Source: https://patents.google.com/patent/US8501308B2/en
Timestamp: 2018-12-19 12:34:10
Document Index: 796153068

Matched Legal Cases: ['§119', 'Application No. 2', 'Application No. 09173916', 'Application No. 11', 'Application No. 10010696', 'Application No. 2003', 'Application No. 2005', 'Application No. 2']

US8501308B2 - Grafted cyclodextrin - Google Patents
US8501308B2
US8501308B2 US11403457 US40345706A US8501308B2 US 8501308 B2 US8501308 B2 US 8501308B2 US 11403457 US11403457 US 11403457 US 40345706 A US40345706 A US 40345706A US 8501308 B2 US8501308 B2 US 8501308B2
US11403457
US20060182917A1 (en )
This application is a divisional of application Ser. No. 10/672,297, filed Sep. 25, 2003, which issued as U.S. Pat. No. 7,166,671 on Jan. 23, 2007, which claims priority under 35 U.S.C. §119(e) to provisional application Ser. No. 60/432,523, filed Dec. 10, 2002, which applications are incorporated herein by reference.
ethylene-maleic anhydride copolymer/LDPE blend and β-CD grafted
ethylene-maleic anhydride copolymer/LDPE blend.
Concentration ⁢ ⁢ of ⁢ ⁢ Compound ⁢ ⁢ in ⁢ ⁢ ppm = ( Peak ⁢ ⁢ Area ⁢ × RF ) ÷ Sample ⁢ ⁢ Wt . ⁢ Concentration ⁢ ⁢ of ⁢ ⁢ Compound ⁢ ⁢ in ⁢ ⁢ ppm = Peak ⁢ ⁢ Area Calibration Curve ⁢ ⁢ Slope ÷ Sample ⁢ ⁢ Wt .
and flavor compounds in CD grafted low density polyolefins
and commercial contact layer LDPE following eight days
β Grafted EMA/ β Grafted EMA/ Control
LDPE - 1A LDPE - 1B Resin
A 0.25±0.002 g sample of milled shavings is placed into a 22-mL glass vial. The vial is immediately capped using a Teflon® faced butyl rubber septa and aluminum crimp top. Volatiles are desorbed from the sample into the headspace by heating the vial at 85° C. for 24-hours. The vial is transferred to a heated (85° C.) headspace sampler (Hewlett Packard model 19395A) attached to a Hewlett Packard Model HP-5880 II GC equipped with a flame ionization detector (FID), and computerized data collection. J&W Scientific capillary column (DB-5, 30 m×0.25 mm I.D., 1.0 μm film) with hydrogen carrier flow set at a split ratio of 20:1. HRGC is used to measure the acetaldehyde concentration in the headspace of the vial. The aldehyde peak area is integrated to quantitate the concentration, and then the concentration is calculated from a four-point standard calibration covering the concentration range of the samples. Sample concentrations are reported in ppm (μg/g—weight/weight). The aldehyde concentration is calculated from the calibration curve slope or response factor (RF) prepared for each aldehyde analyte.
Concentration ⁢ ⁢ of ⁢ ⁢ Compound ⁢ ⁢ in ⁢ ⁢ ppm = ( Peak ⁢ ⁢ Area ⁢ × RF ) ÷ Sample ⁢ ⁢ Wt . ⁢ Concentration ⁢ ⁢ of ⁢ ⁢ Compound ⁢ ⁢ in ⁢ ⁢ ppm = Peak ⁢ ⁢ Area Calibration Curve ⁢ ⁢ Slope ÷ Sample ⁢ ⁢ le ⁢ ⁢ Wt .
treated water in contact with closure liner compositions containing
CD grafted LDPE and non-CD grafted LDPE. Aldehyde
concentrations are μgm/L or parts per billion is shown.
CD grafted polyolefin and closure liner
wt % compositions are shown.
Sample CD Graft Composition
Disc samples (0.10 cm thick.times.1.27 cm diameter and weighing 128 mg) are tested in a closed-volume vapor permeation device (refer to FIG. 7). The experimental aluminum measurement cell has two compartments (i.e., cells) separated by the disc under study (effective disc area=5.3 cm.sup.2) and capped at both ends using Teflon® faced butyl rubber septa and aluminum crimp-tops.
The standard concentrations of TCA were prepared by diluting a stock solution of TCA prepared in methanol at 50 mg/mL in a 1% Triton×100 aqueous solution. The dilutions were prepared so that 5 uL additions of the diluted stock provided the masses (pg) to the test 20 mL headspace vials. The following SPME GC/ECD instrument conditions were used in the TCA analysis.
SPME Conditions: Heat @50° C. for 30 min
Insert SPME for 30 min @50° C.
Ave. Film under steady-state conditions,
Thickness per unit area
(mils) gm/100
±0.05 gm/m2 · day inch2 · day
1. A container comprising an enclosed volume, the volume surrounded by a polyolefin web, the web comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly substituted covalently bonded groups derived from a cyclodextrin compound, the web comprising about 100 parts by weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin; wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring.
2. The container of claim 1 wherein the web comprises a laminate comprising a paperboard layer and a bonded polyolefin layer.
3. The container of claim 1 wherein the volume enclosed by the web is filled with a liquid food.
4. The container of claim 3 wherein web has a capacity of about 100 mL to 3 liters and the liquid food comprises a citrus juice.
5. The container of claim 1 wherein the polyolefin comprises a polyolefin having melt index of about 0.5 to 100 g-10 min−1.
6. The container of claim 1 wherein the polyolefin comprises a polyolefin having a melt index of about 0.7 to 200 g-10 min−1.
7. The container of claim 1 wherein the polyolefin comprises a polyethylene chip.
8. The container of claim 1 wherein the modified polyolefin comprises a modified polyethylene.
9. The container of claim 1 wherein the polyolefin comprises a polypropylene.
10. The container of claim 1 wherein the modified polyolefin comprises a modified polypropylene.
11. The container of claim 1 wherein the polyolefin comprises a poly(ethylene-co-propylene).
12. The container of claim 1 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).
13. The container of claim 1 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.05 to 2 weight percent maleic anhydride.
14. The container of claim 1 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.1 to 1 weight percent maleic anhydride.
15. The container of claim 7 wherein the polyethylene comprises a low-density polyethylene.
16. The container of claim 7 wherein the polyethylene comprises a linear low-density polyethylene.
17. The container of claim 7 wherein the polyethylene comprises a high-density polyethylene.
18. A film comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly instituted groups derived from a cyclodextrin compound, the film comprising about 100 parts weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin; wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring and wherein the cyclodextrin compound has a substituent substantially on at least one —OH group at the −2, −3 or the −6 position of the glucose moiety in the cyclodextrin.
20. The film of claim 18 wherein the polyolefin comprises a melt index of about 15 to 100 g-10 min−1.
21. The film of claim 18 wherein the polyolefin comprises a melt index of about 1.7 to 200 g-10 min−1.
22. The film of claim 18 wherein the polyolefin comprises a polyethylene.
23. The film of claim 18 wherein the modified polyolefin comprises a modified polyethylene.
24. The film of claim 18 wherein the polyolefin comprises a polypropylene.
25. The film of claim 18 wherein the modified polyolefin comprises a modified polypropylene.
26. The film of claim 18 wherein the polyolefin comprises a poly(ethylene-co-propylene).
27. The film of claim 18 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).
28. The film of claim 18 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.05 to 5 weight percent maleic anhydride.
29. The film of claim 18 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.1 to 2 weight percent maleic anhydride.
30. The film of claim 22 wherein the polyethylene comprises a low-density polyethylene.
31. The film of claim 22 wherein the polyethylene comprises a linear low-density polyethylene.
32. The film of claim 22 wherein the polyethylene comprises a high-density polyethylene.
33. A bottle cap comprising a closure shell for an enclosed volume, the volume surrounded by a polyolefin bottle, the closure shell comprising a web comprising a cap liner laminate comprising a paperboard layer bonded to polyolefin layer, the polyolefin layer comprising a blend of a polyolefin resin and a modified polyolefin resin, the modified polyolefin resin comprising a polymethylene backbone having randomly substituted covalently bonded groups derived from a cyclodextrin compound, the web comprising about 100 parts by weight of the polyolefin resin and about 0.01 to 10 parts by weight of the modified polyolefin per part by weight of the resin; wherein the cyclodextrin compound is substantially free of a compound in the central pore of the cyclodextrin ring.
34. The bottle cap of claim 33, wherein threads along inner surface of the bottle cap mate with threads along the top, external surface of the bottle.
35. The bottle cap of claim 33, wherein side walls extend from the bottom surface of said bottle cap and form a substantially cylindrical cavity.
36. The bottle cap of claim 33 wherein the polyolefin comprises a polyolefin having a melt index of about 0.5 to 100 g-10 min−1.
37. The bottle cap of claim 33 wherein the polyolefin comprises a polyolefin having a melt index of about 0.7 to 200 g-10 min−1.
38. The bottle cap of claim 33 wherein the polyolefin comprises a polyethylene.
39. The bottle cap of claim 33 wherein the modified polyolefin comprises a modified polyethylene.
40. The bottle cap of claim 33 wherein the polyolefin comprises a polypropylene.
41. The bottle cap of claim 33 wherein the modified polyolefin comprises a modified polypropylene.
42. The bottle cap of claim 33 wherein the polyolefin comprises a poly(ethylene-co-propylene).
43. The bottle cap of claim 33 wherein the modified polyolefin comprises a modified poly(ethylene-co-propylene).
44. The bottle cap of claim 33 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.02 to 2 weight percent maleic anhydride.
45. The bottle cap of claim 33 wherein the modified polyolefin comprises a cyclodextrin bonded to a maleic acid modified polyolefin wherein the polyolefin comprises about 0.02 to 1 weight percent maleic anhydride.
46. The bottle cap of claim 38 wherein the polyethylene comprises a low-density polyethylene.
47. The bottle cap of claim 38 wherein the polyethylene comprises a linear low-density polyethylene.
48. The bottle cap of claim 38 wherein the polyethylene comprises a high-density polyethylene.
49. The film of claim 18 wherein the film encloses a food material.
50. The film of claim 49 wherein the food is a solid food.
51. The film of claim 49 wherein the food comprises ripening material.
52. The film of claim 51 wherein the ripening material is a fruit, vegetable, herb, or flower.
53. The film of claim 49 wherein the film comprises a multilayer structure.
54. The film of claim 53 wherein the structure contacting the food comprises the modified polyolefin resin.
US11403457 2002-12-10 2006-04-13 Grafted cyclodextrin Active 2027-07-11 US8501308B2 (en)
US11403457 US8501308B2 (en) 2002-12-10 2006-04-13 Grafted cyclodextrin
US20060182917A1 true US20060182917A1 (en) 2006-08-17
US8501308B2 true US8501308B2 (en) 2013-08-06
WO2018047205A1 (en) * 2016-09-09 2018-03-15 RESILIA S.r.l. A process to remove bad smell and odours from plastic materials
US3929542A (en) 1970-11-03 1975-12-30 Basf Farben & Fasern Non-woven webs of filaments of synthetic high molecular weight polymers and process for the manufacture thereof
EP0270309A1 (en) 1986-12-01 1988-06-08 Du Pont Canada Inc. Process for the dyeing of polymers of propylene, butene-1 and 4-methyl-pentene-1
US4833202A (en) * 1987-05-05 1989-05-23 A. E. Staley Manufacturing Company Multi-ethylenic monomers from glycosides
CA2063453A1 (en) 1990-05-21 1991-11-22 Masanobu Yoshinaga Method of synthesizing cyclodextrin polymers and process for producing cyclodextrin membranes
US5322877A (en) 1992-03-13 1994-06-21 Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha Ternary resin composition and production thereof
JP2001500815A (en) 1996-02-20 2001-01-23 セルレジン・テクノロジーズ・エルエルシー Thermoplastic fuel tank with reduced divergence of the fuel vapor
US6774188B1 (en) 1999-09-10 2004-08-10 Atofina Crosslinkable compositions of functionalized polyolefin powders
JP2008100027A (en) 2006-10-20 2008-05-01 Kashin Kin Puff
JP2002543243A (en) 1999-04-29 2002-12-17 ビーエーエスエフ アクチェンゲゼルシャフト Superabsorbent polymers comprising odor control compounds
US20060183857A1 (en) 2002-12-10 2006-08-17 Cellresin Technologies, Llc Grafted cyclodextrin
"Notice of Allowance Received", mailed Aug. 3, 2012 in U.S. Appl. No. 11/761,017, "Grafted Cyclodextrin," (17 pages).
"Office Action Received for Canadian Application No. 2,452,293," corresponding to U.S. Appl. No. 11/761,017, mailed Mar. 6, 2012, (3 pages).
Berejka, "Electron Beam Grafting of Polymers", Ionicorp, Huntington, New York, Advances in radiation chemistry of polymers, IAEA, pp. 85-89 (Nov. 2004).
Chung, T. C., "Functionalization by Post-Polymerization Processes", Functionalization of Polyolefins, Chapter 5, Copyright 2002, pp. 65-78.
European Search Report dated Jan. 29, 2010 from the European Patent Office in EP Patent Application No. 09173916.9, which corresponds to U.S. Appl. No. 10/672,297, filed Sep. 25, 2003, which is a parent application to the present Application No. 11/403,480 (3 pages).
Extended European Search Report, dated Mar. 3, 2011, European Patent Application No. 10010696.2, (5 pages).
File history (as of Oct. 21, 2010) for co-pending U.S. Appl. No. 11/761,017, filed Jun. 11, 2007, entitled "Grafted Cyclodextrin", which claims priority to the same parent application (U.S. Appl. No. 10/672,297, now U.S. Pat. No. 7,166,671) as the present application (U.S. Appl. No. 11/403,457) (183 pages).
File history (as of Oct. 21, 2010) for co-pending U.S. Appl. No. 11/761,105, filed Jun. 11, 2007, entitled "Grafted Cyclodextrin", which claims priority to the same parent application (U.S. Appl. No. 10/672,297, now U.S. Pat. No. 7,166,671) as the present application (U.S. Appl. No. 11/403,457) (311 pages).
Japanese Office Action dated Aug. 11, 2009 from the Japanese Patent Office in JP Patent Application No. 2003-397846, mailed Aug. 24, 2009 (5 pages).
Japanese Office Action dated Sep. 22, 2011 from the Japanese Patent Office in JP Patent Application No. 2005-316721, mailed Sep. 22, 2011 (5 pages).
Le Thuaut, P. et al. Grafting cyclodextrins onto polypropylene nonwoven fabrics for the manufacture of reactive filters. I. Synthesis parameters J. Applied Polymer Science 2000, v. 77, pp. 2118-2125. *
Moad, "Chemical modification of starch by reactive extrusion", Progress in Polymer Science, 36:218-237 (2011).
Moad, Graeme, "Chemical modification of starch by reactive extrusion," journal homepage: www.elsevier.com/locate/ppolysci; 2010, 20 pages.
Office Action dated May 24, 2011 for co-pending Canadian Patent Application No. 2,452,293, filed Dec. 5, 2003 entitled "Grafted Cyclodextrin" (4 pages).
Office Actions and Responses in co-pending U.S. Appl. No. 11/403,480, "Grafted Cyclodextrin" (38 pages).
Partial File history (from Apr. 14, 2011 to Aug. 24, 2011) for co-pending U.S. Appl. No. 11/761,017, filed Jun. 11, 2007, entitled "Grafted Cyclodextrin", which claims priority to the same parent application (U.S. Appl. No. 10/672,297, now U.S. Pat. No. 7,166,671) as the present application (U.S. Appl. No. 11/403,457) (37 pages).
Partial File history (from Apr. 14, 2011 to Aug. 24, 2011) for co-pending U.S. Appl. No. 11/761,105, filed Jun. 11, 2007, entitled "Grafted Cyclodextrin", which claims priority to the same parent application (U.S. Appl. No. 10/672,297, now U.S. Pat. No. 7,166,671) as the present application (U.S. Appl. No. 11/403,457) (67 pages).
Partial File history (from Oct. 21, 2010 to Apr. 14, 2011) for co-pending U.S. Appl. No. 11/761,017, filed Jun. 11, 2007, entitled "Grafted Cyclodextrin", which claims priority to the same parent application (U.S. Appl. No. 10/672,297, now U.S. Pat. No. 7,166,671) as the present application (U.S. Appl. No. 11/403,457) (41 pages).
Partial File history (from Oct. 21, 2010 to Apr. 14, 2011) for co-pending U.S. Appl. No. 11/761,105, filed Jun. 11, 2007, entitled "Grafted Cyclodextrin", which claims priority to the same parent application (U.S. Appl. No. 10/672,297, now U.S. Pat. No. 7,166,671) as the present application (U.S. Appl. No. 11/403,457) (19 pages).
Rosiak, "Radiation Polymerization in Solution", Institute of Applied Radiation Chemistry, Technical University of Lodz, Lodz, Poland, Advances in radiation chemistry of polymers, IAEA, pp. 41-60 (Nov. 2004).
Sankhe, S. et al., "Characterization of Erucamide Profiles in Multilayer Linear Low-Density Polyethylene and Propylene-Ethylene Copolymer Films Using Synchrotron-Based FT-1R Microspectroscopy," Applied Spectroscopy, vol. 56, No. 2, pp. 205-211 (2002).
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WOOD, WILLARD E.;BEAVERSON, NEIL J.;SEETHAMRAJU, KASYAP V.;SIGNING DATES FROM 20031027 TO 20031028;REEL/FRAME:030775/0819