Granted Patent
B2
US 12,234,356 · App. 17/550,638 · Granted Feb 25, 2025
Epoxy compositions containing polyrotaxane additives having improved impact strength
Inventors:
Hasmukh A. Patel (Katy, TX); Ali Zein Khater (Houston, TX); Peter Boul (Houston, TX); Pulickel M. Ajayan (Houston, TX); Muhammad M. Rahman (Houston, TX)
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Abstract
This document relates to epoxy compositions containing a sliding-ring polymer (polyrotaxane) additive and a thermally-curable epoxy resin. The epoxy compositions exhibit increased flexural toughness and impact resistance as compared to the same epoxy composition that does not contain the additive. This document also relates to 3D-printed epoxy compositions containing a sliding-ring polymer (polyrotaxane) additive and a thermally-curable epoxy resin.
Claims (34)
1. An epoxy composition comprising:
a thermally-curable epoxy resin;
about 1 wt % to about 25 wt % of fumed silica; and
a sliding-ring polymer additive that is a cross-linked polyrotaxane bead, wherein the cross-linked polyrotaxane bead comprises:
a linear polymer;
at least one ring compound substituted with polyurethane, polycaprolactone, or a combination thereof, wherein the linear polymer is threaded through the opening of the ring compound; and
stopper groups disposed at both end terminals of the linear polymer.
2. The epoxy composition of claim 1 , wherein the thermally-curable epoxy resin is present in an amount of about 50 wt % to about 95 wt %, about 55 wt % to about 95 wt %, about 60 wt % to about 90 wt %, about 65 wt % to about 90 wt %, about 75 wt % to about 85 wt %, or about 80 wt % to about 85 wt % of the epoxy composition.
3. The epoxy composition of claim 1 , wherein the fumed silica is present in an amount of about 1 wt % to about 10 wt %, about 5 wt % to about 15 wt %, or about 5 wt % to about 10 wt % of the epoxy composition.
4. The epoxy composition of claim 1 , wherein the fumed silica is present in an amount of about 7.5 wt % of the epoxy composition.
5. The epoxy composition of claim 1 , wherein the cross-linked polyrotaxane beads are surface-functionalized with epoxide rings.
6. The epoxy composition of claim 1 , wherein the sliding-ring polymer additive is present in an amount of about 1 wt % to about 25 wt %, about 1 wt % to about 15 wt %, about 2 wt % to about 10 wt %, about 2.5 wt % to about 5 wt %, about 5 wt % to about 20 wt %, or about 10 wt % to about 15 wt % of the epoxy composition.
7. The epoxy composition of claim 1 , further comprising a curing agent.
8. The epoxy composition of claim 7 , wherein the curing agent is an etheramine or an aliphatic or aromatic diamine, triamine, tetraamine, or combinations thereof.
9. The epoxy composition of claim 7 , wherein the epoxy resin and the curing agent are present in a ratio of about 75:25.
10. The epoxy composition of claim 1 , wherein the epoxy composition is able to be 3D-printed.
11. The epoxy composition of claim 1 , wherein the epoxy composition exhibits increased strain tolerance or flexural strain as compared to the same epoxy composition without the sliding-ring polymer additive.
12. The epoxy composition of claim 1 , wherein the epoxy composition exhibits a strain tolerance or flexural strain of about 0.2 to about 0.3.
13. The epoxy composition of claim 1 , wherein the epoxy composition exhibits improved flexural toughness as compared to the same composition without the sliding-ring polymer additive.
14. The epoxy composition of claim 1 , wherein the epoxy composition has a flexural toughness of about 10 J·m 3 to about 20 J·m 3 or about 11 J·m 3 to about 15 J·m 3 .
15. The epoxy composition of claim 1 , wherein the epoxy composition has a flexural toughness of about 12 J·m 3 .
16. The epoxy composition of claim 1 , wherein the epoxy composition exhibits improved impact resistance as compared to the same composition without the sliding-ring polymer additive.
17. A method for enhancing the impact resistance of an epoxy composition, the method comprising adding a sliding-ring polymer additive that is a cross-linked polyrotaxane bead to a thermally-curable epoxy resin, the cross-linked polyrotaxane bead comprising:
a linear polymer;
at least one ring compound substituted with polyurethane, polycaprolactone, or a combination thereof, wherein the linear polymer is threaded through the opening of the ring compound; and
stopper groups disposed at both end terminals of the linear polymer.
18. The method of claim 17 , wherein the epoxy composition further comprises about 1 wt % to about 25 wt % of the composition fumed silica.
19. The method of claim 17 , wherein the epoxy composition exhibits improved impact resistance as compared to the same composition without the sliding-ring polymer additive.
20. A method for enhancing the flexural toughness of an epoxy composition, the method comprising adding a sliding-ring polymer additive that is a cross-linked polyrotaxane bead to a thermally-curable epoxy resin, the cross-linked polyrotaxane bead comprising:
a linear polymer;
at least one ring compound substituted with polyurethane, polycaprolactone, or a combination thereof, wherein the linear polymer is threaded through the opening of the ring compound; and
stopper groups disposed at both end terminals of the linear polymer.
21. The method of claim 20 , wherein the epoxy composition further comprises about 1 wt % to about 25 wt % of the composition fumed silica.
22. The method of claim 20 , wherein the epoxy composition exhibits improved flexural toughness as compared to the same composition without the sliding-ring polymer additive.
Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Aug 24, 2022
From: KHATER, ALI ZEIN; AJAYAN, PULICKEL M.; RAHMAN, MUHAMMAD M.
To: WILLIAM MARSH RICE UNIVERSITY
Reel/Frame 060882/0499 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 1, 2022
From: ARAMCO SERVICES COMPANY
To: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
Reel/Frame 060066/0887 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 1, 2022
From: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 060067/0052 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 23, 2021
From: PATEL, HASMUKH A.; BOUL, PETER
To: ARAMCO SERVICES COMPANY
Reel/Frame 058469/0453 →
Continuity (1)
References Cited (299)
US 1811799A
· Lukens
· 1931
[cited by applicant]
US 2705050A
· Davis et al.
· 1955
[cited by applicant]
US 3301797A
· Drucket et al.
· 1967
[cited by applicant]
US 3481903A
· Alelio
· 1969
[cited by applicant]
US 3887009A
· Miller et al.
· 1975
[cited by applicant]
US 3938594A
· Rhudy et al.
· 1976
[cited by applicant]
US 4137182A
· Golinkin
· 1979
[cited by applicant]
US 4272430A
· Pieh et al.
· 1981
[cited by applicant]
US 4615809A
· King
· 1986
[cited by applicant]
US 4771112A
· Engelbrecht
· 1988
[cited by applicant]
US 4797433A
· Lahalih
· 1989
[cited by applicant]
US 4883126A
· Leland
· 1989
[cited by applicant]
US 5007481A
· Williams et al.
· 1991
[cited by applicant]
US 5062897A
· Katsunnata
· 1991
[cited by applicant]
US 5159828A
· Steiger
· 1992
[cited by applicant]
US 5352290A
· Takeshita et al.
· 1994
[cited by applicant]
US 5401312A
· Hanst
· 1995
[cited by applicant]
US 5645637A
· Yaniv
· 1997
[cited by applicant]
US 5891983A
· Albrecht
· 1999
[cited by applicant]
US 6089318A
· Laramay et al.
· 2000
[cited by applicant]
US 6324916B1
· Jessop
· 2001
[cited by applicant]
US 6609067B2
· Tare
· 2003
[cited by applicant]
US 6664215B1
· Tomlinson
· 2003
[cited by applicant]
US 6668927B1
· Chatterji et al.
· 2003
[cited by applicant]
US 6828378B2
· Okumura et al.
· 2004
[cited by applicant]
US 6844852B1
· Simons
· 2005
[cited by applicant]
US 7077199B2
· Vinegar et al.
· 2006
[cited by applicant]
US 7497258B2
· Savery et al.
· 2009
[cited by applicant]
US 7523784B2
· Lewis et al.
· 2009
[cited by applicant]
US 7525872B2
· Tang et al.
· 2009
[cited by applicant]
US 7527098B2
· Santra et al.
· 2009
[cited by applicant]
US 7555414B2
· Calhoun
· 2009
[cited by applicant]
US 7612142B2
· Ito et al.
· 2009
[cited by applicant]
US 7622527B2
· Ito et al.
· 2009
[cited by applicant]
US 7637319B2
· Savery et al.
· 2009
[cited by applicant]
US 7654326B1
· Santra et al.
· 2010
[cited by applicant]
US 7773454B2
· Barolak et al.
· 2010
[cited by applicant]
US 7787327B2
· Tang et al.
· 2010
[cited by applicant]
US 7799867B2
· Ito et al.
· 2010
[cited by applicant]
US 7833344B2
· Santra et al.
· 2010
[cited by applicant]
US 7847049B2
· Ito et al.
· 2010
[cited by applicant]
US 7893011B2
· Lewis et al.
· 2011
[cited by applicant]
US 7893168B2
· Ito et al.
· 2011
[cited by applicant]
US 7943718B2
· Ito et al.
· 2011
[cited by applicant]
US 7981943B2
· Ito et al.
· 2011
[cited by applicant]
US 8007911B2
· Ito et al.
· 2011
[cited by applicant]
US 8017688B2
· Ito et al.
· 2011
[cited by applicant]
US 8124569B2
· Khan et al.
· 2012
[cited by applicant]
US 8142562B2
· Klettke et al.
· 2012
[cited by applicant]
US 8309498B2
· Funkhouser et al.
· 2012
[cited by applicant]
US 8382476B2
· Schulte et al.
· 2013
[cited by applicant]
US 8418763B1
· Deen et al.
· 2013
[cited by applicant]
US 8450252B2
· Funkhouser et al.
· 2013
[cited by applicant]
US 8450415B2
· Ito et al.
· 2013
[cited by applicant]
US 8580906B2
· Hayashi et al.
· 2013
[cited by applicant]
US 8587493B2
· Dickey et al.
· 2013
[cited by applicant]
US 8620636B2
· Zhan et al.
· 2013
[cited by applicant]
US 8673364B2
· Jalota et al.
· 2014
[cited by applicant]
US 8770038B2
· Secq
· 2014
[cited by applicant]
US 8899331B2
· Burnham
· 2014
[cited by applicant]
US 9023150B2
· Brenneis et al.
· 2015
[cited by applicant]
US 9068051B2
· Yamasaki et al.
· 2015
[cited by applicant]
US 9085487B2
· Da Silva et al.
· 2015
[cited by applicant]
US 9163499B2
· Adams et al.
· 2015
[cited by applicant]
US 9228993B2
· Shine et al.
· 2016
[cited by applicant]
US 9266972B2
· Yamasaki et al.
· 2016
[cited by applicant]
US 9375699B2
· Ladet
· 2016
[cited by applicant]
US 9428682B2
· Muthusamy et al.
· 2016
[cited by applicant]
US 9617460B2
· Reddy
· 2017
[cited by applicant]
US 9708869B2
· Sarmah et al.
· 2017
[cited by applicant]
US 20030138398A1
· Okumura et al.
· 2003
[cited by applicant]
US 20060048671A1
· Ong
· 2006
[cited by applicant]
US 20080006410A1
· Looney et al.
· 2008
[cited by applicant]
US 20080156225A1
· Bury
· 2008
[cited by applicant]
US 20080287633A1
· Drumheller
· 2008
[cited by applicant]
US 20090030108A1
· Ito et al.
· 2009
[cited by applicant]
US 20090214871A1
· Fukuda et al.
· 2009
[cited by applicant]
US 20090312491A1
· Ito et al.
· 2009
[cited by applicant]
US 20090312492A1
· Ruslim et al.
· 2009
[cited by applicant]
US 20100006288A1
· Santra et al.
· 2010
[cited by applicant]
US 20120006551A1
· Carman et al.
· 2012
[cited by applicant]
US 20130118740A1
· Sherman et al.
· 2013
[cited by applicant]
US 20140096964A1
· Chakraborty et al.
· 2014
[cited by applicant]
US 20140342531A1
· Tominaga et al.
· 2014
[cited by applicant]
US 20150024122A1
· Wu et al.
· 2015
[cited by applicant]
US 20150033719A1
· Lawrence et al.
· 2015
[cited by applicant]
US 20150057196A1
· Debord et al.
· 2015
[cited by applicant]
US 20150152724A1
· Amendt et al.
· 2015
[cited by applicant]
US 20150198008A1
· Smith et al.
· 2015
[cited by applicant]
US 20160102238A1
· Muthusamy et al.
· 2016
[cited by applicant]
US 20200062877A1
· Knopf
· 2020
[cited by examiner]
BR 102018014722
· 2020
[cited by applicant]
CN 104204035
· 2014
[cited by applicant]
CN 107522436
· 2017
[cited by applicant]
CN 109133754
· 2019
[cited by applicant]
CN 112456870
· 2021
[cited by applicant]
EP 0383348
· 1990
[cited by applicant]
EP 2820413
· 2015
[cited by applicant]
EP 3060909
· 2016
[cited by applicant]
JP H10158045
· 1998
[cited by applicant]
JP 2006316089A
· 2006
[cited by examiner]
JP 2016088878
· 2016
[cited by applicant]
JP 6647751
· 2020
[cited by applicant]
WO WO2016053319
· 2016
[cited by applicant]
WO WO2016080674
· 2016
[cited by applicant]
WO WO2019090140
· 2019
[cited by applicant]
WO WO2019147559
· 2019
[cited by applicant]
U.S. Appl. No. 16/393,016 filed Apr. 24, 2019, Hakimuddin.
[cited by applicant]
U.S. Appl. No. 16/593,820, filed Oct. 4, 2019, Patel et al.
[cited by applicant]
U.S. Appl. No. 16/668,730, filed Oct. 30, 2019, Patel et al.
[cited by applicant]
U.S. Appl. No. 17/107,428, filed Nov. 30, 2020, Hull et al.
[cited by applicant]
U.S. Appl. No. 17/550,631, filed Dec. 14, 2021, Patel et al.
[cited by applicant]
U.S. Appl. No. 63/289,308, filed Dec. 14, 2021, Hull et al.
[cited by applicant]
Acquah et al., “Carbon Nanotubes and Graphene as Additives in 3D Printing,” Carbon Nanotubes—Current Progress of Their Polymer Composites, InTech, 2016, 26 pages.
[cited by applicant]
Adhikary et al., “Effects of carbon nanotubes on expanded glass and silica aerogel based lightweight concrete,” Nature, Scientific Reports, Jan. 2021, 11:2104, 11 pages.
[cited by applicant]
Andrew, “Global CO
[cited by applicant]
API, “10B-2, Recommended Practice for Testing Well Cements,” American Petroleum Institute, Apr. 2019, 1-124, RP 10B-2, 124 pages.
[cited by applicant]
Arbad et al., “A Review of Recent Research on Contamination of Oil Well Cement with Oil-Based Drilling Fluid and the Need of New and Accurate Correlations,” ChemEngineering, Apr. 2020, 20 pages.
[cited by applicant]
Arts et al., “Seismic monitoring at the Sleipner underground CO
[cited by applicant]
Ashik et al., “A review on methane transformation to hydrogen and nanocarbon: Relevance of catalyst characteristics and experimental parameters on yield,” Renewable and Sustainable Energy Reviews, Sep. 2017, 76:743-767,…
[cited by applicant]
asmi.jp [online], “SeRM Series Products List,” asmi.jp, Advanced Softmaterials Inc., retrieved from URL <www.asmi.jp/en/product#sec_03>, retrieved on Aug. 15, 2019, available on or before Jan. 2013 (via wayback machine …
[cited by applicant]
Bagheri et al., “Rubber-toughened epoxies: a critical review,” Journal of Macromolecular Science, Part C: Polymer Reviews, Aug. 2009, 49.3:201-225, 25 pages.
[cited by applicant]
Bett, “Geothermal Well Cementing, Materials and Placement Techniques,” United Nations University, Geothermal Training Programme, Reports 2010, No. 10, 2010, 32 pages.
[cited by applicant]
Beyer, “Evolution of reservoir properties in the Lower Triassic aquifer sandstones of the Thuringian Syncline in Central Germany,” Dissertation zur Erlangung des akademischen Grades doctor rerum naturalium, Dr. rer. nat…
[cited by applicant]
Bouzalakos et al., “Overview of carbon dioxide (CO
[cited by applicant]
Brichni et al., “Optimisation of Magnesium Oxychloride Cement Properties by Silica Glass,” Adv. Cem. Res., Jul. 2016, 28:10 (654-663), 10 pages.
[cited by applicant]
Bruns and Stoddart, “The Nature of the Mechanical Bond: from molecules to machines,” Wiley, 2017, 786 pages.
[cited by applicant]
Buchanan et al., “Metal 3D printing in construction: A review of methods, research, applications, opportunities and challenges,” Engineering Structures, Feb. 2019, 180:332-348, 36 pages.
[cited by applicant]
Cao et al., “Study of the in-situ growth of carbon nanofibers on cement clinker,” Mater. Res. Express, May 2020, 7:5 (055306), 10 pages.
[cited by applicant]
Capper et al., “Internal antiplasticisation in highly crosslinked amine cured multifunctional epoxy resins,” Polymer, 2018, 146:321-330, 11 pages.
[cited by applicant]
Carey et al., “Fracture-permeability behavior of shale,” Journal of Unconventional Oil and Gas Resources, Sep. 2015, 11, 53 pages.
[cited by applicant]
Ceglar et al., “Deepwater outcrop analogue study: basal Bunkers Sandstone, Donkey Bore Syncline, Northern Flinders Ranges, Australia,” Petroleum Exploration Society of Australia (PESA), presented at the PESA Eastern Aus…
[cited by applicant]
Chambers et al., “Liquid crystal elastomer—nanoparticle systems for actuation,” Journal of Materials Chemistry, 2009, 19.11:1524-1531, 7 pages.
[cited by applicant]
Chatham et al., “A review of the process physics and material screening methods for polymer powder bed fusion additive manufacturing,” Progress in Polymer Science, Jun. 2019, 93:68-95, 28 pages.
[cited by applicant]
Chen et al., “Enhancement of mechanical and wear resistance performance in hBN reinforced epoxy nanocomposites,” Polym. Int., 2017, 66: 659, 25 pages.
[cited by applicant]
Chen et al., “Rapid control of phase growth by nanoparticles,” Nature Communications, May 2014, 5.1, 9 pages.
[cited by applicant]
Cho et al., “Cell-Encapsulating Hydrogel Puzzle: Polyrotaxane-Based Self-Healing Hydrogels,” Chem. Eur. J., 2019, 26:4 (913-920), 22 pages.
[cited by applicant]
Choi et al., “Highly elastic binders integrating polyrotaxanes for silicon microparticle anodes in lithium ion batteries,” Science, Jul. 2017, 357.6348:279-283, 5 pages.
[cited by applicant]
Cordero et al., “Strengthening of ferrous binder jet 3D printed components through bronze infiltration,” Additive Manufacturing, May 2017, 15:87-92, 6 pages.
[cited by applicant]
Cui et al., “Electrical and mechanical properties of electrically conductive adhesives from epoxy, micro-silver flakes, and nano-hexagonal boron nitride particles after humid and thermal aging,” International Journal of…
[cited by applicant]
Davidson et al., “3D Printable and Reconfigurable Liquid Crystal Elastomers with Light-Induced Shape Memory via Dynamic Bond Exchange,” Advanced Materials, Jan. 2020, 6 pages.
[cited by applicant]
DebRoy et al., “Additive manufacturing of metallic components—process, structure and properties,” Progress in Materials Science, Mar. 2018, 92:112-224, 114 pages.
[cited by applicant]
DebRoy et al., “Scientific, technological and economic issues in metal printing and their solutions,” Nature Materials, Jul. 2019, 18, 7 pages.
[cited by applicant]
Dowling et al., “A review of critical repeatability and reproducibility issues in powder bed fusion,” Materials & Design, Jan. 2020, 186, 18 pages.
[cited by applicant]
Eiken et al., “Lessons learned from 14 years of CCS operations: Sleipner, In Salah and Snøhvit,” Energy Procedia, 2011, 4: 5541-5548, 8 pages.
[cited by applicant]
El-Wardany et al., “Challenges in three-dimensional printing of high-conductivity copper,” Journal of Electronic Packaging, Jun. 2018, 140.2:020907, 12 pages.
[cited by applicant]
Enayatpour et al., “Advanced Modeling of Cement Displacement Complexities,” SPE/IADC-184702-MS, Society of Petroleum Engineers (SPE), presented at the SPE/IADC Drill Conference and Exhibition, Mar. 2017, 21 pages.
[cited by applicant]
EPA, “UIC Pressure Falloff Testing Guideline,” EPA Region 6, Aug. 8, 2002, 29 pages.
[cited by applicant]
Fayazfar et al., “A critical review of powder-based additive manufacturing of ferrous alloys: Process parameters, microstructure and mechanical properties,” Materials & Design, Apr. 2018, 144:98-128, 31 pages.
[cited by applicant]
Foldyna et al., “Dispersion of carbon nanotubes for application in cement composites,” Science Direct, Procedia Engineering, 2016, 149:94-99, 6 pages.
[cited by applicant]
Funkhouser and Norman, “Synthetic Polymer Fracturing Fluid for High-Temperature Application,” SPE 80236, Society of Petroleum Engineers (SPE), International Symposium on Oilfield Chemistry, Feb. 5-7, 2003, 6 pages.
[cited by applicant]
Gaillard et al., “Novel Associative Acrylamide-based Polymers for Proppant Transport in Hydraulic Fracturing Fluids,” SPE 164072, Society of Petroleum Engineers (SPE), SPE International Symposium on Oilfield Chemistry, …
[cited by applicant]
Gelebart et al., “Photoresponsive fiber array: toward mimicking the collective motion of cilia for transport applications,” Advanced Functional Materials, Aug. 2016, 26.29:5322-5327, 6 pages.
[cited by applicant]
Genedy et al., “Examining epoxy-based nanocomposites in wellbore seal repair for effective CO
[cited by applicant]
Gislason et al., “Carbon Storage in Basalt,” Science, 2014, 344:6182 (373-374), 3 pages.
[cited by applicant]
Gladman et al., “Biomimetic 4D printing,” Nature Materials, Apr. 2016, 15.4:413-418, 7 pages.
[cited by applicant]
Global Status of CCS Report, Dec. 11, 2020, Global CCS Institute, 44 pages.
[cited by applicant]
Goeppert et al., “Air as the renewable carbon source of the future: an overview of CO
[cited by applicant]
Gojny et al., “Carbon nanotube-reinforced epoxy-composites: enhanced stiffness and fracture toughness at low nanotube content,” Compos. Sci. Technol., 2004, 64:2363-2371, 9 pages.
[cited by applicant]
Gong et al., “Analysis of defect generation in Ti—6Al—4V parts made using powder bed fusion additive manufacturing processes,” Additive Manufacturing, Oct. 2014, 1, 60 pages.
[cited by applicant]
Gorsse et al., “Additive manufacturing of metals: a brief review of the characteristic microstructures and properties of steels, Ti—6Al—4V and high-entropy alloys,” Science and Technology of Advanced Materials, Dec. 201…
[cited by applicant]
Guo et al., “Shape memory epoxy composites with high mechanical performance manufactured by multi-material direct ink writing,” Compos. Part A Appl. Sci. Manuf., 2020, 135: 105903, 8 pages.
[cited by applicant]
Gupta and Carman, “Fracturing Fluid for Extreme Temperature Conditions is Just as Easy as the Rest,” SPE 140176, Society of Petroleum Engineers (SPE), SPE Hydraulic Fracturing Technology Conference, Jan. 24-26, 2011, 5 …
[cited by applicant]
Hannis et al., “CO
[cited by applicant]
Harada et al., “Preparation and properties of inclusion complexes of polyethylene glycol with α-cyclodextrin,” Macromolecules, 1993, 26:5698-5703, 6 pages.
[cited by applicant]
Harada et al., “Supramolecular polymeric materials via cyclodextrin—guest interactions,” Accounts of Chemical Research, Jul. 2014, 47.7:2128-2140, 13 pages.
[cited by applicant]
Hart et al., “Material properties and applications of mechanically interlocked polymers,” Nat. Rev. Mater., 2021, 6:6 (508-530), 23 pages.
[cited by applicant]
Hepburn et al., “The technological and economic prospects for CO
[cited by applicant]
Herzog et al., “Additive Manufacturing of Metals,” Acta Mater. 2016, 117:371-392, 22 pages.
[cited by applicant]
Hitzler et al., “In-plane anisotropy of selective laser-melted stainless steel: The importance of the rotation angle increment and the limitation window,” Proceedings of the Institution of Mechanical Engineers, Part L: …
[cited by applicant]
Hojjatzadeh et al., “Direct observation of pore formation mechanisms during LPBF additive manufacturing process and high energy density laser welding,” International Journal of Machine Tools and Manufacture 153:103555, …
[cited by applicant]
Houben et al., “Plasticization behavior of crown-ether containing polyimide membranes for the separation of CO
[cited by applicant]
Hoyos-Palacio et al., “Catalytic effect of Fe, Ni, Co and Mo on the CNTs production,” IOP Conference Series: Materials Science and Engineering, 2014, 59:012005, 9 pages.
[cited by applicant]
Huang et al., “Finite element analysis of thermal behavior of metal powder during selective laser melting,” International Journal of Thermal Sciences, Jun. 2016, 104:146-157, 12 pages.
[cited by applicant]
Hull et al., “Chemomechanical Effects of Oxidizer-CO
[cited by applicant]
Hull et al., “Oxidative Kerogen Degradation: A Potential Approach to Hydraulic Fracturing in Unconventionals,” Energy Fuels, 2019, 33: 4758-4766, 8 pages.
[cited by applicant]
Hull et al., “Synthesis and structural characterization of CO
[cited by applicant]
Hur et al., “Reactive force fields for modeling oxidative degradation of organic matter in geological formations,” RSC Adv. 2021, 11:29298-29307, 23 pages.
[cited by applicant]
IEAGHG, “Case Studies of CO
[cited by applicant]
IPCC, “Special Report on Carbon Dioxide Capture and Storage,” in Metz et al., Working Group III of the Intergovernmental Panel on Climate Change, 2005, 443 pages.
[cited by applicant]
Isaka et al., “Influence of long-term operation of supercritical carbon dioxide based enhanced geothermal system on mineralogical and microstructurally-induced mechanical alteration of surrounding rock mass,” Renewable …
[cited by applicant]
Isfahani et al., “Dispersion of multi-walled carbon nanotubes and its effects on the properties of cement composites,” Cement and Concrete Composites, Nov. 2016, 74:154-163, 10 pages.
[cited by applicant]
Isobe et al., “Thermally dissociable pseudo-polyrotaxane as a supramolecular shrinkage suppressor for epoxy-amine curing system,” Journal of Polymer Science Part A: Polymer Chemistry, Mar. 2008, 46.6:2305-2308, 4 pages.
[cited by applicant]
Jafariesfad et al., “Cement Sheath Modification Using Nanomaterials for Long-term Zonal Isolation of Oil Wells: Review,” Journal of Petroleum Science and Engineering., 2017, 156:662-672, 28 pages.
[cited by applicant]
Jiang et al., “Highly Stretchable and Instantly Recoverable Slide-Ring Gels Consisting of Enzymatically Synthesized Polyrotaxane with Low Host Coverage,” Chem. Mater., 2018, 30:15 (5013), 10 pages.
[cited by applicant]
Jin et al., “Synthesis and application of epoxy resins: A review,” J. Ind. Eng. Chem., Sep. 2015, 29:1-11, 11 pages.
[cited by applicant]
Kato et al., “Organic-Inorganic Hybrid Slide-Ring Gels: Polyrotaxanes Consisting of Poly(dimethylsiloxane) and γ-Cyclodextrin and Subsequent Topological Cross-Linking,” Macromolecules, Aug. 18, 2009, 42:7129-7136, 8 pag…
[cited by applicant]
Khuenkaew et al., “Resistance spot welding of SUS316L austenitic/SUS425 ferritic stainless steels: weldment characteristics, mechanical properties, phase transformation and solidification,” Metals, Jun. 2019, 9.6, 17 pa…
[cited by applicant]
Kim et al., “Development of CO
[cited by applicant]
Koyanagi et al., “Movable Cross-Linked Polymeric Materials from Bulk Polymerization of Reactive Polyrotaxane Cross-Linker with Acrylate Monomers,” Macromolecules 2017, 50:5695-5700, 6 pages.
[cited by applicant]
Kuo et al., “Bonding behavior of repair material using fly-ash/ground granulated blast furnace slag-based geopolymer,” Materials, Jan. 2019, 12.10, 16 pages.
[cited by applicant]
Ladva et al., “The Cement-to-Formation Interface in Zonal Isolation,” IADC/SPE 88016, Society of Petroleum Engineers (SPE), presented at the IADC/SPE Asia Pacific Drilling Technology Conference and Exhibition in Kuala L…
[cited by applicant]
Levenfeld et al., “Effect of residual carbon on the sintering process of M2 high speed steel parts obtained by a modified metal injection molding process,” Metallurgical and Materials Transactions, Jun. 2002, A:33.6 (18…
[cited by applicant]
Lewis et al., “Direct ink writing of three-dimensional ceramic structures,” Journal of the American Ceramic Society, Dec. 2006, 89.12:3599-3609, 11 pages.
[cited by applicant]
Li et al., “Contamination of Cement Slurries with Diesel-Based Drilling Fluids in a Shale Gas Well,” J. Nat. Gas Sci. Eng., Aug. 2015, 27:1312-1320, 9 pages.
[cited by applicant]
Li et al., “Residual stress in metal additive manufacturing,” Procedia Cirp, Jan. 2018, 71:348-353, 6 pages.
[cited by applicant]
Li et al., “Slide-ring shape memory polymers with movable cross-links,” React. Funct. Polym., 2017, 119:26-36, 25 pages.
[cited by applicant]
Li et al., “The pore-fracture system properties of coalbed methane reservoirs in the Panguan Syncline, Guizhou, China,” Geoscience Frontiers, 2012, 3:6 (853-862), 10 pages.
[cited by applicant]
Lin et al., “Rapid macroscale shape morphing of 3D-printed polyrotaxane monoliths amplified from pH-controlled nanoscale ring motions,” J. Mater. Chem., 2018, C:6 (11956), 5 pages.
[cited by applicant]
Lin et al., “Ring Shuttling Controls Macroscopic Motion in a Three-Dimensional Printed Polyrotaxane Monolith,” Chem. Int. Ed., 2017, 56:4452-4457, 7 pages.
[cited by applicant]
Liu et al., “A novel method to evaluate cement shale bond strength,” SPE-173802-MS, Society of Petroleum Engineers (SPE), presented at the SPE International Symposium on Oilfield Chemistry, The Woodlands, Texas, Apr. 13…
[cited by applicant]
Liu et al., “Graphene Lubricant,” Applied Materials Today, 2020, 20:2020 (100662), 31 pages.
[cited by applicant]
Loizzo et al., “Reusing O&G-Depleted Reservoirs for CO2 Storage: Pros and Cons,” SPE 124317, Society of Petroleum Engineers (SPE), presented at the 2009 SPE Offshore Europe and Gas Conference & Exhibition, Sep. 8-11, 20…
[cited by applicant]
Luo et al., “A survey of finite element analysis of temperature and thermal stress fields in powder bed fusion additive manufacturing,” Additive Manufacturing, May 2018, 21:318-332, 15 pages.
[cited by applicant]
Mather et al., “Michael addition reactions in macromolecular design for emerging technologies,” Progress in Polymer Science, May 2006, 31.5:487-531, 45 pages.
[cited by applicant]
Mayumi et al., “Structure and dynamics of polyrotaxane and slide-ring materials,” Polymer, 2010, 51:959-967, 9 pages.
[cited by applicant]
Mikhalchan et al., “Aligned carbon nanotube-epoxy composites: the effect of nanotube organization on strength, stiffness, and toughness,” J. Mater. Sci., 2016, 51:10005-10025, 21 pages.
[cited by applicant]
Mostafaei et al., “Binder jet 3D printing—Process parameters, materials, properties, modeling, and challenges,” Progress in Materials Science, Jun. 2021, 119:100707, 141 pages.
[cited by applicant]
Nakahata et al., “Self-Healing Materials Formed by Cross-Linked Polyrotaxanes with Reversible Bonds,” Chem, 2016, 1:5 (766-775), 11 pages.
[cited by applicant]
Nelson and Guillot, “Well Cementing,” Second Edition, Schlumberger, 2006, 807 pages.
[cited by applicant]
Obayi et al., “Effect of grain sizes on mechanical properties and biodegradation behavior of pure iron for cardiovascular stent application,” Biomatter, Jan. 2016, 6.1:e959874, 10 pages.
[cited by applicant]
Ohm et al., “Liquid Crystalline Elastomers as Actuators and Sensors,” Advanced Materials, Aug. 2010, 22: 3366-3387, 22 pages.
[cited by applicant]
Oliveira et al., “Processing parameters in laser powder bed fusion metal additive manufacturing,” Materials & Design, Aug. 2020, 193, 12 pages.
[cited by applicant]
Opedal et al., “Experimental study on the cement-formation bonding,” SPE 168138, Society of Petroleum Engineers (SPE), presented at the SPE International Symposium and Exhibition on Formation Damage Control, Lafayette, …
[cited by applicant]
Pau et al., “High-resolution simulation and characterization of density-driven flow in CO
[cited by applicant]
Payenberg et al., “Architecture of a deep-water, salt-withdrawal mini-basin, Donkey Bore Syncline, Australia,” in Nilse et al., Atlas of Deep-Water Outcrops, 2008, 6 pages.
[cited by applicant]
Peerzada et al., “Additive Manufacturing of Epoxy Resins: Materials, Methods, and Latest Trends,” Ind. Eng. Chem. Res., 2020, 59:14, 52 pages.
[cited by applicant]
Prabhakar et al., “Enhancing the Gel Transition Time and Right-Angle-Set Property of Oil Well Cement Slurries by Incorporating CSA Cement and Gypsum,” IPTC-19224-MS, International Petroleum Technology Conference, Mar. 2…
[cited by applicant]
Prajapati et al., “Measurement of anisotropic thermal conductivity and inter-layer thermal contact resistance in polymer fused deposition modeling (FDM),” Additive Manufacturing, May 2018, 21:84-90, 7 pages.
[cited by applicant]
Pruksawan et al., “Homogeneously Dispersed Polyrotaxane in Epoxy Adhesive and Its Improvement in the Fracture Toughness,” Macromolecules, 2019, 52:2464-2475, 12 pages.
[cited by applicant]
Radonjic and Oyibo, “Experimental evaluation of wellbore cement-formation shear bond strength in presence of drilling fluid contamination,” International Conference on porous media and their applications in science, eng…
[cited by applicant]
Ramsdale-Capper et al., “Internal antiplasticisation in highly crosslinked amine cured multifunctional epoxy resins,” Polymer, Jun. 2018, 146:321-330, 10 pages.
[cited by applicant]
Reddy et al., “Relating Cement Additive Performance to Mix Water Composition for Deep Water and Salt Zone Applications,” SPE-180344-MS, Society of Petroleum Engineers (SPE), SPE Deepwater Drilling and Completions Confer…
[cited by applicant]
Rimdusit et al., “Shape memory polymers from benzoxazine-modified epoxy,” Smart Mater. Struct., 2013, 22:075033, 13 pages.
[cited by applicant]
Ringrose, “How to store CO
[cited by applicant]
Roca et al., “Policy needed for additive manufacturing,” Nature Materials, Aug. 2016, 15:8, 4 pages.
[cited by applicant]
Saed et al., “Molecularly-engineered, 4D-Printed liquid crystal elastomer actuators,” Advanced Functional Materials, 2019, 29.3, 9 pages.
[cited by applicant]
Sajadi et al., “Direct ink writing of cement structures modified with nanoscale additive,” Advanced Engineering Materials, Aug. 2019, 21.8:1801380, 10 pages.
[cited by applicant]
Seo et al., “Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin,” Chem. Eng. J., 2019, 356:303-311, 30 pages.
[cited by applicant]
Seo et al., “Enhanced Mechanical Strength, Flexibility, and Shape-Restoring Rate of a Drug-Eluting Shape-Memory Polymer by Incorporation of Supramolecular Cross-Linkers,” ACS Macro Lett., 2020, 9, 389-395, 7 pages.
[cited by applicant]
Simao et al., “Cementing Solutions for Salt- and CO
[cited by applicant]
Singh et al., “Powder bed fusion process in additive manufacturing: An overview,” Materials Today: Proceedings, Jan. 2020, 26:3058-3070, 13 pages.
[cited by applicant]
Snow et al., “Invited Review Article: Review of the formation and impact of flaws in powder bed fusion additive manufacturing,” Additive Manufacturing, Jul. 2020, 15 pages.
[cited by applicant]
Soto et al., “Self-assembly of a supramolecular network with pseudo-rotaxane cross-linking nodes and its transformation into a mechanically locked structure by rotaxane formation,” Chemical Communications, 2016, 52:1414…
[cited by applicant]
Sun et al., “Short-aramid-fiber toughening of epoxy adhesive joint between carbon fiber composites and metal substrates with different surface morphology,” Compos. Part B Eng., 2015, 77:38-45, 30 pages.
[cited by applicant]
Tagliaferri et al., “Direct ink writing of energy materials,” Materials Advances, 2021, 2.2:540-563, 24 pages.
[cited by applicant]
Tao et al., “A Brief Review of Gas Migration in Oilwell Cement Slurries,” Energies, 2021, 14:2369, 22 pages.
[cited by applicant]
Telschow et al., “Cement Formation—A Success Story in a Black Box: High Temperature Phase Formation of Portland Cement Clinker,” Industrial & Engineering Chemistry Research (I&EC Research), American Chemical Society (AC…
[cited by applicant]
Tong et al., “Committed Emissions from Existing Energy Infrastructure Jeopardize 1.5° C Climate Target,” Nature, 2019, 572:7769 (373-377), 17 pages.
[cited by applicant]
Tran et al., “3D printing of highly pure copper,” Metals, Jul. 2019, 9.7:756, 24 pages.
[cited by applicant]
Ürk et al., “Structure-controlled growth of vertically-aligned carbon nanotube forests using iron-nickel bimetallic catalysts,” Materials Advances, 2021, 2:2021-2030, 10 pages.
[cited by applicant]
Utela et al., “A review of process development steps for new material systems in three dimensional printing (3DP),” Journal of Manufacturing Processes, Jul. 2008, 10.2:96-104, 9 pages.
[cited by applicant]
Vyavahare et al., “Fused deposition modelling: A review,” Rapid Prototyping Journal, Jan. 2020, 26 pages.
[cited by applicant]
Wang et al., “Molecular Simulation of CO
[cited by applicant]
Wang et al., “Relaxation and Reinforcing Effects of Polyrotaxane in an Epoxy Resin Matrix,” Macromolecules, 2006, 39:3 (1046-1052), 7 pages.
[cited by applicant]
Weir et al., “Reservoir storage and containment of greenhouse gases,” Transport in Porous Media, Energy Convers. Mgmt, 36, 531-534 1995, 7 pages.
[cited by applicant]
Welch et al., “Shear strength and permeability of the cement-casing interface,” International Journal of Greenhouse Gas Control, Apr. 2020, 95, 29 pages.
[cited by applicant]
Wenz et al., “Cyclodextrin Rotaxanes and Polyrotaxanes,” Chem. Rev., 2006, 106:782-817, 36 pages.
[cited by applicant]
Wimpenny et al., “Advances in 3D printing & additive manufacturing technologies,” Singapore: Springer, 2017, 195 pages.
[cited by applicant]
Wu et al., “A Crown Ether-Containing Copolyimide Membrane with Improved Free Volume for CO
[cited by applicant]
Wu et al., “High-strain slide-ring shape-memory polycaprolactone-based polyurethane,” Soft Matter, 2018, 14:4558, 28 pages.
[cited by applicant]
Yakovlev et al., “Modification of Cement Matrix Using Carbon Nanotube Dispersions and Nanosilica,” Science Direct, Procedia Engineering, Modern Building Materials, Structures and Techniques, MBMST 2016, 2017, 172:1261-1…
[cited by applicant]
Zhan et al., “In situ-grown carbon nanotubes enhanced cement-based materials with multifunctionality,” Cement and Concrete Composites, Apr. 2020, 108:103518, 11 pages.
[cited by applicant]
Zhang et al., “Dibenzo-21-crown-7-ether contained 6FDA-based polyimide membrane with improved gas selectivity,” Separation and Purification Technology, 2021, 264:118454, 13 pages.
[cited by applicant]
Zhang et al., “Three-Dimensional Printing of Continuous Flax Fiber-Reinforced Thermoplastic Composites by Five-Axis Machine,” Materials, 2020, 13:1678, 11 pages.
[cited by applicant]
Zoback, “Reservoir geomechanics,” Cambridge University Press, 2010, 2 pages.
[cited by applicant]