IP Library › Granted Patent US 12,662,587
Granted Patent B2
US 12,662,587 · App. 17/759,125 · Granted Jun 23, 2026

Biodegradable compositions and articles made from cellulose acetate

Inventors: Wayne Ken Shih (Kingsport, TN); Stephanie Kay Clendennen (Kingsport, TN); Jeffrey Michael Clauson (Kingsport, TN); Gaurav Amarpuri (Johnson City, TN)
Assignee: Eastman Chemical Company
C08K5/11C08J9/0023C08J9/0061C08J9/0066C08J9/0085C08J9/0095C08J9/08C08J9/122C08J9/141C08J9/34C08K3/26C08K5/0016C08K5/0033C08K5/005C08K11/005C08L1/12C08L67/04C08L71/02C08J2203/02C08J2203/06C08J2203/14C08J2300/16C08J2301/12C08K2003/265C08K2201/018C08L2201/06Y02P20/582Y02W30/62Y02W90/10
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Quick Facts
Patent No.
US 12,662,587
App. No.
17/759,125
Filed
Jul 20, 2022
Granted
Jun 23, 2026
Kind
B2
Art Unit
1762
USPC
524/35
Abstract

A thermoformable and biodegradable cellulose acetate composition comprising at least one cellulose acetate and either polyethylene glycol or m ethoxy polyethylene glycol are disclosed. The compositions are formed into films, sheets, and articles.

Claims (23)

1 . A composition comprising:

(1) a cellulose acetate,

wherein the cellulose acetate has an acetyl degree of substitution (“DS Ac ”) in the range of from 2.2 to 2.6, and wherein the number average molecular weight (“M n ”) of the cellulose acetate is between 20,000 and 100,000, wherein the M n is measured using gel permeation chromatography with a polystyrene equivalent and using N-methyl-2-pyrrolidone (NMP) as the solvent,

(2) from 17-23 wt % of a polyethylene glycol 400 (“PEG400”), and

(3) a stabilizer, which comprises a combination of (i) a secondary antioxidant which is a phosphite compound; and (ii) one or more primary antioxidants, (iii) citric acid, or a combination thereof,

wherein the secondary antioxidant is present at from 0.01 to 0.8 wt %,

wherein the primary antioxidant is present at from 0.05 to 0.7 wt %,

wherein the citric acid is present at from 0.05 to 0.2 wt %,

all weight percentage is based on the total weight of the composition,

wherein the composition is melt processable, biodegradable, and disintegrable.

2 . The composition of claim 1 , wherein the composition further comprises a filler in an amount of from 1 to 60 wt %, based on the total weight of the composition.

3 . The composition of claim 2 , wherein the filler is a carbohydrate, a cellulosic filler, an inorganic filler, a food byproduct, a desiccant, an alkaline filler, or combinations thereof.

4 . The composition of claim 1 , wherein the composition further comprises a biodegradable polymer other than a cellulose acetate.

5 . The composition of claim 1 , wherein when the composition is formed into a film having a thickness of 0.38 mm, the film exhibits greater than 5% disintegration after 6 weeks and greater than 90% disintegration after 12 weeks according to Disintegration Test Protocol, as described in the specification.

6 . The composition of claim 1 , wherein when the composition is formed into a film having a thickness of 0.38 mm, the film exhibits greater than 10% disintegration after 6 weeks and greater than 90% disintegration after 12 weeks according to Disintegration Test Protocol, as described in the specification.

7 . The composition of claim 1 , wherein when the composition is formed into a film having a thickness of 0.76 mm, the film exhibits greater than 90% disintegration after 12 weeks according to Disintegration Test Protocol, as described in the specification.

8 . An article comprising the composition of claim 1 .

9 . The article of claim 8 , wherein the article meets the criteria established by the United States Food and Drug Administration for designation as food contact compliant.

10 . The article of claim 8 , wherein the article is formed from an orienting process, an extrusion process, an injection molding process, a blow molding process, or a thermoforming process.

11 . The article of claim 10 , wherein the article is formed from a thermoforming process, and the film or sheet used to form the article is from 0.25 to 4.1 mm thick.

12 . The article of claim 8 , wherein when the article is clear, the article exhibits a haze of less than 10%.

13 . The article of claim 8 , wherein the gel count is less than 8.0% area, as determined according to the gel count test protocol described in the specification.

14 . The article of claim 8 , wherein the article exhibits greater than 90% disintegration after 12 weeks according to disintegration test protocol for films, as described in the specification.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 26, 2022
From: SHIH, WAYNE KEN; CLENDENNEN, STEPHANIE KAY; CLAUSON, JEFFREY MICHAEL; AMARPURI, GAURAV
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 061546/0760 →
Continuity (4)
Provisional Application 62706274 · Aug 7, 2020
Provisional Application 63051942 · Jul 15, 2020
Provisional Application 62963313 · Jan 20, 2020
Related Publication 20230075066A1 · Mar 9, 2023
References Cited (79)
US 2280863A · Stern · 1942 [cited by applicant]
US 4180536A · Howell, Jr. et al. · 1979 [cited by applicant]
US 5292783A · Buchanan et al. · 1994 [cited by applicant]
US 5594068A · Buchanan et al. · 1997 [cited by applicant]
US 5970988A · Buchanan et al. · 1999 [cited by applicant]
US 6190499B1 · Oriaran · 2001 [cited by examiner]
US 6221924B1 · Mori et al. · 2001 [cited by applicant]
US 6571802B1 · Yamashita · 2003 [cited by applicant]
US 9062186B2 · Longdon et al. · 2015 [cited by applicant]
US 10518444B2 · Pawloski et al. · 2019 [cited by applicant]
US 20040030043A1 · Aranishi et al. · 2004 [cited by applicant]
US 20060267243A1 · Tindall · 2006 [cited by applicant]
US 20080281010A1 · Lefas et al. · 2008 [cited by applicant]
US 20120238673A1 · Longdon et al. · 2012 [cited by applicant]
US 20190077885A1 · Matsumura et al. · 2019 [cited by applicant]
CN 103102510A · 2013 [cited by applicant]
CN 105585740A · 2016 [cited by applicant]
EP 2500378 · 2012 [cited by applicant]
EP 2599827A1 · 2013 [cited by examiner]
GB 248949A · 1926 [cited by applicant]
GB 2489491A · 2012 [cited by examiner]
JP 2001103845A · 2001 [cited by applicant]
JP 2003002998A · 2003 [cited by applicant]
JP 2006028429A · 2006 [cited by examiner]
WO WO9410238 · 1994 [cited by applicant]
WO WO9422632 · 1994 [cited by applicant]
WO WO9428062 · 1994 [cited by applicant]
WO WO9965977 · 1999 [cited by applicant]
WO WO2013149612A2 · 2013 [cited by applicant]
WO WO2017077054A1 · 2017 [cited by examiner]
WO WO2021150542A1 · 2021 [cited by applicant]
WO WO2023220007A1 · 2023 [cited by applicant]
Odian, G., Principles of Polymerization, Third edition, John Wiley & Sons, Inc., 1991, pp. 19-24. [cited by examiner]
Author Unknown, “Eastman CA Cellulose Acetate, Sustained-Release”, Gustav Parmentier GmbH product bulletin, obtained from http://www.parmentier.de/elo/gpf/ca-product-information-sheet.pdf, Feb. 3, 2006. [cited by examiner]
Clarivate Analytics English Equivalent Abstract of JP 2006-028429, Imanishi, Feb. 2, 2006. [cited by examiner]
Co-pending U.S. Appl. No. 17/759,047, filed Jul. 19, 2022; Sapia et al. [cited by applicant]
ASTM D871; “Standard Test Methods of Testing Cellulose Acetate”; Published Jan. 2019. [cited by applicant]
ASTM D3575; “Standard Test Methods for Flexible Cellular Materials Made from Olefin Polymers”; Published Mar. 2020. [cited by applicant]
ASTMD6290; “Standard Test Method for Color Determination of Plastic Pellets”; Jun. 2019. [cited by applicant]
ASTMD6400; “Standard Specification for Labeling of Plastics Designed to be Aerobically Composted in Municipal or Industrial Facilities”; Published Dec. 2022. [cited by applicant]
ASTMD6474; “Standard Test Method for Determining Molecular Weight Distribution and Molecular Weight Averages of Polyolefins by High Temperature Gel Permeation Chromatography”; Published Apr. 2020. [cited by applicant]
ASTMD6691; “Standard Test Method for Determining Aerobic Biodegradation of Plastic Materials in the Marine Environment by a Defined Microbial Consortium or Natural Sea Water Inoculum”; Published Jan. 2018. [cited by applicant]
ASTMD7310; “Standard Practice for Defect Detection and Rating of Plastic Films Using Optical Sensors”; Published Sep. 2021. [cited by applicant]
ASTMD7481; “Standard Test Methods for Determining Loose and Tapped Bulk Densities of Powders using a Graduated Cylinder”; Published Jul. 2018. [cited by applicant]
ASTME308; “Standard Practice for Computing the Colors of Objects by Using the CIE Systems”; Published Aug. 2022. [cited by applicant]
Buchanan, Charles et al.; “The Influence of Degree of Substitution on Blend Miscibility and Biodegradation of Cellulose Acetate Blends”; Journal of Environmental Polymer Degradation, vol. 4, No. 3, (1996): pp. 179-195. [cited by applicant]
Gedon, Steve et al.; “Cellulose Esters, Inorganic Esters”; Kirk-Othmer, Encyclopedia of Chemical Technology, 5th Edition, vol. 5 (2004) pp. 394-444. [cited by applicant]
Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the Declaration with a date of filing Jan. 20, 2021 received in PCT/US2021/014079. [cited by applicant]
Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the Declaration with a date of mailing Oct. 27, 2022 received in PCT/US2022/037528. [cited by applicant]
Phuong, Vu Thanh, et al.; “Cellulose Acetate Blends—Effect of Plasticizers on Properties and Biodegradability”; Journal of Renewable Materials, vol. 2, No. 1 (Mar. 1, 2014) pp. 35-41. [cited by applicant]
Warth, Holger et al.; “Thermoplastic Cellulose Acetate and Cellulose Acetate Compounds Prepared by Reactive Processing”; Journal of Applied Polymer Science, vol. 64, No. 2, 11 (Apr. 1997), pp. 231-242. [cited by applicant]
Yuan, Jinghua et al.; “Effects of Polyethylene Glycol on Morphology, Thermomechanical Properties, and Water Vapor Permeability of Cellulose Acetate-Free Films”; Pharmaceutical Technology 25: (2001) pp. 62-73. [cited by applicant]
USPTO Office Action dated Nov. 27, 2024 received in Co-pending U.S. Appl. No. 17/759,047. [cited by applicant]
Co-pending U.S. Appl. No. 18/578,336, filed Jan. 11, 2024; Aden et al. [cited by applicant]
Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the Declaration with a date of mailing Jan. 22, 2024 received in PCT/US2023/074775. [cited by applicant]
Biodegradable Products Institute, Important PFAS Announcement, Mar. 28, 2018; 2 pages. [cited by applicant]
Chiang, Sue et al, “Avoiding Hidden Hazards, A Purchaser's Guide to Safer Foodware”; Center for Environmental Health, 2018; 43 pages. [cited by applicant]
Co-pending U.S. Appl. No. 17/759,109, filed Jan. 2021, 2021; Shih. [cited by applicant]
Co-pending U.S. Appl. No. 17/759,125, filed Jan. 20, 2021; Shih et al. [cited by applicant]
Dreux, Xavier et al.; “Viscoelastic behaviour of cellulose acetate/triacetin blends by rheology in the melt state”; Carbohydrate Polymers, 222, (2019), 8 pages. [cited by applicant]
H.R.535—116th Congress (2019-2020): PFAS Action Act of 2019, H.R.535, 116th Cong. (2020), https://www.congress.gov/bill/116th-congress/house-bill/535. [cited by applicant]
Hopman, CH. et al.; AIP Conference Proceedings 1593, 116 (2014); https.//doi.org/10.1063/1.4873746 Published Online: Feb. 17, 2015. [cited by applicant]
Kamide, K. and Saito, Masatoshi; “Thermal Analysis of Cellulose Acetate Solids with Total Degrees of Substitution of 0.49, 1.75, 2.46, and 2.92”; Polymer Journal , vol. 17, No. 8; pp. 919-928 ( 1985). [cited by applicant]
Kirk-Othmer, Encyclopedia of Chemical Technology, 5 [cited by applicant]
Kirk-Othmer, Encyclopedia of Chemical Technology, 5 [cited by applicant]
Machulek, Jr., Amilcar et al. Fundamental Mechanistic Studies of the Photo-Fenton Reaction for the Degradation of Organic Pollutants, interchopen.com. 2012; 24 pages. [cited by applicant]
Notification of Transmittal of the European Search Report, date of receipt Apr. 10, 2025 received in European Application No. 24221666.1. [cited by applicant]
Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the Declaration date of mailing Apr. 15, 2021 received in International Application No.… [cited by applicant]
Notification of Transmittal of the International Search Report and the Written Opinion of the International Searching Authority, or the Declaration with a date of mailing Apr. 26, 2021 received in PCT/US2021/014078. [cited by applicant]
Reglero, Ruiz, Jose Antonio, et al. Polymer Engineering Science, 55(9), pp. 2018-2029, 2015. [cited by applicant]
Rosa DS, Guedes CGF, Casarin F, Bragança FC. 2005. The effect of the Mw of PEG in PCL/CA blends. Polymer Testing 2005(24):542-8. [cited by applicant]
USPTO Office Action dated Jan. 2, 2026 received in co-pending U.S. Appl. No. 17/759,047. [cited by applicant]
USPTO Office Action dated Jul. 11, 2025 received in co-pending U.S. Appl. No. 17/759,047. [cited by applicant]
USPTO Office Action dated Mar. 25, 2025 received in co-pending U.S. Appl. No. 17/759,125. [cited by applicant]
USPTO Office Action dated Sep. 5, 2025 received in co-pending U.S. Appl. No. 17/759,125. [cited by applicant]
Wood, Paul M.; “Pathways for producing of Fenton's reagent by wood-rotting fungi”; FEMS Microbiology Reviews 13 (1994) 313-320. [cited by applicant]
Zepnik, Stefan et al.; “Cellulose Acetate for Thermoplastic Foam Extrusion, Chapter 2”; Intech; 2013; pp. 17-44. [cited by applicant]
Zepnik, Stefan et al.; “Extensional Flow Properties of Externally Plasticized Cellulose Acetate: Influence of Plasticizer Content”; Polymers, 5; 2013; pp. 873-889. [cited by applicant]
Zepnik, Stefan et al.; “Foam extrusion behavior, morphology, and physical foam properties of organic cellulose ester”; J. Mater. Res, vol. 28, No. 17; 2013; pp. 2394-2400. [cited by applicant]