CA1251069A - Hydrogel contact lenses for extended wear - Google Patents
Hydrogel contact lenses for extended wearInfo
- Publication number
- CA1251069A CA1251069A CA000453077A CA453077A CA1251069A CA 1251069 A CA1251069 A CA 1251069A CA 000453077 A CA000453077 A CA 000453077A CA 453077 A CA453077 A CA 453077A CA 1251069 A CA1251069 A CA 1251069A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- tpt
- triazine
- tris
- monomer
- 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.)
- Expired
Links
- 239000000017 hydrogel Substances 0.000 title claims abstract description 18
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000003999 initiator Substances 0.000 claims abstract description 14
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000004132 cross linking Methods 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 6
- ZOCXRFWBGJJJGK-UHFFFAOYSA-N 2,4,6-tris(prop-1-enoxy)-1,3,5-triazine Chemical compound CC=COC1=NC(OC=CC)=NC(OC=CC)=N1 ZOCXRFWBGJJJGK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 230000000379 polymerizing effect Effects 0.000 claims abstract 4
- 239000007983 Tris buffer Substances 0.000 claims abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 11
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 10
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 10
- -1 hydroxyalkyl acrylate Chemical compound 0.000 claims description 6
- 230000008961 swelling Effects 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000005395 methacrylic acid group Chemical group 0.000 abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 8
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000005266 casting Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- JOBUGABETFOCAT-UHFFFAOYSA-N 4,5,6-tris(prop-1-enoxy)triazine Chemical compound CC=COC1=NN=NC(OC=CC)=C1OC=CC JOBUGABETFOCAT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/20—Esters of polyhydric alcohols or phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
- C08F226/10—N-Vinyl-pyrrolidone
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8311788 | 1983-04-29 | ||
| GB838311788A GB8311788D0 (en) | 1983-04-29 | 1983-04-29 | Hydrogel contact lenses |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1251069A true CA1251069A (en) | 1989-03-14 |
Family
ID=10541933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000453077A Expired CA1251069A (en) | 1983-04-29 | 1984-04-27 | Hydrogel contact lenses for extended wear |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US4451630A (en, 2012) |
| EP (1) | EP0127937A1 (en, 2012) |
| JP (1) | JPS60209720A (en, 2012) |
| CA (1) | CA1251069A (en, 2012) |
| GB (2) | GB8311788D0 (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3565358D1 (en) * | 1984-04-11 | 1988-11-10 | Intermedics Intraocular Inc | Ultraviolet light absorbing intraocular implants |
| US4620954A (en) * | 1985-06-07 | 1986-11-04 | Ciba Vision Care Corp. | Hydrogel from ultraviolet-initiated copolymerization |
| US4640941A (en) * | 1985-11-25 | 1987-02-03 | Alcon Laboratories | Hydrogels containing siloxane comonomers |
| US4640965A (en) * | 1986-01-07 | 1987-02-03 | Alcon Laboratories, Inc. | Hydrogel compositions using p-(2-hydroxyhexafluoroisopropyl) styrene as a comonomer |
| US4848353A (en) * | 1986-09-05 | 1989-07-18 | Minnesota Mining And Manufacturing Company | Electrically-conductive, pressure-sensitive adhesive and biomedical electrodes |
| JPH0643467B2 (ja) * | 1987-12-08 | 1994-06-08 | 呉羽化学工業株式会社 | 光学材料の製造方法 |
| US5258490A (en) * | 1987-12-14 | 1993-11-02 | Chang Sing Hsiung | Non-irritating soft gas permeable contact lens and process for producing same |
| US4992517A (en) * | 1989-04-19 | 1991-02-12 | Gaf Chemicals Corporation | Process for production of copolymers of maleic anhydride and an alkyl vinyl ether in a sterically hindered monoether solvent |
| US20070110378A1 (en) * | 2003-08-04 | 2007-05-17 | Zarian James R | Light-emitting form exhibiting an aura |
| US7235592B2 (en) | 2004-10-12 | 2007-06-26 | Zimmer Gmbh | PVA hydrogel |
| EP1858984A1 (en) * | 2005-02-23 | 2007-11-28 | Zimmer Technology, Inc. | Blend hydrogels and methods of making |
| EP2340855A1 (en) * | 2005-12-07 | 2011-07-06 | Zimmer, Inc. | Methods of modifying hydrogels using irradiation |
| DE602006017160D1 (de) | 2005-12-22 | 2010-11-11 | Zimmer Inc | Perfluorcyclobutanvernetzte Hydrogele |
| US8110242B2 (en) | 2006-03-24 | 2012-02-07 | Zimmer, Inc. | Methods of preparing hydrogel coatings |
| US7731988B2 (en) * | 2007-08-03 | 2010-06-08 | Zimmer, Inc. | Multi-polymer hydrogels |
| US8062739B2 (en) | 2007-08-31 | 2011-11-22 | Zimmer, Inc. | Hydrogels with gradient |
| US7947784B2 (en) | 2007-11-16 | 2011-05-24 | Zimmer, Inc. | Reactive compounding of hydrogels |
| US8034362B2 (en) | 2008-01-04 | 2011-10-11 | Zimmer, Inc. | Chemical composition of hydrogels for use as articulating surfaces |
| CN104861112B (zh) * | 2015-05-29 | 2017-03-08 | 天津大学 | 一种具有二氧化碳响应性的形状记忆抗撕裂水凝胶及其制备方法和应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3220960A (en) * | 1960-12-21 | 1965-11-30 | Wichterle Otto | Cross-linked hydrophilic polymers and articles made therefrom |
| GB1385677A (en) * | 1971-02-05 | 1975-02-26 | Carle J T De | Hydrophilic polymers and contact lenses manufactured therefrom |
| US3937680A (en) * | 1973-05-29 | 1976-02-10 | Global Vision, Inc. | Hydrophilic gel terpolymers from hydrophilic n-vinyl monomers, hydroxyalkyl acrylates or methacrylates and polymerizable unsaturated carboxylic acids |
| US4121896A (en) * | 1976-03-24 | 1978-10-24 | Shepherd Thomas H | Apparatus for the production of contact lenses |
| JPS598177B2 (ja) * | 1979-07-20 | 1984-02-23 | 呉羽化学工業株式会社 | ゲル濾過用ゲル |
-
1983
- 1983-04-29 GB GB838311788A patent/GB8311788D0/en active Pending
- 1983-06-16 US US06/505,419 patent/US4451630A/en not_active Expired - Fee Related
-
1984
- 1984-04-12 US US06/599,739 patent/US4492776A/en not_active Expired - Fee Related
- 1984-04-24 EP EP84302750A patent/EP0127937A1/en not_active Withdrawn
- 1984-04-24 GB GB08410415A patent/GB2138831B/en not_active Expired
- 1984-04-27 CA CA000453077A patent/CA1251069A/en not_active Expired
- 1984-05-01 JP JP59086285A patent/JPS60209720A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0127937A1 (en) | 1984-12-12 |
| US4451630A (en) | 1984-05-29 |
| JPH0117126B2 (en, 2012) | 1989-03-29 |
| JPS60209720A (ja) | 1985-10-22 |
| GB2138831B (en) | 1986-08-06 |
| GB2138831A (en) | 1984-10-31 |
| US4492776A (en) | 1985-01-08 |
| GB8311788D0 (en) | 1983-06-02 |
| GB8410415D0 (en) | 1984-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |