Self-degrading fibers and associated methods of use and manufacture

Illllllllllllllllllllllllllllllllllllllllllllllllll

US007267170B2

(12;

United States Patent

Mang et al.

(io) Patent No.: (45) Date of Patent:

US 7,267,170 B2 Sep.11, 2007

(54) SELF-DEGRADING FIBERS AND

ASSOCIATED METHODS OF USE AND
MANUFACTURE

(75) Inventors: Michael N. Mang, Eden Prairie, MN (US); Bradley L. Todd, Duncan, OK (US)

(73) Assignee: Halliburton Energy Services, Inc.,

Duncan, OK (US)

( * ) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 287 days.

(21) Appl. No.: 11/048,417

(22) Filed: Jan. 31, 2005

(65) Prior Publication Data

US 2006/0169449 Al Aug. 3, 2006

(51) Int. CI.

E21B 43/04 (2006.01)
E21B 43/267 (2006.01)
E21B 33/138 (2006.01)

(52) U.S. CI 166/279; 166/278; 166/280.1;

166/293; 166/308.3

(58) Field of Classification Search None

See application file for complete search history.

(56) References Cited

U.S. PATENT DOCUMENTS

2.238.671 A 4/1941 Woodhouse 166/21

2,703,316 A 3/1955 Palmer 260/78.3

3,173,484 A 3/1965 Huitt et al 166/280.1

3,195,635 A 7/1965 Fast 166/280.1

3,272,650 A 9/1966 MacVittie 134/7

3,302,719 A 2/1967 Fischer 166/280.2

3,364,995 A 1/1968 Atkins et al 166/280.1

3,366,178 A 1/1968 Malone et al 166/280.1

3,455,390 A 7/1969 Gallus 166/295

3,784,585 A 1/1974 Schmitt et al 260/861

3,819,525 A 6/1974 Hattenbran 252/132

3,828,854 A 8/1974 Templeton et al 166/307

3,868,998 A 3/1975 Lybarger et al 166/278

3,912,692 A 10/1975 Casey et al 260/78.3

3.948.672 A 4/1976 Harnsberger 106/90

3,955,993 A 5/1976 Curtice et al 106/90

3,960,736 A 6/1976 Free et al 252/8.55 R

3,968,840 A 7/1976 Tate 166/280.1

3,998,272 A 12/1976 Maly 166/281

3,998,744 A 12/1976 Arnold et al 507/269

4,068,718 A 1/1978 Cooke, Jr. et al 166/280.2

4,169,798 A 10/1979 DeMartino 252/8.55 R

4,172,066 A 10/1979 Zweigle et al 260/29.6 TA

4,261,421 A 4/1981 Watanabe 166/281

4,322,381 A 3/1982 Joh 264/41

4,323,627 A 4/1982 Joh 428/398

4,342,711 A 8/1982 Joh et al 264/41

4,385,017 A 5/1983 Joh et al 264/41

4,387,769 A 6/1983 Erbstoesser et al 166/295

4,388,256 A 6/1983 Ishida et al 264/41

4,460,052 A 7/1984 Gockel 175/72

4,470,915 A 9/1984 Conway 252/8.55 R

Gockel 252/8.5 LC

Erbstoesser et al. ... 252/8.55 R

Armbruster 166/280

Bellis et al 252/8.551

Erbstoesser et al 166/284

Armbruster 166/280

Dewitz 422/142

Hollenbeck et al 166/307

Pober 166/295

Lai et al 524/555

Cantu et al 166/281

Repetti et al 264/41

Welch et al 356/70

Cantu et al 166/295

Himes et al 166/250

Clark etal 166/279

Cantu et al 166/279

Casadetal 166/295

Tackett, Jr 166/295

Gruberetal 528/354

Sinclair 524/108

Gruberetal 528/354

Surjaatmadia 166/305

Cole et al 166/278

Surjaatmadja et al 166/308

Card et al 166/280

U.S. PATENT DOCUMENTS

5,359,026 A 10/1994 Graber 528/354

5,360,068 A 11/1994 Sprant et al 166/259

5,363,916 A 11/1994 Himes et al 166/276

5,373.901 A 12/1994 Norman et al 166/300

5,386,874 A 2/1995 Laramay et al 166/300

5,396,957 A 3/1995 Surjaatmadja et al 166/308

5,402,846 A 4/1995 Jennings, Jr. et al 166/259

5,439,055 A 8/1995 Card et al 166/280

5,460,226 A 10/1995 Lawton et al 166/300

5,464,060 A 11/1995 Hale et al 166/293

5,475,080 A 12/1995 Graber et al 528/354

5,484,881 A 1/1996 Graber et al 528/354

5,497,830 A 3/1996 Boles et al 166/300

5,499,678 A 3/1996 Surjaatmadja et al 166/298

5,501,275 A 3/1996 Card et al 166/280

5,505,787 A 4/1996 Yamaguchi 134/4

5,512,071 A 4/1996 Yam et al 51/307

5,536,807 A 7/1996 Graber et al 528/354

5,591,700 A 1/1997 Harris et al 507/204

5,594,095 A 1/1997 Graber et al 528/354

5,604,186 A 2/1997 Hunt et al 507/204

5,607,905 A 3/1997 Dobson, Jr. et al 507/211

5,670,473 A 9/1997 Scepanski 510/445

5,697,440 A 12/1997 Weaver et al 166/281

5,698,322 A 12/1997 Tsai et al 428/373

5.765.642 A 6/1998 Surjaatmadja 166/297

5.791.415 A 8/1998 Nguyen et al 166/280

5,833,000 A 11/1998 Weaver et al 166/276

5,849,401 A 12/1998 El-Afandi et al 428/215

5,853,048 A 12/1998 Weaver et al 166/279

5.893.416 A 4/1999 Read 166/304

5,908,073 A 6/1999 Nguyen et al 166/276

5,924,488 A 7/1999 Nguyen et al 166/280

5,964,291 A 10/1999 Bourne et al 166/279

6,004,400 A 12/1999 Bishop et al 134/2

6,024,170 A 2/2000 McCabe et al 166/300

6,028,113 A 2/2000 Scepanski 514/643

6.047.772 A 4/2000 Weaver et al 166/276

6,114,410 A 9/2000 Betzold 523/130

6,123,965 A 9/2000 Jacob et al 424/489

6,131,661 A 10/2000 Conner et al 166/300

6,135,987 A 10/2000 Tsai et al 604/365

6,143,698 A 11/2000 Murphey et al 507/145

6,162,766 A 12/2000 Muir et al 507/267

6,169,058 Bl 1/2001 Le et al 507/222

6,172,011 Bl 1/2001 Cardetal 507/204

6,189,615 Bl 2/2001 Sydansk 166/270

6,202,751 Bl 3/2001 Chatterji et al 166/276

6.209.643 Bl 4/2001 Nguyen et al 166/276

6,209,646 Bl 4/2001 Reddy et al 166/300

6.214.773 Bl 4/2001 Harris et al 507/271

6,242,390 Bl 6/2001 Mitchell et al 507/211

6,260,622 Bl 7/2001 Blok et al 166/305.1

6,311,773 Bl 11/2001 Todd et al 166/280

6,323,307 Bl 11/2001 Bigg et al 528/354

6,326,458 Bl 12/2001 Graber et al 528/354

6,328,105 Bl 12/2001 Betzold 166/280

6,357,527 Bl 3/2002 Norman et al 166/300

6,364,945 Bl 4/2002 Chatterji et al 106/677

6,380,138 Bl 4/2002 Ischy et al 507/204

6,387,986 Bl 5/2002 Moradi-Araghi et al. ... 523/211

6,390,195 Bl 5/2002 Nguyen et al 166/276

6,394,185 Bl 5/2002 Constien 166/296

6,422,314 Bl 7/2002 Todd et al 166/312

6,454,003 Bl 9/2002 Chang et al 166/270

6,485,947 Bl 11/2002 Rajgarhia et al 435/139

6,488,763 B2 12/2002 Brothers et al 106/692

6,494,263 B2 12/2002 Todd 166/312

6,508,305 Bl 1/2003 Brannon et al 166/293

6,527,051 Bl 3/2003 Reddy et al 166/300

6,554,071 Bl 4/2003 Crook et al 166/293

6,569,814 Bl 5/2003 Brady et al 507/201

6,599,863 Bl 7/2003 Palmer et al 507/219

6,667,279 Bl 12/2003 Hessert et al 507/225

6,669,771 B2 12/2003 Tokiwa et al 106/162.7

6,681,856 Bl 1/2004 Chatterji et al 166/294

6,686,328 Bl 2/2004 Binder 510/446

6,702,023 Bl 3/2004 Harris et al 166/307

6,710,019 Bl 3/2004 Sawdon et al 507,136

6,761,218 B2 7/2004 Nguyen et al 166/278

6,763,888 Bl 7/2004 Harris et al 166/305.1

6,817,414 B2 11/2004 Lee 166/278

6,896,058 B2 5/2005 Munoz, Jr. et al 166/279

6,949,491 B2 9/2005 Cooke, Jr 507/219

2001/0016562 Al 8/2001 Muir et al 507/201

2002/0036088 Al 3/2002 Todd 166/300

2002/0125012 Al 9/2002 Dawson et al 166/300

2003/0060374 Al 3/2003 Cooke, Jr 507/200

2003/0114314 Al 6/2003 Ballard et al 507/100

2003/0130133 Al 7/2003 Vollmer 507/100

2003/0188766 Al 10/2003 Banerjee et al 134/7

2003/0234103 Al 12/2003 Lee et al 166/293

2004/0014607 A1 1/2004 Sinclair et al 507/200

2004 0040706 Al 3/2004 Hossaini et al 166/278

2004/0055747 Al 3/2004 Lee 166/278

2004/0094300 Al 5/2004 Sullivan et al 166/308.1

2004/0106525 Al 6/2004 Willbert et al 507/200

2004/0138068 Al 7/2004 Rimmer et al 507/100

2004/0152601 Al 8/2004 Still et al 507/100

2004/0152602 Al 8/2004 Boles 507/100

2004/0170836 Al 9/2004 Bond et al 428/398

2004/0216876 Al 11/2004 Lee 166/280.1

2004/0231845 Al 11/2004 Cooke, Jr 166/279

2004/0261993 Al 12/2004 Nguyen 166/276

2004/0261995 Al 12/2004 Nguyen et al 166/279

2004/0261996 Al 12/2004 Munoz, Jr. et al 166/279

2004/0261999 Al 12/2004 Nguyen 166 292

2005/0006095 Al 1/2005 Justus et al 166/295

2005/0028976 Al 2/2005 Nguyen 166/276

2005/0034861 Al 2/2005 Saini et al 166/278

2005/0034865 Al 2/2005 Todd et al 166/304

2005/0034868 Al 2/2005 Frost et al 166/307

2005/0103496 Al 5/2005 Todd et al 166/278

2005/0252659 Al 11/2005 Sullivan et al 166/280.1

2005/0272613 Al 12/2005 Cooke, Jr 507/219

Yin, et al., Synthesis and Properties of Polymers Derived form Substituted Lactic Acids, American Chemical Society, Ch. 12, 2001 (pp. 147-159).

Cantu, et al, Laboratory and Field Evaluation of a Combined
Fluid-Loss-Control Additive and Gel Breaker for Fracturing Fluids,
SPE 18211, Society of Petroleum Engineers, 1990.
Love, et al, Selectively Placing Many Fractures in Openhole
Horizontal Wells Improves Production, SPE 50422, Society of
Petroleum Engineers, 1998.

McDaniel, et al, Evolving New Stimulation Process Proves Highly Effective in Level 1 Dual-Lateral Completion, SPE 78697, Society of Petroleum Engineers, 2002.

Albertsson, et al, Aliphatic Polyesters: Systhesis, Properties and Applications, Advances in Polymer Science, vol. 157, 2002. Dechy-Cabaret, et al, Controlled Ring-Opening Polymerization of Lactide and Glycolide, American Chemical Society, Chemical Reviews, A-Z, AA-AD, received 2004.

Funkhouser, et al, Synthetic Polymer Fracturing Fluid for HighTemperature Applications, SPE 80236, Society of Petroleum Engineers, 2003.

Chelating Agents, Encyclopedia of Chemical Technology, vol. 5 (764-795), undated.

Vichaibun, et al, A New Assay for the Enzymatic Degradation of Polylactic Acid, Short Report, ScienceAsia, vol. 29, 2003 (pp. 297-300).

Halliburton, SurgiFrac5" Service, A Quick and Cost-Effective Method to Help Boost Production From Openhole Horizontal Completions, Halliburton Communications, H03297, 2002. Halliburton, Cobra FracSM Service, Coiled Tubing Fracturing—Cost-Effective Method for Stimulating Untapped Reserves, H02319R, Halliburton Energy Services, 2000. Halliburton, CobraJet Frac!TM Service, Cost-effective Technology That Can Help Reduce Cost Per BOE Produced, Shorten Cycle Time and Reduce Capex, Halliburton Communications, undated. Polymer Processes, Chemical Technology of Plastics, Resins, Rubbers, Adhesives and Fibers, Interscience Publishers Inc, New York, p. 876, undated.

Mc-Graw-Hill Encyclopedia of Science & Technology, 5th Edition, McGraw-Hill Book Company, New York, p. 461, undated. Thesaurus of Textile Terms Covering Fibrous Materials and Processes, Second Edition, The M.I.T. Press, pp. xiii & 109, undated. Manufacturing: Synthetic and Cellulosic Fiber Formation Technology, American Fiber Manufacturers Association/Fiber Economics Bureau website, undated.

Y. Chiang et al.: "Hydrolysis of Ortho Esters: Further Investigation of the Factors Which Control the Rate-Determining Step," Engineering Information Inc., NY, NY, vol. 105, No. 23 (XP-002322842), Nov. 16, 1983.

M. Ahmad, et al.: Ortho Ester Hydrolysis: Direct Evidence for a Three-Stage Reaction Mechanism, Engineering Information Inc., NY, NY, vol. 101, No. 10 (XP-002322843), May 9, 1979.

Skrabal et al., The Hydrolysis Rate of Orthoformic Acid Ethyl Ether, Chemical Institute of the University of Graz, pp. 1-38, Jan. 13, 1921.

Heller, et al., Poly(ortho esters)—From Concept To Reality, Biomacromolecules, vol. 5, No. 5, 2004 (pp. 1625-1632), May 9, 1979.

Schwach-Abdellaoui, et al., Hydrolysis and Erosion Studies of Autocatalyzed Poly(ortho esters) Containing Lactoyl-Lactyl Acid Dimers, American Chemical Society, vol. 32, No. 2, 1999 (pp. 301-307).

Ng, et al., Synthesis and Erosion Studies of Self-Catalyzed Poly(ortho ester)s, American Chemical Society, vol. 30, No. 4, 1997 (pp. 770-772).

Ng, et al., Development Of A Poly(ortho ester) prototype With A Latent Acid In The Polymer Backbone For 5-fluorouracil Delivery, Journal of Controlled Release 65 (2000), (pp. 367-374). Rofhen-Weinhold, et al., Release of BSA from poly(ortho ester) extruded thin strands, Journal of Controlled Release 71, 2001, (pp. 31-37).

Heller, et al., Poly(ortho ester)s—their development and some recent applications, European Journal of Pharmaceutics and Biopharmaceutics, 50, 2000, (pp. 121-128).

Heller, et al., Poly(ortho esters); synthesis, characterizaiton, properties and uses, Advanced Drug Delivery Reviews, 54, 2002, (pp. 1015-1039).

Heller, et al., Poly(ortho esters) For The Pulsed And Continuous Delivery of Peptides And Proteins, Controlled Release and Biomedical Polymers Department, SRI International, (pp. 39-46), undated.

Zignani, et al., Subconjunctival biocompatability of a viscous bioerodable poly(ortho ester), J. Biomed Mater Res, 39, 1998, pp. 277-285.

Toncheva, et al., Use of Block Copolymers of Poly(Ortho Esters) and Poly (Ethylene Glycol), Journal of Drug Targeting, 2003, vol. 11(6), pp. 345-353.

Schwach-Abdellaoui, et al., Control of Molecular Weight For Auto-Catalyzed Poly(ortho ester) Obtained by Polycondensation Reaction, International Journal of Polymer Anal. Charact, 7: 145161, 2002, pp. 145-161.

Heller, et al., Release of Norethindrone from Poly(Ortho Esters), Polymer Engineering and Science, Mid-Aug., 1981, vol. 21, No. 11 (pp. 727-731).

Cordes, et al., Mechanism and Catalysis for Hydrolysis of Acetals, Ketals, and Other Esters, Department of Chemistry, Indiana University, Bloomington, Indiana, Chemical Reviews, 1974, vol. 74, No. 5, pp. 581-603.

Todd, et al., A Chemical "Trigger" Useful for Oilfield Applications, Society of Petroleum Engineers, Inc., SPE 92709, Feb. 4, 2005. Search Report and Written Opinion No. PCT/GB2006/000064, Sep. 1, 2006.