CA2427864A1 - Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers - Google Patents

Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers Download PDF

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Publication number
CA2427864A1
CA2427864A1 CA 2427864 CA2427864A CA2427864A1 CA 2427864 A1 CA2427864 A1 CA 2427864A1 CA 2427864 CA2427864 CA 2427864 CA 2427864 A CA2427864 A CA 2427864A CA 2427864 A1 CA2427864 A1 CA 2427864A1
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CA
Canada
Prior art keywords
methyl ether
glycol methyl
dipropylene glycol
extracting solvent
cured polymer
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 2427864
Other languages
French (fr)
Other versions
CA2427864C (en
Inventor
James D. Ford
Azaam Alli
Ture Kindt-Larsen
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Johnson and Johnson Vision Care Inc
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Individual
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Filing date
Publication date
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Publication of CA2427864A1 publication Critical patent/CA2427864A1/en
Application granted granted Critical
Publication of CA2427864C publication Critical patent/CA2427864C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/02—Chemical treatment or coating of shaped articles made of macromolecular substances with solvents, e.g. swelling agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/32—Post-polymerisation treatment
    • C08G77/34—Purification
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G02B1/041—Lenses
    • G02B1/043—Contact lenses
    • 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
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S134/00—Cleaning and liquid contact with solids
    • Y10S134/901—Contact lens
    • 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]

Abstract

This invention relates to solvents which may be used to extract polymers that are made of hydrophilic and hydrophobic monomers.

Claims (31)

1. A method of extracting cured polymers comprising hydrophobic and hydrophilic monomers, where the method comprises the steps of treating the cured polymer with an extracting solvent, wherein said extracting solvent when measured at 25 °C
(a) swells the cured polymer from about 0% to about 50%, and (b) has Hansen Solubility Parameters within the ranges of ~H = about [~H cured polymer + 2.5] to about [~H cured polymer -8.5]
~P = about [~P cured polymer + 0.5] to about [~P cured polymer -4.0] and ~D = about [~D cured polymer + 2.5] to about [~D cured polymer -2.0].
2. The method of claim 1 wherein said extracting solvent is selected from the group consisting of butyl acetate, propylene glycol methyl ether acetate, dipropylene glycol N-propyl ether, tripropylene glycol N-propyl ether, dipropylene glycol N-butyl ether, dipropylene glycol dimethyl ether dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether, tripropylene glycol methyl ether and mixtures thereof.
3. The method of claim 1 wherein said extracting solvent is selected from the group consisting of butyl acetate, dipropylene glycol dimethyl ether dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether tripropylene glycol methyl ether, and mixtures thereof.
4. The method of claim 1 wherein ~H is about 3.0 to about 14, ~P is about 2 to about 6.6, and ~D is about 14.0 to about 19.
5. The method of claim 1 wherein said extracting solvent comprises dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether, or tripropylene glycol methyl ether.
6. The method of claim 5 wherein said extracting solvent further comprises deionized water.
7. The method of claim 5 wherein said extracting solvent further comprises propylene glycol or deionized water.
8. The method of claim 1 wherein said extracting solvent comprises about 70 to about 98 percent by weight dipropylene glycol methyl ether, or tripropylene glycol methyl ether and about 2 to about 30 percent by weight propylene glycol or deionzed water.
9. The method of claim 1 wherein said extracting solvent comprises about 80 to about 90 percent by weight dipropylene glycol methyl ether, or tripropylene glycol methyl ether and about 10 to about 20 percent by weight propylene glycol or deionzed water.
10. The method of claim 1, claim 8, or claim 9 wherein said cured polymer is an ophthalmic device.
11. The method of claim 1 wherein the swell of the cured polymer is about 15% to about 40%.
12. A method of releasing and extracting cured polymers comprising hydrophobic and hydrophilic monomers, where the method comprises the steps of treating the cured polymer with an extracting solvent, wherein said'extracting solvent when measured at 25 °C
(a) swells the cured polymer to at least about 15% and (b) has Hansen Solubility Parameters within the ranges of ~H = about [~H cured polymer + 2.5] to about [~H cured polymer -8.5]
~P = about [~P cured polymer + 0.5] to about [~P cured polymer -4.0] and ~D = about [~D cured polymer + 2.5] to about [~D cured polymer -2.0].
13. The method of claim 12 wherein said extracting solvent is selected from the group consisting of butyl acetate, propylene glycol methyl ether acetate, dipropylene glycol N-propyl ether, tripropylene glycol N-propyl ether, dipropylene glycol N-butyl ether, dipropylene glycol dimethyl ether dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether, tripropylene glycol methyl ether and mixtures thereof.
14. The method of claim 12 wherein said extracting solvent is selected from the group consisting of butyl acetate, dipropylene glycol dimethyl ether dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether tripropylene glycol methyl ether, and mixtures thereof.
15. The method of claim 12 wherein ~H is about 3.0 to about 14, ~P is about 2 to about 6.6, and 8D is about 14.0 to about 19.
16. The method of claim 12 wherein said extracting solvent comprises dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether, or tripropylene glycol methyl ether.
17. The method of claim 16 wherein said extracting solvent further comprises deionized water.
18. The method of claim 16 wherein said extracting solvent further comprises propylene glycol.
19. The method of claim 12 wherein said extracting solvent comprises about 80 to about 90 percent by weight dipropylene glycol methyl ether, or tripropylene glycol methyl ether and about 10 to about 20 percent by weight propylene glycol or deionzed water.
20. The method of claim 12 wherein said extracting solvent comprises about 70 to about 98 percent by weight dipropylene glycol methyl ether, or tripropylene glycol methyl ether and about 2 to about 30 percent by weight propylene glycol or deionzed water.
21. The method of claim 12 wherein said cured polymer is a contact lens.
22. The method of claim 12 wherein the swell of the cured polymer is about 15% to about 40%.
23. A polymer that is prepared by a method of extracting cured polymers comprising hydrophobic and hydrophilic monomers, where the method comprises the steps of treating the cured polymer with an extracting solvent, wherein said extracting solvent when measured at 25 °C
(a) swells the cured polymer from about 0% to about 50% and (b) has Hansen Solubility Parameters within the ranges of ~H = about [~H cured polymer + 2.5] to about [~H cured polymer -8.5]
~P = about [~P cured polymer + 0.5] to about [~P cured polymer -4.0] and ~D = about [~D cured polymer + 2.5] to about [~D cured polymer -2.0].
24. The polymer of claim 23 wherein said extracting solvent is selected from the group consisting of butyl acetate, propylene glycol methyl ether acetate, dipropylene glycol N-propyl ether, tripropylene glycol N-propyl ether, dipropylene glycol N-butyl ether, dipropylene glycol dimethyl ether dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether, tripropylene glycol methyl ether and mixtures thereof.
25. The polymer of claim 23 wherein said extracting solvent is selected from the group consisting of butyl acetate, dipropylene glycol dimethyl ether dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether tripropylene glycol methyl ether, and mixtures thereof.
26. The polymer of claim 23 wherein ~H is about 3.0 to about 14, ~P is about 2 to about 6.6, and ~D is about 14.0 to about 19.
27. The polymer of claim 23 wherein said extracting solvent comprises dipropylene glycol methyl ether acetate, dipropylene glycol methyl ether, or tripropylene glycol methyl ether.
28. The polymer of claim 27 wherein said extracting solvent further comprises deionized water.
29. The polymer of claim 27 wherein said extracting solvent further comprises propylene glycol.
30. The polymer of claim 23 wherein said extracting solvent comprises about 80 to about 90 percent by weight dipropylene glycol methyl ether, or tripropylene glycol methyl ether and about 10 to about 20 percent by weight propylene glycol or deionzed water.
31. The polymer of claim 23 wherein said extracting solvent comprises about 70 to about 98 percent by weight dipropylene glycol methyl ether, or tripropylene glycol methyl ether and about 2 to about 30 percent by weight propylene glycol or deionzed water.
CA 2427864 2000-11-03 2001-10-30 Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers Expired - Lifetime CA2427864C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US24551800P 2000-11-03 2000-11-03
US60/245,518 2000-11-03
PCT/US2001/047536 WO2002036669A2 (en) 2000-11-03 2001-10-30 Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers

Publications (2)

Publication Number Publication Date
CA2427864A1 true CA2427864A1 (en) 2002-05-10
CA2427864C CA2427864C (en) 2010-08-17

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Family Applications (1)

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CA 2427864 Expired - Lifetime CA2427864C (en) 2000-11-03 2001-10-30 Solvents useful in the preparation of polymers containing hydrophilic and hydrophobic monomers

Country Status (13)

Country Link
US (2) US6765083B2 (en)
EP (1) EP1358256B1 (en)
JP (1) JP4769408B2 (en)
KR (1) KR20040005856A (en)
CN (1) CN1230465C (en)
AR (1) AR034273A1 (en)
AU (2) AU2733102A (en)
BR (1) BR0115118A (en)
CA (1) CA2427864C (en)
DE (1) DE60123130T2 (en)
HK (1) HK1057380A1 (en)
TW (1) TW593445B (en)
WO (1) WO2002036669A2 (en)

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US20070138669A1 (en) * 2005-12-21 2007-06-21 Yu-Chin Lai Process for Casting and Extracting Biomedical Devices
US8414804B2 (en) 2006-03-23 2013-04-09 Johnson & Johnson Vision Care, Inc. Process for making ophthalmic lenses
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US8507577B2 (en) * 2006-10-31 2013-08-13 Johnson & Johnson Vision Care, Inc. Process for forming clear, wettable silicone hydrogel articles
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US7759298B2 (en) * 2006-12-14 2010-07-20 The Boeing Company Thickened composition and method for removing adhesive residue
EP2126614B1 (en) * 2007-03-22 2019-04-24 Novartis AG Silicone-containing prepolymers with hydrophilic polymeric chains
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EP2152251A2 (en) 2007-04-27 2010-02-17 Medtronic, INC. Increased drug loading capacity of polymeric material
US7897202B2 (en) * 2007-05-18 2011-03-01 The Boeing Company Gelled solvent composition and method for restoring epoxy graphite composite materials
US20090032988A1 (en) * 2007-07-31 2009-02-05 Diana Zanini Ophthalmic lens processing to decrease dynamic contact angle
DE102007050428A1 (en) 2007-10-22 2009-04-23 Catena Additives Gmbh & Co. Kg Process for the preparation of granules starting from triethanolamine and an alkali or alkaline earth perchlorate
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CN102839518B (en) * 2011-06-22 2017-06-20 海尔集团公司 A kind of dry-cleaning method of Domestic dry washing machine and clothing
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Also Published As

Publication number Publication date
BR0115118A (en) 2004-10-19
DE60123130D1 (en) 2006-10-26
AU2733102A (en) 2002-05-15
JP2004512939A (en) 2004-04-30
US20050004345A1 (en) 2005-01-06
EP1358256A2 (en) 2003-11-05
US20020193559A1 (en) 2002-12-19
US7112652B2 (en) 2006-09-26
EP1358256B1 (en) 2006-09-13
CN1484669A (en) 2004-03-24
AU2002227331B2 (en) 2005-10-13
WO2002036669A3 (en) 2003-03-06
CA2427864C (en) 2010-08-17
DE60123130T2 (en) 2007-09-13
US6765083B2 (en) 2004-07-20
JP4769408B2 (en) 2011-09-07
HK1057380A1 (en) 2004-04-02
KR20040005856A (en) 2004-01-16
AR034273A1 (en) 2004-02-18
WO2002036669A2 (en) 2002-05-10
CN1230465C (en) 2005-12-07
TW593445B (en) 2004-06-21

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