming partially crystalline polyester articles
US4482586A (en) 1982-09-07 1984-11-13 The Goodyear Tire & Rubber Company Multi-layer polyisophthalate and polyterephthalate articles and process therefor
US4472552A (en) * 1982-09-27 1984-09-18 W. R. Grace & Co. Continuous process for making solid, free-flowing water dispersible PVA-aldehyde reaction product
US4459400A (en) 1983-12-12 1984-07-10 Eastman Kodak Company Poly(ester-amide) compositions
US5334644A (en) * 1985-02-15 1994-08-02 Eastman Chemical Company Aqueous additive systems, methods and polymeric particles
US4975120A (en) * 1986-02-07 1990-12-04 Eastman Kodak Company Aqueous additive systems, methods and polymeric particles
US5190579A (en) * 1985-02-15 1993-03-02 Eastman Kodak Company Aqueous additive systems, methods and polymeric particles
US4615914A (en) 1985-10-07 1986-10-07 The Dow Chemical Company Treatment of the interior surfaces of resinous enclosure members
US5096493A (en) * 1986-02-07 1992-03-17 Eastman Kodak Company Aqueous additive systems, methods and polymeric particles
US4837115A (en) 1986-07-30 1989-06-06 Toyo Seikan Kaisha, Ltd. Thermoplastic polyester composition having improved flavor-retaining property and vessel formed therefrom
US4780257A (en) 1987-05-29 1988-10-25 Devtech, Inc. One piece self-standing blow molded plastic bottles
US4850494A (en) 1988-06-20 1989-07-25 Hoover Universal, Inc. Blow molded container with self-supporting base reinforced by hollow ribs
GB9008847D0 (en) 1990-04-19 1990-06-13 Metacol Limited The incorporation of additives into polyesters
US5266416A (en) 1991-02-20 1993-11-30 The Furukawa Electric Co., Ltd. Aluminum-stabilized superconducting wire
CA2056839C (en) 1991-12-03 1996-11-19 Allan Wilfred Duff Polyolefin bottles with glossy surface
US5258233A (en) 1992-04-02 1993-11-02 Eastman Kodak Company Polyester/polyamide blend having improved flavor retaining property and clarity
MX9307372A (en) 1992-11-24 1994-07-29 Commw Scient Ind Res Org OXYGEN SWEEPING COMPOSITIONS.
US5350788A (en) 1993-03-11 1994-09-27 E. I. Du Pont De Nemours And Company Method for reducing odors in recycled plastics and compositions relating thereto
US5362784A (en) 1993-05-28 1994-11-08 E. I. Du Pont De Nemours And Company Aldehyde scavenging compositions and methods relating thereto
US5352368A (en) * 1993-09-23 1994-10-04 Isolyser Co., Inc. Aldehyde treatment system
DE4414128A1 (en) * 1994-04-22 1995-10-26 Consortium Elektrochem Ind Partially acylated beta-cyclodextrins
US5883161A (en) * 1994-06-23 1999-03-16 Cellresin Technologies, Llc Moisture barrier material comprising a thermoplastic and a compatible cyclodextrin derivative
US5837339A (en) * 1994-06-23 1998-11-17 Cellresin Technologies, Llc Rigid polymeric beverage bottles with improved resistance to permeant elution
US5776842A (en) 1994-06-23 1998-07-07 Cellresin Technologies, Llc Cellulosic web with a contaminant barrier or trap
US5492947A (en) * 1994-06-23 1996-02-20 Aspen Research Corporation Barrier material comprising a thermoplastic and a compatible cyclodextrin derivative
US5663223A (en) * 1994-08-11 1997-09-02 Zapata Technologies, Inc. Flavor protectant closure liner compositions
DE4442699B4 (en) 1994-11-29 2004-07-08 Amcor Ltd., Abbotsford Process for producing a hot-washable PET reusable mineral water container
KR19990028447A (en) 1995-06-26 1999-04-15 에머리 아이. 발라이 Molded plastic container for food and drink and its manufacturing method
US5650469A (en) 1995-10-25 1997-07-22 Eastman Chemical Company Polyester/polyamide blend having improved flavor retaining property and clarity
US5814714A (en) 1995-11-30 1998-09-29 The Dow Chemical Company Mono-olefin/polyene interpolymers, method of preparation, compositions containing the same, and articles made thereof
US5882565A (en) * 1995-12-11 1999-03-16 Cellresin Technologies, Llc Barrier material comprising a thermoplastic and a compatible cyclodextrin derivative
TW336248B (en) 1996-02-05 1998-07-11 Eastman Kodak Co Polyester/polyesteramide blends the invention relates to polyester/polyesteramide blends
US5942297A (en) 1996-03-07 1999-08-24 Cryovac, Inc. By-product absorbers for oxygen scavenging systems
US5898058A (en) 1996-05-20 1999-04-27 Wellman, Inc. Method of post-polymerization stabilization of high activity catalysts in continuous polyethylene terephthalate production
US6042908A (en) 1996-08-22 2000-03-28 Eastman Chemical Company Process for improving the flavor retaining property of polyester/polyamide blend containers for ozonated water
US5971742A (en) 1996-09-18 1999-10-26 Pyramid Composites Manufacturing Limited Partnership Apparatus for molding composite articles
US5916883A (en) * 1996-11-01 1999-06-29 Poly-Med, Inc. Acylated cyclodextrin derivatives
EP0878502A2 (en) 1997-05-05 1998-11-18 Ciba SC Holding AG Formulations of Vitamin E for stabilisation of polymeric organic materials
US5919872A (en) * 1997-06-12 1999-07-06 Shell Oil Company Process for crystallizing blends of polyethylene terephthalate and polyethylene isophthalate
US6162857A (en) * 1997-07-21 2000-12-19 Eastman Chemical Company Process for making polyester/platelet particle compositions displaying improved dispersion
US5977212A (en) 1997-11-21 1999-11-02 W. R. Grace & Co.-Conn. Oxygen scavenging compositions
US5874517A (en) 1997-12-23 1999-02-23 Hoechst Celanese Corporation Method to reduce regenerated acetaldehyde in pet resin
US6007885A (en) 1998-03-19 1999-12-28 W.R. Grace & Co.-Conn. Oxygen scavenging compositions and methods for making same
FR2789685B1 (en) * 1999-02-15 2001-05-04 Univ Lille Sciences Tech PROCESS FOR MANUFACTURING SOLUBLE AND INSOLUBLE POLYMERS BASED ON CYCLODEXTRIN (S) AND / OR DERIVATIVES OF CYCLODEXTRIN (S) AND SOLUBLE POLYMERS BASED ON CYCLODEXTRIN (S) AND / OR DERIVATIVES OF CYCLODEXTRIN (S)
US6328798B1 (en) * 1999-02-19 2001-12-11 Equistar Chemicals, Lp Coated polymeric particles having improved anti-block characteristics, method of making such particles, and apparatus therefor
GB9909956D0 (en) 1999-04-29 1999-06-30 Univ Aston Thermoplastic moulding compositions and polymer additives
US6191209B1 (en) * 1999-06-30 2001-02-20 Ciba Specialty Chemicals Corporation Polyester compositions of low residual aldehyde content
MXPA01013391A (en) 1999-06-30 2002-07-02 Dow Chemical Co Extruded products from polyethylene terephthalate with reduced acetaldehyde content and process of their production.
ATE339471T1 (en) * 1999-06-30 2006-10-15 Ciba Sc Holding Ag POLYESTER COMPOSITIONS WITH LOW RESIDUAL DEHYDE CONTENT
US6274212B1 (en) 2000-02-22 2001-08-14 The Coca-Cola Company Method to decrease the acetaldehyde content of melt-processed polyesters
EP1355986B1 (en) * 2000-12-29 2007-01-24 Ciba SC Holding AG Polyester compositions of low residual aldehyde content
KR100859738B1 (en) * 2001-08-15 2008-09-23 셀레신 테크놀로지스,엘엘씨 Packaging materials having improved barrier properties
EP1291383B1 (en) * 2001-08-23 2004-03-31 Cellresin Technologies, LLC Container having improved organoleptic barrier properties
US20030207056A1 (en) * 2002-05-03 2003-11-06 Will Wood Sealing element for vessel or container closures having improved barrier properties
US6709746B2 (en) * 2002-06-05 2004-03-23 Arteva North America S.á.r.l. Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials
US7166671B2 (en) * 2002-12-10 2007-01-23 Cellresin Technologies, Llc Grafted cyclodextrin

Also Published As

Publication number Publication date
ATE409718T1 (en) 2008-10-15
WO2003104308A1 (en) 2003-12-18
CN100569836C (en) 2009-12-16
ES2310619T3 (en) 2009-01-16
KR20050043798A (en) 2005-05-11
DE60229171D1 (en) 2008-11-13
US20050182234A1 (en) 2005-08-18
KR100943925B1 (en) 2010-02-24
JP2005528514A (en) 2005-09-22
US7018712B2 (en) 2006-03-28
US6709746B2 (en) 2004-03-23
EP1513887A1 (en) 2005-03-16
CN1628143A (en) 2005-06-15
AU2002362111A1 (en) 2003-12-22
US6974603B2 (en) 2005-12-13
US20040161602A1 (en) 2004-08-19
JP4264062B2 (en) 2009-05-13
US6878457B2 (en) 2005-04-12
EP1513887B8 (en) 2008-11-19
US20030232208A1 (en) 2003-12-18
JP2008239991A (en) 2008-10-09
US20040151856A1 (en) 2004-08-05
CA2487437C (en) 2010-11-02
JP4806794B2 (en) 2011-11-02
HK1077314A1 (en) 2006-02-10
MXPA04012017A (en) 2005-10-05
EP1513887B1 (en) 2008-10-01
AU2002362111A8 (en) 2003-12-22

Similar Documents

Publication Publication Date Title
CA2487437A1 (en) Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials
JP5270583B2 (en) Combination of substituted cyclodextrin compound and activated carbon
US20020176953A1 (en) Oxygen scavenging polymer compositions containing ethylene vinyl alchohol copolymers
KR19990028447A (en) Molded plastic container for food and drink and its manufacturing method
CN111004482A (en) High-gas-barrier resin composition and product prepared from same
JPS614752A (en) Gas-barrier molding material having excellent stretchability
Beeva et al. Controlling the barrier properties of polyethylene terephthalate. A review
KR20040050062A (en) Container having improved organoleptic barrier properties
JP2001031768A (en) Oxygen barrier polymer
JP2005008867A (en) Masterbatch and method for producing oxygen absorbing molded product
JP3864111B2 (en) Co-injection stretch blow molded container
Wadekar et al. Recent developments in solid state polymerization of poly (ethylene terephthalate)
US20230383098A1 (en) Titanium dioxide catalyzed butadiene polymer based oxygen scavenging system
JP5084318B2 (en) Blow molding container
CN114643767A (en) Wear-resistant light-transmitting multilayer container and manufacturing method thereof
JPH08323844A (en) Polyester hollow container
JP2001047569A (en) Multi-layer container
MXPA99002736A (en) Transparent oxygen-scavenging article including biaxially-oriented polyester

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20210831

MKLA Lapsed

Effective date: 20191209